#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105083.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_2105083 loop_ _publ_author_name 'Mocilac, Pavle' 'Donnelly, Katie' 'Gallagher, John F.' _publ_section_title ; Structural systematics and conformational analyses of a 3 \\times 3 isomer grid of fluoro-N-(pyridyl)benzamides: physicochemical correlations, polymorphism and isomorphous relationships ; _journal_coeditor_code GP5047 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 189 _journal_page_last 203 _journal_paper_doi 10.1107/S0108768112006799 _journal_volume 68 _journal_year 2012 _chemical_formula_moiety 'C12 H9 F N2 O' _chemical_formula_sum 'C12 H9 F N2 O' _chemical_formula_weight 216.21 _chemical_melting_point 350 _chemical_name_common Fmo _chemical_name_systematic 3-Fluoro-N-(pyridin-2-yl)benzamide _space_group_IT_number 2 _symmetry_cell_setting triclinic _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 _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 102.286(3) _cell_angle_beta 97.356(3) _cell_angle_gamma 117.074(4) _cell_formula_units_Z 4 _cell_length_a 10.4219(4) _cell_length_b 10.7183(4) _cell_length_c 11.0188(3) _cell_measurement_reflns_used 8483 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.55 _cell_volume 1034.49(8) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 294.0(10) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.919 _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini Ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 14851 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 27.92 _diffrn_reflns_theta_min 2.24 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 60 _diffrn_standards_number 14852 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_T_max 0.9717 _exptl_absorpt_correction_T_min 0.9560 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.291 _refine_diff_density_min -0.248 _refine_ls_extinction_coef 0.061(4) _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 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 4555 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0464 _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^)+(0.0528P)^2^+0.2446P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1152 _refine_ls_wR_factor_ref 0.1244 _reflns_number_gt 3732 _reflns_number_total 4555 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 11-003 is Fmo in P-1 [Z'=2] at RT with Mo 40kV30mA to 0.80\%A CELL 0.71073 10.4219 10.7183 11.0188 102.286 97.356 117.074 ZERR 4 0.0004 0.0004 0.0003 0.003 0.003 0.004 LATT 1 SFAC C H N O F UNIT 48 36 8 4 4 MERG 3 FMAP 2 L.S. 8 3 LIST 4 ACTA 52 CONF BOND $H HTAB EQIV $2 X,1+Y,Z HTAB N1A N22B HTAB N1B N22A HTAB C26A O1A HTAB C26B O1B HTAB C25A O1B_$2 RTAB OC O1A C1A RTAB NC N1A C1A