#------------------------------------------------------------------------------ #$Date: 2020-08-25 04:36:20 +0300 (Tue, 25 Aug 2020) $ #$Revision: 255617 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/52/7705262.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_7705262 loop_ _publ_author_name 'Xu, Bo-Wei' 'Niu, Ru-Jie' 'Liu, Quan' 'Yang, Junyi' 'Zhang, Wen-Hua' 'Young, David James' _publ_section_title ; Similarities and differences between Mn(II) and Zn(II) coordination polymers supported by porphyrin-based ligands: Synthesis, structures and nonlinear optical properties ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D0DT02450C _journal_year 2020 _chemical_formula_moiety 'C44 H32 Mn N8 O4' _chemical_formula_sum 'C44 H32 Mn N8 O4' _chemical_formula_weight 791.71 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2020-06-16 deposited with the CCDC. 2020-08-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.826(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.8600(14) _cell_length_b 9.1501(12) _cell_length_c 20.476(3) _cell_measurement_reflns_used 1860 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 22.58 _cell_measurement_theta_min 2.45 _cell_volume 1793.8(4) _computing_cell_refinement 'Bruker D8 Quest' _computing_data_collection 'Bruker D8 Quest' _computing_data_reduction 'Bruker D8 Quest' _computing_molecular_graphics 'SHELXL-2013 (Sheldrick, 2013)' _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker D8 Quest' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.2115 _diffrn_reflns_av_unetI/netI 0.1180 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 25696 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.027 _diffrn_reflns_theta_max 25.027 _diffrn_reflns_theta_min 2.049 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.427 _exptl_absorpt_correction_T_max 0.958 _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Sheldrick, G.M. SADABS (Program for Scaling and Correction of Area Detector Data), version 2008/1; University of G\"ottingen: G\"ottingen, Germany, 2008. ; _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.466 _exptl_crystal_description block _exptl_crystal_F_000 818 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _refine_diff_density_max 1.250 _refine_diff_density_min -0.998 _refine_diff_density_rms 0.347 _refine_ls_extinction_coef 0.18(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 260 _refine_ls_number_reflns 3161 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.149 _refine_ls_R_factor_all 0.1752 _refine_ls_R_factor_gt 0.1266 