#------------------------------------------------------------------------------ #$Date: 2023-03-23 11:19:04 +0200 (Thu, 23 Mar 2023) $ #$Revision: 282003 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106952.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_8106952 loop_ _publ_author_name 'Ji, Xiangdong' 'Gao, Wei' 'Mu, Ying' _publ_section_title ; Crystal structure of (((1E,1′E)-(cyclohexane-1,2-diylbis(azanylylidene-\k2 N,N′))bis(methanylylidene))bis(2,1-phenylene))bis((2,6-diisopropylphenyl)amide-\k2 N′′,N′′′)manganese(II), C44H54N4Mn ; _journal_issue 2 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 605 _journal_page_last 607 _journal_paper_doi 10.1515/ncrs-2015-0208 _journal_volume 231 _journal_year 2016 _chemical_formula_sum 'C44 H54 Mn N4' _chemical_formula_weight 693.88 _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 105.252(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 15.315(3) _cell_length_b 14.259(3) _cell_length_c 18.118(3) _cell_measurement_reflns_used 3060 _cell_measurement_temperature 185(2) _cell_measurement_theta_max 25.49 _cell_measurement_theta_min 2.48 _cell_volume 3817.2(13) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 185(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 11174 _diffrn_reflns_theta_full 26.05 _diffrn_reflns_theta_max 26.05 _diffrn_reflns_theta_min 2.11 _exptl_absorpt_coefficient_mu 0.381 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1484 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.460 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3742 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0472 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.8318P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1177 _refine_ls_wR_factor_ref 0.1287 _reflns_number_gt 2962 _reflns_number_total 3742 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL exp_C44H54N4Mn REM C2/c CELL 0.71073 15.3146 14.2587 18.1185 90.000 105.252 90.000 ZERR 8.00 0.0028 0.0027 0.0034 0.000 0.003 0.000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N Mn UNIT 176 216 16 4 L.S. 16 BOND $H FMAP 2 PLAN 20 SIZE 0.12 0.13 0.15 FREE N2 C15 FREE N1 C15 FREE N1 C14 FREE N1 C7 FREE N1 C9 TEMP -88.5 WGHT 0.069900 0.908700 FVAR 0.08807 MN1 4 0.000000 0.110878 0.750000 10.50000 0.02791 0.01950 = 0.02718 0.00000 0.01134 0.00000 N1 3 0.091864 0.175363 0.699430 11.00000 0.02900 0.02175 = 0.02325 -0.00089 0.00853 -0.00243 N2 3 0.002779 -0.009492 0.677412 11.00000 0.02477 0.02399 = 0.03126 -0.00095 0.00684 -0.00066 C8 1 0.131088 0.263255 0.731197 11.00000 0.03046 0.02202 = 0.02721 -0.00043 0.01204 -0.00389 C9 1 0.197391 0.263966 0.802059 11.00000 0.03080 0.02525 = 0.02887 -0.00068 0.00947 -0.00261 C13 1 0.127590 0.141889 0.642597 11.00000 0.02708 0.02472 = 0.02393 0.00359 0.00513 0.00396 C7 1 0.106131 0.347720 0.689733 11.00000 0.03202 0.02868 = 0.03133 0.00161 0.00862 -0.00390 C14 1 0.202906 0.185789 0.624215 11.00000 0.03580 