# 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_exp_370
_database_code_depnum_ccdc_archive 'CCDC 1818325'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT601_exp_370             
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .         35 Ang**3
RESPONSE: This void is relatively small to include water molecule (40 ang***3. The higest difference peak = 0.89. Using Olex2 program to analyze the electron density map indicated that there is no electron density in the voids. I think the void is empty
;
# Added during the CSD deposition process: Saturday 20 January 2018 07:36 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 Br2 Cl4 Cu N2'
_chemical_formula_weight         519.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1'

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

_cell_length_a                   15.5239(16)
_cell_length_b                   14.3008(8)
_cell_length_c                   7.9558(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.373(12)
_cell_angle_gamma                90.00
_cell_volume                     1554.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1555
_cell_measurement_theta_min      2.9260
_cell_measurement_theta_max      28.7713

_exptl_crystal_description       parrallelpiped
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             988
_exptl_absorpt_coefficient_mu    7.220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3569
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         26.29
_reflns_number_total             1639
_reflns_number_gt                1360
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_structure_solution    'shelxtl, Bruker,2002'
_computing_structure_refinement  'shelxtl, Bruker,2002'
_computing_molecular_graphics    'shelxtl, Bruker,2002'
_computing_publication_material  'shelxtl, Bruker,2002'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0339P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1639
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0697
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.11576(4) 0.0000 0.22219(7) 0.02389(16) Uani 1 2 d S . .
Br1 Br 0.14730(3) 0.36023(3) -0.06822(5) 0.04983(16) Uani 1 1 d . . .
Cl3 Cl -0.04703(8) 0.0000 0.15372(14) 0.0255(3) Uani 1 2 d S . .
Cl2 Cl 0.28017(9) 0.0000 0.33590(17) 0.0338(3) Uani 1 2 d S . .
Cl1 Cl 0.12283(8) 0.11985(7) 0.57024(12) 0.0430(3) Uani 1 1 d . . .
N1 N 0.12064(18) 0.14339(18) 0.2433(4) 0.0257(6) Uani 1 1 d . . .
C4 C 0.1320(2) 0.2909(2) 0.1174(5) 0.0320(8) Uani 1 1 d . . .
C1 C 0.1218(2) 0.1876(2) 0.3917(4) 0.0297(8) Uani 1 1 d . . .
C5 C 0.1266(2) 0.1951(2) 0.1072(5) 0.0304(8) Uani 1 1 d . . .
H5A H 0.1269 0.1650 0.0039 0.036 Uiso 1 1 calc R . .
C3 C 0.1306(3) 0.3358(3) 0.2690(5) 0.0414(9) Uani 1 1 d . . .
H3A H 0.1330 0.4008 0.2765 0.050 Uiso 1 1 calc R . .
C2 C 0.1255(3) 0.2837(3) 0.4093(5) 0.0405(9) Uani 1 1 d . . .
H2A H 0.1245 0.3124 0.5132 0.049 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0288(3) 0.0175(3) 0.0271(3) 0.000 0.0146(3) 0.000
Br1 0.0686(3) 0.0334(2) 0.0480(3) 0.00813(17) 0.0281(2) -0.0082(2)
Cl3 0.0301(6) 0.0248(6) 0.0245(5) 0.000 0.0154(5) 0.000
Cl2 0.0308(7) 0.0290(6) 0.0410(7) 0.000 0.0166(6) 0.000
Cl1 0.0584(6) 0.0414(6) 0.0345(5) -0.0047(4) 0.0264(5) -0.0144(5)
