#------------------------------------------------------------------------------ #$Date: 2014-01-12 09:24:12 +0000 (Sun, 12 Jan 2014) $ #$Revision: 92192 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238872.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_2238872 loop_ _publ_author_name 'Kaur, Manpreet' 'Jasinski, Jerry P.' 'Anderson, Brian J.' 'Yathirajan, H. S.' 'Narayana, B.' _publ_section_title ; N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-phenylacetamide ; _journal_coeditor_code HG5356 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1726 _journal_page_last o1727 _journal_paper_doi 10.1107/S1600536813029590 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C19 H19 N3 O2' _chemical_formula_moiety 'C19 H19 N3 O2' _chemical_formula_sum 'C19 H19 N3 O2' _chemical_formula_weight 321.37 _chemical_name_common ; N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)- 2-phenylacetamide ; _chemical_name_systematic N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-phenylacetamide _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 100.833(6) _cell_angle_beta 92.527(5) _cell_angle_gamma 116.812(7) _cell_formula_units_Z 4 _cell_length_a 10.1258(7) _cell_length_b 10.4671(8) _cell_length_c 17.8888(12) _cell_measurement_reflns_used 4663 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 72.2643 _cell_measurement_theta_min 4.8640 _cell_volume 1643.9(2) _computing_cell_refinement 'CrysAlisPro (Agilent, 2012)' _computing_data_collection 'CrysAlisPro (Agilent, 2012)' _computing_data_reduction 'CrysAlisRed (Agilent, 2012)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2008)' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 16.0416 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device_type 'Agilent Xcalibur (Eos, Gemini)' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 10216 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.414 _diffrn_reflns_theta_min 4.868 _exptl_absorpt_coefficient_mu 0.693 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.87598 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlisPro and CrysAlisRed; Agilent, 2012) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.298 _exptl_crystal_description irregular _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.297 _refine_diff_density_min -0.230 _refine_ls_extinction_coef 0.0080(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 438 _refine_ls_number_reflns 6333 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0462 _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^)+(0.0717P)^2^+0.2800P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1234 _refine_ls_wR_factor_ref 0.1302 _reflns_number_gt 5485 _reflns_number_total 6333 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL HSY-630 in P-1 #2 CELL 1.54184 10.12581 10.46706 17.88877 100.8326 92.5273 116.8118 ZERR 4 0.00068 0.00079 0.00118 0.006 0.0054 0.0071 LATT 1 SFAC C H N O UNIT 76 76 12 8 EQIV $1 1-X,1-Y,-Z EQIV $2 1-X,1-Y,1-Z EQIV $3 -1+X,-1+Y,+Z L.S. 15 PLAN 15 HTAB N1A O2B HTAB C14A O1A_$1 HTAB N1B O2A HTAB C2B O1B_$2 HTAB C4B O1B_$2 HTAB C8B O2A HTAB C14B O1A_$3 REM reset to P-1 #2 BOND $h MORE -1 fmap 2 acta CONF REM J:/yathirajan%202013/HSY-630-MK/HSY-630.hkl WGHT 0.071700 0.280000 EXTI 0.007981 FVAR 7.87002 O1A 4 0.534842 0.153158 0.111126 11.00000 0.02969 0.04113 = 0.02985 0.01208 0.01062 0.01741 O2A 4 0.186703 0.299537 0.189007 11.00000 