#------------------------------------------------------------------------------ #$Date: 2019-04-25 03:46:02 +0300 (Thu, 25 Apr 2019) $ #$Revision: 214761 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/83/7058334.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_7058334 loop_ _publ_author_name 'Fujita, Hikaru' 'Jing, Haoyu' 'Krayer, Michael' 'Allu, Srinivasarao' 'Veeraraghavaiah, Gorre' 'Wu, Zhiyuan' 'Jiang, Jianbing' 'Diers, James R.' 'Magdaong, Nikki Cecil M.' 'Mandal, Amit K.' 'Roy, Arpita' 'Niedzwiedzki, Dariusz M.' 'Kirmaier, Christine' 'Bocian, David F.' 'Holten, Dewey' 'Lindsey, Jonathan S.' _publ_section_title ; Annulated bacteriochlorins for near-infrared photophysical studies ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ01113G _journal_year 2019 _chemical_formula_moiety 'C30 H36 Br2 N4 O4 Pd' _chemical_formula_sum 'C30 H36 Br2 N4 O4 Pd' _chemical_formula_weight 782.85 _chemical_name_common 'ZW50 Pd-DHDP' _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_update_record ; 2019-02-27 deposited with the CCDC. 2019-04-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.1060(9) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 13.0158(3) _cell_length_b 8.1799(2) _cell_length_c 14.3232(3) _cell_measurement_reflns_used 505 _cell_measurement_temperature 100.(2) _cell_measurement_theta_max 34.3261 _cell_measurement_theta_min 2.8646 _cell_volume 1521.05(6) _computing_cell_refinement 'APEX3 v2016.5-0 (Bruker AXS)' _computing_data_collection 'Bruker Instrument Service v2013.12.0.0' _computing_data_reduction 'SAINT V8.37A (Bruker AXS Inc., 2015)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 786)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 100.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker-Nonius X8 Kappa APEX II' _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 0.0223 _diffrn_reflns_av_unetI/netI 0.0140 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 71519 _diffrn_reflns_theta_full 40.43 _diffrn_reflns_theta_max 40.43 _diffrn_reflns_theta_min 2.85 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 3.279 _exptl_absorpt_correction_T_max 0.65 _exptl_absorpt_correction_T_min 0.43 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.363 _exptl_crystal_size_mid 0.212 _exptl_crystal_size_min 0.142 _refine_diff_density_max 0.799 _refine_diff_density_min -0.824 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 9654 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0211 _refine_ls_R_factor_gt 0.0174 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0191P)^2^+0.5858P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0431 _reflns_number_gt 8790 _reflns_number_total 9654 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj01113g2.cif _cod_data_source_block rds642 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Numerical' changed to 'numerical' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 7058334 _shelx_res_file ; rds642_0m.res created by SHELXL-2014/7 TITL rds642_0m in P2(1)/c CELL 0.71073 13.0158 8.1799 14.3232 90 94.106 90 ZERR 2 0.0003 0.0002 0.0003 0 0.0009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br N O Pd UNIT 60 72 4 8 8 2 list 4 acta L.S. 8 PLAN 10 SIZE 0.142 0.212 0.363 TEMP -173.15 BOND $h more -1 conf fmap 2 OMIT 1 0 0 WGHT 0.019100 0.585800 FVAR 0.44968 PD1 6 0.000000 0.500000 0.500000 10.50000 0.00539 0.00568 = 0.00709 -0.00050 0.00069 -0.00015 BR1 3 0.266716 0.130508 0.259219 11.00000 0.01366 0.01758 = 0.01141 -0.00258 0.00417 0.00405 N2 4 0.126797 0.408299 0.448024 11.00000 0.00690 0.00851 = 0.00953 -0.00109 0.00088 0.00036 N1 4 -0.076485 0.307819 0.441936 11.00000 0.00746 0.00770 = 0.00782 -0.00048 0.00095 -0.00033 C7 1 0.226715 0.264971 0.356304 11.00000 0.00901 0.01125 = 0.00954 -0.00037 0.00296 0.00149 C1 1 -0.145255 0.213024 0.474635 11.00000 0.00791 0.00776 = 0.00847 0.00034 0.00105 -0.00011 C8 1 0.289862 0.321901 0.434212 11.00000 0.00716 0.01211 = 0.01179 0.00029 0.00173 0.00098 C9 1 0.224040 0.410279 0.488060 11.00000 0.00736 0.01033 = 0.01122 -0.00053 0.00047 -0.00003 AFIX 43 H9 2 0.244711 0.464398 0.545019 11.00000 -1.20000 AFIX 0 C12 1 -0.302789 0.059749 0.405669 11.00000 0.00940 0.01771 = 0.01688 -0.00083 0.00068 -0.00401 AFIX 137 H12A 2 -0.317288 0.015334 0.466896 11.00000 -1.50000 H12B 2 -0.325641 -0.018214 0.356538 11.00000 -1.50000 H12C 2 -0.339644 0.163357 0.395251 11.00000 -1.50000 AFIX 0 C13 1 0.397812 0.283187 0.459482 11.00000 0.00797 0.01782 = 0.01420 0.00085 0.00126 0.00176 C4 1 -0.060373 0.259534 0.347661 11.00000 0.00870 0.00884 = 0.00730 0.00013 0.00041 -0.00062 C6 1 0.126479 0.316833 0.366861 11.00000 0.00790 0.00941 = 0.00855 0.00012 0.00169 0.00043 C5 1 0.033388 0.264814 0.313974 11.00000 0.00907 0.01139 = 0.00782 0.00004 0.00134 -0.00031 AFIX 43 H5 2 0.038870 0.232016 0.250899 11.00000 -1.20000 AFIX 0 C3 1 -0.155167 0.169055 0.311724 11.00000 0.00971 0.01127 = 0.00820 -0.00021 -0.00074 -0.00159 AFIX 23 H3A 2 -0.139497 