# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_MB
_database_code_depnum_ccdc_archive 'CCDC 2085189'
loop_
_audit_author_name
_audit_author_address
'Manoj Kumar Bharty'
;Banaras Hindu University
India
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2023-06-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_MB                  
;
PROBLEM: D-H Bond Without Acceptor  O2       --H2       .     Please Check 
RESPONSE: The methanol molecule pertaining to O2 is disordered over two positions with lower occupancies inside the intermolecular cavity. Hence, there is no such established hydrogen bonding with this methanol O-H bond. This level B alerts are related to the hydrogen atom attached with the lattice bromide.It is very difficult to locate hydrogen atoms accurately using X-ray data because these atoms have low scattering power.
;
# end Validation Reply Form
_audit_creation_date             2023-06-20
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_name_systematic        Zn-Mannu
_chemical_formula_moiety         'Br, C18 H25 N10 O2 S2 Zn, C H4 O'
_chemical_formula_sum            'C19 H29 Br N10 O3 S2 Zn'
_chemical_formula_weight         654.939
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Zn 0.31207 1.46666 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.1195(4)
_cell_length_b                   8.5613(4)
_cell_length_c                   9.9222(4)
_cell_angle_alpha                97.183(2)
_cell_angle_beta                 109.571(2)
_cell_angle_gamma                99.479(2)
_cell_volume                     628.84(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6871
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.46
_exptl_absorpt_coefficient_mu    2.776
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             334.573
_exptl_crystal_recrystallization_method 
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.9908
_diffrn_reflns_Laue_measured_fraction_max 0.9918
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11554
_diffrn_reflns_point_group_measured_fraction_full 0.9908
_diffrn_reflns_point_group_measured_fraction_max 0.9918
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.22
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.9908
_diffrn_measured_fraction_theta_max 0.9918
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2290
_reflns_number_total             2554
_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.
;
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.7259
_refine_diff_density_min         -0.8818
_refine_diff_density_rms         0.1041
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             9.1715
_refine_ls_goodness_of_fit_ref   1.0658
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     285
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.0479
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+1.2987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0880
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
O2 \\sim C10: within 1.7A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 1.7A
Uanis(O2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(H9A) \\sim Ueq, Uanis(H9B) \\sim Ueq, Uanis(H5B) \\sim Ueq, Uanis(H8A)
\\sim Ueq, Uanis(H4A) \\sim Ueq, Uanis(H4B) \\sim Ueq, Uanis(H5A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(H5) \\sim Ueq, Uanis(H6) \\sim Ueq, Uanis(H7) \\sim Ueq, Uanis(H4) \\sim
Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
3. Rigid body (RIGU) restrains
 H5A, H9B, H5B, H8B, H4A, H4B, H8A, H4, H9A, H5, H6, H7
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
4. Others
 Fixed Sof: O2(0.5) H2(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5)
5.a Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
5.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
Br01 Br 0.5 1.0 0.0 0.02722(14) Uani 1.000000 2 S T P .
Zn1 Zn 0.5 1.0 0.5 0.01998(14) Uani 1.000000 2 S T P .
S1 S 0.74423(9) 0.66359(8) 0.55927(8) 0.01836(17) Uani 1.000000 1 . . . .
O1 O 0.5187(2) 0.5657(2) 0.2840(2) 0.0153(4) Uani 1.000000 1 . . . .
N2 N 0.4895(3) 0.7973(3) 0.3826(2) 0.0127(4) Uani 1.000000 1 . . . .
N1 N 0.3650(3) 0.7556(3) 0.2415(2) 0.0143(5) Uani 1.000000 1 . . . .
N5 N 0.4945(3) 0.8876(3) 0.6587(3) 0.0156(5) Uani 1.000000 1 . . . .
H5A H 0.573(6) 0.816(5) 0.673(4) 0.024(9) Uani 1.000000 1 . U . .
H5B H 0.523(5) 0.956(5) 0.741(5) 0.035(10) Uani 1.000000 1 . U . .
N4 N 0.2382(3) 0.9493(3) 0.4351(3) 0.0151(5) Uani 1.000000 1 . . . .
H4A H 0.195(6) 1.040(6) 0.418(5) 0.033(10) Uani 1.000000 1 . U . .
H4B H 0.184(5) 0.864(5) 0.354(5) 0.028(10) Uani 1.000000 1 . U . .
C3 C 0.2875(4) 0.5206(3) 0.0429(3) 0.0170(6) Uani 1.000000 1 . . . .
C4 C 0.3118(4) 0.3665(4) 0.0072(4) 0.0255(7) Uani 1.000000 1 . . . .
H4 H 0.409(6) 0.323(5) 0.082(5) 0.049(13) Uani 1.000000 1 . U . .