0.04553 0.03494 = 0.01834 0.00784 0.01039 0.02653 N1A 3 0.307910 0.086411 0.150505 11.00000 0.02572 0.02158 = 0.02267 0.00912 0.00694 0.01156 AFIX 43 H1A 2 0.248696 0.039387 0.180007 11.00000 -1.20000 AFIX 0 N2A 3 0.167581 0.285755 0.057586 11.00000 0.03178 0.02770 = 0.01782 0.00597 0.00637 0.01765 N3A 3 0.214844 0.221282 -0.004545 11.00000 0.03204 0.02810 = 0.01612 0.00320 0.00500 0.01611 C1A 1 0.448944 0.102442 0.156135 11.00000 0.02698 0.02146 = 0.02509 0.00496 0.00514 0.01245 C2A 1 0.494591 0.053452 0.223477 11.00000 0.03330 0.03107 = 0.03547 0.01384 0.00665 0.01857 AFIX 23 H2AA 2 0.414147 0.021396 0.254223 11.00000 -1.20000 H2AB 2 0.513783 -0.028724 0.204320 11.00000 -1.20000 AFIX 0 C3A 1 0.633933 0.180339 0.272446 11.00000 0.03331 0.03635 = 0.02721 0.01458 0.00599 0.02156 C4A 1 0.623836 0.272966 0.335636 11.00000 0.03616 0.04492 = 0.03133 0.01320 0.00983 0.02420 AFIX 43 H4A 2 0.530759 0.251376 0.350683 11.00000 -1.20000 AFIX 0 C5A 1 0.750051 0.397681 0.377094 11.00000 0.05087 0.04498 = 0.02822 0.00700 0.00495 0.02678 AFIX 43 H5A 2 0.741161 0.458858 0.419320 11.00000 -1.20000 AFIX 0 C6A 1 0.888881 0.430163 0.355134 11.00000 0.03904 0.04423 = 0.03340 0.01184 -0.00422 0.01560 AFIX 43 H6A 2 0.973552 0.514025 0.382217 11.00000 -1.20000 AFIX 0 C7A 1 0.901607 0.337885 0.292927 11.00000 0.02993 0.05641 = 0.03873 0.01818 0.00584 0.02230 AFIX 43 H7A 2 0.995061 0.359055 0.278512 11.00000 -1.20000 AFIX 0 C8A 1 0.775399 0.213937 0.252024 11.00000 0.03652 0.04859 = 0.02931 0.01156 0.00858 0.02718 AFIX 43 H8A 2 0.784993 0.152181 0.210352 11.00000 -1.20000 AFIX 0 C9A 1 0.254869 0.143759 0.098268 11.00000 0.02111 0.02013 = 0.01978 0.00381 0.00351 0.00821 C10A 1 0.256518 0.126946 0.020987 11.00000 0.02599 0.02077 = 0.02199 0.00322 0.00465 0.00988 C11A 1 0.200635 0.247205 0.123889 11.00000 0.02179 0.02197 = 0.01930 0.00660 0.00390 0.00943 C12A 1 0.175983 0.426611 0.059388 11.00000 0.02871 0.02552 = 0.01919 0.00519 -0.00062 0.01402 C13A 1 0.274227 0.520086 0.018694 11.00000 0.03009 0.03133 = 0.02526 0.00753 0.00418 0.01258 AFIX 43 H13A 2 0.333837 0.491169 -0.010671 11.00000 -1.20000 AFIX 0 C14A 1 0.282353 0.657260 0.022394 11.00000 0.04240 0.02764 = 0.03545 0.01173 0.00259 0.00924 AFIX 43 H14A 2 0.345730 0.719693 -0.005695 11.00000 -1.20000 AFIX 0 C15A 1 0.196162 0.701128 0.067874 11.00000 0.05817 0.02846 = 0.03706 0.00467 -0.00283 0.02332 AFIX 43 H15A 2 0.203092 0.793709 0.071031 11.00000 -1.20000 AFIX 0 C16A 1 0.099922 0.607546 0.108549 11.00000 0.05420 0.04370 = 0.02966 0.00563 0.00558 0.03526 AFIX 43 H16A 2 0.042923 0.637838 0.139360 11.00000 -1.20000 AFIX 0 C17A 1 0.087654 0.468553 0.103770 11.00000 0.03719 0.03643 = 0.02494 0.01083 0.00670 0.02158 AFIX 43 H17A 2 0.020903 0.404588 0.130081 11.00000 -1.20000 AFIX 0 C18A 1 0.122078 0.178069 -0.079283 11.00000 0.03653 0.03497 = 0.01902 0.00545 0.00134 0.01460 AFIX 137 H18A 2 0.024317 0.100349 -0.078412 11.00000 -1.50000 H18B 2 0.167541 0.144367 -0.118971 11.00000 -1.50000 H18C 2 0.113685 0.261220 -0.089362 11.00000 -1.50000 AFIX 0 C19A 1 0.291420 0.025044 -0.034251 11.00000 0.04853 0.03430 = 0.02390 0.00185 0.00865 0.02371 AFIX 137 H19A 2 0.200185 -0.054196 -0.063792 11.00000 -1.50000 H19B 2 0.342100 -0.014020 -0.006423 11.00000 -1.50000 H19C 2 0.354497 0.077596 -0.068178 11.00000 -1.50000 AFIX 0 O1B 4 0.315917 0.347876 0.463369 11.00000 0.03451 0.03859 = 0.02293 0.00952 -0.00287 0.00526 O2B 4 0.099344 -0.056122 0.245549 11.00000 0.02864 0.02636 = 0.02780 0.00492 0.01169 0.01051 N1B 3 0.210770 0.254964 0.338111 11.00000 0.02438 0.02223 = 0.01903 0.00720 0.00402 0.00643 AFIX 43 H1B 2 0.220658 0.267893 0.292203 11.00000 -1.20000 AFIX 0 N2B 3 -0.088029 -0.109888 0.323057 11.00000 0.02200 0.02327 = 0.02278 0.00356 0.00664 0.00760 N3B 3 -0.131480 -0.026616 0.377360 11.00000 0.02550 0.02550 = 0.02361 0.00519 0.00955 0.00955 C1B 1 0.314604 0.359011 0.396592 11.00000 0.02385 0.02401 = 0.02425 0.00641 0.00387 0.01028 C2B 1 0.427795 0.494908 0.372493 11.00000 0.02288 0.02425 = 0.02907 0.00560 0.00586 0.00752 AFIX 23 H2BA 2 0.523798 0.534796 0.404429 11.00000 -1.20000 H2BB 2 0.440561 0.467309 0.319485 11.00000 -1.20000 AFIX 0 C3B 1 0.376140 0.611503 0.380344 11.00000 0.01940 0.02141 = 0.02818 0.00667 0.00877 0.00443 C4B 1 0.403301 0.707088 0.451490 11.00000 0.02591 0.03265 = 0.02687 0.00488 0.00638 0.00991 AFIX 43 H4B 2 0.450458 0.697106 0.494178 11.00000 -1.20000 AFIX 0 C5B 1 0.360806 0.816712 0.459258 11.00000 0.03786 0.03417 = 0.03701 -0.00105 0.01170 0.01462 AFIX 43 H5B 2 0.379145 0.879645 0.507112 11.00000 -1.20000 AFIX 0 C6B 1 0.291008 0.833247 0.396063 11.00000 0.04204 0.03371 = 0.05102 0.01133 0.01694 0.02244 AFIX 43 H6B 2 0.264017 0.908083 0.401276 11.00000 -1.20000 AFIX 0 C7B 1 0.261691 0.738124 0.325300 11.00000 0.03578 0.04034 = 0.03887 0.01621 0.00936 0.01933 AFIX 43 H7B 2 0.214057 0.748226 0.282830 11.00000 -1.20000 AFIX 0 C8B 1 0.303534 0.627172 0.317658 11.00000 0.02926 0.02810 = 0.02628 0.00522 0.00587 0.01018 AFIX 43 H8B 2 0.282651 0.562749 0.270028 11.00000 -1.20000 AFIX 0 C9B 1 0.087123 0.126413 0.347685 11.00000 0.02202 0.02333 = 0.01918 0.00596 0.00308 0.00930 C10B 1 -0.018689 0.115224 0.394615 11.00000 0.02448 0.02402 = 0.02191 0.00606 0.00317 0.01011 C11B 1 0.043946 -0.015227 0.299564 11.00000 0.02055 0.02428 = 0.02020 0.00797 0.00288 0.00973 C12B 1 -0.203717 -0.237745 0.270728 11.00000 0.02369 0.02294 = 0.02180 0.00712 0.00596 0.00510 C13B 1 -0.179984 -0.358039 0.246508 11.00000 0.03351 0.02736 = 0.03047 0.00922 0.00733 0.01089 AFIX 43 H13B 2 -0.092789 -0.357379 0.265753 11.00000 -1.20000 AFIX 0 C14B 1 -0.287986 -0.480028 0.193041 11.00000 0.04865 0.02349 = 0.03637 0.00321 0.01374 0.00681 AFIX 43 H14B 2 -0.272912 -0.561417 0.176159 11.00000 -1.20000 AFIX 0 C15B 1 -0.417024 -0.480873 0.165006 11.00000 0.03404 0.03943 = 0.02868 -0.00098 0.00698 -0.00579 AFIX 43 H15B 2 -0.488513 -0.562538 0.128900 11.00000 -1.20000 AFIX 0 C16B 1 -0.441099 -0.360942 0.190205 11.00000 0.02421 0.05781 = 0.03005 0.00531 0.00233 0.00779 AFIX 43 H16B 2 -0.529148 -0.362669 0.171419 11.00000 -1.20000 AFIX 0 C17B 1 -0.334188 -0.237889 0.243491 11.00000 0.02892 0.03723 = 0.02984 0.00652 0.00616 0.01267 AFIX 43 H17B 2 -0.349824 -0.156924 0.260625 11.00000 -1.20000 AFIX 0 C18B 1 -0.219148 -0.099911 0.433000 11.00000 0.03727 0.03449 = 0.03390 0.01190 0.01828 0.01254 AFIX 137 H18D 2 -0.296741 -0.195718 0.406925 11.00000 -1.50000 H18E 2 -0.263201 -0.042666 0.458437 11.00000 -1.50000 H18F 2 -0.155334 -0.109699 0.470340 11.00000 -1.50000 AFIX 0 C19B 1 -0.024494 0.228599 0.456419 11.00000 0.03654 0.03155 = 0.02978 0.00311 0.00953 0.01675 AFIX 137 H19D 2 -0.121609 0.223302 0.450059 11.00000 -1.50000 H19E 2 0.050244 0.324505 0.453440 11.00000 -1.50000 H19F 2 -0.005867 0.211210 0.505672 11.00000 -1.50000 AFIX 0 HKLF 4 REM HSY-630 in P-1 #2 REM R1 = 0.0462 for 5485 Fo > 