# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Br2 N2 O2 Zn'
_chemical_formula_weight         439.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   20.940(13)
_cell_length_b                   9.168(4)
_cell_length_c                   16.491(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.673(7)
_cell_angle_gamma                90.00
_cell_volume                     2877(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3713
_cell_measurement_theta_min      2.5919
_cell_measurement_theta_max      27.4816

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.1800
_exptl_crystal_size_min          0.0800
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.029
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    7.260
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5553
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Mercury2
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11213
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3261
_reflns_number_gt                2295
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1172P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3261
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1800
_refine_ls_wR_factor_gt          0.1662
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.090
_refine_ls_shift/su_mean         0.015

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 0.18207(3) 0.07592(7) 0.03678(4) 0.0478(2) Uani 1 1 d . . .
Br2 Br 0.27644(3) 0.19249(7) 0.15505(4) 0.0627(3) Uani 1 1 d . . .
Br1 Br 0.13560(4) -0.11887(8) 0.09233(5) 0.0684(3) Uani 1 1 d . . .
N1 N -0.1108(2) -0.7559(5) -0.4810(3) 0.0475(10) Uani 1 1 d . . .
O2 O 0.2121(2) -0.0102(5) -0.0510(3) 0.0549(10) Uani 1 1 d . . .
C3 C -0.1303(3) -0.6164(7) -0.4950(4) 0.0589(16) Uani 1 1 d . . .
H3A H -0.1764 -0.5942 -0.5335 0.071 Uiso 1 1 calc R . .
C8 C 0.1531(4) -0.3466(8) -0.2496(6) 0.080(2) Uani 1 1 d . . .
H8A H 0.1990 -0.3734 -0.2130 0.096 Uiso 1 1 calc R . .
N2 N 0.1341(2) -0.2087(5) -0.2540(3) 0.0454(10) Uani 1 1 d . . .
C12 C 0.1611(3) -0.0538(7) -0.1222(4) 0.0513(14) Uani 1 1 d . . .
C9 C 0.0204(3) -0.2712(7) -0.3578(4) 0.0539(14) Uani 1 1 d . . .
H9A H -0.0243 -0.2406 -0.3969 0.065 Uiso 1 1 calc R . .
C10 C 0.0697(3) -0.1688(7) -0.3082(4) 0.0595(16) Uani 1 1 d . . .
H10A H 0.0574 -0.0707 -0.3130 0.071 Uiso 1 1 calc R . .
C6 C 0.0363(3) -0.4177(6) -0.3501(4) 0.0476(13) Uani 1 1 d . . .
O1 O 0.0991(3) -0.0550(7) -0.1370(4) 0.0790(15) Uani 1 1 d . . .
C11 C 0.1847(3) -0.1024(7) -0.1944(4) 0.0533(14) Uani 1 1 d . . .
H11A H 0.1874 -0.0184 -0.2285 0.064 Uiso 1 1 calc R . .
H11B H 0.2309 -0.1463 -0.1667 0.064 Uiso 1 1 calc R . .
C5 C -0.0162(3) -0.5314(6) -0.3980(4) 0.0442(12) Uani 1 1 d . . .
C1 C -0.0454(3) -0.7835(7) -0.4274(6) 0.071(2) Uani 1 1 d . . .
H1A H -0.0306 -0.8801 -0.4192 0.085 Uiso 1 1 calc R . .
C4 C -0.0842(3) -0.5036(7) -0.4544(5) 0.0614(16) Uani 1 1 d . . .
H4A H -0.0999 -0.4076 -0.4656 0.074 Uiso 1 1 calc R . .
C7 C 0.1052(4) -0.4525(8) -0.2991(6) 0.089(3) Uani 1 1 d . . .
H7A H 0.1201 -0.5484 -0.2977 0.107 Uiso 1 1 calc R . .
C2 C 0.0029(3) -0.6759(8) -0.3824(5) 0.072(2) Uani 1 1 d . . .
H2A H 0.0479 -0.7012 -0.3418 0.086 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0519(4) 0.0478(4) 0.0397(4) -0.0005(3) 0.0152(3) 0.0006(3)
Br2 0.0702(5) 0.0521(4) 0.0470(4) -0.0005(3) 0.0059(3) -0.0026(3)
Br1 0.0878(5) 0.0615(5) 0.0596(5) 0.0006(3) 0.0343(4) -0.0165(3)
N1 0.052(3) 0.044(3) 0.046(3) -0.003(2) 0.019(2) 0.003(2)
O2 0.057(2) 0.059(3) 0.049(2) -0.0100(19) 0.0225(19) -0.0109(18)
C3 0.049(3) 0.055(4) 0.055(4) 0.007(3) 0.005(3) -0.001(3)
C8 0.052(4) 0.053(4) 0.096(6) -0.012(4) -0.006(4) 0.005(3)
N2 0.053(3) 0.044(3) 0.037(2) -0.0089(19) 0.017(2) -0.0065(19)
C12 0.056(3) 0.056(3) 0.047(3) -0.006(3) 0.026(3) -0.009(3)
C9 0.051(3) 0.050(3) 0.050(3) -0.004(3) 0.010(3) 0.011(2)
C10 0.065(4) 0.045(3) 0.054(4) -0.001(3) 0.010(3) 0.005(3)
C6 0.046(3) 0.047(3) 0.046(3) -0.005(2) 0.015(2) 0.005(2)
O1 0.063(3) 0.115(4) 0.065(3) -0.035(3) 0.033(2) -0.024(3)
C11 0.058(3) 0.056(4) 0.046(3) -0.005(3) 0.022(3) -0.012(3)
C5 0.047(3) 0.042(3) 0.043(3) -0.004(2) 0.017(2) 0.005(2)
C1 0.054(4) 0.044(3) 0.095(6) -0.010(3) 0.010(3) 0.007(3)
C4 0.056(3) 0.045(3) 0.064(4) 0.003(3) 0.006(3) 0.001(3)
C7 0.070(4) 0.039(4) 0.107(7) -0.009(4) -0.014(4) 0.004(3)
C2 0.041(3) 0.062(4) 0.088(5) -0.006(4) 0.004(3) 0.012(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 1.967(4) . ?
Zn1 N1 2.074(5) 2_564 ?
Zn1 Br2 2.3735(12) . ?
Zn1 Br1 2.3916(12) . ?
N1 C1 1.308(8) . ?
N1 C3 1.333(8) . ?
N1 Zn1 2.074(5) 2_544 ?
O2 C12 1.278(7) . ?
C3 C4 1.382(9) . ?
C8 N2 1.318(8) . ?
C8 C7 1.390(10) . ?
N2 C10 1.321(8) . ?
N2 C11 1.472(7) . ?
C12 O1 1.217(7) . ?
C12 C11 1.532(8) . ?
C9 C6 1.377(8) . ?
C9 C10 1.383(9) . ?
C6 C7 1.370(9) . ?
C6 C5 1.480(8) . ?
C5 C4 1.362(8) . ?
C5 C2 1.377(9) . ?
C1 C2 1.385(9) . ?

