# 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_jh_n2s2_a
_database_code_depnum_ccdc_archive 'CCDC 1569176'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
_audit_creation_date             2017-08-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H18 Cu N3 O3 S2, N O3'
_chemical_formula_sum            'C8 H18 Cu N4 O6 S2'
_chemical_formula_weight         393.92
_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'
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'
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1896(2)
_cell_length_b                   12.3669(3)
_cell_length_c                   12.9821(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.1510(10)
_cell_angle_gamma                90.00
_cell_volume                     1452.28(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8418
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.318
_cell_measurement_theta_min      2.979
_exptl_absorpt_coefficient_mu    1.824
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1171 before and 0.0330 after correction.
The Ratio of minimum to maximum transmission is 0.7971.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11688
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.29
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3364
_reflns_number_total             3568
_reflns_threshold_expression     >2σ(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0405P)²+0.5902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0718
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1A(0.02) H1B(0.02) H2A(0.019) H2B(0.019) H3A(0.017) H3B(0.017)
 H4A(0.016) H4B(0.016) H5A(0.016) H5B(0.016) H6A(0.016) H6B(0.016) H7A(0.016)
 H7B(0.016) H8A(0.018) H8B(0.018)
 Fixed X: H1A(0.1319) H1B(-0.0419) H2A(-0.0907) H2B(0.0466) H3A(0.262)
 H3B(0.3394) H4A(0.3542) H4B(0.4907) H5A(0.6124) H5B(0.4738) H6A(0.5233)
 H6B(0.5282) H7A(0.2871) H7B(0.274) H8A(0.0555) H8B(0.0365)
 Fixed Y: H1A(0.2185) H1B(0.2107) H2A(0.1331) H2B(0.0678) H3A(0.0111)
 H3B(0.0835) H4A(0.1191) H4B(0.0918) H5A(0.2839) H5B(0.2725) H6A(0.4572)
 H6B(0.4502) H7A(0.4988) H7B(0.3698) H8A(0.5241) H8B(0.4319)
 Fixed Z: H1A(0.6826) H1B(0.6848) H2A(0.5209) H2B(0.584) H3A(0.4973)
 H3B(0.4202) H4A(0.6393) H4B(0.5819) H5A(0.6588) H5B(0.7181) H6A(0.7105)
 H6B(0.5878) H7A(0.762) H7B(0.7518) H8A(0.664) H8B(0.7471)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.227610(19) 0.329584(14) 0.517223(13) 0.00749(7) Uani 1 1 d . . .
S1 S 0.12063(4) 0.16652(3) 0.44852(3) 0.01129(9) Uani 1 1 d . . .
S2 S 0.00447(4) 0.35813(3) 0.57846(3) 0.01404(9) Uani 1 1 d . . .
O1 O 0.22214(12) 0.42171(9) 0.38021(9) 0.0140(2) Uani 1 1 d . . .
O2 O 0.31171(13) 0.27889(10) 0.31427(9) 0.0164(2) Uani 1 1 d . . .
O3 O 0.24909(13) 0.42031(10) 0.21682(9) 0.0184(2) Uani 1 1 d . . .
N1 N 0.41917(14) 0.24727(10) 0.56000(10) 0.0100(2) Uani 1 1 d . . .
N2 N 0.31791(14) 0.44260(11) 0.61974(10) 0.0111(2) Uani 1 1 d . . .
N3 N 0.26163(14) 0.37260(11) 0.30232(10) 0.0115(2) Uani 1 1 d . . .
C1 C 0.03208(18) 0.22338(14) 0.63917(13) 0.0164(3) Uani 1 1 d . . .
H1A H 0.1319 0.2185 0.6826 0.020 Uiso 1 1 calc R . .
H1B H -0.0419 0.2107 0.6848 0.020 Uiso 1 1 calc R . .
C2 C 0.01525(18) 0.13875(13) 0.55244(13) 0.0154(3) Uani 1 1 d . . .
H2A H -0.0907 0.1331 0.5209 0.019 Uiso 1 1 calc R . .
H2B H 0.0466 0.0678 0.5840 0.019 Uiso 1 1 calc R . .
C3 C 0.28903(17) 0.08606(13) 0.48158(13) 0.0145(3) Uani 1 1 d . . .
H3A H 0.2620 0.0111 0.4973 0.017 Uiso 1 1 calc R . .
H3B H 0.3394 0.0835 0.4202 0.017 Uiso 1 1 calc R . .
C4 C 0.39516(17) 0.13059(13) 0.57454(12) 0.0129(3) Uani 1 1 d . . .
