#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:47 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306587 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577412.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1577412 loop_ _publ_author_name 'Wang, Haiwen' 'Bhaduri, Nilanjan' 'Greaney, Michael F.' _publ_section_title ; Trifluoromethylation of pyridines through skeletal rearrangement ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC04438G _journal_year 2026 _chemical_formula_moiety 'C25 H23 N O' _chemical_formula_sum 'C25 H23 N O' _chemical_formula_weight 353.44 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-09-01 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _audit_update_record ; 2025-09-11 deposited with the CCDC. 2026-06-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.1212(9) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 10.29270(10) _cell_length_b 20.50005(19) _cell_length_c 18.53109(19) _cell_measurement_reflns_used 8448 _cell_measurement_temperature 99.98(10) _cell_measurement_theta_max 75.6640 _cell_measurement_theta_min 4.7240 _cell_volume 3910.07(7) _computing_cell_refinement 'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 44.117a 64-bit (release 07-07-2025))' _computing_data_reduction 'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.98(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.960 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -5.00 21.00 0.50 0.75 -- 43.87 30.00 30.00 52 2 \w 22.00 133.00 0.50 0.75 -- 43.87 30.00 30.00 222 3 \w 8.00 135.00 0.50 0.75 -- 46.33 60.00 0.00 254 4 \w -34.00 -6.00 0.50 0.75 -- 46.33 0.00-180.00 56 5 \w 161.00 198.00 0.50 4.00 -- 108.20 40.00 -30.00 74 6 \w 19.00 45.00 0.50 4.00 -- 108.20 50.00 -60.00 52 7 \w 23.00 198.00 0.50 4.00 -- 108.20 60.00 -60.00 350 8 \w 48.00 111.00 0.50 4.00 -- 108.20 20.00 30.00 126 9 \w 137.00 198.00 0.50 4.00 -- 108.20 50.00 -60.00 122 10 \w 94.00 120.00 0.50 4.00 -- 108.20 50.00 -60.00 52 11 \w 78.00 198.00 0.50 4.00 -- 108.20 60.00 150.00 240 12 \w 59.00 198.00 0.50 4.00 -- 108.20 40.00 150.00 278 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC11 (RINC): quarter-chi single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0156098000 _diffrn_orient_matrix_UB_12 0.0494939000 _diffrn_orient_matrix_UB_13 -0.0619338000 _diffrn_orient_matrix_UB_21 0.0457090000 _diffrn_orient_matrix_UB_22 -0.0551954000 _diffrn_orient_matrix_UB_23 -0.0502295000 _diffrn_orient_matrix_UB_31 -0.1417370000 _diffrn_orient_matrix_UB_32 -0.0124271000 _diffrn_orient_matrix_UB_33 -0.0232928000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_unetI/netI 0.0414 _diffrn_reflns_Laue_measured_fraction_full 0.960 _diffrn_reflns_Laue_measured_fraction_max 0.960 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 21995 _diffrn_reflns_point_group_measured_fraction_full 0.960 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 66.600 _diffrn_reflns_theta_max 66.599 _diffrn_reflns_theta_min 3.215 _diffrn_source 'Rotating-anode X-ray tube (dual wavelength)' _diffrn_source_type 'Rigaku (Cu) X-ray DW Source' _exptl_absorpt_coefficient_mu 0.561 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.931 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.201 _exptl_crystal_description block _exptl_crystal_F_000 1504 _exptl_crystal_size_max 0.073 _exptl_crystal_size_mid 0.052 _exptl_crystal_size_min 0.044 _refine_diff_density_max 0.323 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.034 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 487 _refine_ls_number_reflns 6625 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0405 _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^)+(0.0498P)^2^+0.8042P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0991 _refine_ls_wR_factor_ref 0.1047 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5486 _reflns_number_total 6625 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc04438g2.cif _cod_data_source_block s6746l _cod_database_code 1577412 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula 'C H N O' _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C19B(H19A,H19B), C12B(H12A,H12B), C19A(H19C,H19D), C12A(H12C,H12D) 2.b Aromatic/amide H refined with riding coordinates: C8B(H8B), C11A(H11A), C11B(H11B), C10B(H10B), C9B(H9B), C5A(H5A), C10A(H10A), C4A(H4A), C1B(H1B), C9A(H9A), C18B(H18B), C8A(H8A), C21B(H21B), C25B(H25B), C14B(H14B), C25A(H25A), C5B(H5B), C3A(H3A), C1A(H1A), C2B(H2B), C14A(H14A), C15A(H15A), C18A(H18A), C24A(H24A), C16A(H16A), C17B(H17B), C15B(H15B), C2A(H2A), C4B(H4B), C21A(H21A), C16B(H16B), C3B(H3B), C23A(H23A), C22B(H22B), C24B(H24B), C17A(H17A), C23B(H23B), C22A(H22A) ; _shelx_res_file ; TITL s6746l_a.res in P2(1)/c s6746l.res created by SHELXL-2019/3 at 09:27:29 on 01-Sep-2025 REM Old TITL s6746l in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.147, Rweak 0.019, Alpha 0.028 REM 0.574 for 178 systematic absences, Orientation as input REM Formula found by SHELXT: C1A N1A O1A CELL 1.54184 10.292703 20.500048 18.531093 90 90.1212 90 ZERR 8 0.000102 0.000191 0.000187 0 0.0009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 200 184 8 8 L.S. 14 PLAN 15 TEMP -173 CONF BOND fmap 2 MORE -1 BOND $H ACTA REM REM REM WGHT 0.049800 0.804200 FVAR 2.91256 O1B 4 1.043028 0.358815 0.012266 11.00000 0.03546 0.03491 = 0.05393 0.00071 0.00927 0.00054 O1A 4 0.428601 0.399195 0.401549 11.00000 0.03762 0.03916 = 0.04569 0.00075 -0.00200 -0.00852 N1B 3 0.641927 0.587173 0.072296 11.00000 0.02921 0.02538 = 0.03971 -0.00064 -0.00067 0.00072 N1A 3 0.226213 0.570920 0.668561 11.00000 0.03411 0.02840 = 0.03855 -0.00038 -0.00648 -0.00270 C20B 1 0.605294 0.687044 -0.000870 11.00000 0.02544 0.03229 = 0.03403 0.00012 0.00145 -0.00302 C8B 1 0.820947 0.367371 0.043084 11.00000 0.03216 0.02889 = 0.03308 0.00123 0.00112 0.00038 AFIX 43 H8B 2 0.743021 0.344033 0.052385 11.00000 -1.20000 AFIX 0 C11A 1 0.277988 0.538793 0.612937 11.00000 0.03664 0.02494 = 0.03657 0.00607 -0.00457 -0.00275 AFIX 43 H11A 2 0.369889 0.540730 0.608806 11.00000 -1.20000 AFIX 0 C11B 1 0.730543 0.541216 0.056836 11.00000 0.02614 0.03096 = 0.03269 -0.00032 -0.00194 0.00087 AFIX 43 H11B 2 0.813392 0.556378 0.041794 11.00000 -1.20000 AFIX 0 C10B 1 0.715011 0.475161 0.060297 11.00000 0.02899 0.02966 = 0.03410 0.00024 -0.00116 -0.00140 AFIX 43 H10B 2 0.634324 0.457206 0.075206 11.00000 -1.20000 AFIX 0 C9B 1 0.818913 0.433585 0.041708 11.00000 0.03154 0.03213 = 0.02969 0.00066 -0.00058 -0.00061 AFIX 43 H9B 2 0.896626 0.454369 0.026426 11.00000 -1.20000 AFIX 0 C19B 1 0.671463 0.656353 0.063812 11.00000 0.03352 0.02661 = 0.03606 -0.00291 -0.00321 -0.00055 AFIX 23 H19A 2 0.766621 0.661705 0.058870 11.00000 -1.20000 H19B 2 0.644209 0.679831 0.107943 11.00000 -1.20000 AFIX 0 C13B 1 0.493526 0.557605 0.173873 11.00000 0.03100 0.02559 = 0.04329 0.00114 -0.00007 0.00626 C5A 1 0.130190 0.309056 0.385240 11.00000 0.03574 0.03069 = 0.03197 0.00184 -0.00316 0.00008 AFIX 43 H5A 2 0.092556 0.320264 0.430334 11.00000 -1.20000 AFIX 0 C10A 1 0.214280 0.503354 0.561097 11.00000 0.03880 0.02727 = 0.03771 0.00379 -0.00558 -0.00392 AFIX 43 H10A 2 0.122025 0.501947 0.560814 11.00000 -1.20000 AFIX 0 C12B 1 0.510679 0.569227 0.093714 11.00000 0.02633 0.03074 = 0.04165 -0.00147 -0.00190 0.00172 AFIX 23 H12A 2 0.485448 0.529074 0.067520 11.00000 -1.20000 H12B 2 0.450510 0.604338 0.078524 11.00000 -1.20000 AFIX 0 C4A 1 0.072176 0.261565 0.342513 11.00000 0.03722 0.02970 = 0.04183 0.00195 -0.00547 -0.00235 AFIX 43 H4A 2 -0.004086 0.239926 0.358576 11.00000 -1.20000 AFIX 0 C13A 1 0.040379 0.535134 0.743512 11.00000 0.02842 0.03135 = 0.04261 -0.00523 -0.00761 -0.00300 C1B 1 1.053422 0.230745 0.071420 11.00000 0.04424 0.03626 = 0.03258 -0.00253 0.00185 0.00859 AFIX 43 H1B 2 1.128939 0.256392 0.079497 11.00000 -1.20000 AFIX 0 C7B 1 0.940540 0.331864 0.030535 11.00000 0.03541 0.03002 = 0.03105 -0.00104 0.00099 0.00115 C6A 1 0.243144 0.340433 0.362563 11.00000 0.03744 0.03134 = 0.03415 0.00461 -0.00594 -0.00140 C9A 1 0.284773 0.468963 0.508173 11.00000 0.04358 0.02886 = 0.03568 0.00593 -0.00240 -0.00587 AFIX 43 H9A 2 0.376429 0.474392 0.507640 11.00000 -1.20000 AFIX 0 C18B 1 0.572911 0.586486 0.225544 11.00000 0.03764 0.03411 = 0.04359 0.00370 -0.00227 -0.00013 AFIX 43 H18B 2 0.646517 0.611094 0.210946 11.00000 -1.20000 AFIX 0 C6B 1 0.940990 0.259796 0.044443 11.00000 0.03978 0.03185 = 0.02843 -0.00230 0.00552 0.00443 C20A 1 0.291416 0.677581 0.716643 11.00000 0.02989 0.03401 = 0.03481 -0.00571 -0.00412 -0.00520 C19A 1 0.308519 0.604646 0.721397 11.00000 0.03562 0.03369 = 0.03571 -0.00179 -0.00691 -0.00234 AFIX 23 H19C 2 0.400673 0.593440 0.712534 11.00000 -1.20000 H19D 2 0.285817 0.589737 0.770595 11.00000 -1.20000 AFIX 0 C12A 1 0.086063 0.576205 0.680752 11.00000 0.03379 0.03008 = 0.04750 -0.00213 -0.00806 0.00118 AFIX 23 H12C 2 0.039486 0.562376 0.636529 11.00000 -1.20000 H12D 2 0.063754 0.622419 0.690048 11.00000 -1.20000 AFIX 0 C8A 1 0.231381 0.428343 0.457479 