# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1545787'
_audit_update_record             
;
2017-04-24 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H26 Cl4 Cu2 N8 O7 S2'
_chemical_formula_weight         1039.67

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.629(5)
_cell_length_b                   15.946(5)
_cell_length_c                   16.469(5)
_cell_angle_alpha                92.875(5)
_cell_angle_beta                 99.764(5)
_cell_angle_gamma                101.239(5)
_cell_volume                     1929.4(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1392
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      22.37

_exptl_crystal_description       rod
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.552
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'SADABS 2014/4 Bruker AXS Madison WI USA'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11605
_diffrn_reflns_av_unetI/netI     0.0954
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.259
_diffrn_reflns_theta_max         25.392
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7084
_reflns_number_gt                4458
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT v8.34a'
_computing_data_reduction        'Bruker SAINT v8.34a'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0905P)²+1.2322P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7084
_refine_ls_number_parameters     597
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1847
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7289(9) 0.1342(5) 0.2461(4) 0.0276(16) Uani 1 1 d . . . . .
C2 C 0.7615(9) 0.0714(5) 0.3002(4) 0.0321(18) Uani 1 1 d . . . . .
H2 H 0.8461 0.0864 0.3490 0.039 Uiso 1 1 calc R U . . .
C3 C 0.6708(10) -0.0105(5) 0.2818(5) 0.0316(17) Uani 1 1 d . . . . .
C4 C 0.5403(9) -0.0305(5) 0.2089(4) 0.0248(16) Uani 1 1 d . . . . .
C5 C 0.5102(8) 0.0352(4) 0.1587(4) 0.0190(14) Uani 1 1 d . . . . .
C6 C 0.2544(10) 0.0774(5) -0.0343(4) 0.0280(16) Uani 1 1 d . . . . .
C7 C 0.1491(9) -0.0025(5) -0.0676(4) 0.0261(16) Uani 1 1 d . . . . .
C8 C 0.1613(9) -0.0728(5) -0.0234(4) 0.0259(16) Uani 1 1 d . . . . .
C9 C 0.2730(9) -0.0636(4) 0.0539(4) 0.0218(15) Uani 1 1 d . . . . .
C10 C 0.3770(8) 0.0195(4) 0.0821(4) 0.0197(14) Uani 1 1 d . . . . .
C11 C 0.4357(8) -0.1127(4) 0.1788(4) 0.0220(15) Uani 1 1 d . . . . .
C12 C 0.3019(9) -0.1301(4) 0.1062(4) 0.0240(15) Uani 1 1 d . . . . .
C13 C 0.3129(9) -0.2515(4) 0.1608(4) 0.0232(15) Uani 1 1 d . . . . .
C14 C 0.2748(9) -0.3446(4) 0.1695(4) 0.0232(15) Uani 1 1 d . . . . .
C15 C 0.2912(9) -0.3824(5) 0.2447(4) 0.0258(16) Uani 1 1 d . . . . .
C16 C 0.2517(11) -0.4714(5) 0.2451(5) 0.0361(19) Uani 1 1 d . . . . .
H16 H 0.2668 -0.4962 0.2950 0.043 Uiso 1 1 calc R U . . .
C17 C 0.1902(10) -0.5232(5) 0.1721(5) 0.036(2) Uani 1 1 d . . . . .
C18 C 0.1756(9) -0.4878(5) 0.0976(5) 0.0325(18) Uani 1 1 d . . . . .
H18 H 0.1383 -0.5229 0.0484 0.039 Uiso 1 1 calc R U . . .
C19 C 0.2162(9) -0.4002(4) 0.0961(4) 0.0274(16) Uani 1 1 d . . . . .
H19 H 0.2048 -0.3767 0.0454 0.033 Uiso 1 1 calc R U . . .
C20 C 0.9281(10) -0.2905(5) 0.5067(5) 0.0362(19) Uani 1 1 d . . . . .
H20 H 0.9740 -0.2340 0.5285 0.043 Uiso 1 1 calc R U . . .
C21 C 0.8949(11) -0.3530(5) 0.5607(5) 0.039(2) Uani 1 1 d . . . . .
C22 C 0.8214(11) -0.4366(5) 0.5310(5) 0.0362(19) Uani 1 1 d . . . . .
C23 C 0.7843(9) -0.4559(4) 0.4451(4) 0.0253(16) Uani 1 1 d . . . . .
C24 C 0.8292(9) -0.3892(5) 0.3952(4) 0.0248(16) Uani 1 1 d . . . . .
C25 C 0.8016(11) -0.3464(5) 0.1813(4) 0.0341(18) Uani 1 1 d . . . . .
C26 C 0.7244(10) -0.4253(5) 0.1372(4) 0.0301(17) Uani 1 1 d . . . . .
H26 H 0.7012 -0.4302 0.0797 0.036 Uiso 1 1 calc R U . . .
C27 C 0.6834(10) -0.4951(5) 0.1794(4) 0.0318(17) Uani 1 1 d . . . . .
H27 H 0.6331 -0.5486 0.1509 0.038 Uiso 1 1 calc R U . . .
C28 C 0.7171(8) -0.4864(4) 0.2661(4) 0.0223(15) Uani 1 1 d . . . . .
C29 C 0.7903(9) -0.4068(4) 0.3048(4) 0.0221(15) Uani 1 1 d . . . . .
C30 C 0.7065(9) -0.5377(4) 0.4038(4) 0.0231(15) Uani 1 1 d . . . . .
C31 C 0.6739(9) -0.5522(4) 0.3187(4) 0.0258(16) Uani 1 1 d . . . . .
C32 C 0.5681(9) -0.6753(4) 0.3701(4) 0.0261(16) Uani 1 1 d . . . . .
C33 C 0.4972(9) -0.7628(4) 0.3808(4) 0.0254(16) Uani 1 1 d . . . . .
C34 C 0.5646(10) -0.7972(5) 0.4519(5) 0.0343(18) Uani 1 1 d . . . . .
C35 C 0.4946(12) -0.8807(6) 0.4683(5) 0.051(2) Uani 1 1 d . . . . .
H35 H 0.5421 -0.9022 0.5168 0.061 Uiso 1 1 calc R U . . .
C36 C 0.3591(13) -0.9294(6) 0.4141(6) 0.053(3) Uani 1 1 d . . . . .
C37 C 0.2888(11) -0.9005(5) 0.3409(5) 0.042(2) Uani 1 1 d . . . . .
