#------------------------------------------------------------------------------ #$Date: 2022-12-24 20:12:14 +0000 (Sat, 24 Dec 2022) $ #$Revision: 280037 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519436.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_4519436 loop_ _publ_author_name 'Khaoula Chair' 'Cesar Augusto Luna Caceres' 'Sanil Rajak' 'Olivier Schott' 'Gustavo E. Ram\'irez-Caballero' 'Thierry Maris' 'Garry S. Hanan' 'Adam Duong' _publ_section_title ; Photocatalytic Carbon Dioxide Reduction and Density Functional Theory Investigation of 2,6-(Pyridin-2-yl)-1,3,5-triazine-2,4-diamine and Its Cobalt and Nickel Complexes ; _journal_name_full 'ACS Applied Energy Materials' _journal_page_first 11077 _journal_page_last 11090 _journal_paper_doi 10.1021/acsaem.2c01702 _journal_volume 5 _journal_year 2022 _chemical_formula_moiety 'C22 H22 N22 Ni, 2(Cl O4)' _chemical_formula_sum 'C22 H22 Cl2 N22 Ni O8' _chemical_formula_weight 852.22 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2017-10-02 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _cell_angle_alpha 90 _cell_angle_beta 98.829(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.6780(8) _cell_length_b 10.7344(4) _cell_length_c 16.0745(7) _cell_measurement_reflns_used 4929 _cell_measurement_temperature 150 _cell_measurement_theta_max 60.678 _cell_measurement_theta_min 4.638 _cell_volume 3184.7(2) _computing_cell_refinement ; SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.' ; _computing_data_collection ; APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.' ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 150 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.24 _diffrn_detector_type 'Bruker Photon 100 CMOS Detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_unetI/netI 0.0257 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3669 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.666 _diffrn_reflns_theta_min 4.145 _diffrn_source 'Metal Jet' _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _exptl_absorpt_coefficient_mu 4.852 _exptl_absorpt_correction_T_max 0.121 _exptl_absorpt_correction_T_min 0.031 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2012/1 (Bruker,2012) was used for absorption correction. For component 1: wR2(int) was 0.1216 before and 0.0482 after correction. The Ratio of minimum to maximum transmission not present. The \l/2 correction factor is Not present For component 2: wR2(int) was 0.1851 before and 0.0692 after correction. The Ratio of minimum to maximum transmission is 0.26. The \l/2 correction factor is Not present Final HKLF 4 output contains 39508 reflections, Rint = 0.0550 (35345 with I > 3sig(I), Rint = 0.0546) ; _exptl_crystal_colour 'clear light blue' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 