#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105084.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_2105084 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 358 _chemical_name_common Foo _chemical_name_systematic 2-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 64.412(4) _cell_angle_beta 68.453(4) _cell_angle_gamma 86.091(4) _cell_formula_units_Z 4 _cell_length_a 9.7560(4) _cell_length_b 10.7699(5) _cell_length_c 11.9694(2) _cell_measurement_reflns_used 5781 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.55 _cell_volume 1048.87(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 0.999 _diffrn_measured_fraction_theta_max 0.933 _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 0.0119 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9959 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 29.48 _diffrn_reflns_theta_min 2.20 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 60 _diffrn_standards_number 9959 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_T_max 0.9721 _exptl_absorpt_correction_T_min 0.9585 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.306 _refine_diff_density_min -0.225 _refine_ls_extinction_coef 0.035(3) _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 1.037 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 5437 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0437 _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^)+(0.0447P)^2^+0.216P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1058 _refine_ls_wR_factor_ref 0.1141 _reflns_number_gt 4377 _reflns_number_total 5437 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 10-128 is Foo in P-1 [Z'=2] at Rt with Mo 40kV30mA to 0.80\%A CELL 0.71073 9.7560 10.7699 11.9694 64.412 68.453 86.091 ZERR 4 0.0004 0.0005 0.0002 0.004 0.004 0.004 LATT 1 SFAC C H N O F UNIT 48 36 8 4 4 MERG 3 FMAP 2 L.S. 8 LIST 4 ACTA 56 CONF BOND $H HTAB EQIV $2 X,Y,Z-1 EQIV $3 -X,-Y,2-Z HTAB N1A N22B HTAB N1B N22A HTAB N1A F12A HTAB N1B F12B HTAB C26A O1A HTAB C26B O1B HTAB C16B C11A_$2 HTAB C16B C12A_$2 HTAB C16B C13A_$2 HTAB C16B C14A_$2 HTAB C16B C15A_$2 HTAB C16B C16A_$2 HTAB C23A C11B HTAB C23A C12B HTAB C23A C13B HTAB C23A C14B HTAB C23A C15B HTAB C23A C16B HTAB C23B C11A HTAB C23B C12A HTAB C23B C13A HTAB C23B C14A HTAB C23B C15A HTAB C23B C16A HTAB C24B C21A_$3 HTAB C24B N22A_$3 HTAB C24B C23A_$3 HTAB C24B C24A_$3 HTAB C24B C25A_$3 HTAB C24B C26A_$3 RTAB OC O1A C1A RTAB NC N1A C1A RTAB NC N1A C11A RTAB CC C1A C21A RTAB NF N22A F12A RTAB CF C24A F12A RTAB OC O1B C1B RTAB NC N1B C1B RTAB NC N1B C11B RTAB CC C1B C21B RTAB NF N22B F12B RTAB CF C24B F12B RTAB OCN O1A C1A N1A RTAB CNC C1A N1A C11A RTAB NCC N1A C1A C21A RTAB CCN C1A C11A C12A RTAB CCC C1A C11A C16A RTAB NCN N1A C21A N22A RTAB NCC