# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jk198
_database_code_depnum_ccdc_archive 'CCDC 1887964'
loop_
_audit_author_name
_audit_author_address
'Robert Fayzullin'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS
Russia
;
_audit_update_record             
;
2018-12-30 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H14 Mn N2 O2 S2 1+, Br 1-'
_chemical_formula_sum            'C16 H14 Br Mn N2 O2 S2'
_exptl_crystal_recrystallization_method 
'vapor diffusion of diethyl ether into a DCM/MeOH (1:1) solution'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            'bright yellow'
_diffrn_ambient_temperature      101(2)
_chemical_formula_weight         465.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'
_chemical_absolute_configuration .

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'

_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.
;

_cell_length_a                   17.4339(6)
_cell_length_b                   11.9674(3)
_cell_length_c                   18.4715(7)
_cell_angle_alpha                90
_cell_angle_beta                 117.847(5)
_cell_angle_gamma                90
_cell_volume                     3407.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    13202
_cell_measurement_theta_min      2.6930
_cell_measurement_theta_max      30.2820
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    3.376
_shelx_estimated_absorpt_T_min   0.486
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_T_max  1.000
_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_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27368
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.110
_diffrn_reflns_theta_max         30.314
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4504
_reflns_number_gt                4098
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 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)'
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+5.1353P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4504
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 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_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
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_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
_geom_torsion_publ_flag
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) . . . . ?

_refine_diff_density_max         0.693
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.091

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jk357
_database_code_depnum_ccdc_archive 'CCDC 1887966'
loop_
_audit_author_name
_audit_author_address
'Robert Fayzullin'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS
Russia
;
_audit_update_record             
;
2018-12-30 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

# start Validation Reply
_vrf_PLAT112_jk357               
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         I         96 %Fit  
RESPONSE: Pseudo lattice centering/translation was reported. 
No obvious space group change is needed.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H14 Mn N2 O2 S2 1+, C H O2 1-, C H2 O2'
_chemical_formula_sum            'C18 H17 Mn N2 O6 S2'
_exptl_crystal_recrystallization_method 
'vapor diffusion of hexane into a dichloromethane solution'
_chemical_melting_point          ?

_exptl_crystal_description       plank
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      93(2)
_chemical_formula_weight         476.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration .

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'

_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.
;

_cell_length_a                   8.46572(14)
_cell_length_b                   14.8583(2)
_cell_length_c                   15.3199(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.6737(15)
_cell_angle_gamma                90
_cell_volume                     1905.00(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    22739
_cell_measurement_theta_min      2.7260
_cell_measurement_theta_max      32.4570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    0.952
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_T_max  1.000
_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_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59612
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.597
_diffrn_reflns_theta_max         32.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6441
_reflns_number_gt                5437
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 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)'
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.5840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6441
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.20509(2) 0.50108(2) 0.85997(2) 0.00686(5) Uani 1 1 d . . . . .
S1 S 0.43471(3) 0.50022(2) 0.80047(2) 0.01017(6) Uani 1 1 d . . . . .
S2 S -0.05323(3) 0.50367(2) 0.88368(2) 0.00890(6) Uani 1 1 d . . . . .
O1 O 0.29993(9) 0.36423(5) 0.99713(5) 0.01623(15) Uani 1 1 d . . . . .
O2 O 0.33101(10) 0.62440(6) 1.00427(5) 0.01912(16) Uani 1 1 d . . . . .
N1 N 0.12366(10) 0.41221(5) 0.75933(5) 0.00925(15) Uani 1 1 d . . . . .
N2 N 0.13305(10) 0.59959(5) 0.76731(5) 0.00881(15) Uani 1 1 d . . . . .
C1 C 0.26259(11) 0.41534(7) 0.94074(6) 0.01042(17) Uani 1 1 d . . . . .
C2 C 0.27925(12) 0.57837(7) 0.94594(7) 0.01125(17) Uani 1 1 d . . . . .
C11 C 0.39134(14) 0.41379(8) 0.71692(8) 0.0206(2) Uani 1 1 d . . . . .
H11A H 0.421854 0.436182 0.660931 0.025 Uiso 1 1 calc R U . . .
H11B H 0.457944 0.360323 0.735260 0.025 Uiso 1 1 calc R U . . .
C12 C 0.21926(13) 0.38582(7) 0.70059(7) 0.01298(18) Uani 1 1 d . . . . .
C13 C 0.16314(14) 0.33089(7) 0.62884(7) 0.0182(2) Uani 1 1 d . . . . .
H13 H 0.232627 0.312429 0.588986 0.022 Uiso 1 1 calc R U . . .
C14 C 0.00492(15) 0.30352(8) 0.61628(7) 0.0196(2) Uani 1 1 d . . . . .
H14 H -0.035779 0.266868 0.567201 0.023 Uiso 1 1 calc R U . . .
C15 C -0.09322(13) 0.33023(7) 0.67613(7) 0.01505(19) Uani 1 1 d . . . . .
H15 H -0.202030 0.312088 0.668765 0.018 Uiso 1 1 calc R U . . .
C16 C -0.02986(12) 0.38413(6) 0.74734(6) 0.01024(17) Uani 1 1 d . . . . .
C17 C -0.13083(12) 0.40871(7) 0.81615(7) 0.01143(18) Uani 1 1 d . . . . .
H17A H -0.138471 0.356028 0.854852 0.014 Uiso 1 1 calc R U . . .
H17B H -0.240072 0.423215 0.786632 0.014 Uiso 1 1 calc R U . . .
C21 C 0.40715(12) 0.60246(7) 0.73542(7) 0.0151(2) Uani 1 1 d . . . . .
H21A H 0.468996 0.651588 0.768213 0.018 Uiso 1 1 calc R U . . .
H21B H 0.450448 0.593168 0.679571 0.018 Uiso 1 1 calc R U . . .
C22 C 0.23553(12) 0.63068(7) 0.71422(7) 0.01150(18) Uani 1 1 d . . . . .
C23 C 0.18701(14) 0.68980(7) 0.64502(7) 0.0169(2) Uani 1 1 d . . . . .
H23 H 0.261080 0.710885 0.608884 0.020 Uiso 1 1 calc R U . . .
C24 C 0.02869(14) 0.71755(7) 0.62953(7) 0.0180(2) Uani 1 1 d . . . . .
H24 H -0.007067 0.757430 0.582191 0.022 Uiso 1 1 calc R U . . .
C25 C -0.07672(13) 0.68662(7) 0.68365(7) 0.01387(19) Uani 1 1 d . . . . .
H25 H -0.185530 0.704823 0.673910 0.017 Uiso 1 1 calc R U . . .
C26 C -0.02044(11) 0.62837(6) 0.75260(6) 0.00962(17) Uani 1 1 d . . . . .
C27 C -0.12971(11) 0.59869(7) 0.81566(6) 0.01082(17) Uani 1 1 d . . . . .
H27A H -0.234531 0.582202 0.781591 0.013 Uiso 1 1 calc R U . . .
H27B H -0.147085 0.649819 0.854548 0.013 Uiso 1 1 calc R U . . .
O31 O 0.56055(10) 0.30635(6) 0.55718(6) 0.02302(18) Uani 1 1 d . . . . .
O32 O 0.45301(10) 0.27682(5) 0.41727(5) 0.02033(17) Uani 1 1 d . . . . .
C3 C 0.49008(11) 0.25773(8) 0.49613(7) 0.0152(2) Uani 1 1 d . . . . .
H3 H 0.461886 0.198991 0.512817 0.018 Uiso 1 1 calc R U . . .
O41 O 0.67048(11) 0.45121(6) 0.50162(5) 0.02099(17) Uani 1 1 d D . . . .
H41 H 0.629(3) 0.4007(13) 0.5250(14) 0.079(7) Uiso 1 1 d D . . . .
O42 O 0.68457(10) 0.50329(5) 0.64063(6) 0.01577(16) Uani 1 1 d . . . . .
C4 C 0.70169(14) 0.51107(7) 0.56376(8) 0.0167(2) Uani 1 1 d . . . . .
H4 H 0.742396 0.567078 0.547141 0.020 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C2 1.7884(10) . ?
Mn1 C1 1.7914(10) . ?
Mn1 N2 2.0660(8) . ?
Mn1 N1 2.0677(8) . ?
Mn1 S1 2.2681(3) . ?
Mn1 S2 2.2705(3) . ?
S1 C11 1.8112(11) . ?
S1 C21 1.8124(10) . ?
S2 C17 1.8131(10) . ?
S2 C27 1.8152(10) . ?
O1 C1 1.1579(12) . ?
O2 C2 1.1576(13) . ?
N1 C16 1.3509(12) . ?
N1 C12 1.3559(13) . ?
N2 C26 1.3541(12) . ?
N2 C22 1.3566(13) . ?
C11 C12 1.4992(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3937(14) . ?
C13 C14 1.3852(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3851(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3938(14) . ?
C15 H15 0.9500 . ?
C16 C17 1.4989(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C21 C22 1.4999(14) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.3903(14) . ?
C23 C24 1.3881(16) . ?
C23 H23 0.9500 . ?
C24 C25 1.3849(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.3929(13) . ?
C25 H25 0.9500 . ?
C26 C27 1.5010(13) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
O31 C3 1.2587(13) . ?
O32 C3 1.2345(13) . ?
C3 H3 0.9500 . ?
O41 C4 1.3005(14) . ?
O41 H41 0.925(16) . ?
O42 C4 1.2136(14) . ?
C4 H4 0.9500 . ?