1.777 _exptl_crystal_description block _exptl_crystal_F_000 1736 _exptl_crystal_recrystallization_method 'crystallized from Et2O' _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _refine_diff_density_max 1.074 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.202 _refine_ls_extinction_coef 0.0065(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)' _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 251 _refine_ls_number_reflns 3669 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.105 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0487 _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^)+(0.0953P)^2^+1.1928P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1266 _refine_ls_wR_factor_ref 0.1268 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 3638 _reflns_number_total 3669 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 3-ada138.cif _cod_data_source_block ada138 _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. Automatic conversion script Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas ; _cod_database_code 4519436 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -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 Ni1 Ni 0.500000 0.36104(4) 0.250000 0.02747(16) Uani 1 2 d S T P . . Cl1 Cl 0.28481(3) 0.57499(5) 0.46713(3) 0.03557(17) Uani 1 1 d . . . . . O2 O 0.34551(10) 0.62899(16) 0.52267(11) 0.0407(4) Uani 1 1 d . . . . . O3 O 0.22315(9) 0.56342(18) 0.51098(11) 0.0433(4) Uani 1 1 d . . . . . N1 N 0.60698(10) 0.36141(14) 0.24156(12) 0.0285(4) Uani 1 1 d . . . . . N2 N 0.51183(10) 0.20858(16) 0.16231(11) 0.0301(4) Uani 1 1 d . . . . . N9 N 0.65065(11) 0.63081(17) 0.36785(12) 0.0324(4) Uani 1 1 d . . . . . N7 N 0.54403(10) 0.50531(17) 0.33881(11) 0.0301(4) Uani 1 1 d . . . . . O1 O 0.30512(11) 0.45269(18) 0.44197(12) 0.0474(4) Uani 1 1 d . . . . . O4 O 0.26710(12) 0.6526(2) 0.39427(13) 0.0518(5) Uani 1 1 d . . . . . N8 N 0.54658(11) 0.68054(18) 0.43145(13) 0.0360(4) Uani 1 1 d . . . . . N5 N 0.39399(11) 0.14192(19) 0.12642(15) 0.0404(5) Uani 1 1 d . . . . . H5A H 0.361724 0.085051 0.107165 0.048 Uiso 1 1 calc R . . . . H5B H 0.379748 0.214575 0.143265 0.048 Uiso 1 1 calc R . . . . N11 N 0.64881(12) 0.80380(19) 0.45128(13) 0.0407(4) Uani 1 1 d . . . . . H11A H 0.627428 0.853250 0.483583 0.049 Uiso 1 1 calc R . . . . H11B H 0.693055 0.820418 0.442067 0.049 Uiso 1 1 calc R . . . . N4 N 0.60714(10) 0.07625(17) 0.12958(12) 0.0331(4) Uani 1 1 d . . . . . N6 N 0.57723(12) -0.12221(19) 0.08263(15) 0.0410(5) Uani 1 1 d . . . . . H6A H 0.545402 -0.181351 0.066853 0.049 Uiso 1 1 calc R . . . . H6B H 0.623707 -0.136388 0.083212 0.049 Uiso 1 1 calc R . . . . N3 N 0.48365(11) 0.00601(18) 0.10372(13) 0.0379(4) Uani 1 1 d . . . . . N10 N 0.44786(11) 0.55292(19) 