N1A C21A C26A RTAB CCC C11A C12A C13A RTAB CNC C21A N22A C23A RTAB OCC O1A C1A C11A RTAB CCC C1A C11A C12A RTAB CCC C1A C11A C16A RTAB FCC F12A C12A C11A RTAB FCC F12A C12A C13A RTAB OCN O1B C1B N1B RTAB CNC C1B N1B C11B RTAB NCC N1B C1B C21B RTAB CCN C1B C11B C12B RTAB CCC C1B C11B C16B RTAB NCN N1B C21B N22B RTAB NCC N1B C21B C26B RTAB CCC C11B C12B C13B RTAB CNC C21B N22B C23B RTAB OCC O1B C1B C11B RTAB CCC C1B C11B C12B RTAB CCC C1B C11B C16B RTAB FCC F12B C12B C11B RTAB FCC F12B C12B C13B RTAB OCCC O1A C1A C11A C12A RTAB OCCC O1A C1A C11A C26A RTAB CNCN C1A N1A C21A N22A RTAB CNCC C1A N1A C21A C26A RTAB OCCC O1B C1B C11B C12B RTAB OCCC O1B C1B C11B C26B RTAB CNCN C1B N1B C21B N22B RTAB CNCC C1B N1B C21B C26B SIZE 0.28 0.35 0.42 TEMP 21 PLAN 10 MPLA 6 C11A C12A C13A C14A C15A C16A F12A MPLA 5 O1A N1A C1A C11A C21A F12A MPLA 6 C21A N22A C23A C24A C25A C26A F12A MPLA 6 C11A C12A C13A C14A C15A C16A MPLA 3 O1A N1A C1A C11A C21A MPLA 6 C21A N22A C23A C24A C25A C26A MPLA 6 C11B C12B C13B C14B C15B C16B F12B MPLA 5 O1B N1B C1B C11B C21B F12B MPLA 6 C21B N22B C23B C24B C25B C26B F12B MPLA 6 C11B C12B C13B C14B C15B C16B MPLA 3 O1B N1B C1B C11B C21B MPLA 6 C21B N22B C23B C24B C25B C26B WGHT 0.044700 0.216000 EXTI 0.035396 FVAR 9.14144 MOLE 1 F12A 5 0.446084 0.158098 0.997467 11.00000 0.05230 0.08009 = 0.07341 -0.01702 -0.00195 0.00497 O1A 4 0.146473 0.366648 1.051310 11.00000 0.16359 0.05405 = 0.07997 -0.04446 -0.07519 0.04510 C1A 1 0.171783 0.265125 1.030408 11.00000 0.05911 0.04049 = 0.04843 -0.02332 -0.02535 0.01124 N1A 3 0.177460 0.258153 0.918719 11.00000 0.05791 0.03399 = 0.04372 -0.01981 -0.02289 0.01200 H1A 2 0.190481 0.178781 0.915536 11.00000 0.05231 C11A 1 0.197305 0.134740 1.133956 11.00000 0.04794 0.03895 = 0.04247 -0.02140 -0.02086 0.00701 C12A 1 0.334498 0.087078 1.116104 11.00000 0.04511 0.04856 = 0.05002 -0.02003 -0.01506 0.00374 C13A 1 0.362492 -0.026789 1.213338 11.00000 0.05470 0.05643 = 0.07629 -0.02791 -0.03680 0.01698 AFIX 43 H13A 2 0.457001 -0.055439 1.198102 11.00000 -1.20000 AFIX 0 C14A 1 0.248292 -0.097190 1.333146 11.00000 0.07942 0.04730 = 0.05911 -0.01526 -0.04071 0.00796 AFIX 43 H14A 2 0.265088 -0.174558 1.400139 11.00000 -1.20000 AFIX 0 C15A 1 0.109177 -0.054164 1.354870 11.00000 0.06822 0.05310 = 0.04401 -0.01434 -0.01546 -0.00441 AFIX 43 H15A 2 0.031740 -0.103471 1.435889 11.00000 -1.20000 AFIX 0 C16A 1 0.083689 0.062203 1.256778 11.00000 0.04678 0.05331 = 0.05116 -0.02567 -0.01634 0.00616 AFIX 43 H16A 2 -0.010267 0.092138 1.273169 11.00000 -1.20000 AFIX 0 C21A 1 0.153692 0.362298 0.808249 11.00000 0.04128 0.03532 = 0.04167 -0.01610 -0.01562 0.00595 N22A 3 0.172276 0.324486 0.711434 11.00000 0.05120 0.04334 = 0.04336 -0.02094 -0.02002 0.01243 C23A 1 0.145920 0.415147 0.604242 11.00000 