# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shelx
_audit_block_doi                 10.5517/cc13w044
_database_code_depnum_ccdc_archive 'CCDC 1038845'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        6-chloro-4-phenyl-2-(pyridin-2-yl)quinazoline
_chemical_name_common            PPQZC
_chemical_melting_point          487.1
_chemical_formula_moiety         'C19 H12 Cl N3'
_chemical_formula_sum            'C19 H12 Cl N3'
_chemical_formula_weight         317.77

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.5774(10)
_cell_length_b                   9.8402(14)
_cell_length_c                   11.5850(16)
_cell_angle_alpha                96.481(12)
_cell_angle_beta                 103.287(12)
_cell_angle_gamma                112.462(13)
_cell_volume                     757.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1739
_cell_measurement_theta_min      3.2547
_cell_measurement_theta_max      28.9590

_exptl_crystal_description       'block shaped'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            5409
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.261
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3100
_reflns_number_gt                2274
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXS-2014 (Sheldrick, 2014)'
_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)+(0.0424P)²+0.1236P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3100
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Cl1 Cl 0.25481(8) 0.26391(6) 0.39012(6) 0.0715(2) Uani 1 1 d . . . . .
N1 N 0.34847(19) 0.61687(15) 0.01450(14) 0.0435(4) Uani 1 1 d . . . . .
N2 N 0.69553(19) 0.76104(15) 0.12104(13) 0.0396(3) Uani 1 1 d . . . . .
N3 N 0.3751(2) 0.80905(18) -0.13998(14) 0.0528(4) Uani 1 1 d . . . . .
C1 C 0.5228(2) 0.72936(18) 0.03177(16) 0.0390(4) Uani 1 1 d . . . . .
C2 C 0.6870(2) 0.67504(18) 0.20058(16) 0.0371(4) Uani 1 1 d . . . . .
C3 C 0.4771(2) 0.47132(18) 0.28797(17) 0.0441(4) Uani 1 1 d . . . . .
H3 H 0.5852 0.4887 0.3543 0.053 Uiso 1 1 calc R U . . .
C4 C 0.2921(3) 0.36289(19) 0.27591(18) 0.0466(5) Uani 1 1 d . . . . .
C5 C 0.1271(3) 0.33153(19) 0.1761(2) 0.0525(5) Uani 1 1 d . . . . .
H5 H 0.0035 0.2548 0.1691 0.063 Uiso 1 1 calc R U . . .
C6 C 0.1481(2) 0.41338(19) 0.08943(19) 0.0497(5) Uani 1 1 d . . . . .
H6 H 0.0385 0.3923 0.0229 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5017(2) 0.55674(17) 0.19823(16) 0.0379(4) Uani 1 1 d . . . . .
C8 C 0.3352(2) 0.53039(18) 0.09945(17) 0.0406(4) Uani 1 1 d . . . . .
C9 C 0.8775(2) 0.70685(18) 0.29322(15) 0.0387(4) Uani 1 1 d . . . . .
C10 C 0.9976(2) 0.85274(19) 0.36049(17) 0.0466(5) Uani 1 1 d . . . . .
H10 H 0.9577 0.9296 0.3478 0.056 Uiso 1 1 calc R U . . .
C11 C 1.1760(3) 0.8844(2) 0.44614(18) 0.0557(5) Uani 1 1 d . . . . .
H11 H 1.2550 0.9822 0.4918 0.067 Uiso 1 1 calc R U . . .
C12 C 1.2375(3) 0.7722(2) 0.46427(18) 0.0576(5) Uani 1 1 d . . . . .
H12 H 1.3581 0.7941 0.5221 0.069 Uiso 1 1 calc R U . . .
C13 C 1.1213(3) 0.6276(2) 0.3972(2) 0.0618(6) Uani 1 1 d . . . . .
H13 H 1.1638 0.5519 0.4090 0.074 Uiso 1 1 calc R U . . .
C14 C 0.9403(3) 0.5941(2) 0.31175(19) 0.0541(5) Uani 1 1 d . . . . .
H14 H 0.8612 0.4958 0.2669 0.065 Uiso 1 1 calc R U . . .
C15 C 0.5422(2) 0.83111(18) -0.05506(16) 0.0392(4) Uani 1 1 d . . . . .
C16 C 0.3923(3) 0.9023(3) -0.21564(19) 0.0627(6) Uani 1 1 d . . . . .
H16 H 0.2766 0.8890 -0.2742 0.075 Uiso 1 1 calc R U . . .
C17 C 0.5683(3) 1.0165(2) -0.21338(19) 0.0601(5) Uani 1 1 d . . . . .
H17 H 0.5716 1.0779 -0.2690 0.072 Uiso 1 1 calc R U . . .
C18 C 0.7390(3) 1.0377(2) -0.12726(19) 0.0598(5) Uani 1 1 d . . . . .
H18 H 0.8616 1.1132 -0.1235 0.072 Uiso 1 1 calc R U . . .
C19 C 0.7256(3) 0.9447(2) -0.04603(18) 0.0513(5) Uani 1 1 d . . . . .
H19 H 0.8393 0.9584 0.0145 0.062 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.7412(19) . ?
N1 C1 1.312(2) . ?
N1 C8 1.368(2) . ?
N2 C2 1.316(2) . ?
N2 C1 1.368(2) . ?
N3 C16 1.331(2) . ?
N3 C15 1.337(2) . ?
C1 C15 1.490(2) . ?
C2 C7 1.433(2) . ?
C2 C9 1.484(2) . ?
C3 C4 1.362(2) . ?
C3 C7 1.410(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(3) . ?
C5 C6 1.356(3) . ?
C5 H5 0.9300 . ?
C6 C8 1.412(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.410(2) . ?
C9 C14 1.383(2) . ?
C9 C10 1.385(2) . ?
C10 C11 1.379(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C19 1.383(2) . ?
C16 C17 1.369(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 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
C1 N1 C8 116.61(14) . . ?
C2 N2 C1 117.79(14) . . ?
C16 N3 C15 117.01(16) . . ?
N1 C1 N2 126.17(16) . . ?
N1 C1 C15 118.58(15) . . ?
N2 C1 C15 115.21(14) . . ?
N2 C2 C7 121.46(15) . . ?
N2 C2 C9 116.96(14) . . ?
C7 C2 C9 121.57(15) . . ?
C4 C3 C7 118.88(17) . . ?
C4 C3 H3 120.6 . . ?
C7 C3 H3 120.6 . . ?
C3 C4 C5 122.05(17) . . ?
C3 C4 Cl1 119.67(15) . . ?
C5 C4 Cl1 118.23(14) . . ?
C6 C5 C4 119.76(16) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C8 120.51(17) . . ?
C5 C6 H6 119.7 . . ?
C8 C6 H6 119.7 . . ?
C8 C7 C3 119.69(15) . . ?
C8 C7 C2 115.70(16) . . ?
C3 C7 C2 124.59(15) . . ?
N1 C8 C7 121.93(14) . . ?
N1 C8 C6 119.03(16) . . ?
C7 C8 C6 119.02(17) . . ?
C14 C9 C10 119.21(16) . . ?
C14 C9 C2 121.21(15) . . ?
C10 C9 C2 119.56(15) . . ?
C11 C10 C9 120.24(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.33(18) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.00(18) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.17(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.04(18) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
N3 C15 C19 121.93(16) . . ?
N3 C15 C1 117.20(14) . . ?
C19 C15 C1 120.86(16) . . ?
N3 C16 C17 124.61(19) . . ?
N3 C16 H16 117.7 . . ?
C17 C16 H16 117.7 . . ?
C18 C17 C16 118.19(19) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C17 C18 C19 118.62(18) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C15 119.62(18) . . ?
C18 C19 H19 120.2 . . ?
C15 C19 H19 120.2 . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1430166'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H30 Cl2 N12 O4 Zn2'
_chemical_formula_sum            'C42 H30 Cl2 N12 O4 Zn2'
_chemical_formula_weight         968.46

