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

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

data_1x70_ratio290K
_database_code_depnum_ccdc_archive 'CCDC 1469392'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br1.35 Cl0.65 N2 Zn'
_chemical_formula_weight         352.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_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                   10.6574(16)
_cell_length_b                   14.801(2)
_cell_length_c                   7.7136(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.635(3)
_cell_angle_gamma                90
_cell_volume                     1205.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_F_000             681
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    6.608
_shelx_estimated_absorpt_T_min   0.289
_shelx_estimated_absorpt_T_max   0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4753
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8568
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.369
_diffrn_reflns_theta_max         29.697
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1708
_reflns_number_gt                1071
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+2.5821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1708
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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_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 0.0000 0.29891(4) 0.2500 0.0431(2) Uani 1 2 d S T P . .
Br1 Br -0.0118(3) 0.21578(16) -0.0026(4) 0.0624(7) Uani 0.673(5) 1 d . . P A 1
Cl1 Cl -0.0281(15) 0.2173(7) -0.0103(19) 0.064(4) Uani 0.327(5) 1 d . . P A 2
N1 N 0.1208(3) 0.4049(2) 0.2238(4) 0.0427(7) Uani 1 1 d . . . . .
C1 C 0.0676(4) 0.4869(2) 0.2341(5) 0.0421(9) Uani 1 1 d . . . . .
C2 C 0.1347(5) 0.5648(3) 0.2115(6) 0.0636(12) Uani 1 1 d . . . . .
H2 H 0.0976 0.6213 0.2203 0.076 Uiso 1 1 calc R U . . .
C3 C 0.2568(5) 0.5576(4) 0.1759(7) 0.0818(17) Uani 1 1 d . . . . .
H3 H 0.3033 0.6094 0.1600 0.098 Uiso 1 1 calc R U . . .
C4 C 0.3101(5) 0.4749(4) 0.1639(7) 0.0774(15) Uani 1 1 d . . . . .
H4 H 0.3930 0.4696 0.1397 0.093 Uiso 1 1 calc R U . . .
C5 C 0.2394(4) 0.3988(3) 0.1881(5) 0.0596(11) Uani 1 1 d . . . . .
H5 H 0.2755 0.3420 0.1793 0.071 Uiso 1 1 calc R U . . .


_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 N1 2.057(3) 2 ?
Zn1 N1 2.057(3) . ?
Zn1 Br1 2.294(3) 2 ?
Zn1 Br1 2.294(3) . ?
Zn1 Cl1 2.328(13) 2 ?
Zn1 Cl1 2.328(13) . ?
N1 C5 1.332(5) . ?
N1 C1 1.345(4) . ?
C1 C2 1.381(5) . ?
C1 C1 1.493(8) 2 ?
C2 C3 1.369(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(6) . ?
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
N1 Zn1 N1 80.53(17) 2 . ?
N1 Zn1 Br1 106.86(10) 2 2 ?
N1 Zn1 Br1 121.91(12) . 2 ?
N1 Zn1 Br1 121.91(12) 2 . ?
N1 Zn1 Br1 106.86(10) . . ?
Br1 Zn1 Br1 115.13(14) 2 . ?
N1 Zn1 Cl1 108.8(3) 2 2 ?
N1 Zn1 Cl1 118.1(4) . 2 ?
N1 Zn1 Cl1 118.1(4) 2 . ?
N1 Zn1 Cl1 108.8(3) . . ?
Cl1 Zn1 Cl1 117.5(6) 2 . ?
C5 N1 C1 119.5(3) . . ?
C5 N1 Zn1 126.3(3) . . ?
C1 N1 Zn1 114.0(2) . . ?
N1 C1 C2 121.1(4) . . ?
N1 C1 C1 115.7(2) . 2 ?
C2 C1 C1 123.2(3) . 2 ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.0(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.4(5) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?

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
C5 N1 C1 C2 -1.2(6) . . . . ?
Zn1 N1 C1 C2 -177.2(3) . . . . ?
C5 N1 C1 C1 177.1(4) . . . 2 ?
Zn1 N1 C1 C1 1.2(5) . . . 2 ?
N1 C1 C2 C3 0.8(6) . . . . ?
C1 C1 C2 C3 -177.4(4) 2 . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C1 N1 C5 C4 1.0(6) . . . . ?
Zn1 N1 C5 C4 176.4(3) . . . . ?
C3 C4 C5 N1 -0.3(7) . . . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4

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

data_1x80_ratio290K
_database_code_depnum_ccdc_archive 'CCDC 1469393'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br1.51 Cl0.49 N2 Zn'
_chemical_formula_weight         359.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_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                   10.7037(16)
_cell_length_b                   14.806(2)
_cell_length_c                   7.7392(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.673(3)
_cell_angle_gamma                90
_cell_volume                     1215.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.965
_exptl_crystal_F_000             693
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    7.066
_shelx_estimated_absorpt_T_min   0.305
_shelx_estimated_absorpt_T_max   0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4828
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6639
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.362
_diffrn_reflns_theta_max         29.185
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1655
_reflns_number_gt                1302
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+0.6794P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1655
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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_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 0.0000 0.29896(2) 0.2500 0.04382(16) Uani 1 2 d S T P . .
Br1 Br -0.0114(2) 0.21469(12) -0.0032(3) 0.0598(5) Uani 0.756(4) 1 d . . P A 1
Cl1 Cl -0.0418(16) 0.2219(7) -0.014(2) 0.056(3) Uani 0.244(4) 1 d . . P A 2
N1 N 0.12005(18) 0.40500(13) 0.2239(3) 0.0438(5) Uani 1 1 d . . . . .
C1 C 0.0669(2) 0.48690(15) 0.2336(3) 0.0438(5) Uani 1 1 d . . . . .
C2 C 0.1345(3) 0.5650(2) 0.2119(4) 0.0657(8) Uani 1 1 d . . . . .
H2 H 0.0978 0.6214 0.2204 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2565(3) 0.5576(3) 0.1777(5) 0.0832(11) Uani 1 1 d . . . . .
H3 H 0.3032 0.6094 0.1632 0.100 Uiso 1 1 calc R U . . .
C4 C 0.3096(3) 0.4745(3) 0.1649(5) 0.0771(10) Uani 1 1 d . . . . .
H4 H 0.3920 0.4690 0.1402 0.093 Uiso 1 1 calc R U . . .
C5 C 0.2388(3) 0.3988(2) 0.1893(4) 0.0606(7) Uani 1 1 d . . . . .
H5 H 0.2747 0.3420 0.1814 0.073 Uiso 1 1 calc R U . . .


_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 N1 2.0558(19) 2 ?
Zn1 N1 2.0559(19) . ?
Zn1 Br1 2.313(2) . ?
Zn1 Br1 2.313(2) 2 ?
Zn1 Cl1 2.332(15) . ?
Zn1 Cl1 2.332(15) 2 ?
N1 C5 1.337(3) . ?
N1 C1 1.346(3) . ?
C1 C2 1.386(3) . ?
C1 C1 1.487(5) 2 ?
C2 C3 1.371(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
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
N1 Zn1 N1 80.42(11) 2 . ?
N1 Zn1 Br1 122.16(8) 2 . ?
N1 Zn1 Br1 106.96(7) . . ?
N1 Zn1 Br1 106.96(7) 2 2 ?
N1 Zn1 Br1 122.16(8) . 2 ?
Br1 Zn1 Br1 114.69(10) . 2 ?
N1 Zn1 Cl1 114.2(4) 2 . ?
N1 Zn1 Cl1 109.7(3) . . ?
N1 Zn1 Cl1 109.7(3) 2 2 ?
N1 Zn1 Cl1 114.2(4) . 2 ?
Cl1 Zn1 Cl1 121.4(6) . 2 ?
C5 N1 C1 119.5(2) . . ?
C5 N1 Zn1 126.24(19) . . ?
C1 N1 Zn1 114.09(16) . . ?
N1 C1 C2 120.9(3) . . ?
N1 C1 C1 115.68(13) . 2 ?
C2 C1 C1 123.43(18) . 2 ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?

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
C5 N1 C1 C2 -1.4(4) . . . . ?
Zn1 N1 C1 C2 -177.6(2) . . . . ?
C5 N1 C1 C1 177.9(3) . . . 2 ?
Zn1 N1 C1 C1 1.7(3) . . . 2 ?
N1 C1 C2 C3 0.9(4) . . . . ?
C1 C1 C2 C3 -178.3(3) 2 . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C1 N1 C5 C4 0.7(4) . . . . ?
Zn1 N1 C5 C4 176.4(2) . . . . ?
C3 C4 C5 N1 0.4(5) . . . . ?

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4

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

data_1x90_ratio300K
_database_code_depnum_ccdc_archive 'CCDC 1469394'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br1.75 Cl0.25 N2 Zn'
_chemical_formula_weight         370.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_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                   10.755(6)
_cell_length_b                   14.818(8)
_cell_length_c                   7.775(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.568(9)
_cell_angle_gamma                90
_cell_volume                     1228.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.003
_exptl_crystal_F_000             710
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    7.725
_shelx_estimated_absorpt_T_min   0.230
_shelx_estimated_absorpt_T_max   0.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4669
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15529
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.353
_diffrn_reflns_theta_max         29.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1792
_reflns_number_gt                1247
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.4802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1792
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_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 0.0000 0.29909(2) 0.2500 0.04328(17) Uani 1 2 d S T P . .
Br1 Br -0.01260(10) 0.21471(7) -0.00418(15) 0.0601(3) Uani 0.877(4) 1 d . . P A
1
Cl1 Cl -0.0563(13) 0.2252(10) -0.015(2) 0.045(3) Uani 0.123(4) 1 d . . P A 2
N1 N 0.11980(19) 0.40528(13) 0.2246(2) 0.0418(5) Uani 1 1 d . . . . .
C1 C 0.0664(3) 0.48714(16) 0.2341(3) 0.0429(6) Uani 1 1 d . . . . .
C2 C 0.1337(3) 0.5648(2) 0.2130(4) 0.0643(8) Uani 1 1 d . . . . .
H2 H 0.0969 0.6212 0.2214 0.077 Uiso 1 1 calc R U . . .
C3 C 0.2555(4) 0.5579(3) 0.1797(5) 0.0812(11) Uani 1 1 d . . . . .
H3 H 0.3019 0.6097 0.1657 0.097 Uiso 1 1 calc R U . . .
C4 C 0.3084(3) 0.4745(3) 0.1670(4) 0.0756(10) Uani 1 1 d . . . . .
H4 H 0.3904 0.4689 0.1428 0.091 Uiso 1 1 calc R U . . .
C5 C 0.2377(3) 0.3993(2) 0.1908(4) 0.0594(7) Uani 1 1 d . . . . .
H5 H 0.2734 0.3425 0.1831 0.071 Uiso 1 1 calc R U . . .


