# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_ls40_0ma
_database_code_depnum_ccdc_archive 'CCDC 1577585'
_audit_update_record             
;
2018-10-31 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_audit_creation_date             2017-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H10 Cl2 Cu N5 O2 S, C2 H Cl2 O2'
_chemical_formula_sum            'C10 H11 Cl4 Cu N5 O4 S'
_chemical_formula_weight         502.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.8439(9)
_cell_length_b                   11.9326(9)
_cell_length_c                   11.6222(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.322(3)
_cell_angle_gamma                90.00
_cell_volume                     1800.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      51.91
_cell_measurement_theta_min      3.12
_exptl_absorpt_coefficient_mu    1.949
_exptl_absorpt_correction_T_max  0.8597
_exptl_absorpt_correction_T_min  0.7586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_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    1.854
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35405
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.32
_diffrn_ambient_temperature      119.91
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3186
_reflns_number_total             3672
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3672
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0255P)²+0.8917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0560
_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 C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl3-C10 \\sim Cl4-C10 \\sim Cl4X-C10
 with sigma of 0.01
3. Others
 Fixed Sof: H10A(0.5) H10(0.5) Cl4(0.5) Cl4X(0.5)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10A), C10(H10)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), N2(H2), N4(H4)
4.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
4.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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
C1 C 0.76035(14) 0.12102(16) 0.28513(17) 0.0127(4) Uani 1 d . . .
C2 C 0.66597(15) 0.10348(15) 0.39904(16) 0.0117(4) Uani 1 d . . .
C3 C 0.82603(15) 0.12255(17) 0.40293(17) 0.0154(4) Uani 1 d . . .
H3 H 0.8989 0.1297 0.4305 0.019 Uiso 1 calc . . R
C4 C 0.57888(15) 0.08680(17) 0.44423(17) 0.0152(4) Uani 1 d . . .
H4A H 0.5142 0.0826 0.3742 0.023 Uiso 1 calc . . GR
H4B H 0.5759 0.1498 0.4970 0.023 Uiso 1 calc . . GR
H4C H 0.5891 0.0169 0.4913 0.023 Uiso 1 calc . . GR
C5 C 0.77324(15) 0.12455(16) 0.16729(17) 0.0134(4) Uani 1 d . . .
H5 H 0.8384 0.1325 0.1580 0.016 Uiso 1 calc . . R
C6 C 0.59665(14) 0.11734(15) -0.13224(16) 0.0104(4) Uani 1 d . . .
C7 C 0.38127(14) 0.22421(16) 0.10586(15) 0.0115(4) Uani 1 d . . .
C8 C 0.26800(14) 0.21282(17) 0.09538(18) 0.0159(4) Uani 1 d . . .
H8 H 0.2626 0.1569 0.1569 0.019 Uiso 1 calc . . R
Cl1 Cl 0.20127(4) 0.16140(5) -0.05505(5) 0.02948(14) Uani 1 d . . .
Cl2 Cl 0.21445(4) 0.34138(5) 0.11864(5) 0.02757(13) Uani 1 d . . .
Cu1 Cu 0.557833(16) 0.109664(19) 0.109866(19) 0.01015(7) Uani 1 d . . .
N1 N 0.65941(12) 0.10996(13) 0.28322(13) 0.0107(3) Uani 1 d . . .
N2 N 0.76568(12) 0.11171(14) 0.47401(14) 0.0141(3) Uani 1 d . . .
H2 H 0.7879 0.1103 0.5547 0.017 Uiso 1 calc . . R
N3 N 0.68811(12) 0.11588(13) 0.07578(13) 0.0110(3) Uani 1 d . . .
N4 N 0.68825(12) 0.11626(13) -0.04176(13) 0.0120(3) Uani 1 d . . .
H4 H 0.7461 0.1158 -0.0572 0.014 Uiso 1 calc . . R
N5 N 0.59636(12) 0.11624(13) -0.24592(13) 0.0125(3) Uani 1 d . . .
H5A H 0.6550 0.1148 -0.2597 0.015 Uiso 1 calc . . R
H5B H 0.5376 0.1169 -0.3079 0.015 Uiso 1 calc . . R
O1 O 0.43042(10) 0.13241(11) 0.13937(11) 0.0134(3) Uani 1 d . . .
O2 O 0.41340(10) 0.31247(11) 0.07824(11) 0.0141(3) Uani 1 d . . .
S1 S 0.48277(4) 0.12298(4) -0.10169(4) 0.01125(11) Uani 1 d . . .
C9 C 0.86419(14) 0.07317(16) -0.18070(16) 0.0128(4) Uani 1 d B . .
C10 C 0.96184(14) 0.01723(16) -0.18804(17) 0.0132(4) Uani 1 d . . D
H10A H 1.0182 0.0194 -0.1061 0.016 Uiso 0.50 calc A 2 R
H10 H 1.0179 0.0272 -0.1067 0.016 Uiso 0.50 calc A 1 R
Cl3 Cl 1.00384(4) 0.07954(5) -0.30111(4) 0.02206(12) Uani 1 d B . D
Cl4 Cl 0.9291(8) -0.1240(5) -0.2348(13) 0.036(2) Uani 0.50 d B 2 D
Cl4X Cl 0.9385(8) -0.1288(5) -0.2120(13) 0.0292(12) Uani 0.50 d B 1 D
O3 O 0.86359(10) 0.07943(14) -0.07341(12) 0.0232(3) Uani 1 d . . .
O4 O 0.79481(10) 0.10374(12) -0.27677(11) 0.0175(3) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.355(3) . ?
C1 C5 1.442(2) . ?
C1 N1 1.396(2) . ?
C2 C4 1.486(2) . ?
C2 N1 1.320(2) . ?
C2 N2 1.356(3) . ?
C3 H3 0.9500 . ?
C3 N2 1.370(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5 0.9500 . ?
C5 N3 1.288(2) . ?
C6 N4 1.337(2) . ?
C6 N5 1.320(2) . ?
C6 S1 1.7335(18) . ?
C7 C8 1.536(2) . ?
C7 O1 1.277(2) . ?
C7 O2 1.229(2) . ?
C8 H8 1.0000 . ?
C8 Cl1 1.779(2) . ?
C8 Cl2 1.765(2) . ?
Cu1 N1 2.0171(15) . ?
Cu1 N3 1.9778(15) . ?
Cu1 O1 1.9294(12) . ?
Cu1 S1 2.3186(5) . ?
N2 H2 0.8800 . ?
N3 N4 1.367(2) . ?
N4 H4 0.8800 . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C9 C10 1.536(3) . ?
C9 O3 1.252(2) . ?
C9 O4 1.248(2) . ?
C10 H10A 1.0000 . ?
C10 H10 1.0000 . ?
C10 Cl3 1.7745(17) . ?
C10 Cl4 1.780(5) . ?
C10 Cl4X 1.776(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C5 134.27(18) . . ?
C3 C1 N1 109.52(16) . . ?
N1 C1 C5 116.17(16) . . ?
N1 C2 C4 126.26(17) . . ?
N1 C2 N2 110.20(16) . . ?
N2 C2 C4 123.52(16) . . ?
C1 C3 H3 127.1 . . ?
C1 C3 N2 105.79(17) . . ?
N2 C3 H3 127.1 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C5 H5 123.1 . . ?
N3 C5 C1 113.72(17) . . ?
N3 C5 H5 123.1 . . ?
N4 C6 S1 121.39(13) . . ?
N5 C6 N4 117.36(16) . . ?
N5 C6 S1 121.24(14) . . ?
O1 C7 C8 111.68(16) . . ?
O2 C7 C8 120.49(17) . . ?
O2 C7 O1 127.74(16) . . ?
C7 C8 H8 109.3 . . ?
C7 C8 Cl1 106.02(12) . . ?
C7 C8 Cl2 112.49(14) . . ?
Cl1 C8 H8 109.3 . . ?
Cl2 C8 H8 109.3 . . ?
Cl2 C8 Cl1 110.36(11) . . ?
N1 Cu1 S1 163.60(4) . . ?
N3 Cu1 N1 80.33(6) . . ?
N3 Cu1 S1 83.63(4) . . ?
O1 Cu1 N1 100.69(6) . . ?
O1 Cu1 N3 169.70(6) . . ?
O1 Cu1 S1 94.48(4) . . ?
C1 N1 Cu1 111.28(11) . . ?
C2 N1 C1 105.99(15) . . ?
C2 N1 Cu1 142.74(13) . . ?
C2 N2 C3 108.49(15) . . ?
C2 N2 H2 125.8 . . ?
C3 N2 H2 125.8 . . ?
C5 N3 Cu1 118.29(12) . . ?
C5 N3 N4 120.43(16) . . ?
N4 N3 Cu1 121.21(12) . . ?
C6 N4 N3 117.13(15) . . ?
C6 N4 H4 121.4 . . ?
N3 N4 H4 121.4 . . ?
C6 N5 H5A 120.0 . . ?
C6 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C7 O1 Cu1 119.32(11) . . ?
C6 S1 Cu1 96.31(6) . . ?
O3 C9 C10 113.05(16) . . ?
O4 C9 C10 119.74(15) . . ?
O4 C9 O3 127.17(17) . . ?
C9 C10 H10A 110.3 . . ?
C9 C10 H10 107.7 . . ?
C9 C10 Cl3 112.33(13) . . ?
C9 C10 Cl4 107.0(4) . . ?
C9 C10 Cl4X 108.6(3) . . ?
H10A C10 H10 5.4 . . ?
Cl3 C10 H10A 110.3 . . ?
Cl3 C10 H10 107.7 . . ?
Cl3 C10 Cl4 106.5(4) . . ?
Cl3 C10 Cl4X 112.6(4) . . ?
Cl4 C10 H10A 110.3 . . ?
Cl4 C10 H10 115.7 . . ?
Cl4X C10 H10A 102.3 . . ?
Cl4X C10 H10 107.7 . . ?
Cl4X C10 Cl4 8.3(9) . . ?

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 Cl3 0.88 2.90 3.4443(17) 121.8 1_556
N2 H2 O4 0.88 1.93 2.7839(19) 163.5 1_556
N4 H4 O3 0.88 1.76 2.615(2) 165.1 .
N5 H5A O4 0.88 2.02 2.895(2) 174.7 .
N5 H5B O2 0.88 1.96 2.779(2) 154.4 4_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
C1 C3 N2 C2 0.2(2) . . . . ?
C1 C5 N3 Cu1 3.9(2) . . . . ?
C1 C5 N3 N4 -179.07(16) . . . . ?
C3 C1 C5 N3 176.9(2) . . . . ?
C3 C1 N1 C2 -0.8(2) . . . . ?
C3 C1 N1 Cu1 179.09(13) . . . . ?
C4 C2 N1 C1 -177.61(18) . . . . ?
C4 C2 N1 Cu1 2.5(3) . . . . ?
C4 C2 N2 C3 177.85(18) . . . . ?
C5 C1 C3 N2 -177.2(2) . . . . ?
C5 C1 N1 C2 177.25(17) . . . . ?
C5 C1 N1 Cu1 -2.8(2) . . . . ?
C5 N3 N4 C6 -174.03(17) . . . . ?
C8 C7 O1 Cu1 160.47(11) . . . . ?
Cu1 N3 N4 C6 2.9(2) . . . . ?
N1 C1 C3 N2 0.4(2) . . . . ?
N1 C1 C5 N3 -0.5(3) . . . . ?
N1 C2 N2 C3 -0.8(2) . . . . ?
N1 Cu1 N3 C5 -4.34(14) . . . . ?
N1 Cu1 N3 N4 178.65(14) . . . . ?
N1 Cu1 O1 C7 112.30(13) . . . . ?
N1 Cu1 S1 C6 16.53(18) . . . . ?
N2 C2 N1 C1 1.0(2) . . . . ?
N2 C2 N1 Cu1 -178.91(15) . . . . ?
N3 Cu1 N1 C1 3.62(12) . . . . ?
N3 Cu1 N1 C2 -176.5(2) . . . . ?
N3 Cu1 O1 C7 17.5(4) . . . . ?
N3 Cu1 S1 C6 4.41(8) . . . . ?
N4 C6 S1 Cu1 -4.91(16) . . . . ?
N5 C6 N4 N3 -179.14(16) . . . . ?
N5 C6 S1 Cu1 176.48(15) . . . . ?
O1 C7 C8 Cl1 -86.27(16) . . . . ?
O1 C7 C8 Cl2 153.04(13) . . . . ?
O1 Cu1 N1 C1 -165.96(12) . . . . ?
O1 Cu1 N1 C2 13.9(2) . . . . ?
O1 Cu1 N3 C5 92.3(3) . . . . ?
O1 Cu1 N3 N4 -84.7(3) . . . . ?
O1 Cu1 S1 C6 174.23(7) . . . . ?
O2 C7 C8 Cl1 90.72(18) . . . . ?
O2 C7 C8 Cl2 -30.0(2) . . . . ?
O2 C7 O1 Cu1 -16.2(2) . . . . ?
S1 C6 N4 N3 2.2(2) . . . . ?
S1 Cu1 N1 C1 -8.6(3) . . . . ?
S1 Cu1 N1 C2 171.29(15) . . . . ?
S1 Cu1 N3 C5 172.22(14) . . . . ?
S1 Cu1 N3 N4 -4.80(13) . . . . ?
S1 Cu1 O1 C7 -61.44(13) . . . . ?
O3 C9 C10 Cl3 -143.14(15) . . . . ?
O3 C9 C10 Cl4 100.3(5) . . . . ?
O3 C9 C10 Cl4X 91.7(5) . . . . ?
O4 C9 C10 Cl3 38.9(2) . . . . ?
O4 C9 C10 Cl4 -77.7(5) . . . . ?
O4 C9 C10 Cl4X -86.3(5) . . . . ?


