# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1001894'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 F2 N2 O4 Zn'
_chemical_formula_weight         345.56

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'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   12.2658(16)
_cell_length_b                   20.425(3)
_cell_length_c                   9.6121(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2408.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2332
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.28

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7054
_exptl_absorpt_correction_T_max  0.7733
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4323
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         28.29
_reflns_number_total             1486
_reflns_number_gt                1431
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0217P)²+1.3403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(16)
_refine_ls_number_reflns         1486
_refine_ls_number_parameters     96
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.102
_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
Zn1 Zn 0.2500 0.2500 1.11992(5) 0.02243(11) Uani 1 2 d S . .
F1 F -0.13134(14) 0.47682(7) 0.8576(2) 0.0421(4) Uani 1 1 d . . .
O1 O 0.14104(15) 0.31961(10) 1.0669(2) 0.0361(5) Uani 1 1 d . . .
O2 O 0.11887(17) 0.23142(10) 0.9387(2) 0.0364(5) Uani 1 1 d . . .
N1 N -0.15743(17) 0.30947(10) 0.7532(2) 0.0241(4) Uani 1 1 d . . .
C1 C -0.0015(2) 0.32071(13) 0.9013(2) 0.0233(6) Uani 1 1 d . . .
C2 C -0.0213(2) 0.38691(13) 0.9182(3) 0.0267(5) Uani 1 1 d . . .
H2 H 0.0226 0.4130 0.9743 0.032 Uiso 1 1 calc R . .
C3 C -0.1099(2) 0.41237(11) 0.8473(3) 0.0277(5) Uani 1 1 d . . .
C4 C -0.1773(2) 0.37387(12) 0.7682(2) 0.0260(5) Uani 1 1 d . . .
H4 H -0.2374 0.3925 0.7244 0.031 Uiso 1 1 calc R . .
C5 C -0.0696(2) 0.28402(13) 0.8170(3) 0.0251(5) Uani 1 1 d . . .
H5 H -0.0539 0.2399 0.8040 0.030 Uiso 1 1 calc R . .
C6 C 0.0934(2) 0.28764(14) 0.9716(3) 0.0273(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0168(19) 14 ?
Zn1 O1 2.0168(19) . ?
Zn1 N1 2.099(2) 9 ?
Zn1 N1 2.099(2) 6 ?
Zn1 O2 2.401(2) . ?
Zn1 O2 2.401(2) 14 ?
Zn1 C6 2.513(3) 14 ?
F1 C3 1.346(3) . ?
O1 C6 1.268(3) . ?
O2 C6 1.231(4) . ?
N1 C4 1.345(3) . ?
N1 C5 1.344(3) . ?
N1 Zn1 2.099(2) 9_454 ?
C1 C2 1.383(4) . ?
C1 C5 1.384(4) . ?
C1 C6 1.506(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C4 H4 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
O1 Zn1 O1 150.73(12) 14 . ?
O1 Zn1 N1 101.75(9) 14 9 ?
O1 Zn1 N1 96.01(8) . 9 ?
O1 Zn1 N1 96.01(8) 14 6 ?
O1 Zn1 N1 101.75(9) . 6 ?
N1 Zn1 N1 104.77(12) 9 6 ?
O1 Zn1 O2 98.58(8) 14 . ?
O1 Zn1 O2 58.95(8) . . ?
N1 Zn1 O2 153.71(7) 9 . ?
N1 Zn1 O2 89.36(8) 6 . ?
O1 Zn1 O2 58.95(8) 14 14 ?
O1 Zn1 O2 98.58(8) . 14 ?
N1 Zn1 O2 89.36(8) 9 14 ?
N1 Zn1 O2 153.71(7) 6 14 ?
O2 Zn1 O2 87.00(11) . 14 ?
O1 Zn1 C6 30.04(9) 14 14 ?
O1 Zn1 C6 125.39(10) . 14 ?
N1 Zn1 C6 96.29(8) 9 14 ?
N1 Zn1 C6 125.65(9) 6 14 ?
O2 Zn1 C6 93.00(8) . 14 ?
O2 Zn1 C6 28.91(8) 14 14 ?
C6 O1 Zn1 97.18(17) . . ?
C6 O2 Zn1 80.59(16) . . ?
C4 N1 C5 118.3(2) . . ?
C4 N1 Zn1 122.23(17) . 9_454 ?
C5 N1 Zn1 119.23(17) . 9_454 ?
C2 C1 C5 119.5(2) . . ?
C2 C1 C6 121.4(2) . . ?
C5 C1 C6 119.1(2) . . ?
C3 C2 C1 116.6(2) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
F1 C3 C4 118.9(2) . . ?
F1 C3 C2 119.0(2) . . ?
C4 C3 C2 122.1(2) . . ?
N1 C4 C3 120.7(2) . . ?
N1 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C1 122.8(2) . . ?
N1 C5 H5 118.6 . . ?
C1 C5 H5 118.6 . . ?
O2 C6 O1 123.3(2) . . ?
O2 C6 C1 119.9(2) . . ?
O1 C6 C1 116.7(2) . . ?

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 Zn1 O1 C6 43.98(15) 14 . . . ?
N1 Zn1 O1 C6 171.33(17) 9 . . . ?
N1 Zn1 O1 C6 -82.18(17) 6 . . . ?
O2 Zn1 O1 C6 -0.14(15) . . . . ?
O2 Zn1 O1 C6 81.07(16) 14 . . . ?
C6 Zn1 O1 C6 69.2(2) 14 . . . ?
O1 Zn1 O2 C6 -159.72(17) 14 . . . ?
O1 Zn1 O2 C6 0.15(16) . . . . ?
N1 Zn1 O2 C6 -19.3(3) 9 . . . ?
N1 Zn1 O2 C6 104.30(17) 6 . . . ?
O2 Zn1 O2 C6 -101.75(18) 14 . . . ?
C6 Zn1 O2 C6 -130.04(16) 14 . . . ?
C5 C1 C2 C3 -0.3(4) . . . . ?
C6 C1 C2 C3 179.2(2) . . . . ?
C1 C2 C3 F1 -178.5(2) . . . . ?
C1 C2 C3 C4 2.3(4) . . . . ?
C5 N1 C4 C3 -0.4(4) . . . . ?
Zn1 N1 C4 C3 -174.67(19) 9_454 . . . ?
F1 C3 C4 N1 178.7(2) . . . . ?
C2 C3 C4 N1 -2.0(4) . . . . ?
C4 N1 C5 C1 2.5(4) . . . . ?
Zn1 N1 C5 C1 176.94(19) 9_454 . . . ?
C2 C1 C5 N1 -2.1(4) . . . . ?
C6 C1 C5 N1 178.4(2) . . . . ?
Zn1 O2 C6 O1 -0.2(3) . . . . ?
Zn1 O2 C6 C1 -177.8(2) . . . . ?
Zn1 O1 C6 O2 0.3(3) . . . . ?
Zn1 O1 C6 C1 177.91(18) . . . . ?
C2 C1 C6 O2 -169.1(3) . . . . ?
C5 C1 C6 O2 10.4(4) . . . . ?
C2 C1 C6 O1 13.2(4) . . . . ?
C5 C1 C6 O1 -167.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1001896'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 Cl4 N4 O15 Zn2'
_chemical_formula_weight         883.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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/c

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                   14.8972(5)
_cell_length_b                   16.8530(4)
_cell_length_c                   14.5964(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.614(5)
_cell_angle_gamma                90.00
_cell_volume                     3185.92(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2981
_cell_measurement_theta_min      3.4800
_cell_measurement_theta_max      72.1254

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1784
_exptl_absorpt_coefficient_mu    5.646
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3981
_exptl_absorpt_correction_T_max  0.6021
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5918
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/net      0.0374
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.31
_diffrn_reflns_theta_max         72.27
_reflns_number_total             3074
_reflns_number_gt                2671
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0756P)²+1.4837P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3074
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.40533(3) 0.12229(2) 0.29006(3) 0.02359(15) Uani 1 1 d . . .
N1 N 0.32422(18) -0.04368(15) -0.16101(19) 0.0260(5) Uani 1 1 d . . .
N2 N 0.78017(19) 0.29172(15) 0.7410(2) 0.0272(5) Uani 1 1 d . . .
O1 O 0.33172(15) 0.07818(13) 0.13640(16) 0.0267(4) Uani 1 1 d . . .
O2 O 0.47658(15) 0.03702(13) 0.13967(17) 0.0307(5) Uani 1 1 d . . .
O3 O 0.48605(17) 0.17723(14) 0.44656(17) 0.0322(5) Uani 1 1 d . . .
O4 O 0.5899(2) 0.26319(15) 0.42656(19) 0.0425(6) Uani 1 1 d . . .
O5 O 0.5000 0.19262(17) 0.2500 0.0244(6) Uani 1 2 d S . .
H5A H 0.5290 0.2198 0.3064 0.037 Uiso 1 1 d R . .
C1 C 0.3816(2) 0.04924(17) 0.0953(2) 0.0244(6) Uani 1 1 d . . .
C2 C 0.3224(2) 0.02913(18) -0.0208(2) 0.0249(6) Uani 1 1 d . . .
C3 C 0.2338(2) 0.06873(18) -0.0916(2) 0.0274(6) Uani 1 1 d . . .
H3 H 0.2017 0.1048 -0.0689 0.033 Uiso 1 1 calc R . .
C4 C 0.1947(2) 0.05270(19) -0.1972(2) 0.0285(6) Uani 1 1 d . . .
C5 C 0.2401(2) -0.00345(19) -0.2304(2) 0.0288(6) Uani 1 1 d . . .
H5 H 0.2119 -0.0135 -0.3021 0.035 Uiso 1 1 calc R . .
C6 C 0.3651(2) -0.02641(18) -0.0585(2) 0.0262(6) Uani 1 1 d . . .
H6 H 0.4248 -0.0528 -0.0104 0.031 Uiso 1 1 calc R . .
C7 C 0.5624(2) 0.22364(18) 0.4807(2) 0.0274(6) Uani 1 1 d . . .
C8 C 0.6298(2) 0.23106(18) 0.5990(2) 0.0257(6) Uani 1 1 d . . .
C9 C 0.6111(2) 0.1901(2) 0.6695(3) 0.0323(7) Uani 1 1 d . . .
H9 H 0.5549 0.1561 0.6464 0.039 Uiso 1 1 calc R . .
C10 C 0.6786(3) 0.2013(2) 0.7758(3) 0.0347(7) Uani 1 1 d . . .
C11 C 0.7617(3) 0.25293(19) 0.8096(3) 0.0325(7) Uani 1 1 d . . .
H11 H 0.8052 0.2606 0.8815 0.039 Uiso 1 1 calc R . .
C12 C 0.7157(2) 0.28051(19) 0.6379(2) 0.0270(6) Uani 1 1 d . . .
H12 H 0.7290 0.3070 0.5900 0.032 Uiso 1 1 calc R . .
Cl1 Cl 0.08811(6) 0.10563(6) -0.29348(6) 0.0396(2) Uani 1 1 d . . .
Cl2 Cl 0.66130(8) 0.15075(7) 0.87079(8) 0.0604(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.087(2) . ?
Zn1 O2 2.104(2) 2_655 ?
Zn1 O5 2.1333(16) . ?
Zn1 N1 2.140(2) 6_556 ?
Zn1 N2 2.184(2) 8_455 ?
Zn1 O3 2.192(2) . ?
N1 C6 1.339(4) . ?
N1 C5 1.342(4) . ?
N1 Zn1 2.140(2) 6 ?
N2 C11 1.334(4) . ?
N2 C12 1.340(4) . ?
N2 Zn1 2.184(2) 8_556 ?
O1 C1 1.261(3) . ?
O2 C1 1.248(3) . ?
O2 Zn1 2.104(2) 2_655 ?
O3 C7 1.262(4) . ?
O4 C7 1.248(4) . ?
O5 Zn1 2.1333(16) 2_655 ?
O5 H5A 0.8500 . ?
C1 C2 1.513(4) . ?
C2 C3 1.381(4) . ?
C2 C6 1.389(4) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 Cl1 1.756(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.514(4) . ?
C8 C9 1.377(4) . ?
C8 C12 1.392(4) . ?
C9 C10 1.383(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(4) . ?
C10 Cl2 1.752(3) . ?
C11 H11 0.9300 . ?
C12 H12 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
O1 Zn1 O2 98.59(9) . 2_655 ?
O1 Zn1 O5 88.32(7) . . ?
O2 Zn1 O5 90.36(8) 2_655 . ?
O1 Zn1 N1 93.13(9) . 6_556 ?
O2 Zn1 N1 83.60(9) 2_655 6_556 ?
O5 Zn1 N1 173.93(8) . 6_556 ?
O1 Zn1 N2 88.50(9) . 8_455 ?
O2 Zn1 N2 170.25(9) 2_655 8_455 ?
O5 Zn1 N2 96.57(9) . 8_455 ?
N1 Zn1 N2 89.36(9) 6_556 8_455 ?
O1 Zn1 O3 175.30(9) . . ?
O2 Zn1 O3 83.37(9) 2_655 . ?
O5 Zn1 O3 87.39(7) . . ?
N1 Zn1 O3 91.33(9) 6_556 . ?
N2 Zn1 O3 90.07(9) 8_455 . ?
C6 N1 C5 118.2(3) . . ?
C6 N1 Zn1 119.16(19) . 6 ?
C5 N1 Zn1 122.1(2) . 6 ?
C11 N2 C12 118.4(3) . . ?
C11 N2 Zn1 122.6(2) . 8_556 ?
C12 N2 Zn1 118.9(2) . 8_556 ?
C1 O1 Zn1 121.91(18) . . ?
C1 O2 Zn1 126.9(2) . 2_655 ?
C7 O3 Zn1 126.6(2) . . ?
Zn1 O5 Zn1 112.50(13) 2_655 . ?
Zn1 O5 H5A 118.4 2_655 . ?
Zn1 O5 H5A 97.1 . . ?
O2 C1 O1 126.9(3) . . ?
O2 C1 C2 115.3(2) . . ?
O1 C1 C2 117.7(2) . . ?
C3 C2 C6 119.0(3) . . ?
C3 C2 C1 122.8(3) . . ?
C6 C2 C1 117.9(3) . . ?
C4 C3 C2 117.5(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 Cl1 120.7(2) . . ?
C5 C4 Cl1 118.2(2) . . ?
N1 C5 C4 121.1(3) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
N1 C6 C2 123.0(3) . . ?
N1 C6 H6 118.5 . . ?
C2 C6 H6 118.5 . . ?
O4 C7 O3 126.5(3) . . ?
O4 C7 C8 116.0(3) . . ?
O3 C7 C8 117.5(3) . . ?
C9 C8 C12 118.7(3) . . ?
C9 C8 C7 123.1(3) . . ?
C12 C8 C7 118.2(3) . . ?
C8 C9 C10 117.8(3) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 Cl2 120.8(2) . . ?
C11 C10 Cl2 118.5(3) . . ?
N2 C11 C10 121.2(3) . . ?
N2 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
N2 C12 C8 123.2(3) . . ?
N2 C12 H12 118.4 . . ?
C8 C12 H12 118.4 . . ?