0.06091 0.05448 = 0.04573 -0.02290 -0.02451 0.01536 AFIX 43 H23A 2 0.157245 0.389422 0.536763 11.00000 -1.20000 AFIX 0 C24A 1 0.103212 0.543679 0.588226 11.00000 0.07084 0.04794 = 0.05223 -0.01387 -0.03071 0.01432 AFIX 43 H24A 2 0.085607 0.603486 0.512259 11.00000 -1.20000 AFIX 0 C25A 1 0.087193 0.581473 0.688097 11.00000 0.08121 0.03802 = 0.06579 -0.02056 -0.03546 0.01834 AFIX 43 H25A 2 0.059403 0.668450 0.679650 11.00000 -1.20000 AFIX 0 C26A 1 0.112155 0.491007 0.800376 11.00000 0.06911 0.03836 = 0.05307 -0.02232 -0.02721 0.01321 AFIX 43 H26A 2 0.101608 0.515108 0.868710 11.00000 -1.20000 AFIX 0 MOLE 2 F12B 5 0.506833 0.291215 0.542754 11.00000 0.06920 0.07551 = 0.07904 -0.03149 -0.04062 -0.00430 O1B 4 0.322172 -0.033663 0.551000 11.00000 0.11193 0.04972 = 0.06007 -0.03288 -0.03598 0.00801 C1B 1 0.327217 0.067309 0.570713 11.00000 0.05186 0.04508 = 0.04818 -0.02582 -0.02089 0.00785 N1B 3 0.291273 0.062395 0.693864 11.00000 0.06190 0.03624 = 0.04480 -0.02202 -0.02009 0.00938 H1B 2 0.271911 0.138647 0.702228 11.00000 0.05378 C11B 1 0.367830 0.210015 0.457612 11.00000 0.04546 0.04713 = 0.04339 -0.02375 -0.01461 0.00736 C12B 1 0.453517 0.314984 0.446345 11.00000 0.04323 0.05651 = 0.05375 -0.02637 -0.01710 0.00369 C13B 1 0.487716 0.444569 0.340280 11.00000 0.05426 0.05641 = 0.07081 -0.02100 -0.01410 -0.00911 AFIX 43 H13B 2 0.545706 0.512992 0.335666 11.00000 -1.20000 AFIX 0 C14B 1 0.434723 0.471321 0.241096 11.00000 0.07808 0.05725 = 0.05923 -0.00776 -0.01969 -0.00152 AFIX 43 H14B 2 0.456394 0.558675 0.169154 11.00000 -1.20000 AFIX 0 C15B 1 0.350024 0.369687 0.247835 11.00000 0.08653 0.06767 = 0.05304 -0.01871 -0.03360 0.00815 AFIX 43 H15B 2 0.314270 0.388233 0.180707 11.00000 -1.20000 AFIX 0 C16B 1 0.318187 0.240442 0.354041 11.00000 0.06697 0.05666 = 0.05039 -0.02588 -0.02542 0.00477 AFIX 43 H16B 2 0.262307 0.171751 0.356917 11.00000 -1.20000 AFIX 0 C21B 1 0.259858 -0.055038 0.816140 11.00000 0.04326 0.03667 = 0.04671 -0.01963 -0.01856 0.00493 N22B 3 0.208796 -0.026425 0.921556 11.00000 0.05770 0.03745 = 0.04507 -0.01934 -0.01913 0.00432 C23B 1 0.179161 -0.132367 1.042735 11.00000 0.06145 0.04368 = 0.04531 -0.01766 -0.01748 -0.00075 AFIX 43 H23B 2 0.141720 -0.113889 1.116867 11.00000 -1.20000 AFIX 0 C24B 1 0.200984 -0.266505 1.063481 11.00000 0.05863 0.04032 = 0.05331 -0.01077 -0.02169 -0.00006 AFIX 43 H24B 2 0.180850 -0.336863 1.149116 11.00000 -1.20000 AFIX 0 C25B 1 0.253497 -0.293771 0.953896 11.00000 0.07287 0.03565 = 0.06985 -0.02101 -0.02723 0.01056 AFIX 43 H25B 2 0.268877 -0.383843 0.964952 11.00000 -1.20000 AFIX 0 C26B 1 0.283394 -0.188338 0.827920 11.00000 0.06975 0.04231 = 0.05824 -0.02796 -0.02299 0.01293 AFIX 43 H26B 2 0.318217 -0.205543 0.753009 11.00000 -1.20000 HKLF 4 REM 10-128 is Foo in P-1 [Z'=2] at