# 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_sample_11
_database_code_depnum_ccdc_archive 'CCDC 1497278'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-03-07 downloaded from the CCDC.
;
_audit_creation_date             2016-08-02
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 Cu2 N6 O11 S4'
_chemical_formula_sum            'C16 H20 Cu2 N6 O11 S4'
_chemical_formula_weight         727.70
_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'
Cu Cu -1.9646 0.5888 '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'
S S 0.3331 0.5567 '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                   13.5205(8)
_cell_length_b                   11.0919(6)
_cell_length_c                   16.2446(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.219(5)
_cell_angle_gamma                90
_cell_volume                     2421.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1850
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      133
_cell_measurement_theta_min      10
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.054
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9210
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         4.837
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  100
_diffrn_standards_number         20
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3697
_reflns_number_total             4226
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.040
_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)+(0.0464P)²+1.7015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O1WA(H1WA,H1WB), O1WB(H1WC,H1WD), O2WB(H2WA,H2WB), N2A(H2A), N2B(H2B),
 N3A(H3AA,H3AB), N3B(H3BA,H3BB)
2.b Aromatic/amide H refined with riding coordinates:
 C5A(H5A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1A Cu 0.09948(3) 0.72069(4) 0.38864(2) 0.01384(12) Uani 1 1 d . . . . .
Cu1B Cu 0.35676(3) 0.37897(4) 0.80706(2) 0.01290(12) Uani 1 1 d . . . . .
S1A S 0.06043(6) 0.80064(6) 0.25982(4) 0.01815(17) Uani 1 1 d . . . . .
S1B S 0.36690(6) 0.18511(6) 0.85181(4) 0.01539(16) Uani 1 1 d . . . . .
S2A S 0.19955(5) 0.13947(6) 0.58572(4) 0.01237(16) Uani 1 1 d . . . . .
S2B S 0.35729(5) 0.74641(6) 0.43630(4) 0.01178(15) Uani 1 1 d . . . . .
O1A O 0.10120(15) 0.64246(17) 0.49490(12) 0.0140(4) Uani 1 1 d . . . . .
O1B O 0.34550(16) 0.53893(18) 0.76703(12) 0.0164(4) Uani 1 1 d . . . . .
O1WA O 0.06266(16) 0.87495(19) 0.43816(13) 0.0193(5) Uani 1 1 d . . . . .
H1WA H 0.0026 0.8960 0.4442 0.027(10) Uiso 1 1 d R . . . .
H1WB H 0.1098 0.9147 0.4650 0.09(2) Uiso 1 1 d R . . . .
O1WB O 0.49430(15) 0.44635(18) 0.89529(12) 0.0169(4) Uani 1 1 d . . . . .
H1WC H 0.5137 0.3918 0.9338 0.025 Uiso 1 1 d R . . . .
H1WD H 0.4804 0.5137 0.9213 0.025 Uiso 1 1 d R . . . .
O2A O 0.20035(15) 0.13009(18) 0.67524(12) 0.0157(4) Uani 1 1 d . . . . .
O2B O 0.26310(15) 0.81199(18) 0.41759(12) 0.0155(4) Uani 1 1 d . . . . .
O2WB O 0.26949(15) 0.43987(18) 0.89116(12) 0.0175(4) Uani 1 1 d . . . . .
H2WA H 0.2858 0.4204 0.9434 0.043(13) Uiso 1 1 d R . . . .
H2WB H 0.2648 0.5167 0.8830 0.054(15) Uiso 1 1 d R . . . .
O3A O 0.29594(15) 0.11751(18) 0.55582(12) 0.0162(4) Uani 1 1 d . . . . .
O3B O 0.44205(15) 0.83027(18) 0.44781(12) 0.0165(4) Uani 1 1 d . . . . .
O4A O 0.12302(15) 0.05980(18) 0.54205(12) 0.0162(4) Uani 1 1 d . . . . .
O4B O 0.37146(16) 0.65200(19) 0.37726(12) 0.0179(4) Uani 1 1 d . . . . .
N1A N 0.12254(18) 0.5701(2) 0.33189(14) 0.0147(5) Uani 1 1 d . . . . .
N1B N 0.39960(18) 0.3207(2) 0.70294(15) 0.0126(5) Uani 1 1 d . . . . .
N2A N 0.1214(2) 0.5753(2) 0.24638(14) 0.0168(5) Uani 1 1 d . . . . .
H2A H 0.1388 0.5158 0.2203 0.023(10) Uiso 1 1 d R . . . .
N2B N 0.42491(19) 0.2004(2) 0.70046(14) 0.0134(5) Uani 1 1 d . . . . .
H2B H 0.4543 0.1725 0.6601 0.016 Uiso 1 1 d R . . . .
N3A N 0.0875(2) 0.6747(2) 0.12424(15) 0.0175(5) Uani 1 1 d . . . . .
H3AA H 0.1030 0.6104 0.0990 0.021 Uiso 1 1 d R . . . .
H3AB H 0.0690 0.7382 0.0963 0.021 Uiso 1 1 d R . . . .
N3B N 0.41164(19) 0.0101(2) 0.75083(15) 0.0148(5) Uani 1 1 d . . . . .
H3BA H 0.4005 -0.0349 0.7919 0.023(10) Uiso 1 1 d R . . . .
H3BB H 0.4331 -0.0150 0.7101 0.023(10) Uiso 1 1 d R . . . .
C1A C 0.1201(2) 0.5296(3) 0.51195(18) 0.0141(6) Uani 1 1 d . . . . .
C1B C 0.3498(2) 0.5789(3) 0.69280(17) 0.0134(6) Uani 1 1 d . . . . .
C2A C 0.1213(2) 0.4896(3) 0.59526(18) 0.0155(6) Uani 1 1 d . . . . .
H2AA H 0.108(3) 0.548(4) 0.639(2) 0.025(10) Uiso 1 1 d . . . . .
C2B C 0.3269(2) 0.7024(3) 0.67721(18) 0.0140(6) Uani 1 1 d . . . . .
H2BA H 0.312(3) 0.750(3) 0.719(2) 0.015(8) Uiso 1 1 d . . . . .
C3A C 0.1428(2) 0.3728(3) 0.61831(18) 0.0158(6) Uani 1 1 d . . . . .
H3A H 0.147(2) 0.342(3) 0.674(2) 0.015(8) Uiso 1 1 d . . . . .
C3B C 0.3274(2) 0.7505(3) 0.59908(18) 0.0138(6) Uani 1 1 d . . . . .
H3B H 0.309(2) 0.836(3) 0.5854(19) 0.010(8) Uiso 1 1 d . . . . .
C4A C 0.1648(2) 0.2879(3) 0.55857(18) 0.0138(6) Uani 1 1 d . . . . .
C4B C 0.3528(2) 0.6782(3) 0.53354(17) 0.0132(6) Uani 1 1 d . . . . .
C5A C 0.1618(2) 0.3222(3) 0.47657(17) 0.0142(6) Uani 1 1 d . . . . .
H5A H 0.1744 0.2640 0.4361 0.017 Uiso 1 1 calc R . . . .
C5B C 0.3768(2) 0.5584(3) 0.54631(17) 0.0125(6) Uani 1 1 d . . . . .
H5B H 0.395(3) 0.512(3) 0.502(2) 0.018(9) Uiso 1 1 d . . . . .
C6A C 0.1404(2) 0.4415(3) 0.45213(17) 0.0140(6) Uani 1 1 d . . . . .
C6B C 0.3752(2) 0.5066(3) 0.62523(17) 0.0127(6) Uani 1 1 d . . . . .
C7A C 0.1393(2) 0.4659(3) 0.36471(17) 0.0143(6) Uani 1 1 d . . . . .
H7A H 0.149(2) 0.393(3) 0.3309(19) 0.008(7) Uiso 1 1 d . . . . .
C7B C 0.3998(2) 0.3808(3) 0.63414(17) 0.0119(6) Uani 1 1 d . . . . .
H7B H 0.422(2) 0.338(3) 0.586(2) 0.007(7) Uiso 1 1 d . . . . .
C8A C 0.0922(2) 0.6761(3) 0.20606(18) 0.0160(6) Uani 1 1 d . . . . .
C8B C 0.4030(2) 0.1269(3) 0.76213(17) 0.0138(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1A S1A 2.2814(8) . ?
Cu1A O1A 1.930(2) . ?
Cu1A O1WA 1.977(2) . ?
Cu1A O2B 2.432(2) . ?
Cu1A N1A 1.950(2) . ?
Cu1B S1B 2.2692(8) . ?
Cu1B O1B 1.890(2) . ?
Cu1B O1WB 2.344(2) . ?
Cu1B O2WB 2.016(2) . ?
Cu1B N1B 1.956(2) . ?
S1A C8A 1.713(3) . ?
S1B C8B 1.712(3) . ?
S2A O2A 1.457(2) . ?
S2A O3A 1.460(2) . ?
S2A O4A 1.482(2) . ?
S2A C4A 1.755(3) . ?
S2B O2B 1.470(2) . ?
S2B O3B 1.472(2) . ?
S2B O4B 1.447(2) . ?
S2B C4B 1.759(3) . ?
O1A C1A 1.301(4) . ?
O1B C1B 1.292(3) . ?
O1WA H1WA 0.8602 . ?
O1WA H1WB 0.8545 . ?
O1WB H1WC 0.8893 . ?
O1WB H1WD 0.8890 . ?
O2WB H2WA 0.8802 . ?
O2WB H2WB 0.8637 . ?
N1A N2A 1.389(3) . ?
N1A C7A 1.283(4) . ?
N1B N2B 1.380(3) . ?
N1B C7B 1.301(4) . ?
N2A H2A 0.8324 . ?
N2A C8A 1.334(4) . ?
N2B H2B 0.8601 . ?
N2B C8B 1.349(4) . ?
N3A H3AA 0.8601 . ?
N3A H3AB 0.8601 . ?
N3A C8A 1.324(4) . ?
N3B H3BA 0.8594 . ?
N3B H3BB 0.8002 . ?
N3B C8B 1.316(4) . ?
C1A C2A 1.423(4) . ?
C1A C6A 1.426(4) . ?
C1B C2B 1.420(4) . ?
C1B C6B 1.431(4) . ?
C2A H2AA 0.99(4) . ?
C2A C3A 1.370(4) . ?
C2B H2BA 0.90(4) . ?
C2B C3B 1.377(4) . ?
C3A H3A 0.96(4) . ?
C3A C4A 1.407(4) . ?
C3B H3B 1.00(4) . ?
C3B C4B 1.405(4) . ?
C4A C5A 1.382(4) . ?
C4B C5B 1.378(4) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.403(4) . ?
C5B H5B 0.94(4) . ?
C5B C6B 1.407(4) . ?
C6A C7A 1.444(4) . ?
C6B C7B 1.438(4) . ?
C7A H7A 0.99(3) . ?
C7B H7B 0.98(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
S1A Cu1A O2B 97.51(5) . . ?
O1A Cu1A S1A 167.00(7) . . ?
O1A Cu1A O1WA 90.25(9) . . ?
O1A Cu1A O2B 95.26(8) . . ?
O1A Cu1A N1A 92.90(9) . . ?
O1WA Cu1A S1A 89.62(7) . . ?
O1WA Cu1A O2B 79.91(8) . . ?
N1A Cu1A S1A 86.12(7) . . ?
N1A Cu1A O1WA 173.84(10) . . ?
N1A Cu1A O2B 105.05(9) . . ?
S1B Cu1B O1WB 95.16(6) . . ?
O1B Cu1B S1B 178.24(7) . . ?
O1B Cu1B O1WB 86.56(8) . . ?
O1B Cu1B O2WB 83.53(8) . . ?
O1B Cu1B N1B 91.88(9) . . ?
O2WB Cu1B S1B 96.89(6) . . ?
O2WB Cu1B O1WB 87.86(8) . . ?