0.086045 0.264492 11.00000 -1.20000 H3B 2 -0.208880 0.244330 0.284583 11.00000 -1.20000 AFIX 0 O2 5 0.426998 0.336654 0.546399 11.00000 0.00775 0.02526 = 0.01492 -0.00157 -0.00114 0.00228 O1 5 0.454487 0.208983 0.410998 11.00000 0.01215 0.03999 = 0.02135 -0.00766 0.00143 0.01014 C14 1 0.530967 0.293303 0.579834 11.00000 0.00887 0.03462 = 0.01808 0.00045 -0.00173 0.00356 AFIX 23 H14A 2 0.581066 0.342402 0.539171 11.00000 -1.20000 H14B 2 0.539682 0.173085 0.579256 11.00000 -1.20000 AFIX 0 C15 1 0.548564 0.357717 0.678115 11.00000 0.01495 0.05358 = 0.01722 -0.00119 -0.00211 0.00161 AFIX 137 H15A 2 0.536675 0.476019 0.678198 11.00000 -1.50000 H15B 2 0.619619 0.334838 0.701786 11.00000 -1.50000 H15C 2 0.500853 0.304235 0.718352 11.00000 -1.50000 AFIX 0 C10 1 -0.172512 0.212729 0.573290 11.00000 0.01435 0.01366 = 0.00937 -0.00021 0.00350 -0.00230 AFIX 137 H10A 2 -0.124417 0.282902 0.610698 11.00000 -1.50000 H10B 2 -0.168341 0.100936 0.597871 11.00000 -1.50000 H10C 2 -0.242812 0.254154 0.576567 11.00000 -1.50000 AFIX 0 C2 1 -0.187396 0.088937 0.403058 11.00000 0.00852 0.00866 = 0.00940 -0.00045 0.00014 -0.00173 C11 1 -0.126043 -0.069716 0.422475 11.00000 0.01543 0.00828 = 0.01528 0.00015 0.00007 0.00026 AFIX 137 H11A 2 -0.052799 -0.049202 0.415546 11.00000 -1.50000 H11B 2 -0.150944 -0.154133 0.377869 11.00000 -1.50000 H11C 2 -0.135310 -0.106862 0.486376 11.00000 -1.50000 AFIX 0 HKLF 4 REM rds642_0m in P2(1)/c REM R1 = 0.0174 for 8790 Fo > 4sig(Fo) and 0.0211 for all 9654 data REM 191 parameters refined using 0 restraints END WGHT 0.0191 0.5858 REM Highest difference peak 0.799, deepest hole -0.824, 1-sigma level 0.076 Q1 1 0.2857 0.1467 0.2984 11.00000 0.05 0.80 Q2 1 -0.0123 0.2631 0.3323 11.00000 0.05 0.77 Q3 1 0.2830 0.1983 0.2600 11.00000 0.05 0.75 Q4 1 -0.0036 0.4764 0.4590 11.00000 0.05 0.71 Q5 1 0.0802 0.2969 0.3407 11.00000 0.05 0.66 Q6 1 -0.1094 0.2606 0.4608 11.00000 0.05 0.66 Q7 1 0.2599 0.3603 0.4655 11.00000 0.05 0.64 Q8 1 0.1776 0.2965 0.3574 11.00000 0.05 0.58 Q9 1 0.1264 0.3629 0.4114 11.00000 0.05 0.56 Q10 1 0.3450 0.3006 0.4472 11.00000 0.05 0.55 ; _shelx_res_checksum 15385 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 Pd Pd1 0 0.5 0.5 0.00604(10) Uani d . P S 1 Br Br1 0.26672(2) 0.13051(2) 0.25922(2) 0.01406(2) Uani d . . . 1 N N2 0.12680(4) 0.40830(7) 0.44802(4) 0.00830(8) Uani d . . . 1 N N1 -0.07649(4) 0.30782(7) 0.44194(4) 0.00764(8) Uani d . . . 1 C C7 0.22671(5) 0.26497(9) 0.35630(5) 0.00982(10) Uani d . . . 