# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_JTM651_0m
_audit_block_doi                 10.5517/ccdc.csd.cc204fj4
_database_code_depnum_ccdc_archive 'CCDC 1851305'
_audit_update_record             
;
2018-06-24 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-[(1E)-[(2Z)-2-[(ethylsulfanyl)({[(1E)-(ethylsulfanyl)[(Z)-2-[(2-hydroxyphenyl)methylidene]hydrazin-1-ylidene]methyl]disulfanyl})methylidene]hydrazin-1-ylidene]methyl]phenol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2 S4'
_chemical_formula_sum            'C20 H22 N4 O2 S4'
_chemical_formula_weight         478.65

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.712(2)
_cell_length_b                   9.1025(8)
_cell_length_c                   10.4517(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.353(1)
_cell_angle_gamma                90
_cell_volume                     2175.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3730
_cell_measurement_theta_min      2.4083
_cell_measurement_theta_max      28.8667
_cell_measurement_temperature    100(2)

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   0.803
_exptl_transmission_factor_max   0.928
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.462
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;

The diffraction data were collected in three sets of 
363 frames (0.5° width in ω) at φ = 0, 120 
and 240°. A scan time of 40 sec/frame was used. 
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10130
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.781
_diffrn_reflns_theta_max         28.963
_diffrn_reflns_theta_full        28.250
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2776
_reflns_number_gt                2211
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_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)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2776
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
S1 S 0.46079(2) 0.55099(5) 0.27341(4) 0.01508(13) Uani 1 1 d . . . . .
S2 S 0.53842(2) 0.76642(5) 0.46335(4) 0.01608(13) Uani 1 1 d . . . . .
O1 O 0.32975(6) 0.35714(15) 0.29593(13) 0.0211(3) Uani 1 1 d . . . . .
H1 H 0.3569(11) 0.426(3) 0.322(3) 0.049(7) Uiso 1 1 d . . . . .
N1 N 0.38644(6) 0.58427(16) 0.42841(14) 0.0155(3) Uani 1 1 d . . . . .
N2 N 0.43462(6) 0.67535(16) 0.48203(14) 0.0163(3) Uani 1 1 d . . . . .
C1 C 0.28631(7) 0.39303(19) 0.35268(16) 0.0164(4) Uani 1 1 d . . . . .
C2 C 0.23573(8) 0.3081(2) 0.32014(18) 0.0195(4) Uani 1 1 d . . . . .
H2 H 0.2330(9) 0.226(2) 0.260(2) 0.025(6) Uiso 1 1 d . . . . .
C3 C 0.19002(8) 0.3404(2) 0.37463(19) 0.0222(4) Uani 1 1 d . . . . .
H3 H 0.1571(11) 0.283(2) 0.348(2) 0.038(7) Uiso 1 1 d . . . . .
C4 C 0.19402(8) 0.4566(2) 0.46254(19) 0.0220(4) Uani 1 1 d . . . . .
H4 H 0.1638(9) 0.478(2) 0.502(2) 0.026(5) Uiso 1 1 d . . . . .
C5 C 0.24471(8) 0.5399(2) 0.49740(17) 0.0183(4) Uani 1 1 d . . . . .
H5 H 0.2478(8) 0.622(2) 0.5588(18) 0.012(4) Uiso 1 1 d . . . . .
C6 C 0.29151(7) 0.51044(19) 0.44307(16) 0.0151(4) Uani 1 1 d . . . . .
C7 C 0.34406(7) 0.59962(19) 0.48305(17) 0.0153(4) Uani 1 1 d . . . . .
H7 H 0.3454(8) 0.672(2) 0.5500(17) 0.009(4) Uiso 1 1 d . . . . .
C8 C 0.47338(7) 0.66772(18) 0.41603(16) 0.0139(3) Uani 1 1 d . . . . .
C9 C 0.52940(8) 0.8502(2) 0.61482(18) 0.0190(4) Uani 1 1 d . . . . .
H9A H 0.5265(9) 0.777(2) 0.669(2) 0.022(5) Uiso 1 1 d . . . . .
H9B H 0.4917(9) 0.905(2) 0.591(2) 0.026(5) Uiso 1 1 d . . . . .
C10 C 0.58083(8) 0.9508(2) 0.6730(2) 0.0216(4) Uani 1 1 d . . . . .
H10A H 0.6169(9) 0.904(2) 0.6954(19) 0.019(5) Uiso 1 1 d . . . . .
H10B H 0.5727(10) 1.000(2) 0.755(2) 0.037(6) Uiso 1 1 d . . . . .
H10C H 0.5827(9) 1.034(2) 0.608(2) 0.026(6) Uiso 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
S1 C8 1.7900(17) . ?
S1 S1 2.0444(8) 2_655 ?
S2 C8 1.7398(17) . ?
S2 C9 1.8204(18) . ?
O1 C1 1.358(2) . ?
O1 H1 0.88(3) . ?
N1 C7 1.288(2) . ?
N1 N2 1.4027(19) . ?
N2 C8 1.289(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.410(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.97(2) . ?
C3 C4 1.387(3) . ?
C3 H3 0.92(2) . ?
C4 C5 1.386(3) . ?
C4 H4 0.94(2) . ?
C5 C6 1.400(2) . ?
C5 H5 0.976(19) . ?
C6 C7 1.453(2) . ?
C7 H7 0.955(18) . ?
C9 C10 1.518(3) . ?
C9 H9A 0.89(2) . ?
C9 H9B 1.00(2) . ?
C10 H10A 0.93(2) . ?
C10 H10B 1.03(2) . ?
C10 H10C 1.02(2) . ?

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
C8 S1 S1 103.75(6) . 2_655 ?
C8 S2 C9 99.45(8) . . ?
C1 O1 H1 105.8(16) . . ?
C7 N1 N2 114.03(14) . . ?
C8 N2 N1 112.03(14) . . ?
O1 C1 C2 117.66(16) . . ?
O1 C1 C6 122.23(16) . . ?
C2 C1 C6 120.10(16) . . ?
C3 C2 C1 120.01(17) . . ?
C3 C2 H2 120.4(12) . . ?
C1 C2 H2 119.6(12) . . ?
C2 C3 C4 120.75(17) . . ?
C2 C3 H3 116.9(14) . . ?
C4 C3 H3 122.3(14) . . ?
C5 C4 C3 119.58(17) . . ?
C5 C4 H4 118.5(13) . . ?
C3 C4 H4 121.9(13) . . ?
C4 C5 C6 120.91(17) . . ?
C4 C5 H5 120.2(11) . . ?
C6 C5 H5 118.9(11) . . ?
C5 C6 C1 118.63(16) . . ?
C5 C6 C7 119.20(16) . . ?
C1 C6 C7 122.16(15) . . ?
N1 C7 C6 121.48(16) . . ?
N1 C7 H7 121.5(11) . . ?
C6 C7 H7 117.0(11) . . ?
N2 C8 S2 121.61(13) . . ?
N2 C8 S1 119.50(13) . . ?
S2 C8 S1 118.89(9) . . ?
C10 C9 S2 109.55(13) . . ?
C10 C9 H9A 112.5(14) . . ?
S2 C9 H9A 107.1(13) . . ?
C10 C9 H9B 111.8(12) . . ?
S2 C9 H9B 107.2(11) . . ?
H9A C9 H9B 108.5(17) . . ?
C9 C10 H10A 114.4(12) . . ?
C9 C10 H10B 106.7(13) . . ?
H10A C10 H10B 110.7(17) . . ?
C9 C10 H10C 110.5(12) . . ?
H10A C10 H10C 107.9(17) . . ?
H10B C10 H10C 106.4(16) . . ?

