#------------------------------------------------------------------------------ #$Date: 2018-03-13 08:43:31 +0200 (Tue, 13 Mar 2018) $ #$Revision: 206927 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/90/1549064.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_1549064 loop_ _publ_author_name 'Andrews, M. Crawford' 'Peng, Ping' 'Rajput, Amit' 'Cozzolino, Anthony F.' _publ_section_title ; Modulation of the carboxamidine redox potential through photoinduced spiropyran or fulgimide isomerisation ; _journal_name_full 'Photochemical & Photobiological Sciences' _journal_paper_doi 10.1039/C7PP00347A _journal_year 2018 _chemical_formula_sum 'C35 H35 N4 O2' _chemical_formula_weight 543.67 _chemical_properties_physical ', Photo-sensitive' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2016-06-14T10:08:10-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2017-05-09 deposited with the CCDC. 2018-03-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.450(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 19.675(11) _cell_length_b 16.984(10) _cell_length_c 8.859(5) _cell_measurement_reflns_used 1390 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 19.64 _cell_measurement_theta_min 2.40 _cell_volume 2947(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_number 4169 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 23.243 _diffrn_reflns_theta_max 23.243 _diffrn_reflns_theta_min 1.587 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 0.7449 _exptl_absorpt_correction_T_min 0.3520 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details TWINABS _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.225 _exptl_crystal_description plate _exptl_crystal_F_000 1156 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dichloromethane' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.524 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.113 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 377 _refine_ls_number_reflns 4169 _refine_ls_number_restraints 336 _refine_ls_restrained_S_all 0.946 _refine_ls_R_factor_all 0.2281 _refine_ls_R_factor_gt 0.1172 _refine_ls_shift/su_max 3.338 _refine_ls_shift/su_mean 0.014 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1774P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2797 _refine_ls_wR_factor_ref 0.3399 _reflns_number_gt 1802 _reflns_number_total 4169 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7pp00347a2.cif _cod_data_source_block coz14_03 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1549064 _shelx_estimated_absorpt_t_min 0.97 _shelx_estimated_absorpt_t_max 0.996 _shelx_res_file ; coz14_03_a.res created by SHELXL-2014/7 TITL coz14_03_a.res in P2(1)/c REM Old TITL coz14_03 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.263, Rweak 0.082, Alpha 0.080, Orientation as input REM Formula found by SHELXT: C37 N2 O2 CELL 0.71073 19.6746 16.9844 8.8594 90 95.45 90 ZERR 4 0.0114 0.0103 0.0052 0 0.009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 140 140 16 8 SIZE 0.40 0.20 0.05 RIGU L.S. 10 PLAN 20 TEMP -173 BOND $H LIST 6 FMAP 2 ACTA LIST 4 XNPD 0.005 WGHT 0.177400 FVAR 0.33105 O1 4 0.583284 0.472080 0.477213 11.00000 0.05466 0.03844 = 0.01322 0.00587 0.00690 -0.00370 O2 4 0.769865 0.396342 0.791087 11.00000 0.05613 0.07666 = 0.03353 0.02258 0.00583 -0.00232 N1 3 0.849902 0.612571 0.233805 11.00000 0.06716 0.03664 = 0.02685 0.00546 0.02117 -0.00454 N2 3 0.895451 0.503877 0.106751 11.00000 0.08076 0.03508 = 0.03162 0.00684 0.01223 -0.00188 N3 3 0.685624 0.442314 0.610906 11.00000 0.05188 0.03615 = 0.00719 -0.00298 0.00979 0.00141 N4 3 0.502814 0.393584 1.012483 11.00000 0.07637 0.08830 = 0.02613 0.00496 0.00372 -0.01411 C1 1 0.883770 0.582377 0.134114 11.00000 0.05795 0.03225 = 0.02053 0.00778 0.01073 -0.00515 C2 1 0.920232 0.639775 0.033560 11.00000 0.06854 0.04246 = 0.01923 0.00854 0.01409 -0.01042 C3 1 0.885524 0.718900 0.024211 11.00000 0.09910 0.04694 = 0.04686 0.02126 0.02494 -0.00122 AFIX 137 H3A 2 0.839484 0.713308 -0.027471 11.00000 -1.50000 H3B 2 0.911974 0.755447 -0.032725 11.00000 -1.50000 H3C 2 0.882532 0.739430 0.126747 11.00000 -1.50000 AFIX 0 C4 1 0.925109 0.606632 -0.125660 11.00000 0.08112 0.06634 = 0.02493 0.00791 0.01361 -0.00673 AFIX 137 H4A 2 0.950345 0.556818 -0.118460 11.00000 -1.50000 H4B 2 0.949031 0.644362 -0.185478 11.00000 -1.50000 H4C 2 0.879073 0.597490 -0.175011 11.00000 -1.50000 AFIX 0 C5 1 0.992740 0.647118 0.107647 11.00000 0.07251 0.05966 = 0.05612 0.00220 0.01032 -0.01058 AFIX 137 H5A 2 0.991962 0.669734 0.209234 11.00000 -1.50000 H5B 2 1.019092 0.681454 0.046055 11.00000 -1.50000 H5C 2 1.013983 0.594906 0.115490 11.00000 -1.50000 AFIX 0 C6 1 0.895844 0.440237 0.210586 11.00000 0.07404 0.03513 = 0.03388 0.01218 0.01746 0.00552 C7 1 0.868019 0.370277 0.167603 11.00000 0.07261 0.04345 = 0.04935 0.00013 0.03146 -0.00476 AFIX 43 H7 2 0.846787 0.363719 0.067535 11.00000 -1.20000 AFIX 0 C8 1 0.870220 0.308580 0.267590 11.00000 0.10156 0.04698 = 0.06554 0.01014 0.04960 0.00776 AFIX 43 H8 2 0.854868 0.257919 0.234128 11.00000 -1.20000 AFIX 0 C9 1 0.895063 0.320358 0.418633 11.00000 0.11729 0.05428 = 0.06547 0.01717 0.04373 0.00805 AFIX 43 