RTAB NC N1A C21A RTAB CC C1A C11A RTAB NC N22A F13A RTAB OCN O1A C1A N1A RTAB CNC C1A N1A C21A RTAB NCC N1A C1A C11A RTAB NCN N1A C21A N22A RTAB NCC N1A C21A C26A RTAB CCC C1A C11A C12A RTAB CCC C1A C11A C16A RTAB CCC C11A C12A C13A RTAB OCC O1A C1A C11A RTAB OCCC O1A C1A C11A C12A RTAB OCCC O1A C1A C11A C16A RTAB CNCN C1A N1A C21A N22A RTAB CNCC C1A N1A C21A C26A RTAB OC O1B C1B RTAB NC N1B C1B RTAB NC N1B C21B RTAB CC C1B C11B RTAB NC N22B F13B RTAB OCN O1B C1B N1B RTAB CNC C1B N1B C21B RTAB NCC N1B C1B C11B RTAB NCN N1B C21B N22B RTAB NCC N1B C21B C26B RTAB CCC C1B C11B C12B RTAB CCC C1B C11B C16B RTAB CCC C11B C12B C13B RTAB OCC O1B C1B C11B RTAB OCCC O1B C1B C11B C12B RTAB OCCC O1B C1B C11B C16B RTAB CNCN C1B N1B C21B N22B RTAB CNCC C1B N1B C21B C26B SIZE 0.35 0.28 0.44 TEMP 21 PLAN 10 MPLA 6 C11A C12A C13A C14A C15A C16A F13A MPLA 5 O1A N1A C1A C11A C21A MPLA 6 C21A N22A C23A C24A C25A C26A MPLA 6 C11A C12A C13A C14A C15A C16A F13A MPLA 3 O1A N1A C1A C11A C21A MPLA 6 C21A N22A C23A C24A C25A C26A MPLA 6 C11B C12B C13B C14B C15B C16B F13B MPLA 5 O1B N1B C1B C11B C21B MPLA 6 C21B N22B C23B C24B C25B C26B MPLA 6 C11B C12B C13B C14B C15B C16B F13B MPLA 3 O1B N1B C1B C11B C21B MPLA 6 C21B N22B C23B C24B C25B C26B WGHT 0.052800 0.244600 EXTI 0.061017 FVAR 8.90497 MOLE 1 F13A 5 -0.292399 0.416653 0.067701 11.00000 0.05828 0.10721 = 0.09774 0.01050 -0.00140 0.03642 O1A 4 0.188185 0.880557 0.353448 11.00000 0.10403 0.05895 = 0.06836 0.02438 0.00167 0.04727 C1A 1 0.184516 0.768278 0.363052 11.00000 0.05931 0.05261 = 0.04977 0.02152 0.01450 0.03279 N1A 3 0.261964 0.760216 0.467866 11.00000 0.05506 0.04090 = 0.04837 0.01534 0.00813 0.02582 H1A 2 0.235025 0.670629 0.470139 11.00000 0.05873 C11A 1 0.087798 0.624187 0.259855 11.00000 0.05639 0.05483 = 0.04133 0.02053 0.01394 0.03036 C12A 1 -0.058406 0.587391 0.208542 11.00000 0.05983 0.06874 = 0.05005 0.02092 0.01566 0.03890 AFIX 43 H12A 2 -0.093329 0.651536 0.236167 11.00000 -1.20000 AFIX 0 C13A 1 -0.149500 0.454253 0.116307 11.00000 0.05229 0.07342 = 0.05559 0.01941 0.00880 0.02702 C14A 1 -0.102201 0.358288 0.069736 11.00000 0.06957 0.05967 = 0.05425 0.01117 0.01151 0.02469 AFIX 43 H14A 2 -0.166846 0.268958 0.006492 11.00000 -1.20000 AFIX 0 C15A 1 0.043060 0.397202 0.118722 11.00000 0.07592 0.06188 = 0.05813 0.01607 0.02082 0.03942 AFIX 43 H15A 2 0.077876 0.334172 0.087083 11.00000 -1.20000 AFIX 0 C16A 1 0.138759 0.528766 0.214502 11.00000 0.05725 0.06028 = 0.05369 0.02004 0.01460 0.03353 AFIX 43 H16A 2 0.236543 0.553029 0.248221 11.00000 -1.20000 AFIX 0 C21A 1 0.340215 0.871229 0.585816 11.00000 0.04433 0.04323 = 0.05163 0.01492 0.01171 0.02495 N22A 3 0.363023 0.820750 0.682242 11.00000 0.06409 0.04760 = 0.04975 0.01295 0.00403 0.03011 C23A 1 0.428992 0.917735 