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
C7 N1 N2 C8 -173.33(15) . . . . ?
O1 C1 C2 C3 -179.67(16) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 C7 -179.49(16) . . . . ?
O1 C1 C6 C5 -179.83(15) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
O1 C1 C6 C7 -0.9(3) . . . . ?
C2 C1 C6 C7 178.22(16) . . . . ?
N2 N1 C7 C6 -177.85(14) . . . . ?
C5 C6 C7 N1 -174.57(16) . . . . ?
C1 C6 C7 N1 6.5(3) . . . . ?
N1 N2 C8 S2 -178.50(11) . . . . ?
N1 N2 C8 S1 0.6(2) . . . . ?
C9 S2 C8 N2 3.10(17) . . . . ?
C9 S2 C8 S1 -176.00(10) . . . . ?
S1 S1 C8 N2 -170.49(13) 2_655 . . . ?
S1 S1 C8 S2 8.63(11) 2_655 . . . ?
C8 S2 C9 C10 -177.21(13) . . . . ?

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
O1 H1 N1 0.88(3) 1.85(3) 2.648(2) 150(2) .

_refine_diff_density_max         0.497
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_JTM637_0m
_database_code_depnum_ccdc_archive 'CCDC 1851310'
_audit_update_record             
;
2018-06-24 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 Cl2 N2 O2 S3 Sn'
_chemical_formula_sum            'C12 H16 Cl2 N2 O2 S3 Sn'
_chemical_formula_weight         506.04

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5293(4)
_cell_length_b                   9.3173(5)
_cell_length_c                   12.6067(6)
_cell_angle_alpha                100.635(1)
_cell_angle_beta                 108.831(1)
_cell_angle_gamma                94.334(1)
_cell_volume                     922.06(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9371
_cell_measurement_theta_min      2.5249
_cell_measurement_theta_max      29.1802
_cell_measurement_temperature    100(2)

_exptl_crystal_description       tablet
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   0.716
_exptl_transmission_factor_max   0.862
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.020
_shelx_estimated_absorpt_T_min   0.592
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;

The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, colllected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 10 sec/frame.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            18013
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_max         29.180
_diffrn_reflns_theta_full        28.500
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4898
_reflns_number_gt                3803
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.99 Å). 
All were included as riding contributions with isotropic displacement 
parameters 1.2 - 1.5 times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4898
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0632
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.917
_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
Sn1 Sn 0.84133(2) 0.29008(2) 0.20203(2) 0.01577(6) Uani 1 1 d . . . . .
Cl1 Cl 0.83683(9) 0.12069(8) 0.03538(6) 0.02521(16) Uani 1 1 d . . . . .
Cl2 Cl 1.12499(8) 0.28009(8) 0.31784(6) 0.02126(15) Uani 1 1 d . . . . .
S1 S 0.53760(9) 0.16258(8) 0.44252(6) 0.02065(15) Uani 1 1 d . . . . .
S2 S 0.70136(9) 0.10901(8) 0.27422(6) 0.02160(16) Uani 1 1 d . . . . .
S3 S 0.44793(9) 0.21979(8) 0.03940(6) 0.02195(16) Uani 1 1 d . . . . .
O1 O 0.9201(2) 0.4706(2) 0.15654(15) 0.0197(4) Uani 1 1 d . . . . .
O2 O 0.5992(2) 0.3411(2) 0.10662(15) 0.0192(4) Uani 1 1 d . . . . .
N1 N 0.8066(3) 0.4373(2) 0.34631(18) 0.0138(5) Uani 1 1 d . . . . .
N2 N 0.7114(3) 0.3829(2) 0.40672(18) 0.0168(5) Uani 1 1 d . . . . .
C1 C 0.9799(3) 0.6061(3) 0.2228(2) 0.0170(6) Uani 1 1 d . . . . .
C2 C 1.0613(3) 0.7052(3) 0.1793(2) 0.0211(6) Uani 1 1 d . . . . .
H2 H 1.0786 0.6719 0.1086 0.025 Uiso 1 1 calc R U . . .
C3 C 1.1164(4) 0.8497(3) 0.2377(2) 0.0244(6) Uani 1 1 d . . . . .
H3 H 1.1685 0.9154 0.2057 0.029 Uiso 1 1 calc R U . . .
C4 C 1.0970(4) 0.9013(3) 0.3429(3) 0.0258(7) Uani 1 1 d . . . . .
H4 H 1.1361 1.0012 0.3827 0.031 Uiso 1 1 calc R U . . .
C5 C 1.0212(3) 0.8066(3) 0.3881(2) 0.0215(6) Uani 1 1 d . . . . .
