# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cuc3
_audit_block_doi                 10.5517/ccdc.csd.cc23sbx5
_database_code_depnum_ccdc_archive 'CCDC 1959817'
loop_
_audit_author_name
_audit_author_address
'Nattamai S. P. Bhuvanesh'
;Department of Chemistry Texas A and M University, College Station,USA
United States of America
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;
_audit_creation_date             2018-06-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 Cl2 Cu2 N6 O4 S2, 2(Cl), 6(H2 O)'
_chemical_formula_sum            'C26 H38 Cl4 Cu2 N6 O10 S2'
_chemical_formula_weight         927.62
_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'
Cl Cl 0.1484 0.1585 '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'

_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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5171(5)
_cell_length_b                   9.6401(6)
_cell_length_c                   13.3389(8)
_cell_angle_alpha                101.493(2)
_cell_angle_beta                 98.976(2)
_cell_angle_gamma                99.952(2)
_cell_volume                     914.63(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.597
_cell_measurement_theta_min      2.400
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.661
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.3525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1159 before and 0.0606 after correction. The Ratio of minimum to maximum transmission is 0.8188. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.106
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18310
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.643
_diffrn_reflns_theta_min         2.205
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3550
_reflns_number_total             4245
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.107
_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)+(0.0099P)²+1.7359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0725
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B), O4(H4A,H4B), O5(H5A,H5B)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Cu1 Cu 0.18333(4) 0.46121(3) 0.56620(2) 0.00925(9) Uani 1 1 d . . . . .
Cl1 Cl 0.00507(8) 0.32720(6) 0.41134(4) 0.01053(13) Uani 1 1 d . . . . .
S1 S 0.03247(9) 0.31755(7) 0.65274(5) 0.01268(14) Uani 1 1 d . . . . .
O1 O 0.3366(2) 0.57519(18) 0.49145(13) 0.0112(4) Uani 1 1 d . . . . .
O2 O 0.7531(2) 0.93237(18) 0.61538(13) 0.0127(4) Uani 1 1 d . . . . .
N1 N 0.3586(3) 0.5478(2) 0.70039(16) 0.0102(4) Uani 1 1 d . . . . .
N2 N 0.3288(3) 0.4888(2) 0.78408(16) 0.0120(5) Uani 1 1 d . . . . .
H2 H 0.403332 0.522500 0.845275 0.014 Uiso 1 1 calc R . . . .
N3 N 0.1632(3) 0.3227(2) 0.85109(17) 0.0160(5) Uani 1 1 d . . . . .
H3 H 0.243369 0.362349 0.909677 0.019 Uiso 1 1 calc R . . . .
C1 C 0.4970(3) 0.6551(3) 0.71921(19) 0.0109(5) Uani 1 1 d . . . . .
H1 H 0.569168 0.686636 0.787863 0.013 Uiso 1 1 calc R . . . .
C2 C 0.5474(3) 0.7296(3) 0.64075(19) 0.0108(5) Uani 1 1 d . . . . .
C3 C 0.4638(3) 0.6848(3) 0.53168(19) 0.0101(5) Uani 1 1 d . . . . .
C4 C 0.5355(3) 0.7753(3) 0.4656(2) 0.0105(5) Uani 1 1 d . . . . .
C5 C 0.6768(4) 0.8977(3) 0.5103(2) 0.0122(5) Uani 1 1 d . . . . .
C6 C 0.6877(4) 0.8487(3) 0.6749(2) 0.0129(5) Uani 1 1 d . . . . .
H6 H 0.742917 0.873755 0.746895 0.016 Uiso 1 1 calc R . . . .
C7 C 0.4634(3) 0.7478(3) 0.3578(2) 0.0125(5) Uani 1 1 d . . . . .
H7 H 0.368826 0.664855 0.325139 0.015 Uiso 1 1 calc R . . . .
C8 C 0.5298(4) 0.8407(3) 0.2996(2) 0.0152(6) Uani 1 1 d . . . . .