C5 C 0.2061(5) 0.2761(5) -0.1306(4) 0.0352(8) Uani 1.000000 1 . . . .
H5 H 0.209(8) 0.159(7) -0.175(7) 0.09(2) Uani 1.000000 1 . U . .
N3 N 0.0839(4) 0.3277(4) -0.2298(3) 0.0330(7) Uani 1.000000 1 . . . .
C6 C 0.0671(5) 0.4782(4) -0.1956(4) 0.0333(8) Uani 1.000000 1 . . . .
H6 H -0.023(7) 0.523(6) -0.271(6) 0.083(19) Uani 1.000000 1 . U . .
C7 C 0.1648(4) 0.5790(4) -0.0612(4) 0.0268(7) Uani 1.000000 1 . . . .
H7 H 0.154(7) 0.696(6) -0.034(5) 0.059(14) Uani 1.000000 1 . U . .
C2 C 0.3877(3) 0.6191(3) 0.1876(3) 0.0145(5) Uani 1.000000 1 . . . .
C1 C 0.5813(3) 0.6821(3) 0.4089(3) 0.0132(5) Uani 1.000000 1 . . . .
C8 C 0.1845(4) 0.8957(4) 0.5541(3) 0.0204(6) Uani 1.000000 1 . . . .
H8A H 0.198(7) 1.012(6) 0.627(5) 0.053(13) Uani 1.000000 1 . U . .
H8B H 0.054(7) 0.827(6) 0.516(5) 0.054(13) Uani 1.000000 1 . U . .
C9 C 0.3102(4) 0.7928(3) 0.6238(3) 0.0203(6) Uani 1.000000 1 . . . .
H9A H 0.292(5) 0.680(5) 0.549(4) 0.035(10) Uani 1.000000 1 . U . .
H9B H 0.288(5) 0.767(5) 0.721(5) 0.046(12) Uani 1.000000 1 . U . .
O2 O 0.0434(15) 1.0053(14) 0.0395(10) 0.092(2) Uani 0.500000 1 . U P -1
H2 H 0.132(18) 0.97(3) 0.092(4) 0.138(4) Uiso 0.500000 1 GR . P -1
C10 C -0.0472(18) 1.0641(13) 0.1248(14) 0.079(3) Uani 0.500000 1 . U P -1
H10A H -0.173(3) 1.052(11) 0.064(3) 0.119(4) Uiso 0.500000 1 GR . P -1
H10B H -0.039(11) 1.003(8) 0.203(7) 0.119(4) Uiso 0.500000 1 GR . P -1
H10C H 0.007(9) 1.178(3) 0.167(9) 0.119(4) Uiso 0.500000 1 GR . P -1


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
Zn1 N2 1.938(2) . ?
Zn1 N2 1.938(2) 2_676 ?
Zn1 N5 1.954(2) 2_676 ?
Zn1 N5 1.954(2) . ?
Zn1 N4 1.958(2) 2_676 ?
Zn1 N4 1.958(2) . ?
S1 C1 1.675(3) . ?
O1 C2 1.358(3) . ?
O1 C1 1.375(3) . ?
N2 N1 1.384(3) . ?
N2 C1 1.331(3) . ?
N1 C2 1.291(4) . ?
N5 H5A 0.94(4) . ?
N5 H5B 0.88(5) . ?
N5 C9 1.483(4) . ?
N4 H4A 0.92(5) . ?
N4 H4B 0.94(5) . ?
N4 C8 1.486(4) . ?
C3 C4 1.386(4) . ?
C3 C7 1.382(4) . ?
C3 C2 1.457(4) . ?
C4 H4 1.04(4) . ?
C4 C5 1.391(4) . ?
C5 H5 1.05(5) . ?
C5 N3 1.322(5) . ?
N3 C6 1.332(5) . ?
C6 H6 1.02(5) . ?
C6 C7 1.389(5) . ?
C7 H7 1.03(5) . ?
C8 H8A 1.12(5) . ?
C8 H8B 1.04(5) . ?
C8 C9 1.507(5) . ?
C9 H9A 1.10(4) . ?
C9 H9B 1.08(5) . ?
O2 H2 0.8400 . ?
O2 C10 1.393(17) . ?
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
N2 Zn1 N2 180.0 2_676 . ?
N5 Zn1 N2 90.65(10) 2_676 . ?
N5 Zn1 N2 89.35(10) . . ?
N5 Zn1 N2 90.65(10) . 2_676 ?
N5 Zn1 N2 89.35(10) 2_676 2_676 ?
N5 Zn1 N5 180.0 2_676 . ?
N4 Zn1 N2 89.68(10) 2_676 2_676 ?
N4 Zn1 N2 89.68(10) . . ?
N4 Zn1 N2 90.32(10) 2_676 . ?
N4 Zn1 N2 90.32(10) . 2_676 ?