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
O2 Zn1 O1 C1 -38.3(2) 2_655 . . . ?
O5 Zn1 O1 C1 51.8(2) . . . . ?
N1 Zn1 O1 C1 -122.3(2) 6_556 . . . ?
N2 Zn1 O1 C1 148.4(2) 8_455 . . . ?
O2 Zn1 O3 C7 84.7(3) 2_655 . . . ?
O5 Zn1 O3 C7 -6.0(3) . . . . ?
N1 Zn1 O3 C7 168.1(3) 6_556 . . . ?
N2 Zn1 O3 C7 -102.5(3) 8_455 . . . ?
O1 Zn1 O5 Zn1 -63.37(6) . . . 2_655 ?
O2 Zn1 O5 Zn1 35.21(6) 2_655 . . 2_655 ?
N2 Zn1 O5 Zn1 -151.67(7) 8_455 . . 2_655 ?
O3 Zn1 O5 Zn1 118.56(6) . . . 2_655 ?
Zn1 O2 C1 O1 -61.1(4) 2_655 . . . ?
Zn1 O2 C1 C2 116.8(2) 2_655 . . . ?
Zn1 O1 C1 O2 5.9(4) . . . . ?
Zn1 O1 C1 C2 -171.91(19) . . . . ?
O2 C1 C2 C3 -149.6(3) . . . . ?
O1 C1 C2 C3 28.5(4) . . . . ?
O2 C1 C2 C6 24.1(4) . . . . ?
O1 C1 C2 C6 -157.8(3) . . . . ?
C6 C2 C3 C4 -2.4(4) . . . . ?
C1 C2 C3 C4 171.3(3) . . . . ?
C2 C3 C4 C5 2.7(5) . . . . ?
C2 C3 C4 Cl1 -175.1(2) . . . . ?
C6 N1 C5 C4 -1.9(4) . . . . ?
Zn1 N1 C5 C4 -173.7(2) 6 . . . ?
C3 C4 C5 N1 -0.6(5) . . . . ?
Cl1 C4 C5 N1 177.3(2) . . . . ?
C5 N1 C6 C2 2.3(4) . . . . ?
Zn1 N1 C6 C2 174.3(2) 6 . . . ?
C3 C2 C6 N1 -0.1(5) . . . . ?
C1 C2 C6 N1 -174.1(3) . . . . ?
Zn1 O3 C7 O4 20.0(5) . . . . ?
Zn1 O3 C7 C8 -158.2(2) . . . . ?
O4 C7 C8 C9 -178.7(3) . . . . ?
O3 C7 C8 C9 -0.3(5) . . . . ?
O4 C7 C8 C12 0.0(4) . . . . ?
O3 C7 C8 C12 178.5(3) . . . . ?
C12 C8 C9 C10 0.7(5) . . . . ?
C7 C8 C9 C10 179.4(3) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C8 C9 C10 Cl2 -179.3(3) . . . . ?
C12 N2 C11 C10 0.8(5) . . . . ?
Zn1 N2 C11 C10 177.0(3) 8_556 . . . ?
C9 C10 C11 N2 -1.6(5) . . . . ?
Cl2 C10 C11 N2 178.5(3) . . . . ?
C11 N2 C12 C8 0.8(5) . . . . ?
Zn1 N2 C12 C8 -175.6(2) 8_556 . . . ?
C9 C8 C12 N2 -1.5(5) . . . . ?
C7 C8 C12 N2 179.7(3) . . . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.009 348 106 ' '
2 0.500 0.500 0.061 348 106 ' '
_platon_squeeze_details          
;
;


_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        72.27
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.113
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1001897'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 Cl2 N2 O5.50 Zn'
_chemical_formula_weight         405.48

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'
O O 0.0106 0.0060 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   7.7158(8)
_cell_length_b                   7.7397(8)
_cell_length_c                   25.946(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.273(2)
_cell_angle_gamma                90.00
_cell_volume                     1533.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2866
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.36

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    1.977
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7174
_exptl_absorpt_correction_T_max  0.7427
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11194
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         28.38
_reflns_number_total             3848
_reflns_number_gt                3034
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0556P)²+0.2277P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3848
_refine_ls_number_parameters     204
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.38252(4) -0.13226(4) 0.401679(12) 0.02900(12) Uani 1 1 d . . .
Cl1 Cl 0.21703(19) 0.55505(13) 0.20357(3) 0.0803(4) Uani 1 1 d . . .
Cl2 Cl 0.15712(13) -0.32544(15) 0.59301(3) 0.0622(3) Uani 1 1 d . . .
O1 O 0.3926(3) 0.1666(3) 0.41902(9) 0.0483(6) Uani 1 1 d . . .
O2 O 0.2908(3) 0.0424(3) 0.34538(9) 0.0477(6) Uani 1 1 d . . .
O3 O -0.3250(3) -0.1143(3) 0.38516(11) 0.0623(7) Uani 1 1 d . . .
O4 O -0.4150(3) -0.2140(4) 0.45460(9) 0.0558(6) Uani 1 1 d . . .
N1 N 0.3334(3) 0.6536(3) 0.35349(9) 0.0323(5) Uani 1 1 d . . .
N2 N 0.1933(3) -0.1801(3) 0.44898(9) 0.0303(5) Uani 1 1 d . . .
C1 C 0.3161(4) 0.3459(3) 0.34498(11) 0.0337(6) Uani 1 1 d . . .
C2 C 0.3461(4) 0.4952(3) 0.37422(11) 0.0329(6) Uani 1 1 d . . .
H2 H 0.3766 0.4849 0.4101 0.040 Uiso 1 1 calc R . .
C3 C 0.2950(4) 0.6680(4) 0.30186(11) 0.0387(7) Uani 1 1 d . . .
H3 H 0.2877 0.7772 0.2867 0.046 Uiso 1 1 calc R . .
C4 C 0.2662(5) 0.5249(4) 0.27079(11) 0.0453(8) Uani 1 1 d . . .
C5 C 0.2756(5) 0.3619(4) 0.29188(12) 0.0451(8) Uani 1 1 d . . .
H5 H 0.2551 0.2648 0.2708 0.054 Uiso 1 1 calc R . .
C6 C 0.3348(4) 0.1751(4) 0.37190(12) 0.0363(7) Uani 1 1 d . . .
C7 C -0.1099(4) -0.1981(4) 0.45544(11) 0.0339(6) Uani 1 1 d . . .
C8 C 0.0259(4) -0.1657(4) 0.42808(11) 0.0335(6) Uani 1 1 d . . .
H8 H -0.0001 -0.1321 0.3934 0.040 Uiso 1 1 calc R . .
C9 C 0.2319(4) -0.2284(3) 0.49887(11) 0.0328(6) Uani 1 1 d . . .
H9 H 0.3485 -0.2379 0.5138 0.039 Uiso 1 1 calc R . .
C10 C 0.1022(4) -0.2641(4) 0.52832(11) 0.0370(7) Uani 1 1 d . . .
C11 C -0.0716(4) -0.2486(4) 0.50653(12) 0.0391(7) Uani 1 1 d . . .
H11 H -0.1608 -0.2718 0.5261 0.047 Uiso 1 1 calc R . .
C12 C -0.2959(4) -0.1736(4) 0.42938(13) 0.0415(7) Uani 1 1 d . . .
O5 O 0.3362(6) 0.0228(5) 0.21698(13) 0.1136(14) Uani 1 1 d D . .
H5A H 0.3500 0.1287 0.2100 0.170 Uiso 1 1 d RD . .
H5B H 0.3464 -0.0495 0.1929 0.170 Uiso 1 1 d RD . .
O6 O 0.0000 0.0017(8) 0.2500 0.186(4) Uani 1 2 d SD . .
H6A H 0.0704 0.0316 0.2292 0.279 Uiso 0.50 1 d PRD . .
H6B H -0.1023 -0.0288 0.2364 0.279 Uiso 0.50 1 d PRD . .