11.00000 0.03756 0.03355 = 0.03692 0.00511 -0.00461 -0.00429 AFIX 43 H8A 2 0.139516 0.424456 0.454891 11.00000 -1.20000 AFIX 0 C21B 1 0.580926 0.652393 -0.063687 11.00000 0.03980 0.04013 = 0.03590 -0.00256 0.00240 -0.00726 AFIX 43 H21B 2 0.603345 0.607512 -0.066483 11.00000 -1.20000 AFIX 0 C25B 1 0.571823 0.752816 0.001842 11.00000 0.03423 0.03312 = 0.04355 0.00115 -0.00027 0.00028 AFIX 43 H25B 2 0.585813 0.776866 0.044984 11.00000 -1.20000 AFIX 0 C7A 1 0.309851 0.391355 0.408002 11.00000 0.03804 0.03242 = 0.03383 0.00749 -0.00486 -0.00440 C14B 1 0.388585 0.520207 0.196879 11.00000 0.03598 0.03310 = 0.05270 0.00383 -0.00076 -0.00012 AFIX 43 H14B 2 0.335315 0.498943 0.162185 11.00000 -1.20000 AFIX 0 C25A 1 0.227269 0.712280 0.770072 11.00000 0.03890 0.04637 = 0.03232 -0.00608 -0.00475 -0.00042 AFIX 43 H25A 2 0.194250 0.689924 0.811022 11.00000 -1.20000 AFIX 0 C5B 1 0.832658 0.221117 0.031319 11.00000 0.04358 0.03133 = 0.04343 -0.00385 0.00278 0.00242 AFIX 43 H5B 2 0.755415 0.240398 0.012993 11.00000 -1.20000 AFIX 0 C3A 1 0.126546 0.245861 0.275937 11.00000 0.04375 0.03657 = 0.03811 -0.00267 -0.00736 -0.00480 AFIX 43 H3A 2 0.085798 0.214447 0.245754 11.00000 -1.20000 AFIX 0 C1A 1 0.298224 0.322574 0.297010 11.00000 0.04112 0.04765 = 0.04010 -0.00098 0.00097 -0.00869 AFIX 43 H1A 2 0.376769 0.342553 0.281728 11.00000 -1.20000 AFIX 0 C2B 1 1.055399 0.164303 0.086557 11.00000 0.05930 0.04175 = 0.03676 0.00170 0.00488 0.02001 AFIX 43 H2B 2 1.131454 0.144892 0.106205 11.00000 -1.20000 AFIX 0 C14A 1 0.071088 0.469240 0.747862 11.00000 0.04187 0.03307 = 0.04166 -0.00458 0.00096 0.00023 AFIX 43 H14A 2 0.122543 0.449653 0.711292 11.00000 -1.20000 AFIX 0 C15A 1 0.027225 0.431953 0.805104 11.00000 0.05132 0.03711 = 0.04880 0.00134 -0.00189 -0.00615 AFIX 43 H15A 2 0.047887 0.386834 0.807379 11.00000 -1.20000 AFIX 0 C18A 1 -0.033235 0.563008 0.798112 11.00000 0.03242 0.04055 = 0.05537 -0.01559 -0.00603 0.00142 AFIX 43 H18A 2 -0.054405 0.608077 0.796065 11.00000 -1.20000 AFIX 0 C24A 1 0.210808 0.779188 0.764382 11.00000 0.03806 0.04489 = 0.05046 -0.01809 -0.00703 0.00355 AFIX 43 H24A 2 0.167481 0.802473 0.801552 11.00000 -1.20000 AFIX 0 C16A 1 -0.046357 0.460077 0.858834 11.00000 0.04299 0.06194 = 0.04079 -0.00062 -0.00249 -0.01502 AFIX 43 H16A 2 -0.076508 0.434352 0.898013 11.00000 -1.20000 AFIX 0 C17B 1 0.545033 0.579508 0.298487 11.00000 0.05334 0.03875 = 0.04070 0.00266 -0.00537 0.00520 AFIX 43 H17B 2 0.599544 0.599587 0.333451 11.00000 -1.20000 AFIX 0 C15B 1 0.360751 0.513553 0.269405 11.00000 0.04242 0.04257 = 0.05756 0.01401 0.00855 0.00262 AFIX 43 H15B 2 0.288068 0.488330 0.284145 11.00000 -1.20000 AFIX 0 C2A 1 0.239646 0.275975 0.253866 11.00000 0.04978 0.05217 = 0.03794 -0.00678 0.00274 -0.00708 AFIX 43 H2A 2 0.277418 0.264644 0.208845 11.00000 -1.20000 AFIX 0 C4B 1 0.836362 0.154394 0.044790 11.00000 0.05545 0.03081 = 0.05676 -0.00707 0.00929 -0.00062 AFIX 43 H4B 2 0.762611 0.128109 0.034477 11.00000 -1.20000 AFIX 0 C21A 1 0.337257 0.711007 0.656621 11.00000 0.04658 0.03603 = 0.04990 -0.00551 0.01344 -0.00661 AFIX 43 H21A 2 0.381070 0.687925 0.619471 11.00000 -1.20000 AFIX 0 C16B 1 0.438403 0.543510 0.320630 11.00000 0.05372 0.04348 = 0.04501 0.01351 0.00709 0.00984 AFIX 43 H16B 2 0.418803 0.539437 0.370500 11.00000 -1.20000 AFIX 0 C3B 1 0.946871 0.126466 0.073059 11.00000 0.07091 0.02768 = 0.04986 0.00057 0.01594 0.01092 AFIX 43 H3B 2 0.948584 0.081071 0.083324 11.00000 -1.20000 AFIX 0 C23A 1 0.257158 0.811904 0.704956 11.00000 0.04155 0.03021 = 0.07743 -0.01058 -0.00776 -0.00377 AFIX 43 H23A 2 0.246501 0.857807 0.701137 11.00000 -1.20000 AFIX 0 C22B 1 0.523941 0.683042 -0.122434 11.00000 0.04776 0.06823 = 0.03286 0.00137 -0.00155 -0.01950 AFIX 43 H22B 2 0.505156 0.658675 -0.164795 11.00000 -1.20000 AFIX 0 C24B 1 0.518300 0.783466 -0.057840 11.00000 0.03689 0.04400 = 0.06058 0.01605 -0.00324 0.00179 AFIX 43 H24B 2 0.498151 0.828654 -0.055879 11.00000 -1.20000 AFIX 0 C17A 1 -0.076084 0.525487 0.855639 11.00000 0.03481 0.06913 = 0.04582 -0.01884 0.00261 -0.00582 AFIX 43 H17A 2 -0.126047 0.544974 0.892907 11.00000 -1.20000 AFIX 0 C23B 1 0.494231 0.748710 -0.119916 11.00000 0.03967 0.07010 = 0.04953 0.02722 -0.00929 -0.01188 AFIX 43 H23B 2 0.457402 0.769732 -0.160811 11.00000 -1.20000 AFIX 0 C22A 1 0.319518 0.777558 0.650647 11.00000 0.05702 0.03588 = 0.06798 0.00457 0.01562 -0.01102 AFIX 43 H22A 2 0.350178 0.799921 0.609137 11.00000 -1.20000 AFIX 0 HKLF 4 REM s6746l_a.res in P2(1)/c REM wR2 = 0.1047, GooF = S = 1.019, Restrained GooF = 1.019 for all data REM R1 = 0.0405 for 5486 Fo > 4sig(Fo) and 0.0510 for all 6625 data REM 487 parameters refined using 0 restraints END WGHT 0.0498 0.8042 REM Highest difference peak 0.323, deepest hole -0.149, 1-sigma level 0.034 Q1 1 0.2667 0.4960 0.4818 11.00000 0.05 0.22 Q2 1 0.2239 0.5033 0.4045 11.00000 0.05 0.17 Q3 1 0.1084 0.4953 0.4893 11.00000 0.05 0.17 Q4 1 0.4489 0.4489 0.4787 11.00000 0.05 0.16 Q5 1 0.4612 0.4375 0.4682 11.00000 0.05 0.16 Q6 1 0.2741 0.3710 0.5207 11.00000 0.05 0.16 Q7 1 0.4600 0.4270 0.5387 11.00000 0.05 0.16 Q8 1 0.3575 0.5413 0.4623 11.00000 0.05 0.14 Q9 1 0.2770 0.6874 0.6828 11.00000 0.05 0.14 Q10 1 0.6449 0.6684 0.0233 11.00000 0.05 0.14 Q11 1 0.2883 0.6471 0.7184 11.00000 0.05 0.13 Q12 1 0.3089 0.4178 0.5624 11.00000 0.05 0.13 Q13 1 0.2908 0.6922 0.7429 11.00000 0.05 0.13 Q14 1 0.3639 0.4102 0.4938 11.00000 0.05 0.12 Q15 1 1.0111 0.2354 0.0390 11.00000 0.05 0.12 ; _shelx_res_checksum 7188 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.364 _oxdiff_exptl_absorpt_empirical_full_min 0.790 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1B O 1.04303(10) 0.35881(5) 0.01227(6) 0.0414(3) Uani 1 1 d . . . . . O1A O 0.42860(10) 0.39920(5) 0.40155(6) 0.0408(3) Uani 1 1 d . . . . . N1B N 0.64193(11) 0.58717(6) 0.07230(7) 0.0314(3) Uani 1 1 d . . . . . N1A N 0.22621(12) 0.57092(6) 0.66856(7) 0.0337(3) Uani 1 1 d . . . . . C20B C 0.60529(13) 0.68704(7) -0.00087(8) 0.0306(3) Uani 1 1 d . . . . . C8B C 0.82095(14) 0.36737(7) 0.04308(8) 0.0314(3) Uani 1 1 d . . . . . H8B H 0.743021 0.344033 0.052385 0.038 Uiso 1 1 calc R U . . . C11A C 0.27799(14) 0.53879(7) 0.61294(8) 0.0327(3) Uani 1 1 d . . . . . H11A H 0.369889 0.540730 0.608806 0.039 Uiso 1 1 calc R U . . . C11B C 0.73054(13) 0.54122(7) 0.05684(7) 0.0299(3) Uani 1 1 d . . . . . H11B H 0.813392 0.556378 0.041794 0.036 Uiso 1 1 calc R U . . . C10B C 0.71501(13) 0.47516(7) 0.06030(8) 0.0309(3) Uani 1 1 d . . . . . H10B H 0.634324 0.457206 0.075206 0.037 Uiso 1 1 calc R U . . . C9B C 0.81891(14) 0.43359(7) 0.04171(7) 0.0311(3) Uani 1 1 d . . . . . H9B H 0.896626 0.454369 0.026426 0.037 Uiso 1 1 calc R U . . . C19B C 0.67146(14) 0.65635(7) 0.06381(8) 0.0321(3) Uani 1 1 d . . . . . H19A H 0.766621 0.661705 0.058870 0.038 Uiso 1 1 calc R U . . . H19B H 0.644209 0.679831 0.107943 0.038 Uiso 1 1 calc R U . . . C13B C 0.49353(14) 0.55761(7) 0.17387(8) 0.0333(3) Uani 1 1 d . . . . . C5A C 0.13019(14) 0.30906(7) 0.38524(8) 0.0328(3) Uani 1 1 d . . . . . H5A H 0.092556 0.320264 0.430334 0.039 Uiso 1 1 calc R U . . . C10A C 0.21428(15) 0.50335(7) 0.56110(8) 0.0346(3) Uani 1 1 d . . . . . H10A H 0.122025 0.501947 0.560814 0.042 Uiso 1 1 calc R U . . . C12B C 0.51068(13) 0.56923(7) 0.09371(8) 0.0329(3) Uani 1 1 d . . . . . H12A H 0.485448 0.529074 0.067520 0.039 Uiso 1 1 calc R U . . . H12B H 0.450510 0.604338 0.078524 0.039 Uiso 1 1 calc R U . . . C4A C 0.07218(15) 0.26156(7) 0.34251(8) 0.0363(3) Uani 1 1 d . . . . . H4A H -0.004086 0.239926 0.358576 0.044 Uiso 1 1 calc R U . . . C13A C 0.04038(14) 0.53513(7) 0.74351(8) 0.0341(3) Uani 1 1 d . . . . . C1B C 1.05342(16) 0.23075(8) 0.07142(8) 0.0377(3) Uani 1 1 d . . . . . H1B H 1.128939 0.256392 0.079497 0.045 Uiso 1 1 calc R U . . . C7B C 0.94054(14) 0.33186(7) 0.03054(7) 0.0322(3) Uani 1 1 d . . . . . C6A C 0.24314(14) 0.34043(7) 0.36256(8) 0.0343(3) Uani 1 1 d . . . . . C9A C 0.28477(15) 0.46896(7) 0.50817(8) 0.0360(3) Uani 1 1 d . . . . . H9A H 0.376429 0.474392 0.507640 0.043 Uiso 1 1 calc R U . . . C18B C 0.57291(15) 0.58649(7) 0.22554(9) 0.0385(3) Uani 1 1 d . . . . . H18B H 0.646517 0.611094 0.210946 0.046 Uiso 1 1 calc R U . . . C6B C 0.94099(14) 0.25980(7) 0.04444(8) 0.0333(3) Uani 1 1 d . . . . . C20A C 0.29142(14) 0.67758(7) 0.71664(8) 0.0329(3) Uani 1 1 d . . . . . C19A C 0.30852(15) 0.60465(7) 0.72140(8) 0.0350(3) Uani 1 1 d . . . . . H19C H 0.400673 0.593440 0.712534 0.042 Uiso 1 1 calc R U . . . H19D H 0.285817 0.589737 0.770595 0.042 Uiso 1 1 calc R U . . . C12A C 0.08606(14) 0.57621(7) 0.68075(9) 0.0371(3) Uani 1 1 d . . . . . H12C H 0.039486 0.562376 0.636529 0.045 Uiso 1 1 calc R U . . . H12D H 0.063754 0.622419 0.690048 0.045 Uiso 1 1 calc R U . . . C8A C 0.23138(15) 0.42834(7) 0.45748(8) 0.0360(3) Uani 1 1 d . . . . . H8A H 0.139516 0.424456 0.454891 0.043 Uiso 1 1 calc R U . . . C21B C 0.58093(15) 0.65239(8) -0.06369(8) 0.0386(3) Uani 1 1 d . . . . . H21B H 0.603345 0.607512 -0.066483 0.046 Uiso 1 1 calc R U . . . C25B C 