# 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_cu-h2ca-29
_database_code_depnum_ccdc_archive 'CCDC 1433294'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-06-21 downloaded from the CCDC.
;

_audit_creation_date             2014-10-14T14:58:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C10 H12 Cl2 Cu1 O6'
_chemical_formula_sum            'C10 H12 Cl2 Cu O6'
_chemical_formula_weight         362.64

#------------------ UNIT CELL INFORMATION -----------------------------------#

_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                   17.8431(10)
_cell_length_b                   7.6498(4)
_cell_length_c                   10.3003(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.903(6)
_cell_angle_gamma                90
_cell_volume                     1337.87(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    792
_cell_measurement_theta_min      4.5056
_cell_measurement_theta_max      75.5698

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    6.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68601
_exptl_absorpt_correction_T_max  1

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'CCD, ω scans'
_diffrn_reflns_number            2868
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.35
_diffrn_reflns_theta_max         75.75
_diffrn_reflns_theta_full        75.75
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_reflns_number_total             1367
_reflns_number_gt                1056
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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)+(0.0712P)²+0.4244P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1367
_refine_ls_number_parameters     88
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1452
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.708

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
Cu1 Cu 0.5 0.45346(9) 0.25 0.0348(3) Uani 1 d S . .
Cl1 Cl 0.37468(5) -0.04705(12) -0.04594(8) 0.0393(3) Uani 1 d . . .
O1 O 0.45046(15) 0.2596(3) 0.1263(2) 0.0368(6) Uani 1 d . . .
O2 O 0.44954(15) -0.3523(3) 0.1273(2) 0.0355(5) Uani 1 d . . .
C1 C 0.46992(18) 0.1113(4) 0.1775(3) 0.0302(7) Uani 1 d . . .
C2 C 0.44213(19) -0.0463(4) 0.1151(3) 0.0300(7) Uani 1 d . . .
C3 C 0.46982(17) -0.2033(5) 0.1779(3) 0.0306(7) Uani 1 d . . .
O3 O 0.3953(2) 0.4541(5) 0.3381(3) 0.0541(8) Uani 1 d D . .
H3 H 0.410(4) 0.410(9) 0.413(4) 0.10(2) Uiso 1 d D . .
C4 C 0.3322(2) 0.5683(7) 0.3057(4) 0.0754(17) Uani 1 d . . .
H4A H 0.3048 0.5577 0.2089 0.091 Uiso 1 calc R . .
H4B H 0.3527 0.6864 0.3218 0.091 Uiso 1 calc R . .
C5 C 0.2748(2) 0.5457(7) 0.3790(4) 0.083(2) Uani 1 d R . .
H5A H 0.2335 0.6305 0.3475 0.124 Uiso 1 calc R . .
H5B H 0.3002 0.5615 0.475 0.124 Uiso 1 calc R . .
H5C H 0.2528 0.4302 0.3628 0.124 Uiso 1 calc R . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.978(2) . ?
Cu1 O1 1.978(2) 2_655 ?
Cu1 O2 1.979(2) 2_665 ?
Cu1 O2 1.979(2) 1_565 ?
Cu1 O3 2.314(3) 2_655 ?
Cu1 O3 2.314(3) . ?
Cl1 C2 1.724(3) . ?
O1 C1 1.254(4) . ?
O2 C3 1.259(4) . ?
O2 Cu1 1.979(2) 1_545 ?
C1 C2 1.384(5) . ?
C1 C1 1.548(5) 2_655 ?
C2 C3 1.381(5) . ?
C3 C3 1.543(5) 2_655 ?
O3 C4 1.382(5) . ?
O3 H3 0.81(2) . ?
C4 C5 1.4579 . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 H5A 0.96 . ?
C5 H5B 0.96 . ?
C5 H5C 0.96 . ?

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 O1 82.84(14) . 2_655 ?
O1 Cu1 O2 179.37(11) . 2_665 ?
O1 Cu1 O2 97.24(10) 2_655 2_665 ?
O1 Cu1 O2 97.24(10) . 1_565 ?
O1 Cu1 O2 179.37(11) 2_655 1_565 ?
O2 Cu1 O2 82.68(14) 2_665 1_565 ?
O1 Cu1 O3 90.22(11) . 2_655 ?
O1 Cu1 O3 89.95(12) 2_655 2_655 ?
O2 Cu1 O3 89.16(11) 2_665 2_655 ?
O2 Cu1 O3 90.67(12) 1_565 2_655 ?
O1 Cu1 O3 89.95(12) . . ?
O1 Cu1 O3 90.22(11) 2_655 . ?
O2 Cu1 O3 90.67(12) 2_665 . ?
O2 Cu1 O3 89.16(11) 1_565 . ?
O3 Cu1 O3 179.78(18) 2_655 . ?
C1 O1 Cu1 113.36(19) . . ?
C3 O2 Cu1 113.49(19) . 1_545 ?
O1 C1 C2 125.4(3) . . ?
O1 C1 C1 115.19(17) . 2_655 ?
C2 C1 C1 119.40(18) . 2_655 ?
C3 C2 C1 120.9(3) . . ?
C3 C2 Cl1 119.4(2) . . ?
C1 C2 Cl1 119.6(3) . . ?
O2 C3 C2 125.2(3) . . ?
O2 C3 C3 115.17(17) . 2_655 ?
C2 C3 C3 119.61(18) . 2_655 ?
C4 O3 Cu1 127.0(3) . . ?
C4 O3 H3 120(6) . . ?
Cu1 O3 H3 108(5) . . ?
O3 C4 C5 116.7(2) . . ?
O3 C4 H4A 108.1 . . ?
C5 C4 H4A 108.1 . . ?
O3 C4 H4B 108.1 . . ?
C5 C4 H4B 108.1 . . ?
H4A C4 H4B 107.3 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 O1 C1 0.85(19) 2_655 . . . ?
O2 Cu1 O1 C1 99(10) 2_665 . . . ?
O2 Cu1 O1 C1 -178.5(2) 1_565 . . . ?
O3 Cu1 O1 C1 90.8(3) 2_655 . . . ?
O3 Cu1 O1 C1 -89.4(3) . . . . ?
Cu1 O1 C1 C2 177.9(3) . . . . ?
Cu1 O1 C1 C1 -2.1(5) . . . 2_655 ?
O1 C1 C2 C3 177.2(3) . . . . ?
C1 C1 C2 C3 -2.8(6) 2_655 . . . ?
O1 C1 C2 Cl1 -0.4(5) . . . . ?
C1 C1 C2 Cl1 179.6(3) 2_655 . . . ?
Cu1 O2 C3 C2 -178.6(3) 1_545 . . . ?
Cu1 O2 C3 C3 1.1(5) 1_545 . . 2_655 ?
C1 C2 C3 O2 -178.0(3) . . . . ?
Cl1 C2 C3 O2 -0.3(5) . . . . ?
C1 C2 C3 C3 2.4(6) . . . 2_655 ?
Cl1 C2 C3 C3 -180.0(3) . . . 2_655 ?
O1 Cu1 O3 C4 -100.8(4) . . . . ?
O1 Cu1 O3 C4 176.4(4) 2_655 . . . ?
O2 Cu1 O3 C4 79.1(4) 2_665 . . . ?
O2 Cu1 O3 C4 -3.5(4) 1_565 . . . ?
O3 Cu1 O3 C4 37.8(4) 2_655 . . . ?
Cu1 O3 C4 C5 -177.85(16) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu-h2ca-71_2
_database_code_depnum_ccdc_archive 'CCDC 1433295'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-06-21 downloaded from the CCDC.
;

_audit_creation_date             2014-10-13T16:30:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C28 H18 Cl6 Cu2 N2 O16'
_chemical_formula_sum            'C28 H18 Cl6 Cu2 N2 O16'
_chemical_formula_weight         978.24

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3314(5)
_cell_length_b                   9.4880(4)
_cell_length_c                   10.3517(6)
_cell_angle_alpha                80.069(4)
_cell_angle_beta                 89.845(4)
_cell_angle_gamma                66.524(5)
_cell_volume                     825.83(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3293
_cell_measurement_theta_min      4.3441
_cell_measurement_theta_max      75.6737

