# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_import
_audit_block_doi                 10.5517/cc14bmhl
_database_code_depnum_ccdc_archive 'CCDC 1052899'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2016-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Cl4 Cu N'
_chemical_formula_sum            'C8 H12 Cl2 Cu0.50 N'
_chemical_formula_weight         224.86

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   C2

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'

_cell_length_a                   10.546(3)
_cell_length_b                   7.245(2)
_cell_length_c                   13.915(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.843(10)
_cell_angle_gamma                90.00
_cell_volume                     1057.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.30

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    1.537
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_T_max  0.735
_exptl_absorpt_process_details   ?

_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  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector_area_resol_mean 'CCD plate'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5892
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.30
_reflns_number_total             1937
_reflns_number_gt                1568
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0618P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(19)
_refine_ls_number_reflns         1937
_refine_ls_number_parameters     106
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   0.788
_refine_ls_restrained_S_all      0.788
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.14538(7) 0.0000 0.0432(2) Uani 1 2 d S . .
Cl1 Cl 0.88134(10) -0.07233(13) 0.06524(7) 0.0476(3) Uani 1 1 d . . .
Cl2 Cl 0.96750(14) 0.35218(17) 0.11420(10) 0.0758(4) Uani 1 1 d . . .
N1 N 0.6593(3) 0.1917(4) 0.1320(2) 0.0435(9) Uani 1 1 d . . .
H1A H 0.6271 0.2753 0.0894 0.065 Uiso 1 1 calc R . .
H1B H 0.6225 0.0829 0.1186 0.065 Uiso 1 1 calc R . .
H1C H 0.7429 0.1821 0.1289 0.065 Uiso 1 1 calc R . .
C2 C 0.6345(4) 0.2508(6) 0.2323(3) 0.0452(10) Uani 1 1 d . . .
H2 H 0.5420 0.2546 0.2350 0.054 Uiso 1 1 calc R . .
C3 C 0.6891(4) 0.1112(6) 0.3044(3) 0.0446(11) Uani 1 1 d . . .
C1 C 0.6867(5) 0.4468(6) 0.2501(4) 0.0691(15) Uani 1 1 d . . .
H1D H 0.6485 0.5278 0.2008 0.104 Uiso 1 1 calc R . .
H1E H 0.7775 0.4460 0.2484 0.104 Uiso 1 1 calc R . .
H1F H 0.6669 0.4891 0.3122 0.104 Uiso 1 1 calc R . .
C4 C 0.8189(5) 0.0830(7) 0.3222(3) 0.0606(13) Uani 1 1 d . . .
H4 H 0.8748 0.1518 0.2890 0.073 Uiso 1 1 calc R . .
C8 C 0.6087(5) 0.0060(8) 0.3550(3) 0.0661(15) Uani 1 1 d . . .
H8 H 0.5210 0.0226 0.3438 0.079 Uiso 1 1 calc R . .
C6 C 0.7863(8) -0.1474(8) 0.4396(4) 0.087(2) Uani 1 1 d . . .
H6 H 0.8190 -0.2320 0.4859 0.105 Uiso 1 1 calc R . .
C7 C 0.6573(7) -0.1235(9) 0.4221(4) 0.0853(19) Uani 1 1 d . . .
H7 H 0.6024 -0.1942 0.4552 0.102 Uiso 1 1 calc R . .
C5 C 0.8665(6) -0.0484(8) 0.3898(4) 0.0763(16) Uani 1 1 d . . .
H5 H 0.9539 -0.0681 0.4006 0.092 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 0.0498(5) 0.0364(4) 0.0429(4) 0.000 0.0018(3) 0.000
Cl1 0.0545(7) 0.0419(6) 0.0479(6) -0.0026(5) 0.0126(5) -0.0022(5)
Cl2 0.0892(10) 0.0569(7) 0.0847(9) -0.0337(7) 0.0262(8) -0.0250(7)
N1 0.051(2) 0.038(2) 0.0397(17) 0.0025(15) -0.0009(14) 0.0019(16)
C2 0.044(2) 0.047(2) 0.046(2) -0.006(2) 0.0051(19) 0.008(2)
C3 0.051(2) 0.048(3) 0.0347(19) -0.006(2) 0.0033(17) -0.007(2)
C1 0.083(4) 0.043(3) 0.077(3) -0.012(3) -0.012(3) 0.006(3)
C4 0.065(3) 0.072(3) 0.044(2) 0.010(2) 0.002(2) 0.008(3)
C8 0.076(4) 0.077(4) 0.046(3) -0.004(3) 0.011(3) -0.022(3)
C6 0.151(7) 0.066(4) 0.042(3) 0.006(3) -0.006(4) 0.010(4)
C7 0.131(6) 0.071(4) 0.054(3) 0.009(3) 0.011(4) -0.032(4)
C5 0.088(4) 0.087(4) 0.050(3) 0.006(3) -0.008(3) 0.032(4)