N1 0.0261(15) 0.0196(14) 0.0311(15) -0.0032(11) 0.0134(13) -0.0040(12)
C4 0.033(2) 0.0239(18) 0.037(2) 0.0030(15) 0.0142(17) -0.0027(16)
C1 0.0316(19) 0.0272(19) 0.0302(18) -0.0057(14) 0.0146(15) -0.0063(15)
C5 0.034(2) 0.0260(19) 0.0344(19) -0.0026(15) 0.0191(17) -0.0032(16)
C3 0.049(2) 0.0197(18) 0.057(2) -0.0035(17) 0.027(2) -0.0022(17)
C2 0.050(2) 0.032(2) 0.045(2) -0.0135(17) 0.0274(19) -0.0037(18)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.056(3) 6 ?
Cu1 N1 2.056(3) . ?
Cu1 Cl2 2.2666(13) . ?
Cu1 Cl3 2.3184(12) . ?
Cu1 Cl3 2.6551(12) 5 ?
Br1 C4 1.885(3) . ?
Cl3 Cu1 2.6551(12) 5 ?
Cl1 C1 1.713(3) . ?
N1 C1 1.332(4) . ?
N1 C5 1.350(4) . ?
C4 C5 1.373(5) . ?
C4 C3 1.376(5) . ?
C1 C2 1.380(5) . ?
C5 H5A 0.9300 . ?
C3 C2 1.376(5) . ?
C3 H3A 0.9300 . ?
C2 H2A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 171.74(14) 6 . ?
N1 Cu1 Cl2 88.66(7) 6 . ?
N1 Cu1 Cl2 88.66(7) . . ?
N1 Cu1 Cl3 90.74(7) 6 . ?
N1 Cu1 Cl3 90.74(7) . . ?
Cl2 Cu1 Cl3 171.37(4) . . ?
N1 Cu1 Cl3 94.11(7) 6 5 ?
N1 Cu1 Cl3 94.11(7) . 5 ?
Cl2 Cu1 Cl3 102.89(5) . 5 ?
Cl3 Cu1 Cl3 85.73(4) . 5 ?
Cu1 Cl3 Cu1 94.27(4) . 5 ?
C1 N1 C5 118.3(3) . . ?
C1 N1 Cu1 122.0(2) . . ?
C5 N1 Cu1 119.6(2) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 Br1 120.4(3) . . ?
C3 C4 Br1 120.1(3) . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 Cl1 117.2(3) . . ?
C2 C1 Cl1 119.7(3) . . ?
N1 C5 C4 121.6(3) . . ?
N1 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 Cl3 Cu1 -94.06(7) 6 . . 5 ?
N1 Cu1 Cl3 Cu1 94.06(7) . . . 5 ?
Cl2 Cu1 Cl3 Cu1 180.0 . . . 5 ?
Cl3 Cu1 Cl3 Cu1 0.0 5 . . 5 ?
N1 Cu1 N1 C1 -27.0(12) 6 . . . ?
Cl2 Cu1 N1 C1 -98.2(3) . . . . ?
Cl3 Cu1 N1 C1 73.2(3) . . . . ?
Cl3 Cu1 N1 C1 159.0(3) 5 . . . ?
N1 Cu1 N1 C5 150.4(9) 6 . . . ?
Cl2 Cu1 N1 C5 79.3(2) . . . . ?
Cl3 Cu1 N1 C5 -109.3(2) . . . . ?
Cl3 Cu1 N1 C5 -23.5(2) 5 . . . ?
C5 N1 C1 C2 2.2(5) . . . . ?
Cu1 N1 C1 C2 179.7(3) . . . . ?
C5 N1 C1 Cl1 -175.6(2) . . . . ?
Cu1 N1 C1 Cl1 1.9(4) . . . . ?
C1 N1 C5 C4 -1.1(5) . . . . ?
Cu1 N1 C5 C4 -178.6(3) . . . . ?
C3 C4 C5 N1 -0.6(5) . . . . ?
Br1 C4 C5 N1 176.6(2) . . . . ?
C5 C4 C3 C2 1.2(5) . . . . ?
Br1 C4 C3 C2 -176.0(3) . . . . ?
C4 C3 C2 C1 -0.1(6) . . . . ?
N1 C1 C2 C3 -1.6(6) . . . . ?
Cl1 C1 C2 C3 176.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.29
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.091
####################################################################### 
# 
# 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_exp_1408
_database_code_depnum_ccdc_archive 'CCDC 1818328'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;

_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 Cl6 Cu N2'
_chemical_formula_sum            'C10 H6 Cl6 Cu N2'
_chemical_formula_weight         430.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'

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

_cell_length_a                   8.1852(4)
_cell_length_b                   12.5785(6)
_cell_length_c                   14.5850(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.223(4)
_cell_angle_gamma                90.00
_cell_volume                     1501.29(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1169
_cell_measurement_theta_min      1169
_cell_measurement_theta_max      29.3466

