# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_1_2014ncs0359
_database_code_depnum_ccdc_archive 'CCDC 2082368'
loop_
_audit_author_name
_audit_author_address
'Peter Horton'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2021-05-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H26 Cu N6 O2 S2, Cl O4, C2 H3 N'
_chemical_formula_sum            'C30 H29 Cl Cu N7 O6 S2'
_chemical_formula_weight         746.71
_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                   15.4602(11)
_cell_length_b                   9.7669(7)
_cell_length_c                   21.9107(15)
_cell_angle_alpha                90
_cell_angle_beta                 109.196(2)
_cell_angle_gamma                90
_cell_volume                     3124.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17705
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.779
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20514
_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         27.485
_diffrn_reflns_theta_min         2.509
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
scan:
	Number of images: 151
	           Slice: -78.0000 - 73.0000
	     Image width: 1.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 18.0000
	             Phi: -30.0000
	             XTD: 45.0378
	          2theta: -17.3203
scan:
	Number of images: 91
	           Slice: -80.0000 - 11.0000
	     Image width: 1.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -180.0000
	             XTD: 45.0378
	          2theta: -17.3203
scan:
	Number of images: 53
	           Slice: -107.0000 - -54.0000
	     Image width: 1.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -18.0000
	             Phi: 150.0000
	             XTD: 45.0378
	          2theta: -17.3203
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.005028
_diffrn_orient_matrix_UB_12      -0.007466
_diffrn_orient_matrix_UB_13      0.067896
_diffrn_orient_matrix_UB_21      0.097372
_diffrn_orient_matrix_UB_22      0.031427
_diffrn_orient_matrix_UB_23      -0.003755
_diffrn_orient_matrix_UB_31      -0.012539
_diffrn_orient_matrix_UB_32      0.041419
_diffrn_orient_matrix_UB_33      0.021512
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5054
_reflns_number_total             7140
_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       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         7140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.025
_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)+(0.0536P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1133
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C23(H23), C24(H24), C26(H26), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C27(H27A,H27B,H27C), C52(H52A,H52B,H52C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.74744(2) 0.54591(3) 0.25489(2) 0.01922(10) Uani 1 1 d . . . . .
C1 C 0.95054(15) 0.5661(3) 0.35035(13) 0.0190(5) Uani 1 1 d . . . . .
C2 C 0.84915(15) 0.3928(3) 0.38027(13) 0.0185(5) Uani 1 1 d . . . . .
C3 C 0.85981(16) 0.2853(3) 0.42359(13) 0.0198(6) Uani 1 1 d . . . . .
H3 H 0.918460 0.264746 0.453596 0.024 Uiso 1 1 calc R U . . .
C4 C 0.78441(16) 0.2085(3) 0.42268(13) 0.0212(6) Uani 1 1 d . . . . .
H4 H 0.790985 0.133081 0.451223 0.025 Uiso 1 1 calc R U . . .
C5 C 0.69789(16) 0.2430(3) 0.37917(13) 0.0199(5) Uani 1 1 d . . . . .
C6 C 0.69410(16) 0.3513(3) 0.33817(13) 0.0201(6) Uani 1 1 d . . . . .
H6 H 0.635759 0.376236 0.308973 0.024 Uiso 1 1 calc R U . . .
C7 C 0.61213(16) 0.1665(3) 0.37809(14) 0.0240(6) Uani 1 1 d . . . . .
H7A H 0.576192 0.223294 0.397771 0.036 Uiso 1 1 calc R U . . .
H7B H 0.629286 0.080963 0.402502 0.036 Uiso 1 1 calc R U . . .
H7C H 0.575444 0.145609 0.333292 0.036 Uiso 1 1 calc R U . . .
C8 C 1.11389(16) 0.5507(3) 0.42185(13) 0.0206(6) Uani 1 1 d . . . . .
C9 C 1.20911(16) 0.5894(3) 0.42467(14) 0.0217(6) Uani 1 1 d . . . . .
C10 C 1.22980(17) 0.6356(3) 0.37091(14) 0.0241(6) Uani 1 1 d . . . . .
H10 H 1.182184 0.652912 0.331345 0.029 Uiso 1 1 calc R U . . .
C11 C 1.32108(18) 0.6561(3) 0.37574(15) 0.0275(6) Uani 1 1 d . . . . .
H11 H 1.335939 0.684664 0.338944 0.033 Uiso 1 1 calc R U . . .
C12 C 1.38993(17) 0.6349(3) 0.43389(15) 0.0273(7) Uani 1 1 d . . . . .
H12 H 1.451892 0.649475 0.436732 0.033 Uiso 1 1 calc R U . . .
C13 C 1.36992(16) 0.5927(3) 0.48820(14) 0.0257(6) Uani 1 1 d . . . . .
H13 H 1.417690 0.580329 0.528204 0.031 Uiso 1 1 calc R U . . .
C14 C 1.27921(15) 0.5685(3) 0.48359(14) 0.0211(6) Uani 1 1 d . . . . .
H14 H 1.264897 0.537932 0.520304 0.025 Uiso 1 1 calc R U . . .
N1 N 0.76803(13) 0.4256(2) 0.33643(10) 0.0182(5) Uani 1 1 d . . . . .
N2 N 0.92978(14) 0.4677(2) 0.38555(12) 0.0213(5) Uani 1 1 d . . . . .
N3 N 1.04261(13) 0.6092(2) 0.37310(11) 0.0205(5) Uani 1 1 d . . . . .
O1 O 1.10104(11) 0.4684(2) 0.46062(9) 0.0264(4) Uani 1 1 d . . . . .
S1 S 0.88412(4) 0.64615(7) 0.28405(3) 0.02128(16) Uani 1 1 d . . . . .
C21 C 0.54467(15) 0.5572(3) 0.15972(13) 0.0187(5) Uani 1 1 d . . . . .
C22 C 0.65198(15) 0.4030(3) 0.12511(13) 0.0183(5) Uani 1 1 d . . . . .
C23 C 0.64741(17) 0.3200(3) 0.07255(14) 0.0240(6) Uani 1 1 d . . . . .
H23 H 0.590404 0.305352 0.039466 0.029 Uiso 1 1 calc R U . . .
C24 C 0.72599(17) 0.2590(3) 0.06859(14) 0.0237(6) Uani 1 1 d . . . . .
H24 H 0.723563 0.201447 0.033120 0.028 Uiso 1 1 calc R U . . .
C25 C 0.80926(16) 0.2833(3) 0.11764(13) 0.0209(6) Uani 1 1 d . . . . .
C26 C 0.80698(16) 0.3677(3) 0.16697(13) 0.0202(6) Uani 1 1 d . . . . .
H26 H 0.863486 0.385603 0.200040 0.024 Uiso 1 1 calc R U . . .
C27 C 0.89820(17) 0.2206(3) 0.11602(15) 0.0294(7) Uani 1 1 d . . . . .
H27A H 0.949416 0.257884 0.151569 0.044 Uiso 1 1 calc R U . . .
H27B H 0.906826 0.242480 0.074740 0.044 Uiso 1 1 calc R U . . .
H27C H 0.895855 0.121054 0.120687 0.044 Uiso 1 1 calc R U . . .
C28 C 0.38184(16) 0.5252(3) 0.09175(13) 0.0205(6) Uani 1 1 d . . . . .
C29 C 0.28691(15) 0.5759(3) 0.08147(13) 0.0204(6) Uani 1 1 d . . . . .
C30 C 0.26830(17) 0.7064(3) 0.09947(14) 0.0235(6) Uani 1 1 d . . . . .
H30 H 0.317311 0.766757 0.120365 0.028 Uiso 1 1 calc R U . . .
C31 C 0.17828(17) 0.7489(3) 0.08699(14) 0.0246(6) Uani 1 1 d . . . . .
H31 H 0.165670 0.837475 0.099902 0.030 Uiso 1 1 calc R U . . .
C32 C 0.10676(17) 0.6608(3) 0.05546(14) 0.0265(6) Uani 1 1 d . . . . .
H32 H 0.045112 0.690113 0.045808 0.032 Uiso 1 1 calc R U . . .
C33 C 0.12543(17) 0.5302(3) 0.03809(15) 0.0291(7) Uani 1 1 d . . . . .
H33 H 0.076396 0.469761 0.017403 0.035 Uiso 1 1 calc R U . . .
C34 C 0.21557(16) 0.4871(3) 0.05079(14) 0.0242(6) Uani 1 1 d . . . . .
H34 H 0.228160 0.397856 0.038612 0.029 Uiso 1 1 calc R U . . .
N21 N 0.73059(13) 0.4282(2) 0.17272(11) 0.0184(5) Uani 1 1 d . . . . .
N22 N 0.56783(14) 0.4605(2) 0.12470(11) 0.0200(5) Uani 1 1 d . . . . .
N23 N 0.45173(13) 0.5919(2) 0.13814(11) 0.0198(5) Uani 1 1 d . . . . .
O21 O 0.39599(11) 0.4290(2) 0.05948(10) 0.0279(5) Uani 1 1 d . . . . .
S21 S 0.61043(4) 0.64421(7) 0.22416(3) 0.02098(16) Uani 1 1 d . . . . .
Cl41 Cl 0.39739(4) 0.40860(7) 0.26439(4) 0.02666(17) Uani 1 1 d . . . . .
O41 O 0.44017(14) 0.3433(2) 0.22201(11) 0.0371(5) Uani 1 1 d . . . . .
O42 O 0.36772(14) 0.5438(2) 0.24097(11) 0.0368(5) Uani 1 1 d . . . . .
O43 O 0.31952(13) 0.3282(2) 0.26517(11) 0.0377(5) Uani 1 1 d . . . . .
O44 O 0.46244(13) 0.4172(2) 0.32869(11) 0.0432(6) Uani 1 1 d . . . . .
C51 C 0.40593(17) 0.9229(3) 0.25370(15) 0.0259(6) Uani 1 1 d . . . . .
C52 C 0.3767(2) 0.9919(3) 0.30161(16) 0.0351(7) Uani 1 1 d . . . . .
H52A H 0.382657 1.091069 0.297447 0.053 Uiso 1 1 calc R U . . .
H52B H 0.414984 0.962599 0.344836 0.053 Uiso 1 1 calc R U . . .
H52C H 0.312592 0.969033 0.295177 0.053 Uiso 1 1 calc R U . . .
N51 N 0.42851(15) 0.8685(3) 0.21523(13) 0.0338(6) Uani 1 1 d . . . . .
H23A H 0.4357(16) 0.644(3) 0.1641(13) 0.011(7) Uiso 1 1 d . . . . .
H2 H 0.975(2) 0.445(3) 0.4156(16) 0.033(9) Uiso 1 1 d . . . . .
H22 H 0.5208(19) 0.427(3) 0.0953(15) 0.027(8) Uiso 1 1 d . . . . .
H3A H 1.056(2) 0.671(4) 0.3469(17) 0.047(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.074(2) . ?
Cu1 S1 2.2235(7) . ?
Cu1 N21 2.079(2) . ?
Cu1 S21 2.2191(7) . ?
C1 N2 1.335(3) . ?
C1 N3 1.409(3) . ?
C1 S1 1.672(3) . ?
C2 C3 1.388(4) . ?
C2 N1 1.344(3) . ?
C2 N2 1.417(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.405(3) . ?
C5 C6 1.377(4) . ?
C5 C7 1.516(3) . ?
C6 H6 0.9500 . ?
C6 N1 1.365(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.501(3) . ?
C8 N3 1.381(3) . ?
C8 O1 1.232(3) . ?
C9 C10 1.393(4) . ?
C9 C14 1.401(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(3) . ?
C14 H14 0.9500 . ?
N2 H2 0.82(3) . ?
N3 H3A 0.90(4) . ?
C21 N22 1.338(3) . ?
C21 N23 1.399(3) . ?
C21 S21 1.675(3) . ?
C22 C23 1.391(4) . ?
C22 N21 1.339(3) . ?
C22 N22 1.414(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.400(4) . ?
C25 C26 1.369(4) . ?
C25 C27 1.516(3) . ?
C26 H26 0.9500 . ?
C26 N21 1.363(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.494(3) . ?
C28 N23 1.379(3) . ?
C28 O21 1.238(3) . ?
C29 C30 1.392(4) . ?
C29 C34 1.390(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.390(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.392(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.389(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.393(3) . ?
C34 H34 0.9500 . ?
N22 H22 0.86(3) . ?
N23 H23A 0.86(3) . ?
Cl41 O41 1.453(2) . ?
Cl41 O42 1.436(2) . ?
Cl41 O43 1.4422(19) . ?
Cl41 O44 1.439(2) . ?
C51 C52 1.440(4) . ?
C51 N51 1.144(4) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 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
N1 Cu1 S1 98.04(6) . . ?
N1 Cu1 N21 111.87(9) . . ?
N1 Cu1 S21 111.55(6) . . ?
N21 Cu1 S1 109.21(6) . . ?
N21 Cu1 S21 98.12(6) . . ?
S21 Cu1 S1 128.23(3) . . ?
N2 C1 N3 114.7(2) . . ?
N2 C1 S1 129.99(19) . . ?
N3 C1 S1 115.32(19) . . ?
C3 C2 N2 115.6(2) . . ?
N1 C2 C3 122.8(2) . . ?
N1 C2 N2 121.6(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C7 121.7(2) . . ?
C6 C5 C4 117.0(2) . . ?
C6 C5 C7 121.3(2) . . ?
C5 C6 H6 117.6 . . ?
N1 C6 C5 124.8(2) . . ?
N1 C6 H6 117.6 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 116.7(2) . . ?
O1 C8 C9 120.9(2) . . ?
O1 C8 N3 122.3(2) . . ?
C10 C9 C8 122.8(2) . . ?
C10 C9 C14 120.2(2) . . ?
C14 C9 C8 116.9(2) . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C2 N1 Cu1 126.42(17) . . ?
C2 N1 C6 116.5(2) . . ?
C6 N1 Cu1 115.63(16) . . ?
C1 N2 C2 134.1(2) . . ?
C1 N2 H2 111(2) . . ?
C2 N2 H2 115(2) . . ?
C1 N3 H3A 113(2) . . ?
C8 N3 C1 127.3(2) . . ?
C8 N3 H3A 119(2) . . ?
C1 S1 Cu1 107.33(9) . . ?
N22 C21 N23 114.6(2) . . ?
N22 C21 S21 129.71(18) . . ?
N23 C21 S21 115.69(19) . . ?
C23 C22 N22 115.5(2) . . ?
N21 C22 C23 122.6(2) . . ?
N21 C22 N22 122.0(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 120.5 . . ?
C23 C24 C25 119.0(3) . . ?
C25 C24 H24 120.5 . . ?
C24 C25 C27 121.7(2) . . ?
C26 C25 C24 116.9(2) . . ?
C26 C25 C27 121.4(2) . . ?
C25 C26 H26 117.2 . . ?
N21 C26 C25 125.6(2) . . ?
N21 C26 H26 117.2 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N23 C28 C29 116.6(2) . . ?
O21 C28 C29 121.0(2) . . ?
O21 C28 N23 122.4(2) . . ?
C30 C29 C28 123.0(2) . . ?
C34 C29 C28 116.7(2) . . ?
C34 C29 C30 120.2(2) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.3(2) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 120.2 . . ?
C30 C31 C32 119.6(3) . . ?
C32 C31 H31 120.2 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.1(2) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 119.8 . . ?
C32 C33 C34 120.5(3) . . ?
C34 C33 H33 119.8 . . ?
C29 C34 C33 119.4(3) . . ?
C29 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C22 N21 Cu1 126.83(17) . . ?
C22 N21 C26 116.2(2) . . ?
C26 N21 Cu1 117.01(17) . . ?
C21 N22 C22 134.1(2) . . ?
C21 N22 H22 112.0(19) . . ?
C22 N22 H22 113.9(19) . . ?
C21 N23 H23A 114.1(16) . . ?
C28 N23 C21 127.1(2) . . ?
C28 N23 H23A 116.3(16) . . ?
C21 S21 Cu1 106.89(9) . . ?
O42 Cl41 O41 109.52(13) . . ?
O42 Cl41 O43 109.59(13) . . ?
O42 Cl41 O44 109.55(14) . . ?
O43 Cl41 O41 109.01(13) . . ?
O44 Cl41 O41 109.44(13) . . ?
O44 Cl41 O43 109.72(14) . . ?
N51 C51 C52 179.4(3) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?

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
N23 H23A O42 0.86(3) 2.47(3) 2.985(3) 120(2) . yes
N23 H23A N51 0.86(3) 2.48(3) 3.268(4) 153(2) . yes
N2 H2 O1 0.82(3) 1.88(3) 2.618(3) 148(3) . yes
N22 H22 O21 0.86(3) 1.83(3) 2.588(3) 146(3) . yes
N3 H3A O41 0.90(4) 2.28(4) 3.163(3) 168(3) 2_655 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
C2 C3 C4 C5 -1.8(4) . . . . ?
C3 C2 N1 Cu1 -162.8(2) . . . . ?
C3 C2 N1 C6 3.0(4) . . . . ?
C3 C2 N2 C1 172.1(3) . . . . ?
C3 C4 C5 C6 1.7(4) . . . . ?
C3 C4 C5 C7 -177.2(2) . . . . ?
C4 C5 C6 N1 0.9(4) . . . . ?
C5 C6 N1 Cu1 164.2(2) . . . . ?
C5 C6 N1 C2 -3.1(4) . . . . ?
C7 C5 C6 N1 179.7(2) . . . . ?
C8 C9 C10 C11 -173.4(2) . . . . ?
C8 C9 C14 C13 175.3(2) . . . . ?
C9 C8 N3 C1 163.2(2) . . . . ?
C9 C10 C11 C12 -2.0(4) . . . . ?
C10 C9 C14 C13 -0.6(4) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 1.4(4) . . . . ?
C12 C13 C14 C9 -1.2(4) . . . . ?
C14 C9 C10 C11 2.2(4) . . . . ?
N1 C2 C3 C4 -0.6(4) . . . . ?
N1 C2 N2 C1 -8.5(5) . . . . ?
N2 C1 N3 C8 8.4(4) . . . . ?
N2 C1 S1 Cu1 -5.2(3) . . . . ?
N2 C2 C3 C4 178.7(2) . . . . ?
N2 C2 N1 Cu1 17.9(4) . . . . ?
N2 C2 N1 C6 -176.3(2) . . . . ?
N3 C1 N2 C2 -178.1(3) . . . . ?
N3 C1 S1 Cu1 175.29(17) . . . . ?
N3 C8 C9 C10 -24.3(4) . . . . ?
N3 C8 C9 C14 159.9(2) . . . . ?
O1 C8 C9 C10 154.3(3) . . . . ?
O1 C8 C9 C14 -21.5(4) . . . . ?
O1 C8 N3 C1 -15.3(4) . . . . ?
S1 C1 N2 C2 2.4(5) . . . . ?
S1 C1 N3 C8 -172.1(2) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C22 N21 Cu1 -178.53(19) . . . . ?
C23 C22 N21 C26 0.1(4) . . . . ?
C23 C22 N22 C21 -169.1(3) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
C23 C24 C25 C27 -179.5(3) . . . . ?
C24 C25 C26 N21 0.9(4) . . . . ?
C25 C26 N21 Cu1 177.8(2) . . . . ?
C25 C26 N21 C22 -0.9(4) . . . . ?
C27 C25 C26 N21 -179.7(2) . . . . ?
C28 C29 C30 C31 178.2(3) . . . . ?
C28 C29 C34 C33 -178.1(3) . . . . ?
C29 C28 N23 C21 174.9(2) . . . . ?
C29 C30 C31 C32 -1.0(4) . . . . ?
C30 C29 C34 C33 0.2(4) . . . . ?
C30 C31 C32 C33 1.6(4) . . . . ?
C31 C32 C33 C34 -1.3(5) . . . . ?
C32 C33 C34 C29 0.4(4) . . . . ?
C34 C29 C30 C31 0.1(4) . . . . ?
N21 C22 C23 C24 0.6(4) . . . . ?
N21 C22 N22 C21 10.3(5) . . . . ?
N22 C21 N23 C28 9.8(4) . . . . ?
N22 C21 S21 Cu1 -9.5(3) . . . . ?
N22 C22 C23 C24 -179.9(2) . . . . ?
N22 C22 N21 Cu1 2.1(4) . . . . ?
N22 C22 N21 C26 -179.3(2) . . . . ?
N23 C21 N22 C22 173.9(3) . . . . ?
N23 C21 S21 Cu1 171.81(17) . . . . ?
N23 C28 C29 C30 21.0(4) . . . . ?
N23 C28 C29 C34 -160.8(3) . . . . ?
O21 C28 C29 C30 -158.3(3) . . . . ?
O21 C28 C29 C34 19.9(4) . . . . ?
O21 C28 N23 C21 -5.8(4) . . . . ?
S21 C21 N22 C22 -4.7(5) . . . . ?
S21 C21 N23 C28 -171.4(2) . . . . ?

