#------------------------------------------------------------------------------ #$Date: 2019-02-22 01:09:21 +0200 (Fri, 22 Feb 2019) $ #$Revision: 213770 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/30/7123040.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_7123040 loop_ _publ_author_name 'Sarbajna, Abir' 'Patil, Pradnya H.' 'Dinh, Minh Hoan' 'Gladkovskaya, Olga' 'Fayzullin, Robert R.' 'Lapointe, S\'ebastien' 'Khaskin, Eugene' 'Khusnutdinova, Julia R.' _publ_section_title ; Facile and reversible double dearomatization of pyridines in non-phosphine MnI complexes with N,S-donor pyridinophane ligand ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC00424F _journal_year 2019 _chemical_formula_moiety 'C16 H13 Mn N2 O2 S2' _chemical_formula_sum 'C16 H13 Mn N2 O2 S2' _chemical_formula_weight 384.34 _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-01-02 deposited with the CCDC. 2019-02-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.355(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.7117(3) _cell_length_b 13.0041(2) _cell_length_c 8.82065(19) _cell_measurement_reflns_used 13926 _cell_measurement_temperature 94(2) _cell_measurement_theta_max 30.3840 _cell_measurement_theta_min 2.1900 _cell_volume 1523.69(5) _computing_cell_refinement 'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)' _computing_molecular_graphics ; WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009); ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009) ; _computing_publication_material 'enCIFer (Allen, 2004)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 94(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'XtaLAB Pro: Kappa dual offset/far' _diffrn_measurement_method '\w scans' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_unetI/netI 0.0220 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 30423 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.997 _diffrn_reflns_theta_min 2.192 _diffrn_source 'microfocus sealed X-ray tube' _exptl_absorpt_coefficient_mu 1.150 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.773 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015). Numerical absorption correction based on gaussian integration over a multifaceted crystal model. Empirical absorption correction using spherical harmonics, frame scaling and detector area scaling, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.675 _exptl_crystal_description prism _exptl_crystal_F_000 784 _exptl_crystal_recrystallization_method 'vapor diffusion of pentane into a benzene solution' _exptl_crystal_size_max 0.110 _exptl_crystal_size_mid 0.053 _exptl_crystal_size_min 0.037 _refine_diff_density_max 