# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 1949548'
loop_
_audit_author_name
_audit_author_address
'Aditya Upadhyay Ray J. Butcher'
;IISER Bhopal
India
;

_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_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            'C15 H18 N O2 S Se Zn'
_chemical_formula_weight         420.69

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   8.4306(14)
_cell_length_b                   9.2108(16)
_cell_length_c                   10.5745(18)
_cell_angle_alpha                76.941(6)
_cell_angle_beta                 88.026(5)
_cell_angle_gamma                75.718(6)
_cell_volume                     775.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    164(2)
_cell_measurement_reflns_used    4284
_cell_measurement_theta_min      2.494
_cell_measurement_theta_max      30.033

_exptl_crystal_description       rectangle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    '\f and \w scans'
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_F_000             422
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    4.070
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      164(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4284
_diffrn_reflns_av_unetI/netI     0.0858
_diffrn_reflns_av_R_equivalents  0.05
_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       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.494
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4284
_reflns_number_gt                2825
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.1000P)²] 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         4284
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.882
_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
Se1 Se 0.79033(5) -0.13029(5) 0.76288(4) 0.02310(15) Uani 1 1 d . . . . .
Zn1 Zn 0.53787(6) -0.08742(5) 0.88501(4) 0.01598(15) Uani 1 1 d . . . . .
S1 S 0.30416(14) -0.32422(13) 1.01016(11) 0.0230(3) Uani 1 1 d . . . . .
O1 O 0.3856(3) 0.1019(3) 0.9289(2) 0.0176(6) Uani 1 1 d . . . . .
O2 O 0.4262(4) -0.2654(3) 0.9151(3) 0.0223(7) Uani 1 1 d . . . . .
N1 N 0.4274(4) 0.0030(4) 0.6888(3) 0.0172(7) Uani 1 1 d . . . . .
C1 C 0.6950(5) 0.0477(5) 0.6321(4) 0.0200(9) Uani 1 1 d . . . . .
C2 C 0.7939(6) 0.1342(6) 0.5571(4) 0.0278(11) Uani 1 1 d . . . . .
H10 H 0.909568 0.100670 0.568094 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7250(7) 0.2692(6) 0.4661(5) 0.0345(12) Uani 1 1 d . . . . .
H1 H 0.792941 0.326870 0.414830 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5569(6) 0.3177(6) 0.4517(4) 0.0318(11) Uani 1 1 d . . . . .
H2 H 0.509393 0.411086 0.391845 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4567(6) 0.2333(5) 0.5223(4) 0.0252(10) Uani 1 1 d . . . . .
H3 H 0.341288 0.267670 0.510074 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5251(5) 0.0970(5) 0.6120(4) 0.0186(9) Uani 1 1 d . . . . .