H5 H 1.0093 0.8418 0.4604 0.026 Uiso 1 1 calc R U . . .
C6 C 0.9599(3) 0.6579(3) 0.3307(2) 0.0161(5) Uani 1 1 d . . . . .
C7 C 0.8720(3) 0.5739(3) 0.3838(2) 0.0170(6) Uani 1 1 d . . . . .
H7 H 0.8609 0.6238 0.4533 0.020 Uiso 1 1 calc R U . . .
C8 C 0.6610(3) 0.2427(3) 0.3767(2) 0.0168(6) Uani 1 1 d . . . . .
C9 C 0.5354(4) 0.3168(3) 0.5536(2) 0.0223(6) Uani 1 1 d . . . . .
H9A H 0.6500 0.3711 0.5941 0.027 Uiso 1 1 calc R U . . .
H9B H 0.4627 0.3858 0.5186 0.027 Uiso 1 1 calc R U . . .
C10 C 0.4693(4) 0.2572(4) 0.6381(3) 0.0290(7) Uani 1 1 d . . . . .
H10A H 0.3574 0.2008 0.5968 0.043 Uiso 1 1 calc R U . . .
H10B H 0.4630 0.3397 0.6966 0.043 Uiso 1 1 calc R U . . .
H10C H 0.5449 0.1929 0.6751 0.043 Uiso 1 1 calc R U . . .
C11 C 0.3794(4) 0.2600(3) -0.0993(2) 0.0281(7) Uani 1 1 d . . . . .
H11A H 0.4631 0.2398 -0.1360 0.042 Uiso 1 1 calc R U . . .
H11B H 0.3649 0.3643 -0.0922 0.042 Uiso 1 1 calc R U . . .
H11C H 0.2725 0.1982 -0.1462 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2896(4) 0.2822(4) 0.0899(3) 0.0451(10) Uani 1 1 d . . . . .
H12A H 0.2757 0.3822 0.0782 0.068 Uiso 1 1 calc R U . . .
H12B H 0.3209 0.2831 0.1720 0.068 Uiso 1 1 calc R U . . .
H12C H 0.1840 0.2160 0.0475 0.068 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
Sn1 O1 2.0109(18) . ?
Sn1 O2 2.1662(17) . ?
Sn1 N1 2.183(2) . ?
Sn1 Cl1 2.3709(7) . ?
Sn1 Cl2 2.4078(7) . ?
Sn1 S2 2.4624(7) . ?
S1 C8 1.739(3) . ?
S1 C9 1.818(3) . ?
S2 C8 1.760(3) . ?
S3 O2 1.5427(19) . ?
S3 C12 1.762(3) . ?
S3 C11 1.776(3) . ?
O1 C1 1.338(3) . ?
N1 C7 1.286(3) . ?
N1 N2 1.406(3) . ?
N2 C8 1.289(3) . ?
C1 C2 1.404(4) . ?
C1 C6 1.426(4) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.363(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.432(4) . ?
C7 H7 0.9500 . ?
C9 C10 1.523(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
O1 Sn1 O2 81.51(7) . . ?
O1 Sn1 N1 87.84(7) . . ?
O2 Sn1 N1 83.41(7) . . ?
O1 Sn1 Cl1 95.51(5) . . ?
O2 Sn1 Cl1 89.66(5) . . ?
N1 Sn1 Cl1 171.79(6) . . ?
O1 Sn1 Cl2 90.05(6) . . ?
O2 Sn1 Cl2 169.84(5) . . ?
N1 Sn1 Cl2 90.67(6) . . ?
Cl1 Sn1 Cl2 96.81(3) . . ?
O1 Sn1 S2 165.95(5) . . ?
O2 Sn1 S2 89.59(5) . . ?
N1 Sn1 S2 80.32(6) . . ?
Cl1 Sn1 S2 95.29(2) . . ?
Cl2 Sn1 S2 97.56(2) . . ?
C8 S1 C9 102.32(13) . . ?
C8 S2 Sn1 94.60(9) . . ?
O2 S3 C12 102.91(14) . . ?
O2 S3 C11 102.76(13) . . ?
C12 S3 C11 99.94(16) . . ?
C1 O1 Sn1 127.72(16) . . ?
S3 O2 Sn1 122.08(10) . . ?
C7 N1 N2 115.8(2) . . ?
C7 N1 Sn1 124.29(17) . . ?
N2 N1 Sn1 119.89(15) . . ?
C8 N2 N1 115.6(2) . . ?
O1 C1 C2 116.8(2) . . ?
O1 C1 C6 124.7(2) . . ?
C2 C1 C6 118.4(2) . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 116.1(2) . . ?
C1 C6 C7 125.3(2) . . ?
N1 C7 C6 126.2(2) . . ?
N1 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
N2 C8 S1 120.0(2) . . ?
N2 C8 S2 128.9(2) . . ?
S1 C8 S2 111.13(15) . . ?
C10 C9 S1 108.7(2) . . ?
C10 C9 H9A 110.0 . . ?
S1 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
S1 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S3 C11 H11A 109.5 . . ?
S3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S3 C12 H12A 109.5 . . ?
S3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C12 S3 O2 Sn1 128.43(16) . . . . ?
C11 S3 O2 Sn1 -128.06(13) . . . . ?
C7 N1 N2 C8 -172.9(2) . . . . ?
Sn1 N1 N2 C8 5.3(3) . . . . ?
Sn1 O1 C1 C2 166.08(17) . . . . ?
Sn1 O1 C1 C6 -17.0(4) . . . . ?
O1 C1 C2 C3 175.4(2) . . . . ?
C6 C1 C2 C3 -1.8(4) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C6 C7 -175.5(3) . . . . ?
O1 C1 C6 C5 -176.2(2) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
O1 C1 C6 C7 -0.6(4) . . . . ?
C2 C1 C6 C7 176.3(2) . . . . ?
N2 N1 C7 C6 -173.6(2) . . . . ?
Sn1 N1 C7 C6 8.3(4) . . . . ?
C5 C6 C7 N1 -179.9(3) . . . . ?
C1 C6 C7 N1 4.4(4) . . . . ?
N1 N2 C8 S1 -178.36(16) . . . . ?
N1 N2 C8 S2 2.6(4) . . . . ?
C9 S1 C8 N2 -5.6(3) . . . . ?
C9 S1 C8 S2 173.61(14) . . . . ?
Sn1 S2 C8 N2 -7.3(3) . . . . ?
Sn1 S2 C8 S1 173.56(12) . . . . ?
C8 S1 C9 C10 -166.0(2) . . . . ?