H8 H 0.479731 0.822485 0.227146 0.018 Uiso 1 1 calc R . . . .
C9 C 0.6710(4) 0.9622(3) 0.3471(2) 0.0159(6) Uani 1 1 d . . . . .
H9 H 0.715914 1.025587 0.306276 0.019 Uiso 1 1 calc R . . . .
C10 C 0.7456(4) 0.9912(3) 0.4520(2) 0.0144(6) Uani 1 1 d . . . . .
H10 H 0.841918 1.073338 0.483747 0.017 Uiso 1 1 calc R . . . .
C11 C 0.1826(4) 0.3781(3) 0.7701(2) 0.0123(5) Uani 1 1 d . . . . .
C12 C 0.0181(4) 0.1999(3) 0.8512(2) 0.0239(7) Uani 1 1 d . . . . .
H12A H -0.039514 0.148007 0.778411 0.029 Uiso 1 1 calc R . . . .
H12B H -0.078471 0.235597 0.885371 0.029 Uiso 1 1 calc R . . . .
C13 C 0.0967(5) 0.0981(3) 0.9081(3) 0.0322(8) Uani 1 1 d . . . . .
H13A H 0.191521 0.062276 0.873782 0.048 Uiso 1 1 calc GR . . . .
H13B H -0.001528 0.016326 0.907294 0.048 Uiso 1 1 calc GR . . . .
H13C H 0.151684 0.149223 0.980447 0.048 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.69336(9) 0.47793(8) 0.91920(5) 0.02042(16) Uani 1 1 d . . . . .
O3 O 0.9646(3) 0.6899(2) 0.83104(16) 0.0285(5) Uani 1 1 d . . . . .
H3A H 0.968021 0.661340 0.766960 0.043 Uiso 1 1 d G . . . .
H3B H 0.899561 0.622965 0.850671 0.043 Uiso 1 1 d G . . . .
O4 O 0.6889(3) 0.2185(2) 1.03836(17) 0.0281(5) Uani 1 1 d . . . . .
H4A H 0.793484 0.247002 1.079242 0.042 Uiso 1 1 d G . . . .
H4B H 0.677554 0.287832 1.008832 0.042 Uiso 1 1 d G . . . .
O5 O 0.5760(3) -0.0448(2) 0.88012(16) 0.0286(5) Uani 1 1 d . . . . .
H5A H 0.621984 0.030672 0.928644 0.043 Uiso 1 1 d G . . . .
H5B H 0.495673 -0.094058 0.904735 0.043 Uiso 1 1 d G . . . .


_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 Cl1 2.2817(6) . ?
Cu1 Cl1 2.6726(7) 2_566 ?
Cu1 S1 2.2448(7) . ?
Cu1 O1 1.9712(17) . ?
Cu1 N1 1.981(2) . ?
S1 C11 1.709(3) . ?
O1 C3 1.259(3) . ?
O2 C5 1.379(3) . ?
O2 C6 1.327(3) . ?
N1 N2 1.381(3) . ?
N1 C1 1.287(3) . ?
N2 H2 0.8800 . ?
N2 C11 1.354(3) . ?
N3 H3 0.8800 . ?
N3 C11 1.314(3) . ?
N3 C12 1.465(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.444(3) . ?
C2 C3 1.438(3) . ?
C2 C6 1.364(3) . ?
C3 C4 1.456(3) . ?
C4 C5 1.402(3) . ?
C4 C7 1.409(4) . ?
C5 C10 1.389(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.377(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.402(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(4) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.499(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8498 . ?
O4 H4A 0.8502 . ?
O4 H4B 0.8501 . ?
O5 H5A 0.8503 . ?
O5 H5B 0.8503 . ?

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
Cl1 Cu1 Cl1 96.38(2) . 2_566 ?
S1 Cu1 Cl1 98.54(2) . 2_566 ?
S1 Cu1 Cl1 90.52(2) . . ?
O1 Cu1 Cl1 87.39(5) . 2_566 ?
