#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:02:21 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304784 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064314.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_7064314 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 'C22 H16 N4 O2 Zn, 2(C2 H3 N)' _chemical_formula_sum 'C26 H22 N6 O2 Zn' _chemical_formula_weight 515.86 _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 mixed _atom_sites_solution_primary dual _audit_creation_date 2023-12-13 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2025-10-17 deposited with the CCDC. 2025-12-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 110.305(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.5829(5) _cell_length_b 9.6101(5) _cell_length_c 12.9002(8) _cell_measurement_reflns_used 9927 _cell_measurement_temperature 100.00 _cell_measurement_theta_max 28.33 _cell_measurement_theta_min 2.27 _cell_volume 1114.19(11) _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 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.0459 _diffrn_reflns_av_unetI/netI 0.0283 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 16792 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.876 _diffrn_reflns_theta_min 2.707 _diffrn_source_current 1.4 _diffrn_source_power 0.07 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.141 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6427 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1113 before and 0.0622 after correction. The Ratio of minimum to maximum transmission is 0.8619. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear dark red' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.538 _exptl_crystal_description plate _exptl_crystal_F_000 532 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.191 _exptl_crystal_size_min 0.032 _refine_diff_density_max 1.120 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.076 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2657 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0322 _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^)+(0.0441P)^2^+1.0971P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.0891 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2427 _reflns_number_total 2657 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj04118j2.cif _cod_data_source_block mo_ncsu_pn69_0m_a _cod_database_code 7064314 _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 0.964 _shelx_estimated_absorpt_t_min 0.622 _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, All O(H) groups 2.a Secondary CH2 refined with riding coordinates: C10(H10A,H10B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C6(H6), C7(H7), C11(H11) 2.c Idealised Me refined as