#------------------------------------------------------------------------------ #$Date: 2015-12-30 10:21:14 +0000 (Wed, 30 Dec 2015) $ #$Revision: 171761 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238888.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2238888 loop_ _publ_author_name 'Sapnakumari, M.' 'Narayana, B.' 'Yathirajan, H.S.' 'Jasinski, Jerry P.' 'Butcher, Ray J.' _publ_section_title ; Ethyl 6-(4-chlorophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate ; _journal_coeditor_code LH5662 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1839 _journal_page_last o1840 _journal_paper_doi 10.1107/S1600536813031851 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C21 H18 Cl F O3' _chemical_formula_moiety 'C21 H18 Cl F O3' _chemical_formula_sum 'C21 H18 Cl F O3' _chemical_formula_weight 372.80 _chemical_name_systematic ; Ethyl 6-(4-chlorophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _cell_angle_alpha 77.250(3) _cell_angle_beta 87.320(3) _cell_angle_gamma 67.342(4) _cell_formula_units_Z 4 _cell_length_a 11.6611(5) _cell_length_b 13.1823(5) _cell_length_c 13.2251(5) _cell_measurement_reflns_used 6709 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 75.5164 _cell_measurement_theta_min 3.4266 _cell_volume 1828.15(14) _computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)' _computing_data_collection 'CrysAlis PRO (Agilent, 2012)' _computing_data_reduction 'CrysAlis RED (Agilent, 2012)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 123(2) _diffrn_detector_area_resol_mean 10.5081 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measurement_device_type 'Agilent Xcalibur (Ruby, Gemini)' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 13437 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 75.702 _diffrn_reflns_theta_min 3.429 _exptl_absorpt_coefficient_mu 2.089 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.50779 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO and CrysAlis RED; Agilent, 2012) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 776 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.678 _refine_diff_density_min -0.395 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 617 _refine_ls_number_reflns 7365 _refine_ls_number_restraints 177 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0554 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+1.2352P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1456 _refine_ls_wR_factor_ref 0.1483 _reflns_number_gt 6861 _reflns_number_total 7365 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh5662.cif _[local]_cod_data_source_block I _cod_database_code 2238888 #BEGIN Tags that were not found in dictionaries: _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; TITL I P -1 R = 0.06 CELL 1.54178 11.6611 13.1823 13.2251 77.25 87.32 67.342 ZERR 4 0.0005 0.0005 0.0005 0.003 0.003 0.004 LATT 1 SFAC C H Cl F O UNIT 84 72 4 4 12 EQIV $1 1-X,1-Y,-Z EQIV $2 1-X,1-Y,1-Z EQIV $3 +X,+Y,1+Z EQIV $4 2-X,1-Y,1-Z EQIV $5 +X,-1+Y,+Z SADI 0.005 C7A C3A C7A C3C DELU 0.002 0.002 C13A > C18B L.S. 15 PLAN 15 TEMP -150(2) HTAB C11A O1A_$1 HTAB C11A O1C_$1 HTAB C8A O1B HTAB C9A O2B HTAB C14A O2B_$2 HTAB C14C O2B_$2 HTAB C2A O1B HTAB C2A O2B_$2 HTAB C2C O1B HTAB C2C O2B_$2 HTAB C2B O1A_$3 HTAB C2B O1C_$3 HTAB C2B O2C_$4 HTAB C8B O1A_$3 HTAB C8B O1C_$3 HTAB C9B O2A_$3 HTAB C14B O2A_$4 HTAB C20B Cl1A_$5 BOND $H MORE -1 MORE -1 fmap 2 acta CONF OMIT 0 5 5 OMIT 0 3 5 OMIT -9 -7 2 OMIT 9 5 3 OMIT 0 2 8 REM F:/Papers%20in%20Progress-Oct-2013/ActaE-YBN-BYN%20Papers/BNY-508-Ray REM -To%20ActaE-LH5662/BNY-508b-Lough-Update-1/lh5662.hkl WGHT 0.063100 1.235200 FVAR 4.47868 0.68430 F1A 4 0.409027 0.183159 0.397053 11.00000 0.08907 0.07225 = 0.04491 -0.00736 0.00470 -0.06328 C7A 1 0.557245 0.417236 0.267810 11.00000 0.03132 0.03149 = 0.03054 -0.01132 0.00026 -0.01388 C8A 1 0.566700 0.374898 0.375168 11.00000 0.04030 0.04302 = 0.02943 -0.01132 -0.00062 -0.02321 AFIX 43 H8A 2 0.607199 0.400813 0.418407 11.00000 -1.20000 AFIX 0 C9A 1 0.517608 0.295518 0.419166 11.00000 0.05293 0.05182 = 0.02970 -0.00675 0.00076 -0.03115 AFIX 43 H9A 2 0.525361 0.265797 0.491945 11.00000 -1.20000 AFIX 0 C10A 1 0.457514 0.260737 0.355312 11.00000 0.05125 0.04416 = 0.03993 -0.00954 0.00540 -0.03217 C11A 1 0.442913 0.301809 0.249749 11.00000 0.04579 0.04216 = 0.03694 -0.01378 -0.00130 -0.02524 AFIX 43 H11A 2 0.399291 0.277312 0.207820 11.00000 -1.20000 AFIX 0 C12A 1 0.493712 0.380053 0.206223 11.00000 0.04125 0.03640 = 0.02930 -0.01048 -0.00137 -0.01934 AFIX 43 H12A 2 0.485301 0.408993 0.133316 11.00000 -1.20000 AFIX 66 PART 1 C13A 1 0.698734 0.731972 0.291494 21.00000 0.04968 0.04128 = 0.02801 -0.01488 0.00837 -0.02858 C14A 1 0.594075 0.823711 0.305996 21.00000 0.04285 0.05206 = 0.03169 -0.01968 0.00717 -0.02844 AFIX 43 H14A 2 0.515044 0.835201 0.278648 21.00000 -1.20000 AFIX 