O1 Cu1 Cl1 90.43(5) . . ?
O1 Cu1 S1 173.85(6) . . ?
O1 Cu1 N1 91.60(8) . . ?
N1 Cu1 Cl1 169.91(6) . . ?
N1 Cu1 Cl1 93.59(6) . 2_566 ?
N1 Cu1 S1 86.44(6) . . ?
Cu1 Cl1 Cu1 83.62(2) . 2_566 ?
C11 S1 Cu1 97.10(9) . . ?
C3 O1 Cu1 126.65(16) . . ?
C6 O2 C5 118.7(2) . . ?
N2 N1 Cu1 116.96(15) . . ?
C1 N1 Cu1 127.27(18) . . ?
C1 N1 N2 115.8(2) . . ?
N1 N2 H2 120.7 . . ?
C11 N2 N1 118.7(2) . . ?
C11 N2 H2 120.7 . . ?
C11 N3 H3 117.6 . . ?
C11 N3 C12 124.9(2) . . ?
C12 N3 H3 117.6 . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.0(2) . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 124.7(2) . . ?
C6 C2 C1 116.0(2) . . ?
C6 C2 C3 119.3(2) . . ?
O1 C3 C2 124.6(2) . . ?
O1 C3 C4 119.4(2) . . ?
C2 C3 C4 115.9(2) . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 C7 118.1(2) . . ?
C7 C4 C3 122.4(2) . . ?
O2 C5 C4 121.4(2) . . ?
O2 C5 C10 116.5(2) . . ?
C10 C5 C4 122.1(2) . . ?
O2 C6 C2 125.2(2) . . ?
O2 C6 H6 117.4 . . ?
C2 C6 H6 117.4 . . ?
C4 C7 H7 119.9 . . ?
C8 C7 C4 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.5 . . ?
C5 C10 H10 120.8 . . ?
C9 C10 C5 118.5(2) . . ?
C9 C10 H10 120.8 . . ?
N2 C11 S1 120.67(19) . . ?
N3 C11 S1 122.9(2) . . ?
N3 C11 N2 116.4(2) . . ?
N3 C12 H12A 109.6 . . ?
N3 C12 H12B 109.6 . . ?
N3 C12 C13 110.3(2) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H3A O3 H3B 109.5 . . ?
H4A O4 H4B 104.5 . . ?
H5A O5 H5B 104.5 . . ?

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
Cu1 S1 C11 N2 4.0(2) . . . . ?
Cu1 S1 C11 N3 -176.7(2) . . . . ?
Cu1 O1 C3 C2 13.9(4) . . . . ?
Cu1 O1 C3 C4 -166.31(17) . . . . ?
Cu1 N1 N2 C11 -0.7(3) . . . . ?
Cu1 N1 C1 C2 -0.9(4) . . . . ?
O1 C3 C4 C5 179.8(2) . . . . ?
O1 C3 C4 C7 2.2(4) . . . . ?
O2 C5 C10 C9 -178.8(2) . . . . ?
N1 N2 C11 S1 -2.7(3) . . . . ?
N1 N2 C11 N3 178.0(2) . . . . ?
N1 C1 C2 C3 -6.9(4) . . . . ?
N1 C1 C2 C6 174.6(2) . . . . ?
N2 N1 C1 C2 -179.8(2) . . . . ?
C1 N1 N2 C11 178.3(2) . . . . ?
C1 C2 C3 O1 0.0(4) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C1 C2 C6 O2 -179.4(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 C7 -177.9(2) . . . . ?
C3 C2 C6 O2 2.1(4) . . . . ?
C3 C4 C5 O2 1.7(4) . . . . ?
C3 C4 C5 C10 -177.3(2) . . . . ?
C3 C4 C7 C8 176.7(2) . . . . ?
C4 C5 C10 C9 0.3(4) . . . . ?
C4 C7 C8 C9 0.8(4) . . . . ?
C5 O2 C6 C2 -0.7(4) . . . . ?
C5 C4 C7 C8 -0.9(4) . . . . ?