0.03025 = 0.03595 0.00268 0.01545 -0.00063 AFIX 43 H14 2 0.230781 0.237681 0.654178 11.00000 -1.20000 AFIX 0 C12 1 0.149788 0.429661 0.719857 11.00000 0.04621 0.02267 = 0.04365 0.00572 0.01065 -0.00577 AFIX 43 H12 2 0.134153 0.486640 0.692382 11.00000 -1.20000 AFIX 0 C1 1 0.222498 0.174727 0.848691 11.00000 0.03779 0.02718 = 0.02769 0.00054 0.00312 -0.00362 AFIX 13 H1 2 0.201683 0.120372 0.813595 11.00000 -1.20000 AFIX 0 C19 1 -0.025460 -0.098113 0.706857 11.00000 0.02883 0.02154 = 0.04452 -0.00365 0.01240 -0.00171 AFIX 13 H19 2 -0.091741 -0.093686 0.702731 11.00000 -1.20000 AFIX 0 C15 1 0.095192 0.058773 0.599721 11.00000 0.02637 0.02975 = 0.02271 0.00076 0.00381 0.00469 C22 1 0.039492 -0.012062 0.621096 11.00000 0.02737 0.02713 = 0.03013 -0.00831 0.00247 0.00128 AFIX 43 H22 2 0.028567 -0.066869 0.590216 11.00000 -1.20000 AFIX 0 C21 1 -0.028955 -0.275217 0.709369 11.00000 0.04826 0.02304 = 0.08376 -0.00858 0.02670 -0.00497 AFIX 23 H21A 2 -0.093661 -0.275878 0.709161 11.00000 -1.20000 H21B 2 -0.016481 -0.332391 0.682859 11.00000 -1.20000 AFIX 0 C20 1 -0.009236 -0.188182 0.666953 11.00000 0.04343 0.02544 = 0.05786 -0.00851 0.01939 -0.00434 AFIX 23 H20A 2 0.054462 -0.189992 0.664226 11.00000 -1.20000 H20B 2 -0.048622 -0.188627 0.613993 11.00000 -1.20000 AFIX 0 C16 1 0.131140 0.032629 0.538244 11.00000 0.04106 0.03657 = 0.02641 -0.00414 0.00745 0.00718 AFIX 43 H16 2 0.106694 -0.020871 0.508742 11.00000 -1.20000 AFIX 0 C4 1 0.073476 0.377164 0.546794 11.00000 0.06495 0.07060 = 0.03736 0.01159 0.01412 0.01548 AFIX 137 H4A 2 0.025950 0.373073 0.498635 11.00000 -1.50000 H4B 2 0.122640 0.333837 0.545253 11.00000 -1.50000 H4C 2 0.097034 0.441371 0.553840 11.00000 -1.50000 AFIX 0 C11 1 0.215789 0.430870 0.789110 11.00000 0.04447 0.02735 = 0.04633 -0.00490 0.00741 -0.01179 AFIX 43 H11 2 0.245326 0.487812 0.808364 11.00000 -1.20000 AFIX 0 C5 1 0.034014 0.350869 0.613597 11.00000 0.04417 0.02842 = 0.03853 0.00733 0.00334 -0.00440 AFIX 13 H5 2 0.006771 0.286887 0.603374 11.00000 -1.20000 AFIX 0 C2 1 0.173120 0.169997 0.911805 11.00000 0.04837 0.05038 = 0.04873 0.01555 0.01674 -0.00225 AFIX 137 H2A 2 0.189957 0.224326 0.945699 11.00000 -1.50000 H2B 2 0.190150 0.112226 0.941394 11.00000 -1.50000 H2C 2 0.107613 0.170406 0.888764 11.00000 -1.50000 AFIX 0 C17 1 0.199334 0.080760 0.519387 11.00000 0.05421 0.04950 = 0.03401 -0.00096 0.02608 0.00443 AFIX 43 H17 2 0.220391 0.063186 0.476499 11.00000 -1.20000 AFIX 0 C18 1 0.236811 0.156467 0.565310 11.00000 0.04106 0.04279 = 0.04245 0.00682 0.02367 -0.00032 AFIX 43 H18 2 0.287023 0.188519 0.555586 11.00000 -1.20000 AFIX 0 C10 1 0.237859 0.348969 0.829398 11.00000 0.03977 0.03270 = 0.03389 -0.00194 0.00360 -0.00620 AFIX 43 H10 2 0.282013 0.350299 0.877316 11.00000 -1.20000 AFIX 0 C3 1 0.324651 0.163894 0.883507 11.00000 0.04121 0.03905 = 0.04802 0.00613 0.00738 0.00454 AFIX 137 H3A 2 0.355783 0.165626 0.842688 11.00000 -1.50000 H3B 2 0.336836 0.103842 0.910577 