65 C15A 1 0.605048 0.898637 0.360512 21.00000 0.05385 0.04399 = 0.03444 -0.01694 0.00586 -0.02489 AFIX 43 H15A 2 0.533518 0.961336 0.370423 21.00000 -1.20000 AFIX 65 C16A 1 0.720681 0.881826 0.400526 21.00000 0.06460 0.04210 = 0.02349 -0.01240 0.00412 -0.03682 C17A 1 0.825341 0.790088 0.386025 21.00000 0.05306 0.04787 = 0.03415 -0.01066 -0.00101 -0.03339 AFIX 43 H17A 2 0.904370 0.778599 0.413373 21.00000 -1.20000 AFIX 65 C18A 1 0.814369 0.715160 0.331509 21.00000 0.04610 0.04219 = 0.03833 -0.01490 0.00271 -0.02416 AFIX 43 H18A 2 0.885899 0.652461 0.321598 21.00000 -1.20000 AFIX 66 PART 0 PART 2 C13C 1 0.663182 0.754994 0.283162 -21.00000 0.02193 0.02246 = 0.02206 -0.00556 -0.00325 -0.01011 C14C 1 0.575202 0.845523 0.317319 -21.00000 0.04539 0.04003 = 0.02866 -0.02686 0.01601 -0.02090 AFIX 43 H14C 2 0.489914 0.870570 0.297107 -21.00000 -1.20000 AFIX 65 C15C 1 0.612012 0.899405 0.381048 -21.00000 0.05991 0.04810 = 0.02492 -0.02373 0.01452 -0.03331 AFIX 43 H15C 2 0.551881 0.961278 0.404393 -21.00000 -1.20000 AFIX 65 C16C 1 0.736800 0.862758 0.410622 -21.00000 0.06408 0.04427 = 0.04001 -0.01682 0.01079 -0.04418 C17C 1 0.824781 0.772228 0.376465 -21.00000 0.04877 0.05621 = 0.04913 -0.02466 -0.00716 -0.03260 AFIX 43 H17C 2 0.910069 0.747182 0.396678 -21.00000 -1.20000 AFIX 65 C18C 1 0.787973 0.718346 0.312736 -21.00000 0.03180 0.04799 = 0.03436 -0.01626 -0.01639 -0.01644 AFIX 43 H18C 2 0.848104 0.656473 0.289391 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 O1A 5 0.708775 0.606125 -0.028739 21.00000 0.04593 0.05393 = 0.02845 -0.01591 0.00358 -0.02642 O2A 5 0.862222 0.746402 0.045316 21.00000 0.04396 0.05670 = 0.04261 -0.00994 0.00391 -0.03121 O3A 5 0.655130 0.835299 0.028627 21.00000 0.04706 0.03785 = 0.05576 -0.00829 0.00040 -0.02023 C1A 1 0.642219 0.681342 0.217095 21.00000 0.04057 0.03604 = 0.02855 -0.01164 0.00302 -0.02150 AFIX 13 H1A 2 0.559822 0.737818 0.185649 21.00000 -1.20000 AFIX 0 C2A 1 0.628387 0.575183 0.282549 21.00000 0.02399 0.02816 = 0.02419 -0.00802 -0.00384 -0.00849 AFIX 23 H2AA 2 0.700779 0.534390 0.332259 21.00000 -1.20000 H2AB 2 0.552917 0.598455 0.323327 21.00000 -1.20000 AFIX 0 C3A 1 0.619087 0.495242 0.219982 21.00000 0.01340 0.02139 = 0.03004 -0.00744 -0.00715 0.00046 C4A 1 0.643243 0.509447 0.117797 21.00000 0.04087 0.03493 = 0.03117 -0.01487 -0.00107 -0.01802 AFIX 43 H4A 2 0.624650 0.464981 0.078564 21.00000 -1.20000 AFIX 0 C5A 1 0.696271 0.589451 0.065107 21.00000 0.03304 0.03560 = 0.02805 -0.01234 -0.00211 -0.01402 C6A 1 0.735463 0.651225 0.132979 21.00000 0.03808 0.03851 = 0.02876 -0.01292 0.00161 -0.02082 AFIX 13 H6A 2 0.816386 0.597141 0.169052 21.00000 -1.20000 AFIX 0 C19A 1 0.760647 0.748250 0.063850 21.00000 0.04062 0.03925 = 0.02557 -0.01184 0.00113 -0.02091 C20A 1 0.667684 0.932926 -0.043909 21.00000 0.05949 0.03395 = 0.06406 -0.00625 -0.00372 -0.01954 AFIX 23 H20A 2 0.744305 0.941357 -0.025334 21.00000 -1.20000 H20B 2 0.595725 1.002642 -0.038985 21.00000 -1.20000 AFIX 0 C21A 1 0.673512 0.915203 -0.153514 21.00000 0.07888 0.04985 = 0.05459 0.00834 -0.01966 -0.03008 AFIX 33 H21A 2 0.681751 0.979958 -0.201619 21.00000 -1.50000 H21B 2 0.597166 0.907594 -0.171753 21.00000 -1.50000 H21C 2 0.745395 0.846575 -0.158176 21.00000 -1.50000 AFIX 0 CL1A 3 0.735620 0.973984 0.468464 21.00000 0.11198 0.06867 = 0.05353 -0.03294 0.01036 -0.06428 SAME 0.005 0.04 O1A > Cl1A PART 0 PART 2 O1C 5 0.706779 0.608649 -0.024809 -21.00000 0.08955 0.04637 = 0.01905 -0.01201 0.00703 -0.04343 O2C 5 0.848812 0.726394 0.076030 -21.00000 0.03809 0.06153 = 0.04608 -0.01327 0.01459 -0.03544 O3C 5 0.664258 0.854500 0.005582 -21.00000 0.06339 0.04585 = 0.04396 -0.00447 -0.00875 -0.03876 C1C 1 0.710777 0.637589 0.235501 -21.00000 0.01642 0.02583 = 0.02625 -0.01108 -0.00357 -0.00612 AFIX 13 H1C 2 0.801994 0.590824 0.244645 -21.00000 -1.20000 AFIX 0 C2C 1 0.625970 0.576721 0.284471 -21.00000 0.08577 0.05075 = 0.02679 -0.01865 0.01476 -0.05253 AFIX 23 H2CA 2 0.667428 0.523400 0.349627 -21.00000 -1.20000 H2CB 2 0.547867 0.633171 0.302935 -21.00000 -1.20000 AFIX 0 C3C 1 0.593476 0.512445 0.216315 -21.00000 0.00272 0.01844 = 0.02351 -0.00711 -0.00508 0.00325 C4C 1 0.640029 0.510717 0.120626 -21.00000 0.02847 0.03817 = 0.02386 -0.01222 0.00049 -0.01941 AFIX 43 H4C 2 0.652076 0.448574 0.090317 -21.00000 -1.20000 AFIX 0 C5C 1 0.671644 0.603884 0.064122 -21.00000 0.02585 0.03315 = 0.02390 -0.01204 0.00197 -0.01337 C6C 1 0.662435 0.693908 0.123007 -21.00000 0.01282 0.02815 = 0.02409 -0.01061 0.00208 -0.00588 AFIX 13 H6C 2 0.573546 0.746529 0.122396 -21.00000 -1.20000 AFIX 0 C19C 1 0.738463 0.758908 0.067676 -21.00000 0.03646 0.04011 = 0.02745 -0.02031 0.01205 -0.02283 C20C 1 0.738026 0.911156 -0.059576 -21.00000 0.06560 0.04468 = 0.04913 -0.01013 0.01580 -0.02679 AFIX 23 H20C 2 0.798242 0.860399 -0.099576 -21.00000 -1.20000 H20D 2 0.783376 0.937991 -0.017093 -21.00000 -1.20000 AFIX 0 C21C 1 0.639389 1.008431 -0.130203 -21.00000 0.10451 0.08960 = 0.08658 0.03969 0.00015 -0.02846 AFIX 33 H21D 2 0.677899 1.055403 -0.174729 -21.00000 -1.50000 H21E 2 0.577481 1.053695 -0.088334 -21.00000 -1.50000 H21F 2 0.598702 0.979394 -0.173435 -21.00000 -1.50000 AFIX 0 CL1C 3 0.775624 0.938632 0.486167 -21.00000 0.08067 0.06171 = 0.05242 -0.03071 0.00402 -0.04723 PART 0 CL1B 3 0.719256 0.054076 1.167675 11.00000 0.08087 0.05814 = 0.03887 -0.00490 0.00890 -0.04373 F1B 4 1.159551 0.766170 0.778089 11.00000 0.05278 0.04992 = 0.06855 -0.02581 0.00438 -0.03344 O1B 5 0.759780 0.445317 0.514770 11.00000 0.06973 0.06537 = 0.02917 -0.01455 -0.00283 -0.04194 O2B 5 0.660397 0.248830 0.661335 11.00000 0.05893 0.07981 = 0.07133 -0.04025 0.01586 -0.04717 O3B 5 0.861980 0.204846 0.634667 11.00000 0.04579 0.05461 = 0.07334 -0.03960 -0.00720 -0.01361 C1B 1 0.847993 0.335551 0.788614 11.00000 0.03751 0.03587 = 0.03162 -0.01255 -0.00249 -0.01859 AFIX 13 H1B 2 0.931497 0.286696 0.768703 11.00000 -1.20000 AFIX 0 C2B 1 0.860047 0.440195 0.812826 11.00000 0.03505 0.03307 = 0.02712 -0.01057 -0.00200 -0.01684 AFIX 23 H2BA 2 0.782063 0.484251 0.842620 11.00000 -1.20000 H2BB 2 0.928344 0.415463 0.865651 11.00000 -1.20000 AFIX 0 C3B 1 0.885696 0.514897 0.718288 11.00000 0.03141 0.03062 = 0.03054 -0.01106 -0.00067 -0.01264 C4B 1 0.849505 0.516344 0.622574 11.00000 0.04210 0.03858 = 0.02775 -0.00836 -0.00045 -0.02087 AFIX 43 H4B 2 0.864509 0.566777 0.565225 11.00000 -1.20000 AFIX 0 C5B 1 0.788551 0.444491 0.602616 11.00000 0.04082 0.04163 = 0.02835 -0.01312 -0.00077 -0.01963 C6B 1 0.756631 0.370183 0.695332 11.00000 0.03510 0.03935 = 0.03106 -0.01439 0.00034 -0.01837 AFIX 13 H6B 2 0.671778 0.414414 0.716599 11.00000 -1.20000 AFIX 0 C7B 1 0.953419 0.585495 0.733335 11.00000 0.03353 0.02962 = 0.03259 -0.01030 -0.00161 -0.01366 C8B 1 0.953903 0.615936 0.828683 11.00000 0.03881 0.03921 = 0.03642 -0.01681 0.00332 -0.01961 AFIX 43 H8B 2 0.906818 0.594003 0.883459 11.00000 -1.20000 AFIX 0 C9B 1 1.022420 0.677689 0.843681 11.00000 0.04221 0.04419 = 0.04513 -0.02400 0.00312 -0.02140 AFIX 43 H9B 2 1.022582 0.698309 0.908102 11.00000 -1.20000 AFIX 0 C10B 1 1.090089 0.708421 0.763347 11.00000 0.03780 0.03263 = 0.05273 -0.01515 -0.00176 -0.01764 C11B 1 1.091866 0.681285 0.668115 11.00000 0.04028 0.03499 = 0.04323 -0.00805 0.00195 -0.01990 AFIX 43 H11B 2 1.138687 0.704339 0.613725 11.00000 -1.20000 AFIX 0 C12B 1 1.023342 0.619433 0.654217 11.00000 0.03938 0.03580 = 0.03308 -0.00962 -0.00034 -0.01825 AFIX 43 H12B 2 1.023877 0.599586 0.589319 11.00000 -1.20000 AFIX 0 C13B 1 0.811778 0.267335 0.883805 11.00000 0.03970 0.03556 = 0.03089 -0.01270 -0.00316 -0.02169 C14B 1 0.904654 0.178187 0.946577 11.00000 0.03636 0.04742 = 0.03607 -0.00848 -0.00280 -0.02005 AFIX 43 H14B 2 0.989003 0.161229 0.929183 11.00000 -1.20000 AFIX 0 C15B 1 0.877183 0.113170 1.034242 11.00000 0.04731 0.04338 = 0.03744 -0.00321 -0.00459 -0.01787 AFIX 43 H15B 2 0.942038 0.052508 1.076720 11.00000 -1.20000 AFIX 0 C16B 1 0.754978 0.137394 1.059123 11.00000 0.05446 0.04031 = 0.03044 -0.00971 0.00257 -0.03010 C17B 1 0.660213 0.226519 0.999807 11.00000 0.04174 0.05235 = 0.04274 -0.01204 0.00452 -0.02281 AFIX 43 H17B 2 0.576134 0.243767 1.018198 11.00000 -1.20000 AFIX 0 C18B 1 0.689953 0.290929 0.912309 11.00000 0.03925 0.04262 = 0.04302 -0.00441 -0.00188 -0.01448 AFIX 43 H18B 2 0.624981 0.352722 0.871029 11.00000 -1.20000 AFIX 0 C19B 1 0.751670 0.268283 0.662919 11.00000 0.04823 0.04466 = 0.03173 -0.01615 0.00024 -0.02643 C20B 1 0.871503 0.104346 0.600902 11.00000 0.08499 0.04500 = 0.07682 -0.03498 -0.02162 -0.00852 AFIX 23 H20E 2 0.787121 0.107020 0.588894 11.00000 -1.20000 H20F 2 0.914538 0.101646 0.534633 11.00000 -1.20000 AFIX 0 C21B 1 0.938741 0.005646 0.677314 11.00000 0.11769 0.05381 = 0.09425 -0.01298 -0.02811 -0.02770 AFIX 33 H21G 2 0.944329 -0.061317 0.653404 11.00000 -1.50000 H21H 2 0.895428 0.007925 0.742597 11.00000 -1.50000 H21I 2 1.022639 0.002551 0.688414 11.00000 -1.50000 AFIX 0 HKLF 4 REM I P -1 R = 0.06 REM R1 = 0.0554 for 6861 Fo > 4sig(Fo) and 0.0584 for all 7365 data REM 617 parameters refined using 177 restraints END WGHT 0.0631 1.2370 REM Highest difference peak 0.678, deepest hole -0.395, 1-sigma level 0.051 Q1 1 0.7989 0.0057 1.1707 11.00000 0.05 0.68 Q2 1 0.8465 0.3271 0.7091 11.00000 0.05 0.54 Q3 1 0.7677 0.3850 0.7973 11.00000 0.05 0.37 Q4 1 0.9877 0.0202 0.6024 11.00000 0.05 0.31 Q5 1 0.7560 0.2995 0.9121 11.00000 0.05 0.30 Q6 1 0.8166 0.3767 0.5355 11.00000 0.05 0.29 Q7 1 0.8177 0.4773 0.6153 11.00000 0.05 0.26 Q8 1 0.6960 0.2423 0.7128 11.00000 0.05 0.25 Q9 1 0.9241 0.5433 0.7287 11.00000 0.05 0.24 Q10 1 0.6443 0.6251 0.2533 11.00000 0.05 0.23 Q11 1 0.6565 0.5575 0.0947 11.00000 0.05 0.23 Q12 1 0.7144 0.6197 0.0965 11.00000 0.05 0.23 Q13 1 0.3428 0.2570 0.3970 11.00000 0.05 0.22 Q14 1 0.5241 0.4029 0.2376 11.00000 0.05 0.22 Q15 1 0.7599 0.2432 0.8814 11.00000 0.05 0.22 REM The information below was added by Olex2. REM REM R1 = 0.0554 for 6861 Fo > 4sig(Fo) and 0.0584 for all 13446 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.68, deepest hole -0.39 REM Mean Shift 0, Max Shift 0. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0584 REM R1_gt = 0.0554 REM wR_ref = 0.1483 REM GOOF = 1.093 REM Shift_max = 0 REM Shift_mean = 0 REM Reflections_all = 13446 REM Reflections_gt = 6861 REM Parameters = n/a REM Hole = -0.39 REM Peak = 0.68 REM Flack = n/a ; #END Tags that were not found in dictionaries loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F F1A 0.40903(18) 0.18316(15) 0.39705(12) 0.0598(4) Uani d 1 . . C C7A 0.55724(18) 0.41724(17) 0.26781(15) 0.0298(4) Uani d 1 . . C C8A 0.5667(2) 0.37490(19) 0.37517(16) 0.0347(4) Uani d 1 . . H H8A 0.6072 0.4008 0.4184 0.042 Uiso calc 1 . . C C9A 0.5176(2) 0.2955(2) 0.41917(17) 0.0418(5) Uani d 1 . . H H9A 0.5254 0.2658 0.4919 0.050 Uiso calc 1 . . C C10A 0.4575(2) 0.2607(2) 0.35531(19) 0.0409(5) Uani d 1 . . C C11A 0.4429(2) 0.3018(2) 0.24975(18) 0.0381(5) Uani d 1 . . H H11A 0.3993 0.2773 0.2078 0.046 Uiso calc 1 . . C C12A 0.4937(2) 0.38005(18) 0.20622(16) 0.0336(4) Uani d 1 . . H H12A 0.4853 0.4090 0.1333 0.040 Uiso calc 1 . . C C13A 0.6987(4) 0.7320(5) 0.2915(6) 0.0352(12) Uani d 0.684(5) A 1 C C14A 0.5941(4) 0.8237(6) 0.3060(7) 0.0375(10) Uani d 0.684(5) A 1 H H14A 0.5150 0.8352 0.2786 0.045 Uiso calc 0.684(5) A 1 C C15A 0.6050(5) 0.8986(7) 0.3605(8) 0.0410(14) Uani d 0.684(5) A 1 H H15A 0.5335 0.9613 0.3704 0.049 Uiso calc 0.684(5) A 1 C C16A 0.7207(5) 0.8818(6) 0.4005(8) 0.0376(13) Uani d 0.684(5) A 1 C C17A 0.8253(4) 0.7901(6) 0.3860(6) 0.0403(10) Uani d 0.684(5) A 1 H H17A 0.9044 0.7786 0.4134 0.048 Uiso calc 0.684(5) A 1 C C18A 0.8144(4) 0.7152(4) 0.3315(5) 0.0390(11) Uani d 0.684(5) A 1 H H18A 0.8859 0.6525 0.3216 0.047 Uiso calc 0.684(5) A 1 C C13C 0.6632(8) 0.7550(10) 0.2832(12) 0.0214(16) Uani d 0.316(5) A 2 C C14C 0.5752(8) 0.8455(13) 0.3173(15) 0.0339(19) Uani d 0.316(5) A 2 H H14C 0.4899 0.8706 0.2971 0.041 Uiso calc 0.316(5) A 2 C C15C 0.6120(11) 0.8994(15) 0.3810(17) 0.038(2) Uani d 0.316(5) A 2 H H15C 0.5519 0.9613 0.4044 0.046 Uiso calc 0.316(5) A 2 C C16C 0.7368(12) 0.8628(15) 0.4106(17) 0.041(3) Uani d 0.316(5) A 2 C C17C 0.8248(9) 0.7722(14) 0.3765(16) 0.045(3) Uani d 0.316(5) A 2 H H17C 0.9101 0.7472 0.3967 0.054 Uiso calc 0.316(5) A 2 C C18C 0.7880(8) 0.7183(11) 0.3127(12) 0.036(2) Uani d 0.316(5) A 2 H H18C 0.8481 0.6565 0.2894 0.043 Uiso calc 0.316(5) A 2 O O1A 0.7088(8) 0.6061(9) -0.0287(5) 0.039(2) Uani d 0.684(5) A 1 O O2A 0.8622(4) 0.7464(5) 0.0453(4) 0.0443(9) Uani d 0.684(5) A 1 O O3A 0.6551(4) 0.8353(4) 0.0286(5) 0.0460(9) Uani d 0.684(5) A 1 C C1A 0.6422(4) 0.6813(3) 0.2171(2) 0.0323(7) Uani d 0.684(5) A 1 H H1A 0.5598 0.7378 0.1856 0.039 Uiso calc 0.684(5) A 1 C C2A 0.6284(5) 0.5752(5) 0.2825(5) 0.0254(11) Uani d 0.684(5) A 1 H H2AA 0.7008 0.5344 0.3323 0.030 Uiso calc 0.684(5) A 1 H H2AB 0.5529 0.5985 0.3233 0.030 Uiso calc 0.684(5) A 1 C C3A 0.6191(10) 0.4952(7) 0.2200(6) 0.0232(17) Uani d 0.684(5) A 1 C C4A 0.6432(19) 0.5094(11) 0.1178(8) 0.033(3) Uani d 0.684(5) A 1 H H4A 0.6247 0.4650 0.0786 0.040 Uiso calc 0.684(5) A 1 C C5A 0.6963(16) 0.5895(10) 0.0651(6) 0.031(2) Uani d 0.684(5) A 1 C C6A 0.7355(4) 0.6512(3) 0.1330(2) 0.0323(7) Uani d 0.684(5) A 1 H H6A 0.8164 0.5971 0.1691 0.039 Uiso calc 0.684(5) A 1 C C19A 0.7606(5) 0.7482(7) 0.0639(9) 0.0326(13) Uani d 0.684(5) A 1 C C20A 0.6677(5) 0.9329(3) -0.0439(3) 0.0526(10) Uani d 0.684(5) A 1 H H20A 0.7443 0.9414 -0.0253 0.063 Uiso calc 0.684(5) A 1 H H20B 0.5957 1.0026 -0.0390 0.063 Uiso calc 0.684(5) A 1 C C21A 0.6735(5) 0.9152(4) -0.1535(3) 0.0620(12) Uani d 0.684(5) A 1 H H21A 0.6818 0.9800 -0.2016 0.093 Uiso calc 0.684(5) A 1 H H21B 0.5972 0.9076 -0.1718 0.093 Uiso calc 0.684(5) A 1 H H21C 0.7454 0.8466 -0.1582 0.093 Uiso calc 0.684(5) A 1 Cl Cl1A 0.7356(3) 0.9740(2) 0.4685(2) 0.0659(7) Uani d 0.684(5) A 1 O O1C 0.707(2) 0.609(2) -0.0248(11) 0.046(5) Uani d 0.316(5) A 2 O O2C 0.8488(8) 0.7264(10) 0.0760(8) 0.0437(19) Uani d 0.316(5) A 2 O O3C 0.6643(10) 0.8545(9) 0.0056(10) 0.046(2) Uani d 0.316(5) A 2 C C1C 0.7108(6) 0.6376(5) 0.2355(4) 0.0224(11) Uani d 0.316(5) A 2 H H1C 0.8020 0.5908 0.2446 0.027 Uiso calc 0.316(5) A 2 C C2C 0.6260(19) 0.5767(16) 0.2845(12) 0.045(4) Uani d 0.316(5) A 2 H H2CA 0.6674 0.5234 0.3496 0.054 Uiso calc 0.316(5) A 2 H H2CB 0.5479 0.6332 0.3029 0.054 Uiso calc 0.316(5) A 2 C C3C 0.593(2) 0.5124(13) 0.2163(12) 0.017(3) Uani d 0.316(5) A 2 C C4C 0.640(4) 0.511(2) 0.1206(16) 0.027(6) Uani d 0.316(5) A 2 H H4C 0.6521 0.4486 0.0903 0.033 Uiso calc 0.316(5) A 2 C C5C 0.672(3) 0.604(2) 0.0641(12) 0.026(4) Uani d 0.316(5) A 2 C C6C 0.6624(6) 0.6939(5) 0.1230(4) 0.0215(12) Uani