_refine_diff_density_max         1.247
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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_JTM639_0m
_audit_block_doi                 10.5517/ccdc.csd.cc204fn8
_database_code_depnum_ccdc_archive 'CCDC 1851309'
_audit_update_record             
;
2018-06-24 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N4 O2 S4 Sn'
_chemical_formula_sum            'C20 H20 N4 O2 S4 Sn'
_chemical_formula_weight         595.33

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'
Sn Sn -0.6537 1.4246 '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        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   7.7957(7)
_cell_length_b                   24.197(2)
_cell_length_c                   12.3003(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.157(1)
_cell_angle_gamma                90
_cell_volume                     2276.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.3838
_cell_measurement_theta_max      29.4254
_cell_measurement_temperature    100(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   0.742
_exptl_transmission_factor_max   0.862
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.515
_shelx_estimated_absorpt_T_min   0.712
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;

The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, colllected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 25 sec/frame.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22190
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.683
_diffrn_reflns_theta_max         29.523
_diffrn_reflns_theta_full        29.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3134
_reflns_number_gt                2684
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_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. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.99 Å). 
All were included as riding contributions with isotropic displacement 
parameters 1.2 - 1.5 times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3134
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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
Sn1 Sn 0.5000 0.31991(2) 0.2500 0.02009(10) Uani 1 2 d S T P . .
S1 S 0.73504(9) 0.39068(3) 0.27971(6) 0.02645(16) Uani 1 1 d . . . . .
S2 S 0.82007(11) 0.46199(3) 0.47061(6) 0.03199(18) Uani 1 1 d . . . . .
O1 O 0.3252(3) 0.25912(8) 0.26758(16) 0.0270(4) Uani 1 1 d . . . . .
N1 N 0.5665(3) 0.32157(8) 0.4299(2) 0.0225(5) Uani 1 1 d . . . . .
N2 N 0.6503(3) 0.36806(10) 0.48247(18) 0.0251(5) Uani 1 1 d . . . . .
C1 C 0.3471(3) 0.22207(11) 0.3500(2) 0.0228(5) Uani 1 1 d . . . . .
C2 C 0.2623(4) 0.17094(12) 0.3270(3) 0.0286(6) Uani 1 1 d . . . . .
H2 H 0.2005 0.1631 0.2542 0.034 Uiso 1 1 calc R U . . .
C3 C 0.2683(4) 0.13242(13) 0.4089(2) 0.0322(6) Uani 1 1 d . . . . .
H3 H 0.2108 0.0980 0.3917 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3564(4) 0.14223(12) 0.5171(3) 0.0292(6) Uani 1 1 d . . . . .
H4 H 0.3571 0.1152 0.5732 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4412(4) 0.19102(12) 0.5407(2) 0.0266(6) Uani 1 1 d . . . . .
H5 H 0.5019 0.1977 0.6143 0.032 Uiso 1 1 calc R U . . .
C6 C 0.4420(3) 0.23250(11) 0.4585(2) 0.0215(5) Uani 1 1 d . . . . .
C7 C 0.5356(3) 0.28197(11) 0.4937(2) 0.0239(5) Uani 1 1 d . . . . .
H7 H 0.5790 0.2862 0.5709 0.029 Uiso 1 1 calc R U . . .
C8 C 0.7189(3) 0.40030(11) 0.4176(2) 0.0240(5) Uani 1 1 d . . . . .
C9 C 0.8251(5) 0.45697(15) 0.6189(3) 0.0389(7) Uani 1 1 d . . . . .
H9A H 0.8615 0.4191 0.6439 0.047 Uiso 1 1 calc R U . . .
H9B H 0.9143 0.4829 0.6581 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6534(6) 0.46953(16) 0.6511(3) 0.0528(10) Uani 1 1 d . . . . .
H10A H 0.6054 0.5037 0.6148 0.079 Uiso 1 1 calc R U . . .
H10B H 0.6708 0.4740 0.7317 0.079 Uiso 1 1 calc R U . . .
H10C H 0.5718 0.4391 0.6278 0.079 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
Sn1 O1 2.045(2) 2_655 ?
Sn1 O1 2.045(2) . ?
Sn1 N1 2.173(2) 2_655 ?
Sn1 N1 2.173(2) . ?
Sn1 S1 2.4827(7) 2_655 ?
Sn1 S1 2.4827(7) . ?
S1 C8 1.741(3) . ?
S2 C8 1.754(3) . ?
S2 C9 1.821(3) . ?
O1 C1 1.339(3) . ?
N1 C7 1.290(3) . ?
N1 N2 1.395(3) . ?
N2 C8 1.302(4) . ?
C1 C2 1.406(4) . ?
C1 C6 1.418(4) . ?
C2 C3 1.367(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.357(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.426(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.425(4) . ?
C7 H7 0.9500 . ?
C9 C10 1.499(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
O1 Sn1 O1 87.99(11) 2_655 . ?
O1 Sn1 N1 86.46(8) 2_655 2_655 ?
O1 Sn1 N1 95.07(8) . 2_655 ?
O1 Sn1 N1 95.07(8) 2_655 . ?
O1 Sn1 N1 86.46(8) . . ?
N1 Sn1 N1 177.89(11) 2_655 . ?
O1 Sn1 S1 165.58(6) 2_655 2_655 ?
O1 Sn1 S1 91.36(6) . 2_655 ?
N1 Sn1 S1 79.25(6) 2_655 2_655 ?
N1 Sn1 S1 99.27(6) . 2_655 ?
O1 Sn1 S1 91.36(6) 2_655 . ?
O1 Sn1 S1 165.58(6) . . ?
N1 Sn1 S1 99.27(6) 2_655 . ?
N1 Sn1 S1 79.25(6) . . ?
S1 Sn1 S1 92.79(4) 2_655 . ?
C8 S1 Sn1 92.60(9) . . ?
C8 S2 C9 103.69(14) . . ?
C1 O1 Sn1 124.87(17) . . ?
C7 N1 N2 116.3(2) . . ?
C7 N1 Sn1 124.72(19) . . ?
N2 N1 Sn1 119.00(16) . . ?
C8 N2 N1 114.2(2) . . ?
O1 C1 C2 116.8(3) . . ?
O1 C1 C6 124.1(2) . . ?
C2 C1 C6 119.1(2) . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C7 125.4(2) . . ?
C1 C6 C5 118.0(2) . . ?
C7 C6 C5 116.6(2) . . ?
N1 C7 C6 125.7(3) . . ?
N1 C7 H7 117.1 . . ?
C6 C7 H7 117.1 . . ?
N2 C8 S1 129.2(2) . . ?
N2 C8 S2 119.4(2) . . ?
S1 C8 S2 111.35(15) . . ?
C10 C9 S2 113.8(3) . . ?
C10 C9 H9A 108.8 . . ?
S2 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
S2 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C7 N1 N2 C8 163.2(3) . . . . ?
Sn1 N1 N2 C8 -16.2(3) . . . . ?
Sn1 O1 C1 C2 -152.8(2) . . . . ?
Sn1 O1 C1 C6 30.5(3) . . . . ?
O1 C1 C2 C3 -175.4(3) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
O1 C1 C6 C7 -4.0(4) . . . . ?
C2 C1 C6 C7 179.4(3) . . . . ?
O1 C1 C6 C5 174.3(2) . . . . ?
C2 C1 C6 C5 -2.3(4) . . . . ?
C4 C5 C6 C1 1.5(4) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
N2 N1 C7 C6 175.7(2) . . . . ?
Sn1 N1 C7 C6 -4.9(4) . . . . ?
C1 C6 C7 N1 -9.3(4) . . . . ?
C5 C6 C7 N1 172.4(3) . . . . ?
N1 N2 C8 S1 -5.6(4) . . . . ?
N1 N2 C8 S2 177.14(19) . . . . ?
Sn1 S1 C8 N2 19.3(3) . . . . ?
Sn1 S1 C8 S2 -163.29(13) . . . . ?
C9 S2 C8 N2 8.3(3) . . . . ?
C9 S2 C8 S1 -169.40(17) . . . . ?
C8 S2 C9 C10 -78.0(3) . . . . ?

