#------------------------------------------------------------------------------ #$Date: 2021-06-05 22:29:16 +0300 (Sat, 05 Jun 2021) $ #$Revision: 266172 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158014.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_7158014 loop_ _publ_author_name 'Jin, Jiang' 'Li, Yinghua' 'Xiang, Shiqun' 'Fan, Weibin' 'Guo, Shiwei' 'Huang, Deguang' _publ_section_title ; Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using methyl tert-butyl ether as a new methylene precursor. ; _journal_issue 18 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4076 _journal_page_last 4081 _journal_paper_doi 10.1039/d1ob00120e _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C33 H30 N2' _chemical_formula_sum 'C33 H30 N2' _chemical_formula_weight 454.59 _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 _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-01-15 deposited with the CCDC. 2021-04-06 downloaded from the CCDC. ; _cell_angle_alpha 86.297(4) _cell_angle_beta 89.697(4) _cell_angle_gamma 87.381(4) _cell_formula_units_Z 2 _cell_length_a 5.5415(2) _cell_length_b 10.2343(5) _cell_length_c 21.6380(10) _cell_measurement_reflns_used 3109 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 72.4790 _cell_measurement_theta_min 4.0820 _cell_volume 1223.32(9) _computing_cell_refinement 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.5594 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_unetI/netI 0.0426 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 9490 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 69.995 _diffrn_reflns_theta_min 4.095 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.545 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.77580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description prism _exptl_crystal_F_000 484 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.502 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 316 _refine_ls_number_reflns 4590 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0648 _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^)+(0.1277P)^2^+0.2633P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1837 _refine_ls_wR_factor_ref 0.2001 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3594 _reflns_number_total 4590 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00120e2.cif _cod_data_source_block Compound3j _cod_depositor_comments 'Adding full bibliography for 7158011--7158015.cif.' _cod_database_code 7158014 _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_min 0.899 _shelx_estimated_absorpt_t_max 0.948 _shelx_res_file ; TITL full.res in P-1 full.res created by SHELXL-2018/3 at 17:56:49 on 18-Nov-2020 CELL 1.54184 5.5415 10.2343 21.638 86.297 89.697 87.381 ZERR 2 0.0002 0.0005 0.001 0.004 0.004 0.004 LATT 1 SFAC C H N UNIT 66 60 4 TEMP -173 SIZE 