_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
Zn1 O4 2.027(2) 1_655 ?
Zn1 O2 2.041(2) . ?
Zn1 N2 2.071(2) . ?
Zn1 N1 2.078(2) 1_545 ?
Zn1 O1 2.356(2) . ?
Zn1 O3 2.361(3) 1_655 ?
Zn1 C12 2.503(3) 1_655 ?
Zn1 C6 2.512(3) . ?
Cl1 C4 1.746(3) . ?
Cl2 C10 1.737(3) . ?
O1 C6 1.241(4) . ?
O2 C6 1.256(4) . ?
O3 C12 1.226(4) . ?
O3 Zn1 2.361(3) 1_455 ?
O4 C12 1.243(4) . ?
O4 Zn1 2.027(2) 1_455 ?
N1 C3 1.334(4) . ?
N1 C2 1.336(3) . ?
N1 Zn1 2.078(2) 1_565 ?
N2 C8 1.332(3) . ?
N2 C9 1.339(3) . ?
C1 C5 1.374(4) . ?
C1 C2 1.384(4) . ?
C1 C6 1.492(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.371(4) . ?
C7 C11 1.373(4) . ?
C7 C12 1.507(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9300 . ?
C12 Zn1 2.503(3) 1_455 ?
O5 H5A 0.8500 . ?
O5 H5B 0.8500 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8501 . ?

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
O4 Zn1 O2 147.76(11) 1_655 . ?
O4 Zn1 N2 94.76(9) 1_655 . ?
O2 Zn1 N2 109.94(10) . . ?
O4 Zn1 N1 102.40(10) 1_655 1_545 ?
O2 Zn1 N1 94.77(9) . 1_545 ?
N2 Zn1 N1 97.52(9) . 1_545 ?
O4 Zn1 O1 100.15(10) 1_655 . ?
O2 Zn1 O1 58.98(8) . . ?
N2 Zn1 O1 93.95(9) . . ?
N1 Zn1 O1 153.68(9) 1_545 . ?
O4 Zn1 O3 58.51(9) 1_655 1_655 ?
O2 Zn1 O3 94.20(10) . 1_655 ?
N2 Zn1 O3 153.08(9) . 1_655 ?
N1 Zn1 O3 91.96(10) 1_545 1_655 ?
O1 Zn1 O3 88.33(9) . 1_655 ?
O4 Zn1 C12 29.53(10) 1_655 1_655 ?
O2 Zn1 C12 121.18(11) . 1_655 ?
N2 Zn1 C12 124.14(10) . 1_655 ?
N1 Zn1 C12 99.11(10) 1_545 1_655 ?
O1 Zn1 C12 93.82(10) . 1_655 ?
O3 Zn1 C12 29.01(9) 1_655 1_655 ?
O4 Zn1 C6 124.65(11) 1_655 . ?
O2 Zn1 C6 29.79(9) . . ?
N2 Zn1 C6 105.48(10) . . ?
N1 Zn1 C6 124.36(9) 1_545 . ?
O1 Zn1 C6 29.32(9) . . ?
O3 Zn1 C6 89.43(9) 1_655 . ?
C12 Zn1 C6 107.74(11) 1_655 . ?
C6 O1 Zn1 82.33(18) . . ?
C6 O2 Zn1 96.36(19) . . ?
C12 O3 Zn1 81.9(2) . 1_455 ?
C12 O4 Zn1 97.0(2) . 1_455 ?
C3 N1 C2 118.3(2) . . ?
C3 N1 Zn1 122.16(18) . 1_565 ?
C2 N1 Zn1 119.52(18) . 1_565 ?
C8 N2 C9 119.0(3) . . ?
C8 N2 Zn1 117.97(19) . . ?
C9 N2 Zn1 123.04(19) . . ?
C5 C1 C2 118.1(3) . . ?
C5 C1 C6 122.8(3) . . ?
C2 C1 C6 119.1(3) . . ?
N1 C2 C1 123.3(3) . . ?
N1 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
N1 C3 C4 121.2(3) . . ?
N1 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 Cl1 118.3(2) . . ?
C5 C4 Cl1 120.8(2) . . ?
C4 C5 C1 118.3(3) . . ?
C4 C5 H5 120.8 . . ?
C1 C5 H5 120.8 . . ?
O1 C6 O2 121.8(3) . . ?
O1 C6 C1 120.3(3) . . ?
O2 C6 C1 117.9(3) . . ?
O1 C6 Zn1 68.34(16) . . ?
O2 C6 Zn1 53.85(15) . . ?
C1 C6 Zn1 169.4(2) . . ?
C8 C7 C11 118.5(3) . . ?
C8 C7 C12 119.6(3) . . ?
C11 C7 C12 121.8(3) . . ?
N2 C8 C7 122.9(3) . . ?
N2 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
N2 C9 C10 121.1(3) . . ?
N2 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 Cl2 119.8(2) . . ?
C11 C10 Cl2 120.4(2) . . ?
C7 C11 C10 118.7(3) . . ?
C7 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
O3 C12 O4 122.5(3) . . ?
O3 C12 C7 120.1(3) . . ?
O4 C12 C7 117.4(3) . . ?
O3 C12 Zn1 69.08(19) . 1_455 ?
O4 C12 Zn1 53.51(16) . 1_455 ?
C7 C12 Zn1 170.2(2) . 1_455 ?
H5A O5 H5B 116.7 . . ?
H6A O6 H6B 116.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Zn1 O1 C6 149.4(2) 1_655 . . . ?
O2 Zn1 O1 C6 -4.11(19) . . . . ?
N2 Zn1 O1 C6 -115.0(2) . . . . ?
N1 Zn1 O1 C6 0.8(3) 1_545 . . . ?
O3 Zn1 O1 C6 91.8(2) 1_655 . . . ?
C12 Zn1 O1 C6 120.3(2) 1_655 . . . ?
O4 Zn1 O2 C6 -51.4(3) 1_655 . . . ?
N2 Zn1 O2 C6 86.4(2) . . . . ?
N1 Zn1 O2 C6 -173.8(2) 1_545 . . . ?
O1 Zn1 O2 C6 4.05(19) . . . . ?
O3 Zn1 O2 C6 -81.5(2) 1_655 . . . ?
C12 Zn1 O2 C6 -70.1(2) 1_655 . . . ?
O4 Zn1 N2 C8 -171.6(2) 1_655 . . . ?
O2 Zn1 N2 C8 29.4(2) . . . . ?
N1 Zn1 N2 C8 -68.4(2) 1_545 . . . ?
O1 Zn1 N2 C8 87.8(2) . . . . ?
O3 Zn1 N2 C8 -178.1(2) 1_655 . . . ?
C12 Zn1 N2 C8 -174.85(19) 1_655 . . . ?
C6 Zn1 N2 C8 60.4(2) . . . . ?
O4 Zn1 N2 C9 6.7(2) 1_655 . . . ?
O2 Zn1 N2 C9 -152.2(2) . . . . ?
N1 Zn1 N2 C9 109.9(2) 1_545 . . . ?
O1 Zn1 N2 C9 -93.8(2) . . . . ?
O3 Zn1 N2 C9 0.3(3) 1_655 . . . ?
C12 Zn1 N2 C9 3.5(3) 1_655 . . . ?
C6 Zn1 N2 C9 -121.2(2) . . . . ?
C3 N1 C2 C1 -2.1(5) . . . . ?
Zn1 N1 C2 C1 -179.8(2) 1_565 . . . ?
C5 C1 C2 N1 1.7(5) . . . . ?
C6 C1 C2 N1 179.6(3) . . . . ?
C2 N1 C3 C4 1.1(5) . . . . ?
Zn1 N1 C3 C4 178.8(3) 1_565 . . . ?
N1 C3 C4 C5 0.1(6) . . . . ?
N1 C3 C4 Cl1 -179.9(3) . . . . ?
C3 C4 C5 C1 -0.5(6) . . . . ?
Cl1 C4 C5 C1 179.5(3) . . . . ?
C2 C1 C5 C4 -0.3(5) . . . . ?
C6 C1 C5 C4 -178.2(3) . . . . ?
Zn1 O1 C6 O2 6.7(3) . . . . ?
Zn1 O1 C6 C1 -173.1(3) . . . . ?
Zn1 O2 C6 O1 -7.8(4) . . . . ?
Zn1 O2 C6 C1 172.1(2) . . . . ?
C5 C1 C6 O1 171.0(3) . . . . ?
C2 C1 C6 O1 -6.8(5) . . . . ?
C5 C1 C6 O2 -8.9(5) . . . . ?
C2 C1 C6 O2 173.3(3) . . . . ?
C5 C1 C6 Zn1 28.1(14) . . . . ?
C2 C1 C6 Zn1 -149.8(11) . . . . ?
O4 Zn1 C6 O1 -37.5(2) 1_655 . . . ?
O2 Zn1 C6 O1 172.9(3) . . . . ?
N2 Zn1 C6 O1 69.7(2) . . . . ?
N1 Zn1 C6 O1 -179.59(18) 1_545 . . . ?
O3 Zn1 C6 O1 -87.6(2) 1_655 . . . ?
C12 Zn1 C6 O1 -64.7(2) 1_655 . . . ?
O4 Zn1 C6 O2 149.57(19) 1_655 . . . ?
N2 Zn1 C6 O2 -103.2(2) . . . . ?
N1 Zn1 C6 O2 7.5(2) 1_545 . . . ?
O1 Zn1 C6 O2 -172.9(3) . . . . ?
O3 Zn1 C6 O2 99.5(2) 1_655 . . . ?
C12 Zn1 C6 O2 122.4(2) 1_655 . . . ?
O4 Zn1 C6 C1 108.4(12) 1_655 . . . ?
O2 Zn1 C6 C1 -41.1(11) . . . . ?
N2 Zn1 C6 C1 -144.4(12) . . . . ?
N1 Zn1 C6 C1 -33.6(12) 1_545 . . . ?
O1 Zn1 C6 C1 145.9(13) . . . . ?
O3 Zn1 C6 C1 58.3(12) 1_655 . . . ?
C12 Zn1 C6 C1 81.2(12) 1_655 . . . ?
C9 N2 C8 C7 0.0(4) . . . . ?
Zn1 N2 C8 C7 178.5(2) . . . . ?
C11 C7 C8 N2 -0.3(5) . . . . ?
C12 C7 C8 N2 178.2(3) . . . . ?
C8 N2 C9 C10 0.5(4) . . . . ?
Zn1 N2 C9 C10 -177.9(2) . . . . ?
N2 C9 C10 C11 -0.7(4) . . . . ?
N2 C9 C10 Cl2 -179.7(2) . . . . ?
C8 C7 C11 C10 0.2(4) . . . . ?
C12 C7 C11 C10 -178.3(3) . . . . ?
C9 C10 C11 C7 0.3(5) . . . . ?
Cl2 C10 C11 C7 179.3(2) . . . . ?
Zn1 O3 C12 O4 3.3(3) 1_455 . . . ?
Zn1 O3 C12 C7 -176.0(3) 1_455 . . . ?
Zn1 O4 C12 O3 -3.9(4) 1_455 . . . ?
Zn1 O4 C12 C7 175.5(2) 1_455 . . . ?
C8 C7 C12 O3 -4.7(5) . . . . ?
C11 C7 C12 O3 173.7(3) . . . . ?
C8 C7 C12 O4 175.9(3) . . . . ?
C11 C7 C12 O4 -5.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1001898'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H14 Cl4 N4 O9 Zn2'
_chemical_formula_weight         774.93