H37 H 0.1980 -0.9371 0.3033 0.051 Uiso 1 1 calc R U . . .
C38 C 0.3512(9) -0.8176(4) 0.3223(4) 0.0247(15) Uani 1 1 d . . . . .
N1 N 0.6070(8) 0.1179(4) 0.1776(3) 0.0262(13) Uani 1 1 d . . . . .
N2 N 0.3668(7) 0.0898(4) 0.0382(3) 0.0241(13) Uani 1 1 d . . . . .
N3 N 0.4347(8) -0.1922(4) 0.2099(3) 0.0282(14) Uani 1 1 d D . . . .
N4 N 0.2321(8) -0.2153(3) 0.0965(3) 0.0244(13) Uani 1 1 d . . . . .
N5 N 0.8977(7) -0.3075(4) 0.4256(3) 0.0218(12) Uani 1 1 d . . . . .
N6 N 0.8399(7) -0.3341(4) 0.2636(3) 0.0265(13) Uani 1 1 d . . . . .
N7 N 0.6410(8) -0.6150(4) 0.4347(3) 0.0258(13) Uani 1 1 d . . . . .
N8 N 0.5895(8) -0.6381(4) 0.3004(4) 0.0263(14) Uani 1 1 d . . . . .
O1 O 0.3681(8) -0.3847(4) 0.4032(3) 0.0479(15) Uani 1 1 d . . . . .
O2 O 0.2342(7) -0.2679(4) 0.3491(3) 0.0421(14) Uani 1 1 d . . . . .
O1W O -0.0518(7) -0.2919(4) -0.0227(3) 0.0441(14) Uiso 1 1 d . . . . .
O3 O 0.5447(6) -0.2718(3) 0.3415(3) 0.0316(12) Uani 1 1 d . . . . .
O4 O 0.3733(6) -0.7495(3) 0.1825(3) 0.0305(12) Uani 1 1 d . . . . .
O5 O 0.1663(7) -0.7101(4) 0.2640(3) 0.0409(14) Uani 1 1 d . . . . .
O6 O 0.1067(7) -0.8526(4) 0.1899(3) 0.0467(15) Uani 1 1 d . . . . .
S1 S 0.3633(2) -0.32106(12) 0.34245(10) 0.0278(4) Uani 1 1 d . . . . .
S2 S 0.2368(2) -0.78063(12) 0.23232(11) 0.0273(4) Uani 1 1 d . . . . .
Cu1 Cu 0.53383(11) 0.19975(5) 0.09359(5) 0.0265(2) Uani 1 1 d . . . . .
Cu2 Cu 0.93631(12) -0.22278(6) 0.33729(5) 0.0288(3) Uani 1 1 d . . . . .
Cl1 Cl 0.7817(2) 0.30300(12) 0.14201(13) 0.0416(5) Uani 1 1 d . . . . .
Cl2 Cl 0.4379(3) 0.27882(13) -0.00821(12) 0.0396(5) Uani 1 1 d . . . . .
Cl3 Cl 0.9567(3) -0.14345(13) 0.22894(13) 0.0481(6) Uani 1 1 d . . . . .
Cl4 Cl 0.9934(3) -0.10936(13) 0.42888(14) 0.0542(6) Uani 1 1 d . . . . .
H1 H 0.814(9) 0.194(5) 0.257(4) 0.030(19) Uiso 1 1 d . . . . .
H3 H 0.700(8) -0.055(4) 0.322(4) 0.027(18) Uiso 1 1 d . . . . .
H6 H 0.236(9) 0.121(5) -0.070(4) 0.029(19) Uiso 1 1 d . . . . .
H7 H 0.054(10) -0.011(5) -0.127(5) 0.05(2) Uiso 1 1 d . . . . .
H8 H 0.094(9) -0.117(5) -0.046(4) 0.02(2) Uiso 1 1 d . . . . .
H9 H 0.526(9) -0.668(5) 0.253(4) 0.03(2) Uiso 1 1 d . . . . .
H17 H 0.174(11) -0.579(6) 0.174(5) 0.05(3) Uiso 1 1 d . . . . .
H21 H 0.893(9) -0.341(4) 0.607(4) 0.02(2) Uiso 1 1 d . . . . .
H22 H 0.805(8) -0.473(4) 0.567(4) 0.016(17) Uiso 1 1 d . . . . .
H25 H 0.876(11) -0.296(6) 0.159(5) 0.06(3) Uiso 1 1 d . . . . .
H34 H 0.661(9) -0.762(4) 0.487(4) 0.023(18) Uiso 1 1 d . . . . .
H36 H 0.313(9) -0.981(5) 0.419(4) 0.021(18) Uiso 1 1 d . . . . .
H3A H 0.503(9) -0.209(5) 0.255(3) 0.05(3) 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
C1 N1 1.313(8) . ?
C1 C2 1.405(10) . ?
C1 H1 1.03(7) . ?
C2 C3 1.346(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(10) . ?
C3 H3 1.02(7) . ?
C4 C5 1.397(9) . ?
C4 C11 1.412(9) . ?
C5 N1 1.373(8) . ?
C5 C10 1.456(8) . ?
C6 N2 1.328(8) . ?
C6 C7 1.397(10) . ?
C6 H6 0.94(7) . ?
C7 C8 1.376(10) . ?
C7 H7 1.10(7) . ?
C8 C9 1.391(9) . ?
C8 H8 0.82(7) . ?
C9 C10 1.417(9) . ?
C9 C12 1.426(9) . ?
C10 N2 1.371(8) . ?
C11 N3 1.389(9) . ?
C11 C12 1.411(9) . ?
C12 N4 1.350(8) . ?
C13 N3 1.318(8) . ?
C13 N4 1.347(8) . ?
C13 C14 1.474(9) . ?
C14 C15 1.402(9) . ?
C14 C19 1.414(9) . ?
C15 C16 1.392(10) . ?
C15 S1 1.784(7) . ?
C16 C17 1.381(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(10) . ?
C17 H17 0.88(8) . ?
C18 C19 1.373(10) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 N5 1.321(9) . ?
C20 C21 1.383(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(11) . ?
C21 H21 0.79(7) . ?
C22 C23 1.401(9) . ?
C22 H22 0.85(7) . ?
C23 C24 1.401(9) . ?
C23 C30 1.411(9) . ?
C24 N5 1.342(9) . ?
C24 C29 1.470(9) . ?
C25 N6 1.335(9) . ?
C25 C26 1.390(10) . ?
C25 H25 1.01(9) . ?
C26 C27 1.354(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.403(9) . ?
C27 H27 0.9300 . ?
C28 C29 1.361(9) . ?
C28 C31 1.419(9) . ?
C29 N6 1.393(8) . ?
C30 C31 1.380(9) . ?
C30 N7 1.392(8) . ?
C31 N8 1.390(9) . ?
C32 N8 1.337(8) . ?
C32 N7 1.362(8) . ?
C32 C33 1.426(9) . ?
C33 C34 1.381(10) . ?
C33 C38 1.451(9) . ?
C34 C35 1.392(11) . ?
C34 H34 0.93(7) . ?
C35 C36 1.332(12) . ?
C35 H35 0.9300 . ?
C36 C37 1.375(12) . ?
C36 H36 0.84(7) . ?
C37 C38 1.383(10) . ?
C37 H37 0.9300 . ?
C38 S2 1.775(7) . ?
N1 Cu1 2.033(6) . ?
N2 Cu1 2.026(6) . ?
N3 H3A 0.912(10) . ?
N5 Cu2 2.052(6) . ?
N6 Cu2 2.034(6) . ?
N8 H9 0.91(7) . ?
O1 S1 1.462(5) . ?
O2 S1 1.433(5) . ?
O3 S1 1.454(5) . ?
O4 S2 1.460(5) . ?
O4 Cu1 2.275(5) 1_545 ?
O5 S2 1.449(5) . ?
O6 S2 1.424(5) . ?
Cu1 Cl1 2.251(2) . ?
Cu1 Cl2 2.257(2) . ?
Cu1 O4 2.275(5) 1_565 ?
Cu2 Cl4 2.221(2) . ?
Cu2 Cl3 2.248(2) . ?