d 0.316(5) A 2 H H6C 0.5735 0.7465 0.1224 0.026 Uiso calc 0.316(5) A 2 C C19C 0.7385(9) 0.7589(13) 0.0677(19) 0.030(2) Uani d 0.316(5) A 2 C C20C 0.7380(9) 0.9112(7) -0.0596(7) 0.052(2) Uani d 0.316(5) A 2 H H20C 0.7982 0.8604 -0.0996 0.062 Uiso calc 0.316(5) A 2 H H20D 0.7834 0.9380 -0.0171 0.062 Uiso calc 0.316(5) A 2 C C21C 0.6394(13) 1.0084(12) -0.1302(11) 0.106(6) Uani d 0.316(5) A 2 H H21D 0.6779 1.0554 -0.1747 0.159 Uiso calc 0.316(5) A 2 H H21E 0.5775 1.0537 -0.0883 0.159 Uiso calc 0.316(5) A 2 H H21F 0.5987 0.9794 -0.1734 0.159 Uiso calc 0.316(5) A 2 Cl Cl1C 0.7756(6) 0.9386(5) 0.4862(5) 0.0558(11) Uani d 0.316(5) A 2 Cl Cl1B 0.71926(7) 0.05408(6) 1.16767(5) 0.05522(19) Uani d 1 . . F F1B 1.15955(14) 0.76617(13) 0.77809(13) 0.0508(4) Uani d 1 . . O O1B 0.75978(18) 0.44532(17) 0.51477(12) 0.0490(4) Uani d 1 . . O O2B 0.66040(19) 0.2488(2) 0.66133(17) 0.0602(5) Uani d 1 . . O O3B 0.86198(17) 0.20485(17) 0.63467(17) 0.0551(5) Uani d 1 . . C C1B 0.8480(2) 0.33555(18) 0.78861(16) 0.0326(4) Uani d 1 . . H H1B 0.9315 0.2867 0.7687 0.039 Uiso calc 1 . . C C2B 0.86005(19) 0.44019(17) 0.81283(15) 0.0298(4) Uani d 1 . . H H2BA 0.7821 0.4843 0.8426 0.036 Uiso calc 1 . . H H2BB 0.9283 0.4155 0.8657 0.036 Uiso calc 1 . . C C3B 0.88570(19) 0.51490(17) 0.71829(16) 0.0298(4) Uani d 1 . . C C4B 0.8495(2) 0.51634(19) 0.62257(16) 0.0342(4) Uani d 1 . . H H4B 0.8645 0.5668 0.5652 0.041 Uiso calc 1 . . C C5B 0.7886(2) 0.44449(19) 0.60262(16) 0.0348(4) Uani d 1 . . C C6B 0.7566(2) 0.37018(18) 0.69533(16) 0.0328(4) Uani d 1 . . H H6B 0.6718 0.4144 0.7166 0.039 Uiso calc 1 . . C C7B 0.95342(19) 0.58550(17) 0.73334(16) 0.0308(4) Uani d 1 . . C C8B 0.9539(2) 0.61594(19) 0.82868(17) 0.0354(4) Uani d 1 . . H H8B 0.9068 0.5940 0.8835 0.042 Uiso calc 1 . . C C9B 1.0224(2) 0.6777(2) 0.84368(19) 0.0400(5) Uani d 1 . . H H9B 1.0226 0.6983 0.9081 0.048 Uiso calc 1 . . C C10B 1.0901(2) 0.70842(19) 0.76335(19) 0.0387(4) Uani d 1 . . C C11B 1.0919(2) 0.68128(19) 0.66812(18) 0.0379(4) Uani d 1 . . H H11B 1.1387 0.7043 0.6137 0.046 Uiso calc 1 . . C C12B 1.0233(2) 0.61943(18) 0.65422(17) 0.0345(4) Uani d 1 . . H H12B 1.0239 0.5996 0.5893 0.041 Uiso calc 1 . . C C13B 0.8118(2) 0.26734(18) 0.88381(16) 0.0321(4) Uani d 1 . . C C14B 0.9047(2) 0.1782(2) 0.94658(17) 0.0387(4) Uani d 1 . . H H14B 0.9890 0.1612 0.9292 0.046 Uiso calc 1 . . C C15B 0.8772(2) 0.1132(2) 1.03424(19) 0.0433(5) Uani d 1 . . H H15B 0.9420 0.0525 1.0767 0.052 Uiso calc 1 . . C C16B 0.7550(2) 0.13739(19) 1.05912(17) 0.0378(4) Uani d 1 . . C C17B 0.6602(2) 0.2265(2) 0.99981(19) 0.0440(5) Uani d 1 . . H H17B 0.5761 0.2438 1.0182 0.053 Uiso calc 1 . . C C18B 0.6900(2) 0.2909(2) 0.91231(19) 0.0427(5) Uani d 1 . . H H18B 0.6250 0.3527 0.8710 0.051 Uiso calc 1 . . C C19B 0.7517(2) 0.2683(2) 0.66292(17) 0.0375(5) Uani d 1 . . C C20B 0.8715(4) 0.1043(2) 0.6009(3) 0.0696(9) Uani d 1 . . H H20E 0.7871 0.1070 0.5889 0.083 Uiso calc 1 . . H H20F 0.9145 0.1016 0.5346 0.083 Uiso calc 1 . . C C21B 0.9387(5) 0.0056(3) 0.6773(4) 0.0896(13) Uani d 1 . . H H21G 0.9443 -0.0613 0.6534 0.134 Uiso calc 1 . . H H21H 0.8954 0.0079 0.7426 0.134 Uiso calc 1 . . H H21I 1.0226 0.0026 0.6884 0.134 Uiso calc 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1A 0.0891(12) 0.0722(11) 0.0449(8) -0.0633(10) 0.0047(8) -0.0074(7) C7A 0.0313(10) 0.0315(9) 0.0305(10) -0.0139(8) 0.0003(7) -0.0113(8) C8A 0.0403(11) 0.0430(11) 0.0294(10) -0.0232(9) -0.0006(8) -0.0113(8) C9A 0.0529(13) 0.0518(13) 0.0297(10) -0.0312(11) 0.0008(9) -0.0068(9) C10A 0.0513(13) 0.0442(12) 0.0399(12) -0.0322(11) 0.0054(10) -0.0095(9) C11A 0.0458(12) 0.0422(11) 0.0369(11) -0.0252(10) -0.0013(9) -0.0138(9) C12A 0.0413(11) 0.0364(10) 0.0293(10) -0.0193(9) -0.0014(8) -0.0105(8) C13A 0.050(3) 0.041(3) 0.028(2) -0.029(2) 0.008(3) -0.015(3) C14A 0.043(2) 0.052(3) 0.032(3) -0.0284(19) 0.007(2) -0.020(2) C15A 0.054(2) 0.044(2) 0.034(4) -0.0249(17) 0.0059(17) -0.0169(19) C16A 0.065(3) 0.042(3) 0.023(2) -0.0368(17) 0.0041(19) -0.012(2) C17A 0.053(2) 0.048(2) 0.034(3) -0.0334(17) -0.0010(19) -0.0107(18) C18A 0.046(2) 0.042(2) 0.038(3) -0.0242(18) 0.003(2) -0.015(2) C13C 0.022(4) 0.022(4) 0.022(3) -0.010(3) -0.003(3) -0.006(3) C14C 0.045(3) 0.040(5) 0.029(5) -0.021(3) 0.016(4) -0.027(4) C15C 0.060(4) 0.048(5) 0.025(7) -0.033(4) 0.015(3) -0.024(4) C16C 0.064(4) 0.044(6) 0.040(8) -0.044(4) 0.011(5) -0.017(6) C17C 0.049(4) 0.056(7) 0.049(6) -0.033(4) -0.007(4) -0.025(5) C18C 0.032(3) 0.048(4) 0.034(5) -0.016(3) -0.016(4) -0.016(3) O1A 0.046(4) 0.054(5) 0.028(2) -0.026(3) 0.004(2) -0.016(3) O2A 0.0440(16) 0.057(2) 0.043(3) -0.0312(13) 0.0039(15) -0.0099(17) O3A 0.0471(15) 0.038(2) 0.056(2) -0.0202(15) 0.0004(15) -0.0083(13) C1A 0.0406(19) 0.0360(16) 0.0286(14) -0.0215(15) 0.0030(12) -0.0116(11) C2A 0.024(2) 0.028(2) 0.0242(19) -0.0085(19) -0.0038(18) -0.0080(15) C3A 0.013(4) 0.021(2) 0.0300(18) 