# 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_1
_audit_block_doi                 10.5517/cc1k37vr
_database_code_depnum_ccdc_archive 'CCDC 1433094'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 Cl2 N5 O S Zn'
_chemical_formula_weight         385.57

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   15.220(3)
_cell_length_b                   6.8071(14)
_cell_length_c                   15.097(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.90(3)
_cell_angle_gamma                90.00
_cell_volume                     1407.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4477
_cell_measurement_theta_min      2.5320
_cell_measurement_theta_max      28.0955

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    2.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6591
_exptl_absorpt_correction_T_max  0.7720
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  'rigaku saturn'
_diffrn_measurement_method       'ω 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            13199
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0705
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         28.05
_reflns_number_total             3285
_reflns_number_gt                2627
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0612P)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         3285
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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 0.19950(3) 0.40098(5) 0.50439(3) 0.01457(13) Uani 1 1 d . . .
Cl2 Cl 0.28007(6) 0.59500(10) 0.63406(6) 0.01755(19) Uani 1 1 d . . .
Cl1 Cl 0.08706(5) 0.20620(11) 0.51524(6) 0.0199(2) Uani 1 1 d . . .
S1 S 0.38119(6) 0.13651(11) 0.62076(6) 0.01729(19) Uani 1 1 d . . .
N1 N 0.14493(18) 0.5931(3) 0.3869(2) 0.0155(6) Uani 1 1 d . . .
N4 N 0.30432(19) 0.0938(3) 0.41986(19) 0.0149(6) Uani 1 1 d . . .
O1 O 0.52466(16) -0.3401(3) 0.63456(17) 0.0219(5) Uani 1 1 d . . .
N5 N 0.41185(18) -0.1411(3) 0.5183(2) 0.0149(6) Uani 1 1 d . . .
N3 N 0.25662(18) 0.2733(3) 0.41692(18) 0.0139(5) Uani 1 1 d . . .
C9 C 0.4623(2) -0.0605(4) 0.6879(2) 0.0177(7) Uani 1 1 d . . .
H9A H 0.5260 -0.0084 0.7316 0.021 Uiso 1 1 calc R . .
H9B H 0.4363 -0.1303 0.7272 0.021 Uiso 1 1 calc R . .
N2 N 0.22890(19) 0.2692(4) 0.2518(2) 0.0192(6) Uani 1 1 d . . .
H2A H 0.2614 0.1621 0.2595 0.023 Uiso 1 1 calc R . .
H2B H 0.2027 0.3252 0.1950 0.023 Uiso 1 1 calc R . .
C6 C 0.2192(2) 0.3480(4) 0.3273(2) 0.0143(6) Uani 1 1 d . . .
C5 C 0.1659(2) 0.5377(4) 0.3119(2) 0.0128(6) Uani 1 1 d . . .
C7 C 0.3592(2) 0.0307(4) 0.5067(2) 0.0128(6) Uani 1 1 d . . .
C8 C 0.4710(2) -0.1981(4) 0.6130(2) 0.0165(7) Uani 1 1 d . . .
C2 C 0.0778(2) 0.8926(4) 0.3026(3) 0.0185(7) Uani 1 1 d . . .
H2C H 0.0483 1.0129 0.3013 0.022 Uiso 1 1 calc R . .
C1 C 0.1026(2) 0.7663(4) 0.3826(2) 0.0188(7) Uani 1 1 d . . .
H1A H 0.0892 0.8041 0.4347 0.023 Uiso 1 1 calc R . .
C4 C 0.1421(2) 0.6555(4) 0.2298(2) 0.0179(7) Uani 1 1 d . . .
H4B H 0.1556 0.6148 0.1782 0.021 Uiso 1 1 calc R . .
C3 C 0.0975(2) 0.8366(4) 0.2260(2) 0.0183(7) Uani 1 1 d . . .
H3A H 0.0814 0.9187 0.1719 0.022 Uiso 1 1 calc R . .
C10 C 0.4055(2) -0.2600(4) 0.4347(2) 0.0209(7) Uani 1 1 d . . .
H10A H 0.4474 -0.3725 0.4586 0.031 Uiso 1 1 calc R . .