1.102 _refine_diff_density_min -0.648 _refine_diff_density_rms 0.087 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.312 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 3981 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.312 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0477 _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^)+(0.0153P)^2^+3.8202P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1076 _refine_ls_wR_factor_ref 0.1088 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3704 _reflns_number_total 3981 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc00424f2.cif _cod_data_source_block jk344 _cod_original_cell_volume 1523.69(6) _cod_database_code 7123040 _shelx_shelxl_version_number 2018/3 _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 0.884 _shelx_estimated_absorpt_t_max 0.959 _shelx_res_file ; TITL jk344 in P2(1)/c shelx.res created by SHELXL-2018/3 at 10:19:02 on 02-Jan-2019 CELL 0.71073 13.711709 13.004102 8.820650 90.0000 104.3547 90.0000 ZERR 4.00 0.000319 0.000231 0.000190 0.0000 0.0023 0.0000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S MN UNIT 64 52 8 8 8 4 MERG 2 OMIT -2.00 58.00 OMIT -11 1 8 SADI 0.01 C11 H11 C27 H27 MORE -1 FMAP 2 PLAN 10 SIZE 0.037 0.053 0.110 ACTA BOND $H CONF LIST 4 L.S. 20 TEMP -179.15 WGHT 0.015300 3.820200 FVAR 0.49642 0.51438 MN1 6 0.243597 0.538796 0.417453 11.00000 0.01952 0.01522 = 0.01616 -0.00177 0.00066 -0.00022 S1 5 0.129318 0.435838 0.490543 11.00000 0.02316 0.02969 = 0.01805 -0.00125 0.00388 -0.00608 S2 5 0.361842 0.603902 0.300911 11.00000 0.02363 0.01826 = 0.02059 0.00081 0.00197 -0.00423 O2 4 0.333589 0.611438 0.738299 11.00000 0.03432 0.04521 = 0.02161 -0.01099 0.00640 -0.01146 O1 4 0.117171 0.724623 0.371289 11.00000 0.03837 0.03106 = 0.05306 -0.01411 -0.00681 0.01457 N1 3 0.175907 0.488836 0.195773 11.00000 0.02283 0.01284 = 0.01561 0.00016 0.00080 0.00213 N2 3 0.327093 0.406138 0.434017 11.00000 0.02155 0.01645 = 0.01846 0.00032 -0.00231 -0.00074 C2 1 0.300331 0.581524 0.611490 11.00000 0.02131 0.02437 = 0.02161 -0.00233 0.00571 -0.00357 C1 1 0.167131 0.651360 0.389130 11.00000 0.02521 0.02487 = 0.02723 -0.00843 -0.00163 0.00009 C11 1 0.071258 0.376865 0.307845 11.00000 0.02730 0.02564 = 0.01899 -0.00007 -0.00167 -0.00308 PART 1 AFIX 23 H11A 2 0.085662 0.302205 0.316766 21.00000 -1.20000 H11B 2 -0.002541 0.385428 0.288678 21.00000 -1.20000 AFIX 0 PART 2 H11 2 0.024254 0.332119 0.306972 -21.00000 0.01598 PART 0 C12 1 0.101942 0.415574 0.173407 11.00000 0.01944 0.01517 = 0.01837 -0.00069 0.00319 0.00134 C13 1 0.055883 0.380711 0.019929 11.00000 0.02105 0.01718 = 0.02261 -0.00330 0.00331 -0.00027 AFIX 43 