0.000(3) -0.0071(18) -0.0074(15) C4A 0.041(9) 0.035(5) 0.031(3) -0.018(5) -0.001(5) -0.015(4) C5A 0.033(7) 0.036(3) 0.0280(17) -0.014(4) -0.0021(17) -0.0123(15) C6A 0.0381(19) 0.0385(15) 0.0288(13) -0.0208(15) 0.0016(11) -0.0129(10) C19A 0.041(2) 0.039(2) 0.026(2) -0.0209(18) 0.001(2) -0.0118(19) C20A 0.059(3) 0.0339(17) 0.064(2) -0.0195(19) -0.004(2) -0.0062(15) C21A 0.079(3) 0.050(2) 0.0546(18) -0.030(2) -0.020(2) 0.0083(17) Cl1A 0.112(2) 0.0687(14) 0.0535(11) -0.0643(14) 0.0104(11) -0.0329(11) O1C 0.090(13) 0.046(10) 0.019(5) -0.043(9) 0.007(6) -0.012(5) O2C 0.038(3) 0.062(5) 0.046(6) -0.035(3) 0.015(3) -0.013(4) O3C 0.063(4) 0.046(4) 0.044(5) -0.039(3) -0.009(3) -0.004(2) C1C 0.016(3) 0.026(3) 0.026(2) -0.006(2) -0.004(2) -0.0111(18) C2C 0.086(12) 0.051(8) 0.027(4) -0.053(9) 0.015(7) -0.019(5) C3C 0.003(7) 0.018(5) 0.024(4) 0.003(5) -0.005(3) -0.007(3) C4C 0.028(15) 0.038(9) 0.024(7) -0.019(11) 0.000(9) -0.012(7) C5C 0.026(11) 0.033(6) 0.024(3) -0.013(8) 0.002(4) -0.012(3) C6C 0.013(3) 0.028(3) 0.024(2) -0.006(2) 0.0021(18) -0.0106(17) C19C 0.036(4) 0.040(4) 0.027(4) -0.023(3) 0.012(4) -0.020(3) C20C 0.066(6) 0.045(4) 0.049(4) -0.027(4) 0.016(4) -0.010(3) C21C 0.105(9) 0.090(10) 0.087(9) -0.028(7) 0.000(7) 0.040(7) Cl1C 0.081(3) 0.062(3) 0.052(2) -0.047(2) 0.0040(16) -0.031(2) Cl1B 0.0809(5) 0.0581(4) 0.0389(3) -0.0437(4) 0.0089(3) -0.0049(3) F1B 0.0528(8) 0.0499(8) 0.0685(10) -0.0334(7) 0.0044(7) -0.0258(7) O1B 0.0697(12) 0.0654(11) 0.0292(7) -0.0419(10) -0.0028(7) -0.0146(7) O2B 0.0589(11) 0.0798(14) 0.0713(13) -0.0472(11) 0.0159(10) -0.0402(11) O3B 0.0458(10) 0.0546(11) 0.0733(13) -0.0136(8) -0.0072(9) -0.0396(10) C1B 0.0375(10) 0.0359(10) 0.0316(9) -0.0186(8) -0.0025(7) -0.0126(7) C2B 0.0351(10) 0.0331(9) 0.0271(8) -0.0168(8) -0.0020(7) -0.0106(7) C3B 0.0314(9) 0.0306(9) 0.0305(9) -0.0126(7) -0.0007(7) -0.0111(7) C4B 0.0421(11) 0.0386(11) 0.0277(9) -0.0209(9) -0.0005(8) -0.0084(8) C5B 0.0408(11) 0.0416(11) 0.0284(8) -0.0196(9) -0.0008(8) -0.0131(8) C6B 0.0351(10) 0.0393(11) 0.0311(8) -0.0184(8) 0.0003(7) -0.0144(7) C7B 0.0335(10) 0.0296(9) 0.0326(9) -0.0137(8) -0.0016(7) -0.0103(7) C8B 0.0388(11) 0.0392(11) 0.0364(10) -0.0196(9) 0.0033(8) -0.0168(9) C9B 0.0422(12) 0.0442(12) 0.0451(11) -0.0214(9) 0.0031(9) -0.0240(10) C10B 0.0378(11) 0.0326(10) 0.0527(12) -0.0176(9) -0.0018(9) -0.0152(9) C11B 0.0403(11) 0.0350(11) 0.0432(10) -0.0199(9) 0.0019(9) -0.0080(9) C12B 0.0394(11) 0.0358(10) 0.0331(9) -0.0183(8) -0.0003(8) -0.0096(8) C13B 0.0397(10) 0.0356(9) 0.0309(9) -0.0217(8) -0.0032(7) -0.0127(7) C14B 0.0364(10) 0.0474(12) 0.0361(10) -0.0200(9) -0.0028(8) -0.0085(8) C15B 0.0473(11) 0.0434(12) 0.0374(11) -0.0179(10) -0.0046(9) -0.0032(8) C16B 0.0545(11) 0.0403(11) 0.0304(10) -0.0301(9) 0.0026(8) -0.0097(7) C17B 0.0417(11) 0.0523(13) 0.0427(11) -0.0228(9) 0.0045(9) -0.0120(9) C18B 0.0392(10) 0.0426(12) 0.0430(11) -0.0145(9) -0.0019(9) -0.0044(9) C19B 0.0482(12) 0.0447(12) 0.0317(10) -0.0264(10) 0.0002(9) -0.0161(9) C20B 0.085(2) 0.0450(15) 0.077(2) -0.0085(15) -0.0216(17) -0.0350(15) C21B 0.118(3) 0.0538(19) 0.094(3) -0.028(2) -0.028(2) -0.0130(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C8A C7A C12A 118.40(19) C8A C7A C3A 120.5(4) C8A C7A C3C 123.7(7) C12A C7A C3A 121.0(4) C12A C7A C3C 117.2(7) C7A C8A H8A 119.6 C9A C8A C7A 120.72(19) C9A C8A H8A 119.6 C8A C9A H9A 120.7 C10A C9A C8A 118.6(2) C10A C9A H9A 120.7 F1A C10A C9A 119.4(2) F1A C10A C11A 117.7(2) C9A C10A C11A 122.9(2) C10A C11A H11A 121.0 C10A C11A C12A 118.1(2) C12A C11A H11A 121.0 C7A C12A H12A 119.4 C11A C12A C7A 121.2(2) C11A C12A H12A 119.4 C14A C13A C18A 120.0 C14A C13A C1A 101.1(3) C18A C13A C1A 138.6(3) C13A C14A H14A 120.0 C15A C14A C13A 120.0 C15A C14A H14A 120.0 C14A C15A H15A 120.0 C14A C15A C16A 120.0 C16A C15A H15A 120.0 C15A C16A C17A 120.0 C15A C16A Cl1A 120.5(2) C17A C16A Cl1A 119.5(2) C16A C17A H17A 120.0 C16A C17A C18A 120.0 C18A C17A H17A 120.0 C13A C18A H18A 120.0 C17A C18A C13A 120.0 C17A C18A H18A 120.0 C14C C13C C18C 120.0 C14C C13C C1C 154.5(6) C18C C13C C1C 84.1(5) C13C C14C H14C 120.0 C13C C14C C15C 120.0 C15C C14C H14C 120.0 C14C C15C H15C 120.0 C16C C15C C14C 120.0 C16C C15C H15C 120.0 C15C C16C C17C 120.0 C15C C16C Cl1C 117.0(6) C17C C16C Cl1C 123.0(6) C16C C17C H17C 120.0 C16C C17C C18C 120.0 C18C C17C H17C 120.0 C13C C18C H18C 120.0 C17C C18C C13C 120.0 C17C C18C H18C 120.0 C19A O3A C20A 116.4(4) C13A C1A H1A 110.6 C2A C1A C13A 107.7(4) C2A C1A H1A 110.6 C6A C1A C13A 106.7(3) C6A C1A H1A 110.6 C6A C1A C2A 110.6(4) C1A C2A H2AA 108.7 C1A C2A H2AB 108.7 H2AA C2A H2AB 107.6 C3A C2A C1A 114.3(3) C3A C2A H2AA 108.7 C3A C2A H2AB 108.7 C7A C3A C2A 117.5(5) C4A C3A C7A 120.6(6) C4A C3A C2A 120.6(4) C3A C4A H4A 118.4 C3A C4A C5A 123.3(7) C5A C4A H4A 118.4 O1A C5A C4A 121.7(7) O1A C5A C6A 121.8(7) C4A C5A C6A 116.5(6) C1A C6A H6A 106.9 C5A C6A C1A 110.4(5) C5A C6A H6A 