H10B H 0.4257 -0.1826 0.3937 0.031 Uiso 1 1 calc R . .
H10C H 0.3394 -0.3027 0.3971 0.031 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0182(2) 0.0137(2) 0.0140(2) -0.00028(13) 0.00907(17) -0.00045(14)
Cl2 0.0208(4) 0.0149(4) 0.0178(4) -0.0037(3) 0.0092(3) -0.0024(3)
Cl1 0.0203(4) 0.0213(4) 0.0186(4) 0.0004(3) 0.0090(3) -0.0055(3)
S1 0.0200(4) 0.0152(4) 0.0149(4) -0.0023(3) 0.0061(3) 0.0033(3)
N1 0.0153(13) 0.0149(13) 0.0174(15) 0.0011(10) 0.0081(11) 0.0023(10)
N4 0.0177(13) 0.0116(12) 0.0158(15) -0.0004(10) 0.0078(11) 0.0023(10)
O1 0.0231(12) 0.0153(11) 0.0273(14) 0.0030(10) 0.0109(11) 0.0049(10)
N5 0.0192(13) 0.0099(11) 0.0179(15) -0.0009(11) 0.0102(12) 0.0009(10)
N3 0.0180(13) 0.0101(12) 0.0146(15) -0.0020(10) 0.0081(11) -0.0003(10)
C9 0.0215(16) 0.0144(14) 0.0149(17) -0.0003(13) 0.0059(13) 0.0002(13)
N2 0.0269(15) 0.0174(13) 0.0152(15) 0.0007(11) 0.0110(12) 0.0062(11)
C6 0.0138(14) 0.0141(14) 0.0153(17) -0.0008(12) 0.0066(13) -0.0015(12)
C5 0.0125(14) 0.0121(14) 0.0145(16) 0.0001(12) 0.0064(12) -0.0016(12)
C7 0.0142(14) 0.0102(13) 0.0166(16) -0.0017(12) 0.0091(12) -0.0024(11)
C8 0.0173(15) 0.0146(14) 0.0183(18) 0.0022(13) 0.0084(13) -0.0020(12)
C2 0.0155(15) 0.0109(14) 0.027(2) -0.0007(13) 0.0067(14) 0.0007(12)
C1 0.0181(15) 0.0179(15) 0.0205(18) -0.0007(13) 0.0085(14) 0.0008(13)
C4 0.0199(16) 0.0179(15) 0.0169(18) -0.0011(13) 0.0089(14) -0.0018(13)
C3 0.0174(15) 0.0152(15) 0.0196(18) 0.0047(13) 0.0056(13) -0.0031(13)
C10 0.0250(17) 0.0202(16) 0.0216(19) -0.0038(14) 0.0140(15) 0.0022(14)

_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 N3 2.063(2) . ?
Zn1 N1 2.064(3) . ?
Zn1 Cl1 2.2267(8) . ?
Zn1 Cl2 2.2323(10) . ?
S1 C7 1.759(3) . ?
S1 C9 1.805(3) . ?
N1 C1 1.332(3) . ?
N1 C5 1.357(4) . ?
N4 C7 1.282(4) . ?
N4 N3 1.412(3) . ?
O1 C8 1.214(3) . ?
N5 C8 1.371(4) . ?
N5 C7 1.385(3) . ?
N5 C10 1.467(4) . ?
N3 C6 1.319(4) . ?
C9 C8 1.518(4) . ?
N2 C6 1.326(4) . ?
C6 C5 1.489(4) . ?
C5 C4 1.384(4) . ?
C2 C3 1.370(4) . ?
C2 C1 1.394(4) . ?
C4 C3 1.397(4) . ?

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
N3 Zn1 N1 80.81(10) . . ?
N3 Zn1 Cl1 110.40(7) . . ?
N1 Zn1 Cl1 114.01(8) . . ?
N3 Zn1 Cl2 125.93(7) . . ?
N1 Zn1 Cl2 103.88(8) . . ?
Cl1 Zn1 Cl2 115.67(4) . . ?
C7 S1 C9 92.11(14) . . ?