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 N1 111.30(19) . 2_564 ?
O2 Zn1 Br2 111.91(13) . . ?
N1 Zn1 Br2 103.16(14) 2_564 . ?
O2 Zn1 Br1 106.73(13) . . ?
N1 Zn1 Br1 113.13(13) 2_564 . ?
Br2 Zn1 Br1 110.72(5) . . ?
C1 N1 C3 117.4(5) . . ?
C1 N1 Zn1 120.8(4) . 2_544 ?
C3 N1 Zn1 121.7(4) . 2_544 ?
C12 O2 Zn1 113.7(4) . . ?
N1 C3 C4 122.2(6) . . ?
N2 C8 C7 120.7(6) . . ?
C10 N2 C8 120.1(5) . . ?
C10 N2 C11 121.0(5) . . ?
C8 N2 C11 118.8(5) . . ?
O1 C12 O2 126.8(6) . . ?
O1 C12 C11 120.3(5) . . ?
O2 C12 C11 112.9(5) . . ?
C6 C9 C10 121.0(5) . . ?
N2 C10 C9 120.8(6) . . ?
C9 C6 C7 115.8(5) . . ?
C9 C6 C5 122.7(5) . . ?
C7 C6 C5 121.3(5) . . ?
N2 C11 C12 109.7(5) . . ?
C4 C5 C2 116.5(5) . . ?
C4 C5 C6 124.3(5) . . ?
C2 C5 C6 119.0(5) . . ?
N1 C1 C2 123.3(6) . . ?
C5 C4 C3 120.7(6) . . ?
C6 C7 C8 121.0(6) . . ?
C5 C2 C1 119.7(6) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.265
_refine_diff_density_min         -1.099
_refine_diff_density_rms         0.185
_database_code_depnum_ccdc_archive 'CCDC 994628'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O2 Zn'
_chemical_formula_weight         350.49