0.57182(14) 0.75282(7) 0.00184(9) 0.0370(3) Uani 1 1 d . . . . . H25B H 0.585813 0.776866 0.044984 0.044 Uiso 1 1 calc R U . . . C7A C 0.30985(15) 0.39136(7) 0.40800(8) 0.0348(3) Uani 1 1 d . . . . . C14B C 0.38859(15) 0.52021(7) 0.19688(9) 0.0406(4) Uani 1 1 d . . . . . H14B H 0.335315 0.498943 0.162185 0.049 Uiso 1 1 calc R U . . . C25A C 0.22727(15) 0.71228(8) 0.77007(8) 0.0392(3) Uani 1 1 d . . . . . H25A H 0.194250 0.689924 0.811022 0.047 Uiso 1 1 calc R U . . . C5B C 0.83266(16) 0.22112(7) 0.03132(9) 0.0394(3) Uani 1 1 d . . . . . H5B H 0.755415 0.240398 0.012993 0.047 Uiso 1 1 calc R U . . . C3A C 0.12655(15) 0.24586(8) 0.27594(8) 0.0395(3) Uani 1 1 d . . . . . H3A H 0.085798 0.214447 0.245754 0.047 Uiso 1 1 calc R U . . . C1A C 0.29822(16) 0.32257(8) 0.29701(9) 0.0430(4) Uani 1 1 d . . . . . H1A H 0.376769 0.342553 0.281728 0.052 Uiso 1 1 calc R U . . . C2B C 1.05540(18) 0.16430(8) 0.08656(9) 0.0459(4) Uani 1 1 d . . . . . H2B H 1.131454 0.144892 0.106205 0.055 Uiso 1 1 calc R U . . . C14A C 0.07109(15) 0.46924(7) 0.74786(9) 0.0389(3) Uani 1 1 d . . . . . H14A H 0.122543 0.449653 0.711292 0.047 Uiso 1 1 calc R U . . . C15A C 0.02722(17) 0.43195(8) 0.80510(9) 0.0457(4) Uani 1 1 d . . . . . H15A H 0.047887 0.386834 0.807379 0.055 Uiso 1 1 calc R U . . . C18A C -0.03324(15) 0.56301(8) 0.79811(9) 0.0428(4) Uani 1 1 d . . . . . H18A H -0.054405 0.608077 0.796065 0.051 Uiso 1 1 calc R U . . . C24A C 0.21081(16) 0.77919(8) 0.76438(9) 0.0445(4) Uani 1 1 d . . . . . H24A H 0.167481 0.802473 0.801552 0.053 Uiso 1 1 calc R U . . . C16A C -0.04636(17) 0.46008(9) 0.85883(9) 0.0486(4) Uani 1 1 d . . . . . H16A H -0.076508 0.434352 0.898013 0.058 Uiso 1 1 calc R U . . . C17B C 0.54503(17) 0.57951(8) 0.29849(9) 0.0443(4) Uani 1 1 d . . . . . H17B H 0.599544 0.599587 0.333451 0.053 Uiso 1 1 calc R U . . . C15B C 0.36075(17) 0.51355(8) 0.26941(10) 0.0475(4) Uani 1 1 d . . . . . H15B H 0.288068 0.488330 0.284145 0.057 Uiso 1 1 calc R U . . . C2A C 0.23965(17) 0.27597(9) 0.25387(9) 0.0466(4) Uani 1 1 d . . . . . H2A H 0.277418 0.264644 0.208845 0.056 Uiso 1 1 calc R U . . . C4B C 0.83636(18) 0.15439(8) 0.04479(10) 0.0477(4) Uani 1 1 d . . . . . H4B H 0.762611 0.128109 0.034477 0.057 Uiso 1 1 calc R U . . . C21A C 0.33726(17) 0.71101(8) 0.65662(10) 0.0442(4) Uani 1 1 d . . . . . H21A H 0.381070 0.687925 0.619471 0.053 Uiso 1 1 calc R U . . . C16B C 0.43840(17) 0.54351(8) 0.32063(10) 0.0474(4) Uani 1 1 d . . . . . H16B H 0.418803 0.539437 0.370500 0.057 Uiso 1 1 calc R U . . . C3B C 0.94687(19) 0.12647(8) 0.07306(10) 0.0495(4) Uani 1 1 d . . . . . H3B H 0.948584 0.081071 0.083324 0.059 Uiso 1 1 calc R U . . . C23A C 0.25716(16) 0.81190(8) 0.70496(11) 0.0497(4) Uani 1 1 d . . . . . H23A H 0.246501 0.857807 0.701137 0.060 Uiso 1 1 calc R U . . . C22B C 0.52394(17) 0.68304(10) -0.12243(9) 0.0496(4) Uani 1 1 d . . . . . H22B H 0.505156 0.658675 -0.164795 0.060 Uiso 1 1 calc R U . . . C24B C 0.51830(16) 0.78347(9) -0.05784(10) 0.0472(4) Uani 1 1 d . . . . . H24B H 0.498151 0.828654 -0.055879 0.057 Uiso 1 1 calc R U . . . C17A C -0.07608(16) 0.52549(10) 0.85564(10) 0.0499(4) Uani 1 1 d . . . . . H17A H -0.126047 0.544974 0.892907 0.060 Uiso 1 1 calc R U . . . C23B C 0.49423(17) 0.74871(10) -0.11992(10) 0.0531(5) Uani 1 1 d . . . . . H23B H 0.457402 0.769732 -0.160811 0.064 Uiso 1 1 calc R U . . . C22A C 0.31952(19) 0.77756(9) 0.65065(11) 0.0536(5) Uani 1 1 d . . . . . H22A H 0.350178 0.799921 0.609137 0.064 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1B 0.0355(6) 0.0349(6) 0.0539(7) 0.0007(5) 0.0093(5) 0.0005(4) O1A 0.0376(6) 0.0392(6) 0.0457(6) 0.0008(5) -0.0020(5) -0.0085(4) N1B 0.0292(6) 0.0254(6) 0.0397(7) -0.0006(5) -0.0007(5) 0.0007(4) N1A 0.0341(6) 0.0284(6) 0.0386(7) -0.0004(5) -0.0065(5) -0.0027(5) C20B 0.0254(7) 0.0323(7) 0.0340(7) 0.0001(6) 0.0015(5) -0.0030(5) C8B 0.0322(7) 0.0289(7) 0.0331(7) 0.0012(6) 0.0011(6) 0.0004(5) C11A 0.0366(8) 0.0249(7) 0.0366(8) 0.0061(6) -0.0046(6) -0.0027(6) C11B 0.0261(7) 0.0310(7) 0.0327(7) -0.0003(5) -0.0019(5) 0.0009(5) C10B 0.0290(7) 0.0297(7) 0.0341(7) 0.0002(6) -0.0012(5) -0.0014(5) C9B 0.0315(7) 0.0321(7) 0.0297(7) 0.0007(6) -0.0006(5) -0.0006(6) C19B 0.0335(7) 0.0266(7) 0.0361(7) -0.0029(6) -0.0032(6) -0.0006(5) C13B 0.0310(7) 0.0256(7) 0.0433(8) 0.0011(6) -0.0001(6) 0.0063(5) C5A 0.0357(8) 0.0307(7) 0.0320(7) 0.0018(6) -0.0032(6) 0.0001(6) C10A 0.0388(8) 0.0273(7) 0.0377(8) 0.0038(6) -0.0056(6) -0.0039(6) C12B 0.0263(7) 0.0307(7) 0.0417(8) -0.0015(6) -0.0019(6) 