C6 O2 C5 C4 -1.2(4) . . . . ?
C6 O2 C5 C10 177.9(2) . . . . ?
C6 C2 C3 O1 178.4(3) . . . . ?
C6 C2 C3 C4 -1.4(4) . . . . ?
C7 C4 C5 O2 179.4(2) . . . . ?
C7 C4 C5 C10 0.3(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C5 -0.5(4) . . . . ?
C11 N3 C12 C13 136.9(3) . . . . ?
C12 N3 C11 S1 2.7(4) . . . . ?
C12 N3 C11 N2 -178.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jhcrcu2a
_audit_block_doi                 10.5517/ccdc.csd.cc23sby6
_database_code_depnum_ccdc_archive 'CCDC 1959818'
loop_
_audit_author_name
_audit_author_address
'Nattamai S. P. Bhuvanesh'
;Department of Chemistry Texas A and M University, College Station,USA
United States of America
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;
_audit_creation_date             2017-01-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 Cl2 Cu N3 O2 S, 0.34(H2 O)'
_chemical_formula_sum            'C11 H9.68 Cl2 Cu N3 O2.34 S'
_chemical_formula_weight         387.84
_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'
Cl Cl 0.1484 0.1585 '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'

_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      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_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                   9.3084(5)
_cell_length_b                   11.1550(6)
_cell_length_c                   13.8573(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.420(2)
_cell_angle_gamma                90
_cell_volume                     1357.01(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.507
_cell_measurement_theta_min      2.325
_shelx_estimated_absorpt_T_max   0.718
_shelx_estimated_absorpt_T_min   0.332
_exptl_absorpt_coefficient_mu    2.162
_exptl_absorpt_correction_T_max  0.5629
_exptl_absorpt_correction_T_min  0.2900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1461 before and 0.0735 after correction.
The Ratio of minimum to maximum transmission is 0.5152.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             778
_exptl_crystal_size_max          0.655
_exptl_crystal_size_mid          0.434
_exptl_crystal_size_min          0.164
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26689
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         2.953
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2540
_reflns_number_total             3106
_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       ?
_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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0203P)²+2.9323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0792
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O3(0.34) H3C(0.34) H3D(0.34)
3.a Free rotating group:
 O3(H3C,H3D)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
3.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cu1 Cu 0.45598(4) 0.76243(3) 0.69912(3) 0.01275(11) Uani 1 1 d . . . . .
Cl1 Cl 0.24774(8) 0.86185(6) 0.59854(6) 0.01622(16) Uani 1 1 d . . . . .
Cl2 Cl 0.58202(8) 0.72093(7) 0.56309(6) 0.01934(17) Uani 1 1 d . . . . .
S1 S 0.57229(8) 0.93788(7) 0.76303(6) 0.01716(17) Uani 1 1 d . . . . .
O1 O 0.3463(2) 0.60669(17) 0.66654(15) 0.0140(4) Uani 1 1 d . . . . .
O2 O 0.4954(2) 0.26854(18) 0.76394(16) 0.0181(5) Uani 1 1 d . . . . .
N1 N 0.6215(3) 0.6831(2) 0.81329(19) 0.0140(5) Uani 1 1 d . . . . .
N2 N 0.7320(3) 0.7587(2) 0.87474(19) 0.0169(5) Uani 1 1 d . . . . .
H2 H 0.8114 0.7290 0.9230 0.020 Uiso 1 1 calc R . . . .
N3 N 0.8225(3) 0.9457(2) 0.92440(19) 0.0188(6) Uani 1 1 d . . . . .
H3A H 0.8976 0.9124 0.9736 0.023 Uiso 1 1 calc R . . . .
H3B H 0.8176 1.0242 0.9179 0.023 Uiso 1 1 calc R . . . .
C1 C 0.6425(3) 0.5706(3) 0.8329(2) 0.0146(6) Uani 1 1 d . . . . .
H1 H 0.7319 0.5462 0.8861 0.018 Uiso 1 1 calc R . . . .
