#------------------------------------------------------------------------------ #$Date: 2021-07-05 21:06:10 +0300 (Mon, 05 Jul 2021) $ #$Revision: 267222 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060687.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_7060687 loop_ _publ_author_name 'Ge, Yuxi' 'Huang, Bin' _publ_section_title ; Light-emitting analogues based on triphenylamine modified quinoxaline and pyridine[2,3-b]pyrazine exhibiting different mechanochromic luminescence ; _journal_issue 25 _journal_name_full 'New Journal of Chemistry' _journal_page_first 11304 _journal_page_last 11312 _journal_paper_doi 10.1039/D1NJ01350E _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C37 H26 N4' _chemical_formula_sum 'C37 H26 N4' _chemical_formula_weight 526.62 _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 2021-04-29 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-04-29 deposited with the CCDC. 2021-05-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 116.751(13) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 19.065(14) _cell_length_b 8.994(7) _cell_length_c 17.864(14) _cell_measurement_reflns_used 1789 _cell_measurement_temperature 296.15 _cell_measurement_theta_max 21.955 _cell_measurement_theta_min 2.393 _cell_volume 2735(4) _computing_cell_refinement 'SAINT V8.40A (Bruker, 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.968 _diffrn_measured_fraction_theta_max 0.951 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_unetI/netI 0.0982 _diffrn_reflns_Laue_measured_fraction_full 0.968 _diffrn_reflns_Laue_measured_fraction_max 0.951 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 18449 _diffrn_reflns_point_group_measured_fraction_full 0.968 _diffrn_reflns_point_group_measured_fraction_max 0.951 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.523 _diffrn_reflns_theta_min 1.196 _diffrn_source_current 0.6 _diffrn_source_power 0.03 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.3898 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1652 before and 0.0648 after correction. The Ratio of minimum to maximum transmission is 0.5228. The \l/2 correction factor is Not present. ; _exptl_crystal_density_diffrn 1.279 _exptl_crystal_description plate _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.218 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 370 _refine_ls_number_reflns 5982 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.970 _refine_ls_R_factor_all 0.1393 _refine_ls_R_factor_gt 0.0591 _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^)+(0.0759P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1389 _refine_ls_wR_factor_ref 0.1814 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2892 _reflns_number_total 5982 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01350e2.cif _cod_data_source_block a_CCDC1 _cod_depositor_comments 'Adding full bibliography for 7060684--7060687.cif.' _cod_database_code 7060687 _shelx_shelxl_version_number 2018/3 _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_estimated_absorpt_t_max 0.996 _shelx_estimated_absorpt_t_min 0.992 