H9 2 0.892294 0.279156 0.490312 11.00000 -1.20000 AFIX 0 C10 1 0.922639 0.389159 0.462638 11.00000 0.10711 0.06250 = 0.04952 0.02539 0.02267 0.00978 AFIX 43 H10 2 0.941700 0.395393 0.564535 11.00000 -1.20000 AFIX 0 C11 1 0.924172 0.453301 0.360745 11.00000 0.07068 0.05278 = 0.04116 0.00963 0.00921 0.00533 AFIX 43 H11 2 0.943340 0.502676 0.392045 11.00000 -1.20000 AFIX 0 C12 1 0.809009 0.565792 0.327414 11.00000 0.06271 0.02624 = 0.02812 0.00301 0.01965 0.00172 C13 1 0.760431 0.513299 0.264419 11.00000 0.06238 0.02663 = 0.02376 0.00197 0.01717 0.00727 AFIX 43 H13 2 0.754161 0.506280 0.157620 11.00000 -1.20000 AFIX 0 C14 1 0.720774 0.470807 0.358168 11.00000 0.05595 0.03525 = 0.01281 -0.00170 0.01024 -0.00275 AFIX 43 H14 2 0.688312 0.433347 0.316810 11.00000 -1.20000 AFIX 0 C15 1 0.730004 0.484812 0.517882 11.00000 0.04853 0.02511 = 0.01499 -0.00107 0.01364 0.00758 C16 1 0.775068 0.536902 0.574942 11.00000 0.05226 0.04109 = 0.01520 -0.00300 0.01613 -0.00379 AFIX 43 H16 2 0.780180 0.545216 0.681456 11.00000 -1.20000 AFIX 0 C17 1 0.815264 0.579961 0.484234 11.00000 0.07816 0.04513 = 0.02727 -0.00319 0.02044 -0.01240 AFIX 43 H17 2 0.846433 0.618312 0.527479 11.00000 -1.20000 AFIX 0 C18 1 0.710278 0.399889 0.744124 11.00000 0.05706 0.05228 = 0.01953 0.00624 0.00502 -0.00137 C19 1 0.648100 0.362292 0.797110 11.00000 0.05517 0.04041 = 0.00943 -0.00215 0.00631 0.00045 C20 1 0.589257 0.399338 0.714153 11.00000 0.05376 0.02569 = 0.00790 -0.00225 0.00705 -0.00513 C21 1 0.616585 0.441839 0.585795 11.00000 0.05285 0.01846 = 0.00981 -0.00479 0.00865 0.00312 C22 1 0.650582 0.293277 0.879557 11.00000 0.07517 0.04180 = 0.01735 0.00070 0.00852 0.00454 C23 1 0.587479 0.244480 0.895805 11.00000 0.08031 0.03833 = 0.04739 0.00909 0.01412 0.00034 AFIX 137 H23A 2 0.565548 0.262495 0.984414 11.00000 -1.50000 H23B 2 0.600359 0.188992 0.908988 11.00000 -1.50000 H23C 2 0.555601 0.250302 0.804553 11.00000 -1.50000 AFIX 0 C24 1 0.714236 0.259971 0.958629 11.00000 0.08288 0.06047 = 0.04164 0.02326 0.01091 0.00459 AFIX 137 H24A 2 0.723439 0.208436 0.915170 11.00000 -1.50000 H24B 2 0.708708 0.253985 1.066802 11.00000 -1.50000 H24C 2 0.752501 0.295550 0.946011 11.00000 -1.50000 AFIX 0 C25 1 0.523015 0.403920 0.727805 11.00000 0.05255 0.03848 = 0.00818 -0.00259 0.00377 -0.00209 AFIX 43 H25 2 0.496371 0.422691 0.640126 11.00000 -1.20000 AFIX 0 C26 1 0.483736 0.384769 0.856259 11.00000 0.05160 0.02825 = 0.00941 0.00905 0.00792 0.00271 C27 1 0.415930 0.365662 0.831209 11.00000 0.03629 0.01118 = 0.00619 0.00243 0.00539 0.00639 C28 1 0.389807 0.359200 0.970737 11.00000 0.05807 