H13 2 0.004585 0.329876 0.004040 11.00000 -1.20000 AFIX 0 C14 1 0.085574 0.420546 -0.105315 11.00000 0.02547 0.02288 = 0.01768 -0.00537 0.00331 0.00100 AFIX 43 H14 2 0.055353 0.396908 -0.208143 11.00000 -1.20000 AFIX 0 C15 1 0.160461 0.496073 -0.081475 11.00000 0.02703 0.02352 = 0.01768 0.00078 0.00453 0.00157 AFIX 43 H15 2 0.181420 0.524644 -0.167361 11.00000 -1.20000 AFIX 0 C16 1 0.203362 0.528285 0.069873 11.00000 0.02258 0.01596 = 0.01954 0.00155 0.00105 0.00158 C17 1 0.280279 0.613453 0.103863 11.00000 0.03225 0.02432 = 0.02022 0.00548 -0.00099 -0.00529 AFIX 23 H17A 2 0.245192 0.680611 0.091813 11.00000 -1.20000 H17B 2 0.321907 0.610536 0.026909 11.00000 -1.20000 AFIX 0 C21 1 0.218003 0.338358 0.586984 11.00000 0.03387 0.02771 = 0.02217 0.00814 0.00052 -0.00437 AFIX 23 H21A 2 0.249416 0.360319 0.695583 11.00000 -1.20000 H21B 2 0.181641 0.273132 0.591714 11.00000 -1.20000 AFIX 0 C22 1 0.298157 0.320930 0.501885 11.00000 0.03075 0.01979 = 0.01734 0.00307 -0.00394 -0.00227 C23 1 0.342705 0.226170 0.496840 11.00000 0.04962 0.01694 = 0.02407 0.00365 -0.00491 -0.00031 AFIX 43 H23 2 0.319275 0.167254 0.540821 11.00000 -1.20000 AFIX 0 C24 1 0.422498 0.218613 0.426173 11.00000 0.04308 0.01924 = 0.02674 -0.00254 -0.00563 0.00777 AFIX 43 H24 2 0.454729 0.154248 0.423136 11.00000 -1.20000 AFIX 0 C25 1 0.454931 0.303973 0.360664 11.00000 0.02622 0.02701 = 0.02541 -0.00442 -0.00230 0.00505 AFIX 43 H25 2 0.510340 0.299274 0.314278 11.00000 -1.20000 AFIX 0 C26 1 0.404747 0.399096 0.363115 11.00000 0.02108 0.02040 = 0.01705 -0.00339 -0.00100 -0.00150 C27 1 0.433722 0.490573 0.293103 11.00000 0.03140 0.02576 = 0.02515 -0.00099 0.00450 0.00484 PART 2 AFIX 23 H27A 2 0.430201 0.475489 0.181863 -21.00000 -1.20000 H27B 2 0.504962 0.505608 0.344964 -21.00000 -1.20000 AFIX 0 PART 1 H27 2 0.483114 0.495696 0.248402 21.00000 0.03307 PART 0 HKLF 4 REM jk344 in P2(1)/c REM wR2 = 0.1088, GooF = S = 1.312, Restrained GooF = 1.312 for all data REM R1 = 0.0477 for 3704 Fo > 4sig(Fo) and 0.0518 for all 3981 data REM 217 parameters refined using 1 restraints END WGHT 0.0153 3.8203 REM Highest difference peak 1.102, deepest hole -0.648, 1-sigma level 0.087 Q1 1 0.1576 0.3814 0.5161 11.00000 0.05 1.10 Q2 1 0.1979 0.5527 0.4555 11.00000 0.05 0.53 Q3 1 0.3049 0.6330 0.3193 11.00000 0.05 0.47 Q4 1 0.2364 0.3004 0.5187 11.00000 0.05 0.47 Q5 1 0.1582 0.6187 0.4752 11.00000 0.05 0.45 Q6 1 0.3438 0.5503 0.7549 11.00000 0.05 0.43 Q7 1 0.1651 0.5199 -0.0086 11.00000 0.05 0.43 Q8 1 0.0814 0.6837 0.4723 11.00000 0.05 0.41 Q9 1 0.2455 0.5053 0.4988 11.00000 0.05 0.40 Q10 1 0.0645 0.4178 0.0941 11.00000 0.05 0.40 ; _shelx_res_checksum 94800 