_refine_diff_density_max         1.624
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.133

####################################################################### 
# 
# 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_JTM643_0m
_audit_block_doi                 10.5517/ccdc.csd.cc204fm7
_database_code_depnum_ccdc_archive 'CCDC 1851308'
_audit_update_record             
;
2018-06-24 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Mn N4 O2 S4'
_chemical_formula_sum            'C20 H20 Mn N4 O2 S4'
_chemical_formula_weight         531.58

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   7.7764(10)
_cell_length_b                   24.056(3)
_cell_length_c                   12.1308(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.462(2)
_cell_angle_gamma                90
_cell_volume                     2197.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6888
_cell_measurement_theta_min      2.4236
_cell_measurement_theta_max      28.9473
_cell_measurement_temperature    100(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'intense green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             1092
_exptl_transmission_factor_min   0.771
_exptl_transmission_factor_max   0.888
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    1.007
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;

The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, colllected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 30 sec/frame.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            21217
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.693
_diffrn_reflns_theta_max         29.175
_diffrn_reflns_theta_full        29.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2959
_reflns_number_gt                2333
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_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. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.99 Å). 
All were included as riding contributions with isotropic displacement 
parameters 1.2 - 1.5 times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0677P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2959
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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 0.5000 0.31207(2) 0.2500 0.01610(13) Uani 1 2 d S T P . .
S1 S 0.71320(6) 0.38132(2) 0.27017(4) 0.02118(14) Uani 1 1 d . . . . .
S2 S 0.81615(7) 0.45927(2) 0.45926(4) 0.02487(15) Uani 1 1 d . . . . .
O1 O 0.32798(18) 0.25590(6) 0.25096(11) 0.0219(3) Uani 1 1 d . . . . .
N1 N 0.5578(2) 0.31863(7) 0.41826(14) 0.0184(3) Uani 1 1 d . . . . .
N2 N 0.6370(2) 0.36705(7) 0.47422(13) 0.0207(4) Uani 1 1 d . . . . .
C1 C 0.3413(2) 0.21874(8) 0.33384(16) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.2534(3) 0.16767(9) 0.30807(18) 0.0260(5) Uani 1 1 d . . . . .
H2 H 0.1930 0.1594 0.2316 0.031 Uiso 1 1 calc R U . . .
C3 C 0.2539(3) 0.12981(10) 0.39170(19) 0.0279(5) Uani 1 1 d . . . . .
H3 H 0.1933 0.0955 0.3721 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3411(3) 0.13988(9) 0.50571(18) 0.0240(4) Uani 1 1 d . . . . .
H4 H 0.3390 0.1131 0.5629 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4292(3) 0.18900(8) 0.53269(17) 0.0220(4) Uani 1 1 d . . . . .
H5 H 0.4882 0.1964 0.6098 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4347(3) 0.22939(8) 0.44824(16) 0.0188(4) Uani 1 1 d . . . . .
C7 C 0.5246(3) 0.27994(9) 0.48457(17) 0.0215(4) Uani 1 1 d . . . . .
H7 H 0.5639 0.2860 0.5643 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7081(3) 0.39720(9) 0.40886(16) 0.0198(4) Uani 1 1 d . . . . .
C9 C 0.8302(3) 0.45660(10) 0.61134(18) 0.0309(5) Uani 1 1 d . . . . .
H9A H 0.8599 0.4182 0.6388 0.037 Uiso 1 1 calc R U . . .
H9B H 0.9280 0.4811 0.6517 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6611(3) 0.47407(11) 0.6410(2) 0.0387(6) Uani 1 1 d . . . . .
H10A H 0.6791 0.4737 0.7239 0.058 Uiso 1 1 calc R U . . .
H10B H 0.5656 0.4482 0.6063 0.058 Uiso 1 1 calc R U . . .
H10C H 0.6288 0.5117 0.6120 0.058 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 O1 1.9036(15) . ?
Mn1 O1 1.9036(15) 2_655 ?
Mn1 N1 1.9836(16) . ?
Mn1 N1 1.9836(16) 2_655 ?
Mn1 S1 2.3196(6) . ?
Mn1 S1 2.3196(6) 2_655 ?
S1 C8 1.735(2) . ?
S2 C8 1.747(2) . ?
S2 C9 1.822(2) . ?
O1 C1 1.330(2) . ?
N1 C7 1.298(3) . ?
N1 N2 1.410(2) . ?
N2 C8 1.296(3) . ?
C1 C2 1.403(3) . ?
C1 C6 1.420(3) . ?
C2 C3 1.363(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.420(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.417(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.507(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
O1 Mn1 O1 89.55(9) . 2_655 ?
O1 Mn1 N1 91.67(6) . . ?
O1 Mn1 N1 94.81(6) 2_655 . ?
O1 Mn1 N1 94.81(6) . 2_655 ?
O1 Mn1 N1 91.67(6) 2_655 2_655 ?
N1 Mn1 N1 170.88(9) . 2_655 ?
O1 Mn1 S1 173.72(4) . . ?
O1 Mn1 S1 91.46(5) 2_655 . ?
N1 Mn1 S1 82.07(5) . . ?
N1 Mn1 S1 91.36(5) 2_655 . ?
O1 Mn1 S1 91.46(5) . 2_655 ?
O1 Mn1 S1 173.72(4) 2_655 2_655 ?
N1 Mn1 S1 91.36(5) . 2_655 ?
N1 Mn1 S1 82.07(5) 2_655 2_655 ?
S1 Mn1 S1 88.20(3) . 2_655 ?
C8 S1 Mn1 94.10(7) . . ?
C8 S2 C9 103.08(10) . . ?
C1 O1 Mn1 124.04(12) . . ?
C7 N1 N2 115.13(16) . . ?
C7 N1 Mn1 123.49(14) . . ?
N2 N1 Mn1 121.37(12) . . ?
C8 N2 N1 111.69(16) . . ?
O1 C1 C2 118.60(17) . . ?
O1 C1 C6 122.81(18) . . ?
C2 C1 C6 118.55(18) . . ?
C3 C2 C1 120.58(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 122.0(2) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 118.48(19) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 121.56(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C1 123.44(18) . . ?
C7 C6 C5 117.66(17) . . ?
C1 C6 C5 118.77(18) . . ?
N1 C7 C6 125.58(18) . . ?
N1 C7 H7 117.2 . . ?
C6 C7 H7 117.2 . . ?
N2 C8 S1 125.91(16) . . ?
N2 C8 S2 120.37(15) . . ?
S1 C8 S2 113.70(12) . . ?
C10 C9 S2 113.35(16) . . ?
C10 C9 H9A 108.9 . . ?
S2 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
S2 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C7 N1 N2 C8 163.17(17) . . . . ?
Mn1 N1 N2 C8 -17.7(2) . . . . ?
Mn1 O1 C1 C2 -154.46(15) . . . . ?
Mn1 O1 C1 C6 28.1(3) . . . . ?
O1 C1 C2 C3 -175.8(2) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
O1 C1 C6 C7 -1.0(3) . . . . ?
C2 C1 C6 C7 -178.45(19) . . . . ?
O1 C1 C6 C5 174.76(18) . . . . ?
C2 C1 C6 C5 -2.7(3) . . . . ?
C4 C5 C6 C7 178.04(19) . . . . ?
C4 C5 C6 C1 2.0(3) . . . . ?
N2 N1 C7 C6 175.34(18) . . . . ?
Mn1 N1 C7 C6 -3.8(3) . . . . ?
C1 C6 C7 N1 -11.7(3) . . . . ?
C5 C6 C7 N1 172.54(19) . . . . ?
N1 N2 C8 S1 -1.3(2) . . . . ?
N1 N2 C8 S2 -179.54(13) . . . . ?
Mn1 S1 C8 N2 14.48(19) . . . . ?
Mn1 S1 C8 S2 -167.16(10) . . . . ?
C9 S2 C8 N2 10.3(2) . . . . ?
C9 S2 C8 S1 -168.15(11) . . . . ?
C8 S2 C9 C10 -80.99(19) . . . . ?