4sig(Fo) and 0.0526 for all 6333 data REM 438 parameters refined using 0 restraints END WGHT 0.0717 0.2759 REM Highest difference peak 0.297, deepest hole -0.230, 1-sigma level 0.053 Q1 1 0.3173 0.1790 0.0789 11.00000 0.05 0.30 Q2 1 0.2133 0.0988 0.0595 11.00000 0.05 0.27 Q3 1 0.2186 0.1765 0.1170 11.00000 0.05 0.25 Q4 1 -0.1764 -0.2820 0.2478 11.00000 0.05 0.24 Q5 1 0.2002 0.3725 0.0694 11.00000 0.05 0.23 Q6 1 -0.3085 -0.1019 0.4213 11.00000 0.05 0.22 Q7 1 0.0212 0.1381 0.3512 11.00000 0.05 0.22 Q8 1 0.2804 0.6980 0.0673 11.00000 0.05 0.22 Q9 1 0.1546 0.1926 0.3449 11.00000 0.05 0.21 Q10 1 0.4673 0.0761 0.1929 11.00000 0.05 0.21 Q11 1 0.4948 0.1670 0.0547 11.00000 0.05 0.21 Q12 1 0.3094 0.5925 0.3519 11.00000 0.05 0.20 Q13 1 0.3587 0.4401 0.3840 11.00000 0.05 0.20 Q14 1 0.3664 0.3359 0.4361 11.00000 0.05 0.20 Q15 1 -0.2108 -0.1871 0.4304 11.00000 0.05 0.19 ; _[local]_cod_data_source_file hg5356.cif _[local]_cod_data_source_block I _cod_database_code 2238872 _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_hkl_checksum 93352 _shelx_res_checksum 21067 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 O O1A 0.53484(12) 0.15316(13) 0.11113(6) 0.0325(3) Uani d 1 O O2A 0.18670(13) 0.29954(12) 0.18901(6) 0.0295(3) Uani d 1 N N1A 0.30791(13) 0.08641(13) 0.15051(7) 0.0224(3) Uani d 1 H H1A 0.2487 0.0394 0.1800 0.027 Uiso calc 1 N N2A 0.16758(14) 0.28576(14) 0.05759(7) 0.0241(3) Uani d 1 N N3A 0.21484(14) 0.22128(14) -0.00455(7) 0.0249(3) Uani d 1 C C1A 0.44894(16) 0.10244(16) 0.15614(8) 0.0241(3) Uani d 1 C C2A 0.49459(18) 0.05345(18) 0.22348(10) 0.0309(3) Uani d 1 H H2AA 0.4141 0.0214 0.2542 0.037 Uiso calc 1 H H2AB 0.5138 -0.0287 0.2043 0.037 Uiso calc 1 C C3A 0.63393(18) 0.18034(18) 0.27245(9) 0.0291(3) Uani d 1 C C4A 0.62384(19) 0.2730(2) 0.33564(10) 0.0346(4) Uani d 1 H H4A 0.5308 0.2514 0.3507 0.042 Uiso calc 1 C C5A 0.7501(2) 0.3977(2) 0.37709(10) 0.0399(4) Uani d 1 H H5A 0.7412 0.4589 0.4193 0.048 Uiso calc 1 C C6A 0.8889(2) 0.4302(2) 0.35513(10) 0.0403(4) Uani d 1 H H6A 0.9736 0.5140 0.3822 0.048 Uiso calc 1 C C7A 0.90161(19) 0.3379(2) 0.29293(11) 0.0398(4) Uani d 1 H H7A 0.9951 0.3591 0.2785 0.048 Uiso calc 1 C C8A 0.77540(19) 0.2139(2) 0.25202(10) 0.0348(4) Uani d 1 H H8A 0.7850 0.1522 0.2104 0.042 Uiso calc 1 C C9A 0.25487(15) 0.14376(15) 0.09827(8) 0.0210(3) Uani d 1 C C10A 0.25652(16) 0.12695(16) 0.02099(8) 0.0236(3) Uani d 1 C C11A 0.20064(15) 0.24720(15) 0.12389(8) 0.0210(3) Uani d 1 C C12A 0.17598(16) 0.42661(16) 0.05939(8) 0.0241(3) Uani d 1 C C13A 0.27423(17) 0.52009(18) 0.01869(9) 0.0295(3) Uani d 1 H H13A 0.3338 0.4912 -0.0107 0.035 Uiso calc 1 C C14A 0.2824(2) 0.65726(19) 0.02239(10) 0.0374(4) Uani d 1 H H14A 0.3457 0.7197 -0.0057 0.045 Uiso calc 1 C C15A 0.1962(2) 0.70113(19) 0.06787(11) 0.0408(4) Uani d 1 H H15A 0.2031 0.7937 0.0710 0.049 Uiso calc 1 C C16A 0.0999(2) 0.6075(2) 0.10855(10) 0.0381(4) Uani d 1 H H16A 0.0429 0.6378 0.1394 0.046 Uiso calc 1 C C17A 0.08765(18) 0.46855(18) 0.10377(9) 0.0305(3) Uani d 1 H H17A 0.0209 0.4046 0.1301 0.037 Uiso calc 1 C C18A 0.12208(19) 0.17807(18) -0.07928(8) 0.0312(3) Uani d 1 H H18A 0.0243 0.1003 -0.0784 0.047 Uiso calc 1 H H18B 0.1675 0.1444 -0.1190 0.047 Uiso calc 1 H H18C 0.1137 0.2612 -0.0894 0.047 Uiso calc 1 C C19A 0.2914(2) 0.02504(19) -0.03425(9) 0.0345(4) Uani d 1 H H19A 0.2002 -0.0542 -0.0638 0.052 Uiso calc 1 H H19B 0.3421 -0.0140 -0.0064 0.052 Uiso calc 1 H H19C 