# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_00
_database_code_depnum_ccdc_archive 'CCDC 2005990'
loop_
_audit_author_name
_audit_author_address
'Kou-Lin Zhang'
;Yangzhou University
China
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2021-01-08 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            'C14 H16 Cu N3 O8 S'
_chemical_formula_weight         449.92

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   15.1069(18)
_cell_length_b                   10.2825(11)
_cell_length_c                   20.870(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3241.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.5873
_cell_measurement_theta_max      27.5039

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    1.530
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_T_max  0.682
_exptl_absorpt_process_details   sadabs
_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  'Bruker APEXII area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26598
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3725
_reflns_number_gt                3101
_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)+(0.0459P)²+3.8535P] 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_number_reflns         3725
_refine_ls_number_parameters     244
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.40991(15) 0.5477(2) 0.17309(11) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.39867(15) 0.4152(2) 0.18523(11) 0.0208(5) Uani 1 1 d . . . . .
C3 C 0.47281(16) 0.3341(2) 0.18723(12) 0.0260(5) Uani 1 1 d . . . . .
H3 H 0.465291 0.245481 0.194147 0.031 Uiso 1 1 calc R U . . .
C4 C 0.55697(16) 0.3834(2) 0.17911(13) 0.0276(5) Uani 1 1 d . . . . .
H4 H 0.605721 0.328189 0.179635 0.033 Uiso 1 1 calc R U . . .
C5 C 0.56829(15) 0.5162(2) 0.17016(11) 0.0218(5) Uani 1 1 d . . . . .
C6 C 0.49558(15) 0.5966(2) 0.16685(11) 0.0213(5) Uani 1 1 d . . . . .
H6 H 0.503747 0.685237 0.160316 0.026 Uiso 1 1 calc R U . . .
C7 C 0.33481(15) 0.6425(2) 0.16298(11) 0.0215(5) Uani 1 1 d . . . . .
C8 C 0.08473(17) 0.5764(2) 0.07215(13) 0.0271(5) Uani 1 1 d . . . . .
H8 H 0.136031 0.595607 0.049404 0.033 Uiso 1 1 calc R U . . .
C9 C 0.00494(17) 0.6242(2) 0.04968(13) 0.0288(5) Uani 1 1 d . . . . .
C10 C -0.07111(17) 0.5974(3) 0.08447(14) 0.0341(6) Uani 1 1 d . . . . .
H10 H -0.125668 0.628855 0.070868 0.041 Uiso 1 1 calc R U . . .
C11 C -0.06496(17) 0.5232(3) 0.13968(14) 0.0338(6) Uani 1 1 d . . . . .
H11 H -0.115120 0.504231 0.163758 0.041 Uiso 1 1 calc R U . . .
C12 C 0.01704(17) 0.4783(3) 0.15817(12) 0.0277(5) Uani 1 1 d . . . . .
H12 H 0.020943 0.427992 0.195107 0.033 Uiso 1 1 calc R U . . .
C13 C 0.0029(2) 0.7012(3) -0.01150(14) 0.0380(7) Uani 1 1 d . . . . .
H13A H 0.041296 0.659980 -0.042746 0.046 Uiso 1 1 calc R U . . .
H13B H -0.056780 0.700881 -0.028561 0.046 Uiso 1 1 calc R U . . .
C14 C -0.02302(18) 0.9348(3) -0.00544(12) 0.0302(6) Uani 1 1 d . . . . .
Cu1 Cu 0.20838(2) 0.42575(3) 0.15121(2) 0.02202(10) Uani 1 1 d . . . . .
N1 N 0.09143(12) 0.50339(18) 0.12552(10) 0.0227(4) Uani 1 1 d . . . . .
N2 N 0.03143(16) 0.8351(2) -0.00201(12) 0.0400(6) Uani 1 1 d . . . . .
H2A H 0.086319 0.849730 0.006213 0.048 Uiso 1 1 calc R U . . .
N3 N 0.31377(13) 0.3604(2) 0.19762(11) 0.0274(5) Uani 1 1 d . . . . .
H3A H 0.267577 0.409302 0.197763 0.033 Uiso 1 1 calc R U . . .
H3B H 0.308699 0.278449 0.204951 0.033 Uiso 1 1 calc R U . . .
O1 O 0.25857(11) 0.60349(16) 0.14819(8) 0.0270(4) Uani 1 1 d . . . . .
O2 O 0.35514(11) 0.76091(16) 0.16788(10) 0.0305(4) Uani 1 1 d . . . . .
O3 O 0.70836(16) 0.5456(3) 0.10137(13) 0.0634(7) Uani 1 1 d . . . . .
O4 O 0.66703(15) 0.7213(2) 0.16826(15) 0.0634(7) Uani 1 1 d . . . . .
O5 O 0.72639(16) 0.5255(3) 0.21413(14) 0.0812(10) Uani 1 1 d . . . . .
O6 O -0.10280(14) 0.9281(2) -0.01681(12) 0.0493(6) Uani 1 1 d . . . . .
O1W O 0.25755(16) 0.3862(2) 0.05084(10) 0.0511(6) Uani 1 1 d D . . . .
H1WB H 0.248651 0.326852 0.023805 0.061 Uiso 1 1 d DR U . . .
H1WA H 0.283325 0.450595 0.034428 0.061 Uiso 1 1 d DR U . . .
O2W O 0.23096(17) 0.8099(2) 0.46112(12) 0.0632(7) Uani 1 1 d D . . . .
H2WA H 0.225102 0.770112 0.425429 0.076 Uiso 1 1 d DR U . . .
H2WB H 0.256175 0.882179 0.454463 0.076 Uiso 1 1 d DR U . . .
S1 S 0.67649(4) 0.58261(7) 0.16342(3) 0.03016(16) 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
C1 C6 1.395(3) . ?
C1 C2 1.396(3) . ?
C1 C7 1.511(3) . ?
C2 C3 1.397(3) . ?
C2 N3 1.425(3) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 S1 1.777(2) . ?
C6 H6 0.9300 . ?
C7 O1 1.258(3) . ?
C7 O2 1.259(3) . ?
C8 N1 1.347(3) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(4) . ?
C9 C13 1.503(4) . ?
C10 C11 1.385(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 N1 1.339(3) . ?
C12 H12 0.9300 . ?
C13 N2 1.456(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O6 1.230(3) . ?
C14 N2 1.316(3) . ?
C14 C14 1.528(5) 5_575 ?
Cu1 O2 1.9787(16) 7_655 ?
Cu1 O1 1.9796(17) . ?
Cu1 N3 1.981(2) . ?
Cu1 N1 2.0114(19) . ?
Cu1 O1W 2.259(2) . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
O3 S1 1.433(2) . ?
O4 S1 1.437(2) . ?
O5 S1 1.426(2) . ?
O1W H1WB 0.8416 . ?
O1W H1WA 0.8414 . ?
O2W H2WA 0.8543 . ?
O2W H2WB 0.8469 . ?

