#------------------------------------------------------------------------------ #$Date: 2019-10-07 12:37:42 +0300 (Mon, 07 Oct 2019) $ #$Revision: 219131 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234423.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_7234423 loop_ _publ_author_name 'Liang Xu' 'Hai Zhu' 'Guankui Long' 'Jun Zhao' 'Dongsheng Li' 'Rakesh Ganguly' 'Yongxin Li' 'Qing-Hua Xu' 'Qichun Zhang' _publ_section_title ; 4-Diphenylamino-phenyl substituted pyrazine: nonlinear optical switching by protonation ; _journal_name_full 'Journal of Materials Chemistry C' _journal_page_first 9191 _journal_page_last 9196 _journal_paper_doi 10.1039/C5TC01657F _journal_volume 3 _journal_year 2015 _chemical_formula_sum 'C46 H36 N4' _chemical_formula_weight 644.79 _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 _cell_angle_alpha 90 _cell_angle_beta 93.751(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.3955(13) _cell_length_b 19.271(4) _cell_length_c 28.780(6) _cell_measurement_reflns_used 1330 _cell_measurement_temperature 103.(2) _cell_measurement_theta_max 20.8933 _cell_measurement_theta_min 2.3756 _cell_volume 3539.5(13) _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_collection 'APEX2 (Bruker AXS Inc., 2014)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_molecular_graphics 'XP (Bruker AXS Inc., 2014)' _computing_publication_material 'APEX2 (Bruker AXS Inc., 2014)' _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' _diffrn_ambient_temperature 103.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.2003 _diffrn_reflns_av_unetI/netI 0.2410 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 26250 _diffrn_reflns_theta_full 25.74 _diffrn_reflns_theta_max 25.74 _diffrn_reflns_theta_min 2.11 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/4 (Bruker AXS Inc.)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1360 _exptl_crystal_size_max 0.420 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.247 _refine_diff_density_min -0.281 _refine_ls_extinction_coef 0.0057(5) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 454 _refine_ls_number_reflns 6729 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.977 _refine_ls_R_factor_all 0.2386 _refine_ls_R_factor_gt 0.0827 _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^)+(0.0514P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1344 _refine_ls_wR_factor_ref 0.1827 _reflns_number_gt 2584 _reflns_number_total 6729 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file J-Mater-Chem-C-2015-3-9191.cif _cod_data_source_block II _cod_original_cell_volume 3539.5(12) _cod_database_code 7234423 _shelx_res_file ; TITL zqc2 in P2(1)/c CELL 0.71073 6.39550 19.27140 28.77970 90.0000 93.7506 90.0000 ZERR 4.00 0.00130 0.00380 