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C15(H15), C20(H20), C23(H23), C37(H37), C18(H18), C26(H26), C14(H14), C12(H12), C17(H17), C27(H27), C30(H30), C8(H8), C33(H33), C2(H2), C6(H6), C36(H36), C35(H35), C9(H9), C11(H11), C28(H28), C29(H29), C34(H34), C10(H10), C3(H3), C5(H5), C4(H4) ; _shelx_res_file ; TITL a_a.res in P2(1)/c a.res created by SHELXL-2018/3 at 08:15:55 on 29-Apr-2021 REM Old TITL A in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.196, Rweak 0.012, Alpha 0.032 REM 0.429 for 310 systematic absences, Orientation as input REM Formula found by SHELXT: C37 N4 CELL 0.71073 19.0648 8.9939 17.8641 90 116.751 90 ZERR 4 0.0144 0.0069 0.0135 0 0.013 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N UNIT 148 104 16 L.S. 20 555 PLAN 5 SIZE 0.08 0.05 0.1 TEMP 23 CONF BOND list 4 fmap 2 MORE -1 ACTA BOND $H OMIT -10 4 2 REM REM REM WGHT 0.075900 FVAR 0.34913 N3 3 0.335366 0.338397 0.372734 11.00000 0.04311 0.04478 = 0.03472 0.00329 0.01885 0.00385 N2 3 0.457514 0.342247 0.487872 11.00000 0.04106 0.05592 = 0.03886 0.00188 0.02003 0.00080 N4 3 0.261145 0.350733 0.477976 11.00000 0.04233 0.06244 = 0.03212 -0.00121 0.01809 -0.00213 N1 3 0.694012 0.336370 0.973878 11.00000 0.03969 0.07584 = 0.03057 0.00388 0.01316 0.00494 C21 1 0.377959 0.344562 0.457777 11.00000 0.04163 0.04216 = 0.03294 0.00086 0.01931 0.00155 C24 1 0.219878 0.336103 0.395613 11.00000 0.04528 0.04482 = 0.03321 0.00095 0.02081 0.00193 C25 1 0.133521 0.321401 0.363972 11.00000 0.04224 0.05101 = 0.02922 0.00556 0.01649 -0.00221 C32 1 0.212845 0.338448 0.249102 11.00000 0.04137 0.04430 = 0.03342 0.00020 0.01961 -0.00225 C19 1 0.468592 0.366786 0.629171 11.00000 0.04205 0.04453 = 0.03304 0.00436 0.01638 0.00147 C15 1 0.596001 0.443268 0.749249 11.00000 0.04609 0.04601 = 0.03893 0.00356 0.02187 -0.00092 AFIX 43 H15 2 0.608286 0.495858 0.711883 11.00000 -1.20000 AFIX 0 C22 1 0.341406 0.355927 0.510088 11.00000 0.04119 0.05521 = 0.03204 0.00012 0.01869 0.00075 C20 1 0.498956 0.353746 0.570063 11.00000 0.03935 0.05304 = 0.03765 0.00505 0.01658 0.00184 AFIX 43 H20 2 0.553336 0.353245 0.591241 11.00000 -1.20000 AFIX 0 C7 1 0.677689 0.355835 1.042646 11.00000 0.04358 0.05349 = 0.03388 -0.00399 0.01563 -0.00701 C31 1 0.257607 0.335793 0.342263 11.00000 0.04196 0.04072 = 0.03344 0.00150 0.01791 0.00187 C16 1 0.523379 0.371432 0.720229 11.00000 0.03968 0.04371 = 0.03374 0.00321 0.01627 0.00121 C13 1 0.633815 0.355402 0.889334 11.00000 0.04177 0.05328 = 0.03021 -0.00075 0.01566 0.00057 C23 1 0.388519 0.366875 0.597316 11.00000 0.04943 0.06500 = 0.03504 -0.00180 0.02422 0.00213 AFIX 43 H23 2 0.365278 0.374138 0.633123 11.00000 -1.20000 AFIX 0 C37 1 0.154149 0.441140 0.208418 11.00000 0.05059 0.04551 = 0.04142 0.00398 0.02251 0.00288 AFIX 43 H37 2 0.140742 0.507928 0.239612 11.00000 -1.20000 AFIX 0 C18 1 0.560716 0.289673 0.862408 11.00000 0.04727 0.05492 = 0.03891 0.00499 0.02167 -0.00583 AFIX 43 H18 2 0.548102 0.239573 0.900275 11.00000 -1.20000 AFIX 0 C26 1 0.094664 0.415027 0.394438 11.00000 0.04558 0.05462 = 0.04429 -0.00442 0.02297 -0.00516 AFIX 43 H26 2 0.122830 0.488088 0.433200 11.00000 -1.20000 AFIX 0 C1 1 0.771169 0.302096 0.985435 11.00000 0.04459 0.05750 = 0.03601 