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1886P)^2^+1.9108P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2949 _refine_ls_wR_factor_ref 0.3296 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2216 _reflns_number_total 3161 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02450c2.cif _cod_data_source_block MN-THPP _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7705262 _shelx_shelxl_version_number 2016/6 _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_min 0.919 _shelx_estimated_absorpt_t_max 0.959 _shelx_res_file ; TITL mo_b170808a_0m_a.res in P2(1)/n MN.res created by SHELXL-2016/6 at 10:33:11 on 04-Sep-2017 REM Old TITL mo_b170808a_0m in P2(1)/c REM SHELXT solution in P2(1)/n REM R1 0.244, Rweak 0.120, Alpha 0.147, Orientation as input REM Formula found by SHELXT: C50 Mn N6 CELL 0.71073 9.8600 9.1501 20.4760 90.000 103.826 90.000 ZERR 2.000 0.0014 0.0012 0.0030 0.000 0.004 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H MN N O UNIT 88 64 2 16 8 TEMP -153.150 SIZE 0.10 0.20 0.20 L.S. 10 BOND $H LIST 4 SHEL 99999 0.84 ACTA FMAP 2 PLAN -40 WGHT 0.188600 1.910800 EXTI 0.182531 FVAR 0.48681 MN1 3 0.500000 0.500000 0.500000 10.50000 0.05442 0.02173 = 0.01830 -0.00364 0.00963 -0.01425 O1 5 0.200963 0.138202 0.032022 11.00000 0.06000 0.03232 = 0.02887 -0.00203 0.00108 0.00230 AFIX 3 H1O1 2 0.196403 0.221262 0.015342 11.00000 -1.20000 AFIX 0 O2 5 0.937296 1.342285 0.329255 11.00000 0.15956 0.07241 = 0.06264 -0.02142 0.04366 -0.06676 AFIX 3 H1O2 2 0.965006 1.426215 0.324165 11.00000 -1.20000 AFIX 0 N1 4 0.400271 0.313353 0.454064 11.00000 0.03067 0.01668 = 0.01370 -0.00582 0.00040 0.00104 N2 4 0.551076 0.560127 0.409552 11.00000 0.03313 0.01352 = 0.01154 0.00013 -0.00194 -0.00517 N4 4 0.734842 1.190934 0.427680 11.00000 0.04630 0.02773 = 0.04235 0.00457 0.00489 -0.00582 N6 4 0.464848 0.138562 0.188831 11.00000 0.03722 0.05651 = 0.02934 -0.02124 -0.00421 0.01990 C1 1 0.330022 0.102748 0.075742 11.00000 0.04141 0.02986 = 0.01588 -0.00422 -0.00583 0.00424 AFIX 23 H1A 2 0.406746 0.134991 0.055536 11.00000 -1.20000 H1B 2 0.336908 -0.004629 0.081521 11.00000 -1.20000 AFIX 0 C2 1 0.346680 0.174546 0.143975 11.00000 0.02331 0.02281 = 0.02140 -0.00517 0.00329 -0.00349 C3 1 0.249402 0.264400 0.159716 11.00000 0.03986 0.02649 = 0.01705 0.00043 -0.00306 0.01088 AFIX 43 H3 2 0.166071 0.286445 0.126947 11.00000 -1.20000 AFIX 0 C4 1 0.271973 0.323526 0.223408 11.00000 0.03876 0.02804 = 0.01902 -0.00067 0.00748 0.01124 AFIX 43 H4 2 0.202362 0.382324 0.235467 11.00000 -1.20000 AFIX 0 C5 1 0.397307 0.296342 0.269724 11.00000 0.03394 0.01075 = 0.01959 -0.00738 0.00278 -0.00424 