0.00550 0.0000 0.0055 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N UNIT 184 144 16 omit 0 1 3 omit 0 2 1 omit 0 1 2 omit 0 0 2 L.S. 6 ACTA BOND FMAP 2 PLAN 5 SIZE 0.060 0.120 0.420 TEMP -170 WGHT 0.051400 EXTI 0.005725 FVAR 0.12498 MOLE 1 C1 1 0.207315 0.425129 0.406816 11.00000 0.04735 0.01953 = 0.02552 -0.00036 -0.00370 -0.00388 C2 1 0.004434 0.437138 0.417882 11.00000 0.05331 0.02721 = 0.02229 -0.00047 0.00030 -0.00406 AFIX 43 H2 2 -0.096816 0.453265 0.394756 11.00000 -1.20000 AFIX 0 C3 1 -0.052188 0.425415 0.463590 11.00000 0.04824 0.03418 = 0.03288 -0.00588 0.00827 -0.00167 AFIX 43 H3 2 -0.191672 0.433975 0.471566 11.00000 -1.20000 AFIX 0 C4 1 0.095663 0.401407 0.496867 11.00000 0.06992 0.02941 = 0.01979 0.00074 0.00350 -0.00778 AFIX 43 H4 2 0.057896 0.393723 0.527830 11.00000 -1.20000 AFIX 0 C5 1 0.296329 0.388649 0.485407 11.00000 0.06239 0.02900 = 0.03048 0.00380 -0.00052 0.00569 AFIX 43 H5 2 0.396871 0.371496 0.508331 11.00000 -1.20000 AFIX 0 C6 1 0.354054 0.400773 0.440033 11.00000 0.04099 0.03451 = 0.03284 0.00234 0.00533 0.00063 AFIX 43 H6 2 0.493738 0.392246 0.432184 11.00000 -1.20000 AFIX 0 C7 1 0.168663 0.410176 0.321155 11.00000 0.04498 0.02946 = 0.02189 -0.00343 -0.00018 -0.00218 C8 1 0.072641 0.345896 0.324403 11.00000 0.05931 0.02390 = 0.03195 -0.00058 0.00142 -0.00100 AFIX 43 H8 2 0.079602 0.321853 0.353280 11.00000 -1.20000 AFIX 0 C9 1 -0.033096 0.316763 0.285736 11.00000 0.06052 0.03092 = 0.04418 -0.00665 0.01015 -0.00631 AFIX 43 H9 2 -0.099640 0.273008 0.288437 11.00000 -1.20000 AFIX 0 C10 1 -0.043386 0.350325 0.243261 11.00000 0.06198 0.04549 = 0.03583 -0.01366 -0.00183 -0.00885 AFIX 43 H10 2 -0.115830 0.330000 0.216785 11.00000 -1.20000 AFIX 0 C11 1 0.054436 0.414530 0.239968 11.00000 0.06199 0.04391 = 0.02449 -0.00546 0.00266 0.00339 AFIX 43 H11 2 0.048522 0.438331 0.211004 11.00000 -1.20000 AFIX 0 C12 1 0.159796 0.443799 0.278438 11.00000 0.06626 0.03096 = 0.02101 -0.00204 0.00249 0.00020 AFIX 43 H12 2 0.227008 0.487428 0.275675 11.00000 -1.20000 AFIX 0 C13 1 0.441671 0.488012 0.357690 11.00000 0.03994 0.02929 = 0.02231 0.00323 0.00476 -0.00455 C14 1 0.462534 0.543986 0.389115 11.00000 0.04162 0.03337 = 0.02186 0.00348 0.00388 0.00032 AFIX 43 H14 2 0.365205 0.549759 0.412375 11.00000 -1.20000 AFIX 0 C15 1 0.625268 0.590382 0.385896 11.00000 0.04891 0.02493 = 0.01503 0.00215 0.00007 -0.00277 AFIX 43 H15 2 0.642304 0.626614 0.408205 11.00000 -1.20000 AFIX 0 C16 1 0.765321 0.585734 0.350950 11.00000 0.03838 0.02484 = 0.01963 0.00468 -0.00230 0.00122 C17 1 0.740141 0.529795 0.320096 11.00000 0.03496 0.02739 = 0.02142 -0.00244 0.01043 0.00102 AFIX 43 H17 2 0.833061 0.524998 0.295858 11.00000 -1.20000 AFIX 0 C18 1 0.584086 0.481722 0.324103 11.00000 0.04572 0.02378 = 0.02420 -0.00203 