_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 N1 2.059(2) 2 ?
Zn1 N1 2.059(2) . ?
Zn1 Br1 2.3274(16) 2 ?
Zn1 Br1 2.3274(16) . ?
Zn1 Cl1 2.340(18) . ?
Zn1 Cl1 2.341(18) 2 ?
N1 C5 1.331(3) . ?
N1 C1 1.348(3) . ?
C1 C2 1.381(4) . ?
C1 C1 1.482(5) 2 ?
C2 C3 1.371(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
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
N1 Zn1 N1 80.37(12) 2 . ?
N1 Zn1 Br1 107.23(6) 2 2 ?
N1 Zn1 Br1 121.64(6) . 2 ?
N1 Zn1 Br1 121.64(6) 2 . ?
N1 Zn1 Br1 107.23(6) . . ?
Br1 Zn1 Br1 115.01(7) 2 . ?
N1 Zn1 Cl1 110.4(3) 2 . ?
N1 Zn1 Cl1 111.5(4) . . ?
N1 Zn1 Cl1 111.5(4) 2 2 ?
N1 Zn1 Cl1 110.4(3) . 2 ?
Cl1 Zn1 Cl1 124.2(7) . 2 ?
C5 N1 C1 119.6(2) . . ?
C5 N1 Zn1 126.30(19) . . ?
C1 N1 Zn1 113.94(17) . . ?
N1 C1 C2 120.6(3) . . ?
N1 C1 C1 115.85(14) . 2 ?
C2 C1 C1 123.49(19) . 2 ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?

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
C5 N1 C1 C2 -1.5(4) . . . . ?
Zn1 N1 C1 C2 -177.63(19) . . . . ?
C5 N1 C1 C1 177.9(2) . . . 2 ?
Zn1 N1 C1 C1 1.7(3) . . . 2 ?
N1 C1 C2 C3 1.0(4) . . . . ?
C1 C1 C2 C3 -178.3(3) 2 . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C1 N1 C5 C4 0.8(4) . . . . ?
Zn1 N1 C5 C4 176.4(2) . . . . ?
C3 C4 C5 N1 0.4(5) . . . . ?

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-4

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

data_1x0_100K
_database_code_depnum_ccdc_archive 'CCDC 1469395'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Cl2 N2 Zn'
_chemical_formula_weight         292.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5299(6)
_cell_length_b                   8.7931(7)
_cell_length_c                   9.0498(7)
_cell_angle_alpha                112.8348(19)
_cell_angle_beta                 94.457(2)
_cell_angle_gamma                95.707(2)
_cell_volume                     545.06(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.706
_shelx_estimated_absorpt_T_min   0.614
_shelx_estimated_absorpt_T_max   0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5845
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9415
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.462
_diffrn_reflns_theta_max         31.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3228
_reflns_number_gt                2831
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+0.2188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3228
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0577
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_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 0.26656(2) 0.22541(2) 0.32548(2) 0.01243(6) Uani 1 1 d . . . . .
Cl2 Cl 0.53773(5) 0.32895(5) 0.29830(5) 0.01665(9) Uani 1 1 d . . . . .
Cl3 Cl 0.03340(5) 0.29330(5) 0.21261(5) 0.01723(9) Uani 1 1 d . . . . .
N1 N 0.21992(18) 0.20318(17) 0.53753(16) 0.0122(3) Uani 1 1 d . . . . .
N2 N 0.28753(18) -0.02430(17) 0.25930(16) 0.0124(3) Uani 1 1 d . . . . .
C1 C 0.1723(2) 0.3209(2) 0.6691(2) 0.0151(3) Uani 1 1 d . . . . .
H1 H 0.1591 0.4270 0.6686 0.018 Uiso 1 1 calc R U . . .
C2 C 0.1416(2) 0.2919(2) 0.8061(2) 0.0169(3) Uani 1 1 d . . . . .
H2 H 0.1067 0.3765 0.8975 0.020 Uiso 1 1 calc R U . . .
C3 C 0.1628(2) 0.1372(2) 0.8070(2) 0.0175(3) Uani 1 1 d . . . . .
H3 H 0.1447 0.1154 0.9001 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2109(2) 0.0146(2) 0.67060(19) 0.0150(3) Uani 1 1 d . . . . .
H4 H 0.2254 -0.0921 0.6688 0.018 Uiso 1 1 calc R U . . .
C5 C 0.2373(2) 0.05082(19) 0.53664(19) 0.0112(3) Uani 1 1 d . . . . .
C6 C 0.2806(2) -0.0745(2) 0.38274(18) 0.0116(3) Uani 1 1 d . . . . .
C7 C 0.3099(2) -0.2347(2) 0.3632(2) 0.0146(3) Uani 1 1 d . . . . .
H7 H 0.3051 -0.2686 0.4507 0.018 Uiso 1 1 calc R U . . .
C8 C 0.3462(2) -0.3443(2) 0.2135(2) 0.0164(3) Uani 1 1 d . . . . .
H8 H 0.3662 -0.4543 0.1976 0.020 Uiso 1 1 calc R U . . .
C9 C 0.3530(2) -0.2917(2) 0.0876(2) 0.0164(3) Uani 1 1 d . . . . .
H9 H 0.3775 -0.3646 -0.0156 0.020 Uiso 1 1 calc R U . . .
C10 C 0.3231(2) -0.1301(2) 0.11615(19) 0.0149(3) Uani 1 1 d . . . . .
H10 H 0.3281 -0.0933 0.0306 0.018 Uiso 1 1 calc R U . . .


_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 N1 2.0558(13) . ?
Zn1 N2 2.0658(14) . ?
Zn1 Cl3 2.2103(4) . ?
Zn1 Cl2 2.2228(5) . ?
N1 C1 1.342(2) . ?
N1 C5 1.3560(19) . ?
N2 C10 1.335(2) . ?
N2 C6 1.3538(19) . ?
C1 C2 1.391(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.487(2) . ?
C6 C7 1.392(2) . ?
C7 C8 1.391(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 H10 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
N1 Zn1 N2 80.51(5) . . ?
N1 Zn1 Cl3 112.81(4) . . ?
N2 Zn1 Cl3 118.37(4) . . ?
N1 Zn1 Cl2 120.27(4) . . ?
N2 Zn1 Cl2 102.55(4) . . ?
Cl3 Zn1 Cl2 116.683(17) . . ?
C1 N1 C5 119.44(14) . . ?
C1 N1 Zn1 126.55(11) . . ?
C5 N1 Zn1 113.99(10) . . ?
C10 N2 C6 119.52(14) . . ?
C10 N2 Zn1 126.53(11) . . ?
C6 N2 Zn1 113.62(11) . . ?
N1 C1 C2 121.88(15) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 118.90(16) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.37(15) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.92(15) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.47(15) . . ?
N1 C5 C6 115.71(13) . . ?
C4 C5 C6 122.79(14) . . ?
N2 C6 C7 121.16(15) . . ?
N2 C6 C5 115.69(13) . . ?
C7 C6 C5 123.14(14) . . ?
C8 C7 C6 118.97(14) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 119.46(15) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 118.36(16) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
N2 C10 C9 122.53(15) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?

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
C5 N1 C1 C2 0.6(2) . . . . ?
Zn1 N1 C1 C2 179.13(12) . . . . ?
N1 C1 C2 C3 0.7(2) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C1 N1 C5 C4 -1.5(2) . . . . ?
Zn1 N1 C5 C4 179.83(12) . . . . ?
C1 N1 C5 C6 176.75(14) . . . . ?
Zn1 N1 C5 C6 -1.95(17) . . . . ?
C3 C4 C5 N1 1.0(2) . . . . ?
C3 C4 C5 C6 -177.09(15) . . . . ?
C10 N2 C6 C7 0.0(2) . . . . ?
Zn1 N2 C6 C7 -173.80(12) . . . . ?
C10 N2 C6 C5 -179.07(14) . . . . ?
Zn1 N2 C6 C5 7.13(17) . . . . ?
N1 C5 C6 N2 -3.5(2) . . . . ?
C4 C5 C6 N2 174.67(14) . . . . ?
N1 C5 C6 C7 177.43(14) . . . . ?
C4 C5 C6 C7 -4.4(2) . . . . ?
N2 C6 C7 C8 -0.2(2) . . . . ?
C5 C6 C7 C8 178.77(15) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C6 N2 C10 C9 0.3(2) . . . . ?
Zn1 N2 C10 C9 173.18(12) . . . . ?
C8 C9 C10 N2 -0.3(3) . . . . ?

