# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_MBIIT-13-F
_database_code_depnum_ccdc_archive 'CCDC 1827268'
loop_
_audit_author_name
_audit_author_address
'Dr Manjit K. Bhattacharyya'
'Department of Chemistry, Cotton University, Panbazar, Guwahati-781001'
_audit_update_record             
;
2018-03-03 deposited with the CCDC.	2020-03-05 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         ?
_chemical_formula_sum            'C10 H20 Cu N2 O10 S'
_chemical_formula_weight         423.88

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'
Cu Cu 0.3201 1.2651 '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                   7.782(5)
_cell_length_b                   9.410(5)
_cell_length_c                   11.461(5)
_cell_angle_alpha                87.598(5)
_cell_angle_beta                 83.605(5)
_cell_angle_gamma                77.477(5)
_cell_volume                     814.1(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5723
_cell_measurement_theta_min      1.788
_cell_measurement_theta_max      24.492

_exptl_crystal_description       neddle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             438
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    1.524
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_process_details   'face indexing'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9079
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.788
_diffrn_reflns_theta_max         24.492
_diffrn_reflns_theta_full        24.492
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2591
_reflns_number_gt                2313
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+1.0650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2591
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0749
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Cu01 Cu 0.22536(4) 0.27864(3) 0.28470(3) 0.02352(13) Uani 1 1 d . . . . .
S1 S 0.16905(9) 0.78735(7) 0.33214(6) 0.02344(18) Uani 1 1 d . . . . .
O5 O 0.2456(3) 0.7305(3) 0.6381(2) 0.0366(6) Uani 1 1 d . . . . .
O1 O 0.3845(3) 0.3889(2) 0.36401(19) 0.0268(5) Uani 1 1 d . . . . .
O9 O 0.1399(3) 0.8769(2) 0.22641(17) 0.0352(5) Uani 1 1 d . . . . .
O10 O 0.3296(3) 0.6712(2) 0.30892(18) 0.0326(5) Uani 1 1 d . . . . .
O3 O 0.2064(3) 0.1573(2) 0.43822(18) 0.0277(5) Uani 1 1 d . . . . .
O7 O 0.0163(3) 0.7197(2) 0.36743(19) 0.0365(5) Uani 1 1 d . . . . .
O8 O 0.1933(3) 0.8770(2) 0.42887(18) 0.0392(5) Uani 1 1 d . . . . .
O2 O 0.0119(3) 0.4317(2) 0.3507(2) 0.0383(6) Uani 1 1 d . . . . .
O6 O 0.6471(4) 0.6426(3) 0.4007(2) 0.0473(7) Uani 1 1 d . . . . .
N2 N 0.2635(3) 0.3891(2) 0.12702(19) 0.0237(5) Uani 1 1 d . . . . .
N1 N 0.4458(3) 0.1393(2) 0.20615(19) 0.0243(5) Uani 1 1 d . . . . .
O4 O 0.0540(3) 0.1715(2) 0.2120(2) 0.0291(5) Uani 1 1 d . . . . .
C6 C 0.3888(4) 0.3132(3) 0.0489(2) 0.0264(6) Uani 1 1 d . . . . .
C5 C 0.4990(4) 0.1793(3) 0.0962(2) 0.0255(6) Uani 1 1 d . . . . .
C7 C 0.4139(5) 0.3623(4) -0.0661(3) 0.0399(8) Uani 1 1 d . . . . .
H7 H 0.4991 0.3081 -0.1196 0.048 Uiso 1 1 calc R U . . .
C2 C 0.7006(4) -0.0543(4) 0.2002(3) 0.0431(8) Uani 1 1 d . . . . .
H2 H 0.7681 -0.1328 0.2380 0.052 Uiso 1 1 calc R U . . .
C1 C 0.5452(4) 0.0245(3) 0.2564(3) 0.0330(7) Uani 1 1 d . . . . .
H1 H 0.5083 -0.0035 0.3322 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7533(4) -0.0149(4) 0.0886(3) 0.0452(9) Uani 1 1 d . . . . .
H3 H 0.8572 -0.0670 0.0490 0.054 Uiso 1 1 calc R U . . .
C10 C 0.1672(4) 0.5164(3) 0.0934(3) 0.0307(7) Uani 1 1 d . . . . .