0.00912 0.01703 -0.00079 C14 1 0.649495 0.436741 0.832768 11.00000 0.03900 0.05218 = 0.04136 -0.00049 0.01703 -0.00501 AFIX 43 H14 2 0.696827 0.487725 0.851411 11.00000 -1.20000 AFIX 0 C12 1 0.622968 0.459723 1.040232 11.00000 0.05787 0.04842 = 0.04498 0.00025 0.02095 -0.00278 AFIX 43 H12 2 0.596018 0.516736 0.992262 11.00000 -1.20000 AFIX 0 C17 1 0.506352 0.299096 0.778430 11.00000 0.04108 0.05746 = 0.04067 0.00006 0.01776 -0.00890 AFIX 43 H17 2 0.457207 0.255593 0.760902 11.00000 -1.20000 AFIX 0 C27 1 0.014745 0.401938 0.368307 11.00000 0.04573 0.06548 = 0.05990 -0.00251 0.02972 -0.00042 AFIX 43 H27 2 -0.010449 0.466280 0.389135 11.00000 -1.20000 AFIX 0 C30 1 0.089763 0.211931 0.306952 11.00000 0.05575 0.05688 = 0.05070 -0.00961 0.02844 -0.01035 AFIX 43 H30 2 0.114405 0.147324 0.285612 11.00000 -1.20000 AFIX 0 C8 1 0.716408 0.270692 1.115064 11.00000 0.05097 0.06439 = 0.04085 0.00477 0.01795 -0.00097 AFIX 43 H8 2 0.751967 0.198034 1.117189 11.00000 -1.20000 AFIX 0 C33 1 0.231308 0.238862 0.201553 11.00000 0.05576 0.06499 = 0.04011 -0.00126 0.02588 0.00534 AFIX 43 H33 2 0.270773 0.168915 0.227969 11.00000 -1.20000 AFIX 0 C2 1 0.781917 0.206069 0.930674 11.00000 0.05081 0.06128 = 0.04426 0.00626 0.02275 0.00112 AFIX 43 H2 2 0.738699 0.161562 0.887291 11.00000 -1.20000 AFIX 0 C6 1 0.836983 0.364887 1.051635 11.00000 0.05117 0.07697 = 0.04250 0.00385 0.01575 -0.00992 AFIX 43 H6 2 0.830918 0.429472 1.088964 11.00000 -1.20000 AFIX 0 C36 1 0.114861 0.446119 0.121617 11.00000 0.05273 0.05989 = 0.04607 0.01333 0.01872 0.00069 AFIX 43 H36 2 0.076096 0.517167 0.094875 11.00000 -1.20000 AFIX 0 C35 1 0.133324 0.345833 0.075171 11.00000 0.05859 0.07857 = 0.03341 -0.00050 0.01707 -0.01554 AFIX 43 H35 2 0.106537 0.347816 0.016943 11.00000 -1.20000 AFIX 0 C9 1 0.702450 0.293251 1.183537 11.00000 0.06407 0.07807 = 0.03894 0.00889 0.02249 -0.00930 AFIX 43 H9 2 0.729963 0.238106 1.232136 11.00000 -1.20000 AFIX 0 C11 1 0.608144 0.479236 1.108634 11.00000 0.06533 0.05891 = 0.05848 -0.01307 0.03581 -0.00904 AFIX 43 H11 2 0.570927 0.548537 1.106085 11.00000 -1.20000 AFIX 0 C28 1 -0.027413 0.293572 0.311452 11.00000 0.04230 0.08031 = 0.06526 -0.00405 0.02498 -0.01238 AFIX 43 H28 2 -0.081259 0.285042 0.293243 11.00000 -1.20000 AFIX 0 C29 1 0.010348 0.198331 0.281820 11.00000 0.05791 0.07600 = 0.06103 -0.02147 0.02904 -0.02717 AFIX 43 H29 2 -0.017930 0.123681 0.244331 11.00000 -1.20000 AFIX 0 C34 1 0.191377 0.242846 0.114981 11.00000 0.06718 0.07405 = 0.04255 -0.01338 0.02929 -0.00600 AFIX 43 H34 2 0.203989 0.175197 0.083546 11.00000 -1.20000 AFIX 0 C10 1 0.648085 0.396808 1.180439 11.00000 0.07533 0.07445 = 0.04553 -0.01192 0.03597 -0.01969 AFIX 43 H10 2 0.638390 0.411021 1.226513 11.00000 -1.20000 AFIX 0 C3 1 0.856619 0.176439 0.940437 11.00000 0.06249 0.06756 = 0.06918 0.01566 0.03910 0.00995 AFIX 43 H3 2 0.863039 0.113535 0.902658 11.00000 -1.20000 AFIX 0 C5 1 0.911315 0.329959 1.061077 11.00000 0.04191 0.09617 = 0.05367 0.01871 0.01234 -0.01520 AFIX 43 H5 2 0.955113 0.369177 1.106163 11.00000 -1.20000 AFIX 0 C4 1 0.921670 0.238230 1.004984 11.00000 0.04702 0.08712 = 0.07815 0.03239 0.03174 0.00703 AFIX 43 H4 2 0.971739 