_refine_diff_density_max         0.542
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-4

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

data_1x10_100K
_database_code_depnum_ccdc_archive 'CCDC 1469396'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br0.19 Cl1.81 N2 Zn'
_chemical_formula_weight         300.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5668(10)
_cell_length_b                   8.8117(11)
_cell_length_c                   9.0830(11)
_cell_angle_alpha                113.0052(18)
_cell_angle_beta                 94.6504(19)
_cell_angle_gamma                95.7870(19)
_cell_volume                     549.79(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_F_000             299
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.313
_shelx_estimated_absorpt_T_min   0.399
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6016
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12004
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.457
_diffrn_reflns_theta_max         30.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3324
_reflns_number_gt                3008
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0209P)²+0.2888P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3324
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0201
_refine_ls_wR_factor_ref         0.0484
_refine_ls_wR_factor_gt          0.0471
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.002
_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_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 0.76769(2) 0.72447(2) 0.82506(2) 0.01263(5) Uani 1 1 d . . . . .
Br2 Br 0.53288(4) 0.79361(4) 0.71173(3) 0.01720(9) Uani 0.1305(15) 1 d . . P A
1
Br3 Br 1.03902(4) 0.82885(4) 0.79828(4) 0.01673(10) Uani 0.0554(14) 1 d . . P A
1
Cl2 Cl 0.53288(4) 0.79361(4) 0.71173(3) 0.01720(9) Uani 0.8695(15) 1 d . . P A
2
Cl3 Cl 1.03902(4) 0.82885(4) 0.79828(4) 0.01673(10) Uani 0.9446(14) 1 d . . P A
2
N2 N 0.72070(15) 0.70240(14) 1.03638(14) 0.0124(2) Uani 1 1 d . . . . .
N8 N 0.78865(15) 0.47506(14) 0.75898(13) 0.0124(2) Uani 1 1 d . . . . .
C1 C 0.73763(17) 0.55006(17) 1.03512(16) 0.0118(2) Uani 1 1 d . . . . .
C3 C 0.67248(18) 0.81991(18) 1.16769(17) 0.0155(3) Uani 1 1 d . . . . .
H3 H 0.6594 0.9259 1.1674 0.019 Uiso 1 1 calc R U . . .
C4 C 0.64118(19) 0.79100(19) 1.30389(17) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.6059 0.8754 1.3949 0.021 Uiso 1 1 calc R U . . .
C5 C 0.66238(19) 0.63638(19) 1.30448(17) 0.0175(3) Uani 1 1 d . . . . .
H5 H 0.6438 0.6145 1.3969 0.021 Uiso 1 1 calc R U . . .
C6 C 0.71099(19) 0.51398(18) 1.16865(16) 0.0156(3) Uani 1 1 d . . . . .
H6 H 0.7258 0.4075 1.1670 0.019 Uiso 1 1 calc R U . . .
C7 C 0.78139(17) 0.42448(16) 0.88161(15) 0.0116(2) Uani 1 1 d . . . . .
C9 C 0.82465(19) 0.36897(18) 0.61552(16) 0.0153(3) Uani 1 1 d . . . . .
H9 H 0.8301 0.4056 0.5303 0.018 Uiso 1 1 calc R U . . .
C10 C 0.8542(2) 0.20769(18) 0.58743(17) 0.0170(3) Uani 1 1 d . . . . .
H10 H 0.8786 0.1347 0.4846 0.020 Uiso 1 1 calc R U . . .
C11 C 0.84733(19) 0.15510(17) 0.71292(17) 0.0165(3) Uani 1 1 d . . . . .
H11 H 0.8674 0.0454 0.6970 0.020 Uiso 1 1 calc R U . . .
C12 C 0.81072(19) 0.26462(17) 0.86191(17) 0.0148(2) Uani 1 1 d . . . . .
H12 H 0.8058 0.2308 0.9490 0.018 Uiso 1 1 calc R U . . .


_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 N2 2.0584(11) . ?
Zn1 N8 2.0664(12) . ?
Zn1 Br3 2.2350(4) . ?
Zn1 Br2 2.2360(4) . ?
N2 C3 1.3451(18) . ?
N2 C1 1.3570(17) . ?
N8 C9 1.3427(18) . ?
N8 C7 1.3548(16) . ?
C1 C6 1.3932(18) . ?
C1 C7 1.4904(19) . ?
C3 C4 1.3903(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.3921(18) . ?
C9 C10 1.3874(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3908(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 H12 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
N2 Zn1 N8 80.47(4) . . ?
N2 Zn1 Br3 120.53(3) . . ?
N8 Zn1 Br3 102.50(3) . . ?
N2 Zn1 Br2 112.54(3) . . ?
N8 Zn1 Br2 118.73(3) . . ?
Br3 Zn1 Br2 116.556(15) . . ?
C3 N2 C1 119.38(12) . . ?
C3 N2 Zn1 126.65(9) . . ?
C1 N2 Zn1 113.95(9) . . ?
C9 N8 C7 119.40(11) . . ?
C9 N8 Zn1 126.41(9) . . ?
C7 N8 Zn1 113.86(9) . . ?
N2 C1 C6 121.44(12) . . ?
N2 C1 C7 115.83(11) . . ?
C6 C1 C7 122.71(12) . . ?
N2 C3 C4 122.00(13) . . ?
N2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 118.79(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 119.48(13) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 118.89(13) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N8 C7 C12 121.30(12) . . ?
N8 C7 C1 115.42(11) . . ?
C12 C7 C1 123.28(12) . . ?
N8 C9 C10 122.27(12) . . ?
N8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C9 C10 C11 118.62(13) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 119.37(13) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C7 119.05(12) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?

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
C3 N2 C1 C6 -1.80(19) . . . . ?
Zn1 N2 C1 C6 179.79(10) . . . . ?
C3 N2 C1 C7 176.68(12) . . . . ?
Zn1 N2 C1 C7 -1.73(14) . . . . ?
C1 N2 C3 C4 0.8(2) . . . . ?
Zn1 N2 C3 C4 178.95(10) . . . . ?
N2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
N2 C1 C6 C5 1.3(2) . . . . ?
C7 C1 C6 C5 -177.02(12) . . . . ?
C9 N8 C7 C12 0.07(19) . . . . ?
Zn1 N8 C7 C12 -173.74(10) . . . . ?
C9 N8 C7 C1 -179.03(12) . . . . ?
Zn1 N8 C7 C1 7.16(14) . . . . ?
N2 C1 C7 N8 -3.67(17) . . . . ?
C6 C1 C7 N8 174.79(12) . . . . ?
N2 C1 C7 C12 177.25(12) . . . . ?
C6 C1 C7 C12 -4.3(2) . . . . ?
C7 N8 C9 C10 0.3(2) . . . . ?
Zn1 N8 C9 C10 173.26(11) . . . . ?
N8 C9 C10 C11 -0.4(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C7 0.1(2) . . . . ?
N8 C7 C12 C11 -0.3(2) . . . . ?
C1 C7 C12 C11 178.74(13) . . . . ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4

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

data_1x30_100K
_database_code_depnum_ccdc_archive 'CCDC 1469397'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br0.62 Cl1.38 N2 Zn'
_chemical_formula_weight         320.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6518(5)
_cell_length_b                   8.8233(6)
_cell_length_c                   9.1333(6)
_cell_angle_alpha                113.5232(13)
_cell_angle_beta                 95.1819(15)
_cell_angle_gamma                95.9954(15)
_cell_volume                     556.37(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.910
_exptl_crystal_F_000             314
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.729
_shelx_estimated_absorpt_T_min   0.351
_shelx_estimated_absorpt_T_max   0.649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5757
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7827
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.458
_diffrn_reflns_theta_max         30.625
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3406
_reflns_number_gt                3098
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0224P)²+0.2037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3406
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0175
_refine_ls_wR_factor_ref         0.0448
_refine_ls_wR_factor_gt          0.0436
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_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_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 0.77052(2) 0.22246(2) 0.32426(2) 0.01377(5) Uani 1 1 d . . . . .
Br2 Br 0.53297(2) 0.29300(2) 0.20930(2) 0.01759(6) Uani 0.4329(14) 1 d . . P A
1
Br3 Br 1.04210(3) 0.32870(3) 0.29901(3) 0.01699(8) Uani 0.1862(14) 1 d . . P A
1
Cl2 Cl 0.53297(2) 0.29300(2) 0.20930(2) 0.01759(6) Uani 0.5671(14) 1 d . . P A
2
Cl3 Cl 1.04210(3) 0.32870(3) 0.29901(3) 0.01699(8) Uani 0.8138(14) 1 d . . P A
2
N1 N 0.72246(14) 0.20001(13) 0.53305(13) 0.01363(19) Uani 1 1 d . . . . .
N2 N 0.79150(14) -0.02701(13) 0.25742(13) 0.01348(19) Uani 1 1 d . . . . .
C1 C 0.67271(17) 0.31707(16) 0.66299(16) 0.0166(2) Uani 1 1 d . . . . .
H1 H 0.6594 0.4229 0.6628 0.020 Uiso 1 1 calc R U . . .
C2 C 0.64005(17) 0.28813(17) 0.79778(16) 0.0182(2) Uani 1 1 d . . . . .
H2 H 0.6043 0.3725 0.8881 0.022 Uiso 1 1 calc R U . . .
C3 C 0.66061(18) 0.13383(18) 0.79780(16) 0.0192(3) Uani 1 1 d . . . . .
H3 H 0.6409 0.1119 0.8892 0.023 Uiso 1 1 calc R U . . .
C4 C 0.71021(17) 0.01134(16) 0.66311(15) 0.0164(2) Uani 1 1 d . . . . .
H4 H 0.7243 -0.0952 0.6609 0.020 Uiso 1 1 calc R U . . .
C5 C 0.73878(15) 0.04807(15) 0.53141(15) 0.0128(2) Uani 1 1 d . . . . .
C6 C 0.78350(15) -0.07764(15) 0.37866(14) 0.0123(2) Uani 1 1 d . . . . .
C7 C 0.81213(17) -0.23726(16) 0.35874(16) 0.0160(2) Uani 1 1 d . . . . .
H7 H 0.8059 -0.2711 0.4449 0.019 Uiso 1 1 calc R U . . .
C8 C 0.85005(18) -0.34671(16) 0.21026(16) 0.0179(2) Uani 1 1 d . . . . .
H8 H 0.8699 -0.4565 0.1939 0.021 Uiso 1 1 calc R U . . .
C9 C 0.85861(18) -0.29391(16) 0.08650(16) 0.0184(2) Uani 1 1 d . . . . .
H9 H 0.8843 -0.3666 -0.0157 0.022 Uiso 1 1 calc R U . . .
C10 C 0.82881(17) -0.13267(16) 0.11516(15) 0.0165(2) Uani 1 1 d . . . . .
H10 H 0.8351 -0.0959 0.0309 0.020 Uiso 1 1 calc R U . . .