0.40737(13) 0.0387(4) Uani 1 1 d . . . . . H10A H 0.427039 0.599636 0.441765 0.046 Uiso 1 1 calc R . . . . H10B H 0.424844 0.487943 0.382880 0.046 Uiso 1 1 calc R . . . . C5 C 0.65105(11) 0.44599(19) 0.28431(12) 0.0297(4) Uani 1 1 d . . . . . C9 C 0.61306(11) 0.53493(19) 0.33325(13) 0.0299(4) Uani 1 1 d . . . . . C2 C 0.70899(12) 0.26555(19) 0.19438(13) 0.0316(4) Uani 1 1 d . . . . . H2 H 0.727908 0.203372 0.161744 0.038 Uiso 1 1 calc R . . . . C1 C 0.63532(11) 0.27224(19) 0.19799(12) 0.0291(4) Uani 1 1 d . . . . . C10 C 0.51419(12) 0.5805(2) 0.39240(13) 0.0322(4) Uani 1 1 d . . . . . C4 C 0.72559(11) 0.4438(2) 0.28571(13) 0.0315(4) Uani 1 1 d . . . . . H4 H 0.756056 0.503483 0.317252 0.038 Uiso 1 1 calc R . . . . C11 C 0.61405(12) 0.7034(2) 0.41620(14) 0.0341(4) Uani 1 1 d . . . . . C3 C 0.75421(13) 0.3523(2) 0.23985(15) 0.0330(4) Uani 1 1 d . . . . . H3 H 0.804981 0.348895 0.239487 0.040 Uiso 1 1 calc R . . . . C7 C 0.46442(12) 0.1180(2) 0.13007(14) 0.0334(4) Uani 1 1 d . . . . . C6 C 0.58150(11) 0.1792(2) 0.15928(12) 0.0294(4) Uani 1 1 d . . . . . C8 C 0.55506(13) -0.0113(2) 0.10561(14) 0.0353(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 Ni1 0.0239(2) 0.0279(2) 0.0308(2) 0.000 0.00491(16) 0.000 Cl1 0.0295(3) 0.0413(3) 0.0356(3) -0.00086(18) 0.00377(19) 0.00054(19) O2 0.0346(9) 0.0464(10) 0.0406(8) -0.0079(6) 0.0041(7) -0.0029(7) O3 0.0330(8) 0.0530(10) 0.0447(9) 0.0049(7) 0.0084(7) 0.0013(7) N1 0.0262(8) 0.0284(8) 0.0316(8) -0.0006(6) 0.0064(6) -0.0007(6) N2 0.0277(8) 0.0298(8) 0.0330(8) -0.0011(6) 0.0055(6) 0.0006(7) N9 0.0299(9) 0.0305(9) 0.0374(9) -0.0025(6) 0.0073(7) -0.0020(7) N7 0.0286(8) 0.0295(8) 0.0325(8) -0.0024(6) 0.0055(6) 0.0001(7) O1 0.0470(10) 0.0460(10) 0.0491(9) -0.0110(7) 0.0073(8) -0.0004(8) O4 0.0438(10) 0.0654(13) 0.0457(10) 0.0151(8) 0.0056(8) 0.0039(9) N8 0.0354(10) 0.0309(9) 0.0437(9) -0.0053(7) 0.0126(8) -0.0006(7) N5 0.0279(10) 0.0426(11) 0.0495(11) -0.0119(8) 0.0021(8) -0.0014(7) N11 0.0393(10) 0.0339(10) 0.0518(11) -0.0111(8) 0.0161(8) -0.0056(8) N4 0.0303(9) 0.0309(9) 0.0385(9) -0.0047(7) 0.0067(7) -0.0007(7) N6 0.0355(10) 0.0311(9) 0.0565(12) -0.0096(8) 0.0076(9) -0.0007(8) N3 0.0330(9) 0.0337(9) 0.0469(10) -0.0080(8) 0.0055(8) -0.0033(8) N10 0.0328(9) 0.0384(10) 0.0476(10) -0.0083(8) 0.0146(8) -0.0036(8) C5 0.0287(9) 0.0289(9) 0.0321(9) -0.0005(7) 0.0059(7) 0.0001(7) C9 0.0289(9) 0.0291(9) 0.0319(9) -0.0004(7) 0.0052(7) 0.0000(7) C2 0.0291(10) 0.0305(9) 0.0363(10) -0.0003(7) 0.0085(8) 0.0009(8) C1 0.0281(9) 0.0279(9) 0.0318(9) 0.0002(7) 0.0063(7) 0.0007(7) C10 0.0298(10) 0.0315(9) 0.0363(10) 0.0016(7) 0.0085(8) 0.0023(8) C4 0.0262(9) 0.0317(10) 0.0366(9) -0.0022(7) 0.0054(7) -0.0022(7) C11 0.0350(11) 0.0305(10) 0.0375(10) -0.0020(8) 0.0080(8) -0.0019(8) C3 0.0270(10) 0.0346(11) 