N4 Zn1 N5 94.17(10) . 2_676 ?
N4 Zn1 N5 94.17(10) 2_676 . ?
N4 Zn1 N5 85.83(10) 2_676 2_676 ?
N4 Zn1 N5 85.83(10) . . ?
N4 Zn1 N4 180.0 2_676 . ?
C1 O1 C2 104.9(2) . . ?
N1 N2 Zn1 117.83(17) . . ?
C1 N2 Zn1 132.82(18) . . ?
C1 N2 N1 109.3(2) . . ?
C2 N1 N2 105.3(2) . . ?
H5A N5 Zn1 112(2) . . ?
H5B N5 Zn1 111(3) . . ?
H5B N5 H5A 109(4) . . ?
C9 N5 Zn1 109.38(18) . . ?
C9 N5 H5A 108(2) . . ?
C9 N5 H5B 107(3) . . ?
H4A N4 Zn1 110(3) . . ?
H4B N4 Zn1 112(2) . . ?
H4B N4 H4A 112(4) . . ?
C8 N4 Zn1 109.00(18) . . ?
C8 N4 H4A 106(3) . . ?
C8 N4 H4B 106(2) . . ?
C7 C3 C4 118.7(3) . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 C7 120.4(3) . . ?
H4 C4 C3 120(2) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 H4 122(2) . . ?
H5 C5 C4 127(4) . . ?
N3 C5 C4 124.2(3) . . ?
N3 C5 H5 108(4) . . ?
C6 N3 C5 117.0(3) . . ?
H6 C6 N3 119(3) . . ?
C7 C6 N3 123.7(3) . . ?
C7 C6 H6 118(3) . . ?
C6 C7 C3 118.4(3) . . ?
H7 C7 C3 117(3) . . ?
H7 C7 C6 124(3) . . ?
N1 C2 O1 112.8(2) . . ?
C3 C2 O1 119.5(2) . . ?
C3 C2 N1 127.6(3) . . ?
O1 C1 S1 121.24(19) . . ?
N2 C1 S1 131.1(2) . . ?
N2 C1 O1 107.6(2) . . ?
H8A C8 N4 103(2) . . ?
H8B C8 N4 112(3) . . ?
H8B C8 H8A 111(3) . . ?
C9 C8 N4 107.0(2) . . ?
C9 C8 H8A 114(3) . . ?
C9 C8 H8B 108(2) . . ?
C8 C9 N5 106.5(2) . . ?
H9A C9 N5 108(2) . . ?
H9A C9 C8 112(2) . . ?
H9B C9 N5 111(2) . . ?
H9B C9 C8 109(2) . . ?
H9B C9 H9A 110(3) . . ?
C10 O2 H2 109.5 . . ?
H10A C10 O2 109.5 . . ?
H10B C10 O2 109.5 . . ?
H10B C10 H10A 109.5 . . ?
H10C C10 O2 109.5 . . ?
H10C C10 H10A 109.5 . . ?
H10C C10 H10B 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
Zn1 N2 N1 C2 179.0(2) . . . . ?
Zn1 N2 N1 C2 179.0(2) 2_676 . . . ?
Zn1 N2 C1 S1 1.5(3) . . . . ?
Zn1 N2 C1 S1 1.5(3) 2_676 . . . ?
Zn1 N2 C1 O1 -178.9(2) . . . . ?
Zn1 N2 C1 O1 -178.9(2) 2_676 . . . ?
Zn1 N5 C9 C8 -39.60(19) . . . . ?
Zn1 N5 C9 C8 -39.60(19) 2_676 . . . ?
Zn1 N4 C8 C9 -39.08(18) . . . . ?
Zn1 N4 C8 C9 -39.08(18) 2_676 . . . ?
S1 C1 O1 C2 179.0(2) . . . . ?
S1 C1 N2 N1 -178.6(2) . . . . ?
O1 C2 N1 N2 0.5(2) . . . . ?
O1 C2 C3 C4 6.4(3) . . . . ?
O1 C2 C3 C7 -174.2(3) . . . . ?
O1 C1 N2 N1 0.9(2) . . . . ?
N2 N1 C2 C3 178.44(19) . . . . ?
N1 C2 C3 C4 -171.4(3) . . . . ?
N1 C2 C3 C7 8.0(4) . . . . ?
N5 C9 C8 N4 51.1(2) . . . . ?
C3 C4 C5 N3 0.0(4) . . . . ?
C3 C7 C6 N3 0.5(4) . . . . ?
C4 C5 N3 C6 2.4(5) . . . . ?
C5 N3 C6 C7 -2.7(4) . . . . ?