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 C1 C2 122.9(7) . . ?
N1 C1 H1 118(4) . . ?
C2 C1 H1 119(4) . . ?
C3 C2 C1 120.3(7) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 118.4(7) . . ?
C2 C3 H3 118(4) . . ?
C4 C3 H3 123(4) . . ?
C5 C4 C3 118.7(7) . . ?
C5 C4 C11 115.0(6) . . ?
C3 C4 C11 126.3(7) . . ?
N1 C5 C4 122.1(6) . . ?
N1 C5 C10 116.0(6) . . ?
C4 C5 C10 122.0(6) . . ?
N2 C6 C7 123.5(7) . . ?
N2 C6 H6 125(4) . . ?
C7 C6 H6 112(4) . . ?
C8 C7 C6 118.9(7) . . ?
C8 C7 H7 119(4) . . ?
C6 C7 H7 123(4) . . ?
C7 C8 C9 120.3(7) . . ?
C7 C8 H8 114(5) . . ?
C9 C8 H8 126(5) . . ?
C8 C9 C10 117.0(6) . . ?
C8 C9 C12 126.8(6) . . ?
C10 C9 C12 116.1(6) . . ?
N2 C10 C9 123.0(6) . . ?
N2 C10 C5 115.2(6) . . ?
C9 C10 C5 121.7(6) . . ?
N3 C11 C12 104.4(6) . . ?
N3 C11 C4 130.9(6) . . ?
C12 C11 C4 124.7(6) . . ?
N4 C12 C11 108.2(6) . . ?
N4 C12 C9 131.2(6) . . ?
C11 C12 C9 120.4(6) . . ?
N3 C13 N4 109.5(6) . . ?
N3 C13 C14 126.9(6) . . ?
N4 C13 C14 123.5(6) . . ?
C15 C14 C19 117.3(6) . . ?
C15 C14 C13 125.2(6) . . ?
C19 C14 C13 117.4(6) . . ?
C16 C15 C14 120.0(6) . . ?
C16 C15 S1 117.3(5) . . ?
C14 C15 S1 122.7(5) . . ?
C17 C16 C15 120.7(7) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.3(7) . . ?
C18 C17 H17 121(6) . . ?
C16 C17 H17 119(6) . . ?
C17 C18 C19 119.6(7) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C14 121.9(6) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
N5 C20 C21 123.0(7) . . ?
N5 C20 H20 118.5 . . ?
C21 C20 H20 118.5 . . ?
C22 C21 C20 120.4(7) . . ?
C22 C21 H21 116(5) . . ?
C20 C21 H21 121(5) . . ?
C21 C22 C23 117.7(7) . . ?
C21 C22 H22 117(4) . . ?
C23 C22 H22 126(4) . . ?
C24 C23 C22 118.0(6) . . ?
C24 C23 C30 116.6(6) . . ?
C22 C23 C30 125.4(7) . . ?
N5 C24 C23 123.2(6) . . ?
N5 C24 C29 117.1(6) . . ?
C23 C24 C29 119.5(6) . . ?
N6 C25 C26 124.3(7) . . ?
N6 C25 H25 108(5) . . ?
C26 C25 H25 125(5) . . ?
C27 C26 C25 118.9(7) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C26 C27 C28 119.7(7) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 117.9(6) . . ?
C29 C28 C31 115.6(6) . . ?
C27 C28 C31 126.4(6) . . ?
C28 C29 N6 124.0(6) . . ?
C28 C29 C24 123.0(6) . . ?
N6 C29 C24 112.9(6) . . ?
C31 C30 N7 107.1(6) . . ?
C31 C30 C23 122.4(6) . . ?
N7 C30 C23 130.5(6) . . ?
C30 C31 N8 106.3(6) . . ?
C30 C31 C28 122.8(6) . . ?
N8 C31 C28 130.9(6) . . ?
N8 C32 N7 107.7(6) . . ?
N8 C32 C33 129.3(6) . . ?
N7 C32 C33 122.9(6) . . ?
C34 C33 C32 119.0(6) . . ?
C34 C33 C38 117.5(6) . . ?
C32 C33 C38 123.4(6) . . ?
C33 C34 C35 121.9(7) . . ?
C33 C34 H34 116(4) . . ?
C35 C34 H34 122(4) . . ?
C36 C35 C34 119.5(8) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C37 121.8(8) . . ?
C35 C36 H36 125(5) . . ?
C37 C36 H36 113(5) . . ?
C36 C37 C38 120.9(8) . . ?
C36 C37 H37 119.5 . . ?
C38 C37 H37 119.5 . . ?
C37 C38 C33 118.3(7) . . ?
C37 C38 S2 118.4(5) . . ?
C33 C38 S2 123.1(5) . . ?
C1 N1 C5 117.6(6) . . ?
C1 N1 Cu1 129.0(5) . . ?
C5 N1 Cu1 113.4(4) . . ?
C6 N2 C10 117.3(6) . . ?
C6 N2 Cu1 128.6(5) . . ?
C10 N2 Cu1 114.1(4) . . ?
C13 N3 C11 109.7(6) . . ?
C13 N3 H3A 119(5) . . ?
C11 N3 H3A 132(5) . . ?
C13 N4 C12 108.3(5) . . ?
C20 N5 C24 117.6(6) . . ?
C20 N5 Cu2 127.9(5) . . ?
C24 N5 Cu2 114.4(4) . . ?
C25 N6 C29 115.1(6) . . ?
C25 N6 Cu2 129.2(5) . . ?
C29 N6 Cu2 115.3(4) . . ?
C32 N7 C30 108.8(5) . . ?
C32 N8 C31 110.2(6) . . ?
C32 N8 H9 116(5) . . ?
C31 N8 H9 132(5) . . ?
S2 O4 Cu1 140.2(3) . 1_545 ?
O2 S1 O3 112.8(3) . . ?
O2 S1 O1 114.1(4) . . ?
O3 S1 O1 111.2(3) . . ?
O2 S1 C15 107.0(3) . . ?
O3 S1 C15 106.1(3) . . ?
O1 S1 C15 104.9(3) . . ?
O6 S2 O5 116.8(4) . . ?
O6 S2 O4 111.0(3) . . ?
O5 S2 O4 110.5(3) . . ?
O6 S2 C38 106.7(3) . . ?
O5 S2 C38 104.0(3) . . ?
O4 S2 C38 107.1(3) . . ?
N2 Cu1 N1 81.2(2) . . ?
N2 Cu1 Cl1 162.89(16) . . ?
N1 Cu1 Cl1 93.37(17) . . ?
N2 Cu1 Cl2 93.16(16) . . ?
N1 Cu1 Cl2 174.23(17) . . ?
Cl1 Cu1 Cl2 91.70(8) . . ?
N2 Cu1 O4 104.1(2) . 1_565 ?
N1 Cu1 O4 89.1(2) . 1_565 ?
Cl1 Cu1 O4 92.00(14) . 1_565 ?
Cl2 Cu1 O4 93.50(14) . 1_565 ?
N6 Cu2 N5 80.0(2) . . ?
N6 Cu2 Cl4 168.65(17) . . ?
N5 Cu2 Cl4 92.77(16) . . ?
N6 Cu2 Cl3 92.93(17) . . ?
N5 Cu2 Cl3 172.72(16) . . ?
Cl4 Cu2 Cl3 93.91(9) . . ?