C7 C 0.2656(5) 0.2152(5) 0.8613(4) 0.0151(8) Uani 1 1 d . . . . .
C8 C 0.2051(5) 0.3507(5) 0.9057(4) 0.0194(9) Uani 1 1 d . . . . .
H9 H 0.250162 0.360307 0.983658 0.023 Uiso 1 1 calc R U . . .
C9 C 0.0830(5) 0.4698(5) 0.8406(4) 0.0216(9) Uani 1 1 d . . . . .
H8 H 0.044520 0.559321 0.874029 0.026 Uiso 1 1 calc R U . . .
C10 C 0.0155(5) 0.4592(5) 0.7252(4) 0.0218(9) Uani 1 1 d . . . . .
H4 H -0.069458 0.540434 0.679568 0.026 Uiso 1 1 calc R U . . .
C11 C 0.0754(5) 0.3275(5) 0.6788(4) 0.0203(9) Uani 1 1 d . . . . .
H7 H 0.031362 0.320446 0.599579 0.024 Uiso 1 1 calc R U . . .
C12 C 0.1977(5) 0.2050(5) 0.7440(4) 0.0165(8) Uani 1 1 d . . . . .
C13 C 0.2486(5) 0.0651(5) 0.6877(4) 0.0197(9) Uani 1 1 d . . . . .
H6 H 0.197834 -0.015685 0.737611 0.024 Uiso 1 1 calc R U . . .
H5 H 0.206376 0.091691 0.597019 0.024 Uiso 1 1 calc R U . . .
C14 C 0.1414(5) -0.1634(5) 1.0203(5) 0.0292(11) Uani 1 1 d . . . . .
H13 H 0.186045 -0.081606 1.039033 0.044 Uiso 1 1 calc R U . . .
H15 H 0.068382 -0.193893 1.089906 0.044 Uiso 1 1 calc R U . . .
H14 H 0.079851 -0.125734 0.937555 0.044 Uiso 1 1 calc R U . . .
C15 C 0.3903(6) -0.3590(6) 1.1687(4) 0.0351(12) Uani 1 1 d . . . . .
H17 H 0.489258 -0.443391 1.178980 0.053 Uiso 1 1 calc R U . . .
H18 H 0.310573 -0.386809 1.233438 0.053 Uiso 1 1 calc R U . . .
H16 H 0.418454 -0.265927 1.180863 0.053 Uiso 1 1 calc R U . . .
H30 H 0.438(5) -0.078(5) 0.666(4) 0.019(13) 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
Se1 C1 1.910(4) . ?
Se1 Zn1 2.4455(7) . ?
Zn1 O1 2.031(3) . ?
Zn1 O2 2.044(3) . ?
Zn1 O1 2.058(3) 2_657 ?
Zn1 N1 2.199(3) . ?
S1 O2 1.524(3) . ?
S1 C14 1.774(5) . ?
S1 C15 1.779(4) . ?
O1 C7 1.347(4) . ?
N1 C6 1.441(5) . ?
N1 C13 1.474(5) . ?
N1 H30 0.82(5) . ?
C1 C2 1.399(6) . ?
C1 C6 1.400(6) . ?
C2 C3 1.397(7) . ?
C2 H10 0.9500 . ?
C3 C4 1.379(7) . ?
C3 H1 0.9500 . ?
C4 C5 1.376(6) . ?
C4 H2 0.9500 . ?
C5 C6 1.396(6) . ?
C5 H3 0.9500 . ?
C7 C8 1.405(6) . ?
C7 C12 1.415(5) . ?
C8 C9 1.373(6) . ?
C8 H9 0.9500 . ?
C9 C10 1.397(6) . ?
C9 H8 0.9500 . ?
C10 C11 1.384(6) . ?
C10 H4 0.9500 . ?
C11 C12 1.390(6) . ?
C11 H7 0.9500 . ?
C12 C13 1.502(6) . ?
C13 H6 0.9900 . ?
C13 H5 0.9900 . ?
C14 H13 0.9800 . ?
C14 H15 0.9800 . ?
C14 H14 0.9800 . ?
C15 H17 0.9800 . ?
C15 H18 0.9800 . ?
C15 H16 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
C1 Se1 Zn1 89.33(13) . . ?
O1 Zn1 O2 110.65(12) . . ?
O1 Zn1 O1 78.17(11) . 2_657 ?
O2 Zn1 O1 100.80(11) . 2_657 ?
O1 Zn1 N1 85.28(12) . . ?
O2 Zn1 N1 91.02(13) . . ?
O1 Zn1 N1 162.23(13) 2_657 . ?
O1 Zn1 Se1 133.82(8) . . ?
O2 Zn1 Se1 113.84(8) . . ?
O1 Zn1 Se1 104.61(8) 2_657 . ?
N1 Zn1 Se1 82.22(9) . . ?
O2 S1 C14 107.1(2) . . ?
O2 S1 C15 106.8(2) . . ?
C14 S1 C15 98.0(2) . . ?
C7 O1 Zn1 132.9(2) . . ?
C7 O1 Zn1 125.2(2) . 2_657 ?
Zn1 O1 Zn1 101.83(11) . 2_657 ?
S1 O2 Zn1 136.61(18) . . ?