_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_7_2014ncs0431
_database_code_depnum_ccdc_archive 'CCDC 2082371'
loop_
_audit_author_name
_audit_author_address
'Peter Horton'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2016-05-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H16 N8 Ni S2, O, 2(Cl O4), 0.5(C4 H8 O2)'
_chemical_formula_sum            'C14 H22 Cl2 N8 Ni O10 S2'
_chemical_formula_weight         656.12
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.5374(10)
_cell_length_b                   17.6166(11)
_cell_length_c                   10.1978(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.5720(10)
_cell_angle_gamma                90
_cell_volume                     2489.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16286
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.818
_exptl_absorpt_coefficient_mu    1.228
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Blade
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17829
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         3.121
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: -99.0000 - 81.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 150.0000
	             XTD: 34.9628
	          2theta: -9.0698
scan:
	Number of images: 70
	           Slice: -45.0000 - 25.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -90.0000
	             XTD: 34.9628
	          2theta: -9.0698
scan:
	Number of images: 81
	           Slice: -56.0000 - 25.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 90.0000
	             XTD: 34.9628
	          2theta: -9.0698
scan:
	Number of images: 105
	           Slice: -25.0000 - 80.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -150.0000
	             XTD: 34.9628
	          2theta: -9.0698
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.057560
_diffrn_orient_matrix_UB_12      -0.033853
_diffrn_orient_matrix_UB_13      -0.027335
_diffrn_orient_matrix_UB_21      -0.013893
_diffrn_orient_matrix_UB_22      0.018292
_diffrn_orient_matrix_UB_23      -0.051909
_diffrn_orient_matrix_UB_31      0.078815
_diffrn_orient_matrix_UB_32      0.066057
_diffrn_orient_matrix_UB_33      0.002183
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2416
_reflns_number_total             2849
_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       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2849
_refine_ls_number_restraints     371
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.197
_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)+(0.0725P)²+4.3790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1352
_refine_special_details          
;
The perchlorate anion is disordered, along with a water molecule and ethyl acetate over symmetry sites. As such various geometrical (DFIX, SAME, BUMP) and displacement (DELU, SIMU, RIGU) restraints used. Also due to the disorder the ethyl acetate and water atoms were left isotropic and displacement constraints (EADP) applied.
 It was not possible to locate the hydrogen atoms of the disordered water molecules but they have been included in the formula.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C51-C52 = C53-C54
 1.52 with sigma of 0.02
 O52-C52 = O52-C53
 1.45 with sigma of 0.02
 C52-O51
 1.2 with sigma of 0.01
 C51-O52 = C54-O52 = C52-C53 = C51-O51 = O51-O52
 2.3 with sigma of 0.02
3. Restrained planarity
 C51, C52, O51, O52
 with sigma of 0.001
4. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Cl21 \\sim O21 \\sim O22 \\sim O23 \\sim O24 \\sim Cl26 \\sim O26 \\sim O27
\\sim O28 \\sim O29 \\sim C51 \\sim C52 \\sim C53 \\sim C54: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uiso(C51) = Uiso(C52) = Uiso(C53) = Uiso(C54) = Uiso(O51) = Uiso(O52)
Uiso(O11) = Uiso(O12)
6. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Same fragment restrains
{Cl21, O21, O22, O23, O24} sigma for 1-2: 0.01, 1-3: 0.04
as
{Cl26, O26, O27, O28, O29}
8. Others
 Sof(Cl26)=Sof(O26)=Sof(O27)=Sof(O28)=Sof(O29)=1-FVAR(1)
 Sof(Cl21)=Sof(O21)=Sof(O22)=Sof(O23)=Sof(O24)=FVAR(1)
 Sof(O12)=0.5*(1-FVAR(3))
 Sof(O11)=0.5*FVAR(3)
 Fixed Sof: C51(0.25) H51A(0.25) H51B(0.25) H51C(0.25) C52(0.25) C53(0.25)
 H53A(0.25) H53B(0.25) C54(0.25) H54A(0.25) H54B(0.25) H54C(0.25) O51(0.25)
 O52(0.25)
9.a Rotating group:
 N4(H4A,H4B)
9.b Secondary CH2 refined with riding coordinates:
 C53(H53A,H53B)
9.c Me refined with riding coordinates:
 C51(H51A,H51B,H51C), C54(H54A,H54B,H54C)
9.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), N2(H2)
9.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Ni1 Ni 0.5000 0.83528(3) 0.2500 0.02452(17) Uani 1 2 d S TU P . .
S1 S 0.58121(6) 0.92383(4) 0.38233(8) 0.0355(2) Uani 1 1 d . U . . .
C1 C 0.5888(2) 0.88604(19) 0.5394(3) 0.0360(7) Uani 1 1 d . U . . .
C2 C 0.6101(2) 0.75137(17) 0.4880(3) 0.0316(6) Uani 1 1 d . U . . .
C3 C 0.6535(2) 0.6877(2) 0.5579(4) 0.0427(7) Uani 1 1 d . U . . .
H3 H 0.6669 0.6836 0.6548 0.051 Uiso 1 1 calc R . . . .
C4 C 0.6768(2) 0.6296(2) 0.4814(5) 0.0479(8) Uani 1 1 d . U . . .
H4 H 0.7019 0.5832 0.5249 0.058 Uiso 1 1 calc R . . . .
C5 C 0.6641(2) 0.63881(19) 0.3447(4) 0.0450(8) Uani 1 1 d . U . . .
H5 H 0.6826 0.5998 0.2935 0.054 Uiso 1 1 calc R . . . .
C6 C 0.6233(2) 0.70648(17) 0.2798(3) 0.0339(6) Uani 1 1 d . U . . .
N1 N 0.5972(2) 0.9323(2) 0.6435(3) 0.0525(8) Uani 1 1 d . U . . .
H1A H 0.6003 0.9140 0.7250 0.063 Uiso 1 1 calc R . . . .
H1B H 0.5997 0.9817 0.6317 0.063 Uiso 1 1 calc R . . . .
N2 N 0.58524(19) 0.81065(16) 0.5634(3) 0.0355(6) Uani 1 1 d . U . . .
H2 H 0.5653 0.7973 0.6335 0.043 Uiso 1 1 calc R . . . .
N3 N 0.58888(16) 0.75964(13) 0.3505(3) 0.0267(5) Uani 1 1 d . U . . .
N4 N 0.6119(2) 0.72011(17) 0.1449(3) 0.0416(6) Uani 1 1 d . U . . .
H4A H 0.6214 0.7697 0.1481 0.050 Uiso 1 1 d GR . . . .
H4B H 0.6454 0.6970 0.0963 0.050 Uiso 1 1 d GR . . . .
O11 O 0.4561(13) 0.2327(11) 0.2108(18) 0.0445(16) Uiso 0.148(6) 1 d . U . A -1
O12 O 0.5118(8) 0.2667(4) 0.2610(13) 0.0445(16) Uiso 0.352(6) 1 d . U . A -2
Cl21 Cl 0.7741(5) 0.3882(4) 0.4743(7) 0.0439(12) Uani 0.524(8) 1 d D U . B 1
O21 O 0.7036(11) 0.3298(8) 0.4205(15) 0.048(2) Uani 0.524(8) 1 d D U . B 1
O22 O 0.7407(6) 0.4353(5) 0.5628(8) 0.069(2) Uani 0.524(8) 1 d D U . B 1
O23 O 0.7822(7) 0.4383(5) 0.3670(7) 0.080(2) Uani 0.524(8) 1 d D U . B 1
O24 O 0.8637(5) 0.3572(4) 0.5475(10) 0.085(2) Uani 0.524(8) 1 d D U . B 1
Cl26 Cl 0.7678(5) 0.3898(4) 0.4558(7) 0.0358(10) Uani 0.476(8) 1 d D U . B 2
O26 O 0.7137(12) 0.3236(8) 0.3948(16) 0.048(3) Uani 0.476(8) 1 d D U . B 2
O27 O 0.7650(7) 0.3987(5) 0.5918(7) 0.064(2) Uani 0.476(8) 1 d D U . B 2
O28 O 0.7234(8) 0.4546(4) 0.3744(9) 0.081(2) Uani 0.476(8) 1 d D U . B 2
O29 O 0.8587(5) 0.3873(4) 0.4375(9) 0.067(2) Uani 0.476(8) 1 d D U . B 2
C51 C 0.5130(14) 0.5059(12) 0.068(2) 0.093(3) Uiso 0.25 1 d D U . C -1
H51A H 0.5301 0.5551 0.1133 0.139 Uiso 0.25 1 calc R . . C -1
H51B H 0.5651 0.4889 0.0322 0.139 Uiso 0.25 1 calc R . . C -1
H51C H 0.4532 0.5109 -0.0083 0.139 Uiso 0.25 1 calc R . . C -1
C52 C 0.4994(5) 0.4509(8) 0.1658(15) 0.093(3) Uiso 0.25 1 d D U . C -1
C53 C 0.500(2) 0.4618(13) 0.3917(19) 0.093(3) Uiso 0.25 1 d D U . C -1
H53A H 0.5584 0.4350 0.4477 0.111 Uiso 0.25 1 calc R . . C -1
H53B H 0.4475 0.4239 0.3606 0.111 Uiso 0.25 1 calc R . . C -1
C54 C 0.4714(19) 0.5193(14) 0.478(2) 0.093(3) Uiso 0.25 1 d D U . C -1
H54A H 0.4593 0.4942 0.5573 0.139 Uiso 0.25 1 calc R . . C -1
H54B H 0.5235 0.5564 0.5112 0.139 Uiso 0.25 1 calc R . . C -1
H54C H 0.4127 0.5453 0.4240 0.139 Uiso 0.25 1 calc R . . C -1
O51 O 0.4785(9) 0.3867(8) 0.1419(16) 0.093(3) Uiso 0.25 1 d D U . C -1
O52 O 0.5163(10) 0.4905(8) 0.2892(12) 0.093(3) Uiso 0.25 1 d D U . C -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
Ni1 S1 2.1647(8) . ?
Ni1 S1 2.1647(8) 2_655 ?
Ni1 N3 1.923(2) . ?
Ni1 N3 1.922(2) 2_655 ?
S1 C1 1.707(3) . ?
C1 N1 1.315(4) . ?
C1 N2 1.354(4) . ?
C2 C3 1.376(4) . ?
C2 N2 1.408(4) . ?
C2 N3 1.349(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.359(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(5) . ?
C6 N3 1.366(4) . ?
C6 N4 1.356(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2 0.8800 . ?
N4 H4A 0.8836 . ?
N4 H4B 0.8911 . ?
Cl21 O21 1.439(6) . ?
Cl21 O22 1.415(6) . ?
Cl21 O23 1.437(7) . ?
Cl21 O24 1.402(7) . ?
Cl26 O26 1.440(6) . ?
Cl26 O27 1.409(6) . ?
Cl26 O28 1.444(7) . ?
Cl26 O29 1.391(7) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C51 C52 1.447(15) . ?
C52 O51 1.178(9) . ?
C52 O52 1.394(13) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C53 C54 1.483(17) . ?
C53 O52 1.248(16) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 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
S1 Ni1 S1 87.80(4) 2_655 . ?
N3 Ni1 S1 90.84(7) 2_655 2_655 ?
N3 Ni1 S1 169.76(7) 2_655 . ?
N3 Ni1 S1 90.85(7) . . ?
N3 Ni1 S1 169.76(7) . 2_655 ?
N3 Ni1 N3 92.25(14) 2_655 . ?
C1 S1 Ni1 99.92(12) . . ?
N1 C1 S1 118.7(3) . . ?
N1 C1 N2 117.5(3) . . ?
N2 C1 S1 123.9(2) . . ?
C3 C2 N2 118.3(3) . . ?
N3 C2 C3 123.5(3) . . ?
N3 C2 N2 118.2(2) . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.4(3) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
N3 C6 C5 120.2(3) . . ?
N4 C6 C5 122.2(3) . . ?
N4 C6 N3 117.5(3) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 C2 126.7(3) . . ?
C1 N2 H2 116.6 . . ?
C2 N2 H2 116.6 . . ?
C2 N3 Ni1 122.35(19) . . ?
C2 N3 C6 118.0(3) . . ?
C6 N3 Ni1 119.2(2) . . ?
C6 N4 H4A 99.7 . . ?
C6 N4 H4B 124.3 . . ?
H4A N4 H4B 111.6 . . ?
O22 Cl21 O21 108.7(7) . . ?
O22 Cl21 O23 104.4(7) . . ?
O23 Cl21 O21 111.2(8) . . ?
O24 Cl21 O21 111.4(9) . . ?
O24 Cl21 O22 109.3(6) . . ?
O24 Cl21 O23 111.6(7) . . ?
O26 Cl26 O28 107.5(9) . . ?
O27 Cl26 O26 109.9(7) . . ?
O27 Cl26 O28 109.8(7) . . ?
O29 Cl26 O26 109.5(8) . . ?
O29 Cl26 O27 116.5(7) . . ?
O29 Cl26 O28 103.1(7) . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C52 C51 H51A 109.5 . . ?
C52 C51 H51B 109.5 . . ?
C52 C51 H51C 109.5 . . ?
O51 C52 C51 125.5(15) . . ?
O51 C52 O52 129.1(14) . . ?
O52 C52 C51 105.4(11) . . ?
H53A C53 H53B 107.9 . . ?
C54 C53 H53A 109.1 . . ?
C54 C53 H53B 109.1 . . ?
O52 C53 H53A 109.1 . . ?
O52 C53 H53B 109.1 . . ?
O52 C53 C54 112.4(17) . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C53 O52 C52 121.8(14) . . ?

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
N1 H1A O24 0.88 2.43 3.305(10) 170.4 4_656
N1 H1A O27 0.88 2.28 2.895(8) 127.2 4_656
N1 H1B O23 0.88 2.22 2.898(7) 133.7 7_666
N1 H1B O29 0.88 2.54 3.393(9) 163.6 7_666
N2 H2 O11 0.88 1.79 2.661(18) 171.2 5_666
N2 H2 O11 0.88 2.04 2.841(18) 150.0 6_566
N2 H2 O12 0.88 2.10 2.929(12) 156.3 5_666
N2 H2 O12 0.88 2.04 2.890(13) 160.9 6_566
N4 H4A O29 0.88 2.30 3.127(7) 155.9 4_655
N4 H4B O21 0.89 2.25 3.103(13) 159.8 6_565
N4 H4B O26 0.89 2.56 3.400(15) 156.8 6_565
N4 H4B O27 0.89 2.43 3.218(7) 147.3 6_565

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
Ni1 S1 C1 N1 -152.7(3) . . . . ?
Ni1 S1 C1 N2 26.3(3) . . . . ?
S1 C1 N2 C2 25.1(4) . . . . ?
C2 C3 C4 C5 5.2(5) . . . . ?
C3 C2 N2 C1 144.3(3) . . . . ?
C3 C2 N3 Ni1 163.4(2) . . . . ?
C3 C2 N3 C6 -8.7(4) . . . . ?
C3 C4 C5 C6 -2.6(5) . . . . ?
C4 C5 C6 N3 -5.8(5) . . . . ?
C4 C5 C6 N4 177.6(3) . . . . ?
C5 C6 N3 Ni1 -161.2(2) . . . . ?
C5 C6 N3 C2 11.2(4) . . . . ?
N1 C1 N2 C2 -155.9(3) . . . . ?
N2 C2 C3 C4 179.5(3) . . . . ?
N2 C2 N3 Ni1 -15.6(4) . . . . ?
N2 C2 N3 C6 172.3(3) . . . . ?
N3 C2 C3 C4 0.5(5) . . . . ?
N3 C2 N2 C1 -36.6(4) . . . . ?
N4 C6 N3 Ni1 15.6(3) . . . . ?
N4 C6 N3 C2 -172.0(3) . . . . ?
C51 C52 O52 C53 172(2) . . . . ?
C54 C53 O52 C52 -149.1(18) . . . . ?
O51 C52 O52 C53 -8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_4_2014ncs0935
_database_code_depnum_ccdc_archive 'CCDC 2082369'
loop_
_audit_author_name
_audit_author_address
'Peter Horton'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2016-05-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 N6 S2 Zn, 2(Cl O4)'
_chemical_formula_sum            'C14 H18 Cl2 N6 O8 S2 Zn'
_chemical_formula_weight         598.73
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C34 H50 N6 O2 S2 Zn (ClO4)2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.1243(2)
_cell_length_b                   11.4452(3)
_cell_length_c                   18.1830(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.109(3)
_cell_angle_gamma                90
_cell_volume                     1066.21(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4960
_cell_measurement_theta_min      2.0540
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0074
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7361
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.103
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -109.00   71.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000    0.0000    0.0000 360

#__ type_ start__ end____ width___ exp.time_
  2 omega  -69.00   22.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -72.0000  150.0000 182

#__ type_ start__ end____ width___ exp.time_
  3 omega  -57.00   14.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -72.0000  -30.0000 142

#__ type_ start__ end____ width___ exp.time_
  4 omega  -79.00   19.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -54.0000    0.0000 196

#__ type_ start__ end____ width___ exp.time_
  5 omega  -27.00    1.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   72.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega  -22.00    3.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -72.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega  -94.00   32.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   18.0000  -60.0000 252
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_UB_11      -0.0536030000
_diffrn_orient_matrix_UB_12      0.0571268000
_diffrn_orient_matrix_UB_13      -0.0006776000
_diffrn_orient_matrix_UB_21      0.1038893000
_diffrn_orient_matrix_UB_22      0.0191469000
_diffrn_orient_matrix_UB_23      -0.0221728000
_diffrn_orient_matrix_UB_31      -0.0741879000
_diffrn_orient_matrix_UB_32      -0.0144352000
_diffrn_orient_matrix_UB_33      -0.0320877000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.6366 3973 10214
2 0.3634 3992 10214