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                   21.042(14)
_cell_length_b                   8.881(5)
_cell_length_c                   16.352(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.670(9)
_cell_angle_gamma                90.00
_cell_volume                     2798(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3886
_cell_measurement_theta_min      2.0022
_cell_measurement_theta_max      27.4045

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.1500
_exptl_crystal_size_mid          0.1200
_exptl_crystal_size_min          0.0600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    2.134
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8879
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn70
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10721
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         27.41
_reflns_number_total             3127
_reflns_number_gt                2622
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1633P)²+11.3840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3127
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2459
_refine_ls_wR_factor_gt          0.2330
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.010

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 0.18547(4) 0.07084(8) 0.04253(5) 0.0452(3) Uani 1 1 d . . .
Cl2 Cl 0.14146(8) -0.12176(16) 0.09963(10) 0.0444(4) Uani 1 1 d . . .
Cl3 Cl 0.27423(8) 0.19397(15) 0.15241(9) 0.0448(4) Uani 1 1 d . . .
O1 O 0.2153(2) -0.0155(6) -0.0459(3) 0.0524(11) Uani 1 1 d . . .
C12 C 0.1662(3) -0.0643(7) -0.1172(5) 0.0486(14) Uani 1 1 d . . .
O2 O 0.1057(3) -0.0729(8) -0.1284(4) 0.0789(19) Uani 1 1 d . . .
N1 N -0.1131(2) -0.7613(6) -0.4847(4) 0.0465(11) Uani 1 1 d . . .
N2 N 0.1376(2) -0.2133(6) -0.2533(3) 0.0433(11) Uani 1 1 d . . .
C6 C 0.0386(3) -0.4223(6) -0.3521(4) 0.0435(13) Uani 1 1 d . . .
C8 C 0.0733(4) -0.1673(8) -0.3044(5) 0.0560(16) Uani 1 1 d . . .
H8A H 0.0624 -0.0655 -0.3061 0.067 Uiso 1 1 calc R . .
C10 C 0.1553(4) -0.3573(9) -0.2523(6) 0.068(2) Uani 1 1 d . . .
H10A H 0.2008 -0.3871 -0.2187 0.082 Uiso 1 1 calc R . .
C2 C -0.0835(3) -0.5020(8) -0.4519(5) 0.0568(17) Uani 1 1 d . . .
H2A H -0.0981 -0.4021 -0.4602 0.068 Uiso 1 1 calc R . .
C5 C -0.0152(3) -0.5377(7) -0.3985(4) 0.0447(13) Uani 1 1 d . . .
C11 C 0.1884(3) -0.1067(8) -0.1915(5) 0.0516(15) Uani 1 1 d . . .
H11A H 0.1912 -0.0170 -0.2238 0.062 Uiso 1 1 calc R . .
H11B H 0.2340 -0.1530 -0.1665 0.062 Uiso 1 1 calc R . .
C7 C 0.0227(3) -0.2691(7) -0.3550(5) 0.0542(15) Uani 1 1 d . . .
H7A H -0.0217 -0.2353 -0.3907 0.065 Uiso 1 1 calc R . .
C1 C -0.1293(3) -0.6161(8) -0.4924(5) 0.0512(15) Uani 1 1 d . . .
H1A H -0.1749 -0.5899 -0.5277 0.061 Uiso 1 1 calc R . .
C9 C 0.1062(4) -0.4631(9) -0.3014(6) 0.072(2) Uani 1 1 d . . .
H9A H 0.1192 -0.5635 -0.2999 0.086 Uiso 1 1 calc R . .
C3 C -0.0469(4) -0.7946(8) -0.4352(7) 0.075(2) Uani 1 1 d . . .
H3A H -0.0334 -0.8950 -0.4297 0.089 Uiso 1 1 calc R . .
C4 C 0.0023(3) -0.6869(8) -0.3917(7) 0.079(3) Uani 1 1 d . . .
H4A H 0.0478 -0.7160 -0.3575 0.094 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0439(5) 0.0434(5) 0.0455(5) 0.0002(3) 0.0152(4) -0.0004(3)
Cl2 0.0529(8) 0.0408(7) 0.0449(8) 0.0051(5) 0.0253(7) -0.0078(6)
Cl3 0.0467(8) 0.0365(7) 0.0358(7) -0.0007(5) 0.0004(6) -0.0017(5)
O1 0.045(2) 0.057(3) 0.053(3) -0.012(2) 0.017(2) -0.010(2)
C12 0.045(3) 0.051(3) 0.048(4) -0.010(3) 0.017(3) -0.013(3)
O2 0.047(3) 0.118(5) 0.073(4) -0.035(3) 0.026(3) -0.023(3)
N1 0.037(2) 0.045(3) 0.057(3) -0.004(2) 0.018(2) 0.000(2)
N2 0.039(2) 0.047(3) 0.039(3) -0.004(2) 0.011(2) -0.004(2)
C6 0.041(3) 0.040(3) 0.043(3) -0.001(2) 0.010(3) 0.005(2)
C8 0.058(4) 0.043(3) 0.059(4) -0.002(3) 0.015(3) 0.004(3)
C10 0.045(4) 0.058(4) 0.078(5) -0.011(4) 0.000(3) 0.003(3)
C2 0.036(3) 0.047(3) 0.074(5) 0.002(3) 0.008(3) 0.008(2)
C5 0.036(3) 0.048(3) 0.047(3) -0.007(3) 0.013(3) 0.005(2)
C11 0.048(3) 0.056(4) 0.050(4) -0.012(3) 0.019(3) -0.014(3)
C7 0.045(3) 0.045(3) 0.061(4) -0.001(3) 0.010(3) 0.007(3)
C1 0.035(3) 0.047(3) 0.058(4) 0.002(3) 0.004(3) 0.004(2)
C9 0.044(4) 0.043(3) 0.105(7) -0.009(4) 0.006(4) 0.008(3)
C3 0.046(4) 0.040(3) 0.112(7) -0.008(4) 0.005(4) 0.007(3)
C4 0.033(3) 0.046(4) 0.118(7) -0.005(4) -0.010(4) 0.009(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.950(5) . ?
Zn1 N1 2.069(5) 2_564 ?
Zn1 Cl3 2.2841(17) . ?
Zn1 Cl2 2.3129(17) . ?
O1 C12 1.284(8) . ?
C12 O2 1.213(8) . ?
C12 C11 1.514(9) . ?
N1 C1 1.326(8) . ?
N1 C3 1.332(9) . ?
N1 Zn1 2.069(5) 2_544 ?
N2 C8 1.336(9) . ?
N2 C10 1.330(9) . ?
N2 C11 1.481(8) . ?
C6 C9 1.377(9) . ?
C6 C7 1.398(8) . ?
C6 C5 1.489(9) . ?
C8 C7 1.390(10) . ?
C10 C9 1.389(10) . ?
C2 C5 1.387(8) . ?
C2 C1 1.372(9) . ?
C5 C4 1.368(9) . ?
C3 C4 1.380(10) . ?