0.0017(5) C4A 0.0372(8) 0.0297(7) 0.0418(8) 0.0019(6) -0.0055(6) -0.0023(6) C13A 0.0284(7) 0.0313(7) 0.0426(8) -0.0052(6) -0.0076(6) -0.0030(5) C1B 0.0442(9) 0.0363(8) 0.0326(7) -0.0025(6) 0.0019(6) 0.0086(6) C7B 0.0354(8) 0.0300(7) 0.0311(7) -0.0010(6) 0.0010(6) 0.0012(6) C6A 0.0374(8) 0.0313(7) 0.0341(7) 0.0046(6) -0.0059(6) -0.0014(6) C9A 0.0436(8) 0.0289(7) 0.0357(8) 0.0059(6) -0.0024(6) -0.0059(6) C18B 0.0376(8) 0.0341(8) 0.0436(8) 0.0037(6) -0.0023(6) -0.0001(6) C6B 0.0398(8) 0.0319(7) 0.0284(7) -0.0023(6) 0.0055(6) 0.0044(6) C20A 0.0299(7) 0.0340(8) 0.0348(7) -0.0057(6) -0.0041(6) -0.0052(6) C19A 0.0356(8) 0.0337(8) 0.0357(8) -0.0018(6) -0.0069(6) -0.0023(6) C12A 0.0338(8) 0.0301(7) 0.0475(9) -0.0021(6) -0.0081(6) 0.0012(6) C8A 0.0376(8) 0.0336(8) 0.0369(8) 0.0051(6) -0.0046(6) -0.0043(6) C21B 0.0398(8) 0.0401(8) 0.0359(8) -0.0026(6) 0.0024(6) -0.0073(6) C25B 0.0342(8) 0.0331(8) 0.0436(8) 0.0012(6) -0.0003(6) 0.0003(6) C7A 0.0380(8) 0.0324(7) 0.0338(7) 0.0075(6) -0.0049(6) -0.0044(6) C14B 0.0360(8) 0.0331(8) 0.0527(9) 0.0038(7) -0.0008(7) -0.0001(6) C25A 0.0389(8) 0.0464(9) 0.0323(7) -0.0061(6) -0.0048(6) -0.0004(7) C5B 0.0436(9) 0.0313(8) 0.0434(8) -0.0038(6) 0.0028(7) 0.0024(6) C3A 0.0437(9) 0.0366(8) 0.0381(8) -0.0027(6) -0.0074(6) -0.0048(6) C1A 0.0411(9) 0.0477(9) 0.0401(9) -0.0010(7) 0.0010(7) -0.0087(7) C2B 0.0593(11) 0.0417(9) 0.0368(8) 0.0017(7) 0.0049(7) 0.0200(8) C14A 0.0419(8) 0.0331(8) 0.0417(8) -0.0046(6) 0.0010(6) 0.0002(6) C15A 0.0513(10) 0.0371(9) 0.0488(9) 0.0013(7) -0.0019(7) -0.0061(7) C18A 0.0324(8) 0.0405(9) 0.0554(10) -0.0156(7) -0.0060(7) 0.0014(6) C24A 0.0381(8) 0.0449(9) 0.0505(10) -0.0181(8) -0.0070(7) 0.0036(7) C16A 0.0430(9) 0.0619(11) 0.0408(9) -0.0006(8) -0.0025(7) -0.0150(8) C17B 0.0533(10) 0.0388(8) 0.0407(9) 0.0027(7) -0.0054(7) 0.0052(7) C15B 0.0424(9) 0.0426(9) 0.0576(10) 0.0140(8) 0.0086(8) 0.0026(7) C2A 0.0498(10) 0.0522(10) 0.0379(8) -0.0068(7) 0.0027(7) -0.0071(8) C4B 0.0555(10) 0.0308(8) 0.0568(10) -0.0071(7) 0.0093(8) -0.0006(7) C21A 0.0466(9) 0.0360(8) 0.0499(9) -0.0055(7) 0.0134(7) -0.0066(7) C16B 0.0537(10) 0.0435(9) 0.0450(9) 0.0135(7) 0.0071(8) 0.0098(8) C3B 0.0709(12) 0.0277(8) 0.0499(10) 0.0006(7) 0.0159(9) 0.0109(8) C23A 0.0415(9) 0.0302(8) 0.0774(13) -0.0106(8) -0.0078(8) -0.0038(7) C22B 0.0478(10) 0.0682(12) 0.0329(8) 0.0014(8) -0.0015(7) -0.0195(8) C24B 0.0369(9) 0.0440(9) 0.0606(11) 0.0160(8) -0.0032(7) 0.0018(7) C17A 0.0348(8) 0.0691(12) 0.0458(9) -0.0188(9) 0.0026(7) -0.0058(8) C23B 0.0397(9) 0.0701(13) 0.0495(10) 0.0272(9) -0.0093(7) -0.0119(8) C22A 0.0570(11) 0.0359(9) 0.0680(12) 0.0046(8) 0.0156(9) -0.0110(8) 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 6 2 3 0.0291 -6 -2 -3 0.0436 -2 9 8 0.0109 2 -9 -8 0.0363 0 11 -7 0.0218 0 -11 7 0.0218 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11B N1B C19B 121.15(12) . . ? C11B N1B C12B 120.79(12) . . ? C12B N1B C19B 117.95(11) . . ? C11A N1A C19A 121.13(12) . . ? C11A N1A C12A 123.40(12) . . ? C12A N1A C19A 115.46(12) . . ? C21B C20B C19B 122.15(13) . . ? C21B C20B C25B 118.83(14) . . ? C25B C20B C19B 118.99(13) . . ? C9B C8B H8B 119.6 . . ? C9B C8B C7B 120.81(13) . . ? C7B C8B H8B 119.6 . . ? N1A C11A H11A 116.1 . . ? N1A C11A C10A 127.70(14) . . ? C10A C11A H11A 116.1 . . ? N1B C11B H11B 116.3 . . ? N1B C11B C10B 127.33(13) . . ? C10B C11B H11B 116.3 . . ? C11B C10B H10B 120.0 . . ? C11B C10B C9B 119.93(13) . . ? C9B C10B H10B 120.0 . . ? C8B C9B C10B 127.66(13) . . ? C8B C9B H9B 116.2 . . ? C10B C9B H9B 116.2 . . ? N1B C19B C20B 113.31(12) . . ? N1B C19B H19A 108.9 . . ? N1B C19B H19B 108.9 . . ? C20B C19B H19A 108.9 . . ? C20B C19B H19B 108.9 . . ? H19A C19B H19B 107.7 . . ? C18B C13B C12B 122.61(13) . . ? C18B C13B C14B 118.62(15) . . ? C14B C13B C12B 118.61(14) . . ? C4A C5A H5A 119.7 . . ? C4A C5A C6A 120.62(14) . . ? C6A C5A H5A 119.7 . . ? C11A C10A H10A 119.8 . . ? C11A C10A C9A 120.43(14) . . ? C9A C10A H10A 119.8 . . ? N1B C12B C13B 114.65(12) . . ? N1B C12B H12A 108.6 . . ? N1B C12B H12B 108.6 . . ? C13B C12B H12A 108.6 . . ? C13B C12B H12B 108.6 . . ? H12A C12B H12B 107.6 . . ? C5A C4A H4A 120.2 . . ? C5A C4A C3A 119.58(14) . . ? C3A C4A H4A 120.2 . . ? C14A C13A C12A 121.00(14) . . ? C18A C13A C12A 120.17(14) . . ? C18A C13A C14A 118.83(15) . . ? C6B C1B H1B 119.9 . . ? C2B C1B H1B 119.9 . . ? C2B C1B C6B 120.18(16) . . ? O1B C7B C8B 122.95(13) . . ? O1B C7B C6B 118.95(13) . . ? C8B C7B C6B 118.00(12) . . ? C5A C6A C7A 122.06(13) . . ? C1A C6A C5A 