H10 H 0.0830 0.5696 0.1480 0.037 Uiso 1 1 calc R U . . .
C9 C 0.1878(4) 0.5720(4) -0.0194(3) 0.0406(8) Uani 1 1 d . . . . .
H9 H 0.1198 0.6614 -0.0404 0.049 Uiso 1 1 calc R U . . .
C4 C 0.6525(4) 0.1020(4) 0.0346(3) 0.0381(8) Uani 1 1 d . . . . .
H4 H 0.6863 0.1290 -0.0421 0.046 Uiso 1 1 calc R U . . .
C8 C 0.3117(5) 0.4916(4) -0.1000(3) 0.0464(9) Uani 1 1 d . . . . .
H8 H 0.3258 0.5252 -0.1773 0.056 Uiso 1 1 calc R U . . .
H4A H 0.080(7) 0.104(5) 0.215(5) 0.080 Uiso 1 1 d . U . . .
H4B H -0.023(6) 0.193(5) 0.248(4) 0.080 Uiso 1 1 d . U . . .
H3A H 0.201(6) 0.068(5) 0.430(4) 0.080 Uiso 1 1 d . U . . .
H2A H 0.013(7) 0.505(5) 0.366(4) 0.080 Uiso 1 1 d . U . . .
H3B H 0.140(7) 0.194(6) 0.478(4) 0.080 Uiso 1 1 d . U . . .
H2B H -0.074(6) 0.417(5) 0.363(4) 0.080 Uiso 1 1 d . U . . .
H1A H 0.377(7) 0.383(5) 0.423(4) 0.080 Uiso 1 1 d . U . . .
H1B H 0.367(7) 0.464(5) 0.350(4) 0.080 Uiso 1 1 d . U . . .
H6A H 0.574(7) 0.660(6) 0.376(5) 0.080 Uiso 1 1 d . U . . .
H6B H 0.687(7) 0.693(6) 0.391(5) 0.080 Uiso 1 1 d . U . . .
H5A H 0.237(7) 0.770(6) 0.588(4) 0.080 Uiso 1 1 d . U . . .
H5B H 0.339(6) 0.706(5) 0.640(4) 0.080 Uiso 1 1 d . 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
Cu01 O2 2.045(2) . ?
Cu01 N1 2.062(2) . ?
Cu01 O3 2.066(2) . ?
Cu01 N2 2.071(2) . ?
Cu01 O1 2.080(2) . ?
Cu01 O4 2.095(3) . ?
S1 O9 1.457(2) . ?
S1 O8 1.474(2) . ?
S1 O7 1.477(2) . ?
S1 O10 1.478(2) . ?
O5 H5A 0.67(5) . ?
O5 H5B 0.72(5) . ?
O1 H1A 0.67(5) . ?
O1 H1B 0.70(5) . ?
O3 H3A 0.86(5) . ?
O3 H3B 0.69(5) . ?
O2 H2A 0.72(5) . ?
O2 H2B 0.71(5) . ?
O6 H6A 0.65(5) . ?
O6 H6B 0.62(5) . ?
N2 C10 1.335(4) . ?
N2 C6 1.349(4) . ?
N1 C1 1.335(4) . ?
N1 C5 1.346(4) . ?
O4 H4A 0.62(5) . ?
O4 H4B 0.69(5) . ?
C6 C7 1.385(4) . ?
C6 C5 1.481(4) . ?
C5 C4 1.391(4) . ?
C7 C8 1.369(5) . ?
C7 H7 0.9300 . ?
C2 C3 1.360(5) . ?
C2 C1 1.380(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C3 C4 1.373(5) . ?
C3 H3 0.9300 . ?
C10 C9 1.379(4) . ?
C10 H10 0.9300 . ?
C9 C8 1.378(5) . ?
C9 H9 0.9300 . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?

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 Cu01 N1 174.44(9) . . ?
O2 Cu01 O3 89.61(10) . . ?
N1 Cu01 O3 95.72(9) . . ?
O2 Cu01 N2 94.89(10) . . ?
N1 Cu01 N2 79.75(9) . . ?
O3 Cu01 N2 175.43(8) . . ?
O2 Cu01 O1 87.81(10) . . ?
N1 Cu01 O1 90.81(10) . . ?
O3 Cu01 O1 87.97(9) . . ?
N2 Cu01 O1 91.45(9) . . ?