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             790
_exptl_absorpt_coefficient_mu    6.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53764
_exptl_absorpt_correction_T_max  1

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54179
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'CCD, ω scans'
_diffrn_reflns_number            6802
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.35
_diffrn_reflns_theta_max         75.85
_diffrn_reflns_theta_full        75.85
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_reflns_number_total             3371
_reflns_number_gt                2993
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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)+(0.0722P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3371
_refine_ls_number_parameters     260
_refine_ls_number_restraints     6
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1053
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.502

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
Cu1 Cu 0.19483(3) 0.82906(4) 0.57459(3) 0.04117(13) Uani 1 d . . .
Cl1 Cl 0.47025(6) 0.97903(6) 0.19859(4) 0.04202(15) Uani 1 d . . .
O1 O 0.32066(17) 0.90983(18) 0.66759(14) 0.0395(3) Uani 1 d . . .
O2 O 0.29381(18) 0.89420(19) 0.42129(14) 0.0409(3) Uani 1 d . . .
C1 C 0.4090(2) 0.9544(2) 0.59480(19) 0.0325(3) Uani 1 d . . .
C2 C 0.3934(2) 0.9445(2) 0.45067(19) 0.0327(4) Uani 1 d . . .
C3 C 0.4857(2) 0.9909(2) 0.36100(18) 0.0330(4) Uani 1 d . . .
Cl2 Cl -0.15713(6) 0.67517(6) 0.33415(5) 0.04416(15) Uani 1 d . . .
Cl3 Cl -0.10137(6) 0.70786(6) 0.93892(5) 0.04537(15) Uani 1 d . . .
O3 O 0.07583(18) 0.7947(2) 0.72075(15) 0.0441(3) Uani 1 d . . .
O4 O 0.04698(19) 0.7877(2) 0.47132(15) 0.0464(4) Uani 1 d . . .
O5 O -0.34105(19) 0.5929(2) 0.54853(17) 0.0482(4) Uani 1 d . . .
O6 O -0.3172(2) 0.6059(2) 0.80321(17) 0.0498(4) Uani 1 d . . .
C4 C -0.0273(2) 0.7467(2) 0.6878(2) 0.0353(4) Uani 1 d . . .
C5 C -0.0426(2) 0.7414(2) 0.5441(2) 0.0356(4) Uani 1 d . . .
C6 C -0.1467(2) 0.6884(2) 0.49770(19) 0.0355(4) Uani 1 d . . .
C7 C -0.2441(2) 0.6402(2) 0.5836(2) 0.0355(4) Uani 1 d . . .
C8 C -0.2310(2) 0.6483(2) 0.7315(2) 0.0373(4) Uani 1 d . . .
C9 C -0.1199(2) 0.7017(2) 0.77448(19) 0.0355(4) Uani 1 d . . .
O7 O 0.3802(2) 0.5800(2) 0.63301(17) 0.0493(4) Uani 1 d D . .
H7A H 0.365(4) 0.511(4) 0.585(3) 0.071(10) Uiso 1 d D . .
H7B H 0.480(3) 0.575(4) 0.624(4) 0.076(10) Uiso 1 d D . .
N1 N 0.3690(3) 0.7065(3) 1.1063(2) 0.0590(5) Uani 1 d . . .
H1 H 0.4591 0.6318 1.1313 0.071 Uiso 1 calc R . .
C10 C 0.3458(4) 0.7912(4) 0.9856(3) 0.0642(7) Uani 1 d . . .
H10 H 0.4274 0.7701 0.9302 0.077 Uiso 1 calc R . .
C11 C 0.2029(4) 0.9090(3) 0.9424(3) 0.0594(7) Uani 1 d . . .
H11 H 0.1884 0.9692 0.8586 0.071 Uiso 1 calc R . .
C12 C 0.0784(3) 0.9390(3) 1.0240(2) 0.0508(5) Uani 1 d . . .
C13 C 0.1098(4) 0.8507(3) 1.1504(2) 0.0575(6) Uani 1 d . . .
H13 H 0.0313 0.8704 1.2088 0.069 Uiso 1 calc R . .
C14 C 0.2550(4) 0.7349(3) 1.1901(3) 0.0608(7) Uani 1 d . . .
H14 H 0.2747 0.6761 1.2749 0.073 Uiso 1 calc R . .
O8 O 0.3264(3) 0.4872(3) 0.9094(2) 0.0782(6) Uani 1 d D . .
H9A H 0.260(5) 0.557(5) 0.838(4) 0.123(19) Uiso 1 d D . .
H9B H 0.272(5) 0.472(6) 0.981(3) 0.120(18) Uiso 1 d D . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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 O3 1.9333(14) . ?
Cu1 O4 1.9455(15) . ?
Cu1 O2 1.9652(14) . ?
Cu1 O1 1.9673(14) . ?
Cu1 O7 2.2799(18) . ?
Cl1 C3 1.7145(19) . ?
O1 C1 1.261(2) . ?
O2 C2 1.261(2) . ?
C1 C3 1.391(3) 2_676 ?
C1 C2 1.522(3) . ?
C2 C3 1.398(3) . ?
C3 C1 1.391(3) 2_676 ?
Cl2 C6 1.725(2) . ?
Cl3 C9 1.725(2) . ?
O3 C4 1.286(2) . ?
O4 C5 1.278(2) . ?
O5 C7 1.238(3) . ?
O6 C8 1.229(2) . ?
C4 C9 1.376(3) . ?
C4 C5 1.506(3) . ?
C5 C6 1.379(3) . ?
C6 C7 1.419(3) . ?
C7 C8 1.554(3) . ?
C8 C9 1.424(3) . ?
O7 H7A 0.944(18) . ?
O7 H7B 0.918(18) . ?
N1 C10 1.331(4) . ?
N1 C14 1.343(4) . ?
N1 H1 0.86 . ?
C10 C11 1.368(5) . ?
C10 H10 0.93 . ?
C11 C12 1.399(3) . ?
C11 H11 0.93 . ?
C12 C13 1.388(4) . ?
C12 C12 1.478(6) 2_577 ?
C13 C14 1.368(5) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
O8 H9A 0.937(19) . ?
O8 H9B 0.921(19) . ?

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
O3 Cu1 O4 84.65(6) . . ?
O3 Cu1 O2 172.01(7) . . ?
O4 Cu1 O2 94.62(6) . . ?
O3 Cu1 O1 96.66(6) . . ?
O4 Cu1 O1 169.93(7) . . ?
O2 Cu1 O1 82.69(6) . . ?
O3 Cu1 O7 90.78(7) . . ?
O4 Cu1 O7 98.94(7) . . ?
O2 Cu1 O7 97.19(6) . . ?
O1 Cu1 O7 91.03(6) . . ?
C1 O1 Cu1 113.42(13) . . ?
C2 O2 Cu1 113.15(13) . . ?
O1 C1 C3 124.17(18) . 2_676 ?
O1 C1 C2 114.96(16) . . ?
C3 C1 C2 120.87(17) 2_676 . ?
O2 C2 C3 124.58(18) . . ?
O2 C2 C1 115.55(16) . . ?
C3 C2 C1 119.87(17) . . ?
C1 C3 C2 119.27(18) 2_676 . ?
C1 C3 Cl1 120.43(14) 2_676 . ?
C2 C3 Cl1 120.31(14) . . ?
C4 O3 Cu1 111.83(13) . . ?
C5 O4 Cu1 111.75(14) . . ?
O3 C4 C9 124.16(19) . . ?
O3 C4 C5 115.60(17) . . ?
C9 C4 C5 120.24(17) . . ?
O4 C5 C6 123.69(19) . . ?
O4 C5 C4 115.49(17) . . ?
C6 C5 C4 120.81(17) . . ?
C5 C6 C7 120.88(18) . . ?
C5 C6 Cl2 120.33(15) . . ?
C7 C6 Cl2 118.77(15) . . ?
O5 C7 C6 124.3(2) . . ?
O5 C7 C8 117.13(17) . . ?
C6 C7 C8 118.53(16) . . ?
O6 C8 C9 124.9(2) . . ?
O6 C8 C7 116.87(18) . . ?
C9 C8 C7 118.24(16) . . ?
C4 C9 C8 121.27(19) . . ?
C4 C9 Cl3 119.91(15) . . ?
C8 C9 Cl3 118.81(15) . . ?
Cu1 O7 H7A 112(2) . . ?
Cu1 O7 H7B 112(2) . . ?
H7A O7 H7B 109(3) . . ?
C10 N1 C14 121.6(3) . . ?
C10 N1 H1 119.2 . . ?
C14 N1 H1 119.2 . . ?
N1 C10 C11 120.5(3) . . ?
N1 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 117.1(3) . . ?
C13 C12 C12 122.4(3) . 2_577 ?
C11 C12 C12 120.5(3) . 2_577 ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
N1 C14 C13 119.8(3) . . ?
N1 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
H9A O8 H9B 112(3) . . ?