0.218547 1.010724 11.00000 -1.20000 AFIX 0 HKLF 4 REM a_a.res in P2(1)/c REM wR2 = 0.1814, GooF = S = 0.970, Restrained GooF = 0.970 for all data REM R1 = 0.0591 for 2892 Fo > 4sig(Fo) and 0.1393 for all 5982 data REM 370 parameters refined using 0 restraints END WGHT 0.0757 0.0000 REM Highest difference peak 0.218, deepest hole -0.215, 1-sigma level 0.051 Q1 1 -0.0179 0.0603 0.2515 11.00000 0.05 0.22 Q2 1 1.0098 0.2278 1.1504 11.00000 0.05 0.19 Q3 1 0.9490 0.3860 1.2038 11.00000 0.05 0.19 Q4 1 0.5697 0.5400 0.8794 11.00000 0.05 0.18 Q5 1 0.1679 0.1168 0.3017 11.00000 0.05 0.18 ; _shelx_res_checksum 75647 _olex2_submission_special_instructions 'No special instructions were received' 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 N3 N 0.33537(11) 0.3384(2) 0.37273(13) 0.0404(5) Uani 1 1 d . . . . . N2 N 0.45751(11) 0.3422(2) 0.48787(13) 0.0445(6) Uani 1 1 d . . . . . N4 N 0.26115(11) 0.3507(2) 0.47798(13) 0.0451(6) Uani 1 1 d . . . . . N1 N 0.69401(11) 0.3364(3) 0.97388(13) 0.0497(6) Uani 1 1 d . . . . . C21 C 0.37796(13) 0.3446(3) 0.45778(15) 0.0380(6) Uani 1 1 d . . . . . C24 C 0.21988(14) 0.3361(3) 0.39561(15) 0.0399(6) Uani 1 1 d . . . . . C25 C 0.13352(14) 0.3214(3) 0.36397(15) 0.0407(6) Uani 1 1 d . . . . . C32 C 0.21285(14) 0.3384(3) 0.24910(15) 0.0387(6) Uani 1 1 d . . . . . C19 C 0.46859(14) 0.3668(3) 0.62917(15) 0.0401(6) Uani 1 1 d . . . . . C15 C 0.59600(13) 0.4433(3) 0.74925(16) 0.0426(6) Uani 1 1 d . . . . . H15 H 0.608286 0.495858 0.711883 0.051 Uiso 1 1 calc R U . . . C22 C 0.34141(14) 0.3559(3) 0.51009(15) 0.0420(6) Uani 1 1 d . . . . . C20 C 0.49896(14) 0.3537(3) 0.57006(16) 0.0436(6) Uani 1 1 d . . . . . H20 H 0.553336 0.353245 0.591241 0.052 Uiso 1 1 calc R U . . . C7 C 0.67769(14) 0.3558(3) 1.04265(16) 0.0443(7) Uani 1 1 d . . . . . C31 C 0.25761(13) 0.3358(3) 0.34226(15) 0.0384(6) Uani 1 1 d . . . . . C16 C 0.52338(13) 0.3714(3) 0.72023(15) 0.0391(6) Uani 1 1 d . . . . . C13 C 0.63381(14) 0.3554(3) 0.88933(15) 0.0420(6) Uani 1 1 d . . . . . C23 C 0.38852(14) 0.3669(3) 0.59732(16) 0.0479(7) Uani 1 1 d . . . . . H23 H 0.365278 0.374138 0.633123 0.057 Uiso 1 1 calc R U . . . C37 C 0.15415(14) 0.4411(3) 0.20842(16) 0.0452(7) Uani 1 1 d . . . . . H37 H 0.140742 0.507928 0.239612 0.054 Uiso 1 1 calc R U . . . C18 C 0.56072(14) 0.2897(3) 0.86241(16) 0.0462(7) Uani 1 1 d . . . . . H18 H 0.548102 0.239573 0.900275 0.055 Uiso 1 1 calc R U . . . C26 C 0.09466(14) 0.4150(3) 0.39444(17) 0.0471(7) Uani 1 1 d . . . . . H26 H 0.122830 0.488088 0.433200 0.057 Uiso 1 1 calc R U . . . C1 C 0.77117(14) 0.3021(3) 0.98544(16) 0.0465(7) Uani 1 1 d . . . . . C14 C 0.64950(14) 0.4367(3) 0.83277(16) 0.0446(7) Uani 1 1 d . . . . . H14 H 0.696827 0.487725 0.851411 0.053 Uiso 1 1 calc R U . . . C12 C 0.62297(15) 0.4597(3) 1.04023(18) 0.0512(7) Uani 1 1 d . . . . . H12 H 0.596018 0.516736 0.992262 0.061 Uiso 1 1 calc R U . . . C17 C 0.50635(14) 0.2991(3) 0.77843(16) 0.0466(7) Uani 1 1 d . . . . . H17 H 0.457207 0.255593 0.760902 0.056 Uiso 1 1 calc R U . . . C27 C 0.01475(15) 0.4019(3) 0.36831(18) 0.0548(8) Uani 1 1 d . . . . . H27 H -0.010449 0.466280 0.389135 0.066 Uiso 1 1 calc R U . . . C30 C 