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
C2 Mn1 C1 85.37(5) . . ?
C2 Mn1 N2 94.91(4) . . ?
C1 Mn1 N2 178.60(4) . . ?
C2 Mn1 N1 178.77(4) . . ?
C1 Mn1 N1 94.94(4) . . ?
N2 Mn1 N1 84.80(3) . . ?
C2 Mn1 S1 94.17(3) . . ?
C1 Mn1 S1 96.52(3) . . ?
N2 Mn1 S1 84.83(2) . . ?
N1 Mn1 S1 84.62(2) . . ?
C2 Mn1 S2 96.37(3) . . ?
C1 Mn1 S2 93.98(3) . . ?
N2 Mn1 S2 84.62(2) . . ?
N1 Mn1 S2 84.79(2) . . ?
S1 Mn1 S2 165.674(13) . . ?
C11 S1 C21 102.13(6) . . ?
C11 S1 Mn1 101.15(4) . . ?
C21 S1 Mn1 99.74(3) . . ?
C17 S2 C27 102.16(5) . . ?
C17 S2 Mn1 99.81(3) . . ?
C27 S2 Mn1 100.96(3) . . ?
C16 N1 C12 118.61(8) . . ?
C16 N1 Mn1 120.29(6) . . ?
C12 N1 Mn1 120.95(7) . . ?
C26 N2 C22 118.50(8) . . ?
C26 N2 Mn1 120.96(6) . . ?
C22 N2 Mn1 120.26(6) . . ?
O1 C1 Mn1 175.53(9) . . ?
O2 C2 Mn1 176.22(9) . . ?
C12 C11 S1 113.75(7) . . ?
C12 C11 H11A 108.8 . . ?
S1 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
S1 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N1 C12 C13 121.75(10) . . ?
N1 C12 C11 118.12(9) . . ?
C13 C12 C11 120.07(9) . . ?
C14 C13 C12 119.28(10) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 119.21(10) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 118.97(10) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N1 C16 C15 122.19(9) . . ?
N1 C16 C17 117.91(8) . . ?
C15 C16 C17 119.83(9) . . ?
C16 C17 S2 113.26(7) . . ?
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 . . ?
C22 C21 S1 113.17(7) . . ?
C22 C21 H21A 108.9 . . ?
S1 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
S1 C21 H21B 108.9 . . ?
H21A C21 H21B 107.8 . . ?
N2 C22 C23 122.02(9) . . ?
N2 C22 C21 117.46(9) . . ?
C23 C22 C21 120.46(9) . . ?
C24 C23 C22 118.99(10) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 119.46(10) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 118.85(10) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
N2 C26 C25 122.16(9) . . ?
N2 C26 C27 117.98(8) . . ?
C25 C26 C27 119.81(9) . . ?
C26 C27 S2 113.38(7) . . ?
C26 C27 H27A 108.9 . . ?
S2 C27 H27A 108.9 . . ?
C26 C27 H27B 108.9 . . ?
S2 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
O32 C3 O31 128.13(11) . . ?
O32 C3 H3 115.9 . . ?
O31 C3 H3 115.9 . . ?
C4 O41 H41 108.6(14) . . ?
O42 C4 O41 127.19(10) . . ?
O42 C4 H4 116.4 . . ?
O41 C4 H4 116.4 . . ?

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
_geom_torsion_publ_flag
C21 S1 C11 C12 -90.93(9) . . . . ?
Mn1 S1 C11 C12 11.70(9) . . . . ?
C16 N1 C12 C13 -0.02(15) . . . . ?
Mn1 N1 C12 C13 -175.53(8) . . . . ?
C16 N1 C12 C11 -177.17(9) . . . . ?
Mn1 N1 C12 C11 7.31(13) . . . . ?
S1 C11 C12 N1 -13.09(14) . . . . ?
S1 C11 C12 C13 169.70(9) . . . . ?
N1 C12 C13 C14 0.98(16) . . . . ?
C11 C12 C13 C14 178.08(11) . . . . ?
C12 C13 C14 C15 -1.01(17) . . . . ?
C13 C14 C15 C16 0.12(16) . . . . ?
C12 N1 C16 C15 -0.93(14) . . . . ?
Mn1 N1 C16 C15 174.62(7) . . . . ?
C12 N1 C16 C17 175.94(8) . . . . ?
Mn1 N1 C16 C17 -8.51(12) . . . . ?
C14 C15 C16 N1 0.88(15) . . . . ?
C14 C15 C16 C17 -175.93(10) . . . . ?
N1 C16 C17 S2 20.38(12) . . . . ?
C15 C16 C17 S2 -162.68(8) . . . . ?
C27 S2 C17 C16 83.25(8) . . . . ?
Mn1 S2 C17 C16 -20.31(7) . . . . ?
C11 S1 C21 C22 82.07(9) . . . . ?
Mn1 S1 C21 C22 -21.67(8) . . . . ?
C26 N2 C22 C23 -0.87(15) . . . . ?
Mn1 N2 C22 C23 173.10(8) . . . . ?
C26 N2 C22 C21 176.20(9) . . . . ?
Mn1 N2 C22 C21 -9.83(12) . . . . ?
S1 C21 C22 N2 22.15(12) . . . . ?
S1 C21 C22 C23 -160.73(9) . . . . ?
N2 C22 C23 C24 -0.30(16) . . . . ?
C21 C22 C23 C24 -177.28(10) . . . . ?
C22 C23 C24 C25 0.65(17) . . . . ?
C23 C24 C25 C26 0.14(16) . . . . ?
C22 N2 C26 C25 1.72(14) . . . . ?
Mn1 N2 C26 C25 -172.21(7) . . . . ?
C22 N2 C26 C27 -175.75(8) . . . . ?
Mn1 N2 C26 C27 10.33(12) . . . . ?
C24 C25 C26 N2 -1.37(15) . . . . ?
C24 C25 C26 C27 176.06(10) . . . . ?
N2 C26 C27 S2 -16.41(12) . . . . ?
C25 C26 C27 S2 166.06(8) . . . . ?
C17 S2 C27 C26 -88.93(8) . . . . ?
Mn1 S2 C27 C26 13.74(7) . . . . ?

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
O41 H41 O31 0.925(16) 1.620(16) 2.5422(12) 174(2) . yes

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.067

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jk330
_database_code_depnum_ccdc_archive 'CCDC 1887967'
loop_
_audit_author_name
_audit_author_address
'Robert Fayzullin'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS
Russia
;
_audit_update_record             
;
2018-12-30 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C28 H12 D24 K Mn N2 O5 S2'
_chemical_formula_sum            'C28 H12 D24 K Mn N2 O5 S2'
_exptl_crystal_recrystallization_method 
'vapor diffusion of pentane into a THF-d8 solution at -30 °C'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_diffrn_ambient_temperature      93(2)
_chemical_formula_weight         662.89

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'
D D 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'
K K 0.2009 0.2494 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration .

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'

_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.
;

_cell_length_a                   9.3544(2)
_cell_length_b                   16.4310(4)
_cell_length_c                   19.2887(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.431(2)
_cell_angle_gamma                90
_cell_volume                     2955.84(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    13914
_cell_measurement_theta_min      2.3750
_cell_measurement_theta_max      29.1650
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    0.769
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_T_max  1.000
_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_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52162
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.352
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6427
_reflns_number_gt                5519
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 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)'
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+5.3215P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6427
_refine_ls_number_parameters     416
_refine_ls_number_restraints     211
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.59492(4) 0.28170(2) 0.25878(2) 0.01838(11) Uani 1 1 d . . . . .
S1 S 0.57765(7) 0.41964(4) 0.25159(3) 0.02661(16) Uani 1 1 d . . . . .
S2 S 0.67871(7) 0.15240(4) 0.27868(3) 0.02372(15) Uani 1 1 d . . . . .
O1 O 0.3211(2) 0.24879(15) 0.31897(12) 0.0407(5) Uani 1 1 d . . . . .
O2 O 0.4373(3) 0.25986(19) 0.12225(12) 0.0566(7) Uani 1 1 d . . . . .
N2 N 0.7901(2) 0.29997(13) 0.21990(11) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.6989(2) 0.30408(12) 0.35398(10) 0.0174(4) Uani 1 1 d . . . . .
C1 C 0.4305(3) 0.26344(17) 0.29540(14) 0.0272(6) Uani 1 1 d . . . . .
C2 C 0.5031(3) 0.26676(19) 0.17551(15) 0.0313(6) Uani 1 1 d . . . . .
C11 C 0.6752(3) 0.44557(17) 0.32872(15) 0.0270(6) Uani 1 1 d D . . . .
H11 H 0.685(3) 0.4992(17) 0.3398(17) 0.031(8) Uiso 1 1 d D . . . .
C12 C 0.7257(3) 0.38401(16) 0.37310(13) 0.0205(5) Uani 1 1 d . . . . .
C13 C 0.8037(3) 0.39918(17) 0.43896(14) 0.0259(6) Uani 1 1 d . . . . .
H13 H 0.827172 0.453452 0.452467 0.031 Uiso 1 1 calc R U . . .
C14 C 0.8442(3) 0.33638(18) 0.48216(14) 0.0278(6) Uani 1 1 d . . . . .
H14 H 0.894791 0.347118 0.525823 0.033 Uiso 1 1 calc R U . . .
C15 C 0.8115(3) 0.25555(17) 0.46240(13) 0.0243(5) Uani 1 1 d . . . . .
H15 H 0.838746 0.211254 0.492197 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7384(3) 0.24275(15) 0.39825(13) 0.0199(5) Uani 1 1 d . . . . .
C17 C 0.6953(3) 0.15920(16) 0.37341(14) 0.0279(6) Uani 1 1 d . . . . .
H17A H 0.602396 0.144762 0.391478 0.033 Uiso 1 1 calc R U . . .
H17B H 0.767717 0.119376 0.392184 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7005(3) 0.43237(19) 0.18371(16) 0.0351(7) Uani 1 1 d . . . . .
H21A H 0.648037 0.423958 0.137710 0.042 Uiso 1 1 calc R U . . .
H21B H 0.738595 0.488607 0.185229 0.042 Uiso 1 1 calc R U . . .
C22 C 0.8233(3) 0.37293(17) 0.19258(15) 0.0301(6) Uani 1 1 d . . . . .
C23 C 0.9563(4) 0.3909(2) 0.17137(17) 0.0398(7) Uani 1 1 d . . . . .
H23 H 0.976786 0.442909 0.153017 0.048 Uiso 1 1 calc R U . . .
C24 C 1.0613(3) 0.3296(2) 0.17777(17) 0.0391(7) Uani 1 1 d . . . . .
H24 H 1.154771 0.340398 0.163974 0.047 Uiso 1 1 calc R U . . .
C25 C 1.0310(3) 0.2552(2) 0.20336(15) 0.0328(6) Uani 1 1 d . . . . .
H25 H 1.102583 0.214103 0.206324 0.039 Uiso 1 1 calc R U . . .
C26 C 0.8905(3) 0.23815(17) 0.22616(14) 0.0245(5) Uani 1 1 d . . . . .
C27 C 0.8544(3) 0.16590(17) 0.25533(15) 0.0287(6) Uani 1 1 d D . . . .
H27 H 0.907(4) 0.1196(19) 0.2566(19) 0.047(10) Uiso 1 1 d D . . . .
K1 K 0.06421(6) 0.28483(4) 0.37023(3) 0.02686(14) Uani 1 1 d . . . . .
O3 O 0.2339(2) 0.29214(14) 0.49072(13) 0.0453(6) Uani 1 1 d . . . . .
C31 C 0.2347(3) 0.3567(2) 0.54031(19) 0.0412(8) Uani 1 1 d . . . . .
D31A D 0.192517 0.338278 0.583140 0.049 Uiso 1 1 calc R U . . .
D31B D 0.178420 0.403608 0.520887 0.049 Uiso 1 1 calc R U . . .
C32 C 0.3913(3) 0.3807(2) 0.55621(18) 0.0406(7) Uani 1 1 d . . . . .
D32A D 0.408128 0.437390 0.541536 0.049 Uiso 1 1 calc R U . . .
D32B D 0.419822 0.375494 0.606523 0.049 Uiso 1 1 calc R U . . .
C33 C 0.4736(4) 0.3210(2) 0.51432(19) 0.0470(8) Uani 1 1 d . . . . .
D33A D 0.497822 0.345189 0.469677 0.056 Uiso 1 1 calc R U . . .
D33B D 0.562785 0.302748 0.540738 0.056 Uiso 1 1 calc R U . . .
C34 C 0.3697(4) 0.2532(2) 0.5030(2) 0.0489(9) Uani 1 1 d . . . . .
D34A D 0.391896 0.219935 0.462370 0.059 Uiso 1 1 calc R U . . .
D34B D 0.371139 0.217644 0.544474 0.059 Uiso 1 1 calc R U . . .
O4 O 0.1362(2) 0.44488(14) 0.37300(14) 0.0463(6) Uani 1 1 d D U . . .
C41 C 0.0542(3) 0.5086(2) 0.3406(2) 0.0446(8) Uani 1 1 d D U . . .
D41A D 0.026286 0.548992 0.375193 0.054 Uiso 0.785(9) 1 calc R U P A 1
D41B D -0.033358 0.487306 0.314663 0.054 Uiso 0.785(9) 1 calc R U P A 1
D41C D -0.015194 0.529778 0.372425 0.054 Uiso 0.215(9) 1 calc R U P A 2
D41D D 0.000187 0.488511 0.297846 0.054 Uiso 0.215(9) 1 calc R U P A 2
C42 C 0.1581(5) 0.5465(4) 0.2906(3) 0.0415(13) Uani 0.785(9) 1 d D U P A 1
D42A D 0.168479 0.511846 0.249267 0.050 Uiso 0.785(9) 1 calc R U P A 1
D42B D 0.128200 0.601960 0.275543 0.050 Uiso 0.785(9) 1 calc R U P A 1