0.0380(10) 0.0009(7) 0.0064(8) 0.0004(8) C7 0.0304(10) 0.0351(10) 0.0346(10) -0.0031(8) 0.0044(8) -0.0015(8) C6 0.0285(9) 0.0303(9) 0.0299(8) -0.0002(7) 0.0058(7) -0.0003(8) C8 0.0352(10) 0.0314(10) 0.0391(10) -0.0029(8) 0.0056(8) -0.0023(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0140 0.0070 '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' Cl Cl 0.3280 0.5430 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -1.3350 3.2900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0390 0.0250 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 N1 Ni1 N1 179.77(9) 2_655 . N1 Ni1 N2 104.04(7) 2_655 . N1 Ni1 N2 76.13(7) 2_655 2_655 N1 Ni1 N2 104.04(7) . 2_655 N1 Ni1 N2 76.14(7) . . N1 Ni1 N7 76.43(7) 2_655 2_655 N1 Ni1 N7 103.41(7) . 2_655 N1 Ni1 N7 103.41(7) 2_655 . N1 Ni1 N7 76.43(7) . . N2 Ni1 N2 83.47(9) . 2_655 N7 Ni1 N2 100.04(6) . 2_655 N7 Ni1 N2 152.36(7) 2_655 2_655 N7 Ni1 N2 152.36(7) . . N7 Ni1 N2 100.04(6) 2_655 . N7 Ni1 N7 89.46(9) 2_655 . O3 Cl1 O2 109.87(11) . . O1 Cl1 O2 108.78(11) . . O1 Cl1 O3 108.81(12) . . O4 Cl1 O2 109.32(12) . . O4 Cl1 O3 110.31(12) . . O4 Cl1 O1 109.73(13) . . C5 N1 Ni1 120.10(14) . . C5 N1 C1 119.33(19) . . C1 N1 Ni1 120.42(14) . . C7 N2 Ni1 130.77(15) . . C6 N2 Ni1 113.02(14) . . C6 N2 C7 113.23(18) . . C9 N9 C11 114.02(19) . . C9 N7 Ni1 113.19(13) . . C9 N7 C10 113.08(18) . . C10 N7 Ni1 133.31(15) . . C10 N8 C11 115.46(19) . . H5A N5 H5B 120.0 . . C7 N5 H5A 120.0 . . C7 N5 H5B 120.0 . . H11A N11 H11B 120.0 . . C11 N11 H11A 120.0 . . C11 N11 H11B 120.0 . . C6 N4 C8 113.31(19) . . H6A N6 H6B 120.0 . . C8 N6 H6A 120.0 . . C8 N6 H6B 120.0 . . C7 N3 C8 115.47(19) . . H10A N10 H10B 120.0 . . C10 N10 H10A 120.0 . . C10 N10 H10B 120.0 . . N1 C5 C9 113.64(18) . . N1 C5 C4 122.10(19) . . C4 C5 C9 124.15(19) . . N9 C9 N7 127.6(2) . . N9 C9 C5 117.26(19) . . N7 C9 C5 115.11(18) . . C1 C2 H2 121.0 . . C3 C2 H2 121.0 . . C3 C2 C1 118.1(2) . . N1 C1 C2 122.12(19) . . N1 C1 C6 113.75(18) . . C2 C1 C6 124.03(18) . . N8 C10 N7 124.9(2) . . N10 C10 N7 117.7(2) . . N10 C10 N8 117.36(19) . . C5 C4 H4 120.9 . . C3 C4 C5 118.1(2) . . C3 C4 H4 120.9 . . N8 C11 N9 124.7(2) . . N11 C11 N9 116.7(2) . . N11 C11 N8 118.6(2) . . C2 C3 H3 119.9 . . C4 C3 C2 120.2(2) . . C4 C3 H3 119.9 . . N5 C7 N2 117.3(2) . . N5 C7 N3 118.0(2) . . N3 C7 N2 124.7(2) . . N2 C6 C1 115.05(18) . . N4 C6 N2 127.9(2) . . N4 C6 C1 117.02(18) . . N6 C8 N4 117.1(2) . . N6 C8 N3 117.9(2) . . N3 C8 N4 125.0(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Ni1 N1 2.0234(19) 2_655 Ni1 N1 2.0234(19) . Ni1 N2 2.1931(17) 2_655 Ni1 N2 2.1931(17) . Ni1 N7 2.1800(17) 2_655 Ni1 N7 2.1801(17) . Cl1 O2 1.4519(18) . Cl1 O3 1.4449(18) . Cl1 O1 1.4416(19) . Cl1 O4 1.434(2) . N1 C5 1.342(3) . N1 C1 1.342(3) . N2 C7 1.363(3) . N2 C6 