0.08976(16) 0.2119(3) 0.30695(17) 0.0528(7) Uani 1 1 d . . . . . H30 H 0.114405 0.147324 0.285612 0.063 Uiso 1 1 calc R U . . . C8 C 0.71641(15) 0.2707(3) 1.11506(17) 0.0531(7) Uani 1 1 d . . . . . H8 H 0.751967 0.198034 1.117189 0.064 Uiso 1 1 calc R U . . . C33 C 0.23131(16) 0.2389(3) 0.20155(17) 0.0520(7) Uani 1 1 d . . . . . H33 H 0.270773 0.168915 0.227969 0.062 Uiso 1 1 calc R U . . . C2 C 0.78192(16) 0.2061(3) 0.93067(18) 0.0516(7) Uani 1 1 d . . . . . H2 H 0.738699 0.161562 0.887291 0.062 Uiso 1 1 calc R U . . . C6 C 0.83698(15) 0.3649(4) 1.05163(18) 0.0589(8) Uani 1 1 d . . . . . H6 H 0.830918 0.429472 1.088964 0.071 Uiso 1 1 calc R U . . . C36 C 0.11486(15) 0.4461(3) 0.12162(18) 0.0542(8) Uani 1 1 d . . . . . H36 H 0.076096 0.517167 0.094875 0.065 Uiso 1 1 calc R U . . . C35 C 0.13332(17) 0.3458(4) 0.07517(18) 0.0582(8) Uani 1 1 d . . . . . H35 H 0.106537 0.347816 0.016943 0.070 Uiso 1 1 calc R U . . . C9 C 0.70245(17) 0.2933(4) 1.18354(18) 0.0606(8) Uani 1 1 d . . . . . H9 H 0.729963 0.238106 1.232136 0.073 Uiso 1 1 calc R U . . . C11 C 0.60814(17) 0.4792(3) 1.1086(2) 0.0579(8) Uani 1 1 d . . . . . H11 H 0.570927 0.548537 1.106085 0.070 Uiso 1 1 calc R U . . . C28 C -0.02741(17) 0.2936(4) 0.3115(2) 0.0623(9) Uani 1 1 d . . . . . H28 H -0.081259 0.285042 0.293243 0.075 Uiso 1 1 calc R U . . . C29 C 0.01035(17) 0.1983(4) 0.2818(2) 0.0641(9) Uani 1 1 d . . . . . H29 H -0.017930 0.123681 0.244331 0.077 Uiso 1 1 calc R U . . . C34 C 0.19138(17) 0.2428(4) 0.11498(18) 0.0595(8) Uani 1 1 d . . . . . H34 H 0.203989 0.175197 0.083546 0.071 Uiso 1 1 calc R U . . . C10 C 0.64809(18) 0.3968(4) 1.18044(19) 0.0618(8) Uani 1 1 d . . . . . H10 H 0.638390 0.411021 1.226513 0.074 Uiso 1 1 calc R U . . . C3 C 0.85662(17) 0.1764(3) 0.9404(2) 0.0628(9) Uani 1 1 d . . . . . H3 H 0.863039 0.113535 0.902658 0.075 Uiso 1 1 calc R U . . . C5 C 0.91131(16) 0.3300(4) 1.0611(2) 0.0674(10) Uani 1 1 d . . . . . H5 H 0.955113 0.369177 1.106163 0.081 Uiso 1 1 calc R U . . . C4 C 0.92167(18) 0.2382(4) 1.0050(2) 0.0694(10) Uani 1 1 d . . . . . H4 H 0.971739 0.218547 1.010724 0.083 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 N3 0.0431(12) 0.0448(12) 0.0347(12) 0.0033(9) 0.0188(9) 0.0038(10) N2 0.0411(11) 0.0559(14) 0.0389(13) 0.0019(10) 0.0200(10) 0.0008(10) N4 0.0423(12) 0.0624(14) 0.0321(12) -0.0012(10) 0.0181(10) -0.0021(10) N1 0.0397(11) 0.0758(16) 0.0306(12) 0.0039(11) 0.0132(10) 0.0049(11) C21 0.0416(13) 0.0422(15) 0.0329(14) 0.0009(11) 0.0193(12) 0.0015(11) C24 0.0453(13) 0.0448(15) 0.0332(14) 0.0009(11) 0.0208(12) 0.0019(12) C25 0.0422(13) 0.0510(16) 0.0292(13) 0.0056(12) 0.0165(11) -0.0022(12) C32 0.0414(13) 0.0443(15) 0.0334(13) 0.0002(12) 0.0196(11) -0.0023(12) C19 0.0420(13) 0.0445(15) 0.0330(14) 0.0044(11) 0.0164(11) 0.0015(11) C15 0.0461(14) 0.0460(15) 0.0389(15) 0.0036(12) 0.0219(12) -0.0009(12) C22 0.0412(13) 0.0552(16) 0.0320(14) 0.0001(12) 0.0187(12) 0.0007(12) C20 0.0393(13) 0.0530(16) 0.0376(15) 0.0050(12) 0.0166(12) 0.0018(12) C7 0.0436(14) 0.0535(16) 0.0339(15) -0.0040(12) 0.0156(12) -0.0070(13) C31 0.0420(14) 0.0407(14) 0.0334(14) 0.0015(11) 0.0179(11) 0.0019(11) C16 0.0397(13) 0.0437(15) 