N1B Cu1B S1B 87.18(7) . . ?
N1B Cu1B O1WB 110.15(9) . . ?
N1B Cu1B O2WB 161.18(10) . . ?
C8A S1A Cu1A 96.22(11) . . ?
C8B S1B Cu1B 95.59(10) . . ?
O2A S2A O3A 114.20(12) . . ?
O2A S2A O4A 111.38(12) . . ?
O2A S2A C4A 106.90(13) . . ?
O3A S2A O4A 110.09(12) . . ?
O3A S2A C4A 107.30(13) . . ?
O4A S2A C4A 106.56(13) . . ?
O2B S2B O3B 111.02(12) . . ?
O2B S2B C4B 106.59(13) . . ?
O3B S2B C4B 105.07(13) . . ?
O4B S2B O2B 113.28(13) . . ?
O4B S2B O3B 112.61(12) . . ?
O4B S2B C4B 107.69(13) . . ?
C1A O1A Cu1A 127.30(18) . . ?
C1B O1B Cu1B 129.31(18) . . ?
Cu1A O1WA H1WA 124.3 . . ?
Cu1A O1WA H1WB 116.5 . . ?
H1WA O1WA H1WB 117.6 . . ?
Cu1B O1WB H1WC 111.5 . . ?
Cu1B O1WB H1WD 111.3 . . ?
H1WC O1WB H1WD 107.3 . . ?
S2B O2B Cu1A 125.70(12) . . ?
Cu1B O2WB H2WA 117.8 . . ?
Cu1B O2WB H2WB 105.4 . . ?
H2WA O2WB H2WB 113.4 . . ?
N2A N1A Cu1A 116.87(18) . . ?
C7A N1A Cu1A 127.3(2) . . ?
C7A N1A N2A 115.8(2) . . ?
N2B N1B Cu1B 116.26(17) . . ?
C7B N1B Cu1B 127.0(2) . . ?
C7B N1B N2B 116.6(2) . . ?
N1A N2A H2A 120.2 . . ?
C8A N2A N1A 119.8(2) . . ?
C8A N2A H2A 120.0 . . ?
N1B N2B H2B 120.4 . . ?
C8B N2B N1B 119.2(2) . . ?
C8B N2B H2B 120.4 . . ?
H3AA N3A H3AB 120.0 . . ?
C8A N3A H3AA 120.0 . . ?
C8A N3A H3AB 120.0 . . ?
H3BA N3B H3BB 123.4 . . ?
C8B N3B H3BA 116.0 . . ?
C8B N3B H3BB 120.2 . . ?
O1A C1A C2A 119.0(3) . . ?
O1A C1A C6A 124.2(3) . . ?
C2A C1A C6A 116.8(3) . . ?
O1B C1B C2B 117.8(3) . . ?
O1B C1B C6B 124.2(3) . . ?
C2B C1B C6B 118.0(2) . . ?
C1A C2A H2AA 120(2) . . ?
C3A C2A C1A 122.3(3) . . ?
C3A C2A H2AA 118(2) . . ?
C1B C2B H2BA 120(2) . . ?
C3B C2B C1B 121.0(3) . . ?
C3B C2B H2BA 119(2) . . ?
C2A C3A H3A 126(2) . . ?
C2A C3A C4A 119.9(3) . . ?
C4A C3A H3A 114(2) . . ?
C2B C3B H3B 123.1(18) . . ?
C2B C3B C4B 120.2(3) . . ?
C4B C3B H3B 116.7(18) . . ?
C3A C4A S2A 121.7(2) . . ?
C5A C4A S2A 118.6(2) . . ?
C5A C4A C3A 119.6(3) . . ?
C3B C4B S2B 118.0(2) . . ?
C5B C4B S2B 121.3(2) . . ?
C5B C4B C3B 120.6(3) . . ?
C4A C5A H5A 119.5 . . ?
C4A C5A C6A 121.1(3) . . ?
C6A C5A H5A 119.5 . . ?
C4B C5B H5B 119(2) . . ?
C4B C5B C6B 120.2(3) . . ?
C6B C5B H5B 120(2) . . ?
C1A C6A C7A 124.0(3) . . ?
C5A C6A C1A 120.2(3) . . ?
C5A C6A C7A 115.8(3) . . ?
C1B C6B C7B 122.6(3) . . ?
C5B C6B C1B 119.9(3) . . ?
C5B C6B C7B 117.5(3) . . ?
N1A C7A C6A 124.1(3) . . ?
N1A C7A H7A 122.1(18) . . ?
C6A C7A H7A 113.7(18) . . ?
N1B C7B C6B 124.2(3) . . ?
N1B C7B H7B 117.5(19) . . ?
C6B C7B H7B 118.2(19) . . ?
N2A C8A S1A 120.2(2) . . ?
N3A C8A S1A 122.3(2) . . ?
N3A C8A N2A 117.6(3) . . ?
N2B C8B S1B 120.7(2) . . ?
N3B C8B S1B 121.8(2) . . ?
N3B C8B N2B 117.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1WA H1WA O4A 0.86 1.81 2.665(3) 179.5 3_566
O1WA H1WB O4A 0.85 2.04 2.724(3) 137.1 1_565
O1WB H1WD O3B 0.89 1.87 2.738(3) 165.0 4_576
O2WB H2WA O3A 0.88 1.86 2.735(3) 169.6 4_566
N2A H2A O2A 0.83 1.99 2.817(3) 169.3 4_565
N2B H2B O3B 0.86 2.36 3.177(3) 158.7 3_666
N3A H3AA O1WA 0.86 2.62 3.055(3) 112.9 4_575
N3A H3AA O4A 0.86 2.13 2.986(3) 172.0 4_565
N3A H3AB O1A 0.86 2.19 2.940(3) 145.1 4_575
N3B H3BA O4B 0.86 1.97 2.826(3) 173.8 4_566

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
Cu1A S1A C8A N2A 3.9(3) . . . . ?
Cu1A S1A C8A N3A -177.3(2) . . . . ?
Cu1A O1A C1A C2A 177.7(2) . . . . ?
Cu1A O1A C1A C6A -2.0(4) . . . . ?
Cu1A N1A N2A C8A -8.8(4) . . . . ?
Cu1A N1A C7A C6A 2.3(4) . . . . ?
Cu1B S1B C8B N2B 7.0(2) . . . . ?
Cu1B S1B C8B N3B -173.7(2) . . . . ?
Cu1B O1B C1B C2B 172.5(2) . . . . ?
Cu1B O1B C1B C6B -7.0(4) . . . . ?
Cu1B N1B N2B C8B 11.3(3) . . . . ?
Cu1B N1B C7B C6B 5.4(4) . . . . ?
S2A C4A C5A C6A -176.1(2) . . . . ?
S2B C4B C5B C6B 178.3(2) . . . . ?
O1A C1A C2A C3A -178.5(3) . . . . ?
O1A C1A C6A C5A 178.8(3) . . . . ?
O1A C1A C6A C7A -2.2(5) . . . . ?
O1B C1B C2B C3B -178.3(3) . . . . ?
O1B C1B C6B C5B 179.3(3) . . . . ?
O1B C1B C6B C7B -0.6(5) . . . . ?
O1WB Cu1B O1B C1B 120.0(2) . . . . ?
O2A S2A C4A C3A -0.6(3) . . . . ?
O2A S2A C4A C5A 177.7(2) . . . . ?
O2B S2B C4B C3B -50.5(3) . . . . ?
O2B S2B C4B C5B 131.7(2) . . . . ?
O2WB Cu1B O1B C1B -151.7(3) . . . . ?
O3A S2A C4A C3A -123.5(2) . . . . ?
O3A S2A C4A C5A 54.7(3) . . . . ?
O3B S2B O2B Cu1A 178.08(12) . . . . ?
O3B S2B C4B C3B 67.4(3) . . . . ?
O3B S2B C4B C5B -110.4(3) . . . . ?
O4A S2A C4A C3A 118.6(2) . . . . ?
O4A S2A C4A C5A -63.1(3) . . . . ?
O4B S2B O2B Cu1A 50.22(17) . . . . ?
O4B S2B C4B C3B -172.4(2) . . . . ?
O4B S2B C4B C5B 9.8(3) . . . . ?
N1A N2A C8A S1A 2.3(4) . . . . ?
N1A N2A C8A N3A -176.6(3) . . . . ?
N1B Cu1B O1B C1B 10.0(3) . . . . ?
N1B N2B C8B S1B -12.6(4) . . . . ?
N1B N2B C8B N3B 168.1(3) . . . . ?
N2A N1A C7A C6A -178.0(3) . . . . ?
N2B N1B C7B C6B 179.9(3) . . . . ?
C1A C2A C3A C4A 0.0(5) . . . . ?
C1A C6A C7A N1A 2.0(5) . . . . ?
C1B C2B C3B C4B -1.4(5) . . . . ?
C1B C6B C7B N1B 1.2(4) . . . . ?
C2A C1A C6A C5A -0.9(4) . . . . ?
C2A C1A C6A C7A 178.1(3) . . . . ?
C2A C3A C4A S2A 176.4(2) . . . . ?
C2A C3A C4A C5A -1.8(4) . . . . ?
C2B C1B C6B C5B -0.1(4) . . . . ?
C2B C1B C6B C7B 179.9(3) . . . . ?
C2B C3B C4B S2B -177.3(2) . . . . ?
C2B C3B C4B C5B 0.5(4) . . . . ?
C3A C4A C5A C6A 2.2(4) . . . . ?
C3B C4B C5B C6B 0.6(4) . . . . ?
C4A C5A C6A C1A -0.8(4) . . . . ?
C4A C5A C6A C7A -179.9(3) . . . . ?
C4B S2B O2B Cu1A -68.03(16) . . . . ?
C4B C5B C6B C1B -0.8(4) . . . . ?
C4B C5B C6B C7B 179.2(3) . . . . ?
C5A C6A C7A N1A -179.0(3) . . . . ?
C5B C6B C7B N1B -178.7(3) . . . . ?
C6A C1A C2A C3A 1.3(4) . . . . ?
C6B C1B C2B C3B 1.2(4) . . . . ?
C7A N1A N2A C8A 171.5(3) . . . . ?
C7B N1B N2B C8B -163.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shi_3089
_database_code_depnum_ccdc_archive 'CCDC 1497276'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-03-07 downloaded from the CCDC.