Rt with Mo 40kV30mA to 0.80\%A REM R1 = 0.0437 for 4377 Fo > 4sig(Fo) and 0.0547 for all 5437 data REM 298 parameters refined using 0 restraints END WGHT 0.0447 0.2160 REM Highest difference peak 0.306, deepest hole -0.225, 1-sigma level 0.032 Q1 1 0.2427 0.3767 0.9867 11.00000 0.05 0.31 Q2 1 0.3415 0.1465 0.5149 11.00000 0.05 0.21 Q3 1 0.1093 0.4156 0.8167 11.00000 0.05 0.20 Q4 1 0.0756 0.3202 1.0652 11.00000 0.05 0.18 Q5 1 0.3145 -0.1151 0.8197 11.00000 0.05 0.18 Q6 1 0.1838 0.1918 1.0853 11.00000 0.05 0.18 Q7 1 0.1396 0.0760 1.1783 11.00000 0.05 0.17 Q8 1 0.3790 0.2177 0.3890 11.00000 0.05 0.17 Q9 1 0.0828 0.4645 0.6227 11.00000 0.05 0.16 Q10 1 0.4363 0.3867 0.4085 11.00000 0.05 0.16 ; _cod_data_source_file gp5047.cif _cod_data_source_block Foo-10-128 _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_original_cell_volume 1048.88(7) _cod_database_code 2105084 _cod_database_fobs_code 2105084 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 F12A 0.44608(10) 0.15810(11) 0.99747(10) 0.0817(3) Uani d . 1 1 O O1A 0.14647(19) 0.36665(12) 1.05131(13) 0.0859(4) Uani d . 1 1 C C1A 0.17178(16) 0.26512(13) 1.03041(13) 0.0466(3) Uani d . 1 1 N N1A 0.17746(13) 0.25815(11) 0.91872(11) 0.0433(2) Uani d . 1 1 H H1A 0.1905(17) 0.1788(17) 0.9155(15) 0.052(4) Uiso d . 1 1 C C11A 0.19731(14) 0.13474(12) 1.13396(12) 0.0407(3) Uani d . 1 1 C C12A 0.33450(15) 0.08708(14) 1.11610(14) 0.0493(3) Uani d . 1 1 C C13A 0.36249(18) -0.02679(16) 1.21334(17) 0.0597(4) Uani d . 1 1 H H13A 0.4570 -0.0554 1.1981 0.072 Uiso calc R 1 1 C C14A 0.24829(19) -0.09719(15) 1.33315(16) 0.0604(4) Uani d . 1 1 H H14A 0.2651 -0.1746 1.4001 0.073 Uiso calc R 1 1 C C15A 0.10918(19) -0.05416(16) 1.35487(15) 0.0590(4) Uani d . 1 1 H H15A 0.0317 -0.1035 1.4359 0.071 Uiso calc R 1 1 C C16A 0.08369(16) 0.06220(14) 1.25678(14) 0.0500(3) Uani d . 1 1 H H16A -0.0103 0.0921 1.2732 0.060 Uiso calc R 1 1 C C21A 0.15369(13) 0.36230(12) 0.80825(12) 0.0398(3) Uani d . 1 1 N N22A 0.17228(12) 0.32449(11) 0.71143(10) 0.0449(2) Uani d . 1 1 C C23A 0.14592(16) 0.41515(15) 0.60424(14) 0.0524(3) Uani d . 1 1 H H23A 0.1572 0.3894 0.5368 0.063 Uiso calc R 1 1 C C24A 0.10321(18) 0.54368(15) 0.58823(15) 0.0581(4) Uani d . 1 1 H H24A 0.0856 0.6035 0.5123 0.070 Uiso calc R 1 1 C C25A 0.08719(19) 0.58147(14) 0.68810(16) 0.0607(4) Uani d . 1 1 H H25A 0.0594 0.6685 0.6797 0.073 Uiso calc R 1 1 C C26A 0.11215(17) 0.49101(13) 0.80038(14) 0.0517(3) Uani d . 1 1 H H26A 0.1016 0.5151 0.8687 0.062 Uiso calc R 1 1 F F12B 0.50683(11) 0.29122(10) 0.54275(10) 0.0708(3) Uani d . 1 1 O O1B 0.32217(15) -0.03366(11) 0.55100(11) 0.0693(3) Uani d . 1 1 C C1B 0.32722(15) 0.06731(14) 0.57071(13) 0.0458(3) Uani d . 1 1 N N1B 0.29127(13) 0.06240(11) 0.69386(11) 0.0462(3) Uani d . 