0.0337(14) 0.0032(11) 0.0163(11) 0.0012(11) C13 0.0418(13) 0.0533(16) 0.0302(13) -0.0008(12) 0.0157(11) 0.0006(12) C23 0.0494(15) 0.0650(18) 0.0350(14) -0.0018(13) 0.0242(12) 0.0021(14) C37 0.0506(15) 0.0455(16) 0.0414(16) 0.0040(12) 0.0225(12) 0.0029(13) C18 0.0473(15) 0.0549(16) 0.0389(15) 0.0050(12) 0.0217(12) -0.0058(13) C26 0.0456(14) 0.0546(16) 0.0443(16) -0.0044(13) 0.0230(13) -0.0052(13) C1 0.0446(14) 0.0575(17) 0.0360(15) 0.0091(13) 0.0170(12) -0.0008(13) C14 0.0390(13) 0.0522(16) 0.0414(15) -0.0005(13) 0.0170(12) -0.0050(12) C12 0.0579(16) 0.0484(17) 0.0450(17) 0.0003(13) 0.0210(14) -0.0028(14) C17 0.0411(14) 0.0575(17) 0.0407(15) 0.0001(13) 0.0178(12) -0.0089(13) C27 0.0457(15) 0.0655(19) 0.0599(19) -0.0025(15) 0.0297(14) -0.0004(14) C30 0.0557(16) 0.0569(18) 0.0507(17) -0.0096(14) 0.0284(14) -0.0104(14) C8 0.0510(16) 0.0644(19) 0.0408(16) 0.0048(14) 0.0180(13) -0.0010(14) C33 0.0558(16) 0.0650(18) 0.0401(16) -0.0013(14) 0.0259(13) 0.0053(14) C2 0.0508(16) 0.0613(18) 0.0443(16) 0.0063(14) 0.0228(13) 0.0011(14) C6 0.0512(16) 0.077(2) 0.0425(17) 0.0038(15) 0.0158(14) -0.0099(15) C36 0.0527(16) 0.0599(19) 0.0461(18) 0.0133(15) 0.0187(14) 0.0007(14) C35 0.0586(17) 0.079(2) 0.0334(15) -0.0005(15) 0.0171(14) -0.0155(17) C9 0.0641(19) 0.078(2) 0.0389(17) 0.0089(15) 0.0225(15) -0.0093(17) C11 0.0653(18) 0.0589(19) 0.058(2) -0.0131(16) 0.0358(16) -0.0090(15) C28 0.0423(15) 0.080(2) 0.065(2) -0.0041(17) 0.0250(15) -0.0124(16) C29 0.0579(18) 0.076(2) 0.061(2) -0.0215(17) 0.0290(16) -0.0272(17) C34 0.0672(19) 0.074(2) 0.0426(17) -0.0134(16) 0.0293(15) -0.0060(17) C10 0.075(2) 0.074(2) 0.0455(18) -0.0119(16) 0.0360(16) -0.0197(18) C3 0.0625(19) 0.068(2) 0.069(2) 0.0157(17) 0.0391(17) 0.0099(16) C5 0.0419(16) 0.096(3) 0.054(2) 0.0187(18) 0.0123(14) -0.0152(16) C4 0.0470(17) 0.087(2) 0.078(2) 0.032(2) 0.0317(18) 0.0070(17) 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' 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 C31 N3 C21 116.9(2) . . ? C20 N2 C21 116.1(2) . . ? C24 N4 C22 117.4(2) . . ? C7 N1 C13 121.1(2) . . ? C7 N1 C1 121.3(2) . . ? C1 N1 C13 117.5(2) . . ? N3 C21 C22 121.4(2) . . ? N2 C21 N3 116.0(2) . . ? N2 C21 C22 122.6(2) . . ? N4 C24 C25 115.7(2) . . ? N4 C24 C31 121.0(2) . . ? C31 C24 C25 123.4(2) . . ? C26 C25 C24 119.6(2) . . ? C26 C25 C30 117.9(2) . . ? C30 C25 C24 122.5(2) . . ? C37 C32 C31 121.4(2) . . ? C37 C32 C33 118.7(2) . . ? C33 C32 C31 119.9(2) . . ? C20 C19 C16 119.7(2) . . ? C23 C19 C20 116.3(2) . . ? C23 C19 C16 123.9(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C14 C15 C16 120.5(3) . . ? N4 C22 C21 121.0(2) . . ? N4 C22 C23 120.0(2) . . ? C21 C22 C23 118.9(2) . . ? N2 C20 C19 126.4(2) . . ? N2 C20 H20 116.8 . . ? C19 C20 H20 116.8 . . ? C12 C7 N1 121.0(2) . . ? C12 C7 C8 118.4(3) . . ? C8 C7 N1 120.6(3) . . ? N3 C31 C24 122.0(2) . . ? N3 C31 C32 115.4(2) . . ? C24 C31 C32 122.5(2) . . ? C15 C16 C19 120.6(2) . . ? C17 C16 C19 121.5(2) . . ? C17 C16 C15 117.8(2) . . ? C18 C13 N1 121.1(2) . . ? C14 C13 N1 119.8(2) . . ? C14 C13 C18 119.1(2) . . ? C19 C23 C22 119.8(2) . . ? C19 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C32 C37 H37 119.6 . . ? C32 