118.92(14) . . ? C1A C6A C7A 118.99(13) . . ? C10A C9A H9A 117.5 . . ? C8A C9A C10A 125.08(15) . . ? C8A C9A H9A 117.5 . . ? C13B C18B H18B 119.9 . . ? C17B C18B C13B 120.26(15) . . ? C17B C18B H18B 119.9 . . ? C1B C6B C7B 119.01(14) . . ? C5B C6B C1B 118.98(14) . . ? C5B C6B C7B 122.01(14) . . ? C25A C20A C19A 121.49(14) . . ? C25A C20A C21A 118.77(14) . . ? C21A C20A C19A 119.72(13) . . ? N1A C19A C20A 111.17(12) . . ? N1A C19A H19C 109.4 . . ? N1A C19A H19D 109.4 . . ? C20A C19A H19C 109.4 . . ? C20A C19A H19D 109.4 . . ? H19C C19A H19D 108.0 . . ? N1A C12A C13A 112.68(12) . . ? N1A C12A H12C 109.1 . . ? N1A C12A H12D 109.1 . . ? C13A C12A H12C 109.1 . . ? C13A C12A H12D 109.1 . . ? H12C C12A H12D 107.8 . . ? C9A C8A H8A 118.9 . . ? C9A C8A C7A 122.17(14) . . ? C7A C8A H8A 118.9 . . ? C20B C21B H21B 119.9 . . ? C22B C21B C20B 120.19(16) . . ? C22B C21B H21B 119.9 . . ? C20B C25B H25B 119.7 . . ? C24B C25B C20B 120.55(16) . . ? C24B C25B H25B 119.7 . . ? O1A C7A C6A 119.00(14) . . ? O1A C7A C8A 123.25(14) . . ? C8A C7A C6A 117.75(13) . . ? C13B C14B H14B 119.5 . . ? C15B C14B C13B 120.99(16) . . ? C15B C14B H14B 119.5 . . ? C20A C25A H25A 119.6 . . ? C24A C25A C20A 120.75(15) . . ? C24A C25A H25A 119.6 . . ? C6B C5B H5B 119.7 . . ? C6B C5B C4B 120.54(16) . . ? C4B C5B H5B 119.7 . . ? C4A C3A H3A 120.0 . . ? C2A C3A C4A 119.97(14) . . ? C2A C3A H3A 120.0 . . ? C6A C1A H1A 119.7 . . ? C2A C1A C6A 120.58(15) . . ? C2A C1A H1A 119.7 . . ? C1B C2B H2B 119.9 . . ? C3B C2B C1B 120.10(16) . . ? C3B C2B H2B 119.9 . . ? C13A C14A H14A 119.8 . . ? C15A C14A C13A 120.45(15) . . ? C15A C14A H14A 119.8 . . ? C14A C15A H15A 119.9 . . ? C16A C15A C14A 120.21(16) . . ? C16A C15A H15A 119.9 . . ? C13A C18A H18A 119.8 . . ? C17A C18A C13A 120.44(16) . . ? C17A C18A H18A 119.8 . . ? C25A C24A H24A 120.0 . . ? C23A C24A C25A 120.06(15) . . ? C23A C24A H24A 120.0 . . ? C15A C16A H16A 120.0 . . ? C17A C16A C15A 119.91(16) . . ? C17A C16A H16A 120.0 . . ? C18B C17B H17B 119.7 . . ? C16B C17B C18B 120.54(16) . . ? C16B C17B H17B 119.7 . . ? C14B C15B H15B 119.9 . . ? C14B C15B C16B 120.20(16) . . ? C16B C15B H15B 119.9 . . ? C3A C2A C1A 120.29(15) . . ? C3A C2A H2A 119.9 . . ? C1A C2A H2A 119.9 . . ? C5B C4B H4B 120.0 . . ? C3B C4B C5B 119.99(17) . . ? C3B C4B H4B 120.0 . . ? C20A C21A H21A 119.8 . . ? C22A C21A C20A 120.41(15) . . ? C22A C21A H21A 119.8 . . ? C17B C16B H16B 120.3 . . ? C15B C16B C17B 119.35(16) . . ? C15B C16B H16B 120.3 . . ? C2B C3B H3B 119.9 . . ? C4B C3B C2B 120.16(16) . . ? C4B C3B H3B 119.9 . . ? C24A C23A H23A 120.2 . . ? C24A C23A C22A 119.68(16) . . ? C22A C23A H23A 120.2 . . ? C21B C22B H22B 119.7 . . ? C23B C22B C21B 120.57(16) . . ? C23B C22B H22B 119.7 . . ? C25B C24B H24B 119.9 . . ? C23B C24B C25B 120.23(16) . . ? C23B C24B H24B 119.9 . . ? C18A C17A H17A 119.9 . . ? C16A C17A C18A 120.14(15) . . ? C16A C17A H17A 119.9 . . ? C22B C23B H23B 120.2 . . ? C24B C23B C22B 119.58(16) . . ? C24B C23B H23B 120.2 . . ? C21A C22A C23A 120.31(17) . . ? C21A C22A H22A 119.8 . . ? C23A C22A H22A 119.8 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1B C7B 1.2386(18) . ? O1A C7A 1.2388(18) . ? N1B C11B 1.3426(18) . ? N1B C19B 1.4590(18) . ? N1B C12B 1.4561(18) . ? N1A C11A 1.3351(19) . ? N1A C19A 1.4666(18) . ? N1A C12A 1.4646(19) . ? C20B C19B 1.514(2) . ? C20B C21B 1.386(2) . ? C20B C25B 1.393(2) . ? C8B H8B 0.9500 . ? C8B C9B 1.358(2) . ? C8B C7B 1.449(2) . ? C11A H11A 0.9500 . ? C11A C10A 1.370(2) . ? C11B H11B 0.9500 . ? C11B C10B 1.365(2) . ? C10B H10B 0.9500 . ? C10B C9B 1.411(2) . ? C9B H9B 0.9500 . ? C19B H19A 0.9900 . ? C19B H19B 0.9900 . ? C13B C12B 1.515(2) . ? C13B C18B 1.390(2) . ? C13B C14B 1.392(2) . ? C5A H5A 0.9500 . ? C5A C4A 1.389(2) . ? C5A C6A 1.394(2) . ? C10A H10A 0.9500 . ? C10A C9A 1.410(2) . ? C12B H12A 0.9900 . ? C12B H12B 0.9900 . ? C4A H4A 0.9500 . ? C4A C3A 1.393(2) . ? C13A C12A 1.512(2) . ? C13A C14A 1.390(2) . ? C13A C18A 1.388(2) . ? C1B H1B 0.9500 . ? C1B C6B 1.393(2) . ? C1B C2B 1.391(2) . ? C7B C6B 1.500(2) . ? C6A C7A 1.506(2) . ? C6A C1A 1.391(2) . ? C9A H9A 0.9500 . ? C9A C8A 1.370(2) . ? C18B H18B 0.9500 . ? C18B C17B 1.390(2) . ? C6B C5B 1.389(2) . ? C20A C19A 1.508(2) . ? C20A C25A 1.387(2) . ? C20A C21A 1.390(2) . ? C19A H19C 0.9900 . ? C19A H19D 0.9900 . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C8A H8A 0.9500 . ? C8A C7A 1.439(2) . ? C21B H21B 0.9500 . ? C21B C22B 1.386(2) . ? C25B H25B 0.9500 . ? C25B C24B 1.385(2) . ? C14B H14B 0.9500 . ? C14B C15B 1.382(3) . ? C25A H25A 0.9500 . ? C25A C24A 1.386(2) . ? C5B H5B 0.9500 . ? C5B C4B 1.391(2) . ? C3A H3A 0.9500 . ? C3A C2A 1.380(2) . ? C1A H1A 0.9500 . ? C1A C2A 1.383(2) . ? C2B H2B 0.9500 . ? C2B C3B 1.382(3) . ? C14A H14A 0.9500 . ? C14A C15A 1.384(2) . ? C15A H15A 0.9500 . ? C15A C16A 1.379(3) . ? C18A H18A 0.9500 . ? C18A C17A 1.387(3) . ? C24A H24A 0.9500 . ? C24A C23A 1.376(3) . ? C16A H16A 0.9500 . ? C16A C17A 1.377(3) . ? C17B H17B 0.9500 . ? C17B C16B 1.385(3) . ? C15B H15B 0.9500 . ? C15B C16B 1.383(3) . ? C2A H2A 0.9500 . ? C4B H4B 0.9500 . ? C4B C3B 1.376(3) . ? C21A H21A 0.9500 . ? C21A C22A 1.381(3) . ? C16B H16B 0.9500 . ? C3B H3B 0.9500 . ? C23A H23A 0.9500 . ? C23A C22A 1.387(3) . ? C22B H22B 0.9500 . ? C22B C23B 1.381(3) . ? C24B H24B 0.9500 . ? C24B C23B 1.375(3) . ? C17A H17A 0.9500 . ? C23B H23B 0.9500 . ? C22A H22A 0.9500 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1B C7B C6B C1B 31.4(2) . . . . ? O1B C7B C6B C5B -148.68(15) . . . . ? N1B C11B C10B C9B 179.72(13) . . . . ? N1A C11A C10A C9A -176.14(13) . . . . ? C20B C21B C22B C23B 1.9(2) . . . . ? C20B C25B C24B C23B 1.8(2) . . . . ? C8B C7B C6B C1B -145.26(14) . . . . ? C8B C7B C6B C5B 34.7(2) . . . . ? C11A N1A C19A C20A 112.38(15) . . . . ? C11A N1A C12A C13A 107.55(15) . . . . ? C11A C10A C9A C8A 174.87(14) . . . . ? C11B N1B C19B C20B 106.45(15) . . . . ? C11B N1B C12B C13B 87.50(16) . . . . ? C11B C10B C9B C8B 178.95(14) . . . . ? C9B C8B C7B O1B -6.1(2) . . . . ? C9B C8B C7B C6B 170.36(13) . . . . ? C19B N1B C11B C10B -178.00(14) . . . . ? C19B N1B C12B C13B -96.28(15) . . . . ? C19B C20B C21B C22B -177.88(14) . . . . ? C19B C20B C25B C24B 176.11(14) . . . . ? C13B C18B C17B C16B 0.3(2) . . . . ? C13B C14B C15B C16B -0.8(2) . . . . ? C5A C4A C3A C2A 2.0(2) . . . . ? C5A C6A C7A O1A 152.10(14) . . . . ? C5A C6A C7A C8A -27.5(2) . . . . ? C5A C6A C1A C2A 2.1(2) . . . . ? C10A C9A C8A C7A -175.80(14) . . . . ? C12B N1B C11B C10B -1.9(2) . . . . ? C12B N1B C19B C20B -69.76(16) . . . . ? C12B C13B C18B C17B 173.48(14) . . . . ? C12B C13B C14B C15B -173.39(14) . . . . ? C4A C5A C6A C7A -178.99(13) . . . . ? C4A C5A C6A C1A -1.2(2) . . . . ? C4A C3A C2A C1A -1.1(3) . . . . ? C13A C14A C15A C16A -0.7(2) . . . . ? C13A C18A C17A C16A -0.3(2) . . . . ? C1B C6B C5B C4B -0.1(2) . . . . ? C1B C2B C3B C4B -0.2(2) . . . . ? C7B C8B C9B C10B -172.58(14) . . . . ? C7B C6B C5B C4B 179.98(14) . . . . ? C6A C5A C4A C3A -0.9(2) . . . . ? C6A C1A C2A C3A -1.0(3) . . . . ? C9A C8A C7A O1A -9.0(2) . . . . ? C9A C8A C7A C6A 170.53(13) . . . . ? C18B C13B C12B N1B 25.84(19) . . . . ? C18B C13B C14B C15B 2.2(2) . . . . ? C18B C17B C16B C15B 1.0(2) . . . . ? C6B C1B C2B C3B 1.7(2) . . . . ? C6B C5B C4B C3B 1.7(2) . . . . ? C20A C25A C24A C23A 0.6(2) . . . . ? C20A C21A C22A C23A 0.8(3) . . . . ? C19A N1A C11A C10A 177.51(14) . . . . ? C19A N1A C12A C13A -73.50(15) . . . . ? C19A C20A C25A C24A -179.10(14) . . . . ? C19A C20A C21A C22A 178.41(16) . . . . ? C12A N1A C11A C10A -3.6(2) . . . . ? C12A N1A C19A C20A -66.59(16) . . . . ? C12A C13A C14A C15A -179.13(14) . . . . ? C12A C13A C18A C17A 179.63(14) . . . . ? C21B C20B C19B N1B -32.53(19) . . . . ? C21B C20B C25B C24B -1.7(2) . . . . ? C21B C22B C23B C24B -1.8(3) . . . . ? C25B C20B C19B N1B 149.74(13) . . . . ? C25B C20B C21B C22B -0.1(2) . . . . ? C25B C24B C23B C22B -0.1(3) . . . . ? C7A C6A C1A C2A 180.00(15) . . . . ? C14B C13B C12B N1B -158.78(12) . . . . ? C14B C13B C18B C17B -1.9(2) . . . . ? C14B C15B C16B C17B -0.8(3) . . . . ? C25A C20A C19A N1A 108.66(16) . . . . ? C25A C20A C21A C22A 0.3(2) . . . . ? C25A C24A C23A C22A 0.4(3) . . . . ? C5B C4B C3B C2B -1.5(3) . . . . ? C1A C6A C7A O1A -25.7(2) . . . . ? C1A C6A C7A C8A 154.71(14) . . . . ? C2B C1B C6B C7B 178.33(13) . . . . ? C2B C1B C6B C5B -1.6(2) . . . . ? C14A C13A C12A N1A -52.13(18) . . . . ? C14A C13A C18A C17A -0.5(2) . . . . ? C14A C15A C16A C17A -0.1(3) . . . . ? C15A C16A C17A C18A 0.6(3) . . . . ? C18A C13A C12A N1A 127.74(14) . . . . ? C18A C13A C14A C15A 1.0(2) . . . . ? C24A C23A C22A C21A -1.2(3) . . . . ? C21A C20A C19A N1A -69.44(18) . . . . ? C21A C20A C25A C24A -1.0(2) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 6.3152 2.1791 3.3412 -0.0005 0.0006 -1.0000 -6.3152 -2.1791 -3.3412 0.0005 -0.0006 1.0000 -2.1215 8.6863 8.2962 -0.1170 -0.9931 -0.0005 2.1215 -8.6863 -8.2962 0.1170 0.9931 0.0005 0.2443 10.6924 -7.1437 0.9755 -0.2202 -0.0011 -0.2443 -10.6924 7.1437 -0.9755 0.2202 0.0011