1 1 H H1B 0.2719(17) 0.1386(17) 0.7022(15) 0.054(4) Uiso d . 1 1 C C11B 0.36783(14) 0.21001(13) 0.45761(13) 0.0446(3) Uani d . 1 1 C C12B 0.45352(15) 0.31498(15) 0.44635(14) 0.0506(3) Uani d . 1 1 C C13B 0.48772(18) 0.44457(17) 0.34028(17) 0.0653(4) Uani d . 1 1 H H13B 0.5457 0.5130 0.3357 0.078 Uiso calc R 1 1 C C14B 0.4347(2) 0.47132(18) 0.24110(18) 0.0731(5) Uani d . 1 1 H H14B 0.4564 0.5587 0.1692 0.088 Uiso calc R 1 1 C C15B 0.3500(2) 0.36969(18) 0.24784(17) 0.0697(4) Uani d . 1 1 H H15B 0.3143 0.3882 0.1807 0.084 Uiso calc R 1 1 C C16B 0.31819(18) 0.24044(16) 0.35404(14) 0.0559(3) Uani d . 1 1 H H16B 0.2623 0.1718 0.3569 0.067 Uiso calc R 1 1 C C21B 0.25986(14) -0.05504(12) 0.81614(13) 0.0412(3) Uani d . 1 1 N N22B 0.20880(13) -0.02642(11) 0.92156(11) 0.0463(3) Uani d . 1 1 C C23B 0.17916(17) -0.13237(14) 1.04274(14) 0.0513(3) Uani d . 1 1 H H23B 0.1417 -0.1139 1.1169 0.062 Uiso calc R 1 1 C C24B 0.20098(17) -0.26650(14) 1.06348(15) 0.0540(3) Uani d . 1 1 H H24B 0.1809 -0.3369 1.1491 0.065 Uiso calc R 1 1 C C25B 0.25350(19) -0.29377(14) 0.95390(16) 0.0604(4) Uani d . 1 1 H H25B 0.2689 -0.3838 0.9650 0.072 Uiso calc R 1 1 C C26B 0.28339(18) -0.18834(14) 0.82792(15) 0.0552(3) Uani d . 1 1 H H26B 0.3182 -0.2055 0.7530 0.066 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 F12A 0.0523(5) 0.0801(7) 0.0734(6) 0.0050(5) -0.0019(5) -0.0170(5) O1A 0.1636(14) 0.0540(6) 0.0800(8) 0.0451(8) -0.0752(9) -0.0445(6) C1A 0.0591(8) 0.0405(6) 0.0484(7) 0.0112(6) -0.0254(6) -0.0233(6) N1A 0.0579(7) 0.0340(5) 0.0437(6) 0.0120(5) -0.0229(5) -0.0198(4) C11A 0.0479(7) 0.0390(6) 0.0425(6) 0.0070(5) -0.0209(5) -0.0214(5) C12A 0.0451(7) 0.0486(7) 0.0500(7) 0.0037(5) -0.0151(6) -0.0200(6) C13A 0.0547(8) 0.0564(8) 0.0763(10) 0.0170(7) -0.0368(8) -0.0279(8) C14A 0.0794(11) 0.0473(8) 0.0591(9) 0.0080(7) -0.0407(8) -0.0153(7) C15A 0.0682(10) 0.0531(8) 0.0440(7) -0.0044(7) -0.0155(7) -0.0143(6) C16A 0.0468(7) 0.0533(8) 0.0512(7) 0.0062(6) -0.0163(6) -0.0257(6) C21A 0.0413(6) 0.0353(6) 0.0417(6) 0.0060(5) -0.0156(5) -0.0161(5) N22A 0.0512(6) 0.0433(6) 0.0434(6) 0.0124(5) -0.0200(5) -0.0209(5) C23A 0.0609(8) 0.0545(8) 0.0457(7) 0.0154(6) -0.0245(6) -0.0229(6) C24A 0.0708(10) 0.0479(7) 0.0522(8) 0.0143(7) -0.0307(7) -0.0139(6) C25A 0.0812(11) 0.0380(7) 0.0658(9) 0.0183(7) -0.0355(8) -0.0206(7) C26A 0.0691(9) 0.0384(6) 0.0531(8) 0.0132(6) -0.0272(7) -0.0223(6) F12B 0.0692(6) 0.0755(6) 0.0790(6) -0.0043(5) -0.0406(5) -0.0315(5) O1B 0.1119(10) 0.0497(6) 0.0601(6) 0.0080(6) -0.0360(6) -0.0329(5) C1B 0.0519(7) 0.0451(7) 0.0482(7) 0.0079(5) -0.0209(6) -0.0258(6) N1B 0.0619(7) 0.0362(5) 0.0448(6) 0.0094(5) -0.0201(5) -0.0220(5) C11B 0.0455(7) 0.0471(7) 0.0434(7) 0.0074(5) -0.0146(5) -0.0238(6) C12B 0.0432(7) 0.0565(8) 0.0538(8) 0.0037(6) -0.0171(6) -0.0264(6) C13B 