H4A H 0.3542 0.1191 0.6393 0.016 Uiso 1 1 calc R . .
H4B H 0.4907 0.0918 0.5819 0.016 Uiso 1 1 calc R . .
C5 C 0.50590(17) 0.30000(13) 0.65410(12) 0.0136(3) Uani 1 1 d . . .
H5A H 0.6124 0.2839 0.6588 0.016 Uiso 1 1 calc R . .
H5B H 0.4738 0.2725 0.7181 0.016 Uiso 1 1 calc R . .
C6 C 0.47983(16) 0.42096(13) 0.64418(13) 0.0137(3) Uani 1 1 d . . .
H6A H 0.5233 0.4572 0.7105 0.016 Uiso 1 1 calc R . .
H6B H 0.5282 0.4502 0.5878 0.016 Uiso 1 1 calc R . .
C7 C 0.24835(17) 0.43887(13) 0.71436(12) 0.0131(3) Uani 1 1 d . . .
H7A H 0.2871 0.4988 0.7620 0.016 Uiso 1 1 calc R . .
H7B H 0.2740 0.3698 0.7518 0.016 Uiso 1 1 calc R . .
C8 C 0.08145(17) 0.44859(14) 0.68500(12) 0.0154(3) Uani 1 1 d . . .
H8A H 0.0555 0.5241 0.6640 0.018 Uiso 1 1 calc R . .
H8B H 0.0365 0.4319 0.7471 0.018 Uiso 1 1 calc R . .
O4 O 0.37704(14) 0.65764(10) 0.56133(12) 0.0219(3) Uani 1 1 d . . .
O5 O 0.20319(13) 0.70879(11) 0.64383(10) 0.0195(3) Uani 1 1 d . . .
O6 O 0.33522(15) 0.82855(9) 0.57780(10) 0.0186(3) Uani 1 1 d . . .
N4 N 0.30502(14) 0.73183(11) 0.59508(10) 0.0120(2) Uani 1 1 d . . .
H1 H 0.463(2) 0.2544(18) 0.5092(18) 0.019(5) Uiso 1 1 d . . .
H2 H 0.308(2) 0.506(2) 0.5969(17) 0.020(5) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 S1 2.3494(4) . ?
Cu1 S2 2.3529(4) . ?
Cu1 O1 2.1054(11) . ?
Cu1 N1 2.0245(13) . ?
Cu1 N2 2.0060(13) . ?
S1 C2 1.8266(16) . ?
S1 C3 1.8263(16) . ?
S2 C1 1.8417(17) . ?
S2 C8 1.8220(16) . ?
O1 N3 1.2854(17) . ?
O2 N3 1.2464(18) . ?
O3 N3 1.2444(17) . ?
N1 C4 1.4769(19) . ?
N1 C5 1.4865(19) . ?
N2 C6 1.4900(19) . ?
N2 C7 1.4820(19) . ?
C1 C2 1.525(2) . ?
C3 C4 1.515(2) . ?
C5 C6 1.517(2) . ?
C7 C8 1.519(2) . ?
O4 N4 1.2547(18) . ?
O5 N4 1.2514(17) . ?
O6 N4 1.2569(17) . ?

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
S1 Cu1 S2 85.743(15) . . ?
O1 Cu1 S1 101.40(3) . . ?
O1 Cu1 S2 108.17(3) . . ?
N1 Cu1 S1 87.59(4) . . ?
N1 Cu1 S2 138.60(4) . . ?
N1 Cu1 O1 113.20(5) . . ?
N2 Cu1 S1 161.16(4) . . ?
N2 Cu1 S2 87.39(4) . . ?
N2 Cu1 O1 97.41(5) . . ?
N2 Cu1 N1 86.00(5) . . ?
C2 S1 Cu1 97.00(5) . . ?
C3 S1 Cu1 95.62(5) . . ?
C3 S1 C2 105.17(8) . . ?
C1 S2 Cu1 86.92(5) . . ?
C8 S2 Cu1 95.95(5) . . ?
C8 S2 C1 103.00(8) . . ?
N3 O1 Cu1 116.16(9) . . ?
C4 N1 Cu1 112.59(9) . . ?
C4 N1 C5 113.21(12) . . ?
C5 N1 Cu1 108.62(9) . . ?
C6 N2 Cu1 107.28(9) . . ?
C7 N2 Cu1 109.86(9) . . ?
C7 N2 C6 112.23(12) . . ?
O2 N3 O1 119.38(12) . . ?
O3 N3 O1 118.88(13) . . ?