_exptl_crystal_description       parallelpiped
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    2.506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87321
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3288
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         26.30
_reflns_number_total             1529
_reflns_number_gt                1278
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_structure_solution    'shelxtl, Bruker,2002'
_computing_structure_refinement  'shelxtl, Bruker,2002'
_computing_molecular_graphics    'shelxtl, Bruker,2002'
_computing_publication_material  'shelxtl, Bruker,2002'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0259P)²+0.1393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1529
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0665
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.29970(3) 0.7500 0.02960(15) Uani 1 2 d S . .
Cl3 Cl 0.75582(8) 0.35809(6) 0.74291(4) 0.03945(19) Uani 1 1 d . . .
Cl1 Cl 0.63567(10) 0.09100(6) 0.65101(5) 0.0524(2) Uani 1 1 d . . .
Cl2 Cl 0.34279(9) 0.43138(6) 0.39453(5) 0.0484(2) Uani 1 1 d . . .
N1 N 0.4865(2) 0.27019(16) 0.61428(13) 0.0289(5) Uani 1 1 d . . .
C1 C 0.5560(3) 0.1851(2) 0.57663(17) 0.0335(6) Uani 1 1 d . . .
C5 C 0.4212(3) 0.3432(2) 0.55756(17) 0.0323(6) Uani 1 1 d . . .
H5A H 0.3708 0.4026 0.5823 0.039 Uiso 1 1 calc R . .
C4 C 0.4264(3) 0.3329(2) 0.46390(16) 0.0317(6) Uani 1 1 d . . .
C3 C 0.4989(3) 0.2451(2) 0.42591(18) 0.0397(7) Uani 1 1 d . . .
H3A H 0.5034 0.2374 0.3626 0.048 Uiso 1 1 calc R . .
C2 C 0.5644(3) 0.1692(2) 0.48322(18) 0.0403(7) Uani 1 1 d . . .
H2A H 0.6133 0.1085 0.4598 0.048 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0326(3) 0.0372(3) 0.0189(2) 0.000 -0.00010(17) 0.000
Cl3 0.0331(4) 0.0562(5) 0.0290(3) 0.0005(3) 0.0013(3) -0.0041(3)
Cl1 0.0680(5) 0.0477(5) 0.0414(4) 0.0048(4) -0.0020(4) 0.0193(4)
Cl2 0.0573(5) 0.0542(5) 0.0334(4) 0.0113(4) -0.0075(3) 0.0010(4)
N1 0.0316(12) 0.0326(12) 0.0225(11) -0.0006(10) 0.0008(9) 0.0019(9)
C1 0.0320(14) 0.0366(15) 0.0319(14) -0.0015(13) -0.0034(11) 0.0006(12)
C5 0.0352(15) 0.0328(14) 0.0290(14) -0.0021(13) 0.0032(11) 0.0004(12)
C4 0.0318(14) 0.0374(15) 0.0259(13) 0.0045(13) -0.0021(11) -0.0052(12)
C3 0.0390(16) 0.0586(19) 0.0216(13) -0.0078(14) -0.0005(11) -0.0032(14)
C2 0.0464(17) 0.0437(17) 0.0311(15) -0.0117(14) 0.0027(13) 0.0074(14)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.0147(19) 2_656 ?
Cu1 N1 2.0147(19) . ?
Cu1 Cl3 2.2235(6) . ?
Cu1 Cl3 2.2235(6) 2_656 ?
Cl1 C1 1.724(3) . ?
Cl2 C4 1.731(3) . ?
N1 C1 1.335(3) . ?
N1 C5 1.340(3) . ?
C1 C2 1.380(3) . ?
C5 C4 1.374(3) . ?
C5 H5A 0.9300 . ?
C4 C3 1.376(4) . ?
C3 C2 1.371(4) . ?
C3 H3A 0.9300 . ?
C2 H2A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 158.77(12) 2_656 . ?
N1 Cu1 Cl3 94.28(6) 2_656 . ?
N1 Cu1 Cl3 92.69(6) . . ?
N1 Cu1 Cl3 92.69(6) 2_656 2_656 ?
N1 Cu1 Cl3 94.28(6) . 2_656 ?
Cl3 Cu1 Cl3 141.42(4) . 2_656 ?
C1 N1 C5 117.6(2) . . ?
C1 N1 Cu1 122.46(17) . . ?
C5 N1 Cu1 119.55(16) . . ?
N1 C1 C2 123.6(2) . . ?
N1 C1 Cl1 116.76(19) . . ?
C2 C1 Cl1 119.7(2) . . ?
N1 C5 C4 121.9(2) . . ?
N1 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 Cl2 119.6(2) . . ?
C3 C4 Cl2 120.5(2) . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 N1 C1 -32.12(19) 2_656 . . . ?
Cl3 Cu1 N1 C1 77.01(19) . . . . ?
Cl3 Cu1 N1 C1 -140.96(19) 2_656 . . . ?
N1 Cu1 N1 C5 155.21(19) 2_656 . . . ?
Cl3 Cu1 N1 C5 -95.66(18) . . . . ?
Cl3 Cu1 N1 C5 46.36(18) 2_656 . . . ?
C5 N1 C1 C2 0.3(4) . . . . ?
Cu1 N1 C1 C2 -172.5(2) . . . . ?
C5 N1 C1 Cl1 -178.74(18) . . . . ?
Cu1 N1 C1 Cl1 8.4(3) . . . . ?
C1 N1 C5 C4 -0.9(4) . . . . ?
Cu1 N1 C5 C4 172.13(19) . . . . ?
N1 C5 C4 C3 0.6(4) . . . . ?
N1 C5 C4 Cl2 -178.83(18) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
Cl2 C4 C3 C2 179.7(2) . . . . ?
C4 C3 C2 C1 -0.7(4) . . . . ?
N1 C1 C2 C3 0.5(4) . . . . ?
Cl1 C1 C2 C3 179.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_exp_376
_database_code_depnum_ccdc_archive 'CCDC 1818326'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;