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 Mn1 Mn 0.24360(3) 0.53880(3) 0.41745(5) 0.01763(11) Uani 1 1 d . . . . . S1 S 0.12932(6) 0.43584(6) 0.49054(9) 0.02385(17) Uani 1 1 d . . . . . S2 S 0.36184(6) 0.60390(5) 0.30091(8) 0.02144(16) Uani 1 1 d . . . . . O2 O 0.33359(18) 0.6114(2) 0.7383(3) 0.0338(6) Uani 1 1 d . . . . . O1 O 0.1172(2) 0.7246(2) 0.3713(3) 0.0440(7) Uani 1 1 d . . . . . N1 N 0.17591(18) 0.48884(17) 0.1958(3) 0.0178(5) Uani 1 1 d . . . . . N2 N 0.32709(18) 0.40614(18) 0.4340(3) 0.0201(5) Uani 1 1 d . . . . . C2 C 0.3003(2) 0.5815(2) 0.6115(3) 0.0224(6) Uani 1 1 d . . . . . C1 C 0.1671(2) 0.6514(2) 0.3891(4) 0.0272(7) Uani 1 1 d . . . . . C11 C 0.0713(2) 0.3769(2) 0.3078(3) 0.0253(6) Uani 1 1 d D . . . . H11A H 0.085662 0.302205 0.316766 0.030 Uiso 0.51(4) 1 calc R U P A 1 H11B H -0.002541 0.385428 0.288678 0.030 Uiso 0.51(4) 1 calc R U P A 1 H11 H 0.024(5) 0.332(5) 0.307(8) 0.016(18) Uiso 0.49(4) 1 d D . P A 2 C12 C 0.1019(2) 0.4156(2) 0.1734(3) 0.0179(5) Uani 1 1 d . . . . . C13 C 0.0559(2) 0.3807(2) 0.0199(3) 0.0207(6) Uani 1 1 d . . . . . H13 H 0.004585 0.329876 0.004040 0.025 Uiso 1 1 calc R U . . . C14 C 0.0856(2) 0.4205(2) -0.1053(3) 0.0224(6) Uani 1 1 d . . . . . H14 H 0.055353 0.396908 -0.208143 0.027 Uiso 1 1 calc R U . . . C15 C 0.1605(2) 0.4961(2) -0.0815(3) 0.0229(6) Uani 1 1 d . . . . . H15 H 0.181420 0.524644 -0.167361 0.028 Uiso 1 1 calc R U . . . C16 C 0.2034(2) 0.5283(2) 0.0699(3) 0.0201(5) Uani 1 1 d . . . . . C17 C 0.2803(3) 0.6135(2) 0.1039(4) 0.0269(6) Uani 1 1 d . . . . . H17A H 0.245192 0.680611 0.091813 0.032 Uiso 1 1 calc R U . . . H17B H 0.321907 0.610536 0.026909 0.032 Uiso 1 1 calc R U . . . C21 C 0.2180(3) 0.3384(3) 0.5870(4) 0.0291(7) Uani 1 1 d . . . . . H21A H 0.249416 0.360319 0.695583 0.035 Uiso 1 1 calc R U . . . H21B H 0.181641 0.273132 0.591714 0.035 Uiso 1 1 calc R U . . . C22 C 0.2982(2) 0.3209(2) 0.5019(3) 0.0244(6) Uani 1 1 d . . . . . C23 C 0.3427(3) 0.2262(2) 0.4968(4) 0.0327(8) Uani 1 1 d . . . . . H23 H 0.319275 0.167254 0.540821 0.039 Uiso 1 1 calc R U . . . C24 C 0.4225(3) 0.2186(3) 0.4262(4) 0.0322(8) Uani 1 1 d . . . . . H24 H 0.454729 0.154248 0.423136 0.039 Uiso 1 1 calc R U . . . C25 C 0.4549(2) 0.3040(2) 0.3607(4) 0.0277(7) Uani 1 1 d . . . . . H25 H 0.510340 0.299274 0.314278 0.033 Uiso 1 1 calc R U . . . C26 C 0.4047(2) 0.3991(2) 0.3631(3) 0.0205(6) Uani 1 1 d . . . . . C27 C 0.4337(3) 0.4906(3) 0.2931(4) 0.0279(7) Uani 1 1 d D . . . . H27A H 0.430201 0.475489 0.181863 0.033 Uiso 0.49(4) 1 calc R U P A 2 H27B H 0.504962 0.505608 0.344964 0.033 Uiso 0.49(4) 1 calc R U P A 2 H27 H 0.483(5) 0.496(6) 0.248(9) 0.03(2) Uiso 0.51(4) 1 d D . P A 1 