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

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

data_Zn5
_database_code_depnum_ccdc_archive 'CCDC 1477759'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl2 N2 O Zn'
_chemical_formula_weight         362.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   11.311(3)
_cell_length_b                   9.796(3)
_cell_length_c                   14.305(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.827(3)
_cell_angle_gamma                90.00
_cell_volume                     1517.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    11102
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      26.93

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    1.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7841
_exptl_absorpt_correction_T_max  0.8128
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11102
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         26.93
_reflns_number_total             3041
_reflns_number_gt                2371
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0451P)²+0.1131P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3041
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.98008(3) 0.77879(3) 0.19679(2) 0.04388(13) Uani 1 1 d . . .
N1 N 1.04437(19) 0.9629(2) 0.15649(15) 0.0439(5) Uani 1 1 d . . .
N2 N 0.81647(18) 0.88698(19) 0.13986(14) 0.0369(5) Uani 1 1 d . . .
O1 O 0.77068(18) 0.63258(18) 0.09371(16) 0.0610(6) Uani 1 1 d . . .
Cl1 Cl 1.07627(7) 0.61907(8) 0.13577(5) 0.0621(2) Uani 1 1 d . . .
Cl2 Cl 1.00494(7) 0.76377(7) 0.35641(5) 0.0529(2) Uani 1 1 d . . .
C1 C 0.9546(2) 1.0494(2) 0.11014(17) 0.0388(6) Uani 1 1 d . . .
C2 C 0.9816(3) 1.1728(3) 0.0748(2) 0.0530(7) Uani 1 1 d . . .
H2A H 0.9187 1.2323 0.0431 0.064 Uiso 1 1 calc R . .
C3 C 1.1040(3) 1.2065(3) 0.0873(2) 0.0680(10) Uani 1 1 d . . .
H3A H 1.1240 1.2890 0.0636 0.082 Uiso 1 1 calc R . .
C4 C 1.1943(3) 1.1192(4) 0.1339(2) 0.0691(10) Uani 1 1 d . . .
H4A H 1.2769 1.1406 0.1427 0.083 Uiso 1 1 calc R . .
C5 C 1.1613(3) 0.9979(3) 0.1682(2) 0.0614(8) Uani 1 1 d . . .
H5A H 1.2234 0.9380 0.2009 0.074 Uiso 1 1 calc R . .
C6 C 0.8265(2) 1.0037(2) 0.10153(17) 0.0393(6) Uani 1 1 d . . .
C7 C 0.7206(3) 1.0930(3) 0.0489(2) 0.0653(9) Uani 1 1 d . . .
H7A H 0.6442 1.0503 0.0490 0.098 Uiso 1 1 calc R . .
H7B H 0.7222 1.1061 -0.0173 0.098 Uiso 1 1 calc R . .
H7C H 0.7275 1.1798 0.0811 0.098 Uiso 1 1 calc R . .
C8 C 0.7021(2) 0.8330(3) 0.14639(18) 0.0381(6) Uani 1 1 d . . .
C9 C 0.6802(2) 0.6951(3) 0.1238(2) 0.0440(6) Uani 1 1 d . . .
C10 C 0.5741(3) 0.6340(3) 0.1329(2) 0.0544(7) Uani 1 1 d . . .
H10A H 0.5582 0.5426 0.1165 0.065 Uiso 1 1 calc R . .
C11 C 0.4914(3) 0.7101(3) 0.1669(2) 0.0591(8) Uani 1 1 d . . .
H11A H 0.4196 0.6694 0.1727 0.071 Uiso 1 1 calc R . .
C12 C 0.5145(3) 0.8443(3) 0.1918(2) 0.0588(8) Uani 1 1 d . . .
H12A H 0.4591 0.8943 0.2152 0.071 Uiso 1 1 calc R . .
C13 C 0.6203(3) 0.9054(3) 0.1821(2) 0.0517(7) Uani 1 1 d . . .
H13A H 0.6364 0.9964 0.1999 0.062 Uiso 1 1 calc R . .
C14 C 0.7497(3) 0.4968(3) 0.0560(3) 0.0783(10) Uani 1 1 d . . .
H14A H 0.8206 0.4661 0.0378 0.117 Uiso 1 1 calc R . .
H14B H 0.6784 0.4957 -0.0002 0.117 Uiso 1 1 calc R . .
H14C H 0.7361 0.4373 0.1052 0.117 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.083(2) . ?
Zn1 N1 2.087(2) . ?
Zn1 Cl2 2.2233(10) . ?
Zn1 Cl1 2.2233(8) . ?
N1 C5 1.329(3) . ?
N1 C1 1.341(3) . ?
N2 C6 1.287(3) . ?
N2 C8 1.425(3) . ?
O1 C9 1.365(3) . ?
O1 C14 1.429(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.487(3) . ?
C2 C3 1.383(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.350(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.499(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.377(3) . ?
C8 C9 1.395(4) . ?
C9 C10 1.380(4) . ?
C10 C11 1.389(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.368(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.380(4) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 78.08(8) . . ?
N2 Zn1 Cl2 105.61(6) . . ?
N1 Zn1 Cl2 112.97(6) . . ?
N2 Zn1 Cl1 133.23(6) . . ?
N1 Zn1 Cl1 104.50(7) . . ?
Cl2 Zn1 Cl1 115.21(3) . . ?
C5 N1 C1 118.9(2) . . ?
C5 N1 Zn1 127.0(2) . . ?
C1 N1 Zn1 114.06(16) . . ?
C6 N2 C8 123.4(2) . . ?
C6 N2 Zn1 116.14(16) . . ?
C8 N2 Zn1 120.40(15) . . ?
C9 O1 C14 118.6(2) . . ?
N1 C1 C2 121.2(2) . . ?
N1 C1 C6 115.5(2) . . ?
C2 C1 C6 123.2(3) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
N1 C5 C4 122.6(3) . . ?
N1 C5 H5A 118.7 . . ?
C4 C5 H5A 118.7 . . ?
N2 C6 C1 115.9(2) . . ?
N2 C6 C7 125.2(2) . . ?
C1 C6 C7 118.9(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 119.4(2) . . ?
C13 C8 N2 123.6(2) . . ?
C9 C8 N2 116.6(2) . . ?
O1 C9 C10 126.0(2) . . ?
O1 C9 C8 114.1(2) . . ?
C10 C9 C8 120.0(2) . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12A 120.1 . . ?
C13 C12 H12A 120.1 . . ?
C8 C13 C12 120.6(3) . . ?
C8 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.926
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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_Zn1
_database_code_depnum_ccdc_archive 'CCDC 1494305'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 Cl2 N2 Zn'
_chemical_formula_weight         332.52

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   9.5582(5)
_cell_length_b                   10.9115(5)
_cell_length_c                   13.6401(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.856(4)
_cell_angle_gamma                90.00
_cell_volume                     1420.82(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5269
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    2.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6567
_exptl_absorpt_correction_T_max  0.6803
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5269
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         27.56
_reflns_number_total             3241
_reflns_number_gt                2416
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3241
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   0.808
_refine_ls_restrained_S_all      0.808
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.63234(4) 0.76832(3) 0.02832(3) 0.03703(16) Uani 1 1 d . . .
Cl1 Cl 0.76556(12) 0.60507(10) 0.04558(8) 0.0667(3) Uani 1 1 d . . .
Cl2 Cl 0.62421(12) 0.85233(10) -0.11779(7) 0.0637(3) Uani 1 1 d . . .
N1 N 0.4341(3) 0.7536(2) 0.0781(2) 0.0408(6) Uani 1 1 d . . .
N2 N 0.6499(3) 0.8811(2) 0.14838(19) 0.0356(6) Uani 1 1 d . . .