;
_audit_creation_date             2016-08-02
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H19 Cu N3 O6 S4'
_chemical_formula_sum            'C12 H19 Cu N3 O6 S4'
_chemical_formula_weight         493.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H30 N4 O4 S2 Cu1'
_chemical_oxdiff_usercomment     S.A._20
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.3750(3)
_cell_length_b                   12.3166(9)
_cell_length_c                   13.7976(12)
_cell_angle_alpha                75.444(7)
_cell_angle_beta                 77.550(6)
_cell_angle_gamma                76.945(5)
_cell_volume                     1006.90(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2830
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6180
_cell_measurement_theta_min      2.0870
_exptl_absorpt_coefficient_mu    1.532
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             506
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6669
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.55
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  37.00   1.00   10.00    --   17.94 -38.00 -30.00   88
  2  ω    -15.00  16.00   1.00   10.00    --  -15.76 -99.00 150.00   31
  3  ω     -1.00  87.00   1.00   10.00    --   17.94  38.00 150.00   88
  4  ω     -7.00  19.00   1.00   10.00    --   17.94  19.00 150.00   26
  5  ω    -81.00  10.00   1.00   10.00    --  -15.76 -77.00 -90.00   91
  6  ω     43.00  71.00   1.00   10.00    --   17.94 178.00 -90.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0432348000
_diffrn_orient_matrix_UB_12      -0.0518420000
_diffrn_orient_matrix_UB_13      0.0312688000
_diffrn_orient_matrix_UB_21      -0.0076002000
_diffrn_orient_matrix_UB_22      0.0291595000
_diffrn_orient_matrix_UB_23      0.0392442000
_diffrn_orient_matrix_UB_31      -0.1072327000
_diffrn_orient_matrix_UB_32      -0.0110918000
_diffrn_orient_matrix_UB_33      0.0196322000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3037
_reflns_number_total             3554
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0601
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0476P)²+3.6690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1376
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S3X-S3Y
 0.6 with sigma of 0.01
 S3X-O5 \\sim S3-O5 \\sim S3Y-O5
 with sigma of 0.01
 C11X-C10X \\sim C10Y-C11Y \\sim C11-C10
 with sigma of 0.01
 S3-C11 \\sim S3Y-C11Y \\sim S3X-C11X \\sim S3-C10 \\sim S3Y-C10Y \\sim S3X-C10X
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uiso(S3) = Uiso(S3X) = Uiso(S3Y)
Uiso(C11) = Uiso(C11Y) = Uiso(C11X) = Uiso(C10) = Uiso(C10Y) = Uiso(C10X)
4. Others
 Fixed Sof: S3(0.4) S3X(0.4) S3Y(0.2) C10(0.4) H10A(0.4) H10B(0.4) H10C(0.4)
 C10X(0.4) H10D(0.4) H10E(0.4) H10F(0.4) C10Y(0.2) H10G(0.2) H10H(0.2)
 H10I(0.2) C11(0.4) H11A(0.4) H11B(0.4) H11C(0.4) C11X(0.4) H11D(0.4) H11E(0.4)
 H11F(0.4) C11Y(0.2) H11G(0.2) H11H(0.2) H11I(0.2)
5.a Riding coordinates:
 C10(H10A,H10B,H10C), C10X(H10D,H10E,H10F), C10Y(H10G,H10H,H10I), C11(H11A,
 H11B,H11C), C11X(H11D,H11E,H11F), C11Y(H11G,H11H,H11I), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C7(H7)
5.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.61728(10) 0.27935(6) 0.73534(5) 0.0320(2) Uani 1 d A . .
S1 S 0.9236(2) 0.23084(13) 0.80593(11) 0.0375(4) Uani 1 d A . .
S2 S 0.1791(2) 0.17358(12) 0.32844(10) 0.0313(3) Uani 1 d . . .
S3 S 0.3462(6) 0.5119(3) 0.7599(3) 0.0347(6) Uiso 0.40 d A 1 D
S3X S 0.2885(6) 0.4876(3) 0.7905(4) 0.0347(6) Uiso 0.40 d A 2 D
S3Y S 0.3265(11) 0.5016(6) 0.8112(6) 0.0347(6) Uiso 0.20 d A 3 D
S4 S 0.3043(2) 0.20364(13) 0.97233(11) 0.0392(4) Uani 1 d A . .
O1 O 0.3909(6) 0.3378(3) 0.6563(3) 0.0411(10) Uani 1 d . . .
O2 O -0.0089(6) 0.1169(4) 0.3706(3) 0.0446(10) Uani 1 d . . .
O3 O 0.1269(7) 0.2755(4) 0.2522(3) 0.0523(11) Uani 1 d . . .
O4 O 0.3708(6) 0.0953(4) 0.2946(3) 0.0403(10) Uani 1 d . . .
O5 O 0.5121(7) 0.4051(4) 0.8083(4) 0.0506(11) Uani 1 d . . D
O6 O 0.4255(6) 0.1474(4) 0.8858(3) 0.0408(10) Uani 1 d . . .
N1 N 0.7509(6) 0.1621(4) 0.6578(3) 0.0262(9) Uani 1 d . . .
N2 N 0.9460(6) 0.0935(4) 0.6819(3) 0.0302(10) Uani 1 d A . .
H2 H 1.0052 0.0364 0.6539 0.036 Uiso 1 calc . . R
N3 N 1.2270(7) 0.0540(4) 0.7713(3) 0.0350(11) Uani 1 d A . .
H3A H 1.2844 -0.0020 0.7417 0.042 Uiso 1 calc . . R
H3B H 1.2912 0.0678 0.8144 0.042 Uiso 1 calc . . R
C1 C 0.3477(8) 0.2979(4) 0.5856(4) 0.0304(12) Uani 1 d A . .
C2 C 0.1579(9) 0.3482(5) 0.5434(4) 0.0378(13) Uani 1 d . . .
H2A H 0.0649 0.4091 0.5677 0.045 Uiso 1 calc . . R
C3 C 0.1046(9) 0.3107(5) 0.4675(4) 0.0359(13) Uani 1 d . . .
H3 H -0.0222 0.3465 0.4411 0.043 Uiso 1 calc . . R
C4 C 0.2412(8) 0.2185(5) 0.4295(4) 0.0299(11) Uani 1 d . . .
C5 C 0.4265(8) 0.1672(4) 0.4691(4) 0.0294(11) Uani 1 d A . .
H5 H 0.5174 0.1065 0.4438 0.035 Uiso 1 calc . . R
C6 C 0.4841(8) 0.2033(4) 0.5470(4) 0.0267(11) Uani 1 d . . .
C7 C 0.6816(8) 0.1433(4) 0.5837(4) 0.0276(11) Uani 1 d A . .
H7 H 0.7663 0.0863 0.5514 0.033 Uiso 1 calc . . R
C8 C 1.0404(8) 0.1188(4) 0.7503(4) 0.0291(11) Uani 1 d . . .
C10 C 0.370(3) 0.6182(13) 0.8183(14) 0.063(2) Uiso 0.40 d A 1 D
H10A H 0.3595 0.5891 0.8903 0.095 Uiso 0.40 d A 1 R
H10B H 0.2548 0.6825 0.8052 0.095 Uiso 0.40 d A 1 R
H10C H 0.5088 0.6416 0.7915 0.095 Uiso 0.40 d A 1 R
C10X C 0.401(3) 0.5834(15) 0.6867(10) 0.063(2) Uiso 0.40 d A 2 D
H10D H 0.5246 0.6034 0.7025 0.095 Uiso 0.40 d A 2 R
H10E H 0.2930 0.6508 0.6717 0.095 Uiso 0.40 d A 2 R
H10F H 0.4461 0.5487 0.6287 0.095 Uiso 0.40 d A 2 R
C10Y C 0.397(7) 0.613(2) 0.7129(19) 0.063(2) Uiso 0.20 d A 3 D
H10G H 0.5262 0.6340 0.7226 0.095 Uiso 0.20 d A 3 R
H10H H 0.2795 0.6775 0.7125 0.095 Uiso 0.20 d A 3 R
H10I H 0.4245 0.5898 0.6493 0.095 Uiso 0.20 d A 3 R
C11 C 0.091(2) 0.4832(15) 0.8207(14) 0.063(2) Uiso 0.40 d A 1 D
H11A H 0.0641 0.4191 0.8006 0.095 Uiso 0.40 d A 1 R
H11B H -0.0184 0.5487 0.8022 0.095 Uiso 0.40 d A 1 R
H11C H 0.0859 0.4660 0.8929 0.095 Uiso 0.40 d A 1 R
C11X C 0.275(3) 0.5571(15) 0.8884(10) 0.063(2) Uiso 0.40 d A 2 D
H11D H 0.2148 0.5130 0.9519 0.095 Uiso 0.40 d A 2 R
H11E H 0.1842 0.6310 0.8753 0.095 Uiso 0.40 d A 2 R
H11F H 0.4195 0.5657 0.8917 0.095 Uiso 0.40 d A 2 R
C11Y C 0.177(6) 0.572(2) 0.9045(18) 0.063(2) Uiso 0.20 d A 3 D
H11G H 0.1670 0.5199 0.9692 0.095 Uiso 0.20 d A 3 R
H11H H 0.0325 0.6039 0.8891 0.095 Uiso 0.20 d A 3 R
H11I H 0.2468 0.6327 0.9069 0.095 Uiso 0.20 d A 3 R
C12 C 0.5067(12) 0.2030(7) 1.0429(5) 0.062(2) Uani 1 d . . .
H12A H 0.4383 0.2318 1.1028 0.093 Uiso 1 d A . R
H12B H 0.6077 0.2504 1.0020 0.093 Uiso 1 d . . R
H12C H 0.5837 0.1265 1.0621 0.093 Uiso 1 d . . R
C13 C 0.1647(11) 0.1017(6) 1.0612(5) 0.0546(17) Uani 1 d . . .
H13A H 0.0652 0.0810 1.0287 0.082 Uiso 1 d A . R
H13B H 0.2674 0.0350 1.0846 0.082 Uiso 1 d . . R
H13C H 0.0846 0.1337 1.1179 0.082 Uiso 1 d . . R


_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 S1 2.2628(15) . ?
Cu1 O1 1.898(4) . ?
Cu1 O5 1.970(4) . ?
Cu1 O6 2.560(4) . ?
Cu1 N1 1.946(4) . ?
S1 C8 1.694(5) . ?
S2 O2 1.461(4) . ?
S2 O3 1.447(4) . ?
S2 O4 1.445(4) . ?
S2 C4 1.769(5) . ?
S3 O5 1.591(5) . ?
S3 C10 1.750(10) . ?
S3 H10D 1.7128 . ?
S3 H10E 1.8417 . ?
S3 H10F 1.7625 . ?
S3 H10I 1.6284 . ?
S3 C11 1.731(10) . ?
S3X O5 1.580(5) . ?
S3X C10X 1.745(10) . ?
S3X H11A 1.7829 . ?
S3X H11C 1.7071 . ?
S3X C11X 1.751(10) . ?
S3Y O5 1.477(7) . ?
S3Y H10A 1.7859 . ?
S3Y C10Y 1.735(11) . ?
S3Y H11C 1.7677 . ?
S3Y H11F 1.7732 . ?
S3Y C11Y 1.728(11) . ?
S4 O6 1.509(4) . ?
S4 C12 1.774(7) . ?
S4 C13 1.770(6) . ?
O1 C1 1.300(6) . ?
N1 N2 1.391(6) . ?
N1 C7 1.285(6) . ?
N2 H2 0.8600 . ?
N2 C8 1.352(6) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C8 1.319(6) . ?
C1 C2 1.403(7) . ?
C1 C6 1.432(7) . ?
C2 H2A 0.9300 . ?
C2 C3 1.377(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.408(7) . ?
C4 C5 1.364(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(7) . ?
C6 C7 1.434(7) . ?
C7 H7 0.9300 . ?
C10 H10A 0.9601 . ?
C10 H10B 0.9601 . ?
C10 H10C 0.9599 . ?
C10X H10D 0.9599 . ?
C10X H10E 0.9600 . ?
C10X H10F 0.9600 . ?
C10X H10I 0.4973 . ?
C10Y H10D 0.7815 . ?
C10Y H10E 0.9316 . ?
C10Y H10G 0.9600 . ?
C10Y H10H 0.9600 . ?
C10Y H10I 0.9600 . ?
C11 H11A 0.9601 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9598 . ?
C11X H10A 0.7418 . ?
C11X H11D 0.9600 . ?
C11X H11E 0.9600 . ?
C11X H11F 0.9600 . ?
C11X H11I 0.9931 . ?
C11Y H10A 1.1956 . ?
C11Y H11D 0.8772 . ?
C11Y H11E 0.7401 . ?
C11Y H11G 0.9600 . ?
C11Y H11H 0.9601 . ?
C11Y H11I 0.9601 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9599 . ?
C13 H13B 0.9601 . ?
C13 H13C 0.9603 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 Cu1 O6 90.38(10) . . ?
O1 Cu1 S1 169.24(15) . . ?
O1 Cu1 O5 90.40(16) . . ?
O1 Cu1 O6 100.38(16) . . ?
O1 Cu1 N1 92.45(16) . . ?
O5 Cu1 S1 89.62(13) . . ?
O5 Cu1 O6 89.52(17) . . ?
N1 Cu1 S1 86.52(12) . . ?