_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 N1 2.0552(10) . ?
Zn1 N2 2.0646(11) . ?
Zn1 Br3 2.2589(3) . ?
Zn1 Br2 2.2818(3) . ?
N1 C1 1.3437(16) . ?
N1 C5 1.3537(16) . ?
N2 C10 1.3396(16) . ?
N2 C6 1.3531(15) . ?
C1 C2 1.3915(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3868(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3907(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3941(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.4913(17) . ?
C6 C7 1.3899(17) . ?
C7 C8 1.3929(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3879(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3877(18) . ?
C9 H9 0.9500 . ?
C10 H10 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
N1 Zn1 N2 80.36(4) . . ?
N1 Zn1 Br3 121.24(3) . . ?
N2 Zn1 Br3 102.17(3) . . ?
N1 Zn1 Br2 111.90(3) . . ?
N2 Zn1 Br2 119.29(3) . . ?
Br3 Zn1 Br2 116.496(10) . . ?
C1 N1 C5 119.27(11) . . ?
C1 N1 Zn1 126.51(9) . . ?
C5 N1 Zn1 114.18(8) . . ?
C10 N2 C6 119.33(11) . . ?
C10 N2 Zn1 126.32(8) . . ?
C6 N2 Zn1 113.98(8) . . ?
N1 C1 C2 122.04(12) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.76(12) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.57(12) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 118.67(12) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.66(11) . . ?
N1 C5 C6 115.72(10) . . ?
C4 C5 C6 122.59(11) . . ?
N2 C6 C7 121.50(11) . . ?
N2 C6 C5 115.29(10) . . ?
C7 C6 C5 123.20(11) . . ?
C6 C7 C8 118.86(11) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 119.39(12) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 118.59(12) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
N2 C10 C9 122.34(12) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?

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
C5 N1 C1 C2 1.09(19) . . . . ?
Zn1 N1 C1 C2 178.73(9) . . . . ?
N1 C1 C2 C3 0.36(19) . . . . ?
C1 C2 C3 C4 -1.04(19) . . . . ?
C2 C3 C4 C5 0.30(19) . . . . ?
C1 N1 C5 C4 -1.87(18) . . . . ?
Zn1 N1 C5 C4 -179.79(9) . . . . ?
C1 N1 C5 C6 176.33(11) . . . . ?
Zn1 N1 C5 C6 -1.58(13) . . . . ?
C3 C4 C5 N1 1.18(19) . . . . ?
C3 C4 C5 C6 -176.90(12) . . . . ?
C10 N2 C6 C7 -0.37(18) . . . . ?
Zn1 N2 C6 C7 -173.87(9) . . . . ?
C10 N2 C6 C5 -179.22(11) . . . . ?
Zn1 N2 C6 C5 7.28(13) . . . . ?
N1 C5 C6 N2 -3.85(16) . . . . ?
C4 C5 C6 N2 174.34(11) . . . . ?
N1 C5 C6 C7 177.32(11) . . . . ?
C4 C5 C6 C7 -4.49(19) . . . . ?
N2 C6 C7 C8 0.08(19) . . . . ?
C5 C6 C7 C8 178.84(12) . . . . ?
C6 C7 C8 C9 0.11(19) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C6 N2 C10 C9 0.48(19) . . . . ?
Zn1 N2 C10 C9 173.09(10) . . . . ?
C8 C9 C10 N2 -0.3(2) . . . . ?

_refine_diff_density_max         0.515
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-4

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

data_1x50_100K
_database_code_depnum_ccdc_archive 'CCDC 1469398'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br0.88 Cl1.12 N2 Zn'
_chemical_formula_weight         331.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6883(8)
_cell_length_b                   8.8529(9)
_cell_length_c                   9.1701(9)
_cell_angle_alpha                113.6995(13)
_cell_angle_beta                 95.3265(14)
_cell_angle_gamma                95.9991(14)
_cell_volume                     562.12(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    5.546
_shelx_estimated_absorpt_T_min   0.296
_shelx_estimated_absorpt_T_max   0.490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5621
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11998
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.453
_diffrn_reflns_theta_max         29.647
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3162
_reflns_number_gt                2907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²+0.1402P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3162
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0175
_refine_ls_wR_factor_ref         0.0450
_refine_ls_wR_factor_gt          0.0441
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_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 0.77002(2) 0.72075(2) 0.82374(2) 0.01478(5) Uani 1 1 d . . . . .
Br2 Br 0.53187(2) 0.79153(2) 0.70859(2) 0.01866(7) Uani 0.5457(15) 1 d . . P A
1
Br3 Br 1.04276(3) 0.82752(3) 0.79767(3) 0.01788(8) Uani 0.3351(15) 1 d . . P A
1
Cl2 Cl 0.53187(2) 0.79153(2) 0.70859(2) 0.01866(7) Uani 0.4543(15) 1 d . . P A
2
Cl3 Cl 1.04276(3) 0.82752(3) 0.79767(3) 0.01788(8) Uani 0.6649(15) 1 d . . P A
2
N2 N 0.72232(14) 0.69934(14) 1.03222(13) 0.0144(2) Uani 1 1 d . . . . .
N8 N 0.79129(14) 0.47209(14) 0.75772(13) 0.0144(2) Uani 1 1 d . . . . .
C1 C 0.73841(16) 0.54803(16) 1.03073(16) 0.0135(2) Uani 1 1 d . . . . .
C3 C 0.67236(17) 0.81652(17) 1.16146(17) 0.0178(3) Uani 1 1 d . . . . .
H3 H 0.6587 0.9217 1.1609 0.021 Uiso 1 1 calc R U . . .
C4 C 0.64005(18) 0.78838(19) 1.29582(17) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.6044 0.8728 1.3857 0.024 Uiso 1 1 calc R U . . .
C5 C 0.66072(18) 0.63495(19) 1.29631(17) 0.0208(3) Uani 1 1 d . . . . .
H5 H 0.6412 0.6137 1.3876 0.025 Uiso 1 1 calc R U . . .
C6 C 0.71027(17) 0.51222(18) 1.16217(17) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.7246 0.4062 1.1603 0.022 Uiso 1 1 calc R U . . .
C7 C 0.78328(16) 0.42240(16) 0.87882(15) 0.0134(2) Uani 1 1 d . . . . .
C9 C 0.82928(18) 0.36611(17) 0.61596(16) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.8361 0.4024 0.5319 0.021 Uiso 1 1 calc R U . . .
C10 C 0.85891(19) 0.20567(18) 0.58789(17) 0.0195(3) Uani 1 1 d . . . . .
H10 H 0.8848 0.1327 0.4863 0.023 Uiso 1 1 calc R U . . .
C11 C 0.84992(19) 0.15390(17) 0.71159(18) 0.0196(3) Uani 1 1 d . . . . .
H11 H 0.8696 0.0445 0.6956 0.024 Uiso 1 1 calc R U . . .
C12 C 0.81188(18) 0.26334(17) 0.85901(17) 0.0176(3) Uani 1 1 d . . . . .
H12 H 0.8055 0.2299 0.9449 0.021 Uiso 1 1 calc R U . . .


_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 N2 2.0573(11) . ?
Zn1 N8 2.0643(11) . ?
Zn1 Br3 2.2821(3) . ?
Zn1 Br2 2.2963(3) . ?
N2 C3 1.3445(17) . ?
N2 C1 1.3528(17) . ?
N8 C9 1.3427(17) . ?
N8 C7 1.3528(16) . ?
C1 C6 1.3934(18) . ?
C1 C7 1.4902(18) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.3895(18) . ?
C9 C10 1.3858(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 H12 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
N2 Zn1 N8 80.31(4) . . ?
N2 Zn1 Br3 121.49(3) . . ?
N8 Zn1 Br3 102.10(3) . . ?
N2 Zn1 Br2 111.76(3) . . ?
N8 Zn1 Br2 119.58(3) . . ?
Br3 Zn1 Br2 116.337(11) . . ?
C3 N2 C1 119.33(12) . . ?
C3 N2 Zn1 126.46(9) . . ?
C1 N2 Zn1 114.16(9) . . ?
C9 N8 C7 119.34(11) . . ?
C9 N8 Zn1 126.30(9) . . ?
C7 N8 Zn1 113.97(9) . . ?
N2 C1 C6 121.63(12) . . ?
N2 C1 C7 115.71(11) . . ?
C6 C1 C7 122.65(12) . . ?
N2 C3 C4 121.99(13) . . ?
N2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 118.81(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 119.55(13) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 118.66(13) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
N8 C7 C12 121.35(12) . . ?
N8 C7 C1 115.37(11) . . ?
C12 C7 C1 123.27(12) . . ?
N8 C9 C10 122.32(13) . . ?
N8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C11 118.52(13) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C10 C11 C12 119.48(12) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 119.00(13) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?