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 N1 110.0(2) . 2_564 ?
O1 Zn1 Cl3 111.49(14) . . ?
N1 Zn1 Cl3 103.52(16) 2_564 . ?
O1 Zn1 Cl2 107.99(15) . . ?
N1 Zn1 Cl2 112.13(15) 2_564 . ?
Cl3 Zn1 Cl2 111.71(7) . . ?
C12 O1 Zn1 115.1(4) . . ?
O2 C12 O1 124.9(6) . . ?
O2 C12 C11 120.3(6) . . ?
O1 C12 C11 114.7(5) . . ?
C1 N1 C3 116.0(6) . . ?
C1 N1 Zn1 122.9(4) . 2_544 ?
C3 N1 Zn1 121.0(5) . 2_544 ?
C8 N2 C10 120.7(6) . . ?
C8 N2 C11 120.2(6) . . ?
C10 N2 C11 118.9(6) . . ?
C9 C6 C7 116.9(6) . . ?
C9 C6 C5 121.0(6) . . ?
C7 C6 C5 122.0(6) . . ?
N2 C8 C7 121.0(6) . . ?
N2 C10 C9 120.2(6) . . ?
C5 C2 C1 119.0(6) . . ?
C4 C5 C2 116.8(6) . . ?
C4 C5 C6 120.1(5) . . ?
C2 C5 C6 123.2(6) . . ?
N2 C11 C12 109.6(5) . . ?
C8 C7 C6 119.8(6) . . ?
N1 C1 C2 124.7(6) . . ?
C6 C9 C10 121.3(7) . . ?
N1 C3 C4 123.0(6) . . ?
C5 C4 C3 120.5(6) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.41
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         2.128
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.154
_database_code_depnum_ccdc_archive 'CCDC 994629'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Br2 N2 O2 Zn'
_chemical_formula_weight         439.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   21.005(4)
_cell_length_b                   9.1974(9)
_cell_length_c                   16.531(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.679(8)
_cell_angle_gamma                90.00
_cell_volume                     2901.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.4576
_cell_measurement_theta_max      27.4565