rotating group: C12(H12A,H12B,H12C) ; _shelx_res_file ; TITL mo_NCSU_PN69_0m_a.res in P2(1)/c mo_ncsu_pn69_0m_a.res created by SHELXL-2019/1 at 10:05:42 on 13-Dec-2023 REM Old TITL mo_NCSU_PN69_0m in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.074, Rweak 0.002, Alpha 0.015 REM 0.389 for 146 systematic absences, Orientation as input REM Formula found by SHELXT: C26 N6 O2 Zn CELL 0.71073 9.5829 9.6101 12.9002 90 110.305 90 ZERR 2 0.0005 0.0005 0.0008 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O Zn UNIT 52 44 12 4 2 L.S. 10 PLAN 5 SIZE 0.032 0.191 0.46 TEMP -173.15 CONF BOND LIST 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.044100 1.097100 FVAR 0.61609 ZN1 5 0.500000 0.500000 0.500000 10.50000 0.01474 0.01066 = 0.01043 0.00244 0.00497 -0.00040 O1 4 0.517033 0.170071 0.873975 11.00000 0.03067 0.01421 = 0.01378 0.00195 0.01175 0.00319 H1 2 0.459180 0.223371 0.870903 11.00000 -1.50000 N1 3 0.341847 0.603791 0.373668 11.00000 0.01781 0.01104 = 0.01208 -0.00030 0.00535 0.00119 N2 3 0.338964 0.384597 0.532591 11.00000 0.01832 0.01086 = 0.01263 -0.00051 0.00725 -0.00148 N3 3 0.329437 0.402281 0.877201 11.00000 0.06683 0.02302 = 0.04009 0.00812 0.03472 0.01230 C1 1 0.364941 0.706572 0.307815 11.00000 0.02559 0.01112 = 0.01103 0.00053 0.00657 0.00373 C2 1 0.223361 0.749814 0.228679 11.00000 0.02646 0.01905 = 0.01427 0.00366 0.00514 0.00621 AFIX 43 H2 2 0.207960 0.819788 0.173810 11.00000 -1.20000 AFIX 0 C3 1 0.116766 0.671622 0.247593 11.00000 0.02114 0.02229 = 0.01827 0.00179 0.00252 0.00535 AFIX 43 H3 2 0.012706 0.675869 0.208225 11.00000 -1.20000 AFIX 0 C4 1 0.192263 0.580289 0.339495 11.00000 0.01834 0.01629 = 0.01494 -0.00054 0.00377 0.00309 C5 1 0.189310 0.397576 0.477265 11.00000 0.01818 0.01548 = 0.01935 -0.00384 0.01003 -0.00380 C6 1 0.109181 0.305289 0.525474 11.00000 0.02181 0.02041 = 0.02425 -0.00191 0.01182 -0.00636 AFIX 43 H6 2 0.004250 0.295014 0.502942 11.00000 -1.20000 AFIX 0 C7 1 0.212033 0.236549 0.608614 11.00000 0.02642 0.01675 = 0.02215 -0.00198 0.01498 -0.00672 AFIX 43 H7 2 0.192923 0.168887 0.655700 11.00000 -1.20000 AFIX 0 C8 1 0.357778 0.285485 0.612653 11.00000 0.02527 0.01062 = 0.01437 -0.00212 0.01142 -0.00353 C9 1 0.495736 0.239019 0.685578 11.00000 0.02783 0.01069 = 0.01123 -0.00053 0.01038 0.00000 C10 1 0.495822 0.121565 0.764245 11.00000 0.03254 0.01227 = 0.01454 0.00183 0.01174 0.00037 AFIX 23 H10A 2 0.399993 0.071089 0.735265 11.00000 -1.20000 H10B 2 0.576183 0.055170 0.767395 11.00000 -1.20000 AFIX 0 C11 1 0.122386 0.485678 0.387324 11.00000 0.01516 0.02024 = 0.01926 -0.00237 0.00514 0.00036 AFIX 43 H11 2 0.017085 0.480391 0.355118 11.00000 -1.20000 AFIX 0 C12 1 0.229727 0.587324 0.979048 11.00000 0.05589 0.02052 = 0.04070 -0.00173 0.03218 0.00072 AFIX 137 