106.9 C19A C6A C1A 116.2(5) C19A C6A C5A 109.0(6) C19A C6A H6A 106.9 O2A C19A O3A 124.9(4) O2A C19A C6A 123.7(4) O3A C19A C6A 111.4(4) O3A C20A H20A 109.8 O3A C20A H20B 109.8 O3A C20A C21A 109.5(4) H20A C20A H20B 108.2 C21A C20A H20A 109.8 C21A C20A H20B 109.8 C20A C21A H21A 109.5 C20A C21A H21B 109.5 C20A C21A H21C 109.5 H21A C21A H21B 109.5 H21A C21A H21C 109.5 H21B C21A H21C 109.5 C19C O3C C20C 110.8(8) C13C C1C H1C 115.3 C2C C1C C13C 104.3(10) C2C C1C H1C 115.3 C6C C1C C13C 97.9(6) C6C C1C H1C 115.3 C6C C1C C2C 107.0(8) C1C C2C H2CA 108.5 C1C C2C H2CB 108.5 H2CA C2C H2CB 107.5 C3C C2C C1C 114.9(8) C3C C2C H2CA 108.5 C3C C2C H2CB 108.5 C7A C3C C2C 118.0(9) C4C C3C C7A 117.5(11) C4C C3C C2C 119.9(10) C3C C4C H4C 119.9 C3C C4C C5C 120.2(13) C5C C4C H4C 119.9 O1C C5C C4C 122.1(13) O1C C5C C6C 121.6(13) C4C C5C C6C 116.3(11) C1C C6C H6C 109.3 C5C C6C C1C 109.5(11) C5C C6C H6C 109.3 C19C C6C C1C 111.4(9) C19C C6C C5C 107.9(13) C19C C6C H6C 109.3 O2C C19C O3C 125.5(8) O2C C19C C6C 124.4(8) O3C C19C C6C 110.1(7) O3C C20C H20C 111.3 O3C C20C H20D 111.3 O3C C20C C21C 102.4(8) H20C C20C H20D 109.2 C21C C20C H20C 111.3 C21C C20C H20D 111.3 C20C C21C H21D 109.5 C20C C21C H21E 109.5 C20C C21C H21F 109.5 H21D C21C H21E 109.5 H21D C21C H21F 109.5 H21E C21C H21F 109.5 C19B O3B C20B 117.5(2) C2B C1B H1B 107.6 C6B C1B H1B 107.6 C6B C1B C2B 110.35(17) C13B C1B H1B 107.6 C13B C1B C2B 111.21(16) C13B C1B C6B 112.24(17) C1B C2B H2BA 109.0 C1B C2B H2BB 109.0 H2BA C2B H2BB 107.8 C3B C2B C1B 112.74(16) C3B C2B H2BA 109.0 C3B C2B H2BB 109.0 C4B C3B C2B 120.95(18) C4B C3B C7B 120.86(19) C7B C3B C2B 118.18(17) C3B C4B H4B 118.4 C3B C4B C5B 123.3(2) C5B C4B H4B 118.4 O1B C5B C4B 121.9(2) O1B C5B C6B 120.09(19) C4B C5B C6B 117.97(17) C1B C6B H6B 107.9 C5B C6B C1B 112.02(17) C5B C6B H6B 107.9 C19B C6B C1B 111.75(18) C19B C6B C5B 109.21(17) C19B C6B H6B 107.9 C8B C7B C3B 121.13(19) C12B C7B C3B 120.62(18) C12B C7B C8B 118.19(19) C7B C8B H8B 119.6 C9B C8B C7B 120.7(2) C9B C8B H8B 119.6 C8B C9B H9B 120.7 C10B C9B C8B 118.7(2) C10B C9B H9B 120.7 F1B C10B C9B 119.1(2) F1B C10B C11B 118.2(2) C9B C10B C11B 122.8(2) C10B C11B H11B 121.0 C10B C11B C12B 118.0(2) C12B C11B H11B 121.0 C7B C12B H12B 119.2 C11B C12B C7B 121.6(2) C11B C12B H12B 119.2 C14B C13B C1B 118.9(2) C14B C13B C18B 117.8(2) C18B C13B C1B 123.3(2) C13B C14B H14B 119.3 C13B C14B C15B 121.4(2) C15B C14B H14B 119.3 C14B C15B H15B 120.4 C16B C15B C14B 119.3(2) C16B C15B H15B 120.4 C15B C16B Cl1B 119.63(19) C17B C16B Cl1B 119.30(19) C17B C16B C15B 121.1(2) C16B C17B H17B 120.7 C16B C17B C18B 118.7(2) C18B C17B H17B 120.7 C13B C18B C17B 121.7(2) C13B C18B H18B 119.1 C17B C18B H18B 119.1 O2B C19B O3B 124.3(2) O2B C19B C6B 124.5(2) O3B C19B C6B 111.16(19) O3B C20B H20E 109.6 O3B C20B H20F 109.6 H20E C20B H20F 108.1 C21B C20B O3B 110.5(3) C21B C20B H20E 109.6 C21B C20B H20F 109.6 C20B C21B H21G 109.5 C20B C21B H21H 109.5 C20B C21B H21I 109.5 H21G C21B H21H 109.5 H21G C21B H21I 109.5 H21H C21B H21I 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1A C10A 1.355(3) C7A C8A 1.399(3) C7A C12A 1.402(3) C7A C3A 1.490(4) C7A C3C 1.491(5) C8A H8A 0.9500 C8A C9A 1.387(3) C9A H9A 0.9500 C9A C10A 1.374(3) C10A C11A 1.374(3) C11A H11A 0.9500 C11A C12A 1.387(3) C12A H12A 0.9500 C13A C14A 1.3900 C13A C18A 1.3900 C13A C1A 1.593(4) C14A H14A 0.9500 C14A C15A 1.3900 C15A H15A 0.9500 C15A C16A 1.3900 C16A C17A 1.3900 C16A Cl1A 1.724(3) C17A H17A 0.9500 C17A C18A 1.3900 C18A H18A 0.9500 C13C C14C 1.3900 C13C C18C 1.3900 C13C C1C 1.684(9) C14C H14C 0.9500 C14C C15C 1.3900 C15C H15C 0.9500 C15C C16C 1.3900 C16C C17C 1.3900 C16C Cl1C 1.742(7) C17C H17C 0.9500 C17C C18C 1.3900 C18C H18C 0.9500 O1A C5A 1.224(5) O2A C19A 1.190(5) O3A C19A 1.333(5) O3A C20A 1.478(5) C1A H1A 1.0000 C1A C2A 1.536(4) C1A C6A 1.525(4) C2A H2AA 0.9900 C2A H2AB 0.9900 C2A C3A 1.513(4) C3A C4A 1.354(5) C4A H4A 0.9500 C4A C5A 1.455(5) C5A C6A 1.525(6) C6A H6A 1.0000 C6A C19A 1.519(4) C20A H20A 0.9900 C20A H20B 0.9900 C20A C21A 1.513(6) C21A H21A 0.9800 C21A H21B 0.9800 C21A H21C 0.9800 O1C C5C 1.224(6) O2C C19C 1.191(6) O3C C19C 1.334(6) O3C C20C 1.477(6) C1C H1C 1.0000 C1C C2C 1.537(6) C1C C6C 1.533(5) C2C H2CA 0.9900 C2C H2CB 0.9900 C2C C3C 1.513(5) C3C C4C 1.355(6) C4C H4C 0.9500 C4C C5C 1.456(6) C5C C6C 1.526(6) C6C H6C 1.0000 C6C C19C 1.518(5) C20C H20C 0.9900 C20C H20D 0.9900 C20C C21C 1.508(7) C21C H21D 0.9800 C21C H21E 0.9800 C21C H21F 0.9800 Cl1B C16B 1.744(2) F1B C10B 1.352(2) O1B C5B 1.221(3) O2B C19B 1.189(3) O3B C19B 1.326(3) O3B C20B 1.453(3) C1B H1B 1.0000 C1B C2B 1.541(3) C1B C6B 1.538(3) C1B C13B 1.522(3) C2B H2BA 0.9900 C2B H2BB 0.9900 C2B C3B 1.507(3) C3B C4B 1.347(3) C3B C7B 1.481(3) C4B H4B 0.9500 C4B C5B 1.456(3) C5B C6B 1.520(3) C6B H6B 1.0000 C6B C19B 1.519(3) C7B C8B 1.406(3) C7B C12B 1.398(3) C8B H8B 0.9500 C8B C9B 1.388(3) C9B H9B 0.9500 C9B C10B 1.376(3) C10B C11B 1.380(3) C11B H11B 0.9500 C11B C12B 1.385(3) C12B H12B 0.9500 C13B C14B 1.384(3) C13B C18B 1.385(3) C14B H14B 0.9500 C14B C15B 1.385(3) C15B H15B 0.9500 C15B C16B 1.376(4) C16B C17B 1.375(4) C17B H17B 0.9500 C17B C18B 1.391(3) C18B H18B 0.9500 C20B H20E 0.9900 C20B H20F 0.9900 C20B C21B 1.427(5) C21B H21G 0.9800 C21B H21H 0.9800 C21B H21I 0.9800 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C8A H8A O1B . 