0.02156 = 0.01027 -0.00183 0.01064 0.00046 C29 1 0.442540 0.376833 1.079196 11.00000 0.05931 0.03316 = 0.01225 0.00144 0.00858 -0.00112 C30 1 0.427609 0.378503 1.235904 11.00000 0.07239 0.04830 = 0.00889 -0.00291 0.00500 0.00246 AFIX 43 H30 2 0.462056 0.390448 1.315103 11.00000 -1.20000 AFIX 0 C31 1 0.362907 0.362468 1.265743 11.00000 0.07176 0.04178 = 0.01049 -0.00691 0.01374 0.00738 AFIX 43 H31 2 0.352402 0.363731 1.368185 11.00000 -1.20000 AFIX 0 C32 1 0.311138 0.344256 1.153773 11.00000 0.05978 0.04129 = 0.01584 -0.00284 0.01284 0.01414 AFIX 43 H32 2 0.266770 0.332522 1.181451 11.00000 -1.20000 AFIX 0 C33 1 0.323399 0.342895 0.999208 11.00000 0.05372 0.02622 = 0.01210 -0.00353 0.01222 -0.00265 AFIX 43 H33 2 0.288519 0.331591 0.920556 11.00000 -1.20000 AFIX 0 C34 1 0.379018 0.349181 0.683592 11.00000 0.06567 0.03826 = 0.00527 0.00075 0.00435 -0.00253 AFIX 137 H34A 2 0.380412 0.395675 0.618450 11.00000 -1.50000 H34B 2 0.331435 0.336211 0.697064 11.00000 -1.50000 H34C 2 0.400453 0.304605 0.636271 11.00000 -1.50000 AFIX 0 C35 1 0.568601 0.420049 1.084242 11.00000 0.06000 0.05746 = 0.00874 0.00758 0.00656 -0.00176 AFIX 137 H35A 2 0.599984 0.375213 1.096707 11.00000 -1.50000 H35B 2 0.562471 0.442673 1.183803 11.00000 -1.50000 H35C 2 0.587573 0.460054 1.020457 11.00000 -1.50000 AFIX 0 HKLF 4 REM coz14_03_a.res in P2(1)/c REM R1 = 0.1172 for 1802 Fo > 4sig(Fo) and 0.2281 for all 4169 data REM 377 parameters refined using 336 restraints END WGHT 0.1746 0.0000 REM Highest difference peak 0.524, deepest hole -0.443, 1-sigma level 0.113 Q1 1 0.4328 0.3487 0.8286 11.00000 0.05 0.52 Q2 1 0.6381 0.4198 0.8341 11.00000 0.05 0.51 Q3 1 0.7887 0.5401 0.2725 11.00000 0.05 0.47 Q4 1 0.4224 0.3199 1.0284 11.00000 0.05 0.40 Q5 1 0.8171 0.4612 0.3032 11.00000 0.05 0.39 Q6 1 0.6556 0.4053 0.9957 11.00000 0.05 0.39 Q7 1 0.8606 0.5062 0.3852 11.00000 0.05 0.35 Q8 1 0.6077 0.3945 0.7703 11.00000 0.05 0.34 Q9 1 0.7291 0.5601 0.5633 11.00000 0.05 0.33 Q10 1 0.7398 0.5788 0.1943 11.00000 0.05 0.33 Q11 1 0.5000 0.5000 0.5000 10.50000 0.05 0.32 Q12 1 0.3393 0.3932 0.9926 11.00000 0.05 0.32 Q13 1 0.8009 0.5762 0.1658 11.00000 0.05 0.32 Q14 1 0.9403 0.5582 0.1591 11.00000 0.05 0.32 Q15 1 0.7937 0.4014 0.3830 11.00000 0.05 0.30 Q16 1 0.4794 0.3398 1.1108 11.00000 0.05 0.30 Q17 1 0.5673 0.4363 0.7405 11.00000 0.05 0.30 Q18 1 0.8317 0.6673 0.2081 11.00000 0.05 0.30 Q19 1 0.7838 0.6406 0.1928 11.00000 0.05 0.29 Q20 1 0.5925 0.3754 0.6753 11.00000 0.05 0.29 ; _shelx_res_checksum 91785 loop_ _symmetry_equiv_pos_as_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_calc_flag