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
C3 N2 C1 C6 -2.20(19) . . . . ?
Zn1 N2 C1 C6 -179.87(10) . . . . ?
C3 N2 C1 C7 176.31(11) . . . . ?
Zn1 N2 C1 C7 -1.36(14) . . . . ?
C1 N2 C3 C4 1.4(2) . . . . ?
Zn1 N2 C3 C4 178.73(10) . . . . ?
N2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
N2 C1 C6 C5 1.4(2) . . . . ?
C7 C1 C6 C5 -177.00(12) . . . . ?
C9 N8 C7 C12 -0.64(19) . . . . ?
Zn1 N8 C7 C12 -173.94(10) . . . . ?
C9 N8 C7 C1 -179.38(11) . . . . ?
Zn1 N8 C7 C1 7.32(14) . . . . ?
N2 C1 C7 N8 -4.02(17) . . . . ?
C6 C1 C7 N8 174.47(11) . . . . ?
N2 C1 C7 C12 177.26(12) . . . . ?
C6 C1 C7 C12 -4.2(2) . . . . ?
C7 N8 C9 C10 0.8(2) . . . . ?
Zn1 N8 C9 C10 173.16(10) . . . . ?
N8 C9 C10 C11 -0.4(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
N8 C7 C12 C11 0.2(2) . . . . ?
C1 C7 C12 C11 178.83(12) . . . . ?
C10 C11 C12 C7 0.1(2) . . . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4

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

data_1x70_100K_twin
_database_code_depnum_ccdc_archive 'CCDC 1469399'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br1.37 Cl0.64 N2 Zn'
_chemical_formula_weight         353.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7335(13)
_cell_length_b                   8.9213(15)
_cell_length_c                   9.2304(16)
_cell_angle_alpha                114.064(4)
_cell_angle_beta                 95.245(4)
_cell_angle_gamma                96.005(4)
_cell_volume                     571.95(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_F_000             341
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    7.028
_shelx_estimated_absorpt_T_min   0.320
_shelx_estimated_absorpt_T_max   0.603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.547137
_exptl_absorpt_correction_T_max  0.746069
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3448
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         30.570
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3448
_reflns_number_gt                2545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3448
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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_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 0.76818(6) 0.71752(6) 0.82290(6) 0.01466(15) Uani 1 1 d . . . . .
Br2 Br 0.52958(7) 0.78843(7) 0.70773(7) 0.01849(17) Uani 0.727(4) 1 d . . P A 1
Br3 Br 1.04331(7) 0.82505(7) 0.79527(7) 0.01696(18) Uani 0.638(4) 1 d . . P A 1
Cl2 Cl 0.52958(7) 0.78843(7) 0.70773(7) 0.01849(17) Uani 0.273(4) 1 d . . P A 2
Cl3 Cl 1.04331(7) 0.82505(7) 0.79527(7) 0.01696(18) Uani 0.362(4) 1 d . . P A 2
N2 N 0.7217(4) 0.6984(4) 1.0304(4) 0.0140(7) Uani 1 1 d . . . . .
N8 N 0.7904(4) 0.4703(4) 0.7590(5) 0.0145(7) Uani 1 1 d . . . . .
C1 C 0.7375(5) 0.5495(5) 1.0305(5) 0.0132(9) Uani 1 1 d . . . . .
C3 C 0.6721(5) 0.8164(6) 1.1597(6) 0.0181(9) Uani 1 1 d . . . . .
H3 H 0.6588 0.9208 1.1590 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6403(6) 0.7901(6) 1.2924(6) 0.0197(10) Uani 1 1 d . . . . .
H4 H 0.6044 0.8750 1.3812 0.024 Uiso 1 1 calc R U . . .
C5 C 0.6608(6) 0.6386(6) 1.2956(6) 0.0206(10) Uani 1 1 d . . . . .
H5 H 0.6413 0.6192 1.3871 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7110(6) 0.5151(6) 1.1614(5) 0.0174(9) Uani 1 1 d . . . . .
H6 H 0.7264 0.4103 1.1600 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7822(6) 0.4226(5) 0.8790(5) 0.0137(9) Uani 1 1 d . . . . .
C9 C 0.8292(5) 0.3643(6) 0.6179(5) 0.0177(9) Uani 1 1 d . . . . .
H9 H 0.8369 0.3993 0.5341 0.021 Uiso 1 1 calc R U . . .
C10 C 0.8581(6) 0.2055(6) 0.5917(6) 0.0203(10) Uani 1 1 d . . . . .
H10 H 0.8839 0.1319 0.4906 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8490(6) 0.1551(6) 0.7149(6) 0.0207(10) Uani 1 1 d . . . . .
H11 H 0.8691 0.0467 0.6992 0.025 Uiso 1 1 calc R U . . .
C12 C 0.8105(6) 0.2634(5) 0.8604(6) 0.0173(9) Uani 1 1 d . . . . .
H12 H 0.8034 0.2310 0.9460 0.021 Uiso 1 1 calc R U . . .


_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 N2 2.051(4) . ?
Zn1 N8 2.068(4) . ?
Zn1 Br2 2.3172(8) . ?
Zn1 Br3 2.3204(8) . ?
N2 C1 1.347(5) . ?
N2 C3 1.350(5) . ?
N8 C7 1.343(6) . ?
N8 C9 1.344(5) . ?
C1 C6 1.390(6) . ?
C1 C7 1.495(6) . ?
C3 C4 1.376(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.402(6) . ?
C9 C10 1.383(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(7) . ?
C11 H11 0.9500 . ?
C12 H12 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
N2 Zn1 N8 80.00(15) . . ?
N2 Zn1 Br2 111.86(10) . . ?
N8 Zn1 Br2 120.18(10) . . ?
N2 Zn1 Br3 121.56(10) . . ?
N8 Zn1 Br3 102.09(10) . . ?
Br2 Zn1 Br3 116.01(3) . . ?
C1 N2 C3 118.9(4) . . ?
C1 N2 Zn1 114.6(3) . . ?
C3 N2 Zn1 126.4(3) . . ?
C7 N8 C9 119.5(4) . . ?
C7 N8 Zn1 114.2(3) . . ?
C9 N8 Zn1 125.9(3) . . ?
N2 C1 C6 122.3(4) . . ?
N2 C1 C7 115.5(4) . . ?
C6 C1 C7 122.2(4) . . ?
N2 C3 C4 122.0(4) . . ?
N2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 118.7(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 118.5(4) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N8 C7 C12 121.7(4) . . ?
N8 C7 C1 115.2(4) . . ?
C12 C7 C1 123.1(4) . . ?
N8 C9 C10 121.7(5) . . ?
N8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C11 119.1(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 118.4(4) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?

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
C3 N2 C1 C6 -2.5(6) . . . . ?
Zn1 N2 C1 C6 179.9(3) . . . . ?
C3 N2 C1 C7 176.4(4) . . . . ?
Zn1 N2 C1 C7 -1.3(5) . . . . ?
C1 N2 C3 C4 1.1(6) . . . . ?
Zn1 N2 C3 C4 178.5(3) . . . . ?
N2 C3 C4 C5 0.6(7) . . . . ?
C3 C4 C5 C6 -1.1(7) . . . . ?
N2 C1 C6 C5 2.0(7) . . . . ?
C7 C1 C6 C5 -176.8(4) . . . . ?
C4 C5 C6 C1 -0.2(7) . . . . ?
C9 N8 C7 C12 -1.0(7) . . . . ?
Zn1 N8 C7 C12 -174.3(3) . . . . ?
C9 N8 C7 C1 -179.8(4) . . . . ?
Zn1 N8 C7 C1 6.9(5) . . . . ?
N2 C1 C7 N8 -3.8(6) . . . . ?
C6 C1 C7 N8 175.1(4) . . . . ?
N2 C1 C7 C12 177.4(4) . . . . ?
C6 C1 C7 C12 -3.7(7) . . . . ?
C7 N8 C9 C10 1.1(6) . . . . ?
Zn1 N8 C9 C10 173.6(3) . . . . ?
N8 C9 C10 C11 -0.8(7) . . . . ?
C9 C10 C11 C12 0.3(7) . . . . ?
C10 C11 C12 C7 -0.2(7) . . . . ?
N8 C7 C12 C11 0.5(7) . . . . ?
C1 C7 C12 C11 179.2(4) . . . . ?

_refine_diff_density_max         1.321
_refine_diff_density_min         -1.139
_refine_diff_density_rms         0.182