_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_ls44__2_0ma
_database_code_depnum_ccdc_archive 'CCDC 1845470'
_audit_update_record             
;
2018-10-31 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_audit_creation_date             2018-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H14 Cl2 Cu N5 O3 S, H2 O, C2 H Cl2 O2'
_chemical_formula_sum            'C11 H17 Cl4 Cu N5 O6 S'
_chemical_formula_weight         552.70
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5477(3)
_cell_length_b                   17.3408(6)
_cell_length_c                   15.7754(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.6740(10)
_cell_angle_gamma                90
_cell_volume                     2054.62(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3567
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      2.33
_cell_measurement_theta_min      26.10
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.724
_exptl_absorpt_coefficient_mu    1.724
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_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    1.787
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30340
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.349
_diffrn_ambient_temperature      119.91
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3629
_reflns_number_total             4197
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.056
_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)+(0.0263P)²+1.1765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0626
_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) groups, All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), N2(H2), N4(H4), N5(H5), C9(H2WA,H2WB)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5A)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.54895(3) 0.40927(2) 0.85186(2) 0.01145(8) Uani 1 1 d . . . . .
Cl1 Cl 0.21516(9) 0.47039(3) 0.58432(4) 0.03462(16) Uani 1 1 d . . . . .
Cl2 Cl 0.12757(7) 0.30976(3) 0.55814(4) 0.02287(13) Uani 1 1 d . . . . .
S1 S 0.52118(7) 0.28146(3) 0.88667(3) 0.01492(12) Uani 1 1 d . . . . .
O1 O 0.34613(18) 0.41383(8) 0.76205(9) 0.0138(3) Uani 1 1 d . . . . .
O1W O 0.74040(18) 0.40544(8) 0.75652(9) 0.0165(3) Uani 1 1 d . . . . .
H1WA H 0.833081 0.428578 0.773755 0.025 Uiso 1 1 d R . . . .
H1WB H 0.772141 0.361039 0.747725 0.025 Uiso 1 1 d R . . . .
O2 O 0.40073(19) 0.30079(8) 0.70053(10) 0.0195(3) Uani 1 1 d . . . . .
N1 N 0.5828(2) 0.52563(10) 0.86402(11) 0.0134(4) Uani 1 1 d . . . . .
N2 N 0.6276(2) 0.65061(10) 0.86904(11) 0.0157(4) Uani 1 1 d . . . . .
H2 H 0.622751 0.699543 0.854176 0.019 Uiso 1 1 d R . . . .
N3 N 0.6896(2) 0.41464(9) 0.96654(11) 0.0125(4) Uani 1 1 d . . . . .
N4 N 0.7246(2) 0.34931(9) 1.01373(11) 0.0147(4) Uani 1 1 d . . . . .
H4 H 0.796447 0.349886 1.061185 0.018 Uiso 1 1 d R . . . .
N5 N 0.6664(2) 0.22261(10) 1.03361(11) 0.0157(4) Uani 1 1 d . . . . .
H5 H 0.721842 0.228774 1.084909 0.019 Uiso 1 1 d R . . . .
C1 C 0.6879(3) 0.54396(12) 0.93880(13) 0.0138(4) Uani 1 1 d . . . . .
C2 C 0.7152(3) 0.62179(12) 0.94233(14) 0.0161(4) Uani 1 1 d . . . . .
H2A H 0.781094 0.650004 0.986428 0.019 Uiso 1 1 calc R . . . .
C3 C 0.5499(3) 0.59169(11) 0.82291(14) 0.0141(4) Uani 1 1 d . . . . .
C4 C 0.4518(3) 0.60108(13) 0.73748(14) 0.0209(5) Uani 1 1 d . . . . .
H4A H 0.522547 0.579569 0.694285 0.031 Uiso 1 1 calc GR . . . .
H4B H 0.430342 0.656011 0.726026 0.031 Uiso 1 1 calc GR . . . .
H4C H 0.337678 0.573882 0.735591 0.031 Uiso 1 1 calc GR . . . .
C5 C 0.7439(3) 0.48137(12) 0.99477(13) 0.0148(4) Uani 1 1 d . . . . .
H5A H 0.814276 0.488360 1.047552 0.018 Uiso 1 1 calc R . . . .
C6 C 0.6437(3) 0.28372(12) 0.98396(13) 0.0136(4) Uani 1 1 d . . . . .
C7 C 0.6053(3) 0.14555(12) 1.00844(15) 0.0227(5) Uani 1 1 d . . . . .
H7A H 0.478861 0.147484 0.987226 0.034 Uiso 1 1 calc GR . . . .
H7B H 0.621539 0.110987 1.057749 0.034 Uiso 1 1 calc GR . . . .
H7C H 0.674271 0.126300 0.963407 0.034 Uiso 1 1 calc GR . . . .
C8 C 0.3206(3) 0.36204(11) 0.70445(13) 0.0126(4) Uani 1 1 d . . . . .
C9 C 0.1676(3) 0.38244(12) 0.63596(14) 0.0178(5) Uani 1 1 d . . . . .
H9 H 0.056606 0.389814 0.664760 0.021 Uiso 1 1 calc R . . . .
H2WA H 0.038566 0.530062 0.808266 0.027 Uiso 1 1 d R . . . .
H2WB H 0.133256 0.467742 0.800506 0.027 Uiso 1 1 d R . . . .
Cl3 Cl 1.02453(7) 0.27902(3) 0.86385(4) 0.02570(14) Uani 1 1 d . . . . .
Cl4 Cl 1.07622(10) 0.11390(4) 0.84507(4) 0.03945(18) Uani 1 1 d . . . . .
O3 O 0.8449(2) 0.26317(9) 0.69549(10) 0.0241(4) Uani 1 1 d . . . . .
O4 O 0.9287(2) 0.14343(8) 0.66821(9) 0.0196(3) Uani 1 1 d . . . . .
C10 C 1.0670(3) 0.20377(12) 0.79320(14) 0.0198(5) Uani 1 1 d . . . . .
H10 H 1.187294 0.213448 0.773937 0.024 Uiso 1 1 calc R . . . .
C11 C 0.9318(3) 0.20336(12) 0.71251(13) 0.0161(5) Uani 1 1 d . . . . .
O2W O 0.04258(18) 0.48358(8) 0.82047(10) 0.0184(3) 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
Cu1 S1 2.2980(6) . ?
Cu1 O1 1.9820(14) . ?
Cu1 O1W 2.1874(14) . ?
Cu1 N1 2.0404(17) . ?
Cu1 N3 2.0070(17) . ?
Cl1 C9 1.782(2) . ?
Cl2 C9 1.765(2) . ?
S1 C6 1.712(2) . ?
O1 C8 1.279(2) . ?
O1W H1WA 0.8287 . ?
O1W H1WB 0.8222 . ?
O2 C8 1.227(2) . ?
N1 C1 1.392(3) . ?
N1 C3 1.328(3) . ?
N2 H2 0.8801 . ?
N2 C2 1.368(3) . ?
N2 C3 1.354(3) . ?
N3 N4 1.367(2) . ?
N3 C5 1.292(3) . ?
N4 H4 0.8799 . ?
N4 C6 1.353(3) . ?
N5 H5 0.8799 . ?
N5 C6 1.319(3) . ?
N5 C7 1.456(3) . ?
C1 C2 1.366(3) . ?
C1 C5 1.436(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.481(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.543(3) . ?
C9 H9 1.0000 . ?
Cl3 C10 1.766(2) . ?
Cl4 C10 1.758(2) . ?
O3 C11 1.242(3) . ?
O4 C11 1.251(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.550(3) . ?
O2W H2WA 0.8286 . ?
O2W H2WB 0.8280 . ?

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 S1 97.30(4) . . ?
O1 Cu1 O1W 91.47(6) . . ?
O1 Cu1 N1 96.22(6) . . ?
O1 Cu1 N3 160.86(6) . . ?
O1W Cu1 S1 102.54(4) . . ?
N1 Cu1 S1 160.88(5) . . ?
N1 Cu1 O1W 90.55(6) . . ?
N3 Cu1 S1 83.22(5) . . ?
N3 Cu1 O1W 107.15(6) . . ?
N3 Cu1 N1 79.59(7) . . ?
C6 S1 Cu1 97.94(7) . . ?
C8 O1 Cu1 122.10(13) . . ?
Cu1 O1W H1WA 110.7 . . ?
Cu1 O1W H1WB 111.6 . . ?
H1WA O1W H1WB 105.0 . . ?
C1 N1 Cu1 111.16(13) . . ?
C3 N1 Cu1 142.35(15) . . ?
C3 N1 C1 106.28(17) . . ?
C2 N2 H2 125.5 . . ?
C3 N2 H2 125.5 . . ?
C3 N2 C2 109.01(17) . . ?
N4 N3 Cu1 120.60(12) . . ?
C5 N3 Cu1 118.29(14) . . ?
C5 N3 N4 121.11(17) . . ?
N3 N4 H4 121.6 . . ?
C6 N4 N3 116.82(17) . . ?
C6 N4 H4 121.6 . . ?
C6 N5 H5 118.1 . . ?
C6 N5 C7 123.80(18) . . ?
C7 N5 H5 118.1 . . ?
N1 C1 C5 117.20(18) . . ?
C2 C1 N1 109.35(18) . . ?
C2 C1 C5 133.5(2) . . ?
N2 C2 H2A 127.2 . . ?
C1 C2 N2 105.56(18) . . ?
C1 C2 H2A 127.2 . . ?
N1 C3 N2 109.79(18) . . ?
N1 C3 C4 126.29(19) . . ?
N2 C3 C4 123.85(18) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 C1 113.62(19) . . ?
N3 C5 H5A 123.2 . . ?
C1 C5 H5A 123.2 . . ?
N4 C6 S1 121.04(16) . . ?
N5 C6 S1 122.77(16) . . ?
N5 C6 N4 116.19(19) . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C9 112.72(17) . . ?
O2 C8 O1 127.14(19) . . ?
O2 C8 C9 120.12(18) . . ?
Cl1 C9 H9 108.3 . . ?
Cl2 C9 Cl1 108.76(12) . . ?
Cl2 C9 H9 108.3 . . ?
C8 C9 Cl1 110.23(14) . . ?
C8 C9 Cl2 112.85(14) . . ?
C8 C9 H9 108.3 . . ?
Cl3 C10 H10 107.1 . . ?
Cl4 C10 Cl3 111.26(12) . . ?
Cl4 C10 H10 107.1 . . ?
C11 C10 Cl3 112.08(15) . . ?
C11 C10 Cl4 111.76(15) . . ?
C11 C10 H10 107.1 . . ?
O3 C11 O4 126.3(2) . . ?
O3 C11 C10 117.66(19) . . ?
O4 C11 C10 115.90(18) . . ?
H2WA O2W H2WB 104.3 . . ?

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
_geom_hbond_publ_flag
O1W H1WA O2W 0.83 1.93 2.757(2) 176.4 1_655 yes
O1W H1WB O3 0.82 1.99 2.790(2) 165.2 . yes
N2 H2 O2 0.88 1.96 2.826(2) 169.2 2_656 yes
N4 H4 O4 0.88 1.88 2.754(2) 173.5 4_566 yes
N5 H5 O3 0.88 1.90 2.778(2) 177.1 4_566 yes
C2 H2A Cl2 0.95 2.96 3.469(2) 115.2 2_656 yes
C2 H2A Cl3 0.95 2.93 3.870(2) 172.9 3_767 yes
C4 H4B S1 0.98 2.86 3.707(2) 145.7 2_656 yes
C4 H4C Cl1 0.98 3.06 3.648(2) 120.2 . yes
C5 H5A O2W 0.95 2.30 3.245(3) 172.7 3_667 yes
C7 H7C Cl1 0.98 2.95 3.687(2) 132.9 2_646 yes
O2W H2WA O4 0.83 2.01 2.785(2) 155.1 2_656 yes
O2W H2WB O1 0.83 2.00 2.8247(19) 170.9 . yes
C10 H10 O2 1.00 2.57 3.470(3) 149.9 1_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 S1 C6 N4 -2.39(17) . . . . ?
Cu1 S1 C6 N5 178.27(16) . . . . ?
Cu1 O1 C8 O2 7.9(3) . . . . ?
Cu1 O1 C8 C9 -173.55(12) . . . . ?
Cu1 N1 C1 C2 176.80(14) . . . . ?
Cu1 N1 C1 C5 -3.4(2) . . . . ?
Cu1 N1 C3 N2 -174.63(16) . . . . ?
Cu1 N1 C3 C4 2.3(4) . . . . ?
Cu1 N3 N4 C6 -7.3(2) . . . . ?
Cu1 N3 C5 C1 2.1(2) . . . . ?
O1 C8 C9 Cl1 60.0(2) . . . . ?
O1 C8 C9 Cl2 -178.19(14) . . . . ?
O2 C8 C9 Cl1 -121.32(18) . . . . ?
O2 C8 C9 Cl2 0.5(3) . . . . ?
N1 C1 C2 N2 -0.5(2) . . . . ?
N1 C1 C5 N3 1.0(3) . . . . ?
N3 N4 C6 S1 6.2(2) . . . . ?
N3 N4 C6 N5 -174.44(17) . . . . ?
N4 N3 C5 C1 -177.12(17) . . . . ?
C1 N1 C3 N2 -0.8(2) . . . . ?
C1 N1 C3 C4 176.15(19) . . . . ?
C2 N2 C3 N1 0.5(2) . . . . ?
C2 N2 C3 C4 -176.56(19) . . . . ?
C2 C1 C5 N3 -179.2(2) . . . . ?
C3 N1 C1 C2 0.8(2) . . . . ?
C3 N1 C1 C5 -179.33(17) . . . . ?
C3 N2 C2 C1 0.1(2) . . . . ?
C5 N3 N4 C6 171.89(18) . . . . ?
C5 C1 C2 N2 179.7(2) . . . . ?
C7 N5 C6 S1 6.0(3) . . . . ?
C7 N5 C6 N4 -173.36(18) . . . . ?
Cl3 C10 C11 O3 18.2(3) . . . . ?
Cl3 C10 C11 O4 -165.62(16) . . . . ?
Cl4 C10 C11 O3 143.84(17) . . . . ?
Cl4 C10 C11 O4 -39.9(2) . . . . ?