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 0.0195(2) 0.0152(2) 0.0162(2) -0.00177(16) 0.00066(15) -0.00022(16) S1 0.0232(4) 0.0297(4) 0.0181(3) -0.0013(3) 0.0039(3) -0.0061(3) S2 0.0236(3) 0.0183(3) 0.0206(3) 0.0008(3) 0.0020(3) -0.0042(3) O2 0.0343(13) 0.0452(14) 0.0216(11) -0.0110(10) 0.0064(10) -0.0115(11) O1 0.0384(15) 0.0311(13) 0.0531(17) -0.0141(12) -0.0068(12) 0.0146(11) N1 0.0228(12) 0.0128(10) 0.0156(11) 0.0002(8) 0.0008(9) 0.0021(9) N2 0.0216(12) 0.0165(11) 0.0185(11) 0.0003(9) -0.0023(9) -0.0007(9) C2 0.0213(14) 0.0244(14) 0.0216(14) -0.0023(11) 0.0057(11) -0.0036(11) C1 0.0252(15) 0.0249(15) 0.0272(16) -0.0084(12) -0.0016(12) 0.0001(12) C11 0.0273(15) 0.0256(15) 0.0190(14) -0.0001(12) -0.0017(12) -0.0031(12) C12 0.0194(13) 0.0152(12) 0.0184(13) -0.0007(10) 0.0032(10) 0.0013(10) C13 0.0211(13) 0.0172(13) 0.0226(14) -0.0033(11) 0.0033(11) -0.0003(11) C14 0.0255(14) 0.0229(14) 0.0177(13) -0.0054(11) 0.0033(11) 0.0010(12) C15 0.0270(15) 0.0235(14) 0.0177(13) 0.0008(11) 0.0045(11) 0.0016(12) C16 0.0226(13) 0.0160(12) 0.0195(13) 0.0015(10) 0.0010(10) 0.0016(11) C17 0.0323(16) 0.0243(15) 0.0202(14) 0.0055(12) -0.0010(12) -0.0053(12) C21 0.0339(17) 0.0277(16) 0.0222(15) 0.0081(12) 0.0005(13) -0.0044(13) C22 0.0307(16) 0.0198(14) 0.0173(13) 0.0031(11) -0.0039(11) -0.0023(12) C23 0.050(2) 0.0169(14) 0.0241(16) 0.0037(12) -0.0049(14) -0.0003(14) C24 0.043(2) 0.0192(14) 0.0267(16) -0.0025(12) -0.0056(14) 0.0078(13) C25 0.0262(15) 0.0270(15) 0.0254(15) -0.0044(12) -0.0023(12) 0.0050(13) C26 0.0211(13) 0.0204(13) 0.0171(13) -0.0034(10) -0.0010(10) -0.0015(11) C27 0.0314(17) 0.0258(15) 0.0252(15) -0.0010(12) 0.0045(13) 0.0048(13) 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' S S 0.1246 0.1234 '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 C1 Mn1 C2 88.86(14) C1 Mn1 N1 90.86(12) C2 Mn1 N1 178.88(12) C1 Mn1 N2 175.95(12) C2 Mn1 N2 95.19(12) N1 Mn1 N2 85.09(9) C1 Mn1 S1 95.78(12) C2 Mn1 S1 94.51(10) N1 Mn1 S1 84.43(7) N2 Mn1 S1 84.06(7) C1 Mn1 S2 95.22(12) C2 Mn1 S2 97.29(10) N1 Mn1 S2 83.82(7) N2 Mn1 S2 84.16(8) S1 Mn1 S2 164.01(3) C11 S1 C21 102.72(16) C11 S1 Mn1 100.47(11) C21 S1 Mn1 96.63(11) C27 S2 C17 103.52(16) C27 S2 Mn1 99.88(12) C17 S2 Mn1 96.78(11) C16 N1 C12 119.4(2) C16 N1 Mn1 120.54(19) C12 N1 Mn1 120.10(19) C22 N2 C26 119.4(3) C22 N2 Mn1 119.7(2) C26 N2 Mn1 120.5(2) O2 C2 Mn1 177.1(3) O1 C1 Mn1 179.7(4) C12 C11 S1 115.9(2) C12 C11 H11A 108.3 S1 C11 H11A 108.3 C12 C11 H11B 108.3 S1 C11 H11B 108.3 H11A C11 H11B 107.4 C12 C11 H11 126(5) S1 C11 H11 117(5) N1 C12 C13 119.9(3) N1 C12 C11 118.7(2) C13 C12 C11 121.4(3) C14 C13 C12 119.8(3) C14 C13 H13 120.1 C12 C13 H13 120.1 C13 C14 C15 119.9(3) C13 C14 H14 