1 C C1 -0.14525(5) 0.21302(8) 0.47464(5) 0.00802(9) Uani d . . . 1 C C8 0.28986(5) 0.32190(9) 0.43421(5) 0.01030(10) Uani d . . . 1 C C9 0.22404(5) 0.41028(9) 0.48806(5) 0.00965(9) Uani d . . . 1 H H9 0.2447 0.4644 0.545 0.012 Uiso calc U . R 1 C C12 -0.30279(6) 0.05975(10) 0.40567(6) 0.01468(12) Uani d . . . 1 H H12A -0.3173 0.0153 0.4669 0.022 Uiso calc U . R 1 H H12B -0.3256 -0.0182 0.3565 0.022 Uiso calc U . R 1 H H12C -0.3396 0.1634 0.3953 0.022 Uiso calc U . R 1 C C13 0.39781(5) 0.28319(10) 0.45948(5) 0.01331(11) Uani d . . . 1 C C4 -0.06037(5) 0.25953(8) 0.34766(4) 0.00829(9) Uani d . . . 1 C C6 0.12648(5) 0.31683(8) 0.36686(5) 0.00857(9) Uani d . . . 1 C C5 0.03339(5) 0.26481(8) 0.31397(5) 0.00939(9) Uani d . . . 1 H H5 0.0389 0.232 0.2509 0.011 Uiso calc U . R 1 C C3 -0.15517(5) 0.16906(9) 0.31172(5) 0.00979(10) Uani d . . . 1 H H3A -0.1395 0.086 0.2645 0.012 Uiso calc U . R 1 H H3B -0.2089 0.2443 0.2846 0.012 Uiso calc U . R 1 O O2 0.42700(4) 0.33665(8) 0.54640(4) 0.01607(10) Uani d . . . 1 O O1 0.45449(5) 0.20898(11) 0.41100(5) 0.02449(14) Uani d . . . 1 C C14 0.53097(6) 0.29330(13) 0.57983(6) 0.02065(16) Uani d . . . 1 H H14A 0.5811 0.3424 0.5392 0.025 Uiso calc U . R 1 H H14B 0.5397 0.1731 0.5793 0.025 Uiso calc U . R 1 C C15 0.54856(7) 0.35772(17) 0.67812(7) 0.0287(2) Uani d . . . 1 H H15A 0.5367 0.476 0.6782 0.043 Uiso calc U . R 1 H H15B 0.6196 0.3348 0.7018 0.043 Uiso calc U . R 1 H H15C 0.5009 0.3042 0.7184 0.043 Uiso calc U . R 1 C C10 -0.17251(6) 0.21273(9) 0.57329(5) 0.01233(11) Uani d . . . 1 H H10A -0.1244 0.2829 0.6107 0.018 Uiso calc U . R 1 H H10B -0.1683 0.1009 0.5979 0.018 Uiso calc U . R 1 H H10C -0.2428 0.2542 0.5766 0.018 Uiso calc U . R 1 C C2 -0.18740(5) 0.08894(8) 0.40306(5) 0.00889(9) Uani d . . . 1 C C11 -0.12604(6) -0.06972(9) 0.42248(6) 0.01305(11) Uani d . . . 1 H H11A -0.0528 -0.0492 0.4155 0.02 Uiso calc U . R 1 H H11B -0.1509 -0.1541 0.3779 0.02 Uiso calc U . R 1 H H11C -0.1353 -0.1069 0.4864 0.02 Uiso calc U . R 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 Pd1 0.00539(2) 0.00568(2) 0.00709(2) -0.00015(2) 0.00069(2) -0.00050(2) Br1 0.01366(3) 0.01758(3) 0.01141(3) 0.00405(2) 0.00417(2) -0.00258(2) N2 0.00690(18) 0.0085(2) 0.0095(2) 0.00036(15) 0.00088(15) -0.00109(16) N1 0.00746(18) 0.00770(19) 0.0078(2) -0.00033(15) 0.00095(15) -0.00048(15) C7 0.0090(2) 0.0113(2) 0.0095(2) 0.00149(19) 0.00296(18) -0.00037(19) C1 0.0079(2) 0.0078(2) 0.0085(2) -0.00011(17) 0.00105(17) 0.00034(17) C8 