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

data_ls39_0ma
_database_code_depnum_ccdc_archive 'CCDC 1845471'
_audit_update_record             
;
2018-10-31 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_audit_creation_date             2018-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 Cl2 Cu N5 O3 S, C2 H Cl2 O2'
_chemical_formula_sum            'C18 H21 Cl4 Cu N5 O5 S'
_chemical_formula_weight         624.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5794(11)
_cell_length_b                   17.6082(16)
_cell_length_c                   15.4996(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.502(4)
_cell_angle_gamma                90
_cell_volume                     2519.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3103
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      48.45
_cell_measurement_theta_min      5.23
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.414
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_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    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1268
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29389
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.263
_diffrn_ambient_temperature      119.96
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3513
_reflns_number_total             4441
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4441
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.041
_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)+(0.0267P)²+3.9361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0832
_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 C(H,H,H,H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O3-H3A
 0.87 with sigma of 0.01
 Cu1-H3A
 2.792559 with sigma of 0.02
 C17-H3A
 1.88675 with sigma of 0.02
 O2X-C13 \\sim O2-C13
 with sigma of 0.01
 C18-C17 \\sim C18-C17X
 with sigma of 0.01
 O3-C17 \\sim O3-C17X
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C17X) = Uanis(C17)
4. Others
 Sof(H3B)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C17X)=Sof(H17C)=Sof(H17D)=1-FVAR(1)
 Sof(H3A)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
 Fixed Sof: O2(0.5) O2X(0.5)
5.a Riding coordinates:
 O3(H3A,H3B), N2(H2), N4(H4), N5(H5), C18(H18A,H18B,H18C), C18(H18D,H18E,H18F)
5.b Ternary CH refined with riding coordinates:
 C14(H14), C16(H16)
5.c Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C17X(H17C,H17D)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5A), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
5.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 0.91373(4) 0.06519(2) 0.88919(3) 0.01396(11) Uani 1 1 d D . . . .
Cl1 Cl 0.57725(10) 0.29876(5) 0.98376(6) 0.0277(2) Uani 1 1 d . . . . .
Cl2 Cl 0.75848(12) 0.32701(5) 0.86533(7) 0.0360(3) Uani 1 1 d . . . . .
S1 S 0.69381(8) 0.00476(4) 0.85861(6) 0.01566(19) Uani 1 1 d . . . . .
O1 O 0.8592(2) 0.16406(12) 0.92402(15) 0.0196(5) Uani 1 1 d . . . . .
O2 O 0.6418(7) 0.1448(4) 0.9479(5) 0.0310(18) Uani 0.5 1 d D . P A 1
O2X O 0.6176(6) 0.1550(4) 0.8966(5) 0.0327(18) Uani 0.5 1 d D . P A 2
O3 O 0.9031(3) 0.09491(13) 0.74547(15) 0.0264(6) Uani 1 1 d D . . . .
H3A H 0.830356 0.118259 0.714585 0.040 Uiso 0.852(6) 1 d DR . P B 1
H3B H 0.869306 0.136989 0.724335 0.040 Uiso 0.148(6) 1 d R . P B 2
N1 N 1.1295(3) 0.08702(14) 0.92285(17) 0.0158(6) Uani 1 1 d . . . . .
N2 N 1.3531(3) 0.11891(16) 0.9304(2) 0.0254(7) Uani 1 1 d . . . . .
H2 H 1.431024 0.147090 0.936522 0.030 Uiso 1 1 d R . . . .
N3 N 0.9899(3) -0.03927(14) 0.88190(17) 0.0146(6) Uani 1 1 d . . . . .
N4 N 0.8969(3) -0.09969(14) 0.85936(18) 0.0166(6) Uani 1 1 d . . . . .
H4 H 0.928807 -0.146179 0.856090 0.020 Uiso 1 1 d R . . . .
N5 N 0.6658(3) -0.14332(14) 0.81635(18) 0.0174(6) Uani 1 1 d . . . . .
H5 H 0.705473 -0.188693 0.820046 0.021 Uiso 1 1 d R . . . .
C1 C 1.2070(3) 0.02234(18) 0.9120(2) 0.0173(7) Uani 1 1 d . . . . .
C2 C 1.3461(4) 0.0421(2) 0.9164(2) 0.0247(8) Uani 1 1 d . . . . .
H2A H 1.422285 0.009442 0.910955 0.030 Uiso 1 1 calc R . . . .
C3 C 1.2216(4) 0.14469(19) 0.9335(2) 0.0205(8) Uani 1 1 d . . . . .
C4 C 1.1886(4) 0.22547(18) 0.9471(3) 0.0248(8) Uani 1 1 d . . . . .
H4A H 1.083928 0.231593 0.937912 0.037 Uiso 1 1 calc GR . . . .
H4B H 1.220751 0.257261 0.904207 0.037 Uiso 1 1 calc GR . . . .
H4C H 1.239236 0.240876 1.008221 0.037 Uiso 1 1 calc GR . . . .
C5 C 1.1274(3) -0.04723(18) 0.8940(2) 0.0164(7) Uani 1 1 d . . . . .
H5A H 1.172059 -0.095018 0.891197 0.020 Uiso 1 1 calc R . . . .
C6 C 0.7540(3) -0.08430(17) 0.8423(2) 0.0151(7) Uani 1 1 d . . . . .
C7 C 0.5115(3) -0.13873(18) 0.7828(2) 0.0175(7) Uani 1 1 d . . . . .
C8 C 0.4280(4) -0.1892(2) 0.8157(2) 0.0258(8) Uani 1 1 d . . . . .
H8 H 0.472694 -0.224180 0.861419 0.031 Uiso 1 1 calc R . . . .
C9 C 0.2785(4) -0.1884(2) 0.7817(3) 0.0355(10) Uani 1 1 d . . . . .
H9 H 0.220811 -0.223058 0.804203 0.043 Uiso 1 1 calc R . . . .
C10 C 0.2139(4) -0.1380(2) 0.7161(3) 0.0361(10) Uani 1 1 d . . . . .
H10 H 0.111446 -0.137408 0.693503 0.043 Uiso 1 1 calc R . . . .
C11 C 0.2979(4) -0.0878(2) 0.6825(3) 0.0330(10) Uani 1 1 d . . . . .
H11 H 0.252591 -0.052593 0.637212 0.040 Uiso 1 1 calc R . . . .
C12 C 0.4474(4) -0.08870(18) 0.7145(2) 0.0228(8) Uani 1 1 d . . . . .
H12 H 0.505155 -0.055557 0.690069 0.027 Uiso 1 1 calc R . . . .
C13 C 0.7382(4) 0.18668(19) 0.9315(2) 0.0223(8) Uani 1 1 d D . . . .
C14 C 0.7376(3) 0.27102(17) 0.9562(2) 0.0163(7) Uani 1 1 d . . . . .
H14 H 0.821860 0.280883 1.009036 0.020 Uiso 1 1 calc R . . . .
C17 C 1.0009(4) 0.0809(2) 0.6930(3) 0.0281(11) Uani 0.852(6) 1 d D . P B 1
H17A H 1.076465 0.045131 0.725634 0.034 Uiso 0.852(6) 1 calc R . P B 1
H17B H 1.049362 0.129084 0.685296 0.034 Uiso 0.852(6) 1 calc R . P B 1
C18 C 0.9300(5) 0.0487(3) 0.6030(3) 0.0608(14) Uani 1 1 d D . . . .
H18A H 0.945707 0.082737 0.556498 0.091 Uiso 0.852(6) 1 d R . P B 1
H18B H 0.970867 -0.001403 0.596688 0.091 Uiso 0.852(6) 1 d R . P B 1
H18C H 0.825847 0.043707 0.596688 0.091 Uiso 0.852(6) 1 d R . P B 1
H18D H 0.848877 0.033697 0.552518 0.091 Uiso 0.148(6) 1 d R . P B 2
H18E H 0.947017 0.103367 0.600068 0.091 Uiso 0.148(6) 1 d R . P B 2
H18F H 1.017287 0.020917 0.600068 0.091 Uiso 0.148(6) 1 d R . P B 2
Cl3 Cl 0.98945(13) -0.41864(5) 0.93869(7) 0.0436(3) Uani 1 1 d . . . . .
Cl4 Cl 1.13344(12) -0.37849(5) 0.80372(9) 0.0482(3) Uani 1 1 d . . . . .
O4 O 1.0023(2) -0.24127(12) 0.85952(15) 0.0195(5) Uani 1 1 d . . . . .
O5 O 0.7772(2) -0.28851(12) 0.82320(16) 0.0221(5) Uani 1 1 d . . . . .
C15 C 0.9129(4) -0.29391(17) 0.8385(2) 0.0171(7) Uani 1 1 d . . . . .
C16 C 0.9683(4) -0.37523(18) 0.8327(2) 0.0203(8) Uani 1 1 d . . . . .
H16 H 0.893839 -0.404051 0.786853 0.024 Uiso 1 1 calc R . . . .
C17X C 0.895(3) 0.0309(7) 0.6874(9) 0.0281(11) Uani 0.148(6) 1 d D . P B 2
H17C H 0.795306 0.009876 0.673429 0.034 Uiso 0.148(6) 1 calc R . P B 2
H17D H 0.961910 -0.008822 0.719353 0.034 Uiso 0.148(6) 1 calc R . P B 2


_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 2.2937(9) . ?
Cu1 O1 1.935(2) . ?
Cu1 O3 2.264(2) . ?
Cu1 N1 2.028(3) . ?
Cu1 N3 1.993(3) . ?
Cl1 C14 1.770(3) . ?
Cl2 C14 1.773(3) . ?
S1 C6 1.713(3) . ?
O1 C13 1.260(4) . ?
O2 C13 1.260(6) . ?
O2X C13 1.266(6) . ?
O3 H3A 0.8401 . ?
O3 H3B 0.8394 . ?
O3 C17 1.416(4) . ?
O3 C17X 1.431(10) . ?
N1 C1 1.394(4) . ?
N1 C3 1.327(4) . ?
N2 H2 0.8800 . ?
N2 C2 1.369(4) . ?
N2 C3 1.352(4) . ?
N3 N4 1.371(4) . ?
N3 C5 1.288(4) . ?
N4 H4 0.8800 . ?
N4 C6 1.351(4) . ?
N5 H5 0.8799 . ?
N5 C6 1.332(4) . ?
N5 C7 1.432(4) . ?
C1 C2 1.362(5) . ?
C1 C5 1.430(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.484(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9500 . ?
C7 C8 1.381(5) . ?
C7 C12 1.388(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.367(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.534(4) . ?
C14 H14 1.0000 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.491(6) . ?
C18 H18A 0.9798 . ?
C18 H18B 0.9801 . ?
C18 H18C 0.9800 . ?
C18 H18D 0.9801 . ?
C18 H18E 0.9799 . ?
C18 H18F 0.9800 . ?
C18 C17X 1.469(11) . ?
Cl3 C16 1.774(3) . ?
Cl4 C16 1.757(4) . ?
O4 C15 1.245(4) . ?
O5 C15 1.261(4) . ?
C15 C16 1.538(4) . ?
C16 H16 1.0000 . ?
C17X H17C 0.9900 . ?
C17X H17D 0.9900 . ?