0.3545 0.0776 -0.0682 0.052 Uiso calc 1 O O1B 0.31592(13) 0.34788(13) 0.46337(6) 0.0366(3) Uani d 1 O O2B 0.09934(12) -0.05612(12) 0.24555(6) 0.0285(3) Uani d 1 N N1B 0.21077(13) 0.25496(13) 0.33811(7) 0.0233(3) Uani d 1 H H1B 0.2207 0.2679 0.2922 0.028 Uiso calc 1 N N2B -0.08803(13) -0.10989(13) 0.32306(7) 0.0240(3) Uani d 1 N N3B -0.13148(14) -0.02662(14) 0.37736(7) 0.0257(3) Uani d 1 C C1B 0.31460(16) 0.35901(16) 0.39659(8) 0.0243(3) Uani d 1 C C2B 0.42779(16) 0.49491(16) 0.37249(9) 0.0268(3) Uani d 1 H H2BA 0.5238 0.5348 0.4044 0.032 Uiso calc 1 H H2BB 0.4406 0.4673 0.3195 0.032 Uiso calc 1 C C3B 0.37614(16) 0.61150(16) 0.38034(9) 0.0247(3) Uani d 1 C C4B 0.40330(17) 0.70709(18) 0.45149(9) 0.0302(3) Uani d 1 H H4B 0.4505 0.6971 0.4942 0.036 Uiso calc 1 C C5B 0.3608(2) 0.8167(2) 0.45926(11) 0.0384(4) Uani d 1 H H5B 0.3791 0.8796 0.5071 0.046 Uiso calc 1 C C6B 0.2910(2) 0.8332(2) 0.39606(11) 0.0398(4) Uani d 1 H H6B 0.2640 0.9081 0.4013 0.048 Uiso calc 1 C C7B 0.26169(19) 0.7381(2) 0.32530(11) 0.0366(4) Uani d 1 H H7B 0.2141 0.7482 0.2828 0.044 Uiso calc 1 C C8B 0.30353(17) 0.62717(17) 0.31766(9) 0.0293(3) Uani d 1 H H8B 0.2827 0.5627 0.2700 0.035 Uiso calc 1 C C9B 0.08712(15) 0.12641(16) 0.34769(8) 0.0219(3) Uani d 1 C C10B -0.01869(16) 0.11522(16) 0.39461(8) 0.0239(3) Uani d 1 C C11B 0.04395(15) -0.01523(16) 0.29956(8) 0.0216(3) Uani d 1 C C12B -0.20372(16) -0.23775(16) 0.27073(8) 0.0247(3) Uani d 1 C C13B -0.17998(19) -0.35804(17) 0.24651(9) 0.0313(3) Uani d 1 H H13B -0.0928 -0.3574 0.2658 0.038 Uiso calc 1 C C14B -0.2880(2) -0.48003(18) 0.19304(10) 0.0404(4) Uani d 1 H H14B -0.2729 -0.5614 0.1762 0.049 Uiso calc 1 C C15B -0.4170(2) -0.4809(2) 0.16501(10) 0.0443(5) Uani d 1 H H15B -0.4885 -0.5625 0.1289 0.053 Uiso calc 1 C C16B -0.44110(19) -0.3609(2) 0.19021(10) 0.0426(5) Uani d 1 H H16B -0.5291 -0.3627 0.1714 0.051 Uiso calc 1 C C17B -0.33419(18) -0.23789(19) 0.24349(10) 0.0332(4) Uani d 1 H H17B -0.3498 -0.1569 0.2606 0.040 Uiso calc 1 C C18B -0.2191(2) -0.09991(19) 0.43300(10) 0.0359(4) Uani d 1 H H18D -0.2967 -0.1957 0.4069 0.054 Uiso calc 1 H H18E -0.2632 -0.0427 0.4584 0.054 Uiso calc 1 H H18F -0.1553 -0.1097 0.4703 0.054 Uiso calc 1 C C19B -0.02449(19) 0.22860(18) 0.45642(9) 0.0327(4) Uani d 1 H H19D -0.1216 0.2233 0.4501 0.049 Uiso calc 1 H H19E 0.0502 0.3245 0.4534 0.049 Uiso calc 1 H H19F -0.0059 0.2112 0.5057 0.049 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 O1A 0.0297(6) 0.0411(7) 0.0298(6) 0.0174(5) 0.0106(5) 0.0121(5) O2A 0.0455(6) 0.0349(6) 0.0183(5) 0.0265(5) 0.0104(4) 0.0078(4) N1A 0.0257(6) 0.0216(6) 0.0227(6) 0.0116(5) 0.0069(5) 0.0091(5) N2A 0.0318(6) 0.0277(6) 0.0178(6) 0.0176(5) 0.0064(5) 0.0060(5) N3A 0.0320(6) 0.0281(6) 0.0161(6) 0.0161(5) 0.0050(5) 0.0032(5) C1A 0.0270(7) 0.0215(7) 0.0251(7) 0.0124(6) 0.0051(6) 0.0050(5) C2A 0.0333(8) 0.0311(8) 0.0355(9) 0.0186(7) 0.0066(7) 0.0138(7) C3A 0.0333(8) 0.0364(8) 0.0272(8) 0.0216(7) 0.0060(6) 0.0146(6) C4A 0.0362(9) 0.0449(10) 0.0313(8) 0.0242(8) 0.0098(7) 0.0132(7) C5A 0.0509(10) 0.0450(10) 0.0282(8) 0.0268(9) 0.0049(7) 0.0070(7) C6A 0.0390(9) 0.0442(10) 0.0334(9) 0.0156(8) -0.0042(7) 0.0118(8) C7A 0.0299(8) 0.0564(11) 0.0387(9) 0.0223(8) 0.0058(7) 0.0182(8) C8A 0.0365(9) 0.0486(10) 0.0293(8) 0.0272(8) 0.0086(7) 0.0116(7) C9A 0.0211(6) 0.0201(7) 0.0198(7) 0.0082(5) 0.0035(5) 0.0038(5) C10A 0.0260(7) 0.0208(7) 0.0220(7) 0.0099(6) 0.0047(5) 0.0032(5) C11A 