#------------------------------------------------------------------------------ #$Date: 2024-11-21 01:11:35 +0200 (Thu, 21 Nov 2024) $ #$Revision: 296022 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/32/1573236.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_1573236 loop_ _publ_author_name 'Dai, Hui' 'Liang, Yaohui' 'Long, Xiang' 'Tang, Tianyi' 'Xie, Haozhi' 'Ma, Zhiwei' 'Li, Gaoyu' 'Yang, Zhiyong' 'Zhao, Juan' 'Chi, Zhenguo' _publ_section_title ; Effective Design Strategy for Thermally Activated Delayed Fluorescence Emitters with Aggregation-Induced emission to Enable Sky-blue OLEDs Achieving EQE Nearly 30% ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC06613H _journal_year 2024 _chemical_formula_moiety 'C37 H24 N2 O' _chemical_formula_sum 'C37 H24 N2 O' _chemical_formula_weight 512.58 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2024-08-12 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2024-09-27 deposited with the CCDC. 2024-11-18 downloaded from the CCDC. ; _cell_angle_alpha 97.448(14) _cell_angle_beta 93.423(14) _cell_angle_gamma 90.73(2) _cell_formula_units_Z 2 _cell_length_a 6.499(3) _cell_length_b 11.218(4) _cell_length_c 17.798(8) _cell_measurement_reflns_used 475 _cell_measurement_temperature 150.00 _cell_measurement_theta_max 43.02 _cell_measurement_theta_min 3.46 _cell_volume 1284.1(9) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 150.0 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Ga K\a' _diffrn_radiation_wavelength 1.34138 _diffrn_reflns_av_R_equivalents 0.0733 _diffrn_reflns_av_unetI/netI 0.0830 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 17318 _diffrn_reflns_theta_full 59.78 _diffrn_reflns_theta_max 59.78 _diffrn_reflns_theta_min 2.18 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.396 _exptl_absorpt_correction_T_max 0.7516 _exptl_absorpt_correction_T_min 0.5666 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1467 before and 0.0652 after correction. The Ratio of minimum to maximum transmission is 0.7539. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_description PRISM _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.008 _exptl_crystal_size_min 0.005 _refine_diff_density_max 0.306 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.085 _refine_ls_extinction_coef 0.0120(15) _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 1.019 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 362 _refine_ls_number_reflns 5672 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0614 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0931P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1470 _refine_ls_wR_factor_ref 0.1763 _reflns_number_gt 3319 _reflns_number_total 5672 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d4sc06613h2.cif _cod_data_source_block b24051503a0247_0m _cod_database_code 1573236 _olex2_refinement_description ; 1. Others Fixed Uiso: H2(0.05) H3(0.053) H4(0.049) H5(0.044) H9(0.043) H10(0.042) H15(0.045) H16(0.048) H17(0.047) H18(0.044) H20(0.046) H21(0.047) H23(0.045) H24(0.044) H27(0.053) H28(0.058) H29(0.064) H30(0.064) H31(0.053) H33(0.047) H34(0.057) H35(0.061) H36(0.059) H37(0.047) Fixed X: H2(0.741) H3(0.6781) H4(0.3892) H5(0.1604) H9(0.338) H10(0.0283) H15(-0.4747) H16(-0.7024) H17(-0.6344) H18(-0.3419) H20(0.8881) H21(1.0828) H23(0.5774) H24(0.3795) H27(1.1529) H28(1.0464) H29(0.7352) H30(0.5339) H31(0.6433) H33(0.1659) H34(0.2202) H35(-0.0002) H36(-0.2818) H37(-0.3313) Fixed Y: H2(0.8652) H3(1.0663) H4(1.161) H5(1.0565) H9(0.5202) H10(0.5103) H15(0.9647) H16(0.8393) H17(0.6369) H18(0.5517) H20(0.7207) H21(0.5904) H23(0.3827) H24(0.5148) H27(0.2141) H28(0.0965) H29(0.1327) H30(0.2929) H31(0.4148) H33(1.0179) H34(1.2261) H35(1.3448) H36(1.2564) H37(1.0483) Fixed Z: H2(0.3516) H3(0.3948) H4(0.3478) H5(0.256) H9(0.1532) H10(0.0782) H15(0.0625) H16(-0.0203) H17(-0.0528) H18(-0.0005) H20(0.271) H21(0.3357) H23(0.347) H24(0.2847) H27(0.4464) H28(0.5353) H29(0.591) H30(0.5606) H31(0.4738) H33(0.077) H34(0.1009) H35(0.1757) H36(0.2241) H37(0.2036) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn O1 O 1.1682(3) 0.39208(18) 0.37903(12) 0.0584(5) Uani 1 d . . . N1 N 0.4905(3) 0.72205(16) 0.24357(11) 0.0358(5) Uani 1 d . . . N2 N -0.1144(3) 0.88674(16) 0.12863(10) 0.0342(5) Uani 1 d . . . C1 C 0.4903(3) 0.8431(2) 0.27540(13) 0.0348(5) Uani 1 d . . . C2 C 0.6251(4) 0.9041(2) 0.33150(13) 0.0418(6) Uani 1 d . . . H2 H 0.7410 0.8652 0.3516 0.050 Uiso 1 calc . . R C3 C 0.5861(4) 1.0228(2) 0.35732(14) 0.0438(6) Uani 1 d . . . H3 H 0.6781 1.0663 0.3948 0.053 Uiso 1 calc . . R C4 C 0.4140(3) 1.0795(2) 0.32918(13) 0.0407(6) Uani 1 d . . . H4 H 0.3892 1.1610 0.3478 0.049 Uiso 1 calc . . R C5 C 0.2789(3) 1.0177(2) 0.27420(13) 0.0368(5) Uani 1 d . . . H5 H 0.1604 1.0565 0.2560 0.044 Uiso 1 calc . . R C6 C 0.3160(3) 0.8988(2) 0.24534(12) 0.0337(5) Uani 1 d . . . C7 C 0.2085(3) 0.80683(19) 0.19151(12) 0.0318(5) Uani 1 d . . . C8 C 0.3168(3) 0.6991(2) 0.19332(12) 0.0334(5) Uani 1 d . . . C9 C 0.2566(3) 0.5896(2) 0.15110(13) 0.0359(5) Uani 1 d . . . H9 H 0.3380 0.5202 0.1532 0.043 Uiso 1 calc . . R C10 C 0.0757(3) 0.5845(2) 0.10614(13) 0.0354(5) Uani 1 d . . . H10 H 0.0283 0.5103 0.0782 0.042 Uiso 1 calc . . R C11 C -0.0376(3) 0.68826(19) 0.10167(12) 0.0315(5) Uani 1 d . . . C12 C 0.0288(3) 0.79976(19) 0.14233(12) 0.0320(5) Uani 1 d . . . C13 C -0.2309(3) 0.70848(19) 0.06147(12) 