0.95 2.55 3.478(3) 167.0 C2A H2AA O1B . 0.99 2.44 3.288(6) 143.2 C2A H2AB O2B 2_666 0.99 2.56 3.432(7) 146.8 C2C H2CA O1B . 0.99 2.32 3.278(18) 163.7 C2C H2CB O2B 2_666 0.99 2.42 3.40(2) 169.8 C2B H2BA O1A 1_556 0.99 2.49 3.315(8) 140.2 C2B H2BA O1C 1_556 0.99 2.56 3.380(18) 140.2 C2B H2BB O2C 2_766 0.99 2.58 3.436(10) 144.9 C8B H8B O1A 1_556 0.95 2.50 3.379(8) 153.7 C8B H8B O1C 1_556 0.95 2.54 3.417(19) 153.9 C9B H9B O2A 1_556 0.95 2.54 3.274(6) 133.8 C14B H14B O2A 2_766 0.95 2.54 3.247(5) 131.1 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion F1A C10A C11A C12A -179.1(2) C7A C8A C9A C10A -1.1(4) C7A C3A C4A C5A 176.1(14) C7A C3C C4C C5C 177(3) C8A C7A C12A C11A -1.0(3) C8A C7A C3A C2A -33.0(10) C8A C7A C3A C4A 159.8(12) C8A C7A C3C C2C -8(2) C8A C7A C3C C4C 147(2) C8A C9A C10A F1A 180.0(2) C8A C9A C10A C11A -0.6(4) C9A C10A C11A C12A 1.4(4) C10A C11A C12A C7A -0.6(3) C12A C7A C8A C9A 1.9(3) C12A C7A C3A C2A 150.2(6) C12A C7A C3A C4A -17.0(14) C12A C7A C3C C2C 161.9(14) C12A C7A C3C C4C -42(3) C13A C14A C15A C16A 0.0 C13A C1A C2A C3A -159.9(6) C13A C1A C6A C5A 173.5(7) C13A C1A C6A C19A -61.8(6) C14A C13A C18A C17A 0.0 C14A C13A C1A C2A -104.5(5) C14A C13A C1A C6A 136.7(4) C14A C15A C16A C17A 0.0 C14A C15A C16A Cl1A -179.9(8) C15A C16A C17A C18A 0.0 C16A C17A C18A C13A 0.0 C18A C13A C14A C15A 0.0 C18A C13A C1A C2A 82.8(8) C18A C13A C1A C6A -35.9(9) C13C C14C C15C C16C 0.0 C13C C1C C2C C3C 146.2(15) C13C C1C C6C C5C -169.5(13) C13C C1C C6C C19C 71.2(12) C14C C13C C18C C17C 0.0 C14C C13C C1C C2C -35(2) C14C C13C C1C C6C 74(2) C14C C15C C16C C17C 0.0 C14C C15C C16C Cl1C 177.4(18) C15C C16C C17C C18C 0.0 C16C C17C C18C C13C 0.0 C18C C13C C14C C15C 0.0 C18C C13C C1C C2C 126.7(11) C18C C13C C1C C6C -123.5(8) O1A C5A C6A C1A 141.5(14) O1A C5A C6A C19A 12.7(18) C1A C13A C14A C15A -174.4(6) C1A C13A C18A C17A 171.6(9) C1A C2A C3A C7A -156.4(6) C1A C2A C3A C4A 10.8(15) C1A C6A C19A O2A 130.9(11) C1A C6A C19A O3A -48.1(12) C2A C1A C6A C5A 56.6(7) C2A C1A C6A C19A -178.6(5) C2A C3A C4A C5A 9(3) C3A C7A C8A C9A -174.9(5) C3A C7A C12A C11A 175.8(5) C3A C7A C3C C2C -86(5) C3A C7A C3C C4C 70(5) C3A C4A C5A O1A -174.7(17) C3A C4A C5A C6A 5(3) C4A C5A C6A C1A -38.6(16) C4A C5A C6A C19A -167.4(13) C5A C6A C19A O2A -103.6(14) C5A C6A C19A O3A 77.4(12) C6A C1A C2A C3A -43.6(6) C19A O3A C20A C21A 86.8(10) C20A O3A C19A O2A 4.0(18) C20A O3A C19A C6A -177.1(7) Cl1A C16A C17A C18A 179.9(8) O1C C5C C6C C1C -139(3) O1C C5C C6C C19C -17(4) C1C C13C C14C C15C 159(2) C1C C13C C18C C17C -171.2(11) C1C C2C C3C C7A 156.1(14) C1C C2C C3C C4C 1(3) C1C C6C C19C O2C 41(3) C1C C6C C19C O3C -141.6(17) C2C C1C C6C C5C -61.9(15) C2C C1C C6C C19C 178.8(13) C2C C3C C4C C5C -28(5) C3C C7A C8A C9A 172.2(10) C3C C7A C12A C11A -171.9(9) C3C C7A C3A C2A 76(5) C3C C7A C3A C4A -91(5) C3C C4C C5C O1C -176(3) C3C C4C C5C C6C 6(5) C4C C5C C6C C1C 40(3) C4C C5C C6C C19C 161(3) C5C C6C C19C O2C -79(3) C5C C6C C19C O3C 98(2) C6C C1C C2C C3C 43.2(18) C19C O3C C20C C21C 174.3(19) C20C O3C C19C O2C 5(4) C20C O3C C19C C6C -172.2(15) Cl1C C16C C17C C18C -177.3(19) Cl1B C16B C17B C18B -178.78(19) F1B C10B C11B C12B 178.2(2) O1B C5B C6B C1B 152.6(2) O1B C5B C6B C19B 28.2(3) C1B C2B C3B C4B 26.2(3) C1B C2B C3B C7B -152.95(18) C1B C6B C19B O2B 120.3(3) C1B C6B C19B O3B -60.9(2) C1B C13B C14B C15B 180.0(2) C1B C13B C18B C17B 179.8(2) C2B C1B C6B C5B 51.7(2) C2B C1B C6B C19B 174.65(17) C2B C1B C13B C14B -94.2(2) C2B C1B C13B C18B 84.7(2) C2B C3B C4B C5B -2.4(3) C2B C3B C7B C8B -23.3(3) C2B C3B C7B C12B 153.8(2) C3B C4B C5B O1B -177.9(2) C3B C4B C5B C6B 4.3(3) C3B C7B C8B C9B 176.9(2) C3B C7B C12B C11B -177.1(2) C4B C3B C7B C8B 157.5(2) C4B C3B C7B C12B -25.4(3) C4B C5B C6B C1B -29.6(3) C4B C5B C6B C19B -154.0(2) C5B C6B C19B O2B -115.2(3) C5B C6B C19B O3B 63.6(2) C6B C1B C2B C3B -50.1(2) C6B C1B C13B C14B 141.6(2) C6B C1B C13B C18B -39.5(3) C7B C3B C4B C5B 176.66(19) C7B C8B C9B C10B -0.1(4) C8B C7B C12B C11B 0.1(3) C8B C9B C10B F1B -178.4(2) C8B C9B C10B C11B 0.6(4) C9B C10B C11B C12B -0.7(4) C10B C11B C12B C7B 0.4(3) C12B C7B C8B C9B -0.2(3) C13B C1B C2B C3B -175.38(17) C13B C1B C6B C5B 176.38(17) C13B C1B C6B C19B -60.7(2) C13B C14B C15B C16B 0.3(4) C14B C13B C18B C17B -1.3(3) C14B C15B C16B Cl1B 178.56(18) C14B C15B C16B C17B -1.5(4) C15B C16B C17B C18B 1.3(4) C16B C17B C18B C13B 0.1(4) C18B C13B C14B C15B 1.0(3) C19B O3B C20B C21B -107.9(4) C20B O3B C19B O2B -0.8(4) C20B O3B C19B C6B -179.6(2)