C1 C 0.4153(3) 0.8210(3) 0.1592(2) 0.0384(7) Uani 1 1 d . . .
C2 C 0.2870(4) 0.8267(3) 0.2000(3) 0.0533(9) Uani 1 1 d . . .
H2A H 0.2752 0.8720 0.2567 0.064 Uiso 1 1 calc R . .
C3 C 0.1748(5) 0.7637(4) 0.1550(4) 0.0640(12) Uani 1 1 d . . .
H3A H 0.0864 0.7684 0.1803 0.077 Uiso 1 1 calc R . .
C4 C 0.1953(4) 0.6957(4) 0.0743(3) 0.0595(10) Uani 1 1 d . . .
H4A H 0.1220 0.6512 0.0443 0.071 Uiso 1 1 calc R . .
C5 C 0.3259(4) 0.6933(3) 0.0372(3) 0.0498(8) Uani 1 1 d . . .
H5A H 0.3391 0.6475 -0.0190 0.060 Uiso 1 1 calc R . .
C6 C 0.5418(3) 0.8898(3) 0.1990(2) 0.0372(7) Uani 1 1 d . . .
C7 C 0.5316(4) 0.9628(3) 0.2901(2) 0.0486(8) Uani 1 1 d . . .
H7A H 0.6202 1.0010 0.3063 0.073 Uiso 1 1 calc R . .
H7B H 0.5070 0.9100 0.3428 0.073 Uiso 1 1 calc R . .
H7C H 0.4609 1.0247 0.2800 0.073 Uiso 1 1 calc R . .
C8 C 0.7793(3) 0.9404(3) 0.1761(2) 0.0405(7) Uani 1 1 d . . .
C9 C 0.8374(4) 1.0164(4) 0.1085(3) 0.0550(9) Uani 1 1 d . . .
H9A H 0.7920 1.0299 0.0475 0.066 Uiso 1 1 calc R . .
C10 C 0.9658(4) 1.0729(4) 0.1328(3) 0.0658(11) Uani 1 1 d . . .
H10A H 1.0062 1.1241 0.0876 0.079 Uiso 1 1 calc R . .
C11 C 1.0318(4) 1.0535(4) 0.2216(3) 0.0609(11) Uani 1 1 d . . .
H11A H 1.1156 1.0936 0.2379 0.073 Uiso 1 1 calc R . .
C12 C 0.9755(4) 0.9750(4) 0.2878(3) 0.0558(10) Uani 1 1 d . . .
H12A H 1.0224 0.9610 0.3481 0.067 Uiso 1 1 calc R . .
C13 C 0.8497(4) 0.9168(3) 0.2654(3) 0.0468(8) Uani 1 1 d . . .
H13A H 0.8126 0.8624 0.3098 0.056 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.049(2) . ?
Zn1 N1 2.051(3) . ?
Zn1 Cl2 2.1915(9) . ?
Zn1 Cl1 2.1955(10) . ?
N1 C5 1.324(5) . ?
N1 C1 1.348(4) . ?
N2 C6 1.275(4) . ?
N2 C8 1.430(4) . ?
C1 C2 1.373(5) . ?
C1 C6 1.501(5) . ?
C2 C3 1.390(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.350(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.370(6) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.482(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.378(5) . ?
C8 C13 1.387(5) . ?
C9 C10 1.398(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.354(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.374(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.380(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 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
N2 Zn1 N1 79.78(11) . . ?
N2 Zn1 Cl2 118.26(8) . . ?
N1 Zn1 Cl2 110.02(9) . . ?
N2 Zn1 Cl1 112.19(8) . . ?
N1 Zn1 Cl1 116.19(8) . . ?
Cl2 Zn1 Cl1 115.53(4) . . ?
C5 N1 C1 118.9(3) . . ?
C5 N1 Zn1 127.9(3) . . ?
C1 N1 Zn1 113.1(2) . . ?
C6 N2 C8 122.5(3) . . ?
C6 N2 Zn1 116.2(2) . . ?
C8 N2 Zn1 121.2(2) . . ?
N1 C1 C2 121.0(3) . . ?
N1 C1 C6 115.6(3) . . ?
C2 C1 C6 123.4(3) . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
N1 C5 C4 122.8(4) . . ?
N1 C5 H5A 118.6 . . ?
C4 C5 H5A 118.6 . . ?
N2 C6 C7 125.6(3) . . ?
N2 C6 C1 115.2(3) . . ?
C7 C6 C1 119.1(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 120.4(3) . . ?
C9 C8 N2 117.9(3) . . ?
C13 C8 N2 121.6(3) . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 H9A 120.5 . . ?
C10 C9 H9A 120.5 . . ?
C11 C10 C9 120.5(4) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 C12 120.3(4) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C12 C13 C8 119.2(4) . . ?
C12 C13 H13A 120.4 . . ?
C8 C13 H13A 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_e
_database_code_depnum_ccdc_archive 'CCDC 1494306'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2016-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl2 N2 Zn'
_chemical_formula_weight         346.54

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                   8.108(5)
_cell_length_b                   13.089(8)
_cell_length_c                   15.690(9)
_cell_angle_alpha                71.786(7)
_cell_angle_beta                 76.105(7)
_cell_angle_gamma                84.537(7)
_cell_volume                     1535.1(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    11434
_cell_measurement_theta_min      1.401
_cell_measurement_theta_max      26.809

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.935
_shelx_estimated_absorpt_T_min   0.722
_shelx_estimated_absorpt_T_max   0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7221
_exptl_absorpt_correction_T_max  0.7734
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11434
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.401
_diffrn_reflns_theta_max         26.809
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             5771
_reflns_number_gt                3868
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0512P)²+0.0983P] 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     SHELXL
_refine_ls_extinction_coef       0.0008(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5771
_refine_ls_number_parameters     346
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.035
_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 -0.16311(5) 0.40073(3) 0.31673(3) 0.05359(15) Uani 1 1 d . . . . .
Zn2 Zn 0.46915(5) -0.12865(3) 0.30300(3) 0.05056(15) Uani 1 1 d . . . . .
Cl1 Cl 0.02530(18) 0.26691(9) 0.33857(11) 0.1051(5) Uani 1 1 d . . . . .
Cl2 Cl -0.39595(13) 0.36244(10) 0.28597(7) 0.0753(3) Uani 1 1 d . . . . .
Cl3 Cl 0.19528(13) -0.09059(10) 0.32886(9) 0.0859(4) Uani 1 1 d . . . . .
Cl4 Cl 0.54684(14) -0.28140(8) 0.27246(8) 0.0737(3) Uani 1 1 d . . . . .
N1 N -0.2045(4) 0.4782(2) 0.41703(19) 0.0504(7) Uani 1 1 d . . . . .
N2 N -0.0527(4) 0.5460(2) 0.24146(19) 0.0511(7) Uani 1 1 d . . . . .
N3 N 0.5849(3) -0.1056(2) 0.39930(19) 0.0473(7) Uani 1 1 d . . . . .
N4 N 0.6318(3) -0.0073(2) 0.22088(18) 0.0497(7) Uani 1 1 d . . . . .
C1 C -0.2836(5) 0.4403(3) 0.5057(3) 0.0643(11) Uani 1 1 d . . . . .
H1 H -0.3326 0.3730 0.5265 0.077 Uiso 1 1 calc R U . . .
C2 C -0.2948(5) 0.4979(4) 0.5676(3) 0.0673(11) Uani 1 1 d . . . . .
H2 H -0.3531 0.4705 0.6284 0.081 Uiso 1 1 calc R U . . .
C3 C -0.2193(5) 0.5946(3) 0.5380(3) 0.0646(11) Uani 1 1 d . . . . .