0.0318(5) Uani 1 d . . . C14 C -0.2730(3) 0.8306(2) 0.07955(12) 0.0336(5) Uani 1 d . . . C15 C -0.4476(3) 0.8817(2) 0.04980(13) 0.0372(6) Uani 1 d . . . H15 H -0.4747 0.9647 0.0625 0.045 Uiso 1 calc . . R C16 C -0.5809(3) 0.8070(2) 0.00074(13) 0.0400(6) Uani 1 d . . . H16 H -0.7024 0.8393 -0.0203 0.048 Uiso 1 calc . . R C17 C -0.5410(3) 0.6856(2) -0.01839(13) 0.0388(6) Uani 1 d . . . H17 H -0.6344 0.6369 -0.0528 0.047 Uiso 1 calc . . R C18 C -0.3675(3) 0.6349(2) 0.01202(13) 0.0367(6) Uani 1 d . . . H18 H -0.3419 0.5517 -0.0005 0.044 Uiso 1 calc . . R C19 C 0.6121(3) 0.6338(2) 0.27457(13) 0.0345(5) Uani 1 d . . . C20 C 0.8234(3) 0.6536(2) 0.28799(13) 0.0380(6) Uani 1 d . . . H20 H 0.8881 0.7207 0.2710 0.046 Uiso 1 calc . . R C21 C 0.9388(3) 0.5754(2) 0.32613(13) 0.0392(6) Uani 1 d . . . H21 H 1.0828 0.5904 0.3357 0.047 Uiso 1 calc . . R C22 C 0.8504(3) 0.4758(2) 0.35080(13) 0.0356(5) Uani 1 d . . . C23 C 0.6402(3) 0.4529(2) 0.33315(13) 0.0376(6) Uani 1 d . . . H23 H 0.5774 0.3827 0.3470 0.045 Uiso 1 calc . . R C24 C 0.5226(3) 0.5312(2) 0.29590(13) 0.0369(6) Uani 1 d . . . H24 H 0.3795 0.5148 0.2847 0.044 Uiso 1 calc . . R C25 C 0.9857(3) 0.3967(2) 0.39192(14) 0.0405(6) Uani 1 d . . . C26 C 0.9065(3) 0.3254(2) 0.44899(13) 0.0390(6) Uani 1 d . . . C27 C 1.0262(4) 0.2305(2) 0.46926(14) 0.0441(6) Uani 1 d . . . H27 H 1.1529 0.2141 0.4464 0.053 Uiso 1 calc . . R C28 C 0.9629(4) 0.1603(2) 0.52201(15) 0.0483(7) Uani 1 d . . . H28 H 1.0464 0.0965 0.5353 0.058 Uiso 1 calc . . R C29 C 0.7798(5) 0.1824(3) 0.55545(15) 0.0533(7) Uani 1 d . . . H29 H 0.7352 0.1327 0.5910 0.064 Uiso 1 calc . . R C30 C 0.6601(4) 0.2771(3) 0.53725(15) 0.0536(7) Uani 1 d . . . H30 H 0.5339 0.2929 0.5606 0.064 Uiso 1 calc . . R C31 C 0.7245(4) 0.3488(2) 0.48508(14) 0.0445(6) Uani 1 d . . . H31 H 0.6433 0.4148 0.4738 0.053 Uiso 1 calc . . R C32 C -0.0845(3) 1.0139(2) 0.14057(12) 0.0332(5) Uani 1 d . . . C33 C 0.0773(3) 1.0662(2) 0.10819(13) 0.0395(6) Uani 1 d . . . H33 H 0.1659 1.0179 0.0770 0.047 Uiso 1 calc . . R C34 C 0.1079(4) 1.1898(2) 0.12192(15) 0.0474(7) Uani 1 d . . . H34 H 0.2202 1.2261 0.1009 0.057 Uiso 1 calc . . R C35 C -0.0233(4) 1.2602(2) 0.16579(16) 0.0506(7) Uani 1 d . . . H35 H -0.0002 1.3448 0.1757 0.061 Uiso 1 calc . . R C36 C -0.1885(4) 1.2076(2) 0.19527(15) 0.0488(7) Uani 1 d . . . H36 H -0.2818 1.2564 0.2241 0.059 Uiso 1 calc . . R C37 C -0.2183(3) 1.0844(2) 0.18288(13) 0.0394(6) Uani 1 d . . . H37 H -0.3313 1.0483 0.2036 0.047 Uiso 1 calc . . R 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 O1 0.0333(9) 0.0694(13) 0.0782(14) 0.0300(11) 0.0051(9) 0.0075(8) N1 0.0326(9) 0.0365(11) 0.0374(11) 0.0063(8) -0.0080(8) 0.0001(8) N2 0.0297(9) 0.0358(11) 