_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 Cl2 2.2357(13) . ?
Cu1 Cl2 2.2357(13) 2_755 ?
Cu1 Cl1 2.2604(11) 2_755 ?
Cu1 Cl1 2.2604(11) . ?
N1 C2 1.508(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C2 C3 1.497(6) . ?
C2 C1 1.534(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.382(6) . ?
C3 C8 1.385(6) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C4 C5 1.395(6) . ?
C4 H4 0.9300 . ?
C8 C7 1.385(8) . ?
C8 H8 0.9300 . ?
C6 C5 1.352(8) . ?
C6 C7 1.368(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C5 H5 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
Cl2 Cu1 Cl2 95.84(8) . 2_755 ?
Cl2 Cu1 Cl1 152.17(5) . 2_755 ?
Cl2 Cu1 Cl1 92.92(4) 2_755 2_755 ?
Cl2 Cu1 Cl1 92.92(4) . . ?
Cl2 Cu1 Cl1 152.17(5) 2_755 . ?
Cl1 Cu1 Cl1 91.50(6) 2_755 . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C3 C2 N1 109.7(3) . . ?
C3 C2 C1 114.2(4) . . ?
N1 C2 C1 108.6(4) . . ?
C3 C2 H2 108.1 . . ?
N1 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C4 C3 C8 118.3(4) . . ?
C4 C3 C2 121.8(4) . . ?
C8 C3 C2 119.9(4) . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C7 C8 C3 120.8(5) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C5 C6 C7 120.3(5) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 119.9(6) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?

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
N1 H1C Cl1 0.89 2.56 3.233(3) 132.4 .
N1 H1C Cl2 0.89 2.70 3.484(4) 148.3 .
N1 H1A Cl1 0.89 2.41 3.225(3) 152.0 4_655
N1 H1B Cl2 0.89 2.33 3.178(4) 158.2 3_445

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.30
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_import
_audit_block_doi                 10.5517/cc14bmjm
_database_code_depnum_ccdc_archive 'CCDC 1052900'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2016-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Cl4 Cu1 N1'
_chemical_formula_sum            'C8 H12 Cl2 Cu0.50 N'
_chemical_formula_weight         224.86

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   C2

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'

_cell_length_a                   10.5419(3)
_cell_length_b                   7.2444(2)
_cell_length_c                   13.9027(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.916(2)
_cell_angle_gamma                90.00
_cell_volume                     1056.09(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8104
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             462
_exptl_absorpt_coefficient_mu    1.540
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_T_max  0.724
_exptl_absorpt_process_details   ?