H3 H -0.2231 0.6338 0.5787 0.077 Uiso 1 1 calc R U . . .
C4 C -0.1366(5) 0.6347(3) 0.4465(3) 0.0579(10) Uani 1 1 d . . . . .
H4 H -0.0835 0.7007 0.4252 0.069 Uiso 1 1 calc R U . . .
C5 C -0.1339(4) 0.5752(3) 0.3872(2) 0.0471(8) Uani 1 1 d . . . . .
C6 C -0.0524(4) 0.6119(3) 0.2867(2) 0.0498(9) Uani 1 1 d . . . . .
C7 C 0.0210(6) 0.7216(3) 0.2466(3) 0.0803(13) Uani 1 1 d . . . . .
H7A H 0.0602 0.7366 0.1812 0.120 Uiso 1 1 calc R U . . .
H7B H 0.1147 0.7246 0.2733 0.120 Uiso 1 1 calc R U . . .
H7C H -0.0645 0.7740 0.2596 0.120 Uiso 1 1 calc R U . . .
C8A C 0.0021(5) 0.5809(4) 0.14235(17) 0.0534(14) Uani 0.75 1 d DG . P A 1
C9A C -0.1131(4) 0.6247(4) 0.0870(3) 0.0693(16) Uani 0.75 1 d DG . P A 1
H9A H -0.2263 0.6356 0.1137 0.083 Uiso 0.75 1 calc R U P A 1
C10A C -0.0593(6) 0.6522(4) -0.0082(2) 0.101(2) Uani 0.75 1 d DG . P A 1
H10A H -0.1364 0.6815 -0.0452 0.121 Uiso 0.75 1 calc R U P A 1
C11A C 0.1098(6) 0.6360(4) -0.04807(17) 0.094(2) Uani 0.75 1 d DG . P A 1
H11A H 0.1458 0.6544 -0.1118 0.113 Uiso 0.75 1 calc R U P A 1
C12A C 0.2250(5) 0.5922(4) 0.0073(3) 0.090(2) Uani 0.75 1 d DG . P A 1
H12A H 0.3382 0.5813 -0.0194 0.108 Uiso 0.75 1 calc R U P A 1
C13A C 0.1712(4) 0.5647(4) 0.1025(2) 0.0703(16) Uani 0.75 1 d DG . P A 1
C14A C 0.2983(8) 0.5148(7) 0.1634(5) 0.108(3) Uani 0.75 1 d D . P A 1
H14A H 0.4039 0.4990 0.1259 0.161 Uiso 0.75 1 calc R U P A 1
H14B H 0.2533 0.4496 0.2086 0.161 Uiso 0.75 1 calc R U P A 1
H14C H 0.3172 0.5646 0.1937 0.161 Uiso 0.75 1 calc R U P A 1
C8B C 0.0660(16) 0.5603(14) 0.1485(7) 0.0534(14) Uani 0.25 1 d DG . P A 2
C9B C 0.2395(17) 0.5370(14) 0.1341(8) 0.0693(16) Uani 0.25 1 d DG . P A 2
H9B H 0.2903 0.5090 0.1841 0.083 Uiso 0.25 1 calc R U P A 2
C10B C 0.3372(13) 0.5556(13) 0.0450(9) 0.101(2) Uani 0.25 1 d DG . P A 2
H10B H 0.4533 0.5400 0.0354 0.121 Uiso 0.25 1 calc R U P A 2
C11B C 0.2612(17) 0.5974(13) -0.0296(7) 0.094(2) Uani 0.25 1 d DG . P A 2
H11B H 0.3265 0.6098 -0.0892 0.113 Uiso 0.25 1 calc R U P A 2
C12B C 0.0877(17) 0.6206(13) -0.0152(7) 0.090(2) Uani 0.25 1 d DG . P A 2
H12B H 0.0369 0.6486 -0.0652 0.108 Uiso 0.25 1 calc R U P A 2
C13B C -0.0099(13) 0.6021(12) 0.0739(9) 0.0703(16) Uani 0.25 1 d DG . P A 2
C14B C -0.196(2) 0.628(2) 0.0912(16) 0.108(3) Uani 0.25 1 d D . P A 2
H14D H -0.2374 0.6320 0.0378 0.161 Uiso 0.25 1 calc R U P A 2
H14E H -0.2159 0.6955 0.1041 0.161 Uiso 0.25 1 calc R U P A 2
H14F H -0.2542 0.5723 0.1429 0.161 Uiso 0.25 1 calc R U P A 2
C15 C 0.5533(5) -0.1548(3) 0.4897(3) 0.0578(10) Uani 1 1 d . . . . .
H15 H 0.4713 -0.2075 0.5149 0.069 Uiso 1 1 calc R U . . .
C16 C 0.6375(5) -0.1305(3) 0.5472(3) 0.0604(10) Uani 1 1 d . . . . .
H16 H 0.6126 -0.1662 0.6101 0.072 Uiso 1 1 calc R U . . .
C17 C 0.7587(5) -0.0528(3) 0.5103(3) 0.0627(11) Uani 1 1 d . . . . .
H17 H 0.8178 -0.0357 0.5478 0.075 Uiso 1 1 calc R U . . .
C18 C 0.7925(4) 0.0000(3) 0.4161(3) 0.0550(9) Uani 1 1 d . . . . .
H18 H 0.8733 0.0534 0.3898 0.066 Uiso 1 1 calc R U . . .
C19 C 0.7032(4) -0.0287(3) 0.3627(2) 0.0437(8) Uani 1 1 d . . . . .
C20 C 0.7294(4) 0.0234(3) 0.2613(2) 0.0458(8) Uani 1 1 d . . . . .
C21 C 0.8630(5) 0.1063(3) 0.2141(3) 0.0690(11) Uani 1 1 d . . . . .
H21A H 0.9723 0.0743 0.2212 0.104 Uiso 1 1 calc R U . . .
H21B H 0.8401 0.1641 0.2411 0.104 Uiso 1 1 calc R U . . .
H21C H 0.8622 0.1337 0.1499 0.104 Uiso 1 1 calc R U . . .
