# Electronic Supplementary Material (ESI) for Sustainable Energy & Fuels.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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 2152415'
loop_
_audit_author_name
_audit_author_address
'Dr. Shaikh M Mobin'
;IIT INDORE
India
;
_audit_update_record             
;
2022-02-16 deposited with the CCDC.	2022-05-10 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 N2 Ni O5 S'
_chemical_formula_weight         359.04

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.707(3)
_cell_length_b                   13.874(3)
_cell_length_c                   11.9878(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3444.0(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      28.38

_exptl_crystal_description       block
_exptl_crystal_colour            'light green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.266
_shelx_estimated_absorpt_T_min   0.680
_shelx_estimated_absorpt_T_max   0.777
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1230 before and 0.0713 after correction.
The Ratio of minimum to maximum transmission is 0.9186.
The λ/2 correction factor is Not present.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            27536
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.451
_diffrn_reflns_theta_max         28.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4405
_reflns_number_gt                3872
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'SAINT V8.38A (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+2.3720P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.055(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4405
_refine_ls_number_parameters     197
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_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
Ni1 Ni 0.26155(2) 0.50695(2) 0.53281(3) 0.00844(10) Uani 1 1 d . . . . .
S1 S 0.500000 0.50541(7) 0.51370(9) 0.0120(3) Uani 1 2 d S T P . .
S2 S 0.000000 0.51005(7) 0.34320(9) 0.0125(2) Uani 1 2 d S T P . .
O1 O 0.36200(12) 0.50726(13) 0.5563(2) 0.0133(5) Uani 1 1 d . . . . .
O2 O 0.32629(12) 0.50762(14) 0.3833(2) 0.0137(5) Uani 1 1 d . . . . .
O3 O 0.16838(11) 0.50563(13) 0.4875(2) 0.0119(4) Uani 1 1 d . . . . .
O4 O 0.13989(13) 0.51189(18) 0.3060(2) 0.0255(6) Uani 1 1 d . . . . .
O5 O 0.24813(12) 0.50902(14) 0.69986(19) 0.0127(5) Uani 1 1 d G . . . .
H5A H 0.215663 0.495762 0.740457 0.019 Uiso 1 1 d G U . . .
H5B H 0.280065 0.507474 0.744357 0.019 Uiso 1 1 d G U . . .
N1 N 0.25476(10) 0.66264(15) 0.5303(3) 0.0107(4) Uani 1 1 d . . . . .
N2 N 0.25575(10) 0.35107(15) 0.5312(3) 0.0105(4) Uani 1 1 d . . . . .
C1 C 0.37260(16) 0.50691(18) 0.4515(3) 0.0111(6) Uani 1 1 d . . . . .
C2 C 0.44067(14) 0.50674(19) 0.4146(3) 0.0105(6) Uani 1 1 d . . . . .
C3 C 0.46555(15) 0.50788(19) 0.3084(3) 0.0136(7) Uani 1 1 d . . . . .
H3 H 0.440448 0.508579 0.244110 0.016 Uiso 1 1 calc R U . . .
C4 C 0.12892(16) 0.5089(2) 0.4082(3) 0.0119(6) Uani 1 1 d . . . . .
C5 C 0.05940(14) 0.5084(2) 0.4429(3) 0.0101(6) Uani 1 1 d . . . . .
C6 C 0.03443(13) 0.50673(18) 0.5491(3) 0.0115(7) Uani 1 1 d . . . . .
H6 H 0.059511 0.505724 0.613436 0.014 Uiso 1 1 calc R U . . .
C7 C 0.31304(14) 0.7088(2) 0.5797(2) 0.0132(6) Uani 1 1 d . . . . .
H7A H 0.349603 0.700003 0.530198 0.016 Uiso 1 1 calc R U . . .
H7B H 0.323168 0.678258 0.650384 0.016 Uiso 1 1 calc R U . . .
C8 C 0.19873(15) 0.3178(2) 0.5984(2) 0.0146(6) Uani 1 1 d . . . . .
H8A H 0.160634 0.353779 0.576460 0.018 Uiso 1 1 calc R U . . .
H8B H 0.206594 0.329853 0.676960 0.018 Uiso 1 1 calc R U . . .
C9 C 0.24688(15) 0.7016(2) 0.4160(2) 0.0124(5) Uani 1 1 d . . . . .
H9A H 0.205118 0.682548 0.386643 0.015 Uiso 1 1 calc R U . . .
H9B H 0.279981 0.674887 0.367756 0.015 Uiso 1 1 calc R U . . .
C10 C 0.24801(15) 0.3123(2) 0.4163(2) 0.0128(5) Uani 1 1 d . . . . .