_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a glass fibre oil'
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         PBE
   BASIS SET:      x2c-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   SOLVATION:      Methanol
   RELATIVISTIC:   DKH2
   DATE:           2023-06-19_16-14-31
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
H5A 0.0200
H5B 0.0200
H4A 0.0200
H4B 0.0200
H4 0.1000
H5 0.1000
H6 0.1000
H7 0.1000
H8A 0.0200
H9A 0.0200
H9B 0.0200
O2 0.0100

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
O2 C10 0.0040


####################################################################### 
# 
# 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 2231750'
loop_
_audit_author_name
_audit_author_address
'Dr. Manoj Kumar Bharty'
;Banaras Hindu University, Institute of Science
India
;
_audit_update_record             
;
2022-12-20 deposited with the CCDC.	2023-06-26 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            'C18 H24 Cu N10 O2 S2'
_chemical_formula_weight         540.13

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'
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'
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'

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

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9088(14)
_cell_length_b                   10.2087(9)
_cell_length_c                   11.9734(14)
_cell_angle_alpha                90
_cell_angle_beta                 114.208(5)
_cell_angle_gamma                90
_cell_volume                     1216.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    566(2)
_cell_measurement_reflns_used    2208
_cell_measurement_theta_min      3.287
_cell_measurement_theta_max      25.347

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             558
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      566(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10634
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_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         3.287
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.348
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2208
_reflns_number_gt                2007
_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 XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0707P)²+0.7166P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2208
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1098
_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
Cu1 Cu 0.5000 0.5000 0.0000 0.03638(18) Uani 1 2 d S . P . .
S1 S 0.13832(8) 0.58916(9) -0.22021(7) 0.0618(3) Uani 1 1 d . . . . .
O1 O 0.22702(19) 0.48864(17) -0.37838(16) 0.0426(5) Uani 1 1 d . . . . .
N1 N 0.3816(2) 0.49026(19) -0.19058(18) 0.0372(5) Uani 1 1 d . . . . .
N3 N 0.3416(2) 0.4196(2) 0.03443(19) 0.0424(5) Uani 1 1 d . . . . .
H3A H 0.3560 0.4318 0.1124 0.051 Uiso 1 1 calc R U . . .
H3B H 0.2643 0.4580 -0.0127 0.051 Uiso 1 1 calc R U . . .
N2 N 0.4376(2) 0.4369(2) -0.26700(18) 0.0409(5) Uani 1 1 d . . . . .
N4 N 0.5527(2) 0.3028(2) -0.0014(2) 0.0430(5) Uani 1 1 d . . . . .
H4A H 0.5317 0.2762 -0.0778 0.052 Uiso 1 1 calc R U . . .
H4B H 0.6407 0.2923 0.0414 0.052 Uiso 1 1 calc R U . . .
C2 C 0.3433(2) 0.4380(2) -0.3744(2) 0.0385(5) Uani 1 1 d . . . . .
C1 C 0.2557(3) 0.5202(3) -0.2575(2) 0.0408(6) Uani 1 1 d . . . . .
C3 C 0.3461(3) 0.3928(3) -0.4895(2) 0.0436(6) Uani 1 1 d . . . . .
C8 C 0.3360(3) 0.2792(3) 0.0068(3) 0.0503(7) Uani 1 1 d . . . . .
H8A H 0.2911 0.2655 -0.0809 0.060 Uiso 1 1 calc R U . . .
H8B H 0.2855 0.2336 0.0454 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4773(3) 0.2260(3) 0.0542(3) 0.0511(7) Uani 1 1 d . . . . .
H9A H 0.5201 0.2334 0.1427 0.061 Uiso 1 1 calc R U . . .
H9B H 0.4757 0.1343 0.0325 0.061 Uiso 1 1 calc R U . . .
C4 C 0.2397(3) 0.4181(3) -0.5995(3) 0.0569(8) Uani 1 1 d . . . . .
H4 H 0.1649 0.4642 -0.6023 0.068 Uiso 1 1 calc R U . . .
C7 C 0.4538(3) 0.3242(4) -0.4898(3) 0.0633(8) Uani 1 1 d . . . . .
H7 H 0.5274 0.3057 -0.4170 0.076 Uiso 1 1 calc R U . . .
C5 C 0.2466(4) 0.3733(5) -0.7054(3) 0.0772(11) Uani 1 1 d . . . . .
H5 H 0.1744 0.3910 -0.7794 0.093 Uiso 1 1 calc R U . . .
C6 C 0.4504(4) 0.2829(5) -0.6016(4) 0.0832(12) Uani 1 1 d . . . . .
H6 H 0.5232 0.2356 -0.6017 0.100 Uiso 1 1 calc R U . . .
N5 N 0.3486(4) 0.3073(4) -0.7085(3) 0.0881(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 2.096(2) 3_665 ?
Cu1 N4 2.096(2) . ?
Cu1 N3 2.101(2) . ?
