#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:02:21 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304784 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064316.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_7064316 loop_ _publ_author_name 'Tran, Vy-Phuong' 'Kundu, Arup' 'Scott, Madelyn N.' 'Iwanicki, Ainsley' 'Nalaoh, Phattananawee' 'Diers, James R.' 'Taniguchi, Masahiko' 'Bocian, David F.' 'Schlau-Cohen, Gabriela S.' 'Lindsey, Jonathan S.' _publ_section_title ; Synthesis and characterization of 5,15-bis(hydroxymethyl)porphyrins -- simple compounds distantly inspired by the chlorosomal bacteriochlorophylls ; _journal_issue 4 _journal_name_full 'New Journal of Chemistry' _journal_page_first 1990 _journal_page_last 2004 _journal_paper_doi 10.1039/D5NJ04118J _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C24 H20 N4 Zn' _chemical_formula_sum 'C24 H20 N4 Zn' _chemical_formula_weight 429.81 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-09-22 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _audit_update_record ; 2025-10-17 deposited with the CCDC. 2025-12-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.0770(8) _cell_length_b 15.715(3) _cell_length_c 23.357(3) _cell_measurement_reflns_used 8230 _cell_measurement_temperature 100.00 _cell_measurement_theta_max 28.25 _cell_measurement_theta_min 2.59 _cell_volume 1863.5(5) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0678 _diffrn_reflns_av_unetI/netI 0.0326 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 22740 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.730 _diffrn_reflns_theta_min 2.592 _diffrn_source_current 1.4 _diffrn_source_power 0.07 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.337 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.5423 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1397 before and 0.0849 after correction. The Ratio of minimum to maximum transmission is 0.7272. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear dark violet' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary violet _exptl_crystal_density_diffrn 1.532 _exptl_crystal_description prism _exptl_crystal_F_000 888 _exptl_crystal_size_max 0.678 _exptl_crystal_size_mid 0.102 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.706 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.092 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 134 _refine_ls_number_reflns 1980 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.130 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0469 _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^)+(0.0418P)^2^+3.8991P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1099 _refine_ls_wR_factor_ref 0.1182 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1587 _reflns_number_total 1980 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj04118j2.cif _cod_data_source_block ncsu_pn100_a _cod_original_cell_volume 1863.6(5) _cod_original_sg_symbol_H-M Pbca _cod_database_code 7064316 _shelx_shelxl_version_number 2019/1 _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_max 0.924 _shelx_estimated_absorpt_t_min 0.464 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C11(H11A,H11B) 