0.800020 11.00000 0.07605 0.06378 = 0.05100 0.01120 0.00288 0.03786 AFIX 43 H23A 2 0.444299 0.883408 0.868162 11.00000 -1.20000 AFIX 0 C24A 1 0.475295 1.064297 0.826317 11.00000 0.06832 0.05939 = 0.06007 -0.00162 0.00156 0.03296 AFIX 43 H24A 2 0.518484 1.127553 0.910159 11.00000 -1.20000 AFIX 0 C25A 1 0.456165 1.115165 0.725478 11.00000 0.06097 0.04181 = 0.08172 0.00804 0.01033 0.02390 AFIX 43 H25A 2 0.489209 1.214899 0.740001 11.00000 -1.20000 AFIX 0 C26A 1 0.388301 1.019269 0.602949 11.00000 0.05803 0.04497 = 0.06614 0.02009 0.01507 0.02644 AFIX 43 H26A 2 0.374909 1.052395 0.533479 11.00000 -1.20000 AFIX 0 MOLE 2 F13B 5 0.808340 0.837219 1.156458 11.00000 0.11656 0.12368 = 0.07682 0.03718 0.00629 0.06286 O1B 4 0.505275 0.436987 0.730630 11.00000 0.11127 0.05918 = 0.21374 0.01617 -0.05377 0.04996 C1B 1 0.498778 0.546245 0.727683 11.00000 0.06538 0.05550 = 0.10220 0.02219 0.00281 0.03788 N1B 3 0.389926 0.544110 0.644101 11.00000 0.06354 0.04516 = 0.06777 0.01364 0.00556 0.03353 H1B 2 0.388370 0.626239 0.656184 11.00000 0.05526 C11B 1 0.612077 0.691730 0.820375 11.00000 0.05029 0.05900 = 0.07772 0.02173 0.00908 0.03495 C12B 1 0.658576 0.698115 0.947056 11.00000 0.06399 0.07213 = 0.09174 0.04148 0.01779 0.04139 AFIX 43 H12B 2 0.618722 0.613711 0.972469 11.00000 -1.20000 AFIX 0 C13B 1 0.763856 0.830868 1.033059 11.00000 0.06263 0.08338 = 0.06641 0.02352 0.01065 0.04461 C14B 1 0.826563 0.956426 1.000412 11.00000 0.05784 0.06830 = 0.07957 0.01584 0.01243 0.03175 AFIX 43 H14B 2 0.897420 1.045210 1.061559 11.00000 -1.20000 AFIX 0 C15B 1 0.783410 0.949886 0.875400 11.00000 0.06092 0.06521 = 0.08536 0.02955 0.01836 0.02519 AFIX 43 H15B 2 0.826755 1.034718 0.850952 11.00000 -1.20000 AFIX 0 C16B 1 0.676164 0.818499 0.785405 11.00000 0.05830 0.06948 = 0.06740 0.02602 0.01519 0.03296 AFIX 43 H16B 2 0.647012 0.815411 0.700941 11.00000 -1.20000 AFIX 0 C21B 1 0.264461 0.420921 0.554869 11.00000 0.05949 0.04761 = 0.05853 0.01692 0.01811 0.03106 N22B 3 0.168768 0.454136 0.497044 11.00000 0.05814 0.04683 = 0.05345 0.01738 0.01175 0.02578 C23B 1 0.042072 0.343014 0.415069 11.00000 0.05736 0.05491 = 0.05772 0.01888 0.01626 0.02405 AFIX 43 H23B 2 -0.026286 0.364919 0.375981 11.00000 -1.20000 AFIX 0 C24B 1 0.007015 0.198284 0.385229 11.00000 0.06032 0.05171 = 0.06835 0.01015 0.02244 0.01853 AFIX 43 H24B 2 -0.082482 0.124053 0.327484 11.00000 -1.20000 AFIX 0 C25B 1 0.108090 0.166665 0.443236 11.00000 0.08138 0.04448 = 0.09425 0.01126 0.02935 0.03148 AFIX 43 H25B 2 0.088511 0.069899 0.423873 11.00000 -1.20000 AFIX 0 C26B 1 0.238237 0.277802 0.529921 11.00000 0.07664 0.05171 = 0.09143 0.01446 0.01494 0.03995 AFIX 43 H26B 2 0.307073 0.257630 0.570876 11.00000 -1.20000 HKLF 4 REM 11-003 is Fmo in P-1 [Z'=2] at RT with Mo 40kV30mA to 0.80\%A