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 S1 100.00(7) . . ?
O1 Cu1 O3 97.01(9) . . ?
O1 Cu1 N1 95.17(10) . . ?
O1 Cu1 N3 167.45(10) . . ?
O3 Cu1 S1 96.13(7) . . ?
N1 Cu1 S1 163.21(8) . . ?
N1 Cu1 O3 89.08(10) . . ?
N3 Cu1 S1 83.69(8) . . ?
N3 Cu1 O3 94.50(10) . . ?
N3 Cu1 N1 80.00(10) . . ?
C6 S1 Cu1 97.38(11) . . ?
C13 O1 Cu1 129.3(2) . . ?
Cu1 O3 H3A 119.1 . . ?
Cu1 O3 H3B 120.0 . . ?
C17 O3 Cu1 131.4(2) . . ?
C17 O3 H3A 109.5 . . ?
C17X O3 Cu1 114.7(6) . . ?
C17X O3 H3B 119.9 . . ?
C1 N1 Cu1 110.7(2) . . ?
C3 N1 Cu1 140.8(2) . . ?
C3 N1 C1 106.4(3) . . ?
C2 N2 H2 125.3 . . ?
C3 N2 H2 125.3 . . ?
C3 N2 C2 109.3(3) . . ?
N4 N3 Cu1 120.51(19) . . ?
C5 N3 Cu1 117.9(2) . . ?
C5 N3 N4 121.5(3) . . ?
N3 N4 H4 121.6 . . ?
C6 N4 N3 116.7(3) . . ?
C6 N4 H4 121.7 . . ?
C6 N5 H5 117.4 . . ?
C6 N5 C7 125.1(3) . . ?
C7 N5 H5 117.4 . . ?
N1 C1 C5 116.8(3) . . ?
C2 C1 N1 109.4(3) . . ?
C2 C1 C5 133.8(3) . . ?
N2 C2 H2A 127.3 . . ?
C1 C2 N2 105.4(3) . . ?
C1 C2 H2A 127.3 . . ?
N1 C3 N2 109.5(3) . . ?
N1 C3 C4 126.2(3) . . ?
N2 C3 C4 124.2(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 C1 114.0(3) . . ?
N3 C5 H5A 123.0 . . ?
C1 C5 H5A 123.0 . . ?
N4 C6 S1 121.2(2) . . ?
N5 C6 S1 123.2(2) . . ?
N5 C6 N4 115.5(3) . . ?
C8 C7 N5 118.2(3) . . ?
C8 C7 C12 120.5(3) . . ?
C12 C7 N5 121.1(3) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.6(4) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 120.5 . . ?
C11 C12 C7 119.0(3) . . ?
C11 C12 H12 120.5 . . ?
O1 C13 O2X 125.3(5) . . ?
O1 C13 C14 113.2(3) . . ?
O2 C13 O1 125.1(4) . . ?
O2 C13 C14 117.7(4) . . ?
O2X C13 C14 118.0(4) . . ?
Cl1 C14 Cl2 109.14(17) . . ?
Cl1 C14 H14 108.4 . . ?
Cl2 C14 H14 108.4 . . ?
C13 C14 Cl1 112.9(2) . . ?
C13 C14 Cl2 109.4(2) . . ?
C13 C14 H14 108.4 . . ?
O3 C17 H17A 108.9 . . ?
O3 C17 H17B 108.9 . . ?
O3 C17 C18 113.4(4) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 110.0 . . ?
C17 C18 H18C 108.9 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H18D C18 H18E 109.5 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C17X C18 H18D 109.3 . . ?
C17X C18 H18E 109.3 . . ?
C17X C18 H18F 109.7 . . ?
O4 C15 O5 126.6(3) . . ?
O4 C15 C16 119.0(3) . . ?
O5 C15 C16 114.4(3) . . ?
Cl3 C16 H16 108.8 . . ?
Cl4 C16 Cl3 109.56(18) . . ?
Cl4 C16 H16 108.8 . . ?
C15 C16 Cl3 107.6(2) . . ?
C15 C16 Cl4 113.2(2) . . ?
C15 C16 H16 108.8 . . ?
O3 C17X C18 113.9(8) . . ?
O3 C17X H17C 108.8 . . ?
O3 C17X H17D 108.8 . . ?
C18 C17X H17C 108.8 . . ?
C18 C17X H17D 108.8 . . ?
H17C C17X H17D 107.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3B O5 0.84 1.92 2.711(3) 156.9 2_656 yes
N2 H2 O2 0.88 1.98 2.744(7) 144.4 1_655 yes
N2 H2 O2X 0.88 2.05 2.795(7) 142.2 1_655 yes
N4 H4 O4 0.88 1.81 2.689(3) 175.1 . yes
N5 H5 O5 0.88 1.88 2.761(3) 175.8 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 S1 C6 N4 7.4(3) . . . . ?
Cu1 S1 C6 N5 -175.7(3) . . . . ?
Cu1 O1 C13 O2 26.2(7) . . . . ?
Cu1 O1 C13 O2X -18.7(7) . . . . ?
Cu1 O1 C13 C14 -176.9(2) . . . . ?
Cu1 O3 C17 C18 131.9(3) . . . . ?
Cu1 O3 C17X C18 -163.2(11) . . . . ?
Cu1 N1 C1 C2 167.2(2) . . . . ?
Cu1 N1 C1 C5 -9.3(3) . . . . ?
Cu1 N1 C3 N2 -161.1(3) . . . . ?
Cu1 N1 C3 C4 19.0(6) . . . . ?
Cu1 N3 N4 C6 0.4(4) . . . . ?
Cu1 N3 C5 C1 0.4(4) . . . . ?
O1 C13 C14 Cl1 -170.6(2) . . . . ?
O1 C13 C14 Cl2 67.6(3) . . . . ?
O2 C13 C14 Cl1 -11.9(6) . . . . ?
O2 C13 C14 Cl2 -133.6(5) . . . . ?
O2X C13 C14 Cl1 29.4(6) . . . . ?
O2X C13 C14 Cl2 -92.3(5) . . . . ?
N1 C1 C2 N2 0.3(4) . . . . ?
N1 C1 C5 N3 6.1(4) . . . . ?
N3 N4 C6 S1 -6.1(4) . . . . ?
N3 N4 C6 N5 176.9(3) . . . . ?
N4 N3 C5 C1 176.6(3) . . . . ?
N5 C7 C8 C9 -177.1(3) . . . . ?
N5 C7 C12 C11 178.1(3) . . . . ?
C1 N1 C3 N2 -0.4(4) . . . . ?
C1 N1 C3 C4 179.8(3) . . . . ?
C2 N2 C3 N1 0.6(4) . . . . ?
C2 N2 C3 C4 -179.6(3) . . . . ?
C2 C1 C5 N3 -169.3(4) . . . . ?
C3 N1 C1 C2 0.1(4) . . . . ?
C3 N1 C1 C5 -176.4(3) . . . . ?
C3 N2 C2 C1 -0.5(4) . . . . ?
C5 N3 N4 C6 -175.6(3) . . . . ?
C5 C1 C2 N2 175.9(4) . . . . ?
C6 N5 C7 C8 -134.1(3) . . . . ?
C6 N5 C7 C12 50.5(5) . . . . ?
C7 N5 C6 S1 12.2(5) . . . . ?
C7 N5 C6 N4 -170.7(3) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C8 C7 C12 C11 2.8(5) . . . . ?
C8 C9 C10 C11 0.6(6) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C10 C11 C12 C7 -2.2(5) . . . . ?
C12 C7 C8 C9 -1.7(5) . . . . ?
O4 C15 C16 Cl3 92.2(3) . . . . ?
O4 C15 C16 Cl4 -29.0(4) . . . . ?
O5 C15 C16 Cl3 -85.9(3) . . . . ?
O5 C15 C16 Cl4 152.9(2) . . . . ?


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

data_ls42_0ma
_database_code_depnum_ccdc_archive 'CCDC 1845474'
_audit_update_record             
;
2018-10-31 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_audit_creation_date             2017-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H16 Cl2 Cu N5 O3 S, C2 H6 O, C2 H Cl2 O2'
_chemical_formula_sum            'C18 H23 Cl4 Cu N5 O6 S'
_chemical_formula_weight         642.81
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4329(4)
_cell_length_b                   20.2920(8)
_cell_length_c                   14.1277(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.180(2)
_cell_angle_gamma                90.00
_cell_volume                     2669.58(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2976
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.08
_exptl_absorpt_coefficient_mu    1.339
_exptl_absorpt_correction_T_max  0.8558
_exptl_absorpt_correction_T_min  0.7571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_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    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            61193
_diffrn_reflns_theta_full        24.60
_diffrn_reflns_theta_max         24.60
_diffrn_reflns_theta_min         2.01
_diffrn_ambient_temperature      119.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3944
_reflns_number_total             4454
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4454
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0240
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0209P)²+2.8136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0551
_refine_ls_wR_factor_ref         0.0575
_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 N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O1W-H1WA
 0.83 with sigma of 0.01
 O1W-H1WB
 0.83 with sigma of 0.01
 H1WA-H1WB
 1.312545 with sigma of 0.02
3.a Riding coordinates:
 O1W(H1WA,H1WB), N2(H2), N4(H4), N5(H5), O5(H5B)
;
_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 0.35086(2) 0.023009(11) 1.078694(17) 0.01362(7) Uani 1 d . . .
Cl1 Cl 0.78440(6) 0.14665(3) 1.19966(5) 0.03868(16) Uani 1 d . . .
Cl2 Cl 0.66835(7) 0.16661(3) 1.37524(4) 0.03529(16) Uani 1 d . . .
S1 S 0.42713(5) 0.08860(2) 0.96323(4) 0.01549(11) Uani 1 d . . .
O1 O 0.50531(14) 0.04654(6) 1.18172(9) 0.0160(3) Uani 1 d . . .
O1W O 0.17692(14) 0.09743(7) 1.13235(10) 0.0191(3) Uani 1 d . . D
H1WA H 0.1522 0.0776 1.1778 0.029 Uiso 1 d . . DR
H1WB H 0.2391 0.1234 1.1570 0.029 Uiso 1 d . . DR
O2 O 0.43859(15) 0.15091(7) 1.20531(11) 0.0222(3) Uani 1 d . . .
N1 N 0.26380(17) -0.05063(8) 1.14473(11) 0.0144(4) Uani 1 d . . .
N2 N 0.16725(18) -0.12846(8) 1.22160(12) 0.0173(4) Uani 1 d . . .
H2 H 0.1520 -0.1546 1.2687 0.021 Uiso 1 d . . R
N3 N 0.20883(17) -0.00850(8) 0.97047(11) 0.0137(4) Uani 1 d . . .
N4 N 0.19848(17) 0.01981(8) 0.88206(11) 0.0149(4) Uani 1 d . . .
H4 H 0.1288 0.0093 0.8354 0.018 Uiso 1 d . . R
N5 N 0.28867(17) 0.08664(8) 0.77914(11) 0.0150(4) Uani 1 d . . .
H5 H 0.2152 0.0713 0.7389 0.018 Uiso 1 d . . R
C1 C 0.1521(2) -0.08032(10) 1.08314(14) 0.0151(4) Uani 1 d . . .
C2 C 0.0916(2) -0.12899(10) 1.13030(14) 0.0167(4) Uani 1 d . . .
C3 C -0.0265(2) -0.17662(10) 1.09722(17) 0.0248(5) Uani 1 d . . .
H3A H -0.0786 -0.1624 1.0350 0.037 Uiso 1 calc . . GR
H3B H -0.0927 -0.1782 1.1441 0.037 Uiso 1 calc . . GR
H3C H 0.0142 -0.2205 1.0909 0.037 Uiso 1 calc . . GR
C4 C 0.2691(2) -0.08120(10) 1.22719(15) 0.0170(4) Uani 1 d . . .
H4A H 0.3357 -0.0714 1.2833 0.020 Uiso 1 calc . . R
C5 C 0.1246(2) -0.05580(9) 0.98678(14) 0.0148(4) Uani 1 d . . .
H5A H 0.0511 -0.0728 0.9393 0.018 Uiso 1 calc . . R
C6 C 0.2994(2) 0.06451(9) 0.86910(14) 0.0142(4) Uani 1 d . . .
C7 C 0.3789(2) 0.13152(10) 0.73895(14) 0.0160(4) Uani 1 d . . .
C8 C 0.3936(2) 0.12023(11) 0.64378(15) 0.0199(5) Uani 1 d . . .
H8 H 0.3475 0.0835 0.6102 0.024 Uiso 1 calc . . R
C9 C 0.4758(2) 0.16283(12) 0.59823(16) 0.0269(5) Uani 1 d . . .
H9 H 0.4857 0.1553 0.5332 0.032 Uiso 1 calc . . R
C10 C 0.5436(2) 0.21625(12) 0.64688(16) 0.0275(5) Uani 1 d . . .
H10 H 0.6014 0.2449 0.6158 0.033 Uiso 1 calc . . R
C11 C 0.5268(2) 0.22772(11) 0.74096(17) 0.0245(5) Uani 1 d . . .
H11 H 0.5728 0.2645 0.7743 0.029 Uiso 1 calc . . R
C12 C 0.4435(2) 0.18611(10) 0.78714(16) 0.0202(5) Uani 1 d . . .
H12 H 0.4306 0.1948 0.8513 0.024 Uiso 1 calc . . R
C13 C 0.5230(2) 0.10403(9) 1.21657(14) 0.0147(4) Uani 1 d . . .
C14 C 0.6715(2) 0.11305(10) 1.27680(15) 0.0214(5) Uani 1 d . . .
H14 H 0.7098 0.0691 1.3008 0.026 Uiso 1 calc . . R
O5 O 0.08223(17) -0.21698(7) 1.34847(12) 0.0289(4) Uani 1 d . . .
H5B H 0.0770 -0.2568 1.3321 0.043 Uiso 1 d . . R
C17 C -0.0481(3) -0.19786(12) 1.38024(18) 0.0315(6) Uani 1 d . . .
H17A H -0.1305 -0.2137 1.3336 0.038 Uiso 1 calc . . R
H17B H -0.0531 -0.1492 1.3820 0.038 Uiso 1 calc . . R
C18 C -0.0601(3) -0.22445(14) 1.47715(18) 0.0400(6) Uani 1 d . . .
H18A H -0.0609 -0.2727 1.4749 0.060 Uiso 1 calc . . GR
H18B H -0.1493 -0.2086 1.4966 0.060 Uiso 1 calc . . GR
H18C H 0.0221 -0.2095 1.5235 0.060 Uiso 1 calc . . GR
Cl3 Cl -0.22296(6) 0.04477(3) 0.53799(4) 0.03476(15) Uani 1 d . . .
Cl4 Cl -0.25326(7) -0.08494(3) 0.62063(4) 0.03777(16) Uani 1 d . . .
O3 O -0.02417(15) -0.02121(7) 0.75194(10) 0.0203(3) Uani 1 d . . .
O4 O 0.09102(16) 0.02318(7) 0.64157(10) 0.0237(3) Uani 1 d . . .
C15 C -0.0108(2) -0.00703(9) 0.66791(14) 0.0157(4) Uani 1 d . . .
C16 C -0.1301(2) -0.02757(11) 0.58520(15) 0.0205(5) Uani 1 d . . .
H16 H -0.0838 -0.0481 0.5335 0.025 Uiso 1 calc . . 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 2.3075(5) . ?
Cu1 O1 1.9474(13) . ?
Cu1 O1W 2.4381(14) . ?
Cu1 N1 2.0055(16) . ?
Cu1 N3 1.9718(16) . ?
Cl1 C14 1.777(2) . ?
Cl2 C14 1.769(2) . ?
S1 C6 1.717(2) . ?
O1 C13 1.267(2) . ?
O1W H1WA 0.8232 . ?
O1W H1WB 0.8229 . ?
O2 C13 1.234(2) . ?
N1 C1 1.392(3) . ?
N1 C4 1.314(3) . ?
N2 H2 0.8802 . ?
N2 C2 1.371(3) . ?
N2 C4 1.351(3) . ?
N3 N4 1.364(2) . ?
N3 C5 1.290(3) . ?
N4 H4 0.8799 . ?
N4 C6 1.348(3) . ?
N5 H5 0.8800 . ?
N5 C6 1.336(3) . ?
N5 C7 1.425(3) . ?
C1 C2 1.367(3) . ?
C1 C5 1.434(3) . ?
C2 C3 1.492(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C7 C8 1.392(3) . ?
C7 C12 1.389(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.530(3) . ?
C14 H14 1.0000 . ?
O5 H5B 0.8399 . ?
O5 C17 1.428(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.493(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
Cl3 C16 1.784(2) . ?
Cl4 C16 1.772(2) . ?
O3 C15 1.247(2) . ?
O4 C15 1.246(2) . ?
C15 C16 1.544(3) . ?
C16 H16 1.0000 . ?