_diffrn_oxdiff_twin_integration_method simultaneous
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                7240
_reflns_number_total             7361
_reflns_special_details          
;
 _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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.021(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         7361
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.130
_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)+(0.0880P)²+0.2970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1100
_refine_special_details          
'Refined as a 2-component twin - 180 degrees about direct axis 1 0 0 at 34.8%'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6516(14) 0.3484(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N1-H1A = N1-H1B = N2-H2 = N11-H11A = N11-H11B = N12-H12
 0.87 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C13(H13), C14(H14), C16(H16)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Zn1 Zn 0.73291(11) 0.20823(6) 0.75058(3) 0.01218(16) Uani 1 1 d . . . . .
C1 C 0.8233(10) 0.4755(5) 0.7131(3) 0.0128(10) Uani 1 1 d . . . . .
C2 C 0.4648(10) 0.3687(5) 0.6421(3) 0.0118(10) Uani 1 1 d . . . . .
C3 C 0.2725(11) 0.3957(5) 0.5895(3) 0.0160(11) Uani 1 1 d . . . . .
H3 H 0.2383 0.4747 0.5765 0.019 Uiso 1 1 calc R . . . .
C4 C 0.1339(11) 0.3072(5) 0.5567(3) 0.0153(11) Uani 1 1 d . . . . .
H4 H 0.0002 0.3250 0.5216 0.018 Uiso 1 1 calc R . . . .
C5 C 0.1874(11) 0.1907(6) 0.5745(3) 0.0160(11) Uani 1 1 d . . . . .
C6 C 0.3784(11) 0.1716(5) 0.6276(3) 0.0141(11) Uani 1 1 d . . . . .
H6 H 0.4181 0.0931 0.6406 0.017 Uiso 1 1 calc R . . . .
C7 C 0.0452(12) 0.0922(5) 0.5362(4) 0.0199(12) Uani 1 1 d . . . . .
H7A H -0.1406 0.1115 0.5313 0.030 Uiso 1 1 calc GR . . . .
H7B H 0.0658 0.0204 0.5651 0.030 Uiso 1 1 calc GR . . . .
H7C H 0.1179 0.0805 0.4873 0.030 Uiso 1 1 calc GR . . . .
N1 N 0.9382(9) 0.5783(5) 0.7106(3) 0.0156(10) Uani 1 1 d D . . . .
N2 N 0.6039(9) 0.4638(4) 0.6711(3) 0.0152(9) Uani 1 1 d D . . . .
N3 N 0.5132(9) 0.2581(4) 0.6625(3) 0.0117(9) Uani 1 1 d . . . . .
S1 S 0.9662(3) 0.37342(12) 0.76944(8) 0.0156(3) Uani 1 1 d . . . . .
C11 C 0.8443(10) -0.0574(5) 0.7889(3) 0.0124(10) Uani 1 1 d . . . . .
C12 C 0.5028(10) 0.0468(5) 0.8630(3) 0.0125(10) Uani 1 1 d . . . . .
C13 C 0.3305(12) 0.0190(5) 0.9191(3) 0.0170(11) Uani 1 1 d . . . . .
H13 H 0.3114 -0.0596 0.9350 0.020 Uiso 1 1 calc R . . . .
C14 C 0.1904(11) 0.1062(5) 0.9508(3) 0.0171(11) Uani 1 1 d . . . . .
H14 H 0.0719 0.0878 0.9887 0.021 Uiso 1 1 calc R . . . .
C15 C 0.2188(11) 0.2227(5) 0.9283(3) 0.0146(11) Uani 1 1 d . . . . .
C16 C 0.3963(10) 0.2425(5) 0.8733(3) 0.0140(11) Uani 1 1 d . . . . .
H16 H 0.4254 0.3208 0.8583 0.017 Uiso 1 1 calc R . . . .
C17 C 0.0740(12) 0.3222(5) 0.9623(4) 0.0195(12) Uani 1 1 d . . . . .
H17A H -0.0793 0.3414 0.9315 0.029 Uiso 1 1 calc GR . . . .
H17B H 0.1887 0.3906 0.9659 0.029 Uiso 1 1 calc GR . . . .
H17C H 0.0179 0.2999 1.0115 0.029 Uiso 1 1 calc GR . . . .
N11 N 0.9625(10) -0.1604(4) 0.7887(3) 0.0156(10) Uani 1 1 d D . . . .
N12 N 0.6417(9) -0.0478(4) 0.8347(3) 0.0144(9) Uani 1 1 d D . . . .
N13 N 0.5314(9) 0.1562(4) 0.8395(3) 0.0124(9) Uani 1 1 d . . . . .
S11 S 0.9704(3) 0.04554(12) 0.73201(8) 0.0164(3) Uani 1 1 d . . . . .
O21 O 0.4064(9) 0.8532(5) 0.5542(3) 0.0268(10) Uani 1 1 d . . . . .
O22 O 0.7660(8) 0.7742(4) 0.6194(2) 0.0192(9) Uani 1 1 d . . . . .
O23 O 0.3638(9) 0.6759(4) 0.6176(3) 0.0227(10) Uani 1 1 d . . . . .
O24 O 0.4102(9) 0.8519(4) 0.6828(3) 0.0262(10) Uani 1 1 d . . . . .
Cl21 Cl 0.4867(2) 0.79008(11) 0.61842(7) 0.0137(3) Uani 1 1 d . . . . .
O31 O 0.4140(8) 0.6397(5) 0.7929(3) 0.0251(10) Uani 1 1 d . . . . .
O32 O 0.5532(9) 0.7319(4) 0.9020(3) 0.0251(10) Uani 1 1 d . . . . .
O33 O 0.1384(9) 0.6414(5) 0.8937(3) 0.0273(11) Uani 1 1 d . . . . .
O34 O 0.5199(9) 0.5274(4) 0.8977(3) 0.0290(11) Uani 1 1 d . . . . .
Cl31 Cl 0.4063(2) 0.63355(12) 0.87182(7) 0.0140(3) Uani 1 1 d . . . . .
H1A H 1.03(2) 0.595(12) 0.750(4) 0.08(4) Uiso 1 1 d D . . . .
H1B H 0.889(14) 0.634(6) 0.682(4) 0.02(2) Uiso 1 1 d D . . . .
H2 H 0.551(12) 0.530(4) 0.655(3) 0.007(15) Uiso 1 1 d D . . . .
H11A H 1.081(12) -0.167(7) 0.757(3) 0.019(19) Uiso 1 1 d D . . . .
H11B H 0.902(14) -0.212(6) 0.819(4) 0.02(2) Uiso 1 1 d D . . . .
H12 H 0.591(16) -0.111(5) 0.858(5) 0.03(2) Uiso 1 1 d 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
Zn1 N3 2.021(5) . ?
Zn1 S1 2.2596(16) . ?
Zn1 N13 2.025(5) . ?
Zn1 S11 2.2535(15) . ?
C1 N1 1.316(7) . ?
C1 N2 1.354(7) . ?
C1 S1 1.710(6) . ?
C2 C3 1.396(8) . ?
C2 N2 1.399(7) . ?
C2 N3 1.341(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.367(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(9) . ?
C5 C6 1.379(8) . ?
C5 C7 1.506(8) . ?
C6 H6 0.9500 . ?
C6 N3 1.358(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N1 H1A 0.86(3) . ?
N1 H1B 0.86(3) . ?
N2 H2 0.86(3) . ?
C11 N11 1.325(7) . ?
C11 N12 1.348(7) . ?
C11 S11 1.703(6) . ?
C12 C13 1.399(8) . ?
C12 N12 1.399(7) . ?
C12 N13 1.333(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.364(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.402(8) . ?
C15 C16 1.384(8) . ?
C15 C17 1.499(8) . ?
C16 H16 0.9500 . ?
C16 N13 1.359(7) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N11 H11A 0.85(3) . ?
N11 H11B 0.86(3) . ?
N12 H12 0.88(3) . ?
O21 Cl21 1.426(5) . ?
O22 Cl21 1.443(4) . ?
O23 Cl21 1.451(4) . ?
O24 Cl21 1.429(5) . ?
O31 Cl31 1.438(5) . ?
O32 Cl31 1.456(4) . ?
O33 Cl31 1.440(5) . ?
O34 Cl31 1.423(5) . ?

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
N3 Zn1 S1 99.73(14) . . ?
N3 Zn1 N13 115.51(18) . . ?
N3 Zn1 S11 114.13(14) . . ?
N13 Zn1 S1 113.64(14) . . ?
N13 Zn1 S11 99.33(14) . . ?
S11 Zn1 S1 115.37(5) . . ?
N1 C1 N2 115.9(5) . . ?
N1 C1 S1 116.4(4) . . ?
N2 C1 S1 127.7(4) . . ?
C3 C2 N2 115.7(5) . . ?
N3 C2 C3 121.6(5) . . ?
N3 C2 N2 122.7(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.5(5) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C7 121.1(5) . . ?
C6 C5 C4 116.5(5) . . ?
C6 C5 C7 122.4(6) . . ?
C5 C6 H6 118.0 . . ?
N3 C6 C5 124.0(5) . . ?
N3 C6 H6 118.0 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 N1 H1A 114(10) . . ?
C1 N1 H1B 124(5) . . ?
H1A N1 H1B 119(10) . . ?
C1 N2 C2 134.5(5) . . ?
C1 N2 H2 111(4) . . ?
C2 N2 H2 114(4) . . ?
C2 N3 Zn1 125.6(4) . . ?
C2 N3 C6 118.0(5) . . ?
C6 N3 Zn1 115.8(4) . . ?
C1 S1 Zn1 105.2(2) . . ?
N11 C11 N12 115.6(5) . . ?
N11 C11 S11 115.8(4) . . ?
N12 C11 S11 128.6(4) . . ?
N12 C12 C13 115.2(5) . . ?
N13 C12 C13 121.5(5) . . ?
N13 C12 N12 123.3(5) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.1(5) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 120.9(5) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C17 123.2(5) . . ?
C16 C15 C14 116.1(5) . . ?
C16 C15 C17 120.7(5) . . ?
C15 C16 H16 118.1 . . ?
N13 C16 C15 123.7(5) . . ?
N13 C16 H16 118.1 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 N11 H11A 114(6) . . ?
C11 N11 H11B 116(6) . . ?
H11A N11 H11B 130(8) . . ?
C11 N12 C12 134.0(5) . . ?
C11 N12 H12 118(6) . . ?
C12 N12 H12 107(6) . . ?
C12 N13 Zn1 126.4(4) . . ?
C12 N13 C16 118.6(5) . . ?
C16 N13 Zn1 114.8(4) . . ?
C11 S11 Zn1 105.6(2) . . ?
O21 Cl21 O22 110.1(3) . . ?
O21 Cl21 O23 109.2(3) . . ?
O21 Cl21 O24 109.9(3) . . ?
O22 Cl21 O23 108.5(3) . . ?
O24 Cl21 O22 109.9(3) . . ?
O24 Cl21 O23 109.2(3) . . ?
O31 Cl31 O32 108.3(3) . . ?
O31 Cl31 O33 108.6(3) . . ?
O33 Cl31 O32 109.7(3) . . ?
O34 Cl31 O31 110.7(3) . . ?
O34 Cl31 O32 109.3(3) . . ?
O34 Cl31 O33 110.4(3) . . ?

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
N1 H1A O31 0.86(3) 2.18(8) 2.922(6) 145(11) 1_655
N1 H1B O22 0.86(3) 2.06(4) 2.916(7) 176(8) .
N2 H2 O23 0.86(3) 2.03(3) 2.881(7) 170(6) .
N11 H11A O24 0.85(3) 2.19(4) 3.027(7) 168(8) 1_645
N11 H11B O32 0.86(3) 2.45(5) 3.214(7) 148(7) 1_545
N11 H11B O33 0.86(3) 2.47(6) 3.089(7) 129(6) 1_645
N12 H12 O32 0.88(3) 1.98(4) 2.844(7) 166(8) 1_545

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
C2 C3 C4 C5 -1.3(9) . . . . ?
C3 C2 N2 C1 -168.3(6) . . . . ?
C3 C2 N3 Zn1 -167.5(4) . . . . ?
C3 C2 N3 C6 3.3(8) . . . . ?
C3 C4 C5 C6 2.0(9) . . . . ?
C3 C4 C5 C7 -177.0(6) . . . . ?
C4 C5 C6 N3 0.1(9) . . . . ?
C5 C6 N3 Zn1 169.1(5) . . . . ?
C5 C6 N3 C2 -2.7(9) . . . . ?
C7 C5 C6 N3 179.0(6) . . . . ?
N1 C1 N2 C2 159.7(6) . . . . ?
N1 C1 S1 Zn1 -175.4(4) . . . . ?
N2 C1 S1 Zn1 5.4(5) . . . . ?
N2 C2 C3 C4 177.8(6) . . . . ?
N2 C2 N3 Zn1 13.3(8) . . . . ?
N2 C2 N3 C6 -175.8(5) . . . . ?
N3 C2 C3 C4 -1.4(9) . . . . ?
N3 C2 N2 C1 11.0(10) . . . . ?
S1 C1 N2 C2 -21.0(9) . . . . ?
C12 C13 C14 C15 -0.6(9) . . . . ?
C13 C12 N12 C11 -169.8(6) . . . . ?
C13 C12 N13 Zn1 -171.2(4) . . . . ?
C13 C12 N13 C16 2.5(8) . . . . ?
C13 C14 C15 C16 -0.4(9) . . . . ?
C13 C14 C15 C17 -178.7(6) . . . . ?
C14 C15 C16 N13 2.6(8) . . . . ?
C15 C16 N13 Zn1 170.7(4) . . . . ?
C15 C16 N13 C12 -3.7(8) . . . . ?
C17 C15 C16 N13 -179.0(5) . . . . ?
N11 C11 N12 C12 164.3(6) . . . . ?
N11 C11 S11 Zn1 -177.8(4) . . . . ?
N12 C11 S11 Zn1 1.5(6) . . . . ?
N12 C12 C13 C14 178.9(5) . . . . ?
N12 C12 N13 Zn1 9.5(8) . . . . ?
N12 C12 N13 C16 -176.8(5) . . . . ?
N13 C12 C13 C14 -0.5(9) . . . . ?
N13 C12 N12 C11 9.6(9) . . . . ?
S11 C11 N12 C12 -15.0(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6516(14)
2 0.3484(14)

####################################################################### 
# 
# 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_15_2014ncs0938
_database_code_depnum_ccdc_archive 'CCDC 2082372'
loop_
_audit_author_name
_audit_author_address
'Peter Horton'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2016-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H34 Cu N6 O2 S2, Cl O4, H2 O'
_chemical_formula_sum            'C24 H36 Cl Cu N6 O7 S2'
_chemical_formula_weight         683.70
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H32 N6 O2 S2 Cu Cl O4'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   9.0770(3)
_cell_length_b                   17.2213(8)
_cell_length_c                   19.5201(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3051.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10806
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.1750
_cell_measurement_theta_min      2.3540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35113
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         1.577
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   39.00   71.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   72.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  2 omega  -69.00   22.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -72.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -71.00   22.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -72.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega  -95.00  -14.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000    0.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega  -35.00   -8.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   54.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -94.00   71.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   18.0000   30.0000 165

#__ type_ start__ end____ width___ exp.time_
  7 omega  -69.00   -6.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -72.0000  120.0000 63
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_UB_11      -0.0103819000
_diffrn_orient_matrix_UB_12      0.0399254000
_diffrn_orient_matrix_UB_13      -0.0075189000
_diffrn_orient_matrix_UB_21      -0.0768754000
_diffrn_orient_matrix_UB_22      -0.0042198000
_diffrn_orient_matrix_UB_23      0.0053442000
_diffrn_orient_matrix_UB_31      0.0094870000
_diffrn_orient_matrix_UB_32      0.0091773000
_diffrn_orient_matrix_UB_33      0.0351465000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4976
_reflns_number_total             6990
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.130
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details 
;
 Flack x determined using 1590 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6990
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0662
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+4.0840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1439
_refine_special_details          
'There is some minor disorder of the perchlorate ion and water molecule, that is not readily modelled. As a result some displacement restraints (RIGU) have been used on these atoms.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid body (RIGU) restrains
 Cl41, O41, O42, O43, O44, O51
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Free rotating group:
 O51(H51A,H51B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), N2(H2), N3(H3A), C21(H21), C23(H23), C24(H24),
 N22(H22), N23(H23A)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.59261(10) 0.38690(6) 0.28264(5) 0.0256(2) Uani 1 1 d . . . . .
C1 C 0.4630(8) 0.5421(5) 0.2712(4) 0.0283(18) Uani 1 1 d . . . . .
H1 H 0.4663 0.5271 0.2244 0.034 Uiso 1 1 calc R . . . .
C2 C 0.3955(8) 0.6116(5) 0.2865(4) 0.0292(16) Uani 1 1 d . . . . .
C3 C 0.3897(9) 0.6307(4) 0.3562(4) 0.0274(17) Uani 1 1 d . . . . .
H3 H 0.3449 0.6780 0.3701 0.033 Uiso 1 1 calc R . . . .
C4 C 0.4474(8) 0.5824(5) 0.4042(4) 0.0273(18) Uani 1 1 d . . . . .
H4 H 0.4422 0.5953 0.4515 0.033 Uiso 1 1 calc R . . . .
C5 C 0.5141(8) 0.5140(4) 0.3833(4) 0.0222(16) Uani 1 1 d . . . . .
C6 C 0.5909(8) 0.3920(4) 0.4420(3) 0.0243(15) Uani 1 1 d . . . . .
C7 C 0.6297(8) 0.4090(5) 0.5676(4) 0.0238(17) Uani 1 1 d . . . . .
C8 C 0.3293(10) 0.6623(5) 0.2322(4) 0.039(2) Uani 1 1 d . . . . .
H8A H 0.2257 0.6723 0.2432 0.059 Uiso 1 1 calc GR . . . .
H8B H 0.3359 0.6360 0.1878 0.059 Uiso 1 1 calc GR . . . .
H8C H 0.3830 0.7116 0.2302 0.059 Uiso 1 1 calc GR . . . .
C9 C 0.6533(10) 0.3602(5) 0.6318(4) 0.033(2) Uani 1 1 d . . . . .
C10 C 0.5323(11) 0.2988(5) 0.6369(4) 0.043(2) Uani 1 1 d . . . . .
H10A H 0.5433 0.2699 0.6798 0.064 Uiso 1 1 calc GR . . . .
H10B H 0.5403 0.2629 0.5981 0.064 Uiso 1 1 calc GR . . . .
H10C H 0.4357 0.3241 0.6359 0.064 Uiso 1 1 calc GR . . . .
C11 C 0.6484(12) 0.4139(5) 0.6938(4) 0.046(3) Uani 1 1 d . . . . .
H11A H 0.7272 0.4526 0.6901 0.069 Uiso 1 1 calc GR . . . .
H11B H 0.6619 0.3834 0.7357 0.069 Uiso 1 1 calc GR . . . .
H11C H 0.5528 0.4404 0.6954 0.069 Uiso 1 1 calc GR . . . .
C12 C 0.8060(10) 0.3230(6) 0.6283(5) 0.044(2) Uani 1 1 d . . . . .
H12A H 0.8805 0.3636 0.6221 0.066 Uiso 1 1 calc GR . . . .
H12B H 0.8099 0.2868 0.5897 0.066 Uiso 1 1 calc GR . . . .
H12C H 0.8255 0.2950 0.6710 0.066 Uiso 1 1 calc GR . . . .
N1 N 0.5244(7) 0.4938(4) 0.3169(3) 0.0262(14) Uani 1 1 d . . . . .
N2 N 0.5770(7) 0.4683(4) 0.4357(3) 0.0256(14) Uani 1 1 d . . . . .
H2 H 0.6134 0.4951 0.4702 0.031 Uiso 1 1 calc R . . . .
N3 N 0.6256(7) 0.3664(4) 0.5074(3) 0.0273(16) Uani 1 1 d . . . . .
H3A H 0.6479 0.3168 0.5111 0.033 Uiso 1 1 calc R . . . .
O1 O 0.6165(6) 0.4786(3) 0.5677(3) 0.0308(13) Uani 1 1 d . . . . .
S1 S 0.5708(2) 0.32352(12) 0.38182(9) 0.0292(5) Uani 1 1 d . . . . .
C21 C 0.9091(9) 0.3969(4) 0.3052(4) 0.0270(16) Uani 1 1 d . . . . .
H21 H 0.8739 0.3967 0.3510 0.032 Uiso 1 1 calc R . . . .
C22 C 1.0596(8) 0.4042(5) 0.2944(4) 0.0272(18) Uani 1 1 d . . . . .
C23 C 1.1082(9) 0.4027(4) 0.2277(4) 0.0300(18) Uani 1 1 d . . . . .
H23 H 1.2102 0.4081 0.2180 0.036 Uiso 1 1 calc R . . . .
C24 C 1.0094(8) 0.3935(5) 0.1754(4) 0.0261(17) Uani 1 1 d . . . . .
H24 H 1.0421 0.3916 0.1292 0.031 Uiso 1 1 calc R . . . .
C25 C 0.8602(8) 0.3870(5) 0.1910(4) 0.0238(16) Uani 1 1 d . . . . .
C26 C 0.6237(8) 0.3626(4) 0.1259(4) 0.0263(18) Uani 1 1 d . . . . .
C27 C 0.6629(9) 0.3558(5) -0.0006(4) 0.0275(18) Uani 1 1 d . . . . .
C28 C 1.1615(9) 0.4138(5) 0.3542(4) 0.034(2) Uani 1 1 d . . . . .
H28A H 1.2435 0.3771 0.3501 0.051 Uiso 1 1 calc GR . . . .
H28B H 1.1077 0.4037 0.3968 0.051 Uiso 1 1 calc GR . . . .
H28C H 1.2001 0.4670 0.3549 0.051 Uiso 1 1 calc GR . . . .
C29 C 0.5869(9) 0.3370(4) -0.0680(4) 0.0287(17) Uani 1 1 d . . . . .
C30 C 0.4487(9) 0.2877(5) -0.0577(4) 0.035(2) Uani 1 1 d . . . . .
H30A H 0.4718 0.2435 -0.0280 0.053 Uiso 1 1 calc GR . . . .
H30B H 0.4141 0.2687 -0.1022 0.053 Uiso 1 1 calc GR . . . .
H30C H 0.3716 0.3194 -0.0364 0.053 Uiso 1 1 calc GR . . . .
C31 C 0.6956(9) 0.2912(6) -0.1121(4) 0.038(2) Uani 1 1 d . . . . .
H31A H 0.7861 0.3215 -0.1181 0.058 Uiso 1 1 calc GR . . . .
H31B H 0.6515 0.2808 -0.1570 0.058 Uiso 1 1 calc GR . . . .
H31C H 0.7190 0.2419 -0.0895 0.058 Uiso 1 1 calc GR . . . .
C32 C 0.5473(11) 0.4134(5) -0.1014(4) 0.046(3) Uani 1 1 d . . . . .
H32A H 0.4863 0.4440 -0.0700 0.069 Uiso 1 1 calc GR . . . .
H32B H 0.4923 0.4035 -0.1437 0.069 Uiso 1 1 calc GR . . . .
H32C H 0.6375 0.4421 -0.1121 0.069 Uiso 1 1 calc GR . . . .
N21 N 0.8095(7) 0.3900(4) 0.2534(3) 0.0249(14) Uani 1 1 d . . . . .
N22 N 0.7654(6) 0.3811(4) 0.1339(3) 0.0251(14) Uani 1 1 d . . . . .
H22 H 0.8096 0.3921 0.0950 0.030 Uiso 1 1 calc R . . . .
N23 N 0.5802(7) 0.3518(4) 0.0584(3) 0.0259(14) Uani 1 1 d . . . . .
H23A H 0.4864 0.3408 0.0525 0.031 Uiso 1 1 calc R . . . .
O21 O 0.7933(6) 0.3739(3) 0.0010(3) 0.0318(13) Uani 1 1 d . . . . .
S21 S 0.4947(2) 0.34679(13) 0.18500(10) 0.0293(5) Uani 1 1 d . . . . .
Cl41 Cl 0.2046(2) 0.49815(12) 0.55840(10) 0.0311(5) Uani 1 1 d . U . . .
O41 O 0.2822(7) 0.4547(4) 0.5069(3) 0.0411(15) Uani 1 1 d . U . . .
O42 O 0.2574(8) 0.4758(4) 0.6239(3) 0.0504(17) Uani 1 1 d . U . . .
O43 O 0.0500(6) 0.4831(4) 0.5533(4) 0.0532(19) Uani 1 1 d . U . . .
O44 O 0.2310(6) 0.5796(3) 0.5479(3) 0.0339(14) Uani 1 1 d . U . . .
O51 O 0.1885(13) 0.2967(4) 0.5071(4) 0.088(3) Uani 1 1 d . U . . .
H51A H 0.1834 0.3469 0.5114 0.132 Uiso 1 1 d G . . . .
H51B H 0.2784 0.2833 0.4971 0.132 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 N1 2.054(7) . ?
Cu1 S1 2.231(2) . ?
Cu1 N21 2.050(6) . ?
Cu1 S21 2.213(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(11) . ?
C1 N1 1.341(10) . ?
C2 C3 1.401(11) . ?
C2 C8 1.499(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.358(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(11) . ?
C5 N1 1.344(9) . ?
C5 N2 1.412(9) . ?
C6 N2 1.326(9) . ?
C6 N3 1.386(9) . ?
C6 S1 1.675(8) . ?
C7 C9 1.523(11) . ?
C7 N3 1.386(9) . ?
C7 O1 1.205(9) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.528(12) . ?
C9 C11 1.524(11) . ?
C9 C12 1.528(11) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N2 H2 0.8800 . ?
N3 H3A 0.8800 . ?
C21 H21 0.9500 . ?
C21 C22 1.387(10) . ?
C21 N21 1.362(9) . ?
C22 C23 1.374(10) . ?
C22 C28 1.499(10) . ?
C23 H23 0.9500 . ?
C23 C24 1.368(10) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(10) . ?
C25 N21 1.304(9) . ?
C25 N22 1.410(9) . ?
C26 N22 1.335(9) . ?
C26 N23 1.387(9) . ?
C26 S21 1.666(8) . ?
C27 C29 1.520(11) . ?
C27 N23 1.378(10) . ?
C27 O21 1.224(9) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.528(11) . ?
C29 C31 1.529(11) . ?
C29 C32 1.511(11) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
N22 H22 0.8800 . ?
N23 H23A 0.8800 . ?
Cl41 O41 1.438(6) . ?
Cl41 O42 1.419(7) . ?
Cl41 O43 1.431(6) . ?
Cl41 O44 1.437(6) . ?
O51 H51A 0.8700 . ?
O51 H51B 0.8700 . ?