H12A 2 0.295334 0.668775 0.995507 11.00000 -1.50000 H12B 2 0.226436 0.547787 1.048188 11.00000 -1.50000 H12C 2 0.129299 0.615304 0.932153 11.00000 -1.50000 AFIX 0 C13 1 0.286350 0.483485 0.921548 11.00000 0.03779 0.01953 = 0.02771 0.00585 0.01723 0.00325 HKLF 4 REM mo_NCSU_PN69_0m_a.res in P2(1)/c REM wR2 = 0.0891, GooF = S = 1.058, Restrained GooF = 1.058 for all data REM R1 = 0.0322 for 2427 Fo > 4sig(Fo) and 0.0352 for all 2657 data REM 164 parameters refined using 0 restraints END WGHT 0.0441 1.0971 REM Highest difference peak 1.120, deepest hole -0.317, 1-sigma level 0.076 Q1 1 0.0197 0.6682 0.9569 11.00000 0.05 1.12 Q2 1 -0.1015 0.6325 0.1783 11.00000 0.05 0.73 Q3 1 0.4911 0.1837 0.7205 11.00000 0.05 0.41 Q4 1 0.1479 0.6223 0.2917 11.00000 0.05 0.41 Q5 1 0.1255 0.1248 0.6871 11.00000 0.05 0.40 ; _shelx_res_checksum 82135 _olex2_submission_special_instructions 'No special instructions were received' 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_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 Zn1 Zn 0.500000 0.500000 0.500000 0.01179(10) Uani 1 2 d S . P . . O1 O 0.51703(16) 0.17007(13) 0.87397(10) 0.0185(3) Uani 1 1 d . . . . . H1 H 0.459(3) 0.223(3) 0.871(2) 0.028 Uiso 1 1 d . U . . . N1 N 0.34185(16) 0.60379(14) 0.37367(12) 0.0136(3) Uani 1 1 d . . . . . N2 N 0.33896(16) 0.38460(14) 0.53259(12) 0.0134(3) Uani 1 1 d . . . . . N3 N 0.3294(3) 0.4023(2) 0.87720(18) 0.0391(5) Uani 1 1 d . . . . . C1 C 0.3649(2) 0.70657(17) 0.30781(14) 0.0159(3) Uani 1 1 d . . . . . C2 C 0.2234(2) 0.74981(19) 0.22868(15) 0.0204(4) Uani 1 1 d . . . . . H2 H 0.207960 0.819788 0.173810 0.025 Uiso 1 1 calc R U . . . C3 C 0.1168(2) 0.6716(2) 0.24759(16) 0.0217(4) Uani 1 1 d . . . . . H3 H 0.012706 0.675869 0.208225 0.026 Uiso 1 1 calc R U . . . C4 C 0.19226(19) 0.58029(18) 0.33950(14) 0.0170(3) Uani 1 1 d . . . . . C5 C 0.18931(19) 0.39758(18) 0.47727(15) 0.0167(3) Uani 1 1 d . . . . . C6 C 0.1092(2) 0.30529(19) 0.52547(16) 0.0212(4) Uani 1 1 d . . . . . H6 H 0.004250 0.295014 0.502942 0.025 Uiso 1 1 calc R U . . . C7 C 0.2120(2) 0.23655(19) 0.60861(16) 0.0200(4) Uani 1 1 d . . . . . H7 H 0.192923 0.168887 0.655700 0.024 Uiso 1 1 calc R U . . . C8 C 0.3578(2) 0.28548(17) 0.61265(14) 0.0156(3) Uani 1 1 d . . . . . C9 C 0.4957(2) 0.23902(17) 0.68558(14) 0.0156(3) Uani 1 1 d . . . . . C10 C 0.4958(2) 0.12157(18) 0.76425(15) 0.0188(4) Uani 1 1 d . . . . . H10A H 0.399993 0.071089 0.735265 0.023 Uiso 1 1 calc R U . . . H10B H 0.576183 0.055170 0.767395 0.023 Uiso 1 1 calc R U . . . C11 C 0.1224(2) 0.48568(18) 0.38732(16) 0.0184(4) Uani 1 1 d . . . . . H11 H 0.017085 0.480391 0.355118 0.022 Uiso 1 1 calc R U . . . C12 C 0.2297(3) 0.5873(2) 0.9790(2) 0.0350(5) Uani 1 1 d . . . . . H12A H 0.295334 0.668775 0.995507 0.052 Uiso 1 1 calc R U . . . H12B H 0.226436 0.547787 1.048188 0.052 Uiso 1 1 calc R U . . . H12C H 0.129299 0.615304 0.932153 0.052 Uiso 1 1 calc R U . . . C13 C 0.2863(3) 0.4835(2) 0.92155(19) 0.0268(4) Uani 1 1 d . . . . . 