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'
O O 0.0106 0.0060 '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'
Zn Zn 0.2839 1.4301 '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/c

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                   12.0840(17)
_cell_length_b                   9.8218(14)
_cell_length_c                   11.9104(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.035(3)
_cell_angle_gamma                90.00
_cell_volume                     1410.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1561
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      28.13

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    2.140
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6993
_exptl_absorpt_correction_T_max  0.7396
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5127
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         28.30
_reflns_number_total             1756
_reflns_number_gt                1486
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0277P)²+2.6859P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1756
_refine_ls_number_parameters     105
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.161
_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
Zn1 Zn 0.5000 0.40669(9) 0.2500 0.0179(3) Uani 1 2 d S . .
Cl1 Cl 0.41787(13) 0.09185(17) -0.14836(12) 0.0325(4) Uani 1 1 d . . .
O2 O 0.1079(4) -0.0502(5) 0.1305(4) 0.0436(13) Uani 1 1 d . . .
N1 N 0.4094(3) 0.2622(4) 0.1516(4) 0.0170(9) Uani 1 1 d . . .
C1 C 0.2607(4) 0.1009(6) 0.1354(5) 0.0226(12) Uani 1 1 d . . .
C5 C 0.2885(5) 0.0645(6) 0.0283(5) 0.0254(12) Uani 1 1 d . . .
H5 H 0.2477 -0.0029 -0.0141 0.030 Uiso 1 1 calc R . .
O1 O 0.1422(4) 0.0677(5) 0.2851(5) 0.0404(12) Uani 1 1 d . . .
C3 C 0.4366(4) 0.2282(5) 0.0481(4) 0.0191(11) Uani 1 1 d . . .
H3 H 0.4975 0.2723 0.0172 0.023 Uiso 1 1 calc R . .
C4 C 0.3780(5) 0.1302(6) -0.0145(5) 0.0215(11) Uani 1 1 d . . .
C2 C 0.3234(4) 0.1986(6) 0.1942(5) 0.0202(11) Uani 1 1 d . . .
H2 H 0.3048 0.2217 0.2680 0.024 Uiso 1 1 calc R . .
C6 C 0.1639(5) 0.0363(6) 0.1883(6) 0.0306(15) Uani 1 1 d . . .
O3 O 0.188(3) 0.760(4) 0.956(3) 0.108(12) Uani 0.25 1 d PD . .
H3B H 0.2035 0.7017 0.9055 0.162 Uiso 0.25 1 d PRD . .
H3A H 0.2483 0.7770 1.0069 0.162 Uiso 0.25 1 d PRD . .


_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
Zn1 O2 2.041(5) 3 ?
Zn1 O2 2.041(5) 4 ?
Zn1 N1 2.099(4) . ?
Zn1 N1 2.099(4) 2_655 ?
Zn1 O1 2.351(5) 4 ?
Zn1 O1 2.351(5) 3 ?
Zn1 C6 2.507(6) 4 ?
Zn1 C6 2.507(6) 3 ?
Cl1 C4 1.740(6) . ?
O2 C6 1.260(8) . ?
O2 Zn1 2.041(5) 3_445 ?
N1 C3 1.340(7) . ?
N1 C2 1.342(7) . ?
C1 C2 1.382(8) . ?
C1 C5 1.388(9) . ?
C1 C6 1.508(8) . ?
C5 C4 1.386(8) . ?
C5 H5 0.9500 . ?
O1 C6 1.239(9) . ?
O1 Zn1 2.351(5) 3_445 ?
C3 C4 1.382(8) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C6 Zn1 2.507(6) 3_445 ?
O3 O3 1.78(7) 7_567 ?
O3 H3B 0.8544 . ?
O3 H3A 0.9307 . ?

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 Zn1 O2 156.1(3) 3 4 ?
O2 Zn1 N1 94.86(18) 3 . ?
O2 Zn1 N1 101.28(19) 4 . ?
O2 Zn1 N1 101.28(19) 3 2_655 ?
O2 Zn1 N1 94.86(18) 4 2_655 ?
N1 Zn1 N1 94.9(2) . 2_655 ?
O2 Zn1 O1 103.4(2) 3 4 ?
O2 Zn1 O1 59.33(19) 4 4 ?
N1 Zn1 O1 90.54(17) . 4 ?
N1 Zn1 O1 154.20(17) 2_655 4 ?
O2 Zn1 O1 59.33(19) 3 3 ?
O2 Zn1 O1 103.4(2) 4 3 ?
N1 Zn1 O1 154.20(17) . 3 ?
N1 Zn1 O1 90.54(17) 2_655 3 ?
O1 Zn1 O1 95.4(2) 4 3 ?
O2 Zn1 C6 131.0(2) 3 4 ?
O2 Zn1 C6 30.0(2) 4 4 ?
N1 Zn1 C6 96.60(17) . 4 ?
N1 Zn1 C6 124.9(2) 2_655 4 ?
O1 Zn1 C6 29.3(2) 4 4 ?
O1 Zn1 C6 100.88(18) 3 4 ?
O2 Zn1 C6 30.0(2) 3 3 ?
O2 Zn1 C6 131.0(2) 4 3 ?
N1 Zn1 C6 124.9(2) . 3 ?
N1 Zn1 C6 96.60(17) 2_655 3 ?
O1 Zn1 C6 100.88(18) 4 3 ?
O1 Zn1 C6 29.3(2) 3 3 ?
C6 Zn1 C6 119.0(3) 4 3 ?
C6 O2 Zn1 95.9(4) . 3_445 ?
C3 N1 C2 118.6(5) . . ?
C3 N1 Zn1 121.9(3) . . ?
C2 N1 Zn1 119.4(4) . . ?
C2 C1 C5 119.0(5) . . ?
C2 C1 C6 119.6(6) . . ?
C5 C1 C6 121.4(5) . . ?
C4 C5 C1 117.6(5) . . ?
C4 C5 H5 121.2 . . ?
C1 C5 H5 121.2 . . ?
C6 O1 Zn1 82.3(4) . 3_445 ?
N1 C3 C4 121.3(5) . . ?
N1 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 120.6(5) . . ?
C3 C4 Cl1 118.7(4) . . ?
C5 C4 Cl1 120.7(4) . . ?
N1 C2 C1 122.9(5) . . ?
N1 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
O1 C6 O2 122.4(6) . . ?
O1 C6 C1 120.4(6) . . ?
O2 C6 C1 117.2(6) . . ?
O1 C6 Zn1 68.3(3) . 3_445 ?
O2 C6 Zn1 54.1(3) . 3_445 ?
C1 C6 Zn1 171.3(5) . 3_445 ?
O3 O3 H3B 97.5 7_567 . ?
H3B O3 H3A 112.5 . . ?

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
O2 Zn1 N1 C3 1.8(4) 3 . . . ?
O2 Zn1 N1 C3 164.0(4) 4 . . . ?
N1 Zn1 N1 C3 -100.0(4) 2_655 . . . ?
O1 Zn1 N1 C3 105.2(4) 4 . . . ?
O1 Zn1 N1 C3 1.5(7) 3 . . . ?
C6 Zn1 N1 C3 134.0(4) 4 . . . ?
C6 Zn1 N1 C3 1.5(5) 3 . . . ?
O2 Zn1 N1 C2 179.8(4) 3 . . . ?
O2 Zn1 N1 C2 -17.9(4) 4 . . . ?
N1 Zn1 N1 C2 78.0(4) 2_655 . . . ?
O1 Zn1 N1 C2 -76.7(4) 4 . . . ?
O1 Zn1 N1 C2 179.5(4) 3 . . . ?
C6 Zn1 N1 C2 -48.0(4) 4 . . . ?
C6 Zn1 N1 C2 179.6(4) 3 . . . ?
C2 C1 C5 C4 -0.7(8) . . . . ?
C6 C1 C5 C4 179.2(5) . . . . ?
C2 N1 C3 C4 0.2(8) . . . . ?
Zn1 N1 C3 C4 178.2(4) . . . . ?
N1 C3 C4 C5 0.3(8) . . . . ?
N1 C3 C4 Cl1 179.8(4) . . . . ?
C1 C5 C4 C3 0.0(8) . . . . ?
C1 C5 C4 Cl1 -179.5(4) . . . . ?
C3 N1 C2 C1 -0.9(8) . . . . ?
Zn1 N1 C2 C1 -179.0(4) . . . . ?
C5 C1 C2 N1 1.2(8) . . . . ?
C6 C1 C2 N1 -178.7(5) . . . . ?
Zn1 O1 C6 O2 0.4(6) 3_445 . . . ?
Zn1 O1 C6 C1 -179.1(5) 3_445 . . . ?
Zn1 O2 C6 O1 -0.5(7) 3_445 . . . ?
Zn1 O2 C6 C1 179.0(4) 3_445 . . . ?
C2 C1 C6 O1 -1.9(8) . . . . ?
C5 C1 C6 O1 178.2(6) . . . . ?
C2 C1 C6 O2 178.6(5) . . . . ?
C5 C1 C6 O2 -1.4(8) . . . . ?



_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1001899'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26.50 H24 Br4 N4 O11.50 Zn2'
_chemical_formula_weight         1032.88

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   14.910(3)
_cell_length_b                   17.044(3)
_cell_length_c                   14.696(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.49(2)
_cell_angle_gamma                90.00
_cell_volume                     3218.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3121
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.70

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    2.132
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2012
_exptl_absorpt_coefficient_mu    6.524
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3864
_exptl_absorpt_correction_T_max  0.4411
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9114
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2847
_reflns_number_gt                2355
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 

 A minor position of Br atom was removed in the final refinement and the highest electron 
 density peak (2.033) was found around the Br atom with the distance of 0.959 Å.
;