O2 Cu01 O4 89.47(10) . . ?
N1 Cu01 O4 92.04(10) . . ?
O3 Cu01 O4 90.49(9) . . ?
N2 Cu01 O4 90.30(9) . . ?
O1 Cu01 O4 176.88(8) . . ?
O9 S1 O8 110.14(13) . . ?
O9 S1 O7 110.29(13) . . ?
O8 S1 O7 109.06(13) . . ?
O9 S1 O10 109.41(12) . . ?
O8 S1 O10 109.01(13) . . ?
O7 S1 O10 108.91(12) . . ?
H5A O5 H5B 105(5) . . ?
Cu01 O1 H1A 114(4) . . ?
Cu01 O1 H1B 113(4) . . ?
H1A O1 H1B 107(6) . . ?
Cu01 O3 H3A 116(3) . . ?
Cu01 O3 H3B 110(4) . . ?
H3A O3 H3B 114(5) . . ?
Cu01 O2 H2A 126(4) . . ?
Cu01 O2 H2B 122(4) . . ?
H2A O2 H2B 111(5) . . ?
H6A O6 H6B 109(7) . . ?
C10 N2 C6 119.0(2) . . ?
C10 N2 Cu01 126.9(2) . . ?
C6 N2 Cu01 113.82(18) . . ?
C1 N1 C5 118.7(2) . . ?
C1 N1 Cu01 126.70(19) . . ?
C5 N1 Cu01 114.35(18) . . ?
Cu01 O4 H4A 112(5) . . ?
Cu01 O4 H4B 102(4) . . ?
H4A O4 H4B 110(6) . . ?
N2 C6 C7 121.2(3) . . ?
N2 C6 C5 115.3(2) . . ?
C7 C6 C5 123.5(3) . . ?
N1 C5 C4 121.2(3) . . ?
N1 C5 C6 115.8(2) . . ?
C4 C5 C6 123.0(3) . . ?
C8 C7 C6 119.2(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
N2 C10 C9 122.5(3) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C8 C9 C10 118.3(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?

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
C10 N2 C6 C7 -2.6(4) . . . . ?
Cu01 N2 C6 C7 171.0(2) . . . . ?
C10 N2 C6 C5 175.3(2) . . . . ?
Cu01 N2 C6 C5 -11.1(3) . . . . ?
C1 N1 C5 C4 1.1(4) . . . . ?
Cu01 N1 C5 C4 175.6(2) . . . . ?
C1 N1 C5 C6 -176.1(3) . . . . ?
Cu01 N1 C5 C6 -1.6(3) . . . . ?
N2 C6 C5 N1 8.6(4) . . . . ?
C7 C6 C5 N1 -173.5(3) . . . . ?
N2 C6 C5 C4 -168.6(3) . . . . ?
C7 C6 C5 C4 9.3(5) . . . . ?
N2 C6 C7 C8 1.3(5) . . . . ?
C5 C6 C7 C8 -176.4(3) . . . . ?
C5 N1 C1 C2 0.3(5) . . . . ?
Cu01 N1 C1 C2 -173.5(2) . . . . ?
C3 C2 C1 N1 -1.1(5) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C6 N2 C10 C9 1.7(4) . . . . ?
Cu01 N2 C10 C9 -171.0(2) . . . . ?
N2 C10 C9 C8 0.6(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
N1 C5 C4 C3 -1.7(5) . . . . ?
C6 C5 C4 C3 175.3(3) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
C10 C9 C8 C7 -1.9(5) . . . . ?

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
O5 H5B O1 0.72(5) 2.14(5) 2.852(4) 174(5) 2_666
O5 H5A O8 0.67(5) 2.08(5) 2.741(3) 174(6) .
O6 H6B O7 0.62(5) 2.61(5) 3.093(4) 137(6) 1_655
O6 H6A O10 0.65(5) 2.11(5) 2.748(4) 168(6) .
O1 H1B O10 0.70(5) 1.95(5) 2.658(3) 178(6) .
O1 H1A O6 0.67(5) 2.02(5) 2.690(4) 178(6) 2_666
O2 H2B O5 0.71(5) 2.12(5) 2.760(4) 149(5) 2_566
O3 H3B O7 0.69(5) 2.12(5) 2.791(3) 164(5) 2_566
O2 H2A O7 0.72(5) 2.03(5) 2.732(3) 166(5) .