C6 1 0.486829 0.201365 0.250084 11.00000 0.04446 0.06602 = 0.01724 -0.00945 -0.00421 0.01972 AFIX 43 H6 2 0.570964 0.177733 0.281978 11.00000 -1.20000 AFIX 0 C7 1 0.886391 1.346420 0.382675 11.00000 0.09837 0.10932 = 0.05210 0.01396 0.02128 -0.06181 AFIX 23 H7A 2 0.808077 1.416892 0.375902 11.00000 -1.20000 H7B 2 0.959452 1.377816 0.422287 11.00000 -1.20000 AFIX 0 C8 1 0.833488 1.188275 0.394430 11.00000 0.06487 0.04561 = 0.02218 0.00135 -0.00374 -0.02632 C9 1 0.887408 1.058964 0.375546 11.00000 0.03165 0.07466 = 0.03096 -0.00469 0.01435 -0.02316 AFIX 43 H9 2 0.958550 1.060862 0.351401 11.00000 -1.20000 AFIX 0 C10 1 0.835295 0.926279 0.392644 11.00000 0.04795 0.03048 = 0.02275 -0.00435 0.01143 -0.01536 AFIX 43 H10 2 0.872385 0.836310 0.381568 11.00000 -1.20000 AFIX 0 C11 1 0.729663 0.927887 0.425697 11.00000 0.02747 0.02239 = 0.01777 -0.00577 0.00480 -0.00550 C12 1 0.682301 1.062614 0.439588 11.00000 0.02807 0.02609 = 0.04050 0.00295 0.00988 -0.00786 AFIX 43 H12 2 0.604729 1.064358 0.459580 11.00000 -1.20000 AFIX 0 C13 1 0.335405 0.212082 0.483938 11.00000 0.02795 0.01097 = 0.02280 -0.00034 0.00929 -0.00355 C14 1 0.262015 0.109617 0.432630 11.00000 0.03529 0.02976 = 0.02353 -0.00397 0.00290 -0.00995 AFIX 43 H14 2 0.206023 0.028935 0.439117 11.00000 -1.20000 AFIX 0 C15 1 0.290514 0.153765 0.373262 11.00000 0.05008 0.02214 = 0.01611 -0.00616 0.00182 -0.01455 AFIX 43 H15 2 0.257953 0.108600 0.330612 11.00000 -1.20000 AFIX 0 C16 1 0.378096 0.280064 0.387215 11.00000 0.02807 0.01939 = 0.01279 -0.00574 -0.00502 0.00153 C17 1 0.428275 0.359293 0.338941 11.00000 0.03417 0.01176 = 0.00972 -0.00445 0.00185 -0.00241 C18 1 0.505987 0.491123 0.349350 11.00000 0.03912 0.01902 = 0.01248 0.00211 -0.00047 0.00366 C19 1 0.542039 0.575570 0.298157 11.00000 0.04875 0.02615 = 0.01498 0.00023 0.00410 -0.01183 AFIX 43 H19 2 0.523688 0.551163 0.251773 11.00000 -1.20000 AFIX 0 C20 1 0.607492 0.697573 0.327294 11.00000 0.05665 0.02829 = 0.02308 0.00374 0.02056 -0.00940 AFIX 43 H20 2 0.643418 0.774543 0.305211 11.00000 -1.20000 AFIX 0 C21 1 0.612377 0.688700 0.397880 11.00000 0.03713 0.01523 = 0.01994 -0.00022 0.00675 -0.00256 C22 1 0.669387 0.794969 0.447295 11.00000 0.02641 0.01306 = 0.02127 -0.00327 0.00277 -0.00246 HKLF 4 REM mo_b170808a_0m_a.res in P2(1)/n REM R1 = 0.1266 for 2216 Fo > 4sig(Fo) and 0.1752 for all 3161 data REM 260 parameters refined using 0 restraints END WGHT 0.1576 1.8447 REM Highest difference peak 1.250, deepest hole -0.998, 1-sigma level 0.347 Q1 1 0.9193 1.2730 0.3577 11.00000 0.05 1.25 Q2 1 0.8473 1.1575 0.3657 11.00000 0.05 1.18 Q3 1 0.8631 1.4199 