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 O1W 99.42(4) . . ?
O1 Cu1 S1 96.12(4) . . ?
O1 Cu1 O1W 94.36(5) . . ?
O1 Cu1 N1 98.51(6) . . ?
O1 Cu1 N3 173.62(6) . . ?
N1 Cu1 S1 162.86(5) . . ?
N1 Cu1 O1W 88.34(6) . . ?
N3 Cu1 S1 83.62(5) . . ?
N3 Cu1 O1W 91.96(6) . . ?
N3 Cu1 N1 80.85(7) . . ?
C6 S1 Cu1 97.11(7) . . ?
C13 O1 Cu1 123.55(12) . . ?
Cu1 O1W H1WA 103.2 . . ?
Cu1 O1W H1WB 93.4 . . ?
H1WA O1W H1WB 104.8 . . ?
C1 N1 Cu1 110.92(12) . . ?
C4 N1 Cu1 143.49(14) . . ?
C4 N1 C1 105.54(16) . . ?
C2 N2 H2 125.7 . . ?
C4 N2 H2 125.7 . . ?
C4 N2 C2 108.63(17) . . ?
N4 N3 Cu1 120.92(12) . . ?
C5 N3 Cu1 117.67(13) . . ?
C5 N3 N4 121.39(16) . . ?
N3 N4 H4 121.4 . . ?
C6 N4 N3 117.31(16) . . ?
C6 N4 H4 121.3 . . ?
C6 N5 H5 115.3 . . ?
C6 N5 C7 129.36(17) . . ?
C7 N5 H5 115.3 . . ?
N1 C1 C5 116.59(17) . . ?
C2 C1 N1 109.98(17) . . ?
C2 C1 C5 133.43(19) . . ?
N2 C2 C3 123.39(18) . . ?
C1 C2 N2 104.92(17) . . ?
C1 C2 C3 131.65(19) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 N2 110.93(18) . . ?
N1 C4 H4A 124.5 . . ?
N2 C4 H4A 124.5 . . ?
N3 C5 C1 113.87(17) . . ?
N3 C5 H5A 123.1 . . ?
C1 C5 H5A 123.1 . . ?
N4 C6 S1 120.65(15) . . ?
N5 C6 S1 125.31(15) . . ?
N5 C6 N4 114.04(17) . . ?
C8 C7 N5 115.92(18) . . ?
C12 C7 N5 123.88(18) . . ?
C12 C7 C8 120.09(19) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
O1 C13 C14 112.25(17) . . ?
O2 C13 O1 128.11(18) . . ?
O2 C13 C14 119.61(17) . . ?
Cl1 C14 H14 109.3 . . ?
Cl2 C14 Cl1 109.48(11) . . ?
Cl2 C14 H14 109.3 . . ?
C13 C14 Cl1 106.86(14) . . ?
C13 C14 Cl2 112.46(15) . . ?
C13 C14 H14 109.3 . . ?
C17 O5 H5B 109.4 . . ?
O5 C17 H17A 109.1 . . ?
O5 C17 H17B 109.1 . . ?
O5 C17 C18 112.65(19) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C15 C16 119.08(18) . . ?
O4 C15 O3 126.71(19) . . ?
O4 C15 C16 114.21(17) . . ?
Cl3 C16 H16 108.4 . . ?
Cl4 C16 Cl3 109.94(11) . . ?
Cl4 C16 H16 108.4 . . ?
C15 C16 Cl3 108.41(14) . . ?
C15 C16 Cl4 113.25(14) . . ?
C15 C16 H16 108.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA Cl4 0.82 2.86 3.4583(15) 131.4 3_557
O1W H1WA O3 0.82 2.03 2.8093(19) 157.0 3_557
O1W H1WB O2 0.82 1.98 2.7424(19) 154.3 .
N2 H2 O5 0.88 1.88 2.746(2) 166.5 .
N4 H4 O3 0.88 1.82 2.693(2) 171.2 .
N5 H5 O4 0.88 1.92 2.785(2) 165.5 .
O5 H5B O2 0.84 1.95 2.785(2) 179.0 2_547

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 C6 N4 0.27(16) . . . . ?
Cu1 S1 C6 N5 -179.73(16) . . . . ?
Cu1 O1 C13 O2 13.0(3) . . . . ?
Cu1 O1 C13 C14 -165.10(13) . . . . ?
Cu1 N1 C1 C2 -178.19(13) . . . . ?
Cu1 N1 C1 C5 2.4(2) . . . . ?
Cu1 N1 C4 N2 176.90(16) . . . . ?
Cu1 N3 N4 C6 7.5(2) . . . . ?
Cu1 N3 C5 C1 -2.3(2) . . . . ?
S1 Cu1 O1 C13 64.86(15) . . . . ?
S1 Cu1 N1 C1 -27.9(2) . . . . ?
S1 Cu1 N1 C4 155.15(17) . . . . ?
S1 Cu1 N3 N4 -5.73(13) . . . . ?
S1 Cu1 N3 C5 175.58(14) . . . . ?
O1 Cu1 S1 C6 176.12(8) . . . . ?
O1 Cu1 N1 C1 -176.26(12) . . . . ?
O1 Cu1 N1 C4 6.8(2) . . . . ?
O1 Cu1 N3 N4 -93.7(6) . . . . ?
O1 Cu1 N3 C5 87.6(6) . . . . ?
O1 C13 C14 Cl1 93.88(17) . . . . ?
O1 C13 C14 Cl2 -145.96(15) . . . . ?
O1W Cu1 S1 C6 -88.41(7) . . . . ?
O1W Cu1 O1 C13 -35.12(15) . . . . ?
O1W Cu1 N1 C1 89.57(13) . . . . ?
O1W Cu1 N1 C4 -87.3(2) . . . . ?
O1W Cu1 N3 N4 93.53(14) . . . . ?
O1W Cu1 N3 C5 -85.16(14) . . . . ?
O2 C13 C14 Cl1 -84.4(2) . . . . ?
O2 C13 C14 Cl2 35.7(2) . . . . ?
N1 Cu1 S1 C6 27.60(18) . . . . ?
N1 Cu1 O1 C13 -124.09(15) . . . . ?
N1 Cu1 N3 N4 -178.47(14) . . . . ?
N1 Cu1 N3 C5 2.84(14) . . . . ?
N1 C1 C2 N2 0.3(2) . . . . ?
N1 C1 C2 C3 -177.7(2) . . . . ?
N1 C1 C5 N3 -0.2(3) . . . . ?
N3 Cu1 S1 C6 2.52(8) . . . . ?
N3 Cu1 O1 C13 152.1(5) . . . . ?
N3 Cu1 N1 C1 -2.68(13) . . . . ?
N3 Cu1 N1 C4 -179.6(2) . . . . ?
N3 N4 C6 S1 -4.6(2) . . . . ?
N3 N4 C6 N5 175.40(16) . . . . ?
N4 N3 C5 C1 179.06(16) . . . . ?
N5 C7 C8 C9 177.96(18) . . . . ?
N5 C7 C12 C11 -178.47(18) . . . . ?
C1 N1 C4 N2 -0.1(2) . . . . ?
C2 N2 C4 N1 0.3(2) . . . . ?
C2 C1 C5 N3 -179.4(2) . . . . ?
C4 N1 C1 C2 -0.1(2) . . . . ?
C4 N1 C1 C5 -179.51(17) . . . . ?
C4 N2 C2 C1 -0.3(2) . . . . ?
C4 N2 C2 C3 177.88(19) . . . . ?
C5 N3 N4 C6 -173.85(18) . . . . ?
C5 C1 C2 N2 179.5(2) . . . . ?
C5 C1 C2 C3 1.5(4) . . . . ?
C6 N5 C7 C8 146.8(2) . . . . ?
C6 N5 C7 C12 -37.0(3) . . . . ?
C7 N5 C6 S1 2.7(3) . . . . ?
C7 N5 C6 N4 -177.27(18) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C7 C12 C11 -2.4(3) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C7 1.4(3) . . . . ?
C12 C7 C8 C9 1.6(3) . . . . ?
O3 C15 C16 Cl3 109.32(18) . . . . ?
O3 C15 C16 Cl4 -13.0(2) . . . . ?
O4 C15 C16 Cl3 -70.4(2) . . . . ?
O4 C15 C16 Cl4 167.29(15) . . . . ?