H10A H 0.281165 0.339231 0.368382 0.015 Uiso 1 1 calc R U . . .
H10B H 0.206288 0.331478 0.386937 0.015 Uiso 1 1 calc R U . . .
C11 C 0.19728(14) 0.69615(19) 0.5994(2) 0.0120(6) Uani 1 1 d . . . . .
H11A H 0.205428 0.683766 0.677822 0.014 Uiso 1 1 calc R U . . .
H11B H 0.158984 0.660525 0.577708 0.014 Uiso 1 1 calc R U . . .
C12 C 0.31388(14) 0.3042(2) 0.5813(3) 0.0139(6) Uani 1 1 d . . . . .
H12A H 0.323720 0.334530 0.652183 0.017 Uiso 1 1 calc R U . . .
H12B H 0.350644 0.313301 0.532281 0.017 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
Ni1 O3 2.004(2) . ?
Ni1 O5 2.022(2) . ?
Ni1 O1 2.099(2) . ?
Ni1 N1 2.165(2) . ?
Ni1 N2 2.166(2) . ?
Ni1 O2 2.239(3) . ?
Ni1 C1 2.498(3) . ?
S1 C2 1.709(3) 4_655 ?
S1 C2 1.709(3) . ?
S2 C5 1.716(3) 4 ?
S2 C5 1.716(3) . ?
O1 C1 1.276(5) . ?
O2 C1 1.260(4) . ?
O3 C4 1.255(4) . ?
O4 C4 1.246(4) . ?
O5 H5A 0.8502 . ?
O5 H5B 0.8498 . ?
N1 C9 1.482(4) . ?
N1 C7 1.489(3) . ?
N1 C11 1.523(4) . ?
N2 C10 1.487(4) . ?
N2 C12 1.494(3) . ?
N2 C8 1.502(4) . ?
C1 C2 1.477(4) . ?
C2 C3 1.373(5) . ?
C3 C3 1.427(6) 4_655 ?
C3 H3 0.9300 . ?
C4 C5 1.499(4) . ?
C5 C6 1.374(4) . ?
C6 C6 1.426(6) 4 ?
C6 H6 0.9300 . ?
C7 C8 1.548(4) 8 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.540(5) 8 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.532(4) 8 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
O3 Ni1 O5 97.83(11) . . ?
O3 Ni1 O1 171.98(11) . . ?
O5 Ni1 O1 90.19(10) . . ?
O3 Ni1 N1 86.72(8) . . ?
O5 Ni1 N1 89.47(11) . . ?
O1 Ni1 N1 93.68(7) . . ?
O3 Ni1 N2 86.28(8) . . ?
O5 Ni1 N2 90.87(11) . . ?
O1 Ni1 N2 93.34(7) . . ?
N1 Ni1 N2 172.97(9) . . ?
O3 Ni1 O2 111.08(11) . . ?
O5 Ni1 O2 151.09(10) . . ?
O1 Ni1 O2 60.91(9) . . ?
N1 Ni1 O2 91.36(10) . . ?
N2 Ni1 O2 91.74(9) . . ?
O3 Ni1 C1 141.30(12) . . ?
O5 Ni1 C1 120.88(11) . . ?
O1 Ni1 C1 30.69(11) . . ?
N1 Ni1 C1 93.13(9) . . ?
N2 Ni1 C1 92.72(9) . . ?
O2 Ni1 C1 30.23(11) . . ?
C2 S1 C2 91.9(2) 4_655 . ?
C5 S2 C5 91.6(2) 4 . ?
C1 O1 Ni1 92.2(2) . . ?
C1 O2 Ni1 86.3(2) . . ?
C4 O3 Ni1 146.3(3) . . ?
Ni1 O5 H5A 132.3 . . ?
Ni1 O5 H5B 121.0 . . ?
H5A O5 H5B 104.5 . . ?
C9 N1 C7 107.5(2) . . ?
C9 N1 C11 107.8(2) . . ?
C7 N1 C11 106.6(2) . . ?
C9 N1 Ni1 112.56(19) . . ?
C7 N1 Ni1 111.78(16) . . ?
C11 N1 Ni1 110.35(17) . . ?
C10 N2 C12 107.6(2) . . ?
C10 N2 C8 107.5(2) . . ?
C12 N2 C8 106.5(3) . . ?
C10 N2 Ni1 112.01(19) . . ?
C12 N2 Ni1 112.74(17) . . ?
C8 N2 Ni1 110.23(16) . . ?
O2 C1 O1 120.5(3) . . ?
O2 C1 C2 122.1(3) . . ?
O1 C1 C2 117.3(3) . . ?