O1 O 0.5833(3) 0.4721(3) 0.4772(5) 0.0352(14) Uani 1 d O2 O 0.7699(3) 0.3963(4) 0.7911(6) 0.0553(18) Uani 1 d N1 N 0.8499(4) 0.6126(4) 0.2338(7) 0.0425(18) Uani 1 d N2 N 0.8955(4) 0.5039(4) 0.1068(7) 0.0487(19) Uani 1 d N3 N 0.6856(3) 0.4423(4) 0.6109(6) 0.0313(15) Uani 1 d N4 N 0.5028(4) 0.3936(5) 1.0125(8) 0.064(2) Uani 1 d C1 C 0.8838(4) 0.5824(5) 0.1341(9) 0.0365(19) Uani 1 d C2 C 0.9202(5) 0.6398(5) 0.0336(9) 0.043(2) Uani 1 d C3 C 0.8855(5) 0.7189(5) 0.0242(11) 0.063(3) Uani 1 d H3A H 0.8395 0.7133 -0.0275 0.095 Uiso 1 calc H3B H 0.912 0.7554 -0.0327 0.095 Uiso 1 calc H3C H 0.8825 0.7394 0.1267 0.095 Uiso 1 calc C4 C 0.9251(5) 0.6066(6) -0.1257(9) 0.057(3) Uani 1 d H4A H 0.9503 0.5568 -0.1185 0.085 Uiso 1 calc H4B H 0.949 0.6444 -0.1855 0.085 Uiso 1 calc H4C H 0.8791 0.5975 -0.175 0.085 Uiso 1 calc C5 C 0.9927(5) 0.6471(6) 0.1076(11) 0.062(3) Uani 1 d H5A H 0.992 0.6697 0.2092 0.094 Uiso 1 calc H5B H 1.0191 0.6815 0.0461 0.094 Uiso 1 calc H5C H 1.014 0.5949 0.1155 0.094 Uiso 1 calc C6 C 0.8958(5) 0.4402(5) 0.2106(9) 0.047(2) Uani 1 d C7 C 0.8680(5) 0.3703(5) 0.1676(11) 0.053(2) Uani 1 d H7 H 0.8468 0.3637 0.0675 0.064 Uiso 1 calc C8 C 0.8702(5) 0.3086(6) 0.2676(12) 0.069(3) Uani 1 d H8 H 0.8549 0.2579 0.2341 0.082 Uiso 1 calc C9 C 0.8951(6) 0.3204(6) 0.4186(13) 0.077(3) Uani 1 d H9 H 0.8923 0.2792 0.4903 0.092 Uiso 1 calc C10 C 0.9226(6) 0.3892(6) 0.4626(12) 0.072(3) Uani 1 d H10 H 0.9417 0.3954 0.5645 0.086 Uiso 1 calc C11 C 0.9242(5) 0.4533(6) 0.3607(10) 0.055(2) Uani 1 d H11 H 0.9433 0.5027 0.392 0.066 Uiso 1 calc C12 C 0.8090(4) 0.5658(5) 0.3274(9) 0.038(2) Uani 1 d C13 C 0.7604(4) 0.5133(5) 0.2644(9) 0.0368(19) Uani 1 d H13 H 0.7542 0.5063 0.1576 0.044 Uiso 1 calc C14 C 0.7208(4) 0.4708(5) 0.3582(8) 0.0342(19) Uani 1 d H14 H 0.6883 0.4333 0.3168 0.041 Uiso 1 calc C15 C 0.7300(4) 0.4848(4) 0.5179(8) 0.0289(18) Uani 1 d C16 C 0.7751(4) 0.5369(5) 0.5749(8) 0.035(2) Uani 1 d H16 H 0.7802 0.5452 0.6815 0.042 Uiso 1 calc C17 C 0.8153(5) 0.5800(5) 0.4842(9) 0.049(2) Uani 1 d H17 H 0.8464 0.6183 0.5275 0.059 Uiso 1 calc C18 C 0.7103(5) 0.3999(5) 0.7441(9) 0.043(2) Uani 1 d C19 C 0.6481(4) 0.3623(5) 0.7971(8) 0.0348(18) Uani 1 d C20 C 0.5893(4) 0.3993(4) 0.7142(8) 0.0289(17) Uani 1 d C21 C 0.6166(4) 0.4418(4) 0.5858(8) 0.0267(17) Uani 1 d C22 C 0.6506(5) 0.2933(5) 0.8796(8) 0.045(2) Uani 1 d C23 C 0.5875(5) 0.2445(5) 0.8958(10) 0.055(2) Uani 1 d H23A H 0.5655 0.2625 0.9844 0.082 Uiso 1 calc H23B H 0.6004 0.189 0.909 0.082 Uiso 1 calc H23C H 0.5556 0.2503 0.8046 0.082 Uiso 1 calc C24 C 0.7142(5) 0.2600(6) 0.9586(10) 0.061(3) Uani 