0.00707 -0.00220 AFIX 43 H18 2 0.574174 0.443398 0.303313 11.00000 -1.20000 AFIX 0 C19 1 0.942052 0.636314 0.349505 11.00000 0.03781 0.02598 = 0.01941 0.00212 0.00123 0.00586 C20 1 1.023538 0.658371 0.306268 11.00000 0.03825 0.02331 = 0.01613 -0.00193 0.00149 0.00756 C21 1 1.287283 0.716507 0.347906 11.00000 0.04503 0.02243 = 0.01532 -0.00189 0.00178 0.00439 C22 1 1.469412 0.758303 0.348832 11.00000 0.04529 0.02299 = 0.02391 -0.00222 0.00491 -0.00076 AFIX 43 H22 2 1.527935 0.770569 0.320464 11.00000 -1.20000 AFIX 0 C23 1 1.563213 0.781512 0.390775 11.00000 0.04566 0.02309 = 0.03202 -0.00332 0.00053 0.00198 C24 1 1.756021 0.826390 0.390748 11.00000 0.05189 0.03603 = 0.04064 -0.00506 0.00267 -0.00763 AFIX 137 H24A 2 1.727349 0.871450 0.404777 11.00000 -1.50000 H24B 2 1.794318 0.833277 0.358653 11.00000 -1.50000 H24C 2 1.871846 0.803641 0.408798 11.00000 -1.50000 AFIX 0 C25 1 1.470648 0.763765 0.432963 11.00000 0.04600 0.02419 = 0.02463 -0.00239 -0.00290 0.00292 C26 1 1.576254 0.788607 0.478724 11.00000 0.06613 0.03038 = 0.03129 -0.00392 -0.00913 -0.00386 AFIX 137 H26A 2 1.490256 0.775760 0.504342 11.00000 -1.50000 H26B 2 1.592075 0.839164 0.477898 11.00000 -1.50000 H26C 2 1.714622 0.766936 0.483482 11.00000 -1.50000 AFIX 0 C27 1 1.295554 0.723934 0.432255 11.00000 0.04027 0.02967 = 0.01592 -0.00162 0.00347 0.00224 AFIX 43 H27 2 1.237101 0.712353 0.460757 11.00000 -1.20000 AFIX 0 C28 1 1.197935 0.699204 0.389614 11.00000 0.03284 0.02353 = 0.02000 -0.00008 -0.00141 0.00505 C29 1 0.914716 0.643597 0.259834 11.00000 0.05207 0.01824 = 0.01932 0.00062 0.00120 -0.00652 C30 1 0.702958 0.656475 0.251343 11.00000 0.04519 0.02892 = 0.01908 0.00403 0.00746 -0.00018 AFIX 43 H30 2 0.623169 0.672444 0.275917 11.00000 -1.20000 AFIX 0 C31 1 0.605009 0.646280 0.207063 11.00000 0.03922 0.02817 = 0.02498 -0.00236 0.00109 -0.00034 AFIX 43 H31 2 0.460675 0.656988 0.201243 11.00000 -1.20000 AFIX 0 C32 1 0.720060 0.620352 0.171529 11.00000 0.04854 0.02305 = 0.01430 0.00072 0.00356 -0.00055 C33 1 0.931069 0.607487 0.179852 11.00000 0.05017 0.02939 = 0.02397 0.00345 0.00348 0.00324 AFIX 43 H33 2 1.010488 0.590951 0.155377 11.00000 -1.20000 AFIX 0 C34 1 1.028517 0.618535 0.223801 11.00000 0.04505 0.02147 = 0.02491 0.00184 -0.00401 -0.00576 AFIX 43 H34 2 1.173723 0.608922 0.229290 11.00000 -1.20000 AFIX 0 C35 1 0.672882 0.544886 0.103417 11.00000 0.05457 0.02146 = 0.01919 -0.00035 -0.00179 -0.00014 C36 1 0.692991 0.546041 0.055497 11.00000 0.05605 0.02659 = 0.02403 -0.00254 -0.00340 0.00006 AFIX 43 H36 2 0.666474 0.587554 0.038309 11.00000 -1.20000 AFIX 0 C37 1 0.751980 0.486152 0.033106 11.00000 0.05647 0.03700 = 0.02765 -0.00879 0.00126 0.00112 AFIX 43 H37 2 0.767148 0.487221 0.000497 11.00000 -1.20000 AFIX 0 C38 1 0.789092 0.425068 0.057184 