O2 C1 Ni1 63.43(18) . . ?
O1 C1 Ni1 57.11(17) . . ?
C2 C1 Ni1 174.4(3) . . ?
C3 C2 C1 129.5(3) . . ?
C3 C2 S1 112.0(2) . . ?
C1 C2 S1 118.5(3) . . ?
C2 C3 C3 112.04(18) . 4_655 ?
C2 C3 H3 124.0 . . ?
C3 C3 H3 124.0 4_655 . ?
O4 C4 O3 128.9(3) . . ?
O4 C4 C5 116.7(3) . . ?
O3 C4 C5 114.5(3) . . ?
C6 C5 C4 128.3(3) . . ?
C6 C5 S2 112.1(2) . . ?
C4 C5 S2 119.7(2) . . ?
C5 C6 C6 112.11(17) . 4 ?
C5 C6 H6 123.9 . . ?
C6 C6 H6 123.9 4 . ?
N1 C7 C8 110.5(2) . 8 ?
N1 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 8 . ?
N1 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 8 . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C7 110.3(2) . 8_545 ?
N2 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 8_545 . ?
N2 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 8_545 . ?
H8A C8 H8B 108.1 . . ?
N1 C9 C10 110.7(2) . 8 ?
N1 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 8 . ?
N1 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 8 . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C9 110.8(2) . 8_545 ?
N2 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 8_545 . ?
N2 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 8_545 . ?
H10A C10 H10B 108.1 . . ?
N1 C11 C12 109.8(2) . 8 ?
N1 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 8 . ?
N1 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 8 . ?
H11A C11 H11B 108.2 . . ?
N2 C12 C11 111.2(2) . 8_545 ?
N2 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 8_545 . ?
N2 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 8_545 . ?
H12A C12 H12B 108.0 . . ?

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
Ni1 O2 C1 O1 -0.7(2) . . . . ?
Ni1 O2 C1 C2 180.0(2) . . . . ?
Ni1 O1 C1 O2 0.8(3) . . . . ?
Ni1 O1 C1 C2 -179.9(2) . . . . ?
O2 C1 C2 C3 0.5(4) . . . . ?
O1 C1 C2 C3 -178.9(3) . . . . ?
O2 C1 C2 S1 -179.8(2) . . . . ?
O1 C1 C2 S1 0.9(3) . . . . ?
C2 S1 C2 C3 0.2(3) 4_655 . . . ?
C2 S1 C2 C1 -179.59(13) 4_655 . . . ?
C1 C2 C3 C3 179.6(2) . . . 4_655 ?
S1 C2 C3 C3 -0.1(2) . . . 4_655 ?
Ni1 O3 C4 O4 3.2(6) . . . . ?
Ni1 O3 C4 C5 -177.2(2) . . . . ?
O4 C4 C5 C6 -179.0(3) . . . . ?
O3 C4 C5 C6 1.4(4) . . . . ?
O4 C4 C5 S2 1.0(4) . . . . ?
O3 C4 C5 S2 -178.64(19) . . . . ?
C5 S2 C5 C6 -0.1(3) 4 . . . ?
C5 S2 C5 C4 179.95(14) 4 . . . ?
C4 C5 C6 C6 -180.0(2) . . . 4 ?
S2 C5 C6 C6 0.0(2) . . . 4 ?
C9 N1 C7 C8 67.3(3) . . . 8 ?
C11 N1 C7 C8 -48.1(3) . . . 8 ?
Ni1 N1 C7 C8 -168.71(19) . . . 8 ?
C10 N2 C8 C7 47.2(3) . . . 8_545 ?
C12 N2 C8 C7 -67.9(3) . . . 8_545 ?
Ni1 N2 C8 C7 169.52(19) . . . 8_545 ?
C7 N1 C9 C10 -48.4(3) . . . 8 ?
C11 N1 C9 C10 66.1(3) . . . 8 ?
Ni1 N1 C9 C10 -171.9(2) . . . 8 ?
C12 N2 C10 C9 48.0(3) . . . 8_545 ?
C8 N2 C10 C9 -66.3(3) . . . 8_545 ?
Ni1 N2 C10 C9 172.4(2) . . . 8_545 ?
C9 N1 C11 C12 -47.2(3) . . . 8 ?
C7 N1 C11 C12 67.9(3) . . . 8 ?
Ni1 N1 C11 C12 -170.52(19) . . . 8 ?
C10 N2 C12 C11 -67.0(3) . . . 8_545 ?
C8 N2 C12 C11 48.0(3) . . . 8_545 ?
Ni1 N2 C12 C11 169.02(19) . . . 8_545 ?

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.069