0.0072(2) 0.0121(2) 0.0118(2) 0.00098(19) 0.00173(18) 0.0003(2) C9 0.0074(2) 0.0103(2) 0.0112(2) -0.00003(18) 0.00047(18) -0.00053(19) C12 0.0094(2) 0.0177(3) 0.0169(3) -0.0040(2) 0.0007(2) -0.0008(2) C13 0.0080(2) 0.0178(3) 0.0142(3) 0.0018(2) 0.0013(2) 0.0008(2) C4 0.0087(2) 0.0088(2) 0.0073(2) -0.00062(18) 0.00041(17) 0.00013(18) C6 0.0079(2) 0.0094(2) 0.0086(2) 0.00043(18) 0.00169(17) 0.00012(18) C5 0.0091(2) 0.0114(2) 0.0078(2) -0.00031(18) 0.00134(17) 0.00004(19) C3 0.0097(2) 0.0113(2) 0.0082(2) -0.00159(19) -0.00074(18) -0.00021(19) O2 0.00775(19) 0.0253(3) 0.0149(2) 0.00228(19) -0.00114(16) -0.0016(2) O1 0.0121(2) 0.0400(4) 0.0214(3) 0.0101(2) 0.0014(2) -0.0077(3) C14 0.0089(3) 0.0346(5) 0.0181(3) 0.0036(3) -0.0017(2) 0.0004(3) C15 0.0150(3) 0.0536(7) 0.0172(4) 0.0016(4) -0.0021(3) -0.0012(4) C10 0.0143(3) 0.0137(3) 0.0094(2) -0.0023(2) 0.0035(2) -0.0002(2) C2 0.0085(2) 0.0087(2) 0.0094(2) -0.00173(18) 0.00014(18) -0.00045(18) C11 0.0154(3) 0.0083(2) 0.0153(3) 0.0003(2) 0.0001(2) 0.0001(2) 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' Br Br -0.2901 2.4595 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 '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 N2 Pd1 N2 . 3_566 179.999(16) N2 Pd1 N1 . . 87.14(2) N2 Pd1 N1 3_566 . 92.85(2) N2 Pd1 N1 . 3_566 92.86(2) N2 Pd1 N1 3_566 3_566 87.14(2) N1 Pd1 N1 . 3_566 180.0 C9 N2 C6 . . 108.04(6) C9 N2 Pd1 . . 127.51(5) C6 N2 Pd1 . . 124.20(4) C1 N1 C4 . . 109.03(5) C1 N1 Pd1 . . 130.75(5) C4 N1 Pd1 . . 120.19(4) C6 C7 C8 . . 108.06(6) C6 C7 Br1 . . 124.89(5) C8 C7 Br1 . . 126.92(5) N1 C1 C10 . . 124.34(6) N1 C1 C2 . . 112.42(6) C10 C1 C2 . . 122.94(6) C9 C8 C7 . . 105.14(6) C9 C8 C13 . . 126.40(7) C7 C8 C13 . . 128.15(6) N2 C9 C8 . . 110.65(6) N2 C9 H9 . . 124.7 C8 C9 H9 . . 124.7 C2 C12 H12A . . 109.5 C2 C12 H12B . . 109.5 H12A C12 H12B . . 109.5 C2 C12 H12C . . 109.5 H12A C12 H12C . . 109.5 H12B C12 H12C . . 109.5 O1 C13 O2 . . 123.29(7) O1 C13 C8 . . 125.52(7) O2 C13 C8 . . 111.16(6) C5 C4 N1 . . 121.72(6) C5 C4 C3 . . 129.71(6) N1 C4 C3 . . 106.66(5) N2 C6 C7 . . 108.08(6) N2 C6 C5 . . 123.49(6) C7 C6 C5 . . 127.64(6) C4 C5 C6 . . 124.70(6) C4 C5 H5 . . 117.6 C6 C5 H5 . . 117.6 C4 C3 C2 . . 100.67(5) C4 C3 H3A . . 111.6 C2 C3 H3A . . 111.6 C4 C3 H3B . . 111.6 C2 C3 H3B . . 111.6 H3A C3 H3B . . 109.4 C13 O2 C14 . . 114.91(6) O2 C14 C15 . . 107.45(7) O2 C14 H14A . . 110.2 C15 C14 H14A . . 110.2 O2 C14 H14B . . 110.2 C15 C14 H14B . . 110.2 H14A C14 H14B . . 