C1 N1 C5 119.4(3) . . ?
C1 N1 Zn1 127.3(2) . . ?
C5 N1 Zn1 112.87(19) . . ?
C7 N4 N3 114.8(2) . . ?
C8 N5 C7 116.8(3) . . ?
C8 N5 C10 120.5(2) . . ?
C7 N5 C10 122.7(3) . . ?
C6 N3 N4 110.6(2) . . ?
C6 N3 Zn1 112.34(19) . . ?
N4 N3 Zn1 134.33(19) . . ?
C8 C9 S1 107.5(2) . . ?
N3 C6 N2 124.5(3) . . ?
N3 C6 C5 117.2(3) . . ?
N2 C6 C5 118.3(3) . . ?
N1 C5 C4 121.4(3) . . ?
N1 C5 C6 114.9(3) . . ?
C4 C5 C6 123.6(3) . . ?
N4 C7 N5 119.7(3) . . ?
N4 C7 S1 128.6(2) . . ?
N5 C7 S1 111.7(2) . . ?
O1 C8 N5 124.3(3) . . ?
O1 C8 C9 123.9(3) . . ?
N5 C8 C9 111.8(3) . . ?
C3 C2 C1 118.9(3) . . ?
N1 C1 C2 122.0(3) . . ?
C5 C4 C3 118.7(3) . . ?
C2 C3 C4 119.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        28.05
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.702
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.134

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

data_1
_audit_block_doi                 10.5517/cc1k37ws
_database_code_depnum_ccdc_archive 'CCDC 1433095'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 Cl2 N5 O S Zn'
_chemical_formula_weight         399.59

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'
S S 0.1246 0.1234 '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                   11.624(2)
_cell_length_b                   11.064(2)
_cell_length_c                   12.437(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.48(3)
_cell_angle_gamma                90.00
_cell_volume                     1572.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4500
_cell_measurement_theta_min      2.4825
_cell_measurement_theta_max      27.8306

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    2.038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6860
_exptl_absorpt_correction_T_max  0.7920
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  'rigaku saturn'
_diffrn_measurement_method       'ω 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            15684
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.94
_reflns_number_total             3741
_reflns_number_gt                3032
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0372P)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     SHELXL
_refine_ls_extinction_coef       0.0158(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3741
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.614259(16) -0.145029(18) 0.224720(16) 0.01202(8) Uani 1 1 d . . .
S1 S 0.40288(4) 0.02034(4) 0.26255(4) 0.01532(11) Uani 1 1 d . . .
Cl1 Cl 0.71599(4) -0.10883(4) 0.39131(4) 0.01883(11) Uani 1 1 d . . .
Cl2 Cl 0.48129(4) -0.28983(4) 0.20796(4) 0.02282(12) Uani 1 1 d . . .
N1 N 0.71978(12) -0.18716(13) 0.11289(11) 0.0113(3) Uani 1 1 d . . .
O1 O 0.33077(11) 0.34605(12) 0.34379(11) 0.0227(3) Uani 1 1 d . . .
N3 N 0.56124(12) 0.12929(13) 0.15460(12) 0.0124(3) Uani 1 1 d . . .
C9 C 0.36495(15) 0.25269(17) 0.30778(14) 0.0147(4) Uani 1 1 d . . .
C7 C 0.48141(14) 0.13640(15) 0.21216(14) 0.0107(3) Uani 1 1 d . . .
N2 N 0.60222(12) 0.01309(13) 0.13583(11) 0.0113(3) Uani 1 1 d . . .
N5 N 0.68757(13) 0.11598(14) 0.00753(13) 0.0185(3) Uani 1 1 d . . .
H2B H 0.6516 0.1816 0.0182 0.022 Uiso 1 1 calc R . .
H2C H 0.7338 0.1146 -0.0392 0.022 Uiso 1 1 calc R . .
N4 N 0.44710(12) 0.25057(13) 0.24259(12) 0.0118(3) Uani 1 1 d . . .
C10 C 0.50061(15) 0.36230(16) 0.21073(14) 0.0143(4) Uani 1 1 d . . .