0.3524 11.00000 0.05 1.07 Q4 1 0.4104 0.2065 0.1624 11.00000 0.05 1.06 Q5 1 0.8329 1.0151 0.3826 11.00000 0.05 1.02 Q6 1 0.7764 1.1645 0.3953 11.00000 0.05 1.00 Q7 1 0.5865 0.6409 0.3059 11.00000 0.05 0.95 Q8 1 0.9182 1.0366 0.3591 11.00000 0.05 0.94 Q9 1 0.6580 0.6638 0.3331 11.00000 0.05 0.87 Q10 1 0.8673 1.1776 0.4155 11.00000 0.05 0.86 Q11 1 0.6290 0.7493 0.4190 11.00000 0.05 0.85 Q12 1 0.6181 0.6946 0.3643 11.00000 0.05 0.84 Q13 1 0.9233 1.3143 0.3158 11.00000 0.05 0.84 Q14 1 0.8490 1.3092 0.2874 11.00000 0.05 0.82 Q15 1 0.3340 0.3264 0.2530 11.00000 0.05 0.80 Q16 1 1.0281 1.5611 0.3205 11.00000 0.05 0.77 Q17 1 0.7830 1.1016 0.4504 11.00000 0.05 0.76 Q18 1 0.6222 0.7450 0.3117 11.00000 0.05 0.76 Q19 1 0.9022 1.2091 0.2945 11.00000 0.05 0.74 Q20 1 0.3951 0.3188 0.3588 11.00000 0.05 0.72 Q21 1 0.8051 0.9334 0.3627 11.00000 0.05 0.72 Q22 1 0.4259 0.3413 0.2969 11.00000 0.05 0.70 Q23 1 0.7575 1.0188 0.4370 11.00000 0.05 0.70 Q24 1 0.3763 0.2370 0.2689 11.00000 0.05 0.69 Q25 1 0.3299 0.2363 0.3728 11.00000 0.05 0.68 Q26 1 0.5279 0.5279 0.3170 11.00000 0.05 0.68 Q27 1 0.3628 0.2044 0.2218 11.00000 0.05 0.62 Q28 1 0.8131 0.9404 0.4248 11.00000 0.05 0.61 Q29 1 0.6711 0.8791 0.4279 11.00000 0.05 0.59 Q30 1 0.3434 0.2995 0.3207 11.00000 0.05 0.59 Q31 1 0.4576 0.4316 0.3451 11.00000 0.05 0.58 Q32 1 0.5238 0.5082 0.3827 11.00000 0.05 0.56 Q33 1 0.6940 0.7984 0.2724 11.00000 0.05 0.55 Q34 1 0.3008 0.1671 0.4570 11.00000 0.05 0.54 Q35 1 0.3113 0.1258 0.4021 11.00000 0.05 0.53 Q36 1 0.2806 0.1389 0.4016 11.00000 0.05 0.53 Q37 1 0.5221 0.5090 0.4497 11.00000 0.05 0.53 Q38 1 0.6767 0.5659 0.2893 11.00000 0.05 0.52 Q39 1 0.6907 0.7579 0.4664 11.00000 0.05 0.52 Q40 1 0.8310 1.0935 0.3146 11.00000 0.05 0.51 ; _shelx_res_checksum 57810 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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_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 Mn1 Mn 0.500000 0.500000 0.500000 0.0313(7) Uani 1 2 d S . P . . O1 O 0.2010(6) 0.1382(6) 0.0320(3) 0.0420(16) Uani 1 1 d . . . . . H1O1 H 0.196403 0.221262 0.015342 0.050 Uiso 1 1 d R U . . . O2 O 0.9373(11) 1.3423(9) 0.3293(4) 0.095(3) Uani 1 1 d . . . . . H1O2 H 0.965006 1.426215 0.324165 0.114 Uiso 1 1 d R U . . . N1 N 0.4003(6) 0.3134(6) 0.4541(3) 0.0212(14) Uani 1 1 d . . . . . N2 N 0.5511(6) 0.5601(6) 0.4096(3) 0.0206(14) Uani 1 1 d . . . . . N4 N 0.7348(8) 1.1909(7) 0.4277(3) 0.0398(18) Uani 1 1 d . . . . . N6 N 0.4648(7) 0.1386(8) 0.1888(3) 0.043(2) Uani 1 1 d . . . . . C1 C 0.3300(9) 0.1027(9) 0.0757(3) 0.0312(19) Uani 1 1 d . . . . . H1A H 0.406746 0.134991 0.055536 