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 Zn1 0.01474(15) 0.01066(15) 0.01043(15) 0.00244(9) 0.00497(11) -0.00040(9) O1 0.0307(7) 0.0142(6) 0.0138(6) 0.0019(5) 0.0118(5) 0.0032(5) N1 0.0178(7) 0.0110(6) 0.0121(7) -0.0003(5) 0.0053(5) 0.0012(5) N2 0.0183(7) 0.0109(6) 0.0126(7) -0.0005(5) 0.0073(5) -0.0015(5) N3 0.0668(14) 0.0230(9) 0.0401(11) 0.0081(8) 0.0347(11) 0.0123(9) C1 0.0256(9) 0.0111(7) 0.0110(8) 0.0005(6) 0.0066(7) 0.0037(6) C2 0.0265(9) 0.0191(8) 0.0143(8) 0.0037(7) 0.0051(7) 0.0062(7) C3 0.0211(9) 0.0223(9) 0.0183(9) 0.0018(7) 0.0025(7) 0.0053(7) C4 0.0183(8) 0.0163(8) 0.0149(8) -0.0005(6) 0.0038(6) 0.0031(6) C5 0.0182(8) 0.0155(8) 0.0193(8) -0.0038(6) 0.0100(7) -0.0038(6) C6 0.0218(8) 0.0204(8) 0.0243(9) -0.0019(7) 0.0118(7) -0.0064(7) C7 0.0264(9) 0.0167(8) 0.0221(9) -0.0020(7) 0.0150(7) -0.0067(7) C8 0.0253(9) 0.0106(7) 0.0144(8) -0.0021(6) 0.0114(7) -0.0035(6) C9 0.0278(9) 0.0107(7) 0.0112(7) -0.0005(6) 0.0104(7) 0.0000(6) C10 0.0325(9) 0.0123(7) 0.0145(8) 0.0018(6) 0.0117(7) 0.0004(7) C11 0.0152(8) 0.0202(8) 0.0193(9) -0.0024(6) 0.0051(7) 0.0004(6) C12 0.0559(14) 0.0205(9) 0.0407(13) -0.0017(9) 0.0322(12) 0.0007(9) C13 0.0378(11) 0.0195(9) 0.0277(11) 0.0058(8) 0.0172(9) 0.0032(8) 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' O O 0.0106 0.0060 '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 0.00 0.0160 -1.00 1.00 1.00 0.2010 -1.00 0.00 -1.00 0.0490 0.00 -1.00 -1.00 0.0660 0.00 1.00 1.00 0.2350 0.00 -1.00 1.00 0.0860 0.00 1.00 -1.00 0.0910 0.00 0.00 -1.00 0.0810 0.00 0.00 1.00 0.1360 1.00 0.00 0.00 0.0100 1.00 -1.00 -1.00 0.0580 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 O1 Zn1 O1 180.0 4_565 2_656 ? N1 Zn1 O1 90.11(5) 3_666 4_565 ? N1 Zn1 O1 89.89(5) 3_666 2_656 ? N1 Zn1 O1 90.11(5) . 2_656 ? N1 Zn1 O1 89.89(5) . 4_565 ? N1 Zn1 N1 180.0 3_666 . ? N1 Zn1 N2 88.59(6) 3_666 . ? N1 Zn1 N2 91.41(6) . . ? N1 Zn1 N2 88.59(6) . 3_666 ? N1 Zn1 N2 91.41(6) 3_666 3_666 ? N2 Zn1 O1 89.80(5) . 2_656 ? N2 Zn1 O1 90.20(5) . 4_565 ? N2 Zn1 O1 89.80(5) 3_666 4_565 ? N2 Zn1 O1 90.20(5) 3_666 2_656 ? N2 Zn1 N2 180.0 . 3_666 ? Zn1 O1 H1 107(2) 2_646 . ? C10 O1 Zn1 115.85(10) . 2_646 ? C10 O1 H1 109(2) . . ? C1 N1 Zn1 127.42(12) . . ? C4 N1 Zn1 125.32(12) . . ? C4 N1 C1 107.26(14) . . ? C5 N2 Zn1 124.66(11) . . ? C5 N2 C8 107.25(14) . . ? C8 N2 Zn1 128.06(12) . . ? N1 C1 C2 109.32(15) . . ? N1 C1 C9 125.72(15) . 