C43 C 0.2951(5) 0.5474(3) 0.3399(3) 0.0321(12) Uani 0.785(9) 1 d D U P A 1
D43A D 0.381755 0.547730 0.313523 0.039 Uiso 0.785(9) 1 calc R U P A 1
D43B D 0.297343 0.595668 0.370762 0.039 Uiso 0.785(9) 1 calc R U P A 1
C44 C 0.2862(4) 0.4714(3) 0.3805(3) 0.0416(13) Uani 0.785(9) 1 d D U P A 1
D44A D 0.349149 0.429190 0.362478 0.050 Uiso 0.785(9) 1 calc R U P A 1
D44B D 0.316871 0.481356 0.430029 0.050 Uiso 0.785(9) 1 calc R U P A 1
C45 C 0.1555(14) 0.5741(8) 0.3232(11) 0.034(3) Uani 0.215(9) 1 d D U P A 2
D45A D 0.159891 0.617586 0.358793 0.041 Uiso 0.215(9) 1 calc R U P A 2
D45B D 0.126456 0.598348 0.277229 0.041 Uiso 0.215(9) 1 calc R U P A 2
C46 C 0.2977(19) 0.5313(11) 0.3221(15) 0.046(4) Uani 0.215(9) 1 d D U P A 2
D46A D 0.334681 0.535624 0.275510 0.055 Uiso 0.215(9) 1 calc R U P A 2
D46B D 0.368770 0.555636 0.356734 0.055 Uiso 0.215(9) 1 calc R U P A 2
C47 C 0.2717(15) 0.4463(9) 0.3392(12) 0.042(4) Uani 0.215(9) 1 d D U P A 2
D47A D 0.350973 0.424825 0.370936 0.051 Uiso 0.215(9) 1 calc R U P A 2
D47B D 0.263833 0.412601 0.296459 0.051 Uiso 0.215(9) 1 calc R U P A 2
O5 O 0.1078(3) 0.12629(14) 0.41390(13) 0.0481(6) Uani 1 1 d D U . . .
C51 C 0.1122(4) 0.1004(2) 0.4836(2) 0.0498(9) Uani 1 1 d D U . . .
D51A D 0.017837 0.078675 0.494561 0.060 Uiso 0.646(16) 1 calc R U P B 1
D51B D 0.138137 0.146202 0.515524 0.060 Uiso 0.646(16) 1 calc R U P B 1
D51C D 0.026045 0.068034 0.492122 0.060 Uiso 0.354(16) 1 calc R U P B 2
D51D D 0.118148 0.147574 0.515679 0.060 Uiso 0.354(16) 1 calc R U P B 2
C52 C 0.2266(15) 0.0338(8) 0.4906(5) 0.055(3) Uani 0.646(16) 1 d D U P B 1
D52A D 0.322291 0.057286 0.503984 0.066 Uiso 0.646(16) 1 calc R U P B 1
D52B D 0.203604 -0.007007 0.525728 0.066 Uiso 0.646(16) 1 calc R U P B 1
C53 C 0.2226(9) -0.0032(4) 0.4201(3) 0.0457(18) Uani 0.646(16) 1 d D U P B 1
D53A D 0.150061 -0.047089 0.414488 0.055 Uiso 0.646(16) 1 calc R U P B 1
D53B D 0.317461 -0.025207 0.410149 0.055 Uiso 0.646(16) 1 calc R U P B 1
C54 C 0.1813(13) 0.0691(6) 0.3743(5) 0.054(3) Uani 0.646(16) 1 d D U P B 1
D54A D 0.268230 0.094438 0.357550 0.064 Uiso 0.646(16) 1 calc R U P B 1
D54B D 0.118556 0.051335 0.333457 0.064 Uiso 0.646(16) 1 calc R U P B 1
C55 C 0.248(3) 0.0482(17) 0.4931(8) 0.054(5) Uani 0.354(16) 1 d D U P B 2
D55A D 0.327872 0.078491 0.518032 0.065 Uiso 0.354(16) 1 calc R U P B 2
D55B D 0.230548 -0.002567 0.518783 0.065 Uiso 0.354(16) 1 calc R U P B 2
C56 C 0.2785(18) 0.0309(11) 0.4205(7) 0.061(3) Uani 0.354(16) 1 d D U P B 2
D56A D 0.295647 -0.027951 0.413992 0.073 Uiso 0.354(16) 1 calc R U P B 2
D56B D 0.364135 0.061381 0.407979 0.073 Uiso 0.354(16) 1 calc R U P B 2
C57 C 0.146(2) 0.0584(12) 0.3759(9) 0.056(4) Uani 0.354(16) 1 d D U P B 2
D57A D 0.169098 0.073337 0.328313 0.067 Uiso 0.354(16) 1 calc R U P B 2
D57B D 0.070037 0.016342 0.373374 0.067 Uiso 0.354(16) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C1 1.767(3) . ?
Mn1 C2 1.779(3) . ?
Mn1 N1 2.044(2) . ?
Mn1 N2 2.049(2) . ?
Mn1 S1 2.2756(8) . ?
Mn1 S2 2.2867(7) . ?
Mn1 K1 4.7368(7) 1_655 ?
S1 C11 1.737(3) . ?
S1 C21 1.820(3) . ?
S2 C27 1.752(3) . ?
S2 C17 1.825(3) . ?
O1 C1 1.176(3) . ?
O1 K1 2.733(2) . ?
O2 C2 1.162(4) . ?
N2 C22 1.355(4) . ?
N2 C26 1.382(3) . ?
N1 C16 1.354(3) . ?
N1 C12 1.382(3) . ?
N1 K1 3.422(2) 1_655 ?
C11 C12 1.384(4) . ?
C11 H11 0.91(3) . ?
C12 C13 1.437(4) . ?
C13 C14 1.362(4) . ?
C13 K1 3.424(3) 1_655 ?
C13 H13 0.9500 . ?
C14 C15 1.409(4) . ?
C14 K1 3.209(3) 1_655 ?
C14 H14 0.9500 . ?
C15 C16 1.383(4) . ?
C15 K1 3.103(3) 1_655 ?
C15 H15 0.9500 . ?
C16 C17 1.499(4) . ?
C16 K1 3.211(2) 1_655 ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C21 C22 1.508(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.372(4) . ?
C23 C24 1.405(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.356(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.445(4) . ?
C25 K1 3.246(3) 1_655 ?
C25 H25 0.9500 . ?
C26 C27 1.367(4) . ?
C26 K1 3.202(3) 1_655 ?
C27 K1 3.451(3) 1_655 ?
C27 H27 0.91(3) . ?
K1 O3 2.714(2) . ?
K1 O4 2.714(2) . ?
K1 O5 2.758(2) . ?
K1 C47 3.368(14) . ?
O3 C34 1.425(4) . ?
O3 C31 1.428(4) . ?
C31 C32 1.525(4) . ?
C31 D31A 0.9900 . ?
C31 D31B 0.9900 . ?
C32 C33 1.517(5) . ?
C32 D32A 0.9900 . ?
C32 D32B 0.9900 . ?
C33 C34 1.485(5) . ?
C33 D33A 0.9900 . ?
C33 D33B 0.9900 . ?
C34 D34A 0.9900 . ?
C34 D34B 0.9900 . ?
O4 C41 1.415(4) . ?
O4 C44 1.466(4) . ?
O4 C47 1.470(12) . ?
C41 C45 1.490(12) . ?
C41 C42 1.552(5) . ?
C41 D41A 0.9900 . ?
C41 D41B 0.9900 . ?
C41 D41C 0.9900 . ?
C41 D41D 0.9900 . ?
C42 C43 1.537(6) . ?
C42 D42A 0.9900 . ?
C42 D42B 0.9900 . ?
C43 C44 1.479(6) . ?
C43 D43A 0.9900 . ?
C43 D43B 0.9900 . ?
C44 D44A 0.9900 . ?
C44 D44B 0.9900 . ?
C45 C46 1.506(16) . ?
C45 D45A 0.9900 . ?
C45 D45B 0.9900 . ?
C46 C47 1.460(16) . ?
C46 D46A 0.9900 . ?
C46 D46B 0.9900 . ?
C47 D47A 0.9900 . ?
C47 D47B 0.9900 . ?
O5 C57 1.396(13) . ?
O5 C51 1.408(4) . ?
O5 C54 1.420(8) . ?
C51 C52 1.530(8) . ?
C51 C55 1.533(14) . ?
C51 D51A 0.9900 . ?
C51 D51B 0.9900 . ?
C51 D51C 0.9900 . ?
C51 D51D 0.9900 . ?
C52 C53 1.488(10) . ?
C52 D52A 0.9900 . ?
C52 D52B 0.9900 . ?
C53 C54 1.513(10) . ?
C53 D53A 0.9900 . ?
C53 D53B 0.9900 . ?
C54 D54A 0.9900 . ?
C54 D54B 0.9900 . ?
C55 C56 1.479(15) . ?
C55 D55A 0.9900 . ?
C55 D55B 0.9900 . ?
C56 C57 1.521(15) . ?
C56 D56A 0.9900 . ?
C56 D56B 0.9900 . ?
C57 D57A 0.9900 . ?
C57 D57B 0.9900 . ?