N1 Cu1 O5 173.64(18) . . ?
N1 Cu1 O6 95.55(15) . . ?
C8 S1 Cu1 96.47(18) . . ?
O2 S2 C4 106.5(2) . . ?
O3 S2 O2 111.6(3) . . ?
O3 S2 C4 106.6(3) . . ?
O4 S2 O2 111.7(2) . . ?
O4 S2 O3 113.7(3) . . ?
O4 S2 C4 106.1(2) . . ?
O5 S3 C10 102.4(7) . . ?
O5 S3 H10D 99.4 . . ?
O5 S3 H10E 150.5 . . ?
O5 S3 H10F 107.8 . . ?
O5 S3 H10I 119.7 . . ?
O5 S3 C11 104.2(7) . . ?
C10 S3 H10D 59.4 . . ?
C10 S3 H10E 71.6 . . ?
C10 S3 H10F 109.2 . . ?
C10 S3 H10I 89.8 . . ?
H10D S3 H10E 52.2 . . ?
H10D S3 H10F 53.6 . . ?
H10D S3 H10I 39.6 . . ?
H10E S3 H10F 51.5 . . ?
H10E S3 H10I 34.2 . . ?
H10F S3 H10I 20.4 . . ?
C11 S3 C10 101.0(7) . . ?
C11 S3 H10D 152.4 . . ?
C11 S3 H10E 105.3 . . ?
C11 S3 H10F 129.1 . . ?
C11 S3 H10I 131.3 . . ?
O5 S3X C10X 95.8(8) . . ?
O5 S3X H11A 115.5 . . ?
O5 S3X H11C 112.4 . . ?
O5 S3X C11X 95.1(7) . . ?
C10X S3X H11A 128.3 . . ?
C10X S3X H11C 147.6 . . ?
C10X S3X C11X 100.2(7) . . ?
H11A S3X H11C 53.3 . . ?
C11X S3X H11A 115.6 . . ?
C11X S3X H11C 63.0 . . ?
O5 S3Y H10A 110.1 . . ?
O5 S3Y C10Y 107.2(14) . . ?
O5 S3Y H11C 114.3 . . ?
O5 S3Y H11F 96.4 . . ?
O5 S3Y C11Y 134.4(13) . . ?
H10A S3Y H11C 91.5 . . ?
H10A S3Y H11F 13.7 . . ?
C10Y S3Y H10A 84.0 . . ?
C10Y S3Y H11C 137.0 . . ?
C10Y S3Y H11F 87.1 . . ?
H11C S3Y H11F 98.4 . . ?
C11Y S3Y H10A 39.7 . . ?
C11Y S3Y C10Y 102.2(9) . . ?
C11Y S3Y H11C 54.5 . . ?
C11Y S3Y H11F 50.9 . . ?
O6 S4 C12 105.1(3) . . ?
O6 S4 C13 106.6(3) . . ?
C13 S4 C12 98.5(3) . . ?
C1 O1 Cu1 128.9(3) . . ?
S3 O5 Cu1 117.5(3) . . ?
S3X O5 Cu1 119.2(3) . . ?
S3X O5 S3 20.64(19) . . ?
S3Y O5 Cu1 137.2(4) . . ?
S3Y O5 S3 25.1(3) . . ?
S3Y O5 S3X 18.2(3) . . ?
S4 O6 Cu1 114.5(2) . . ?
N2 N1 Cu1 117.2(3) . . ?
C7 N1 Cu1 126.8(3) . . ?
C7 N1 N2 116.0(4) . . ?
N1 N2 H2 120.8 . . ?
C8 N2 N1 118.4(4) . . ?
C8 N2 H2 120.8 . . ?
H3A N3 H3B 120.0 . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
O1 C1 C2 119.6(5) . . ?
O1 C1 C6 123.6(5) . . ?
C2 C1 C6 116.9(5) . . ?
C1 C2 H2A 118.8 . . ?
C3 C2 C1 122.3(5) . . ?
C3 C2 H2A 118.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(5) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 S2 120.4(4) . . ?
C5 C4 S2 120.6(4) . . ?
C5 C4 C3 118.9(5) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.0(5) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C7 122.8(4) . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 C7 117.6(4) . . ?
N1 C7 C6 125.1(5) . . ?
N1 C7 H7 117.4 . . ?
C6 C7 H7 117.4 . . ?
N2 C8 S1 120.9(4) . . ?
N3 C8 S1 121.4(4) . . ?
N3 C8 N2 117.7(5) . . ?
S3 C10 H10A 109.6 . . ?
S3 C10 H10B 109.3 . . ?
S3 C10 H10C 109.5 . . ?
S3 C10 H10G 76.0 . . ?
S3 C10 H11E 101.0 . . ?
S3 C10 H11F 101.1 . . ?
S3 C10 H11I 121.4 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10A C10 H10G 143.3 . . ?
H10A C10 H11E 60.6 . . ?
H10A C10 H11F 21.8 . . ?
H10A C10 H11I 37.7 . . ?
H10B C10 H10C 109.5 . . ?
H10B C10 H10G 102.0 . . ?
H10B C10 H11E 55.9 . . ?
H10B C10 H11F 130.9 . . ?
H10B C10 H11I 71.8 . . ?
H10C C10 H10G 39.9 . . ?
H10C C10 H11E 149.4 . . ?
H10C C10 H11F 94.8 . . ?
H10C C10 H11I 125.6 . . ?
H10G C10 H11E 155.9 . . ?
H10G C10 H11F 122.6 . . ?
H10G C10 H11I 162.6 . . ?
H11E C10 H11F 81.5 . . ?
H11E C10 H11I 29.1 . . ?
H11F C10 H11I 59.4 . . ?
S3X C10X H10D 109.5 . . ?
S3X C10X H10E 109.4 . . ?
S3X C10X H10F 109.5 . . ?
S3X C10X H10G 106.4 . . ?
S3X C10X H10H 96.7 . . ?
S3X C10X H10I 142.3 . . ?
H10D C10X H10E 109.5 . . ?
H10D C10X H10F 109.5 . . ?
H10D C10X H10G 17.6 . . ?
H10D C10X H10H 88.8 . . ?
H10D C10X H10I 97.2 . . ?
H10E C10X H10F 109.5 . . ?
H10E C10X H10G 95.2 . . ?
H10E C10X H10H 30.8 . . ?
H10E C10X H10I 84.9 . . ?
H10F C10X H10G 125.5 . . ?
H10F C10X H10H 139.7 . . ?
H10F C10X H10I 34.2 . . ?
H10G C10X H10H 71.8 . . ?
H10G C10X H10I 106.8 . . ?
H10H C10X H10I 110.4 . . ?
S3Y C10Y H10C 84.5 . . ?
S3Y C10Y H10D 106.0 . . ?
S3Y C10Y H10E 117.1 . . ?
S3Y C10Y H10F 96.7 . . ?
S3Y C10Y H10G 109.4 . . ?
S3Y C10Y H10H 109.4 . . ?
S3Y C10Y H10I 109.6 . . ?
H10C C10Y H10D 63.2 . . ?
H10C C10Y H10E 137.2 . . ?
H10C C10Y H10F 141.4 . . ?
H10C C10Y H10G 35.5 . . ?
H10C C10Y H10H 95.9 . . ?
H10C C10Y H10I 143.7 . . ?
H10D C10Y H10E 132.2 . . ?
H10D C10Y H10F 79.6 . . ?
H10D C10Y H10G 33.0 . . ?
H10D C10Y H10H 136.5 . . ?
H10D C10Y H10I 80.6 . . ?
H10E C10Y H10F 76.0 . . ?
H10E C10Y H10G 131.8 . . ?
H10E C10Y H10H 43.4 . . ?
H10E C10Y H10I 66.8 . . ?
H10F C10Y H10G 111.4 . . ?
H10F C10Y H10H 119.4 . . ?
H10F C10Y H10I 13.5 . . ?
H10G C10Y H10H 109.5 . . ?
H10G C10Y H10I 109.5 . . ?
H10H C10Y H10I 109.5 . . ?
S3 C11 H11A 109.5 . . ?
S3 C11 H11B 109.3 . . ?
S3 C11 H11C 109.6 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S3X C11X H10A 123.6 . . ?
S3X C11X H11D 109.5 . . ?
S3X C11X H11E 109.4 . . ?
S3X C11X H11F 109.5 . . ?
S3X C11X H11G 115.2 . . ?
S3X C11X H11H 91.6 . . ?
S3X C11X H11I 144.5 . . ?
H10A C11X H11D 116.4 . . ?
H10A C11X H11E 84.8 . . ?
H10A C11X H11F 24.9 . . ?
H10A C11X H11G 116.8 . . ?
H10A C11X H11H 126.6 . . ?
H10A C11X H11I 54.1 . . ?
H11D C11X H11E 109.5 . . ?
H11D C11X H11F 109.5 . . ?
H11D C11X H11G 12.7 . . ?
H11D C11X H11H 79.6 . . ?
H11D C11X H11I 99.5 . . ?
H11E C11X H11F 109.5 . . ?
H11E C11X H11G 96.7 . . ?
H11E C11X H11H 43.4 . . ?
H11E C11X H11I 39.3 . . ?
H11F C11X H11G 115.6 . . ?
H11F C11X H11H 151.5 . . ?
H11F C11X H11I 78.1 . . ?
H11G C11X H11H 68.7 . . ?
H11G C11X H11I 89.7 . . ?
H11H C11X H11I 73.7 . . ?
S3Y C11Y H10A 72.7 . . ?
S3Y C11Y H11D 90.7 . . ?
S3Y C11Y H11E 97.2 . . ?
S3Y C11Y H11F 66.1 . . ?
S3Y C11Y H11G 109.6 . . ?
S3Y C11Y H11H 109.2 . . ?
S3Y C11Y H11I 109.6 . . ?
H10A C11Y H11D 87.4 . . ?
H10A C11Y H11E 69.0 . . ?
H10A C11Y H11F 12.4 . . ?
H10A C11Y H11G 102.5 . . ?
H10A C11Y H11H 144.5 . . ?
H10A C11Y H11I 43.0 . . ?
H11D C11Y H11E 151.4 . . ?
H11D C11Y H11F 77.4 . . ?
H11D C11Y H11G 21.5 . . ?
H11D C11Y H11H 127.4 . . ?
H11D C11Y H11I 108.4 . . ?
H11E C11Y H11F 80.8 . . ?
H11E C11Y H11G 148.3 . . ?
H11E C11Y H11H 75.6 . . ?
H11E C11Y H11I 43.2 . . ?
H11F C11Y H11G 94.5 . . ?
H11F C11Y H11H 155.3 . . ?
H11F C11Y H11I 54.6 . . ?
H11G C11Y H11H 109.5 . . ?
H11G C11Y H11I 109.5 . . ?
H11H C11Y H11I 109.5 . . ?
S4 C12 H12A 109.4 . . ?
S4 C12 H12B 109.5 . . ?
S4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S4 C13 H13A 108.8 . . ?
S4 C13 H13B 110.0 . . ?
S4 C13 H13C 109.7 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.86 1.99 2.784(6) 152.1 2_656
N3 H3A O4 0.86 2.25 2.914(6) 133.6 2_756
N3 H3B O6 0.86 1.97 2.803(6) 162.0 1_655

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 S1 C8 N2 4.2(4) . . . . ?
Cu1 S1 C8 N3 -176.5(4) . . . . ?
Cu1 O1 C1 C2 173.6(4) . . . . ?
Cu1 O1 C1 C6 -6.3(8) . . . . ?
Cu1 N1 N2 C8 -5.9(6) . . . . ?
Cu1 N1 C7 C6 -3.0(8) . . . . ?
S1 Cu1 O1 C1 90.4(8) . . . . ?
S1 Cu1 O5 S3 154.0(3) . . . . ?
S1 Cu1 O5 S3X 177.4(4) . . . . ?