Cu1 N3 2.101(2) 3_665 ?
Cu1 N1 2.114(2) . ?
Cu1 N1 2.114(2) 3_665 ?
S1 C1 1.675(3) . ?
O1 C2 1.352(3) . ?
O1 C1 1.387(3) . ?
N1 C1 1.312(4) . ?
N1 N2 1.402(3) . ?
N3 C8 1.467(4) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N2 C2 1.276(3) . ?
N4 C9 1.477(4) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
C2 C3 1.465(3) . ?
C3 C7 1.370(4) . ?
C3 C4 1.377(4) . ?
C8 C9 1.508(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9300 . ?
C7 C6 1.389(5) . ?
C7 H7 0.9300 . ?
C5 N5 1.314(5) . ?
C5 H5 0.9300 . ?
C6 N5 1.330(5) . ?
C6 H6 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
N4 Cu1 N4 180.0 3_665 . ?
N4 Cu1 N3 97.09(9) 3_665 . ?
N4 Cu1 N3 82.91(9) . . ?
N4 Cu1 N3 82.91(9) 3_665 3_665 ?
N4 Cu1 N3 97.09(9) . 3_665 ?
N3 Cu1 N3 180.0 . 3_665 ?
N4 Cu1 N1 90.32(8) 3_665 . ?
N4 Cu1 N1 89.68(8) . . ?
N3 Cu1 N1 90.34(8) . . ?
N3 Cu1 N1 89.66(8) 3_665 . ?
N4 Cu1 N1 89.68(8) 3_665 3_665 ?
N4 Cu1 N1 90.32(8) . 3_665 ?
N3 Cu1 N1 89.66(8) . 3_665 ?
N3 Cu1 N1 90.34(8) 3_665 3_665 ?
N1 Cu1 N1 180.0 . 3_665 ?
C2 O1 C1 104.17(19) . . ?
C1 N1 N2 108.6(2) . . ?
C1 N1 Cu1 132.20(18) . . ?
N2 N1 Cu1 119.09(16) . . ?
C8 N3 Cu1 107.38(17) . . ?
C8 N3 H3A 110.2 . . ?
Cu1 N3 H3A 110.2 . . ?
C8 N3 H3B 110.2 . . ?
Cu1 N3 H3B 110.2 . . ?
H3A N3 H3B 108.5 . . ?
C2 N2 N1 105.5(2) . . ?
C9 N4 Cu1 107.54(17) . . ?
C9 N4 H4A 110.2 . . ?
Cu1 N4 H4A 110.2 . . ?
C9 N4 H4B 110.2 . . ?
Cu1 N4 H4B 110.2 . . ?
H4A N4 H4B 108.5 . . ?
N2 C2 O1 113.4(2) . . ?
N2 C2 C3 128.7(2) . . ?
O1 C2 C3 117.9(2) . . ?
N1 C1 O1 108.4(2) . . ?
N1 C1 S1 131.2(2) . . ?
O1 C1 S1 120.4(2) . . ?
C7 C3 C4 118.7(3) . . ?
C7 C3 C2 120.8(3) . . ?
C4 C3 C2 120.4(3) . . ?
N3 C8 C9 109.0(2) . . ?
N3 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N3 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N4 C9 C8 108.1(2) . . ?
N4 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
N4 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C3 C7 C6 118.3(3) . . ?
C3 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
N5 C5 C4 124.2(3) . . ?
N5 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N5 C6 C7 123.6(4) . . ?
N5 C6 H6 118.2 . . ?
C7 C6 H6 118.2 . . ?
C5 N5 C6 116.8(3) . . ?

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
C1 N1 N2 C2 0.1(3) . . . . ?
Cu1 N1 N2 C2 177.15(16) . . . . ?
N1 N2 C2 O1 0.4(3) . . . . ?
N1 N2 C2 C3 -179.7(2) . . . . ?
C1 O1 C2 N2 -0.8(3) . . . . ?
C1 O1 C2 C3 179.3(2) . . . . ?
N2 N1 C1 O1 -0.6(3) . . . . ?
Cu1 N1 C1 O1 -177.08(15) . . . . ?
N2 N1 C1 S1 -178.6(2) . . . . ?
Cu1 N1 C1 S1 5.0(4) . . . . ?
C2 O1 C1 N1 0.8(3) . . . . ?
C2 O1 C1 S1 179.02(19) . . . . ?
N2 C2 C3 C7 9.3(4) . . . . ?
O1 C2 C3 C7 -170.8(3) . . . . ?
N2 C2 C3 C4 -171.1(3) . . . . ?
O1 C2 C3 C4 8.8(4) . . . . ?
Cu1 N3 C8 C9 41.2(3) . . . . ?
Cu1 N4 C9 C8 41.6(3) . . . . ?