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
N1 C1 C2 C3 2.3(11) . . . . ?
C1 C2 C3 C4 -1.8(11) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C2 C3 C4 C11 178.4(7) . . . . ?
C3 C4 C5 N1 1.6(10) . . . . ?
C11 C4 C5 N1 -177.1(6) . . . . ?
C3 C4 C5 C10 -179.9(6) . . . . ?
C11 C4 C5 C10 1.4(9) . . . . ?
N2 C6 C7 C8 0.0(11) . . . . ?
C6 C7 C8 C9 1.7(10) . . . . ?
C7 C8 C9 C10 -2.7(10) . . . . ?
C7 C8 C9 C12 -179.0(7) . . . . ?
C8 C9 C10 N2 2.2(10) . . . . ?
C12 C9 C10 N2 178.9(6) . . . . ?
C8 C9 C10 C5 -174.5(6) . . . . ?
C12 C9 C10 C5 2.2(9) . . . . ?
N1 C5 C10 N2 0.6(8) . . . . ?
C4 C5 C10 N2 -178.0(6) . . . . ?
N1 C5 C10 C9 177.6(6) . . . . ?
C4 C5 C10 C9 -1.1(10) . . . . ?
C5 C4 C11 N3 177.1(7) . . . . ?
C3 C4 C11 N3 -1.4(12) . . . . ?
C5 C4 C11 C12 -3.3(10) . . . . ?
C3 C4 C11 C12 178.2(7) . . . . ?
N3 C11 C12 N4 -1.0(7) . . . . ?
C4 C11 C12 N4 179.3(6) . . . . ?
N3 C11 C12 C9 -175.6(6) . . . . ?
C4 C11 C12 C9 4.6(10) . . . . ?
C8 C9 C12 N4 -0.7(12) . . . . ?
C10 C9 C12 N4 -177.0(7) . . . . ?
C8 C9 C12 C11 172.5(7) . . . . ?
C10 C9 C12 C11 -3.8(9) . . . . ?
N3 C13 C14 C15 32.0(11) . . . . ?
N4 C13 C14 C15 -152.4(7) . . . . ?
N3 C13 C14 C19 -148.4(7) . . . . ?
N4 C13 C14 C19 27.3(9) . . . . ?
C19 C14 C15 C16 0.5(10) . . . . ?
C13 C14 C15 C16 -179.9(6) . . . . ?
C19 C14 C15 S1 -180.0(5) . . . . ?
C13 C14 C15 S1 -0.3(10) . . . . ?
C14 C15 C16 C17 -2.2(11) . . . . ?
S1 C15 C16 C17 178.2(6) . . . . ?
C15 C16 C17 C18 3.1(12) . . . . ?
C16 C17 C18 C19 -2.3(12) . . . . ?
C17 C18 C19 C14 0.6(11) . . . . ?
C15 C14 C19 C18 0.3(10) . . . . ?
C13 C14 C19 C18 -179.3(6) . . . . ?
N5 C20 C21 C22 -2.3(13) . . . . ?
C20 C21 C22 C23 0.8(13) . . . . ?
C21 C22 C23 C24 1.7(11) . . . . ?
C21 C22 C23 C30 -179.0(7) . . . . ?
C22 C23 C24 N5 -3.2(11) . . . . ?
C30 C23 C24 N5 177.5(6) . . . . ?
C22 C23 C24 C29 -179.3(6) . . . . ?
C30 C23 C24 C29 1.4(9) . . . . ?
N6 C25 C26 C27 0.4(12) . . . . ?
C25 C26 C27 C28 0.8(11) . . . . ?
C26 C27 C28 C29 0.2(10) . . . . ?
C26 C27 C28 C31 176.8(7) . . . . ?
C27 C28 C29 N6 -2.5(10) . . . . ?
C31 C28 C29 N6 -179.4(6) . . . . ?
C27 C28 C29 C24 179.0(6) . . . . ?
C31 C28 C29 C24 2.1(9) . . . . ?
N5 C24 C29 C28 -178.6(6) . . . . ?
C23 C24 C29 C28 -2.3(10) . . . . ?
N5 C24 C29 N6 2.8(8) . . . . ?
C23 C24 C29 N6 179.1(6) . . . . ?
C24 C23 C30 C31 -0.6(10) . . . . ?
C22 C23 C30 C31 -179.9(7) . . . . ?
C24 C23 C30 N7 -176.9(7) . . . . ?
C22 C23 C30 N7 3.8(12) . . . . ?
N7 C30 C31 N8 -0.1(7) . . . . ?
C23 C30 C31 N8 -177.2(6) . . . . ?
N7 C30 C31 C28 177.6(6) . . . . ?
C23 C30 C31 C28 0.5(11) . . . . ?
C29 C28 C31 C30 -1.3(10) . . . . ?
C27 C28 C31 C30 -177.9(7) . . . . ?
C29 C28 C31 N8 175.8(7) . . . . ?
C27 C28 C31 N8 -0.8(12) . . . . ?
N8 C32 C33 C34 147.9(8) . . . . ?
N7 C32 C33 C34 -26.7(10) . . . . ?
N8 C32 C33 C38 -34.9(12) . . . . ?
N7 C32 C33 C38 150.5(7) . . . . ?
C32 C33 C34 C35 176.4(7) . . . . ?
C38 C33 C34 C35 -0.9(12) . . . . ?
C33 C34 C35 C36 0.2(14) . . . . ?
C34 C35 C36 C37 1.7(15) . . . . ?
C35 C36 C37 C38 -2.9(15) . . . . ?
C36 C37 C38 C33 2.1(12) . . . . ?
C36 C37 C38 S2 -172.9(7) . . . . ?
C34 C33 C38 C37 -0.2(10) . . . . ?
C32 C33 C38 C37 -177.4(7) . . . . ?
C34 C33 C38 S2 174.5(6) . . . . ?
C32 C33 C38 S2 -2.7(10) . . . . ?
C2 C1 N1 C5 -0.8(10) . . . . ?
C2 C1 N1 Cu1 177.8(5) . . . . ?
C4 C5 N1 C1 -1.1(9) . . . . ?
C10 C5 N1 C1 -179.7(6) . . . . ?
C4 C5 N1 Cu1 -179.9(5) . . . . ?
C10 C5 N1 Cu1 1.5(7) . . . . ?
C7 C6 N2 C10 -0.5(10) . . . . ?
C7 C6 N2 Cu1 178.0(5) . . . . ?
C9 C10 N2 C6 -0.6(9) . . . . ?
C5 C10 N2 C6 176.3(6) . . . . ?
C9 C10 N2 Cu1 -179.3(5) . . . . ?
C5 C10 N2 Cu1 -2.4(7) . . . . ?
N4 C13 N3 C11 0.9(8) . . . . ?
C14 C13 N3 C11 177.0(6) . . . . ?
C12 C11 N3 C13 0.1(8) . . . . ?
C4 C11 N3 C13 179.8(7) . . . . ?
N3 C13 N4 C12 -1.5(8) . . . . ?
C14 C13 N4 C12 -177.8(6) . . . . ?
C11 C12 N4 C13 1.6(7) . . . . ?
C9 C12 N4 C13 175.4(7) . . . . ?
C21 C20 N5 C24 0.9(11) . . . . ?
C21 C20 N5 Cu2 179.2(6) . . . . ?
C23 C24 N5 C20 1.9(10) . . . . ?
C29 C24 N5 C20 178.0(6) . . . . ?
C23 C24 N5 Cu2 -176.6(5) . . . . ?
C29 C24 N5 Cu2 -0.5(7) . . . . ?
C26 C25 N6 C29 -2.4(11) . . . . ?
C26 C25 N6 Cu2 -175.5(5) . . . . ?
C28 C29 N6 C25 3.6(10) . . . . ?
C24 C29 N6 C25 -177.9(6) . . . . ?
C28 C29 N6 Cu2 177.6(5) . . . . ?
C24 C29 N6 Cu2 -3.8(7) . . . . ?
N8 C32 N7 C30 1.1(8) . . . . ?
C33 C32 N7 C30 176.7(6) . . . . ?
C31 C30 N7 C32 -0.6(8) . . . . ?
C23 C30 N7 C32 176.1(7) . . . . ?
N7 C32 N8 C31 -1.2(8) . . . . ?
C33 C32 N8 C31 -176.4(7) . . . . ?
C30 C31 N8 C32 0.8(8) . . . . ?
C28 C31 N8 C32 -176.7(7) . . . . ?
C16 C15 S1 O2 -119.9(6) . . . . ?
C14 C15 S1 O2 60.5(7) . . . . ?
C16 C15 S1 O3 119.4(6) . . . . ?
C14 C15 S1 O3 -60.2(6) . . . . ?
C16 C15 S1 O1 1.6(7) . . . . ?
C14 C15 S1 O1 -177.9(6) . . . . ?
Cu1 O4 S2 O6 -37.7(6) 1_545 . . . ?
Cu1 O4 S2 O5 -168.9(4) 1_545 . . . ?
Cu1 O4 S2 C38 78.5(5) 1_545 . . . ?
C37 C38 S2 O6 -6.6(7) . . . . ?
C33 C38 S2 O6 178.6(6) . . . . ?
C37 C38 S2 O5 117.4(6) . . . . ?
C33 C38 S2 O5 -57.3(6) . . . . ?
C37 C38 S2 O4 -125.6(6) . . . . ?
C33 C38 S2 O4 59.7(6) . . . . ?