108.5 C14 C15 H15A . . 109.5 C14 C15 H15B . . 109.5 H15A C15 H15B . . 109.5 C14 C15 H15C . . 109.5 H15A C15 H15C . . 109.5 H15B C15 H15C . . 109.5 C1 C10 H10A . . 109.5 C1 C10 H10B . . 109.5 H10A C10 H10B . . 109.5 C1 C10 H10C . . 109.5 H10A C10 H10C . . 109.5 H10B C10 H10C . . 109.5 C1 C2 C12 . . 113.42(6) C1 C2 C11 . . 106.52(5) C12 C2 C11 . . 111.29(6) C1 C2 C3 . . 100.44(5) C12 C2 C3 . . 114.48(6) C11 C2 C3 . . 109.96(6) C2 C11 H11A . . 109.5 C2 C11 H11B . . 109.5 H11A C11 H11B . . 109.5 C2 C11 H11C . . 109.5 H11A C11 H11C . . 109.5 H11B C11 H11C . . 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance Pd1 N2 . 2.0041(6) Pd1 N2 3_566 2.0042(6) Pd1 N1 . 2.0088(6) Pd1 N1 3_566 2.0089(6) Br1 C7 . 1.8757(7) N2 C9 . 1.3517(9) N2 C6 . 1.3822(9) N1 C1 . 1.2969(8) N1 C4 . 1.4366(9) C7 C6 . 1.3904(9) C7 C8 . 1.4164(10) C1 C10 . 1.4813(10) C1 C2 . 1.5171(9) C8 C9 . 1.3950(10) C8 C13 . 1.4603(10) C9 H9 . 0.95 C12 C2 . 1.5239(10) C12 H12A . 0.98 C12 H12B . 0.98 C12 H12C . 0.98 C13 O1 . 1.2117(10) C13 O2 . 1.3482(10) C4 C5 . 1.3447(9) C4 C3 . 1.4980(9) C6 C5 . 1.4462(9) C5 H5 . 0.95 C3 C2 . 1.5477(10) C3 H3A . 0.99 C3 H3B . 0.99 O2 C14 . 1.4469(10) C14 C15 . 1.5052(14) C14 H14A . 0.99 C14 H14B . 0.99 C15 H15A . 0.98 C15 H15B . 0.98 C15 H15C . 0.98 C10 H10A . 0.98 C10 H10B . 0.98 C10 H10C . 0.98 C2 C11 . 1.5386(10) C11 H11A . 0.98 C11 H11B . 0.98 C11 H11C . 0.98 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 C4 N1 C1 C10 172.15(6) Pd1 N1 C1 C10 -9.76(10) C4 N1 C1 C2 -1.80(7) Pd1 N1 C1 C2 176.28(4) C6 C7 C8 C9 -1.35(8) Br1 C7 C8 C9 -177.31(5) C6 C7 C8 C13 172.53(7) Br1 C7 C8 C13 -3.43(11) C6 N2 C9 C8 0.49(8) Pd1 N2 C9 C8 174.81(5) C7 C8 C9 N2 0.54(8) C13 C8 C9 N2 -173.48(7) C9 C8 C13 O1 -178.44(9) C7 C8 C13 O1 8.91(14) C9 C8 C13 O2 3.47(11) C7 C8 C13 O2 -169.19(7) C1 N1 C4 C5 -143.32(7) Pd1 N1 C4 C5 38.36(8) C1 N1 C4 C3 22.36(7) Pd1 N1 C4 C3 -155.96(4) C9 N2 C6 C7 -1.34(8) Pd1 N2 C6 C7 -175.90(5) C9 N2 C6 C5 169.14(6) Pd1 N2 C6 C5 -5.42(9) C8 C7 C6 N2 1.68(8) Br1 C7 C6 N2 177.74(5) C8 C7 C6 C5 -168.29(7) Br1 C7 C6 C5 7.77(11) N1 C4 C5 C6 0.45(11) C3 C4 C5 C6 -161.61(7) N2 C6 C5 C4 -18.47(11) C7 C6 C5 C4 150.08(7) C5 C4 C3 C2 132.06(7) N1 C4 C3 C2 -32.07(7) O1 C13 O2 C14 -2.31(13) C8 C13 O2 C14 175.83(7) C13 O2 C14 C15 -178.16(8) N1 C1 C2 C12 -140.86(6) C10 C1 C2 C12 45.09(9) N1 C1 C2 C11 96.38(7) C10 C1 C2 C11 -77.67(8) N1 C1 C2 C3 -18.25(7) C10 C1 C2 C3 167.70(6) C4 C3 C2 C1 29.00(6) C4 C3 C2 C12 150.86(6) C4 C3 C2 C11 -82.99(6)