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.1800
_exptl_crystal_size_min          0.0800
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.012
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    7.198
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.2482
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Mercury2
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11155
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3320
_reflns_number_gt                2056
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3320
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_refine_ls_shift/su_max          0.062
_refine_ls_shift/su_mean         0.006

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 0.18215(3) 0.07561(7) 0.03674(4) 0.0476(2) Uani 1 1 d . . .
Br2 Br 0.27647(3) 0.19215(7) 0.15473(4) 0.0624(2) Uani 1 1 d . . .
Br1 Br 0.13564(4) -0.11897(7) 0.09225(4) 0.0682(2) Uani 1 1 d . . .
O2 O -0.21229(18) 0.9903(4) -0.4489(2) 0.0519(9) Uani 1 1 d . . .
N1 N 0.1109(2) 0.2438(5) -0.0191(3) 0.0461(10) Uani 1 1 d . . .
C4 C 0.1305(3) 0.3828(7) -0.0048(4) 0.0564(15) Uani 1 1 d . . .
H4A H 0.1766 0.4047 0.0332 0.068 Uiso 1 1 calc R . .
C12 C -0.1619(3) 0.9462(6) -0.3782(4) 0.0503(13) Uani 1 1 d . . .
C8 C -0.1529(3) 0.6542(7) -0.2492(5) 0.077(2) Uani 1 1 d . . .
H8A H -0.1991 0.6279 -0.2840 0.092 Uiso 1 1 calc R . .
N2 N -0.1336(2) 0.7912(5) -0.2460(3) 0.0465(10) Uani 1 1 d . . .
C9 C -0.0200(3) 0.7286(6) -0.1425(4) 0.0519(14) Uani 1 1 d . . .
H9A H 0.0248 0.7585 -0.1043 0.062 Uiso 1 1 calc R . .
O1 O -0.0994(2) 0.9439(6) -0.3630(3) 0.0781(14) Uani 1 1 d . . .
C11 C -0.1846(3) 0.8986(6) -0.3053(3) 0.0496(13) Uani 1 1 d . . .
H11A H -0.1866 0.9825 -0.2709 0.060 Uiso 1 1 calc R . .
H11B H -0.2309 0.8554 -0.3322 0.060 Uiso 1 1 calc R . .
C10 C -0.0688(3) 0.8311(7) -0.1911(4) 0.0589(15) Uani 1 1 d . . .
H10A H -0.0564 0.9289 -0.1857 0.071 Uiso 1 1 calc R . .
C6 C -0.0360(3) 0.5838(6) -0.1493(3) 0.0457(12) Uani 1 1 d . . .
C3 C 0.0839(3) 0.4965(6) -0.0451(4) 0.0589(15) Uani 1 1 d . . .
H3A H 0.0992 0.5922 -0.0331 0.071 Uiso 1 1 calc R . .
C5 C 0.0159(2) 0.4678(6) -0.1022(3) 0.0426(12) Uani 1 1 d . . .
C1 C 0.0452(3) 0.2162(7) -0.0727(5) 0.072(2) Uani 1 1 d . . .
H1A H 0.0303 0.1200 -0.0816 0.086 Uiso 1 1 calc R . .
C2 C -0.0025(3) 0.3249(7) -0.1166(5) 0.0689(19) Uani 1 1 d . . .
H2A H -0.0477 0.2999 -0.1563 0.083 Uiso 1 1 calc R . .
C7 C -0.1044(3) 0.5485(8) -0.2006(5) 0.089(3) Uani 1 1 d . . .
H7A H -0.1188 0.4524 -0.2032 0.107 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0476(4) 0.0530(4) 0.0377(3) -0.0002(3) 0.0134(3) 0.0003(3)
Br2 0.0647(4) 0.0588(4) 0.0445(3) -0.0007(3) 0.0038(3) -0.0025(3)
Br1 0.0831(5) 0.0679(5) 0.0563(4) 0.0012(3) 0.0319(3) -0.0165(3)
O2 0.053(2) 0.059(2) 0.043(2) 0.0101(17) 0.0189(17) 0.0136(18)
N1 0.042(2) 0.048(3) 0.045(2) 0.001(2) 0.014(2) 0.000(2)
C4 0.042(3) 0.061(4) 0.051(3) -0.005(3) 0.005(3) 0.003(3)
C12 0.051(3) 0.053(4) 0.045(3) 0.002(2) 0.018(3) 0.008(3)
C8 0.050(3) 0.059(4) 0.087(5) 0.007(4) -0.006(3) -0.004(3)
N2 0.051(2) 0.053(3) 0.036(2) 0.0071(19) 0.018(2) 0.005(2)
C9 0.043(3) 0.051(4) 0.047(3) 0.006(2) 0.004(2) -0.005(3)
O1 0.054(2) 0.125(4) 0.060(3) 0.034(3) 0.028(2) 0.022(2)
C11 0.052(3) 0.055(4) 0.043(3) 0.004(2) 0.021(3) 0.011(3)
C10 0.059(3) 0.053(4) 0.048(3) -0.001(3) 0.006(3) -0.009(3)
C6 0.040(3) 0.051(3) 0.042(3) 0.004(2) 0.012(2) -0.005(2)
C3 0.051(3) 0.043(3) 0.063(4) -0.006(3) 0.005(3) -0.007(3)
C5 0.040(3) 0.046(3) 0.038(3) 0.004(2) 0.013(2) -0.003(2)
C1 0.047(3) 0.048(4) 0.099(5) 0.007(3) 0.009(3) -0.009(3)
C2 0.037(3) 0.060(4) 0.085(5) 0.008(3) 0.001(3) -0.010(3)
C7 0.061(4) 0.049(4) 0.106(6) 0.007(4) -0.015(4) -0.001(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 1.973(4) 2_544 ?
Zn1 N1 2.082(4) . ?
Zn1 Br2 2.3772(9) . ?
Zn1 Br1 2.3975(9) . ?
O2 C12 1.272(6) . ?
O2 Zn1 1.973(4) 2_564 ?
N1 C1 1.315(7) . ?
N1 C4 1.334(7) . ?
C4 C3 1.396(8) . ?
C12 O1 1.228(6) . ?
C12 C11 1.534(7) . ?
C8 N2 1.318(8) . ?
C8 C7 1.395(9) . ?
N2 C10 1.335(7) . ?
N2 C11 1.486(7) . ?
C9 C6 1.367(7) . ?
C9 C10 1.377(8) . ?
C6 C7 1.368(8) . ?
C6 C5 1.491(7) . ?
C3 C5 1.370(7) . ?
C5 C2 1.362(8) . ?
C1 C2 1.386(8) . ?