_refine_diff_density_max         0.915
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_JTM641_0m
_audit_block_doi                 10.5517/ccdc.csd.cc204fl6
_database_code_depnum_ccdc_archive 'CCDC 1851307'
_audit_update_record             
;
2018-06-24 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 N2 O4 S2 V'
_chemical_formula_sum            'C12 H17 N2 O4 S2 V'
_chemical_formula_weight         368.33

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'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0281(17)
_cell_length_b                   10.127(2)
_cell_length_c                   11.104(2)
_cell_angle_alpha                110.554(3)
_cell_angle_beta                 110.250(3)
_cell_angle_gamma                94.785(3)
_cell_volume                     771.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4306
_cell_measurement_theta_min      2.3697
_cell_measurement_theta_max      28.8641
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            'dark yellow-brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   0.736
_exptl_transmission_factor_max   0.928
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.929
_shelx_estimated_absorpt_T_min   0.808
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;

The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, colllected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 20 sec/frame.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14305
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.140
_diffrn_reflns_theta_max         28.909
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4010
_reflns_number_gt                3086
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_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. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.99 Å) while that 
attached to oxygen was placed in a location derived from a difference 
map and its coordinates adjusted to give O---H = 0.87 %A. All were included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0791P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4010
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
V1 V 0.68868(5) 0.72275(4) 0.38291(4) 0.01580(13) Uani 1 1 d . . . . .
S1 S 0.71962(9) 0.87852(6) 0.61547(6) 0.02074(16) Uani 1 1 d . . . . .
S2 S 0.72737(9) 0.81997(7) 0.85392(6) 0.02044(16) Uani 1 1 d . . . . .
O1 O 0.6114(2) 0.55213(17) 0.21982(17) 0.0172(4) Uani 1 1 d . . . . .
O2 O 0.8985(2) 0.76464(19) 0.41203(18) 0.0210(4) Uani 1 1 d . . . . .
O3 O 0.5979(2) 0.85201(18) 0.32357(18) 0.0196(4) Uani 1 1 d . . . . .
N1 N 0.7265(3) 0.5795(2) 0.4896(2) 0.0150(4) Uani 1 1 d . . . . .
N2 N 0.7235(3) 0.6142(2) 0.6237(2) 0.0165(4) Uani 1 1 d . . . . .
C1 C 0.6819(3) 0.4350(3) 0.1935(2) 0.0165(5) Uani 1 1 d . . . . .
C2 C 0.6617(3) 0.3532(3) 0.0565(2) 0.0192(5) Uani 1 1 d . . . . .
H2 H 0.6039 0.3833 -0.0165 0.023 Uiso 1 1 calc R U . . .
C3 C 0.7267(3) 0.2271(3) 0.0271(3) 0.0197(5) Uani 1 1 d . . . . .
H3 H 0.7121 0.1715 -0.0664 0.024 Uiso 1 1 calc R U . . .
C4 C 0.8128(3) 0.1814(3) 0.1330(3) 0.0200(5) Uani 1 1 d . . . . .
H4 H 0.8583 0.0962 0.1120 0.024 Uiso 1 1 calc R U . . .
C5 C 0.8314(3) 0.2607(3) 0.2681(3) 0.0169(5) Uani 1 1 d . . . . .
H5 H 0.8892 0.2291 0.3400 0.020 Uiso 1 1 calc R U . . .
C6 C 0.7658(3) 0.3883(2) 0.3014(2) 0.0155(5) Uani 1 1 d . . . . .
C7 C 0.7681(3) 0.4560(2) 0.4399(2) 0.0157(5) Uani 1 1 d . . . . .
H7 H 0.8028 0.4065 0.4999 0.019 Uiso 1 1 calc R U . . .
C8 C 0.7229(3) 0.7508(3) 0.6847(2) 0.0163(5) Uani 1 1 d . . . . .
C9 C 0.7937(3) 0.6842(3) 0.9214(3) 0.0200(5) Uani 1 1 d . . . . .
H9A H 0.6923 0.5968 0.8739 0.024 Uiso 1 1 calc R U . . .
H9B H 0.9011 0.6556 0.9041 0.024 Uiso 1 1 calc R U . . .
C10 C 0.8402(4) 0.7508(3) 1.0781(3) 0.0253(6) Uani 1 1 d . . . . .
H10A H 0.7380 0.7887 1.0945 0.038 Uiso 1 1 calc R U . . .
H10B H 0.9498 0.8300 1.1254 0.038 Uiso 1 1 calc R U . . .
H10C H 0.8627 0.6766 1.1156 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6842(4) 0.9867(3) 0.3335(3) 0.0243(6) Uani 1 1 d . . . . .
H11A H 0.6254 0.9961 0.2444 0.036 Uiso 1 1 calc R U . . .
H11B H 0.8137 0.9898 0.3536 0.036 Uiso 1 1 calc R U . . .
H11C H 0.6729 1.0668 0.4093 0.036 Uiso 1 1 calc R U . . .
O4 O 0.3938(2) 0.64689(18) 0.35832(18) 0.0192(4) Uani 1 1 d . . . . .
H4A H 0.3533 0.5637 0.3569 0.023 Uiso 1 1 d R U . . .
C12 C 0.2373(3) 0.6877(3) 0.2825(3) 0.0239(6) Uani 1 1 d . . . . .
H12A H 0.2057 0.6387 0.1815 0.036 Uiso 1 1 calc R U . . .
H12B H 0.2651 0.7930 0.3112 0.036 Uiso 1 1 calc R U . . .
H12C H 0.1340 0.6593 0.3032 0.036 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
V1 O2 1.5904(18) . ?
V1 O3 1.7639(17) . ?
V1 O1 1.8699(17) . ?
V1 N1 2.152(2) . ?
V1 O4 2.3177(18) . ?
V1 S1 2.4183(9) . ?
S1 C8 1.719(2) . ?
S2 C8 1.746(2) . ?
S2 C9 1.818(3) . ?
O1 C1 1.340(3) . ?
O3 C11 1.427(3) . ?
N1 C7 1.301(3) . ?
N1 N2 1.414(3) . ?
N2 C8 1.311(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.416(3) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.413(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.440(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.519(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O4 C12 1.434(3) . ?
O4 H4A 0.8700 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
O2 V1 O3 102.95(9) . . ?
O2 V1 O1 99.83(8) . . ?
O3 V1 O1 104.39(8) . . ?
O2 V1 N1 94.44(8) . . ?
O3 V1 N1 158.58(8) . . ?
O1 V1 N1 84.55(8) . . ?
O2 V1 O4 172.98(8) . . ?
O3 V1 O4 83.67(7) . . ?
O1 V1 O4 80.53(7) . . ?
N1 V1 O4 78.60(7) . . ?
O2 V1 S1 96.04(7) . . ?
O3 V1 S1 88.15(6) . . ?
O1 V1 S1 156.89(6) . . ?
N1 V1 S1 77.54(6) . . ?
O4 V1 S1 81.69(5) . . ?
C8 S1 V1 98.73(8) . . ?
C8 S2 C9 104.66(12) . . ?
C1 O1 V1 129.95(15) . . ?
C11 O3 V1 131.42(16) . . ?
C7 N1 N2 113.57(19) . . ?
C7 N1 V1 122.23(16) . . ?
N2 N1 V1 124.01(14) . . ?
C8 N2 N1 112.12(19) . . ?
O1 C1 C2 119.5(2) . . ?
O1 C1 C6 120.5(2) . . ?
C2 C1 C6 119.8(2) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 118.3(2) . . ?
C1 C6 C7 122.4(2) . . ?
N1 C7 C6 125.4(2) . . ?
N1 C7 H7 117.3 . . ?
C6 C7 H7 117.3 . . ?
N2 C8 S1 126.61(19) . . ?
N2 C8 S2 120.26(18) . . ?
S1 C8 S2 113.12(14) . . ?
C10 C9 S2 107.58(18) . . ?
C10 C9 H9A 110.2 . . ?
S2 C9 H9A 110.2 . . ?
C10 C9 H9B 110.2 . . ?
S2 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 O4 V1 124.71(14) . . ?
C12 O4 H4A 106.4 . . ?
V1 O4 H4A 123.2 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O2 V1 O1 C1 50.6(2) . . . . ?
O3 V1 O1 C1 156.83(19) . . . . ?
N1 V1 O1 C1 -42.96(19) . . . . ?
O4 V1 O1 C1 -122.3(2) . . . . ?
S1 V1 O1 C1 -82.1(2) . . . . ?
O2 V1 O3 C11 -16.7(2) . . . . ?
O1 V1 O3 C11 -120.5(2) . . . . ?
N1 V1 O3 C11 126.8(2) . . . . ?
O4 V1 O3 C11 160.9(2) . . . . ?
S1 V1 O3 C11 79.1(2) . . . . ?
C7 N1 N2 C8 165.4(2) . . . . ?
V1 N1 N2 C8 -9.7(3) . . . . ?
V1 O1 C1 C2 -150.60(18) . . . . ?
V1 O1 C1 C6 33.6(3) . . . . ?
O1 C1 C2 C3 -176.8(2) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 172.2(2) . . . . ?
O1 C1 C6 C5 177.2(2) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
O1 C1 C6 C7 4.6(3) . . . . ?
C2 C1 C6 C7 -171.2(2) . . . . ?
N2 N1 C7 C6 174.4(2) . . . . ?
V1 N1 C7 C6 -10.4(3) . . . . ?
C5 C6 C7 N1 174.1(2) . . . . ?
C1 C6 C7 N1 -13.2(4) . . . . ?
N1 N2 C8 S1 1.7(3) . . . . ?
N1 N2 C8 S2 -177.78(15) . . . . ?
V1 S1 C8 N2 5.0(2) . . . . ?
V1 S1 C8 S2 -175.51(10) . . . . ?
C9 S2 C8 N2 14.9(2) . . . . ?
C9 S2 C8 S1 -164.66(13) . . . . ?
C8 S2 C9 C10 168.03(17) . . . . ?