_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  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7146
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2434
_reflns_number_gt                2067
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0851P)²+0.5012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.028(19)
_refine_ls_number_reflns         2434
_refine_ls_number_parameters     106
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.08896(6) 0.0000 0.0480(2) Uani 1 2 d S . .
Cl1 Cl 0.38125(9) 0.30692(12) 0.06554(7) 0.0512(3) Uani 1 1 d . . .
Cl2 Cl 0.46742(15) -0.11742(17) 0.11444(10) 0.0798(4) Uani 1 1 d . . .
N1 N 0.1599(3) 0.0433(4) 0.1324(2) 0.0493(7) Uani 1 1 d . . .
H1A H 0.1279 -0.0397 0.0893 0.074 Uiso 1 1 calc R . .
H1B H 0.2436 0.0532 0.1296 0.074 Uiso 1 1 calc R . .
H1C H 0.1231 0.1522 0.1192 0.074 Uiso 1 1 calc R . .
C2 C 0.1349(4) -0.0170(5) 0.2319(3) 0.0498(9) Uani 1 1 d . . .
H2 H 0.0423 -0.0207 0.2342 0.060 Uiso 1 1 calc R . .
C3 C 0.1890(4) 0.1229(5) 0.3042(3) 0.0493(9) Uani 1 1 d . . .
C1 C 0.1863(6) -0.2111(6) 0.2499(4) 0.0731(13) Uani 1 1 d . . .
H1D H 0.1478 -0.2924 0.2007 0.110 Uiso 1 1 calc R . .
H1E H 0.1666 -0.2529 0.3122 0.110 Uiso 1 1 calc R . .
H1F H 0.2771 -0.2108 0.2481 0.110 Uiso 1 1 calc R . .
C4 C 0.3193(5) 0.1518(7) 0.3219(3) 0.0625(11) Uani 1 1 d . . .
H4 H 0.3749 0.0832 0.2883 0.075 Uiso 1 1 calc R . .
C5 C 0.3673(6) 0.2815(9) 0.3889(4) 0.0840(16) Uani 1 1 d . . .
H5 H 0.4549 0.3002 0.3998 0.101 Uiso 1 1 calc R . .
C8 C 0.1079(5) 0.2290(8) 0.3551(4) 0.0691(13) Uani 1 1 d . . .
H8 H 0.0201 0.2131 0.3439 0.083 Uiso 1 1 calc R . .
C7 C 0.1577(7) 0.3580(9) 0.4221(4) 0.0881(19) Uani 1 1 d . . .
H7 H 0.1030 0.4285 0.4555 0.106 Uiso 1 1 calc R . .
C6 C 0.2866(8) 0.3828(9) 0.4396(4) 0.092(2) Uani 1 1 d . . .
H6 H 0.3194 0.4680 0.4856 0.110 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 0.0551(4) 0.0394(3) 0.0494(4) 0.000 0.0050(2) 0.000
Cl1 0.0567(6) 0.0447(5) 0.0539(5) 0.0028(4) 0.0146(4) 0.0025(4)
Cl2 0.0938(9) 0.0589(6) 0.0905(9) 0.0332(6) 0.0278(7) 0.0246(6)
N1 0.0575(18) 0.0470(18) 0.0429(15) -0.0049(12) 0.0030(12) -0.0049(13)
C2 0.0465(19) 0.050(2) 0.052(2) 0.0064(16) 0.0029(15) -0.0061(16)
C3 0.060(2) 0.049(2) 0.0394(16) 0.0040(15) 0.0077(14) 0.0048(17)
C1 0.089(4) 0.044(2) 0.084(3) 0.015(2) -0.002(3) -0.004(2)
C4 0.062(2) 0.075(3) 0.050(2) -0.0076(19) 0.0035(19) -0.012(2)
C5 0.096(4) 0.091(4) 0.062(3) -0.007(3) -0.009(3) -0.028(3)
C8 0.076(3) 0.076(3) 0.056(3) 0.003(2) 0.012(2) 0.016(3)
C7 0.128(6) 0.074(4) 0.062(3) -0.008(3) 0.010(3) 0.029(4)
C6 0.157(7) 0.065(3) 0.050(3) -0.010(2) -0.011(3) -0.011(4)