_shelxl_version_number           2013-4

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

data_1x90_100K
_database_code_depnum_ccdc_archive 'CCDC 1469400'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br1.71 Cl0.29 N2 Zn'
_chemical_formula_weight         368.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.785(4)
_cell_length_b                   8.976(5)
_cell_length_c                   9.255(5)
_cell_angle_alpha                114.285(7)
_cell_angle_beta                 95.568(7)
_cell_angle_gamma                95.950(8)
_cell_volume                     579.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.112
_exptl_crystal_F_000             354
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    8.052
_shelx_estimated_absorpt_T_min   0.220
_shelx_estimated_absorpt_T_max   0.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5000
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7501
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         30.186
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3114
_reflns_number_gt                2388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0211P)²+18.0428P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3114
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1482
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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_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 0.76751(14) 0.71514(15) 0.82256(14) 0.0175(3) Uani 1 1 d . . . . .
Br2 Br 0.52808(13) 0.78609(15) 0.70712(13) 0.0212(3) Uani 0.856(11) 1 d . . P A
1
Br3 Br 1.04334(12) 0.82338(14) 0.79433(13) 0.0192(3) Uani 0.855(11) 1 d . . P A
1
Cl2 Cl 0.52808(13) 0.78609(15) 0.70712(13) 0.0212(3) Uani 0.144(11) 1 d . . P A
2
Cl3 Cl 1.04334(12) 0.82338(14) 0.79433(13) 0.0192(3) Uani 0.145(11) 1 d . . P A
2
N2 N 0.7198(9) 0.6990(10) 1.0305(10) 0.0166(16) Uani 1 1 d . . . . .
N8 N 0.7910(9) 0.4688(11) 0.7592(10) 0.0173(16) Uani 1 1 d . . . . .
C1 C 0.7370(11) 0.5472(12) 1.0285(11) 0.0157(18) Uani 1 1 d . . . . .
C3 C 0.6718(11) 0.8152(13) 1.1571(12) 0.021(2) Uani 1 1 d . . . . .
H3 H 0.6589 0.9188 1.1561 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6398(12) 0.7899(14) 1.2909(12) 0.024(2) Uani 1 1 d . . . . .
H4 H 0.6046 0.8746 1.3798 0.028 Uiso 1 1 calc R U . . .
C5 C 0.6603(13) 0.6389(14) 1.2924(12) 0.024(2) Uani 1 1 d . . . . .
H5 H 0.6404 0.6193 1.3832 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7101(12) 0.5168(14) 1.1604(12) 0.021(2) Uani 1 1 d . . . . .
H6 H 0.7255 0.4131 1.1603 0.025 Uiso 1 1 calc R U . . .
C7 C 0.7817(11) 0.4220(12) 0.8784(11) 0.0152(17) Uani 1 1 d . . . . .
C9 C 0.8280(12) 0.3624(13) 0.6212(12) 0.021(2) Uani 1 1 d . . . . .
H9 H 0.8334 0.3965 0.5371 0.026 Uiso 1 1 calc R U . . .
C10 C 0.8590(13) 0.2048(13) 0.5922(13) 0.022(2) Uani 1 1 d . . . . .
H10 H 0.8869 0.1329 0.4917 0.027 Uiso 1 1 calc R U . . .
C11 C 0.8480(12) 0.1549(13) 0.7151(13) 0.023(2) Uani 1 1 d . . . . .
H11 H 0.8656 0.0464 0.6992 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8114(12) 0.2644(13) 0.8599(12) 0.021(2) Uani 1 1 d . . . . .
H12 H 0.8064 0.2335 0.9462 0.025 Uiso 1 1 calc R U . . .


_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 N2 2.054(8) . ?
Zn1 N8 2.075(8) . ?
Zn1 Br2 2.3326(16) . ?
Zn1 Br3 2.3470(18) . ?
N2 C3 1.327(13) . ?
N2 C1 1.376(12) . ?
N8 C9 1.323(13) . ?
N8 C7 1.338(11) . ?
C1 C6 1.386(13) . ?
C1 C7 1.485(13) . ?
C3 C4 1.387(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(15) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.400(13) . ?
C9 C10 1.379(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(15) . ?
C11 H11 0.9500 . ?
C12 H12 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
N2 Zn1 N8 80.5(3) . . ?
N2 Zn1 Br2 111.0(2) . . ?
N8 Zn1 Br2 120.7(2) . . ?
N2 Zn1 Br3 122.2(2) . . ?
N8 Zn1 Br3 101.9(2) . . ?
Br2 Zn1 Br3 115.86(7) . . ?
C3 N2 C1 119.9(8) . . ?
C3 N2 Zn1 126.9(7) . . ?
C1 N2 Zn1 113.2(6) . . ?
C9 N8 C7 118.7(9) . . ?
C9 N8 Zn1 126.8(7) . . ?
C7 N8 Zn1 114.2(7) . . ?
N2 C1 C6 120.3(9) . . ?
N2 C1 C7 116.1(8) . . ?
C6 C1 C7 123.5(9) . . ?
N2 C3 C4 122.1(10) . . ?
N2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 118.8(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 119.5(9) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 119.4(10) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N8 C7 C12 121.4(9) . . ?
N8 C7 C1 115.5(8) . . ?
C12 C7 C1 123.1(8) . . ?
N8 C9 C10 123.9(9) . . ?
N8 C9 H9 118.0 . . ?
C10 C9 H9 118.0 . . ?
C9 C10 C11 117.6(10) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 H10 121.2 . . ?
C12 C11 C10 119.3(9) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C7 119.1(9) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?

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
C3 N2 C1 C6 -2.1(13) . . . . ?
Zn1 N2 C1 C6 179.6(7) . . . . ?
C3 N2 C1 C7 176.8(8) . . . . ?
Zn1 N2 C1 C7 -1.5(9) . . . . ?
C1 N2 C3 C4 0.8(14) . . . . ?
Zn1 N2 C3 C4 178.8(7) . . . . ?
N2 C3 C4 C5 0.6(15) . . . . ?
C3 C4 C5 C6 -0.7(15) . . . . ?
N2 C1 C6 C5 2.0(14) . . . . ?
C7 C1 C6 C5 -176.8(8) . . . . ?
C4 C5 C6 C1 -0.6(14) . . . . ?
C9 N8 C7 C12 0.5(13) . . . . ?
Zn1 N8 C7 C12 -174.0(7) . . . . ?
C9 N8 C7 C1 -179.1(8) . . . . ?
Zn1 N8 C7 C1 6.4(9) . . . . ?
N2 C1 C7 N8 -3.4(11) . . . . ?
C6 C1 C7 N8 175.5(8) . . . . ?
N2 C1 C7 C12 177.1(8) . . . . ?
C6 C1 C7 C12 -4.1(13) . . . . ?
C7 N8 C9 C10 -0.5(14) . . . . ?
Zn1 N8 C9 C10 173.2(7) . . . . ?
N8 C9 C10 C11 1.0(15) . . . . ?
C9 C10 C11 C12 -1.6(15) . . . . ?
C10 C11 C12 C7 1.6(14) . . . . ?
N8 C7 C12 C11 -1.1(14) . . . . ?
C1 C7 C12 C11 178.4(8) . . . . ?

_refine_diff_density_max         1.422
_refine_diff_density_min         -1.651
_refine_diff_density_rms         0.234

_shelxl_version_number           2013-4

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

data_1x100_100K
_database_code_depnum_ccdc_archive 'CCDC 1469401'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br2 N2 Zn'
_chemical_formula_weight         381.37

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.882(6)
_cell_length_b                   9.046(7)
_cell_length_c                   9.355(7)
_cell_angle_alpha                114.689(14)
_cell_angle_beta                 95.786(16)
_cell_angle_gamma                95.861(15)
_cell_volume                     595.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.128
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    8.743
_shelx_estimated_absorpt_T_min   0.128
_shelx_estimated_absorpt_T_max   0.420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3805
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6347
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.427
_diffrn_reflns_theta_max         31.044
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3478
_reflns_number_gt                2301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1155P)²+3.8218P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3478
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2251
_refine_ls_wR_factor_gt          0.1996
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_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 0.73168(15) 0.78555(13) 0.17736(15) 0.0252(3) Uani 1 1 d . . . . .
Br1 Br 0.45618(13) 0.67703(12) 0.20534(13) 0.0281(3) Uani 1 1 d . . . . .
Br2 Br 0.97179(14) 0.71513(12) 0.29354(13) 0.0298(3) Uani 1 1 d . . . . .
N1 N 0.7083(11) 1.0308(9) 0.2402(10) 0.0243(16) Uani 1 1 d . . . . .
N2 N 0.7810(11) 0.8020(9) -0.0293(10) 0.0243(16) Uani 1 1 d . . . . .
C1 C 0.6717(13) 1.1380(11) 0.3792(12) 0.0255(19) Uani 1 1 d . . . . .
H1 H 0.6671 1.1050 0.4629 0.031 Uiso 1 1 calc R U . . .
C2 C 0.6396(14) 1.2976(12) 0.4071(13) 0.029(2) Uani 1 1 d . . . . .
H2 H 0.6101 1.3697 0.5057 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6527(14) 1.3457(12) 0.2849(14) 0.032(2) Uani 1 1 d . . . . .
H3 H 0.6369 1.4539 0.3008 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6883(14) 1.2368(12) 0.1418(13) 0.031(2) Uani 1 1 d . . . . .
H4 H 0.6917 1.2676 0.0566 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7200(12) 1.0787(10) 0.1207(11) 0.0212(18) Uani 1 1 d . . . . .
C6 C 0.7621(12) 0.9527(11) -0.0270(12) 0.0235(19) Uani 1 1 d . . . . .
C7 C 0.7915(14) 0.9835(12) -0.1589(13) 0.030(2) Uani 1 1 d . . . . .
H7 H 0.7783 1.0875 -0.1570 0.035 Uiso 1 1 calc R U . . .
C8 C 0.8399(15) 0.8621(14) -0.2920(14) 0.035(2) Uani 1 1 d . . . . .
H8 H 0.8558 0.8818 -0.3822 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8650(14) 0.7105(12) -0.2923(13) 0.028(2) Uani 1 1 d . . . . .
H9 H 0.9042 0.6282 -0.3791 0.034 Uiso 1 1 calc R U . . .
C10 C 0.8290(13) 0.6852(12) -0.1567(14) 0.029(2) Uani 1 1 d . . . . .
H10 H 0.8395 0.5815 -0.1568 0.035 Uiso 1 1 calc R U . . .