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
O3 Cu1 O1 C1 -175.97(14) . . . . ?
O4 Cu1 O1 C1 -79.0(4) . . . . ?
O2 Cu1 O1 C1 -3.99(14) . . . . ?
O7 Cu1 O1 C1 93.12(14) . . . . ?
O3 Cu1 O2 C2 90.1(4) . . . . ?
O4 Cu1 O2 C2 174.47(14) . . . . ?
O1 Cu1 O2 C2 4.23(14) . . . . ?
O7 Cu1 O2 C2 -85.89(15) . . . . ?
Cu1 O1 C1 C3 -176.89(15) . . . 2_676 ?
Cu1 O1 C1 C2 3.1(2) . . . . ?
Cu1 O2 C2 C3 176.74(16) . . . . ?
Cu1 O2 C2 C1 -3.7(2) . . . . ?
O1 C1 C2 O2 0.4(3) . . . . ?
C3 C1 C2 O2 -179.57(17) 2_676 . . . ?
O1 C1 C2 C3 180.00(17) . . . . ?
C3 C1 C2 C3 0.0(3) 2_676 . . . ?
O2 C2 C3 C1 179.53(18) . . . 2_676 ?
C1 C2 C3 C1 0.0(3) . . . 2_676 ?
O2 C2 C3 Cl1 -1.0(3) . . . . ?
C1 C2 C3 Cl1 179.53(14) . . . . ?
O4 Cu1 O3 C4 6.79(15) . . . . ?
O2 Cu1 O3 C4 91.9(4) . . . . ?
O1 Cu1 O3 C4 176.75(14) . . . . ?
O7 Cu1 O3 C4 -92.12(15) . . . . ?
O3 Cu1 O4 C5 -7.43(15) . . . . ?
O2 Cu1 O4 C5 -179.44(15) . . . . ?
O1 Cu1 O4 C5 -105.4(3) . . . . ?
O7 Cu1 O4 C5 82.52(15) . . . . ?
Cu1 O3 C4 C9 174.78(16) . . . . ?
Cu1 O3 C4 C5 -5.0(2) . . . . ?
Cu1 O4 C5 C6 -172.90(16) . . . . ?
Cu1 O4 C5 C4 6.6(2) . . . . ?
O3 C4 C5 O4 -1.1(3) . . . . ?
C9 C4 C5 O4 179.07(18) . . . . ?
O3 C4 C5 C6 178.41(18) . . . . ?
C9 C4 C5 C6 -1.4(3) . . . . ?
O4 C5 C6 C7 -179.34(19) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
O4 C5 C6 Cl2 2.2(3) . . . . ?
C4 C5 C6 Cl2 -177.26(14) . . . . ?
C5 C6 C7 O5 179.26(19) . . . . ?
Cl2 C6 C7 O5 -2.3(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
Cl2 C6 C7 C8 178.41(13) . . . . ?
O5 C7 C8 O6 0.5(3) . . . . ?
C6 C7 C8 O6 179.89(19) . . . . ?
O5 C7 C8 C9 179.73(18) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
O3 C4 C9 C8 -179.39(19) . . . . ?
C5 C4 C9 C8 0.4(3) . . . . ?
O3 C4 C9 Cl3 0.1(3) . . . . ?
C5 C4 C9 Cl3 179.90(14) . . . . ?
O6 C8 C9 C4 179.8(2) . . . . ?
C7 C8 C9 C4 0.7(3) . . . . ?
O6 C8 C9 Cl3 0.3(3) . . . . ?
C7 C8 C9 Cl3 -178.81(13) . . . . ?
C14 N1 C10 C11 -1.2(4) . . . . ?
N1 C10 C11 C12 -1.5(4) . . . . ?
C10 C11 C12 C13 3.4(4) . . . . ?
C10 C11 C12 C12 -177.1(3) . . . 2_577 ?
C11 C12 C13 C14 -2.8(4) . . . . ?
C12 C12 C13 C14 177.7(3) 2_577 . . . ?
C10 N1 C14 C13 1.8(4) . . . . ?
C12 C13 C14 N1 0.3(4) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu-h2ca-96
_database_code_depnum_ccdc_archive 'CCDC 1433296'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-06-21 downloaded from the CCDC.
;

_audit_creation_date             2015-02-06T11:39:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C8 H3 Cl2 Cu1 N1 O4'
_chemical_formula_sum            'C8 H3 Cl2 Cu N O4'
_chemical_formula_weight         311.55

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5779(3)
_cell_length_b                   8.2261(4)
_cell_length_c                   16.7585(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.337(4)
_cell_angle_gamma                90
_cell_volume                     1041.68(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2547
_cell_measurement_theta_min      5.2897
_cell_measurement_theta_max      75.5098

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    7.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82595
_exptl_absorpt_correction_T_max  1

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'CCD, ω scans'
_diffrn_reflns_number            4736
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.29
_diffrn_reflns_theta_max         75.69
_diffrn_reflns_theta_full        75.69
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_reflns_number_total             2146
_reflns_number_gt                1888
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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)+(0.0790P)²+0.5205P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2146
_refine_ls_number_parameters     157
_refine_ls_number_restraints     9
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1292
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.801

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
Cu1 Cu 0.04967(5) 0.35037(6) 0.41280(3) 0.03915(19) Uani 1 d . . .
Cl1 Cl 0.57741(11) 0.17017(11) 0.58082(5) 0.0472(2) Uani 1 d . . .
Cl2 Cl 0.52182(11) 0.55348(12) 0.24991(5) 0.0479(2) Uani 1 d . . .
O1 O 0.2300(3) 0.4428(3) 0.34864(15) 0.0402(5) Uani 1 d . . .
O2 O 0.2546(3) 0.2952(3) 0.48650(15) 0.0420(5) Uani 1 d . . .
O3 O 0.8721(3) 0.3039(3) 0.48831(16) 0.0458(6) Uani 1 d . . .
O4 O 0.8482(3) 0.4428(3) 0.34850(15) 0.0401(5) Uani 1 d . . .
C1 C 0.3865(4) 0.4119(4) 0.3768(2) 0.0348(6) Uani 1 d . . .
C2 C 0.3991(4) 0.3218(4) 0.4567(2) 0.0337(6) Uani 1 d . . .
C3 C 0.5646(4) 0.2779(4) 0.4926(2) 0.0364(6) Uani 1 d . . .
C4 C 0.7161(4) 0.3259(4) 0.4580(2) 0.0351(6) Uani 1 d . . .
C5 C 0.7023(4) 0.4123(4) 0.37732(19) 0.0340(6) Uani 1 d . . .
C6 C 0.5370(4) 0.4529(4) 0.34032(19) 0.0345(6) Uani 1 d . . .
N1 N 0.0251(6) 0.1072(5) 0.3580(3) 0.0636(9) Uani 1 d . . .
C7 C -0.0095(6) -0.0229(5) 0.3454(3) 0.0538(9) Uani 1 d D . .
C8 C -0.0545(9) -0.1912(6) 0.3307(4) 0.0772(16) Uani 1 d D . .
H8A H -0.079(12) -0.249(6) 0.377(2) 0.41(12) Uiso 1 d D . .
H8B H 0.045(5) -0.244(5) 0.311(4) 0.11(3) Uiso 1 d D . .
H8C H -0.156(6) -0.204(6) 0.296(4) 0.14(3) Uiso 1 d D . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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 O3 1.954(2) 1_455 ?
Cu1 O4 1.955(2) 1_455 ?
Cu1 O1 1.955(2) . ?
Cu1 O2 1.963(2) . ?
Cu1 N1 2.203(4) . ?
Cl1 C3 1.719(3) . ?
Cl2 C6 1.722(3) . ?
O1 C1 1.268(4) . ?
O2 C2 1.257(4) . ?
O3 C4 1.264(4) . ?
O3 Cu1 1.954(2) 1_655 ?
O4 C5 1.264(4) . ?
O4 Cu1 1.955(2) 1_655 ?
C1 C6 1.376(4) . ?
C1 C2 1.528(5) . ?
C2 C3 1.397(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.524(5) . ?
C5 C6 1.396(4) . ?
N1 C7 1.118(6) . ?
C7 C8 1.442(6) . ?
C8 H8A 0.947(19) . ?
C8 H8B 0.947(18) . ?
C8 H8C 0.941(18) . ?