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
C6 C1 C2 118.8(2) . . ?
C6 C1 C7 116.8(2) . . ?
C2 C1 C7 124.3(2) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 N3 121.9(2) . . ?
C3 C2 N3 118.7(2) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 S1 119.93(18) . . ?
C4 C5 S1 120.13(18) . . ?
C5 C6 C1 121.3(2) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O1 C7 O2 123.5(2) . . ?
O1 C7 C1 121.0(2) . . ?
O2 C7 C1 115.4(2) . . ?
N1 C8 C9 122.9(2) . . ?
N1 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
C8 C9 C10 118.3(2) . . ?
C8 C9 C13 119.5(2) . . ?
C10 C9 C13 122.2(2) . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
N1 C12 C11 123.2(2) . . ?
N1 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
N2 C13 C9 112.2(2) . . ?
N2 C13 H13A 109.2 . . ?
C9 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C9 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O6 C14 N2 125.4(3) . . ?
O6 C14 C14 121.6(3) . 5_575 ?
N2 C14 C14 113.0(3) . 5_575 ?
O2 Cu1 O1 169.18(8) 7_655 . ?
O2 Cu1 N3 90.76(8) 7_655 . ?
O1 Cu1 N3 91.20(8) . . ?
O2 Cu1 N1 87.76(7) 7_655 . ?
O1 Cu1 N1 87.80(7) . . ?
N3 Cu1 N1 166.12(9) . . ?
O2 Cu1 O1W 99.68(8) 7_655 . ?
O1 Cu1 O1W 90.63(8) . . ?
N3 Cu1 O1W 97.35(9) . . ?
N1 Cu1 O1W 96.50(9) . . ?
C12 N1 C8 117.7(2) . . ?
C12 N1 Cu1 121.66(17) . . ?
C8 N1 Cu1 120.50(16) . . ?
C14 N2 C13 123.0(2) . . ?
C14 N2 H2A 118.5 . . ?
C13 N2 H2A 118.5 . . ?
C2 N3 Cu1 120.05(15) . . ?
C2 N3 H3A 120.0 . . ?
Cu1 N3 H3A 31.9 . . ?
C2 N3 H3B 120.0 . . ?
Cu1 N3 H3B 110.4 . . ?
H3A N3 H3B 120.0 . . ?
C7 O1 Cu1 129.60(15) . . ?
C7 O2 Cu1 134.05(16) . 7_665 ?
Cu1 O1W H1WB 134.4 . . ?
Cu1 O1W H1WA 112.8 . . ?
H1WB O1W H1WA 111.8 . . ?
H2WA O2W H2WB 108.9 . . ?
O5 S1 O3 112.6(2) . . ?
O5 S1 O4 114.16(19) . . ?
O3 S1 O4 111.12(18) . . ?
O5 S1 C5 105.61(13) . . ?
O3 S1 C5 106.17(13) . . ?
O4 S1 C5 106.53(12) . . ?