_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)+(0.0256P)²+6.5494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2847
_refine_ls_number_parameters     195
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.090
_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
Br1 Br 0.36317(3) 0.36297(3) 0.19339(3) 0.01860(12) Uani 1 1 d . . .
Br2 Br 0.46462(3) -0.09622(3) 0.37957(3) 0.03101(15) Uani 1 1 d U . .
Zn1 Zn 0.13284(3) 0.13193(3) 0.28808(3) 0.00977(12) Uani 1 1 d . . .
O1 O 0.0833(2) 0.00908(16) -0.0753(2) 0.0176(7) Uani 1 1 d . . .
O2 O 0.20705(19) -0.07649(16) -0.0534(2) 0.0139(6) Uani 1 1 d . . .
O3 O 0.41413(19) 0.28420(16) 0.6400(2) 0.0123(6) Uani 1 1 d . . .
O4 O 0.55318(18) 0.32581(16) 0.63272(19) 0.0117(6) Uani 1 1 d . . .
O5 O 0.0000 0.0634(2) 0.2500 0.0105(8) Uani 1 2 d SD . .
H5 H 0.0252 0.0285 0.2980 0.016 Uiso 1 1 d RD . .
N1 N 0.2091(2) 0.04696(19) 0.2393(2) 0.0106(7) Uani 1 1 d . . .
N2 N 0.2617(2) 0.20912(19) 0.3358(2) 0.0113(7) Uani 1 1 d . . .
C1 C 0.2165(3) -0.0180(2) 0.0984(3) 0.0119(9) Uani 1 1 d . . .
C2 C 0.1700(3) 0.0328(2) 0.1359(3) 0.0118(8) Uani 1 1 d . . .
H2 H 0.1076 0.0587 0.0864 0.014 Uiso 1 1 calc R . .
C3 C 0.2962(3) 0.0098(2) 0.3085(3) 0.0141(9) Uani 1 1 d . . .
H3 H 0.3258 0.0202 0.3818 0.017 Uiso 1 1 calc R . .
C4 C 0.3443(3) -0.0434(3) 0.2763(3) 0.0170(9) Uani 1 1 d . . .
C5 C 0.3056(3) -0.0581(2) 0.1697(3) 0.0158(9) Uani 1 1 d . . .
H5A H 0.3388 -0.0941 0.1469 0.019 Uiso 1 1 calc R . .
C6 C 0.1656(3) -0.0291(2) -0.0205(3) 0.0102(8) Uani 1 1 d . . .
C7 C 0.4044(3) 0.2786(2) 0.4763(3) 0.0104(8) Uani 1 1 d . . .
C8 C 0.4214(3) 0.3190(2) 0.4044(3) 0.0122(8) Uani 1 1 d . . .
H8 H 0.4773 0.3552 0.4272 0.015 Uiso 1 1 calc R . .
C9 C 0.3536(3) 0.3046(2) 0.2980(3) 0.0111(8) Uani 1 1 d . . .
C10 C 0.2760(3) 0.2495(2) 0.2665(3) 0.0118(8) Uani 1 1 d . . .
H10 H 0.2314 0.2399 0.1932 0.014 Uiso 1 1 calc R . .
C11 C 0.3247(3) 0.2244(2) 0.4395(3) 0.0110(8) Uani 1 1 d . . .
H11 H 0.3138 0.1968 0.4892 0.013 Uiso 1 1 calc R . .
C12 C 0.4630(3) 0.2970(2) 0.5930(3) 0.0086(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.896(4) . ?
Br2 C4 1.889(4) . ?
Zn1 O4 2.095(2) 8_455 ?
Zn1 O3 2.098(3) 7_556 ?
Zn1 O5 2.116(2) . ?
Zn1 N2 2.132(3) . ?
Zn1 N1 2.175(3) . ?
Zn1 O2 2.220(3) 6_556 ?
O1 C6 1.255(5) . ?
O2 C6 1.253(5) . ?
O2 Zn1 2.220(3) 6 ?
O3 C12 1.251(4) . ?
O3 Zn1 2.098(3) 7_556 ?
O4 C12 1.263(4) . ?
O4 Zn1 2.095(2) 8_556 ?
O5 Zn1 2.116(2) 2 ?
O5 H5 0.8499 . ?
N1 C3 1.335(5) . ?
N1 C2 1.345(5) . ?
N2 C10 1.334(5) . ?
N2 C11 1.349(5) . ?
C1 C5 1.385(5) . ?
C1 C2 1.387(6) . ?
C1 C6 1.523(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(6) . ?
C5 H5A 0.9500 . ?
C7 C11 1.380(5) . ?
C7 C8 1.388(5) . ?
C7 C12 1.510(5) . ?
C8 C9 1.387(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?

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
O4 Zn1 O3 99.51(10) 8_455 7_556 ?
O4 Zn1 O5 87.97(8) 8_455 . ?
O3 Zn1 O5 90.15(10) 7_556 . ?
O4 Zn1 N2 93.69(11) 8_455 . ?
O3 Zn1 N2 83.63(11) 7_556 . ?
O5 Zn1 N2 173.74(11) . . ?
O4 Zn1 N1 88.40(11) 8_455 . ?
O3 Zn1 N1 169.59(10) 7_556 . ?
O5 Zn1 N1 96.93(11) . . ?
N2 Zn1 N1 89.15(12) . . ?
O4 Zn1 O2 174.21(10) 8_455 6_556 ?
O3 Zn1 O2 82.95(10) 7_556 6_556 ?
O5 Zn1 O2 86.78(8) . 6_556 ?
N2 Zn1 O2 91.78(11) . 6_556 ?
N1 Zn1 O2 89.81(11) . 6_556 ?
C6 O2 Zn1 126.7(2) . 6 ?
C12 O3 Zn1 126.6(3) . 7_556 ?
C12 O4 Zn1 121.3(2) . 8_556 ?
Zn1 O5 Zn1 112.96(17) . 2 ?
Zn1 O5 H5 101.9 . . ?
Zn1 O5 H5 124.4 2 . ?
C3 N1 C2 118.2(3) . . ?
C3 N1 Zn1 122.3(2) . . ?
C2 N1 Zn1 119.5(3) . . ?
C10 N2 C11 118.2(3) . . ?
C10 N2 Zn1 122.3(2) . . ?
C11 N2 Zn1 119.1(3) . . ?
C5 C1 C2 119.2(4) . . ?
C5 C1 C6 122.4(4) . . ?
C2 C1 C6 118.4(3) . . ?
N1 C2 C1 123.0(4) . . ?
N1 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
N1 C3 C4 121.6(4) . . ?
N1 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 Br2 119.0(3) . . ?
C5 C4 Br2 120.1(3) . . ?
C1 C5 C4 117.0(4) . . ?
C1 C5 H5A 121.5 . . ?
C4 C5 H5A 121.5 . . ?
O2 C6 O1 126.9(3) . . ?
O2 C6 C1 117.8(3) . . ?
O1 C6 C1 115.3(3) . . ?
C11 C7 C8 119.1(3) . . ?
C11 C7 C12 118.1(3) . . ?
C8 C7 C12 122.5(3) . . ?
C9 C8 C7 117.4(4) . . ?
C9 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 Br1 118.8(3) . . ?
C8 C9 Br1 120.6(3) . . ?
N2 C10 C9 121.9(3) . . ?
N2 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
N2 C11 C7 122.7(4) . . ?
N2 C11 H11 118.6 . . ?
C7 C11 H11 118.6 . . ?
O3 C12 O4 126.5(3) . . ?
O3 C12 C7 115.3(3) . . ?
O4 C12 C7 118.2(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
O4 Zn1 O5 Zn1 -64.14(7) 8_455 . . 2 ?
O3 Zn1 O5 Zn1 35.37(7) 7_556 . . 2 ?
N1 Zn1 O5 Zn1 -152.28(8) . . . 2 ?
O2 Zn1 O5 Zn1 118.30(7) 6_556 . . 2 ?
O4 Zn1 N1 C3 161.7(3) 8_455 . . . ?
O3 Zn1 N1 C3 22.0(8) 7_556 . . . ?
O5 Zn1 N1 C3 -110.5(3) . . . . ?
N2 Zn1 N1 C3 68.0(3) . . . . ?
O2 Zn1 N1 C3 -23.8(3) 6_556 . . . ?
O4 Zn1 N1 C2 -15.9(3) 8_455 . . . ?
O3 Zn1 N1 C2 -155.6(6) 7_556 . . . ?
O5 Zn1 N1 C2 71.9(3) . . . . ?
N2 Zn1 N1 C2 -109.6(3) . . . . ?
O2 Zn1 N1 C2 158.6(3) 6_556 . . . ?
O4 Zn1 N2 C10 -13.0(3) 8_455 . . . ?
O3 Zn1 N2 C10 -112.1(3) 7_556 . . . ?
N1 Zn1 N2 C10 75.4(3) . . . . ?
O2 Zn1 N2 C10 165.2(3) 6_556 . . . ?
O4 Zn1 N2 C11 159.7(3) 8_455 . . . ?
O3 Zn1 N2 C11 60.5(3) 7_556 . . . ?
N1 Zn1 N2 C11 -112.0(3) . . . . ?
O2 Zn1 N2 C11 -22.2(3) 6_556 . . . ?
C3 N1 C2 C1 -0.5(6) . . . . ?
Zn1 N1 C2 C1 177.2(3) . . . . ?
C5 C1 C2 N1 2.0(6) . . . . ?
C6 C1 C2 N1 -179.6(3) . . . . ?
C2 N1 C3 C4 -1.7(6) . . . . ?
Zn1 N1 C3 C4 -179.3(3) . . . . ?
N1 C3 C4 C5 2.4(6) . . . . ?
N1 C3 C4 Br2 -177.7(3) . . . . ?
C2 C1 C5 C4 -1.2(6) . . . . ?
C6 C1 C5 C4 -179.6(4) . . . . ?
C3 C4 C5 C1 -0.9(6) . . . . ?
Br2 C4 C5 C1 179.3(3) . . . . ?
Zn1 O2 C6 O1 -16.2(6) 6 . . . ?
Zn1 O2 C6 C1 161.1(2) 6 . . . ?
C5 C1 C6 O2 0.0(6) . . . . ?
C2 C1 C6 O2 -178.4(4) . . . . ?
C5 C1 C6 O1 177.6(4) . . . . ?
C2 C1 C6 O1 -0.7(5) . . . . ?
C11 C7 C8 C9 2.5(5) . . . . ?
C12 C7 C8 C9 -171.4(3) . . . . ?
C7 C8 C9 C10 -3.0(6) . . . . ?
C7 C8 C9 Br1 174.8(3) . . . . ?
C11 N2 C10 C9 1.1(6) . . . . ?
Zn1 N2 C10 C9 173.8(3) . . . . ?
C8 C9 C10 N2 1.2(6) . . . . ?
Br1 C9 C10 N2 -176.7(3) . . . . ?
C10 N2 C11 C7 -1.5(6) . . . . ?
Zn1 N2 C11 C7 -174.5(3) . . . . ?
C8 C7 C11 N2 -0.3(6) . . . . ?
C12 C7 C11 N2 173.8(3) . . . . ?
Zn1 O3 C12 O4 62.1(5) 7_556 . . . ?
Zn1 O3 C12 C7 -115.3(3) 7_556 . . . ?
Zn1 O4 C12 O3 -6.0(5) 8_556 . . . ?
Zn1 O4 C12 C7 171.3(2) 8_556 . . . ?
C11 C7 C12 O3 -24.1(5) . . . . ?
C8 C7 C12 O3 149.8(4) . . . . ?
C11 C7 C12 O4 158.2(3) . . . . ?
C8 C7 C12 O4 -27.8(5) . . . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.185 0.250 -0.065 307.7 91.0
2 0.685 0.750 -0.065 307.7 91.0
_platon_squeeze_details          
; 
The unit cell contains 10 methanol molecules 
which have been treated as a diffuse contribution to 
the overall scattering without specific atom positions by SQUEEZE/PLATON.
;

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.033
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.117
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1001900'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 Br4 N4 O12 Zn'
_chemical_formula_weight         943.47

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   15.3861(15)
_cell_length_b                   6.8845(7)
_cell_length_c                   29.387(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.112(2)
_cell_angle_gamma                90.00
_cell_volume                     3112.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2739
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.33