_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 N2 2.072(9) . ?
Zn1 N1 2.078(8) . ?
Zn1 Br2 2.3618(19) . ?
Zn1 Br1 2.375(2) . ?
N1 C1 1.340(13) . ?
N1 C5 1.364(11) . ?
N2 C10 1.342(14) . ?
N2 C6 1.378(10) . ?
C1 C2 1.411(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.368(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.474(14) . ?
C6 C7 1.409(14) . ?
C7 C8 1.393(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.404(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.430(16) . ?
C9 H9 0.9500 . ?
C10 H10 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
N2 Zn1 N1 80.2(3) . . ?
N2 Zn1 Br2 110.6(2) . . ?
N1 Zn1 Br2 120.7(2) . . ?
N2 Zn1 Br1 122.8(2) . . ?
N1 Zn1 Br1 101.9(2) . . ?
Br2 Zn1 Br1 115.87(7) . . ?
C1 N1 C5 118.9(7) . . ?
C1 N1 Zn1 126.4(6) . . ?
C5 N1 Zn1 114.6(6) . . ?
C10 N2 C6 119.9(8) . . ?
C10 N2 Zn1 127.0(6) . . ?
C6 N2 Zn1 113.1(6) . . ?
N1 C1 C2 123.0(9) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 117.6(10) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C4 C3 C2 119.8(9) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.1(9) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 120.4(9) . . ?
N1 C5 C6 114.9(7) . . ?
C4 C5 C6 124.7(8) . . ?
N2 C6 C7 120.0(9) . . ?
N2 C6 C5 117.0(8) . . ?
C7 C6 C5 122.9(8) . . ?
C8 C7 C6 120.3(9) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.7(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 117.3(10) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
N2 C10 C9 122.6(8) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?

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
C5 N1 C1 C2 1.8(15) . . . . ?
Zn1 N1 C1 C2 -173.0(8) . . . . ?
N1 C1 C2 C3 -2.1(16) . . . . ?
C1 C2 C3 C4 2.7(16) . . . . ?
C2 C3 C4 C5 -3.1(16) . . . . ?
C1 N1 C5 C4 -2.1(14) . . . . ?
Zn1 N1 C5 C4 173.3(7) . . . . ?
C1 N1 C5 C6 179.6(8) . . . . ?
Zn1 N1 C5 C6 -5.1(10) . . . . ?
C3 C4 C5 N1 2.8(15) . . . . ?
C3 C4 C5 C6 -179.0(10) . . . . ?
C10 N2 C6 C7 0.6(14) . . . . ?
Zn1 N2 C6 C7 179.9(7) . . . . ?
C10 N2 C6 C5 -176.2(9) . . . . ?
Zn1 N2 C6 C5 3.1(10) . . . . ?
N1 C5 C6 N2 1.3(12) . . . . ?
C4 C5 C6 N2 -177.0(9) . . . . ?
N1 C5 C6 C7 -175.4(9) . . . . ?
C4 C5 C6 C7 6.3(15) . . . . ?
N2 C6 C7 C8 0.0(15) . . . . ?
C5 C6 C7 C8 176.6(10) . . . . ?
C6 C7 C8 C9 -2.1(16) . . . . ?
C7 C8 C9 C10 3.6(16) . . . . ?
C6 N2 C10 C9 1.0(14) . . . . ?
Zn1 N2 C10 C9 -178.1(7) . . . . ?
C8 C9 C10 N2 -3.1(15) . . . . ?

_refine_diff_density_max         2.033
_refine_diff_density_min         -1.749
_refine_diff_density_rms         0.264

_shelxl_version_number           2013-4

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

data_1x50_320K
_database_code_depnum_ccdc_archive 'CCDC 1469402'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br0.90 Cl1.10 N2 Zn'
_chemical_formula_weight         332.48

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_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                   10.6281(12)
_cell_length_b                   14.7546(16)
_cell_length_c                   7.6742(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.2146(16)
_cell_angle_gamma                90
_cell_volume                     1193.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    320(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_F_000             649
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    5.283
_shelx_estimated_absorpt_T_min   0.547
_shelx_estimated_absorpt_T_max   0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5884
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      320(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9629
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.374
_diffrn_reflns_theta_max         29.142
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1612
_reflns_number_gt                1333
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²+2.6296P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1612
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_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_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 0.0000 0.29823(3) 0.2500 0.04741(18) Uani 1 2 d S T P . .
Br1 Br -0.0084(7) 0.2155(3) 0.0002(7) 0.0673(9) Uani 0.450(4) 1 d . . P A 1
Cl1 Cl -0.0278(13) 0.2182(5) -0.0082(14) 0.068(2) Uani 0.550(4) 1 d . . P A 2
N1 N 0.1211(2) 0.40450(17) 0.2235(3) 0.0467(6) Uani 1 1 d . . . . .
C1 C 0.0674(3) 0.48645(19) 0.2332(4) 0.0460(7) Uani 1 1 d . . . . .
C2 C 0.1353(4) 0.5646(3) 0.2106(5) 0.0721(11) Uani 1 1 d . . . . .
H2 H 0.0979 0.6212 0.2186 0.086 Uiso 1 1 calc R U . . .
C3 C 0.2590(5) 0.5575(4) 0.1760(6) 0.0916(16) Uani 1 1 d . . . . .
H3 H 0.3063 0.6094 0.1614 0.110 Uiso 1 1 calc R U . . .
C4 C 0.3119(4) 0.4738(4) 0.1633(6) 0.0860(14) Uani 1 1 d . . . . .
H4 H 0.3948 0.4680 0.1382 0.103 Uiso 1 1 calc R U . . .
C5 C 0.2408(3) 0.3982(3) 0.1883(5) 0.0661(9) Uani 1 1 d . . . . .
H5 H 0.2770 0.3411 0.1806 0.079 Uiso 1 1 calc R U . . .


_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 N1 2.054(2) 2 ?
Zn1 N1 2.054(2) . ?
Zn1 Br1 2.265(5) 2 ?
Zn1 Br1 2.265(5) . ?
Zn1 Cl1 2.294(10) . ?
Zn1 Cl1 2.294(10) 2 ?
N1 C5 1.337(4) . ?
N1 C1 1.343(4) . ?
C1 C2 1.383(4) . ?
C1 C1 1.487(7) 2 ?
C2 C3 1.378(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(6) . ?
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
N1 Zn1 N1 80.51(15) 2 . ?
N1 Zn1 Br1 106.62(14) 2 2 ?
N1 Zn1 Br1 122.44(19) . 2 ?
N1 Zn1 Br1 122.44(19) 2 . ?
N1 Zn1 Br1 106.62(14) . . ?
Br1 Zn1 Br1 114.8(2) 2 . ?
N1 Zn1 Cl1 117.6(3) 2 . ?
N1 Zn1 Cl1 108.7(2) . . ?
N1 Zn1 Cl1 108.7(2) 2 2 ?
N1 Zn1 Cl1 117.6(3) . 2 ?
Cl1 Zn1 Cl1 118.1(4) . 2 ?
C5 N1 C1 119.7(3) . . ?
C5 N1 Zn1 126.2(3) . . ?
C1 N1 Zn1 114.0(2) . . ?
N1 C1 C2 120.8(3) . . ?
N1 C1 C1 115.76(17) . 2 ?
C2 C1 C1 123.4(2) . 2 ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.7(4) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?

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
C5 N1 C1 C2 -1.2(4) . . . . ?
Zn1 N1 C1 C2 -177.3(2) . . . . ?
C5 N1 C1 C1 178.0(3) . . . 2 ?
Zn1 N1 C1 C1 1.9(4) . . . 2 ?
N1 C1 C2 C3 0.6(5) . . . . ?
C1 C1 C2 C3 -178.5(4) 2 . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C1 N1 C5 C4 0.7(5) . . . . ?
Zn1 N1 C5 C4 176.3(3) . . . . ?
C3 C4 C5 N1 0.5(6) . . . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4

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

data_1x70_320K
_database_code_depnum_ccdc_archive 'CCDC 1469403'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br1.36 Cl0.64 N2 Zn'
_chemical_formula_weight         352.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_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                   10.7082(5)
_cell_length_b                   14.7769(7)
_cell_length_c                   7.7285(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.3492(14)
_cell_angle_gamma                90
_cell_volume                     1212.87(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    321(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.932
_exptl_crystal_F_000             682
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    6.607
_shelx_estimated_absorpt_T_min   0.338
_shelx_estimated_absorpt_T_max   0.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5670
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      321(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8584
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.362
_diffrn_reflns_theta_max         30.578
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1863
_reflns_number_gt                1327
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+0.2994P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1863
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_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 0.0000 0.29855(2) 0.2500 0.04894(15) Uani 1 2 d S T P . .
Br1 Br -0.0103(3) 0.21445(12) -0.0024(3) 0.0663(5) Uani 0.679(3) 1 d . . P A 1
Cl1 Cl -0.0391(13) 0.2212(5) -0.0111(15) 0.063(2) Uani 0.321(3) 1 d . . P A 2
N1 N 0.12000(16) 0.40475(12) 0.2243(2) 0.0483(4) Uani 1 1 d . . . . .
C1 C 0.0669(2) 0.48689(13) 0.2337(3) 0.0484(5) Uani 1 1 d . . . . .
C2 C 0.1348(3) 0.56478(18) 0.2119(3) 0.0722(7) Uani 1 1 d . . . . .
H2 H 0.0981 0.6214 0.2200 0.087 Uiso 1 1 calc R U . . .
C3 C 0.2565(3) 0.5572(3) 0.1784(4) 0.0924(10) Uani 1 1 d . . . . .
H3 H 0.3033 0.6091 0.1639 0.111 Uiso 1 1 calc R U . . .
C4 C 0.3099(3) 0.4741(3) 0.1658(4) 0.0849(9) Uani 1 1 d . . . . .
H4 H 0.3924 0.4686 0.1417 0.102 Uiso 1 1 calc R U . . .
C5 C 0.2387(2) 0.3987(2) 0.1899(3) 0.0672(6) Uani 1 1 d . . . . .
H5 H 0.2744 0.3417 0.1820 0.081 Uiso 1 1 calc R U . . .


