#------------------------------------------------------------------------------ #$Date: 2019-02-22 01:09:21 +0200 (Fri, 22 Feb 2019) $ #$Revision: 213770 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/30/7123037.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_7123037 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 H14 Mn N2 O2 S2 1+, Br 1-' _chemical_formula_sum 'C16 H14 Br Mn N2 O2 S2' _chemical_formula_weight 465.26 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-I 2ya' _space_group_name_H-M_alt 'I 1 2/a 1' _symmetry_space_group_name_Hall '-I 2ya' _symmetry_space_group_name_H-M 'I 1 2/a 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2018-12-30 deposited with the CCDC. 2019-02-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 117.847(5) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 17.4339(6) _cell_length_b 11.9674(3) _cell_length_c 18.4715(7) _cell_measurement_reflns_used 13202 _cell_measurement_temperature 101(2) _cell_measurement_theta_max 30.2820 _cell_measurement_theta_min 2.6930 _cell_volume 3407.6(2) _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 101(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.880 _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 0.0670 _diffrn_reflns_av_unetI/netI 0.0385 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.880 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 27368 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.880 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.314 _diffrn_reflns_theta_min 2.110 _diffrn_source 'microfocus sealed X-ray tube' _exptl_absorpt_coefficient_mu 3.376 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.461 _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 'bright yellow' _exptl_crystal_density_diffrn 1.814 _exptl_crystal_description needle _exptl_crystal_F_000 1856 _exptl_crystal_recrystallization_method 'vapor diffusion of diethyl ether into a DCM/MeOH (1:1) solution' _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.049 _exptl_crystal_size_min 0.043 _refine_diff_density_max 0.693 _refine_diff_density_min -0.614 _refine_diff_density_rms 0.091 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 4504 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0260 _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^)+(0.0287P)^2^+5.1353P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.0692 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4098 _reflns_number_total 4504 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc00424f2.cif _cod_data_source_block jk198 _cod_original_cell_volume 3407.5(2) _cod_database_code 7123037 _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 0.486 _shelx_estimated_absorpt_t_max 0.868 _shelx_res_file ; TITL jk198 in I2/a shelx.res created by SHELXL-2018/3 at 13:53:13 on 29-Dec-2018 CELL 0.71073 17.433867 11.967350 18.471501 90.0000 117.8473 90.0000 ZERR 8.00 0.000639 0.000330 0.000716 0.0000 0.0048 0.0000 LATT 2 SYMM 1/2 - X, Y, - Z SFAC C H N O S MN BR UNIT 128 112 16 16 16 8 8 MERG 2 OMIT 4 0 6 MORE -1 FMAP 2 PLAN 22 SIZE 0.043 0.049 0.250 ACTA BOND $H CONF LIST 4 L.S. 20 TEMP -172.15 WGHT 0.028700 5.135300 FVAR 0.20560 BR1 7 0.302568 0.786572 0.386269 11.00000 0.01126 0.01520 = 0.01256 0.00077 0.00614 0.00070 MN1 6 0.576105 0.704545 0.722779 11.00000 0.01010 0.00766 = 0.01044 0.00103 0.00727 0.00070 S1 5 0.439724 0.763186 0.689522 11.00000 0.01313 0.01014 = 0.01167 0.00363 0.00840 0.00450 S2 5 0.696676 0.600153 0.759093 11.00000 0.00900 0.01339 = 0.01230 0.00073 0.00691 0.00039 O1 4 0.596034 0.819708 0.591315 11.00000 0.01854 0.01700 = 0.01656 0.00335 0.01230 -0.00007 O2 4 0.667919 0.893864 0.831405 11.00000 0.03483 0.01985 = 0.02848 -0.01150 0.02210 -0.01100 N1 3 0.512284 0.574445 0.644895 11.00000 0.01120 0.01104 = 0.00993 0.00246 0.00763 0.00180 N2 3 0.565405 0.614708 0.812593 11.00000 0.00933 0.00781 = 0.01030 -0.00051 0.00568 -0.00014 C21 1 0.411691 0.667563 0.750825 11.00000 0.01066 0.01355 = 0.01221 0.00361 0.00759 0.00283 AFIX 23 H21A 2 0.382026 0.709975 0.776536 11.00000 -1.20000 H21B 2 0.370658 0.610594 0.714359 11.00000 -1.20000 AFIX 0 C13 1 0.382411 0.502571 0.533626 11.00000 0.01153 0.02454 = 0.01413 -0.00248 0.00659 -0.00153 AFIX 43 H13 2 0.322873 0.512147 0.495632 11.00000 -1.20000 AFIX 0 C16 1 0.554562 0.479264 0.644814 11.00000 0.01300 0.01014 = 0.01264 0.00114 0.00895 0.00110 C23 1 0.482326 0.550596 0.877808 11.00000 0.01236 0.01206 = 0.01276 0.00106 0.00918 0.00147 AFIX 43 H23 2 0.429196 0.550349 0.880446 11.00000 -1.20000 AFIX 0 C14 1 0.425544 0.405244 0.533444 11.00000 0.01818 0.01992 = 0.01895 -0.00896 0.01061 -0.00576 AFIX 43 H14 2 0.395839 0.347419 0.495306 11.00000 -1.20000 AFIX 0 C25 1 0.630246 0.494446 0.929587 11.00000 0.01074 0.01080 = 0.00857 -0.00071 0.00303 0.00090 AFIX 43 H25 2 0.679288 0.453256 0.967270 11.00000 -1.20000 AFIX 0 C17 1 0.649135 0.469145 0.705656 11.00000 0.01495 0.01281 = 0.01570 -0.00131 0.00574 0.00385 AFIX 23 H17A 2 0.681568 0.443838 0.676699 11.00000 -1.20000 H17B 2 0.655869 0.411359 0.746564 11.00000 -1.20000 AFIX 0 C27 1 0.717444 0.566708 0.862717 11.00000 0.00876 0.01731 = 0.01093 0.00088 