# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
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#######################################################################

data_hard19
_database_code_depnum_ccdc_archive 'CCDC 1552238'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_audit_creation_date             2017-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 Cl Cu N2 O4 S'
_chemical_formula_sum            'C13 H13 Cl Cu N2 O4 S'
_chemical_formula_weight         392.30
_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 0.0140 0.0070 '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 0.3290 0.5400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -2.7970 3.6880 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4250 '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                   7.9081(2)
_cell_length_b                   13.4568(4)
_cell_length_c                   14.0019(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.2800(10)
_cell_angle_gamma                90
_cell_volume                     1444.01(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.702
_cell_measurement_theta_min      2.857
_shelx_estimated_absorpt_T_max   0.426
_shelx_estimated_absorpt_T_min   0.183
_exptl_absorpt_coefficient_mu    10.277
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.4003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1479 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.5324.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25548
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.667
_diffrn_reflns_theta_min         4.025
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3254
_reflns_number_total             3292
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.043
_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)+(0.0413P)²+0.9871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0704
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H1D)=Sof(H1E)=Sof(H1F)=1-FVAR(1)
 Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C13(H13), C7(H7), C4(H4), C11(H11), C3(H3), C12(H12)
3.b Disordered Me refined with riding coordinates:
 C1(H1A,H1B,H1C,H1D,H1E,H1F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.58011(3) 0.30251(2) 0.68613(2) 0.00907(8) Uani 1 1 d . . . . .
Cl1 Cl 0.78795(5) 0.18525(3) 0.71042(3) 0.01201(9) Uani 1 1 d . . . . .
S1 S 0.28304(4) 0.26835(3) 0.50454(3) 0.00956(9) Uani 1 1 d . . . . .
O3 O 0.47076(14) 0.25227(8) 0.55314(8) 0.0110(2) Uani 1 1 d . . . . .
O2 O 0.16999(14) 0.23909(8) 0.56717(8) 0.0142(2) Uani 1 1 d . . . . .
O1 O 0.23947(15) 0.22244(9) 0.40798(8) 0.0145(2) Uani 1 1 d . . . . .
O4 O 0.38303(16) 0.21808(10) 0.75321(10) 0.0160(2) Uani 1 1 d . . . . .
N1 N 0.44461(16) 0.43302(9) 0.65254(9) 0.0094(2) Uani 1 1 d . . . . .
N2 N 0.67177(16) 0.37166(9) 0.81426(9) 0.0106(2) Uani 1 1 d . . . . .
C8 C 0.46380(19) 0.48871(11) 0.72916(11) 0.0112(3) Uani 1 1 d . . . . .
H8 H 0.3996 0.5487 0.7265 0.013 Uiso 1 1 calc R . . . .
C6 C 0.25724(19) 0.39833(11) 0.48753(11) 0.0100(3) Uani 1 1 d . . . . .
C9 C 0.58604(19) 0.45772(11) 0.82004(11) 0.0106(3) Uani 1 1 d . . . . .
C10 C 0.6158(2) 0.51442(11) 0.90537(11) 0.0133(3) Uani 1 1 d . . . . .
H10 H 0.5523 0.5739 0.9076 0.016 Uiso 1 1 calc R . . . .
C13 C 0.7920(2) 0.34068(12) 0.89356(11) 0.0129(3) Uani 1 1 d . . . . .
H13 H 0.8527 0.2804 0.8899 0.015 Uiso 1 1 calc R . . . .
C7 C 0.14564(19) 0.43121(12) 0.39987(11) 0.0121(3) Uani 1 1 d . . . . .
H7 H 0.0938 0.3841 0.3508 0.015 Uiso 1 1 calc R . . . .
C4 C 0.30470(19) 0.56804(11) 0.54233(11) 0.0117(3) Uani 1 1 d . . . . .
H4 H 0.3620 0.6156 0.5895 0.014 Uiso 1 1 calc R . . . .