0.0218(6) 0.0220(7) 0.0193(7) 0.0094(6) 0.0039(5) 0.0066(5) C12A 0.0287(7) 0.0255(7) 0.0192(7) 0.0140(6) -0.0006(6) 0.0052(5) C13A 0.0301(8) 0.0313(8) 0.0253(7) 0.0126(7) 0.0042(6) 0.0075(6) C14A 0.0424(9) 0.0276(8) 0.0354(9) 0.0092(7) 0.0026(7) 0.0117(7) C15A 0.0582(11) 0.0285(8) 0.0371(9) 0.0233(8) -0.0028(8) 0.0047(7) C16A 0.0542(11) 0.0437(10) 0.0297(8) 0.0353(9) 0.0056(8) 0.0056(7) C17A 0.0372(8) 0.0364(9) 0.0249(7) 0.0216(7) 0.0067(6) 0.0108(6) C18A 0.0365(8) 0.0350(8) 0.0190(7) 0.0146(7) 0.0013(6) 0.0055(6) C19A 0.0485(10) 0.0343(9) 0.0239(8) 0.0237(8) 0.0086(7) 0.0018(6) O1B 0.0345(6) 0.0386(6) 0.0229(6) 0.0053(5) -0.0029(5) 0.0095(5) O2B 0.0286(5) 0.0264(5) 0.0278(6) 0.0105(4) 0.0117(4) 0.0049(4) N1B 0.0244(6) 0.0222(6) 0.0190(6) 0.0064(5) 0.0040(5) 0.0072(5) N2B 0.0220(6) 0.0233(6) 0.0228(6) 0.0076(5) 0.0066(5) 0.0036(5) N3B 0.0255(6) 0.0255(6) 0.0236(6) 0.0096(5) 0.0096(5) 0.0052(5) C1B 0.0239(7) 0.0240(7) 0.0242(7) 0.0103(6) 0.0039(5) 0.0064(6) C2B 0.0229(7) 0.0243(7) 0.0291(8) 0.0075(6) 0.0059(6) 0.0056(6) C3B 0.0194(6) 0.0214(7) 0.0282(7) 0.0044(5) 0.0088(6) 0.0067(6) C4B 0.0259(7) 0.0326(8) 0.0269(8) 0.0099(6) 0.0064(6) 0.0049(6) C5B 0.0379(9) 0.0342(9) 0.0370(9) 0.0146(7) 0.0117(7) -0.0011(7) C6B 0.0420(9) 0.0337(9) 0.0510(11) 0.0224(8) 0.0169(8) 0.0113(8) C7B 0.0358(9) 0.0403(9) 0.0389(9) 0.0193(8) 0.0094(7) 0.0162(7) C8B 0.0293(8) 0.0281(8) 0.0263(8) 0.0102(6) 0.0059(6) 0.0052(6) C9B 0.0220(7) 0.0233(7) 0.0192(6) 0.0093(6) 0.0031(5) 0.0060(5) C10B 0.0245(7) 0.0240(7) 0.0219(7) 0.0101(6) 0.0032(5) 0.0061(6) C11B 0.0205(6) 0.0243(7) 0.0202(7) 0.0097(6) 0.0029(5) 0.0080(5) C12B 0.0237(7) 0.0229(7) 0.0218(7) 0.0051(6) 0.0060(6) 0.0071(6) C13B 0.0335(8) 0.0274(8) 0.0305(8) 0.0109(7) 0.0073(6) 0.0092(6) C14B 0.0487(10) 0.0235(8) 0.0364(9) 0.0068(7) 0.0137(8) 0.0032(7) C15B 0.0340(9) 0.0394(10) 0.0287(9) -0.0058(8) 0.0070(7) -0.0010(7) C16B 0.0242(8) 0.0578(12) 0.0300(9) 0.0078(8) 0.0023(7) 0.0053(8) C17B 0.0289(8) 0.0372(9) 0.0298(8) 0.0127(7) 0.0062(6) 0.0065(7) C18B 0.0373(9) 0.0345(9) 0.0339(9) 0.0125(7) 0.0183(7) 0.0119(7) C19B 0.0365(8) 0.0315(8) 0.0298(8) 0.0168(7) 0.0095(7) 0.0031(6) 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' N N 0.0311 0.0180 '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 C1A N1A H1A 118.7 C1A N1A C9A 122.53(12) C9A N1A H1A 118.7 N3A N2A C12A 118.71(12) C11A N2A N3A 109.01(11) C11A N2A C12A 122.24(12) N2A N3A C18A 114.99(12) C10A N3A N2A 107.00(11) C10A N3A C18A 121.64(12) O1A C1A N1A 123.06(14) O1A C1A C2A 121.64(14) N1A C1A C2A 115.30(13) C1A C2A H2AA 109.8 C1A C2A H2AB 109.8 H2AA C2A H2AB 108.2 C3A C2A C1A 109.43(13) C3A C2A H2AA 109.8 C3A C2A H2AB 109.8 C4A C3A C2A 120.74(14) C4A C3A C8A 118.09(16) C8A C3A C2A 121.00(15) C3A C4A H4A 119.3 C3A C4A C5A 121.35(16) C5A C4A H4A 119.3 C4A C5A H5A 120.2 C6A C5A C4A 119.60(17) C6A C5A H5A 120.2 C5A C6A H6A 120.0 C7A C6A C5A 119.93(17) C7A C6A H6A 120.0 C6A C7A H7A 120.0 C6A C7A C8A 120.08(16) C8A C7A H7A 120.0 C3A C8A H8A 119.5 C7A C8A C3A 120.94(16) C7A C8A H8A 119.5 N1A C9A C11A 121.51(12) C10A C9A N1A 129.66(13) C10A C9A C11A 108.58(13) N3A C10A C19A 120.26(13) C9A C10A N3A 109.52(13) C9A C10A C19A 130.20(14) O2A C11A N2A 123.95(13) O2A C11A C9A 130.81(13) N2A C11A C9A 105.21(12) C13A C12A N2A 120.23(13) C17A C12A N2A 118.71(13) C17A C12A C13A 121.04(14) C12A C13A H13A 120.4 C14A C13A C12A 119.21(15) C14A C13A H13A 120.4 C13A C14A H14A 