1 d H24A H 0.7234 0.2084 0.9152 0.092 Uiso 1 calc H24B H 0.7087 0.254 1.0668 0.092 Uiso 1 calc H24C H 0.7525 0.2956 0.946 0.092 Uiso 1 calc C25 C 0.5230(4) 0.4039(5) 0.7278(8) 0.0330(19) Uani 1 d H25 H 0.4964 0.4227 0.6401 0.04 Uiso 1 calc C26 C 0.4837(4) 0.3848(4) 0.8563(8) 0.0294(18) Uani 1 d C27 C 0.4159(4) 0.3657(4) 0.8312(7) 0.0177(15) Uani 1 d C28 C 0.3898(4) 0.3592(4) 0.9707(8) 0.0295(17) Uani 1 d C29 C 0.4425(4) 0.3768(5) 1.0792(8) 0.0346(19) Uani 1 d C30 C 0.4276(5) 0.3785(5) 1.2359(8) 0.043(2) Uani 1 d H30 H 0.4621 0.3904 1.3151 0.052 Uiso 1 calc C31 C 0.3629(5) 0.3625(5) 1.2657(8) 0.041(2) Uani 1 d H31 H 0.3524 0.3637 1.3682 0.049 Uiso 1 calc C32 C 0.3111(4) 0.3443(5) 1.1538(8) 0.038(2) Uani 1 d H32 H 0.2668 0.3325 1.1815 0.046 Uiso 1 calc C33 C 0.3234(4) 0.3429(4) 0.9992(8) 0.0301(18) Uani 1 d H33 H 0.2885 0.3316 0.9206 0.036 Uiso 1 calc C34 C 0.3790(4) 0.3492(5) 0.6836(7) 0.036(2) Uani 1 d H34A H 0.3804 0.3957 0.6185 0.055 Uiso 1 calc H34B H 0.3314 0.3362 0.6971 0.055 Uiso 1 calc H34C H 0.4005 0.3046 0.6363 0.055 Uiso 1 calc C35 C 0.5686(4) 0.4200(5) 1.0842(8) 0.042(2) Uani 1 d H35A H 0.6 0.3752 1.0967 0.063 Uiso 1 calc H35B H 0.5625 0.4427 1.1838 0.063 Uiso 1 calc H35C H 0.5876 0.4601 1.0205 0.063 Uiso 1 calc 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 0.055(3) 0.038(3) 0.013(3) 0.006(2) 0.007(2) -0.004(3) O2 0.056(3) 0.077(5) 0.034(3) 0.023(3) 0.006(3) -0.002(3) N1 0.067(4) 0.037(4) 0.027(4) 0.005(3) 0.021(3) -0.005(3) N2 0.081(5) 0.035(3) 0.032(4) 0.007(3) 0.012(4) -0.002(3) N3 0.052(3) 0.036(4) 0.007(3) -0.003(2) 0.010(2) 0.001(3) N4 0.076(4) 0.088(6) 0.026(3) 0.005(3) 0.004(3) -0.014(4) C1 0.058(5) 0.032(4) 0.021(4) 0.008(3) 0.011(3) -0.005(3) C2 0.069(5) 0.042(4) 0.019(4) 0.009(3) 0.014(3) -0.010(4) C3 0.099(7) 0.047(5) 0.047(6) 0.021(4) 0.025(5) -0.001(5) C4 0.081(6) 0.066(6) 0.025(4) 0.008(4) 0.014(4) -0.007(5) C5 0.073(5) 0.060(6) 0.056(6) 0.002(5) 0.010(4) -0.011(5) C6 0.074(6) 0.035(4) 0.034(4) 0.012(3) 0.017(4) 0.006(4) C7 0.073(6) 0.043(4) 0.049(5) 0.000(4) 0.031(4) -0.005(4) C8 0.102(7) 0.047(5) 0.066(5) 0.010(4) 0.050(5) 0.008(5) C9 0.117(8) 0.054(5) 0.065(5) 0.017(4) 0.044(6) 0.008(5) C10 0.107(8) 0.062(5) 0.050(5) 0.025(4) 0.023(5) 0.010(5) C11 0.071(6) 0.053(5) 0.041(4) 0.010(4) 0.009(4) 0.005(5) C12 0.063(5) 0.026(4) 0.028(4) 0.003(3) 0.020(3) 0.002(4) C13 0.062(5) 0.027(4) 0.024(4) 0.002(3) 0.017(3) 0.007(4) C14 0.056(5) 0.035(4) 0.013(3) -0.002(3) 0.010(3) -0.003(4) C15 0.049(4) 0.025(4) 0.015(3) -0.001(3) 0.014(3) 0.008(3) C16 0.052(4) 0.041(5) 0.015(4) -0.003(3) 0.016(3) -0.004(4) C17 0.078(6) 