_refine_diff_density_max         0.620
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.132

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1545788'
_audit_update_record             
;
2017-04-24 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 Cl2 Cu N4 O4 P0 S'
_chemical_formula_weight         528.84

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'
P P 0.1023 0.0942 '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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.124(5)
_cell_length_b                   32.652(5)
_cell_length_c                   7.379(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 93.140(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1954.5(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2246
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.61

_exptl_crystal_description       flake
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.536
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   'SADABS 2014/4 Bruker AXS Madison WI USA'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14405
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.247
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4856
_reflns_number_gt                3330
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT v8.34a'
_computing_data_reduction        'Bruker SAINT v8.34a'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+9.5305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4856
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0808
_refine_ls_wR_factor_ref         0.1903
_refine_ls_wR_factor_gt          0.1745
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2663(8) 0.20048(19) 0.4303(10) 0.0389(15) Uani 1 1 d . . . . .
C2 C 1.3672(8) 0.1677(2) 0.4743(11) 0.0434(17) Uani 1 1 d . . . . .
C3 C 1.3154(7) 0.12859(19) 0.4369(10) 0.0362(15) Uani 1 1 d . . . . .
C4 C 1.1582(7) 0.12311(16) 0.3520(8) 0.0278(12) Uani 1 1 d . . . . .
C5 C 1.0621(7) 0.15794(17) 0.3098(8) 0.0277(12) Uani 1 1 d . . . . .
C6 C 0.6713(8) 0.1897(2) 0.1016(10) 0.0395(15) Uani 1 1 d . . . . .
C7 C 0.5923(8) 0.1534(2) 0.0569(10) 0.0406(16) Uani 1 1 d . . . . .
C8 C 0.6672(8) 0.1168(2) 0.0906(10) 0.0397(16) Uani 1 1 d . . . . .
C9 C 0.8289(7) 0.11683(17) 0.1765(8) 0.0286(12) Uani 1 1 d . . . . .
C10 C 0.8994(7) 0.15504(17) 0.2211(8) 0.0304(13) Uani 1 1 d . . . . .
C11 C 1.0817(7) 0.08491(16) 0.3059(8) 0.0274(12) Uani 1 1 d . . . . .
C12 C 0.9270(7) 0.08183(16) 0.2205(8) 0.0281(12) Uani 1 1 d . . . . .
C13 C 1.0246(7) 0.01886(17) 0.2639(8) 0.0259(12) Uani 1 1 d . . . . .
C14 C 1.0449(7) -0.02597(16) 0.2682(7) 0.0246(11) Uani 1 1 d . . . . .
C15 C 1.2048(8) -0.0402(2) 0.3079(10) 0.0388(15) Uani 1 1 d . . . . .
C16 C 1.2392(8) -0.0818(2) 0.3211(11) 0.0428(17) Uani 1 1 d . . . . .
C17 C 1.1190(8) -0.11041(18) 0.2794(10) 0.0389(15) Uani 1 1 d . . . . .
C18 C 0.9613(8) -0.09677(18) 0.2295(9) 0.0330(14) Uani 1 1 d . . . . .
C19 C 0.9210(7) -0.05539(17) 0.2246(8) 0.0282(12) Uani 1 1 d . . . . .
N1 N 1.1189(6) 0.19644(14) 0.3478(7) 0.0320(11) Uani 1 1 d . . . . .
N2 N 0.8224(6) 0.19104(14) 0.1841(7) 0.0319(11) Uani 1 1 d . . . . .
N3 N 1.1383(6) 0.04536(14) 0.3334(7) 0.0277(10) Uani 1 1 d . . . . .
N4 N 0.8945(6) 0.04096(14) 0.1983(7) 0.0264(10) Uani 1 1 d . . . . .
O1 O 0.6972(5) -0.01343(13) 0.0373(6) 0.0405(11) Uani 1 1 d . . . . .
O2 O 0.6573(5) -0.02669(14) 0.3536(7) 0.0426(11) Uani 1 1 d . . . . .
O1W O 0.4805(8) 0.04422(19) 0.2862(9) 0.0752(18) Uiso 1 1 d . . . . .
O3 O 0.6280(6) -0.08155(14) 0.1347(8) 0.0562(15) Uani 1 1 d . . . . .
S1 S 0.70734(18) -0.04393(5) 0.1834(2) 0.0332(4) Uani 1 1 d . . . . .
Cl1 Cl 0.7806(2) 0.28367(5) 0.1122(3) 0.0524(5) Uani 1 1 d . . . . .
Cl2 Cl 1.1156(2) 0.29136(5) 0.3793(3) 0.0513(5) Uani 1 1 d . . . . .
Cu1 Cu 0.95686(10) 0.24072(2) 0.26118(11) 0.0362(2) Uani 1 1 d . . . . .
H1 H 1.295(7) 0.2257(19) 0.456(8) 0.029(16) Uiso 1 1 d . . . . .
H2 H 1.456(10) 0.172(2) 0.553(12) 0.07(3) Uiso 1 1 d . . . . .
H3 H 1.373(8) 0.1036(19) 0.469(9) 0.037(18) Uiso 1 1 d . . . . .
H4 H 0.821(11) 0.028(3) 0.090(13) 0.09(3) Uiso 1 1 d . . . . .
H6 H 0.622(7) 0.2136(16) 0.082(7) 0.015(13) Uiso 1 1 d . . . . .
H7 H 0.489(9) 0.1536(19) -0.014(9) 0.040(18) Uiso 1 1 d . . . . .
H8 H 0.625(8) 0.093(2) 0.072(9) 0.04(2) Uiso 1 1 d . . . . .
H15 H 1.283(8) -0.0243(19) 0.330(9) 0.030(17) Uiso 1 1 d . . . . .
H16 H 1.339(9) -0.090(2) 0.322(10) 0.04(2) Uiso 1 1 d . . . . .
H17 H 1.141(7) -0.1422(17) 0.278(8) 0.025(15) Uiso 1 1 d . . . . .
H18 H 0.875(7) -0.1181(17) 0.207(8) 0.021(14) 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
C1 N1 1.320(8) . ?
C1 C2 1.375(9) . ?
C1 H1 0.87(6) . ?
C2 C3 1.369(9) . ?
C2 H2 0.91(9) . ?
C3 C4 1.403(8) . ?
C3 H3 0.96(6) . ?
C4 C5 1.404(8) . ?
C4 C11 1.426(7) . ?
C5 N1 1.363(7) . ?
C5 C10 1.445(8) . ?
C6 N2 1.341(8) . ?
C6 C7 1.378(9) . ?
C6 H6 0.88(5) . ?
C7 C8 1.358(9) . ?
C7 H7 0.96(7) . ?
C8 C9 1.426(8) . ?
C8 H8 0.87(7) . ?
C9 C10 1.405(7) . ?
C9 C12 1.421(8) . ?
C10 N2 1.353(7) . ?
C11 C12 1.378(8) . ?
C11 N3 1.382(7) . ?
C12 N4 1.368(7) . ?
C13 N3 1.347(7) . ?
C13 N4 1.347(7) . ?
C13 C14 1.473(7) . ?
C14 C15 1.396(8) . ?
C14 C19 1.416(7) . ?
C15 C16 1.389(9) . ?
C15 H15 0.83(6) . ?
C16 C17 1.375(9) . ?
C16 H16 0.86(7) . ?
C17 C18 1.387(9) . ?
C17 H17 1.05(6) . ?
C18 C19 1.390(8) . ?
C18 H18 1.00(6) . ?
C19 S1 1.785(6) . ?
N1 Cu1 2.035(5) . ?
N2 Cu1 2.020(5) . ?
N4 H4 1.06(9) . ?
O1 S1 1.466(5) . ?
O2 S1 1.455(5) . ?
O3 S1 1.424(4) . ?
Cl1 Cu1 2.2480(19) . ?
Cl2 Cu1 2.2435(18) . ?