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
O3 Cu1 O4 83.43(10) 1_455 1_455 ?
O3 Cu1 O1 167.58(12) 1_455 . ?
O4 Cu1 O1 95.44(9) 1_455 . ?
O3 Cu1 O2 95.62(10) 1_455 . ?
O4 Cu1 O2 169.90(11) 1_455 . ?
O1 Cu1 O2 83.31(9) . . ?
O3 Cu1 N1 92.97(14) 1_455 . ?
O4 Cu1 N1 94.90(14) 1_455 . ?
O1 Cu1 N1 99.45(14) . . ?
O2 Cu1 N1 95.19(14) . . ?
C1 O1 Cu1 113.0(2) . . ?
C2 O2 Cu1 112.4(2) . . ?
C4 O3 Cu1 112.4(2) . 1_655 ?
C5 O4 Cu1 112.4(2) . 1_655 ?
O1 C1 C6 124.7(3) . . ?
O1 C1 C2 114.7(3) . . ?
C6 C1 C2 120.6(3) . . ?
O2 C2 C3 124.4(3) . . ?
O2 C2 C1 115.7(3) . . ?
C3 C2 C1 119.9(3) . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 Cl1 120.9(2) . . ?
C2 C3 Cl1 119.6(2) . . ?
O3 C4 C3 124.8(3) . . ?
O3 C4 C5 115.0(3) . . ?
C3 C4 C5 120.2(3) . . ?
O4 C5 C6 124.3(3) . . ?
O4 C5 C4 115.4(3) . . ?
C6 C5 C4 120.3(3) . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 Cl2 120.4(2) . . ?
C5 C6 Cl2 120.3(2) . . ?
C7 N1 Cu1 163.5(4) . . ?
N1 C7 C8 178.9(6) . . ?
C7 C8 H8A 114(4) . . ?
C7 C8 H8B 109(3) . . ?
H8A C8 H8B 105(4) . . ?
C7 C8 H8C 113(3) . . ?
H8A C8 H8C 104(4) . . ?
H8B C8 H8C 111(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
O3 Cu1 O1 C1 92.7(5) 1_455 . . . ?
O4 Cu1 O1 C1 176.9(2) 1_455 . . . ?
O2 Cu1 O1 C1 6.9(2) . . . . ?
N1 Cu1 O1 C1 -87.2(2) . . . . ?
O3 Cu1 O2 C2 -176.1(2) 1_455 . . . ?
O4 Cu1 O2 C2 -92.0(6) 1_455 . . . ?
O1 Cu1 O2 C2 -8.5(2) . . . . ?
N1 Cu1 O2 C2 90.4(3) . . . . ?
Cu1 O1 C1 C6 175.3(3) . . . . ?
Cu1 O1 C1 C2 -4.4(3) . . . . ?
Cu1 O2 C2 C3 -173.0(3) . . . . ?
Cu1 O2 C2 C1 8.4(3) . . . . ?
O1 C1 C2 O2 -2.8(4) . . . . ?
C6 C1 C2 O2 177.5(3) . . . . ?
O1 C1 C2 C3 178.5(3) . . . . ?
C6 C1 C2 C3 -1.2(5) . . . . ?
O2 C2 C3 C4 -174.3(3) . . . . ?
C1 C2 C3 C4 4.3(5) . . . . ?
O2 C2 C3 Cl1 3.8(5) . . . . ?
C1 C2 C3 Cl1 -177.7(2) . . . . ?
Cu1 O3 C4 C3 169.0(3) 1_655 . . . ?
Cu1 O3 C4 C5 -11.0(4) 1_655 . . . ?
C2 C3 C4 O3 174.4(3) . . . . ?
Cl1 C3 C4 O3 -3.7(5) . . . . ?
C2 C3 C4 C5 -5.7(5) . . . . ?
Cl1 C3 C4 C5 176.3(2) . . . . ?
Cu1 O4 C5 C6 -174.9(3) 1_655 . . . ?
Cu1 O4 C5 C4 5.4(3) 1_655 . . . ?
O3 C4 C5 O4 3.9(4) . . . . ?
C3 C4 C5 O4 -176.1(3) . . . . ?
O3 C4 C5 C6 -175.8(3) . . . . ?
C3 C4 C5 C6 4.2(5) . . . . ?
O1 C1 C6 C5 180.0(3) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
O1 C1 C6 Cl2 0.0(5) . . . . ?
C2 C1 C6 Cl2 179.6(2) . . . . ?
O4 C5 C6 C1 179.2(3) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
O4 C5 C6 Cl2 -0.8(5) . . . . ?
C4 C5 C6 Cl2 178.9(2) . . . . ?
O3 Cu1 N1 C7 -11.2(14) 1_455 . . . ?
O4 Cu1 N1 C7 -94.8(14) 1_455 . . . ?
O1 Cu1 N1 C7 168.8(14) . . . . ?
O2 Cu1 N1 C7 84.8(14) . . . . ?
Cu1 N1 C7 C8 -3E1(3) . . . . ?

####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 1433297'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-06-21 downloaded from the CCDC.
;

_audit_creation_date             2014-10-14T15:29:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C6 H4 Cl2 Cu1 O6'
_chemical_formula_sum            'C6 H4 Cl2 Cu O6'
_chemical_formula_weight         306.53

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0866(6)
_cell_length_b                   4.8324(4)
_cell_length_c                   12.9148(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.388(8)
_cell_angle_gamma                90
_cell_volume                     478.91(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1626
_cell_measurement_theta_min      3.6036
_cell_measurement_theta_max      75.6288

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    2.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             302
_exptl_absorpt_coefficient_mu    8.484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71513
_exptl_absorpt_correction_T_max  1

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54179
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'CCD, ω scans'
_diffrn_reflns_number            4605
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         75.81
_diffrn_reflns_theta_full        75.81
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_reflns_number_total             1047
_reflns_number_gt                960
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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)+(0.0646P)²+3.8061P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1047
_refine_ls_number_parameters     79
_refine_ls_number_restraints     3
_refine_ls_R_factor_gt           0.073
_refine_ls_wR_factor_ref         0.1913
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.032
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.592