11.00000 -1.50000 H3C 2 0.346640 0.215287 0.919513 11.00000 -1.50000 AFIX 0 C6 1 -0.040813 0.418891 0.617123 11.00000 0.05083 0.07870 = 0.04706 0.01185 0.01498 0.01499 AFIX 137 H6A 2 -0.066161 0.401713 0.659606 11.00000 -1.50000 H6B 2 -0.088502 0.416326 0.568981 11.00000 -1.50000 H6C 2 -0.016166 0.482623 0.625062 11.00000 -1.50000 HKLF 4 REM ffff in C2/c REM R1 = 0.0472 for 2962 Fo > 4sig(Fo) and 0.0627 for all 3742 data REM 226 parameters refined using 0 restraints END WGHT 0.0698 0.9169 REM Highest difference peak 0.460, deepest hole -0.206, 1-sigma level 0.063 Q1 1 0.0473 0.1456 0.7274 11.00000 0.05 0.46 Q2 1 0.1885 0.2627 0.7584 11.00000 0.05 0.37 Q3 1 0.0000 -0.1040 0.7500 10.50000 0.05 0.35 Q4 1 0.1060 0.0976 0.6194 11.00000 0.05 0.32 Q5 1 0.1068 0.1637 0.6632 11.00000 0.05 0.31 Q6 1 -0.0191 0.0587 0.7051 11.00000 0.05 0.31 Q7 1 0.0007 0.3806 0.6195 11.00000 0.05 0.31 Q8 1 -0.0383 0.0656 0.7570 11.00000 0.05 0.30 Q9 1 0.0873 0.0253 0.6321 11.00000 0.05 0.29 Q10 1 0.0026 -0.2367 0.6894 11.00000 0.05 0.28 Q11 1 0.2067 0.2202 0.8298 11.00000 0.05 0.27 Q12 1 -0.0445 0.4618 0.6639 11.00000 0.05 0.27 Q13 1 0.1224 0.0417 0.5794 11.00000 0.05 0.27 Q14 1 0.1188 0.2182 0.7130 11.00000 0.05 0.26 Q15 1 -0.0111 0.1405 0.7011 11.00000 0.05 0.26 Q16 1 0.2039 0.1826 0.5830 11.00000 0.05 0.25 Q17 1 0.1469 0.1817 0.6218 11.00000 0.05 0.25 Q18 1 -0.0573 0.4071 0.5906 11.00000 0.05 0.25 Q19 1 0.2038 0.1427 0.8387 11.00000 0.05 0.25 Q20 1 0.1922 0.3861 0.8166 11.00000 0.05 0.24 ; _cod_data_source_file suppl_ncrs-2015-0208_suppl.cif _cod_data_source_block C44H54N4Mn _cod_depositor_comments ; The following automatic conversions were performed: data item '_symmetry_cell_setting' value 'Monoclinic' was changed to 'monoclinic' 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_original_cell_volume 3817.1(12) _cod_original_sg_symbol_H-M 'C2/c ' _cod_original_formula_sum 'C44 H54 Mn1 N4' _cod_database_code 8106952 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.0000 0.11088(3) 0.7500 0.02400(16) Uani 1 2 d S . . N1 N 0.09185(12) 0.17536(12) 0.69942(9) 0.0243(4) Uani 1 1 d . . . N2 N 0.00279(12) -0.00950(12) 0.67741(10) 0.0267(4) Uani 1 1 d . . . C8 C 0.13109(15) 0.26326(14) 0.73117(12) 0.0257(5) Uani 1 1 d . . . C9 C 0.19741(15) 0.26397(15) 0.80207(12) 0.0279(5) Uani 1 1 d . . . C13 C 0.12759(15) 0.14189(15) 0.64261(12) 0.0255(5) Uani 1 1 d . . . C7 C 0.10614(16) 0.34772(16) 0.68972(12) 0.0305(5) Uani 1 1 d . . . C14 C 0.20289(16) 0.18576(16) 0.62418(13) 0.0328(5) Uani 1 1 d . . . H14 H 0.2302 0.2366 0.6535 0.039 Uiso 1 1 calc R . . C12 C 0.14980(17) 0.42963(16) 0.71985(14) 0.0377(6) Uani 1 1 d . . . H12 H 0.1345 0.4854 0.6930 0.045 Uiso 1 1 calc R . . C1 C 0.22248(16) 0.17476(16) 0.84870(13) 0.0319(5) Uani 1 1 d . . . H1 H 0.2021 0.1215 0.8143 0.038 Uiso 1 1 calc R . . C19 C -0.02543(16) -0.09814(14) 0.70684(13) 0.0310(5) Uani 1 1 d . . . H19 H -0.0904 -0.0938 0.7028 0.037 Uiso 1 1 calc R . . C15 C 