O3 H3A O8 0.86(5) 1.81(5) 2.668(3) 174(4) 1_545
O3 H3A S1 0.86(5) 2.98(5) 3.815(3) 164(4) 1_545
O4 H4B O5 0.69(5) 2.06(5) 2.747(3) 175(6) 2_566
O4 H4A O9 0.62(5) 2.09(5) 2.710(3) 175(7) 1_545
C4 H4 O9 0.93 2.37 3.258(4) 158.6 2_665
C7 H7 O10 0.93 2.44 3.224(4) 141.9 2_665
C7 H7 O10 0.93 2.44 3.224(4) 141.9 2_665
C4 H4 O9 0.93 2.37 3.258(4) 158.6 2_665
O4 H4A O9 0.62(5) 2.09(5) 2.710(3) 175(7) 1_545
O4 H4B O5 0.69(5) 2.06(5) 2.747(3) 175(6) 2_566
O3 H3A S1 0.86(5) 2.98(5) 3.815(3) 164(4) 1_545
O3 H3A O8 0.86(5) 1.81(5) 2.668(3) 174(4) 1_545
O2 H2A O7 0.72(5) 2.03(5) 2.732(3) 166(5) .
O3 H3B O7 0.69(5) 2.12(5) 2.791(3) 164(5) 2_566
O2 H2B O5 0.71(5) 2.12(5) 2.760(4) 149(5) 2_566
O1 H1A O6 0.67(5) 2.02(5) 2.690(4) 178(6) 2_666
O1 H1B O10 0.70(5) 1.95(5) 2.658(3) 178(6) .
O6 H6A O10 0.65(5) 2.11(5) 2.748(4) 168(6) .
O6 H6B O7 0.62(5) 2.61(5) 3.093(4) 137(6) 1_655
O5 H5A O8 0.67(5) 2.08(5) 2.741(3) 174(6) .
O5 H5B O1 0.72(5) 2.14(5) 2.852(4) 174(5) 2_666

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1959920'
loop_
_audit_author_name
_audit_author_address
'Dr Manjit K. Bhattacharyya'
;Cotton University
India
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Mn N4 O8 S'
_chemical_formula_weight         431.29

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'
Mn Mn 0.3368 0.7283 '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           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                   17.1442(15)
_cell_length_b                   8.3999(8)
_cell_length_c                   12.5573(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.503(4)
_cell_angle_gamma                90
_cell_volume                     1802.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6121
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      21.96

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.896
_shelx_estimated_absorpt_T_min   0.775
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14730
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.702
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        24.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3135
_reflns_number_gt                2975
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0879P)²+3.1054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3135
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1483
_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 0.84850(2) 0.04374(5) 0.70077(3) 0.0204(2) Uani 1 1 d . . . . .
S1 S 0.88501(6) 0.42370(11) 0.66607(7) 0.0371(3) Uani 1 1 d . . . . .
O1 O 0.83925(16) 0.2791(3) 0.6438(2) 0.0466(7) Uani 1 1 d . . . . .
O2 O 0.92059(16) 0.1146(4) 0.8316(2) 0.0470(7) Uani 1 1 d . . . . .
O3 O 0.94618(17) -0.0029(4) 0.6132(2) 0.0516(7) Uani 1 1 d . . . . .
O4 O 0.8465(2) -0.1874(3) 0.7679(2) 0.0562(8) Uani 1 1 d . . . . .
O5 O 0.8349(2) 0.5601(4) 0.6385(3) 0.0611(9) Uani 1 1 d . . . . .
O6 O 0.91170(18) 0.4285(3) 0.7802(2) 0.0487(7) Uani 1 1 d . . . . .
O7 O 0.9527(2) 0.4293(4) 0.6023(3) 0.0662(10) Uani 1 1 d . . . . .
O8 O 0.92506(19) -0.2607(4) 0.4744(2) 0.0542(7) Uani 1 1 d . . . . .
N1 N 0.77576(19) -0.0283(4) 0.5631(3) 0.0411(8) Uani 1 1 d . . . . .
N2 N 0.5893(3) -0.1701(11) 0.2144(4) 0.123(3) Uani 1 1 d . . . . .
N3 N 0.7454(2) 0.0914(4) 0.7965(3) 0.0445(8) Uani 1 1 d . . . . .