0.00488 0.00083 AFIX 23 H27A 2 0.749370 0.495071 0.879721 11.00000 -1.20000 H27B 2 0.754423 0.625599 0.900572 11.00000 -1.20000 AFIX 0 C22 1 0.489662 0.609857 0.816512 11.00000 0.00955 0.00840 = 0.00980 -0.00145 0.00520 0.00039 C1 1 0.586580 0.775978 0.642727 11.00000 0.01150 0.01055 = 0.01530 -0.00164 0.00766 0.00115 C24 1 0.553382 0.491963 0.934940 11.00000 0.01319 0.01316 = 0.00964 0.00035 0.00633 -0.00078 AFIX 43 H24 2 0.549607 0.450717 0.977106 11.00000 -1.20000 AFIX 0 C2 1 0.631750 0.818799 0.790027 11.00000 0.01900 0.01473 = 0.01804 0.00180 0.01494 0.00095 C26 1 0.634715 0.557569 0.868763 11.00000 0.00911 0.00925 = 0.01023 -0.00219 0.00465 0.00021 C11 1 0.384872 0.694726 0.590850 11.00000 0.01331 0.01828 = 0.00933 0.00189 0.00549 0.00624 AFIX 23 H11A 2 0.323666 0.680798 0.577365 11.00000 -1.20000 H11B 2 0.385238 0.744677 0.548291 11.00000 -1.20000 AFIX 0 C12 1 0.427325 0.585885 0.590038 11.00000 0.01084 0.01632 = 0.01079 0.00182 0.00762 0.00142 C15 1 0.512477 0.393209 0.589508 11.00000 0.01769 0.01290 = 0.01808 -0.00224 0.01117 -0.00024 AFIX 43 H15 2 0.542969 0.327092 0.590198 11.00000 -1.20000 AFIX 0 HKLF 4 REM jk198 in I2/a REM wR2 = 0.0692, GooF = S = 1.049, Restrained GooF = 1.049 for all data REM R1 = 0.0260 for 4098 Fo > 4sig(Fo) and 0.0297 for all 4504 data REM 217 parameters refined using 0 restraints END WGHT 0.0287 5.1354 REM Highest difference peak 0.693, deepest hole -0.614, 1-sigma level 0.091 Q1 1 0.3596 0.7842 0.3961 11.00000 0.05 0.69 Q2 1 0.2476 0.7802 0.3810 11.00000 0.05 0.64 Q3 1 0.4889 0.5825 0.8500 11.00000 0.05 0.61 Q4 1 0.5882 0.4909 0.9294 11.00000 0.05 0.52 Q5 1 0.3184 0.7894 0.3423 11.00000 0.05 0.49 Q6 1 0.6007 0.4794 0.6778 11.00000 0.05 0.49 Q7 1 0.6718 0.5605 0.8633 11.00000 0.05 0.48 Q8 1 0.3440 0.7903 0.4428 11.00000 0.05 0.47 Q9 1 0.5336 0.6986 0.7177 11.00000 0.05 0.46 Q10 1 0.3076 0.8769 0.4181 11.00000 0.05 0.45 Q11 1 0.2550 0.7848 0.3287 11.00000 0.05 0.45 Q12 1 0.4534 0.6364 0.7857 11.00000 0.05 0.45 Q13 1 0.6315 0.7093 0.7283 11.00000 0.05 0.45 Q14 1 0.5246 0.6177 0.8207 11.00000 0.05 0.43 Q15 1 0.7446 0.6038 0.7671 11.00000 0.05 0.42 Q16 1 0.4891 0.7521 0.7036 11.00000 0.05 0.42 Q17 1 0.6351 0.5164 0.8970 11.00000 0.05 0.42 Q18 1 0.4659 0.5801 0.6111 11.00000 0.05 0.41 Q19 1 0.4035 0.6372 0.5882 11.00000 0.05 0.40 Q20 1 0.6416 0.7612 0.7852 11.00000 0.05 0.40 Q21 1 0.5971 0.5834 0.8350 11.00000 0.05 0.39 Q22 1 0.5903 0.7069 0.6833 11.00000 0.05 0.39 ; _shelx_res_checksum 92898 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' '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 