_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_ls45_0m
_database_code_depnum_ccdc_archive 'CCDC 1845473'
_audit_update_record             
;
2018-10-31 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_audit_creation_date             2017-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H12 Cl2 Cu N5 O2 S, C2 H Cl2 O2, C2 H6 O'
_chemical_formula_sum            'C13 H19 Cl4 Cu N5 O5 S'
_chemical_formula_weight         562.73
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.9820(6)
_cell_length_b                   9.8523(6)
_cell_length_c                   13.4982(9)
_cell_angle_alpha                103.683(3)
_cell_angle_beta                 94.647(3)
_cell_angle_gamma                110.613(3)
_cell_volume                     1068.42(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2987
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      23.87
_cell_measurement_theta_min      2.09
_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_T_max  0.7893
_exptl_absorpt_correction_T_min  0.7330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_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    1.749
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             570
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0079
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            67667
_diffrn_reflns_theta_full        25.42
_diffrn_reflns_theta_max         25.42
_diffrn_reflns_theta_min         2.30
_diffrn_ambient_temperature      120.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3874
_reflns_number_total             3924
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0165
_refine_ls_R_factor_gt           0.0163
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0198P)²+0.7038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0426
_refine_ls_wR_factor_ref         0.0427
_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 N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 N2(H2), N4(H4), N5(H5), O5(H5B)
;
_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 0.682441(18) 0.492934(17) 0.464055(12) 0.00970(5) Uani 1 d . . .
Cl1 Cl 0.18216(4) 0.06285(4) 0.34343(3) 0.02263(9) Uani 1 d . . .
Cl2 Cl 0.23669(5) 0.11289(4) 0.56826(3) 0.02295(9) Uani 1 d . . .
S1 S 0.61040(4) 0.43306(4) 0.28779(2) 0.01287(7) Uani 1 d . . .
O2 O 0.59314(11) 0.17792(11) 0.43631(8) 0.0176(2) Uani 1 d . . .
O1 O 0.48043(11) 0.34715(10) 0.48468(7) 0.01185(19) Uani 1 d . . .
N1 N 0.80568(13) 0.56631(12) 0.60849(9) 0.0110(2) Uani 1 d . . .
N2 N 0.92116(14) 0.66405(13) 0.77217(9) 0.0133(2) Uani 1 d . . .
H2 H 0.9338 0.6822 0.8400 0.016 Uiso 1 d . . R
N3 N 0.89869(13) 0.61438(12) 0.44069(9) 0.0104(2) Uani 1 d . . .
N4 N 0.92436(13) 0.61628(12) 0.34253(8) 0.0119(2) Uani 1 d . . .
H4 H 1.0187 0.6709 0.3308 0.014 Uiso 1 d . . R
N5 N 0.82731(14) 0.52545(13) 0.16960(9) 0.0147(2) Uani 1 d . . .
H5 H 0.9264 0.5766 0.1627 0.018 Uiso 1 d . . R
C1 C 0.96402(15) 0.66599(14) 0.61587(10) 0.0102(3) Uani 1 d . . .
C2 C 1.03664(16) 0.72835(15) 0.71798(10) 0.0119(3) Uani 1 d . . .
C3 C 1.19863(18) 0.84606(17) 0.76942(12) 0.0174(3) Uani 1 d . . .
H3A H 1.194(2) 0.942(3) 0.7888(16) 0.040(6) Uiso 1 d . . .
H3B H 1.270(3) 0.846(2) 0.7266(18) 0.046(6) Uiso 1 d . . .
H3C H 1.239(3) 0.831(3) 0.828(2) 0.054(7) Uiso 1 d . . .
C4 C 0.78507(16) 0.56834(15) 0.70383(11) 0.0126(3) Uani 1 d . . .
H4A H 0.6937(19) 0.5133(17) 0.7216(12) 0.008(4) Uiso 1 d . . .
C5 C 1.01363(16) 0.68639(14) 0.51992(10) 0.0106(3) Uani 1 d . . .
H5A H 1.120(2) 0.7447(17) 0.5154(12) 0.010(4) Uiso 1 d . . .
C6 C 0.79774(16) 0.53051(15) 0.26431(10) 0.0117(3) Uani 1 d . . .
C7 C 0.70646(18) 0.44072(18) 0.07578(11) 0.0187(3) Uani 1 d . . .
H7A H 0.626(2) 0.485(2) 0.0691(15) 0.032(5) Uiso 1 d . . .
H7B H 0.759(2) 0.442(2) 0.0189(16) 0.034(5) Uiso 1 d . . .
H7C H 0.655(2) 0.336(2) 0.0744(14) 0.029(5) Uiso 1 d . . .
C8 C 0.47992(16) 0.21344(15) 0.45966(10) 0.0117(3) Uani 1 d . . .
C9 C 0.31978(16) 0.08306(15) 0.45432(11) 0.0137(3) Uani 1 d . . .
H9 H 0.3331(19) -0.0086(18) 0.4445(12) 0.012(4) Uiso 1 d . . .
Cl3 Cl 1.40816(4) 0.94163(4) 0.11268(3) 0.01997(8) Uani 1 d . . .
Cl4 Cl 1.51643(4) 0.72412(4) 0.17858(3) 0.02024(8) Uani 1 d . . .
O3 O 1.13381(12) 0.68991(12) 0.14327(8) 0.0195(2) Uani 1 d . . .
O4 O 1.23033(11) 0.74451(11) 0.31229(7) 0.0142(2) Uani 1 d . . .
C10 C 1.24169(16) 0.75327(15) 0.22256(10) 0.0122(3) Uani 1 d . . .
C11 C 1.41275(16) 0.84953(16) 0.21018(11) 0.0135(3) Uani 1 d . . .
H11 H 1.4715(19) 0.9242(18) 0.2737(13) 0.013(4) Uiso 1 d . . .
O5 O 0.98349(13) 0.75491(14) 0.98644(8) 0.0268(3) Uani 1 d . . .
H5B H 1.0363 0.7289 1.0274 0.040 Uiso 1 d . . R
C12 C 0.89160(19) 0.82848(18) 1.04253(12) 0.0216(3) Uani 1 d . . .
H12A H 0.859(2) 0.784(2) 1.0983(14) 0.023(4) Uiso 1 d . . .
H12B H 0.956(2) 0.937(2) 1.0720(15) 0.034(5) Uiso 1 d . . .
C13 C 0.7449(2) 0.8069(2) 0.96931(14) 0.0286(4) Uani 1 d . . .
H13A H 0.678(3) 0.699(3) 0.9377(17) 0.041(6) Uiso 1 d . . .
H13B H 0.683(3) 0.857(2) 1.0053(18) 0.045(6) Uiso 1 d . . .
H13C H 0.774(2) 0.850(2) 0.9165(16) 0.032(5) Uiso 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 S1 2.2903(4) . ?
Cu1 O1 1.9670(9) . ?
Cu1 N1 1.9923(11) . ?
Cu1 N3 1.9863(11) . ?
Cl1 C9 1.7873(14) . ?
Cl2 C9 1.7706(14) . ?
S1 C6 1.7166(13) . ?
O2 C8 1.2274(17) . ?
O1 C8 1.2784(17) . ?
N1 C1 1.3944(17) . ?
N1 C4 1.3114(18) . ?
N2 H2 0.8800 . ?
N2 C2 1.3754(18) . ?
N2 C4 1.3522(18) . ?
N3 N4 1.3666(15) . ?
N3 C5 1.2881(18) . ?
N4 H4 0.8800 . ?
N4 C6 1.3524(18) . ?
N5 H5 0.8801 . ?
N5 C6 1.3196(18) . ?
N5 C7 1.4554(18) . ?
C1 C2 1.3690(19) . ?
C1 C5 1.4388(18) . ?
C2 C3 1.4870(19) . ?
C3 H3A 0.93(2) . ?
C3 H3B 0.90(2) . ?
C3 H3C 0.90(3) . ?
C4 H4A 0.898(16) . ?
C5 H5A 0.940(16) . ?
C7 H7A 0.97(2) . ?
C7 H7B 0.93(2) . ?
C7 H7C 0.96(2) . ?
C8 C9 1.5371(18) . ?
C9 H9 0.932(16) . ?
Cl3 C11 1.7719(14) . ?
Cl4 C11 1.7892(14) . ?
O3 C10 1.2506(17) . ?
O4 C10 1.2442(17) . ?
C10 C11 1.5423(18) . ?
C11 H11 0.954(17) . ?
O5 H5B 0.8401 . ?
O5 C12 1.4293(18) . ?
C12 H12A 0.973(19) . ?
C12 H12B 0.98(2) . ?
C12 C13 1.500(2) . ?
C13 H13A 0.99(2) . ?
C13 H13B 0.96(2) . ?
C13 H13C 0.92(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 S1 95.73(3) . . ?
O1 Cu1 N1 98.90(4) . . ?
O1 Cu1 N3 171.15(4) . . ?
N1 Cu1 S1 164.29(3) . . ?
N3 Cu1 S1 84.31(3) . . ?
N3 Cu1 N1 80.35(5) . . ?
C6 S1 Cu1 96.88(5) . . ?
C8 O1 Cu1 110.61(8) . . ?
C1 N1 Cu1 111.77(9) . . ?
C4 N1 Cu1 141.42(10) . . ?
C4 N1 C1 106.12(11) . . ?
C2 N2 H2 125.7 . . ?
C4 N2 H2 125.7 . . ?
C4 N2 C2 108.61(11) . . ?
N4 N3 Cu1 120.29(8) . . ?
C5 N3 Cu1 118.11(9) . . ?
C5 N3 N4 121.57(11) . . ?
N3 N4 H4 121.6 . . ?
C6 N4 N3 116.84(11) . . ?
C6 N4 H4 121.6 . . ?
C6 N5 H5 117.9 . . ?
C6 N5 C7 124.17(12) . . ?
C7 N5 H5 117.9 . . ?
N1 C1 C5 116.31(11) . . ?
C2 C1 N1 109.48(12) . . ?
C2 C1 C5 134.16(12) . . ?
N2 C2 C3 122.95(12) . . ?
C1 C2 N2 105.07(12) . . ?
C1 C2 C3 131.89(13) . . ?
C2 C3 H3A 110.8(13) . . ?
C2 C3 H3B 110.2(14) . . ?
C2 C3 H3C 113.1(16) . . ?
H3A C3 H3B 109.4(19) . . ?
H3A C3 H3C 106.5(19) . . ?
H3B C3 H3C 107(2) . . ?
N1 C4 N2 110.72(12) . . ?
N1 C4 H4A 124.9(10) . . ?
N2 C4 H4A 124.4(10) . . ?
N3 C5 C1 113.21(12) . . ?
N3 C5 H5A 123.5(9) . . ?
C1 C5 H5A 123.3(9) . . ?
N4 C6 S1 121.54(10) . . ?
N5 C6 S1 122.34(10) . . ?
N5 C6 N4 116.12(12) . . ?
N5 C7 H7A 111.6(12) . . ?
N5 C7 H7B 108.3(12) . . ?
N5 C7 H7C 110.6(11) . . ?
H7A C7 H7B 109.2(17) . . ?
H7A C7 H7C 110.4(16) . . ?
H7B C7 H7C 106.6(16) . . ?
O2 C8 O1 126.59(12) . . ?
O2 C8 C9 116.45(12) . . ?
O1 C8 C9 116.92(11) . . ?
Cl1 C9 H9 106.7(10) . . ?
Cl2 C9 Cl1 110.78(7) . . ?
Cl2 C9 H9 107.4(10) . . ?
C8 C9 Cl1 107.84(9) . . ?
C8 C9 Cl2 112.55(9) . . ?
C8 C9 H9 111.4(10) . . ?
O3 C10 C11 117.99(12) . . ?
O4 C10 O3 127.73(13) . . ?
O4 C10 C11 114.23(12) . . ?
Cl3 C11 Cl4 110.47(7) . . ?
Cl3 C11 H11 108.5(10) . . ?
Cl4 C11 H11 107.6(9) . . ?
C10 C11 Cl3 112.24(9) . . ?
C10 C11 Cl4 106.86(9) . . ?
C10 C11 H11 111.0(10) . . ?
C12 O5 H5B 109.2 . . ?
O5 C12 H12A 109.1(10) . . ?
O5 C12 H12B 110.6(12) . . ?
O5 C12 C13 108.55(13) . . ?
H12A C12 H12B 109.3(16) . . ?
C13 C12 H12A 110.0(11) . . ?
C13 C12 H12B 109.2(11) . . ?
C12 C13 H13A 111.2(12) . . ?
C12 C13 H13B 109.7(13) . . ?
C12 C13 H13C 110.9(12) . . ?
H13A C13 H13B 110.5(18) . . ?
H13A C13 H13C 107.8(17) . . ?
H13B C13 H13C 106.6(18) . . ?

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 O5 0.88 1.89 2.7640(16) 170.3 .
N4 H4 O4 0.88 1.84 2.7012(15) 164.9 .
N5 H5 O3 0.88 1.88 2.7606(15) 177.1 .
O5 H5B O3 0.84 1.91 2.7390(15) 167.1 1_556

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 C6 N4 -4.03(11) . . . . ?
Cu1 S1 C6 N5 175.38(11) . . . . ?
Cu1 O1 C8 O2 7.31(17) . . . . ?
Cu1 O1 C8 C9 -170.29(9) . . . . ?
Cu1 N1 C1 C2 172.05(8) . . . . ?
Cu1 N1 C1 C5 -5.59(14) . . . . ?
Cu1 N1 C4 N2 -168.73(10) . . . . ?
Cu1 N3 N4 C6 -1.16(15) . . . . ?
Cu1 N3 C5 C1 -0.03(15) . . . . ?
S1 Cu1 O1 C8 77.75(8) . . . . ?
S1 Cu1 N1 C1 16.85(18) . . . . ?
S1 Cu1 N1 C4 -174.65(10) . . . . ?
S1 Cu1 N3 N4 -1.12(9) . . . . ?
S1 Cu1 N3 C5 -178.96(10) . . . . ?
O2 C8 C9 Cl1 -106.92(12) . . . . ?
O2 C8 C9 Cl2 130.59(11) . . . . ?
O1 Cu1 S1 C6 -168.76(5) . . . . ?
O1 Cu1 N1 C1 175.25(8) . . . . ?
O1 Cu1 N1 C4 -16.25(15) . . . . ?
O1 Cu1 N3 N4 89.6(3) . . . . ?
O1 Cu1 N3 C5 -88.2(3) . . . . ?
O1 C8 C9 Cl1 70.93(13) . . . . ?
O1 C8 C9 Cl2 -51.56(14) . . . . ?
N1 Cu1 S1 C6 -10.21(13) . . . . ?
N1 Cu1 O1 C8 -96.50(9) . . . . ?
N1 Cu1 N3 N4 175.46(10) . . . . ?
N1 Cu1 N3 C5 -2.38(10) . . . . ?
N1 C1 C2 N2 0.66(14) . . . . ?
N1 C1 C2 C3 -175.99(14) . . . . ?
N1 C1 C5 N3 3.80(16) . . . . ?
N3 Cu1 S1 C6 2.34(5) . . . . ?
N3 Cu1 O1 C8 -12.1(3) . . . . ?
N3 Cu1 N1 C1 4.18(8) . . . . ?
N3 Cu1 N1 C4 172.68(15) . . . . ?
N3 N4 C6 S1 3.86(16) . . . . ?
N3 N4 C6 N5 -175.59(11) . . . . ?
N4 N3 C5 C1 -177.84(11) . . . . ?
C1 N1 C4 N2 0.16(15) . . . . ?
C2 N2 C4 N1 0.25(15) . . . . ?
C2 C1 C5 N3 -173.09(14) . . . . ?
C4 N1 C1 C2 -0.52(14) . . . . ?
C4 N1 C1 C5 -178.15(11) . . . . ?
C4 N2 C2 C1 -0.56(14) . . . . ?
C4 N2 C2 C3 176.47(13) . . . . ?
C5 N3 N4 C6 176.60(12) . . . . ?
C5 C1 C2 N2 177.70(14) . . . . ?
C5 C1 C2 C3 1.1(3) . . . . ?
C7 N5 C6 S1 1.18(19) . . . . ?
C7 N5 C6 N4 -179.38(13) . . . . ?
O3 C10 C11 Cl3 33.82(15) . . . . ?
O3 C10 C11 Cl4 -87.43(13) . . . . ?
O4 C10 C11 Cl3 -148.58(10) . . . . ?
O4 C10 C11 Cl4 90.17(12) . . . . ?