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
N1 Cu1 S1 97.41(18) . . ?
N1 Cu1 S21 116.06(18) . . ?
N21 Cu1 N1 110.9(3) . . ?
N21 Cu1 S1 109.83(18) . . ?
N21 Cu1 S21 98.88(18) . . ?
S21 Cu1 S1 123.97(9) . . ?
C2 C1 H1 117.3 . . ?
N1 C1 H1 117.3 . . ?
N1 C1 C2 125.4(7) . . ?
C1 C2 C3 115.5(7) . . ?
C1 C2 C8 122.1(7) . . ?
C3 C2 C8 122.4(7) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(7) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(7) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 N2 115.9(7) . . ?
N1 C5 C4 122.3(7) . . ?
N1 C5 N2 121.7(7) . . ?
N2 C6 N3 115.0(6) . . ?
N2 C6 S1 128.5(5) . . ?
N3 C6 S1 116.6(6) . . ?
N3 C7 C9 114.2(7) . . ?
O1 C7 C9 124.1(7) . . ?
O1 C7 N3 121.7(7) . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 C10 109.5(7) . . ?
C7 C9 C11 108.3(7) . . ?
C7 C9 C12 108.8(7) . . ?
C10 C9 C12 111.4(7) . . ?
C11 C9 C10 110.3(8) . . ?
C11 C9 C12 108.4(7) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 Cu1 117.7(5) . . ?
C1 N1 C5 116.8(7) . . ?
C5 N1 Cu1 124.5(5) . . ?
C5 N2 H2 114.4 . . ?
C6 N2 C5 131.2(6) . . ?
C6 N2 H2 114.4 . . ?
C6 N3 H3A 115.9 . . ?
C7 N3 C6 128.2(7) . . ?
C7 N3 H3A 115.9 . . ?
C6 S1 Cu1 104.8(3) . . ?
C22 C21 H21 118.4 . . ?
N21 C21 H21 118.4 . . ?
N21 C21 C22 123.3(7) . . ?
C21 C22 C28 119.9(7) . . ?
C23 C22 C21 117.3(7) . . ?
C23 C22 C28 122.8(7) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.9(7) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 120.5 . . ?
C23 C24 C25 119.0(7) . . ?
C25 C24 H24 120.5 . . ?
C24 C25 N22 115.3(6) . . ?
N21 C25 C24 122.9(7) . . ?
N21 C25 N22 121.7(6) . . ?
N22 C26 N23 114.7(7) . . ?
N22 C26 S21 129.4(6) . . ?
N23 C26 S21 115.8(6) . . ?
N23 C27 C29 117.8(7) . . ?
O21 C27 C29 121.1(7) . . ?
O21 C27 N23 121.2(7) . . ?
C22 C28 H28A 109.5 . . ?
C22 C28 H28B 109.5 . . ?
C22 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 C30 112.2(6) . . ?
C27 C29 C31 107.7(7) . . ?
C30 C29 C31 108.5(7) . . ?
C32 C29 C27 107.2(6) . . ?
C32 C29 C30 110.1(7) . . ?
C32 C29 C31 111.1(7) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C21 N21 Cu1 115.7(5) . . ?
C25 N21 Cu1 126.7(5) . . ?
C25 N21 C21 117.6(6) . . ?
C25 N22 H22 112.9 . . ?
C26 N22 C25 134.2(6) . . ?
C26 N22 H22 112.9 . . ?
C26 N23 H23A 115.4 . . ?
C27 N23 C26 129.3(7) . . ?
C27 N23 H23A 115.4 . . ?
C26 S21 Cu1 105.3(3) . . ?
O42 Cl41 O41 108.9(4) . . ?
O42 Cl41 O43 110.2(4) . . ?
O42 Cl41 O44 109.7(4) . . ?
O43 Cl41 O41 109.7(4) . . ?
O43 Cl41 O44 109.3(4) . . ?
O44 Cl41 O41 109.0(4) . . ?
H51A O51 H51B 109.5 . . ?

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 O1 0.88 1.92 2.607(8) 133.2 .
N2 H2 O21 0.88 2.48 3.224(8) 142.1 2_665
N3 H3A O51 0.88 2.02 2.879(10) 164.9 3_556
N22 H22 O1 0.88 2.38 2.942(9) 121.5 2_664
N22 H22 O21 0.88 1.87 2.610(8) 140.9 .
N23 H23A O44 0.88 2.40 3.069(9) 132.6 2_564
O51 H51A O41 0.87 2.06 2.851(10) 150.1 .

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 C2 C3 C4 -0.2(12) . . . . ?
C2 C1 N1 Cu1 171.8(6) . . . . ?
C2 C1 N1 C5 2.5(11) . . . . ?
C2 C3 C4 C5 0.7(12) . . . . ?
C3 C4 C5 N1 0.4(12) . . . . ?
C3 C4 C5 N2 177.4(7) . . . . ?
C4 C5 N1 Cu1 -170.3(5) . . . . ?
C4 C5 N1 C1 -1.9(11) . . . . ?
C4 C5 N2 C6 147.2(8) . . . . ?
C8 C2 C3 C4 178.2(8) . . . . ?
C9 C7 N3 C6 172.6(7) . . . . ?
N1 C1 C2 C3 -1.5(12) . . . . ?
N1 C1 C2 C8 -179.9(8) . . . . ?
N1 C5 N2 C6 -35.7(12) . . . . ?
N2 C5 N1 Cu1 12.8(10) . . . . ?
N2 C5 N1 C1 -178.8(7) . . . . ?
N2 C6 N3 C7 8.6(11) . . . . ?
N2 C6 S1 Cu1 19.1(8) . . . . ?
N3 C6 N2 C5 -164.8(7) . . . . ?
N3 C6 S1 Cu1 -161.5(5) . . . . ?
N3 C7 C9 C10 -57.1(9) . . . . ?
N3 C7 C9 C11 -177.5(7) . . . . ?
N3 C7 C9 C12 64.9(9) . . . . ?
O1 C7 C9 C10 123.4(8) . . . . ?
O1 C7 C9 C11 3.0(11) . . . . ?
O1 C7 C9 C12 -114.6(8) . . . . ?
O1 C7 N3 C6 -7.9(12) . . . . ?
S1 C6 N2 C5 14.7(12) . . . . ?
S1 C6 N3 C7 -170.9(6) . . . . ?
C21 C22 C23 C24 -0.7(12) . . . . ?
C22 C21 N21 Cu1 -176.3(6) . . . . ?
C22 C21 N21 C25 2.9(12) . . . . ?
C22 C23 C24 C25 1.0(12) . . . . ?
C23 C24 C25 N21 0.7(14) . . . . ?
C23 C24 C25 N22 177.3(7) . . . . ?
C24 C25 N21 Cu1 176.6(6) . . . . ?
C24 C25 N21 C21 -2.6(13) . . . . ?
C24 C25 N22 C26 167.8(8) . . . . ?
C28 C22 C23 C24 179.8(8) . . . . ?
C29 C27 N23 C26 176.8(7) . . . . ?
N21 C21 C22 C23 -1.3(12) . . . . ?
N21 C21 C22 C28 178.3(7) . . . . ?
N21 C25 N22 C26 -15.5(14) . . . . ?
N22 C25 N21 Cu1 0.2(12) . . . . ?
N22 C25 N21 C21 -179.0(7) . . . . ?
N22 C26 N23 C27 1.6(11) . . . . ?
N22 C26 S21 Cu1 11.7(8) . . . . ?
N23 C26 N22 C25 -169.9(8) . . . . ?
N23 C26 S21 Cu1 -171.4(5) . . . . ?
N23 C27 C29 C30 -21.7(10) . . . . ?
N23 C27 C29 C31 -141.0(7) . . . . ?
N23 C27 C29 C32 99.4(8) . . . . ?
O21 C27 C29 C30 158.3(8) . . . . ?
O21 C27 C29 C31 38.9(10) . . . . ?
O21 C27 C29 C32 -80.7(10) . . . . ?
O21 C27 N23 C26 -3.1(13) . . . . ?
S21 C26 N22 C25 7.0(14) . . . . ?
S21 C26 N23 C27 -175.8(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_16_2014ncs0760
_database_code_depnum_ccdc_archive 'CCDC 2082373'
loop_
_audit_author_name
_audit_author_address
'Peter Horton'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2016-05-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H17 Cl Cu N3 O S'
_chemical_formula_sum            'C12 H17 Cl Cu N3 O S'
_chemical_formula_weight         350.33
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5881(9)
_cell_length_b                   6.0555(4)
_cell_length_c                   19.3671(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.012(2)
_cell_angle_gamma                90
_cell_volume                     1449.12(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14590
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.1
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.619
_exptl_absorpt_coefficient_mu    1.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14550
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
scan:
	Number of images: 136
	           Slice: -63.0000 - 73.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 18.0000
	             Phi: 120.0000
	             XTD: 44.8144
	          2theta: -16.8974
scan:
	Number of images: 100
	           Slice: -78.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -60.0000
	             XTD: 44.8144
	          2theta: -16.8974
scan:
	Number of images: 75
	           Slice: -53.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 90.0000
	             XTD: 44.8144
	          2theta: -16.8974
scan:
	Number of images: 45
	           Slice: -27.0000 - 18.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -150.0000
	             XTD: 44.8144
	          2theta: -16.8974
scan:
	Number of images: 44
	           Slice: -15.0000 - 29.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 18.0000
	             Phi: 30.0000
	             XTD: 44.8144
	          2theta: -16.8974
scan:
	Number of images: 20
	           Slice: -39.0000 - -19.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -90.0000
	             XTD: 44.8144
	          2theta: -16.8974
scan:
	Number of images: 50
	           Slice: -56.0000 - -6.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 30.0000
	             XTD: 44.8144
	          2theta: -16.8974
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.031355
_diffrn_orient_matrix_UB_12      0.073234
_diffrn_orient_matrix_UB_13      -0.014260
_diffrn_orient_matrix_UB_21      -0.151886
_diffrn_orient_matrix_UB_22      0.064809
_diffrn_orient_matrix_UB_23      -0.001134
_diffrn_orient_matrix_UB_31      0.007142
_diffrn_orient_matrix_UB_32      0.017597
_diffrn_orient_matrix_UB_33      0.049054
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2880
_reflns_number_total             3348
_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       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.030
_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)+(0.0460P)²+0.4240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.75332(4) 0.63615(9) 0.24129(3) 0.02178(13) Uani 1 1 d . . . . .
Cu1 Cu 0.59646(2) 0.51662(4) 0.26752(2) 0.01717(9) Uani 1 1 d . . . . .
C1 C 0.41989(15) 0.6215(3) 0.35416(10) 0.0153(4) Uani 1 1 d . . . . .
C2 C 0.23576(15) 0.5605(3) 0.37966(10) 0.0159(4) Uani 1 1 d . . . . .
C3 C 0.55366(15) 0.3291(3) 0.40654(10) 0.0156(4) Uani 1 1 d . . . . .
C4 C 0.57349(15) 0.1992(3) 0.46670(10) 0.0170(4) Uani 1 1 d . . . . .
H4 H 0.5273 0.2073 0.5001 0.020 Uiso 1 1 calc R . . . .
C5 C 0.66170(16) 0.0574(4) 0.47737(11) 0.0185(4) Uani 1 1 d . . . . .
H5 H 0.6763 -0.0336 0.5181 0.022 Uiso 1 1 calc R . . . .
C6 C 0.72890(15) 0.0495(4) 0.42772(11) 0.0182(4) Uani 1 1 d . . . . .
C7 C 0.70525(15) 0.1936(4) 0.37159(11) 0.0199(4) Uani 1 1 d . . . . .
H7 H 0.7527 0.1960 0.3389 0.024 Uiso 1 1 calc R . . . .
C8 C 0.82057(17) -0.1131(4) 0.43294(12) 0.0269(5) Uani 1 1 d . . . . .
H8A H 0.8131 -0.1965 0.3889 0.040 Uiso 1 1 calc GR . . . .
H8B H 0.8187 -0.2152 0.4720 0.040 Uiso 1 1 calc GR . . . .
H8C H 0.8896 -0.0335 0.4413 0.040 Uiso 1 1 calc GR . . . .
C9 C 0.11822(15) 0.6339(3) 0.35634(11) 0.0170(4) Uani 1 1 d . . . . .
C10 C 0.04538(17) 0.4741(4) 0.38703(13) 0.0237(5) Uani 1 1 d . . . . .
H10A H 0.0652 0.4759 0.4385 0.036 Uiso 1 1 calc GR . . . .
H10B H 0.0546 0.3245 0.3698 0.036 Uiso 1 1 calc GR . . . .
H10C H -0.0303 0.5194 0.3725 0.036 Uiso 1 1 calc GR . . . .
C11 C 0.08738(15) 0.6324(4) 0.27538(11) 0.0196(4) Uani 1 1 d . . . . .
H11A H 0.1100 0.4924 0.2574 0.029 Uiso 1 1 calc GR . . . .
H11B H 0.1237 0.7551 0.2564 0.029 Uiso 1 1 calc GR . . . .
H11C H 0.0088 0.6489 0.2610 0.029 Uiso 1 1 calc GR . . . .
C12 C 0.10548(15) 0.8682(3) 0.38452(11) 0.0193(4) Uani 1 1 d . . . . .
H12A H 0.0316 0.9207 0.3671 0.029 Uiso 1 1 calc GR . . . .
H12B H 0.1571 0.9677 0.3684 0.029 Uiso 1 1 calc GR . . . .
H12C H 0.1197 0.8652 0.4361 0.029 Uiso 1 1 calc GR . . . .
N1 N 0.61930(13) 0.3314(3) 0.36001(9) 0.0172(3) Uani 1 1 d . . . . .
N2 N 0.45454(13) 0.4461(3) 0.39384(9) 0.0166(3) Uani 1 1 d . . . . .
N3 N 0.31218(13) 0.6746(3) 0.34929(9) 0.0157(3) Uani 1 1 d . . . . .
O1 O 0.26265(11) 0.4125(2) 0.42218(8) 0.0196(3) Uani 1 1 d . . . . .
S1 S 0.50038(4) 0.78428(8) 0.31424(3) 0.01633(12) Uani 1 1 d . . . . .
H2 H 0.408(2) 0.392(4) 0.4118(13) 0.023(6) Uiso 1 1 d . . . . .
H3 H 0.294(2) 0.782(4) 0.3244(14) 0.026(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 Cu1 2.2504(5) . ?
Cu1 N1 2.0863(17) . ?
Cu1 S1 2.2881(6) 2_645 ?
Cu1 S1 2.3080(5) . ?
C1 N2 1.335(3) . ?
C1 N3 1.379(2) . ?
C1 S1 1.7014(19) . ?
C2 C9 1.528(3) . ?
C2 N3 1.402(3) . ?
C2 O1 1.221(2) . ?
C3 C4 1.388(3) . ?
C3 N1 1.334(2) . ?
C3 N2 1.415(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(3) . ?
C6 C7 1.381(3) . ?
C6 C8 1.506(3) . ?
C7 H7 0.9500 . ?
C7 N1 1.351(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.529(3) . ?
C9 C11 1.542(3) . ?
C9 C12 1.539(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N2 H2 0.81(3) . ?
N3 H3 0.82(3) . ?
S1 Cu1 2.2880(6) 2_655 ?