0.0361(11) 0.0044(8) -0.0049(8) -0.0003(8) C1 0.0326(11) 0.0396(13) 0.0327(12) 0.0092(10) -0.0026(9) -0.0012(9) C2 0.0391(12) 0.0478(15) 0.0373(13) 0.0073(11) -0.0095(10) -0.0061(11) C3 0.0429(13) 0.0510(15) 0.0350(13) 0.0015(11) -0.0081(10) -0.0084(11) C4 0.0438(13) 0.0439(14) 0.0331(13) 0.0018(11) 0.0010(10) -0.0035(11) C5 0.0363(11) 0.0419(14) 0.0322(12) 0.0062(10) -0.0002(9) -0.0025(10) C6 0.0328(11) 0.0360(13) 0.0321(12) 0.0051(10) -0.0007(9) -0.0029(9) C7 0.0310(10) 0.0342(12) 0.0301(12) 0.0058(9) -0.0019(9) -0.0021(9) C8 0.0304(10) 0.0391(13) 0.0302(12) 0.0059(10) -0.0032(9) -0.0032(9) C9 0.0338(11) 0.0388(13) 0.0354(13) 0.0071(10) -0.0016(9) 0.0002(10) C10 0.0352(11) 0.0357(13) 0.0349(12) 0.0065(10) -0.0036(9) -0.0031(9) C11 0.0302(10) 0.0345(12) 0.0300(12) 0.0064(9) -0.0020(9) -0.0024(9) C12 0.0284(10) 0.0358(12) 0.0320(12) 0.0076(10) -0.0013(9) -0.0016(9) C13 0.0290(10) 0.0362(13) 0.0304(12) 0.0062(10) -0.0002(9) -0.0041(9) C14 0.0311(10) 0.0370(13) 0.0328(12) 0.0067(10) -0.0016(9) -0.0040(9) C15 0.0319(11) 0.0399(13) 0.0402(13) 0.0092(11) -0.0032(10) 0.0001(10) C16 0.0329(11) 0.0437(14) 0.0434(14) 0.0106(11) -0.0068(10) -0.0049(10) C17 0.0338(11) 0.0436(14) 0.0387(13) 0.0080(11) -0.0054(10) -0.0058(10) C18 0.0329(11) 0.0399(13) 0.0373(13) 0.0084(10) -0.0046(9) -0.0043(10) C19 0.0316(11) 0.0403(13) 0.0317(12) 0.0080(10) -0.0033(9) 0.0012(9) C20 0.0307(11) 0.0454(14) 0.0392(13) 0.0123(11) -0.0012(9) -0.0019(10) C21 0.0289(11) 0.0485(14) 0.0406(14) 0.0084(11) -0.0006(10) 0.0014(10) C22 0.0292(10) 0.0427(13) 0.0354(12) 0.0076(10) -0.0003(9) 0.0016(9) C23 0.0327(11) 0.0429(14) 0.0376(13) 0.0087(11) -0.0016(9) -0.0021(10) C24 0.0295(10) 0.0463(14) 0.0346(13) 0.0074(11) -0.0038(9) -0.0008(10) C25 0.0305(11) 0.0490(15) 0.0423(14) 0.0084(12) -0.0007(10) 0.0021(10) C26 0.0380(12) 0.0421(14) 0.0361(13) 0.0064(11) -0.0052(10) -0.0021(10) C27 0.0411(13) 0.0452(15) 0.0452(15) 0.0085(12) -0.0089(11) 0.0032(11) C28 0.0576(16) 0.0441(15) 0.0423(15) 0.0096(12) -0.0132(12) -0.0036(12) C29 0.0671(18) 0.0609(18) 0.0325(14) 0.0132(13) -0.0055(13) -0.0103(14) C30 0.0540(15) 0.0680(19) 0.0392(15) 0.0084(14) 0.0043(12) -0.0016(14) C31 0.0447(13) 0.0534(16) 0.0352(13) 0.0066(12) 0.0001(11) 0.0028(11) C32 0.0317(11) 0.0347(12) 0.0329(12) 0.0050(10) -0.0021(9) -0.0009(9) C33 0.0357(12) 0.0444(14) 0.0387(13) 0.0070(11) 0.0022(10) -0.0018(10) C34 0.0467(14) 0.0488(16) 0.0482(15) 0.0156(13) -0.0013(12) -0.0100(12) C35 0.0607(16) 0.0375(14) 0.0525(17) 0.0073(12) -0.0069(13) -0.0068(12) C36 0.0539(15) 0.0422(15) 0.0481(16) -0.0028(12) 0.0035(12) 0.0044(12) C37 0.0360(11) 0.0428(14) 0.0392(14) 0.0048(11) 0.0016(10) -0.0010(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 '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 C1 N1 C19 123.43(17) . . ? C8 N1 C1 108.50(17) . . ? C8 N1 C19 125.71(18) . . ? C12 N2 C14 107.67(17) . . ? C12 N2 C32 127.53(16) . . ? C14 N2 C32 122.22(17) . . ? N1 C1 C6 109.24(17) . . ? C2 C1 N1 128.8(2) . . ? C2 C1 C6 121.8(2) . . ? C1 C2 H2 120.8 . . ? C3 C2 C1 118.4(2) . . ? C3 C2 H2 120.8 . . ? C2 C3 H3 119.5 . . ? C2 C3 C4 121.0(2) . . ? C4 C3 H3 119.5 . . ? C3 C4 H4 119.9 . . ? C5 C4 C3 120.3(2) . . ? C5 C4 H4 119.9 . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.3(2) . . ? C6 C5 H5 119.8 . . ? C1 C6 C7 106.1(2) . . ? C5 C6 C1 118.17(18) . . ? C5 C6 C7 135.6(2) . . ? C8 C7 C6 107.58(18) . . ? C8 C7 C12 115.90(19) . . ? C12 C7 C6 136.5(2) . . ? N1 C8 C7 108.53(18) . . ? C9 C8 N1 127.1(2) . . ? C9 C8 C7 124.42(18) . . ? C8 C9 H9 120.9 . . ? C10 C9 C8 118.2(2) . . ? C10 C9 H9 120.9 . . ? C9 C10 H10 120.0 . . ? C9 C10 C11 120.0(2) . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 121.39(18) . . ? C10 C11 C13 131.76(19) . . ? C12 C11 C13 106.84(19) . . ? N2 C12 C7 130.6(2) . . ? N2 C12 C11 109.25(17) . . ? C11 C12 C7 120.0(2) . . ? C14 C13 C11 106.59(17) . . ? C18 C13 C11 133.8(2) . . ? C18 C13 C14 119.6(2) . . ? N2 C14 C13 109.65(18) . . ? C15 C14 N2 128.3(2) . . ? C15 C14 C13 122.08(19) . . ? C14 C15 H15 121.4 . . ? C16 C15 C14 117.3(2) . . ? C16 C15 H15 121.4 . . ? C15 C16 H16 119.3 . . ? C15 C16 C17 121.5(2) . . ? C17 C16 H16 119.3 . . ? C16 C17 H17 119.5 . . ? C18 C17 C16 120.96(19) . . ? C18 C17 H17 119.5 . . ? C13 C18 H18 120.7 . . ? C17 C18 C13 118.5(2) . . ? C17 C18 H18 120.7 . . ? C20 C19 N1 119.5(2) . . ? C20 C19 C24 119.1(2) . . ? C24 C19 N1 121.31(19) . . ? C19 C20 H20 120.1 . . ? C21 C20 C19 119.8(2) . . ? C21 C20 H20 120.1 . . ? C20 C21 H21 119.1 . . ? C20 C21 C22 121.7(2) . . ? C22 C21 H21 119.1 . . ? C21 C22 C23 118.0(2) . . ? C21 C22 C25 118.23(19) . . ? C23 C22 C25 123.7(2) . . ? C22 C23 H23 119.6 . . ? C24 C23 C22 120.8(2) . . ? C24 C23 H23 119.6 . . ? C19 C24 H24 119.8 . . ? C23 C24 C19 120.43(19) . . ? C23 C24 H24 119.8 . . ? O1 C25 C22 118.8(2) . . ? O1 C25 C26 119.3(2) . . ? C26 C25 C22 121.9(2) . . ? C27 C26 C25 117.6(2) . . ? C31 C26 C25 124.4(2) . . ? C31 C26 C27 118.0(2) . . ? C26 C27 H27 119.6 . . ? C28 C27 C26 120.9(3) . . ? C28 C27 H27 119.6 . . ? C27 C28 H28 119.8 . . ? C29 C28 C27 120.3(3) . . ? C29 C28 H28 119.8 . . ? C28 C29 H29 120.1 . . ? C28 C29 C30 119.8(3) . . ? C30 C29 H29 120.1 . . ? C29 C30 H30 120.0 . . ? C31 C30 C29 120.0(3) . . ? C31 C30 H30 120.0 . . ? C26 C31 H31 119.6 . . ? C30 C31 C26 120.8(3) . . ? C30 C31 H31 119.6 . . ? C33 C32 N2 119.8(2) . . ? C37 C32 N2 119.8(2) . . ? C37 C32 C33 120.3(2) . . ? C32 C33 H33 120.4 . . ? C34 C33 C32 119.2(2) . . ? C34 C33 H33 120.4 . . ? C33 C34 H34 119.8 . . ? C35 C34 C33 120.5(2) . . ? C35 C34 H34 119.8 . . ? C34 C35 H35 120.1 . . ? C34 C35 C36 119.8(2) . . ? C36 C35 H35 120.1 . . ? C35 C36 H36 119.9 . . ? C37 C36 C35 120.1(3) . . ? C37 C36 H36 119.9 . . ? C32 C37 C36 120.0(2) . . ? C32 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? 