_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_ls41_0ma
_database_code_depnum_ccdc_archive 'CCDC 1845472'
_audit_update_record             
;
2018-10-31 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_audit_creation_date             2017-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H10 Cl2 Cu N5 O2 S, C2 H Cl2 O2'
_chemical_formula_sum            'C10 H11 Cl4 Cu N5 O4 S'
_chemical_formula_weight         502.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.0981(7)
_cell_length_b                   21.8935(15)
_cell_length_c                   17.1161(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.756(3)
_cell_angle_gamma                90.00
_cell_volume                     3623.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3603
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      2.85
_cell_measurement_theta_min      23.98
_exptl_absorpt_coefficient_mu    1.937
_exptl_absorpt_correction_T_max  0.7599
_exptl_absorpt_correction_T_min  0.6228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_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    1.843
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2008
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            82072
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.11
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5787
_reflns_number_total             6328
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0223
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0197P)²+4.1322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0507
_refine_ls_wR_factor_ref         0.0524
_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
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H) groups
2.a Riding coordinates:
 N2A(H2A), N4A(H4A), N5A(H5AA,H5AB), N2B(H2B), N4B(H4B), N5B(H5BA,H5BB)
2.b Ternary CH refined with riding coordinates:
 C8A(H8A), C8B(H8B), C10A(H10A), C10B(H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C4A(H4AA), C5A(H5A), C4B(H4BA), C5B(H5B)
2.d Idealised Me refined as rotating group:
 C3A(H3AA,H3AB,H3AC), C3B(H3BA,H3BB,H3BC)
;
_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
Cu1A Cu -0.10710(2) 0.483725(10) 0.403753(14) 0.01201(6) Uani 1 d . . .
Cl1A Cl -0.26848(7) 0.42749(3) 0.62915(4) 0.03812(16) Uani 1 d . . .
Cl2A Cl -0.23800(5) 0.56022(3) 0.64475(3) 0.02726(13) Uani 1 d . . .
S1A S -0.10711(5) 0.37995(2) 0.41862(3) 0.01669(11) Uani 1 d . . .
O1A O -0.13773(13) 0.50113(6) 0.50922(8) 0.0143(3) Uani 1 d . . .
O2A O -0.35900(14) 0.49236(6) 0.43611(9) 0.0184(3) Uani 1 d . . .
N1A N -0.11625(16) 0.56844(7) 0.35955(10) 0.0128(3) Uani 1 d . . .
N2A N -0.08770(17) 0.66341(7) 0.32675(11) 0.0164(4) Uani 1 d . . .
H2A H -0.0828 0.7035 0.3300 0.020 Uiso 1 d . . R
N3A N -0.08689(16) 0.46555(7) 0.29481(10) 0.0118(3) Uani 1 d . . .
N4A N -0.08026(16) 0.40618(7) 0.27088(10) 0.0133(3) Uani 1 d . . .
H4A H -0.0714 0.3969 0.2226 0.016 Uiso 1 d . . R
N5A N -0.08150(19) 0.30528(8) 0.30177(11) 0.0224(4) Uani 1 d . . .
H5AA H -0.0617 0.2963 0.2584 0.034 Uiso 1 d . . R
H5AB H -0.0860 0.2772 0.3353 0.034 Uiso 1 d . . R
C1A C -0.08702(19) 0.56928(9) 0.28480(12) 0.0123(4) Uani 1 d . . .
C2A C -0.0682(2) 0.62857(9) 0.26394(12) 0.0150(4) Uani 1 d . . .
C3A C -0.0276(2) 0.65434(10) 0.19397(14) 0.0229(5) Uani 1 d . . .
H3AA H 0.0694 0.6672 0.2124 0.034 Uiso 1 calc . . GR
H3AB H -0.0862 0.6896 0.1719 0.034 Uiso 1 calc . . GR
H3AC H -0.0391 0.6232 0.1514 0.034 Uiso 1 calc . . GR
C4A C -0.1158(2) 0.62573(9) 0.38230(13) 0.0159(4) Uani 1 d . . .
H4AA H -0.1331 0.6389 0.4314 0.019 Uiso 1 calc . . R
C5A C -0.07551(18) 0.51092(9) 0.24909(12) 0.0128(4) Uani 1 d . . .
H5A H -0.0610 0.5062 0.1970 0.015 Uiso 1 calc . . R
C6A C -0.0879(2) 0.36292(9) 0.32489(13) 0.0152(4) Uani 1 d . . .
C7A C -0.2679(2) 0.49828(9) 0.50095(13) 0.0147(4) Uani 1 d . . .
C8A C -0.3136(2) 0.49899(11) 0.57859(13) 0.0235(5) Uani 1 d . . .
H8A H -0.4164 0.5035 0.5629 0.028 Uiso 1 calc . . R
Cu1B Cu -0.39587(2) 0.531179(10) 0.088962(14) 0.01101(6) Uani 1 d . . .
Cl1B Cl -0.24069(5) 0.38612(2) -0.07243(3) 0.02412(12) Uani 1 d . . .
Cl2B Cl -0.22404(6) 0.49895(3) -0.16050(3) 0.02690(13) Uani 1 d . . .
S1B S -0.39004(5) 0.63405(2) 0.06730(3) 0.01504(11) Uani 1 d . . .
O1B O -0.36066(13) 0.49769(6) -0.00928(8) 0.0133(3) Uani 1 d . . .
O2B O -0.14472(14) 0.52969(7) 0.04831(9) 0.0203(3) Uani 1 d . . .
N1B N -0.38174(16) 0.44941(7) 0.14179(10) 0.0121(3) Uani 1 d . . .
N2B N -0.39525(16) 0.35605(7) 0.18462(10) 0.0139(3) Uani 1 d . . .
H2B H -0.3926 0.3159 0.1861 0.017 Uiso 1 d . . R
N3B N -0.42600(15) 0.55489(7) 0.19380(10) 0.0113(3) Uani 1 d . . .
N4B N -0.43698(16) 0.61531(7) 0.21181(10) 0.0133(3) Uani 1 d . . .
H4B H -0.4512 0.6268 0.2580 0.016 Uiso 1 d . . R
N5B N -0.4402(2) 0.71418(8) 0.17205(11) 0.0236(4) Uani 1 d . . .
H5BA H -0.4297 0.7416 0.1390 0.035 Uiso 1 d . . R
H5BB H -0.4677 0.7249 0.2127 0.035 Uiso 1 d . . R
C1B C -0.41663(18) 0.45170(9) 0.21470(12) 0.0120(4) Uani 1 d . . .
C2B C -0.42624(19) 0.39325(9) 0.24187(12) 0.0131(4) Uani 1 d . . .
C3B C -0.4658(2) 0.36863(9) 0.31291(13) 0.0173(4) Uani 1 d . . .
H3BA H -0.4598 0.4012 0.3531 0.026 Uiso 1 calc . . GR
H3BB H -0.4029 0.3354 0.3379 0.026 Uiso 1 calc . . GR
H3BC H -0.5608 0.3531 0.2946 0.026 Uiso 1 calc . . GR
C4B C -0.36967(19) 0.39133(9) 0.12595(12) 0.0131(4) Uani 1 d . . .
H4BA H -0.3462 0.3762 0.0796 0.016 Uiso 1 calc . . R
C5B C -0.43544(19) 0.51208(9) 0.24383(12) 0.0123(4) Uani 1 d . . .
H5B H -0.4530 0.5195 0.2946 0.015 Uiso 1 calc . . R
C6B C -0.4251(2) 0.65580(9) 0.15582(12) 0.0151(4) Uani 1 d . . .
C7B C -0.2311(2) 0.50024(8) -0.00306(12) 0.0130(4) Uani 1 d . . .
C8B C -0.1780(2) 0.46278(9) -0.06359(13) 0.0169(4) Uani 1 d . . .
H8B H -0.0748 0.4614 -0.0429 0.020 Uiso 1 calc . . R
Cl3A Cl 0.05774(8) 0.26167(2) 0.00167(4) 0.03618(15) Uani 1 d . . .
Cl4A Cl 0.27438(6) 0.33476(3) 0.11123(4) 0.04043(16) Uani 1 d . . .
O3A O -0.03643(15) 0.38416(6) 0.12887(9) 0.0208(3) Uani 1 d . . .
O4A O 0.01511(16) 0.28687(6) 0.16581(10) 0.0248(4) Uani 1 d . . .
C9A C 0.0164(2) 0.33325(9) 0.12372(13) 0.0164(4) Uani 1 d . . .
C10A C 0.0949(2) 0.33035(9) 0.05905(13) 0.0186(4) Uani 1 d . . .
H10A H 0.0679 0.3661 0.0214 0.022 Uiso 1 calc . . R
Cl3B Cl -0.41160(7) 0.67607(3) 0.52657(4) 0.03479(15) Uani 1 d . . .
Cl4B Cl -0.67490(7) 0.73572(3) 0.44735(4) 0.03722(16) Uani 1 d . . .
O3B O -0.43753(15) 0.65138(6) 0.35852(9) 0.0218(3) Uani 1 d . . .
O4B O -0.55551(15) 0.73487(6) 0.30269(9) 0.0212(3) Uani 1 d . . .
C9B C -0.4984(2) 0.70017(9) 0.36143(13) 0.0169(4) Uani 1 d . . .
C10B C -0.5014(2) 0.72434(9) 0.44555(13) 0.0210(5) Uani 1 d . . .
H10B H -0.4543 0.7650 0.4540 0.025 Uiso 1 calc . . 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
Cu1A S1A 2.2862(6) . ?
Cu1A O1A 1.9549(13) . ?
Cu1A N1A 1.9951(16) . ?
Cu1A N3A 1.9739(16) . ?
Cl1A C8A 1.783(2) . ?
Cl2A C8A 1.779(2) . ?
S1A C6A 1.711(2) . ?
O1A C7A 1.283(2) . ?
O2A C7A 1.227(2) . ?
N1A C1A 1.394(2) . ?
N1A C4A 1.313(3) . ?
N2A H2A 0.8800 . ?
N2A C2A 1.378(3) . ?
N2A C4A 1.350(3) . ?
N3A N4A 1.370(2) . ?
N3A C5A 1.290(3) . ?
N4A H4A 0.8795 . ?
N4A C6A 1.341(3) . ?
N5A H5AA 0.8463 . ?
N5A H5AB 0.8511 . ?
N5A C6A 1.330(3) . ?
C1A C2A 1.374(3) . ?
C1A C5A 1.436(3) . ?
C2A C3A 1.485(3) . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C4A H4AA 0.9500 . ?
C5A H5A 0.9500 . ?
C7A C8A 1.527(3) . ?
C8A H8A 1.0000 . ?
Cu1B S1B 2.2861(5) . ?
Cu1B O1B 1.9586(13) . ?
Cu1B N1B 1.9921(16) . ?
Cu1B N3B 1.9740(16) . ?
Cl1B C8B 1.785(2) . ?
Cl2B C8B 1.775(2) . ?
S1B C6B 1.720(2) . ?
O1B C7B 1.283(2) . ?
O2B C7B 1.228(2) . ?
N1B C1B 1.392(2) . ?
N1B C4B 1.313(2) . ?
N2B H2B 0.8800 . ?
N2B C2B 1.378(3) . ?
N2B C4B 1.350(3) . ?
N3B N4B 1.370(2) . ?
N3B C5B 1.292(2) . ?
N4B H4B 0.8805 . ?
N4B C6B 1.336(3) . ?
N5B H5BA 0.8521 . ?
N5B H5BB 0.8531 . ?
N5B C6B 1.326(3) . ?
C1B C2B 1.374(3) . ?
C1B C5B 1.445(3) . ?
C2B C3B 1.486(3) . ?
C3B H3BA 0.9800 . ?
C3B H3BB 0.9800 . ?
C3B H3BC 0.9800 . ?
C4B H4BA 0.9500 . ?
C5B H5B 0.9500 . ?
C7B C8B 1.534(3) . ?
C8B H8B 1.0000 . ?
Cl3A C10A 1.776(2) . ?
Cl4A C10A 1.777(2) . ?
O3A C9A 1.249(2) . ?
O4A C9A 1.247(2) . ?
C9A C10A 1.538(3) . ?
C10A H10A 1.0000 . ?
Cl3B C10B 1.771(2) . ?
Cl4B C10B 1.779(2) . ?
O3B C9B 1.241(2) . ?
O4B C9B 1.259(3) . ?
C9B C10B 1.542(3) . ?
C10B H10B 1.0000 . ?