H10A H 0.5823 0.3472 0.2082 0.017 Uiso 1 1 calc R . .
H10B H 0.4973 0.4239 0.2656 0.017 Uiso 1 1 calc R . .
C5 C 0.73614(15) -0.09540(16) 0.04647(13) 0.0108(3) Uani 1 1 d . . .
C8 C 0.32354(16) 0.12799(17) 0.33075(16) 0.0188(4) Uani 1 1 d . . .
H8A H 0.2402 0.1207 0.3036 0.023 Uiso 1 1 calc R . .
H8B H 0.3382 0.1129 0.4089 0.023 Uiso 1 1 calc R . .
C4 C 0.81107(15) -0.10592(17) -0.02835(14) 0.0155(4) Uani 1 1 d . . .
H4A H 0.8216 -0.0416 -0.0738 0.019 Uiso 1 1 calc R . .
C2 C 0.85104(15) -0.30948(17) 0.03282(15) 0.0168(4) Uani 1 1 d . . .
H2A H 0.8887 -0.3832 0.0294 0.020 Uiso 1 1 calc R . .
C6 C 0.67185(14) 0.01742(15) 0.06284(13) 0.0112(3) Uani 1 1 d . . .
C11 C 0.43991(19) 0.40807(18) 0.10112(16) 0.0258(5) Uani 1 1 d . . .
H11A H 0.4772 0.4810 0.0834 0.039 Uiso 1 1 calc R . .
H11B H 0.3593 0.4244 0.1037 0.039 Uiso 1 1 calc R . .
H11C H 0.4444 0.3480 0.0463 0.039 Uiso 1 1 calc R . .
C3 C 0.87008(15) -0.21475(18) -0.03390(15) 0.0182(4) Uani 1 1 d . . .
H3A H 0.9219 -0.2234 -0.0822 0.022 Uiso 1 1 calc R . .
C1 C 0.77451(15) -0.29252(16) 0.10507(14) 0.0144(4) Uani 1 1 d . . .
H1A H 0.7607 -0.3565 0.1496 0.017 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.01560(13) 0.01013(11) 0.01211(12) 0.00089(8) 0.00729(8) -0.00052(8)
S1 0.0160(2) 0.0111(2) 0.0214(2) 0.00061(17) 0.01036(19) -0.00005(17)
Cl1 0.0264(3) 0.0174(2) 0.0128(2) -0.00048(17) 0.00379(18) 0.00422(19)
Cl2 0.0241(3) 0.0167(2) 0.0312(3) -0.00381(19) 0.0144(2) -0.00815(19)
N1 0.0140(7) 0.0099(7) 0.0106(7) 0.0005(6) 0.0038(6) 0.0006(6)
O1 0.0283(8) 0.0159(7) 0.0294(8) -0.0038(6) 0.0199(6) 0.0034(6)
N3 0.0151(8) 0.0091(7) 0.0148(7) 0.0006(6) 0.0074(6) 0.0023(6)
C9 0.0139(9) 0.0158(9) 0.0156(9) 0.0002(7) 0.0060(7) 0.0012(7)
C7 0.0116(8) 0.0109(8) 0.0100(8) -0.0013(6) 0.0028(7) 0.0005(7)
N2 0.0140(7) 0.0078(7) 0.0137(7) 0.0002(6) 0.0071(6) 0.0019(6)
N5 0.0258(9) 0.0115(7) 0.0236(8) 0.0033(6) 0.0191(7) 0.0036(7)
N4 0.0137(8) 0.0097(7) 0.0137(7) -0.0009(6) 0.0074(6) 0.0010(6)
C10 0.0158(9) 0.0104(8) 0.0182(9) -0.0024(7) 0.0072(7) -0.0018(7)
C5 0.0113(8) 0.0107(8) 0.0111(8) -0.0010(6) 0.0039(7) 0.0006(7)
C8 0.0204(10) 0.0172(10) 0.0229(10) 0.0010(8) 0.0148(8) 0.0020(8)
C4 0.0186(9) 0.0149(9) 0.0149(9) 0.0028(7) 0.0082(7) 0.0012(8)
C2 0.0170(9) 0.0147(9) 0.0189(9) -0.0011(7) 0.0039(7) 0.0058(8)
C6 0.0118(8) 0.0109(9) 0.0114(8) 0.0002(6) 0.0039(7) -0.0006(7)
C11 0.0426(13) 0.0141(10) 0.0206(10) 0.0028(8) 0.0056(9) -0.0022(9)
C3 0.0188(10) 0.0212(10) 0.0167(10) -0.0015(7) 0.0092(8) 0.0046(8)
C1 0.0171(9) 0.0116(8) 0.0143(9) 0.0005(7) 0.0020(7) 0.0012(7)

_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 2.0605(15) . ?