Br1 Br 0.30257(2) 0.78657(2) 0.38627(2) 0.01278(6) Uani 1 1 d . . Mn1 Mn 0.57611(2) 0.70454(2) 0.72278(2) 0.00841(7) Uani 1 1 d . . S1 S 0.43972(3) 0.76319(4) 0.68952(3) 0.01061(9) Uani 1 1 d . . S2 S 0.69668(3) 0.60015(4) 0.75909(3) 0.01080(9) Uani 1 1 d . . O1 O 0.59603(9) 0.81971(12) 0.59132(8) 0.0157(3) Uani 1 1 d . . O2 O 0.66792(10) 0.89386(13) 0.83141(9) 0.0248(3) Uani 1 1 d . . N1 N 0.51228(9) 0.57444(12) 0.64489(8) 0.0096(3) Uani 1 1 d . . N2 N 0.56540(9) 0.61471(12) 0.81259(8) 0.0087(3) Uani 1 1 d . . C21 C 0.41169(11) 0.66756(15) 0.75082(10) 0.0112(3) Uani 1 1 d . . H21A H 0.382026 0.709975 0.776536 0.013 Uiso 1 1 calc R U H21B H 0.370658 0.610594 0.714359 0.013 Uiso 1 1 calc R U C13 C 0.38241(12) 0.50257(17) 0.53363(11) 0.0165(4) Uani 1 1 d . . H13 H 0.322873 0.512147 0.495632 0.020 Uiso 1 1 calc R U C16 C 0.55456(11) 0.47926(15) 0.64481(10) 0.0107(3) Uani 1 1 d . . C23 C 0.48233(11) 0.55060(15) 0.87781(10) 0.0111(3) Uani 1 1 d . . H23 H 0.429196 0.550349 0.880446 0.013 Uiso 1 1 calc R U C14 C 0.42554(12) 0.40524(17) 0.53344(12) 0.0182(4) Uani 1 1 d . . H14 H 0.395839 0.347419 0.495306 0.022 Uiso 1 1 calc R U C25 C 0.63025(11) 0.49445(15) 0.92959(10) 0.0106(3) Uani 1 1 d . . H25 H 0.679288 0.453256 0.967270 0.013 Uiso 1 1 calc R U C17 C 0.64913(12) 0.46914(16) 0.70566(11) 0.0151(3) Uani 1 1 d . . H17A H 0.681568 0.443838 0.676699 0.018 Uiso 1 1 calc R U H17B H 0.655869 0.411359 0.746564 0.018 Uiso 1 1 calc R U C27 C 0.71744(11) 0.56671(16) 0.86272(10) 0.0122(3) Uani 1 1 d . . H27A H 0.749370 0.495071 0.879721 0.015 Uiso 1 1 calc R U H27B H 0.754423 0.625599 0.900572 0.015 Uiso 1 1 calc R U C22 C 0.48966(10) 0.60986(14) 0.81651(10) 0.0090(3) Uani 1 1 d . . C1 C 0.58658(11) 0.77598(15) 0.64273(11) 0.0119(3) Uani 1 1 d . . C24 C 0.55338(11) 0.49196(15) 0.93494(10) 0.0116(3) Uani 1 1 d . . H24 H 0.549607 0.450717 0.977106 0.014 Uiso 1 1 calc R U C2 C 0.63175(12) 0.81880(16) 0.79003(11) 0.0148(4) Uani 1 1 d . . C26 C 0.63472(11) 0.55757(14) 0.86876(10) 0.0095(3) Uani 1 1 d . . C11 C 0.38487(12) 0.69473(16) 0.59085(11) 0.0136(3) Uani 1 1 d . . H11A H 0.323666 0.680798 0.577365 0.016 Uiso 1 1 calc R U H11B H 0.385238 0.744677 0.548291 0.016 Uiso 1 1 calc R U C12 C 0.42733(11) 0.58589(15) 0.59004(10) 0.0116(3) Uani 1 1 d . . C15 C 0.51248(12) 0.39321(16) 0.58951(11) 0.0151(4) Uani 1 1 d . . H15 H 0.542969 0.327092 0.590198 0.018 Uiso 1 1 calc R U 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 Br1 0.01126(10) 0.01520(11) 0.01256(10) 0.00077(6) 0.00614(7) 0.00070(6) Mn1 0.01010(13) 0.00766(14) 0.01044(13) 