C22A C 0.6505(9) 0.0329(4) 0.1241(2) 0.0507(14) Uani 0.75 1 d DG . P B 1
C23A C 0.7532(7) -0.0223(3) 0.0676(3) 0.0640(16) Uani 0.75 1 d DG . P B 1
H23A H 0.8151 -0.0831 0.0930 0.077 Uiso 0.75 1 calc R U P B 1
C24A C 0.7635(6) 0.0134(4) -0.0267(3) 0.092(2) Uani 0.75 1 d DG . P B 1
H24A H 0.8323 -0.0236 -0.0645 0.110 Uiso 0.75 1 calc R U P B 1
C25A C 0.6711(8) 0.1042(4) -0.0646(2) 0.096(3) Uani 0.75 1 d DG . P B 1
H25A H 0.6780 0.1281 -0.1277 0.116 Uiso 0.75 1 calc R U P B 1
C26A C 0.5683(7) 0.1594(3) -0.0081(3) 0.084(2) Uani 0.75 1 d DG . P B 1
H26A H 0.5065 0.2202 -0.0334 0.101 Uiso 0.75 1 calc R U P B 1
C27A C 0.5580(7) 0.1237(4) 0.0862(3) 0.0670(18) Uani 0.75 1 d DG . P B 1
C28A C 0.4372(9) 0.1839(5) 0.1516(5) 0.0924(19) Uani 0.75 1 d D . P B 1
H28A H 0.5015 0.2030 0.1883 0.139 Uiso 0.75 1 calc R U P B 1
H28B H 0.3471 0.1374 0.1913 0.139 Uiso 0.75 1 calc R U P B 1
H28C H 0.3899 0.2479 0.1151 0.139 Uiso 0.75 1 calc R U P B 1
C22B C 0.618(3) 0.0565(16) 0.1242(8) 0.0507(14) Uani 0.25 1 d DG . P B 2
C23B C 0.515(3) 0.1479(16) 0.1022(9) 0.0640(16) Uani 0.25 1 d DG . P B 2
H23B H 0.4501 0.1744 0.1485 0.077 Uiso 0.25 1 calc R U P B 2
C24B C 0.509(2) 0.1997(12) 0.0109(11) 0.092(2) Uani 0.25 1 d DG . P B 2
H24B H 0.4405 0.2608 -0.0038 0.110 Uiso 0.25 1 calc R U P B 2
C25B C 0.606(2) 0.1600(13) -0.0584(8) 0.096(3) Uani 0.25 1 d DG . P B 2
H25B H 0.6020 0.1947 -0.1195 0.116 Uiso 0.25 1 calc R U P B 2
C26B C 0.709(2) 0.0687(12) -0.0364(9) 0.084(2) Uani 0.25 1 d DG . P B 2
H26B H 0.7733 0.0422 -0.0828 0.101 Uiso 0.25 1 calc R U P B 2
C27B C 0.714(2) 0.0169(12) 0.0549(10) 0.0670(18) Uani 0.25 1 d DG . P B 2
C28B C 0.806(3) -0.0893(13) 0.0781(13) 0.0924(19) Uani 0.25 1 d D . P B 2
H28D H 0.9133 -0.0858 0.0346 0.139 Uiso 0.25 1 calc R U P B 2
H28E H 0.7390 -0.1443 0.0757 0.139 Uiso 0.25 1 calc R U P B 2
H28F H 0.8263 -0.1058 0.1389 0.139 Uiso 0.25 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.055(3) . ?
Zn1 N1 2.073(3) . ?
Zn1 Cl2 2.1949(15) . ?
Zn1 Cl1 2.2105(16) . ?
Zn2 N4 2.055(3) . ?
Zn2 N3 2.068(3) . ?
Zn2 Cl3 2.1971(17) . ?
Zn2 Cl4 2.1996(16) . ?
N1 C1 1.339(4) . ?
N1 C5 1.341(4) . ?
N2 C6 1.277(4) . ?
N2 C8A 1.445(4) . ?
N2 C8B 1.509(9) . ?
N3 C15 1.334(4) . ?
N3 C19 1.350(4) . ?
N4 C20 1.284(4) . ?
N4 C22A 1.418(4) . ?
N4 C22B 1.512(11) . ?
C1 C2 1.386(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.496(5) . ?
C6 C7 1.493(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8A C9A 1.3900 . ?
C8A C13A 1.3900 . ?
C9A C10A 1.3900 . ?
C9A H9A 0.9300 . ?
C10A C11A 1.3900 . ?
C10A H10A 0.9300 . ?
C11A C12A 1.3900 . ?
C11A H11A 0.9300 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9300 . ?
C13A C14A 1.535(7) . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C8B C9B 1.3900 . ?
C8B C13B 1.3900 . ?
C9B C10B 1.3900 . ?
C9B H9B 0.9300 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9300 . ?
C11B C12B 1.3900 . ?
C11B H11B 0.9300 . ?
C12B C13B 1.3900 . ?
C12B H12B 0.9300 . ?
C13B C14B 1.492(15) . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
C15 C16 1.377(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.494(5) . ?
C20 C21 1.495(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22A C23A 1.3900 . ?
C22A C27A 1.3900 . ?
C23A C24A 1.3900 . ?
C23A H23A 0.9300 . ?
C24A C25A 1.3900 . ?
C24A H24A 0.9300 . ?
C25A C26A 1.3900 . ?
C25A H25A 0.9300 . ?
C26A C27A 1.3900 . ?
C26A H26A 0.9300 . ?
C27A C28A 1.584(7) . ?
C28A H28A 0.9600 . ?
C28A H28B 0.9600 . ?
C28A H28C 0.9600 . ?
C22B C23B 1.3900 . ?
C22B C27B 1.3900 . ?
C23B C24B 1.3900 . ?
C23B H23B 0.9300 . ?
C24B C25B 1.3900 . ?
C24B H24B 0.9300 . ?
C25B C26B 1.3900 . ?
C25B H25B 0.9300 . ?
C26B C27B 1.3900 . ?
C26B H26B 0.9300 . ?
C27B C28B 1.496(14) . ?
C28B H28D 0.9600 . ?
C28B H28E 0.9600 . ?
C28B H28F 0.9600 . ?

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 79.32(12) . . ?
N2 Zn1 Cl2 118.15(9) . . ?
N1 Zn1 Cl2 114.33(9) . . ?
N2 Zn1 Cl1 112.65(10) . . ?
N1 Zn1 Cl1 112.45(9) . . ?
Cl2 Zn1 Cl1 115.01(6) . . ?
N4 Zn2 N3 79.61(12) . . ?
N4 Zn2 Cl3 117.95(10) . . ?
N3 Zn2 Cl3 113.08(9) . . ?
N4 Zn2 Cl4 111.57(9) . . ?
N3 Zn2 Cl4 112.85(9) . . ?
Cl3 Zn2 Cl4 116.39(5) . . ?
C1 N1 C5 118.8(3) . . ?
C1 N1 Zn1 127.7(3) . . ?
C5 N1 Zn1 113.4(2) . . ?
C6 N2 C8A 119.7(3) . . ?
C6 N2 C8B 120.6(7) . . ?
C6 N2 Zn1 115.6(2) . . ?
C8A N2 Zn1 124.2(3) . . ?
C8B N2 Zn1 121.2(7) . . ?
C15 N3 C19 118.8(3) . . ?
C15 N3 Zn2 128.1(2) . . ?
C19 N3 Zn2 113.1(2) . . ?
C20 N4 C22A 121.0(4) . . ?
C20 N4 C22B 120.6(11) . . ?
C20 N4 Zn2 115.7(2) . . ?
C22A N4 Zn2 123.0(4) . . ?
C22B N4 Zn2 122.8(11) . . ?
N1 C1 C2 122.2(4) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 121.4(3) . . ?
N1 C5 C6 115.0(3) . . ?
C4 C5 C6 123.7(3) . . ?
N2 C6 C7 125.0(3) . . ?
N2 C6 C5 116.6(3) . . ?
C7 C6 C5 118.5(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9A C8A C13A 120.0 . . ?
C9A C8A N2 121.0(3) . . ?
C13A C8A N2 118.9(3) . . ?
C10A C9A C8A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C12A C13A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C12A C13A C8A 120.0 . . ?
C12A C13A C14A 119.8(4) . . ?
C8A C13A C14A 120.2(4) . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C9B C8B C13B 120.0 . . ?
C9B C8B N2 125.1(8) . . ?
C13B C8B N2 114.9(8) . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C9B C10B C11B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C12B C11B C10B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C11B C12B C13B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C12B C13B C8B 120.0 . . ?
C12B C13B C14B 121.1(12) . . ?
C8B C13B C14B 118.9(12) . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
N3 C15 C16 122.5(4) . . ?
N3 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C17 C16 C15 118.9(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 118.5(3) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
N3 C19 C18 121.9(3) . . ?
N3 C19 C20 115.4(3) . . ?
C18 C19 C20 122.6(3) . . ?
N4 C20 C19 116.1(3) . . ?
N4 C20 C21 124.8(3) . . ?
C19 C20 C21 119.2(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23A C22A C27A 120.0 . . ?
C23A C22A N4 119.9(3) . . ?
C27A C22A N4 119.9(3) . . ?
C24A C23A C22A 120.0 . . ?
C24A C23A H23A 120.0 . . ?