Zn1 N1 2.0680(15) . ?
Zn1 Cl2 2.2095(6) . ?
Zn1 Cl1 2.2272(8) . ?
S1 C7 1.7559(17) . ?
S1 C8 1.8092(18) . ?
N1 C1 1.340(2) . ?
N1 C5 1.344(2) . ?
O1 C9 1.221(2) . ?
N3 C7 1.273(2) . ?
N3 N2 1.4053(19) . ?
C9 N4 1.361(2) . ?
C9 C8 1.505(2) . ?
C7 N4 1.397(2) . ?
N2 C6 1.322(2) . ?
N5 C6 1.320(2) . ?
N4 C10 1.470(2) . ?
C10 C11 1.504(3) . ?
C5 C4 1.390(2) . ?
C5 C6 1.488(2) . ?
C4 C3 1.394(3) . ?
C2 C3 1.379(3) . ?
C2 C1 1.387(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 79.70(6) . . ?
N2 Zn1 Cl2 125.94(5) . . ?
N1 Zn1 Cl2 105.27(5) . . ?
N2 Zn1 Cl1 108.61(4) . . ?
N1 Zn1 Cl1 112.75(4) . . ?
Cl2 Zn1 Cl1 117.52(3) . . ?
C7 S1 C8 91.62(8) . . ?
C1 N1 C5 119.37(15) . . ?
C1 N1 Zn1 126.32(12) . . ?
C5 N1 Zn1 114.25(11) . . ?
C7 N3 N2 116.98(14) . . ?
O1 C9 N4 122.93(17) . . ?
O1 C9 C8 124.70(16) . . ?
N4 C9 C8 112.37(15) . . ?
N3 C7 N4 118.76(15) . . ?
N3 C7 S1 129.40(14) . . ?
N4 C7 S1 111.83(12) . . ?
C6 N2 N3 110.43(14) . . ?
C6 N2 Zn1 114.13(11) . . ?
N3 N2 Zn1 132.81(10) . . ?
C9 N4 C7 116.28(15) . . ?
C9 N4 C10 121.55(15) . . ?
C7 N4 C10 122.10(13) . . ?
N4 C10 C11 112.06(15) . . ?
N1 C5 C4 121.61(16) . . ?
N1 C5 C6 114.77(14) . . ?
C4 C5 C6 123.59(15) . . ?
C9 C8 S1 107.85(12) . . ?
C5 C4 C3 118.64(16) . . ?
C3 C2 C1 118.61(17) . . ?
N5 C6 N2 123.23(16) . . ?
N5 C6 C5 120.09(15) . . ?
N2 C6 C5 116.67(15) . . ?
C2 C3 C4 119.50(16) . . ?
N1 C1 C2 122.24(17) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.096
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_audit_block_doi                 10.5517/cc1k3cxy
_database_code_depnum_ccdc_archive 'CCDC 1433220'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 Cl2 N5 O2 S Zn'
_chemical_formula_weight         389.59

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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   P21/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                   7.8176(16)
_cell_length_b                   10.961(2)
_cell_length_c                   17.170(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.17(3)
_cell_angle_gamma                90.00
_cell_volume                     1470.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3578
_cell_measurement_theta_min      2.2049
_cell_measurement_theta_max      27.8068

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    2.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7453
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω 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            14754
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         27.94
_reflns_number_total             3520
_reflns_number_gt                2465
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0717P)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         3520
_refine_ls_number_parameters     189
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.939
_refine_ls_shift/su_max          0.015
_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 0.18692(5) 0.79187(4) 0.12923(2) 0.03900(15) Uani 1 1 d . . .