_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 Br2 Cl4 Cu N2'
_chemical_formula_weight         519.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'

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

_cell_length_a                   8.2520(5)
_cell_length_b                   12.8053(8)
_cell_length_c                   14.6136(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.902(5)
_cell_angle_gamma                90.00
_cell_volume                     1544.02(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1207
_cell_measurement_theta_min      2.9310
_cell_measurement_theta_max      29.1464

_exptl_crystal_description       parallelpiped
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             988
_exptl_absorpt_coefficient_mu    7.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3389
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         26.30
_reflns_number_total             1575
_reflns_number_gt                1270
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_structure_solution    'shelxtl, Bruker,2002'
_computing_structure_refinement  'shelxtl, Bruker,2002'
_computing_molecular_graphics    'shelxtl, Bruker,2002'
_computing_publication_material  'shelxtl, Bruker,2002'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0390P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1575
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0792
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.29745(5) 0.2500 0.02894(19) Uani 1 2 d S . .
Br1 Br 0.15421(5) 0.43362(4) 0.61289(3) 0.04344(17) Uani 1 1 d . . .
Cl2 Cl -0.25313(11) 0.35768(9) 0.25623(6) 0.0383(3) Uani 1 1 d . . .
Cl1 Cl -0.13789(15) 0.09201(9) 0.34735(7) 0.0519(3) Uani 1 1 d . . .
N1 N 0.0105(4) 0.2668(2) 0.38550(19) 0.0284(7) Uani 1 1 d . . .
C4 C 0.0689(4) 0.3277(3) 0.5370(2) 0.0293(9) Uani 1 1 d . . .
C5 C 0.0753(4) 0.3383(3) 0.4422(2) 0.0310(9) Uani 1 1 d . . .
H5A H 0.1259 0.3966 0.4176 0.037 Uiso 1 1 calc R . .
C1 C -0.0579(5) 0.1840(3) 0.4219(2) 0.0329(9) Uani 1 1 d . . .
C3 C -0.0017(5) 0.2413(3) 0.5739(2) 0.0394(10) Uani 1 1 d . . .
H3A H -0.0061 0.2330 0.6370 0.047 Uiso 1 1 calc R . .
C2 C -0.0673(5) 0.1656(3) 0.5152(3) 0.0396(10) Uani 1 1 d . . .
H2A H -0.1152 0.1053 0.5378 0.048 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0340(4) 0.0355(4) 0.0173(3) 0.000 -0.0015(2) 0.000
Br1 0.0518(3) 0.0477(3) 0.0305(2) -0.00929(19) -0.00689(19) 0.0004(2)