0.20 0.15 0.10 OMIT 0 140 OMIT 6 2 5 OMIT -6 -2 2 OMIT 6 2 2 OMIT -6 -2 1 OMIT 6 2 3 OMIT 6 4 6 OMIT 6 3 4 OMIT 6 4 7 OMIT 6 5 7 OMIT 6 2 1 OMIT -6 -4 6 L.S. 6 PLAN 2 fmap 2 MORE -1 BOND $H ACTA CONF WGHT 0.127700 0.263300 FVAR 7.61539 N1 3 0.278795 0.765643 0.382228 11.00000 0.03792 0.04198 = 0.02623 -0.00308 0.00124 -0.00899 N2 3 0.638410 0.518407 0.146728 11.00000 0.03138 0.02701 = 0.02849 -0.00433 -0.00414 -0.00383 C1 1 0.461131 0.671386 0.373169 11.00000 0.04597 0.03315 = 0.02323 -0.00056 -0.00495 -0.00602 C2 1 0.604116 0.711060 0.324449 11.00000 0.03917 0.03145 = 0.02468 -0.00444 -0.00640 -0.00608 C3 1 0.506495 0.837180 0.301550 11.00000 0.03176 0.03183 = 0.02443 -0.00561 -0.00530 -0.00786 C4 1 0.567516 0.925650 0.252437 11.00000 0.03792 0.03369 = 0.02634 -0.00346 -0.00100 -0.00732 AFIX 43 H4A 2 0.704789 0.908090 0.227302 11.00000 -1.20000 AFIX 0 C5 1 0.424260 1.039253 0.241120 11.00000 0.04942 0.03218 = 0.03185 0.00092 -0.00175 -0.00480 AFIX 43 H5A 2 0.464601 1.100135 0.208091 11.00000 -1.20000 AFIX 0 C6 1 0.220974 1.065341 0.277750 11.00000 0.04668 0.03632 = 0.03836 -0.00365 -0.00383 0.00461 AFIX 43 H6A 2 0.124654 1.143322 0.268649 11.00000 -1.20000 AFIX 0 C7 1 0.156913 0.981055 0.326591 11.00000 0.03539 0.04349 = 0.03268 -0.00864 -0.00133 -0.00036 AFIX 43 H7A 2 0.019114 0.999698 0.351368 11.00000 -1.20000 AFIX 0 C8 1 0.301520 0.867477 0.338339 11.00000 0.03347 0.03612 = 0.02508 -0.00627 -0.00522 -0.00722 C9 1 0.085858 0.754430 0.427971 11.00000 0.03438 0.05768 = 0.02798 -0.00324 -0.00007 -0.01395 AFIX 23 H9A 2 0.014924 0.667852 0.425615 11.00000 -1.20000 H9B 2 -0.042485 0.822294 0.416977 11.00000 -1.20000 AFIX 0 C10 1 0.163021 0.768865 0.494206 11.00000 0.03425 0.04383 = 0.02784 -0.00391 0.00032 0.00008 C11 1 0.019279 0.719596 0.542015 11.00000 0.04540 0.04873 = 0.03366 -0.00327 0.00457 0.00010 AFIX 43 H11A 2 -0.122561 0.676115 0.532618 11.00000 -1.20000 AFIX 0 C12 1 0.079254 0.732769 0.603389 11.00000 0.07615 0.05777 = 0.02924 -0.00260 0.00874 0.01463 AFIX 43 H12A 2 -0.020576 0.697699 0.635603 11.00000 -1.20000 AFIX 0 C13 1 0.282978 0.796503 0.617727 11.00000 0.07168 0.06403 = 0.03533 -0.01809 -0.01080 0.02904 AFIX 43 H13A 2 0.324209 0.806045 0.659706 11.00000 -1.20000 AFIX 0 C14 1 0.426093 0.846190 0.570604 11.00000 0.05148 0.06817 = 0.05383 -0.02659 -0.01672 0.00411 AFIX 43 H14A 2 0.567141 0.890181 0.580183 11.00000 -1.20000 AFIX 0 C15 1 0.366707 0.832775 0.509097 11.00000 0.04493 0.06478 = 0.04177 -0.01334 -0.00342 -0.00948 AFIX 43 H15A 2 0.467166 0.867893 0.477030 11.00000 -1.20000 AFIX 0 C16 1 0.474278 0.547905 0.413866 11.00000 0.07351 0.04200 = 0.03145 0.00750 0.00238 -0.00536 AFIX 33 H16A 2 0.343846 0.550319 0.444590 11.00000 -1.50000 H16B 2 0.457119 0.472744 0.388631 11.00000 -1.50000 H16C 2 0.630502 0.539551 0.435108 11.00000 -1.50000 AFIX 0 C17 1 0.817478 0.636832 0.297892 