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
O4 H4A N2 0.87 1.96 2.829(3) 174 2_666
C9 H9A O1 0.99 2.41 3.362(3) 160 2_666

_refine_diff_density_max         1.149
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.129

####################################################################### 
# 
# 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_JTM645_0m
_audit_block_doi                 10.5517/ccdc.csd.cc204fk5
_database_code_depnum_ccdc_archive 'CCDC 1851306'
_audit_update_record             
;
2018-06-24 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 Mo N2 O4 S2'
_chemical_formula_sum            'C11 H14 Mo N2 O4 S2'
_chemical_formula_weight         398.30

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'
Mo Mo -1.6832 0.6857 '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'

_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.
;

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'

_cell_length_a                   10.0788(8)
_cell_length_b                   9.8639(8)
_cell_length_c                   14.4725(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.690(1)
_cell_angle_gamma                90
_cell_volume                     1438.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.4989
_cell_measurement_theta_max      29.0221
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   0.765
_exptl_transmission_factor_max   0.862
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.215
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;

The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, colllected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 30 sec/frame.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            27178
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.021
_diffrn_reflns_theta_max         29.167
_diffrn_reflns_theta_full        29.100
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3872
_reflns_number_gt                3256
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_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. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.99 Å) while that 
attached to oxygen was placed in a location derived from a difference 
map and its coordinates adjusted to give O---H = 0.87 %A. All were included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3872
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
Mo1 Mo 0.26176(2) 0.63468(2) 0.34079(2) 0.01338(7) Uani 1 1 d . . . . .
S1 S 0.43550(5) 0.79147(5) 0.39478(4) 0.01821(12) Uani 1 1 d . . . . .
S2 S 0.72472(5) 0.74152(5) 0.43364(3) 0.01692(11) Uani 1 1 d . . . . .
O1 O 0.16806(14) 0.46431(14) 0.33633(11) 0.0203(3) Uani 1 1 d . . . . .
O2 O 0.29977(16) 0.65260(15) 0.22720(11) 0.0235(3) Uani 1 1 d . . . . .
O3 O 0.14157(14) 0.75187(14) 0.36127(10) 0.0190(3) Uani 1 1 d . . . . .
O4 O 0.24879(14) 0.59506(16) 0.49814(10) 0.0194(3) Uani 1 1 d . . . . .
H4A H 0.3091 0.5563 0.5326 0.023 Uiso 1 1 d R U . . .
N1 N 0.43848(15) 0.49679(17) 0.37212(11) 0.0127(3) Uani 1 1 d . . . . .
N2 N 0.56086(16) 0.54843(17) 0.40172(11) 0.0134(3) Uani 1 1 d . . . . .
C1 C 0.1991(2) 0.3339(2) 0.31844(13) 0.0145(4) Uani 1 1 d . . . . .
C2 C 0.0967(2) 0.2468(2) 0.29201(13) 0.0171(4) Uani 1 1 d . . . . .
H2 H 0.0089 0.2805 0.2851 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1230(2) 0.1115(2) 0.27590(14) 0.0180(4) Uani 1 1 d . . . . .
H3 H 0.0526 0.0527 0.2579 0.022 Uiso 1 1 calc R U . . .
C4 C 0.2511(2) 0.0599(2) 0.28561(14) 0.0184(4) Uani 1 1 d . . . . .
H4 H 0.2682 -0.0334 0.2749 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3530(2) 0.14685(19) 0.31117(13) 0.0148(4) Uani 1 1 d . . . . .
H5 H 0.4405 0.1121 0.3177 0.018 Uiso 1 1 calc R U . . .
C6 C 0.32992(19) 0.2854(2) 0.32765(12) 0.0132(4) Uani 1 1 d . . . . .
C7 C 0.4407(2) 0.36703(19) 0.35646(13) 0.0133(4) Uani 1 1 d . . . . .
H7 H 0.5233 0.3221 0.3649 0.016 Uiso 1 1 calc R U . . .
C8 C 0.56658(19) 0.6798(2) 0.40804(12) 0.0133(4) Uani 1 1 d . . . . .
C9 C 0.7022(2) 0.9226(2) 0.44444(15) 0.0216(4) Uani 1 1 d . . . . .
H9A H 0.6636 0.9603 0.3867 0.026 Uiso 1 1 calc R U . . .
H9B H 0.6416 0.9432 0.4959 0.026 Uiso 1 1 calc R U . . .
C10 C 0.8392(2) 0.9840(2) 0.46339(17) 0.0298(5) Uani 1 1 d . . . . .
H10A H 0.8305 1.0818 0.4733 0.045 Uiso 1 1 calc R U . . .
H10B H 0.8966 0.9674 0.4104 0.045 Uiso 1 1 calc R U . . .
H10C H 0.8784 0.9420 0.5187 0.045 Uiso 1 1 calc R U . . .
C11 C 0.1374(2) 0.6160(3) 0.55552(16) 0.0289(5) Uani 1 1 d . . . . .
H11A H 0.0701 0.6686 0.5218 0.043 Uiso 1 1 calc R U . . .
H11B H 0.1651 0.6657 0.6111 0.043 Uiso 1 1 calc R U . . .
H11C H 0.1001 0.5281 0.5733 0.043 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
Mo1 O2 1.7017(16) . ?
Mo1 O3 1.7031(14) . ?
Mo1 O1 1.9284(14) . ?
Mo1 N1 2.2821(16) . ?
Mo1 O4 2.3158(14) . ?
Mo1 S1 2.4568(5) . ?
S1 C8 1.729(2) . ?
S2 C8 1.742(2) . ?
S2 C9 1.807(2) . ?
O1 C1 1.349(2) . ?
O4 C11 1.420(2) . ?
O4 H4A 0.8697 . ?
N1 C7 1.300(2) . ?
N1 N2 1.397(2) . ?
N2 C8 1.300(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.434(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.530(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
O2 Mo1 O3 105.46(7) . . ?
O2 Mo1 O1 100.02(7) . . ?
O3 Mo1 O1 104.37(6) . . ?
O2 Mo1 N1 93.99(6) . . ?
O3 Mo1 N1 157.67(6) . . ?
O1 Mo1 N1 82.42(6) . . ?
O2 Mo1 O4 169.60(6) . . ?
O3 Mo1 O4 83.95(6) . . ?
O1 Mo1 O4 81.51(6) . . ?
N1 Mo1 O4 75.95(5) . . ?
O2 Mo1 S1 94.24(6) . . ?
O3 Mo1 S1 91.33(5) . . ?
O1 Mo1 S1 154.98(5) . . ?
N1 Mo1 S1 76.14(4) . . ?
O4 Mo1 S1 80.91(4) . . ?
C8 S1 Mo1 100.08(7) . . ?
C8 S2 C9 104.36(10) . . ?
C1 O1 Mo1 136.27(13) . . ?
C11 O4 Mo1 127.24(13) . . ?
C11 O4 H4A 106.3 . . ?
Mo1 O4 H4A 126.2 . . ?
C7 N1 N2 113.30(16) . . ?
C7 N1 Mo1 124.54(13) . . ?
N2 N1 Mo1 121.85(12) . . ?
C8 N2 N1 115.03(16) . . ?
O1 C1 C2 117.92(17) . . ?
O1 C1 C6 121.64(18) . . ?
C2 C1 C6 120.43(18) . . ?
C3 C2 C1 119.99(19) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.00(19) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.98(19) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.50(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.08(18) . . ?
C5 C6 C7 117.68(18) . . ?
C1 C6 C7 124.19(18) . . ?
N1 C7 C6 126.05(18) . . ?
N1 C7 H7 117.0 . . ?
C6 C7 H7 117.0 . . ?
N2 C8 S1 126.44(15) . . ?
N2 C8 S2 113.75(14) . . ?
S1 C8 S2 119.81(12) . . ?
C10 C9 S2 107.01(16) . . ?
C10 C9 H9A 110.3 . . ?
S2 C9 H9A 110.3 . . ?
C10 C9 H9B 110.3 . . ?
S2 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
C7 N1 N2 C8 172.58(16) . . . . ?
Mo1 N1 N2 C8 -1.3(2) . . . . ?
Mo1 O1 C1 C2 -158.78(15) . . . . ?
Mo1 O1 C1 C6 22.4(3) . . . . ?
O1 C1 C2 C3 -177.90(18) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 178.21(18) . . . . ?
O1 C1 C6 C5 177.55(18) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
O1 C1 C6 C7 0.2(3) . . . . ?
C2 C1 C6 C7 -178.56(18) . . . . ?
N2 N1 C7 C6 178.43(17) . . . . ?
Mo1 N1 C7 C6 -7.8(3) . . . . ?
C5 C6 C7 N1 177.92(19) . . . . ?
C1 C6 C7 N1 -4.7(3) . . . . ?
N1 N2 C8 S1 6.9(2) . . . . ?
N1 N2 C8 S2 -173.82(12) . . . . ?
Mo1 S1 C8 N2 -7.95(17) . . . . ?
Mo1 S1 C8 S2 172.76(9) . . . . ?
C9 S2 C8 N2 -176.98(14) . . . . ?
C9 S2 C8 S1 2.39(14) . . . . ?
C8 S2 C9 C10 -177.87(15) . . . . ?

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
O4 H4A N2 0.87 1.91 2.778(2) 173 3_666

_refine_diff_density_max         1.604
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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_JTM649_0ma
_audit_block_doi                 10.5517/ccdc.csd.cc204fqb
_database_code_depnum_ccdc_archive 'CCDC 1851311'
_audit_update_record             
;
2018-06-24 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 I2 N3 O2 S2 Sn'
_chemical_formula_sum            'C13 H17 I2 N3 O2 S2 Sn'
_chemical_formula_weight         683.90

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   18.999(11)
_cell_length_b                   8.978(5)
_cell_length_c                   23.512(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4011(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      2.6545
_cell_measurement_theta_max      28.6351
_cell_measurement_temperature    100(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.265
_exptl_crystal_F_000             2560
_exptl_transmission_factor_min   0.435
_exptl_transmission_factor_max   0.746
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.571
_shelx_estimated_absorpt_T_min   0.361
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.84

_exptl_special_details           
;