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
Cu1 Cu 0 0 0.5 0.0383(5) Uani 1 d S . .
Cl1 Cl -0.4312(2) 0.4779(4) 0.67689(13) 0.0394(5) Uani 1 d . . .
O1 O -0.1758(6) 0.2038(12) 0.5856(4) 0.0435(13) Uani 1 d . . .
O2 O -0.7645(6) 0.1930(12) 0.5651(4) 0.0398(12) Uani 1 d . . .
C1 C -0.3294(8) 0.1178(15) 0.5491(5) 0.0312(14) Uani 1 d . . .
C2 C -0.4695(8) 0.2145(14) 0.5813(5) 0.0301(13) Uani 1 d . . .
C3 C -0.6349(8) 0.1113(14) 0.5373(5) 0.0291(13) Uani 1 d . . .
O3 O 0.0681(9) -0.2842(16) 0.6212(5) 0.0588(16) Uani 1 d D . .
H3A H 0.146(14) -0.16(2) 0.669(7) 0.10(4) Uiso 1 d D . .
H3B H 0.023(13) -0.39(2) 0.668(6) 0.07(3) Uiso 1 d D . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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 O3 2.024(7) . ?
Cu1 O3 2.024(7) 3_556 ?
Cu1 O2 2.048(5) 3_456 ?
Cu1 O2 2.048(5) 1_655 ?
Cu1 O1 2.282(5) . ?
Cu1 O1 2.282(5) 3_556 ?
Cl1 C2 1.732(7) . ?
O1 C1 1.252(8) . ?
O2 C3 1.274(8) . ?
O2 Cu1 2.048(5) 1_455 ?
C1 C2 1.405(9) . ?
C1 C3 1.533(9) 3_456 ?
C2 C3 1.372(9) . ?
C3 C1 1.533(9) 3_456 ?
O3 H3A 0.96(2) . ?
O3 H3B 0.95(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
O3 Cu1 O3 180.0000(10) . 3_556 ?
O3 Cu1 O2 90.0(3) . 3_456 ?
O3 Cu1 O2 90.0(2) 3_556 3_456 ?
O3 Cu1 O2 90.0(3) . 1_655 ?
O3 Cu1 O2 90.0(3) 3_556 1_655 ?
O2 Cu1 O2 180.0000(10) 3_456 1_655 ?
O3 Cu1 O1 88.7(2) . . ?
O3 Cu1 O1 91.3(2) 3_556 . ?
O2 Cu1 O1 75.80(18) 3_456 . ?
O2 Cu1 O1 104.20(18) 1_655 . ?
O3 Cu1 O1 91.3(2) . 3_556 ?
O3 Cu1 O1 88.7(2) 3_556 3_556 ?
O2 Cu1 O1 104.20(18) 3_456 3_556 ?
O2 Cu1 O1 75.80(18) 1_655 3_556 ?
O1 Cu1 O1 180.0(2) . 3_556 ?
C1 O1 Cu1 111.7(5) . . ?
C3 O2 Cu1 119.0(5) . 1_455 ?
O1 C1 C2 125.1(6) . . ?
O1 C1 C3 116.8(6) . 3_456 ?
C2 C1 C3 118.1(6) . 3_456 ?
C3 C2 C1 121.9(6) . . ?
C3 C2 Cl1 119.7(5) . . ?
C1 C2 Cl1 118.4(5) . . ?
O2 C3 C2 123.5(6) . . ?
O2 C3 C1 116.5(6) . 3_456 ?
C2 C3 C1 120.0(6) . 3_456 ?
Cu1 O3 H3A 92(7) . . ?
Cu1 O3 H3B 142(7) . . ?
H3A O3 H3B 104(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
O3 Cu1 O1 C1 -94.3(5) . . . . ?
O3 Cu1 O1 C1 85.7(5) 3_556 . . . ?
O2 Cu1 O1 C1 -4.0(5) 3_456 . . . ?
O2 Cu1 O1 C1 176.0(5) 1_655 . . . ?
O1 Cu1 O1 C1 9E1(10) 3_556 . . . ?
Cu1 O1 C1 C2 -176.6(5) . . . . ?
Cu1 O1 C1 C3 3.6(7) . . . 3_456 ?
O1 C1 C2 C3 179.7(7) . . . . ?
C3 C1 C2 C3 -0.5(10) 3_456 . . . ?
O1 C1 C2 Cl1 1.4(10) . . . . ?
C3 C1 C2 Cl1 -178.8(4) 3_456 . . . ?
Cu1 O2 C3 C2 -175.7(5) 1_455 . . . ?
Cu1 O2 C3 C1 3.4(8) 1_455 . . 3_456 ?
C1 C2 C3 O2 179.6(6) . . . . ?
Cl1 C2 C3 O2 -2.2(9) . . . . ?
C1 C2 C3 C1 0.5(10) . . . 3_456 ?
Cl1 C2 C3 C1 178.7(5) . . . 3_456 ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu-ca-iz-117_2
_database_code_depnum_ccdc_archive 'CCDC 1473407'
_audit_update_record             
;
2016-04-11 deposited with the CCDC.
2016-06-21 downloaded from the CCDC.
;

_audit_creation_date             2016-01-22T11:16:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H8 Cl2 Cu1 N4 O4'
_chemical_formula_sum            'C12 H8 Cl2 Cu N4 O4'
_chemical_formula_weight         406.67

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
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                   25.3992(8)
_cell_length_b                   8.1066(2)
_cell_length_c                   14.2791(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.491(3)
_cell_angle_gamma                90
_cell_volume                     2921.24(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3501
_cell_measurement_theta_min      3.1123
_cell_measurement_theta_max      75.7426
_cell_measurement_temperature    293(2)
_exptl_crystal_description       rod
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1624
_exptl_absorpt_coefficient_mu    5.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.62257
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            6948
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_theta_min         3.5
_diffrn_reflns_theta_max         75.92
_diffrn_reflns_theta_full        75.92
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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.
;
_reflns_number_total             2994
_reflns_number_gt                2373
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1075
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         2994
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0662P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.364 0.702 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.965 0.589 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.031 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.049 0.032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1A 0.5 0.71734(4) 0.25 0.03360(15) Uani d S 1 . . Cu
Cl1A 0.45483(3) 0.21816(7) 0.03365(4) 0.05123(18) Uani d . 1 . . Cl
O1A 0.48539(6) 0.50662(16) 0.15751(11) 0.0419(3) Uani d . 1 . . O
O2A 0.48434(6) -0.07058(16) 0.15832(11) 0.0411(3) Uani d . 1 . . O
C1A 0.49018(8) 0.3693(2) 0.19700(14) 0.0338(4) Uani d . 1 . . C
C2A 0.47899(9) 0.2180(2) 0.15173(15) 0.0361(4) Uani d . 1 . . C
C3A 0.48956(8) 0.0681(2) 0.19754(15) 0.0341(4) Uani d . 1 . . C
N1A 0.57712(8) 0.7223(2) 0.23341(14) 0.0382(4) Uani d . 1 . . N
N2A 0.66202(8) 0.6764(2) 0.26052(15) 0.0464(4) Uani d . 1 . . N
H2A 0.6915 0.6289 0.2801 0.056 Uiso calc R 1 . . H
C4A 0.61420(9) 0.6236(3) 0.27385(18) 0.0472(5) Uani d . 1 . . C
H4A 0.6076 0.529 0.3074 0.057 Uiso calc R 1 . . H
C5A 0.65633(10) 0.8195(3) 0.2102(2) 0.0498(5) Uani d . 1 . . C
H5A 0.6832 0.8854 0.1916 0.06 Uiso calc R 1 . . H
C6A 0.60369(9) 0.8461(3) 0.19307(17) 0.0449(5) Uani d . 1 . . C
H6A 0.5879 0.9345 0.1592 0.054 Uiso calc R 1 . . H
Cu1B 0.25 0.75 0 0.03279(15) Uani d S 1 . . Cu
Cl1B 0.29585(3) 1.23215(6) 0.21603(4) 0.04667(17) Uani d . 1 . . Cl
O1B 0.26508(6) 0.95285(15) 0.08412(10) 0.0360(3) Uani d . 1 . . O
O2B 0.23539(6) 0.97147(16) -0.10019(10) 0.0385(3) Uani d . 1 . . O
C1B 0.26022(8) 1.0945(2) 0.04839(14) 0.0313(4) Uani d . 1 . . C
C2B 0.27171(9) 1.2400(2) 0.09835(15) 0.0342(4) Uani d . 1 . . C
C3B 0.23987(8) 1.1048(2) -0.05692(14) 0.0316(4) Uani d . 1 . . C
N1B 0.32735(8) 0.7409(2) -0.01561(13) 0.0376(4) Uani d . 1 . . N
N2B 0.41234(9) 0.7849(3) 0.01073(16) 0.0498(5) Uani d . 1 . . N
H2B 0.4419 0.8313 0.0308 0.06 Uiso calc R 1 . . H
C4B 0.36466(9) 0.8369(3) 0.02614(18) 0.0470(5) Uani d . 1 . . C
H4B 0.3584 0.9292 0.0619 0.056 Uiso calc R 1 . . H
C5B 0.40635(10) 0.6454(3) -0.0423(2) 0.0512(5) Uani d . 1 . . C
H5B 0.4331 0.5806 -0.0626 0.061 Uiso calc R 1 . . H
C6B 0.35350(10) 0.6202(3) -0.05952(17) 0.0467(5) Uani d . 1 . . C
H6B 0.3374 0.5346 -0.0955 0.056 Uiso calc R 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1A N1A 2_655 2.000(2) ?
Cu1A N1A . 2.000(2) ?
Cu1A O1A . 2.1654(15) ?
Cu1A O1A 2_655 2.1654(15) ?
Cu1A O2A 2_665 2.1703(15) ?
Cu1A O2A 1_565 2.1703(15) ?
Cl1A C2A . 1.728(2) ?
O1A C1A . 1.248(2) ?
O2A C3A . 1.256(2) ?
O2A Cu1A 1_545 2.1703(15) ?
C1A C2A . 1.400(3) ?
C1A C1A 2_655 1.539(4) ?
C2A C3A . 1.392(3) ?
C3A C3A 2_655 1.532(4) ?
N1A C4A . 1.318(3) ?
N1A C6A . 1.372(3) ?
N2A C4A . 1.322(3) ?
N2A C5A . 1.363(3) ?
N2A H2A . 0.86 ?
C4A H4A . 0.93 ?
C5A C6A . 1.349(3) ?
C5A H5A . 0.93 ?
C6A H6A . 0.93 ?
Cu1B N1B 7_565 2.003(2) ?
Cu1B N1B . 2.003(2) ?
Cu1B O1B 7_565 2.0468(12) ?
Cu1B O1B . 2.0468(12) ?
Cu1B O2B . 2.2995(14) ?
Cu1B O2B 7_565 2.2995(14) ?
Cl1B C2B . 1.724(2) ?
O1B C1B . 1.257(2) ?
O2B C3B . 1.244(2) ?
C1B C2B . 1.392(3) ?
C1B C3B . 1.536(3) ?
C2B C3B 7_575 1.407(3) ?
C3B C2B 7_575 1.407(3) ?
N1B C4B . 1.316(3) ?
N1B C6B . 1.373(3) ?
N2B C4B . 1.324(3) ?
N2B C5B . 1.361(3) ?
N2B H2B . 0.86 ?
C4B H4B . 0.93 ?
C5B C6B . 1.353(3) ?
C5B H5B . 0.93 ?
C6B H6B . 0.93 ?