11.00000 0.04026 0.03599 = 0.02664 -0.00460 -0.00628 -0.00127 AFIX 23 H17A 2 0.849680 0.554760 0.323888 11.00000 -1.20000 H17B 2 0.961499 0.690163 0.299934 11.00000 -1.20000 AFIX 0 C18 1 0.617489 0.521498 0.210531 11.00000 0.03211 0.02823 = 0.02811 -0.00041 -0.00151 0.00097 C19 1 0.782540 0.603064 0.231775 11.00000 0.03077 0.02992 = 0.02790 -0.00360 -0.00389 -0.00111 C20 1 0.915240 0.653160 0.178916 11.00000 0.02946 0.02620 = 0.02909 -0.00102 -0.00414 -0.00056 C21 1 1.108044 0.737381 0.170433 11.00000 0.03303 0.03108 = 0.04042 -0.00106 -0.00492 -0.00378 AFIX 43 H21A 2 1.176077 0.775519 0.204834 11.00000 -1.20000 AFIX 0 C22 1 1.196961 0.763839 0.111520 11.00000 0.03483 0.03149 = 0.05523 0.00640 0.00355 -0.00465 AFIX 43 H22A 2 1.327758 0.820247 0.105665 11.00000 -1.20000 AFIX 0 C23 1 1.098172 0.709147 0.060091 11.00000 0.04468 0.03775 = 0.03741 0.00918 0.00718 0.00330 AFIX 43 H23A 2 1.161869 0.730160 0.020013 11.00000 -1.20000 AFIX 0 C24 1 0.909399 0.625030 0.066615 11.00000 0.03939 0.03294 = 0.02889 -0.00015 -0.00195 0.00439 AFIX 43 H24A 2 0.843040 0.587400 0.031856 11.00000 -1.20000 AFIX 0 C25 1 0.820828 0.597878 0.126282 11.00000 0.02948 0.02514 = 0.02880 -0.00128 -0.00251 0.00087 C26 1 0.491579 0.444648 0.107355 11.00000 0.03255 0.03231 = 0.03177 -0.00413 -0.00987 -0.00143 AFIX 23 H26A 2 0.489001 0.488388 0.065182 11.00000 -1.20000 H26B 2 0.323758 0.447174 0.123298 11.00000 -1.20000 AFIX 0 C27 1 0.577072 0.302646 0.102981 11.00000 0.02771 0.03026 = 0.02465 -0.00150 -0.00054 -0.00590 C28 1 0.794343 0.250608 0.127207 11.00000 0.02899 0.03490 = 0.03570 -0.00428 -0.00268 -0.00553 AFIX 43 H28A 2 0.897187 0.304771 0.148198 11.00000 -1.20000 AFIX 0 C29 1 0.863176 0.119291 0.121002 11.00000 0.03057 0.03689 = 0.04391 0.00104 0.00374 0.00168 AFIX 43 H29A 2 1.012454 0.084604 0.137825 11.00000 -1.20000 AFIX 0 C30 1 0.715202 0.039125 0.090457 11.00000 0.04496 0.02980 = 0.04313 -0.00665 0.00838 -0.00338 AFIX 43 H30A 2 0.762549 -0.050171 0.086003 11.00000 -1.20000 AFIX 0 C31 1 0.497700 0.090729 0.066530 11.00000 0.04407 0.03554 = 0.03226 -0.00861 0.00146 -0.01151 AFIX 43 H31A 2 0.394839 0.036444 0.045616 11.00000 -1.20000 AFIX 0 C32 1 0.428913 0.220771 0.072836 11.00000 0.03268 0.03482 = 0.02610 -0.00064 -0.00366 -0.00728 AFIX 43 H32A 2 0.278560 0.254755 0.056387 11.00000 -1.20000 AFIX 0 C33 1 0.434405 0.443155 0.245715 11.00000 0.04303 0.03647 = 0.03813 0.00175 0.00319 -0.00769 AFIX 33 H33A 2 0.343043 0.394478 0.216878 11.00000 -1.50000 H33B 2 0.516714 0.381438 0.276023 11.00000 -1.50000 H33C 2 0.323552 0.502243 0.267288 11.00000 -1.50000 AFIX 0 HKLF 4 REM full.res in P-1 REM wR2 = 0.2001, GooF = S = 1.052, Restrained GooF = 1.052 for all data REM R1 = 0.0648 for 3594 Fo > 4sig(Fo) and 0.0842 for all 4590 data REM 316 parameters refined using 0 restraints END WGHT 0.1278 0.2631 REM Highest difference