11.00000 0.05878 0.03065 = 0.03829 -0.00989 -0.00625 0.00696 AFIX 43 H38 2 0.828420 0.384293 0.041384 11.00000 -1.20000 AFIX 0 C39 1 0.768202 0.424098 0.104607 11.00000 0.06600 0.02473 = 0.03486 -0.00129 -0.00896 -0.00170 AFIX 43 H39 2 0.795133 0.382469 0.121639 11.00000 -1.20000 AFIX 0 C40 1 0.708343 0.483265 0.127573 11.00000 0.05660 0.02651 = 0.02479 -0.00080 0.00112 -0.00229 AFIX 43 H40 2 0.691431 0.481654 0.160105 11.00000 -1.20000 AFIX 0 C41 1 0.455017 0.650054 0.108647 11.00000 0.04354 0.02585 = 0.02067 0.00162 -0.00102 0.00292 C42 1 0.461582 0.722307 0.116321 11.00000 0.04600 0.02846 = 0.03126 -0.00462 0.00363 -0.00245 AFIX 43 H42 2 0.579097 0.742452 0.133149 11.00000 -1.20000 AFIX 0 C43 1 0.299427 0.763528 0.099635 11.00000 0.05527 0.02976 = 0.03114 0.00551 0.00902 0.01029 AFIX 43 H43 2 0.302371 0.811729 0.106564 11.00000 -1.20000 AFIX 0 C44 1 0.130508 0.736314 0.072755 11.00000 0.05327 0.03775 = 0.02904 0.00670 0.00186 0.00955 AFIX 43 H44 2 0.020728 0.765790 0.060793 11.00000 -1.20000 AFIX 0 C45 1 0.123948 0.666388 0.063670 11.00000 0.04560 0.04852 = 0.02126 -0.00369 -0.00318 -0.00222 AFIX 43 H45 2 0.009913 0.647108 0.045174 11.00000 -1.20000 AFIX 0 C46 1 0.285736 0.623872 0.081767 11.00000 0.04237 0.03194 = 0.02562 -0.00045 0.00585 -0.00075 AFIX 43 H46 2 0.279635 0.575500 0.075466 11.00000 -1.20000 AFIX 0 N1 3 0.271859 0.440441 0.361185 11.00000 0.05558 0.04006 = 0.01169 -0.00035 0.00437 -0.01127 N2 3 1.025937 0.657624 0.390383 11.00000 0.04487 0.02238 = 0.01911 -0.00172 -0.00146 -0.00200 N3 3 1.195853 0.696232 0.305838 11.00000 0.04164 0.02587 = 0.02142 0.00004 0.00092 -0.00053 N4 3 0.618873 0.606761 0.126766 11.00000 0.05559 0.02823 = 0.01504 -0.00260 -0.00118 0.00597 HKLF 4 REM zqc2 in P2(1)/c REM R1 = 0.0827 for 2584 Fo > 4sig(Fo) and 0.2386 for all 6729 data REM 454 parameters refined using 0 restraints END WGHT 0.0513 0.0000 REM Highest difference peak 0.247, deepest hole -0.281, 1-sigma level 0.059 Q1 1 0.5782 0.4800 0.3606 11.00000 0.05 0.25 Q2 1 0.5984 0.6476 0.1093 11.00000 0.05 0.22 Q3 1 0.2256 0.3026 0.3810 11.00000 0.05 0.22 Q4 1 0.6321 0.5768 0.1122 11.00000 0.05 0.22 Q5 1 0.8389 0.5195 0.1086 11.00000 0.05 0.22 ; _shelx_res_checksum 11781 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_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.2073(9) 0.4251(2) 0.40682(16) 0.0311(13) Uani d . . . 1 . . C C2 0.0044(9) 0.4371(2) 0.41788(16) 0.0344(13) Uani d . . . 1 . . H H2 -0.0968 0.4533 0.3948 0.041 Uiso calc U . R 1 . . C C3 -0.0522(9) 0.4254(2) 0.46359(16) 0.0382(14) Uani d . . . 1 . . H H3 -0.1917 0.434 0.4716 0.046 Uiso calc U . R 1 . . C C4 0.0957(9) 0.4014(2) 0.49687(17) 0.0397(15) Uani d . . . 1 . . H H4 0.0579 0.3937 0.5278 0.048 Uiso calc U . R 1 . . C C5 0.2963(9) 0.3886(2) 0.48541(17) 0.0408(15) Uani d . . . 