1.347(3) . N9 C9 1.320(3) . N9 C11 1.357(3) . N7 C9 1.344(3) . N7 C10 1.361(3) . N8 C10 1.340(3) . N8 C11 1.343(3) . N5 H5A 0.8800 . N5 H5B 0.8800 . N5 C7 1.333(3) . N11 H11A 0.8800 . N11 H11B 0.8800 . N11 C11 1.337(3) . N4 C6 1.323(3) . N4 C8 1.365(3) . N6 H6A 0.8800 . N6 H6B 0.8800 . N6 C8 1.331(3) . N3 C7 1.342(3) . N3 C8 1.343(3) . N10 H10A 0.8800 . N10 H10B 0.8800 . N10 C10 1.331(3) . C5 C9 1.485(3) . C5 C4 1.389(3) . C2 H2 0.9500 . C2 C1 1.388(3) . C2 C3 1.388(3) . C1 C6 1.484(3) . C4 H4 0.9500 . C4 C3 1.384(3) . C3 H3 0.9500 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N5 H5A O3 0.88 2.29 2.982(3) 135.3 4_545 yes N5 H5A O4 0.88 2.51 2.978(3) 114.0 4_545 yes N5 H5B O2 0.88 2.57 3.031(3) 113.5 6_565 yes N5 H5B N1 0.88 2.42 3.173(3) 144.5 2_655 yes N11 H11A N4 0.88 2.55 3.341(3) 150.2 6_566 yes N11 H11B O1 0.88 2.53 3.352(3) 155.9 3 yes N6 H6A N8 0.88 2.27 3.118(3) 161.0 2_645 yes N6 H6B O3 0.88 2.46 3.181(3) 138.9 8 yes N10 H10A O2 0.88 2.17 2.974(3) 151.3 . yes N10 H10B N1 0.88 2.42 3.202(3) 149.0 2_655 yes N10 H10B O1 0.88 2.59 3.005(3) 110.0 . yes 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 Ni1 N1 C5 C9 -1.5(2) . . . . Ni1 N1 C5 C4 174.86(16) . . . . Ni1 N1 C1 C2 -176.56(16) . . . . Ni1 N1 C1 C6 0.0(2) . . . . Ni1 N2 C7 N5 24.7(3) . . . . Ni1 N2 C7 N3 -153.66(18) . . . . Ni1 N2 C6 N4 162.64(18) . . . . Ni1 N2 C6 C1 -14.2(2) . . . . Ni1 N7 C9 N9 168.07(18) . . . . Ni1 N7 C9 C5 -13.9(2) . . . . Ni1 N7 C10 N8 -166.85(17) . . . . Ni1 N7 C10 N10 13.2(3) . . . . N1 C5 C9 N9 -171.18(18) . . . . N1 C5 C9 N7 10.6(3) . . . . N1 C5 C4 C3 1.3(3) . . . . N1 C1 C6 N2 9.9(3) . . . . N1 C1 C6 N4 -167.24(18) . . . . C5 N1 C1 C2 -1.1(3) . . . . C5 N1 C1 C6 175.44(17) . . . . C5 C4 C3 C2 -0.3(3) . . . . C9 N9 C11 N8 2.3(3) . . . . C9 N9 C11 N11 -178.4(2) . . . . C9 N7 C10 N8 5.0(3) . . . . C9 N7 C10 N10 -174.9(2) . . . . C9 C5 C4 C3 177.2(2) . . . . C2 C1 C6 N2 -173.61(19) . . . . C2 C1 C6 N4 9.2(3) . . . . C1 N1 C5 C9 -176.93(17) . . . . C1 N1 C5 C4 -0.6(3) . . . . C1 C2 C3 C4 -1.3(3) . . . . C10 N7 C9 N9 -5.5(3) . . . . C10 N7 C9 C5 172.48(17) . . . . C10 N8 C11 N9 -2.5(3) . . . . C10 N8 C11 N11 178.1(2) . . . . C4 C5 C9 N9 12.6(3) . . . . C4 C5 C9 N7 -165.6(2) . . . . C11 N9 C9 N7 2.2(3) . . . . C11 N9 C9 C5 -175.80(18) . . . . C11 N8 C10 N7 -1.4(3) . . . . C11 N8 C10 N10 178.5(2) . . . . C3 C2 C1 N1 2.1(3) . . . . C3 C2 C1 C6 -174.13(19) . . . . C7 N2 C6 N4 0.0(3) . . . . C7 N2 C6 C1 -176.81(17) . . . . C7 N3 C8 N4 -1.9(3) . . . . C7 N3 C8 N6 177.9(2) . . . . C6 N2 C7 N5 -176.5(2) . . . . C6 N2 C7 N3 5.1(3) . . . . C6 N4 C8 N6 -173.7(2) . . . . C6 N4 C8 N3 6.2(3) . . . . C8 N4 C6 N2 -5.1(3) . . . . C8 N4 C6 C1 171.59(18) . . . . C8 N3 C7 N2 -4.2(3) . . . . C8 N3 C7 N5 177.4(2) . . . . _cod_database_fobs_code 4519436