2.b Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C5(H5), C7(H7), C8(H8) 2.c Idealised Me refined as rotating group: C12(H12A,H12B,H12C) ; _shelx_res_file ; TITL NCSU_PN100_a.res in Pbca ncsu_pn100_a.res created by SHELXL-2019/1 at 16:32:37 on 22-Sep-2025 REM Old TITL NCSU_PN100 in Pbca REM SHELXT solution in Pbca: R1 0.104, Rweak 0.002, Alpha 0.023 REM 0.856 for 359 systematic absences, Orientation as input REM Formula found by SHELXT: C24 N4 Zn CELL 0.71073 5.077 15.7153 23.357 90 90 90 ZERR 4 0.0008 0.0025 0.0034 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N Zn UNIT 96 80 16 4 L.S. 10 PLAN 5 SIZE 0.06 0.102 0.678 TEMP -173.15 CONF BOND LIST 4 MORE -1 BOND $H fmap 2 ACTA REM REM REM WGHT 0.041800 3.899100 FVAR 0.30226 C1 1 0.650257 0.433118 0.381814 11.00000 0.03199 0.01374 = 0.02549 -0.00088 0.00724 -0.00656 C2 1 0.327480 0.525468 0.374215 11.00000 0.02719 0.01350 = 0.02670 0.00132 -0.00092 -0.00722 C3 1 0.386956 0.495160 0.317168 11.00000 0.04076 0.02349 = 0.02472 0.00128 -0.00249 -0.00885 AFIX 43 H3 2 0.302686 0.512100 0.282688 11.00000 -1.20000 AFIX 0 C4 1 0.585248 0.438142 0.322205 11.00000 0.04106 0.01962 = 0.02660 -0.00260 0.00471 -0.00336 AFIX 43 H4 2 0.666066 0.407285 0.291962 11.00000 -1.20000 AFIX 0 C5 1 0.852764 0.383272 0.404763 11.00000 0.02807 0.01631 = 0.03143 -0.00292 0.01016 -0.00402 AFIX 43 H5 2 0.950955 0.350085 0.378302 11.00000 -1.20000 AFIX 0 C6 1 0.925951 0.376889 0.461539 11.00000 0.02326 0.01287 = 0.03435 0.00043 0.00534 -0.00392 C7 1 1.146952 0.328441 0.481842 11.00000 0.02336 0.02006 = 0.04451 0.00113 0.00591 0.00045 AFIX 43 H7 2 1.266697 0.296603 0.459084 11.00000 -1.20000 AFIX 0 C8 1 1.152416 0.336721 0.539612 11.00000 0.02312 0.01986 = 0.04334 0.00453 -0.00281 0.00181 AFIX 43 H8 2 1.275998 0.311238 0.564885 11.00000 -1.20000 AFIX 0 C9 1 0.935320 0.391538 0.555750 11.00000 0.02197 0.01464 = 0.03379 0.00180 -0.00163 -0.00367 C10 1 0.872380 0.415574 0.611791 11.00000 0.02508 0.01722 = 0.02963 0.00285 -0.00673 -0.00718 C11 1 1.019566 0.373557 0.660596 11.00000 0.03323 0.02805 = 0.03377 0.00026 -0.01022 -0.00044 AFIX 23 H11A 2 1.025952 0.413108 0.693558 11.00000 -1.20000 H11B 2 1.202958 0.362067 0.648443 11.00000 -1.20000 AFIX 0 C12 1 0.891637 0.290551 0.679395 11.00000 0.05593 0.03068 = 0.03861 0.01109 -0.01311 -0.00139 AFIX 137 H12A 2 0.901317 0.249097 0.648121 11.00000 -1.50000 H12B 2 0.706751 0.300951 0.689214 11.00000 -1.50000 H12C 2 0.984466 0.268156 0.712954 11.00000 -1.50000 AFIX 0 N1 3 0.490718 0.485625 0.412827 11.00000 0.02399 0.01272 = 0.02267 0.00072 0.00170 -0.00399 N2 3 0.803944 0.415725 0.506976 11.00000 0.02141 0.01500 = 0.02775 -0.00060 0.00280 -0.00337 ZN1 4 0.500000 0.500000 0.500000 10.50000 0.02139 0.01817 = 0.02201 -0.00006 0.00125 -0.00002 HKLF 4 REM NCSU_PN100_a.res in Pbca REM wR2 = 0.1182, GooF = S = 1.130, Restrained GooF = 1.130 for all data REM R1 = 0.0469 for 1587 Fo > 4sig(Fo) and 0.0610 for all 1980 data REM 134 parameters refined using 0 restraints END WGHT 0.0418 3.8850 REM Highest difference peak 0.706, deepest hole -0.574, 1-sigma level 0.092 Q1 1 0.5250 0.4981 0.5440 11.00000 0.05 0.71 Q2 1 0.8668 0.4020 0.4854 11.00000 