0.037 Uiso 1 1 calc R U . . . H1B H 0.336908 -0.004629 0.081521 0.037 Uiso 1 1 calc R U . . . C2 C 0.3467(7) 0.1745(8) 0.1440(3) 0.0229(17) Uani 1 1 d . . . . . C3 C 0.2494(9) 0.2644(8) 0.1597(3) 0.0295(19) Uani 1 1 d . . . . . H3 H 0.166071 0.286445 0.126947 0.035 Uiso 1 1 calc R U . . . C4 C 0.2720(8) 0.3235(8) 0.2234(3) 0.0285(18) Uani 1 1 d . . . . . H4 H 0.202362 0.382324 0.235467 0.034 Uiso 1 1 calc R U . . . C5 C 0.3973(8) 0.2963(7) 0.2697(3) 0.0220(17) Uani 1 1 d . . . . . C6 C 0.4868(9) 0.2014(11) 0.2501(4) 0.045(2) Uani 1 1 d . . . . . H6 H 0.570964 0.177733 0.281978 0.053 Uiso 1 1 calc R U . . . C7 C 0.8864(14) 1.3464(15) 0.3827(5) 0.086(4) Uani 1 1 d . . . . . H7A H 0.808077 1.416892 0.375902 0.103 Uiso 1 1 calc R U . . . H7B H 0.959452 1.377816 0.422287 0.103 Uiso 1 1 calc R U . . . C8 C 0.8335(11) 1.1883(10) 0.3944(4) 0.047(3) Uani 1 1 d . . . . . C9 C 0.8874(9) 1.0590(12) 0.3755(4) 0.045(2) Uani 1 1 d . . . . . H9 H 0.958550 1.060862 0.351401 0.054 Uiso 1 1 calc R U . . . C10 C 0.8353(9) 0.9263(9) 0.3926(4) 0.033(2) Uani 1 1 d . . . . . H10 H 0.872385 0.836310 0.381568 0.040 Uiso 1 1 calc R U . . . C11 C 0.7297(8) 0.9279(8) 0.4257(3) 0.0226(16) Uani 1 1 d . . . . . C12 C 0.6823(8) 1.0626(8) 0.4396(4) 0.0313(19) Uani 1 1 d . . . . . H12 H 0.604729 1.064358 0.459580 0.038 Uiso 1 1 calc R U . . . C13 C 0.3354(7) 0.2121(7) 0.4839(3) 0.0200(16) Uani 1 1 d . . . . . C14 C 0.2620(8) 0.1096(8) 0.4326(3) 0.0302(19) Uani 1 1 d . . . . . H14 H 0.206023 0.028935 0.439117 0.036 Uiso 1 1 calc R U . . . C15 C 0.2905(9) 0.1538(8) 0.3733(3) 0.0305(19) Uani 1 1 d . . . . . H15 H 0.257953 0.108600 0.330612 0.037 Uiso 1 1 calc R U . . . C16 C 0.3781(7) 0.2801(7) 0.3872(3) 0.0218(17) Uani 1 1 d . . . . . C17 C 0.4283(8) 0.3593(7) 0.3389(3) 0.0191(16) Uani 1 1 d . . . . . C18 C 0.5060(8) 0.4911(7) 0.3493(3) 0.0247(17) Uani 1 1 d . . . . . C19 C 0.5420(9) 0.5756(8) 0.2982(3) 0.0306(19) Uani 1 1 d . . . . . H19 H 0.523688 0.551163 0.251773 0.037 Uiso 1 1 calc R U . . . C20 C 0.6075(9) 0.6976(9) 0.3273(4) 0.034(2) Uani 1 1 d . . . . . H20 H 0.643418 0.774543 0.305211 0.041 Uiso 1 1 calc R U . . . C21 C 0.6124(8) 0.6887(7) 0.3979(3) 0.0241(17) Uani 1 1 d . . . . . C22 C 0.6694(7) 0.7950(7) 0.4473(3) 0.0207(16) 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 Mn1 0.0544(13) 0.0217(10) 0.0183(9) -0.0036(6) 0.0096(7) -0.0143(8) O1 0.060(4) 0.032(3) 0.029(3) -0.002(2) 0.001(3) 0.002(3) O2 0.160(9) 0.072(6) 0.063(5) -0.021(4) 0.044(5) -0.067(6) N1 0.031(3) 0.017(3) 0.014(3) -0.006(2) 0.000(2) 0.001(3) N2 0.033(4) 0.014(3) 0.012(3) 0.000(2) -0.002(2) -0.005(3) N4 