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 O1 C25 1.222(3) . ? N1 C1 1.402(3) . ? N1 C8 1.397(2) . ? N1 C19 1.421(3) . ? N2 C12 1.391(3) . ? N2 C14 1.398(2) . ? N2 C32 1.424(3) . ? C1 C2 1.391(3) . ? C1 C6 1.412(3) . ? C2 H2 0.9500 . ? C2 C3 1.382(4) . ? C3 H3 0.9500 . ? C3 C4 1.393(3) . ? C4 H4 0.9500 . ? C4 C5 1.384(3) . ? C5 H5 0.9500 . ? C5 C6 1.395(3) . ? C6 C7 1.454(3) . ? C7 C8 1.410(3) . ? C7 C12 1.413(3) . ? C8 C9 1.393(3) . ? C9 H9 0.9500 . ? C9 C10 1.378(3) . ? C10 H10 0.9500 . ? C10 C11 1.394(3) . ? C11 C12 1.410(3) . ? C11 C13 1.444(3) . ? C13 C14 1.401(3) . ? C13 C18 1.394(3) . ? C14 C15 1.386(3) . ? C15 H15 0.9500 . ? C15 C16 1.385(3) . ? C16 H16 0.9500 . ? C16 C17 1.391(3) . ? C17 H17 0.9500 . ? C17 C18 1.383(3) . ? C18 H18 0.9500 . ? C19 C20 1.389(3) . ? C19 C24 1.390(3) . ? C20 H20 0.9500 . ? C20 C21 1.379(3) . ? C21 H21 0.9500 . ? C21 C22 1.383(3) . ? C22 C23 1.397(3) . ? C22 C25 1.486(3) . ? C23 H23 0.9500 . ? C23 C24 1.378(3) . ? C24 H24 0.9500 . ? C25 C26 1.483(3) . ? C26 C27 1.399(3) . ? C26 C31 1.391(4) . ? C27 H27 0.9500 . ? C27 C28 1.378(3) . ? C28 H28 0.9500 . ? C28 C29 1.373(4) . ? C29 H29 0.9500 . ? C29 C30 1.385(4) . ? C30 H30 0.9500 . ? C30 C31 1.384(4) . ? C31 H31 0.9500 . ? C32 C33 1.388(3) . ? C32 C37 1.375(3) . ? C33 H33 0.9500 . ? C33 C34 1.386(3) . ? C34 H34 0.9500 . ? C34 C35 1.378(4) . ? C35 H35 0.9500 . ? C35 C36 1.381(4) . ? C36 H36 0.9500 . ? C36 C37 1.381(3) . ? C37 H37 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 O1 C25 C26 C27 -18.3(3) . . . . ? O1 C25 C26 C31 159.8(2) . . . . ? N1 C1 C2 C3 -176.0(2) . . . . ? N1 C1 C6 C5 175.2(2) . . . . ? N1 C1 C6 C7 -1.2(2) . . . . ? N1 C8 C9 C10 178.1(2) . . . . ? N1 C19 C20 C21 172.4(2) . . . . ? N1 C19 C24 C23 -173.1(2) . . . . ? N2 C14 C15 C16 178.7(2) . . . . ? N2 C32 C33 C34 -178.30(19) . . . . ? N2 C32 C37 C36 179.3(2) . . . . ? C1 N1 C8 C7 1.6(2) . . . . ? C1 N1 C8 C9 -178.6(2) . . . . ? C1 N1 C19 C20 -53.9(3) . . . . ? C1 N1 C19 C24 122.3(2) . . . . ? C1 C2 C3 C4 1.3(4) . . . . ? C1 C6 C7 C8 2.2(3) . . . . ? C1 C6 C7 C12 -179.8(3) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? C2 C1 C6 C7 -177.4(2) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C3 C4 C5 C6 -1.2(4) . . . . ? C4 C5 C6 C1 1.8(3) . . . . ? C4 C5 C6 C7 177.0(2) . . . . ? C5 C6 C7 C8 -173.3(3) . . . . ? C5 C6 C7 C12 4.6(5) . . . . ? C6 C1 C2 C3 -0.7(4) . . . . ? C6 C7 C8 N1 -2.4(3) . . . . ? C6 C7 C8 C9 177.8(2) . . . . ? C6 C7 C12 N2 0.2(5) . . . . ? C6 C7 C12 C11 -174.7(2) . . . . ? C7 C8 C9 C10 -2.1(4) . . . . ? C8 N1 C1 C2 175.6(2) . . . . ? C8 N1 C1 C6 -0.2(2) . . . . ? C8 N1 C19 C20 145.6(2) . . . . ? C8 N1 C19 C24 -38.2(3) . . . . ? C8 C7 C12 N2 178.1(2) . . . . ? C8 C7 C12 C11 3.1(3) . . . . ? C8 C9 C10 C11 2.3(3) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C9 C10 C11 C13 -178.3(2) . . . . ? C10 C11 C12 N2 -178.9(2) . . . . ? C10 C11 C12 C7 -2.9(3) . . . . ? C10 C11 C13 C14 178.5(2) . . . . ? C10 C11 C13 C18 -2.4(4) . . . . ? C11 C13 C14 N2 0.3(3) . . . . ? C11 C13 C14 C15 179.3(2) . . . . ? C11 C13 C18 C17 -178.5(2) . . . . ? C12 N2 C14 C13 -0.4(3) . . . . ? C12 N2 C14 C15 -179.3(2) . . . . ? C12 N2 C32 C33 54.0(3) . . . . ? C12 N2 C32 C37 -127.3(2) . . . . ? C12 C7 C8 N1 179.19(19) . . . . ? C12 C7 C8 C9 -0.6(3) . . . . ? C12 C11 C13 C14 -0.1(2) . . . . ? C12 C11 C13 C18 179.0(2) . . . . ? C13 C11 C12 N2 -0.2(2) . . . . ? C13 C11 C12 C7 175.8(2) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 N2 C12 C7 -175.0(2) . . . . ? C14 N2 C12 C11 0.4(3) . . . . ? C14 N2 C32 C33 -105.5(2) . . . . ? C14 N2 C32 C37 73.3(3) . . . . ? C14 C13 C18 C17 0.5(3) . . . . ? C14 C15 C16 C17 -0.4(4) . . . . ? C15 C16 C17 C18 1.0(4) . . . . ? C16 C17 C18 C13 -1.1(4) . . . . ? C18 C13 C14 N2 -179.0(2) . . . . ? C18 C13 C14 C15 0.0(3) . . . . ? C19 N1 C1 C2 12.2(4) . . . . ? C19 N1 C1 C6 -163.6(2) . . . . ? C19 N1 C8 C7 164.6(2) . . . . ? C19 N1 C8 C9 -15.6(4) . . . . ? C19 C20 C21 C22 0.9(4) . . . . ? C20 C19 C24 C23 3.1(4) . . . . ? C20 C21 C22 C23 2.7(4) . . . . ? C20 C21 C22 C25 -179.6(2) . . . . ? C21 C22 C23 C24 -3.5(4) . . . . ? C21 C22 C25 O1 -27.1(3) . . . . ? C21 C22 C25 C26 151.7(2) . . . . ? C22 C23 C24 C19 0.6(4) . . . . ? C22 C25 C26 C27 162.9(2) . . . . ? C22 C25 C26 C31 -19.0(3) . . . . ? C23 C22 C25 O1 150.5(2) . . . . ? C23 C22 C25 C26 -30.7(4) . . . . ? C24 C19 C20 C21 -3.8(4) . . . . ? C25 C22 C23 C24 178.9(2) . . . . ? C25 C26 C27 C28 179.9(2) . . . . ? C25 C26 C31 C30 179.4(2) . . . . ? C26 C27 C28 C29 0.3(3) . . . . ? C27 C26 C31 C30 -2.5(3) . . . . ? C27 C28 C29 C30 -1.4(4) . . . . ? C28 C29 C30 C31 0.5(4) . . . . ? C29 C30 C31 C26 1.5(4) . . . . ? C31 C26 C27 C28 1.6(3) . . . . ? C32 N2 C12 C7 23.1(4) . . . . ? C32 N2 C12 C11 -161.5(2) . . . . ? C32 N2 C14 C13 162.6(2) . . . . ? C32 N2 C14 C15 -16.3(4) . . . . ? C32 C33 C34 C35 -1.4(3) . . . . ? C33 C32 C37 C36 -2.0(3) . . . . ? C33 C34 C35 C36 -1.1(4) . . . . ? C34 C35 C36 C37 2.1(4) . . . . ? C35 C36 C37 C32 -0.6(4) . . . . ? C37 C32 C33 C34 3.0(3) . . . . ?