_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 N1 2.0539(17) 2 ?
Zn1 N1 2.0539(17) . ?
Zn1 Br1 2.303(2) 2 ?
Zn1 Br1 2.303(2) . ?
Zn1 Cl1 2.311(11) 2 ?
Zn1 Cl1 2.311(11) . ?
N1 C5 1.334(3) . ?
N1 C1 1.346(3) . ?
C1 C2 1.383(3) . ?
C1 C1 1.487(4) 2 ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
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
N1 Zn1 N1 80.36(10) 2 . ?
N1 Zn1 Br1 107.04(7) 2 2 ?
N1 Zn1 Br1 122.11(9) . 2 ?
N1 Zn1 Br1 122.11(9) 2 . ?
N1 Zn1 Br1 107.04(7) . . ?
Br1 Zn1 Br1 114.69(11) 2 . ?
N1 Zn1 Cl1 109.8(2) 2 2 ?
N1 Zn1 Cl1 114.6(3) . 2 ?
N1 Zn1 Cl1 114.6(3) 2 . ?
N1 Zn1 Cl1 109.8(2) . . ?
Cl1 Zn1 Cl1 120.7(5) 2 . ?
C5 N1 C1 119.4(2) . . ?
C5 N1 Zn1 126.26(16) . . ?
C1 N1 Zn1 114.20(14) . . ?
N1 C1 C2 120.8(2) . . ?
N1 C1 C1 115.60(11) . 2 ?
C2 C1 C1 123.61(16) . 2 ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?

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
C5 N1 C1 C2 -1.4(3) . . . . ?
Zn1 N1 C1 C2 -177.50(17) . . . . ?
C5 N1 C1 C1 177.9(2) . . . 2 ?
Zn1 N1 C1 C1 1.8(3) . . . 2 ?
N1 C1 C2 C3 0.8(4) . . . . ?
C1 C1 C2 C3 -178.4(3) 2 . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C1 N1 C5 C4 0.9(4) . . . . ?
Zn1 N1 C5 C4 176.5(2) . . . . ?
C3 C4 C5 N1 0.2(4) . . . . ?

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

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

data_1x90_320K
_database_code_depnum_ccdc_archive 'CCDC 1469404'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br1.77 Cl0.23 N2 Zn'
_chemical_formula_weight         370.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_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                   10.826(3)
_cell_length_b                   14.850(4)
_cell_length_c                   7.813(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.435(5)
_cell_angle_gamma                90
_cell_volume                     1245.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    320(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_F_000             711
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    7.653
_shelx_estimated_absorpt_T_min   0.272
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3973
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      320(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9979
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         29.122
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1681
_reflns_number_gt                1143
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1681
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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_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 0.0000 0.29899(2) 0.2500 0.04859(19) Uani 1 2 d S T P . .
Br1 Br -0.01265(10) 0.21452(6) -0.00432(13) 0.0657(3) Uani 0.883(4) 1 d . . P A
1
Cl1 Cl -0.0606(12) 0.2271(8) -0.009(2) 0.046(3) Uani 0.117(4) 1 d . . P A 2
N1 N 0.1197(2) 0.40505(14) 0.2250(3) 0.0478(5) Uani 1 1 d . . . . .
C1 C 0.0664(3) 0.48689(16) 0.2344(3) 0.0481(6) Uani 1 1 d . . . . .
C2 C 0.1343(3) 0.5645(2) 0.2133(4) 0.0701(9) Uani 1 1 d . . . . .
H2 H 0.0979 0.6209 0.2212 0.084 Uiso 1 1 calc R U . . .
C3 C 0.2545(4) 0.5576(3) 0.1811(5) 0.0902(12) Uani 1 1 d . . . . .
H3 H 0.3006 0.6093 0.1677 0.108 Uiso 1 1 calc R U . . .
C4 C 0.3077(4) 0.4744(3) 0.1682(5) 0.0841(11) Uani 1 1 d . . . . .
H4 H 0.3893 0.4689 0.1441 0.101 Uiso 1 1 calc R U . . .
C5 C 0.2373(3) 0.3996(2) 0.1918(4) 0.0661(8) Uani 1 1 d . . . . .
H5 H 0.2730 0.3429 0.1844 0.079 Uiso 1 1 calc R U . . .


_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 N1 2.065(2) . ?
Zn1 N1 2.065(2) 2 ?
Zn1 Cl1 2.307(16) 2 ?
Zn1 Cl1 2.307(16) . ?
Zn1 Br1 2.3388(11) 2 ?
Zn1 Br1 2.3388(11) . ?
N1 C5 1.335(4) . ?
N1 C1 1.351(3) . ?
C1 C2 1.388(4) . ?
C1 C1 1.489(6) 2 ?
C2 C3 1.361(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(5) . ?
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
N1 Zn1 N1 80.58(12) . 2 ?
N1 Zn1 Cl1 109.0(3) . 2 ?
N1 Zn1 Cl1 112.4(3) 2 2 ?
N1 Zn1 Cl1 112.4(3) . . ?
N1 Zn1 Cl1 109.0(3) 2 . ?
Cl1 Zn1 Cl1 124.9(6) 2 . ?
N1 Zn1 Br1 121.40(6) . 2 ?
N1 Zn1 Br1 107.28(6) 2 2 ?
N1 Zn1 Br1 107.28(6) . . ?
N1 Zn1 Br1 121.40(6) 2 . ?
Br1 Zn1 Br1 115.14(5) 2 . ?
C5 N1 C1 119.4(2) . . ?
C5 N1 Zn1 126.73(19) . . ?
C1 N1 Zn1 113.80(18) . . ?
N1 C1 C2 120.3(3) . . ?
N1 C1 C1 115.90(15) . 2 ?
C2 C1 C1 123.8(2) . 2 ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 122.5(3) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?

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
C5 N1 C1 C2 -1.3(4) . . . . ?
Zn1 N1 C1 C2 -177.6(2) . . . . ?
C5 N1 C1 C1 177.9(3) . . . 2 ?
Zn1 N1 C1 C1 1.6(3) . . . 2 ?
N1 C1 C2 C3 0.8(4) . . . . ?
C1 C1 C2 C3 -178.4(3) 2 . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C1 N1 C5 C4 0.6(4) . . . . ?
Zn1 N1 C5 C4 176.4(3) . . . . ?
C3 C4 C5 N1 0.6(6) . . . . ?

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.074

_shelxl_version_number           2013-4

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

data_1x100_320K
_database_code_depnum_ccdc_archive 'CCDC 1469405'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br2 N2 Zn'
_chemical_formula_weight         381.37

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_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                   10.8238(18)
_cell_length_b                   14.807(2)
_cell_length_c                   7.8103(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.425(3)
_cell_angle_gamma                90
_cell_volume                     1241.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    320(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.041
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    8.385
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5442
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      320(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3978
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.344
_diffrn_reflns_theta_max         29.076
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1623
_reflns_number_gt                1039
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.3476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1623
_refine_ls_number_parameters     69
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.0000 0.29914(3) 0.2500 0.04576(19) Uani 1 2 d S T P . .
Br1 Br -0.01436(4) 0.21474(3) -0.00469(5) 0.06736(19) Uani 1 1 d . . . . .
N1 N 0.1191(2) 0.40521(18) 0.2254(3) 0.0446(7) Uani 1 1 d . . . . .
C1 C 0.0660(3) 0.4869(2) 0.2347(4) 0.0455(8) Uani 1 1 d . . . . .
C2 C 0.1329(4) 0.5648(3) 0.2151(5) 0.0662(11) Uani 1 1 d . . . . .
H2 H 0.0964 0.6212 0.2239 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2541(5) 0.5578(4) 0.1825(6) 0.0841(15) Uani 1 1 d . . . . .
H3 H 0.3001 0.6097 0.1688 0.101 Uiso 1 1 calc R U . . .
C4 C 0.3073(4) 0.4751(4) 0.1701(6) 0.0781(13) Uani 1 1 d . . . . .
H4 H 0.3892 0.4696 0.1472 0.094 Uiso 1 1 calc R U . . .
C5 C 0.2365(4) 0.3999(3) 0.1922(5) 0.0621(10) Uani 1 1 d . . . . .
H5 H 0.2720 0.3431 0.1837 0.075 Uiso 1 1 calc R U . . .


_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 N1 2.057(3) . ?
Zn1 N1 2.057(3) 2 ?
Zn1 Br1 2.3373(5) . ?
Zn1 Br1 2.3373(5) 2 ?
N1 C5 1.332(4) . ?
N1 C1 1.345(4) . ?
C1 C2 1.381(5) . ?
C1 C1 1.479(7) 2 ?
C2 C3 1.372(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(6) . ?
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
N1 Zn1 N1 80.42(15) . 2 ?
N1 Zn1 Br1 107.60(7) . . ?
N1 Zn1 Br1 120.95(7) 2 . ?
N1 Zn1 Br1 120.95(7) . 2 ?
N1 Zn1 Br1 107.60(7) 2 2 ?
Br1 Zn1 Br1 115.36(3) . 2 ?
C5 N1 C1 119.3(3) . . ?
C5 N1 Zn1 126.7(2) . . ?
C1 N1 Zn1 113.8(2) . . ?
N1 C1 C2 120.8(4) . . ?
N1 C1 C1 115.93(19) . 2 ?
C2 C1 C1 123.3(2) . 2 ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 118.1(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 122.5(4) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?

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
C5 N1 C1 C2 -1.9(5) . . . . ?
Zn1 N1 C1 C2 -178.0(3) . . . . ?
C5 N1 C1 C1 177.8(3) . . . 2 ?
Zn1 N1 C1 C1 1.6(4) . . . 2 ?
N1 C1 C2 C3 1.3(5) . . . . ?
C1 C1 C2 C3 -178.3(4) 2 . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C1 N1 C5 C4 1.3(5) . . . . ?
Zn1 N1 C5 C4 176.9(3) . . . . ?
C3 C4 C5 N1 -0.1(7) . . . . ?

_refine_diff_density_max         0.763
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.090

_shelxl_version_number           2013-4