Cl1 Cl 0.03737(12) 0.95948(8) 0.15333(6) 0.0503(3) Uani 1 1 d . . .
Cl2 Cl 0.31125(13) 0.70276(10) 0.23281(5) 0.0567(3) Uani 1 1 d . . .
S1 S -0.09296(11) 0.60552(9) 0.16261(5) 0.0433(2) Uani 1 1 d . . .
O1 O -0.5403(3) 0.4812(2) 0.10231(13) 0.0447(6) Uani 1 1 d . . .
N2 N 0.1303(4) 0.7170(2) -0.10515(15) 0.0377(7) Uani 1 1 d . . .
H2B H 0.0325 0.6831 -0.1147 0.045 Uiso 1 1 calc R . .
H2C H 0.1925 0.7388 -0.1430 0.045 Uiso 1 1 calc R . .
N1 N 0.3898(3) 0.8245(2) 0.05763(16) 0.0354(6) Uani 1 1 d . . .
N3 N 0.0982(3) 0.7049(2) 0.02898(14) 0.0286(5) Uani 1 1 d . . .
N4 N -0.0614(3) 0.6546(2) 0.00736(14) 0.0315(6) Uani 1 1 d . . .
N5 N -0.3079(3) 0.5644(2) 0.04733(15) 0.0339(6) Uani 1 1 d . . .
H5A H -0.3487 0.5576 0.0003 0.041 Uiso 1 1 calc R . .
C5 C 0.3579(4) 0.7895(3) -0.01661(18) 0.0297(6) Uani 1 1 d . . .
C4 C 0.4794(4) 0.8007(3) -0.0721(2) 0.0366(7) Uani 1 1 d . . .
H4A H 0.4552 0.7755 -0.1231 0.044 Uiso 1 1 calc R . .
C8 C -0.3980(4) 0.5283(3) 0.10826(17) 0.0320(7) Uani 1 1 d . . .
C2 C 0.6695(4) 0.8854(3) 0.0248(2) 0.0436(8) Uani 1 1 d . . .
H2A H 0.7748 0.9188 0.0402 0.052 Uiso 1 1 calc R . .
C7 C -0.3031(4) 0.5509(3) 0.18470(19) 0.0402(8) Uani 1 1 d . . .
H7A H -0.2944 0.4760 0.2147 0.048 Uiso 1 1 calc R . .
H7B H -0.3628 0.6112 0.2149 0.048 Uiso 1 1 calc R . .
C3 C 0.6369(4) 0.8495(3) -0.0517(2) 0.0420(8) Uani 1 1 d . . .
H3A H 0.7201 0.8582 -0.0886 0.050 Uiso 1 1 calc R . .
C38 C -0.1460(4) 0.6132(3) 0.06334(17) 0.0303(7) Uani 1 1 d . . .
C1 C 0.5434(4) 0.8705(3) 0.0772(2) 0.0435(8) Uani 1 1 d . . .
H1A H 0.5658 0.8936 0.1287 0.052 Uiso 1 1 calc R . .
C6 C 0.1850(4) 0.7355(3) -0.03221(17) 0.0287(6) Uani 1 1 d . . .
O2 O 0.2086(5) 0.3463(3) 0.1974(2) 0.0826(10) Uani 1 1 d D . .
H1W H 0.171(8) 0.364(5) 0.2425(19) 0.14(3) Uiso 1 1 d D . .