REM R1 = 0.0464 for 3732 Fo > 4sig(Fo) and 0.0569 for all 4555 data REM 298 parameters refined using 0 restraints END WGHT 0.0528 0.2446 REM Highest difference peak 0.291, deepest hole -0.248, 1-sigma level 0.037 Q1 1 0.4279 0.4186 0.7704 11.00000 0.05 0.29 Q2 1 0.7327 0.7379 1.1336 11.00000 0.05 0.26 Q3 1 0.4970 0.4047 0.6515 11.00000 0.05 0.20 Q4 1 0.3352 0.9387 0.6051 11.00000 0.05 0.16 Q5 1 0.5859 0.6249 0.7604 11.00000 0.05 0.15 Q6 1 0.7785 0.8786 0.8177 11.00000 0.05 0.14 Q7 1 0.3649 0.8211 0.8673 11.00000 0.05 0.14 Q8 1 0.1102 0.5869 0.2542 11.00000 0.05 0.14 Q9 1 0.3315 0.7266 0.6649 11.00000 0.05 0.14 Q10 1 0.5171 1.1021 0.7685 11.00000 0.05 0.14 ; _cod_data_source_file gp5047.cif _cod_data_source_block Fmo-11-003 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_exptl_absorpt_correction_type' value 'Analytical' changed to 'analytical' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2105083 _cod_database_fobs_code 2105083 loop_ _symmetry_equiv_pos_as_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_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity F F13A -0.29240(12) 0.41665(15) 0.06770(12) 0.0957(4) Uani d . 1 1 O O1A 0.18818(16) 0.88056(13) 0.35345(12) 0.0756(4) Uani d . 1 1 C C1A 0.18452(17) 0.76828(16) 0.36305(14) 0.0508(3) Uani d . 1 1 N N1A 0.26196(14) 0.76022(14) 0.46787(11) 0.0476(3) Uani d . 1 1 H H1A 0.2350(19) 0.671(2) 0.4701(16) 0.059(5) Uiso d . 1 1 C C11A 0.08780(17) 0.62419(16) 0.25985(13) 0.0486(3) Uani d . 1 1 C C12A -0.05841(17) 0.58739(18) 0.20854(14) 0.0560(4) Uani d . 1 1 H H12A -0.0933 0.6515 0.2362 0.067 Uiso calc R 1 1 C C13A -0.14950(18) 0.4543(2) 0.11631(16) 0.0628(4) Uani d . 1 1 C C14A -0.1022(2) 0.3583(2) 0.06974(16) 0.0659(4) Uani d . 1 1 H H14A -0.1668 0.2690 0.0065 0.079 Uiso calc R 1 1 C C15A 0.0431(2) 0.39720(19) 0.11872(16) 0.0632(4) Uani d . 1 1 H H15A 0.0779 0.3342 0.0871 0.076 Uiso calc R 1 1 C C16A 0.13876(18) 0.52877(17) 0.21450(15) 0.0548(4) Uani d . 1 1 H H16A 0.2365 0.5530 0.2482 0.066 Uiso calc R 1 1 C C21A 0.34021(15) 0.87123(15) 0.58582(13) 0.0451(3) Uani d . 1 1 N N22A 0.36302(15) 0.82075(13) 0.68224(12) 0.0543(3) Uani d . 1 1 C C23A 0.4290(2) 0.91773(19) 0.80002(16) 0.0649(4) Uani d . 1 1 H H23A 0.4443 0.8834 0.8682 0.078 Uiso calc R 1 1 C C24A 0.4753(2) 1.06430(19) 0.82632(17) 0.0672(5) Uani d . 1 1 H H24A 0.5185 1.1276 0.9102 0.081 Uiso calc R 1 1 C C25A 0.45616(19) 1.11517(18) 0.72548(18) 0.0650(4) Uani d . 1 1 H H25A 0.4892 1.2149 0.7400 0.078 Uiso calc R 1 1 C C26A 0.38830(17) 1.01927(16) 0.60295(16) 0.0556(4) Uani d . 1 1 H H26A 0.3749 1.0524 0.5335 0.067 Uiso calc R 1 1 F F13B 0.80834(16) 0.83722(17) 1.15646(12) 0.1052(4) Uani d . 1 1 O O1B 0.5053(2) 0.43699(16) 0.7306(2) 0.1396(9) Uani d . 1 1 C C1B 0.4988(2) 0.54625(19) 0.7277(2) 0.0735(5) Uani d . 