C5 C 0.33505(18) 0.46640(11) 0.56135(11) 0.0099(3) Uani 1 1 d . . . . .
C11 C 0.7415(2) 0.48172(12) 0.98776(12) 0.0149(3) Uani 1 1 d . . . . .
H11 H 0.7654 0.5188 1.0473 0.018 Uiso 1 1 calc R . . . .
C2 C 0.10888(19) 0.53222(12) 0.38305(11) 0.0121(3) Uani 1 1 d . . . . .
C3 C 0.19209(19) 0.59989(12) 0.45560(12) 0.0126(3) Uani 1 1 d . . . . .
H3 H 0.1708 0.6690 0.4451 0.015 Uiso 1 1 calc R . . . .
C12 C 0.8307(2) 0.39448(12) 0.98154(12) 0.0148(3) Uani 1 1 d . . . . .
H12 H 0.9176 0.3714 1.0367 0.018 Uiso 1 1 calc R . . . .
C1 C -0.0159(2) 0.56708(13) 0.28989(13) 0.0177(3) Uani 1 1 d . . . . .
H1A H -0.0253 0.6397 0.2910 0.021 Uiso 0.41(2) 1 calc R . P . .
H1B H 0.0273 0.5468 0.2330 0.021 Uiso 0.41(2) 1 calc R . P . .
H1C H -0.1309 0.5375 0.2850 0.021 Uiso 0.41(2) 1 calc R . P . .
H1D H -0.0606 0.5096 0.2483 0.021 Uiso 0.59(2) 1 calc R . P . .
H1E H -0.1133 0.6025 0.3063 0.021 Uiso 0.59(2) 1 calc R . P . .
H1F H 0.0450 0.6118 0.2543 0.021 Uiso 0.59(2) 1 calc R . P . .
H4A H 0.307(4) 0.215(2) 0.708(2) 0.045(9) Uiso 1 1 d . . . . .
H4B H 0.343(3) 0.2391(19) 0.801(2) 0.028(6) 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 Cl1 2.2431(4) . ?
Cu1 O3 1.9693(11) . ?
Cu1 O4 2.3073(12) . ?
Cu1 N1 2.0506(13) . ?
Cu1 N2 1.9920(13) . ?
S1 O3 1.4883(11) . ?
S1 O2 1.4526(11) . ?
S1 O1 1.4486(12) . ?
S1 C6 1.7704(15) . ?
O4 H4A 0.76(3) . ?
O4 H4B 0.85(3) . ?
N1 C8 1.287(2) . ?
N1 C5 1.4273(19) . ?
N2 C9 1.3544(19) . ?
N2 C13 1.338(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.456(2) . ?
C6 C7 1.395(2) . ?
C6 C5 1.404(2) . ?
C9 C10 1.388(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.396(2) . ?
C7 H7 0.9500 . ?
C7 C2 1.398(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.403(2) . ?
C4 C3 1.385(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(2) . ?
C2 C3 1.402(2) . ?
C2 C1 1.503(2) . ?
C3 H3 0.9500 . ?
C12 H12 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 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
Cl1 Cu1 O4 97.77(3) . . ?
O3 Cu1 Cl1 92.08(3) . . ?
O3 Cu1 O4 91.87(5) . . ?
O3 Cu1 N1 89.68(5) . . ?
O3 Cu1 N2 171.62(5) . . ?
N1 Cu1 Cl1 163.57(4) . . ?
N1 Cu1 O4 98.50(5) . . ?
N2 Cu1 Cl1 95.85(4) . . ?
N2 Cu1 O4 89.76(5) . . ?
N2 Cu1 N1 81.95(5) . . ?
O3 S1 C6 105.90(7) . . ?
O2 S1 O3 112.18(7) . . ?
O2 S1 C6 106.34(7) . . ?
O1 S1 O3 110.22(7) . . ?
O1 S1 O2 114.06(7) . . ?
O1 S1 C6 107.62(7) . . ?
S1 O3 Cu1 122.57(6) . . ?
Cu1 O4 H4A 99(2) . . ?