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
C1 Mn1 C2 87.89(13) . . ?
C1 Mn1 N1 92.29(10) . . ?
C2 Mn1 N1 177.56(12) . . ?
C1 Mn1 N2 177.44(11) . . ?
C2 Mn1 N2 94.09(11) . . ?
N1 Mn1 N2 85.81(8) . . ?
C1 Mn1 S1 97.68(10) . . ?
C2 Mn1 S1 93.17(10) . . ?
N1 Mn1 S1 84.39(6) . . ?
N2 Mn1 S1 83.85(6) . . ?
C1 Mn1 S2 94.18(10) . . ?
C2 Mn1 S2 99.13(10) . . ?
N1 Mn1 S2 83.29(6) . . ?
N2 Mn1 S2 83.91(6) . . ?
S1 Mn1 S2 163.21(3) . . ?
C1 Mn1 K1 128.70(9) . 1_655 ?
C2 Mn1 K1 140.99(9) . 1_655 ?
N1 Mn1 K1 39.67(6) . 1_655 ?
N2 Mn1 K1 48.98(6) . 1_655 ?
S1 Mn1 K1 94.34(2) . 1_655 ?
S2 Mn1 K1 68.915(19) . 1_655 ?
C11 S1 C21 105.58(15) . . ?
C11 S1 Mn1 99.32(10) . . ?
C21 S1 Mn1 96.46(10) . . ?
C27 S2 C17 103.93(14) . . ?
C27 S2 Mn1 98.94(10) . . ?
C17 S2 Mn1 96.47(9) . . ?
C1 O1 K1 155.6(2) . . ?
C22 N2 C26 120.6(2) . . ?
C22 N2 Mn1 120.65(18) . . ?
C26 N2 Mn1 118.63(17) . . ?
C16 N1 C12 120.3(2) . . ?
C16 N1 Mn1 121.38(16) . . ?
C12 N1 Mn1 118.35(16) . . ?
C16 N1 K1 69.58(13) . 1_655 ?
C12 N1 K1 84.47(13) . 1_655 ?
Mn1 N1 K1 117.92(8) . 1_655 ?
O1 C1 Mn1 177.9(3) . . ?
O2 C2 Mn1 176.2(3) . . ?
C12 C11 S1 118.8(2) . . ?
C12 C11 H11 123(2) . . ?
S1 C11 H11 119(2) . . ?
N1 C12 C11 118.9(2) . . ?
N1 C12 C13 118.1(2) . . ?
C11 C12 C13 123.1(2) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 K1 69.41(16) . 1_655 ?
C12 C13 K1 83.70(15) . 1_655 ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
K1 C13 H13 117.7 1_655 . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 K1 87.19(17) . 1_655 ?
C15 C14 K1 72.93(15) . 1_655 ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
K1 C14 H14 110.1 1_655 . ?
C16 C15 C14 117.9(2) . . ?
C16 C15 K1 81.76(15) . 1_655 ?
C14 C15 K1 81.35(16) . 1_655 ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
K1 C15 H15 106.5 1_655 . ?
N1 C16 C15 122.9(2) . . ?
N1 C16 C17 115.2(2) . . ?
C15 C16 C17 121.8(2) . . ?
N1 C16 K1 87.15(14) . 1_655 ?
C15 C16 K1 73.02(14) . 1_655 ?
C17 C16 K1 112.26(16) . 1_655 ?
C16 C17 S2 112.09(19) . . ?
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 123.2(3) . . ?
N2 C22 C21 114.9(2) . . ?
C23 C22 C21 121.8(3) . . ?
C22 C23 C24 117.6(3) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C25 C24 C23 120.9(3) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 K1 102.7(2) . 1_655 ?
C26 C25 K1 75.34(16) . 1_655 ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
K1 C25 H25 91.9 1_655 . ?
C27 C26 N2 119.1(2) . . ?
C27 C26 C25 123.6(3) . . ?
N2 C26 C25 117.3(2) . . ?
C27 C26 K1 88.61(17) . 1_655 ?
N2 C26 K1 101.28(15) . 1_655 ?
C25 C26 K1 78.76(16) . 1_655 ?
C26 C27 S2 118.8(2) . . ?
C26 C27 K1 68.06(16) . 1_655 ?
S2 C27 K1 113.88(12) . 1_655 ?
C26 C27 H27 126(2) . . ?
S2 C27 H27 114(2) . . ?
K1 C27 H27 100(2) 1_655 . ?
O3 K1 O4 79.19(7) . . ?
O3 K1 O1 81.20(7) . . ?
O4 K1 O1 89.62(7) . . ?
O3 K1 O5 73.58(7) . . ?
O4 K1 O5 151.45(8) . . ?
O1 K1 O5 78.02(8) . . ?
O3 K1 C15 86.41(8) . 1_455 ?
O4 K1 C15 109.74(8) . 1_455 ?
O1 K1 C15 154.64(8) . 1_455 ?
O5 K1 C15 77.29(8) . 1_455 ?
O3 K1 C26 167.90(7) . 1_455 ?
O4 K1 C26 110.96(8) . 1_455 ?
O1 K1 C26 92.04(7) . 1_455 ?
O5 K1 C26 95.28(7) . 1_455 ?
C15 K1 C26 95.86(7) 1_455 1_455 ?
O3 K1 C14 77.01(7) . 1_455 ?
O4 K1 C14 84.38(8) . 1_455 ?
O1 K1 C14 158.11(7) . 1_455 ?
O5 K1 C14 97.54(8) . 1_455 ?
C15 K1 C14 25.72(7) 1_455 1_455 ?
C26 K1 C14 109.77(7) 1_455 1_455 ?
O3 K1 C16 111.43(8) . 1_455 ?
O4 K1 C16 116.27(7) . 1_455 ?
O1 K1 C16 152.44(7) . 1_455 ?
O5 K1 C16 82.25(7) . 1_455 ?
C15 K1 C16 25.22(6) 1_455 1_455 ?
C26 K1 C16 70.72(7) 1_455 1_455 ?
C14 K1 C16 43.74(7) 1_455 1_455 ?
O3 K1 C25 149.37(8) . 1_455 ?
O4 K1 C25 99.74(8) . 1_455 ?
O1 K1 C25 68.18(7) . 1_455 ?
O5 K1 C25 99.32(8) . 1_455 ?
C15 K1 C25 121.74(7) 1_455 1_455 ?
C26 K1 C25 25.89(7) 1_455 1_455 ?
C14 K1 C25 133.58(7) 1_455 1_455 ?
C16 K1 C25 96.62(7) 1_455 1_455 ?
O3 K1 C47 79.1(4) . . ?
O4 K1 C47 25.2(2) . . ?
O1 K1 C47 64.6(2) . . ?
O5 K1 C47 136.4(2) . . ?
C15 K1 C47 134.4(3) 1_455 . ?
C26 K1 C47 107.2(4) 1_455 . ?
C14 K1 C47 108.7(3) 1_455 . ?
C16 K1 C47 140.1(2) 1_455 . ?
C25 K1 C47 87.4(4) 1_455 . ?
O3 K1 N1 126.03(7) . 1_455 ?
O4 K1 N1 99.02(6) . 1_455 ?
O1 K1 N1 152.44(6) . 1_455 ?
O5 K1 N1 103.79(7) . 1_455 ?
C15 K1 N1 42.88(6) 1_455 1_455 ?
C26 K1 N1 60.42(6) 1_455 1_455 ?
C14 K1 N1 49.43(6) 1_455 1_455 ?
C16 K1 N1 23.27(6) 1_455 1_455 ?
C25 K1 N1 84.53(6) 1_455 1_455 ?
O3 K1 C13 91.77(7) . 1_455 ?
O4 K1 C13 69.12(7) . 1_455 ?
O1 K1 C13 158.57(7) . 1_455 ?
O5 K1 C13 119.53(8) . 1_455 ?
C15 K1 C13 42.85(7) 1_455 1_455 ?
C26 K1 C13 97.98(6) 1_455 1_455 ?
C14 K1 C13 23.40(7) 1_455 1_455 ?
C16 K1 C13 48.70(6) 1_455 1_455 ?
C25 K1 C13 116.72(7) 1_455 1_455 ?
N1 K1 C13 41.35(5) 1_455 1_455 ?
C34 O3 C31 105.3(2) . . ?
C34 O3 K1 125.2(2) . . ?
C31 O3 K1 125.36(19) . . ?
O3 C31 C32 106.3(2) . . ?
O3 C31 D31A 110.5 . . ?
C32 C31 D31A 110.5 . . ?
O3 C31 D31B 110.5 . . ?
C32 C31 D31B 110.5 . . ?
D31A C31 D31B 108.7 . . ?
C33 C32 C31 104.2(3) . . ?
C33 C32 D32A 110.9 . . ?
C31 C32 D32A 110.9 . . ?
C33 C32 D32B 110.9 . . ?
C31 C32 D32B 110.9 . . ?
D32A C32 D32B 108.9 . . ?
C34 C33 C32 102.1(3) . . ?
C34 C33 D33A 111.3 . . ?
C32 C33 D33A 111.3 . . ?
C34 C33 D33B 111.3 . . ?
C32 C33 D33B 111.3 . . ?
D33A C33 D33B 109.2 . . ?
O3 C34 C33 104.6(3) . . ?
O3 C34 D34A 110.8 . . ?
C33 C34 D34A 110.8 . . ?
O3 C34 D34B 110.8 . . ?
C33 C34 D34B 110.8 . . ?
D34A C34 D34B 108.9 . . ?
C41 O4 C44 107.8(3) . . ?
C41 O4 C47 104.4(7) . . ?
C41 O4 K1 125.68(19) . . ?
C44 O4 K1 121.6(2) . . ?
C47 O4 K1 103.1(6) . . ?
O4 C41 C45 107.6(6) . . ?
O4 C41 C42 103.1(3) . . ?
O4 C41 D41A 111.1 . . ?
C42 C41 D41A 111.1 . . ?
O4 C41 D41B 111.1 . . ?
C42 C41 D41B 111.1 . . ?
D41A C41 D41B 109.1 . . ?
O4 C41 D41C 110.2 . . ?
C45 C41 D41C 110.2 . . ?
O4 C41 D41D 110.2 . . ?
C45 C41 D41D 110.2 . . ?
D41C C41 D41D 108.5 . . ?
C43 C42 C41 98.7(4) . . ?
C43 C42 D42A 112.0 . . ?
C41 C42 D42A 112.0 . . ?
C43 C42 D42B 112.0 . . ?
C41 C42 D42B 112.0 . . ?
D42A C42 D42B 109.7 . . ?
C44 C43 C42 103.9(4) . . ?