N3 C8 C9 N4 -56.4(3) . . . . ?
C7 C3 C4 C5 -0.2(5) . . . . ?
C2 C3 C4 C5 -179.8(3) . . . . ?
C4 C3 C7 C6 -0.1(5) . . . . ?
C2 C3 C7 C6 179.5(3) . . . . ?
C3 C4 C5 N5 0.2(6) . . . . ?
C3 C7 C6 N5 0.6(7) . . . . ?
C4 C5 N5 C6 0.2(7) . . . . ?
C7 C6 N5 C5 -0.6(7) . . . . ?

_refine_diff_density_max         0.613
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_inhs-h
_database_code_depnum_ccdc_archive 'CCDC 2231639'
loop_
_audit_author_name
_audit_author_address
'Manoj Kumar Bharty'
;Banaras Hindu University
India
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2023-06-26 downloaded from the CCDC.
;
_audit_creation_date             2023-06-13
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 K N3 O2 S'
_chemical_formula_sum            'C7 H6 K N3 O2 S'
_chemical_formula_weight         235.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
K K 0.2009 0.2494 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   4.2204(14)
_cell_length_b                   6.0284(19)
_cell_length_c                   9.659(3)
_cell_angle_alpha                84.14(3)
_cell_angle_beta                 80.32(3)
_cell_angle_gamma                78.44(3)
_cell_volume                     236.73(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    678
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.9229
_cell_measurement_theta_min      3.4513
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             120
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0094
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1676
_diffrn_reflns_point_group_measured_fraction_full 0.671
_diffrn_reflns_point_group_measured_fraction_max 0.555
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.987
_diffrn_reflns_theta_min         3.458
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 16.0938
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.285
_reflns_Friedel_fraction_full    0.344
_reflns_Friedel_fraction_max     0.246
_reflns_number_gt                1339
_reflns_number_total             1389
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.09(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1389
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0759
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
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
K K 0.69628(14) -0.20085(12) 0.98610(9) 0.0409(2) Uani 1 1 d . . . . .
S1 S 0.30373(16) 0.35713(13) 1.01377(9) 0.0375(2) Uani 1 1 d . . . . .
O1 O 0.0153(5) 0.4382(4) 0.7825(3) 0.0307(5) Uani 1 1 d . . . . .
O1W O 1.0054(10) -0.0809(7) 1.1808(4) 0.0615(9) Uani 1 1 d . . . . .
H1WA H 1.130(15) -0.171(11) 1.228(7) 0.08(2) Uiso 1 1 d . . . . .
H1WB H 1.076(12) 0.033(10) 1.167(6) 0.053(15) Uiso 1 1 d . . . . .
N1 N 0.1870(8) 0.0734(5) 0.8344(3) 0.0366(7) Uani 1 1 d . . . . .
N2 N 0.0354(7) 0.0986(5) 0.7136(3) 0.0374(7) Uani 1 1 d . . . . .
N3 N -0.5688(8) 0.6369(6) 0.3547(4) 0.0442(8) Uani 1 1 d . . . . .
C1 C 0.1705(8) 0.2769(6) 0.8731(4) 0.0309(7) Uani 1 1 d . . . . .
C2 C -0.0620(7) 0.3137(6) 0.6880(4) 0.0294(7) Uani 1 1 d . . . . .
C3 C -0.2336(8) 0.4265(6) 0.5740(4) 0.0311(8) Uani 1 1 d . . . . .
C4 C -0.2733(10) 0.3040(7) 0.4664(4) 0.0400(9) Uani 1 1 d . . . . .
H4 H -0.187695 0.145735 0.465987 0.048 Uiso 1 1 calc R U . . .
C5 C -0.4396(10) 0.4148(8) 0.3591(5) 0.0460(10) Uani 1 1 d . . . . .
H5 H -0.462836 0.329137 0.285415 0.055 Uiso 1 1 calc R U . . .
C6 C -0.5293(10) 0.7499(7) 0.4586(5) 0.0456(10) Uani 1 1 d . . . . .
H6 H -0.620857 0.907378 0.456982 0.055 Uiso 1 1 calc R U . . .
C7 C -0.3658(10) 0.6580(7) 0.5693(4) 0.0409(9) Uani 1 1 d . . . . .
H7 H -0.343818 0.749598 0.640250 0.049 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
K K 4.2204(14) 1_455 ?
K K 4.2204(14) 1_655 ?
K S1 3.3303(16) 1_645 ?
K S1 3.4542(16) . ?
K S1 3.3752(15) 1_545 ?
K O1 3.037(3) 1_645 ?
K O1W 2.691(4) . ?
K O1W 3.186(5) 1_455 ?
K H1WA 3.04(6) 1_455 ?
K H1WB 3.06(5) 1_455 ?
K N1 2.939(3) . ?