1 . . H H5 0.3969 0.3715 0.5083 0.049 Uiso calc U . R 1 . . C C6 0.3541(8) 0.4008(2) 0.44003(16) 0.0360(13) Uani d . . . 1 . . H H6 0.4937 0.3922 0.4322 0.043 Uiso calc U . R 1 . . C C7 0.1687(8) 0.4102(2) 0.32115(15) 0.0322(13) Uani d . . . 1 . . C C8 0.0726(8) 0.3459(2) 0.32440(17) 0.0385(14) Uani d . . . 1 . . H H8 0.0796 0.3219 0.3533 0.046 Uiso calc U . R 1 . . C C9 -0.0331(9) 0.3168(2) 0.28574(17) 0.0449(15) Uani d . . . 1 . . H H9 -0.0996 0.273 0.2884 0.054 Uiso calc U . R 1 . . C C10 -0.0434(9) 0.3503(2) 0.24326(17) 0.0480(16) Uani d . . . 1 . . H H10 -0.1158 0.33 0.2168 0.058 Uiso calc U . R 1 . . C C11 0.0544(8) 0.4145(2) 0.23997(16) 0.0435(15) Uani d . . . 1 . . H H11 0.0485 0.4383 0.211 0.052 Uiso calc U . R 1 . . C C12 0.1598(9) 0.4438(2) 0.27844(15) 0.0394(15) Uani d . . . 1 . . H H12 0.227 0.4874 0.2757 0.047 Uiso calc U . R 1 . . C C13 0.4417(8) 0.4880(2) 0.35769(16) 0.0304(13) Uani d . . . 1 . . C C14 0.4625(8) 0.5440(2) 0.38911(15) 0.0322(13) Uani d . . . 1 . . H H14 0.3652 0.5498 0.4124 0.039 Uiso calc U . R 1 . . C C15 0.6253(8) 0.5904(2) 0.38590(15) 0.0297(13) Uani d . . . 1 . . H H15 0.6423 0.6266 0.4082 0.036 Uiso calc U . R 1 . . C C16 0.7653(8) 0.5857(2) 0.35095(15) 0.0278(12) Uani d . . . 1 . . C C17 0.7401(7) 0.5298(2) 0.32010(15) 0.0275(12) Uani d . . . 1 . . H H17 0.8331 0.525 0.2959 0.033 Uiso calc U . R 1 . . C C18 0.5841(8) 0.4817(2) 0.32410(15) 0.0310(13) Uani d . . . 1 . . H H18 0.5742 0.4434 0.3033 0.037 Uiso calc U . R 1 . . C C19 0.9421(8) 0.6363(2) 0.34951(15) 0.0278(12) Uani d . . . 1 . . C C20 1.0235(8) 0.6584(2) 0.30627(15) 0.0259(12) Uani d . . . 1 . . C C21 1.2873(8) 0.7165(2) 0.34791(15) 0.0276(12) Uani d . . . 1 . . C C22 1.4694(8) 0.7583(2) 0.34883(16) 0.0306(13) Uani d . . . 1 . . H H22 1.5279 0.7706 0.3205 0.037 Uiso calc U . R 1 . . C C23 1.5632(8) 0.7815(2) 0.39077(16) 0.0337(13) Uani d . . . 1 . . C C24 1.7560(8) 0.8264(2) 0.39075(16) 0.0429(15) Uani d . . . 1 . . H H24A 1.7273 0.8715 0.4048 0.064 Uiso calc U . R 1 . . H H24B 1.7943 0.8333 0.3587 0.064 Uiso calc U . R 1 . . H H24C 1.8718 0.8036 0.4088 0.064 Uiso calc U . R 1 . . C C25 1.4706(8) 0.7638(2) 0.43296(16) 0.0318(13) Uani d . . . 1 . . C C26 1.5763(8) 0.7886(2) 0.47872(15) 0.0431(15) Uani d . . . 1 . . H H26A 1.4903 0.7758 0.5043 0.065 Uiso calc U . R 1 . . H H26B 1.5921 0.8392 0.4779 0.065 Uiso calc U . R 1 . . H H26C 1.7146 0.7669 0.4835 0.065 Uiso calc U . R 1 . . C C27 1.2956(8) 0.7239(2) 0.43226(15) 0.0285(12) Uani d . . . 1 . . H H27 1.2371 0.7124 0.4608 0.034 Uiso calc U . R 1 . . C C28 1.1979(8) 0.6992(2) 0.38961(15) 0.0256(12) Uani d . . . 1 . . C C29 0.9147(9) 0.6436(2) 0.25983(15) 0.0299(13) Uani d . . . 1 . . C C30 0.7030(8) 0.6565(2) 0.25134(15) 0.0308(13) Uani d . . . 