C44 C43 D43A 111.0 . . ?
C42 C43 D43A 111.0 . . ?
C44 C43 D43B 111.0 . . ?
C42 C43 D43B 111.0 . . ?
D43A C43 D43B 109.0 . . ?
O4 C44 C43 107.0(3) . . ?
O4 C44 D44A 110.3 . . ?
C43 C44 D44A 110.3 . . ?
O4 C44 D44B 110.3 . . ?
C43 C44 D44B 110.3 . . ?
D44A C44 D44B 108.6 . . ?
C41 C45 C46 104.1(10) . . ?
C41 C45 D45A 110.9 . . ?
C46 C45 D45A 110.9 . . ?
C41 C45 D45B 110.9 . . ?
C46 C45 D45B 110.9 . . ?
D45A C45 D45B 109.0 . . ?
C47 C46 C45 106.3(12) . . ?
C47 C46 D46A 110.5 . . ?
C45 C46 D46A 110.5 . . ?
C47 C46 D46B 110.5 . . ?
C45 C46 D46B 110.5 . . ?
D46A C46 D46B 108.7 . . ?
C46 C47 O4 106.2(11) . . ?
C46 C47 K1 154.5(10) . . ?
O4 C47 K1 51.7(5) . . ?
C46 C47 D47A 110.5 . . ?
O4 C47 D47A 110.5 . . ?
K1 C47 D47A 91.4 . . ?
C46 C47 D47B 110.5 . . ?
O4 C47 D47B 110.5 . . ?
K1 C47 D47B 72.6 . . ?
D47A C47 D47B 108.7 . . ?
C57 O5 C51 105.7(9) . . ?
C51 O5 C54 109.5(4) . . ?
C57 O5 K1 129.2(9) . . ?
C51 O5 K1 124.7(2) . . ?
C54 O5 K1 121.8(5) . . ?
O5 C51 C52 105.5(4) . . ?
O5 C51 C55 104.2(8) . . ?
O5 C51 D51A 110.6 . . ?
C52 C51 D51A 110.6 . . ?
O5 C51 D51B 110.6 . . ?
C52 C51 D51B 110.6 . . ?
D51A C51 D51B 108.8 . . ?
O5 C51 D51C 110.9 . . ?
C55 C51 D51C 110.9 . . ?
O5 C51 D51D 110.9 . . ?
C55 C51 D51D 110.9 . . ?
D51C C51 D51D 108.9 . . ?
C53 C52 C51 104.2(5) . . ?
C53 C52 D52A 110.9 . . ?
C51 C52 D52A 110.9 . . ?
C53 C52 D52B 110.9 . . ?
C51 C52 D52B 110.9 . . ?
D52A C52 D52B 108.9 . . ?
C52 C53 C54 101.4(6) . . ?
C52 C53 D53A 111.5 . . ?
C54 C53 D53A 111.5 . . ?
C52 C53 D53B 111.5 . . ?
C54 C53 D53B 111.5 . . ?
D53A C53 D53B 109.3 . . ?
O5 C54 C53 108.6(6) . . ?
O5 C54 D54A 110.0 . . ?
C53 C54 D54A 110.0 . . ?
O5 C54 D54B 110.0 . . ?
C53 C54 D54B 110.0 . . ?
D54A C54 D54B 108.4 . . ?
C56 C55 C51 102.3(10) . . ?
C56 C55 D55A 111.3 . . ?
C51 C55 D55A 111.3 . . ?
C56 C55 D55B 111.3 . . ?
C51 C55 D55B 111.3 . . ?
D55A C55 D55B 109.2 . . ?
C55 C56 C57 105.7(12) . . ?
C55 C56 D56A 110.6 . . ?
C57 C56 D56A 110.6 . . ?
C55 C56 D56B 110.6 . . ?
C57 C56 D56B 110.6 . . ?
D56A C56 D56B 108.7 . . ?
O5 C57 C56 99.8(10) . . ?
O5 C57 D57A 111.8 . . ?
C56 C57 D57A 111.8 . . ?
O5 C57 D57B 111.8 . . ?
C56 C57 D57B 111.8 . . ?
D57A C57 D57B 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 S1 C11 C12 -103.4(2) . . . . ?
Mn1 S1 C11 C12 -3.9(2) . . . . ?
C16 N1 C12 C11 -175.6(2) . . . . ?
Mn1 N1 C12 C11 3.1(3) . . . . ?
K1 N1 C12 C11 122.0(2) 1_655 . . . ?
C16 N1 C12 C13 3.6(3) . . . . ?
Mn1 N1 C12 C13 -177.66(17) . . . . ?
K1 N1 C12 C13 -58.8(2) 1_655 . . . ?
S1 C11 C12 N1 1.1(3) . . . . ?
S1 C11 C12 C13 -178.1(2) . . . . ?
N1 C12 C13 C14 -2.7(4) . . . . ?
C11 C12 C13 C14 176.5(3) . . . . ?
N1 C12 C13 K1 58.9(2) . . . 1_655 ?
C11 C12 C13 K1 -121.9(2) . . . 1_655 ?
C12 C13 C14 C15 0.7(4) . . . . ?
K1 C13 C14 C15 -68.3(2) 1_655 . . . ?
C12 C13 C14 K1 69.1(2) . . . 1_655 ?
C13 C14 C15 C16 0.3(4) . . . . ?
K1 C14 C15 C16 -75.8(2) 1_655 . . . ?
C13 C14 C15 K1 76.2(2) . . . 1_655 ?
C12 N1 C16 C15 -2.7(4) . . . . ?
Mn1 N1 C16 C15 178.61(18) . . . . ?
K1 N1 C16 C15 67.6(2) 1_655 . . . ?
C12 N1 C16 C17 176.3(2) . . . . ?
Mn1 N1 C16 C17 -2.3(3) . . . . ?
K1 N1 C16 C17 -113.3(2) 1_655 . . . ?
C12 N1 C16 K1 -70.3(2) . . . 1_655 ?
Mn1 N1 C16 K1 110.98(13) . . . 1_655 ?
C14 C15 C16 N1 0.7(4) . . . . ?
K1 C15 C16 N1 -75.0(2) 1_655 . . . ?
C14 C15 C16 C17 -178.3(2) . . . . ?
K1 C15 C16 C17 106.1(2) 1_655 . . . ?
C14 C15 C16 K1 75.6(2) . . . 1_655 ?
N1 C16 C17 S2 27.4(3) . . . . ?
C15 C16 C17 S2 -153.6(2) . . . . ?
K1 C16 C17 S2 -70.28(19) 1_655 . . . ?
C27 S2 C17 C16 66.5(2) . . . . ?
Mn1 S2 C17 C16 -34.44(19) . . . . ?
C11 S1 C21 C22 64.9(3) . . . . ?
Mn1 S1 C21 C22 -36.7(2) . . . . ?
C26 N2 C22 C23 -1.6(4) . . . . ?
Mn1 N2 C22 C23 174.2(2) . . . . ?
C26 N2 C22 C21 175.5(2) . . . . ?
Mn1 N2 C22 C21 -8.7(3) . . . . ?
S1 C21 C22 N2 32.8(3) . . . . ?
S1 C21 C22 C23 -150.1(3) . . . . ?
N2 C22 C23 C24 0.9(5) . . . . ?
C21 C22 C23 C24 -176.0(3) . . . . ?
C22 C23 C24 C25 0.7(5) . . . . ?
C23 C24 C25 C26 -1.5(5) . . . . ?
C23 C24 C25 K1 -81.7(3) . . . 1_655 ?
C22 N2 C26 C27 178.6(3) . . . . ?
Mn1 N2 C26 C27 2.7(3) . . . . ?
C22 N2 C26 C25 0.8(4) . . . . ?
Mn1 N2 C26 C25 -175.10(19) . . . . ?
C22 N2 C26 K1 83.9(2) . . . 1_655 ?
Mn1 N2 C26 K1 -92.03(15) . . . 1_655 ?
C24 C25 C26 C27 -177.0(3) . . . . ?
K1 C25 C26 C27 -80.7(3) 1_655 . . . ?
C24 C25 C26 N2 0.7(4) . . . . ?
K1 C25 C26 N2 97.0(2) 1_655 . . . ?
C24 C25 C26 K1 -96.3(3) . . . 1_655 ?
N2 C26 C27 S2 3.9(4) . . . . ?
C25 C26 C27 S2 -178.4(2) . . . . ?
K1 C26 C27 S2 106.05(19) 1_655 . . . ?
N2 C26 C27 K1 -102.2(2) . . . 1_655 ?
C25 C26 C27 K1 75.5(3) . . . 1_655 ?
C17 S2 C27 C26 -106.3(2) . . . . ?
Mn1 S2 C27 C26 -7.2(2) . . . . ?
C17 S2 C27 K1 -29.13(15) . . . 1_655 ?
Mn1 S2 C27 K1 69.88(11) . . . 1_655 ?
C34 O3 C31 C32 27.4(4) . . . . ?
K1 O3 C31 C32 -130.7(2) . . . . ?
O3 C31 C32 C33 -2.9(4) . . . . ?
C31 C32 C33 C34 -21.3(4) . . . . ?
C31 O3 C34 C33 -42.1(4) . . . . ?
K1 O3 C34 C33 116.1(2) . . . . ?
C32 C33 C34 O3 38.8(4) . . . . ?
C47 O4 C41 C45 -33.3(14) . . . . ?
K1 O4 C41 C45 -151.5(9) . . . . ?
C44 O4 C41 C42 34.0(5) . . . . ?
K1 O4 C41 C42 -121.2(3) . . . . ?
O4 C41 C42 C43 -43.5(5) . . . . ?
C41 C42 C43 C44 36.9(5) . . . . ?
C41 O4 C44 C43 -10.0(5) . . . . ?
K1 O4 C44 C43 146.4(3) . . . . ?
C42 C43 C44 O4 -18.5(6) . . . . ?
O4 C41 C45 C46 21(2) . . . . ?
C41 C45 C46 C47 -1(2) . . . . ?
C45 C46 C47 O4 -19(2) . . . . ?
C45 C46 C47 K1 8(5) . . . . ?
C41 O4 C47 C46 32.6(17) . . . . ?
K1 O4 C47 C46 165.3(15) . . . . ?
C41 O4 C47 K1 -132.7(5) . . . . ?
C54 O5 C51 C52 14.3(10) . . . . ?
K1 O5 C51 C52 -143.4(7) . . . . ?
C57 O5 C51 C55 41.9(17) . . . . ?
K1 O5 C51 C55 -131.4(13) . . . . ?
O5 C51 C52 C53 -29.7(11) . . . . ?
C51 C52 C53 C54 31.8(12) . . . . ?
C51 O5 C54 C53 6.3(11) . . . . ?
K1 O5 C54 C53 164.8(6) . . . . ?
C52 C53 C54 O5 -24.4(12) . . . . ?
O5 C51 C55 C56 -17(2) . . . . ?
C51 C55 C56 C57 -11(2) . . . . ?
C51 O5 C57 C56 -47.8(18) . . . . ?
K1 O5 C57 C56 125.2(12) . . . . ?
C55 C56 C57 O5 35(2) . . . . ?