Cl2 0.0338(5) 0.0531(7) 0.0279(5) -0.0004(5) 0.0005(4) 0.0038(5)
Cl1 0.0690(8) 0.0473(7) 0.0392(6) -0.0063(5) -0.0041(5) -0.0210(6)
N1 0.0329(17) 0.0313(19) 0.0210(15) -0.0003(14) -0.0028(13) -0.0005(14)
C4 0.029(2) 0.036(2) 0.0235(18) -0.0030(17) -0.0026(15) 0.0005(17)
C5 0.032(2) 0.037(2) 0.0237(18) 0.0048(18) 0.0004(15) 0.0023(18)
C1 0.037(2) 0.034(2) 0.028(2) -0.0003(17) -0.0040(16) -0.0015(18)
C3 0.044(2) 0.055(3) 0.0192(19) 0.0051(19) -0.0034(17) -0.002(2)
C2 0.045(2) 0.042(3) 0.032(2) 0.012(2) -0.0013(18) -0.010(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 N1 2.019(3) 2 ?
Cu1 N1 2.019(3) . ?
Cu1 Cl2 2.2298(10) 2 ?
Cu1 Cl2 2.2298(10) . ?
Br1 C4 1.882(4) . ?
Cl1 C1 1.729(4) . ?
N1 C1 1.317(5) . ?
N1 C5 1.340(5) . ?
C4 C3 1.365(5) . ?
C4 C5 1.394(5) . ?
C5 H5A 0.9300 . ?
C1 C2 1.388(5) . ?
C3 C2 1.397(5) . ?
C3 H3A 0.9300 . ?
C2 H2A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 157.59(18) 2 . ?
N1 Cu1 Cl2 93.05(9) 2 2 ?
N1 Cu1 Cl2 94.66(9) . 2 ?
N1 Cu1 Cl2 94.66(9) 2 . ?
N1 Cu1 Cl2 93.05(9) . . ?
Cl2 Cu1 Cl2 139.53(7) 2 . ?
C1 N1 C5 118.0(3) . . ?
C1 N1 Cu1 122.7(3) . . ?
C5 N1 Cu1 118.9(2) . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 Br1 120.7(3) . . ?
C5 C4 Br1 119.7(3) . . ?
N1 C5 C4 121.8(4) . . ?
N1 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
N1 C1 C2 124.4(4) . . ?
N1 C1 Cl1 117.1(3) . . ?
C2 C1 Cl1 118.5(3) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C1 C2 C3 117.2(4) . . ?
C1 C2 H2A 121.4 . . ?
C3 C2 H2A 121.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 N1 C1 -32.1(3) 2 . . . ?
Cl2 Cu1 N1 C1 -141.8(3) 2 . . . ?
Cl2 Cu1 N1 C1 78.0(3) . . . . ?
N1 Cu1 N1 C5 154.9(3) 2 . . . ?
Cl2 Cu1 N1 C5 45.2(3) 2 . . . ?
Cl2 Cu1 N1 C5 -95.1(3) . . . . ?
C1 N1 C5 C4 -1.2(5) . . . . ?
Cu1 N1 C5 C4 172.2(3) . . . . ?
C3 C4 C5 N1 1.5(6) . . . . ?
Br1 C4 C5 N1 -177.4(3) . . . . ?
C5 N1 C1 C2 -0.2(6) . . . . ?
Cu1 N1 C1 C2 -173.3(3) . . . . ?
C5 N1 C1 Cl1 -179.1(3) . . . . ?
Cu1 N1 C1 Cl1 7.8(4) . . . . ?
C5 C4 C3 C2 -0.5(6) . . . . ?
Br1 C4 C3 C2 178.4(3) . . . . ?
N1 C1 C2 C3 1.2(6) . . . . ?
Cl1 C1 C2 C3 -180.0(3) . . . . ?
C4 C3 C2 C1 -0.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.108
####################################################################### 
# 
# 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_exp_1407
_database_code_depnum_ccdc_archive 'CCDC 1818327'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;