Cu1 O4 H4B 125.0(17) . . ?
H4A O4 H4B 107(3) . . ?
C8 N1 Cu1 111.11(10) . . ?
C8 N1 C5 118.91(13) . . ?
C5 N1 Cu1 129.96(10) . . ?
C9 N2 Cu1 112.15(10) . . ?
C13 N2 Cu1 128.91(11) . . ?
C13 N2 C9 118.72(13) . . ?
N1 C8 H8 120.7 . . ?
N1 C8 C9 118.57(13) . . ?
C9 C8 H8 120.7 . . ?
C7 C6 S1 117.29(12) . . ?
C7 C6 C5 120.53(14) . . ?
C5 C6 S1 122.03(12) . . ?
N2 C9 C8 115.26(13) . . ?
N2 C9 C10 122.71(14) . . ?
C10 C9 C8 122.00(14) . . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.26(14) . . ?
C11 C10 H10 120.9 . . ?
N2 C13 H13 119.1 . . ?
N2 C13 C12 121.81(14) . . ?
C12 C13 H13 119.1 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C2 121.11(14) . . ?
C2 C7 H7 119.4 . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.73(14) . . ?
C6 C5 N1 120.82(13) . . ?
C4 C5 N1 120.95(13) . . ?
C4 C5 C6 118.22(14) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.08(15) . . ?
C12 C11 H11 120.5 . . ?
C7 C2 C3 117.95(14) . . ?
C7 C2 C1 120.95(14) . . ?
C3 C2 C1 121.10(14) . . ?
C4 C3 C2 121.33(14) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C13 C12 H12 120.3 . . ?
C11 C12 C13 119.41(15) . . ?
C11 C12 H12 120.3 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1A C1 H1D 141.1 . . ?
H1A C1 H1E 56.3 . . ?
H1A C1 H1F 56.3 . . ?
H1B C1 H1C 109.5 . . ?
H1B C1 H1D 56.3 . . ?
H1B C1 H1E 141.1 . . ?
H1B C1 H1F 56.3 . . ?
H1C C1 H1D 56.3 . . ?
H1C C1 H1E 56.3 . . ?
H1C C1 H1F 141.1 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C8 C9 6.22(17) . . . . ?
Cu1 N1 C5 C6 22.19(19) . . . . ?
Cu1 N1 C5 C4 -156.66(11) . . . . ?
Cu1 N2 C9 C8 -7.90(16) . . . . ?
Cu1 N2 C9 C10 174.04(12) . . . . ?
Cu1 N2 C13 C12 -174.03(12) . . . . ?
S1 C6 C7 C2 175.85(11) . . . . ?
S1 C6 C5 N1 2.44(19) . . . . ?
S1 C6 C5 C4 -178.68(11) . . . . ?
O3 S1 C6 C7 141.17(11) . . . . ?
O3 S1 C6 C5 -43.28(14) . . . . ?
O2 S1 O3 Cu1 -51.21(10) . . . . ?
O2 S1 C6 C7 -99.31(12) . . . . ?
O2 S1 C6 C5 76.24(13) . . . . ?
O1 S1 O3 Cu1 -179.48(7) . . . . ?
O1 S1 C6 C7 23.30(14) . . . . ?
O1 S1 C6 C5 -161.15(12) . . . . ?
N1 C8 C9 N2 1.0(2) . . . . ?
N1 C8 C9 C10 179.06(14) . . . . ?
N2 C9 C10 C11 1.1(2) . . . . ?
N2 C13 C12 C11 0.7(2) . . . . ?
C8 N1 C5 C6 -155.87(14) . . . . ?
C8 N1 C5 C4 25.3(2) . . . . ?
C8 C9 C10 C11 -176.85(14) . . . . ?
C6 S1 O3 Cu1 64.39(9) . . . . ?
C6 C7 C2 C3 2.1(2) . . . . ?
C6 C7 C2 C1 -178.03(14) . . . . ?