_refine_diff_density_max         1.404
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.075

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jk344
_database_code_depnum_ccdc_archive 'CCDC 1887968'
loop_
_audit_author_name
_audit_author_address
'Robert Fayzullin'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS
Russia
;
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H13 Mn N2 O2 S2'
_chemical_formula_sum            'C16 H13 Mn N2 O2 S2'
_exptl_crystal_recrystallization_method 
'vapor diffusion of pentane into a benzene solution'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_diffrn_ambient_temperature      94(2)
_chemical_formula_weight         384.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration .

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'

_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.
;

_cell_length_a                   13.7117(3)
_cell_length_b                   13.0041(2)
_cell_length_c                   8.82065(19)
_cell_angle_alpha                90
_cell_angle_beta                 104.355(2)
_cell_angle_gamma                90
_cell_volume                     1523.69(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    94(2)
_cell_measurement_reflns_used    13926
_cell_measurement_theta_min      2.1900
_cell_measurement_theta_max      30.3840
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    1.150
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_T_max  1.000
_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_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30423
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.192
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3981
_reflns_number_gt                3704
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 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)'
_refine_special_details          
;
The apparent geometry of the ligand is averaged over two forms with 
either C11 or C27 arm being deprotonated. 

Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0153P)²+3.8202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3981
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.312
_refine_ls_restrained_S_all      1.312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 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_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
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_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
_geom_torsion_publ_flag
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) . . . . ?

_refine_diff_density_max         1.102
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.087

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jk350
_database_code_depnum_ccdc_archive 'CCDC 1887965'
loop_
_audit_author_name
_audit_author_address
'Robert Fayzullin'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS
Russia
;
_audit_update_record             
;
2018-12-30 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H14 Mn N2 O2 S2 1+, Cl 1-'
_chemical_formula_sum            'C16 H14 Cl Mn N2 O2 S2'
_exptl_crystal_recrystallization_method 
'vapor diffusion of diethyl ether into a DCM solution'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      93(2)
_chemical_formula_weight         420.80

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'
_chemical_absolute_configuration .

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'

_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.
;

_cell_length_a                   18.1969(3)
_cell_length_b                   12.35882(16)
_cell_length_c                   16.6861(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.826(2)
_cell_angle_gamma                90
_cell_volume                     3318.66(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    25942
_cell_measurement_theta_min      2.7530
_cell_measurement_theta_max      31.0250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    1.220
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_T_max  1.000
_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_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45115
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.078
_diffrn_reflns_theta_max         30.872
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4895
_reflns_number_gt                4539
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 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)'
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+3.8511P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4895
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.47798(2) 0.56555(2) 0.33273(2) 0.01090(5) Uani 1 1 d . . . . .
Cl1 Cl 0.14036(2) 0.47046(2) 0.05750(2) 0.01275(6) Uani 1 1 d . . . . .
S1 S 0.44330(2) 0.50115(2) 0.19230(2) 0.01328(6) Uani 1 1 d . . . . .
S2 S 0.51351(2) 0.67423(2) 0.45458(2) 0.01356(6) Uani 1 1 d . . . . .
N1 N 0.39492(6) 0.68608(8) 0.26221(7) 0.01180(17) Uani 1 1 d . . . . .
N2 N 0.56455(6) 0.65478(8) 0.31503(6) 0.01129(17) Uani 1 1 d . . . . .
C11 C 0.34092(7) 0.56173(10) 0.13401(8) 0.0157(2) Uani 1 1 d . . . . .
H11A H 0.325677 0.571587 0.069230 0.019 Uiso 1 1 calc R U . . .
H11B H 0.299720 0.512396 0.137644 0.019 Uiso 1 1 calc R U . . .
C12 C 0.33801(7) 0.66919(10) 0.17441(8) 0.0137(2) Uani 1 1 d . . . . .
C13 C 0.27823(8) 0.74580(11) 0.12535(8) 0.0187(2) Uani 1 1 d . . . . .
H13 H 0.238523 0.732004 0.064263 0.022 Uiso 1 1 calc R U . . .
C14 C 0.27700(8) 0.84294(11) 0.16642(9) 0.0209(2) Uani 1 1 d . . . . .
H14 H 0.236848 0.896699 0.133471 0.025 Uiso 1 1 calc R U . . .
C15 C 0.33495(8) 0.86084(10) 0.25603(8) 0.0181(2) Uani 1 1 d . . . . .
H15 H 0.334860 0.926703 0.285336 0.022 Uiso 1 1 calc R U . . .
C16 C 0.39330(7) 0.78059(9) 0.30233(8) 0.0134(2) Uani 1 1 d . . . . .
C17 C 0.45605(8) 0.79729(10) 0.39999(8) 0.0174(2) Uani 1 1 d . . . . .
H17A H 0.427042 0.823803 0.433723 0.021 Uiso 1 1 calc R U . . .
H17B H 0.495954 0.853829 0.403417 0.021 Uiso 1 1 calc R U . . .
C21 C 0.50136(7) 0.59350(10) 0.15706(8) 0.0148(2) Uani 1 1 d . . . . .
H21A H 0.528536 0.551362 0.127784 0.018 Uiso 1 1 calc R U . . .
H21B H 0.462113 0.644717 0.111613 0.018 Uiso 1 1 calc R U . . .
C22 C 0.56623(7) 0.65633(9) 0.23489(7) 0.01183(19) Uani 1 1 d . . . . .
C23 C 0.62507(7) 0.71618(10) 0.22263(8) 0.0145(2) Uani 1 1 d . . . . .
H23 H 0.626395 0.714318 0.166400 0.017 Uiso 1 1 calc R U . . .
C24 C 0.68180(7) 0.77865(10) 0.29392(8) 0.0148(2) Uani 1 1 d . . . . .
H24 H 0.722217 0.820534 0.286920 0.018 Uiso 1 1 calc R U . . .
C25 C 0.67874(7) 0.77914(9) 0.37524(8) 0.0133(2) Uani 1 1 d . . . . .
H25 H 0.716129 0.822773 0.424217 0.016 Uiso 1 1 calc R U . . .
C26 C 0.62038(7) 0.71512(9) 0.38450(7) 0.01178(19) Uani 1 1 d . . . . .
C27 C 0.61682(7) 0.70996(10) 0.47239(8) 0.0146(2) Uani 1 1 d . . . . .
H27A H 0.632722 0.781113 0.503009 0.018 Uiso 1 1 calc R U . . .
H27B H 0.657224 0.655569 0.512422 0.018 Uiso 1 1 calc R U . . .
O1 O 0.34973(6) 0.44874(7) 0.35900(6) 0.01798(17) Uani 1 1 d . . . . .
C1 C 0.40006(7) 0.49351(9) 0.34769(8) 0.0135(2) Uani 1 1 d . . . . .
O2 O 0.59609(7) 0.39075(9) 0.43361(8) 0.0300(2) Uani 1 1 d . . . . .
C2 C 0.55087(8) 0.45975(11) 0.39406(9) 0.0179(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C1 1.7877(12) . ?
Mn1 C2 1.8025(13) . ?
Mn1 N2 2.0541(10) . ?
Mn1 N1 2.0562(10) . ?
Mn1 S2 2.2646(3) . ?
Mn1 S1 2.2676(3) . ?
S1 C11 1.8127(12) . ?
S1 C21 1.8288(12) . ?
S2 C27 1.8154(12) . ?
S2 C17 1.8295(13) . ?
N1 C16 1.3535(15) . ?
N1 C12 1.3586(15) . ?
N2 C22 1.3518(14) . ?
N2 C26 1.3537(15) . ?
C11 C12 1.5015(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3851(17) . ?
C13 C14 1.3877(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3873(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3936(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.5049(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C21 C22 1.5005(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.3930(15) . ?
C23 C24 1.3894(16) . ?
C23 H23 0.9500 . ?
C24 C25 1.3840(16) . ?
C24 H24 0.9500 . ?
C25 C26 1.3894(16) . ?
C25 H25 0.9500 . ?
C26 C27 1.4992(15) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
O1 C1 1.1585(15) . ?
O2 C2 1.1545(17) . ?