C22A C23A H23A 120.0 . . ?
C23A C24A C25A 120.0 . . ?
C23A C24A H24A 120.0 . . ?
C25A C24A H24A 120.0 . . ?
C26A C25A C24A 120.0 . . ?
C26A C25A H25A 120.0 . . ?
C24A C25A H25A 120.0 . . ?
C27A C26A C25A 120.0 . . ?
C27A C26A H26A 120.0 . . ?
C25A C26A H26A 120.0 . . ?
C26A C27A C22A 120.0 . . ?
C26A C27A C28A 120.5(3) . . ?
C22A C27A C28A 119.5(3) . . ?
C27A C28A H28A 109.5 . . ?
C27A C28A H28B 109.5 . . ?
H28A C28A H28B 109.5 . . ?
C27A C28A H28C 109.5 . . ?
H28A C28A H28C 109.5 . . ?
H28B C28A H28C 109.5 . . ?
C23B C22B C27B 120.0 . . ?
C23B C22B N4 124.6(11) . . ?
C27B C22B N4 115.3(11) . . ?
C22B C23B C24B 120.0 . . ?
C22B C23B H23B 120.0 . . ?
C24B C23B H23B 120.0 . . ?
C23B C24B C25B 120.0 . . ?
C23B C24B H24B 120.0 . . ?
C25B C24B H24B 120.0 . . ?
C26B C25B C24B 120.0 . . ?
C26B C25B H25B 120.0 . . ?
C24B C25B H25B 120.0 . . ?
C25B C26B C27B 120.0 . . ?
C25B C26B H26B 120.0 . . ?
C27B C26B H26B 120.0 . . ?
C26B C27B C22B 120.0 . . ?
C26B C27B C28B 118.9(12) . . ?
C22B C27B C28B 120.5(12) . . ?
C27B C28B H28D 109.5 . . ?
C27B C28B H28E 109.5 . . ?
H28D C28B H28E 109.5 . . ?
C27B C28B H28F 109.5 . . ?
H28D C28B H28F 109.5 . . ?
H28E C28B H28F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.0(6) . . . . ?
Zn1 N1 C1 C2 176.2(3) . . . . ?
N1 C1 C2 C3 -1.8(6) . . . . ?
C1 C2 C3 C4 1.5(6) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C1 N1 C5 C4 2.1(5) . . . . ?
Zn1 N1 C5 C4 -174.7(3) . . . . ?
C1 N1 C5 C6 -178.5(3) . . . . ?
Zn1 N1 C5 C6 4.7(4) . . . . ?
C3 C4 C5 N1 -2.3(6) . . . . ?
C3 C4 C5 C6 178.3(3) . . . . ?
C8A N2 C6 C7 -8.0(6) . . . . ?
C8B N2 C6 C7 17.9(8) . . . . ?
Zn1 N2 C6 C7 179.8(3) . . . . ?
C8A N2 C6 C5 171.5(3) . . . . ?
C8B N2 C6 C5 -162.6(7) . . . . ?
Zn1 N2 C6 C5 -0.8(4) . . . . ?
N1 C5 C6 N2 -2.7(5) . . . . ?
C4 C5 C6 N2 176.6(3) . . . . ?
N1 C5 C6 C7 176.7(3) . . . . ?
C4 C5 C6 C7 -3.9(5) . . . . ?
C6 N2 C8A C9A -90.6(4) . . . . ?
C8B N2 C8A C9A 171(2) . . . . ?
Zn1 N2 C8A C9A 80.9(4) . . . . ?
C6 N2 C8A C13A 92.9(4) . . . . ?
C8B N2 C8A C13A -6(2) . . . . ?
Zn1 N2 C8A C13A -95.5(3) . . . . ?
C13A C8A C9A C10A 0.0 . . . . ?
N2 C8A C9A C10A -176.4(4) . . . . ?
C8A C9A C10A C11A 0.0 . . . . ?
C9A C10A C11A C12A 0.0 . . . . ?
C10A C11A C12A C13A 0.0 . . . . ?
C11A C12A C13A C8A 0.0 . . . . ?
C11A C12A C13A C14A 179.1(5) . . . . ?
C9A C8A C13A C12A 0.0 . . . . ?
N2 C8A C13A C12A 176.5(4) . . . . ?
C9A C8A C13A C14A -179.0(5) . . . . ?
N2 C8A C13A C14A -2.6(6) . . . . ?
C6 N2 C8B C9B 74.9(10) . . . . ?
C8A N2 C8B C9B 169(3) . . . . ?
Zn1 N2 C8B C9B -85.9(10) . . . . ?
C6 N2 C8B C13B -103.8(9) . . . . ?
C8A N2 C8B C13B -9.4(14) . . . . ?
Zn1 N2 C8B C13B 95.4(9) . . . . ?
C13B C8B C9B C10B 0.0 . . . . ?
N2 C8B C9B C10B -178.6(15) . . . . ?
C8B C9B C10B C11B 0.0 . . . . ?
C9B C10B C11B C12B 0.0 . . . . ?
C10B C11B C12B C13B 0.0 . . . . ?
C11B C12B C13B C8B 0.0 . . . . ?
C11B C12B C13B C14B 179.1(18) . . . . ?
C9B C8B C13B C12B 0.0 . . . . ?
N2 C8B C13B C12B 178.8(13) . . . . ?
C9B C8B C13B C14B -179.1(18) . . . . ?
N2 C8B C13B C14B -0.4(19) . . . . ?
C19 N3 C15 C16 -0.4(5) . . . . ?
Zn2 N3 C15 C16 -178.6(3) . . . . ?
N3 C15 C16 C17 -0.1(6) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C15 N3 C19 C18 0.3(5) . . . . ?
Zn2 N3 C19 C18 178.8(2) . . . . ?
C15 N3 C19 C20 -179.2(3) . . . . ?
Zn2 N3 C19 C20 -0.7(4) . . . . ?
C17 C18 C19 N3 0.3(5) . . . . ?
C17 C18 C19 C20 179.7(3) . . . . ?
C22A N4 C20 C19 -177.0(3) . . . . ?
C22B N4 C20 C19 165.7(9) . . . . ?
Zn2 N4 C20 C19 -3.6(4) . . . . ?
C22A N4 C20 C21 3.4(5) . . . . ?
C22B N4 C20 C21 -13.9(10) . . . . ?
Zn2 N4 C20 C21 176.8(3) . . . . ?
N3 C19 C20 N4 2.9(4) . . . . ?
C18 C19 C20 N4 -176.6(3) . . . . ?
N3 C19 C20 C21 -177.5(3) . . . . ?
C18 C19 C20 C21 3.0(5) . . . . ?
C20 N4 C22A C23A 92.3(5) . . . . ?
C22B N4 C22A C23A -175(6) . . . . ?
Zn2 N4 C22A C23A -80.7(5) . . . . ?
C20 N4 C22A C27A -91.6(5) . . . . ?
C22B N4 C22A C27A 1(5) . . . . ?
Zn2 N4 C22A C27A 95.4(4) . . . . ?
C27A C22A C23A C24A 0.0 . . . . ?
N4 C22A C23A C24A 176.1(7) . . . . ?
C22A C23A C24A C25A 0.0 . . . . ?
C23A C24A C25A C26A 0.0 . . . . ?
C24A C25A C26A C27A 0.0 . . . . ?
C25A C26A C27A C22A 0.0 . . . . ?
C25A C26A C27A C28A -178.2(5) . . . . ?
C23A C22A C27A C26A 0.0 . . . . ?
N4 C22A C27A C26A -176.1(7) . . . . ?
C23A C22A C27A C28A 178.2(5) . . . . ?
N4 C22A C27A C28A 2.1(5) . . . . ?