_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 Cl6 Cu N2'
_chemical_formula_weight         430.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'

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

_cell_length_a                   16.4247(8)
_cell_length_b                   14.1799(4)
_cell_length_c                   14.5688(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.219(7)
_cell_angle_gamma                90.00
_cell_volume                     2932.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2725
_cell_measurement_theta_min      2.8646
_cell_measurement_theta_max      29.2577

_exptl_crystal_description       parallelpiped
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1688
_exptl_absorpt_coefficient_mu    2.566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6568
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         26.30
_reflns_number_total             2980
_reflns_number_gt                2520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_structure_solution    'shelxtl, Bruker,2002'
_computing_structure_refinement  'shelxtl, Bruker,2002'
_computing_molecular_graphics    'shelxtl, Bruker,2002'
_computing_publication_material  'shelxtl, Bruker,2002'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0301P)²+1.0748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2980
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.387702(17) 0.919268(19) 0.24811(2) 0.02730(10) Uani 1 1 d . . .
Cl3 Cl 0.20133(4) 0.81352(5) 0.07419(5) 0.04181(17) Uani 1 1 d . . .
Cl4 Cl 0.50957(5) 0.54906(5) 0.39143(6) 0.05121(19) Uani 1 1 d . . .
Cl2 Cl 0.53222(5) 1.27319(5) 0.43557(6) 0.0537(2) Uani 1 1 d . . .
Cl1 Cl 0.22604(5) 1.05094(5) 0.05939(6) 0.0575(2) Uani 1 1 d . . .
N1 N 0.38083(12) 1.06601(13) 0.24343(15) 0.0312(5) Uani 1 1 d . . .
N2 N 0.36741(12) 0.77548(13) 0.23473(14) 0.0270(4) Uani 1 1 d . . .
C6 C 0.28723(14) 0.73694(16) 0.16076(18) 0.0291(5) Uani 1 1 d . . .
C5 C 0.44665(16) 1.11531(17) 0.32679(19) 0.0327(5) Uani 1 1 d . . .
H5A H 0.4944 1.0832 0.3845 0.039 Uiso 1 1 calc R . .
C9 C 0.42104(15) 0.62165(16) 0.29974(18) 0.0309(5) Uani 1 1 d . . .
C10 C 0.43388(15) 0.71703(16) 0.30478(18) 0.0302(5) Uani 1 1 d . . .
H10A H 0.4902 0.7422 0.3582 0.036 Uiso 1 1 calc R . .
C3 C 0.37343(17) 1.26134(18) 0.2455(2) 0.0422(6) Uani 1 1 d . . .
H3A H 0.3716 1.3269 0.2464 0.051 Uiso 1 1 calc R . .
C7 C 0.26927(16) 0.64146(17) 0.1508(2) 0.0363(6) Uani 1 1 d . . .
H7A H 0.2122 0.6178 0.0972 0.044 Uiso 1 1 calc R . .
C8 C 0.33799(17) 0.58244(16) 0.2223(2) 0.0372(6) Uani 1 1 d . . .