C9 N2 C13 C12 0.1(2) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C13 N2 C9 C8 177.04(13) . . . . ?
C13 N2 C9 C10 -1.0(2) . . . . ?
C7 C6 C5 N1 177.85(13) . . . . ?
C7 C6 C5 C4 -3.3(2) . . . . ?
C7 C2 C3 C4 -1.3(2) . . . . ?
C5 N1 C8 C9 -175.37(13) . . . . ?
C5 C6 C7 C2 0.2(2) . . . . ?
C5 C4 C3 C2 -1.8(2) . . . . ?
C3 C4 C5 N1 -177.06(13) . . . . ?
C3 C4 C5 C6 4.1(2) . . . . ?
C1 C2 C3 C4 178.82(14) . . . . ?

_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_hard35
_database_code_depnum_ccdc_archive 'CCDC 1552239'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_audit_creation_date             2016-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 Cu F3 N2 O6 S2'
_chemical_formula_sum            'C14 H11 Cu F3 N2 O6 S2'
_chemical_formula_weight         487.91
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.6171(2)
_cell_length_b                   10.0602(2)
_cell_length_c                   23.5560(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3463.93(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.082
_cell_measurement_theta_min      4.822
_shelx_estimated_absorpt_T_max   0.799
_shelx_estimated_absorpt_T_min   0.626
_exptl_absorpt_coefficient_mu    4.698
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0773 before and 0.0394 after correction.
The Ratio of minimum to maximum transmission is 0.8101.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1960
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker microstar diffractometer equipped with a Platinum 135 CCD Detector,
a Helios optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 110.0 degree
scan in 110 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            66922
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.166
_diffrn_reflns_theta_min         4.822
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker Platinum 135 CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Microstar X8'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Bruker Microstar/FR591 generator'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3332
_reflns_number_total             3413
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2013) V8.34A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.34A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0233
_refine_ls_restrained_S_all      1.055
_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)+(0.0412P)²+2.9437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0679
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.28783(2) 0.44149(2) 0.31188(2) 0.01176(8) Uani 1 1 d . . . . .
S1 S 0.18663(2) 0.63896(3) 0.24147(2) 0.01094(10) Uani 1 1 d . . . . .
S2 S 0.14707(3) 0.25972(4) 0.37482(2) 0.01353(10) Uani 1 1 d . . . . .
F1 F 0.05797(9) 0.40735(14) 0.44835(5) 0.0401(3) Uani 1 1 d . . . . .
F2 F 0.02143(9) 0.20007(16) 0.44931(5) 0.0455(4) Uani 1 1 d . . . . .
F3 F 0.14814(8) 0.26475(12) 0.48664(4) 0.0284(2) Uani 1 1 d . . . . .
O1 O 0.17962(7) 0.52844(11) 0.28326(5) 0.0130(2) Uani 1 1 d . . . . .
O2 O 0.24749(8) 0.74362(11) 0.26113(4) 0.0142(2) Uani 1 1 d . . . . .
O3 O 0.09679(7) 0.68005(11) 0.22376(5) 0.0150(2) Uani 1 1 d . . . . .
O4 O 0.21730(8) 0.36406(11) 0.37751(5) 0.0146(2) Uani 1 1 d . . . . .
O5 O 0.18352(9) 0.12712(12) 0.37934(5) 0.0223(3) Uani 1 1 d . . . . .
O6 O 0.07561(8) 0.28128(13) 0.33453(5) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.36313(9) 0.47936(12) 0.24150(5) 0.0114(3) Uani 1 1 d . . . . .
N2 N 0.40612(9) 0.37483(13) 0.33969(6) 0.0138(3) Uani 1 1 d . . . . .
C1 C 0.42223(12) 0.31193(18) 0.38845(7) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.50887(12) 0.26536(18) 0.40243(7) 0.0219(4) Uani 1 1 d . . . . .
C3 C 0.58002(12) 0.28465(16) 0.36464(7) 0.0179(3) Uani 1 1 d . . . . .