C20 N4 C22B C23B -81.8(14) . . . . ?
C22A N4 C22B C23B -178(6) . . . . ?
Zn2 N4 C22B C23B 86.7(13) . . . . ?
C20 N4 C22B C27B 99.2(12) . . . . ?
C22A N4 C22B C27B 3(4) . . . . ?
Zn2 N4 C22B C27B -92.3(13) . . . . ?
C27B C22B C23B C24B 0.0 . . . . ?
N4 C22B C23B C24B -179(2) . . . . ?
C22B C23B C24B C25B 0.0 . . . . ?
C23B C24B C25B C26B 0.0 . . . . ?
C24B C25B C26B C27B 0.0 . . . . ?
C25B C26B C27B C22B 0.0 . . . . ?
C25B C26B C27B C28B 171.7(18) . . . . ?
C23B C22B C27B C26B 0.0 . . . . ?
N4 C22B C27B C26B 179(2) . . . . ?
C23B C22B C27B C28B -171.6(18) . . . . ?
N4 C22B C27B C28B 7.5(18) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# 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_Zn3
_database_code_depnum_ccdc_archive 'CCDC 1494307'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cl2 N2 Zn'
_chemical_formula_weight         360.57

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   9.0958(4)
_cell_length_b                   11.7426(5)
_cell_length_c                   15.0944(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.7160(10)
_cell_angle_gamma                90.00
_cell_volume                     1611.48(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    24196
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    1.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8089
_exptl_absorpt_correction_T_max  0.8227
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24196
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.58
_reflns_number_total             3722
_reflns_number_gt                2974
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3722
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.16952(3) 0.72371(2) 0.459839(18) 0.03669(15) Uani 1 1 d . . .
Cl1 Cl 0.31135(8) 0.58568(6) 0.41369(6) 0.0595(2) Uani 1 1 d . . .
Cl2 Cl 0.18658(11) 0.76950(8) 0.60089(5) 0.0727(3) Uani 1 1 d . . .
N1 N -0.0497(2) 0.70754(17) 0.42219(14) 0.0353(4) Uani 1 1 d . . .
N2 N 0.15103(19) 0.85233(16) 0.36648(12) 0.0334(4) Uani 1 1 d . . .
C1 C -0.0924(3) 0.78285(18) 0.35975(16) 0.0334(5) Uani 1 1 d . . .
C2 C -0.2351(3) 0.7847(2) 0.32619(19) 0.0416(6) Uani 1 1 d . . .
H2A H -0.2630 0.8371 0.2826 0.050 Uiso 1 1 calc R . .
C3 C -0.3359(3) 0.7084(2) 0.3577(2) 0.0489(7) Uani 1 1 d . . .
H3A H -0.4322 0.7084 0.3352 0.059 Uiso 1 1 calc R . .
C4 C -0.2933(3) 0.6321(2) 0.4228(2) 0.0509(7) Uani 1 1 d . . .
H4A H -0.3599 0.5807 0.4458 0.061 Uiso 1 1 calc R . .
C5 C -0.1478(3) 0.6341(2) 0.45292(19) 0.0450(6) Uani 1 1 d . . .
H5A H -0.1174 0.5822 0.4963 0.054 Uiso 1 1 calc R . .
C6 C 0.0234(2) 0.8627(2) 0.32957(16) 0.0365(5) Uani 1 1 d . . .
C7 C -0.0181(3) 0.9501(3) 0.2616(2) 0.0601(8) Uani 1 1 d . . .
H7A H 0.0666 0.9950 0.2483 0.090 Uiso 1 1 calc R . .
H7B H -0.0934 0.9985 0.2840 0.090 Uiso 1 1 calc R . .
H7C H -0.0542 0.9129 0.2086 0.090 Uiso 1 1 calc R . .
C8 C 0.2743(2) 0.9202(2) 0.33927(16) 0.0342(5) Uani 1 1 d . . .
C9 C 0.3490(3) 0.8886(2) 0.26430(16) 0.0386(5) Uani 1 1 d . . .
C10 C 0.4724(3) 0.9516(3) 0.24247(19) 0.0492(7) Uani 1 1 d . . .
H10A H 0.5227 0.9337 0.1915 0.059 Uiso 1 1 calc R . .
C11 C 0.5206(3) 1.0396(3) 0.2952(2) 0.0547(8) Uani 1 1 d . . .
H11A H 0.6045 1.0798 0.2805 0.066 Uiso 1 1 calc R . .
C12 C 0.4457(3) 1.0691(2) 0.3698(2) 0.0549(7) Uani 1 1 d . . .
H12A H 0.4803 1.1289 0.4051 0.066 Uiso 1 1 calc R . .
C13 C 0.3192(3) 1.0110(2) 0.39326(19) 0.0431(6) Uani 1 1 d . . .
C14 C 0.2980(4) 0.7908(3) 0.2066(2) 0.0557(8) Uani 1 1 d . . .
H14A H 0.2120 0.7571 0.2309 0.084 Uiso 1 1 calc R . .
H14B H 0.3747 0.7348 0.2041 0.084 Uiso 1 1 calc R . .
H14C H 0.2750 0.8182 0.1479 0.084 Uiso 1 1 calc R . .
C15 C 0.2355(4) 1.0464(3) 0.4718(2) 0.0671(9) Uani 1 1 d . . .
H15A H 0.1524 0.9970 0.4781 0.101 Uiso 1 1 calc R . .
H15B H 0.2020 1.1234 0.4640 0.101 Uiso 1 1 calc R . .
H15C H 0.2981 1.0417 0.5240 0.101 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.066(2) . ?
Zn1 N2 2.0691(18) . ?
Zn1 Cl2 2.1969(9) . ?
Zn1 Cl1 2.1979(8) . ?
N1 C5 1.334(3) . ?
N1 C1 1.341(3) . ?
N2 C6 1.278(3) . ?
N2 C8 1.445(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.491(3) . ?
C2 C3 1.378(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(4) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.492(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.388(3) . ?
C8 C13 1.396(4) . ?
C9 C10 1.393(3) . ?
C9 C14 1.506(4) . ?
C10 C11 1.368(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.378(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.393(4) . ?
C12 H12A 0.9300 . ?
C13 C15 1.487(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 79.73(8) . . ?
N1 Zn1 Cl2 109.19(7) . . ?
N2 Zn1 Cl2 118.90(6) . . ?
N1 Zn1 Cl1 114.58(6) . . ?
N2 Zn1 Cl1 111.04(6) . . ?
Cl2 Zn1 Cl1 117.55(4) . . ?
C5 N1 C1 119.2(2) . . ?
C5 N1 Zn1 127.87(17) . . ?
C1 N1 Zn1 112.92(15) . . ?
C6 N2 C8 121.75(19) . . ?
C6 N2 Zn1 114.86(16) . . ?
C8 N2 Zn1 123.22(14) . . ?
N1 C1 C2 121.2(2) . . ?
N1 C1 C6 115.9(2) . . ?
C2 C1 C6 122.9(2) . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 H4A 121.0 . . ?
C5 C4 H4A 121.0 . . ?
N1 C5 C4 122.6(2) . . ?
N1 C5 H5A 118.7 . . ?
C4 C5 H5A 118.7 . . ?
N2 C6 C1 116.6(2) . . ?
N2 C6 C7 125.0(2) . . ?
C1 C6 C7 118.4(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 122.6(2) . . ?
C9 C8 N2 119.1(2) . . ?
C13 C8 N2 118.1(2) . . ?
C8 C9 C10 117.9(2) . . ?
C8 C9 C14 121.8(2) . . ?
C10 C9 C14 120.3(2) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12A 119.4 . . ?
C13 C12 H12A 119.4 . . ?
C12 C13 C8 117.1(3) . . ?