0.045(5) 0.027(4) -0.003(3) 0.020(4) -0.012(5) C18 0.057(4) 0.052(5) 0.020(4) 0.006(3) 0.005(3) -0.001(4) C19 0.055(4) 0.040(4) 0.009(4) -0.002(3) 0.006(3) 0.000(3) C20 0.054(3) 0.026(4) 0.008(3) -0.002(3) 0.007(3) -0.005(3) C21 0.053(4) 0.018(4) 0.010(3) -0.005(3) 0.009(3) 0.003(3) C22 0.075(5) 0.042(4) 0.017(4) 0.001(3) 0.009(4) 0.005(4) C23 0.080(5) 0.038(5) 0.047(6) 0.009(4) 0.014(5) 0.000(4) C24 0.083(5) 0.060(6) 0.042(5) 0.023(5) 0.011(4) 0.005(5) C25 0.053(4) 0.038(5) 0.008(3) -0.003(3) 0.004(3) -0.002(4) C26 0.052(4) 0.028(4) 0.009(3) 0.009(3) 0.008(3) 0.003(3) C27 0.036(3) 0.011(4) 0.006(3) 0.002(3) 0.005(2) 0.006(3) C28 0.058(4) 0.022(4) 0.010(3) -0.002(3) 0.011(3) 0.000(3) C29 0.059(4) 0.033(5) 0.012(3) 0.001(3) 0.009(3) -0.001(4) C30 0.072(5) 0.048(5) 0.009(3) -0.003(3) 0.005(3) 0.002(4) C31 0.072(5) 0.042(5) 0.010(4) -0.007(3) 0.014(3) 0.007(4) C32 0.060(5) 0.041(5) 0.016(3) -0.003(3) 0.013(3) 0.014(4) C33 0.054(4) 0.026(4) 0.012(3) -0.004(3) 0.012(3) -0.003(4) C34 0.066(5) 0.038(5) 0.005(3) 0.001(3) 0.004(3) -0.003(4) C35 0.060(4) 0.057(6) 0.009(4) 0.008(4) 0.007(3) -0.002(4) 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 0 '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' O O 0.0106 0.006 '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 C1 N1 C12 122.4(7) C1 N2 C6 127.8(7) C21 N3 C18 112.9(6) C21 N3 C15 123.9(6) C18 N3 C15 123.1(6) C29 N4 C26 103.6(7) C29 N4 C35 129.0(7) C26 N4 C35 127.2(7) N1 C1 N2 128.5(7) N1 C1 C2 116.9(7) N2 C1 C2 114.5(7) C3 C2 C5 110.7(8) C3 C2 C4 110.2(7) C5 C2 C4 106.9(8) C3 C2 C1 111.2(7) C5 C2 C1 105.8(7) C4 C2 C1 111.9(7) C2 C3 H3A 109.5 C2 C3 H3B 109.5 H3A C3 H3B 109.5 C2 C3 H3C 109.5 H3A C3 H3C 109.5 H3B C3 H3C 109.5 C2 C4 H4A 109.5 C2 C4 H4B 109.5 H4A C4 H4B 109.5 C2 C4 H4C 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 C2 C5 H5A 109.5 C2 C5 H5B 109.5 H5A C5 H5B 109.5 C2 C5 H5C 109.5 H5A C5 H5C 109.5 H5B C5 H5C 109.5 C7 C6 C11 121.2(8) C7 C6 N2 120.7(8) C11 C6 N2 118.0(8) C6 C7 C8 120.3(10) C6 C7 H7 119.9 C8 C7 H7 119.9 C7 C8 C9 119.8(10) C7 C8 H8 120.1 C9 C8 H8 120.1 C10 C9 C8 120.2(10) C10 C9 H9 119.9 C8 C9 H9 119.9 C9 C10 C11 121.4(11) C9 C10 H10 119.3 C11 C10 H10 119.3 C6 C11 C10 116.7(10) C6 C11 H11 121.6 C10 C11 H11 121.6 C13 C12 C17 120.1(8) C13 C12 N1 121.5(7) C17 C12 N1 118.2(8) C12 C13 C14 119.8(7) C12 C13 H13 120.1 C14 C13 H13 120.1 C13 C14 C15 118.6(8) C13 C14 H14 120.7 C15 C14 H14 120.7 C16 C15 C14 120.6(7) C16 C15 N3 122.4(6) C14 C15 N3 117.0(7) C15 C16 C17 122.1(7) C15 C16 H16 119 C17 C16 H16 119 C16 C17 C12 118.8(8) C16 C17 H17 120.6 C12 C17 H17 