H8A H 0.3288 0.5175 0.2185 0.045 Uiso 1 1 calc R . .
C1 C 0.31199(15) 1.11467(17) 0.1634(2) 0.0341(6) Uani 1 1 d . . .
C2 C 0.30512(18) 1.21143(18) 0.1615(2) 0.0424(6) Uani 1 1 d . . .
H2A H 0.2553 1.2422 0.1045 0.051 Uiso 1 1 calc R . .
C4 C 0.44468(16) 1.21246(17) 0.3284(2) 0.0351(6) Uani 1 1 d . . .
Cl6 Cl 0.33871(4) 0.91917(4) 0.36635(5) 0.04065(16) Uani 1 1 d . . .
Cl5 Cl 0.42543(4) 0.91467(4) 0.11674(4) 0.02978(14) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.02845(16) 0.01903(16) 0.03111(18) 0.00058(11) 0.01253(13) 0.00097(11)
Cl3 0.0327(3) 0.0371(3) 0.0430(4) 0.0077(3) 0.0097(3) 0.0030(3)
Cl4 0.0473(4) 0.0344(4) 0.0542(4) 0.0152(3) 0.0124(3) 0.0074(3)
Cl2 0.0550(4) 0.0386(4) 0.0568(5) -0.0157(3) 0.0200(4) -0.0063(3)
Cl1 0.0414(3) 0.0408(4) 0.0573(5) -0.0038(3) 0.0002(3) 0.0052(3)
N1 0.0324(10) 0.0230(10) 0.0367(12) 0.0018(8) 0.0164(10) 0.0040(8)
N2 0.0293(9) 0.0221(10) 0.0298(11) -0.0003(8) 0.0150(8) -0.0024(8)
C6 0.0276(11) 0.0297(13) 0.0287(12) 0.0016(10) 0.0132(10) -0.0004(10)
C5 0.0338(12) 0.0277(12) 0.0348(14) 0.0004(11) 0.0158(11) 0.0046(11)
C9 0.0323(11) 0.0256(12) 0.0332(13) 0.0035(10) 0.0152(10) 0.0002(10)
C10 0.0292(11) 0.0275(12) 0.0305(13) -0.0001(10) 0.0124(10) -0.0026(10)
C3 0.0532(15) 0.0209(13) 0.0532(18) 0.0032(11) 0.0273(14) 0.0055(11)
C7 0.0326(12) 0.0318(13) 0.0377(14) -0.0054(11) 0.0127(11) -0.0088(11)
C8 0.0424(14) 0.0217(12) 0.0460(16) -0.0003(11) 0.0210(12) -0.0030(11)
C1 0.0306(11) 0.0285(13) 0.0404(15) 0.0010(11) 0.0158(11) 0.0031(10)
C2 0.0461(14) 0.0313(14) 0.0441(16) 0.0099(12) 0.0185(13) 0.0120(12)
C4 0.0402(13) 0.0268(12) 0.0415(15) -0.0057(11) 0.0229(12) -0.0001(11)
Cl6 0.0508(4) 0.0313(3) 0.0492(4) 0.0024(3) 0.0322(3) 0.0063(3)
Cl5 0.0279(3) 0.0280(3) 0.0268(3) 0.0006(2) 0.0089(2) -0.0022(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 N2 2.0593(19) . ?
Cu1 N1 2.0831(19) . ?
Cu1 Cl6 2.2382(7) . ?
Cu1 Cl5 2.2903(6) . ?
Cu1 Cl5 2.6867(6) 2_655 ?
Cl3 C6 1.723(2) . ?
Cl4 C9 1.733(2) . ?
Cl2 C4 1.728(2) . ?
Cl1 C1 1.718(2) . ?
N1 C1 1.337(3) . ?
N1 C5 1.346(3) . ?
N2 C6 1.329(3) . ?
N2 C10 1.341(3) . ?
C6 C7 1.378(3) . ?
C5 C4 1.378(3) . ?
C5 H5A 0.9300 . ?
C9 C10 1.365(3) . ?
C9 C8 1.376(3) . ?
C10 H10A 0.9300 . ?
C3 C2 1.369(4) . ?
C3 C4 1.373(3) . ?
C3 H3A 0.9300 . ?
C7 C8 1.369(3) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C1 C2 1.376(3) . ?
C2 H2A 0.9300 . ?
Cl5 Cu1 2.6867(6) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N1 169.22(7) . . ?
N2 Cu1 Cl6 88.20(5) . . ?
N1 Cu1 Cl6 89.50(6) . . ?
N2 Cu1 Cl5 89.52(5) . . ?
N1 Cu1 Cl5 91.95(6) . . ?
Cl6 Cu1 Cl5 175.13(2) . . ?
N2 Cu1 Cl5 96.67(5) . 2_655 ?