1 . . H H30 0.6232 0.6724 0.2759 0.037 Uiso calc U . R 1 . . C C31 0.6050(8) 0.6463(2) 0.20706(15) 0.0308(13) Uani d . . . 1 . . H H31 0.4607 0.657 0.2012 0.037 Uiso calc U . R 1 . . C C32 0.7201(9) 0.6204(2) 0.17153(15) 0.0286(13) Uani d . . . 1 . . C C33 0.9311(8) 0.6075(2) 0.17985(16) 0.0345(13) Uani d . . . 1 . . H H33 1.0105 0.591 0.1554 0.041 Uiso calc U . R 1 . . C C34 1.0285(8) 0.6185(2) 0.22380(15) 0.0308(13) Uani d . . . 1 . . H H34 1.1737 0.6089 0.2293 0.037 Uiso calc U . R 1 . . C C35 0.6729(8) 0.5449(2) 0.10342(15) 0.0319(13) Uani d . . . 1 . . C C36 0.6930(8) 0.5460(2) 0.05550(15) 0.0358(14) Uani d . . . 1 . . H H36 0.6665 0.5876 0.0383 0.043 Uiso calc U . R 1 . . C C37 0.7520(8) 0.4862(2) 0.03311(17) 0.0404(14) Uani d . . . 1 . . H H37 0.7671 0.4872 0.0005 0.049 Uiso calc U . R 1 . . C C38 0.7891(8) 0.4251(2) 0.05718(17) 0.0430(15) Uani d . . . 1 . . H H38 0.8284 0.3843 0.0414 0.052 Uiso calc U . R 1 . . C C39 0.7682(8) 0.4241(2) 0.10461(17) 0.0424(15) Uani d . . . 1 . . H H39 0.7951 0.3825 0.1216 0.051 Uiso calc U . R 1 . . C C40 0.7083(8) 0.4833(2) 0.12757(16) 0.0360(14) Uani d . . . 1 . . H H40 0.6914 0.4817 0.1601 0.043 Uiso calc U . R 1 . . C C41 0.4550(8) 0.6501(2) 0.10865(15) 0.0302(13) Uani d . . . 1 . . C C42 0.4616(8) 0.7223(2) 0.11632(15) 0.0352(13) Uani d . . . 1 . . H H42 0.5791 0.7425 0.1331 0.042 Uiso calc U . R 1 . . C C43 0.2994(9) 0.7635(2) 0.09963(16) 0.0385(14) Uani d . . . 1 . . H H43 0.3024 0.8117 0.1066 0.046 Uiso calc U . R 1 . . C C44 0.1305(9) 0.7363(2) 0.07276(16) 0.0401(14) Uani d . . . 1 . . H H44 0.0207 0.7658 0.0608 0.048 Uiso calc U . R 1 . . C C45 0.1239(8) 0.6664(2) 0.06367(16) 0.0387(14) Uani d . . . 1 . . H H45 0.0099 0.6471 0.0452 0.046 Uiso calc U . R 1 . . C C46 0.2857(8) 0.6239(2) 0.08177(15) 0.0332(13) Uani d . . . 1 . . H H46 0.2796 0.5755 0.0755 0.04 Uiso calc U . R 1 . . N N1 0.2719(7) 0.44044(18) 0.36118(12) 0.0357(11) Uani d . . . 1 . . N N2 1.0259(6) 0.65762(17) 0.39038(12) 0.0289(10) Uani d . . . 1 . . N N3 1.1959(7) 0.69623(17) 0.30584(12) 0.0297(10) Uani d . . . 1 . . N N4 0.6189(7) 0.60676(17) 0.12677(12) 0.0331(11) Uani d . . . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.047(4) 0.020(2) 0.026(3) -0.004(3) -0.004(3) 0.000(2) C2 0.053(4) 0.027(3) 0.022(3) -0.004(3) 0.000(3) 0.000(2) C3 0.048(4) 0.034(3) 0.033(3) -0.002(3) 0.008(3) -0.006(2) C4 0.070(5) 0.029(3) 0.020(3) -0.008(3) 0.003(3) 0.001(2) C5 0.062(4) 0.029(3) 0.030(3) 0.006(3) -0.001(3) 0.004(2) C6 0.041(4) 0.035(3) 0.033(3) 0.001(3) 0.005(3) 0.002(2) C7 0.045(4) 0.029(3) 0.022(3) -0.002(3) 0.000(3) -0.003(2) C8 0.059(4) 0.024(3) 0.032(3) -0.001(3) 0.001(3) -0.001(2) C9 0.061(4) 0.031(3) 0.044(3) -0.006(3) 0.010(3) -0.007(3) C10 0.062(5) 0.045(3) 0.036(3) -0.009(3) -0.002(3) -0.014(3) C11 