1 1 N N1B 0.38993(15) 0.54411(15) 0.64410(13) 0.0580(3) Uani d . 1 1 H H1B 0.3884(18) 0.6262(19) 0.6562(15) 0.055(4) Uiso d . 1 1 C C11B 0.61208(17) 0.69173(18) 0.82037(17) 0.0598(4) Uani d . 1 1 C C12B 0.6586(2) 0.6981(2) 0.94706(19) 0.0702(5) Uani d . 1 1 H H12B 0.6187 0.6137 0.9725 0.084 Uiso calc R 1 1 C C13B 0.7639(2) 0.8309(2) 1.03306(18) 0.0679(5) Uani d . 1 1 C C14B 0.8266(2) 0.9564(2) 1.00041(19) 0.0702(5) Uani d . 1 1 H H14B 0.8974 1.0452 1.0616 0.084 Uiso calc R 1 1 C C15B 0.7834(2) 0.9499(2) 0.87540(19) 0.0720(5) Uani d . 1 1 H H15B 0.8268 1.0347 0.8510 0.086 Uiso calc R 1 1 C C16B 0.67616(19) 0.8185(2) 0.78540(18) 0.0638(4) Uani d . 1 1 H H16B 0.6470 0.8154 0.7009 0.077 Uiso calc R 1 1 C C21B 0.26446(17) 0.42092(16) 0.55487(15) 0.0530(4) Uani d . 1 1 N N22B 0.16877(14) 0.45414(13) 0.49704(12) 0.0529(3) Uani d . 1 1 C C23B 0.04207(18) 0.34301(17) 0.41507(15) 0.0579(4) Uani d . 1 1 H H23B -0.0263 0.3649 0.3760 0.069 Uiso calc R 1 1 C C24B 0.0070(2) 0.19828(18) 0.38523(17) 0.0649(4) Uani d . 1 1 H H24B -0.0825 0.1241 0.3275 0.078 Uiso calc R 1 1 C C25B 0.1081(2) 0.16667(19) 0.4432(2) 0.0744(5) Uani d . 1 1 H H25B 0.0885 0.0699 0.4239 0.089 Uiso calc R 1 1 C C26B 0.2382(2) 0.27780(19) 0.5299(2) 0.0720(5) Uani d . 1 1 H H26B 0.3071 0.2576 0.5709 0.086 Uiso calc R 1 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 F13A 0.0583(6) 0.1072(9) 0.0977(9) 0.0364(6) -0.0014(6) 0.0105(7) O1A 0.1040(10) 0.0589(7) 0.0684(7) 0.0473(7) 0.0017(7) 0.0244(6) C1A 0.0593(8) 0.0526(8) 0.0498(8) 0.0328(7) 0.0145(6) 0.0215(6) N1A 0.0551(7) 0.0409(6) 0.0484(6) 0.0258(5) 0.0081(5) 0.0153(5) C11A 0.0564(8) 0.0548(8) 0.0413(7) 0.0304(7) 0.0139(6) 0.0205(6) C12A 0.0598(9) 0.0687(10) 0.0500(8) 0.0389(8) 0.0157(7) 0.0209(7) C13A 0.0523(9) 0.0734(11) 0.0556(9) 0.0270(8) 0.0088(7) 0.0194(8) C14A 0.0696(11) 0.0597(10) 0.0542(9) 0.0247(8) 0.0115(8) 0.0112(7) C15A 0.0759(11) 0.0619(10) 0.0581(9) 0.0394(9) 0.0208(8) 0.0161(8) C16A 0.0573(9) 0.0603(9) 0.0537(8) 0.0335(7) 0.0146(7) 0.0200(7) C21A 0.0443(7) 0.0432(7) 0.0516(7) 0.0250(6) 0.0117(6) 0.0149(6) N22A 0.0641(8) 0.0476(7) 0.0498(7) 0.0301(6) 0.0040(6) 0.0129(5) C23A 0.0761(11) 0.0638(10) 0.0510(8) 0.0379(9) 0.0029(8) 0.0112(7) C24A 0.0683(10) 0.0594(10) 0.0601(9) 0.0330(8) 0.0016(8) -0.0016(8) C25A 0.0610(9) 0.0418(8) 0.0817(11) 0.0239(7) 0.0103(8) 0.0080(8) C26A 0.0580(9) 0.0450(8) 0.0661(9) 0.0264(7) 0.0151(7) 0.0201(7) F13B 0.1166(10) 0.1237(11) 0.0768(8) 0.0629(9) 0.0063(7) 0.0372(7) O1B 0.1113(13) 0.0592(9) 0.214(2) 0.0500(9) -0.0538(13) 0.0162(11) C1B 0.0654(10) 0.0555(9) 0.1022(14) 0.0379(8) 0.0028(10) 0.0222(9) N1B 0.0635(8) 0.0452(7) 0.0678(8) 0.0335(6) 0.0056(6) 0.0136(6) C11B 0.0503(8) 0.0590(9) 0.0777(11) 0.0350(7) 0.0091(8) 0.0217(8) C12B 