H2W H 0.266(8) 0.386(4) 0.164(3) 0.14(3) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0354(2) 0.0558(3) 0.0257(2) -0.01102(16) -0.00060(16) -0.00024(18)
Cl1 0.0460(5) 0.0566(6) 0.0483(5) -0.0158(4) 0.0007(4) 0.0045(4)
Cl2 0.0440(5) 0.1002(8) 0.0255(4) -0.0074(4) -0.0033(4) 0.0185(5)
S1 0.0365(5) 0.0655(6) 0.0274(4) 0.0038(4) -0.0043(4) -0.0100(4)
O1 0.0375(13) 0.0622(15) 0.0344(12) -0.0032(11) 0.0033(10) -0.0169(12)
N2 0.0347(15) 0.0562(18) 0.0222(13) -0.0013(12) 0.0015(11) -0.0115(13)
N1 0.0298(14) 0.0438(15) 0.0324(14) -0.0076(12) -0.0028(11) -0.0022(12)
N3 0.0249(13) 0.0391(15) 0.0217(12) -0.0023(10) -0.0004(10) -0.0042(10)
N4 0.0288(13) 0.0402(15) 0.0253(13) -0.0019(11) -0.0006(11) -0.0054(11)
N5 0.0290(13) 0.0440(15) 0.0284(13) 0.0004(12) -0.0011(11) -0.0053(12)
C5 0.0290(15) 0.0308(16) 0.0291(15) -0.0012(12) -0.0020(12) -0.0002(12)
C4 0.0325(17) 0.0435(19) 0.0340(17) 0.0013(14) 0.0028(14) -0.0026(14)
C8 0.0326(17) 0.0348(17) 0.0287(15) 0.0006(13) 0.0022(13) -0.0004(13)
C2 0.0292(17) 0.0428(19) 0.058(2) 0.0017(17) -0.0090(16) -0.0022(15)
C7 0.0361(18) 0.057(2) 0.0278(15) 0.0011(15) 0.0024(14) -0.0042(16)
C3 0.0305(17) 0.044(2) 0.051(2) 0.0057(17) 0.0037(15) -0.0009(15)
C38 0.0315(16) 0.0320(16) 0.0273(15) -0.0002(12) -0.0016(13) -0.0008(13)
C1 0.0370(19) 0.048(2) 0.045(2) -0.0067(16) -0.0071(16) -0.0009(16)
C6 0.0292(15) 0.0306(16) 0.0264(15) -0.0008(12) 0.0020(12) 0.0019(12)
O2 0.079(3) 0.090(2) 0.080(3) 0.005(2) 0.030(2) -0.011(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 N3 2.065(2) . ?
Zn1 N1 2.074(3) . ?
Zn1 Cl2 2.2205(11) . ?
Zn1 Cl1 2.2248(10) . ?
S1 C38 1.741(3) . ?
S1 C7 1.802(3) . ?
O1 C8 1.228(4) . ?
N2 C6 1.324(4) . ?
N2 H2B 0.8600 . ?
N2 H2C 0.8600 . ?
N1 C1 1.333(4) . ?
N1 C5 1.345(4) . ?
N3 C6 1.315(4) . ?
N3 N4 1.401(3) . ?
N4 C38 1.271(4) . ?
N5 C8 1.342(4) . ?
N5 C38 1.392(4) . ?
N5 H5A 0.8600 . ?
C5 C4 1.377(4) . ?
C5 C6 1.491(4) . ?
C4 C3 1.375(5) . ?
C4 H4A 0.9300 . ?
C8 C7 1.503(4) . ?
C2 C1 1.369(5) . ?
C2 C3 1.386(5) . ?
C2 H2A 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C3 H3A 0.9300 . ?
C1 H1A 0.9300 . ?
O2 H1W 0.862(10) . ?
O2 H2W 0.863(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Zn1 N1 79.96(10) . . ?
N3 Zn1 Cl2 125.99(8) . . ?
N1 Zn1 Cl2 103.25(8) . . ?
N3 Zn1 Cl1 111.97(8) . . ?
N1 Zn1 Cl1 112.76(8) . . ?
Cl2 Zn1 Cl1 115.56(4) . . ?
C38 S1 C7 92.12(15) . . ?
C6 N2 H2B 120.0 . . ?
C6 N2 H2C 120.0 . . ?
H2B N2 H2C 120.0 . . ?
C1 N1 C5 118.7(3) . . ?
C1 N1 Zn1 128.1(2) . . ?
C5 N1 Zn1 113.2(2) . . ?
C6 N3 N4 111.7(2) . . ?
C6 N3 Zn1 112.4(2) . . ?
N4 N3 Zn1 132.08(18) . . ?