0.062(4) 0.044(3) 0.024(3) 0.003(3) 0.003(3) -0.005(2) C12 0.066(4) 0.031(3) 0.021(3) 0.000(3) 0.002(3) -0.002(2) C13 0.040(4) 0.029(3) 0.022(3) -0.005(3) 0.005(3) 0.003(2) C14 0.042(4) 0.033(3) 0.022(3) 0.000(3) 0.004(3) 0.003(2) C15 0.049(4) 0.025(2) 0.015(3) -0.003(3) 0.000(3) 0.002(2) C16 0.038(4) 0.025(2) 0.020(3) 0.001(2) -0.002(3) 0.005(2) C17 0.035(3) 0.027(2) 0.021(3) 0.001(2) 0.010(3) -0.002(2) C18 0.046(4) 0.024(2) 0.024(3) -0.002(3) 0.007(3) -0.002(2) C19 0.038(4) 0.026(3) 0.019(3) 0.006(2) 0.001(3) 0.002(2) C20 0.038(4) 0.023(2) 0.016(3) 0.008(2) 0.001(3) -0.002(2) C21 0.045(4) 0.022(2) 0.015(3) 0.004(2) 0.002(3) -0.002(2) C22 0.045(4) 0.023(2) 0.024(3) -0.001(3) 0.005(3) -0.002(2) C23 0.046(4) 0.023(2) 0.032(3) 0.002(3) 0.001(3) -0.003(2) C24 0.052(4) 0.036(3) 0.041(3) -0.008(3) 0.003(3) -0.005(2) C25 0.046(4) 0.024(2) 0.025(3) 0.003(3) -0.003(3) -0.002(2) C26 0.066(4) 0.030(3) 0.031(3) -0.004(3) -0.009(3) -0.004(2) C27 0.040(4) 0.030(2) 0.016(3) 0.002(3) 0.003(3) -0.002(2) C28 0.033(3) 0.024(2) 0.020(3) 0.005(2) -0.001(3) 0.000(2) C29 0.052(4) 0.018(2) 0.019(3) -0.007(3) 0.001(3) 0.001(2) C30 0.045(4) 0.029(3) 0.019(3) 0.000(3) 0.007(3) 0.004(2) C31 0.039(4) 0.028(2) 0.025(3) 0.000(2) 0.001(3) -0.002(2) C32 0.049(4) 0.023(2) 0.014(3) -0.001(3) 0.004(3) 0.001(2) C33 0.050(4) 0.029(3) 0.024(3) 0.003(3) 0.003(3) 0.003(2) C34 0.045(4) 0.021(2) 0.025(3) -0.006(2) -0.004(3) 0.002(2) C35 0.055(4) 0.021(2) 0.019(3) 0.000(3) -0.002(3) 0.000(2) C36 0.056(4) 0.027(2) 0.024(3) 0.000(3) -0.003(3) -0.003(2) C37 0.056(4) 0.037(3) 0.028(3) 0.001(3) 0.001(3) -0.009(2) C38 0.059(4) 0.031(3) 0.038(3) 0.007(3) -0.006(3) -0.010(2) C39 0.066(4) 0.025(3) 0.035(3) -0.002(3) -0.009(3) -0.001(2) C40 0.057(4) 0.027(2) 0.025(3) -0.002(3) 0.001(3) -0.001(2) C41 0.044(4) 0.026(3) 0.021(3) 0.003(3) -0.001(3) 0.002(2) C42 0.046(4) 0.028(3) 0.031(3) -0.002(3) 0.004(3) -0.005(2) C43 0.055(4) 0.030(3) 0.031(3) 0.010(3) 0.009(3) 0.006(2) C44 0.053(4) 0.038(3) 0.029(3) 0.010(3) 0.002(3) 0.007(2) C45 0.046(4) 0.049(3) 0.021(3) -0.002(3) -0.003(3) -0.004(2) C46 0.042(4) 0.032(3) 0.026(3) -0.001(3) 0.006(3) 0.000(2) N1 0.056(3) 0.040(2) 0.012(2) -0.011(2) 0.004(2) -0.0003(18) N2 0.045(3) 0.022(2) 0.019(2) -0.002(2) -0.001(2) -0.0017(17) N3 0.042(3) 0.026(2) 0.021(2) -0.001(2) 0.001(2) 0.0000(17) N4 0.056(3) 0.028(2) 0.015(2) 0.006(2) -0.001(2) -0.0026(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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C2 C1 C6 . . 120.4(5) C2 C1 N1 . . 120.7(5) C6 C1 N1 . . 118.8(5) C1 C2 C3 . . 119.6(5) C4 C3 C2 . . 119.8(5) C5 C4 C3 . . 120.2(5) C4 C5 C6 . . 120.2(5) C1 C6 C5 . . 119.7(5) C12 C7 C8 . . 118.9(4) C12 C7 N1 . . 121.2(4) C8 C7 N1 . . 119.8(4) C9 C8 C7 . . 120.2(5) C10 C9 C8 . . 