C2 C 0.5366(3) 0.4795(3) 0.7779(2) 0.0136(6) Uani 1 1 d . . . . .
C3 C 0.3931(3) 0.5042(3) 0.6977(2) 0.0119(6) Uani 1 1 d . . . . .
C4 C 0.3042(3) 0.3995(3) 0.6527(2) 0.0133(6) Uani 1 1 d . . . . .
C5 C 0.3571(3) 0.2850(3) 0.6865(2) 0.0149(6) Uani 1 1 d . . . . .
C6 C 0.5767(3) 0.3640(3) 0.8053(2) 0.0161(6) Uani 1 1 d . . . . .
H6 H 0.6708 0.3509 0.8585 0.019 Uiso 1 1 calc R . . . .
C7 C 0.1635(3) 0.4087(3) 0.5730(2) 0.0160(6) Uani 1 1 d . . . . .
H7 H 0.1243 0.4855 0.5479 0.019 Uiso 1 1 calc R . . . .
C8 C 0.0826(3) 0.3074(3) 0.5312(2) 0.0167(6) Uani 1 1 d . . . . .
H8 H -0.0121 0.3142 0.4773 0.020 Uiso 1 1 calc R . . . .
C9 C 0.1398(4) 0.1944(3) 0.5681(2) 0.0187(7) Uani 1 1 d . . . . .
H9 H 0.0829 0.1248 0.5391 0.022 Uiso 1 1 calc R . . . .
C10 C 0.2768(4) 0.1822(3) 0.6456(2) 0.0180(6) Uani 1 1 d . . . . .
H10 H 0.3153 0.1052 0.6705 0.022 Uiso 1 1 calc R . . . .
C11 C 0.7174(3) 0.8779(3) 0.8604(2) 0.0157(6) Uani 1 1 d . . . . .
O3 O 0.51(3) 1.000(13) 0.494(12) 0.036(9) Uani 0.34 1 d . . P A -1
H3C H 0.5060 0.9295 0.5205 0.054 Uiso 0.34 1 d G . P A -1
H3D H 0.4860 1.0540 0.5337 0.054 Uiso 0.34 1 d G . P A -1


_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 Cl1 2.2656(8) . ?
Cu1 Cl2 2.5719(8) . ?
Cu1 S1 2.2692(8) . ?
Cu1 O1 1.9892(19) . ?
Cu1 N1 2.010(2) . ?
S1 C11 1.698(3) . ?
O1 C3 1.249(3) . ?
O2 C5 1.387(4) . ?
O2 C6 1.322(4) . ?
N1 N2 1.383(3) . ?
N1 C1 1.285(4) . ?
N2 H2 0.8800 . ?
N2 C11 1.344(4) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C11 1.318(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.445(4) . ?
C2 C3 1.452(4) . ?
C2 C6 1.360(4) . ?
C3 C4 1.447(4) . ?
C4 C5 1.393(4) . ?
C4 C7 1.409(4) . ?
C5 C10 1.383(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.375(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.398(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(4) . ?
C10 H10 0.9500 . ?
O3 H3C 0.8701 . ?
O3 H3D 0.8702 . ?

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
Cl1 Cu1 Cl2 98.20(3) . . ?
Cl1 Cu1 S1 91.00(3) . . ?
S1 Cu1 Cl2 99.59(3) . . ?
O1 Cu1 Cl1 91.06(6) . . ?
O1 Cu1 Cl2 90.06(6) . . ?
O1 Cu1 S1 169.74(6) . . ?
O1 Cu1 N1 89.72(9) . . ?
N1 Cu1 Cl1 167.15(7) . . ?
N1 Cu1 Cl2 94.62(7) . . ?
N1 Cu1 S1 86.06(7) . . ?
C11 S1 Cu1 96.93(11) . . ?
C3 O1 Cu1 128.89(18) . . ?
C6 O2 C5 118.7(2) . . ?
N2 N1 Cu1 115.75(18) . . ?