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
O1A Cu1A S1A 94.93(4) . . ?
O1A Cu1A N1A 99.59(6) . . ?
O1A Cu1A N3A 176.95(6) . . ?
N1A Cu1A S1A 164.70(5) . . ?
N3A Cu1A S1A 84.73(5) . . ?
N3A Cu1A N1A 80.52(6) . . ?
C6A S1A Cu1A 96.23(7) . . ?
C7A O1A Cu1A 108.58(12) . . ?
C1A N1A Cu1A 111.19(12) . . ?
C4A N1A Cu1A 141.23(14) . . ?
C4A N1A C1A 106.04(16) . . ?
C2A N2A H2A 125.7 . . ?
C4A N2A H2A 125.7 . . ?
C4A N2A C2A 108.54(16) . . ?
N4A N3A Cu1A 120.06(12) . . ?
C5A N3A Cu1A 118.00(13) . . ?
C5A N3A N4A 121.90(16) . . ?
N3A N4A H4A 121.7 . . ?
C6A N4A N3A 116.50(16) . . ?
C6A N4A H4A 121.8 . . ?
H5AA N5A H5AB 119.8 . . ?
C6A N5A H5AA 121.7 . . ?
C6A N5A H5AB 117.9 . . ?
N1A C1A C5A 116.34(16) . . ?
C2A C1A N1A 109.45(17) . . ?
C2A C1A C5A 134.11(18) . . ?
N2A C2A C3A 123.64(18) . . ?
C1A C2A N2A 104.98(17) . . ?
C1A C2A C3A 131.29(18) . . ?
C2A C3A H3AA 109.5 . . ?
C2A C3A H3AB 109.5 . . ?
C2A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
N1A C4A N2A 110.99(18) . . ?
N1A C4A H4AA 124.5 . . ?
N2A C4A H4AA 124.5 . . ?
N3A C5A C1A 113.25(17) . . ?
N3A C5A H5A 123.4 . . ?
C1A C5A H5A 123.4 . . ?
N4A C6A S1A 122.47(15) . . ?
N5A C6A S1A 120.94(15) . . ?
N5A C6A N4A 116.58(18) . . ?
O1A C7A C8A 117.42(18) . . ?
O2A C7A O1A 125.59(18) . . ?
O2A C7A C8A 116.91(17) . . ?
Cl1A C8A H8A 108.5 . . ?
Cl2A C8A Cl1A 110.48(12) . . ?
Cl2A C8A H8A 108.5 . . ?
C7A C8A Cl1A 108.33(15) . . ?
C7A C8A Cl2A 112.33(15) . . ?
C7A C8A H8A 108.5 . . ?
O1B Cu1B S1B 102.12(4) . . ?
O1B Cu1B N1B 92.65(6) . . ?
O1B Cu1B N3B 173.00(6) . . ?
N1B Cu1B S1B 163.17(5) . . ?
N3B Cu1B S1B 84.62(5) . . ?
N3B Cu1B N1B 80.41(6) . . ?
C6B S1B Cu1B 96.22(7) . . ?
C7B O1B Cu1B 110.22(12) . . ?
C1B N1B Cu1B 111.78(12) . . ?
C4B N1B Cu1B 140.84(14) . . ?
C4B N1B C1B 106.41(16) . . ?
C2B N2B H2B 125.6 . . ?
C4B N2B H2B 125.6 . . ?
C4B N2B C2B 108.79(16) . . ?
N4B N3B Cu1B 120.14(12) . . ?
C5B N3B Cu1B 118.17(13) . . ?
C5B N3B N4B 121.69(16) . . ?
N3B N4B H4B 121.6 . . ?
C6B N4B N3B 116.72(16) . . ?
C6B N4B H4B 121.7 . . ?
H5BA N5B H5BB 118.8 . . ?
C6B N5B H5BA 119.7 . . ?
C6B N5B H5BB 121.3 . . ?
N1B C1B C5B 115.78(16) . . ?
C2B C1B N1B 109.31(16) . . ?
C2B C1B C5B 134.91(18) . . ?
N2B C2B C3B 122.49(17) . . ?
C1B C2B N2B 104.90(16) . . ?
C1B C2B C3B 132.57(18) . . ?
C2B C3B H3BA 109.5 . . ?
C2B C3B H3BB 109.5 . . ?
C2B C3B H3BC 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
N1B C4B N2B 110.59(17) . . ?
N1B C4B H4BA 124.7 . . ?
N2B C4B H4BA 124.7 . . ?
N3B C5B C1B 113.14(17) . . ?
N3B C5B H5B 123.4 . . ?
C1B C5B H5B 123.4 . . ?
N4B C6B S1B 122.14(15) . . ?
N5B C6B S1B 121.10(15) . . ?
N5B C6B N4B 116.76(18) . . ?
O1B C7B C8B 117.86(17) . . ?
O2B C7B O1B 125.40(18) . . ?
O2B C7B C8B 116.73(17) . . ?
Cl1B C8B H8B 108.0 . . ?
Cl2B C8B Cl1B 110.45(11) . . ?
Cl2B C8B H8B 108.0 . . ?
C7B C8B Cl1B 112.05(13) . . ?
C7B C8B Cl2B 110.13(14) . . ?
C7B C8B H8B 108.0 . . ?
O3A C9A C10A 114.00(17) . . ?
O4A C9A O3A 127.58(19) . . ?
O4A C9A C10A 118.38(17) . . ?
Cl3A C10A Cl4A 110.27(11) . . ?
Cl3A C10A H10A 109.3 . . ?
Cl4A C10A H10A 109.3 . . ?
C9A C10A Cl3A 111.25(14) . . ?
C9A C10A Cl4A 107.40(14) . . ?
C9A C10A H10A 109.3 . . ?
O3B C9B O4B 127.26(19) . . ?
O3B C9B C10B 118.43(18) . . ?
O4B C9B C10B 114.24(17) . . ?
Cl3B C10B Cl4B 110.76(11) . . ?
Cl3B C10B H10B 107.6 . . ?
Cl4B C10B H10B 107.6 . . ?
C9B C10B Cl3B 112.52(14) . . ?
C9B C10B Cl4B 110.40(15) . . ?
C9B C10B H10B 107.6 . . ?

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
N2A H2A O4A 0.88 1.94 2.794(2) 162.2 2
N4A H4A O3A 0.88 1.76 2.638(2) 173.2 .
N5A H5AA O4A 0.85 1.97 2.800(2) 168.6 .
N5A H5AB Cl3A 0.85 2.93 3.6136(19) 139.3 4_566
N2B H2B O4B 0.88 1.87 2.719(2) 160.2 2_445
N4B H4B O3B 0.88 1.77 2.634(2) 166.7 .
N5B H5BA Cl3B 0.85 2.68 3.5314(18) 175.9 4_575
N5B H5BB O4B 0.85 2.00 2.840(2) 168.5 .

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
Cu1A S1A C6A N4A -0.89(17) . . . . ?
Cu1A S1A C6A N5A 179.92(16) . . . . ?
Cu1A O1A C7A O2A -7.4(2) . . . . ?
Cu1A O1A C7A C8A 169.26(14) . . . . ?
Cu1A N1A C1A C2A -168.55(13) . . . . ?
Cu1A N1A C1A C5A 8.2(2) . . . . ?
Cu1A N1A C4A N2A 163.32(15) . . . . ?
Cu1A N3A N4A C6A -0.1(2) . . . . ?
Cu1A N3A C5A C1A -3.1(2) . . . . ?
S1A Cu1A O1A C7A -84.14(12) . . . . ?
S1A Cu1A N1A C1A -22.9(3) . . . . ?
S1A Cu1A N1A C4A 174.10(15) . . . . ?
S1A Cu1A N3A N4A -0.34(12) . . . . ?
S1A Cu1A N3A C5A -177.99(14) . . . . ?
O1A Cu1A S1A C6A 177.51(8) . . . . ?
O1A Cu1A N1A C1A 175.70(12) . . . . ?
O1A Cu1A N1A C4A 12.7(2) . . . . ?
O1A Cu1A N3A N4A -84.0(11) . . . . ?
O1A Cu1A N3A C5A 98.4(11) . . . . ?
O1A C7A C8A Cl1A -71.6(2) . . . . ?
O1A C7A C8A Cl2A 50.7(2) . . . . ?
O2A C7A C8A Cl1A 105.33(18) . . . . ?
O2A C7A C8A Cl2A -132.35(17) . . . . ?
N1A Cu1A S1A C6A 15.94(19) . . . . ?
N1A Cu1A O1A C7A 91.01(13) . . . . ?
N1A Cu1A N3A N4A -176.27(14) . . . . ?
N1A Cu1A N3A C5A 6.08(14) . . . . ?
N1A C1A C2A N2A -0.5(2) . . . . ?
N1A C1A C2A C3A 176.0(2) . . . . ?
N1A C1A C5A N3A -3.6(2) . . . . ?
N3A Cu1A S1A C6A 0.55(8) . . . . ?
N3A Cu1A O1A C7A -0.8(12) . . . . ?
N3A Cu1A N1A C1A -7.40(12) . . . . ?
N3A Cu1A N1A C4A -170.4(2) . . . . ?
N3A N4A C6A S1A 0.8(2) . . . . ?
N3A N4A C6A N5A -179.99(16) . . . . ?
N4A N3A C5A C1A 179.26(15) . . . . ?
C1A N1A C4A N2A -0.2(2) . . . . ?
C2A N2A C4A N1A -0.2(2) . . . . ?
C2A C1A C5A N3A 172.2(2) . . . . ?
C4A N1A C1A C2A 0.4(2) . . . . ?
C4A N1A C1A C5A 177.22(17) . . . . ?
C4A N2A C2A C1A 0.4(2) . . . . ?
C4A N2A C2A C3A -176.47(19) . . . . ?
C5A N3A N4A C6A 177.43(17) . . . . ?
C5A C1A C2A N2A -176.5(2) . . . . ?
C5A C1A C2A C3A 0.1(4) . . . . ?
Cu1B S1B C6B N4B 4.04(17) . . . . ?
Cu1B S1B C6B N5B -176.76(17) . . . . ?
Cu1B O1B C7B O2B -13.3(2) . . . . ?
Cu1B O1B C7B C8B 165.62(13) . . . . ?
Cu1B N1B C1B C2B 170.65(12) . . . . ?
Cu1B N1B C1B C5B -8.8(2) . . . . ?
Cu1B N1B C4B N2B -166.72(15) . . . . ?
Cu1B N3B N4B C6B -0.5(2) . . . . ?
Cu1B N3B C5B C1B 2.2(2) . . . . ?
S1B Cu1B O1B C7B 78.98(12) . . . . ?
S1B Cu1B N1B C1B 35.0(2) . . . . ?
S1B Cu1B N1B C4B -158.53(15) . . . . ?
S1B Cu1B N3B N4B 2.47(12) . . . . ?
S1B Cu1B N3B C5B -177.83(14) . . . . ?
O1B Cu1B S1B C6B 178.94(8) . . . . ?
O1B Cu1B N1B C1B -173.42(12) . . . . ?
O1B Cu1B N1B C4B -7.0(2) . . . . ?
O1B Cu1B N3B N4B 167.1(4) . . . . ?
O1B Cu1B N3B C5B -13.2(6) . . . . ?
O1B C7B C8B Cl1B -47.7(2) . . . . ?
O1B C7B C8B Cl2B 75.70(19) . . . . ?
O2B C7B C8B Cl1B 131.37(16) . . . . ?
O2B C7B C8B Cl2B -105.27(18) . . . . ?
N1B Cu1B S1B C6B -30.19(18) . . . . ?
N1B Cu1B O1B C7B -92.91(12) . . . . ?
N1B Cu1B N3B N4B 174.74(14) . . . . ?
N1B Cu1B N3B C5B -5.55(14) . . . . ?
N1B C1B C2B N2B 0.6(2) . . . . ?
N1B C1B C2B C3B -176.8(2) . . . . ?
N1B C1B C5B N3B 4.6(2) . . . . ?
N3B Cu1B S1B C6B -2.95(8) . . . . ?
N3B Cu1B O1B C7B -85.4(5) . . . . ?
N3B Cu1B N1B C1B 7.50(12) . . . . ?
N3B Cu1B N1B C4B 173.9(2) . . . . ?
N3B N4B C6B S1B -2.9(2) . . . . ?
N3B N4B C6B N5B 177.90(17) . . . . ?
N4B N3B C5B C1B -178.12(15) . . . . ?
C1B N1B C4B N2B 0.2(2) . . . . ?
C2B N2B C4B N1B 0.2(2) . . . . ?
C2B C1B C5B N3B -174.7(2) . . . . ?
C4B N1B C1B C2B -0.5(2) . . . . ?
C4B N1B C1B C5B -179.92(16) . . . . ?
C4B N2B C2B C1B -0.5(2) . . . . ?
C4B N2B C2B C3B 177.21(18) . . . . ?
C5B N3B N4B C6B 179.77(18) . . . . ?
C5B C1B C2B N2B 179.9(2) . . . . ?
C5B C1B C2B C3B 2.5(4) . . . . ?
O3A C9A C10A Cl3A -136.77(16) . . . . ?
O3A C9A C10A Cl4A 102.48(18) . . . . ?
O4A C9A C10A Cl3A 45.2(2) . . . . ?
O4A C9A C10A Cl4A -75.6(2) . . . . ?
O3B C9B C10B Cl3B 0.6(2) . . . . ?
O3B C9B C10B Cl4B -123.70(17) . . . . ?
O4B C9B C10B Cl3B -176.71(15) . . . . ?
O4B C9B C10B Cl4B 59.0(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