0.0543(9) 0.0564(9) 0.0708(10) -0.0091(7) -0.0141(8) -0.0210(8) C14B 0.0781(11) 0.0573(9) 0.0592(10) -0.0015(8) -0.0197(9) -0.0078(8) C15B 0.0865(12) 0.0677(10) 0.0530(9) 0.0081(9) -0.0336(9) -0.0187(8) C16B 0.0670(9) 0.0567(8) 0.0504(8) 0.0048(7) -0.0254(7) -0.0259(7) C21B 0.0433(6) 0.0367(6) 0.0467(7) 0.0049(5) -0.0186(5) -0.0196(5) N22B 0.0577(7) 0.0374(5) 0.0451(6) 0.0043(5) -0.0191(5) -0.0193(5) C23B 0.0615(8) 0.0437(7) 0.0453(7) -0.0008(6) -0.0175(6) -0.0177(6) C24B 0.0586(8) 0.0403(7) 0.0533(8) -0.0001(6) -0.0217(7) -0.0108(6) C25B 0.0729(10) 0.0356(7) 0.0699(10) 0.0106(6) -0.0272(8) -0.0210(7) C26B 0.0698(9) 0.0423(7) 0.0582(8) 0.0129(6) -0.0230(7) -0.0280(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 124.86(12) O1A C1A C11A 119.68(12) N1A C1A C11A 115.45(10) C1A N1A C21A 127.63(10) C1A N1A H1A 117.9(10) C21A N1A H1A 114.3(10) C12A C11A C16A 117.21(12) C12A C11A C1A 122.16(12) C16A C11A C1A 120.49(12) F12A C12A C13A 119.37(13) F12A C12A C11A 117.57(12) C13A C12A C11A 123.05(13) C14A C13A C12A 118.59(14) C14A C13A H13A 120.7 C12A C13A H13A 120.7 C13A C14A C15A 120.34(14) C13A C14A H14A 119.8 C15A C14A H14A 119.8 C14A C15A C16A 120.26(14) C14A C15A H15A 119.9 C16A C15A H15A 119.9 C15A C16A C11A 120.52(13) C15A C16A H16A 119.7 C11A C16A H16A 119.7 N22A C21A C26A 122.99(11) N22A C21A N1A 113.10(10) C26A C21A N1A 123.90(11) C21A N22A C23A 117.39(11) N22A C23A C24A 123.76(13) N22A C23A H23A 118.1 C24A C23A H23A 118.1 C23A C24A C25A 117.90(13) C23A C24A H24A 121.1 C25A C24A H24A 121.1 C26A C25A C24A 120.20(13) C26A C25A H25A 119.9 C24A C25A H25A 119.9 C25A C26A C21A 117.74(13) C25A C26A H26A 121.1 C21A C26A H26A 121.1 O1B C1B N1B 124.18(13) O1B C1B C11B 120.95(12) N1B C1B C11B 114.81(11) C1B N1B C21B 127.86(11) C1B N1B H1B 118.1(10) C21B N1B H1B 113.4(10) C12B C11B C16B 116.72(13) C12B C11B C1B 124.88(12) C16B C11B C1B 118.40(12) F12B C12B C13B 117.83(13) F12B C12B C11B 119.51(13) C13B C12B C11B 122.65(14) C12B C13B C14B 118.93(15) C12B C13B H13B 120.5 C14B C13B H13B 120.5 C15B C14B C13B 120.34(16) C15B C14B H14B 119.8 C13B C14B H14B 119.8 C14B C15B C16B 119.86(16) C14B C15B H15B 120.1 C16B C15B H15B 120.1 C15B C16B C11B 121.49(15) C15B C16B H16B 119.3 C11B C16B H16B 119.3 N22B C21B C26B 122.80(12) N22B C21B N1B 113.34(10) C26B C21B N1B 123.83(12) C21B N22B C23B 117.48(11) N22B C23B C24B 123.65(13) N22B C23B H23B 118.2 C24B C23B H23B 118.2 C23B C24B C25B 117.98(13) C23B C24B H24B 121.0 C25B C24B H24B 121.0 C24B C25B C26B 120.23(13) C24B C25B H25B 119.9 C26B C25B H25B 119.9 C25B C26B C21B 117.86(13) C25B C26B H26B 121.1 C21B C26B H26B 121.