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 S1 114.59(2) . 2_645 ?
Cl1 Cu1 S1 114.25(2) . . ?
N1 Cu1 Cl1 112.57(5) . . ?
N1 Cu1 S1 92.15(5) . . ?
N1 Cu1 S1 103.38(5) . 2_645 ?
S1 Cu1 S1 116.958(13) 2_645 . ?
N2 C1 N3 115.72(17) . . ?
N2 C1 S1 124.41(14) . . ?
N3 C1 S1 119.80(15) . . ?
N3 C2 C9 115.84(17) . . ?
O1 C2 C9 122.75(17) . . ?
O1 C2 N3 121.41(17) . . ?
C4 C3 N2 116.16(17) . . ?
N1 C3 C4 122.53(17) . . ?
N1 C3 N2 121.10(18) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.09(18) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.39(19) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C8 122.20(19) . . ?
C7 C6 C5 116.88(18) . . ?
C7 C6 C8 120.88(18) . . ?
C6 C7 H7 117.8 . . ?
N1 C7 C6 124.50(18) . . ?
N1 C7 H7 117.8 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 C10 108.64(17) . . ?
C2 C9 C11 109.90(16) . . ?
C2 C9 C12 108.89(16) . . ?
C10 C9 C11 109.78(17) . . ?
C10 C9 C12 109.55(16) . . ?
C12 C9 C11 110.05(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 N1 Cu1 125.74(13) . . ?
C3 N1 C7 117.46(17) . . ?
C7 N1 Cu1 116.70(13) . . ?
C1 N2 C3 132.78(17) . . ?
C1 N2 H2 112.7(18) . . ?
C3 N2 H2 114.4(18) . . ?
C1 N3 C2 126.93(18) . . ?
C1 N3 H3 113.1(18) . . ?
C2 N3 H3 119.9(18) . . ?
Cu1 S1 Cu1 114.22(2) 2_655 . ?
C1 S1 Cu1 100.00(7) . . ?
C1 S1 Cu1 112.69(7) . 2_655 ?

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 O1 0.81(3) 1.88(3) 2.585(2) 145(2) .
N3 H3 Cl1 0.82(3) 2.51(3) 3.3188(19) 174(2) 2_655

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
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C3 N1 Cu1 179.22(15) . . . . ?
C4 C3 N1 C7 2.9(3) . . . . ?
C4 C3 N2 C1 160.6(2) . . . . ?
C4 C5 C6 C7 2.8(3) . . . . ?
C4 C5 C6 C8 -175.0(2) . . . . ?
C5 C6 C7 N1 -3.5(3) . . . . ?
C6 C7 N1 Cu1 -175.95(17) . . . . ?
C6 C7 N1 C3 0.7(3) . . . . ?
C8 C6 C7 N1 174.3(2) . . . . ?
C9 C2 N3 C1 -170.66(18) . . . . ?
N1 C3 C4 C5 -3.5(3) . . . . ?
N1 C3 N2 C1 -24.6(3) . . . . ?
N2 C1 N3 C2 -2.0(3) . . . . ?
N2 C1 S1 Cu1 167.18(15) . . . 2_655 ?
N2 C1 S1 Cu1 45.49(18) . . . . ?
N2 C3 C4 C5 171.34(18) . . . . ?
N2 C3 N1 Cu1 4.7(3) . . . . ?
N2 C3 N1 C7 -171.69(18) . . . . ?
N3 C1 N2 C3 173.3(2) . . . . ?
N3 C1 S1 Cu1 -137.75(15) . . . . ?
N3 C1 S1 Cu1 -16.06(18) . . . 2_655 ?
N3 C2 C9 C10 172.85(17) . . . . ?
N3 C2 C9 C11 52.7(2) . . . . ?
N3 C2 C9 C12 -67.9(2) . . . . ?
O1 C2 C9 C10 -7.4(3) . . . . ?
O1 C2 C9 C11 -127.5(2) . . . . ?
O1 C2 C9 C12 111.9(2) . . . . ?
O1 C2 N3 C1 9.5(3) . . . . ?
S1 C1 N2 C3 -9.9(3) . . . . ?
S1 C1 N3 C2 -179.08(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_19_2014ncs0802
_database_code_depnum_ccdc_archive 'CCDC 2082374'
loop_
_audit_author_name
_audit_author_address
'Peter Horton'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2016-05-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H28 Cl2 Cu N8 O2 S2'
_chemical_formula_sum            'C22 H28 Cl2 Cu N8 O2 S2'
_chemical_formula_weight         635.08
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7026(8)
_cell_length_b                   16.3850(11)
_cell_length_c                   7.9196(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.287(2)
_cell_angle_gamma                90
_cell_volume                     1377.58(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    23214
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    1.175
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Dark Orange'
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             654
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20899
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         2.286
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
scan:
	Number of images: 108
	           Slice: -31.0000 - 77.0000
	     Image width: 1.0000
	        Exp time: 70.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 30.0000
	             XTD: 39.8371
	          2theta: -12.9482
scan:
	Number of images: 93
	           Slice: -70.0000 - 23.0000
	     Image width: 1.0000
	        Exp time: 70.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -90.0000
	             XTD: 39.8371
	          2theta: -12.9482
scan:
	Number of images: 84
	           Slice: -61.0000 - 23.0000
	     Image width: 1.0000
	        Exp time: 70.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 90.0000
	             XTD: 39.8371
	          2theta: -12.9482
scan:
	Number of images: 66
	           Slice: -78.0000 - -12.0000
	     Image width: 1.0000
	        Exp time: 70.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 39.8371
	          2theta: -12.9482
scan:
	Number of images: 25
	           Slice: -71.0000 - -46.0000
	     Image width: 1.0000
	        Exp time: 70.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -36.0000
	             Phi: -180.0000
	             XTD: 39.8371
	          2theta: -12.9482
scan:
	Number of images: 126
	           Slice: -103.0000 - 23.0000
	     Image width: 1.0000
	        Exp time: 70.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 150.0000
	             XTD: 39.8371
	          2theta: -12.9482
scan:
	Number of images: 126
	           Slice: -76.0000 - 50.0000
	     Image width: 1.0000
	        Exp time: 70.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 150.0000
	             XTD: 39.8371
	          2theta: -12.9482
scan:
	Number of images: 26
	           Slice: -70.0000 - -44.0000
	     Image width: 1.0000
	        Exp time: 70.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -30.0000
	             XTD: 39.8371
	          2theta: -12.9482
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.108700
_diffrn_orient_matrix_UB_12      -0.063665
_diffrn_orient_matrix_UB_13      -0.018318
_diffrn_orient_matrix_UB_21      0.030006
_diffrn_orient_matrix_UB_22      0.052848
_diffrn_orient_matrix_UB_23      -0.005618
_diffrn_orient_matrix_UB_31      0.026146
_diffrn_orient_matrix_UB_32      -0.005241
_diffrn_orient_matrix_UB_33      0.090343
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2867
_reflns_number_total             3166
_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       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.519
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.025
_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)+(0.1300P)²+0.3914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1671
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.85569(6) 0.47746(4) 0.26292(8) 0.0294(2) Uani 1 1 d . . . . .
Cu1 Cu 1.0000 0.5000 0.5000 0.02305(19) Uani 1 2 d S T P . .
C1 C 0.8989(2) 0.35279(14) 0.6177(3) 0.0247(5) Uani 1 1 d . . . . .
C2 C 1.0758(2) 0.32411(14) 0.5026(3) 0.0243(5) Uani 1 1 d . . . . .
C3 C 1.1823(2) 0.33772(15) 0.4247(3) 0.0274(5) Uani 1 1 d . . . . .
H3 H 1.2102 0.3915 0.4047 0.033 Uiso 1 1 calc R . . . .
C4 C 1.2476(2) 0.26939(17) 0.3766(3) 0.0290(5) Uani 1 1 d . . . . .
H4 H 1.3211 0.2765 0.3226 0.035 Uiso 1 1 calc R . . . .
C5 C 1.2058(2) 0.19102(16) 0.4072(3) 0.0289(5) Uani 1 1 d . . . . .
H5 H 1.2507 0.1451 0.3735 0.035 Uiso 1 1 calc R . . . .
C6 C 1.0981(2) 0.17954(15) 0.4872(3) 0.0267(5) Uani 1 1 d . . . . .
C7 C 0.7197(2) 0.35376(15) 0.7262(3) 0.0267(5) Uani 1 1 d . . . . .
C8 C 0.6023(2) 0.39384(16) 0.7784(3) 0.0298(5) Uani 1 1 d . . . . .
C9 C 0.5739(3) 0.3567(2) 0.9490(4) 0.0435(7) Uani 1 1 d . . . . .
H9A H 0.4937 0.3781 0.9773 0.065 Uiso 1 1 calc GR . . . .
H9B H 0.6415 0.3713 1.0393 0.065 Uiso 1 1 calc GR . . . .
H9C H 0.5687 0.2972 0.9385 0.065 Uiso 1 1 calc GR . . . .
C10 C 0.6183(3) 0.4858(2) 0.7980(5) 0.0471(8) Uani 1 1 d . . . . .
H10A H 0.6345 0.5096 0.6893 0.071 Uiso 1 1 calc GR . . . .
H10B H 0.6894 0.4976 0.8853 0.071 Uiso 1 1 calc GR . . . .
H10C H 0.5412 0.5096 0.8321 0.071 Uiso 1 1 calc GR . . . .
C11 C 0.4941(3) 0.3739(2) 0.6385(4) 0.0464(8) Uani 1 1 d . . . . .
H11A H 0.4804 0.3148 0.6339 0.070 Uiso 1 1 calc GR . . . .
H11B H 0.5155 0.3931 0.5286 0.070 Uiso 1 1 calc GR . . . .
H11C H 0.4171 0.4012 0.6638 0.070 Uiso 1 1 calc GR . . . .
N1 N 0.80969(18) 0.39965(12) 0.6693(3) 0.0265(4) Uani 1 1 d . . . . .
N2 N 0.99708(18) 0.38296(12) 0.5518(3) 0.0251(4) Uani 1 1 d . . . . .
N3 N 1.03772(19) 0.24704(11) 0.5365(2) 0.0238(4) Uani 1 1 d . . . . .
N4 N 1.0524(2) 0.10533(14) 0.5201(3) 0.0308(5) Uani 1 1 d . . . . .
O1 O 0.72844(16) 0.27627(11) 0.7299(2) 0.0282(4) Uani 1 1 d . . . . .
S1 S 0.88980(5) 0.24614(3) 0.63228(7) 0.0250(2) Uani 1 1 d . . . . .
H4A H 0.993(3) 0.097(2) 0.575(4) 0.030(8) Uiso 1 1 d . . . . .
H4B H 1.082(3) 0.072(2) 0.468(4) 0.038(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 Cu1 2.3047(6) . ?
Cu1 Cl1 2.3047(6) 3_766 ?
Cu1 N2 1.962(2) 3_766 ?
Cu1 N2 1.962(2) . ?
C1 N1 1.330(3) . ?
C1 N2 1.326(3) . ?
C1 S1 1.755(2) . ?
C2 C3 1.381(4) . ?
C2 N2 1.369(3) . ?
C2 N3 1.364(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(4) . ?
C6 N3 1.363(3) . ?
C6 N4 1.349(3) . ?
C7 C8 1.521(3) . ?
C7 N1 1.344(3) . ?
C7 O1 1.273(3) . ?
C8 C9 1.546(4) . ?
C8 C10 1.523(4) . ?
C8 C11 1.533(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N3 S1 1.840(2) . ?
N4 H4A 0.83(3) . ?
N4 H4B 0.78(4) . ?
O1 S1 2.0403(19) . ?

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 180.00(2) . 3_766 ?
N2 Cu1 Cl1 89.25(6) . . ?
N2 Cu1 Cl1 90.75(6) . 3_766 ?
N2 Cu1 Cl1 89.25(6) 3_766 3_766 ?
N2 Cu1 Cl1 90.75(6) 3_766 . ?
N2 Cu1 N2 180.0 . 3_766 ?
N1 C1 S1 120.44(19) . . ?
N2 C1 N1 122.8(2) . . ?
N2 C1 S1 116.78(19) . . ?
N2 C2 C3 125.9(2) . . ?
N3 C2 C3 121.4(2) . . ?
N3 C2 N2 112.7(2) . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.5(2) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
N3 C6 C5 118.0(2) . . ?
N4 C6 C5 123.4(2) . . ?
N4 C6 N3 118.6(2) . . ?
N1 C7 C8 120.1(2) . . ?
O1 C7 C8 119.0(2) . . ?
O1 C7 N1 120.8(2) . . ?
C7 C8 C9 109.2(2) . . ?
C7 C8 C10 111.7(2) . . ?
C7 C8 C11 106.6(2) . . ?
C10 C8 C9 109.4(3) . . ?
C10 C8 C11 110.4(3) . . ?
C11 C8 C9 109.5(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 C7 110.7(2) . . ?
C1 N2 Cu1 118.75(17) . . ?
C1 N2 C2 113.3(2) . . ?
C2 N2 Cu1 127.02(17) . . ?
C2 N3 S1 112.51(16) . . ?
C6 N3 C2 122.0(2) . . ?
C6 N3 S1 125.15(17) . . ?
C6 N4 H4A 125(2) . . ?
C6 N4 H4B 110(3) . . ?
H4A N4 H4B 124(4) . . ?
C7 O1 S1 107.19(15) . . ?
C1 S1 N3 84.66(10) . . ?
C1 S1 O1 80.84(10) . . ?
N3 S1 O1 165.48(8) . . ?

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
N4 H4A Cl1 0.83(3) 2.53(4) 3.316(3) 158(3) 4_566
N4 H4B Cl1 0.78(4) 2.54(4) 3.308(3) 166(3) 2_745