C4 C 0.56335(11) 0.34757(16) 0.31320(7) 0.0152(3) Uani 1 1 d . . . . .
C5 C 0.47547(11) 0.39273(15) 0.30245(7) 0.0132(3) Uani 1 1 d . . . . .
C6 C 0.44799(11) 0.45115(15) 0.24812(7) 0.0135(3) Uani 1 1 d . . . . .
C7 C 0.32561(11) 0.50197(15) 0.18669(6) 0.0130(3) Uani 1 1 d . . . . .
C8 C 0.36494(12) 0.44784(16) 0.13802(7) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.32297(12) 0.46436(17) 0.08536(7) 0.0177(3) Uani 1 1 d . . . . .
C10 C 0.24041(12) 0.53253(16) 0.07973(7) 0.0168(3) Uani 1 1 d . . . . .
C11 C 0.20061(11) 0.58484(16) 0.12872(7) 0.0144(3) Uani 1 1 d . . . . .
C12 C 0.24190(12) 0.56938(15) 0.18143(6) 0.0127(3) Uani 1 1 d . . . . .
C13 C 0.19243(14) 0.5475(2) 0.02340(8) 0.0227(4) Uani 1 1 d . . . . .
C14 C 0.09101(12) 0.2851(2) 0.44348(7) 0.0236(4) Uani 1 1 d . . . . .
H11 H 0.1455(14) 0.625(2) 0.1258(8) 0.014(5) Uiso 1 1 d . . . . .
H6 H 0.4931(14) 0.459(2) 0.2196(9) 0.018(5) Uiso 1 1 d . . . . .
H8 H 0.4207(15) 0.399(2) 0.1412(9) 0.019(5) Uiso 1 1 d . . . . .
H3 H 0.6398(17) 0.256(2) 0.3721(9) 0.028(6) Uiso 1 1 d . . . . .
H9 H 0.3470(14) 0.428(2) 0.0539(9) 0.018(5) Uiso 1 1 d . . . . .
H1 H 0.3736(15) 0.300(2) 0.4123(9) 0.022(5) Uiso 1 1 d . . . . .
H4 H 0.6078(14) 0.3565(19) 0.2857(8) 0.011(4) Uiso 1 1 d . . . . .
H2 H 0.5193(16) 0.221(2) 0.4371(10) 0.027(6) Uiso 1 1 d . . . . .
H13A H 0.1362(17) 0.507(2) 0.0249(10) 0.028(6) Uiso 1 1 d . . . . .
H13B H 0.2256(17) 0.514(3) -0.0047(11) 0.033(6) Uiso 1 1 d . . . . .
H13C H 0.1818(19) 0.635(3) 0.0172(11) 0.041(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
Cu1 O1 1.9291(11) . ?
Cu1 O2 2.3787(11) 8_655 ?
Cu1 O4 2.0148(11) . ?
Cu1 N1 2.0261(13) . ?
Cu1 N2 1.9669(13) . ?
S1 O1 1.4885(11) . ?
S1 O2 1.4540(11) . ?
S1 O3 1.4386(11) . ?
S1 C12 1.7729(16) . ?
S2 O4 1.4697(12) . ?
S2 O5 1.4404(13) . ?
S2 O6 1.4278(12) . ?
S2 C14 1.8308(18) . ?
F1 C14 1.326(2) . ?
F2 C14 1.336(2) . ?
F3 C14 1.332(2) . ?
O2 Cu1 2.3788(11) 8_665 ?
N1 C6 1.282(2) . ?
N1 C7 1.4211(19) . ?
N2 C1 1.332(2) . ?
N2 C5 1.352(2) . ?
C1 C2 1.390(2) . ?
C1 H1 0.91(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.94(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.94(2) . ?
C4 C5 1.386(2) . ?
C4 H4 0.92(2) . ?
C5 C6 1.464(2) . ?
C6 H6 0.95(2) . ?
C7 C8 1.394(2) . ?
C7 C12 1.404(2) . ?