C37 C36 120.9(3) . . ? C36 C37 H37 119.6 . . ? C13 C18 H18 120.2 . . ? C13 C18 C17 119.6(2) . . ? C17 C18 H18 120.2 . . ? C25 C26 H26 119.4 . . ? C27 C26 C25 121.2(3) . . ? C27 C26 H26 119.4 . . ? C2 C1 N1 120.2(2) . . ? C2 C1 C6 119.1(3) . . ? C6 C1 N1 120.7(3) . . ? C15 C14 C13 121.0(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C7 C12 H12 119.7 . . ? C11 C12 C7 120.5(3) . . ? C11 C12 H12 119.7 . . ? C16 C17 C18 121.8(2) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C26 C27 H27 120.1 . . ? C28 C27 C26 119.9(3) . . ? C28 C27 H27 120.1 . . ? C25 C30 H30 119.7 . . ? C29 C30 C25 120.7(3) . . ? C29 C30 H30 119.7 . . ? C7 C8 H8 119.7 . . ? C9 C8 C7 120.6(3) . . ? C9 C8 H8 119.7 . . ? C32 C33 H33 119.8 . . ? C34 C33 C32 120.4(3) . . ? C34 C33 H33 119.8 . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 119.9 . . ? C1 C6 H6 120.3 . . ? C5 C6 C1 119.4(3) . . ? C5 C6 H6 120.3 . . ? C37 C36 H36 120.1 . . ? C35 C36 C37 119.9(3) . . ? C35 C36 H36 120.1 . . ? C36 C35 H35 120.1 . . ? C34 C35 C36 119.8(3) . . ? C34 C35 H35 120.1 . . ? C8 C9 H9 119.8 . . ? C10 C9 C8 120.4(3) . . ? C10 C9 H9 119.8 . . ? C12 C11 H11 119.8 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.8 . . ? C27 C28 H28 120.2 . . ? C29 C28 C27 119.6(3) . . ? C29 C28 H28 120.2 . . ? C30 C29 H29 119.7 . . ? C28 C29 C30 120.7(3) . . ? C28 C29 H29 119.7 . . ? C33 C34 H34 119.8 . . ? C35 C34 C33 120.5(3) . . ? C35 C34 H34 119.8 . . ? C9 C10 C11 119.5(3) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C2 C3 H3 119.4 . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3 119.4 . . ? C6 C5 H5 119.3 . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H5 119.3 . . ? C3 C4 C5 118.8(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? 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 N3 C21 1.364(3) . ? N3 C31 1.330(3) . ? N2 C21 1.362(3) . ? N2 C20 1.322(3) . ? N4 C24 1.326(3) . ? N4 C22 1.372(3) . ? N1 C7 1.407(3) . ? N1 C13 1.438(3) . ? N1 C1 1.424(3) . ? C21 C22 1.398(4) . ? C24 C25 1.487(3) . ? C24 C31 1.429(4) . ? C25 C26 1.385(4) . ? C25 C30 1.392(4) . ? C32 C31 1.490(3) . ? C32 C37 1.379(3) . ? C32 C33 1.384(4) . ? C19 C20 1.419(4) . ? C19 C16 1.486(3) . ? C19 C23 1.368(3) . ? C15 H15 0.9300 . ? C15 C16 1.399(3) . ? C15 C14 1.378(4) . ? C22 C23 1.409(3) . ? C20 H20 0.9300 . ? C7 C12 1.387(4) . ? C7 C8 1.395(4) . ? C16 C17 1.383(4) . ? C13 C18 1.385(3) . ? C13 C14 1.385(4) . ? C23 H23 0.9300 . ? C37 H37 0.9300 . ? C37 C36 1.386(4) . ? C18 H18 0.9300 . ? C18 C17 1.390(4) . ? C26 H26 0.9300 . ? C26 C27 1.383(4) . ? C1 C2 1.388(4) . ? C1 C6 1.399(4) . ? C14 H14 0.9300 . ? C12 H12 0.9300 . ? C12 C11 1.384(4) . ? C17 H17 0.9300 . ? C27 H27 0.9300 . ? C27 C28 1.376(4) . ? C30 H30 0.9300 . ? C30 C29 1.377(4) . ? C8 H8 0.9300 . ? C8 C9 1.379(4) . ? C33 H33 0.9300 . ? C33 C34 1.383(4) . ? C2 H2 0.9300 . ? C2 C3 1.381(4) . ? C6 H6 0.9300 . ? C6 C5 1.386(4) . ? C36 H36 0.9300 . ? C36 C35 1.374(4) . ? C35 H35 0.9300 . ? C35 C34 1.371(4) . ? C9 H9 0.9300 . ? C9 C10 1.376(4) . ? C11 H11 0.9300 . ? C11 C10 1.377(4) . ? C28 H28 0.9300 . ? C28 C29 1.369(4) . ? C29 H29 0.9300 . ? C34 H34 0.9300 . ? C10 H10 0.9300 . ? C3 H3 0.9300 . ? C3 C4 1.374(5) . ? C5 H5 0.9300 . ? C5 C4 1.379(5) . ? C4 H4 0.9300 . ? 