C12 C13 C15 120.8(3) . . ?
C8 C13 C15 122.1(2) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_Zn4
_database_code_depnum_ccdc_archive 'CCDC 1494308'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cl2 N2 Zn'
_chemical_formula_weight         374.61

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c   '

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

_cell_length_a                   32.804(14)
_cell_length_b                   13.390(5)
_cell_length_c                   16.187(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.815(8)
_cell_angle_gamma                90.00
_cell_volume                     7060(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    24100
_cell_measurement_theta_min      1.25
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3071
_exptl_absorpt_coefficient_mu    1.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7979
_exptl_absorpt_correction_T_max  0.8360
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24100
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.25
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6209
_reflns_number_gt                5207
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1176P)²+3.5163P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6209
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.165980(11) 0.44551(3) 0.28337(2) 0.04180(16) Uani 1 1 d . . .
Zn2 Zn 0.166270(11) 0.02584(3) 0.53602(2) 0.04107(16) Uani 1 1 d . . .
Cl1 Cl 0.18300(5) 0.59580(9) 0.33079(7) 0.0861(4) Uani 1 1 d . . .
Cl2 Cl 0.15241(4) 0.33565(9) 0.37667(7) 0.0689(3) Uani 1 1 d . . .
Cl3 Cl 0.17520(4) -0.12993(8) 0.57977(7) 0.0703(3) Uani 1 1 d . . .
Cl4 Cl 0.15662(3) 0.13907(7) 0.63020(6) 0.0557(3) Uani 1 1 d . . .
N1 N 0.20872(8) 0.3944(2) 0.20987(17) 0.0414(6) Uani 1 1 d . . .
N2 N 0.13019(8) 0.4380(2) 0.16919(17) 0.0413(6) Uani 1 1 d . . .
N3 N 0.20962(8) 0.0785(2) 0.46441(16) 0.0404(6) Uani 1 1 d . . .
N4 N 0.13150(8) 0.0326(2) 0.42099(16) 0.0376(6) Uani 1 1 d . . .
C1 C 0.19486(10) 0.3895(2) 0.1293(2) 0.0410(7) Uani 1 1 d . . .
C2 C 0.21949(12) 0.3643(3) 0.0686(2) 0.0524(9) Uani 1 1 d . . .
H2A H 0.2091 0.3634 0.0126 0.063 Uiso 1 1 calc R . .
C3 C 0.26104(12) 0.3399(3) 0.0951(3) 0.0571(10) Uani 1 1 d . . .
H3A H 0.2784 0.3215 0.0563 0.068 Uiso 1 1 calc R . .
C4 C 0.27556(12) 0.3436(3) 0.1788(3) 0.0567(10) Uani 1 1 d . . .
H4A H 0.3027 0.3280 0.1973 0.068 Uiso 1 1 calc R . .
C5 C 0.24839(10) 0.3713(3) 0.2345(2) 0.0501(9) Uani 1 1 d . . .
H5A H 0.2579 0.3739 0.2909 0.060 Uiso 1 1 calc R . .
C6 C 0.15010(11) 0.4133(3) 0.1086(2) 0.0475(8) Uani 1 1 d . . .
C7 C 0.13164(15) 0.4042(5) 0.0190(3) 0.0849(16) Uani 1 1 d . . .
H7A H 0.1030 0.4214 0.0144 0.127 Uiso 1 1 calc R . .
H7B H 0.1346 0.3368 0.0004 0.127 Uiso 1 1 calc R . .
H7C H 0.1456 0.4487 -0.0147 0.127 Uiso 1 1 calc R . .
C8 C 0.08709(11) 0.4584(3) 0.1557(2) 0.0471(8) Uani 1 1 d . . .
C9 C 0.07402(13) 0.5558(3) 0.1395(3) 0.0636(11) Uani 1 1 d . . .
C10 C 0.03165(14) 0.5737(4) 0.1299(3) 0.0795(14) Uani 1 1 d . . .
H10A H 0.0222 0.6388 0.1214 0.095 Uiso 1 1 calc R . .
C11 C 0.00378(14) 0.4978(5) 0.1328(3) 0.0828(15) Uani 1 1 d . . .
C12 C 0.01753(13) 0.4018(4) 0.1505(3) 0.0768(14) Uani 1 1 d . . .
H12A H -0.0014 0.3511 0.1553 0.092 Uiso 1 1 calc R . .
C13 C 0.05910(12) 0.3796(3) 0.1610(3) 0.0611(10) Uani 1 1 d . . .
C14 C 0.10472(16) 0.6397(3) 0.1345(4) 0.0914(17) Uani 1 1 d . . .
H14A H 0.1321 0.6131 0.1425 0.137 Uiso 1 1 calc R . .
H14B H 0.1015 0.6882 0.1770 0.137 Uiso 1 1 calc R . .
H14C H 0.1000 0.6710 0.0809 0.137 Uiso 1 1 calc R . .
C15 C -0.04269(15) 0.5204(6) 0.1256(4) 0.125(3) Uani 1 1 d . . .
H15A H -0.0472 0.5899 0.1133 0.188 Uiso 1 1 calc R . .
H15B H -0.0529 0.5047 0.1773 0.188 Uiso 1 1 calc R . .
H15C H -0.0568 0.4807 0.0819 0.188 Uiso 1 1 calc R . .
C16 C 0.07420(15) 0.2738(3) 0.1780(4) 0.100(2) Uani 1 1 d . . .
H16A H 0.0511 0.2301 0.1795 0.151 Uiso 1 1 calc R . .
H16B H 0.0912 0.2716 0.2305 0.151 Uiso 1 1 calc R . .
H16C H 0.0899 0.2528 0.1347 0.151 Uiso 1 1 calc R . .
C17 C 0.19569(10) 0.0882(2) 0.38423(19) 0.0376(7) Uani 1 1 d . . .
C18 C 0.22103(11) 0.1197(3) 0.3259(2) 0.0488(8) Uani 1 1 d . . .
H18A H 0.2109 0.1237 0.2699 0.059 Uiso 1 1 calc R . .
C19 C 0.26113(12) 0.1446(3) 0.3519(3) 0.0570(10) Uani 1 1 d . . .
H19A H 0.2785 0.1647 0.3137 0.068 Uiso 1 1 calc R . .
C20 C 0.27513(12) 0.1393(3) 0.4355(3) 0.0592(10) Uani 1 1 d . . .
H20A H 0.3017 0.1595 0.4546 0.071 Uiso 1 1 calc R . .
C21 C 0.24929(11) 0.1035(3) 0.4911(3) 0.0557(9) Uani 1 1 d . . .
H21A H 0.2592 0.0966 0.5470 0.067 Uiso 1 1 calc R . .
C22 C 0.15135(10) 0.0615(2) 0.36138(19) 0.0382(7) Uani 1 1 d . . .
C23 C 0.13320(13) 0.0706(3) 0.2723(2) 0.0578(10) Uani 1 1 d . . .
H23A H 0.1048 0.0511 0.2670 0.087 Uiso 1 1 calc R . .
H23B H 0.1478 0.0279 0.2383 0.087 Uiso 1 1 calc R . .
H23C H 0.1353 0.1385 0.2543 0.087 Uiso 1 1 calc R . .
C24 C 0.08860(10) 0.0057(3) 0.4050(2) 0.0413(7) Uani 1 1 d . . .
C25 C 0.05887(11) 0.0784(3) 0.4172(2) 0.0500(9) Uani 1 1 d . . .
C26 C 0.01769(12) 0.0506(4) 0.4034(3) 0.0597(11) Uani 1 1 d . . .
H26A H -0.0025 0.0971 0.4116 0.072 Uiso 1 1 calc R . .