0.09520(14) 0.05877(15) 0.59972(12) 0.0267(5) Uani 1 1 d . . . C22 C 0.03948(15) -0.01203(15) 0.62110(12) 0.0292(5) Uani 1 1 d . . . H22 H 0.0288 -0.0657 0.5909 0.035 Uiso 1 1 calc R . . C21 C -0.02894(19) -0.27521(17) 0.70937(16) 0.0499(7) Uani 1 1 d . . . H21A H -0.0923 -0.2759 0.7091 0.060 Uiso 1 1 calc R . . H21B H -0.0167 -0.3312 0.6834 0.060 Uiso 1 1 calc R . . C20 C -0.00925(18) -0.18816(16) 0.66698(16) 0.0410(6) Uani 1 1 d . . . H20A H 0.0532 -0.1899 0.6643 0.049 Uiso 1 1 calc R . . H20B H -0.0479 -0.1886 0.6151 0.049 Uiso 1 1 calc R . . C16 C 0.13117(17) 0.03268(17) 0.53829(12) 0.0349(6) Uani 1 1 d . . . H16 H 0.1073 -0.0197 0.5094 0.042 Uiso 1 1 calc R . . C4 C 0.0735(2) 0.3772(2) 0.54682(15) 0.0575(8) Uani 1 1 d . . . H4A H 0.0269 0.3731 0.4996 0.086 Uiso 1 1 calc R . . H4B H 0.1217 0.3347 0.5454 0.086 Uiso 1 1 calc R . . H4C H 0.0965 0.4401 0.5537 0.086 Uiso 1 1 calc R . . C11 C 0.21577(18) 0.43084(17) 0.78911(14) 0.0402(6) Uani 1 1 d . . . H11 H 0.2447 0.4866 0.8080 0.048 Uiso 1 1 calc R . . C5 C 0.03401(17) 0.35091(17) 0.61360(14) 0.0384(6) Uani 1 1 d . . . H5 H 0.0073 0.2882 0.6036 0.046 Uiso 1 1 calc R . . C2 C 0.17315(19) 0.1700(2) 0.91181(15) 0.0485(7) Uani 1 1 d . . . H2A H 0.1896 0.2232 0.9450 0.073 Uiso 1 1 calc R . . H2B H 0.1899 0.1134 0.9408 0.073 Uiso 1 1 calc R . . H2C H 0.1090 0.1704 0.8893 0.073 Uiso 1 1 calc R . . C17 C 0.19932(19) 0.08078(18) 0.51941(14) 0.0432(6) Uani 1 1 d . . . H17 H 0.2199 0.0636 0.4774 0.052 Uiso 1 1 calc R . . C18 C 0.23678(17) 0.15644(18) 0.56531(14) 0.0396(6) Uani 1 1 d . . . H18 H 0.2859 0.1878 0.5558 0.048 Uiso 1 1 calc R . . C10 C 0.23781(18) 0.34897(16) 0.82934(14) 0.0366(6) Uani 1 1 d . . . H10 H 0.2810 0.3503 0.8762 0.044 Uiso 1 1 calc R . . C3 C 0.32464(17) 0.16391(19) 0.88352(15) 0.0436(6) Uani 1 1 d . . . H3A H 0.3551 0.1655 0.8435 0.065 Uiso 1 1 calc R . . H3B H 0.3366 0.1051 0.9101 0.065 Uiso 1 1 calc R . . H3C H 0.3462 0.2143 0.9187 0.065 Uiso 1 1 calc R . . C6 C -0.0408(2) 0.4189(2) 0.61713(16) 0.0586(8) Uani 1 1 d . . . H6A H -0.0658 0.4019 0.6586 0.088 Uiso 1 1 calc R . . H6B H -0.0874 0.4165 0.5699 0.088 Uiso 1 1 calc R . . H6C H -0.0166 0.4813 0.6251 0.088 Uiso 1 1 calc R . . 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 Mn1 0.0278(3) 0.0194(2) 0.0271(3) 0.000 0.0113(2) 0.000 N1 0.0289(10) 0.0217(9) 0.0232(9) -0.0009(7) 0.0085(8) -0.0024(7) N2 0.0247(10) 0.0239(9) 0.0311(10) -0.0010(7) 0.0069(8) -0.0007(7) C8 0.0304(12) 0.0220(11) 0.0273(11) -0.0004(8) 0.0121(10) -0.0038(9) C9 0.0306(13) 0.0253(11) 0.0287(12) -0.0007(9) 0.0094(10) -0.0026(9) C13 0.0270(12) 0.0247(11) 0.0239(11) 0.0036(8) 0.0052(9) 0.0039(9) C7 0.0320(13) 0.0286(12) 0.0311(12) 0.0016(9) 0.0086(10) -0.0039(10) C14 0.0358(14) 0.0301(12) 0.0359(13) 0.0025(10) 0.0154(11) -0.0007(10) C12 0.0463(16) 0.0225(12) 0.0436(14) 0.0059(10) 0.0107(12) -0.0057(11) C1 0.0377(14) 0.0271(12) 0.0276(12) 0.0004(9) 0.0031(10) -0.0037(10) C19 0.0285(13) 0.0216(11) 