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
C1 Mn1 C2 88.91(5) . . ?
C1 Mn1 N2 177.36(5) . . ?
C2 Mn1 N2 93.47(5) . . ?
C1 Mn1 N1 91.24(5) . . ?
C2 Mn1 N1 179.71(5) . . ?
N2 Mn1 N1 86.39(4) . . ?
C1 Mn1 S2 94.74(4) . . ?
C2 Mn1 S2 95.42(4) . . ?
N2 Mn1 S2 83.91(3) . . ?
N1 Mn1 S2 84.82(3) . . ?
C1 Mn1 S1 96.50(4) . . ?
C2 Mn1 S1 96.21(4) . . ?
N2 Mn1 S1 84.38(3) . . ?
N1 Mn1 S1 83.53(3) . . ?
S2 Mn1 S1 163.950(13) . . ?
C11 S1 C21 99.96(6) . . ?
C11 S1 Mn1 97.48(4) . . ?
C21 S1 Mn1 100.91(4) . . ?
C27 S2 C17 100.77(6) . . ?
C27 S2 Mn1 97.53(4) . . ?
C17 S2 Mn1 100.88(4) . . ?
C16 N1 C12 118.97(10) . . ?
C16 N1 Mn1 121.47(8) . . ?
C12 N1 Mn1 119.51(8) . . ?
C22 N2 C26 119.00(10) . . ?
C22 N2 Mn1 121.52(8) . . ?
C26 N2 Mn1 119.47(7) . . ?
C12 C11 S1 111.55(8) . . ?
C12 C11 H11A 109.3 . . ?
S1 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
S1 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N1 C12 C13 121.69(11) . . ?
N1 C12 C11 116.82(10) . . ?
C13 C12 C11 121.45(11) . . ?
C12 C13 C14 119.26(11) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 119.40(12) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 118.89(12) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N1 C16 C15 121.79(11) . . ?
N1 C16 C17 118.25(10) . . ?
C15 C16 C17 119.96(11) . . ?
C16 C17 S2 113.17(8) . . ?
C16 C17 H17A 108.9 . . ?
S2 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
S2 C17 H17B 108.9 . . ?
H17A C17 H17B 107.8 . . ?
C22 C21 S1 112.57(8) . . ?
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 . . ?
N2 C22 C23 121.78(10) . . ?
N2 C22 C21 118.49(10) . . ?
C23 C22 C21 119.72(10) . . ?
C24 C23 C22 118.97(10) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 119.21(11) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 119.29(10) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
N2 C26 C25 121.70(10) . . ?
N2 C26 C27 117.15(10) . . ?
C25 C26 C27 121.15(10) . . ?
C26 C27 S2 111.38(8) . . ?
C26 C27 H27A 109.4 . . ?
S2 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
S2 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
O1 C1 Mn1 178.28(11) . . ?
O2 C2 Mn1 178.36(12) . . ?

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
_geom_torsion_publ_flag
C21 S1 C11 C12 -69.26(9) . . . . ?
Mn1 S1 C11 C12 33.26(9) . . . . ?
C16 N1 C12 C13 -0.46(16) . . . . ?
Mn1 N1 C12 C13 176.87(9) . . . . ?
C16 N1 C12 C11 -178.24(10) . . . . ?
Mn1 N1 C12 C11 -0.91(13) . . . . ?
S1 C11 C12 N1 -24.39(13) . . . . ?
S1 C11 C12 C13 157.82(10) . . . . ?
N1 C12 C13 C14 0.86(18) . . . . ?
C11 C12 C13 C14 178.54(12) . . . . ?
C12 C13 C14 C15 -0.78(19) . . . . ?
C13 C14 C15 C16 0.33(19) . . . . ?
C12 N1 C16 C15 -0.02(16) . . . . ?
Mn1 N1 C16 C15 -177.30(9) . . . . ?
C12 N1 C16 C17 179.18(10) . . . . ?
Mn1 N1 C16 C17 1.90(14) . . . . ?
C14 C15 C16 N1 0.08(18) . . . . ?
C14 C15 C16 C17 -179.10(12) . . . . ?
N1 C16 C17 S2 -10.29(14) . . . . ?
C15 C16 C17 S2 168.92(9) . . . . ?
C27 S2 C17 C16 112.21(9) . . . . ?
Mn1 S2 C17 C16 12.28(9) . . . . ?
C11 S1 C21 C22 114.74(9) . . . . ?
Mn1 S1 C21 C22 15.04(9) . . . . ?
C26 N2 C22 C23 1.60(16) . . . . ?
Mn1 N2 C22 C23 -179.62(9) . . . . ?
C26 N2 C22 C21 -176.99(10) . . . . ?
Mn1 N2 C22 C21 1.79(14) . . . . ?
S1 C21 C22 N2 -12.29(14) . . . . ?
S1 C21 C22 C23 169.10(9) . . . . ?
N2 C22 C23 C24 -2.11(17) . . . . ?
C21 C22 C23 C24 176.46(11) . . . . ?
C22 C23 C24 C25 0.46(17) . . . . ?
C23 C24 C25 C26 1.58(17) . . . . ?
C22 N2 C26 C25 0.56(16) . . . . ?
Mn1 N2 C26 C25 -178.25(8) . . . . ?
C22 N2 C26 C27 -179.34(10) . . . . ?
Mn1 N2 C26 C27 1.85(13) . . . . ?
C24 C25 C26 N2 -2.16(17) . . . . ?
C24 C25 C26 C27 177.74(11) . . . . ?
N2 C26 C27 S2 -25.73(13) . . . . ?
C25 C26 C27 S2 154.36(9) . . . . ?
C17 S2 C27 C26 -69.87(9) . . . . ?
Mn1 S2 C27 C26 32.78(9) . . . . ?

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.066