C1 N1 Cu1 128.3(2) . . ?
C1 N1 N2 115.8(3) . . ?
N1 N2 H2 120.2 . . ?
C11 N2 N1 119.7(2) . . ?
C11 N2 H2 120.2 . . ?
H3A N3 H3B 120.0 . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.1(3) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 124.3(3) . . ?
C6 C2 C1 116.3(3) . . ?
C6 C2 C3 119.4(3) . . ?
O1 C3 C2 124.4(3) . . ?
O1 C3 C4 120.4(3) . . ?
C4 C3 C2 115.2(2) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 C7 117.6(3) . . ?
C7 C4 C3 121.9(3) . . ?
O2 C5 C4 121.0(3) . . ?
C10 C5 O2 116.3(3) . . ?
C10 C5 C4 122.7(3) . . ?
O2 C6 C2 125.3(3) . . ?
O2 C6 H6 117.4 . . ?
C2 C6 H6 117.4 . . ?
C4 C7 H7 119.8 . . ?
C8 C7 C4 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.4 . . ?
C5 C10 H10 120.9 . . ?
C9 C10 C5 118.2(3) . . ?
C9 C10 H10 120.9 . . ?
N2 C11 S1 121.4(2) . . ?
N3 C11 S1 121.7(2) . . ?
N3 C11 N2 116.9(3) . . ?
H3C O3 H3D 109.4 . . ?

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
N2 H2 Cl1 0.88 2.87 3.339(3) 114.7 4_676
N2 H2 Cl2 0.88 2.68 3.439(3) 145.3 4_676
N3 H3A Cl2 0.88 2.30 3.146(3) 161.7 4_676
N3 H3B Cl2 0.88 2.37 3.185(3) 155.0 2_656
O3 H3C Cl2 0.87 2.45 3.27(14) 157.5 .
O3 H3D Cl2 0.87 2.82 3.25(15) 112.0 3_676

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 C11 N2 1.5(3) . . . . ?
Cu1 S1 C11 N3 -179.7(2) . . . . ?
Cu1 O1 C3 C2 8.8(4) . . . . ?
Cu1 O1 C3 C4 -170.16(19) . . . . ?
Cu1 N1 N2 C11 4.9(3) . . . . ?
Cu1 N1 C1 C2 -5.9(4) . . . . ?
O1 C3 C4 C5 179.2(3) . . . . ?
O1 C3 C4 C7 0.1(4) . . . . ?
O2 C5 C10 C9 -179.4(3) . . . . ?
N1 N2 C11 S1 -4.3(4) . . . . ?
N1 N2 C11 N3 176.9(2) . . . . ?
N1 C1 C2 C3 -2.4(5) . . . . ?
N1 C1 C2 C6 178.1(3) . . . . ?
N2 N1 C1 C2 178.5(3) . . . . ?
C1 N1 N2 C11 -178.9(3) . . . . ?
C1 C2 C3 O1 1.0(5) . . . . ?
C1 C2 C3 C4 -180.0(3) . . . . ?
C1 C2 C6 O2 -179.8(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 C7 -179.0(3) . . . . ?
C3 C2 C6 O2 0.7(5) . . . . ?
C3 C4 C5 O2 0.1(4) . . . . ?
C3 C4 C5 C10 -179.7(3) . . . . ?
C3 C4 C7 C8 179.4(3) . . . . ?
C4 C5 C10 C9 0.3(4) . . . . ?
C4 C7 C8 C9 0.2(4) . . . . ?
C5 O2 C6 C2 -0.4(4) . . . . ?
C5 C4 C7 C8 0.2(4) . . . . ?
C6 O2 C5 C4 0.0(4) . . . . ?
C6 O2 C5 C10 179.8(3) . . . . ?
C6 C2 C3 O1 -179.6(3) . . . . ?
C6 C2 C3 C4 -0.5(4) . . . . ?
C7 C4 C5 O2 179.3(2) . . . . ?
C7 C4 C5 C10 -0.5(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C5 0.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