0.0446(14) -0.0036(9) 0.0124(11) -0.0016(9) C15 0.0263(12) 0.0295(12) 0.0227(11) 0.0008(9) 0.0038(9) 0.0047(9) C22 0.0274(12) 0.0269(11) 0.0301(11) -0.0086(9) 0.0024(10) 0.0013(9) C21 0.0481(17) 0.0228(12) 0.084(2) -0.0088(12) 0.0269(15) -0.0050(11) C20 0.0430(15) 0.0257(12) 0.0577(16) -0.0085(11) 0.0191(13) -0.0043(11) C16 0.0411(14) 0.0363(13) 0.0264(12) -0.0043(10) 0.0074(10) 0.0070(11) C4 0.065(2) 0.071(2) 0.0372(15) 0.0115(14) 0.0141(14) 0.0157(16) C11 0.0445(15) 0.0271(12) 0.0463(15) -0.0050(11) 0.0073(12) -0.0119(11) C5 0.0441(16) 0.0282(12) 0.0387(14) 0.0073(10) 0.0034(12) -0.0046(11) C2 0.0486(17) 0.0502(17) 0.0488(16) 0.0155(13) 0.0166(13) -0.0024(13) C17 0.0542(17) 0.0495(15) 0.0340(13) -0.0011(11) 0.0262(13) 0.0044(13) C18 0.0409(15) 0.0428(14) 0.0423(14) 0.0069(11) 0.0236(12) -0.0005(12) C10 0.0398(14) 0.0328(13) 0.0336(13) -0.0020(10) 0.0034(11) -0.0062(11) C3 0.0413(16) 0.0389(15) 0.0483(15) 0.0061(12) 0.0075(13) 0.0045(12) C6 0.0509(18) 0.079(2) 0.0472(17) 0.0119(15) 0.0150(14) 0.0148(16) 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' Mn Mn 0.3368 0.7283 '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 Mn1 N1 127.64(9) . 2_556 N1 Mn1 N2 87.67(7) . . N1 Mn1 N2 137.63(7) 2_556 . N1 Mn1 N2 137.63(7) . 2_556 N1 Mn1 N2 87.67(7) 2_556 2_556 N2 Mn1 N2 75.42(9) . 2_556 C13 N1 C8 113.25(17) . . C13 N1 Mn1 128.68(14) . . C8 N1 Mn1 117.81(12) . . C22 N2 C19 119.41(18) . . C22 N2 Mn1 125.76(14) . . C19 N2 Mn1 113.77(13) . . C9 C8 C7 120.32(19) . . C9 C8 N1 119.56(18) . . C7 C8 N1 120.06(19) . . C10 C9 C8 118.4(2) . . C10 C9 C1 120.5(2) . . C8 C9 C1 121.05(19) . . N1 C13 C14 122.0(2) . . N1 C13 C15 123.04(19) . . C14 C13 C15 114.94(19) . . C12 C7 C8 118.2(2) . . C12 C7 C5 119.4(2) . . C8 C7 C5 122.3(2) . . C18 C14 C13 123.0(2) . . C7 C12 C11 121.9(2) . . C9 C1 C2 110.53(19) . . C9 C1 C3 113.24(19) . . C2 C1 C3 109.8(2) . . N2 C19 C20 116.69(19) . . N2 C19 C19 104.26(15) . 2_556 C20 C19 C19 112.09(16) . 2_556 C16 C15 C13 119.5(2) . . C16 C15 C22 114.1(2) . . C13 C15 C22 125.42(19) . . N2 C22 C15 127.35(19) . . C21 C21 C20 110.34(19) 2_556 . C19 C20 C21 111.5(2) . . C17 C16 C15 123.1(2) . . C10 C11 C12 119.3(2) . . C6 C5 C7 110.9(2) . . C6 C5 C4 109.7(2) . . C7 C5 C4 112.3(2) . . C16 C17 C18 117.5(2) . . C14 C18 C17 121.5(2) . . C11 C10 C9 121.9(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Mn1 N1 2.0837(17) . Mn1 N1 2.0837(17) 2_556 Mn1 N2 2.1696(18) . Mn1 N2 2.1696(18) 2_556 N1 C13 1.372(3) . N1 C8 1.443(3) . N2 C22 1.288(3) . N2 C19 1.480(3) . C8 C9 1.413(3) . C8 C7 1.417(3) . C9 C10 1.391(3) . C9 C1 1.519(3) . C13 C14 1.427(3) . C13 C15 1.432(3) . C7 C12 1.385(3) . C7 C5 1.524(3) . C14 C18 1.369(3) . C12 C11 1.389(3) . C1 C2 1.529(3) . C1 C3 1.533(3) . C19 C20 1.525(3) . C19 C19 1.553(5) 2_556 C15 C16 1.415(3) . C15 C22 1.439(3) . C21 C21 1.506(6) 2_556 C21 C20 1.531(3) . C16 C17 1.365(3) . C4 C5 1.534(3) . C11 C10 1.371(3) . C5 C6 1.514(4) . C17 C18 1.390(4) .