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
C2 C3 C4 C5 -0.1(3) . . . . ?
C2 N3 S1 C1 -0.90(16) . . . . ?
C2 N3 S1 O1 2.4(4) . . . . ?
C3 C2 N2 Cu1 8.6(3) . . . . ?
C3 C2 N2 C1 177.5(2) . . . . ?
C3 C2 N3 C6 -3.7(3) . . . . ?
C3 C2 N3 S1 -177.60(17) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 N3 -1.2(3) . . . . ?
C4 C5 C6 N4 179.8(2) . . . . ?
C5 C6 N3 C2 3.2(3) . . . . ?
C5 C6 N3 S1 176.27(16) . . . . ?
C6 N3 S1 C1 -174.6(2) . . . . ?
C6 N3 S1 O1 -171.3(3) . . . . ?
C8 C7 N1 C1 -175.0(2) . . . . ?
C8 C7 O1 S1 175.13(16) . . . . ?
N1 C1 N2 Cu1 -8.4(3) . . . . ?
N1 C1 N2 C2 -178.3(2) . . . . ?
N1 C1 S1 N3 179.22(19) . . . . ?
N1 C1 S1 O1 0.06(18) . . . . ?
N1 C7 C8 C9 -134.9(2) . . . . ?
N1 C7 C8 C10 -13.8(3) . . . . ?
N1 C7 C8 C11 106.9(3) . . . . ?
N1 C7 O1 S1 -1.7(3) . . . . ?
N2 C1 N1 C7 178.3(2) . . . . ?
N2 C1 S1 N3 -0.03(18) . . . . ?
N2 C1 S1 O1 -179.19(18) . . . . ?
N2 C2 C3 C4 -177.0(2) . . . . ?
N2 C2 N3 C6 175.50(19) . . . . ?
N2 C2 N3 S1 1.6(2) . . . . ?
N3 C2 C3 C4 2.1(3) . . . . ?
N3 C2 N2 Cu1 -170.58(15) . . . . ?
N3 C2 N2 C1 -1.7(3) . . . . ?
N4 C6 N3 C2 -177.7(2) . . . . ?
N4 C6 N3 S1 -4.7(3) . . . . ?
O1 C7 C8 C9 48.3(3) . . . . ?
O1 C7 C8 C10 169.4(3) . . . . ?
O1 C7 C8 C11 -69.9(3) . . . . ?
O1 C7 N1 C1 1.8(3) . . . . ?
S1 C1 N1 C7 -0.9(3) . . . . ?
S1 C1 N2 Cu1 170.88(11) . . . . ?
S1 C1 N2 C2 1.0(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_6_2014ncs0429
_database_code_depnum_ccdc_archive 'CCDC 2082370'
loop_
_audit_author_name
_audit_author_address
'Peter Horton'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2016-05-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 Cu N8 O2 S2, Cl O4'
_chemical_formula_sum            'C26 H24 Cl Cu N8 O6 S2'
_chemical_formula_weight         707.64
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4870(7)
_cell_length_b                   17.9141(13)
_cell_length_c                   15.3930(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.4260(10)
_cell_angle_gamma                90
_cell_volume                     2773.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    33946
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.1
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    1.094
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Dark Orange'
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Blade
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36950
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.925
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
scan:
	Number of images: 137
	           Slice: -107.0000 - 30.0000
	     Image width: 1.0000
	        Exp time: 80.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -18.0000
	             Phi: -30.0000
	             XTD: 44.8344
	          2theta: -17.1095
scan:
	Number of images: 99
	           Slice: -77.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 80.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -90.0000
	             XTD: 44.8344
	          2theta: -17.1095
scan:
	Number of images: 66
	           Slice: -31.0000 - 35.0000
	     Image width: 1.0000
	        Exp time: 80.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 150.0000
	             XTD: 44.8344
	          2theta: -17.1095
scan:
	Number of images: 75
	           Slice: -53.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 80.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 60.0000
	             XTD: 44.8344
	          2theta: -17.1095
scan:
	Number of images: 56
	           Slice: -31.0000 - 25.0000
	     Image width: 1.0000
	        Exp time: 80.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -180.0000
	             XTD: 44.8344
	          2theta: -17.1095
scan:
	Number of images: 126
	           Slice: -56.0000 - 70.0000
	     Image width: 1.0000
	        Exp time: 80.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 150.0000
	             XTD: 44.8344
	          2theta: -17.1095
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.023896
_diffrn_orient_matrix_UB_12      0.049066
_diffrn_orient_matrix_UB_13      0.083094
_diffrn_orient_matrix_UB_21      -0.033113
_diffrn_orient_matrix_UB_22      -0.042217
_diffrn_orient_matrix_UB_23      0.015406
_diffrn_orient_matrix_UB_31      0.045312
_diffrn_orient_matrix_UB_32      -0.018448
_diffrn_orient_matrix_UB_33      0.046837
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5291
_reflns_number_total             6352
_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       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         6352
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.000
_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)+(0.0583P)²+1.5115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N4-H4A = N24-H24A
 0.88 with sigma of 0.02
 C22-C23 \\sim C22-C223
 with sigma of 0.02
3. Others
 Sof(C223)=Sof(C224)=Sof(H224)=Sof(C225)=Sof(H225)=Sof(C226)=Sof(H226)=
 Sof(C227)=Sof(H227)=Sof(C228)=Sof(H228)=1-FVAR(1)
 Sof(C23)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=
 Sof(H27)=Sof(C28)=Sof(H28)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32),
  C224(H224), C225(H225), C226(H226), C227(H227), C228(H228)
4.b Fitted hexagon refined as free rotating group:
 C23(C24,C25,C26,C27,C28), C223(C224,C225,C226,C227,C228)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.58520(3) 0.33483(2) 0.78447(2) 0.02436(9) Uani 1 1 d . . . . .
C1 C 0.6646(2) 0.43837(11) 0.94990(12) 0.0206(4) Uani 1 1 d . . . . .
C2 C 0.7350(2) 0.50672(11) 1.09700(12) 0.0213(4) Uani 1 1 d . . . . .
C3 C 0.8272(2) 0.56410(11) 1.14922(13) 0.0224(4) Uani 1 1 d . . . . .
C4 C 0.7992(2) 0.59184(12) 1.22690(13) 0.0257(4) Uani 1 1 d . . . . .
H4 H 0.7262 0.5725 1.2448 0.031 Uiso 1 1 calc R . . . .
C5 C 0.8776(2) 0.64734(13) 1.27756(14) 0.0302(5) Uani 1 1 d . . . . .
H5 H 0.8584 0.6660 1.3302 0.036 Uiso 1 1 calc R . . . .
C6 C 0.9844(2) 0.67579(13) 1.25158(15) 0.0316(5) Uani 1 1 d . . . . .
H6 H 1.0370 0.7147 1.2856 0.038 Uiso 1 1 calc R . . . .
C7 C 1.0142(2) 0.64723(13) 1.17574(15) 0.0301(5) Uani 1 1 d . . . . .
H7 H 1.0885 0.6660 1.1588 0.036 Uiso 1 1 calc R . . . .
C8 C 0.9366(2) 0.59155(12) 1.12456(13) 0.0256(4) Uani 1 1 d . . . . .
H8 H 0.9576 0.5721 1.0729 0.031 Uiso 1 1 calc R . . . .
C9 C 0.4884(2) 0.34098(11) 0.94831(12) 0.0207(4) Uani 1 1 d . . . . .
C10 C 0.4040(2) 0.32751(11) 1.00134(13) 0.0234(4) Uani 1 1 d . . . . .
H10 H 0.4154 0.3530 1.0571 0.028 Uiso 1 1 calc R . . . .
C11 C 0.3025(2) 0.27583(13) 0.97105(14) 0.0292(5) Uani 1 1 d . . . . .
H11 H 0.2426 0.2658 1.0058 0.035 Uiso 1 1 calc R . . . .
C12 C 0.2892(2) 0.23950(13) 0.89111(15) 0.0296(5) Uani 1 1 d . . . . .
H12 H 0.2201 0.2040 0.8697 0.036 Uiso 1 1 calc R . . . .
C13 C 0.3789(2) 0.25511(12) 0.84093(13) 0.0249(4) Uani 1 1 d . . . . .
N1 N 0.73891(19) 0.49098(10) 1.00981(11) 0.0211(3) Uani 1 1 d . . . . .
N2 N 0.58882(18) 0.39371(10) 0.98413(11) 0.0219(3) Uani 1 1 d . . . . .
N3 N 0.47806(17) 0.30560(10) 0.86906(10) 0.0212(3) Uani 1 1 d . . . . .
N4 N 0.3696(2) 0.21765(11) 0.76300(12) 0.0291(4) Uani 1 1 d D . . . .
O1 O 0.65378(16) 0.47519(9) 1.12871(9) 0.0274(3) Uani 1 1 d . . . . .
S1 S 0.68147(6) 0.43989(3) 0.84492(3) 0.03057(14) Uani 1 1 d . . . . .
C21 C 0.6426(2) 0.30178(11) 0.59529(12) 0.0214(4) Uani 1 1 d . . . . .
C22 C 0.4387(2) 0.37806(12) 0.57828(13) 0.0246(4) Uani 1 1 d D . . . .
C23 C 0.3540(4) 0.4279(2) 0.5115(2) 0.022(2) Uani 0.486(10) 1 d D . P A 1
C24 C 0.2240(4) 0.4363(3) 0.5154(3) 0.0324(16) Uani 0.486(10) 1 d G . P A 1
H24 H 0.1974 0.4150 0.5640 0.039 Uiso 0.486(10) 1 calc R . P A 1
C25 C 0.1328(3) 0.4760(4) 0.4480(4) 0.0406(16) Uani 0.486(10) 1 d G . P A 1
H25 H 0.0439 0.4817 0.4507 0.049 Uiso 0.486(10) 1 calc R . P A 1
C26 C 0.1716(4) 0.5071(2) 0.3768(3) 0.034(3) Uani 0.486(10) 1 d G . P A 1
H26 H 0.1093 0.5342 0.3308 0.040 Uiso 0.486(10) 1 calc R . P A 1
C27 C 0.3017(5) 0.4987(3) 0.3729(3) 0.0334(14) Uani 0.486(10) 1 d G . P A 1
H27 H 0.3282 0.5200 0.3243 0.040 Uiso 0.486(10) 1 calc R . P A 1
C28 C 0.3929(4) 0.4591(3) 0.4403(3) 0.0271(12) Uani 0.486(10) 1 d G . P A 1
H28 H 0.4817 0.4533 0.4376 0.033 Uiso 0.486(10) 1 calc R . P A 1
C29 C 0.7572(2) 0.31695(12) 0.47318(13) 0.0241(4) Uani 1 1 d . . . . .
C30 C 0.8778(2) 0.30281(13) 0.45761(15) 0.0296(5) Uani 1 1 d . . . . .
H30 H 0.9418 0.2707 0.4957 0.035 Uiso 1 1 calc R . . . .
C31 C 0.9010(3) 0.33819(13) 0.38274(15) 0.0322(5) Uani 1 1 d . . . . .
H31 H 0.9835 0.3309 0.3698 0.039 Uiso 1 1 calc R . . . .
C32 C 0.8069(2) 0.38319(12) 0.32785(13) 0.0275(4) Uani 1 1 d . . . . .
H32 H 0.8233 0.4077 0.2773 0.033 Uiso 1 1 calc R . . . .
C33 C 0.6853(2) 0.39227(14) 0.34798(13) 0.0299(5) Uani 1 1 d . . . . .
N21 N 0.54856(19) 0.35264(10) 0.55346(11) 0.0239(4) Uani 1 1 d . . . . .
N22 N 0.73264(19) 0.28491(10) 0.55102(11) 0.0231(4) Uani 1 1 d . . . . .
N23 N 0.66155(19) 0.35952(12) 0.42070(11) 0.0297(4) Uani 1 1 d . . . . .
N24 N 0.5862(3) 0.43481(16) 0.29569(14) 0.0467(6) Uani 1 1 d D . . . .
O21 O 0.41610(17) 0.36297(9) 0.64978(10) 0.0305(3) Uani 1 1 d . . . . .
S21 S 0.65607(6) 0.25629(3) 0.69374(3) 0.02480(12) Uani 1 1 d . . . . .
C223 C 0.3382(4) 0.4235(2) 0.5048(2) 0.026(2) Uani 0.514(10) 1 d D . P A 2
C224 C 0.2412(5) 0.4633(3) 0.5308(2) 0.0259(13) Uani 0.514(10) 1 d G . P A 2
H224 H 0.2360 0.4600 0.5913 0.031 Uiso 0.514(10) 1 calc R . P A 2
C225 C 0.1518(4) 0.5078(3) 0.4683(3) 0.0306(12) Uani 0.514(10) 1 d G . P A 2
H225 H 0.0855 0.5350 0.4860 0.037 Uiso 0.514(10) 1 calc R . P A 2
C226 C 0.1595(4) 0.5126(2) 0.3797(2) 0.038(3) Uani 0.514(10) 1 d G . P A 2
H226 H 0.0984 0.5431 0.3370 0.045 Uiso 0.514(10) 1 calc R . P A 2
C227 C 0.2565(5) 0.4728(3) 0.3538(2) 0.0339(14) Uani 0.514(10) 1 d G . P A 2
H227 H 0.2617 0.4761 0.2933 0.041 Uiso 0.514(10) 1 calc R . P A 2
C228 C 0.3458(5) 0.4283(3) 0.4163(3) 0.0328(14) Uani 0.514(10) 1 d G . P A 2
H228 H 0.4121 0.4011 0.3985 0.039 Uiso 0.514(10) 1 calc R . P A 2
Cl41 Cl 0.03506(5) 0.36802(3) 0.12743(3) 0.02371(11) Uani 1 1 d . . . . .
O41 O 0.0814(3) 0.37635(14) 0.22311(12) 0.0649(7) Uani 1 1 d . . . . .
O42 O 0.10988(19) 0.30914(10) 0.10130(12) 0.0395(4) Uani 1 1 d . . . . .
O43 O 0.05209(19) 0.43632(9) 0.08396(12) 0.0376(4) Uani 1 1 d . . . . .
O44 O -0.10327(18) 0.34864(10) 0.10144(14) 0.0430(4) Uani 1 1 d . . . . .
H4A H 0.297(2) 0.1957(15) 0.7371(17) 0.034(7) Uiso 1 1 d D . . . .
H21 H 0.555(3) 0.3658(16) 0.502(2) 0.043(8) Uiso 1 1 d . . . . .
H22 H 0.786(3) 0.2525(15) 0.5755(18) 0.027(7) Uiso 1 1 d . . . . .
H1 H 0.789(3) 0.5149(16) 0.9903(19) 0.036(7) Uiso 1 1 d . . . . .
H2 H 0.594(3) 0.4058(16) 1.035(2) 0.041(8) Uiso 1 1 d . . . . .
H4B H 0.416(3) 0.2352(16) 0.731(2) 0.039(8) Uiso 1 1 d . . . . .
H24A H 0.597(3) 0.4501(17) 0.2460(16) 0.054(9) Uiso 1 1 d D . . . .
H24B H 0.510(5) 0.431(3) 0.298(3) 0.093(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 2.0148(17) . ?
Cu1 S1 2.2127(6) . ?
Cu1 O21 2.3703(16) . ?
Cu1 S21 2.2515(6) . ?
C1 N1 1.393(3) . ?
C1 N2 1.337(3) . ?
C1 S1 1.6746(19) . ?
C2 C3 1.482(3) . ?
C2 N1 1.383(2) . ?
C2 O1 1.232(3) . ?
C3 C4 1.400(3) . ?
C3 C8 1.396(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 N2 1.406(3) . ?
C9 N3 1.352(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.364(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.404(3) . ?
C13 N3 1.354(3) . ?
C13 N4 1.354(3) . ?
N1 H1 0.80(3) . ?
N2 H2 0.80(3) . ?
N4 H4A 0.851(17) . ?
N4 H4B 0.84(3) . ?
C21 N21 1.363(3) . ?
C21 N22 1.346(3) . ?
C21 S21 1.6910(19) . ?
C22 C23 1.458(4) . ?
C22 N21 1.389(3) . ?
C22 O21 1.220(2) . ?
C22 C223 1.542(4) . ?
C23 C24 1.3900 . ?
C23 C28 1.3900 . ?
C24 H24 0.9500 . ?
C24 C25 1.3900 . ?
C25 H25 0.9500 . ?
C25 C26 1.3900 . ?
C26 H26 0.9500 . ?
C26 C27 1.3900 . ?
C27 H27 0.9500 . ?
C27 C28 1.3900 . ?
C28 H28 0.9500 . ?
C29 C30 1.376(3) . ?
C29 N22 1.416(2) . ?
C29 N23 1.335(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.396(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.366(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.404(3) . ?
C33 N23 1.348(3) . ?
C33 N24 1.355(3) . ?
N21 H21 0.85(3) . ?
N22 H22 0.82(3) . ?
N24 H24A 0.848(18) . ?
N24 H24B 0.81(5) . ?
C223 C224 1.3900 . ?
C223 C228 1.3900 . ?
C224 H224 0.9500 . ?
C224 C225 1.3900 . ?
C225 H225 0.9500 . ?
C225 C226 1.3900 . ?
C226 H226 0.9500 . ?
C226 C227 1.3900 . ?
C227 H227 0.9500 . ?
C227 C228 1.3900 . ?
C228 H228 0.9500 . ?
Cl41 O41 1.4224(18) . ?
Cl41 O42 1.4382(18) . ?
Cl41 O43 1.4298(17) . ?
Cl41 O44 1.4341(19) . ?

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
N3 Cu1 S1 102.76(5) . . ?
N3 Cu1 O21 101.80(6) . . ?
N3 Cu1 S21 125.50(5) . . ?
S1 Cu1 O21 109.06(5) . . ?
S1 Cu1 S21 126.94(2) . . ?
S21 Cu1 O21 83.50(4) . . ?
N1 C1 S1 115.85(15) . . ?
N2 C1 N1 115.32(16) . . ?
N2 C1 S1 128.82(15) . . ?
N1 C2 C3 118.27(18) . . ?
O1 C2 C3 121.39(17) . . ?
O1 C2 N1 120.30(19) . . ?
C4 C3 C2 116.57(19) . . ?
C8 C3 C2 123.84(18) . . ?
C8 C3 C4 119.6(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 120.1 . . ?
C7 C8 C3 119.7(2) . . ?
C7 C8 H8 120.1 . . ?
C10 C9 N2 114.75(17) . . ?
N3 C9 C10 123.28(19) . . ?
N3 C9 N2 121.96(18) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.42(19) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
N3 C13 C12 122.06(19) . . ?
N4 C13 C12 119.8(2) . . ?
N4 C13 N3 118.1(2) . . ?
C1 N1 H1 115(2) . . ?
C2 N1 C1 128.01(18) . . ?
C2 N1 H1 117(2) . . ?
C1 N2 C9 135.27(17) . . ?
C1 N2 H2 110(2) . . ?
C9 N2 H2 113(2) . . ?
C9 N3 Cu1 122.97(14) . . ?
C9 N3 C13 117.42(17) . . ?
C13 N3 Cu1 119.04(13) . . ?
C13 N4 H4A 118.4(19) . . ?
C13 N4 H4B 115(2) . . ?
H4A N4 H4B 119(3) . . ?
C1 S1 Cu1 103.41(7) . . ?
N21 C21 S21 127.70(16) . . ?
N22 C21 N21 115.36(17) . . ?
N22 C21 S21 116.92(16) . . ?
N21 C22 C23 113.2(2) . . ?
N21 C22 C223 114.8(2) . . ?
O21 C22 C23 122.5(2) . . ?
O21 C22 N21 124.3(2) . . ?
O21 C22 C223 120.8(2) . . ?
C24 C23 C22 116.4(3) . . ?
C24 C23 C28 120.0 . . ?
C28 C23 C22 123.1(3) . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0 . . ?
C28 C27 H27 120.0 . . ?
C23 C28 H28 120.0 . . ?
C27 C28 C23 120.0 . . ?
C27 C28 H28 120.0 . . ?
C30 C29 N22 117.9(2) . . ?
N23 C29 C30 124.76(19) . . ?
N23 C29 N22 117.30(19) . . ?
C29 C30 H30 121.8 . . ?
C29 C30 C31 116.3(2) . . ?
C31 C30 H30 121.8 . . ?
C30 C31 H31 119.5 . . ?
C32 C31 C30 121.0(2) . . ?
C32 C31 H31 119.5 . . ?
C31 C32 H32 120.8 . . ?
C31 C32 C33 118.3(2) . . ?
C33 C32 H32 120.8 . . ?
N23 C33 C32 121.7(2) . . ?
N23 C33 N24 116.6(2) . . ?
N24 C33 C32 121.7(2) . . ?
C21 N21 C22 129.39(17) . . ?
C21 N21 H21 113(2) . . ?
C22 N21 H21 117(2) . . ?
C21 N22 C29 131.20(19) . . ?
C21 N22 H22 114.1(18) . . ?
C29 N22 H22 114.6(18) . . ?
C29 N23 C33 117.89(19) . . ?
C33 N24 H24A 116(2) . . ?
C33 N24 H24B 122(3) . . ?
H24A N24 H24B 116(4) . . ?
C22 O21 Cu1 123.26(15) . . ?
C21 S21 Cu1 107.22(7) . . ?
C224 C223 C22 117.6(3) . . ?
C224 C223 C228 120.0 . . ?
C228 C223 C22 122.3(3) . . ?
C223 C224 H224 120.0 . . ?
C225 C224 C223 120.0 . . ?
C225 C224 H224 120.0 . . ?
C224 C225 H225 120.0 . . ?
C224 C225 C226 120.0 . . ?
C226 C225 H225 120.0 . . ?
C225 C226 H226 120.0 . . ?
C227 C226 C225 120.0 . . ?
C227 C226 H226 120.0 . . ?
C226 C227 H227 120.0 . . ?
C228 C227 C226 120.0 . . ?
C228 C227 H227 120.0 . . ?
C223 C228 H228 120.0 . . ?
C227 C228 C223 120.0 . . ?
C227 C228 H228 120.0 . . ?
O41 Cl41 O42 108.23(13) . . ?
O41 Cl41 O43 110.09(13) . . ?
O41 Cl41 O44 109.67(15) . . ?
O43 Cl41 O42 110.28(11) . . ?
O43 Cl41 O44 109.09(11) . . ?
O44 Cl41 O42 109.47(11) . . ?