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 C1 C2 123.0(6) . . ?
N1 C1 H1 115(4) . . ?
C2 C1 H1 122(4) . . ?
C3 C2 C1 120.4(6) . . ?
C3 C2 H2 119(5) . . ?
C1 C2 H2 119(5) . . ?
C2 C3 C4 118.1(6) . . ?
C2 C3 H3 127(4) . . ?
C4 C3 H3 115(4) . . ?
C3 C4 C5 118.5(5) . . ?
C3 C4 C11 126.3(5) . . ?
C5 C4 C11 115.2(5) . . ?
N1 C5 C4 121.6(5) . . ?
N1 C5 C10 116.4(5) . . ?
C4 C5 C10 122.0(5) . . ?
N2 C6 C7 122.7(6) . . ?
N2 C6 H6 116(4) . . ?
C7 C6 H6 121(4) . . ?
C8 C7 C6 120.9(6) . . ?
C8 C7 H7 118(4) . . ?
C6 C7 H7 120(4) . . ?
C7 C8 C9 118.3(6) . . ?
C7 C8 H8 127(5) . . ?
C9 C8 H8 115(5) . . ?
C10 C9 C12 116.4(5) . . ?
C10 C9 C8 117.3(5) . . ?
C12 C9 C8 126.4(5) . . ?
N2 C10 C9 123.1(5) . . ?
N2 C10 C5 115.9(5) . . ?
C9 C10 C5 121.0(5) . . ?
C12 C11 N3 106.7(5) . . ?
C12 C11 C4 123.2(5) . . ?
N3 C11 C4 130.2(5) . . ?
N4 C12 C11 106.9(5) . . ?
N4 C12 C9 130.9(5) . . ?
C11 C12 C9 122.1(5) . . ?
N3 C13 N4 107.5(5) . . ?
N3 C13 C14 123.8(5) . . ?
N4 C13 C14 128.6(5) . . ?
C15 C14 C19 117.6(5) . . ?
C15 C14 C13 115.9(5) . . ?
C19 C14 C13 126.3(5) . . ?
C16 C15 C14 121.4(6) . . ?
C16 C15 H15 117(4) . . ?
C14 C15 H15 122(4) . . ?
C17 C16 C15 120.7(6) . . ?
C17 C16 H16 116(5) . . ?
C15 C16 H16 120(5) . . ?
C16 C17 C18 118.4(5) . . ?
C16 C17 H17 123(3) . . ?
C18 C17 H17 118(3) . . ?
C17 C18 C19 122.2(5) . . ?
C17 C18 H18 117(3) . . ?
C19 C18 H18 121(3) . . ?
C18 C19 C14 119.3(5) . . ?
C18 C19 S1 115.7(4) . . ?
C14 C19 S1 124.7(4) . . ?
C1 N1 C5 118.4(5) . . ?
C1 N1 Cu1 129.0(4) . . ?
C5 N1 Cu1 112.7(4) . . ?
C6 N2 C10 117.7(5) . . ?
C6 N2 Cu1 128.5(4) . . ?
C10 N2 Cu1 113.8(4) . . ?
C13 N3 C11 109.2(5) . . ?
C13 N4 C12 109.7(4) . . ?
C13 N4 H4 117(5) . . ?
C12 N4 H4 126(5) . . ?
O3 S1 O2 114.1(3) . . ?
O3 S1 O1 113.2(3) . . ?
O2 S1 O1 111.4(3) . . ?
O3 S1 C19 106.5(3) . . ?
O2 S1 C19 104.4(3) . . ?
O1 S1 C19 106.4(3) . . ?
N2 Cu1 N1 81.28(19) . . ?
N2 Cu1 Cl2 172.63(16) . . ?
N1 Cu1 Cl2 93.07(14) . . ?
N2 Cu1 Cl1 92.46(15) . . ?
N1 Cu1 Cl1 168.75(16) . . ?
Cl2 Cu1 Cl1 93.86(7) . . ?

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
N1 C1 C2 C3 -1.6(12) . . . . ?
C1 C2 C3 C4 0.4(11) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C2 C3 C4 C11 -178.6(7) . . . . ?
C3 C4 C5 N1 0.6(9) . . . . ?
C11 C4 C5 N1 179.4(6) . . . . ?
C3 C4 C5 C10 179.5(6) . . . . ?
C11 C4 C5 C10 -1.8(9) . . . . ?
N2 C6 C7 C8 -1.9(12) . . . . ?
C6 C7 C8 C9 1.1(12) . . . . ?
C7 C8 C9 C10 0.2(10) . . . . ?
C7 C8 C9 C12 -179.3(7) . . . . ?
C12 C9 C10 N2 178.6(6) . . . . ?
C8 C9 C10 N2 -1.0(10) . . . . ?
C12 C9 C10 C5 -1.0(9) . . . . ?
C8 C9 C10 C5 179.5(6) . . . . ?
N1 C5 C10 N2 0.6(8) . . . . ?
C4 C5 C10 N2 -178.3(6) . . . . ?
N1 C5 C10 C9 -179.8(6) . . . . ?
C4 C5 C10 C9 1.3(9) . . . . ?
C3 C4 C11 C12 -179.3(6) . . . . ?
C5 C4 C11 C12 2.1(9) . . . . ?
C3 C4 C11 N3 0.9(11) . . . . ?
C5 C4 C11 N3 -177.7(6) . . . . ?
N3 C11 C12 N4 -0.2(7) . . . . ?
C4 C11 C12 N4 180.0(5) . . . . ?
N3 C11 C12 C9 177.9(5) . . . . ?
C4 C11 C12 C9 -2.0(10) . . . . ?
C10 C9 C12 N4 178.9(6) . . . . ?
C8 C9 C12 N4 -1.6(11) . . . . ?
C10 C9 C12 C11 1.3(9) . . . . ?
C8 C9 C12 C11 -179.2(6) . . . . ?
N3 C13 C14 C15 -15.3(9) . . . . ?
N4 C13 C14 C15 166.6(6) . . . . ?
N3 C13 C14 C19 169.1(6) . . . . ?
N4 C13 C14 C19 -9.0(10) . . . . ?
C19 C14 C15 C16 -5.9(10) . . . . ?
C13 C14 C15 C16 178.1(6) . . . . ?
C14 C15 C16 C17 5.9(12) . . . . ?
C15 C16 C17 C18 -2.1(11) . . . . ?
C16 C17 C18 C19 -1.5(11) . . . . ?
C17 C18 C19 C14 1.3(10) . . . . ?
C17 C18 C19 S1 -172.9(5) . . . . ?
C15 C14 C19 C18 2.3(9) . . . . ?
C13 C14 C19 C18 177.8(6) . . . . ?
C15 C14 C19 S1 176.0(5) . . . . ?
C13 C14 C19 S1 -8.5(9) . . . . ?
C2 C1 N1 C5 2.2(11) . . . . ?
C2 C1 N1 Cu1 -176.8(6) . . . . ?
C4 C5 N1 C1 -1.7(9) . . . . ?
C10 C5 N1 C1 179.4(6) . . . . ?
C4 C5 N1 Cu1 177.5(5) . . . . ?
C10 C5 N1 Cu1 -1.5(7) . . . . ?
C7 C6 N2 C10 1.1(11) . . . . ?
C7 C6 N2 Cu1 -179.6(5) . . . . ?
C9 C10 N2 C6 0.3(10) . . . . ?
C5 C10 N2 C6 179.9(6) . . . . ?
C9 C10 N2 Cu1 -179.1(5) . . . . ?
C5 C10 N2 Cu1 0.5(7) . . . . ?
N4 C13 N3 C11 -2.0(6) . . . . ?
C14 C13 N3 C11 179.6(5) . . . . ?
C12 C11 N3 C13 1.3(7) . . . . ?
C4 C11 N3 C13 -178.8(6) . . . . ?
N3 C13 N4 C12 1.9(7) . . . . ?
C14 C13 N4 C12 -179.8(6) . . . . ?
C11 C12 N4 C13 -1.1(7) . . . . ?
C9 C12 N4 C13 -178.9(6) . . . . ?
C18 C19 S1 O3 -9.3(6) . . . . ?
C14 C19 S1 O3 176.8(5) . . . . ?
C18 C19 S1 O2 111.7(5) . . . . ?
C14 C19 S1 O2 -62.2(6) . . . . ?
C18 C19 S1 O1 -130.4(5) . . . . ?
C14 C19 S1 O1 55.7(6) . . . . ?