_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 Cl2 2.2355(11) 2_655 ?
Cu1 Cl2 2.2355(11) . ?
Cu1 Cl1 2.2641(9) . ?
Cu1 Cl1 2.2641(9) 2_655 ?
N1 C2 1.500(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C2 C3 1.498(6) . ?
C2 C1 1.519(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.386(6) . ?
C3 C8 1.396(6) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C4 C5 1.382(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(10) . ?
C5 H5 0.9300 . ?
C8 C7 1.384(9) . ?
C8 H8 0.9300 . ?
C7 C6 1.367(10) . ?
C7 H7 0.9300 . ?
C6 H6 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
Cl2 Cu1 Cl2 96.05(8) 2_655 . ?
Cl2 Cu1 Cl1 152.22(5) 2_655 . ?
Cl2 Cu1 Cl1 92.76(4) . . ?
Cl2 Cu1 Cl1 92.76(4) 2_655 2_655 ?
Cl2 Cu1 Cl1 152.22(5) . 2_655 ?
Cl1 Cu1 Cl1 91.56(5) . 2_655 ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C3 C2 N1 109.3(3) . . ?
C3 C2 C1 114.3(4) . . ?
N1 C2 C1 109.1(4) . . ?
C3 C2 H2 108.0 . . ?
N1 C2 H2 108.0 . . ?
C1 C2 H2 108.0 . . ?
C4 C3 C8 118.3(4) . . ?
C4 C3 C2 121.6(4) . . ?
C8 C3 C2 120.1(4) . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C5 C4 C3 120.7(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.4(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C8 C3 120.2(5) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
C6 C7 C8 120.6(6) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C6 C5 119.8(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?

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
N1 H1B Cl1 0.89 2.56 3.225(3) 132.3 .
N1 H1B Cl2 0.89 2.69 3.478(4) 148.0 .
N1 H1A Cl1 0.89 2.42 3.232(3) 152.6 4_545
N1 H1C Cl2 0.89 2.34 3.181(4) 158.3 3_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_job
_audit_block_doi                 10.5517/cc14bmlp
_database_code_depnum_ccdc_archive 'CCDC 1052902'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2016-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Cl4 Cu N'
_chemical_formula_sum            'C8 H12 Cl2 Cu0.50 N1'
_chemical_formula_weight         224.86

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'C 2 c b'

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

_cell_length_a                   7.2117(10)
_cell_length_b                   10.3511(12)
_cell_length_c                   27.503(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2053.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_absorpt_coefficient_mu    1.584
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_process_details   ?

_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  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4658
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1922
_reflns_number_gt                1609
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0375P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_number_reflns         1922
_refine_ls_number_parameters     106
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0813
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.15650(11) 0.0000 0.5000 0.0245(2) Uani 1 2 d S . .
Cl2 Cl 0.37513(14) 0.12956(9) 0.46670(3) 0.0254(2) Uani 1 1 d . . .
Cl1 Cl -0.05053(16) 0.04830(12) 0.44221(4) 0.0416(3) Uani 1 1 d . . .
N N -0.3945(5) -0.1406(3) 0.43336(11) 0.0236(8) Uani 1 1 d . . .
H0A H -0.4792 -0.1144 0.4547 0.035 Uiso 1 1 calc R . .
H0B H -0.2854 -0.1054 0.4407 0.035 Uiso 1 1 calc R . .
H0C H -0.3851 -0.2263 0.4345 0.035 Uiso 1 1 calc R . .
C2 C -0.4515(6) -0.0998(4) 0.38303(14) 0.0266(10) Uani 1 1 d . . .
H2 H -0.4561 -0.0052 0.3822 0.032 Uiso 1 1 calc R . .
C3 C -0.3081(6) -0.1436(4) 0.34697(14) 0.0256(10) Uani 1 1 d . . .
C1 C -0.6475(6) -0.1512(4) 0.37263(16) 0.0349(11) Uani 1 1 d . . .
H1A H -0.7317 -0.1194 0.3969 0.052 Uiso 1 1 calc R . .
H1B H -0.6463 -0.2439 0.3734 0.052 Uiso 1 1 calc R . .
H1C H -0.6871 -0.1224 0.3411 0.052 Uiso 1 1 calc R . .
C4 C -0.2074(7) -0.0535(5) 0.32020(16) 0.0350(11) Uani 1 1 d . . .
H4 H -0.2301 0.0342 0.3246 0.042 Uiso 1 1 calc R . .
C8 C -0.2726(6) -0.2748(4) 0.33955(16) 0.0309(11) Uani 1 1 d . . .
H8 H -0.3377 -0.3368 0.3571 0.037 Uiso 1 1 calc R . .
C7 C -0.1410(8) -0.3116(5) 0.30616(16) 0.0451(12) Uani 1 1 d . . .
H7 H -0.1191 -0.3991 0.3009 0.054 Uiso 1 1 calc R . .
C6 C -0.0406(7) -0.2211(5) 0.28020(15) 0.0449(13) Uani 1 1 d . . .
H6 H 0.0491 -0.2482 0.2581 0.054 Uiso 1 1 calc R . .
C5 C -0.0720(7) -0.0931(5) 0.28669(16) 0.0426(13) Uani 1 1 d . . .
H5 H -0.0046 -0.0323 0.2692 0.051 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
Cu 0.0171(3) 0.0296(4) 0.0267(3) -0.0016(3) 0.000 0.000
Cl2 0.0205(4) 0.0284(5) 0.0273(5) 0.0045(4) -0.0021(4) 0.0000(5)
Cl1 0.0284(5) 0.0432(7) 0.0532(7) 0.0073(6) -0.0194(5) -0.0097(6)
N 0.0176(18) 0.0295(19) 0.0237(18) 0.0004(14) 0.0015(14) 0.0035(15)
C2 0.024(2) 0.030(2) 0.025(2) -0.0019(19) -0.0041(17) 0.005(2)
C3 0.020(2) 0.035(2) 0.021(2) -0.0014(17) -0.0027(16) 0.007(2)
C1 0.019(2) 0.049(3) 0.037(2) -0.007(2) -0.003(2) 0.003(2)
C4 0.039(3) 0.037(3) 0.029(2) 0.005(2) -0.008(2) -0.003(2)
C8 0.032(2) 0.033(3) 0.027(2) 0.004(2) -0.0005(19) 0.005(2)
C7 0.046(3) 0.058(3) 0.031(3) -0.002(2) -0.004(2) 0.023(3)
C6 0.029(3) 0.080(4) 0.025(3) 0.002(3) 0.005(2) 0.017(3)
C5 0.029(3) 0.067(4) 0.032(3) 0.017(2) -0.003(2) -0.009(3)