C6 N1 C13 118.3(3) . . ?
C6 N1 Zn1 108.8(2) . . ?
C13 N1 Zn1 113.7(3) . . ?
C6 N1 H30 111(3) . . ?
C13 N1 H30 104(3) . . ?
Zn1 N1 H30 99(3) . . ?
C2 C1 C6 118.6(4) . . ?
C2 C1 Se1 120.4(3) . . ?
C6 C1 Se1 120.9(3) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H10 119.6 . . ?
C1 C2 H10 119.6 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H1 120.5 . . ?
C2 C3 H1 120.5 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 H2 119.4 . . ?
C3 C4 H2 119.4 . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H3 120.1 . . ?
C6 C5 H3 120.1 . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 N1 122.7(4) . . ?
C1 C6 N1 117.1(4) . . ?
O1 C7 C8 119.9(4) . . ?
O1 C7 C12 122.5(4) . . ?
C8 C7 C12 117.5(4) . . ?
C9 C8 C7 122.4(4) . . ?
C9 C8 H9 118.8 . . ?
C7 C8 H9 118.8 . . ?
C8 C9 C10 120.0(4) . . ?
C8 C9 H8 120.0 . . ?
C10 C9 H8 120.0 . . ?
C11 C10 C9 118.4(4) . . ?
C11 C10 H4 120.8 . . ?
C9 C10 H4 120.8 . . ?
C10 C11 C12 122.4(4) . . ?
C10 C11 H7 118.8 . . ?
C12 C11 H7 118.8 . . ?
C11 C12 C7 119.2(4) . . ?
C11 C12 C13 117.9(4) . . ?
C7 C12 C13 122.8(4) . . ?
N1 C13 C12 113.4(3) . . ?
N1 C13 H6 108.9 . . ?
C12 C13 H6 108.9 . . ?
N1 C13 H5 108.9 . . ?
C12 C13 H5 108.9 . . ?
H6 C13 H5 107.7 . . ?
S1 C14 H13 109.5 . . ?
S1 C14 H15 109.5 . . ?
H13 C14 H15 109.5 . . ?
S1 C14 H14 109.5 . . ?
H13 C14 H14 109.5 . . ?
H15 C14 H14 109.5 . . ?
S1 C15 H17 109.5 . . ?
S1 C15 H18 109.5 . . ?
H17 C15 H18 109.5 . . ?
S1 C15 H16 109.5 . . ?
H17 C15 H16 109.5 . . ?
H18 C15 H16 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
C14 S1 O2 Zn1 47.1(3) . . . . ?
C15 S1 O2 Zn1 -57.1(3) . . . . ?
C6 C1 C2 C3 1.6(6) . . . . ?
Se1 C1 C2 C3 -176.5(3) . . . . ?
C1 C2 C3 C4 0.6(7) . . . . ?
C2 C3 C4 C5 -1.9(7) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C4 C5 C6 C1 1.3(6) . . . . ?
C4 C5 C6 N1 -179.8(4) . . . . ?
C2 C1 C6 C5 -2.6(6) . . . . ?
Se1 C1 C6 C5 175.5(3) . . . . ?
C2 C1 C6 N1 178.5(4) . . . . ?
Se1 C1 C6 N1 -3.4(5) . . . . ?
C13 N1 C6 C5 -9.8(6) . . . . ?
Zn1 N1 C6 C5 -141.5(3) . . . . ?
C13 N1 C6 C1 169.1(4) . . . . ?
Zn1 N1 C6 C1 37.4(4) . . . . ?
Zn1 O1 C7 C8 -165.5(3) . . . . ?
Zn1 O1 C7 C8 13.0(5) 2_657 . . . ?
Zn1 O1 C7 C12 13.6(6) . . . . ?
Zn1 O1 C7 C12 -168.0(3) 2_657 . . . ?
O1 C7 C8 C9 180.0(4) . . . . ?
C12 C7 C8 C9 0.9(6) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
C8 C9 C10 C11 -0.5(6) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C10 C11 C12 C7 -0.8(6) . . . . ?
C10 C11 C12 C13 177.5(4) . . . . ?
O1 C7 C12 C11 -179.3(4) . . . . ?
C8 C7 C12 C11 -0.2(6) . . . . ?
O1 C7 C12 C13 2.5(6) . . . . ?
C8 C7 C12 C13 -178.5(4) . . . . ?
C6 N1 C13 C12 -64.0(5) . . . . ?
Zn1 N1 C13 C12 65.4(4) . . . . ?
C11 C12 C13 N1 136.5(4) . . . . ?
C7 C12 C13 N1 -45.2(5) . . . . ?

_refine_diff_density_max         0.818
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.158




_publcif_funding_html            
;
;