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    5.990
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.2093
_exptl_absorpt_correction_T_max  0.2666
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18502
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.32
_diffrn_reflns_theta_max         27.89
_reflns_number_total             7290
_reflns_number_gt                4098
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0401P)²+2.4627P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7290
_refine_ls_number_parameters     410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
Zn1 Zn 0.0000 0.48263(11) 0.7500 0.02800(18) Uani 1 2 d S . .
Zn2 Zn 0.0000 0.0000 0.5000 0.03156(19) Uani 1 2 d S . .
Br1 Br 0.37756(3) 0.44132(11) 0.792591(18) 0.0665(2) Uani 1 1 d . . .
Br2 Br 0.38004(3) 0.03222(9) 0.515324(18) 0.05277(17) Uani 1 1 d . . .
Br3 Br 0.46486(3) 0.53374(10) 0.426694(19) 0.0637(2) Uani 1 1 d . . .
Br4 Br 0.50731(4) 0.03939(12) 0.34605(2) 0.0772(2) Uani 1 1 d . . .
O1 O 0.3446(2) 0.4744(7) 0.60831(12) 0.0744(13) Uani 1 1 d . . .
O2 O 0.2042(2) 0.5151(7) 0.59444(11) 0.0625(11) Uani 1 1 d . . .
H2 H 0.2205 0.5222 0.5680 0.094 Uiso 1 1 calc R . .
O3 O 0.2961(2) 0.0625(7) 0.33595(10) 0.0610(11) Uani 1 1 d . . .
H3 H 0.2943 0.0622 0.3081 0.092 Uiso 1 1 calc R . .
O4 O 0.1647(2) -0.0555(7) 0.32914(12) 0.0753(13) Uani 1 1 d . . .
O5 O -0.02940(19) 0.6929(5) 0.70322(10) 0.0494(9) Uani 1 1 d . . .
H5A H 0.0075 0.7711 0.6920 0.074 Uiso 1 1 d R . .
H5B H -0.0708 0.6545 0.6852 0.074 Uiso 1 1 d R . .
O6 O -0.0240(2) 0.2700(6) 0.70172(13) 0.0752(13) Uani 1 1 d . . .
H6A H 0.0139 0.1992 0.6888 0.113 Uiso 1 1 d R . .
H6B H -0.0769 0.2417 0.6966 0.113 Uiso 1 1 d R . .
O7 O 0.04302(18) 0.2162(5) 0.54572(10) 0.0426(8) Uani 1 1 d . . .
H7A H 0.0052 0.2993 0.5538 0.064 Uiso 1 1 d R . .
H7B H 0.0761 0.1730 0.5666 0.064 Uiso 1 1 d R . .
O8 O -0.04790(18) 0.2094(5) 0.45410(10) 0.0398(8) Uani 1 1 d . . .
H8A H -0.0778 0.1476 0.4345 0.060 Uiso 1 1 d R . .
H8B H -0.0114 0.2910 0.4439 0.060 Uiso 1 1 d R . .
O9 O 0.04588(19) 0.4931(5) 0.41602(11) 0.0463(9) Uani 1 1 d . . .
O10 O 0.1399(2) 0.4355(7) 0.36027(11) 0.0699(13) Uani 1 1 d . . .
O11 O 0.8485(2) -0.0110(6) 0.39609(11) 0.0564(10) Uani 1 1 d . . .
O12 O 0.9268(2) 0.0198(5) 0.33304(12) 0.0477(9) Uani 1 1 d . . .
N1 N 0.1398(2) 0.4724(5) 0.72921(11) 0.0307(8) Uani 1 1 d . . .
N2 N 0.1285(2) 0.0063(5) 0.46924(12) 0.0320(9) Uani 1 1 d . . .
N3 N 0.2500(3) 0.5249(6) 0.50884(12) 0.0438(10) Uani 1 1 d . . .
N4 N 0.7047(3) 0.0480(6) 0.25388(13) 0.0461(11) Uani 1 1 d . . .
C1 C 0.2710(3) 0.4892(7) 0.62095(16) 0.0365(11) Uani 1 1 d . . .
C2 C 0.2471(3) 0.4780(6) 0.67002(14) 0.0303(10) Uani 1 1 d . . .
C3 C 0.1619(3) 0.4787(6) 0.68542(14) 0.0307(10) Uani 1 1 d . . .
H3A H 0.1176 0.4840 0.6639 0.037 Uiso 1 1 calc R . .
C4 C 0.2048(3) 0.4613(7) 0.75971(15) 0.0371(11) Uani 1 1 d . . .
H4 H 0.1909 0.4558 0.7905 0.044 Uiso 1 1 calc R . .
C5 C 0.2909(3) 0.4576(7) 0.74746(15) 0.0371(11) Uani 1 1 d . . .
C6 C 0.3134(3) 0.4629(7) 0.70239(15) 0.0370(11) Uani 1 1 d . . .
H6 H 0.3713 0.4566 0.6936 0.044 Uiso 1 1 calc R . .
C7 C 0.2235(3) 0.0045(7) 0.35165(15) 0.0369(11) Uani 1 1 d . . .
C8 C 0.2188(3) 0.0083(6) 0.40282(14) 0.0279(10) Uani 1 1 d . . .
C9 C 0.1388(3) 0.0015(6) 0.42383(14) 0.0310(10) Uani 1 1 d . . .
H9 H 0.0894 -0.0069 0.4056 0.037 Uiso 1 1 calc R . .
C10 C 0.2002(3) 0.0162(7) 0.49493(15) 0.0374(12) Uani 1 1 d . . .
H10 H 0.1945 0.0186 0.5264 0.045 Uiso 1 1 calc R . .
C11 C 0.2830(3) 0.0229(7) 0.47618(15) 0.0362(11) Uani 1 1 d . . .
C12 C 0.2928(3) 0.0209(6) 0.42987(15) 0.0347(11) Uani 1 1 d . . .
H12 H 0.3477 0.0277 0.4168 0.042 Uiso 1 1 calc R . .
C13 C 0.1215(3) 0.4781(7) 0.40007(15) 0.0376(12) Uani 1 1 d . . .
C14 C 0.1974(3) 0.5022(7) 0.43270(14) 0.0329(11) Uani 1 1 d . . .
C15 C 0.1838(3) 0.5120(7) 0.47871(15) 0.0381(11) Uani 1 1 d . . .
H15 H 0.1270 0.5098 0.4896 0.046 Uiso 1 1 calc R . .
C16 C 0.3302(3) 0.5302(7) 0.49319(16) 0.0432(12) Uani 1 1 d . . .
H16 H 0.3760 0.5394 0.5138 0.052 Uiso 1 1 calc R . .
C17 C 0.3487(3) 0.5228(7) 0.44736(15) 0.0359(11) Uani 1 1 d . . .
C18 C 0.2814(3) 0.5073(6) 0.41630(14) 0.0339(11) Uani 1 1 d . . .
H18 H 0.2924 0.5006 0.3852 0.041 Uiso 1 1 calc R . .
C19 C 0.8566(3) 0.0092(7) 0.35437(15) 0.0339(11) Uani 1 1 d . . .
C20 C 0.7738(3) 0.0225(6) 0.32631(14) 0.0281(10) Uani 1 1 d . . .
C21 C 0.7765(3) 0.0339(7) 0.27958(15) 0.0378(11) Uani 1 1 d . . .
H21 H 0.8303 0.0317 0.2652 0.045 Uiso 1 1 calc R . .
C22 C 0.6281(3) 0.0489(8) 0.27449(16) 0.0499(14) Uani 1 1 d . . .
H22 H 0.5781 0.0599 0.2568 0.060 Uiso 1 1 calc R . .
C23 C 0.6196(3) 0.0342(7) 0.32084(16) 0.0409(12) Uani 1 1 d . . .
C24 C 0.6930(3) 0.0238(6) 0.34779(15) 0.0352(11) Uani 1 1 d . . .
H24 H 0.6887 0.0178 0.3793 0.042 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O5 2.046(3) 2_556 ?
Zn1 O5 2.046(3) . ?
Zn1 O6 2.071(3) 2_556 ?
Zn1 O6 2.071(3) . ?
Zn1 N1 2.239(3) . ?
Zn1 N1 2.239(3) 2_556 ?
Zn2 O8 2.106(3) 3_556 ?
Zn2 O8 2.106(3) . ?
Zn2 O7 2.111(3) . ?
Zn2 O7 2.111(3) 3_556 ?
Zn2 N2 2.176(3) 3_556 ?
Zn2 N2 2.176(3) . ?
Br1 C5 1.882(4) . ?
Br2 C11 1.884(4) . ?
Br3 C17 1.890(4) . ?
Br4 C23 1.882(4) . ?
O1 C1 1.197(5) . ?
O2 C1 1.301(5) . ?
O2 H2 0.8200 . ?
O3 C7 1.274(5) . ?
O3 H3 0.8200 . ?
O4 C7 1.193(5) . ?
O5 H5A 0.8497 . ?
O5 H5B 0.8691 . ?
O6 H6A 0.8498 . ?
O6 H6B 0.8501 . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8505 . ?
O8 H8A 0.8502 . ?
O8 H8B 0.8501 . ?
O9 C13 1.259(5) . ?
O10 C13 1.239(6) . ?
O11 C19 1.241(5) . ?
O12 C19 1.251(5) . ?
N1 C3 1.333(5) . ?
N1 C4 1.344(5) . ?
N2 C10 1.337(5) . ?
N2 C9 1.345(5) . ?
N3 C16 1.318(6) . ?
N3 C15 1.352(6) . ?
N4 C22 1.327(6) . ?
N4 C21 1.340(6) . ?
C1 C2 1.491(6) . ?
C2 C3 1.387(6) . ?
C2 C6 1.397(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.373(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.506(6) . ?
C8 C9 1.378(6) . ?
C8 C12 1.389(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.519(6) . ?
C14 C15 1.370(6) . ?
C14 C18 1.380(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.519(6) . ?
C20 C21 1.376(6) . ?
C20 C24 1.396(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(6) . ?
C24 H24 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
O5 Zn1 O5 89.94(19) 2_556 . ?
O5 Zn1 O6 90.05(16) 2_556 2_556 ?
O5 Zn1 O6 177.43(12) . 2_556 ?
O5 Zn1 O6 177.43(12) 2_556 . ?
O5 Zn1 O6 90.05(16) . . ?
O6 Zn1 O6 90.1(3) 2_556 . ?
O5 Zn1 N1 89.67(12) 2_556 . ?
O5 Zn1 N1 92.88(13) . . ?
O6 Zn1 N1 89.68(13) 2_556 . ?
O6 Zn1 N1 87.77(13) . . ?
O5 Zn1 N1 92.88(12) 2_556 2_556 ?
O5 Zn1 N1 89.67(12) . 2_556 ?
O6 Zn1 N1 87.77(13) 2_556 2_556 ?
O6 Zn1 N1 89.68(13) . 2_556 ?
N1 Zn1 N1 176.40(19) . 2_556 ?
O8 Zn2 O8 180.00(12) 3_556 . ?
O8 Zn2 O7 88.06(12) 3_556 . ?
O8 Zn2 O7 91.94(12) . . ?
O8 Zn2 O7 91.94(12) 3_556 3_556 ?
O8 Zn2 O7 88.06(12) . 3_556 ?
O7 Zn2 O7 180.0 . 3_556 ?
O8 Zn2 N2 92.15(12) 3_556 3_556 ?
O8 Zn2 N2 87.85(12) . 3_556 ?
O7 Zn2 N2 91.93(12) . 3_556 ?
O7 Zn2 N2 88.07(12) 3_556 3_556 ?
O8 Zn2 N2 87.85(12) 3_556 . ?
O8 Zn2 N2 92.15(12) . . ?
O7 Zn2 N2 88.07(12) . . ?
O7 Zn2 N2 91.93(12) 3_556 . ?
N2 Zn2 N2 180.00(16) 3_556 . ?
C1 O2 H2 109.5 . . ?
C7 O3 H3 109.5 . . ?
Zn1 O5 H5A 124.1 . . ?
Zn1 O5 H5B 110.8 . . ?
H5A O5 H5B 116.5 . . ?
Zn1 O6 H6A 126.2 . . ?
Zn1 O6 H6B 117.0 . . ?
H6A O6 H6B 116.5 . . ?
Zn2 O7 H7A 116.0 . . ?
Zn2 O7 H7B 113.5 . . ?
H7A O7 H7B 116.3 . . ?
Zn2 O8 H8A 106.2 . . ?
Zn2 O8 H8B 116.6 . . ?
H8A O8 H8B 116.7 . . ?
C3 N1 C4 117.1(4) . . ?
C3 N1 Zn1 120.6(3) . . ?
C4 N1 Zn1 122.3(3) . . ?
C10 N2 C9 117.6(4) . . ?
C10 N2 Zn2 121.1(3) . . ?
C9 N2 Zn2 121.4(3) . . ?
C16 N3 C15 118.6(4) . . ?
C22 N4 C21 118.4(4) . . ?
O1 C1 O2 125.0(4) . . ?
O1 C1 C2 122.1(4) . . ?
O2 C1 C2 113.0(4) . . ?
C3 C2 C6 117.8(4) . . ?
C3 C2 C1 123.4(4) . . ?
C6 C2 C1 118.8(4) . . ?
N1 C3 C2 123.9(4) . . ?
N1 C3 H3A 118.0 . . ?
C2 C3 H3A 118.0 . . ?
N1 C4 C5 122.9(4) . . ?
N1 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C6 C5 C4 119.9(4) . . ?
C6 C5 Br1 120.2(3) . . ?
C4 C5 Br1 119.9(3) . . ?
C5 C6 C2 118.4(4) . . ?
C5 C6 H6 120.8 . . ?
C2 C6 H6 120.8 . . ?
O4 C7 O3 124.9(4) . . ?
O4 C7 C8 121.5(4) . . ?
O3 C7 C8 113.6(4) . . ?
C9 C8 C12 118.5(4) . . ?
C9 C8 C7 119.4(4) . . ?
C12 C8 C7 122.1(4) . . ?
N2 C9 C8 123.4(4) . . ?
N2 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
N2 C10 C11 122.3(4) . . ?
N2 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 Br2 121.3(3) . . ?
C10 C11 Br2 119.0(3) . . ?
C11 C12 C8 118.6(4) . . ?
C11 C12 H12 120.7 . . ?
C8 C12 H12 120.7 . . ?
O10 C13 O9 125.7(4) . . ?
O10 C13 C14 116.4(4) . . ?
O9 C13 C14 117.8(4) . . ?
C15 C14 C18 119.3(4) . . ?
C15 C14 C13 120.6(4) . . ?
C18 C14 C13 120.1(4) . . ?
N3 C15 C14 122.2(4) . . ?
N3 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
N3 C16 C17 122.3(4) . . ?
N3 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C16 C17 C18 119.5(4) . . ?
C16 C17 Br3 120.6(3) . . ?
C18 C17 Br3 119.9(3) . . ?
C14 C18 C17 118.2(4) . . ?
C14 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
O11 C19 O12 126.2(4) . . ?
O11 C19 C20 117.2(4) . . ?
O12 C19 C20 116.6(4) . . ?
C21 C20 C24 118.6(4) . . ?
C21 C20 C19 121.2(4) . . ?
C24 C20 C19 120.1(4) . . ?
N4 C21 C20 122.7(4) . . ?
N4 C21 H21 118.6 . . ?
C20 C21 H21 118.6 . . ?
N4 C22 C23 122.6(4) . . ?
N4 C22 H22 118.7 . . ?
C23 C22 H22 118.7 . . ?
C22 C23 C24 119.6(4) . . ?
C22 C23 Br4 118.6(3) . . ?
C24 C23 Br4 121.7(4) . . ?
C23 C24 C20 118.0(4) . . ?
C23 C24 H24 121.0 . . ?
C20 C24 H24 121.0 . . ?