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 N1 111.21(17) 2_544 . ?
O2 Zn1 Br2 111.69(10) 2_544 . ?
N1 Zn1 Br2 103.14(12) . . ?
O2 Zn1 Br1 107.00(11) 2_544 . ?
N1 Zn1 Br1 113.06(12) . . ?
Br2 Zn1 Br1 110.84(3) . . ?
C12 O2 Zn1 113.8(3) . 2_564 ?
C1 N1 C4 117.6(5) . . ?
C1 N1 Zn1 120.9(4) . . ?
C4 N1 Zn1 121.5(3) . . ?
N1 C4 C3 122.0(5) . . ?
O1 C12 O2 127.0(5) . . ?
O1 C12 C11 119.3(5) . . ?
O2 C12 C11 113.6(4) . . ?
N2 C8 C7 120.3(6) . . ?
C10 N2 C8 120.0(5) . . ?
C10 N2 C11 121.0(5) . . ?
C8 N2 C11 119.0(5) . . ?
C6 C9 C10 121.4(5) . . ?
N2 C11 C12 109.5(4) . . ?
N2 C10 C9 120.5(5) . . ?
C9 C6 C7 116.1(5) . . ?
C9 C6 C5 123.5(5) . . ?
C7 C6 C5 120.3(5) . . ?
C5 C3 C4 120.4(5) . . ?
C2 C5 C3 116.4(5) . . ?
C2 C5 C6 120.5(4) . . ?
C3 C5 C6 123.2(5) . . ?
N1 C1 C2 122.6(6) . . ?
C5 C2 C1 120.9(5) . . ?
C6 C7 C8 121.2(6) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.071
_refine_diff_density_min         -1.209
_refine_diff_density_rms         0.146