120.1 C15 C14 H14 120.1 C16 C15 C14 118.6(3) C16 C15 H15 120.7 C14 C15 H15 120.7 N1 C16 C15 122.5(3) N1 C16 C17 115.9(2) C15 C16 C17 121.6(3) C16 C17 S2 111.9(2) C16 C17 H17A 109.2 S2 C17 H17A 109.2 C16 C17 H17B 109.2 S2 C17 H17B 109.2 H17A C17 H17B 107.9 C22 C21 S1 111.2(2) C22 C21 H21A 109.4 S1 C21 H21A 109.4 C22 C21 H21B 109.4 S1 C21 H21B 109.4 H21A C21 H21B 108.0 N2 C22 C23 122.1(3) N2 C22 C21 115.3(3) C23 C22 C21 122.5(3) C22 C23 C24 118.8(3) C22 C23 H23 120.6 C24 C23 H23 120.6 C25 C24 C23 120.2(3) C25 C24 H24 119.9 C23 C24 H24 119.9 C24 C25 C26 119.3(3) C24 C25 H25 120.4 C26 C25 H25 120.4 N2 C26 C25 120.1(3) N2 C26 C27 118.1(3) C25 C26 C27 121.8(3) C26 C27 S2 116.9(2) C26 C27 H27A 108.1 S2 C27 H27A 108.1 C26 C27 H27B 108.1 S2 C27 H27B 108.1 H27A C27 H27B 107.3 C26 C27 H27 126(5) S2 C27 H27 117(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Mn1 C1 1.782(3) Mn1 C2 1.784(3) Mn1 N1 2.051(2) Mn1 N2 2.056(2) Mn1 S1 2.2726(9) Mn1 S2 2.2866(9) S1 C11 1.784(3) S1 C21 1.816(3) S2 C27 1.784(3) S2 C17 1.823(3) O2 C2 1.165(4) O1 C1 1.161(4) N1 C16 1.358(4) N1 C12 1.370(4) N2 C22 1.364(4) N2 C26 1.365(4) C11 C12 1.444(4) C11 H11A 0.9900 C11 H11B 0.9900 C11 H11 0.87(5) C12 C13 1.419(4) C13 C14 1.370(4) C13 H13 0.9500 C14 C15 1.399(4) C14 H14 0.9500 C15 C16 1.384(4) C15 H15 0.9500 C16 C17 1.507(4) C17 H17A 0.9900 C17 H17B 0.9900 C21 C22 1.494(5) C21 H21A 0.9900 C21 H21B 0.9900 C22 C23 1.381(4) C23 C24 1.390(5) C23 H23 0.9500 C24 C25 1.375(5) C24 H24 0.9500 C25 C26 1.418(4) C25 H25 0.9500 C26 C27 1.441(4) C27 H27A 0.9900 C27 H27B 0.9900 C27 H27 0.87(5) 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 C21 S1 C11 C12 -105.5(3) Mn1 S1 C11 C12 -6.2(3) C16 N1 C12 C13 0.9(4) Mn1 N1 C12 C13 -179.5(2) C16 N1 C12 C11 -178.0(3) Mn1 N1 C12 C11 1.6(3) S1 C11 C12 N1 3.7(4) S1 C11 C12 C13 -175.1(2) N1 C12 C13 C14 0.0(4) C11 C12 C13 C14 178.8(3) C12 C13 C14 C15 -0.6(4) C13 C14 C15 C16 0.4(4) C12 N1 C16 C15 -1.1(4) Mn1 N1 C16 C15 179.3(2) C12 N1 C16 C17 176.1(3) Mn1 N1 C16 C17 -3.5(3) C14 C15 C16 N1 0.4(4) C14 C15 C16 C17 -176.6(3) N1 C16 C17 S2 27.6(3) C15 C16 C17 S2 -155.2(2) C27 S2 C17 C16 68.1(3) Mn1 S2 C17 C16 -33.8(2) C11 S1 C21 C22 65.3(3) Mn1 S1 C21 C22 -37.0(2) C26 N2 C22 C23 -2.3(4) Mn1 N2 C22 C23 170.8(2) C26 N2 C22 C21 175.5(3) Mn1 N2 C22 C21 -11.5(3) S1 C21 C22 N2 34.7(3) S1 C21 C22 C23 -147.6(3) N2 C22 C23 C24 2.9(5) C21 C22 C23 C24 -174.7(3) C22 C23 C24 C25 -1.0(5) C23 C24 C25 C26 -1.3(5) C22 N2 C26 C25 -0.2(4) Mn1 N2 C26 C25 -173.2(2) C22 N2 C26 C27 -179.8(3) Mn1 N2 C26 C27 7.3(3) C24 C25 C26 N2 2.0(4) C24 C25 C26 C27 -178.5(3) N2 C26 C27 S2 -1.9(4) C25 C26 C27 S2 178.5(2) C17 S2 C27 C26 -102.7(3) Mn1 S2 C27 C26 -3.2(3)