N1 Cu1 Cl5 94.09(5) . 2_655 ?
Cl6 Cu1 Cl5 99.01(2) . 2_655 ?
Cl5 Cu1 Cl5 85.52(2) . 2_655 ?
C1 N1 C5 117.5(2) . . ?
C1 N1 Cu1 123.52(16) . . ?
C5 N1 Cu1 118.93(15) . . ?
C6 N2 C10 117.24(19) . . ?
C6 N2 Cu1 122.08(15) . . ?
C10 N2 Cu1 120.59(15) . . ?
N2 C6 C7 124.2(2) . . ?
N2 C6 Cl3 116.52(17) . . ?
C7 C6 Cl3 119.28(17) . . ?
N1 C5 C4 121.3(2) . . ?
N1 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 Cl4 120.01(18) . . ?
C8 C9 Cl4 119.54(18) . . ?
N2 C10 C9 121.8(2) . . ?
N2 C10 H10A 119.1 . . ?
C9 C10 H10A 119.1 . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
C8 C7 C6 118.0(2) . . ?
C8 C7 H7A 121.0 . . ?
C6 C7 H7A 121.0 . . ?
C7 C8 C9 118.3(2) . . ?
C7 C8 H8A 120.9 . . ?
C9 C8 H8A 120.9 . . ?
N1 C1 C2 123.9(2) . . ?
N1 C1 Cl1 117.17(18) . . ?
C2 C1 Cl1 119.0(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 Cl2 119.75(19) . . ?
C5 C4 Cl2 119.8(2) . . ?
Cu1 Cl5 Cu1 94.40(2) . 2_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Cu1 N1 C1 -26.5(5) . . . . ?
Cl6 Cu1 N1 C1 -104.08(18) . . . . ?
Cl5 Cu1 N1 C1 71.28(18) . . . . ?
Cl5 Cu1 N1 C1 156.93(17) 2_655 . . . ?
N2 Cu1 N1 C5 150.8(4) . . . . ?
Cl6 Cu1 N1 C5 73.18(16) . . . . ?
Cl5 Cu1 N1 C5 -111.47(16) . . . . ?
Cl5 Cu1 N1 C5 -25.82(17) 2_655 . . . ?
N1 Cu1 N2 C6 15.4(5) . . . . ?
Cl6 Cu1 N2 C6 93.19(17) . . . . ?
Cl5 Cu1 N2 C6 -82.51(16) . . . . ?
Cl5 Cu1 N2 C6 -167.94(16) 2_655 . . . ?
N1 Cu1 N2 C10 -161.1(4) . . . . ?
Cl6 Cu1 N2 C10 -83.35(16) . . . . ?
Cl5 Cu1 N2 C10 100.95(16) . . . . ?
Cl5 Cu1 N2 C10 15.52(16) 2_655 . . . ?
C10 N2 C6 C7 -1.2(3) . . . . ?
Cu1 N2 C6 C7 -177.84(19) . . . . ?
C10 N2 C6 Cl3 177.98(16) . . . . ?
Cu1 N2 C6 Cl3 1.3(2) . . . . ?
C1 N1 C5 C4 -1.7(3) . . . . ?
Cu1 N1 C5 C4 -179.14(18) . . . . ?
C6 N2 C10 C9 1.2(3) . . . . ?
Cu1 N2 C10 C9 177.90(18) . . . . ?
C8 C9 C10 N2 -0.7(4) . . . . ?
Cl4 C9 C10 N2 179.39(17) . . . . ?
N2 C6 C7 C8 0.7(4) . . . . ?
Cl3 C6 C7 C8 -178.49(18) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C10 C9 C8 C7 0.1(4) . . . . ?
Cl4 C9 C8 C7 -179.96(19) . . . . ?
C5 N1 C1 C2 0.3(4) . . . . ?
Cu1 N1 C1 C2 177.6(2) . . . . ?
C5 N1 C1 Cl1 -177.81(18) . . . . ?
Cu1 N1 C1 Cl1 -0.5(3) . . . . ?
C4 C3 C2 C1 -1.0(4) . . . . ?
N1 C1 C2 C3 1.1(4) . . . . ?
Cl1 C1 C2 C3 179.16(19) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 Cl2 179.8(2) . . . . ?
N1 C5 C4 C3 1.8(4) . . . . ?
N1 C5 C4 Cl2 -178.40(17) . . . . ?
N2 Cu1 Cl5 Cu1 -99.51(5) . . . 2_655 ?
N1 Cu1 Cl5 Cu1 91.16(5) . . . 2_655 ?
Cl6 Cu1 Cl5 Cu1 -161.6(3) . . . 2_655 ?
Cl5 Cu1 Cl5 Cu1 -2.79(3) 2_655 . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.070