_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
Cu Cl1 2.2373(12) . ?
Cu Cl1 2.2373(12) 3_556 ?
Cu Cl2 2.2634(11) . ?
Cu Cl2 2.2634(11) 3_556 ?
N C2 1.505(5) . ?
N H0A 0.8900 . ?
N H0B 0.8900 . ?
N H0C 0.8900 . ?
C2 C3 1.503(6) . ?
C2 C1 1.538(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.393(6) . ?
C3 C8 1.397(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 C5 1.404(7) . ?
C4 H4 0.9300 . ?
C8 C7 1.374(7) . ?
C8 H8 0.9300 . ?
C7 C6 1.383(7) . ?
C7 H7 0.9300 . ?
C6 C5 1.355(7) . ?
C6 H6 0.9300 . ?
C5 H5 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
Cl1 Cu Cl1 96.27(7) . 3_556 ?
Cl1 Cu Cl2 92.58(4) . . ?
Cl1 Cu Cl2 152.22(4) 3_556 . ?
Cl1 Cu Cl2 152.22(4) . 3_556 ?
Cl1 Cu Cl2 92.58(4) 3_556 3_556 ?
Cl2 Cu Cl2 91.69(6) . 3_556 ?
C2 N H0A 109.5 . . ?
C2 N H0B 109.5 . . ?
H0A N H0B 109.5 . . ?
C2 N H0C 109.5 . . ?
H0A N H0C 109.5 . . ?
H0B N H0C 109.5 . . ?
C3 C2 N 109.5(3) . . ?
C3 C2 C1 113.9(3) . . ?
N C2 C1 108.9(3) . . ?
C3 C2 H2 108.1 . . ?
N C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C4 C3 C8 118.6(4) . . ?
C4 C3 C2 120.3(4) . . ?
C8 C3 C2 121.1(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C4 C5 120.9(5) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C7 C8 C3 119.6(4) . . ?
C7 C8 H8 120.2 . . ?
C3 C8 H8 120.2 . . ?
C8 C7 C6 121.2(5) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C5 C6 C7 120.4(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C5 C4 119.2(5) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?

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
N H0C Cl2 0.89 2.56 3.206(3) 130.5 5_445
N H0A Cl2 0.89 2.41 3.214(3) 150.6 3_456

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.076