_refine_diff_density_max         0.782
_refine_diff_density_min         -0.957
_refine_diff_density_rms         0.121

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1545789'
_audit_update_record             
;
2017-04-24 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 Cl0 Cu N4 O8 P S'
_chemical_formula_weight         553.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
P P 0.1023 0.0942 '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'
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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.350(5)
_cell_length_b                   14.076(5)
_cell_length_c                   14.963(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 109.222(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2058.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2154
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      22.8

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_F_000             1124
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.300
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   'SADABS 2014/4 Bruker AXS Madison WI USA'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15003
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.042
_diffrn_reflns_theta_max         28.138
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5045
_reflns_number_gt                3342
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT v8.34a'
_computing_data_reduction        'Bruker SAINT v8.34a'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²+0.3476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5045
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1317(4) 0.3239(3) 0.4213(3) 0.0368(10) Uani 1 1 d . . . . .
C2 C -0.1729(4) 0.4177(3) 0.3959(3) 0.0392(10) Uani 1 1 d . . . . .
C3 C -0.0836(4) 0.4826(3) 0.3804(3) 0.0329(9) Uani 1 1 d . . . . .
C4 C 0.0491(4) 0.4528(2) 0.3886(3) 0.0272(8) Uani 1 1 d . . . . .
C5 C 0.0832(4) 0.3568(2) 0.4126(3) 0.0246(7) Uani 1 1 d . . . . .
C6 C 0.3517(4) 0.1841(3) 0.4459(3) 0.0315(9) Uani 1 1 d . . . . .
C7 C 0.4567(4) 0.2346(3) 0.4288(3) 0.0361(9) Uani 1 1 d . . . . .
C8 C 0.4407(4) 0.3296(3) 0.4078(3) 0.0319(9) Uani 1 1 d . . . . .
C9 C 0.3169(4) 0.3745(2) 0.4035(3) 0.0264(8) Uani 1 1 d . . . . .
C10 C 0.2151(4) 0.3186(2) 0.4201(3) 0.0251(8) Uani 1 1 d . . . . .
C11 C 0.1563(4) 0.5103(2) 0.3756(3) 0.0272(8) Uani 1 1 d . . . . .
C12 C 0.2825(4) 0.4725(2) 0.3849(3) 0.0274(8) Uani 1 1 d . . . . .
C13 C 0.2792(4) 0.6251(3) 0.3535(3) 0.0272(8) Uani 1 1 d . . . . .
C14 C 0.3259(4) 0.7223(2) 0.3428(3) 0.0261(8) Uani 1 1 d . . . . .
C15 C 0.2453(5) 0.7957(3) 0.3587(3) 0.0352(10) Uani 1 1 d . . . . .
C16 C 0.2782(5) 0.8901(3) 0.3567(3) 0.0369(10) Uani 1 1 d . . . . .
C17 C 0.3982(4) 0.9142(3) 0.3401(3) 0.0367(10) Uani 1 1 d . . . . .
C18 C 0.4805(5) 0.8438(3) 0.3235(3) 0.0332(9) Uani 1 1 d . . . . .
C19 C 0.4457(4) 0.7479(3) 0.3240(3) 0.0280(8) Uani 1 1 d . . . . .
N1 N -0.0063(3) 0.2948(2) 0.4290(2) 0.0285(7) Uani 1 1 d . . . . .
N2 N 0.2337(3) 0.2248(2) 0.4412(2) 0.0269(7) Uani 1 1 d . . . . .
N3 N 0.1534(3) 0.6057(2) 0.3552(2) 0.0285(7) Uani 1 1 d . . . . .
N4 N 0.3593(4) 0.5463(2) 0.3708(2) 0.0294(7) Uani 1 1 d . . . . .
O1 O 0.4846(3) 0.6158(2) 0.2135(2) 0.0401(7) Uani 1 1 d . . . . .
O2 O 0.6105(3) 0.60166(19) 0.3795(2) 0.0352(6) Uani 1 1 d . . . . .
O1W O -0.4063(3) 0.1928(2) 0.2652(2) 0.0491(8) Uiso 1 1 d . . . . .
O3 O 0.6719(3) 0.7237(2) 0.2872(3) 0.0548(9) Uani 1 1 d . . . . .
O4 O -0.1020(3) 0.11567(18) 0.4609(2) 0.0368(7) Uani 1 1 d . . . . .
O5 O -0.1336(3) -0.0188(2) 0.3452(2) 0.0495(8) Uani 1 1 d . . . . .
O6 O -0.1717(3) -0.04834(18) 0.4993(2) 0.0413(7) Uani 1 1 d . . . . .
O7 O -0.3351(3) 0.0504(2) 0.3820(3) 0.0576(10) Uani 1 1 d . . . . .
P1 P -0.18009(10) 0.02570(7) 0.42612(8) 0.0317(3) Uani 1 1 d . . . . .
S1 S 0.56356(10) 0.66629(7) 0.29958(7) 0.0316(2) Uani 1 1 d . . . . .
Cu1 Cu 0.06948(5) 0.16276(3) 0.45635(3) 0.02947(15) Uani 1 1 d . . . . .
H1 H -0.189(4) 0.272(3) 0.430(3) 0.027(10) Uiso 1 1 d . . . . .
H2 H -0.268(5) 0.435(3) 0.394(4) 0.064(15) Uiso 1 1 d . . . . .
H3 H -0.112(3) 0.553(3) 0.366(2) 0.019(9) Uiso 1 1 d . . . . .
H4 H 0.432(5) 0.553(4) 0.367(4) 0.063(18) Uiso 1 1 d . . . . .
H6 H 0.367(3) 0.128(3) 0.458(2) 0.014(9) Uiso 1 1 d . . . . .
H7 H 0.540(5) 0.202(3) 0.446(3) 0.046(13) Uiso 1 1 d . . . . .
H8 H 0.511(4) 0.359(3) 0.398(3) 0.033(11) Uiso 1 1 d . . . . .
H15 H 0.185(4) 0.788(3) 0.371(3) 0.014(10) Uiso 1 1 d . . . . .
H16 H 0.229(4) 0.932(3) 0.369(3) 0.021(10) Uiso 1 1 d . . . . .
H17 H 0.426(4) 0.970(3) 0.332(3) 0.034(11) Uiso 1 1 d . . . . .
H18 H 0.551(5) 0.859(4) 0.319(4) 0.061(17) 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
C1 N1 1.330(5) . ?
C1 C2 1.401(6) . ?
C1 H1 0.97(4) . ?
C2 C3 1.373(6) . ?
C2 H2 1.01(5) . ?
C3 C4 1.402(5) . ?
C3 H3 1.03(3) . ?
C4 C5 1.413(5) . ?
C4 C11 1.437(5) . ?
C5 N1 1.353(5) . ?
C5 C10 1.437(5) . ?
C6 N2 1.330(5) . ?
C6 C7 1.391(6) . ?
C6 H6 0.81(4) . ?
C7 C8 1.370(5) . ?
C7 H7 0.93(5) . ?
C8 C9 1.412(5) . ?
C8 H8 0.89(4) . ?
C9 C10 1.401(5) . ?
C9 C12 1.429(5) . ?
C10 N2 1.356(4) . ?
C11 C12 1.374(5) . ?
C11 N3 1.375(4) . ?
C12 N4 1.365(5) . ?
C13 N3 1.340(5) . ?
C13 N4 1.358(5) . ?
C13 C14 1.477(5) . ?
C14 C15 1.397(5) . ?
C14 C19 1.405(5) . ?
C15 C16 1.375(6) . ?
C15 H15 0.71(4) . ?
C16 C17 1.387(6) . ?
C16 H16 0.84(4) . ?
C17 C18 1.382(6) . ?
C17 H17 0.86(4) . ?
C18 C19 1.397(5) . ?
C18 H18 0.78(5) . ?
C19 S1 1.799(4) . ?
N1 Cu1 2.006(3) . ?
N2 Cu1 1.989(3) . ?
N4 H4 0.78(5) . ?
O1 S1 1.462(3) . ?
O2 S1 1.453(3) . ?
O3 S1 1.443(3) . ?
O4 P1 1.500(3) . ?
O4 Cu1 1.917(3) . ?
O5 P1 1.572(3) . ?
O6 P1 1.493(3) . ?
O6 Cu1 1.921(3) 3_556 ?
O7 P1 1.560(3) . ?
Cu1 O6 1.921(3) 3_556 ?