C27 C 0.00624(13) -0.0447(4) 0.3778(3) 0.0666(13) Uani 1 1 d . . .
C28 C 0.03597(12) -0.1162(4) 0.3683(3) 0.0625(11) Uani 1 1 d . . .
H28A H 0.0280 -0.1809 0.3531 0.075 Uiso 1 1 calc R . .
C29 C 0.07793(12) -0.0919(3) 0.3814(2) 0.0533(9) Uani 1 1 d . . .
C30 C 0.07075(13) 0.1727(3) 0.4394(3) 0.0683(12) Uani 1 1 d . . .
H30A H 0.0470 0.2127 0.4452 0.102 Uiso 1 1 calc R . .
H30B H 0.0855 0.2011 0.3973 0.102 Uiso 1 1 calc R . .
H30C H 0.0882 0.1711 0.4914 0.102 Uiso 1 1 calc R . .
C31 C -0.03916(13) -0.0764(5) 0.3624(3) 0.0949(19) Uani 1 1 d . . .
H31A H -0.0563 -0.0202 0.3710 0.142 Uiso 1 1 calc R . .
H31B H -0.0441 -0.1289 0.4003 0.142 Uiso 1 1 calc R . .
H31C H -0.0453 -0.0999 0.3062 0.142 Uiso 1 1 calc R . .
C32 C 0.11023(14) -0.1693(3) 0.3657(3) 0.0736(12) Uani 1 1 d . . .
H32A H 0.1371 -0.1405 0.3776 0.110 Uiso 1 1 calc R . .
H32B H 0.1060 -0.1899 0.3085 0.110 Uiso 1 1 calc R . .
H32C H 0.1079 -0.2261 0.4010 0.110 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.061(3) . ?
Zn1 N2 2.071(3) . ?
Zn1 Cl2 2.1915(12) . ?
Zn1 Cl1 2.2020(14) . ?
Zn2 N3 2.063(3) . ?
Zn2 N4 2.067(3) . ?
Zn2 Cl4 2.1994(11) . ?
Zn2 Cl3 2.2110(13) . ?
N1 C1 1.331(4) . ?
N1 C5 1.351(4) . ?
N2 C6 1.285(5) . ?
N2 C8 1.431(4) . ?
N3 C17 1.330(4) . ?
N3 C21 1.363(4) . ?
N4 C22 1.286(4) . ?
N4 C24 1.446(4) . ?
C1 C2 1.386(5) . ?
C1 C6 1.501(5) . ?
C2 C3 1.417(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.383(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.508(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.388(5) . ?
C8 C13 1.408(5) . ?
C9 C10 1.401(6) . ?
C9 C14 1.518(6) . ?
C10 C11 1.372(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.381(8) . ?
C11 C15 1.545(6) . ?
C12 C13 1.386(6) . ?
C12 H12A 0.9300 . ?
C13 C16 1.515(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.395(4) . ?
C17 C22 1.501(4) . ?
C18 C19 1.374(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.378(6) . ?
C19 H19A 0.9300 . ?
C20 C21 1.392(5) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 C23 1.499(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C29 1.395(5) . ?
C24 C25 1.409(5) . ?
C25 C30 1.358(6) . ?
C25 C26 1.394(5) . ?
C26 C27 1.379(6) . ?
C26 H26A 0.9300 . ?
C27 C28 1.388(7) . ?
C27 C31 1.540(6) . ?
C28 C29 1.406(5) . ?
C28 H28A 0.9300 . ?
C29 C32 1.525(6) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

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 79.69(11) . . ?
N1 Zn1 Cl2 112.50(9) . . ?
N2 Zn1 Cl2 116.25(9) . . ?
N1 Zn1 Cl1 110.07(9) . . ?
N2 Zn1 Cl1 116.68(9) . . ?
Cl2 Zn1 Cl1 115.92(5) . . ?
N3 Zn2 N4 79.77(10) . . ?
N3 Zn2 Cl4 108.61(8) . . ?
N4 Zn2 Cl4 119.01(8) . . ?
N3 Zn2 Cl3 115.39(9) . . ?
N4 Zn2 Cl3 111.57(8) . . ?
Cl4 Zn2 Cl3 116.92(5) . . ?
C1 N1 C5 118.9(3) . . ?
C1 N1 Zn1 113.9(2) . . ?
C5 N1 Zn1 127.1(2) . . ?
C6 N2 C8 121.0(3) . . ?
C6 N2 Zn1 114.1(2) . . ?
C8 N2 Zn1 124.9(2) . . ?
C17 N3 C21 119.3(3) . . ?
C17 N3 Zn2 113.7(2) . . ?
C21 N3 Zn2 127.0(2) . . ?
C22 N4 C24 120.6(3) . . ?
C22 N4 Zn2 114.5(2) . . ?
C24 N4 Zn2 124.85(19) . . ?
N1 C1 C2 123.1(3) . . ?
N1 C1 C6 114.8(3) . . ?
C2 C1 C6 122.0(3) . . ?
C1 C2 C3 117.6(4) . . ?
C1 C2 H2A 121.2 . . ?
C3 C2 H2A 121.2 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 H4A 120.9 . . ?
N1 C5 C4 122.6(4) . . ?
N1 C5 H5A 118.7 . . ?
C4 C5 H5A 118.7 . . ?
N2 C6 C1 117.1(3) . . ?
N2 C6 C7 124.9(4) . . ?
C1 C6 C7 117.9(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 121.8(4) . . ?
C9 C8 N2 119.1(3) . . ?
C13 C8 N2 119.2(3) . . ?
C8 C9 C10 117.6(4) . . ?
C8 C9 C14 120.9(4) . . ?
C10 C9 C14 121.5(4) . . ?
C11 C10 C9 121.7(5) . . ?
C11 C10 H10A 119.2 . . ?
C9 C10 H10A 119.2 . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 C15 120.5(6) . . ?
C12 C11 C15 119.6(6) . . ?
C11 C12 C13 121.1(5) . . ?
C11 C12 H12A 119.4 . . ?
C13 C12 H12A 119.4 . . ?
C12 C13 C8 118.1(4) . . ?
C12 C13 C16 121.2(4) . . ?
C8 C13 C16 120.7(4) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C18 121.8(3) . . ?
N3 C17 C22 115.3(3) . . ?
C18 C17 C22 122.9(3) . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C18 C19 C20 118.9(4) . . ?
C18 C19 H19A 120.5 . . ?
C20 C19 H19A 120.5 . . ?
C19 C20 C21 119.7(4) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
N3 C21 C20 120.7(4) . . ?
N3 C21 H21A 119.6 . . ?
C20 C21 H21A 119.6 . . ?
N4 C22 C23 124.6(3) . . ?
N4 C22 C17 116.7(3) . . ?
C23 C22 C17 118.7(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C24 C25 122.1(3) . . ?
C29 C24 N4 119.3(3) . . ?
C25 C24 N4 118.6(3) . . ?
C30 C25 C26 122.3(4) . . ?
C30 C25 C24 119.9(3) . . ?
C26 C25 C24 117.8(4) . . ?
C27 C26 C25 121.3(4) . . ?
C27 C26 H26A 119.3 . . ?
C25 C26 H26A 119.3 . . ?
C26 C27 C28 120.1(4) . . ?
C26 C27 C31 121.8(5) . . ?
C28 C27 C31 118.1(5) . . ?
C27 C28 C29 120.8(4) . . ?
C27 C28 H28A 119.6 . . ?
C29 C28 H28A 119.6 . . ?
C24 C29 C28 117.9(4) . . ?
C24 C29 C32 121.7(3) . . ?
C28 C29 C32 120.3(4) . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C31 H31A 109.5 . . ?
C27 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C27 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.435
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.114