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
N1A Cu1A N1A 177.68(9) 2_655 . ?
N1A Cu1A O1A 89.18(7) 2_655 . ?
N1A Cu1A O1A 92.65(7) . . ?
N1A Cu1A O1A 92.65(7) 2_655 2_655 ?
N1A Cu1A O1A 89.18(7) . 2_655 ?
O1A Cu1A O1A 75.85(8) . 2_655 ?
N1A Cu1A O2A 91.59(6) 2_655 2_665 ?
N1A Cu1A O2A 86.58(7) . 2_665 ?
O1A Cu1A O2A 179.16(6) . 2_665 ?
O1A Cu1A O2A 104.47(6) 2_655 2_665 ?
N1A Cu1A O2A 86.58(7) 2_655 1_565 ?
N1A Cu1A O2A 91.59(6) . 1_565 ?
O1A Cu1A O2A 104.47(6) . 1_565 ?
O1A Cu1A O2A 179.16(6) 2_655 1_565 ?
O2A Cu1A O2A 75.22(8) 2_665 1_565 ?
C1A O1A Cu1A 115.28(14) . . ?
C3A O2A Cu1A 115.91(14) . 1_545 ?
O1A C1A C2A 124.6(2) . . ?
O1A C1A C1A 116.65(12) . 2_655 ?
C2A C1A C1A 118.70(12) . 2_655 ?
C3A C2A C1A 122.0(2) . . ?
C3A C2A Cl1A 119.18(15) . . ?
C1A C2A Cl1A 118.75(15) . . ?
O2A C3A C2A 124.5(2) . . ?
O2A C3A C3A 116.33(12) . 2_655 ?
C2A C3A C3A 119.12(12) . 2_655 ?
C4A N1A C6A 105.5(2) . . ?
C4A N1A Cu1A 126.63(16) . . ?
C6A N1A Cu1A 126.83(15) . . ?
C4A N2A C5A 107.9(2) . . ?
C4A N2A H2A 126.1 . . ?
C5A N2A H2A 126.1 . . ?
N1A C4A N2A 111.3(2) . . ?
N1A C4A H4A 124.4 . . ?
N2A C4A H4A 124.4 . . ?
C6A C5A N2A 106.0(2) . . ?
C6A C5A H5A 127 . . ?
N2A C5A H5A 127 . . ?
C5A C6A N1A 109.4(2) . . ?
C5A C6A H6A 125.3 . . ?
N1A C6A H6A 125.3 . . ?
N1B Cu1B N1B 180 7_565 . ?
N1B Cu1B O1B 88.52(6) 7_565 7_565 ?
N1B Cu1B O1B 91.48(6) . 7_565 ?
N1B Cu1B O1B 91.48(6) 7_565 . ?
N1B Cu1B O1B 88.52(6) . . ?
O1B Cu1B O1B 180.00(6) 7_565 . ?
N1B Cu1B O2B 87.08(6) 7_565 . ?
N1B Cu1B O2B 92.92(6) . . ?
O1B Cu1B O2B 104.83(5) 7_565 . ?
O1B Cu1B O2B 75.17(5) . . ?
N1B Cu1B O2B 92.92(6) 7_565 7_565 ?
N1B Cu1B O2B 87.08(6) . 7_565 ?
O1B Cu1B O2B 75.17(5) 7_565 7_565 ?
O1B Cu1B O2B 104.83(5) . 7_565 ?
O2B Cu1B O2B 180.00(7) . 7_565 ?
C1B O1B Cu1B 119.50(12) . . ?
C3B O2B Cu1B 111.73(12) . . ?
O1B C1B C2B 124.11(18) . . ?
O1B C1B C3B 116.99(16) . . ?
C2B C1B C3B 118.90(17) . . ?
C1B C2B C3B 121.38(19) . 7_575 ?
C1B C2B Cl1B 119.94(15) . . ?
C3B C2B Cl1B 118.49(15) 7_575 . ?
O2B C3B C2B 124.42(19) . 7_575 ?
O2B C3B C1B 116.15(16) . . ?
C2B C3B C1B 119.42(17) 7_575 . ?
C4B N1B C6B 105.5(2) . . ?
C4B N1B Cu1B 126.35(16) . . ?
C6B N1B Cu1B 127.48(15) . . ?
C4B N2B C5B 108.1(2) . . ?
C4B N2B H2B 126 . . ?
C5B N2B H2B 126 . . ?
N1B C4B N2B 111.2(2) . . ?
N1B C4B H4B 124.4 . . ?
N2B C4B H4B 124.4 . . ?
C6B C5B N2B 105.8(2) . . ?
C6B C5B H5B 127.1 . . ?
N2B C5B H5B 127.1 . . ?
C5B C6B N1B 109.4(2) . . ?
C5B C6B H6B 125.3 . . ?
N1B C6B H6B 125.3 . . ?