0.0640(10) 0.0721(11) 0.0917(13) 0.0414(9) 0.0178(9) 0.0415(10) C13B 0.0626(10) 0.0834(12) 0.0664(10) 0.0446(10) 0.0107(8) 0.0235(9) C14B 0.0578(10) 0.0683(11) 0.0796(12) 0.0318(9) 0.0124(9) 0.0158(9) C15B 0.0609(10) 0.0652(11) 0.0854(13) 0.0252(9) 0.0184(9) 0.0296(9) C16B 0.0583(9) 0.0695(11) 0.0674(10) 0.0330(8) 0.0152(8) 0.0260(8) C21B 0.0595(9) 0.0476(8) 0.0585(8) 0.0311(7) 0.0181(7) 0.0169(7) N22B 0.0581(7) 0.0468(7) 0.0535(7) 0.0258(6) 0.0118(6) 0.0174(5) C23B 0.0574(9) 0.0549(9) 0.0577(9) 0.0240(7) 0.0163(7) 0.0189(7) C24B 0.0603(9) 0.0517(9) 0.0684(10) 0.0185(8) 0.0224(8) 0.0101(8) C25B 0.0814(12) 0.0445(9) 0.0943(13) 0.0315(9) 0.0293(11) 0.0113(9) C26B 0.0766(11) 0.0517(9) 0.0914(13) 0.0399(9) 0.0149(10) 0.0145(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 O1A C1A N1A 124.10(14) O1A C1A C11A 121.53(13) N1A C1A C11A 114.34(12) C1A N1A C21A 126.24(12) C1A N1A H1A 114.9(11) C21A N1A H1A 115.5(11) C16A C11A C12A 119.90(14) C16A C11A C1A 122.62(13) C12A C11A C1A 117.48(13) C13A C12A C11A 118.22(15) C13A C12A H12A 120.9 C11A C12A H12A 120.9 F13A C13A C14A 118.37(16) F13A C13A C12A 118.54(16) C14A C13A C12A 123.09(15) C13A C14A C15A 118.20(16) C13A C14A H14A 120.9 C15A C14A H14A 120.9 C14A C15A C16A 121.05(16) C14A C15A H15A 119.5 C16A C15A H15A 119.5 C15A C16A C11A 119.51(15) C15A C16A H16A 120.2 C11A C16A H16A 120.2 N22A C21A C26A 122.64(13) N22A C21A N1A 113.16(12) C26A C21A N1A 124.19(13) C21A N22A C23A 117.37(13) N22A C23A C24A 123.90(16) N22A C23A H23A 118.1 C24A C23A H23A 118.1 C23A C24A C25A 117.92(15) C23A C24A H24A 121.0 C25A C24A H24A 121.0 C24A C25A C26A 120.10(15) C24A C25A H25A 119.9 C26A C25A H25A 119.9 C25A C26A C21A 117.98(15) C25A C26A H26A 121.0 C21A C26A H26A 121.0 O1B C1B N1B 123.31(18) O1B C1B C11B 120.10(16) N1B C1B C11B 116.57(14) C1B N1B C21B 127.75(14) C1B N1B H1B 116.2(11) C21B N1B H1B 115.0(11) C16B C11B C12B 119.09(17) C16B C11B C1B 122.90(17) C12B C11B C1B 117.97(16) C13B C12B C11B 118.63(17) C13B C12B H12B 120.7 C11B C12B H12B 120.7 C14B C13B F13B 118.47(18) C14B C13B C12B 122.90(17) F13B C13B C12B 118.62(17) C13B C14B C15B 118.58(18) C13B C14B H14B 120.7 C15B C14B H14B 120.7 C14B C15B C16B 120.58(18) C14B C15B H15B 119.7 C16B C15B H15B 119.7 C11B C16B C15B 120.19(17) C11B C16B H16B 119.9 C15B C16B H16B 119.9 N22B C21B C26B 122.49(15) N22B C21B N1B 113.14(12) C26B C21B N1B 124.35(15) C23B N22B C21B 117.57(13) N22B C23B C24B 123.71(16) N22B C23B H23B 118.1 C24B C23B H23B 118.1 C25B C24B C23B 117.88(16) C25B C24B H24B 121.1 C23B C24B H24B 121.1 C24B C25B C26B 120.01(16) C24B C25B H25B 120.0 C26B C25B H25B 120.0 C25B C26B C21B 118.31(17) C25B C26B H26B 120.8 C21B C26B H26B 120.