0.00103(9) 0.00727(10) 0.00070(9) S1 0.0131(2) 0.0101(2) 0.01167(19) 0.00363(15) 0.00840(16) 0.00450(15) S2 0.00900(18) 0.0134(2) 0.01230(19) 0.00073(15) 0.00691(15) 0.00039(15) O1 0.0185(6) 0.0170(7) 0.0166(6) 0.0034(5) 0.0123(5) -0.0001(5) O2 0.0348(8) 0.0198(8) 0.0285(8) -0.0115(6) 0.0221(7) -0.0110(6) N1 0.0112(6) 0.0110(7) 0.0099(6) 0.0025(5) 0.0076(5) 0.0018(5) N2 0.0093(6) 0.0078(7) 0.0103(6) -0.0005(5) 0.0057(5) -0.0001(5) C21 0.0107(7) 0.0135(9) 0.0122(8) 0.0036(6) 0.0076(6) 0.0028(6) C13 0.0115(8) 0.0245(10) 0.0141(8) -0.0025(7) 0.0066(7) -0.0015(7) C16 0.0130(8) 0.0101(8) 0.0126(8) 0.0011(6) 0.0090(6) 0.0011(6) C23 0.0124(8) 0.0121(8) 0.0128(8) 0.0011(6) 0.0092(6) 0.0015(6) C14 0.0182(9) 0.0199(10) 0.0190(9) -0.0090(7) 0.0106(8) -0.0058(7) C25 0.0107(7) 0.0108(8) 0.0086(7) -0.0007(6) 0.0030(6) 0.0009(6) C17 0.0150(8) 0.0128(9) 0.0157(8) -0.0013(7) 0.0057(7) 0.0038(7) C27 0.0088(7) 0.0173(9) 0.0109(8) 0.0009(6) 0.0049(6) 0.0008(6) C22 0.0096(7) 0.0084(8) 0.0098(7) -0.0015(6) 0.0052(6) 0.0004(6) C1 0.0115(8) 0.0105(8) 0.0153(8) -0.0016(6) 0.0077(7) 0.0012(6) C24 0.0132(8) 0.0132(9) 0.0096(7) 0.0004(6) 0.0063(6) -0.0008(6) C2 0.0190(9) 0.0147(9) 0.0180(9) 0.0018(7) 0.0149(7) 0.0010(7) C26 0.0091(7) 0.0093(8) 0.0102(7) -0.0022(6) 0.0047(6) 0.0002(6) C11 0.0133(8) 0.0183(9) 0.0093(8) 0.0019(6) 0.0055(7) 0.0062(7) C12 0.0108(7) 0.0163(9) 0.0108(8) 0.0018(6) 0.0076(6) 0.0014(7) C15 0.0177(9) 0.0129(9) 0.0181(9) -0.0022(7) 0.0112(7) -0.0002(7) 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' Br Br -0.2901 2.4595 '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 88.69(8) C1 Mn1 N2 176.99(7) C2 Mn1 N2 93.63(7) C1 Mn1 N1 90.82(7) C2 Mn1 N1 179.50(7) N2 Mn1 N1 86.86(6) C1 Mn1 S2 93.99(6) C2 Mn1 S2 95.08(6) N2 Mn1 S2 83.91(4) N1 Mn1 S2 85.04(4) C1 Mn1 S1 97.29(6) C2 Mn1 S1 96.36(6) N2 Mn1 S1 84.36(4) N1 Mn1 S1 83.62(4) S2 Mn1 S1 164.09(2) C11 S1 C21 99.89(9) C11 S1 Mn1 97.26(6) C21 S1 Mn1 100.83(6) C27 S2 C17 101.32(9) C27 S2 Mn1 97.72(6) C17 S2 Mn1 100.90(6) C12 N1 C16 119.23(15) C12 N1 Mn1 119.43(12) C16 N1 Mn1 121.27(12) C26 N2 C22 118.68(14) C26 N2 Mn1 119.82(11) C22 N2 Mn1 121.50(11) C22 C21 S1 112.64(12) C22 C21 H21A 109.1 S1 C21 H21A 109.1 C22 C21 H21B 109.1 S1 C21 H21B 109.1 H21A C21 H21B 107.8 C14 C13 C12 119.21(17) C14 C13 H13 120.4 C12 C13 H13 120.4 N1 C16 C15 121.39(16) N1 C16 C17 118.22(15) C15 C16 C17 120.39(16) C24 C23 C22 119.25(15) C24 C23 H23 120.4 C22 C23 H23 120.4 C15 C14 C13 119.33(17) C15 C14 H14 120.3 C13 C14 H14 120.3 C26 C25 C24 119.39(15) C26 C25 H25 120.3 C24 C25 H25 120.3 C16 C17 S2 113.31(13) C16 