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
N1A Cu1A O1A C1A -91.10(16) 2_655 . . . ?
N1A Cu1A O1A C1A 90.33(16) . . . . ?
O1A Cu1A O1A C1A 1.85(12) 2_655 . . . ?
O2A Cu1A O1A C1A 114(4) 2_665 . . . ?
O2A Cu1A O1A C1A -177.35(14) 1_565 . . . ?
Cu1A O1A C1A C2A 175.34(17) . . . . ?
Cu1A O1A C1A C1A -4.7(3) . . . 2_655 ?
O1A C1A C2A C3A 174.2(2) . . . . ?
C1A C1A C2A C3A -5.8(4) 2_655 . . . ?
O1A C1A C2A Cl1A -2.1(3) . . . . ?
C1A C1A C2A Cl1A 177.86(19) 2_655 . . . ?
Cu1A O2A C3A C2A -176.92(17) 1_545 . . . ?
Cu1A O2A C3A C3A 4.7(3) 1_545 . . 2_655 ?
C1A C2A C3A O2A -174.0(2) . . . . ?
Cl1A C2A C3A O2A 2.3(3) . . . . ?
C1A C2A C3A C3A 4.3(4) . . . 2_655 ?
Cl1A C2A C3A C3A -179.38(19) . . . 2_655 ?
N1A Cu1A N1A C4A 140.51(19) 2_655 . . . ?
O1A Cu1A N1A C4A -77.41(19) . . . . ?
O1A Cu1A N1A C4A -1.62(19) 2_655 . . . ?
O2A Cu1A N1A C4A 102.93(19) 2_665 . . . ?
O2A Cu1A N1A C4A 178.02(19) 1_565 . . . ?
N1A Cu1A N1A C6A -26.00(19) 2_655 . . . ?
O1A Cu1A N1A C6A 116.08(19) . . . . ?
O1A Cu1A N1A C6A -168.1(2) 2_655 . . . ?
O2A Cu1A N1A C6A -63.58(19) 2_665 . . . ?
O2A Cu1A N1A C6A 11.5(2) 1_565 . . . ?
C6A N1A C4A N2A -0.7(3) . . . . ?
Cu1A N1A C4A N2A -169.54(16) . . . . ?
C5A N2A C4A N1A 1.3(3) . . . . ?
C4A N2A C5A C6A -1.3(3) . . . . ?
N2A C5A C6A N1A 0.9(3) . . . . ?
C4A N1A C6A C5A -0.2(3) . . . . ?
Cu1A N1A C6A C5A 168.65(17) . . . . ?
N1B Cu1B O1B C1B -86.45(16) 7_565 . . . ?
N1B Cu1B O1B C1B 93.55(16) . . . . ?
O1B Cu1B O1B C1B 14E1(10) 7_565 . . . ?
O2B Cu1B O1B C1B 0.13(15) . . . . ?
O2B Cu1B O1B C1B -179.87(15) 7_565 . . . ?
N1B Cu1B O2B C3B 87.97(15) 7_565 . . . ?
N1B Cu1B O2B C3B -92.03(15) . . . . ?
O1B Cu1B O2B C3B 175.67(14) 7_565 . . . ?
O1B Cu1B O2B C3B -4.33(14) . . . . ?
O2B Cu1B O2B C3B -7E1(10) 7_565 . . . ?
Cu1B O1B C1B C2B -177.07(16) . . . . ?
Cu1B O1B C1B C3B 3.4(3) . . . . ?
O1B C1B C2B C3B -173.12(19) . . . 7_575 ?
C3B C1B C2B C3B 6.4(4) . . . 7_575 ?
O1B C1B C2B Cl1B 1.8(3) . . . . ?
C3B C1B C2B Cl1B -178.72(16) . . . . ?
Cu1B O2B C3B C2B -173.74(17) . . . 7_575 ?
Cu1B O2B C3B C1B 7.1(2) . . . . ?
O1B C1B C3B O2B -7.5(3) . . . . ?
C2B C1B C3B O2B 172.93(19) . . . . ?
O1B C1B C3B C2B 173.28(19) . . . 7_575 ?
C2B C1B C3B C2B -6.2(4) . . . 7_575 ?
N1B Cu1B N1B C4B 0E1(10) 7_565 . . . ?
O1B Cu1B N1B C4B -176.03(19) 7_565 . . . ?
O1B Cu1B N1B C4B 3.97(19) . . . . ?
O2B Cu1B N1B C4B 79.0(2) . . . . ?
O2B Cu1B N1B C4B -101.0(2) 7_565 . . . ?
N1B Cu1B N1B C6B 17E1(10) 7_565 . . . ?
O1B Cu1B N1B C6B -6.8(2) 7_565 . . . ?
O1B Cu1B N1B C6B 173.2(2) . . . . ?
O2B Cu1B N1B C6B -111.72(19) . . . . ?
O2B Cu1B N1B C6B 68.28(19) 7_565 . . . ?
C6B N1B C4B N2B 0.4(3) . . . . ?
Cu1B N1B C4B N2B 171.57(16) . . . . ?
C5B N2B C4B N1B -1.3(3) . . . . ?
C4B N2B C5B C6B 1.6(3) . . . . ?
N2B C5B C6B N1B -1.4(3) . . . . ?
C4B N1B C6B C5B 0.6(3) . . . . ?
Cu1B N1B C6B C5B -170.38(17) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu-ca-iz-116
_database_code_depnum_ccdc_archive 'CCDC 1473408'
_audit_update_record             
;
2016-04-11 deposited with the CCDC.
2016-06-21 downloaded from the CCDC.
;

_audit_creation_date             2016-01-13T10:48:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H4 Cl4 Cu O10, 2(C3 H5 N2)'
_chemical_formula_sum            'C18 H14 Cl4 Cu N4 O10 '
_chemical_formula_weight         651.68

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2635(10)
_cell_length_b                   8.7473(8)
_cell_length_c                   9.1791(7)
_cell_angle_alpha                70.332(8)
_cell_angle_beta                 71.570(9)
_cell_angle_gamma                67.319(10)
_cell_volume                     563.05(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2573
_cell_measurement_theta_min      5.2349
_cell_measurement_theta_max      75.8032
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'dark purple'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             327.0
_exptl_absorpt_coefficient_mu    6.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.66584
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            4503
_diffrn_reflns_av_R_equivalents  0.04
_diffrn_reflns_av_unetI/netI     0.037
_diffrn_reflns_theta_min         5.24
_diffrn_reflns_theta_max         75.99
_diffrn_reflns_theta_full        75.99
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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.
;
_reflns_number_total             2278
_reflns_number_gt                2094
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.127
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_number_reflns         2278
_refine_ls_number_parameters     177
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0821P)²+0.1492P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.031 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.049 0.032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.364 0.702 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.965 0.589 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.5 0 0.5 0.03247(19) Uani d S 1 . . Cu
Cl1 0.16567(10) 0.47097(9) 0.12145(8) 0.0433(2) Uani d . 1 . . Cl
Cl2 0.32633(9) 0.48967(8) 0.74431(8) 0.0400(2) Uani d . 1 . . Cl
O1 0.4449(2) 0.1887(2) 0.6020(2) 0.0329(4) Uani d . 1 . . O
O2 0.3797(3) 0.1841(2) 0.3424(2) 0.0344(4) Uani d . 1 . . O
O3 0.0184(3) 0.7562(2) 0.2784(2) 0.0386(4) Uani d . 1 . . O
O4 0.1037(3) 0.7716(2) 0.5292(3) 0.0429(5) Uani d . 1 . . O
O5 0.2204(3) -0.0502(3) 0.6560(2) 0.0380(4) Uani d D 1 . . O
C1 0.3464(3) 0.3312(3) 0.5310(3) 0.0280(5) Uani d . 1 . . C
C2 0.3091(3) 0.3275(3) 0.3801(3) 0.0297(5) Uani d . 1 . . C
C3 0.2044(3) 0.4728(3) 0.2957(3) 0.0309(5) Uani d . 1 . . C
C4 0.1221(3) 0.6266(3) 0.3450(3) 0.0300(5) Uani d . 1 . . C
C5 0.1670(3) 0.6337(3) 0.4943(3) 0.0307(5) Uani d . 1 . . C
C6 0.2785(3) 0.4809(3) 0.5775(3) 0.0306(5) Uani d . 1 . . C
H5A 0.194(5) -0.129(4) 0.629(5) 0.064(12) Uiso d D 1 . . H
H5B 0.123(4) 0.047(3) 0.651(4) 0.044(9) Uiso d D 1 . . H
N1 0.6329(3) 0.1044(3) 0.8469(3) 0.0398(5) Uani d . 1 . . N
H1 0.5709 0.1533 0.7747 0.048 Uiso calc R 1 . . H
N2 0.7261(4) 0.0518(3) 1.0559(3) 0.0427(5) Uani d . 1 . . N
H2 0.7349 0.0605 1.1435 0.051 Uiso calc R 1 . . H
C7 0.6062(4) 0.1592(4) 0.9720(4) 0.0435(6) Uani d . 1 . . C
H7 0.5177 0.2572 0.997 0.052 Uiso calc R 1 . . H
C8 0.8341(4) -0.0755(4) 0.9817(4) 0.0437(6) Uani d . 1 . . C
H8 0.93 -0.1672 1.0154 0.052 Uiso calc R 1 . . H
C9 0.7748(4) -0.0425(4) 0.8499(4) 0.0417(6) Uani d . 1 . . C
H9 0.8216 -0.1074 0.7753 0.05 Uiso calc R 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 2_656 1.9442(17) ?
Cu1 O2 . 1.9442(17) ?
Cu1 O1 . 1.9999(17) ?
Cu1 O1 2_656 1.9999(17) ?
Cu1 O5 2_656 2.418(2) ?
Cu1 O5 . 2.418(2) ?
Cl1 C3 . 1.733(2) ?
Cl2 C6 . 1.730(2) ?
O1 C1 . 1.283(3) ?
O2 C2 . 1.278(3) ?
O3 C4 . 1.228(3) ?
O4 C5 . 1.225(3) ?
O5 H5A . 0.924(19) ?
O5 H5B . 0.915(18) ?
C1 C6 . 1.367(3) ?
C1 C2 . 1.524(3) ?
C2 C3 . 1.371(4) ?
C3 C4 . 1.410(3) ?
C4 C5 . 1.554(3) ?
C5 C6 . 1.423(4) ?
N1 C7 . 1.314(4) ?
N1 C9 . 1.364(4) ?
N1 H1 . 0.86 ?
N2 C7 . 1.317(4) ?
N2 C8 . 1.364(4) ?
N2 H2 . 0.86 ?
C7 H7 . 0.93 ?
C8 C9 . 1.348(4) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?