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F13A C13A 1.3508(19) O1A C1A 1.2142(17) C1A N1A 1.3638(18) C1A C11A 1.495(2) N1A C21A 1.3990(18) N1A H1A 0.876(18) C11A C16A 1.387(2) C11A C12A 1.391(2) C12A C13A 1.369(2) C12A H12A 0.9300 C13A C14A 1.366(3) C14A C15A 1.370(2) C14A H14A 0.9300 C15A C16A 1.383(2) C15A H15A 0.9300 C16A H16A 0.9300 C21A N22A 1.3324(18) C21A C26A 1.3889(19) N22A C23A 1.336(2) C23A C24A 1.366(2) C23A H23A 0.9300 C24A C25A 1.368(3) C24A H24A 0.9300 C25A C26A 1.372(2) C25A H25A 0.9300 C26A H26A 0.9300 F13B C13B 1.356(2) O1B C1B 1.210(2) C1B N1B 1.355(2) C1B C11B 1.485(2) N1B C21B 1.402(2) N1B H1B 0.870(17) C11B C16B 1.380(2) C11B C12B 1.394(2) C12B C13B 1.366(3) C12B H12B 0.9300 C13B C14B 1.354(3) C14B C15B 1.370(3) C14B H14B 0.9300 C15B C16B 1.380(3) C15B H15B 0.9300 C16B H16B 0.9300 C21B N22B 1.3358(19) C21B C26B 1.387(2) N22B C23B 1.335(2) C23B C24B 1.373(2) C23B H23B 0.9300 C24B C25B 1.370(3) C24B H24B 0.9300 C25B C26B 1.373(3) C25B H25B 0.9300 C26B H26B 0.9300 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 _geom_hbond_publ_flag N1A H1A N22B . 0.876(18) 2.199(18) 3.0721(17) 174.1(15) yes N1B H1B N22A . 0.870(17) 2.183(18) 3.0502(18) 174.9(15) yes C26A H26A O1A . 0.93 2.30 2.844(2) 117 yes C26B H26B O1B . 0.93 2.25 2.836(3) 120 yes C25A H25A O1B 1_565 0.93 2.33 3.235(2) 163 yes 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 N1A C21A 9.2(3) C11A C1A N1A C21A -168.63(13) O1A C1A C11A C16A 134.13(17) N1A C1A C11A C16A -47.96(19) O1A C1A C11A C12A -45.6(2) N1A C1A C11A C12A 132.35(14) C16A C11A C12A C13A 1.9(2) C1A C11A C12A C13A -178.38(13) C11A C12A C13A F13A 178.83(14) C11A C12A C13A C14A -2.1(2) F13A C13A C14A C15A 179.61(16) C12A C13A C14A C15A 0.5(3) C13A C14A C15A C16A 1.2(3) C14A C15A C16A C11A -1.3(2) C12A C11A C16A C15A -0.3(2) C1A C11A C16A C15A -179.96(14) C1A N1A C21A N22A 159.10(14) C1A N1A C21A C26A -20.0(2) C26A C21A N22A C23A 3.1(2) N1A C21A N22A C23A -176.05(14) C21A N22A C23A C24A -0.8(3) N22A C23A C24A C25A -1.7(3) C23A C24A C25A C26A 1.9(3) C24A C25A C26A C21A 0.2(2) N22A C21A C26A C25A -2.9(2) N1A C21A C26A C25A 176.20(14) O1B C1B N1B C21B 4.4(4) C11B C1B N1B C21B -174.48(16) O1B C1B C11B C16B 137.5(2) N1B C1B C11B C16B -43.6(3) O1B C1B C11B C12B -40.2(3) N1B C1B C11B C12B 138.65(18) C16B C11B C12B C13B 1.5(2) C1B C11B C12B C13B 179.32(16) C11B C12B C13B C14B -0.9(3) C11B C12B C13B F13B 179.57(16) F13B C13B C14B C15B 179.05(17) C12B C13B C14B C15B -0.5(3) C13B C14B C15B C16B 1.2(3) C12B C11B C16B C15B -0.8(3) C1B C11B C16B C15B -178.52(16) C14B C15B C16B C11B -0.6(3) C1B N1B C21B N22B 172.50(17) C1B N1B C21B C26B -6.0(3) C26B C21B N22B C23B 1.8(2) N1B C21B N22B C23B -176.72(13) C21B N22B C23B C24B -1.5(2) N22B C23B C24B C25B 0.1(3) C23B C24B C25B C26B 1.2(3) C24B C25B C26B C21B -0.9(3) N22B C21B C26B C25B -0.6(3) N1B C21B C26B C25B 177.76(17)