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
O5 Zn1 N1 C3 -131.7(3) 2_556 . . . ?
O5 Zn1 N1 C3 -41.8(3) . . . . ?
O6 Zn1 N1 C3 138.3(3) 2_556 . . . ?
O6 Zn1 N1 C3 48.2(3) . . . . ?
O5 Zn1 N1 C4 47.8(4) 2_556 . . . ?
O5 Zn1 N1 C4 137.7(4) . . . . ?
O6 Zn1 N1 C4 -42.2(4) 2_556 . . . ?
O6 Zn1 N1 C4 -132.3(4) . . . . ?
O8 Zn2 N2 C10 -46.0(4) 3_556 . . . ?
O8 Zn2 N2 C10 134.0(4) . . . . ?
O7 Zn2 N2 C10 42.1(4) . . . . ?
O7 Zn2 N2 C10 -137.9(4) 3_556 . . . ?
O8 Zn2 N2 C9 134.4(3) 3_556 . . . ?
O8 Zn2 N2 C9 -45.6(3) . . . . ?
O7 Zn2 N2 C9 -137.5(3) . . . . ?
O7 Zn2 N2 C9 42.5(3) 3_556 . . . ?
O1 C1 C2 C3 -174.6(5) . . . . ?
O2 C1 C2 C3 5.1(7) . . . . ?
O1 C1 C2 C6 4.4(7) . . . . ?
O2 C1 C2 C6 -176.0(4) . . . . ?
C4 N1 C3 C2 -1.2(7) . . . . ?
Zn1 N1 C3 C2 178.3(3) . . . . ?
C6 C2 C3 N1 2.3(7) . . . . ?
C1 C2 C3 N1 -178.7(4) . . . . ?
C3 N1 C4 C5 0.4(7) . . . . ?
Zn1 N1 C4 C5 -179.1(4) . . . . ?
N1 C4 C5 C6 -0.8(8) . . . . ?
N1 C4 C5 Br1 -179.9(4) . . . . ?
C4 C5 C6 C2 1.9(7) . . . . ?
Br1 C5 C6 C2 -179.0(4) . . . . ?
C3 C2 C6 C5 -2.6(7) . . . . ?
C1 C2 C6 C5 178.4(4) . . . . ?
O4 C7 C8 C9 -20.4(7) . . . . ?
O3 C7 C8 C9 162.4(4) . . . . ?
O4 C7 C8 C12 160.3(5) . . . . ?
O3 C7 C8 C12 -16.9(7) . . . . ?
C10 N2 C9 C8 -0.7(6) . . . . ?
Zn2 N2 C9 C8 178.9(3) . . . . ?
C12 C8 C9 N2 0.0(7) . . . . ?
C7 C8 C9 N2 -179.3(4) . . . . ?
C9 N2 C10 C11 0.5(7) . . . . ?
Zn2 N2 C10 C11 -179.1(3) . . . . ?
N2 C10 C11 C12 0.5(7) . . . . ?
N2 C10 C11 Br2 -178.9(4) . . . . ?
C10 C11 C12 C8 -1.2(7) . . . . ?
Br2 C11 C12 C8 178.2(3) . . . . ?
C9 C8 C12 C11 1.0(7) . . . . ?
C7 C8 C12 C11 -179.8(4) . . . . ?
O10 C13 C14 C15 -167.4(5) . . . . ?
O9 C13 C14 C15 9.1(7) . . . . ?
O10 C13 C14 C18 10.2(7) . . . . ?
O9 C13 C14 C18 -173.2(4) . . . . ?
C16 N3 C15 C14 0.8(7) . . . . ?
C18 C14 C15 N3 -0.6(7) . . . . ?
C13 C14 C15 N3 177.0(4) . . . . ?
C15 N3 C16 C17 -0.2(7) . . . . ?
N3 C16 C17 C18 -0.6(8) . . . . ?
N3 C16 C17 Br3 179.3(4) . . . . ?
C15 C14 C18 C17 -0.2(7) . . . . ?
C13 C14 C18 C17 -177.8(4) . . . . ?
C16 C17 C18 C14 0.7(7) . . . . ?
Br3 C17 C18 C14 -179.2(3) . . . . ?
O11 C19 C20 C21 -176.3(4) . . . . ?
O12 C19 C20 C21 3.8(7) . . . . ?
O11 C19 C20 C24 3.9(7) . . . . ?
O12 C19 C20 C24 -176.1(4) . . . . ?
C22 N4 C21 C20 -0.7(7) . . . . ?
C24 C20 C21 N4 0.6(7) . . . . ?
C19 C20 C21 N4 -179.2(4) . . . . ?
C21 N4 C22 C23 -0.6(8) . . . . ?
N4 C22 C23 C24 2.0(8) . . . . ?
N4 C22 C23 Br4 179.5(4) . . . . ?
C22 C23 C24 C20 -2.0(7) . . . . ?
Br4 C23 C24 C20 -179.4(3) . . . . ?
C21 C20 C24 C23 0.7(7) . . . . ?
C19 C20 C24 C23 -179.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.106
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1001901'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;