_database_code_depnum_ccdc_archive 'CCDC 994630'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O2 Zn'
_chemical_formula_weight         350.49

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                   21.004(9)
_cell_length_b                   8.861(3)
_cell_length_c                   16.329(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.747(6)
_cell_angle_gamma                90.00
_cell_volume                     2781.9(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3555
_cell_measurement_theta_min      2.5307
_cell_measurement_theta_max      27.5139

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.1500
_exptl_crystal_size_mid          0.1200
_exptl_crystal_size_min          0.0600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    2.147
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8858
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn70
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10667
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3167
_reflns_number_gt                2637
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1538P)²+16.4157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3167
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2416
_refine_ls_wR_factor_gt          0.2273
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.010

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 0.18543(4) 0.07087(8) 0.04252(5) 0.0450(3) Uani 1 1 d . . .
Cl2 Cl 0.14133(8) -0.12171(16) 0.09949(10) 0.0445(4) Uani 1 1 d . . .
Cl3 Cl 0.27425(8) 0.19385(16) 0.15252(9) 0.0449(4) Uani 1 1 d . . .
O1 O -0.2154(2) 0.9845(6) -0.4539(3) 0.0514(11) Uani 1 1 d . . .
C12 C -0.1663(3) 0.9362(7) -0.3834(4) 0.0476(14) Uani 1 1 d . . .
N2 N -0.1377(3) 0.7874(6) -0.2467(3) 0.0433(11) Uani 1 1 d . . .
N1 N 0.1130(3) 0.2386(6) -0.0149(4) 0.0468(12) Uani 1 1 d . . .
C6 C -0.0385(3) 0.5774(7) -0.1483(4) 0.0434(13) Uani 1 1 d . . .
O2 O -0.1056(3) 0.9280(8) -0.3715(4) 0.0793(19) Uani 1 1 d . . .
C11 C -0.1887(3) 0.8939(8) -0.3088(5) 0.0510(15) Uani 1 1 d . . .
H11A H -0.1915 0.9839 -0.2767 0.061 Uiso 1 1 calc R . .
H11B H -0.2343 0.8474 -0.3340 0.061 Uiso 1 1 calc R . .
C5 C 0.0151(3) 0.4621(7) -0.1015(4) 0.0437(13) Uani 1 1 d . . .
C10 C -0.1550(4) 0.6425(9) -0.2472(6) 0.067(2) Uani 1 1 d . . .
H10A H -0.2006 0.6122 -0.2806 0.080 Uiso 1 1 calc R . .
C8 C -0.0731(4) 0.8320(8) -0.1955(5) 0.0544(16) Uani 1 1 d . . .
H8A H -0.0619 0.9339 -0.1939 0.065 Uiso 1 1 calc R . .
C1 C 0.1295(3) 0.3839(8) -0.0072(5) 0.0525(16) Uani 1 1 d . . .
H1A H 0.1753 0.4102 0.0283 0.063 Uiso 1 1 calc R . .
C7 C -0.0225(3) 0.7314(8) -0.1450(5) 0.0541(16) Uani 1 1 d . . .
H7A H 0.0219 0.7655 -0.1090 0.065 Uiso 1 1 calc R . .
C2 C 0.0836(3) 0.4979(8) -0.0482(5) 0.0560(17) Uani 1 1 d . . .
H2A H 0.0982 0.5980 -0.0403 0.067 Uiso 1 1 calc R . .
C9 C -0.1061(4) 0.5374(9) -0.1988(6) 0.072(2) Uani 1 1 d . . .
H9A H -0.1192 0.4369 -0.2004 0.086 Uiso 1 1 calc R . .
C3 C 0.0470(4) 0.2055(8) -0.0644(7) 0.073(2) Uani 1 1 d . . .
H3A H 0.0333 0.1049 -0.0697 0.088 Uiso 1 1 calc R . .
C4 C -0.0023(3) 0.3130(9) -0.1082(7) 0.078(3) Uani 1 1 d . . .
H4A H -0.0478 0.2836 -0.1428 0.093 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0438(5) 0.0439(5) 0.0442(5) 0.0004(3) 0.0144(4) -0.0001(3)
Cl2 0.0537(8) 0.0400(7) 0.0456(8) 0.0050(6) 0.0260(7) -0.0079(6)
Cl3 0.0472(8) 0.0365(7) 0.0357(7) -0.0005(5) 0.0008(6) -0.0018(5)
O1 0.046(2) 0.055(3) 0.051(3) 0.013(2) 0.018(2) 0.009(2)
C12 0.043(3) 0.052(4) 0.047(3) 0.009(3) 0.018(3) 0.013(3)
N2 0.041(2) 0.045(3) 0.041(3) 0.004(2) 0.014(2) 0.004(2)
N1 0.036(2) 0.046(3) 0.057(3) 0.005(2) 0.016(2) 0.001(2)
C6 0.039(3) 0.039(3) 0.045(3) 0.002(2) 0.008(3) -0.003(2)
O2 0.050(3) 0.119(5) 0.074(4) 0.036(3) 0.030(3) 0.026(3)
C11 0.049(3) 0.055(4) 0.051(4) 0.011(3) 0.023(3) 0.014(3)
C5 0.036(3) 0.046(3) 0.045(3) 0.007(3) 0.012(2) -0.004(2)
C10 0.043(3) 0.061(4) 0.075(5) 0.006(4) 0.000(3) -0.008(3)
C8 0.055(4) 0.043(3) 0.055(4) 0.004(3) 0.012(3) -0.004(3)
C1 0.033(3) 0.047(3) 0.063(4) -0.001(3) 0.005(3) -0.004(2)
C7 0.046(3) 0.045(3) 0.058(4) 0.004(3) 0.007(3) -0.005(3)
C2 0.037(3) 0.047(4) 0.071(5) -0.004(3) 0.008(3) -0.009(3)
C9 0.046(4) 0.043(4) 0.101(7) 0.011(4) 0.003(4) -0.008(3)
C3 0.046(4) 0.040(3) 0.109(7) 0.011(4) 0.005(4) -0.004(3)
C4 0.033(3) 0.047(4) 0.117(7) 0.007(4) -0.008(4) -0.008(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.952(4) 2_544 ?
Zn1 N1 2.062(5) . ?
Zn1 Cl3 2.2794(16) . ?
Zn1 Cl2 2.3086(16) . ?
O1 C12 1.270(8) . ?
O1 Zn1 1.952(4) 2_564 ?
C12 O2 1.213(8) . ?
C12 C11 1.518(9) . ?
N2 C8 1.336(8) . ?
N2 C10 1.333(9) . ?
N2 C11 1.480(8) . ?
N1 C1 1.326(8) . ?
N1 C3 1.327(9) . ?
C6 C9 1.371(9) . ?
C6 C7 1.402(9) . ?
C6 C5 1.484(8) . ?
C5 C4 1.363(10) . ?
C5 C2 1.385(8) . ?
C10 C9 1.376(11) . ?
C8 C7 1.378(10) . ?
C1 C2 1.371(9) . ?
C3 C4 1.376(10) . ?