K N1 3.005(4) 1_655 ?
S1 C1 1.702(4) . ?
O1 C1 1.380(4) . ?
O1 C2 1.357(4) . ?
O1W H1WA 0.83(7) . ?
O1W H1WB 0.79(6) . ?
N1 N2 1.404(4) . ?
N1 C1 1.304(5) . ?
N2 C2 1.291(5) . ?
N3 C5 1.340(6) . ?
N3 C6 1.319(6) . ?
C2 C3 1.455(5) . ?
C3 C4 1.386(5) . ?
C3 C7 1.394(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.379(6) . ?
C7 H7 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
K K K 180.0 1_455 1_655 ?
K K H1WA 130.2(12) 1_655 1_455 ?
K K H1WA 49.8(13) 1_455 1_455 ?
K K H1WB 131.8(10) 1_655 1_455 ?
K K H1WB 48.2(10) 1_455 1_455 ?
S1 K K 129.48(3) 1_545 1_655 ?
S1 K K 51.47(3) 1_645 1_655 ?
S1 K K 74.25(3) . 1_455 ?
S1 K K 128.53(3) 1_645 1_455 ?
S1 K K 105.75(3) . 1_655 ?
S1 K K 50.52(3) 1_545 1_455 ?
S1 K S1 155.48(4) 1_645 . ?
S1 K S1 78.01(4) 1_645 1_545 ?
S1 K S1 123.94(4) 1_545 . ?
S1 K H1WA 70.1(13) . 1_455 ?
S1 K H1WA 115.4(13) 1_645 1_455 ?
S1 K H1WA 67.4(12) 1_545 1_455 ?
S1 K H1WB 138.8(11) 1_645 1_455 ?
S1 K H1WB 84.8(11) 1_545 1_455 ?
S1 K H1WB 46.0(11) . 1_455 ?
O1 K K 79.00(5) 1_645 1_655 ?
O1 K K 101.00(5) 1_645 1_455 ?
O1 K S1 144.80(6) 1_645 . ?
O1 K S1 49.45(5) 1_645 1_645 ?
O1 K S1 66.24(6) 1_645 1_545 ?
O1 K O1W 135.52(9) 1_645 1_455 ?
O1 K H1WA 133.4(12) 1_645 1_455 ?
O1 K H1WB 148.3(10) 1_645 1_455 ?
O1W K K 39.61(7) 1_455 1_455 ?
O1W K K 140.39(7) 1_455 1_655 ?
O1W K K 131.00(10) . 1_455 ?
O1W K K 49.00(10) . 1_655 ?
O1W K S1 80.01(10) . . ?
O1W K S1 70.57(8) 1_455 1_545 ?
O1W K S1 77.29(10) . 1_645 ?
O1W K S1 59.59(8) 1_455 . ?
O1W K S1 127.10(9) . 1_545 ?
O1W K S1 129.74(8) 1_455 1_645 ?
O1W K O1 123.05(11) . 1_645 ?
O1W K O1W 91.40(12) . 1_455 ?
O1W K H1WA 15.1(13) 1_455 1_455 ?
O1W K H1WA 82.5(12) . 1_455 ?
O1W K H1WB 14.4(11) 1_455 1_455 ?
O1W K H1WB 84.2(10) . 1_455 ?
O1W K N1 72.60(11) . 1_655 ?
O1W K N1 129.53(12) . . ?
H1WA K H1WB 24.6(16) 1_455 1_455 ?
N1 K K 45.39(7) . 1_455 ?
N1 K K 134.61(7) . 1_655 ?
N1 K K 44.14(7) 1_655 1_655 ?
N1 K K 135.86(7) 1_655 1_455 ?
N1 K S1 89.33(7) . 1_545 ?
N1 K S1 49.55(7) . . ?
N1 K S1 75.32(7) 1_655 . ?
N1 K S1 151.82(7) 1_655 1_545 ?
N1 K S1 89.08(7) 1_655 1_645 ?
N1 K S1 151.40(7) . 1_645 ?
N1 K O1 86.28(8) 1_655 1_645 ?
N1 K O1 101.99(8) . 1_645 ?
N1 K O1W 134.27(10) 1_655 1_455 ?
N1 K O1W 66.88(10) . 1_455 ?
N1 K H1WA 140.3(12) 1_655 1_455 ?
N1 K H1WA 81.9(13) . 1_455 ?
N1 K H1WB 120.0(11) 1_655 1_455 ?
N1 K H1WB 63.5(11) . 1_455 ?
N1 K N1 90.47(10) . 1_655 ?
K S1 K 78.01(4) 1_465 1_565 ?
K S1 K 123.94(4) 1_565 . ?
K S1 K 155.48(4) 1_465 . ?
C1 S1 K 82.72(12) . 1_465 ?