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
C6 C1 C2 C3 -3.5(3) . . . . ?
C7 C1 C2 C3 173.4(2) . . . . ?
C6 C1 C2 N3 174.5(2) . . . . ?
C7 C1 C2 N3 -8.5(4) . . . . ?
C1 C2 C3 C4 1.7(4) . . . . ?
N3 C2 C3 C4 -176.4(2) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 -2.6(4) . . . . ?
C3 C4 C5 S1 177.00(19) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
S1 C5 C6 C1 -178.86(18) . . . . ?
C2 C1 C6 C5 2.3(4) . . . . ?
C7 C1 C6 C5 -174.9(2) . . . . ?
C6 C1 C7 O1 158.0(2) . . . . ?
C2 C1 C7 O1 -19.0(4) . . . . ?
C6 C1 C7 O2 -19.3(3) . . . . ?
C2 C1 C7 O2 163.7(2) . . . . ?
N1 C8 C9 C10 1.2(4) . . . . ?
N1 C8 C9 C13 -178.0(2) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C13 C9 C10 C11 178.5(3) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 N1 0.4(4) . . . . ?
C8 C9 C13 N2 -79.0(3) . . . . ?
C10 C9 C13 N2 101.8(3) . . . . ?
C11 C12 N1 C8 0.1(4) . . . . ?
C11 C12 N1 Cu1 -175.9(2) . . . . ?
C9 C8 N1 C12 -0.9(4) . . . . ?
C9 C8 N1 Cu1 175.10(19) . . . . ?
O6 C14 N2 C13 0.0(4) . . . . ?
C14 C14 N2 C13 -179.2(3) 5_575 . . . ?
C9 C13 N2 C14 -109.9(3) . . . . ?
C1 C2 N3 Cu1 37.1(3) . . . . ?
C3 C2 N3 Cu1 -144.87(19) . . . . ?
O2 C7 O1 Cu1 -169.25(18) . . . . ?
C1 C7 O1 Cu1 13.7(3) . . . . ?
O1 C7 O2 Cu1 -5.0(4) . . . 7_665 ?
C1 C7 O2 Cu1 172.26(16) . . . 7_665 ?
C6 C5 S1 O5 133.3(2) . . . . ?
C4 C5 S1 O5 -46.4(3) . . . . ?
C6 C5 S1 O3 -107.0(2) . . . . ?
C4 C5 S1 O3 73.4(2) . . . . ?
C6 C5 S1 O4 11.5(2) . . . . ?
C4 C5 S1 O4 -168.1(2) . . . . ?

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
C8 H8 O2W 0.93 2.53 3.408(4) 157.8 8_575 yes
O2W H2WB O6 0.85 2.54 3.023(3) 117.2 6_656 yes
O2W H2WB O3 0.85 2.11 2.901(4) 154.5 4_655 yes
N3 H3B O1 0.86 2.38 3.039(3) 133.6 7_655 yes
Cu1 H3A O5 1.33 2.28 3.004(3) 109.8 6_556 yes
O2W H2WA O4 0.85 2.20 3.009(4) 157.7 6_556 yes
O2W H2WA O3 0.85 2.39 3.033(4) 132.7 6_556 yes
N2 H2A O1W 0.86 2.56 3.414(3) 170.1 7_665 yes
N2 H2A O6 0.86 2.31 2.691(3) 107.2 5_575 yes
O1W H1WA O6 0.84 2.16 2.933(3) 153.4 3_565 yes
O1W H1WB O2W 0.84 1.94 2.757(3) 161.7 2_564 yes

_refine_diff_density_max         0.541
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.074