0.046(5) 0.028(4) 0.042(4) 0.005(3) 0.005(3) -0.006(3) N6 0.037(4) 0.057(5) 0.029(4) -0.021(3) -0.004(3) 0.020(4) C1 0.041(5) 0.030(4) 0.016(4) -0.004(3) -0.006(3) 0.004(4) C2 0.023(4) 0.023(4) 0.021(4) -0.005(3) 0.003(3) -0.003(3) C3 0.040(5) 0.026(4) 0.017(4) 0.000(3) -0.003(3) 0.011(4) C4 0.039(5) 0.028(4) 0.019(4) -0.001(3) 0.007(3) 0.011(4) C5 0.034(4) 0.011(3) 0.020(3) -0.007(3) 0.003(3) -0.004(3) C6 0.044(5) 0.066(6) 0.017(4) -0.009(4) -0.004(4) 0.020(5) C7 0.098(10) 0.109(11) 0.052(7) 0.014(7) 0.021(6) -0.062(8) C8 0.065(7) 0.046(6) 0.022(4) 0.001(4) -0.004(4) -0.026(5) C9 0.032(5) 0.075(7) 0.031(5) -0.005(4) 0.014(4) -0.023(5) C10 0.048(5) 0.030(4) 0.023(4) -0.004(3) 0.011(4) -0.015(4) C11 0.027(4) 0.022(4) 0.018(3) -0.006(3) 0.005(3) -0.006(3) C12 0.028(4) 0.026(4) 0.040(5) 0.003(3) 0.010(4) -0.008(3) C13 0.028(4) 0.011(3) 0.023(4) 0.000(3) 0.009(3) -0.004(3) C14 0.035(5) 0.030(4) 0.024(4) -0.004(3) 0.003(3) -0.010(4) C15 0.050(5) 0.022(4) 0.016(4) -0.006(3) 0.002(3) -0.015(4) C16 0.028(4) 0.019(4) 0.013(3) -0.006(3) -0.005(3) 0.002(3) C17 0.034(4) 0.012(3) 0.010(3) -0.004(3) 0.002(3) -0.002(3) C18 0.039(5) 0.019(4) 0.012(3) 0.002(3) 0.000(3) 0.004(3) C19 0.049(5) 0.026(4) 0.015(4) 0.000(3) 0.004(3) -0.012(4) C20 0.057(6) 0.028(4) 0.023(4) 0.004(3) 0.021(4) -0.009(4) C21 0.037(4) 0.015(4) 0.020(4) 0.000(3) 0.007(3) -0.003(3) C22 0.026(4) 0.013(3) 0.021(4) -0.003(3) 0.003(3) -0.002(3) 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' Mn Mn 0.3368 0.7283 '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' 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 N1 Mn1 N1 180.0 . 3_666 ? N1 Mn1 N2 90.2(2) . . ? N1 Mn1 N2 89.8(2) 3_666 . ? N1 Mn1 N2 89.8(2) . 3_666 ? N1 Mn1 N2 90.2(2) 3_666 3_666 ? N2 Mn1 N2 180.0(3) . 3_666 ? N1 Mn1 O1 87.7(2) . 4_666 ? N1 Mn1 O1 92.3(2) 3_666 4_666 ? N2 Mn1 O1 91.3(2) . 4_666 ? N2 Mn1 O1 88.7(2) 3_666 4_666 ? N1 Mn1 O1 92.3(2) . 2 ? N1 Mn1 O1 87.7(2) 3_666 2 ? N2 Mn1 O1 88.7(2) . 2 ? N2 Mn1 O1 91.3(2) 3_666 2 ? O1 Mn1 O1 180.0 4_666 2 ? C1 O1 Mn1 129.7(5) . 2_545 ? C1 O1 H1O1 115.1 . . ? Mn1 O1 H1O1 115.2 2_545 . ? C7 O2 H1O2 106.4 . . ? C13 N1 C16 108.7(5) . . ? C13 N1 Mn1 125.6(4) . . ? C16 N1 Mn1 125.5(5) . . ? C18 N2 C21 107.6(5) . . ? C18 N2 Mn1 125.5(5) . . ? C21 N2 Mn1 125.9(4) . . ? C8 N4 C12 116.6(8) . . ? C2 N6 C6 116.9(7) . . ? O1 C1 C2 111.6(6) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? N6 C2 C3 122.2(6) . . ? N6 C2 C1 114.2(6) . . ? C3 C2 C1 123.6(6) . . ? C2 C3 C4 119.8(7) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 119.4(7) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 