S1 Cu1 O5 S3Y 173.9(7) . . . . ?
S1 Cu1 O6 S4 90.2(2) . . . . ?
S1 Cu1 N1 N2 6.7(3) . . . . ?
S1 Cu1 N1 C7 -170.7(4) . . . . ?
S2 C4 C5 C6 177.9(4) . . . . ?
O1 Cu1 S1 C8 -90.1(7) . . . . ?
O1 Cu1 O5 S3 -15.2(3) . . . . ?
O1 Cu1 O5 S3X 8.2(4) . . . . ?
O1 Cu1 O5 S3Y 4.7(7) . . . . ?
O1 Cu1 O6 S4 -89.7(2) . . . . ?
O1 Cu1 N1 N2 176.0(4) . . . . ?
O1 Cu1 N1 C7 -1.4(5) . . . . ?
O1 C1 C2 C3 179.2(5) . . . . ?
O1 C1 C6 C5 -178.8(5) . . . . ?
O1 C1 C6 C7 0.4(8) . . . . ?
O2 S2 C4 C3 -72.5(5) . . . . ?
O2 S2 C4 C5 110.1(5) . . . . ?
O3 S2 C4 C3 46.8(5) . . . . ?
O3 S2 C4 C5 -130.6(5) . . . . ?
O4 S2 C4 C3 168.4(4) . . . . ?
O4 S2 C4 C5 -9.1(5) . . . . ?
O5 Cu1 S1 C8 179.8(2) . . . . ?
O5 Cu1 O1 C1 -179.6(5) . . . . ?
O5 Cu1 O6 S4 0.6(2) . . . . ?
O5 Cu1 N1 N2 59.5(17) . . . . ?
O5 Cu1 N1 C7 -118.0(15) . . . . ?
O6 Cu1 S1 C8 90.3(2) . . . . ?
O6 Cu1 O1 C1 -90.0(5) . . . . ?
O6 Cu1 O5 S3 -115.6(3) . . . . ?
O6 Cu1 O5 S3X -92.2(4) . . . . ?
O6 Cu1 O5 S3Y -95.7(7) . . . . ?
O6 Cu1 N1 N2 -83.3(3) . . . . ?
O6 Cu1 N1 C7 99.2(4) . . . . ?
N1 Cu1 S1 C8 -5.3(2) . . . . ?
N1 Cu1 O1 C1 6.1(5) . . . . ?
N1 Cu1 O5 S3 101.4(16) . . . . ?
N1 Cu1 O5 S3X 124.8(15) . . . . ?
N1 Cu1 O5 S3Y 121.3(16) . . . . ?
N1 Cu1 O6 S4 176.7(2) . . . . ?
N1 N2 C8 S1 0.3(7) . . . . ?
N1 N2 C8 N3 -179.1(4) . . . . ?
N2 N1 C7 C6 179.5(5) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C1 C6 C7 N1 4.5(8) . . . . ?
C2 C1 C6 C5 1.3(8) . . . . ?
C2 C1 C6 C7 -179.5(5) . . . . ?
C2 C3 C4 S2 -177.5(5) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C4 C5 C6 C1 -1.1(8) . . . . ?
C4 C5 C6 C7 179.7(5) . . . . ?
C5 C6 C7 N1 -176.3(5) . . . . ?
C6 C1 C2 C3 -1.0(9) . . . . ?
C7 N1 N2 C8 171.8(5) . . . . ?
C10 S3 O5 Cu1 -160.2(6) . . . . ?
C10 S3 O5 S3X 99.5(9) . . . . ?
C10 S3 O5 S3Y 52.8(10) . . . . ?
C10X S3X O5 Cu1 -88.3(7) . . . . ?
C10X S3X O5 S3 2.6(9) . . . . ?
C10X S3X O5 S3Y 84.1(16) . . . . ?
C10Y S3Y O5 Cu1 -84.4(15) . . . . ?
C10Y S3Y O5 S3 -39.0(16) . . . . ?
C10Y S3Y O5 S3X -94(2) . . . . ?
C11 S3 O5 Cu1 94.9(7) . . . . ?
C11 S3 O5 S3X -5.5(9) . . . . ?
C11 S3 O5 S3Y -52.1(10) . . . . ?
C11X S3X O5 Cu1 170.9(6) . . . . ?
C11X S3X O5 S3 -98.2(9) . . . . ?
C11X S3X O5 S3Y -16.8(15) . . . . ?
C11Y S3Y O5 Cu1 147.8(17) . . . . ?
C11Y S3Y O5 S3 -167(2) . . . . ?
C11Y S3Y O5 S3X 138(3) . . . . ?
C12 S4 O6 Cu1 -81.5(3) . . . . ?
C13 S4 O6 Cu1 174.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.102
_oxdiff_exptl_absorpt_empirical_full_min 0.881
####################################################################### 
# 
# 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_cu_sa51blue_0m
_database_code_depnum_ccdc_archive 'CCDC 1497279'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-03-07 downloaded from the CCDC.
;
_audit_creation_date             2016-08-02
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H52 Cu4 N12 O20 S8, 4(H2 O)'
_chemical_formula_sum            'C40 H60 Cu4 N12 O24 S8'
_chemical_formula_weight         1603.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cu Cu -1.9646 0.5888 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0020(4)
_cell_length_b                   13.1053(6)
_cell_length_c                   14.1945(7)
_cell_angle_alpha                88.965(3)
_cell_angle_beta                 88.544(3)
_cell_angle_gamma                80.556(3)
_cell_volume                     1467.76(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3240
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      102.01
_cell_measurement_theta_min      6.10
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.086
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2465
_diffrn_reflns_av_unetI/netI     0.0900
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30234
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        50.433
_diffrn_reflns_theta_max         50.433
_diffrn_reflns_theta_min         3.115
_diffrn_ambient_temperature      130.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2096
_reflns_number_total             3010
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.173
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0731
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²+21.9772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1918
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9B) \\sim Ueq, Uanis(C6A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Riding coordinates:
 O1WA(H1WA,H1WB), O1WB(H1WC,H1WD), N2A(H2A), N2B(H2B), O1W(H1WE,H1WF)
3.b Free rotating group:
 O2W(H2WA,H2WB)
3.c Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C9B(H9BA,H9BB)
3.d Aromatic/amide H refined with riding coordinates:
 N3A(H3A), N3B(H3B), C2A(H2AA), C2B(H2BA), C3A(H3AA), C3B(H3BA), C5A(H5A),
 C5B(H5B), C7A(H7A), C7B(H7B)
3.e Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C10B(H10D,H10E,H10F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1A Cu 0.2258(2) 0.54379(14) 0.36514(12) 0.0291(6) Uani 1 1 d . . . . .
Cu1B Cu 0.8458(2) 0.69367(14) -0.12214(12) 0.0299(6) Uani 1 1 d . . . . .
S1A S 0.3390(4) 0.6900(3) 0.3376(2) 0.0310(9) Uani 1 1 d . . . . .
S1B S 0.8851(5) 0.8596(3) -0.1438(2) 0.0328(10) Uani 1 1 d . . . . .
S2A S 0.1363(4) 0.1715(3) 0.7409(2) 0.0290(9) Uani 1 1 d . . . . .
S2B S 0.5474(4) 0.3519(3) 0.2313(2) 0.0288(9) Uani 1 1 d . . . . .
O1A O 0.1325(10) 0.4190(6) 0.3913(5) 0.024(2) Uani 1 1 d . . . . .
O1B O 0.8380(11) 0.5509(6) -0.0961(6) 0.033(2) Uani 1 1 d . . . . .
O1WA O 0.1031(10) 0.5614(6) 0.2479(5) 0.025(2) Uani 1 1 d . . . . .
H1WA H 0.0672 0.6275 0.2375 0.038 Uiso 1 1 d R . . . .
H1WB H 0.0152 0.5291 0.2515 0.038 Uiso 1 1 d R . . . .
O1WB O 0.9766(11) 0.6537(7) -0.2384(6) 0.036(2) Uani 1 1 d . . . . .
H1WC H 0.9073 0.6550 -0.2855 0.055 Uiso 1 1 d R . . . .
H1WD H 1.0473 0.6970 -0.2509 0.055 Uiso 1 1 d R . . . .
O2A O 0.0328(11) 0.2443(6) 0.8051(5) 0.033(2) Uani 1 1 d . . . . .
O2B O 0.4560(11) 0.4340(6) 0.2883(5) 0.034(2) Uani 1 1 d . . . . .
O3A O 0.0567(11) 0.0822(6) 0.7186(6) 0.033(2) Uani 1 1 d . . . . .
O3B O 0.6987(10) 0.2957(6) 0.2808(5) 0.028(2) Uani 1 1 d . . . . .
O4A O 0.3121(10) 0.1420(6) 0.7771(5) 0.031(2) Uani 1 1 d . . . . .
O4B O 0.4405(11) 0.2793(6) 0.1957(6) 0.035(2) Uani 1 1 d . . . . .
N1A N 0.2788(13) 0.5607(8) 0.4970(7) 0.027(3) Uani 1 1 d . . . . .
N1B N 0.7481(13) 0.7342(8) 0.0006(7) 0.028(3) Uani 1 1 d . . . . .
N2A N 0.3310(13) 0.6527(8) 0.5196(7) 0.030(3) Uani 1 1 d . . . . .
H2A H 0.3481 0.6665 0.5787 0.036 Uiso 1 1 d R . . . .
N2B N 0.7328(13) 0.8386(8) 0.0222(7) 0.029(3) Uani 1 1 d . . . . .
H2B H 0.6837 0.8621 0.0755 0.034 Uiso 1 1 d R . . . .
N3A N 0.3913(13) 0.8111(9) 0.4793(7) 0.036(3) Uani 1 1 d . . . . .
H3A H 0.3889 0.8229 0.5402 0.043 Uiso 1 1 calc R . . . .
N3B N 0.7817(14) 1.0029(8) -0.0136(7) 0.033(3) Uani 1 1 d . . . . .
H3B H 0.7392 1.0196 0.0429 0.039 Uiso 1 1 calc R . . . .
C1A C 0.1470(16) 0.3610(10) 0.4687(9) 0.025(3) Uani 1 1 d . . . . .
C1B C 0.7731(17) 0.5077(10) -0.0215(8) 0.025(3) Uani 1 1 d . . . . .
C2A C 0.0926(17) 0.2638(10) 0.4697(9) 0.033(4) Uani 1 1 d . . . . .
H2AA H 0.0548 0.2378 0.4134 0.040 Uiso 1 1 calc R . . . .
C2B C 0.7783(16) 0.4007(10) -0.0167(8) 0.026(3) Uani 1 1 d . . . . .
H2BA H 0.8294 0.3599 -0.0677 0.031 Uiso 1 1 calc R . . . .
C3A C 0.0942(15) 0.2075(10) 0.5510(9) 0.025(3) Uani 1 1 d . . . . .
H3AA H 0.0555 0.1427 0.5506 0.030 Uiso 1 1 calc R . . . .
C3B C 0.7121(16) 0.3519(10) 0.0593(8) 0.029(3) Uani 1 1 d . . . . .
H3BA H 0.7189 0.2788 0.0606 0.035 Uiso 1 1 calc R . . . .
C4A C 0.1502(16) 0.2413(11) 0.6342(9) 0.028(3) Uani 1 1 d . . . . .
C4B C 0.6345(16) 0.4115(10) 0.1346(8) 0.026(3) Uani 1 1 d . . . . .
C5A C 0.2112(17) 0.3350(10) 0.6348(8) 0.029(3) Uani 1 1 d . . . . .
H5A H 0.2538 0.3577 0.6913 0.035 Uiso 1 1 calc R . . . .
C5B C 0.6280(17) 0.5159(11) 0.1326(8) 0.032(4) Uani 1 1 d . . . . .
H5B H 0.5734 0.5556 0.1833 0.038 Uiso 1 1 calc R . . . .