0.05 0.37 Q3 1 0.2922 0.5022 0.5179 11.00000 0.05 0.36 Q4 1 1.0328 0.3600 0.4701 11.00000 0.05 0.31 Q5 1 0.7649 0.4383 0.6181 11.00000 0.05 0.30 ; _shelx_res_checksum 90946 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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 C1 C 0.6503(6) 0.43312(18) 0.38181(13) 0.0237(7) Uani 1 1 d . . . . . C2 C 0.3275(6) 0.52547(18) 0.37422(13) 0.0225(6) Uani 1 1 d . . . . . C3 C 0.3870(8) 0.49516(19) 0.31717(14) 0.0297(7) Uani 1 1 d . . . . . H3 H 0.302686 0.512100 0.282688 0.036 Uiso 1 1 calc R U . . . C4 C 0.5852(7) 0.43814(19) 0.32220(14) 0.0291(7) Uani 1 1 d . . . . . H4 H 0.666066 0.407285 0.291962 0.035 Uiso 1 1 calc R U . . . C5 C 0.8528(6) 0.38327(18) 0.40476(13) 0.0253(7) Uani 1 1 d . . . . . H5 H 0.950955 0.350085 0.378302 0.030 Uiso 1 1 calc R U . . . C6 C 0.9260(6) 0.37689(18) 0.46154(14) 0.0235(6) Uani 1 1 d . . . . . C7 C 1.1470(6) 0.32844(19) 0.48184(15) 0.0293(7) Uani 1 1 d . . . . . H7 H 1.266697 0.296603 0.459084 0.035 Uiso 1 1 calc R U . . . C8 C 1.1524(6) 0.33672(19) 0.53961(15) 0.0288(7) Uani 1 1 d . . . . . H8 H 1.275998 0.311238 0.564885 0.035 Uiso 1 1 calc R U . . . C9 C 0.9353(6) 0.39154(18) 0.55575(14) 0.0235(6) Uani 1 1 d . . . . . C10 C 0.8724(6) 0.41557(18) 0.61179(13) 0.0240(7) Uani 1 1 d . . . . . C11 C 1.0196(7) 0.3736(2) 0.66060(15) 0.0317(8) Uani 1 1 d . . . . . H11A H 1.025952 0.413108 0.693558 0.038 Uiso 1 1 calc R U . . . H11B H 1.202958 0.362067 0.648443 0.038 Uiso 1 1 calc R U . . . C12 C 0.8916(9) 0.2906(2) 0.67939(16) 0.0417(9) Uani 1 1 d . . . . . H12A H 0.901317 0.249097 0.648121 0.063 Uiso 1 1 calc R U . . . H12B H 0.706751 0.300951 0.689214 0.063 Uiso 1 1 calc R U . . . H12C H 0.984466 0.268156 0.712954 0.063 Uiso 1 1 calc R U . . . N1 N 0.4907(5) 0.48563(14) 0.41283(11) 0.0198(5) Uani 1 1 d . . . . . N2 N 0.8039(5) 0.41573(15) 0.50698(10) 0.0214(5) Uani 1 1 d . . . . . Zn1 Zn 0.500000 0.500000 0.500000 0.02052(17) Uani 1 2 d S . P . . 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 C1 0.0320(17) 0.0137(13) 0.0255(15) -0.0009(11) 0.0072(13) -0.0066(12) C2 0.0272(16) 0.0135(12) 0.0267(16) 0.0013(11) -0.0009(13) -0.0072(12) C3 0.0408(19) 0.0235(16) 0.0247(17) 0.0013(12) -0.0025(15) -0.0089(14) C4 0.0411(19) 0.0196(15) 0.0266(16) -0.0026(12) 0.0047(15) -0.0034(14) C5 0.0281(16) 0.0163(13) 0.0314(17) -0.0029(12) 0.0102(14) -0.0040(12) C6 0.0233(15) 0.0129(13) 0.0344(17) 0.0004(12) 0.0053(13) -0.0039(12) C7 0.0234(15) 0.0201(15) 0.0445(19) 0.0011(14) 0.0059(15) 0.0004(13) C8 0.0231(16) 0.0199(15) 0.0433(19) 0.0045(13) -0.0028(15) 0.0018(13) C9 0.0220(15) 0.0146(13) 0.0338(17) 0.0018(12) -0.0016(13) -0.0037(12) C10 0.0251(16) 0.0172(14) 0.0296(17) 0.0028(12) -0.0067(13) -0.0072(12) C11 0.0332(18) 0.0280(17) 0.0338(18) 0.0003(14) -0.0102(15) -0.0004(14) C12 0.056(2) 0.0307(19) 0.039(2) 0.0111(15) -0.0131(19) -0.0014(18) N1 0.0240(13) 0.0127(11) 0.0227(13) 0.0007(9) 0.0017(11) -0.0040(10) N2 0.0214(12) 0.0150(11) 0.0278(13) -0.0006(9) 0.0028(11) -0.0034(10) Zn1 0.0214(3) 0.0182(3) 0.0220(3) -0.00006(18) 0.0012(2) -0.00002(19) 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 -1.00 0.0300 -1.00 0.00 0.00 0.0420 0.00 1.00 -1.00 0.3240 0.00 -1.00 1.00 0.2470 0.00 0.00 1.00 0.0330 0.00 0.00 -1.00 0.0480 1.00 1.00 -1.00 0.3140 1.00 0.00 1.00 0.0010 1.00 0.00 0.00 0.0200 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 C5 C1 C4 124.9(3) . . ? N1 C1 C4 110.2(3) . . ? N1 C1 C5 124.8(3) . . ? C10 C2 C3 125.4(3) 5_666 . ? N1 C2 C3 109.2(3) . . ? N1 C2 C10 125.4(3) . 