116.4(6) . . ? C6 C5 C17 121.7(6) . . ? C4 C5 C17 121.7(6) . . ? N6 C6 C5 125.0(7) . . ? N6 C6 H6 117.5 . . ? C5 C6 H6 117.5 . . ? O2 C7 C8 107.9(11) . . ? O2 C7 H7A 110.1 . . ? C8 C7 H7A 110.1 . . ? O2 C7 H7B 110.1 . . ? C8 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? N4 C8 C9 122.7(8) . . ? N4 C8 C7 112.0(9) . . ? C9 C8 C7 125.2(10) . . ? C8 C9 C10 118.9(8) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 118.9(8) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C12 C11 C10 116.6(7) . . ? C12 C11 C22 120.0(7) . . ? C10 C11 C22 123.4(7) . . ? N4 C12 C11 126.1(8) . . ? N4 C12 H12 117.0 . . ? C11 C12 H12 117.0 . . ? N1 C13 C22 127.6(6) . 3_666 ? N1 C13 C14 108.7(6) . . ? C22 C13 C14 123.6(6) 3_666 . ? C15 C14 C13 106.0(6) . . ? C15 C14 H14 127.0 . . ? C13 C14 H14 127.0 . . ? C14 C15 C16 107.6(6) . . ? C14 C15 H15 126.2 . . ? C16 C15 H15 126.2 . . ? N1 C16 C17 126.1(6) . . ? N1 C16 C15 108.9(6) . . ? C17 C16 C15 124.9(6) . . ? C16 C17 C18 126.9(6) . . ? C16 C17 C5 116.2(6) . . ? C18 C17 C5 116.9(6) . . ? N2 C18 C19 109.4(6) . . ? N2 C18 C17 125.3(6) . . ? C19 C18 C17 125.2(6) . . ? C20 C19 C18 107.5(6) . . ? C20 C19 H19 126.2 . . ? C18 C19 H19 126.2 . . ? C19 C20 C21 107.1(6) . . ? C19 C20 H20 126.4 . . ? C21 C20 H20 126.4 . . ? N2 C21 C22 125.5(6) . . ? N2 C21 C20 108.3(6) . . ? C22 C21 C20 126.2(6) . . ? C13 C22 C21 125.0(6) 3_666 . ? C13 C22 C11 116.6(6) 3_666 . ? C21 C22 C11 118.2(6) . . ? 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 Mn1 N1 2.080(5) . ? Mn1 N1 2.080(5) 3_666 ? Mn1 N2 2.105(5) . ? Mn1 N2 2.105(5) 3_666 ? Mn1 O1 2.310(6) 4_666 ? Mn1 O1 2.310(6) 2 ? O1 C1 1.408(9) . ? O1 H1O1 0.8300 . ? O2 C7 1.309(13) . ? O2 H1O2 0.8300 . ? N1 C13 1.352(9) . ? N1 C16 1.368(8) . ? N2 C18 1.362(8) . ? N2 C21 1.370(9) . ? N4 C8 1.314(12) . ? N4 C12 1.329(10) . ? N6 C2 1.341(9) . ? N6 C6 1.349(10) . ? C1 C2 1.517(9) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.359(10) . ? C3 C4 1.380(10) . ? C3 H3 0.9500 . ? C4 C5 1.389(10) . ? C4 H4 0.9500 . ? C5 C6 1.366(11) . ? C5 C17 1.492(8) . ? C6 H6 0.9500 . ? C7 C8 1.576(14) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.389(14) . ? C9 C10 1.395(12) . ? C9 H9 0.9500 . ? C10 C11 1.371(11) . ? C10 H10 0.9500 . ? C11 C12 1.372(11) . ? C11 C22 1.468(10) . ? C12 H12 0.9500 . ? C13 C22 1.422(9) 3_666 ? C13 C14 1.464(10) . ? C14 C15 1.372(10) . ? C14 H14 0.9500 . ? C15 C16 1.430(10) . ? C15 H15 0.9500 . ? C16 C17 1.408(10) . ? C17 C18 1.418(10) . ? C18 C19 1.414(10) . ? C19 C20 1.354(11) . ? C19 H19 0.9500 . ? C20 C21 1.437(10) . ? C20 H20 0.9500 . ? C21 C22 1.419(9) . ?