The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, colllected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 20 sec/frame.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            72505
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.732
_diffrn_reflns_theta_max         29.391
_diffrn_reflns_theta_full        29.250
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5447
_reflns_number_gt                4487
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_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. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.98 Å). 
All were included as riding contributions with isotropic displacement 
parameters 1.2 - 1.5 times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0227P)²+11.2690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5447
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
I1 I 0.41703(2) 0.86700(3) 0.36847(2) 0.01900(8) Uani 1 1 d . . . . .
I2 I 0.59157(2) 1.09307(3) 0.43438(2) 0.02024(8) Uani 1 1 d . . . . .
Sn1 Sn 0.55916(2) 0.81752(3) 0.38717(2) 0.01389(8) Uani 1 1 d . . . . .
S1 S 0.55030(6) 0.67952(13) 0.47880(5) 0.0185(2) Uani 1 1 d . . . . .
S2 S 0.64300(6) 0.44719(13) 0.52057(5) 0.0209(2) Uani 1 1 d . . . . .
O1 O 0.59098(16) 0.8820(4) 0.30802(14) 0.0190(7) Uani 1 1 d . . . . .
O2 O 0.54502(17) 0.6000(3) 0.34377(14) 0.0187(7) Uani 1 1 d . . . . .
N1 N 0.6667(2) 0.7277(4) 0.39445(15) 0.0152(7) Uani 1 1 d . . . . .
N2 N 0.6810(2) 0.6129(4) 0.43310(16) 0.0163(8) Uani 1 1 d . . . . .
N3 N 0.4818(2) 0.3857(4) 0.33517(16) 0.0175(8) Uani 1 1 d . . . . .
C1 C 0.6549(2) 0.9358(5) 0.29501(19) 0.0171(9) Uani 1 1 d . . . . .
C2 C 0.6604(2) 1.0395(5) 0.25081(19) 0.0193(9) Uani 1 1 d . . . . .
H2 H 0.6189 1.0742 0.2325 0.023 Uiso 1 1 calc R U . . .
C3 C 0.7255(3) 1.0924(5) 0.2333(2) 0.0225(10) Uani 1 1 d . . . . .
H3 H 0.7278 1.1634 0.2035 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7878(3) 1.0432(6) 0.2589(2) 0.0235(10) Uani 1 1 d . . . . .
H4 H 0.8323 1.0787 0.2463 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7832(2) 0.9422(5) 0.3028(2) 0.0202(9) Uani 1 1 d . . . . .
H5 H 0.8251 0.9091 0.3208 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7181(2) 0.8868(5) 0.32171(19) 0.0170(9) Uani 1 1 d . . . . .
C7 C 0.7209(2) 0.7742(5) 0.36565(18) 0.0164(9) Uani 1 1 d . . . . .
H7 H 0.7653 0.7313 0.3741 0.020 Uiso 1 1 calc R U . . .
C8 C 0.6311(2) 0.5882(5) 0.46981(18) 0.0163(9) Uani 1 1 d . . . . .
C9 C 0.7345(3) 0.3937(7) 0.5102(2) 0.0348(13) Uani 1 1 d . . . . .
H9A H 0.7373 0.3144 0.4810 0.042 Uiso 1 1 calc R U . . .
H9B H 0.7616 0.4806 0.4963 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7658(3) 0.3388(7) 0.5647(2) 0.0387(14) Uani 1 1 d . . . . .
H10A H 0.8152 0.3115 0.5583 0.058 Uiso 1 1 calc R U . . .
H10B H 0.7397 0.2513 0.5779 0.058 Uiso 1 1 calc R U . . .
H10C H 0.7632 0.4175 0.5935 0.058 Uiso 1 1 calc R U . . .
C11 C 0.4948(2) 0.5158(5) 0.3580(2) 0.0182(9) Uani 1 1 d . . . . .
H11 H 0.4643 0.5493 0.3873 0.022 Uiso 1 1 calc R U . . .
C12 C 0.5270(3) 0.3208(6) 0.2914(2) 0.0241(10) Uani 1 1 d . . . . .
H12A H 0.4983 0.2909 0.2587 0.036 Uiso 1 1 calc R U . . .
H12B H 0.5512 0.2333 0.3069 0.036 Uiso 1 1 calc R U . . .
H12C H 0.5619 0.3946 0.2793 0.036 Uiso 1 1 calc R U . . .
C13 C 0.4221(3) 0.2964(5) 0.3544(2) 0.0252(11) Uani 1 1 d . . . . .
H13A H 0.3914 0.2744 0.3221 0.038 Uiso 1 1 calc R U . . .
H13B H 0.3957 0.3520 0.3832 0.038 Uiso 1 1 calc R U . . .
H13C H 0.4394 0.2030 0.3709 0.038 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
I1 Sn1 2.7716(15) . ?
I2 Sn1 2.7807(13) . ?
Sn1 O1 2.040(3) . ?
Sn1 N1 2.203(4) . ?
Sn1 O2 2.220(3) . ?
Sn1 S1 2.4910(16) . ?
S1 C8 1.753(5) . ?
S2 C8 1.754(5) . ?
S2 C9 1.820(5) . ?
O1 C1 1.343(5) . ?
O2 C11 1.261(5) . ?
N1 C7 1.301(6) . ?
N1 N2 1.401(5) . ?
N2 C8 1.301(6) . ?
N3 C11 1.309(6) . ?
N3 C13 1.460(6) . ?
N3 C12 1.461(6) . ?
C1 C2 1.399(6) . ?
C1 C6 1.423(6) . ?
C2 C3 1.388(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.446(6) . ?
C7 H7 0.9500 . ?
C9 C10 1.496(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
O1 Sn1 N1 84.26(13) . . ?
O1 Sn1 O2 82.32(13) . . ?
N1 Sn1 O2 79.97(13) . . ?
O1 Sn1 S1 161.79(10) . . ?
N1 Sn1 S1 79.24(10) . . ?
O2 Sn1 S1 87.24(10) . . ?
O1 Sn1 I1 95.66(9) . . ?
N1 Sn1 I1 167.02(10) . . ?
O2 Sn1 I1 87.15(8) . . ?
S1 Sn1 I1 98.69(3) . . ?
O1 Sn1 I2 92.63(10) . . ?
N1 Sn1 I2 95.13(10) . . ?
O2 Sn1 I2 173.26(8) . . ?
S1 Sn1 I2 96.44(5) . . ?
I1 Sn1 I2 97.84(2) . . ?
C8 S1 Sn1 93.97(15) . . ?
C8 S2 C9 102.8(2) . . ?
C1 O1 Sn1 125.3(3) . . ?
C11 O2 Sn1 119.8(3) . . ?
C7 N1 N2 114.8(4) . . ?
C7 N1 Sn1 125.1(3) . . ?
N2 N1 Sn1 120.0(3) . . ?
C8 N2 N1 114.5(4) . . ?
C11 N3 C13 120.7(4) . . ?
C11 N3 C12 122.2(4) . . ?
C13 N3 C12 117.1(4) . . ?
O1 C1 C2 118.4(4) . . ?
O1 C1 C6 123.5(4) . . ?
C2 C1 C6 118.1(4) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.3(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 C7 116.1(4) . . ?
C1 C6 C7 124.2(4) . . ?
N1 C7 C6 124.6(4) . . ?
N1 C7 H7 117.7 . . ?
C6 C7 H7 117.7 . . ?
N2 C8 S1 129.7(3) . . ?
N2 C8 S2 118.7(3) . . ?
S1 C8 S2 111.6(2) . . ?
C10 C9 S2 110.6(4) . . ?
C10 C9 H9A 109.5 . . ?
S2 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
S2 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 N3 124.7(4) . . ?
O2 C11 H11 117.6 . . ?
N3 C11 H11 117.6 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C7 N1 N2 C8 166.3(4) . . . . ?
Sn1 N1 N2 C8 -12.7(5) . . . . ?
Sn1 O1 C1 C2 -148.7(3) . . . . ?
Sn1 O1 C1 C6 34.9(6) . . . . ?
O1 C1 C2 C3 -176.3(4) . . . . ?
C6 C1 C2 C3 0.4(7) . . . . ?
C1 C2 C3 C4 0.5(7) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 C1 0.0(7) . . . . ?
C4 C5 C6 C7 176.1(4) . . . . ?
O1 C1 C6 C5 175.9(4) . . . . ?
C2 C1 C6 C5 -0.6(6) . . . . ?
O1 C1 C6 C7 0.1(7) . . . . ?
C2 C1 C6 C7 -176.4(4) . . . . ?
N2 N1 C7 C6 177.2(4) . . . . ?
Sn1 N1 C7 C6 -3.9(6) . . . . ?
C5 C6 C7 N1 168.6(4) . . . . ?
C1 C6 C7 N1 -15.5(7) . . . . ?
N1 N2 C8 S1 -1.6(6) . . . . ?
N1 N2 C8 S2 -179.9(3) . . . . ?
Sn1 S1 C8 N2 11.8(4) . . . . ?
Sn1 S1 C8 S2 -169.9(2) . . . . ?
C9 S2 C8 N2 8.0(4) . . . . ?
C9 S2 C8 S1 -170.5(3) . . . . ?
C8 S2 C9 C10 150.4(4) . . . . ?
Sn1 O2 C11 N3 180.0(3) . . . . ?
C13 N3 C11 O2 -179.8(4) . . . . ?
C12 N3 C11 O2 2.6(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
C12 H12A O1 0.98 2.45 3.286(6) 143 3_645

_refine_diff_density_max         1.909
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.200