C6A C 0.2102(16) 0.3951(10) 0.5538(9) 0.026(3) Uani 1 1 d . U . . .
C6B C 0.7007(16) 0.5673(10) 0.0566(8) 0.024(3) Uani 1 1 d . . . . .
C7A C 0.2670(14) 0.4945(10) 0.5647(9) 0.023(3) Uani 1 1 d . . . . .
H7A H 0.2975 0.5119 0.6259 0.027 Uiso 1 1 calc R . . . .
C7B C 0.6952(17) 0.6755(10) 0.0646(9) 0.030(4) Uani 1 1 d . . . . .
H7B H 0.6490 0.7070 0.1214 0.036 Uiso 1 1 calc R . . . .
C8A C 0.3587(16) 0.7211(10) 0.4513(8) 0.025(3) Uani 1 1 d . . . . .
C8B C 0.7929(16) 0.9072(11) -0.0394(9) 0.032(4) Uani 1 1 d . . . . .
C9A C 0.4314(18) 0.8928(10) 0.4142(9) 0.037(4) Uani 1 1 d . . . . .
H9AA H 0.4741 0.8610 0.3537 0.044 Uiso 1 1 calc R . . . .
H9AB H 0.5234 0.9246 0.4410 0.044 Uiso 1 1 calc R . . . .
C9B C 0.8355(17) 1.0840(9) -0.0729(8) 0.028(3) Uani 1 1 d . U . . .
H9BA H 0.9235 1.0528 -0.1188 0.034 Uiso 1 1 calc R . . . .
H9BB H 0.8853 1.1322 -0.0333 0.034 Uiso 1 1 calc R . . . .
C10A C 0.283(2) 0.9761(11) 0.3954(10) 0.049(4) Uani 1 1 d . . . . .
H10A H 0.2339 1.0041 0.4553 0.073 Uiso 1 1 calc GR . . . .
H10B H 0.1977 0.9471 0.3610 0.073 Uiso 1 1 calc GR . . . .
H10C H 0.3212 1.0316 0.3575 0.073 Uiso 1 1 calc GR . . . .
C10B C 0.6878(18) 1.1425(11) -0.1246(9) 0.042(4) Uani 1 1 d . . . . .
H10D H 0.6039 1.1770 -0.0792 0.063 Uiso 1 1 calc GR . . . .
H10E H 0.6360 1.0944 -0.1620 0.063 Uiso 1 1 calc GR . . . .
H10F H 0.7269 1.1944 -0.1665 0.063 Uiso 1 1 calc GR . . . .
O1W O 0.5797(12) 1.0678(7) 0.1465(6) 0.045(3) Uani 1 1 d . . . . .
H1WE H 0.5711 1.1305 0.1674 0.067 Uiso 1 1 d R . . . .
H1WF H 0.6105 1.0238 0.1919 0.067 Uiso 1 1 d R . . . .
O2W O 0.2746(18) 0.9066(8) 0.6514(7) 0.077(4) Uani 1 1 d . . . . .
H2WA H 0.2664 0.8514 0.6849 0.115 Uiso 1 1 d G . . . .
H2WB H 0.2049 0.9589 0.6741 0.115 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1A S1A 2.275(4) . ?
Cu1A O1A 1.933(8) . ?
Cu1A O1WA 1.945(8) . ?
Cu1A O2B 2.396(9) . ?
Cu1A N1A 1.955(10) . ?
Cu1B S1B 2.262(4) . ?
Cu1B O1B 1.912(8) . ?
Cu1B O1WB 1.964(8) . ?
Cu1B O4B 16.466(8) 2_566 ?
Cu1B N1B 1.938(10) . ?
S1A C8A 1.689(12) . ?
S1B C8B 1.719(14) . ?
S2A O2A 1.469(8) . ?
S2A O3A 1.464(9) . ?
S2A O4A 1.498(9) . ?
S2A C4A 1.766(13) . ?
S2B O2B 1.445(9) . ?
S2B O3B 1.494(8) . ?
S2B O4B 1.483(9) . ?
S2B C4B 1.753(12) . ?
O1A C1A 1.321(14) . ?
O1B C1B 1.326(13) . ?
O1WA H1WA 0.8787 . ?
O1WA H1WB 0.8784 . ?
O1WB H1WC 0.8779 . ?
O1WB H1WD 0.8779 . ?
N1A N2A 1.386(13) . ?
N1A C7A 1.294(14) . ?
N1B N2B 1.392(14) . ?
N1B C7B 1.288(15) . ?
N2A H2A 0.8799 . ?
N2A C8A 1.347(15) . ?
N2B H2B 0.8799 . ?
N2B C8B 1.378(15) . ?
N3A H3A 0.8800 . ?
N3A C8A 1.318(15) . ?
N3A C9A 1.471(16) . ?
N3B H3B 0.8800 . ?
N3B C8B 1.302(16) . ?
N3B C9B 1.457(15) . ?
C1A C2A 1.412(17) . ?
C1A C6A 1.429(17) . ?
C1B C2B 1.396(16) . ?
C1B C6B 1.422(16) . ?
C2A H2AA 0.9500 . ?
C2A C3A 1.359(16) . ?
C2B H2BA 0.9500 . ?
C2B C3B 1.383(17) . ?
C3A H3AA 0.9500 . ?
C3A C4A 1.380(17) . ?
C3B H3BA 0.9500 . ?
C3B C4B 1.406(17) . ?
C4A C5A 1.394(17) . ?
C4B C5B 1.360(17) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.380(16) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.424(16) . ?
C6A C7A 1.461(17) . ?
C6B C7B 1.418(17) . ?
C7A H7A 0.9500 . ?
C7B H7B 0.9500 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.501(19) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.500(17) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
O1W H1WE 0.8698 . ?
O1W H1WF 0.8699 . ?
O2W H2WA 0.8701 . ?
O2W H2WB 0.8701 . ?

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
S1A Cu1A O2B 93.9(2) . . ?
O1A Cu1A S1A 178.6(3) . . ?
O1A Cu1A O1WA 89.3(3) . . ?
O1A Cu1A O2B 86.1(3) . . ?
O1A Cu1A N1A 93.2(4) . . ?
O1WA Cu1A S1A 92.1(2) . . ?
O1WA Cu1A O2B 90.4(3) . . ?
O1WA Cu1A N1A 159.7(4) . . ?
N1A Cu1A S1A 85.5(3) . . ?
N1A Cu1A O2B 109.8(4) . . ?
S1B Cu1B O4B 104.71(10) . 2_566 ?
O1B Cu1B S1B 173.1(3) . . ?
O1B Cu1B O1WB 89.2(3) . . ?
O1B Cu1B O4B 76.3(2) . 2_566 ?
O1B Cu1B N1B 92.1(4) . . ?
O1WB Cu1B S1B 90.5(3) . . ?
O1WB Cu1B O4B 163.9(2) . 2_566 ?
N1B Cu1B S1B 87.3(3) . . ?
N1B Cu1B O1WB 171.7(4) . . ?
N1B Cu1B O4B 21.8(3) . 2_566 ?
C8A S1A Cu1A 97.4(5) . . ?
C8B S1B Cu1B 97.6(5) . . ?
O2A S2A O4A 110.4(5) . . ?
O2A S2A C4A 105.3(6) . . ?
O3A S2A O2A 113.3(5) . . ?
O3A S2A O4A 113.2(5) . . ?
O3A S2A C4A 106.4(6) . . ?
O4A S2A C4A 107.8(5) . . ?
O2B S2B O3B 111.5(5) . . ?
O2B S2B O4B 114.1(5) . . ?
O2B S2B C4B 106.6(5) . . ?
O3B S2B C4B 103.8(5) . . ?
O4B S2B O3B 111.5(5) . . ?
O4B S2B C4B 108.5(6) . . ?
C1A O1A Cu1A 127.9(8) . . ?
C1B O1B Cu1B 129.2(8) . . ?
Cu1A O1WA H1WA 109.3 . . ?
Cu1A O1WA H1WB 110.2 . . ?
H1WA O1WA H1WB 108.8 . . ?
Cu1B O1WB H1WC 109.5 . . ?
Cu1B O1WB H1WD 110.1 . . ?
H1WC O1WB H1WD 108.8 . . ?
S2B O2B Cu1A 160.5(5) . . ?
N2A N1A Cu1A 116.5(8) . . ?
C7A N1A Cu1A 125.9(9) . . ?
C7A N1A N2A 117.6(10) . . ?
N2B N1B Cu1B 116.5(8) . . ?
C7B N1B Cu1B 127.3(9) . . ?
C7B N1B N2B 116.1(10) . . ?
N1A N2A H2A 120.1 . . ?
C8A N2A N1A 120.4(10) . . ?
C8A N2A H2A 119.5 . . ?
N1B N2B H2B 120.5 . . ?
C8B N2B N1B 120.8(10) . . ?
C8B N2B H2B 118.7 . . ?
C8A N3A H3A 118.2 . . ?
C8A N3A C9A 123.6(11) . . ?
C9A N3A H3A 118.2 . . ?
C8B N3B H3B 118.1 . . ?
C8B N3B C9B 123.7(11) . . ?
C9B N3B H3B 118.1 . . ?
O1A C1A C2A 119.7(11) . . ?
O1A C1A C6A 122.1(11) . . ?
C2A C1A C6A 118.1(11) . . ?
O1B C1B C2B 120.2(11) . . ?
O1B C1B C6B 121.8(11) . . ?
C2B C1B C6B 118.0(11) . . ?
C1A C2A H2AA 119.9 . . ?
C3A C2A C1A 120.1(12) . . ?
C3A C2A H2AA 119.9 . . ?
C1B C2B H2BA 118.8 . . ?
C3B C2B C1B 122.5(11) . . ?
C3B C2B H2BA 118.8 . . ?
C2A C3A H3AA 119.0 . . ?
C2A C3A C4A 122.0(12) . . ?
C4A C3A H3AA 119.0 . . ?
C2B C3B H3BA 120.4 . . ?
C2B C3B C4B 119.3(12) . . ?
C4B C3B H3BA 120.4 . . ?
C3A C4A S2A 121.2(11) . . ?
C3A C4A C5A 119.3(11) . . ?
C5A C4A S2A 119.4(10) . . ?
C3B C4B S2B 120.3(10) . . ?
C5B C4B S2B 119.9(9) . . ?
C5B C4B C3B 119.8(11) . . ?
C4A C5A H5A 119.8 . . ?
C6A C5A C4A 120.4(12) . . ?
C6A C5A H5A 119.8 . . ?
C4B C5B H5B 119.1 . . ?
C4B C5B C6B 121.8(12) . . ?
C6B C5B H5B 119.1 . . ?
C1A C6A C7A 124.6(11) . . ?
C5A C6A C1A 119.9(12) . . ?
C5A C6A C7A 115.4(11) . . ?
C1B C6B C5B 118.5(12) . . ?
C7B C6B C1B 124.6(11) . . ?
C7B C6B C5B 116.9(12) . . ?
N1A C7A C6A 124.7(11) . . ?
N1A C7A H7A 117.6 . . ?
C6A C7A H7A 117.6 . . ?
N1B C7B C6B 124.8(12) . . ?
N1B C7B H7B 117.6 . . ?
C6B C7B H7B 117.6 . . ?
N2A C8A S1A 119.0(10) . . ?
N3A C8A S1A 124.4(10) . . ?
N3A C8A N2A 116.5(11) . . ?
N2B C8B S1B 117.7(10) . . ?
N3B C8B S1B 124.2(10) . . ?
N3B C8B N2B 118.0(12) . . ?
N3A C9A H9AA 108.8 . . ?
N3A C9A H9AB 108.8 . . ?
N3A C9A C10A 113.7(11) . . ?
H9AA C9A H9AB 107.7 . . ?
C10A C9A H9AA 108.8 . . ?
C10A C9A H9AB 108.8 . . ?