120.0 C15A C14A C13A 120.06(16) C15A C14A H14A 120.0 C14A C15A H15A 120.0 C16A C15A C14A 120.08(16) C16A C15A H15A 120.0 C15A C16A H16A 119.8 C15A C16A C17A 120.48(16) C17A C16A H16A 119.8 C12A C17A C16A 119.08(15) C12A C17A H17A 120.5 C16A C17A H17A 120.5 N3A C18A H18A 109.5 N3A C18A H18B 109.5 N3A C18A H18C 109.5 H18A C18A H18B 109.5 H18A C18A H18C 109.5 H18B C18A H18C 109.5 C10A C19A H19A 109.5 C10A C19A H19B 109.5 C10A C19A H19C 109.5 H19A C19A H19B 109.5 H19A C19A H19C 109.5 H19B C19A H19C 109.5 C1B N1B H1B 117.9 C1B N1B C9B 124.10(12) C9B N1B H1B 117.9 N3B N2B C12B 117.75(11) C11B N2B N3B 109.03(11) C11B N2B C12B 122.09(12) N2B N3B C18B 116.82(12) C10B N3B N2B 107.38(11) C10B N3B C18B 124.49(13) O1B C1B N1B 123.34(14) O1B C1B C2B 122.55(14) N1B C1B C2B 114.08(13) C1B C2B H2BA 109.5 C1B C2B H2BB 109.5 H2BA C2B H2BB 108.0 C3B C2B C1B 110.89(12) C3B C2B H2BA 109.5 C3B C2B H2BB 109.5 C4B C3B C2B 119.81(14) C8B C3B C2B 121.54(14) C8B C3B C4B 118.65(15) C3B C4B H4B 119.7 C5B C4B C3B 120.61(16) C5B C4B H4B 119.7 C4B C5B H5B 119.8 C4B C5B C6B 120.31(16) C6B C5B H5B 119.8 C5B C6B H6B 120.1 C7B C6B C5B 119.74(16) C7B C6B H6B 120.1 C6B C7B H7B 120.0 C6B C7B C8B 119.90(17) C8B C7B H7B 120.0 C3B C8B C7B 120.78(15) C3B C8B H8B 119.6 C7B C8B H8B 119.6 N1B C9B C11B 122.38(12) C10B C9B N1B 128.32(13) C10B C9B C11B 108.85(13) N3B C10B C19B 120.50(13) C9B C10B N3B 109.22(13) C9B C10B C19B 130.28(14) O2B C11B N2B 123.28(13) O2B C11B C9B 131.65(13) N2B C11B C9B 105.02(12) C13B C12B N2B 118.52(14) C13B C12B C17B 121.12(14) C17B C12B N2B 120.34(14) C12B C13B H13B 120.4 C12B C13B C14B 119.18(16) C14B C13B H13B 120.4 C13B C14B H14B 119.9 C15B C14B C13B 120.24(17) C15B C14B H14B 119.9 C14B C15B H15B 119.8 C14B C15B C16B 120.34(16) C16B C15B H15B 119.8 C15B C16B H16B 119.9 C15B C16B C17B 120.20(17) C17B C16B H16B 119.9 C12B C17B C16B 118.91(17) C12B C17B H17B 120.5 C16B C17B H17B 120.5 N3B C18B H18D 109.5 N3B C18B H18E 109.5 N3B C18B H18F 109.5 H18D C18B H18E 109.5 H18D C18B H18F 109.5 H18E C18B H18F 109.5 C10B C19B H19D 109.5 C10B C19B H19E 109.5 C10B C19B H19F 109.5 H19D C19B H19E 109.5 H19D C19B H19F 109.5 H19E C19B H19F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1A C1A 1.2217(18) O2A C11A 1.2334(17) N1A H1A 0.8600 N1A C1A 1.3574(19) N1A C9A 1.4069(18) N2A N3A 1.4057(16) N2A C11A 1.3958(18) N2A C12A 1.4320(19) N3A C10A 1.375(2) N3A C18A 1.4673(19) C1A C2A 1.525(2) C2A H2AA 0.9700 C2A H2AB 0.9700 C2A C3A 1.512(2) C3A C4A 1.384(2) C3A C8A 1.396(2) C4A H4A 0.9300 C4A C5A 1.391(3) C5A H5A 0.9300 C5A C6A 1.383(3) C6A H6A 0.9300 C6A C7A 1.382(3) C7A H7A 0.9300 C7A C8A 1.384(3) C8A H8A 0.9300 C9A C10A 1.362(2) C9A C11A 1.4339(19) C10A C19A 1.488(2) C12A C13A 1.389(2) C12A C17A 1.382(2) C13A H13A 0.9300 C13A C14A 1.389(2) C14A H14A 0.9300 C14A C15A 1.385(3) C15A H15A 0.9300 C15A C16A 1.381(3) C16A H16A 0.9300 C16A C17A 1.389(2) C17A H17A 0.9300 C18A H18A 0.9600 C18A H18B 0.9600 C18A H18C 0.9600 C19A H19A 0.9600 C19A H19B 0.9600 C19A H19C 0.9600 O1B C1B 1.2219(19) O2B C11B 1.2412(18) N1B H1B 0.8600 N1B C1B 1.3519(19) N1B C9B 1.4118(18) N2B N3B 1.4008(17) N2B C11B 1.3985(18) N2B C12B 1.4345(18) N3B C10B 1.3678(19) N3B C18B 1.4553(19) C1B C2B 1.525(2) C2B H2BA 0.9700 C2B H2BB 0.9700 C2B C3B 1.517(2) C3B C4B 1.392(2) C3B C8B 1.389(2) C4B H4B 0.9300 C4B C5B 1.383(2) C5B H5B 0.9300 C5B C6B 1.386(3) C6B H6B 0.9300 C6B C7B 1.381(3) C7B H7B 0.9300 C7B C8B 1.391(2) C8B H8B 0.9300 C9B C10B 1.367(2) C9B C11B 1.426(2) C10B C19B 1.486(2) C12B C13B 1.381(2) C12B C17B 1.387(2) C13B H13B 0.9300 C13B C14B 1.389(2) C14B H14B 0.9300 C14B C15B 1.374(3) C15B H15B 0.9300 C15B C16B 1.383(3) C16B H16B 0.9300 C16B C17B 1.389(2) C17B H17B 0.9300 C18B H18D 0.9600 C18B H18E 0.9600 C18B H18F 0.9600 C19B H19D 0.9600 C19B H19E 0.9600 C19B H19F 0.9600 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 N1A H1A O2B . 