O3 N3 O2 121.74(13) . . ?
C2 C1 S2 108.46(11) . . ?
C1 C2 S1 114.73(11) . . ?
C4 C3 S1 112.89(11) . . ?
N1 C4 C3 110.06(12) . . ?
N1 C5 C6 108.01(12) . . ?
N2 C6 C5 109.39(12) . . ?
N2 C7 C8 110.71(12) . . ?
C7 C8 S2 112.44(10) . . ?
O4 N4 O6 119.13(13) . . ?
O5 N4 O4 119.84(14) . . ?
O5 N4 O6 121.02(14) . . ?

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
Cu1 S1 C2 C1 0.05(12) . . . . ?
Cu1 S1 C3 C4 26.58(11) . . . . ?
Cu1 S2 C1 C2 -68.03(10) . . . . ?
Cu1 S2 C8 C7 -19.14(12) . . . . ?
Cu1 O1 N3 O2 -5.99(17) . . . . ?
Cu1 O1 N3 O3 174.21(10) . . . . ?
Cu1 N1 C4 C3 48.57(14) . . . . ?
Cu1 N1 C5 C6 -35.42(14) . . . . ?
Cu1 N2 C6 C5 -40.12(14) . . . . ?
Cu1 N2 C7 C8 -54.33(14) . . . . ?
S1 Cu1 S2 C1 52.85(5) . . . . ?
S1 Cu1 S2 C8 155.62(6) . . . . ?
S1 Cu1 O1 N3 -43.89(10) . . . . ?
S1 Cu1 N1 C4 -25.02(10) . . . . ?
S1 Cu1 N1 C5 -151.21(9) . . . . ?
S1 Cu1 N2 C6 86.47(15) . . . . ?
S1 Cu1 N2 C7 -35.79(19) . . . . ?
S1 C3 C4 N1 -49.99(15) . . . . ?
S2 Cu1 S1 C2 -34.12(6) . . . . ?
S2 Cu1 S1 C3 -140.20(5) . . . . ?
S2 Cu1 O1 N3 -133.12(9) . . . . ?
S2 Cu1 N1 C4 55.77(12) . . . . ?
S2 Cu1 N1 C5 -70.42(11) . . . . ?
S2 Cu1 N2 C6 155.15(9) . . . . ?
S2 Cu1 N2 C7 32.90(9) . . . . ?
S2 C1 C2 S1 48.79(14) . . . . ?
O1 Cu1 S1 C2 -141.82(6) . . . . ?
O1 Cu1 S1 C3 112.10(6) . . . . ?
O1 Cu1 S2 C1 153.47(6) . . . . ?
O1 Cu1 S2 C8 -103.77(7) . . . . ?
O1 Cu1 N1 C4 -126.39(10) . . . . ?
O1 Cu1 N1 C5 107.41(10) . . . . ?
O1 Cu1 N2 C6 -96.86(10) . . . . ?
O1 Cu1 N2 C7 140.89(10) . . . . ?
N1 Cu1 S1 C2 104.99(7) . . . . ?
N1 Cu1 S1 C3 -1.08(6) . . . . ?
N1 Cu1 S2 C1 -28.63(8) . . . . ?
N1 Cu1 S2 C8 74.14(8) . . . . ?
N1 Cu1 O1 N3 48.39(11) . . . . ?
N1 Cu1 N2 C6 16.04(10) . . . . ?
N1 Cu1 N2 C7 -106.21(10) . . . . ?
N1 C5 C6 N2 50.59(16) . . . . ?
N2 Cu1 S1 C2 34.82(14) . . . . ?
N2 Cu1 S1 C3 -71.26(13) . . . . ?
N2 Cu1 S2 C1 -109.59(6) . . . . ?
N2 Cu1 S2 C8 -6.82(7) . . . . ?
N2 Cu1 O1 N3 137.20(10) . . . . ?
N2 Cu1 N1 C4 137.25(10) . . . . ?
N2 Cu1 N1 C5 11.06(10) . . . . ?
N2 C7 C8 S2 48.00(16) . . . . ?
C1 S2 C8 C7 69.07(13) . . . . ?
C2 S1 C3 C4 -72.25(13) . . . . ?
C3 S1 C2 C1 97.83(13) . . . . ?
C4 N1 C5 C6 -161.25(12) . . . . ?
C5 N1 C4 C3 172.25(12) . . . . ?
C6 N2 C7 C8 -173.59(12) . . . . ?
C7 N2 C6 C5 80.64(15) . . . . ?
C8 S2 C1 C2 -163.43(11) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