N4 N 0.5211(3) 0.2144(12) 1.0556(4) 0.128(3) Uani 1 1 d . . . . .
C1 C 0.7148(3) -0.1245(6) 0.5709(4) 0.0524(11) Uani 1 1 d . . . . .
H1 H 0.705876 -0.166307 0.637464 0.063 Uiso 1 1 calc R U . . .
C2 C 0.6640(3) -0.1649(7) 0.4834(4) 0.0607(12) Uani 1 1 d . . . . .
H2 H 0.621017 -0.230234 0.491107 0.073 Uiso 1 1 calc R U . . .
C3 C 0.6792(3) -0.1056(6) 0.3851(3) 0.0545(11) Uani 1 1 d . . . . .
C4 C 0.7437(3) -0.0103(7) 0.3769(3) 0.0530(11) Uani 1 1 d . . . . .
H4 H 0.755838 0.028146 0.310756 0.064 Uiso 1 1 calc R U . . .
C5 C 0.7901(2) 0.0274(5) 0.4678(3) 0.0446(9) Uani 1 1 d . . . . .
H5 H 0.832941 0.094022 0.462155 0.054 Uiso 1 1 calc R U . . .
C6 C 0.6283(3) -0.1424(9) 0.2916(4) 0.0801(19) Uani 1 1 d . . . . .
C7 C 0.6772(3) 0.1513(6) 0.7569(3) 0.0542(11) Uani 1 1 d . . . . .
H7 H 0.671109 0.173762 0.684194 0.065 Uiso 1 1 calc R U . . .
C8 C 0.6158(3) 0.1816(7) 0.8167(4) 0.0618(13) Uani 1 1 d . . . . .
H8 H 0.568812 0.221533 0.785583 0.074 Uiso 1 1 calc R U . . .
C9 C 0.6257(3) 0.1508(7) 0.9257(4) 0.0574(12) Uani 1 1 d . . . . .
C10 C 0.6962(3) 0.0889(6) 0.9677(3) 0.0539(11) Uani 1 1 d . . . . .
H10 H 0.704388 0.066269 1.040233 0.065 Uiso 1 1 calc R U . . .
C11 C 0.7532(3) 0.0618(5) 0.9008(3) 0.0485(10) Uani 1 1 d . . . . .
H11 H 0.800544 0.020025 0.929516 0.058 Uiso 1 1 calc R U . . .
C12 C 0.5658(3) 0.1853(10) 0.9960(4) 0.0808(18) Uani 1 1 d . . . . .
H4B H 0.838600 -0.288795 0.721500 0.080 Uiso 1 1 d . U . . .
H3A H 0.998200 -0.008400 0.654500 0.080 Uiso 1 1 d . U . . .
H2A H 0.937387 0.228601 0.822500 0.080 Uiso 1 1 d . U . . .
H3B H 0.938600 -0.094400 0.564100 0.080 Uiso 1 1 d . U . . .
H4A H 0.871100 -0.218500 0.832900 0.080 Uiso 1 1 d . U . . .
H8A H 0.902479 -0.346684 0.525400 0.080 Uiso 1 1 d . U . . .
H8B H 0.975900 -0.304000 0.459582 0.080 Uiso 1 1 d . U . . .
H2B H 0.969600 0.060802 0.857903 0.080 Uiso 1 1 d . 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 O2 2.065(3) . ?
Mn1 O1 2.104(3) . ?
Mn1 O3 2.111(3) . ?
Mn1 O4 2.118(3) . ?
Mn1 N1 2.138(3) . ?
Mn1 N3 2.250(3) . ?
S1 O5 1.457(3) . ?
S1 O7 1.461(4) . ?
S1 O1 1.461(3) . ?
S1 O6 1.470(3) . ?
O2 H2A 1.009(3) . ?
O2 H2B 0.988(3) . ?
O3 H3A 0.997(3) . ?
O3 H3B 0.987(3) . ?
O4 H4B 1.035(3) . ?
O4 H4A 0.927(3) . ?
O8 H8A 1.059(3) . ?
O8 H8B 0.976(3) . ?
N1 C5 1.326(5) . ?
N1 C1 1.331(5) . ?
N2 C6 1.158(7) . ?
N3 C11 1.329(5) . ?
N3 C7 1.333(6) . ?
N4 C12 1.140(7) . ?