5_666 ? C2 C3 H3 126.5 . . ? C4 C3 C2 107.1(3) . . ? C4 C3 H3 126.5 . . ? C1 C4 H4 126.5 . . ? C3 C4 C1 107.0(3) . . ? C3 C4 H4 126.5 . . ? C1 C5 H5 116.3 . . ? C6 C5 C1 127.3(3) . . ? C6 C5 H5 116.3 . . ? C5 C6 C7 124.5(3) . . ? N2 C6 C5 126.1(3) . . ? N2 C6 C7 109.5(3) . . ? C6 C7 H7 126.5 . . ? C8 C7 C6 107.1(3) . . ? C8 C7 H7 126.5 . . ? C7 C8 H8 126.3 . . ? C7 C8 C9 107.5(3) . . ? C9 C8 H8 126.3 . . ? C10 C9 C8 125.3(3) . . ? N2 C9 C8 108.6(3) . . ? N2 C9 C10 126.2(3) . . ? C2 C10 C11 117.8(3) 5_666 . ? C9 C10 C2 123.9(3) . 5_666 ? C9 C10 C11 118.3(3) . . ? C10 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C10 C11 C12 112.4(3) . . ? H11A C11 H11B 107.9 . . ? C12 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 N1 C2 106.6(3) . . ? C1 N1 Zn1 125.5(2) . . ? C2 N1 Zn1 128.0(2) . . ? C6 N2 C9 107.4(3) . . ? C6 N2 Zn1 124.6(2) . . ? C9 N2 Zn1 127.8(2) . . ? N1 Zn1 N1 180.00(13) . 5_666 ? N2 Zn1 N1 91.44(9) 5_666 5_666 ? N2 Zn1 N1 91.44(9) . . ? N2 Zn1 N1 88.56(9) . 5_666 ? N2 Zn1 N1 88.56(9) 5_666 . ? N2 Zn1 N2 180.0 . 5_666 ? 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 C1 C4 1.433(4) . ? C1 C5 1.399(4) . ? C1 N1 1.364(4) . ? C2 C3 1.447(4) . ? C2 C10 1.412(4) 5_666 ? C2 N1 1.376(4) . ? C3 H3 0.9500 . ? C3 C4 1.353(5) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C5 C6 1.381(5) . ? C6 C7 1.436(5) . ? C6 N2 1.372(4) . ? C7 H7 0.9500 . ? C7 C8 1.356(5) . ? C8 H8 0.9500 . ? C8 C9 1.449(4) . ? C9 C10 1.399(4) . ? C9 N2 1.374(4) . ? C10 C11 1.515(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.522(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N1 Zn1 2.049(3) . ? N2 Zn1 2.040(2) . ? 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 C1 C5 C6 C7 -175.9(3) . . . . ? C1 C5 C6 N2 3.3(5) . . . . ? C2 C3 C4 C1 -0.3(4) . . . . ? C2 C10 C11 C12 90.8(4) 5_666 . . . ? C3 C2 N1 C1 0.9(3) . . . . ? C3 C2 N1 Zn1 -179.09(19) . . . . ? C4 C1 C5 C6 179.1(3) . . . . ? C4 C1 N1 C2 -1.0(3) . . . . ? C4 C1 N1 Zn1 178.90(19) . . . . ? C5 C1 C4 C3 -177.6(3) . . . . ? C5 C1 N1 C2 177.4(3) . . . . ? C5 C1 N1 Zn1 -2.7(4) . . . . ? C5 C6 C7 C8 -179.1(3) . . . . ? C5 C6 N2 C9 178.9(3) . . . . ? C5 C6 N2 Zn1 -5.0(4) . . . . ? C6 C7 C8 C9 -0.7(3) . . . . ? C7 C6 N2 C9 -1.8(3) . . . . ? C7 C6 N2 Zn1 174.35(19) . . . . ? C7 C8 C9 C10 179.8(3) . . . . ? C7 C8 C9 N2 -0.4(3) . . . . ? C8 C9 C10 C2 174.7(3) . . . 5_666 ? C8 C9 C10 C11 -7.8(4) . . . . ? C8 C9 N2 C6 1.3(3) . . . . ? C8 C9 N2 Zn1 -174.61(19) . . . . ? C9 C10 C11 C12 -86.9(4) . . . . ? C10 C2 C3 C4 -178.4(3) 5_666 . . . ? C10 C2 N1 C1 178.9(3) 5_666 . . . ? C10 C2 N1 Zn1 -1.1(4) 5_666 . . . ? C10 C9 N2 C6 -178.8(3) . . . . ? C10 C9 N2 Zn1 5.2(4) . . . . ? N1 C1 C4 C3 0.8(4) . . . . ? N1 C1 C5 C6 0.9(5) . . . . ? N1 C2 C3 C4 -0.3(4) . . . . ? N2 C6 C7 C8 1.5(3) . . . . ? N2 C9 C10 C2 -5.1(5) . . . 5_666 ? N2 C9 C10 C11 172.4(3) . . . . ?