N3B C9B H9BA 109.6 . . ?
N3B C9B H9BB 109.6 . . ?
N3B C9B C10B 110.5(11) . . ?
H9BA C9B H9BB 108.1 . . ?
C10B C9B H9BA 109.6 . . ?
C10B C9B H9BB 109.6 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
H1WE O1W H1WF 109.5 . . ?
H2WA O2W H2WB 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1WA H1WA O2A 0.88 1.84 2.702(11) 167.5 2_566
O1WA H1WB O1WB 0.88 2.40 2.995(11) 125.9 2_665
O1WB H1WC O1A 0.88 1.86 2.612(11) 142.0 2_665
O1WB H1WD O3B 0.88 2.08 2.832(11) 142.8 2_765
N2A H2A O3B 0.88 2.07 2.919(13) 160.9 2_666
N3A H3A O2W 0.88 2.05 2.832(15) 147.9 .
N3B H3B O1W 0.88 1.97 2.816(13) 162.1 .
O1W H1WE O4B 0.87 2.10 2.903(12) 153.9 1_565
O2W H2WB O3A 0.87 1.95 2.815(14) 175.8 1_565

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1A S1A C8A N2A 9.0(11) . . . . ?
Cu1A S1A C8A N3A -167.3(11) . . . . ?
Cu1A O1A C1A C2A -170.1(9) . . . . ?
Cu1A O1A C1A C6A 12.4(16) . . . . ?
Cu1A N1A N2A C8A -6.3(14) . . . . ?
Cu1A N1A C7A C6A -0.4(17) . . . . ?
Cu1B S1B C8B N2B 1.8(10) . . . . ?
Cu1B S1B C8B N3B 179.3(11) . . . . ?
Cu1B O1B C1B C2B 179.1(9) . . . . ?
Cu1B O1B C1B C6B -2.6(18) . . . . ?
Cu1B N1B N2B C8B -3.3(14) . . . . ?
Cu1B N1B C7B C6B 0.6(19) . . . . ?
S2A C4A C5A C6A -174.7(10) . . . . ?
S2B C4B C5B C6B 178.4(10) . . . . ?
O1A C1A C2A C3A -174.6(11) . . . . ?
O1A C1A C6A C5A 175.2(11) . . . . ?
O1A C1A C6A C7A -0.9(19) . . . . ?
O1B C1B C2B C3B -179.8(11) . . . . ?
O1B C1B C6B C5B 177.7(11) . . . . ?
O1B C1B C6B C7B -2(2) . . . . ?
O2A S2A C4A C3A -121.5(11) . . . . ?
O2A S2A C4A C5A 55.3(12) . . . . ?
O2B S2B C4B C3B -171.4(10) . . . . ?
O2B S2B C4B C5B 9.0(13) . . . . ?
O3A S2A C4A C3A -1.1(12) . . . . ?
O3A S2A C4A C5A 175.8(10) . . . . ?
O3B S2B O2B Cu1A -134.0(14) . . . . ?
O3B S2B C4B C3B 70.7(12) . . . . ?
O3B S2B C4B C5B -108.9(11) . . . . ?
O4A S2A C4A C3A 120.6(11) . . . . ?
O4A S2A C4A C5A -62.5(12) . . . . ?
O4B S2B O2B Cu1A -6.5(17) . . . . ?
O4B S2B C4B C3B -48.0(12) . . . . ?
O4B S2B C4B C5B 132.4(11) . . . . ?
N1A N2A C8A S1A -3.3(16) . . . . ?
N1A N2A C8A N3A 173.3(11) . . . . ?
N1B N2B C8B S1B 0.6(16) . . . . ?
N1B N2B C8B N3B -177.0(11) . . . . ?
N2A N1A C7A C6A 178.5(11) . . . . ?
N2B N1B C7B C6B -179.6(11) . . . . ?
C1A C2A C3A C4A -1(2) . . . . ?
C1A C6A C7A N1A -5(2) . . . . ?
C1B C2B C3B C4B 0.7(19) . . . . ?
C1B C6B C7B N1B 3(2) . . . . ?
C2A C1A C6A C5A -2.3(19) . . . . ?
C2A C1A C6A C7A -178.4(11) . . . . ?
C2A C3A C4A S2A 175.2(10) . . . . ?
C2A C3A C4A C5A -1.7(19) . . . . ?
C2B C1B C6B C5B -3.9(18) . . . . ?
C2B C1B C6B C7B 176.2(12) . . . . ?
C2B C3B C4B S2B 179.3(10) . . . . ?
C2B C3B C4B C5B -1.1(19) . . . . ?
C3A C4A C5A C6A 2.2(19) . . . . ?
C3B C4B C5B C6B -1(2) . . . . ?
C4A C5A C6A C1A -0.3(19) . . . . ?
C4A C5A C6A C7A 176.2(11) . . . . ?
C4B S2B O2B Cu1A 113.3(15) . . . . ?
C4B C5B C6B C1B 3.7(19) . . . . ?
C4B C5B C6B C7B -176.4(12) . . . . ?
C5A C6A C7A N1A 178.4(12) . . . . ?
C5B C6B C7B N1B -176.7(12) . . . . ?
C6A C1A C2A C3A 2.9(19) . . . . ?
C6B C1B C2B C3B 1.8(19) . . . . ?
C7A N1A N2A C8A 174.7(11) . . . . ?
C7B N1B N2B C8B 176.9(12) . . . . ?
C8A N3A C9A C10A 99.0(15) . . . . ?
C8B N3B C9B C10B 95.4(15) . . . . ?
C9A N3A C8A S1A -6.2(19) . . . . ?
C9A N3A C8A N2A 177.4(11) . . . . ?
C9B N3B C8B S1B 4.5(19) . . . . ?
C9B N3B C8B N2B -178.0(11) . . . . ?

_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_shi_3118_olpa

_database_code_depnum_ccdc_archive 'CCDC 1497277'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2017-03-07 downloaded from the CCDC.
;
_audit_creation_date             2017-02-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C12.22 H18.65 Cu N3 O5.61 S3.61, C0.78 H2.57 O0.39 S0.39, 0.15(H2 O)'
_chemical_formula_sum            'C13 H21.30 Cu N3 O6.15 S4'
_chemical_formula_weight         509.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N4 O4 S1 Cu1'
_chemical_oxdiff_usercomment     SA_24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6632(4)
_cell_length_b                   11.5805(6)
_cell_length_c                   12.2566(8)
_cell_angle_alpha                86.844(5)
_cell_angle_beta                 72.387(6)
_cell_angle_gamma                79.287(5)
_cell_volume                     1018.63(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4032
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      28.6990
_cell_measurement_theta_min      1.9290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             525
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7072
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.790
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00   3.00   1.00    5.00    --  -15.76 -77.00  30.00   26
  2  ω    -47.00  44.00   1.00    5.00    --   18.10 -77.00 150.00   91
  3  ω      1.00  81.00   1.00    5.00    --   18.10  57.00 -90.00   80
  4  ω    -62.00 -33.00   1.00    5.00    --  -15.44 178.00 -30.00   29
  5  ω     -4.00  22.00   1.00    5.00    --  -15.44 -99.00  30.00   26
  6  ω    -33.00  35.00   1.00    5.00    --   17.79 -57.00   0.00   68
  7  ω     24.00  74.00   1.00    5.00    --   17.79  57.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0340421000
_diffrn_orient_matrix_UB_12      0.0066807000
_diffrn_orient_matrix_UB_13      0.0603564000
_diffrn_orient_matrix_UB_21      -0.0385945000
_diffrn_orient_matrix_UB_22      0.0595945000
_diffrn_orient_matrix_UB_23      -0.0066976000
_diffrn_orient_matrix_UB_31      -0.0842053000
_diffrn_orient_matrix_UB_32      -0.0170163000
_diffrn_orient_matrix_UB_33      -0.0001146000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3180
_reflns_number_total             3601
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+0.8801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0839
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 S4-C13 \\sim S4X-C13X \\sim S4-C12 \\sim S4X-C12X
 with sigma of 0.01
 S4-O6X \\sim S4X-O6
 with sigma of 0.01
 S4-O6 \\sim S4X-O6X
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C12) = Uanis(C13) = Uanis(C13X) = Uanis(C12X)
Uanis(O6X) = Uanis(O6)
Uanis(S4X) = Uanis(S4)
4. Others
 Sof(S4X)=Sof(O6X)=Sof(C12X)=Sof(H12E)=Sof(H12F)=Sof(C13X)=Sof(H13D)=Sof(H13E)=
 Sof(H13F)=1-FVAR(1)
 Sof(S4)=Sof(O6)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C13)=Sof(H13A)=
 Sof(H13B)=Sof(H13C)=Sof(H12D)=FVAR(1)
 Fixed Sof: O1W(0.15) H1WA(0.15) H1WB(0.15)
5.a Riding coordinates:
 O1W(H1WA,H1WB)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C2(H2A), C3(H3A), C5(H5), C7(H7)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C13(H13A,H13B,H13C), C12X(H12D,H12E,H12F), C13X(H13D,H13E,H13F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.57917(5) 0.40245(3) 0.69823(3) 0.02267(12) Uani 1 1 d . . . . .
S1 S 0.81857(11) 0.38344(7) 0.77249(8) 0.0309(2) Uani 1 1 d . . . . .
S2 S 0.23400(10) 0.11581(6) 0.31382(7) 0.02257(19) Uani 1 1 d . . . . .
S3 S 0.30725(10) 0.63473(6) 0.74994(7) 0.02344(19) Uani 1 1 d . . . . .
S4 S 0.2913(2) 0.25838(13) 0.95690(13) 0.0306(3) Uani 0.6079(16) 1 d D . P A 1
O1 O 0.4040(3) 0.42936(17) 0.61610(19) 0.0284(5) Uani 1 1 d . . . . .
O2 O 0.1016(3) 0.0522(2) 0.3919(2) 0.0402(6) Uani 1 1 d . . . . .
O3 O 0.1570(4) 0.1889(2) 0.2357(2) 0.0526(7) Uani 1 1 d . . . . .
O4 O 0.4056(3) 0.0378(2) 0.2582(2) 0.0491(7) Uani 1 1 d . . . . .
O5 O 0.4649(3) 0.55137(17) 0.78232(19) 0.0249(5) Uani 1 1 d . . . . .
O6 O 0.3166(5) 0.2946(3) 0.8328(3) 0.0337(8) Uani 0.6079(16) 1 d D . P A 1
N1 N 0.6964(3) 0.2500(2) 0.6261(2) 0.0199(5) Uani 1 1 d . . . . .
N2 N 0.8509(3) 0.1903(2) 0.6545(2) 0.0223(6) Uani 1 1 d . . . . .
H2 H 0.9009 0.1201 0.6299 0.027 Uiso 1 1 calc R . . . .
N3 N 1.0692(4) 0.1897(2) 0.7474(2) 0.0323(7) Uani 1 1 d . . . . .
H3 H 1.1123 0.2260 0.7901 0.039 Uiso 1 1 calc R . . . .
C1 C 0.3743(4) 0.3580(2) 0.5482(3) 0.0210(7) Uani 1 1 d . . . . .
C2 C 0.2268(4) 0.3940(3) 0.5005(3) 0.0282(8) Uani 1 1 d . . . . .
H2A H 0.1551 0.4685 0.5178 0.034 Uiso 1 1 calc R . . . .
C3 C 0.1858(4) 0.3227(3) 0.4296(3) 0.0258(7) Uani 1 1 d . . . . .
H3A H 0.0872 0.3493 0.4000 0.031 Uiso 1 1 calc R . . . .
C4 C 0.2910(4) 0.2106(2) 0.4014(2) 0.0193(6) Uani 1 1 d . . . . .
C5 C 0.4385(4) 0.1734(2) 0.4437(3) 0.0205(7) Uani 1 1 d . . . . .