peak 0.502, deepest hole -0.439, 1-sigma level 0.064 Q1 1 0.2682 0.4810 0.2329 11.00000 0.05 0.50 Q2 1 0.4574 0.4521 0.2921 11.00000 0.05 0.48 ; _shelx_res_checksum 23330 loop_ _space_group_symop_operation_xyz 'x, y, z' '-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_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 N1 N 0.2788(4) 0.7656(2) 0.38223(9) 0.0351(4) Uani 1 1 d . . . . . N2 N 0.6384(3) 0.51841(17) 0.14673(8) 0.0288(4) Uani 1 1 d . . . . . C1 C 0.4611(4) 0.6714(2) 0.37317(10) 0.0340(5) Uani 1 1 d . . . . . C2 C 0.6041(4) 0.7111(2) 0.32445(10) 0.0315(5) Uani 1 1 d . . . . . C3 C 0.5065(4) 0.8372(2) 0.30155(10) 0.0290(5) Uani 1 1 d . . . . . C4 C 0.5675(4) 0.9257(2) 0.25244(10) 0.0324(5) Uani 1 1 d . . . . . H4A H 0.704789 0.908090 0.227302 0.039 Uiso 1 1 calc R U . . . C5 C 0.4243(5) 1.0393(2) 0.24112(11) 0.0378(5) Uani 1 1 d . . . . . H5A H 0.464601 1.100135 0.208091 0.045 Uiso 1 1 calc R U . . . C6 C 0.2210(5) 1.0653(2) 0.27775(12) 0.0406(6) Uani 1 1 d . . . . . H6A H 0.124654 1.143322 0.268649 0.049 Uiso 1 1 calc R U . . . C7 C 0.1569(4) 0.9811(2) 0.32659(11) 0.0370(5) Uani 1 1 d . . . . . H7A H 0.019114 0.999698 0.351368 0.044 Uiso 1 1 calc R U . . . C8 C 0.3015(4) 0.8675(2) 0.33834(10) 0.0312(5) Uani 1 1 d . . . . . C9 C 0.0859(4) 0.7544(3) 0.42797(11) 0.0396(6) Uani 1 1 d . . . . . H9A H 0.014924 0.667852 0.425615 0.048 Uiso 1 1 calc R U . . . H9B H -0.042485 0.822294 0.416977 0.048 Uiso 1 1 calc R U . . . C10 C 0.1630(4) 0.7689(2) 0.49421(11) 0.0353(5) Uani 1 1 d . . . . . C11 C 0.0193(5) 0.7196(3) 0.54202(12) 0.0427(6) Uani 1 1 d . . . . . H11A H -0.122561 0.676115 0.532618 0.051 Uiso 1 1 calc R U . . . C12 C 0.0793(6) 0.7328(3) 0.60339(13) 0.0550(8) Uani 1 1 d . . . . . H12A H -0.020576 0.697699 0.635603 0.066 Uiso 1 1 calc R U . . . C13 C 0.2830(6) 0.7965(3) 0.61773(13) 0.0573(8) Uani 1 1 d . . . . . H13A H 0.324209 0.806045 0.659706 0.069 Uiso 1 1 calc R U . . . C14 C 0.4261(6) 0.8462(3) 0.57060(15) 0.0570(8) Uani 1 1 d . . . . . H14A H 0.567141 0.890181 0.580183 0.068 Uiso 1 1 calc R U . . . C15 C 0.3667(5) 0.8328(3) 0.50910(14) 0.0498(7) Uani 1 1 d . . . . . H15A H 0.467166 0.867893 0.477030 0.060 Uiso 1 1 calc R U . . . C16 C 0.4743(6) 0.5479(3) 0.41387(12) 0.0493(7) Uani 1 1 d . . . . . H16A H 0.343846 0.550319 0.444590 0.074 Uiso 1 1 calc R U . . . H16B H 0.457119 0.472744 0.388631 0.074 Uiso 1 1 calc R U . . . H16C H 0.630502 0.539551 0.435108 0.074 Uiso 1 1 calc R U . . . C17 C 0.8175(4) 0.6368(2) 0.29789(10) 0.0342(5) Uani 1 1 d . . . . . H17A H 0.849680 0.554760 0.323888 0.041 Uiso 1 1 calc R U . . . H17B H 0.961499 0.690163 0.299934 0.041 Uiso 1 1 calc R U . . . C18 C 0.6175(4) 0.5215(2) 0.21053(10) 0.0296(5) Uani 1 1 d . . . . . C19 C 0.7825(4) 0.6031(2) 0.23178(10) 0.0294(5) Uani 1 1 d . . . . . C20 C 0.9152(4) 0.6532(2) 0.17892(10) 0.0283(4) Uani 1 1 