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
N4 H4A O41 0.851(17) 2.56(2) 3.361(3) 158(2) 4_566
N4 H4A O42 0.851(17) 2.43(2) 3.164(3) 145(2) 4_566
N21 H21 N23 0.85(3) 1.90(3) 2.639(2) 145(3) .
N22 H22 O44 0.82(3) 2.13(3) 2.921(3) 163(2) 4_666
N1 H1 O43 0.80(3) 2.43(3) 3.221(2) 168(3) 3_666
N2 H2 O1 0.80(3) 1.87(3) 2.586(2) 148(3) .
N4 H4B O21 0.84(3) 2.61(3) 3.246(3) 133(3) .
N4 H4B S21 0.84(3) 2.76(3) 3.529(2) 152(3) .
N24 H24A O1 0.848(18) 2.105(19) 2.943(2) 169(3) 1_554

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
C2 C3 C4 C5 -177.73(19) . . . . ?
C2 C3 C8 C7 177.57(19) . . . . ?
C3 C2 N1 C1 178.19(19) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C3 C8 C7 -1.7(3) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C5 C6 C7 C8 1.3(3) . . . . ?
C6 C7 C8 C3 0.2(3) . . . . ?
C8 C3 C4 C5 1.6(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C9 N2 C1 -157.4(2) . . . . ?
C10 C9 N3 Cu1 171.74(15) . . . . ?
C10 C9 N3 C13 0.6(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 N3 -0.4(3) . . . . ?
C11 C12 C13 N4 177.8(2) . . . . ?
C12 C13 N3 Cu1 -171.41(16) . . . . ?
C12 C13 N3 C9 0.1(3) . . . . ?
N1 C1 N2 C9 170.4(2) . . . . ?
N1 C1 S1 Cu1 168.01(14) . . . . ?
N1 C2 C3 C4 164.69(18) . . . . ?
N1 C2 C3 C8 -14.6(3) . . . . ?
N2 C1 N1 C2 -6.1(3) . . . . ?
N2 C1 S1 Cu1 -12.4(2) . . . . ?
N2 C9 C10 C11 -179.68(18) . . . . ?
N2 C9 N3 Cu1 -9.6(3) . . . . ?
N2 C9 N3 C13 179.21(18) . . . . ?
N3 C9 C10 C11 -0.9(3) . . . . ?
N3 C9 N2 C1 23.8(4) . . . . ?
N4 C13 N3 Cu1 10.3(3) . . . . ?
N4 C13 N3 C9 -178.13(18) . . . . ?
O1 C2 C3 C4 -13.1(3) . . . . ?
O1 C2 C3 C8 167.7(2) . . . . ?
O1 C2 N1 C1 -4.0(3) . . . . ?
S1 C1 N1 C2 173.52(16) . . . . ?
S1 C1 N2 C9 -9.2(4) . . . . ?
C22 C23 C24 C25 -172.7(4) . . . . ?
C22 C23 C28 C27 172.2(4) . . . . ?
C22 C223 C224 C225 177.1(4) . . . . ?
C22 C223 C228 C227 -176.9(4) . . . . ?
C23 C22 N21 C21 -174.7(3) . . . . ?
C23 C22 O21 Cu1 -149.6(2) . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C23 C28 C27 0.0 . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C23 0.0 . . . . ?
C28 C23 C24 C25 0.0 . . . . ?
C29 C30 C31 C32 -1.1(3) . . . . ?
C30 C29 N22 C21 162.0(2) . . . . ?
C30 C29 N23 C33 -1.3(3) . . . . ?
C30 C31 C32 C33 -0.8(3) . . . . ?
C31 C32 C33 N23 1.8(3) . . . . ?
C31 C32 C33 N24 -178.7(2) . . . . ?
C32 C33 N23 C29 -0.8(3) . . . . ?
N21 C21 N22 C29 8.4(3) . . . . ?
N21 C21 S21 Cu1 -33.9(2) . . . . ?
N21 C22 C23 C24 159.8(3) . . . . ?
N21 C22 C23 C28 -12.7(4) . . . . ?
N21 C22 O21 Cu1 27.7(3) . . . . ?
N21 C22 C223 C224 -167.1(3) . . . . ?
N21 C22 C223 C228 9.9(4) . . . . ?
N22 C21 N21 C22 175.6(2) . . . . ?
N22 C21 S21 Cu1 148.00(14) . . . . ?
N22 C29 C30 C31 -177.0(2) . . . . ?
N22 C29 N23 C33 177.94(19) . . . . ?
N23 C29 C30 C31 2.2(3) . . . . ?
N23 C29 N22 C21 -17.3(3) . . . . ?
N24 C33 N23 C29 179.6(2) . . . . ?
O21 C22 C23 C24 -22.6(5) . . . . ?
O21 C22 C23 C28 164.9(3) . . . . ?
O21 C22 N21 C21 7.8(4) . . . . ?
O21 C22 C223 C224 17.0(5) . . . . ?
O21 C22 C223 C228 -165.9(3) . . . . ?
S21 C21 N21 C22 -2.5(3) . . . . ?
S21 C21 N22 C29 -173.21(17) . . . . ?
C223 C22 N21 C21 -168.0(3) . . . . ?
C223 C22 O21 Cu1 -156.8(2) . . . . ?
C223 C224 C225 C226 0.0 . . . . ?
C224 C223 C228 C227 0.0 . . . . ?
C224 C225 C226 C227 0.0 . . . . ?
C225 C226 C227 C228 0.0 . . . . ?
C226 C227 C228 C223 0.0 . . . . ?
C228 C223 C224 C225 0.0 . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_21_2015ncs0006
_database_code_depnum_ccdc_archive 'CCDC 2082375'
loop_
_audit_author_name
_audit_author_address
'Peter Horton'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2016-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H25 Cu N5 O2 S2, Cl O4, 0.5(H2 O)'
_chemical_formula_sum            'C17 H26 Cl Cu N5 O6.50 S2'
_chemical_formula_weight         567.54
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H32 N10 O8 S4 Cu Cl'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.3999(3)
_cell_length_b                   14.2258(4)
_cell_length_c                   13.3826(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.462(2)
_cell_angle_gamma                90
_cell_volume                     2360.59(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18211
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5500
_cell_measurement_theta_min      2.1960
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    1.261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30299
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.230
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00   25.00   0.5000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.0000  -72.0000 -150.0000 248

#__ type_ start__ end____ width___ exp.time_
  2 omega  -73.00   49.00   0.5000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.0000    0.0000 -150.0000 244

#__ type_ start__ end____ width___ exp.time_
  3 omega  -72.00   25.00   0.5000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.0000  -72.0000   30.0000 194

#__ type_ start__ end____ width___ exp.time_
  4 omega  -14.00   64.00   0.5000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.0000   54.0000  150.0000 156
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_UB_11      -0.0133219000
_diffrn_orient_matrix_UB_12      0.0179241000
_diffrn_orient_matrix_UB_13      -0.0479200000
_diffrn_orient_matrix_UB_21      0.0553482000
_diffrn_orient_matrix_UB_22      -0.0004259000
_diffrn_orient_matrix_UB_23      -0.0130563000
_diffrn_orient_matrix_UB_31      -0.0057212000
_diffrn_orient_matrix_UB_32      -0.0465534000
_diffrn_orient_matrix_UB_33      -0.0183986000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                8684
_reflns_number_total             10291
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.249
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details 
;
 Flack x determined using 3317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     681
_refine_ls_number_reflns         10291
_refine_ls_number_restraints     157
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1052P)²+0.6975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1579
_refine_special_details          
'Disorder in one perchlorate ion and t-butyl group, resulting in the use of both geometrical (SADI, SAME, BUMP) and displacement (RIGU) restraints.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C29-C34 \\sim C29-C34A
 with sigma of 0.02
 C29-C35 \\sim C29-C35A \\sim C29-C36 \\sim C29-C36A \\sim C29-C37 \\sim
C29-C37A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C29, C34, C35, C36, C37, C34A, C35A, C36A, C37A, Cl51, O51, O52, O53, O54,
 Cl52, O51A, O52A, O53A, O54A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{C34, C35, C36, C37} sigma for 1-2: 0.02, 1-3: 0.04
as
{C34A, C35A, C36A, C37A}
{Cl51, O51, O52, O53, O54} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl52, O51A, O52A, O53A, O54A}
5. Others
 Sof(Cl52)=Sof(O51A)=Sof(O52A)=Sof(O53A)=Sof(O54A)=1-FVAR(1)
 Sof(Cl51)=Sof(O51)=Sof(O52)=Sof(O53)=Sof(O54)=FVAR(1)
 Sof(C34A)=Sof(C35A)=Sof(H35D)=Sof(H35E)=Sof(H35F)=Sof(C36A)=Sof(H36D)=
 Sof(H36E)=Sof(H36F)=Sof(C37A)=Sof(H37D)=Sof(H37E)=Sof(H37F)=1-FVAR(2)
 Sof(C34)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(C36)=Sof(H36A)=Sof(H36B)=
 Sof(H36C)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=FVAR(2)
6.a Free rotating group:
 O61(H61A,H61B)
6.b Me refined with riding coordinates:
 C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C35A(H35D,H35E,
 H35F), C36A(H36D,H36E,H36F), C37A(H37D,H37E,H37F)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), N2(H2A), N3(H3A), N4(H4A), N5(H5), C22(H22), C23(H23),
  C24(H24), N22(H22A), N23(H23A), N24(H24A), N25(H25)
6.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 1.11770(6) 0.15404(7) 0.14020(6) 0.0390(2) Uani 1 1 d . . . . .
Cu2 Cu 0.12584(7) 0.40929(6) -0.09033(7) 0.0396(2) Uani 1 1 d . . . . .
C1 C 0.9653(5) 0.1660(5) -0.0278(5) 0.0388(14) Uani 1 1 d . . . . .
C2 C 0.8681(6) 0.1803(6) -0.0761(7) 0.0490(19) Uani 1 1 d . . . . .
H2 H 0.8648 0.1856 -0.1468 0.059 Uiso 1 1 calc R . . . .
C3 C 0.7756(6) 0.1868(8) -0.0200(7) 0.063(3) Uani 1 1 d . . . . .
H3 H 0.7079 0.1976 -0.0517 0.075 Uiso 1 1 calc R . . . .
C4 C 0.7822(6) 0.1774(8) 0.0814(7) 0.061(3) Uani 1 1 d . . . . .
H4 H 0.7193 0.1801 0.1214 0.074 Uiso 1 1 calc R . . . .
C5 C 0.8843(5) 0.1638(6) 0.1250(6) 0.0411(15) Uani 1 1 d . . . . .
C6 C 1.1627(5) 0.1603(5) -0.0788(5) 0.0341(13) Uani 1 1 d . . . . .
C7 C 1.1739(6) 0.1670(5) -0.2627(5) 0.0388(14) Uani 1 1 d . . . . .
C8 C 0.9543(5) 0.1376(5) 0.3008(5) 0.0400(16) Uani 1 1 d . . . . .
C9 C 0.8032(6) 0.1021(5) 0.4172(6) 0.0414(16) Uani 1 1 d . . . . .
C10 C 1.2518(6) 0.1868(5) -0.3483(6) 0.0410(16) Uani 1 1 d . . . . .
C11 C 1.1871(7) 0.1974(6) -0.4454(6) 0.0477(18) Uani 1 1 d . . . . .
H11A H 1.1471 0.1392 -0.4588 0.072 Uiso 1 1 calc GR . . . .
H11B H 1.2363 0.2099 -0.5007 0.072 Uiso 1 1 calc GR . . . .
H11C H 1.1362 0.2497 -0.4390 0.072 Uiso 1 1 calc GR . . . .
C12 C 1.3301(7) 0.1018(6) -0.3570(6) 0.0527(19) Uani 1 1 d . . . . .
H12A H 1.3685 0.0930 -0.2934 0.079 Uiso 1 1 calc GR . . . .
H12B H 1.3823 0.1139 -0.4101 0.079 Uiso 1 1 calc GR . . . .
H12C H 1.2889 0.0449 -0.3730 0.079 Uiso 1 1 calc GR . . . .
C13 C 1.3145(7) 0.2763(6) -0.3238(6) 0.0475(18) Uani 1 1 d . . . . .
H13A H 1.2641 0.3290 -0.3174 0.071 Uiso 1 1 calc GR . . . .
H13B H 1.3655 0.2895 -0.3776 0.071 Uiso 1 1 calc GR . . . .
H13C H 1.3541 0.2679 -0.2608 0.071 Uiso 1 1 calc GR . . . .
C14 C 0.7810(6) 0.0626(5) 0.5198(6) 0.0412(15) Uani 1 1 d . . . . .
C15 C 0.6645(7) 0.0844(7) 0.5472(7) 0.058(2) Uani 1 1 d . . . . .
H15A H 0.6541 0.1526 0.5493 0.086 Uiso 1 1 calc GR . . . .
H15B H 0.6487 0.0575 0.6129 0.086 Uiso 1 1 calc GR . . . .
H15C H 0.6159 0.0570 0.4970 0.086 Uiso 1 1 calc GR . . . .
C16 C 0.8579(7) 0.0986(7) 0.6009(7) 0.0540(19) Uani 1 1 d . . . . .
H16A H 0.9296 0.0712 0.5911 0.081 Uiso 1 1 calc GR . . . .
H16B H 0.8308 0.0803 0.6667 0.081 Uiso 1 1 calc GR . . . .
H16C H 0.8627 0.1672 0.5970 0.081 Uiso 1 1 calc GR . . . .
C17 C 0.7932(8) -0.0446(6) 0.5072(8) 0.059(2) Uani 1 1 d . . . . .
H17A H 0.7438 -0.0666 0.4546 0.089 Uiso 1 1 calc GR . . . .
H17B H 0.7759 -0.0760 0.5703 0.089 Uiso 1 1 calc GR . . . .
H17C H 0.8675 -0.0594 0.4886 0.089 Uiso 1 1 calc GR . . . .
N1 N 0.9742(4) 0.1596(4) 0.0725(4) 0.0367(12) Uani 1 1 d . . . . .
N2 N 1.0538(4) 0.1599(5) -0.0894(4) 0.0382(12) Uani 1 1 d . . . . .
H2A H 1.0343 0.1543 -0.1525 0.046 Uiso 1 1 calc R . . . .
N3 N 1.2178(4) 0.1631(5) -0.1667(4) 0.0392(12) Uani 1 1 d . . . . .
H3A H 1.2887 0.1624 -0.1622 0.047 Uiso 1 1 calc R . . . .
N4 N 0.8809(5) 0.1521(5) 0.2288(5) 0.0469(14) Uani 1 1 d . . . . .
H4A H 0.8149 0.1550 0.2521 0.056 Uiso 1 1 calc R . . . .
N5 N 0.9117(5) 0.1145(5) 0.3925(5) 0.0445(14) Uani 1 1 d . . . . .
H5 H 0.9585 0.1064 0.4415 0.053 Uiso 1 1 calc R . . . .
O1 O 1.0768(4) 0.1586(4) -0.2783(4) 0.0439(11) Uani 1 1 d . . . . .
O2 O 0.7313(4) 0.1181(5) 0.3559(5) 0.0614(17) Uani 1 1 d . . . . .
S1 S 1.23805(13) 0.15548(17) 0.02648(13) 0.0452(4) Uani 1 1 d . . . . .
S2 S 1.09023(13) 0.14502(16) 0.29762(13) 0.0456(4) Uani 1 1 d . . . . .
C21 C -0.0753(6) 0.4188(5) 0.0204(5) 0.0381(14) Uani 1 1 d . . . . .
C22 C -0.1440(6) 0.4264(5) 0.1035(6) 0.0426(17) Uani 1 1 d . . . . .
H22 H -0.2196 0.4344 0.0951 0.051 Uiso 1 1 calc R . . . .
C23 C -0.0976(6) 0.4216(6) 0.1973(6) 0.0449(16) Uani 1 1 d . . . . .
H23 H -0.1416 0.4268 0.2548 0.054 Uiso 1 1 calc R . . . .
C24 C 0.0123(6) 0.4094(6) 0.2081(6) 0.0477(17) Uani 1 1 d . . . . .
H24 H 0.0447 0.4044 0.2725 0.057 Uiso 1 1 calc R . . . .
C25 C 0.0748(6) 0.4046(5) 0.1214(5) 0.0399(14) Uani 1 1 d . . . . .
C26 C -0.1015(5) 0.4120(5) -0.1671(5) 0.0362(13) Uani 1 1 d . . . . .
C27 C -0.2981(6) 0.4258(6) -0.2104(6) 0.0444(17) Uani 1 1 d . . . . .
C28 C 0.2737(6) 0.3842(6) 0.0843(7) 0.0486(19) Uani 1 1 d . . . . .
C29 C 0.3708(8) 0.3350(7) 0.2389(7) 0.064(2) Uani 1 1 d D U . . .
C30 C -0.3759(6) 0.4220(6) -0.2963(6) 0.0487(18) Uani 1 1 d . . . . .
C31 C -0.3754(7) 0.3212(7) -0.3409(8) 0.062(2) Uani 1 1 d . . . . .
H31A H -0.3121 0.3134 -0.3836 0.092 Uiso 1 1 calc GR . . . .
H31B H -0.4411 0.3114 -0.3808 0.092 Uiso 1 1 calc GR . . . .
H31C H -0.3726 0.2750 -0.2866 0.092 Uiso 1 1 calc GR . . . .
C32 C -0.3436(7) 0.4968(7) -0.3749(7) 0.061(2) Uani 1 1 d . . . . .
H32A H -0.3414 0.5590 -0.3433 0.092 Uiso 1 1 calc GR . . . .
H32B H -0.3966 0.4971 -0.4295 0.092 Uiso 1 1 calc GR . . . .
H32C H -0.2722 0.4816 -0.4014 0.092 Uiso 1 1 calc GR . . . .
C33 C -0.4887(6) 0.4450(7) -0.2546(7) 0.057(2) Uani 1 1 d . . . . .
H33A H -0.5125 0.3935 -0.2113 0.086 Uiso 1 1 calc GR . . . .
H33B H -0.5400 0.4525 -0.3101 0.086 Uiso 1 1 calc GR . . . .
H33C H -0.4852 0.5034 -0.2159 0.086 Uiso 1 1 calc GR . . . .
C34 C 0.4786(9) 0.2951(9) 0.2783(8) 0.057(3) Uani 0.818(18) 1 d D U P A 1
C35 C 0.4959(8) 0.2035(7) 0.2265(8) 0.050(3) Uani 0.818(18) 1 d D U P A 1
H35A H 0.4342 0.1621 0.2385 0.075 Uiso 0.818(18) 1 calc R . P A 1
H35B H 0.5031 0.2143 0.1546 0.075 Uiso 0.818(18) 1 calc R . P A 1
H35C H 0.5617 0.1738 0.2525 0.075 Uiso 0.818(18) 1 calc R . P A 1
C36 C 0.4670(11) 0.2787(11) 0.3925(8) 0.071(4) Uani 0.818(18) 1 d D U P A 1
H36A H 0.4087 0.2337 0.4045 0.106 Uiso 0.818(18) 1 calc R . P A 1
H36B H 0.5348 0.2536 0.4196 0.106 Uiso 0.818(18) 1 calc R . P A 1
H36C H 0.4502 0.3384 0.4254 0.106 Uiso 0.818(18) 1 calc R . P A 1
C37 C 0.5666(10) 0.3627(11) 0.2652(12) 0.081(4) Uani 0.818(18) 1 d D U P A 1
H37A H 0.5498 0.4209 0.3011 0.122 Uiso 0.818(18) 1 calc R . P A 1
H37B H 0.6338 0.3360 0.2919 0.122 Uiso 0.818(18) 1 calc R . P A 1
H37C H 0.5751 0.3765 0.1940 0.122 Uiso 0.818(18) 1 calc R . P A 1
N21 N 0.0309(4) 0.4092(4) 0.0286(4) 0.0357(11) Uani 1 1 d . . . . .
N22 N -0.1292(4) 0.4240(4) -0.0705(4) 0.0372(12) Uani 1 1 d . . . . .
H22A H -0.1977 0.4386 -0.0637 0.045 Uiso 1 1 calc R . . . .
N23 N -0.1880(4) 0.4135(5) -0.2335(4) 0.0407(13) Uani 1 1 d . . . . .
H23A H -0.1726 0.4060 -0.2970 0.049 Uiso 1 1 calc R . . . .
N24 N 0.1826(5) 0.3887(5) 0.1399(5) 0.0492(16) Uani 1 1 d . . . . .
H24A H 0.1959 0.3792 0.2038 0.059 Uiso 1 1 calc R . . . .
N25 N 0.3647(5) 0.3586(6) 0.1389(5) 0.0542(18) Uani 1 1 d . . . . .
H25 H 0.4258 0.3572 0.1059 0.065 Uiso 1 1 calc R . . . .
O21 O -0.3263(4) 0.4345(5) -0.1237(4) 0.0563(16) Uani 1 1 d . . . . .
O22 O 0.2942(6) 0.3411(7) 0.2928(5) 0.084(2) Uani 1 1 d . . . . .
S21 S 0.02138(14) 0.40118(15) -0.21791(13) 0.0446(4) Uani 1 1 d . . . . .
S22 S 0.28984(15) 0.40762(19) -0.03692(17) 0.0543(5) Uani 1 1 d . . . . .
C34A C 0.482(2) 0.314(3) 0.287(2) 0.090(12) Uani 0.182(18) 1 d D U P A 2
C35A C 0.5591(17) 0.274(4) 0.2144(14) 0.111(16) Uani 0.182(18) 1 d D U P A 2
H35D H 0.5263 0.2203 0.1804 0.167 Uiso 0.182(18) 1 calc R . P A 2
H35E H 0.5777 0.3224 0.1650 0.167 Uiso 0.182(18) 1 calc R . P A 2
H35F H 0.6245 0.2541 0.2499 0.167 Uiso 0.182(18) 1 calc R . P A 2
C36A C 0.465(4) 0.238(3) 0.369(4) 0.111(17) Uani 0.182(18) 1 d D U P A 2
H36D H 0.4369 0.1807 0.3384 0.166 Uiso 0.182(18) 1 calc R . P A 2
H36E H 0.5347 0.2248 0.4014 0.166 Uiso 0.182(18) 1 calc R . P A 2
H36F H 0.4144 0.2618 0.4185 0.166 Uiso 0.182(18) 1 calc R . P A 2
C37A C 0.524(3) 0.395(3) 0.341(4) 0.079(13) Uani 0.182(18) 1 d D U P A 2
H37D H 0.4692 0.4180 0.3874 0.118 Uiso 0.182(18) 1 calc R . P A 2
H37E H 0.5888 0.3766 0.3784 0.118 Uiso 0.182(18) 1 calc R . P A 2
H37F H 0.5420 0.4449 0.2934 0.118 Uiso 0.182(18) 1 calc R . P A 2
Cl41 Cl 0.49841(18) 0.59936(16) 0.09634(17) 0.0604(6) Uani 1 1 d . . . . .
O41 O 0.4108(6) 0.5764(6) 0.1620(5) 0.078(2) Uani 1 1 d . . . . .
O42 O 0.5464(6) 0.6862(5) 0.1283(5) 0.0638(16) Uani 1 1 d . . . . .
O43 O 0.5835(6) 0.5284(5) 0.1018(7) 0.078(2) Uani 1 1 d . . . . .
O44 O 0.4619(5) 0.6055(5) -0.0038(5) 0.0646(16) Uani 1 1 d . . . . .
Cl51 Cl 0.8892(11) 0.3802(11) 0.4756(10) 0.046(3) Uani 0.55(5) 1 d D U P B 1
O51 O 0.971(2) 0.334(2) 0.422(2) 0.059(6) Uani 0.55(5) 1 d D U P B 1
O52 O 0.877(3) 0.336(2) 0.5718(13) 0.065(6) Uani 0.55(5) 1 d D U P B 1
O53 O 0.9167(13) 0.4750(10) 0.489(3) 0.070(5) Uani 0.55(5) 1 d D U P B 1
O54 O 0.7919(11) 0.373(2) 0.4233(11) 0.066(6) Uani 0.55(5) 1 d D U P B 1
Cl52 Cl 0.8891(13) 0.3664(12) 0.4725(11) 0.034(3) Uani 0.45(5) 1 d D U P B 2
O51A O 0.980(2) 0.3184(18) 0.435(3) 0.042(5) Uani 0.45(5) 1 d D U P B 2
O52A O 0.893(2) 0.360(2) 0.5793(13) 0.051(6) Uani 0.45(5) 1 d D U P B 2
O53A O 0.894(2) 0.4629(13) 0.4470(17) 0.055(6) Uani 0.45(5) 1 d D U P B 2
O54A O 0.7932(14) 0.323(2) 0.4345(18) 0.068(6) Uani 0.45(5) 1 d D U P B 2
O61 O 0.5415(6) 0.3296(5) 0.0145(6) 0.0699(18) Uani 1 1 d . . . . .
H61A H 0.5375 0.2730 -0.0100 0.105 Uiso 1 1 d G . . . .
H61B H 0.5919 0.3607 -0.0159 0.105 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 N1 1.992(5) . ?
Cu1 S1 2.140(2) . ?
Cu1 S2 2.141(2) . ?
Cu2 N21 1.987(5) . ?
Cu2 S21 2.138(2) . ?
Cu2 S22 2.150(2) . ?
C1 C2 1.379(10) . ?
C1 N1 1.348(9) . ?
C1 N2 1.380(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.366(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.403(10) . ?
C5 N1 1.325(9) . ?
C5 N4 1.399(10) . ?
C6 N2 1.357(8) . ?
C6 N3 1.367(9) . ?
C6 S1 1.685(7) . ?
C7 C10 1.531(10) . ?
C7 N3 1.392(8) . ?
C7 O1 1.227(8) . ?
C8 N4 1.336(9) . ?
C8 N5 1.379(9) . ?
C8 S2 1.690(7) . ?
C9 C14 1.510(11) . ?
C9 N5 1.399(9) . ?
C9 O2 1.227(9) . ?
C10 C11 1.530(10) . ?
C10 C12 1.556(11) . ?
C10 C13 1.526(10) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.525(10) . ?
C14 C16 1.528(11) . ?
C14 C17 1.542(11) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
N4 H4A 0.8800 . ?
N5 H5 0.8800 . ?
C21 C22 1.411(9) . ?
C21 N21 1.328(9) . ?
C21 N22 1.384(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.378(11) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(11) . ?
C24 H24 0.9500 . ?
C24 C25 1.402(10) . ?
C25 N21 1.354(9) . ?
C25 N24 1.376(10) . ?
C26 N22 1.352(8) . ?
C26 N23 1.386(9) . ?
C26 S21 1.681(6) . ?
C27 C30 1.496(11) . ?
C27 N23 1.413(9) . ?
C27 O21 1.221(9) . ?
C28 N24 1.359(10) . ?
C28 N25 1.387(10) . ?
C28 S22 1.670(9) . ?
C29 C34 1.541(13) . ?
C29 N25 1.381(12) . ?
C29 O22 1.200(12) . ?
C29 C34A 1.54(3) . ?
C30 C31 1.554(12) . ?
C30 C32 1.551(13) . ?
C30 C33 1.545(11) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.493(16) . ?
C34 C36 1.554(16) . ?
C34 C37 1.467(17) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
N22 H22A 0.8800 . ?
N23 H23A 0.8800 . ?
N24 H24A 0.8800 . ?
N25 H25 0.8800 . ?
C34A C35A 1.48(3) . ?
C34A C36A 1.55(3) . ?
C34A C37A 1.46(3) . ?
C35A H35D 0.9800 . ?
C35A H35E 0.9800 . ?
C35A H35F 0.9800 . ?
C36A H36D 0.9800 . ?
C36A H36E 0.9800 . ?
C36A H36F 0.9800 . ?
C37A H37D 0.9800 . ?
C37A H37E 0.9800 . ?
C37A H37F 0.9800 . ?
Cl41 O41 1.440(8) . ?
Cl41 O42 1.435(7) . ?
Cl41 O43 1.462(7) . ?
Cl41 O44 1.414(6) . ?
Cl51 O51 1.416(14) . ?
Cl51 O52 1.441(15) . ?
Cl51 O53 1.402(14) . ?
Cl51 O54 1.395(14) . ?
Cl52 O51A 1.410(15) . ?
Cl52 O52A 1.433(16) . ?
Cl52 O53A 1.417(14) . ?
Cl52 O54A 1.427(16) . ?
O61 H61A 0.8701 . ?
O61 H61B 0.8699 . ?