H5 H 0.5108 0.0996 0.4230 0.025 Uiso 1 1 calc R . . . .
C6 C 0.4833(4) 0.2443(2) 0.5178(3) 0.0190(6) Uani 1 1 d . . . . .
C7 C 0.6411(4) 0.1974(2) 0.5559(3) 0.0207(7) Uani 1 1 d . . . . .
H7 H 0.7084 0.1241 0.5282 0.025 Uiso 1 1 calc R . . . .
C8 C 0.9208(4) 0.2445(3) 0.7213(3) 0.0237(7) Uani 1 1 d . . . . .
C9 C 1.1656(5) 0.0720(3) 0.7089(3) 0.0361(9) Uani 1 1 d . . . . .
H9A H 1.1923 0.0670 0.6274 0.054 Uiso 1 1 calc GR . . . .
H9B H 1.0883 0.0160 0.7454 0.054 Uiso 1 1 calc GR . . . .
H9C H 1.2798 0.0552 0.7286 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.1037(4) 0.5769(3) 0.8195(3) 0.0351(9) Uani 1 1 d . . . . .
H10A H 0.1148 0.5000 0.7898 0.053 Uiso 1 1 calc GR . . . .
H10B H -0.0022 0.6276 0.8062 0.053 Uiso 1 1 calc GR . . . .
H10C H 0.0880 0.5718 0.9002 0.053 Uiso 1 1 calc GR . . . .
C11 C 0.2627(5) 0.7582(3) 0.8406(3) 0.0359(9) Uani 1 1 d . . . . .
H11A H 0.2412 0.7324 0.9186 0.054 Uiso 1 1 calc GR . . . .
H11B H 0.1549 0.8115 0.8333 0.054 Uiso 1 1 calc GR . . . .
H11C H 0.3681 0.7974 0.8188 0.054 Uiso 1 1 calc GR . . . .
C12 C 0.5108(7) 0.1558(5) 0.9454(7) 0.0339(10) Uani 0.6079(16) 1 d D . P A 1
H12A H 0.5242 0.0936 0.8933 0.051 Uiso 0.6079(16) 1 calc GR . P A 1
H12B H 0.5091 0.1233 1.0194 0.051 Uiso 0.6079(16) 1 calc GR . P A 1
H12C H 0.6133 0.1971 0.9176 0.051 Uiso 0.6079(16) 1 calc GR . P A 1
C13 C 0.363(3) 0.3738(13) 1.0180(14) 0.0339(10) Uani 0.6079(16) 1 d D . P A 1
H13A H 0.2774 0.4460 1.0193 0.051 Uiso 0.6079(16) 1 calc GR . P A 1
H13B H 0.4855 0.3837 0.9725 0.051 Uiso 0.6079(16) 1 calc GR . P A 1
H13C H 0.3643 0.3528 1.0947 0.051 Uiso 0.6079(16) 1 calc GR . P A 1
S4X S 0.3734(3) 0.2827(2) 0.9042(2) 0.0306(3) Uani 0.3921(16) 1 d D . P A 2
O6X O 0.1767(7) 0.2632(5) 0.9265(5) 0.0337(8) Uani 0.3921(16) 1 d D . P A 2
C12X C 0.4532(13) 0.1410(7) 0.9619(11) 0.0339(10) Uani 0.3921(16) 1 d D . P A 2
H12D H 0.5866 0.1267 0.9421 0.051 Uiso 0.6079(16) 1 calc GR . P A 2
H12E H 0.4138 0.0800 0.9302 0.051 Uiso 0.3921(16) 1 calc GR . P A 2
H12F H 0.4013 0.1417 1.0437 0.051 Uiso 0.3921(16) 1 calc GR . P A 2
C13X C 0.362(6) 0.367(2) 1.027(2) 0.0339(10) Uani 0.3921(16) 1 d D . P A 2
H13D H 0.3322 0.3197 1.0951 0.051 Uiso 0.3921(16) 1 calc GR . P A 2
H13E H 0.2683 0.4359 1.0351 0.051 Uiso 0.3921(16) 1 calc GR . P A 2
H13F H 0.4807 0.3894 1.0171 0.051 Uiso 0.3921(16) 1 calc GR . P A 2
O1W O 0.132(2) 0.0358(15) 1.0487(15) 0.051(5) Uiso 0.15 1 d . . P . .
H1WA H 0.1060 -0.0095 1.0059 0.076 Uiso 0.15 1 d R . P . .
H1WB H 0.1921 0.0855 1.0077 0.076 Uiso 0.15 1 d R . P . .


_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 S1 2.2541(9) . ?
Cu1 O1 1.882(2) . ?
Cu1 O5 1.9726(19) . ?
Cu1 O6 2.650(4) . ?
Cu1 N1 1.951(2) . ?
S1 C8 1.715(3) . ?
S2 O2 1.449(2) . ?
S2 O3 1.431(3) . ?
S2 O4 1.447(2) . ?
S2 C4 1.772(3) . ?
S3 O5 1.538(2) . ?
S3 C10 1.769(3) . ?
S3 C11 1.777(3) . ?
S4 O6 1.520(4) . ?
S4 C12 1.842(5) . ?
S4 C13 1.812(8) . ?
O1 C1 1.299(3) . ?
N1 N2 1.386(3) . ?
N1 C7 1.291(4) . ?
N2 H2 0.8600 . ?
N2 C8 1.340(4) . ?
N3 H3 0.8600 . ?
N3 C8 1.314(4) . ?
N3 C9 1.453(4) . ?
C1 C2 1.411(4) . ?
C1 C6 1.424(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.369(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.396(4) . ?
C4 C5 1.371(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.412(4) . ?
C6 C7 1.430(4) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
S4X O6X 1.506(5) . ?
S4X C12X 1.824(7) . ?
S4X C13X 1.813(8) . ?
C12X H12D 0.9600 . ?
C12X H12E 0.9600 . ?
C12X H12F 0.9600 . ?
C13X H13D 0.9600 . ?
C13X H13E 0.9600 . ?
C13X H13F 0.9600 . ?
O1W H1WA 0.8494 . ?
O1W H1WB 0.8505 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 Cu1 O6 109.36(9) . . ?
O1 Cu1 S1 170.84(7) . . ?
O1 Cu1 O5 90.55(8) . . ?
O1 Cu1 O6 79.75(11) . . ?
O1 Cu1 N1 93.21(9) . . ?
O5 Cu1 S1 90.24(6) . . ?
O5 Cu1 O6 91.24(10) . . ?
N1 Cu1 S1 86.45(7) . . ?
N1 Cu1 O5 175.44(10) . . ?
N1 Cu1 O6 86.91(10) . . ?
C8 S1 Cu1 96.44(11) . . ?
O2 S2 C4 105.35(14) . . ?
O3 S2 O2 113.08(17) . . ?
O3 S2 O4 113.51(17) . . ?
O3 S2 C4 106.83(15) . . ?
O4 S2 O2 111.26(15) . . ?
O4 S2 C4 106.11(14) . . ?
O5 S3 C10 105.05(14) . . ?
O5 S3 C11 103.36(15) . . ?
C10 S3 C11 97.99(16) . . ?
O6 S4 C12 101.5(3) . . ?
O6 S4 C13 104.4(6) . . ?
C13 S4 C12 93.0(8) . . ?
C1 O1 Cu1 128.37(19) . . ?
S3 O5 Cu1 119.96(13) . . ?
S4 O6 Cu1 127.6(2) . . ?
N2 N1 Cu1 117.56(18) . . ?
C7 N1 Cu1 126.2(2) . . ?
C7 N1 N2 116.3(2) . . ?
N1 N2 H2 120.8 . . ?
C8 N2 N1 118.4(2) . . ?
C8 N2 H2 120.8 . . ?
C8 N3 H3 117.8 . . ?
C8 N3 C9 124.5(3) . . ?
C9 N3 H3 117.8 . . ?
O1 C1 C2 119.0(3) . . ?
O1 C1 C6 123.8(3) . . ?
C2 C1 C6 117.2(3) . . ?
C1 C2 H2A 118.9 . . ?
C3 C2 C1 122.1(3) . . ?
C3 C2 H2A 118.9 . . ?
C2 C3 H3A 119.7 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 S2 120.8(2) . . ?
C5 C4 S2 120.0(2) . . ?
C5 C4 C3 119.2(3) . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 123.7(3) . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 117.0(3) . . ?
N1 C7 C6 124.4(3) . . ?
N1 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
N2 C8 S1 120.7(2) . . ?
N3 C8 S1 120.1(2) . . ?
N3 C8 N2 119.1(3) . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S3 C10 H10A 109.5 . . ?
S3 C10 H10B 109.5 . . ?
S3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S3 C11 H11A 109.5 . . ?
S3 C11 H11B 109.5 . . ?
S3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S4 C12 H12A 109.5 . . ?
S4 C12 H12B 109.5 . . ?
S4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S4 C13 H13A 109.5 . . ?
S4 C13 H13B 109.5 . . ?
S4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6X S4X C12X 94.8(4) . . ?
O6X S4X C13X 103.7(13) . . ?
C13X S4X C12X 94.9(10) . . ?
S4X C12X H12D 109.5 . . ?
S4X C12X H12E 109.5 . . ?
S4X C12X H12F 109.5 . . ?
H12D C12X H12E 109.5 . . ?
H12D C12X H12F 109.5 . . ?
H12E C12X H12F 109.5 . . ?
S4X C13X H13D 109.5 . . ?
S4X C13X H13E 109.5 . . ?
S4X C13X H13F 109.5 . . ?
H13D C13X H13E 109.5 . . ?
H13D C13X H13F 109.5 . . ?
H13E C13X H13F 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.86 2.03 2.831(3) 154.1 2_656
N3 H3 O6 0.86 2.09 2.892(5) 155.2 1_655

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 S1 C8 N2 3.0(3) . . . . ?
Cu1 S1 C8 N3 -177.0(3) . . . . ?
Cu1 O1 C1 C2 176.1(2) . . . . ?
Cu1 O1 C1 C6 -4.3(4) . . . . ?
Cu1 N1 N2 C8 -5.8(3) . . . . ?
Cu1 N1 C7 C6 0.9(4) . . . . ?
S2 C4 C5 C6 -177.2(2) . . . . ?
O1 C1 C2 C3 -179.1(3) . . . . ?
O1 C1 C6 C5 179.7(3) . . . . ?
O1 C1 C6 C7 -1.9(5) . . . . ?
O2 S2 C4 C3 -88.4(3) . . . . ?
O2 S2 C4 C5 90.7(3) . . . . ?
O3 S2 C4 C3 32.1(3) . . . . ?
O3 S2 C4 C5 -148.8(3) . . . . ?
O4 S2 C4 C3 153.5(3) . . . . ?
O4 S2 C4 C5 -27.4(3) . . . . ?
O5 Cu1 O1 C1 -170.9(2) . . . . ?
O6 Cu1 O1 C1 -79.7(3) . . . . ?
N1 Cu1 O1 C1 6.6(3) . . . . ?
N1 N2 C8 S1 1.2(4) . . . . ?
N1 N2 C8 N3 -178.8(3) . . . . ?
N2 N1 C7 C6 179.2(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C6 C7 N1 3.6(5) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C7 177.7(3) . . . . ?
C2 C3 C4 S2 177.8(2) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C3 C4 C5 C6 1.9(4) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
C5 C6 C7 N1 -178.0(3) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
C7 N1 N2 C8 175.8(3) . . . . ?
C9 N3 C8 S1 179.7(3) . . . . ?
C9 N3 C8 N2 -0.3(5) . . . . ?
C10 S3 O5 Cu1 81.65(18) . . . . ?
C11 S3 O5 Cu1 -176.12(15) . . . . ?
C12 S4 O6 Cu1 -60.9(3) . . . . ?
C13 S4 O6 Cu1 35.2(8) . . . . ?
_olex2_date_sample_data_collection 2016-02-17
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.785