C17 H17A 108.9 S2 C17 H17A 108.9 C16 C17 H17B 108.9 S2 C17 H17B 108.9 H17A C17 H17B 107.7 C26 C27 S2 111.61(11) C26 C27 H27A 109.3 S2 C27 H27A 109.3 C26 C27 H27B 109.3 S2 C27 H27B 109.3 H27A C27 H27B 108.0 N2 C22 C23 121.79(15) N2 C22 C21 118.24(14) C23 C22 C21 119.94(15) O1 C1 Mn1 177.39(16) C23 C24 C25 118.94(16) C23 C24 H24 120.5 C25 C24 H24 120.5 O2 C2 Mn1 177.89(16) N2 C26 C25 121.91(15) N2 C26 C27 116.78(15) C25 C26 C27 121.31(15) C12 C11 S1 111.81(12) C12 C11 H11A 109.3 S1 C11 H11A 109.3 C12 C11 H11B 109.3 S1 C11 H11B 109.3 H11A C11 H11B 107.9 N1 C12 C13 121.62(17) N1 C12 C11 116.85(16) C13 C12 C11 121.48(16) C14 C15 C16 119.21(17) C14 C15 H15 120.4 C16 C15 H15 120.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Mn1 C1 1.7897(18) Mn1 C2 1.797(2) Mn1 N2 2.0572(14) Mn1 N1 2.0582(15) Mn1 S2 2.2609(5) Mn1 S1 2.2712(5) S1 C11 1.8109(19) S1 C21 1.8297(17) S2 C27 1.8187(17) S2 C17 1.8317(19) O1 C1 1.162(2) O2 C2 1.157(2) N1 C12 1.355(2) N1 C16 1.357(2) N2 C26 1.354(2) N2 C22 1.357(2) C21 C22 1.502(2) C21 H21A 0.9900 C21 H21B 0.9900 C13 C14 1.387(3) C13 C12 1.390(3) C13 H13 0.9500 C16 C15 1.394(2) C16 C17 1.505(2) C23 C24 1.385(2) C23 C22 1.392(2) C23 H23 0.9500 C14 C15 1.387(3) C14 H14 0.9500 C25 C26 1.386(2) C25 C24 1.389(2) C25 H25 0.9500 C17 H17A 0.9900 C17 H17B 0.9900 C27 C26 1.502(2) C27 H27A 0.9900 C27 H27B 0.9900 C24 H24 0.9500 C11 C12 1.502(2) C11 H11A 0.9900 C11 H11B 0.9900 C15 H15 0.9500 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 C11 S1 C21 C22 115.54(13) Mn1 S1 C21 C22 16.11(13) C12 N1 C16 C15 0.1(2) Mn1 N1 C16 C15 -176.92(13) C12 N1 C16 C17 179.29(15) Mn1 N1 C16 C17 2.3(2) C12 C13 C14 C15 0.0(3) N1 C16 C17 S2 -10.1(2) C15 C16 C17 S2 169.18(14) C27 S2 C17 C16 111.91(13) Mn1 S2 C17 C16 11.66(14) C17 S2 C27 C26 -70.58(14) Mn1 S2 C27 C26 32.23(13) C26 N2 C22 C23 1.8(2) Mn1 N2 C22 C23 -179.04(13) C26 N2 C22 C21 -176.21(15) Mn1 N2 C22 C21 2.9(2) C24 C23 C22 N2 -2.1(3) C24 C23 C22 C21 175.93(16) S1 C21 C22 N2 -13.7(2) S1 C21 C22 C23 168.18(13) C22 C23 C24 C25 0.3(3) C26 C25 C24 C23 1.6(3) C22 N2 C26 C25 0.2(2) Mn1 N2 C26 C25 -178.95(13) C22 N2 C26 C27 -179.17(15) Mn1 N2 C26 C27 1.7(2) C24 C25 C26 N2 -1.9(3) C24 C25 C26 C27 177.40(16) S2 C27 C26 N2 -25.1(2) S2 C27 C26 C25 155.50(14) C21 S1 C11 C12 -69.20(14) Mn1 S1 C11 C12 33.18(13) C16 N1 C12 C13 -0.1(2) Mn1 N1 C12 C13 176.97(13) C16 N1 C12 C11 -177.70(15) Mn1 N1 C12 C11 -0.67(19) C14 C13 C12 N1 0.0(3) C14 C13 C12 C11 177.57(17) S1 C11 C12 N1 -24.55(19) S1 C11 C12 C13 157.80(14) C13 C14 C15 C16 0.0(3) N1 C16 C15 C14 0.0(3) C17 C16 C15 C14 -179.25(17)