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
O2 Cu1 O2 180.00(9) 2_656 . ?
O2 Cu1 O1 96.78(7) 2_656 . ?
O2 Cu1 O1 83.22(7) . . ?
O2 Cu1 O1 83.22(7) 2_656 2_656 ?
O2 Cu1 O1 96.78(7) . 2_656 ?
O1 Cu1 O1 180.0000(10) . 2_656 ?
O2 Cu1 O5 91.84(8) 2_656 2_656 ?
O2 Cu1 O5 88.16(8) . 2_656 ?
O1 Cu1 O5 90.49(7) . 2_656 ?
O1 Cu1 O5 89.51(7) 2_656 2_656 ?
O2 Cu1 O5 88.16(8) 2_656 . ?
O2 Cu1 O5 91.84(8) . . ?
O1 Cu1 O5 89.51(7) . . ?
O1 Cu1 O5 90.49(7) 2_656 . ?
O5 Cu1 O5 180 2_656 . ?
C1 O1 Cu1 112.08(15) . . ?
C2 O2 Cu1 113.51(15) . . ?
Cu1 O5 H5A 113(3) . . ?
Cu1 O5 H5B 113(2) . . ?
H5A O5 H5B 107(3) . . ?
O1 C1 C6 125.9(2) . . ?
O1 C1 C2 114.8(2) . . ?
C6 C1 C2 119.3(2) . . ?
O2 C2 C3 124.6(2) . . ?
O2 C2 C1 115.8(2) . . ?
C3 C2 C1 119.5(2) . . ?
C2 C3 C4 122.9(2) . . ?
C2 C3 Cl1 119.79(19) . . ?
C4 C3 Cl1 117.26(18) . . ?
O3 C4 C3 125.0(2) . . ?
O3 C4 C5 117.4(2) . . ?
C3 C4 C5 117.6(2) . . ?
O4 C5 C6 125.8(2) . . ?
O4 C5 C4 116.7(2) . . ?
C6 C5 C4 117.6(2) . . ?
C1 C6 C5 122.8(2) . . ?
C1 C6 Cl2 119.98(19) . . ?
C5 C6 Cl2 117.22(19) . . ?
C7 N1 C9 109.1(2) . . ?
C7 N1 H1 125.5 . . ?
C9 N1 H1 125.5 . . ?
C7 N2 C8 109.1(2) . . ?
C7 N2 H2 125.5 . . ?
C8 N2 H2 125.5 . . ?
N1 C7 N2 108.4(3) . . ?
N1 C7 H7 125.8 . . ?
N2 C7 H7 125.8 . . ?
C9 C8 N2 106.6(3) . . ?
C9 C8 H8 126.7 . . ?
N2 C8 H8 126.7 . . ?
C8 C9 N1 106.8(3) . . ?
C8 C9 H9 126.6 . . ?
N1 C9 H9 126.6 . . ?

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
O2 Cu1 O1 C1 -173.66(17) 2_656 . . . ?
O2 Cu1 O1 C1 6.34(17) . . . . ?
O1 Cu1 O1 C1 -7E1(10) 2_656 . . . ?
O5 Cu1 O1 C1 94.43(18) 2_656 . . . ?
O5 Cu1 O1 C1 -85.57(18) . . . . ?
O2 Cu1 O2 C2 15E1(10) 2_656 . . . ?
O1 Cu1 O2 C2 -6.37(18) . . . . ?
O1 Cu1 O2 C2 173.63(18) 2_656 . . . ?
O5 Cu1 O2 C2 -97.09(18) 2_656 . . . ?
O5 Cu1 O2 C2 82.91(18) . . . . ?
Cu1 O1 C1 C6 176.2(2) . . . . ?
Cu1 O1 C1 C2 -5.2(3) . . . . ?
Cu1 O2 C2 C3 -174.2(2) . . . . ?
Cu1 O2 C2 C1 5.3(3) . . . . ?
O1 C1 C2 O2 0.0(3) . . . . ?
C6 C1 C2 O2 178.7(2) . . . . ?
O1 C1 C2 C3 179.6(2) . . . . ?
C6 C1 C2 C3 -1.7(4) . . . . ?
O2 C2 C3 C4 177.0(2) . . . . ?
C1 C2 C3 C4 -2.5(4) . . . . ?
O2 C2 C3 Cl1 -1.9(4) . . . . ?
C1 C2 C3 Cl1 178.50(18) . . . . ?
C2 C3 C4 O3 -175.2(3) . . . . ?
Cl1 C3 C4 O3 3.8(4) . . . . ?
C2 C3 C4 C5 5.3(4) . . . . ?
Cl1 C3 C4 C5 -175.67(18) . . . . ?
O3 C4 C5 O4 -4.2(4) . . . . ?
C3 C4 C5 O4 175.3(2) . . . . ?
O3 C4 C5 C6 176.3(2) . . . . ?
C3 C4 C5 C6 -4.2(4) . . . . ?
O1 C1 C6 C5 -178.8(2) . . . . ?
C2 C1 C6 C5 2.7(4) . . . . ?
O1 C1 C6 Cl2 1.0(4) . . . . ?
C2 C1 C6 Cl2 -177.58(18) . . . . ?
O4 C5 C6 C1 -179.3(3) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
O4 C5 C6 Cl2 1.0(4) . . . . ?
C4 C5 C6 Cl2 -179.55(17) . . . . ?
C9 N1 C7 N2 -0.2(4) . . . . ?
C8 N2 C7 N1 0.4(4) . . . . ?
C7 N2 C8 C9 -0.5(4) . . . . ?
N2 C8 C9 N1 0.3(4) . . . . ?
C7 N1 C9 C8 0.0(4) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