3_666 ? C9 C1 C2 124.96(16) 3_666 . ? C1 C2 H2 126.4 . . ? C3 C2 C1 107.11(16) . . ? C3 C2 H2 126.4 . . ? C2 C3 H3 126.6 . . ? C2 C3 C4 106.80(16) . . ? C4 C3 H3 126.6 . . ? N1 C4 C3 109.51(16) . . ? N1 C4 C11 125.26(16) . . ? C11 C4 C3 125.21(17) . . ? N2 C5 C6 109.66(16) . . ? N2 C5 C11 125.71(16) . . ? C11 C5 C6 124.63(17) . . ? C5 C6 H6 126.5 . . ? C7 C6 C5 106.93(16) . . ? C7 C6 H6 126.5 . . ? C6 C7 H7 126.4 . . ? C6 C7 C8 107.26(16) . . ? C8 C7 H7 126.4 . . ? N2 C8 C7 108.88(15) . . ? N2 C8 C9 125.00(16) . . ? C9 C8 C7 126.12(16) . . ? C1 C9 C10 117.07(16) 3_666 . ? C8 C9 C1 125.11(15) . 3_666 ? C8 C9 C10 117.82(16) . . ? O1 C10 C9 112.63(14) . . ? O1 C10 H10A 109.1 . . ? O1 C10 H10B 109.1 . . ? C9 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C4 C11 C5 127.55(17) . . ? C4 C11 H11 116.2 . . ? C5 C11 H11 116.2 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? N3 C13 C12 179.4(2) . . ? 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 Zn1 O1 2.3505(12) 2_656 ? Zn1 O1 2.3505(12) 4_565 ? Zn1 N1 2.0576(14) . ? Zn1 N1 2.0575(14) 3_666 ? Zn1 N2 2.0588(14) . ? Zn1 N2 2.0588(14) 3_666 ? O1 H1 0.75(3) . ? O1 C10 1.436(2) . ? N1 C1 1.370(2) . ? N1 C4 1.364(2) . ? N2 C5 1.368(2) . ? N2 C8 1.370(2) . ? N3 C13 1.127(3) . ? C1 C2 1.447(2) . ? C1 C9 1.409(2) 3_666 ? C2 H2 0.9500 . ? C2 C3 1.357(3) . ? C3 H3 0.9500 . ? C3 C4 1.451(2) . ? C4 C11 1.394(3) . ? C5 C6 1.447(2) . ? C5 C11 1.399(3) . ? C6 H6 0.9500 . ? C6 C7 1.351(3) . ? C7 H7 0.9500 . ? C7 C8 1.457(2) . ? C8 C9 1.403(2) . ? C9 C10 1.518(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C12 C13 1.456(3) . ? 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 Zn1 O1 C10 C9 175.24(11) 2_646 . . . ? Zn1 N1 C1 C2 179.40(11) . . . . ? Zn1 N1 C1 C9 0.2(2) . . . 3_666 ? Zn1 N1 C4 C3 -179.10(11) . . . . ? Zn1 N1 C4 C11 2.4(3) . . . . ? Zn1 N2 C5 C6 -177.19(11) . . . . ? Zn1 N2 C5 C11 3.1(2) . . . . ? Zn1 N2 C8 C7 177.05(11) . . . . ? Zn1 N2 C8 C9 -3.4(2) . . . . ? N1 C1 C2 C3 -0.4(2) . . . . ? N1 C4 C11 C5 -0.3(3) . . . . ? N2 C5 C6 C7 -0.7(2) . . . . ? N2 C5 C11 C4 -2.8(3) . . . . ? N2 C8 C9 C1 4.3(3) . . . 3_666 ? N2 C8 C9 C10 -176.08(15) . . . . ? C1 N1 C4 C3 0.24(19) . . . . ? C1 N1 C4 C11 -178.23(17) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? C1 C9 C10 O1 78.6(2) 3_666 . . . ? C2 C3 C4 N1 -0.5(2) . . . . ? C2 C3 C4 C11 177.99(17) . . . . ? C3 C4 C11 C5 -178.50(18) . . . . ? C4 N1 C1 C2 0.07(19) . . . . ? C4 N1 C1 C9 -179.12(16) . . . 3_666 ? C5 N2 C8 C7 -1.38(19) . . . . ? C5 N2 C8 C9 178.21(16) . . . . ? C5 C6 C7 C8 -0.1(2) . . . . ? C6 C5 C11 C4 177.54(18) . . . . ? C6 C7 C8 N2 1.0(2) . . . . ? C6 C7 C8 C9 -178.63(17) . . . . ? C7 C8 C9 C1 -176.18(17) . . . 3_666 ? C7 C8 C9 C10 3.4(3) . . . . ? C8 N2 C5 C6 1.30(19) . . . . ? C8 N2 C5 C11 -178.41(16) . . . . ? C8 C9 C10 O1 -101.02(19) . . . . ? C9 C1 C2 C3 178.83(17) 3_666 . . . ? C11 C5 C6 C7 179.00(17) . . . . ?