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 N1 110.1(2) 2_544 . ?
O1 Zn1 Cl3 111.47(14) 2_544 . ?
N1 Zn1 Cl3 103.49(16) . . ?
O1 Zn1 Cl2 108.08(15) 2_544 . ?
N1 Zn1 Cl2 111.97(15) . . ?
Cl3 Zn1 Cl2 111.70(7) . . ?
C12 O1 Zn1 114.7(4) . 2_564 ?
O2 C12 O1 125.6(6) . . ?
O2 C12 C11 120.1(6) . . ?
O1 C12 C11 114.2(5) . . ?
C8 N2 C10 119.6(6) . . ?
C8 N2 C11 120.8(6) . . ?
C10 N2 C11 119.4(6) . . ?
C1 N1 C3 116.2(6) . . ?
C1 N1 Zn1 122.7(4) . . ?
C3 N1 Zn1 121.1(5) . . ?
C9 C6 C7 116.7(6) . . ?
C9 C6 C5 121.3(6) . . ?
C7 C6 C5 122.0(6) . . ?
N2 C11 C12 109.6(5) . . ?
C4 C5 C2 116.7(6) . . ?
C4 C5 C6 120.2(5) . . ?
C2 C5 C6 123.1(6) . . ?
N2 C10 C9 120.7(6) . . ?
N2 C8 C7 121.8(6) . . ?
N1 C1 C2 124.3(6) . . ?
C8 C7 C6 119.5(6) . . ?
C5 C2 C1 119.1(6) . . ?
C10 C9 C6 121.6(7) . . ?
N1 C3 C4 123.1(7) . . ?
C5 C4 C3 120.5(6) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         2.124
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.156
_database_code_depnum_ccdc_archive 'CCDC 1021644'