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F12A C12A 1.3515(16) O1A C1A 1.2138(15) C1A N1A 1.3519(16) C1A C11A 1.4986(17) N1A C21A 1.4032(15) N1A H1A 0.871(16) C11A C12A 1.3754(18) C11A C16A 1.3890(18) C12A C13A 1.374(2) C13A C14A 1.369(2) C13A H13A 0.9300 C14A C15A 1.372(2) C14A H14A 0.9300 C15A C16A 1.383(2) C15A H15A 0.9300 C16A H16A 0.9300 C21A N22A 1.3360(15) C21A C26A 1.3904(17) N22A C23A 1.3385(16) C23A C24A 1.370(2) C23A H23A 0.9300 C24A C25A 1.376(2) C24A H24A 0.9300 C25A C26A 1.375(2) C25A H25A 0.9300 C26A H26A 0.9300 F12B C12B 1.3547(16) O1B C1B 1.2158(15) C1B N1B 1.3616(16) C1B C11B 1.4979(19) N1B C21B 1.4000(16) N1B H1B 0.870(16) C11B C12B 1.3818(19) C11B C16B 1.3954(19) C12B C13B 1.376(2) C13B C14B 1.377(2) C13B H13B 0.9300 C14B C15B 1.373(3) C14B H14B 0.9300 C15B C16B 1.375(2) C15B H15B 0.9300 C16B H16B 0.9300 C21B N22B 1.3373(16) C21B C26B 1.3920(17) N22B C23B 1.3404(17) C23B C24B 1.3715(19) C23B H23B 0.9300 C24B C25B 1.374(2) C24B H24B 0.9300 C25B C26B 1.375(2) 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_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1A H1A N22B 0.871(16) 2.177(16) 3.0460(14) 175.7(14) yes N1B H1B N22A 0.870(16) 2.193(16) 3.0408(15) 164.8(14) yes N1B H1B F12B 0.870(16) 2.487(16) 2.7981(15) 101.8(12) yes C26A H26A O1A 0.93 2.26 2.8513(18) 121 yes C26B H26B O1B 0.93 2.31 2.8810(19) 119 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 -1.1(2) C11A C1A N1A C21A 178.01(12) O1A C1A C11A C12A -109.55(17) N1A C1A C11A C12A 71.26(17) O1A C1A C11A C16A 65.87(19) N1A C1A C11A C16A -113.32(14) C16A C11A C12A F12A -179.19(12) C1A C11A C12A F12A -3.63(19) C16A C11A C12A C13A -0.2(2) C1A C11A C12A C13A 175.36(13) F12A C12A C13A C14A 179.73(14) C11A C12A C13A C14A 0.8(2) C12A C13A C14A C15A -0.1(2) C13A C14A C15A C16A -1.2(2) C14A C15A C16A C11A 1.7(2) C12A C11A C16A C15A -1.05(19) C1A C11A C16A C15A -176.69(12) C1A N1A C21A N22A 177.88(13) C1A N1A C21A C26A -3.3(2) C26A C21A N22A C23A -1.5(2) N1A C21A N22A C23A 177.29(12) C21A N22A C23A C24A 0.8(2) N22A C23A C24A C25A 0.3(2) C23A C24A C25A C26A -0.7(3) C24A C25A C26A C21A 0.1(2) N22A C21A C26A C25A 1.1(2) N1A C21A C26A C25A -177.61(14) O1B C1B N1B C21B 8.1(2) C11B C1B N1B C21B -174.76(12) O1B C1B C11B C12B -142.07(15) N1B C1B C11B C12B 40.69(18) O1B C1B C11B C16B 36.9(2) N1B C1B C11B C16B -140.30(13) C16B C11B C12B F12B -179.06(12) C1B C11B C12B F12B 0.0(2) C16B C11B C12B C13B 1.0(2) C1B C11B C12B C13B -179.98(13) F12B C12B C13B C14B -179.94(15) C11B C12B C13B C14B 0.0(2) C12B C13B C14B C15B -0.5(3) C13B C14B C15B C16B -0.1(3) C14B C15B C16B C11B 1.2(3) C12B C11B C16B C15B -1.6(2) C1B C11B C16B C15B 179.31(14) C1B N1B C21B N22B -171.38(13) C1B N1B C21B C26B 10.6(2) C26B C21B N22B C23B -0.3(2) N1B C21B N22B C23B -178.40(12) C21B N22B C23B C24B 1.3(2) N22B C23B C24B C25B -1.3(2) C23B C24B C25B C26B 0.3(2) C24B C25B C26B C21B 0.5(2) N22B C21B C26B C25B -0.5(2) N1B C21B C26B C25B 177.33(13)