C8 C9 1.394(2) . ?
C8 H8 0.95(2) . ?
C9 C10 1.394(3) . ?
C9 H9 0.90(2) . ?
C10 C11 1.395(2) . ?
C10 C13 1.509(2) . ?
C11 C12 1.389(2) . ?
C11 H11 0.90(2) . ?
C13 H13A 0.92(3) . ?
C13 H13B 0.89(3) . ?
C13 H13C 0.90(3) . ?

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
O1 Cu1 O2 91.48(4) . 8_655 ?
O1 Cu1 O4 91.38(5) . . ?
O1 Cu1 N1 94.25(5) . . ?
O1 Cu1 N2 172.65(5) . . ?
O4 Cu1 O2 87.20(4) . 8_655 ?
O4 Cu1 N1 168.10(5) . . ?
N1 Cu1 O2 82.18(4) . 8_655 ?
N2 Cu1 O2 94.18(5) . 8_655 ?
N2 Cu1 O4 93.58(5) . . ?
N2 Cu1 N1 81.89(5) . . ?
O1 S1 C12 105.30(7) . . ?
O2 S1 O1 111.86(6) . . ?
O2 S1 C12 105.14(7) . . ?
O3 S1 O1 110.09(6) . . ?
O3 S1 O2 116.28(7) . . ?
O3 S1 C12 107.34(7) . . ?
O4 S2 C14 100.07(8) . . ?
O5 S2 O4 113.57(7) . . ?
O5 S2 C14 103.27(8) . . ?
O6 S2 O4 115.54(7) . . ?
O6 S2 O5 117.41(8) . . ?
O6 S2 C14 103.81(8) . . ?
S1 O1 Cu1 120.89(7) . . ?
S1 O2 Cu1 129.29(7) . 8_665 ?
S2 O4 Cu1 126.90(7) . . ?
C6 N1 Cu1 112.61(11) . . ?
C6 N1 C7 121.29(14) . . ?
C7 N1 Cu1 124.32(10) . . ?
C1 N2 Cu1 127.18(12) . . ?
C1 N2 C5 119.33(14) . . ?
C5 N2 Cu1 113.42(11) . . ?
N2 C1 C2 121.69(16) . . ?
N2 C1 H1 116.9(14) . . ?
C2 C1 H1 121.4(14) . . ?
C1 C2 H2 120.7(14) . . ?
C3 C2 C1 119.05(16) . . ?
C3 C2 H2 120.2(14) . . ?
C2 C3 C4 119.59(16) . . ?
C2 C3 H3 122.6(14) . . ?
C4 C3 H3 117.8(14) . . ?
C3 C4 H4 122.3(12) . . ?
C5 C4 C3 118.13(15) . . ?
C5 C4 H4 119.5(12) . . ?
N2 C5 C4 122.18(15) . . ?
N2 C5 C6 114.49(14) . . ?
C4 C5 C6 123.06(15) . . ?
N1 C6 C5 117.42(14) . . ?
N1 C6 H6 124.8(13) . . ?
C5 C6 H6 117.6(13) . . ?
C8 C7 N1 121.72(15) . . ?
C8 C7 C12 118.39(14) . . ?
C12 C7 N1 119.59(14) . . ?
C7 C8 C9 120.28(15) . . ?
C7 C8 H8 119.2(12) . . ?
C9 C8 H8 120.5(13) . . ?
C8 C9 C10 121.61(15) . . ?
C8 C9 H9 121.0(13) . . ?
C10 C9 H9 117.4(13) . . ?
C9 C10 C11 117.89(15) . . ?
C9 C10 C13 122.34(16) . . ?
C11 C10 C13 119.75(16) . . ?
C10 C11 H11 118.5(12) . . ?
C12 C11 C10 121.05(15) . . ?
C12 C11 H11 120.3(12) . . ?
C7 C12 S1 121.14(12) . . ?
C11 C12 S1 118.09(13) . . ?
C11 C12 C7 120.76(14) . . ?