C38 N4 N3 115.1(3) . . ?
C8 N5 C38 117.3(3) . . ?
C8 N5 H5A 121.3 . . ?
C38 N5 H5A 121.3 . . ?
N1 C5 C4 121.5(3) . . ?
N1 C5 C6 114.7(3) . . ?
C4 C5 C6 123.8(3) . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
O1 C8 N5 124.0(3) . . ?
O1 C8 C7 123.9(3) . . ?
N5 C8 C7 112.1(3) . . ?
C1 C2 C3 118.5(3) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 H2A 120.7 . . ?
C8 C7 S1 107.1(2) . . ?
C8 C7 H7A 110.3 . . ?
S1 C7 H7A 110.3 . . ?
C8 C7 H7B 110.3 . . ?
S1 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
N4 C38 N5 118.9(3) . . ?
N4 C38 S1 130.3(3) . . ?
N5 C38 S1 110.8(2) . . ?
N1 C1 C2 122.9(3) . . ?
N1 C1 H1A 118.5 . . ?
C2 C1 H1A 118.5 . . ?
N3 C6 N2 124.0(3) . . ?
N3 C6 C5 116.7(3) . . ?
N2 C6 C5 119.3(3) . . ?
H1W O2 H2W 134(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
N3 Zn1 N1 C1 -170.1(3) . . . . ?
Cl2 Zn1 N1 C1 -45.2(3) . . . . ?
Cl1 Zn1 N1 C1 80.2(3) . . . . ?
N3 Zn1 N1 C5 7.5(2) . . . . ?
Cl2 Zn1 N1 C5 132.4(2) . . . . ?
Cl1 Zn1 N1 C5 -102.2(2) . . . . ?
N1 Zn1 N3 C6 -14.9(2) . . . . ?
Cl2 Zn1 N3 C6 -114.0(2) . . . . ?
Cl1 Zn1 N3 C6 95.8(2) . . . . ?
N1 Zn1 N3 N4 -170.5(3) . . . . ?
Cl2 Zn1 N3 N4 90.3(3) . . . . ?
Cl1 Zn1 N3 N4 -59.9(3) . . . . ?
C6 N3 N4 C38 174.1(3) . . . . ?
Zn1 N3 N4 C38 -30.1(4) . . . . ?
C1 N1 C5 C4 -0.2(5) . . . . ?
Zn1 N1 C5 C4 -178.1(2) . . . . ?
C1 N1 C5 C6 178.1(3) . . . . ?
Zn1 N1 C5 C6 0.2(3) . . . . ?
N1 C5 C4 C3 -0.5(5) . . . . ?
C6 C5 C4 C3 -178.6(3) . . . . ?
C38 N5 C8 O1 -178.2(3) . . . . ?
C38 N5 C8 C7 1.0(4) . . . . ?
O1 C8 C7 S1 173.9(3) . . . . ?
N5 C8 C7 S1 -5.4(3) . . . . ?
C38 S1 C7 C8 6.4(2) . . . . ?
C5 C4 C3 C2 0.5(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
N3 N4 C38 N5 178.4(2) . . . . ?
N3 N4 C38 S1 -1.8(4) . . . . ?
C8 N5 C38 N4 -176.0(3) . . . . ?
C8 N5 C38 S1 4.1(3) . . . . ?
C7 S1 C38 N4 174.0(3) . . . . ?
C7 S1 C38 N5 -6.1(2) . . . . ?
C5 N1 C1 C2 0.9(5) . . . . ?
Zn1 N1 C1 C2 178.4(3) . . . . ?
C3 C2 C1 N1 -0.9(5) . . . . ?
N4 N3 C6 N2 -2.2(4) . . . . ?
Zn1 N3 C6 N2 -162.9(2) . . . . ?
N4 N3 C6 C5 -179.7(2) . . . . ?
Zn1 N3 C6 C5 19.6(3) . . . . ?
N1 C5 C6 N3 -13.5(4) . . . . ?
C4 C5 C6 N3 164.7(3) . . . . ?
N1 C5 C6 N2 168.9(3) . . . . ?
C4 C5 C6 N2 -12.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.103