C1 C2 1.389(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(7) . ?
C3 C6 1.440(6) . ?
C4 C5 1.375(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C7 C8 1.364(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(7) . ?
C9 C12 1.435(7) . ?
C10 C11 1.358(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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 Mn1 O1 91.38(11) . . ?
O2 Mn1 O3 91.05(12) . . ?
O1 Mn1 O3 92.23(13) . . ?
O2 Mn1 O4 88.58(12) . . ?
O1 Mn1 O4 173.41(12) . . ?
O3 Mn1 O4 94.36(13) . . ?
O2 Mn1 N1 178.76(12) . . ?
O1 Mn1 N1 88.12(12) . . ?
O3 Mn1 N1 87.84(12) . . ?
O4 Mn1 N1 92.05(12) . . ?
O2 Mn1 N3 88.27(12) . . ?
O1 Mn1 N3 88.45(12) . . ?
O3 Mn1 N3 179.05(12) . . ?
O4 Mn1 N3 84.96(13) . . ?
N1 Mn1 N3 92.85(12) . . ?
O5 S1 O7 108.8(2) . . ?
O5 S1 O1 108.10(18) . . ?
O7 S1 O1 111.06(19) . . ?
O5 S1 O6 110.06(19) . . ?
O7 S1 O6 109.5(2) . . ?
O1 S1 O6 109.29(17) . . ?
S1 O1 Mn1 133.72(17) . . ?
Mn1 O2 H2A 109.98(19) . . ?
Mn1 O2 H2B 125.1(2) . . ?
H2A O2 H2B 103.3(3) . . ?
Mn1 O3 H3A 116.8(2) . . ?
Mn1 O3 H3B 113.5(2) . . ?
H3A O3 H3B 110.9(3) . . ?
Mn1 O4 H4B 122.4(2) . . ?
Mn1 O4 H4A 126.0(2) . . ?
H4B O4 H4A 107.1(3) . . ?
H8A O8 H8B 103.6(3) . . ?
C5 N1 C1 118.9(4) . . ?
C5 N1 Mn1 119.5(3) . . ?
C1 N1 Mn1 121.6(3) . . ?
C11 N3 C7 117.2(4) . . ?
C11 N3 Mn1 118.0(3) . . ?
C7 N3 Mn1 124.8(3) . . ?
N1 C1 C2 122.5(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.1(4) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 C6 120.6(5) . . ?
C4 C3 C6 120.2(5) . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.1(4) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
N2 C6 C3 177.8(7) . . ?
N3 C7 C8 123.8(4) . . ?
N3 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 117.9(4) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 C12 119.2(4) . . ?
C8 C9 C12 122.0(5) . . ?
C11 C10 C9 118.5(4) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
N3 C11 C10 123.8(4) . . ?
N3 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
N4 C12 C9 176.7(6) . . ?

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
O5 S1 O1 Mn1 -157.0(2) . . . . ?
O7 S1 O1 Mn1 83.7(3) . . . . ?
O6 S1 O1 Mn1 -37.2(3) . . . . ?
C5 N1 C1 C2 -2.2(7) . . . . ?
Mn1 N1 C1 C2 176.0(4) . . . . ?
N1 C1 C2 C3 1.7(8) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C1 C2 C3 C6 -179.5(5) . . . . ?
C2 C3 C4 C5 -2.0(7) . . . . ?
C6 C3 C4 C5 178.0(5) . . . . ?
C1 N1 C5 C4 0.5(6) . . . . ?
Mn1 N1 C5 C4 -177.7(3) . . . . ?
C3 C4 C5 N1 1.6(7) . . . . ?
C11 N3 C7 C8 -0.7(7) . . . . ?
Mn1 N3 C7 C8 -179.0(4) . . . . ?
N3 C7 C8 C9 1.3(8) . . . . ?
C7 C8 C9 C10 -1.1(8) . . . . ?
C7 C8 C9 C12 177.2(6) . . . . ?
C8 C9 C10 C11 0.5(8) . . . . ?
C12 C9 C10 C11 -177.9(5) . . . . ?
C7 N3 C11 C10 0.0(7) . . . . ?
Mn1 N3 C11 C10 178.4(4) . . . . ?
C9 C10 C11 N3 0.0(8) . . . . ?

_refine_diff_density_max         1.191
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.102