d . . . . . C21 C 1.1080(4) 0.7374(2) 0.17043(11) 0.0348(5) Uani 1 1 d . . . . . H21A H 1.176077 0.775519 0.204834 0.042 Uiso 1 1 calc R U . . . C22 C 1.1970(4) 0.7638(2) 0.11152(13) 0.0408(6) Uani 1 1 d . . . . . H22A H 1.327758 0.820247 0.105665 0.049 Uiso 1 1 calc R U . . . C23 C 1.0982(5) 0.7091(2) 0.06009(12) 0.0406(6) Uani 1 1 d . . . . . H23A H 1.161869 0.730160 0.020013 0.049 Uiso 1 1 calc R U . . . C24 C 0.9094(4) 0.6250(2) 0.06661(11) 0.0340(5) Uani 1 1 d . . . . . H24A H 0.843040 0.587400 0.031856 0.041 Uiso 1 1 calc R U . . . C25 C 0.8208(4) 0.59788(19) 0.12628(10) 0.0279(4) Uani 1 1 d . . . . . C26 C 0.4916(4) 0.4446(2) 0.10735(11) 0.0321(5) Uani 1 1 d . . . . . H26A H 0.489001 0.488388 0.065182 0.039 Uiso 1 1 calc R U . . . H26B H 0.323758 0.447174 0.123298 0.039 Uiso 1 1 calc R U . . . C27 C 0.5771(4) 0.3026(2) 0.10298(9) 0.0274(4) Uani 1 1 d . . . . . C28 C 0.7943(4) 0.2506(2) 0.12721(11) 0.0330(5) Uani 1 1 d . . . . . H28A H 0.897187 0.304771 0.148198 0.040 Uiso 1 1 calc R U . . . C29 C 0.8632(4) 0.1193(2) 0.12100(12) 0.0374(5) Uani 1 1 d . . . . . H29A H 1.012454 0.084604 0.137825 0.045 Uiso 1 1 calc R U . . . C30 C 0.7152(5) 0.0391(2) 0.09046(12) 0.0391(5) Uani 1 1 d . . . . . H30A H 0.762549 -0.050171 0.086003 0.047 Uiso 1 1 calc R U . . . C31 C 0.4977(4) 0.0907(2) 0.06653(11) 0.0367(5) Uani 1 1 d . . . . . H31A H 0.394839 0.036444 0.045616 0.044 Uiso 1 1 calc R U . . . C32 C 0.4289(4) 0.2208(2) 0.07284(10) 0.0311(5) Uani 1 1 d . . . . . H32A H 0.278560 0.254755 0.056387 0.037 Uiso 1 1 calc R U . . . C33 C 0.4344(4) 0.4432(2) 0.24572(12) 0.0392(5) Uani 1 1 d . . . . . H33A H 0.343043 0.394478 0.216878 0.059 Uiso 1 1 calc R U . . . H33B H 0.516714 0.381438 0.276023 0.059 Uiso 1 1 calc R U . . . H33C H 0.323552 0.502243 0.267288 0.059 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 N1 0.0379(10) 0.0420(10) 0.0262(9) -0.0031(8) 0.0012(8) -0.0090(8) N2 0.0314(9) 0.0270(8) 0.0285(9) -0.0043(7) -0.0041(7) -0.0038(7) C1 0.0460(13) 0.0332(11) 0.0232(10) -0.0006(8) -0.0049(9) -0.0060(9) C2 0.0392(12) 0.0315(10) 0.0247(10) -0.0044(8) -0.0064(8) -0.0061(9) C3 0.0318(11) 0.0318(10) 0.0244(10) -0.0056(8) -0.0053(8) -0.0079(8) C4 0.0379(12) 0.0337(11) 0.0263(10) -0.0035(8) -0.0010(8) -0.0073(9) C5 0.0494(14) 0.0322(11) 0.0318(12) 0.0009(9) -0.0017(10) -0.0048(10) C6 0.0467(14) 0.0363(12) 0.0384(13) -0.0036(10) -0.0038(10) 0.0046(10) C7 0.0354(12) 0.0435(12) 0.0327(12) -0.0086(10) -0.0013(9) -0.0004(9) C8 0.0335(11) 0.0361(11) 0.0251(10) -0.0063(8) -0.0052(8) -0.0072(9) C9 0.0344(12) 0.0577(15) 0.0280(12) -0.0032(10) -0.0001(9) -0.0139(10) C10 0.0343(12) 0.0438(12) 0.0278(11) -0.0039(9) 0.0003(9) 0.0001(9) C11 0.0454(14) 0.0487(14) 0.0337(13) -0.0033(10) 0.0046(10) 0.0001(11) C12 0.076(2) 0.0578(16) 0.0292(13) -0.0026(11) 0.0087(13) 0.0146(14) C13 0.072(2) 0.0640(17) 