121.0(5) C9 C10 C11 . . 118.7(5) C12 C11 C10 . . 120.5(5) C11 C12 C7 . . 120.7(5) C18 C13 C14 . . 118.6(4) C18 C13 N1 . . 122.2(4) C14 C13 N1 . . 119.1(4) C15 C14 C13 . . 119.6(5) C14 C15 C16 . . 122.0(4) C15 C16 C17 . . 117.1(4) C15 C16 C19 . . 120.1(4) C17 C16 C19 . . 122.7(4) C18 C17 C16 . . 121.4(4) C17 C18 C13 . . 121.2(4) N2 C19 C20 . . 121.7(4) N2 C19 C16 . . 116.1(4) C20 C19 C16 . . 122.1(4) N3 C20 C19 . . 121.2(4) N3 C20 C29 . . 115.9(4) C19 C20 C29 . . 122.8(5) N3 C21 C28 . . 121.0(4) N3 C21 C22 . . 118.9(4) C28 C21 C22 . . 120.0(4) C23 C22 C21 . . 120.6(5) C22 C23 C25 . . 118.9(5) C22 C23 C24 . . 119.5(5) C25 C23 C24 . . 121.6(4) C27 C25 C23 . . 120.7(4) C27 C25 C26 . . 120.8(5) C23 C25 C26 . . 118.5(5) C25 C27 C28 . . 121.2(5) N2 C28 C21 . . 121.9(4) N2 C28 C27 . . 119.5(4) C21 C28 C27 . . 118.6(4) C30 C29 C34 . . 119.0(4) C30 C29 C20 . . 121.2(5) C34 C29 C20 . . 119.8(5) C29 C30 C31 . . 120.8(5) C32 C31 C30 . . 119.6(5) C33 C32 C31 . . 119.7(4) C33 C32 N4 . . 120.3(4) C31 C32 N4 . . 119.9(5) C32 C33 C34 . . 120.4(5) C33 C34 C29 . . 120.4(5) C40 C35 C36 . . 119.1(4) C40 C35 N4 . . 121.2(4) C36 C35 N4 . . 119.7(4) C37 C36 C35 . . 119.5(4) C38 C37 C36 . . 121.4(4) C37 C38 C39 . . 118.9(4) C38 C39 C40 . . 120.6(4) C39 C40 C35 . . 120.5(4) C46 C41 C42 . . 117.5(5) C46 C41 N4 . . 121.7(4) C42 C41 N4 . . 120.8(5) C43 C42 C41 . . 120.3(5) C42 C43 C44 . . 121.3(5) C45 C44 C43 . . 119.3(5) C44 C45 C46 . . 119.5(5) C41 C46 C45 . . 121.9(4) C7 N1 C13 . . 121.5(4) C7 N1 C1 . . 120.9(4) C13 N1 C1 . . 117.5(4) C19 N2 C28 . . 116.6(4) C20 N3 C21 . . 117.3(4) C41 N4 C35 . . 121.2(4) C41 N4 C32 . . 120.4(4) C35 N4 C32 . . 118.1(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance C1 C2 . 1.376(6) C1 C6 . 1.378(6) C1 N1 . 1.433(5) C2 C3 . 1.405(6) C3 C4 . 1.381(6) C4 C5 . 1.368(7) C5 C6 . 1.400(6) C7 C12 . 1.388(6) C7 C8 . 1.388(6) C7 N1 . 1.415(5) C8 C9 . 1.383(6) C9 C10 . 1.381(6) C10 C11 . 1.393(6) C11 C12 . 1.379(6) C13 C18 . 1.376(6) C13 C14 . 1.408(5) C13 N1 . 1.430(6) C14 C15 . 1.380(6) C15 C16 . 1.393(6) C16 C17 . 1.399(5) C16 C19 . 1.495(6) C17 C18 . 1.372(6) C19 N2 . 1.326(5) C19 C20 . 1.444(6) C20 N3 . 1.322(6) C20 C29 . 1.493(6) C21 N3 . 1.367(5) C21 C28 . 1.403(6) C21 C22 . 1.415(6) C22 C23 . 1.386(6) C23 C25 . 1.427(6) C23 C24 . 1.506(6) C25 C27 . 1.357(6) C25 C26 . 1.518(6) C27 C28 . 1.422(6) C28 N2 . 1.362(6) C29 C30 . 1.383(6) C29 C34 . 1.392(6) C30 C31 . 1.397(6) C31 C32 . 1.391(6) C32 C33 . 1.378(6) C32 N4 . 1.428(5) C33 C34 . 1.389(6) C35 C40 . 1.387(5) C35 C36 . 1.394(6) C35 N4 . 1.422(5) C36 C37 . 1.386(5) C37 C38 . 1.379(6) C38 C39 . 1.380(6) C39 C40 . 1.384(5) C41 C46 . 1.384(6) C41 C42 . 1.410(5) C41 N4 . 1.412(5) C42 C43 . 1.368(6) C43 C44 . 1.390(6) C44 C45 . 1.373(6) C45 C46 . 1.394(6)