0.86 1.97 2.8292(16) 173.2 C14A H14A O1A 2_665 0.93 2.55 3.454(2) 165.2 N1B H1B O2A . 0.86 1.98 2.8115(16) 162.9 C2B H2BA O1B 2_666 0.97 2.55 3.4239(19) 149.8 C4B H4B O1B 2_666 0.93 2.72 3.487(2) 140.8 C8B H8B O2A . 0.93 2.57 3.404(2) 149.8 C14B H14B O1A 1_445 0.93 2.70 3.398(2) 132.0 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 O1A C1A C2A C3A 56.40(19) N1A C1A C2A C3A -123.19(14) N1A C9A C10A N3A -170.40(14) N1A C9A C10A C19A 11.1(3) N1A C9A C11A O2A -1.8(2) N1A C9A C11A N2A 176.26(12) N2A N3A C10A C9A -7.50(16) N2A N3A C10A C19A 171.13(13) N2A C12A C13A C14A -178.87(14) N2A C12A C17A C16A 177.18(14) N3A N2A C11A O2A 172.11(13) N3A N2A C11A C9A -6.14(15) N3A N2A C12A C13A -22.75(19) N3A N2A C12A C17A 158.89(13) C1A N1A C9A C10A 52.2(2) C1A N1A C9A C11A -121.29(15) C1A C2A C3A C4A 93.50(17) C1A C2A C3A C8A -81.70(18) C2A C3A C4A C5A -174.17(15) C2A C3A C8A C7A 174.12(16) C3A C4A C5A C6A -0.2(3) C4A C3A C8A C7A -1.2(2) C4A C5A C6A C7A -0.8(3) C5A C6A C7A C8A 0.8(3) C6A C7A C8A C3A 0.3(3) C8A C3A C4A C5A 1.2(2) C9A N1A C1A O1A -8.2(2) C9A N1A C1A C2A 171.37(13) C10A C9A C11A O2A -176.54(15) C10A C9A C11A N2A 1.55(15) C11A N2A N3A C10A 8.50(15) C11A N2A N3A C18A 146.89(13) C11A N2A C12A C13A 118.93(16) C11A N2A C12A C17A -59.42(19) C11A C9A C10A N3A 3.74(16) C11A C9A C10A C19A -174.72(15) C12A N2A N3A C10A 154.81(12) C12A N2A N3A C18A -66.80(17) C12A N2A C11A O2A 27.2(2) C12A N2A C11A C9A -151.03(13) C12A C13A C14A C15A 1.7(2) C13A C12A C17A C16A -1.2(2) C13A C14A C15A C16A -1.2(3) C14A C15A C16A C17A -0.6(3) C15A C16A C17A C12A 1.7(3) C17A C12A C13A C14A -0.6(2) C18A N3A C10A C9A -142.51(14) C18A N3A C10A C19A 36.1(2) O1B C1B C2B C3B -86.23(18) N1B C1B C2B C3B 91.80(15) N1B C9B C10B N3B 170.33(14) N1B C9B C10B C19B -9.8(3) N1B C9B C11B O2B 1.9(2) N1B C9B C11B N2B -175.40(12) N2B N3B C10B C9B 5.75(16) N2B N3B C10B C19B -174.13(13) N2B C12B C13B C14B -176.98(14) N2B C12B C17B C16B 177.11(14) N3B N2B C11B O2B -171.57(13) N3B N2B C11B C9B 6.02(15) N3B N2B C12B C13B -146.60(14) N3B N2B C12B C17B 35.38(19) C1B N1B C9B C10B 53.7(2) C1B N1B C9B C11B -134.85(15) C1B C2B C3B C4B 83.37(16) C1B C2B C3B C8B -97.55(16) C2B C3B C4B C5B 178.16(14) C2B C3B C8B C7B -177.67(14) C3B C4B C5B C6B -0.3(3) C4B C3B C8B C7B 1.4(2) C4B C5B C6B C7B 1.1(3) C5B C6B C7B C8B -0.6(3) C6B C7B C8B C3B -0.7(2) C8B C3B C4B C5B -1.0(2) C9B N1B C1B O1B 4.1(2) C9B N1B C1B C2B -173.89(13) C10B C9B C11B O2B 174.80(15) C10B C9B C11B N2B -2.50(16) C11B N2B N3B C10B -7.40(16) C11B N2B N3B C18B -152.81(13) C11B N2B C12B C13B 73.50(18) C11B N2B C12B C17B -104.52(17) C11B C9B C10B N3B -2.02(17) C11B C9B C10B C19B 177.85(15) C12B N2B N3B C10B -152.14(13) C12B N2B N3B C18B 62.45(18) C12B N2B C11B O2B -28.7(2) C12B N2B C11B C9B 148.94(13) C12B C13B C14B C15B -0.3(2) C13B C12B C17B C16B -0.9(2) C13B C14B C15B C16B -0.5(3) C14B C15B C16B C17B 0.7(3) C15B C16B C17B C12B 0.0(3) C17B C12B C13B C14B 1.0(2) C18B N3B C10B C9B 147.82(15) C18B N3B C10B C19B -32.1(2)