0.0353(14) -0.0181(13) -0.0108(13) 0.0290(15) C14 0.0515(17) 0.0682(19) 0.0538(18) -0.0266(15) -0.0167(13) 0.0041(14) C15 0.0449(15) 0.0648(17) 0.0418(14) -0.0133(12) -0.0034(11) -0.0095(12) C16 0.0735(19) 0.0420(13) 0.0315(12) 0.0075(10) 0.0024(12) -0.0054(12) C17 0.0403(12) 0.0360(11) 0.0266(11) -0.0046(9) -0.0063(9) -0.0013(9) C18 0.0321(11) 0.0282(10) 0.0281(11) -0.0004(8) -0.0015(8) 0.0010(8) C19 0.0308(11) 0.0299(10) 0.0279(11) -0.0036(8) -0.0039(8) -0.0011(8) C20 0.0295(11) 0.0262(9) 0.0291(11) -0.0010(8) -0.0041(8) -0.0006(8) C21 0.0330(12) 0.0311(10) 0.0404(13) -0.0011(9) -0.0049(9) -0.0038(8) C22 0.0348(12) 0.0315(11) 0.0552(16) 0.0064(10) 0.0036(11) -0.0047(9) C23 0.0447(14) 0.0377(12) 0.0374(13) 0.0092(10) 0.0072(10) 0.0033(10) C24 0.0394(12) 0.0329(11) 0.0289(11) -0.0001(8) -0.0019(9) 0.0044(9) C25 0.0295(11) 0.0251(9) 0.0288(11) -0.0013(8) -0.0025(8) 0.0009(8) C26 0.0326(11) 0.0323(11) 0.0318(11) -0.0041(9) -0.0099(9) -0.0014(8) C27 0.0277(10) 0.0303(10) 0.0247(10) -0.0015(8) -0.0005(8) -0.0059(8) C28 0.0290(11) 0.0349(11) 0.0357(12) -0.0043(9) -0.0027(9) -0.0055(9) C29 0.0306(12) 0.0369(12) 0.0439(13) 0.0010(10) 0.0037(9) 0.0017(9) C30 0.0450(14) 0.0298(11) 0.0431(13) -0.0066(9) 0.0084(10) -0.0034(9) C31 0.0441(13) 0.0355(11) 0.0323(11) -0.0086(9) 0.0015(9) -0.0115(9) C32 0.0327(11) 0.0348(11) 0.0261(10) -0.0006(8) -0.0037(8) -0.0073(8) C33 0.0430(13) 0.0365(12) 0.0381(13) 0.0018(10) 0.0032(10) -0.0077(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' 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 C8 N1 C1 108.63(19) . . ? C8 N1 C9 125.7(2) . . ? C1 N1 C9 125.6(2) . . ? C25 N2 C18 109.09(17) . . ? C25 N2 C26 125.09(18) . . ? C18 N2 C26 125.81(18) . . ? C2 C1 N1 110.2(2) . . ? C2 C1 C16 130.2(2) . . ? N1 C1 C16 119.7(2) . . ? C1 C2 C3 106.4(2) . . ? C1 C2 C17 127.6(2) . . ? C3 C2 C17 126.0(2) . . ? C4 C3 C8 118.8(2) . . ? C4 C3 C2 133.9(2) . . ? C8 C3 C2 107.23(19) . . ? C5 C4 C3 118.9(2) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 C6 120.8(2) . . ? C4 C5 H5A 119.6 . . ? C6 C5 H5A 119.6 . . ? C7 C6 C5 121.8(2) . . ? C7 C6 H6A 119.1 . . ? C5 C6 H6A 119.1 . . ? C6 C7 C8 117.5(2) . . ? C6 C7 H7A 121.2 . . ? C8 C7 H7A 121.2 . . ? N1 C8 C7 130.3(2) . . ? N1 C8 C3 107.6(2) . . ? C7 C8 C3 122.1(2) . . ? N1 C9 C10 114.85(19) . . ? N1 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? N1 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.5 . . ? C15 C10 C11 118.3(2) . . ? C15 C10 C9 122.8(2) . . ? C11 C10 C9 118.8(2) . . ? C10 C11 C12 121.0(3) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C12 119.2(3) . . ? C14 C13 H13A 120.4 . . ? C12 C13 H13A 120.4 . . ? C13 C14 C15 120.7(3) . . ? C13 C14 H14A 119.6 . . ? C15 C14 H14A 119.6 . . ? C10 C15 C14 120.5(3) . . ? C10 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? C1 C16 H16A 109.5 . . ? C1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C2 