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 N3 C21 C22 N4 4.6(4) . . . . ? N3 C21 C22 C23 -177.9(2) . . . . ? N2 C21 C22 N4 -176.8(2) . . . . ? N2 C21 C22 C23 0.6(4) . . . . ? N4 C24 C25 C26 44.9(3) . . . . ? N4 C24 C25 C30 -132.1(3) . . . . ? N4 C24 C31 N3 5.3(4) . . . . ? N4 C24 C31 C32 -172.3(2) . . . . ? N4 C22 C23 C19 177.7(2) . . . . ? N1 C7 C12 C11 -179.2(2) . . . . ? N1 C7 C8 C9 177.7(2) . . . . ? N1 C13 C18 C17 -174.2(2) . . . . ? N1 C13 C14 C15 172.9(2) . . . . ? N1 C1 C2 C3 178.0(2) . . . . ? N1 C1 C6 C5 -179.7(3) . . . . ? C21 N3 C31 C24 -1.3(3) . . . . ? C21 N3 C31 C32 176.4(2) . . . . ? C21 N2 C20 C19 0.6(4) . . . . ? C21 C22 C23 C19 0.2(4) . . . . ? C24 N4 C22 C21 -0.7(4) . . . . ? C24 N4 C22 C23 -178.1(2) . . . . ? C24 C25 C26 C27 -178.1(2) . . . . ? C24 C25 C30 C29 177.3(3) . . . . ? C25 C24 C31 N3 -175.1(2) . . . . ? C25 C24 C31 C32 7.3(4) . . . . ? C25 C26 C27 C28 0.5(4) . . . . ? C25 C30 C29 C28 1.0(5) . . . . ? C32 C37 C36 C35 1.3(4) . . . . ? C32 C33 C34 C35 0.3(4) . . . . ? C19 C16 C17 C18 173.1(3) . . . . ? C15 C16 C17 C18 -3.7(4) . . . . ? C22 N4 C24 C25 176.3(2) . . . . ? C22 N4 C24 C31 -4.1(4) . . . . ? C20 N2 C21 N3 177.6(2) . . . . ? C20 N2 C21 C22 -1.0(4) . . . . ? C20 C19 C16 C15 35.9(4) . . . . ? C20 C19 C16 C17 -140.8(3) . . . . ? C20 C19 C23 C22 -0.6(4) . . . . ? C7 N1 C13 C18 -47.7(4) . . . . ? C7 N1 C13 C14 134.4(3) . . . . ? C7 N1 C1 C2 143.3(3) . . . . ? C7 N1 C1 C6 -37.0(4) . . . . ? C7 C12 C11 C10 0.7(4) . . . . ? C7 C8 C9 C10 2.2(4) . . . . ? C31 N3 C21 N2 177.9(2) . . . . ? C31 N3 C21 C22 -3.4(4) . . . . ? C31 C24 C25 C26 -134.7(3) . . . . ? C31 C24 C25 C30 48.2(4) . . . . ? C31 C32 C37 C36 177.6(2) . . . . ? C31 C32 C33 C34 -178.4(3) . . . . ? C16 C19 C20 N2 177.1(2) . . . . ? C16 C19 C23 C22 -177.3(2) . . . . ? C16 C15 C14 C13 2.1(4) . . . . ? C13 N1 C7 C12 -33.4(4) . . . . ? C13 N1 C7 C8 146.7(3) . . . . ? C13 N1 C1 C2 -38.8(4) . . . . ? C13 N1 C1 C6 141.0(3) . . . . ? C13 C18 C17 C16 0.7(4) . . . . ? C23 C19 C20 N2 0.2(4) . . . . ? C23 C19 C16 C15 -147.5(3) . . . . ? C23 C19 C16 C17 35.8(4) . . . . ? C37 C32 C31 N3 -127.7(3) . . . . ? C37 C32 C31 C24 50.1(3) . . . . ? C37 C32 C33 C34 -0.1(4) . . . . ? C37 C36 C35 C34 -1.0(4) . . . . ? C18 C13 C14 C15 -5.1(4) . . . . ? C26 C25 C30 C29 0.2(4) . . . . ? C26 C27 C28 C29 0.7(5) . . . . ? C1 N1 C7 C12 144.5(3) . . . . ? C1 N1 C7 C8 -35.5(4) . . . . ? C1 N1 C13 C18 134.4(3) . . . . ? C1 N1 C13 C14 -43.6(4) . . . . ? C1 C2 C3 C4 1.3(4) . . . . ? C1 C6 C5 C4 2.1(5) . . . . ? C14 C15 C16 C19 -174.5(2) . . . . ? C14 C15 C16 C17 2.3(4) . . . . ? C14 C13 C18 C17 3.8(4) . . . . ? C12 C7 C8 C9 -2.2(4) . . . . ? C12 C11 C10 C9 -0.7(4) . . . . ? C27 C28 C29 C30 -1.4(5) . . . . ? C30 C25 C26 C27 -0.9(4) . . . . ? C8 C7 C12 C11 0.8(4) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C33 C32 C31 N3 50.7(3) . . . . ? C33 C32 C31 C24 -131.6(3) . . . . ? C33 C32 C37 C36 -0.7(4) . . . . ? C2 C1 C6 C5 0.0(4) . . . . ? C2 C3 C4 C5 0.7(5) . . . . ? C6 C1 C2 C3 -1.7(4) . . . . ? C6 C5 C4 C3 -2.4(5) . . . . ? C36 C35 C34 C33 0.2(4) . . . . ?