_audit_creation_date             2015-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 Br2 N2 O4 Zn, 0.8(H2 O), 0.35(H2 O)'
_chemical_formula_sum            'C12 H8.30 Br2 N2 O5.15 Zn'
_chemical_formula_weight         488.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   7.782(5)
_cell_length_b                   7.787(5)
_cell_length_c                   26.565(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.944(13)
_cell_angle_gamma                90
_cell_volume                     1598.0(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2354
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.440
_shelx_estimated_absorpt_T_min   0.385
_exptl_absorpt_coefficient_mu    6.561
_exptl_absorpt_correction_T_max  0.4394
_exptl_absorpt_correction_T_min  0.3847
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1213 before and 0.0839 after correction.
The Ratio of minimum to maximum transmission is 0.5537.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLORLESS
_exptl_crystal_colour_primary    COLORLESS
_exptl_crystal_density_diffrn    2.029
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             942
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.1256
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            8192
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.402
_diffrn_reflns_theta_min         1.544
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2614
_reflns_number_total             3786
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.900
_refine_diff_density_min         -1.247
_refine_diff_density_rms         0.193
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.1101
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+32.1083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2363
_refine_ls_wR_factor_ref         0.2508
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O5-H5A = O5-H5B
 0.85 with sigma of 0.01
3. Others
 Fixed Sof: O5(0.8) H5A(0.8) H5B(0.8) O6(0.35)
4.a Riding coordinates:
 O5(H5A,H5B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C7(H7), C9(H9), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.61226(18) 0.87890(15) 0.09729(5) 0.0293(3) Uani 1 1 d . . . . .
Br1 Br 0.8535(2) 0.6703(2) -0.09402(5) 0.0593(5) Uani 1 1 d . . . . .
Br2 Br 0.7828(3) 0.5721(2) 0.29616(5) 0.0736(7) Uani 1 1 d . . . . .
O1 O 0.7016(14) 0.0524(10) 0.1531(4) 0.050(3) Uani 1 1 d . . . . .
O2 O 0.6009(14) 0.1763(11) 0.0804(4) 0.051(2) Uani 1 1 d . . . . .
O3 O 1.3161(13) 0.8875(14) 0.1151(4) 0.060(3) Uani 1 1 d . . . . .
O4 O 1.4152(12) 0.8001(13) 0.0456(4) 0.051(2) Uani 1 1 d . . . . .
N1 N 0.8066(13) 0.8284(11) 0.0515(4) 0.032(2) Uani 1 1 d . . . . .
N2 N 0.6600(14) 0.6634(10) 0.1445(3) 0.032(2) Uani 1 1 d . . . . .
C1 C 0.9711(17) 0.8431(13) 0.0722(5) 0.038(3) Uani 1 1 d . . . . .
H1 H 0.9924 0.8776 0.1059 0.045 Uiso 1 1 calc R . . . .
C2 C 1.1112(16) 0.8100(13) 0.0464(4) 0.033(3) Uani 1 1 d . . . . .
C3 C 1.0752(16) 0.7546(14) -0.0041(4) 0.033(3) Uani 1 1 d . . . . .
H3 H 1.1652 0.7283 -0.0228 0.040 Uiso 1 1 calc R . . . .
C4 C 0.9069(16) 0.7398(13) -0.0257(4) 0.031(2) Uani 1 1 d . . . . .
C5 C 0.7712(17) 0.7770(13) 0.0027(4) 0.037(3) Uani 1 1 d . . . . .
H5 H 0.6569 0.7663 -0.0119 0.045 Uiso 1 1 calc R . . . .
C6 C 1.2922(17) 0.8355(15) 0.0719(5) 0.042(3) Uani 1 1 d . . . . .
C7 C 0.7033(15) 0.6789(13) 0.1951(4) 0.031(2) Uani 1 1 d . . . . .
H7 H 0.7166 0.7877 0.2095 0.038 Uiso 1 1 calc R . . . .
C8 C 0.7280(19) 0.5377(15) 0.2256(5) 0.041(3) Uani 1 1 d . . . . .
C9 C 0.7183(18) 0.3739(15) 0.2048(5) 0.043(3) Uani 1 1 d . . . . .
H9 H 0.7393 0.2775 0.2252 0.052 Uiso 1 1 calc R . . . .
C10 C 0.6764(16) 0.3571(12) 0.1525(4) 0.032(2) Uani 1 1 d . . . . .
C11 C 0.6487(15) 0.5061(12) 0.1248(4) 0.028(2) Uani 1 1 d . . . . .
H11 H 0.6203 0.4961 0.0899 0.034 Uiso 1 1 calc R . . . .
C12 C 0.6606(17) 0.1848(14) 0.1265(5) 0.039(3) Uani 1 1 d . . . . .
O5 O 0.662(3) 0.040(2) 0.2839(6) 0.110(7) Uani 0.8 1 d D . P A 1
H5A H 0.7701 0.0526 0.2818 0.166 Uiso 0.8 1 d DR . P A 1
H5B H 0.6546 -0.0047 0.3130 0.166 Uiso 0.8 1 d DR . P A 1
O6 O 0.996(6) 0.021(5) 0.2315(12) 0.085(11) Uani 0.35 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.063(9) 1_565 ?
Zn1 O2 2.358(9) 1_565 ?
Zn1 O3 2.409(11) 1_455 ?
Zn1 O4 2.026(9) 1_455 ?
Zn1 N1 2.089(10) . ?
Zn1 N2 2.101(8) . ?
Zn1 C6 2.524(13) 1_455 ?
Zn1 C12 2.519(11) 1_565 ?
Br1 C4 1.892(11) . ?
Br2 C8 1.890(12) . ?
O1 Zn1 2.063(9) 1_545 ?
O1 C12 1.268(14) . ?
O2 Zn1 2.358(9) 1_545 ?
O2 C12 1.257(15) . ?
O3 Zn1 2.409(11) 1_655 ?
O3 C6 1.211(17) . ?
O4 Zn1 2.026(9) 1_655 ?
O4 C6 1.281(17) . ?
N1 C1 1.335(15) . ?
N1 C5 1.353(14) . ?
N2 C7 1.351(13) . ?
N2 C11 1.331(12) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(19) . ?
C2 C3 1.406(15) . ?
C2 C6 1.500(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(16) . ?
C4 C5 1.401(18) . ?
C5 H5 0.9300 . ?
C6 Zn1 2.524(13) 1_655 ?
C7 H7 0.9300 . ?
C7 C8 1.365(15) . ?
C8 C9 1.389(16) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(16) . ?
C10 C11 1.377(14) . ?
C10 C12 1.508(14) . ?
C11 H11 0.9300 . ?
C12 Zn1 2.519(11) 1_545 ?
O5 H5A 0.8525 . ?
O5 H5B 0.8582 . ?
O6 O6 0.98(6) 2_755 ?

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 Zn1 O2 59.7(3) 1_565 1_565 ?
O1 Zn1 O3 95.1(4) 1_565 1_455 ?
O1 Zn1 N1 109.7(4) 1_565 . ?
O1 Zn1 N2 94.2(3) 1_565 . ?
O1 Zn1 C6 121.1(4) 1_565 1_455 ?
O1 Zn1 C12 30.1(4) 1_565 1_565 ?
O2 Zn1 O3 89.7(4) 1_565 1_455 ?
O2 Zn1 C6 93.9(4) 1_565 1_455 ?
O2 Zn1 C12 29.6(3) 1_565 1_565 ?
O3 Zn1 C6 28.3(4) 1_455 1_455 ?
O3 Zn1 C12 91.4(4) 1_455 1_565 ?
O4 Zn1 O1 147.9(4) 1_455 1_565 ?
O4 Zn1 O2 99.3(4) 1_455 1_565 ?
O4 Zn1 O3 58.5(4) 1_455 1_455 ?
O4 Zn1 N1 95.2(4) 1_455 . ?
O4 Zn1 N2 103.1(4) 1_455 . ?
O4 Zn1 C6 30.3(4) 1_455 1_455 ?
O4 Zn1 C12 124.6(4) 1_455 1_565 ?
N1 Zn1 O2 95.0(4) . 1_565 ?
N1 Zn1 O3 153.7(4) . 1_455 ?
N1 Zn1 N2 96.3(4) . . ?
N1 Zn1 C6 125.4(4) . 1_455 ?
N1 Zn1 C12 105.4(4) . 1_565 ?
N2 Zn1 O2 153.8(3) . 1_565 ?
N2 Zn1 O3 90.5(4) . 1_455 ?
N2 Zn1 C6 98.6(4) . 1_455 ?
N2 Zn1 C12 124.2(4) . 1_565 ?
C12 Zn1 C6 108.4(4) 1_565 1_455 ?
C12 O1 Zn1 95.3(7) . 1_545 ?
C12 O2 Zn1 82.3(7) . 1_545 ?
C6 O3 Zn1 81.1(9) . 1_655 ?
C6 O4 Zn1 96.9(8) . 1_655 ?
C1 N1 Zn1 118.0(8) . . ?
C1 N1 C5 119.6(11) . . ?
C5 N1 Zn1 122.3(8) . . ?
C7 N2 Zn1 121.9(7) . . ?
C11 N2 Zn1 120.1(7) . . ?
C11 N2 C7 118.1(8) . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.7(11) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 116.9(11) . . ?
C1 C2 C6 120.4(11) . . ?
C3 C2 C6 122.6(12) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(12) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 Br1 120.9(9) . . ?
C3 C4 C5 120.2(10) . . ?
C5 C4 Br1 118.9(8) . . ?
N1 C5 C4 119.8(11) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
O3 C6 Zn1 70.6(8) . 1_655 ?
O3 C6 O4 123.3(12) . . ?
O3 C6 C2 120.0(13) . . ?
O4 C6 Zn1 52.8(6) . 1_655 ?
O4 C6 C2 116.7(12) . . ?
C2 C6 Zn1 168.8(10) . 1_655 ?
N2 C7 H7 119.4 . . ?
N2 C7 C8 121.2(10) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 Br2 118.2(8) . . ?
C7 C8 C9 120.4(11) . . ?
C9 C8 Br2 121.4(9) . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.6(10) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 C12 122.5(10) . . ?
C11 C10 C9 117.1(9) . . ?
C11 C10 C12 120.4(10) . . ?
N2 C11 C10 124.5(9) . . ?
N2 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
O1 C12 Zn1 54.6(6) . 1_545 ?
O1 C12 C10 117.8(11) . . ?
O2 C12 Zn1 68.1(6) . 1_545 ?
O2 C12 O1 122.5(10) . . ?
O2 C12 C10 119.5(10) . . ?
C10 C12 Zn1 169.6(9) . 1_545 ?
H5A O5 H5B 106.4 . . ?

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
Zn1 O1 C12 O2 -5.2(15) 1_545 . . . ?
Zn1 O1 C12 C10 171.6(10) 1_545 . . . ?
Zn1 O2 C12 O1 4.6(14) 1_545 . . . ?
Zn1 O2 C12 C10 -172.2(12) 1_545 . . . ?
Zn1 O3 C6 O4 3.8(12) 1_655 . . . ?
Zn1 O3 C6 C2 -176.1(10) 1_655 . . . ?
Zn1 O4 C6 O3 -4.4(14) 1_655 . . . ?
Zn1 O4 C6 C2 175.4(8) 1_655 . . . ?
Zn1 N1 C1 C2 178.6(8) . . . . ?
Zn1 N1 C5 C4 -178.0(7) . . . . ?
Zn1 N2 C7 C8 177.7(10) . . . . ?
Zn1 N2 C11 C10 -179.6(10) . . . . ?
Br1 C4 C5 N1 -179.4(8) . . . . ?
Br2 C8 C9 C10 179.7(10) . . . . ?
N1 C1 C2 C3 -1.3(16) . . . . ?
N1 C1 C2 C6 177.9(10) . . . . ?
N2 C7 C8 Br2 -178.5(9) . . . . ?
N2 C7 C8 C9 4(2) . . . . ?
C1 N1 C5 C4 -0.1(15) . . . . ?
C1 C2 C3 C4 1.4(16) . . . . ?
C1 C2 C6 Zn1 -161(4) . . . 1_655 ?
C1 C2 C6 O3 -0.9(17) . . . . ?
C1 C2 C6 O4 179.3(10) . . . . ?
C2 C3 C4 Br1 178.7(8) . . . . ?
C2 C3 C4 C5 -1.0(16) . . . . ?
C3 C2 C6 Zn1 18(5) . . . 1_655 ?
C3 C2 C6 O3 178.1(11) . . . . ?
C3 C2 C6 O4 -1.7(16) . . . . ?
C3 C4 C5 N1 0.3(16) . . . . ?
C5 N1 C1 C2 0.6(16) . . . . ?
C6 C2 C3 C4 -177.7(10) . . . . ?
C7 N2 C11 C10 0.8(19) . . . . ?
C7 C8 C9 C10 -2(2) . . . . ?
C8 C9 C10 C11 1(2) . . . . ?
C8 C9 C10 C12 -179.2(13) . . . . ?
C9 C10 C11 N2 0.2(19) . . . . ?
C9 C10 C12 Zn1 35(6) . . . 1_545 ?
C9 C10 C12 O1 -6(2) . . . . ?
C9 C10 C12 O2 170.8(13) . . . . ?
C11 N2 C7 C8 -2.7(19) . . . . ?
C11 C10 C12 Zn1 -144(5) . . . 1_545 ?
C11 C10 C12 O1 174.1(13) . . . . ?
C11 C10 C12 O2 -9.0(19) . . . . ?
C12 C10 C11 N2 -180.0(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