C17 C19 113.82(18) . . ? C2 C17 H17A 108.8 . . ? C19 C17 H17A 108.8 . . ? C2 C17 H17B 108.8 . . ? C19 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C19 C18 N2 109.52(19) . . ? C19 C18 C33 129.5(2) . . ? N2 C18 C33 121.0(2) . . ? C18 C19 C20 107.01(19) . . ? C18 C19 C17 127.0(2) . . ? C20 C19 C17 126.03(19) . . ? C21 C20 C25 118.4(2) . . ? C21 C20 C19 134.4(2) . . ? C25 C20 C19 107.14(18) . . ? C22 C21 C20 119.1(2) . . ? C22 C21 H21A 120.4 . . ? C20 C21 H21A 120.4 . . ? C21 C22 C23 121.3(2) . . ? C21 C22 H22A 119.3 . . ? C23 C22 H22A 119.3 . . ? C24 C23 C22 121.3(2) . . ? C24 C23 H23A 119.4 . . ? C22 C23 H23A 119.4 . . ? C23 C24 C25 117.3(2) . . ? C23 C24 H24A 121.4 . . ? C25 C24 H24A 121.4 . . ? N2 C25 C24 130.2(2) . . ? N2 C25 C20 107.24(19) . . ? C24 C25 C20 122.6(2) . . ? N2 C26 C27 114.51(17) . . ? N2 C26 H26A 108.6 . . ? C27 C26 H26A 108.6 . . ? N2 C26 H26B 108.6 . . ? C27 C26 H26B 108.6 . . ? H26A C26 H26B 107.6 . . ? C28 C27 C32 118.6(2) . . ? C28 C27 C26 123.44(19) . . ? C32 C27 C26 118.01(19) . . ? C27 C28 C29 120.5(2) . . ? C27 C28 H28A 119.8 . . ? C29 C28 H28A 119.8 . . ? C30 C29 C28 120.4(2) . . ? C30 C29 H29A 119.8 . . ? C28 C29 H29A 119.8 . . ? C31 C30 C29 119.2(2) . . ? C31 C30 H30A 120.4 . . ? C29 C30 H30A 120.4 . . ? C32 C31 C30 120.5(2) . . ? C32 C31 H31A 119.8 . . ? C30 C31 H31A 119.8 . . ? C31 C32 C27 120.9(2) . . ? C31 C32 H32A 119.5 . . ? C27 C32 H32A 119.5 . . ? C18 C33 H33A 109.5 . . ? C18 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C18 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? 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 N1 C8 1.374(3) . ? N1 C1 1.387(3) . ? N1 C9 1.456(3) . ? N2 C25 1.380(3) . ? N2 C18 1.387(3) . ? N2 C26 1.451(3) . ? C1 C2 1.367(3) . ? C1 C16 1.492(3) . ? C2 C3 1.435(3) . ? C2 C17 1.507(3) . ? C3 C4 1.401(3) . ? C3 C8 1.418(3) . ? C4 C5 1.387(3) . ? C4 H4A 0.9500 . ? C5 C6 1.400(4) . ? C5 H5A 0.9500 . ? C6 C7 1.376(4) . ? C6 H6A 0.9500 . ? C7 C8 1.392(3) . ? C7 H7A 0.9500 . ? C9 C10 1.516(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C15 1.380(4) . ? C10 C11 1.385(3) . ? C11 C12 1.387(4) . ? C11 H11A 0.9500 . ? C12 C13 1.376(5) . ? C12 H12A 0.9500 . ? C13 C14 1.374(5) . ? C13 H13A 0.9500 . ? C14 C15 1.390(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C19 1.509(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.367(3) . ? C18 C33 1.496(3) . ? C19 C20 1.436(3) . ? C20 C21 1.407(3) . ? C20 C25 1.417(3) . ? C21 C22 1.379(4) . ? C21 H21A 0.9500 . ? C22 C23 1.402(4) . ? C22 H22A 0.9500 . ? C23 C24 1.386(4) . ? C23 H23A 0.9500 . ? C24 C25 1.394(3) . ? C24 H24A 0.9500 . ? C26 C27 1.517(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.386(3) . ? C27 C32 1.393(3) . ? C28 C29 1.395(3) . ? C28 H28A 0.9500 . ? C29 C30 1.385(4) . ? C29 H29A 0.9500 . ? C30 C31 1.383(4) . ? C30 H30A 0.9500 . ? C31 C32 1.383(3) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? 