C10 C13 H13A 109.8(14) . . ?
C10 C13 H13B 111.4(16) . . ?
C10 C13 H13C 108.6(17) . . ?
H13A C13 H13B 110(2) . . ?
H13A C13 H13C 106(2) . . ?
H13B C13 H13C 110(2) . . ?
F1 C14 S2 111.64(13) . . ?
F1 C14 F2 107.91(16) . . ?
F1 C14 F3 107.75(15) . . ?
F2 C14 S2 110.01(12) . . ?
F3 C14 S2 111.87(12) . . ?
F3 C14 F2 107.48(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C6 C5 2.57(17) . . . . ?
Cu1 N1 C7 C8 -138.66(13) . . . . ?
Cu1 N1 C7 C12 34.95(19) . . . . ?
Cu1 N2 C1 C2 177.69(13) . . . . ?
Cu1 N2 C5 C4 -177.28(12) . . . . ?
Cu1 N2 C5 C6 -3.09(16) . . . . ?
O1 S1 O2 Cu1 -93.35(9) . . . 8_665 ?
O1 S1 C12 C7 -53.11(14) . . . . ?
O1 S1 C12 C11 127.71(12) . . . . ?
O2 S1 O1 Cu1 -53.32(9) . . . . ?
O2 S1 C12 C7 65.19(14) . . . . ?
O2 S1 C12 C11 -113.99(13) . . . . ?
O3 S1 O1 Cu1 175.77(7) . . . . ?
O3 S1 O2 Cu1 34.32(11) . . . 8_665 ?
O3 S1 C12 C7 -170.40(12) . . . . ?
O3 S1 C12 C11 10.41(14) . . . . ?
O4 S2 C14 F1 58.65(14) . . . . ?
O4 S2 C14 F2 178.43(13) . . . . ?
O4 S2 C14 F3 -62.19(14) . . . . ?
O5 S2 O4 Cu1 88.85(10) . . . . ?
O5 S2 C14 F1 175.98(13) . . . . ?
O5 S2 C14 F2 -64.24(15) . . . . ?
O5 S2 C14 F3 55.14(15) . . . . ?
O6 S2 O4 Cu1 -51.07(11) . . . . ?
O6 S2 C14 F1 -60.99(14) . . . . ?
O6 S2 C14 F2 58.79(15) . . . . ?
O6 S2 C14 F3 178.17(13) . . . . ?
N1 C7 C8 C9 175.61(14) . . . . ?
N1 C7 C12 S1 5.3(2) . . . . ?
N1 C7 C12 C11 -175.57(14) . . . . ?
N2 C1 C2 C3 -0.1(3) . . . . ?
N2 C5 C6 N1 0.3(2) . . . . ?
C1 N2 C5 C4 0.1(2) . . . . ?
C1 N2 C5 C6 174.26(14) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C3 C4 C5 N2 -1.4(2) . . . . ?
C3 C4 C5 C6 -175.12(15) . . . . ?
C4 C5 C6 N1 174.42(14) . . . . ?
C5 N2 C1 C2 0.7(3) . . . . ?
C6 N1 C7 C8 25.0(2) . . . . ?
C6 N1 C7 C12 -161.37(14) . . . . ?
C7 N1 C6 C5 -162.87(13) . . . . ?
C7 C8 C9 C10 -1.2(3) . . . . ?
C8 C7 C12 S1 179.08(12) . . . . ?
C8 C7 C12 C11 -1.8(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C8 C9 C10 C13 -177.92(16) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C11 C12 S1 -179.98(12) . . . . ?
C10 C11 C12 C7 0.8(2) . . . . ?
C12 S1 O1 Cu1 60.36(9) . . . . ?
C12 S1 O2 Cu1 152.87(8) . . . 8_665 ?
C12 C7 C8 C9 1.9(2) . . . . ?
C13 C10 C11 C12 178.16(15) . . . . ?
C14 S2 O4 Cu1 -161.77(9) . . . . ?

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