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 C1 C2 121.0(4) . . ?
N1 C1 H1 112(2) . . ?
C2 C1 H1 126(2) . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 123(3) . . ?
C1 C2 H2 116(3) . . ?
C2 C3 C4 118.7(4) . . ?
C2 C3 H3 121(2) . . ?
C4 C3 H3 120.6(19) . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C11 126.7(3) . . ?
C5 C4 C11 115.7(3) . . ?
N1 C5 C4 122.3(3) . . ?
N1 C5 C10 115.7(3) . . ?
C4 C5 C10 122.0(3) . . ?
N2 C6 C7 122.0(3) . . ?
N2 C6 H6 123(2) . . ?
C7 C6 H6 115(2) . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7 125(3) . . ?
C6 C7 H7 114(3) . . ?
C7 C8 C9 119.1(4) . . ?
C7 C8 H8 116(3) . . ?
C9 C8 H8 124(3) . . ?
C10 C9 C8 117.7(3) . . ?
C10 C9 C12 115.1(3) . . ?
C8 C9 C12 127.2(3) . . ?
N2 C10 C9 122.1(3) . . ?
N2 C10 C5 116.2(3) . . ?
C9 C10 C5 121.7(3) . . ?
C12 C11 N3 110.6(3) . . ?
C12 C11 C4 121.3(3) . . ?
N3 C11 C4 128.2(3) . . ?
N4 C12 C11 105.8(3) . . ?
N4 C12 C9 130.1(3) . . ?
C11 C12 C9 124.1(3) . . ?
N3 C13 N4 111.4(3) . . ?
N3 C13 C14 123.1(3) . . ?
N4 C13 C14 125.2(3) . . ?
C15 C14 C19 117.4(3) . . ?
C15 C14 C13 115.5(3) . . ?
C19 C14 C13 126.9(3) . . ?
C16 C15 C14 123.0(4) . . ?
C16 C15 H15 113(3) . . ?
C14 C15 H15 124(3) . . ?
C15 C16 C17 118.9(4) . . ?
C15 C16 H16 120(3) . . ?
C17 C16 H16 121(3) . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 112(3) . . ?
C16 C17 H17 128(3) . . ?
C17 C18 C19 121.1(4) . . ?
C17 C18 H18 117(4) . . ?
C19 C18 H18 121(4) . . ?
C18 C19 C14 119.7(4) . . ?
C18 C19 S1 115.0(3) . . ?
C14 C19 S1 125.3(3) . . ?
C1 N1 C5 119.5(3) . . ?
C1 N1 Cu1 127.5(3) . . ?
C5 N1 Cu1 112.9(2) . . ?
C6 N2 C10 119.3(3) . . ?
C6 N2 Cu1 127.5(2) . . ?
C10 N2 Cu1 113.2(2) . . ?
C13 N3 C11 104.7(3) . . ?
C13 N4 C12 107.6(3) . . ?
C13 N4 H4 115(4) . . ?
C12 N4 H4 137(4) . . ?
P1 O4 Cu1 132.75(18) . . ?
P1 O6 Cu1 136.98(19) . 3_556 ?
O6 P1 O4 116.11(18) . . ?
O6 P1 O7 105.63(18) . . ?
O4 P1 O7 108.68(18) . . ?
O6 P1 O5 109.11(18) . . ?
O4 P1 O5 109.71(17) . . ?
O7 P1 O5 107.2(2) . . ?
O3 S1 O2 113.16(19) . . ?
O3 S1 O1 113.0(2) . . ?
O2 S1 O1 111.03(17) . . ?
O3 S1 C19 106.04(18) . . ?
O2 S1 C19 107.35(17) . . ?
O1 S1 C19 105.64(18) . . ?
O4 Cu1 O6 96.24(12) . 3_556 ?
O4 Cu1 N2 172.68(12) . . ?
O6 Cu1 N2 90.79(12) 3_556 . ?
O4 Cu1 N1 91.33(12) . . ?
O6 Cu1 N1 168.76(13) 3_556 . ?
N2 Cu1 N1 82.02(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -1.6(7) . . . . ?
C1 C2 C3 C4 1.3(7) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C2 C3 C4 C11 -179.6(4) . . . . ?
C3 C4 C5 N1 -1.1(6) . . . . ?
C11 C4 C5 N1 178.5(3) . . . . ?
C3 C4 C5 C10 178.2(4) . . . . ?
C11 C4 C5 C10 -2.2(5) . . . . ?
N2 C6 C7 C8 1.1(7) . . . . ?
C6 C7 C8 C9 -0.3(6) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
C7 C8 C9 C12 178.5(4) . . . . ?
C8 C9 C10 N2 1.2(6) . . . . ?
C12 C9 C10 N2 -178.2(3) . . . . ?
C8 C9 C10 C5 -176.8(4) . . . . ?
C12 C9 C10 C5 3.8(5) . . . . ?
N1 C5 C10 N2 0.9(5) . . . . ?
C4 C5 C10 N2 -178.4(3) . . . . ?
N1 C5 C10 C9 179.0(3) . . . . ?
C4 C5 C10 C9 -0.3(6) . . . . ?
C3 C4 C11 C12 -179.5(4) . . . . ?
C5 C4 C11 C12 0.9(6) . . . . ?
C3 C4 C11 N3 1.8(7) . . . . ?
C5 C4 C11 N3 -177.7(4) . . . . ?
N3 C11 C12 N4 0.5(4) . . . . ?
C4 C11 C12 N4 -178.3(4) . . . . ?
N3 C11 C12 C9 -178.2(3) . . . . ?
C4 C11 C12 C9 2.9(6) . . . . ?
C10 C9 C12 N4 176.4(4) . . . . ?
C8 C9 C12 N4 -2.9(7) . . . . ?
C10 C9 C12 C11 -5.2(6) . . . . ?
C8 C9 C12 C11 175.5(4) . . . . ?
N3 C13 C14 C15 15.8(6) . . . . ?
N4 C13 C14 C15 -158.2(4) . . . . ?
N3 C13 C14 C19 -168.2(4) . . . . ?
N4 C13 C14 C19 17.8(6) . . . . ?
C19 C14 C15 C16 0.1(7) . . . . ?
C13 C14 C15 C16 176.4(4) . . . . ?
C14 C15 C16 C17 -1.5(7) . . . . ?
C15 C16 C17 C18 1.8(7) . . . . ?
C16 C17 C18 C19 -0.7(7) . . . . ?
C17 C18 C19 C14 -0.8(6) . . . . ?
C17 C18 C19 S1 179.3(3) . . . . ?
C15 C14 C19 C18 1.1(6) . . . . ?
C13 C14 C19 C18 -174.9(4) . . . . ?
C15 C14 C19 S1 -179.0(3) . . . . ?
C13 C14 C19 S1 5.1(6) . . . . ?
C2 C1 N1 C5 0.4(6) . . . . ?
C2 C1 N1 Cu1 -175.9(3) . . . . ?
C4 C5 N1 C1 0.9(6) . . . . ?
C10 C5 N1 C1 -178.4(4) . . . . ?
C4 C5 N1 Cu1 177.7(3) . . . . ?
C10 C5 N1 Cu1 -1.6(4) . . . . ?
C7 C6 N2 C10 -0.7(6) . . . . ?
C7 C6 N2 Cu1 176.3(3) . . . . ?
C9 C10 N2 C6 -0.4(5) . . . . ?
C5 C10 N2 C6 177.7(3) . . . . ?
C9 C10 N2 Cu1 -177.9(3) . . . . ?
C5 C10 N2 Cu1 0.2(4) . . . . ?
N4 C13 N3 C11 0.7(4) . . . . ?
C14 C13 N3 C11 -174.1(3) . . . . ?
C12 C11 N3 C13 -0.7(4) . . . . ?
C4 C11 N3 C13 178.0(4) . . . . ?
N3 C13 N4 C12 -0.4(5) . . . . ?
C14 C13 N4 C12 174.3(4) . . . . ?
C11 C12 N4 C13 -0.1(4) . . . . ?
C9 C12 N4 C13 178.6(4) . . . . ?
Cu1 O6 P1 O4 -98.8(3) 3_556 . . . ?
Cu1 O6 P1 O7 140.7(3) 3_556 . . . ?
Cu1 O6 P1 O5 25.8(3) 3_556 . . . ?
Cu1 O4 P1 O6 102.1(3) . . . . ?
Cu1 O4 P1 O7 -139.1(3) . . . . ?
Cu1 O4 P1 O5 -22.2(3) . . . . ?
C18 C19 S1 O3 1.4(4) . . . . ?
C14 C19 S1 O3 -178.6(3) . . . . ?
C18 C19 S1 O2 122.6(3) . . . . ?
C14 C19 S1 O2 -57.3(4) . . . . ?
C18 C19 S1 O1 -118.9(3) . . . . ?
C14 C19 S1 O1 61.2(4) . . . . ?

_refine_diff_density_max         1.511
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.112

_shelxl_version_number           2014-3