120.6 O2 C18 N3 123.5(8) O2 C18 C19 131.9(8) N3 C18 C19 104.6(7) C22 C19 C20 128.4(8) C22 C19 C18 122.7(8) C20 C19 C18 107.0(6) C25 C20 C19 136.3(7) C25 C20 C21 118.1(7) C19 C20 C21 105.5(7) O1 C21 N3 125.4(7) O1 C21 C20 126.7(7) N3 C21 C20 107.8(6) C19 C22 C24 123.9(8) C19 C22 C23 121.9(8) C24 C22 C23 114.2(7) C22 C23 H23A 109.5 C22 C23 H23B 109.5 H23A C23 H23B 109.5 C22 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 C22 C24 H24A 109.5 C22 C24 H24B 109.5 H24A C24 H24B 109.5 C22 C24 H24C 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 C20 C25 C26 130.7(7) C20 C25 H25 114.6 C26 C25 H25 114.6 C27 C26 N4 110.4(7) C27 C26 C25 120.1(6) N4 C26 C25 128.8(7) C26 C27 C28 108.2(6) C26 C27 C34 125.7(6) C28 C27 C34 126.0(7) C29 C28 C33 125.3(7) C29 C28 C27 106.6(7) C33 C28 C27 128.0(7) C28 C29 N4 111.1(6) C28 C29 C30 117.7(7) N4 C29 C30 131.1(8) C31 C30 C29 117.7(8) C31 C30 H30 121.2 C29 C30 H30 121.2 C30 C31 C32 123.1(7) C30 C31 H31 118.5 C32 C31 H31 118.5 C31 C32 C33 121.0(8) C31 C32 H32 119.5 C33 C32 H32 119.5 C28 C33 C32 115.1(7) C28 C33 H33 122.4 C32 C33 H33 122.4 C27 C34 H34A 109.5 C27 C34 H34B 109.5 H34A C34 H34B 109.5 C27 C34 H34C 109.5 H34A C34 H34C 109.5 H34B C34 H34C 109.5 N4 C35 H35A 109.5 N4 C35 H35B 109.5 H35A C35 H35B 109.5 N4 C35 H35C 109.5 H35A C35 H35C 109.5 H35B C35 H35C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C21 1.224(8) O2 C18 1.208(10) N1 C1 1.264(9) N1 C12 1.447(10) N2 C1 1.378(10) N2 C6 1.419(10) N3 C21 1.355(9) N3 C18 1.428(10) N3 C15 1.449(9) N4 C29 1.403(10) N4 C26 1.407(10) N4 C35 1.458(10) C1 C2 1.543(11) C2 C3 1.506(12) C2 C5 1.518(12) C2 C4 1.530(11) C3 H3A 0.98 C3 H3B 0.98 C3 H3C 0.98 C4 H4A 0.98 C4 H4B 0.98 C4 H4C 0.98 C5 H5A 0.98 C5 H5B 0.98 C5 H5C 0.98 C6 C7 1.348(12) C6 C11 1.410(12) C7 C8 1.370(13) C7 H7 0.95 C8 C9 1.395(15) C8 H8 0.95 C9 C10 1.331(14) C9 H9 0.95 C10 C11 1.417(13) C10 H10 0.95 C11 H11 0.95 C12 C13 1.385(11) C12 C17 1.404(11) C13 C14 1.394(10) C13 H13 0.95 C14 C15 1.429(10) C14 H14 0.95 C15 C16 1.319(10) C16 C17 1.388(11) C16 H16 0.95 C17 H17 0.95 C18 C19 1.495(11) C19 C22 1.380(11) C19 C20 1.454(11) C20 C25 1.323(10) C20 C21 1.490(10) C22 C24 1.487(12) C22 C23 1.511(12) C23 H23A 0.98 C23 H23B 0.98 C23 H23C 0.98 C24 H24A 0.98 C24 H24B 0.98 C24 H24C 0.98 C25 C26 1.471(10) C25 H25 0.95 C26 C27 1.370(10) C27 C28 1.387(9) C27 C34 1.461(9) C28 C29 1.378(10) C28 C33 1.382(10) C29 C30 1.446(10) C30 C31 1.352(11) C30 H30 0.95 C31 C32 1.388(11) C31 H31 0.95 C32 C33 1.413(10) C32 H32 0.95 C33 H33 0.95 C34 H34A 0.98 C34 H34B 0.98 C34 H34C 0.98 C35 H35A 0.98 C35 H35B 0.98 C35 H35C 0.98