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 C8 N1 C1 C2 0.7(3) . . . . ? C9 N1 C1 C2 176.90(19) . . . . ? C8 N1 C1 C16 -178.4(2) . . . . ? C9 N1 C1 C16 -2.2(3) . . . . ? N1 C1 C2 C3 0.0(2) . . . . ? C16 C1 C2 C3 179.0(2) . . . . ? N1 C1 C2 C17 -178.1(2) . . . . ? C16 C1 C2 C17 0.9(4) . . . . ? C1 C2 C3 C4 -178.3(2) . . . . ? C17 C2 C3 C4 -0.2(4) . . . . ? C1 C2 C3 C8 -0.7(2) . . . . ? C17 C2 C3 C8 177.49(19) . . . . ? C8 C3 C4 C5 -0.6(3) . . . . ? C2 C3 C4 C5 176.9(2) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C5 C6 C7 0.9(4) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? C1 N1 C8 C7 176.7(2) . . . . ? C9 N1 C8 C7 0.5(4) . . . . ? C1 N1 C8 C3 -1.1(2) . . . . ? C9 N1 C8 C3 -177.30(19) . . . . ? C6 C7 C8 N1 -178.2(2) . . . . ? C6 C7 C8 C3 -0.6(3) . . . . ? C4 C3 C8 N1 179.16(18) . . . . ? C2 C3 C8 N1 1.1(2) . . . . ? C4 C3 C8 C7 1.1(3) . . . . ? C2 C3 C8 C7 -176.96(19) . . . . ? C8 N1 C9 C10 -110.4(3) . . . . ? C1 N1 C9 C10 74.0(3) . . . . ? N1 C9 C10 C15 22.5(4) . . . . ? N1 C9 C10 C11 -159.6(2) . . . . ? C15 C10 C11 C12 -0.7(4) . . . . ? C9 C10 C11 C12 -178.6(2) . . . . ? C10 C11 C12 C13 0.6(4) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? C11 C10 C15 C14 0.5(4) . . . . ? C9 C10 C15 C14 178.4(3) . . . . ? C13 C14 C15 C10 -0.2(5) . . . . ? C1 C2 C17 C19 116.7(2) . . . . ? C3 C2 C17 C19 -61.1(3) . . . . ? C25 N2 C18 C19 0.6(2) . . . . ? C26 N2 C18 C19 -178.92(19) . . . . ? C25 N2 C18 C33 -179.49(19) . . . . ? C26 N2 C18 C33 1.0(3) . . . . ? N2 C18 C19 C20 -0.4(2) . . . . ? C33 C18 C19 C20 179.7(2) . . . . ? N2 C18 C19 C17 178.55(19) . . . . ? C33 C18 C19 C17 -1.3(4) . . . . ? C2 C17 C19 C18 -64.7(3) . . . . ? C2 C17 C19 C20 114.1(2) . . . . ? C18 C19 C20 C21 -178.4(2) . . . . ? C17 C19 C20 C21 2.6(4) . . . . ? C18 C19 C20 C25 0.1(2) . . . . ? C17 C19 C20 C25 -178.9(2) . . . . ? C25 C20 C21 C22 0.4(3) . . . . ? C19 C20 C21 C22 178.8(2) . . . . ? C20 C21 C22 C23 0.4(3) . . . . ? C21 C22 C23 C24 -0.9(4) . . . . ? C22 C23 C24 C25 0.5(3) . . . . ? C18 N2 C25 C24 179.4(2) . . . . ? C26 N2 C25 C24 -1.1(3) . . . . ? C18 N2 C25 C20 -0.5(2) . . . . ? C26 N2 C25 C20 179.01(18) . . . . ? C23 C24 C25 N2 -179.5(2) . . . . ? C23 C24 C25 C20 0.4(3) . . . . ? C21 C20 C25 N2 179.05(18) . . . . ? C19 C20 C25 N2 0.2(2) . . . . ? C21 C20 C25 C24 -0.8(3) . . . . ? C19 C20 C25 C24 -179.64(19) . . . . ? C25 N2 C26 C27 96.5(2) . . . . ? C18 N2 C26 C27 -84.0(3) . . . . ? N2 C26 C27 C28 -8.5(3) . . . . ? N2 C26 C27 C32 171.71(19) . . . . ? C32 C27 C28 C29 0.5(3) . . . . ? C26 C27 C28 C29 -179.4(2) . . . . ? C27 C28 C29 C30 0.1(4) . . . . ? C28 C29 C30 C31 -0.4(4) . . . . ? C29 C30 C31 C32 0.2(4) . . . . ? C30 C31 C32 C27 0.4(3) . . . . ? C28 C27 C32 C31 -0.7(3) . . . . ? C26 C27 C32 C31 179.1(2) . . . . ?