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
N1 Cu1 S1 107.54(18) . . ?
N1 Cu1 S2 107.56(18) . . ?
S1 Cu1 S2 144.87(7) . . ?
N21 Cu2 S21 106.29(17) . . ?
N21 Cu2 S22 107.37(17) . . ?
S21 Cu2 S22 146.12(8) . . ?
C2 C1 N2 115.2(7) . . ?
N1 C1 C2 122.7(7) . . ?
N1 C1 N2 122.1(6) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(8) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(7) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.2(8) . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 123.1(7) . . ?
N1 C5 N4 123.6(6) . . ?
N4 C5 C4 113.3(6) . . ?
N2 C6 N3 114.5(6) . . ?
N2 C6 S1 129.2(5) . . ?
N3 C6 S1 116.3(5) . . ?
N3 C7 C10 116.9(6) . . ?
O1 C7 C10 121.0(6) . . ?
O1 C7 N3 122.0(6) . . ?
N4 C8 N5 114.5(6) . . ?
N4 C8 S2 130.2(6) . . ?
N5 C8 S2 115.3(5) . . ?
N5 C9 C14 116.4(6) . . ?
O2 C9 C14 122.7(7) . . ?
O2 C9 N5 120.8(7) . . ?
C7 C10 C12 108.1(6) . . ?
C11 C10 C7 108.9(6) . . ?
C11 C10 C12 109.7(6) . . ?
C13 C10 C7 108.5(6) . . ?
C13 C10 C11 111.3(7) . . ?
C13 C10 C12 110.3(7) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 C15 108.8(6) . . ?
C9 C14 C16 113.8(6) . . ?
C9 C14 C17 104.5(7) . . ?
C15 C14 C16 110.4(7) . . ?
C15 C14 C17 108.7(7) . . ?
C16 C14 C17 110.4(7) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 N1 Cu1 121.4(5) . . ?
C5 N1 Cu1 120.9(5) . . ?
C5 N1 C1 117.6(6) . . ?
C1 N2 H2A 111.5 . . ?
C6 N2 C1 137.1(6) . . ?
C6 N2 H2A 111.5 . . ?
C6 N3 C7 126.9(6) . . ?
C6 N3 H3A 116.5 . . ?
C7 N3 H3A 116.5 . . ?
C5 N4 H4A 112.4 . . ?
C8 N4 C5 135.1(6) . . ?
C8 N4 H4A 112.4 . . ?
C8 N5 C9 128.1(6) . . ?
C8 N5 H5 116.0 . . ?
C9 N5 H5 116.0 . . ?
C6 S1 Cu1 102.1(2) . . ?
C8 S2 Cu1 101.3(3) . . ?
N21 C21 C22 123.2(7) . . ?
N21 C21 N22 123.3(6) . . ?
N22 C21 C22 113.4(6) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 C21 117.6(7) . . ?
C23 C22 H22 121.2 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.4(7) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 121.0 . . ?
C23 C24 C25 118.1(7) . . ?
C25 C24 H24 121.0 . . ?
N21 C25 C24 122.4(7) . . ?
N21 C25 N24 123.8(6) . . ?
N24 C25 C24 113.6(7) . . ?
N22 C26 N23 114.2(6) . . ?
N22 C26 S21 129.5(5) . . ?
N23 C26 S21 116.2(5) . . ?
N23 C27 C30 116.5(6) . . ?
O21 C27 C30 123.0(6) . . ?
O21 C27 N23 120.4(7) . . ?
N24 C28 N25 113.6(8) . . ?
N24 C28 S22 129.0(6) . . ?
N25 C28 S22 117.4(6) . . ?
N25 C29 C34 117.5(8) . . ?
N25 C29 C34A 119.3(14) . . ?
O22 C29 C34 120.7(9) . . ?
O22 C29 N25 121.8(8) . . ?
O22 C29 C34A 118.3(14) . . ?
C27 C30 C31 108.9(7) . . ?
C27 C30 C32 109.1(7) . . ?
C27 C30 C33 107.2(6) . . ?
C32 C30 C31 111.8(7) . . ?
C33 C30 C31 109.9(7) . . ?
C33 C30 C32 109.9(8) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C29 C34 C36 107.8(9) . . ?
C35 C34 C29 106.9(9) . . ?
C35 C34 C36 109.9(10) . . ?
C37 C34 C29 111.2(10) . . ?
C37 C34 C35 114.0(11) . . ?
C37 C34 C36 106.9(11) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C21 N21 Cu2 121.8(5) . . ?
C21 N21 C25 118.2(6) . . ?
C25 N21 Cu2 119.9(4) . . ?
C21 N22 H22A 112.4 . . ?
C26 N22 C21 135.2(6) . . ?
C26 N22 H22A 112.4 . . ?
C26 N23 C27 127.3(6) . . ?
C26 N23 H23A 116.4 . . ?
C27 N23 H23A 116.4 . . ?
C25 N24 H24A 112.0 . . ?
C28 N24 C25 136.0(7) . . ?
C28 N24 H24A 112.0 . . ?
C28 N25 H25 116.1 . . ?
C29 N25 C28 127.7(8) . . ?
C29 N25 H25 116.1 . . ?
C26 S21 Cu2 102.6(2) . . ?
C28 S22 Cu2 101.8(3) . . ?
C29 C34A C36A 108(2) . . ?
C35A C34A C29 112.6(19) . . ?
C35A C34A C36A 107(3) . . ?
C37A C34A C29 112(2) . . ?
C37A C34A C35A 113(3) . . ?
C37A C34A C36A 104(3) . . ?
C34A C35A H35D 109.5 . . ?
C34A C35A H35E 109.5 . . ?
C34A C35A H35F 109.5 . . ?
H35D C35A H35E 109.5 . . ?
H35D C35A H35F 109.5 . . ?
H35E C35A H35F 109.5 . . ?
C34A C36A H36D 109.5 . . ?
C34A C36A H36E 109.5 . . ?
C34A C36A H36F 109.5 . . ?
H36D C36A H36E 109.5 . . ?
H36D C36A H36F 109.5 . . ?
H36E C36A H36F 109.5 . . ?
C34A C37A H37D 109.5 . . ?
C34A C37A H37E 109.5 . . ?
C34A C37A H37F 109.5 . . ?
H37D C37A H37E 109.5 . . ?
H37D C37A H37F 109.5 . . ?
H37E C37A H37F 109.5 . . ?
O41 Cl41 O43 111.1(5) . . ?
O42 Cl41 O41 109.1(5) . . ?
O42 Cl41 O43 106.3(4) . . ?
O44 Cl41 O41 110.8(4) . . ?
O44 Cl41 O42 111.0(4) . . ?
O44 Cl41 O43 108.4(5) . . ?
O51 Cl51 O52 109.6(15) . . ?
O53 Cl51 O51 109.7(15) . . ?
O53 Cl51 O52 109.2(15) . . ?
O54 Cl51 O51 109.4(15) . . ?
O54 Cl51 O52 108.5(15) . . ?
O54 Cl51 O53 110.3(12) . . ?
O51A Cl52 O52A 107.5(17) . . ?
O51A Cl52 O53A 110.3(16) . . ?
O51A Cl52 O54A 109.3(16) . . ?
O53A Cl52 O52A 107.8(16) . . ?
O53A Cl52 O54A 111.7(14) . . ?
O54A Cl52 O52A 110.2(17) . . ?
H61A O61 H61B 109.5 . . ?

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 H2A O1 0.88 1.77 2.546(7) 146.0 .
N3 H3A O42 0.88 2.12 2.982(9) 167.0 2_745
N4 H4A O2 0.88 1.82 2.573(8) 142.7 .
N22 H22A O21 0.88 1.78 2.546(8) 143.9 .
N23 H23A O52 0.88 2.11 2.95(2) 158.1 1_454
N23 H23A O52A 0.88 1.96 2.81(2) 161.9 1_454
N24 H24A O22 0.88 1.78 2.551(10) 144.9 .
N25 H25 O61 0.88 1.93 2.794(10) 165.5 .
O61 H61A O42 0.87 2.26 2.996(10) 142.8 2_645
O61 H61A O44 0.87 2.39 3.191(10) 153.1 2_645
O61 H61B O21 0.87 2.06 2.895(9) 161.5 1_655

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 C2 C3 C4 -1.0(14) . . . . ?
C2 C1 N1 Cu1 -172.7(6) . . . . ?
C2 C1 N1 C5 2.7(11) . . . . ?
C2 C1 N2 C6 168.1(8) . . . . ?
C2 C3 C4 C5 1.5(16) . . . . ?
C3 C4 C5 N1 0.0(15) . . . . ?
C3 C4 C5 N4 -178.0(9) . . . . ?
C4 C5 N1 Cu1 173.3(7) . . . . ?
C4 C5 N1 C1 -2.1(12) . . . . ?
C4 C5 N4 C8 180.0(9) . . . . ?
C10 C7 N3 C6 169.6(7) . . . . ?
C14 C9 N5 C8 171.0(7) . . . . ?
N1 C1 C2 C3 -1.2(12) . . . . ?
N1 C1 N2 C6 -11.0(13) . . . . ?
N1 C5 N4 C8 1.9(15) . . . . ?
N2 C1 C2 C3 179.7(8) . . . . ?
N2 C1 N1 Cu1 6.3(10) . . . . ?
N2 C1 N1 C5 -178.3(7) . . . . ?
N2 C6 N3 C7 1.0(11) . . . . ?
N2 C6 S1 Cu1 -2.1(7) . . . . ?
N3 C6 N2 C1 -172.7(8) . . . . ?
N3 C6 S1 Cu1 179.3(5) . . . . ?
N3 C7 C10 C11 -174.7(6) . . . . ?
N3 C7 C10 C12 66.2(8) . . . . ?
N3 C7 C10 C13 -53.5(9) . . . . ?
N4 C5 N1 Cu1 -8.8(11) . . . . ?
N4 C5 N1 C1 175.7(7) . . . . ?
N4 C8 N5 C9 2.0(11) . . . . ?
N4 C8 S2 Cu1 -12.0(8) . . . . ?
N5 C8 N4 C5 -169.6(9) . . . . ?
N5 C8 S2 Cu1 169.2(5) . . . . ?
N5 C9 C14 C15 161.2(7) . . . . ?
N5 C9 C14 C16 37.7(9) . . . . ?
N5 C9 C14 C17 -82.8(8) . . . . ?
O1 C7 C10 C11 2.6(10) . . . . ?
O1 C7 C10 C12 -116.5(8) . . . . ?
O1 C7 C10 C13 123.8(8) . . . . ?
O1 C7 N3 C6 -7.6(12) . . . . ?
O2 C9 C14 C15 -22.8(11) . . . . ?
O2 C9 C14 C16 -146.3(8) . . . . ?
O2 C9 C14 C17 93.2(9) . . . . ?
O2 C9 N5 C8 -5.1(13) . . . . ?
S1 C6 N2 C1 8.7(13) . . . . ?
S1 C6 N3 C7 179.8(6) . . . . ?
S2 C8 N4 C5 11.7(14) . . . . ?
S2 C8 N5 C9 -179.1(6) . . . . ?
C21 C22 C23 C24 -0.4(12) . . . . ?
C22 C21 N21 Cu2 -174.9(5) . . . . ?
C22 C21 N21 C25 1.3(11) . . . . ?
C22 C21 N22 C26 -172.6(8) . . . . ?
C22 C23 C24 C25 1.7(12) . . . . ?
C23 C24 C25 N21 -1.6(13) . . . . ?
C23 C24 C25 N24 -177.6(7) . . . . ?
C24 C25 N21 Cu2 176.5(6) . . . . ?
C24 C25 N21 C21 0.1(11) . . . . ?
C24 C25 N24 C28 -175.2(9) . . . . ?
C30 C27 N23 C26 -178.4(7) . . . . ?
C34 C29 N25 C28 171.2(9) . . . . ?
N21 C21 C22 C23 -1.2(11) . . . . ?
N21 C21 N22 C26 8.4(13) . . . . ?
N21 C25 N24 C28 8.9(14) . . . . ?
N22 C21 C22 C23 179.8(7) . . . . ?
N22 C21 N21 Cu2 3.9(10) . . . . ?
N22 C21 N21 C25 -179.8(7) . . . . ?
N22 C26 N23 C27 -0.1(11) . . . . ?
N22 C26 S21 Cu2 0.7(8) . . . . ?
N23 C26 N22 C21 172.5(7) . . . . ?
N23 C26 S21 Cu2 177.2(5) . . . . ?
N23 C27 C30 C31 65.6(9) . . . . ?
N23 C27 C30 C32 -56.7(10) . . . . ?
N23 C27 C30 C33 -175.6(7) . . . . ?
N24 C25 N21 Cu2 -7.9(10) . . . . ?
N24 C25 N21 C21 175.7(7) . . . . ?
N24 C28 N25 C29 2.5(12) . . . . ?
N24 C28 S22 Cu2 -15.0(8) . . . . ?
N25 C28 N24 C25 -175.3(8) . . . . ?
N25 C28 S22 Cu2 166.9(6) . . . . ?
N25 C29 C34 C35 -64.6(12) . . . . ?
N25 C29 C34 C36 177.4(10) . . . . ?
N25 C29 C34 C37 60.5(14) . . . . ?
N25 C29 C34A C35A -30(3) . . . . ?
N25 C29 C34A C36A -147(3) . . . . ?
N25 C29 C34A C37A 99(3) . . . . ?
O21 C27 C30 C31 -111.0(9) . . . . ?
O21 C27 C30 C32 126.8(9) . . . . ?
O21 C27 C30 C33 7.9(12) . . . . ?
O21 C27 N23 C26 -1.7(13) . . . . ?
O22 C29 C34 C35 112.3(11) . . . . ?
O22 C29 C34 C36 -5.8(16) . . . . ?
O22 C29 C34 C37 -122.7(13) . . . . ?
O22 C29 N25 C28 -5.6(16) . . . . ?
O22 C29 C34A C35A 159(3) . . . . ?
O22 C29 C34A C36A 41(4) . . . . ?
O22 C29 C34A C37A -72(3) . . . . ?
S21 C26 N22 C21 -10.9(13) . . . . ?
S21 C26 N23 C27 -177.2(6) . . . . ?
S22 C28 N24 C25 6.5(14) . . . . ?
S22 C28 N25 C29 -179.1(7) . . . . ?
C34A C29 N25 C28 -176.6(17) . . . . ?

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