C1 S1 K 121.81(13) . 1_565 ?
C1 S1 K 76.19(12) . . ?
C1 O1 K 99.78(18) . 1_465 ?
C2 O1 K 140.59(19) . 1_465 ?
C2 O1 C1 103.7(3) . . ?
K O1W K 91.40(12) . 1_655 ?
K O1W H1WA 125(5) . . ?
K O1W H1WA 72(5) 1_655 . ?
K O1W H1WB 74(4) 1_655 . ?
K O1W H1WB 119(4) . . ?
H1WA O1W H1WB 106(6) . . ?
K N1 K 90.47(10) . 1_455 ?
N2 N1 K 145.9(2) . . ?
N2 N1 K 90.2(2) . 1_455 ?
C1 N1 K 118.2(2) . 1_455 ?
C1 N1 K 102.7(2) . . ?
C1 N1 N2 106.9(3) . . ?
N1 N2 K 64.75(19) . 1_455 ?
C2 N2 K 123.3(2) . 1_455 ?
C2 N2 N1 106.6(3) . . ?
C6 N3 C5 116.5(4) . . ?
O1 C1 S1 120.2(2) . . ?
N1 C1 S1 129.2(3) . . ?
N1 C1 O1 110.6(3) . . ?
O1 C2 C3 120.0(3) . . ?
N2 C2 O1 112.2(3) . . ?
N2 C2 C3 127.8(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 C7 117.8(4) . . ?
C7 C3 C2 122.0(3) . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.4 . . ?
N3 C5 C4 123.1(4) . . ?
N3 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
N3 C6 H6 117.4 . . ?
N3 C6 C7 125.3(4) . . ?
C7 C6 H6 117.4 . . ?
C3 C7 H7 121.0 . . ?
C6 C7 C3 118.0(3) . . ?
C6 C7 H7 121.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1WA N3 0.83(7) 2.03(7) 2.855(5) 174(6) 1_746 yes
O1W H1WB S1 0.79(6) 2.57(6) 3.308(4) 155(5) 1_655 yes
C5 H5 S1 0.95 2.93 3.745(4) 144.4 1_454 yes

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
K S1 C1 O1 -165.4(3) . . . . ?
K S1 C1 O1 -43.8(3) 1_565 . . . ?
K S1 C1 O1 27.2(2) 1_465 . . . ?
K S1 C1 N1 15.8(3) . . . . ?
K S1 C1 N1 -151.6(3) 1_465 . . . ?
K S1 C1 N1 137.4(3) 1_565 . . . ?
K O1 C1 S1 -30.3(3) 1_465 . . . ?
K O1 C1 N1 148.7(2) 1_465 . . . ?
K O1 C2 N2 -125.6(3) 1_465 . . . ?
K O1 C2 C3 54.8(4) 1_465 . . . ?
K N1 N2 K 91.2(4) . . . 1_455 ?
K N1 N2 C2 -149.3(3) . . . . ?
K N1 N2 C2 119.5(2) 1_455 . . . ?
K N1 C1 S1 78.9(3) 1_455 . . . ?
K N1 C1 S1 -18.6(4) . . . . ?
K N1 C1 O1 162.5(2) . . . . ?
K N1 C1 O1 -100.0(3) 1_455 . . . ?
K N2 C2 O1 70.9(3) 1_455 . . . ?
K N2 C2 C3 -109.5(3) 1_455 . . . ?
O1 C2 C3 C4 171.1(3) . . . . ?
O1 C2 C3 C7 -9.6(5) . . . . ?
N1 N2 C2 O1 0.6(4) . . . . ?
N1 N2 C2 C3 -179.9(3) . . . . ?
N2 N1 C1 S1 178.6(3) . . . . ?
N2 N1 C1 O1 -0.3(4) . . . . ?
N2 C2 C3 C4 -8.5(5) . . . . ?
N2 C2 C3 C7 170.8(4) . . . . ?
N3 C6 C7 C3 -0.8(7) . . . . ?
C1 O1 C2 N2 -0.7(3) . . . . ?
C1 O1 C2 C3 179.6(3) . . . . ?
C1 N1 N2 K -119.6(3) . . . 1_455 ?
C1 N1 N2 C2 -0.1(4) . . . . ?
C2 O1 C1 S1 -178.4(2) . . . . ?
C2 O1 C1 N1 0.6(3) . . . . ?
C2 C3 C4 C5 179.6(3) . . . . ?
C2 C3 C7 C6 -178.9(3) . . . . ?
C3 C4 C5 N3 -0.7(6) . . . . ?
C4 C3 C7 C6 0.4(6) . . . . ?
C5 N3 C6 C7 0.4(6) . . . . ?
C6 N3 C5 C4 0.4(6) . . . . ?
C7 C3 C4 C5 0.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