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   22.8212(15)
_cell_length_b                   8.3160(6)
_cell_length_c                   22.1236(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.430(6)
_cell_angle_gamma                90
_cell_volume                     4172.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1886
_cell_measurement_theta_min      3.1300
_cell_measurement_theta_max      29.2548

_exptl_crystal_description       square
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.337
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            9998
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4257
_reflns_number_gt                2721
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXS-2014 (Sheldrick, 2014)'
_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)+(0.0318P)²+6.3140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4257
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.24957(2) 0.16388(6) 0.06563(2) 0.04798(17) Uani 1 1 d . . . . .
Cl1 Cl 0.44630(6) -0.54357(15) 0.14488(6) 0.0877(4) Uani 1 1 d . . . . .
N1 N 0.31786(13) 0.0684(4) 0.13573(12) 0.0387(7) Uani 1 1 d . . . . .
N2 N 0.36615(13) 0.1392(4) 0.23372(12) 0.0385(7) Uani 1 1 d . . . . .
N3 N 0.26161(14) 0.3533(4) 0.12899(13) 0.0452(8) Uani 1 1 d . . . . .
N4 N 0.30540(15) 0.1862(4) -0.00052(13) 0.0527(9) Uani 1 1 d . . . . .
N5 N 0.35658(19) 0.2062(6) 0.00940(15) 0.0768(14) Uani 1 1 d . . . . .
N6A N 0.4047(9) 0.262(5) 0.0191(5) 0.084(8) Uani 0.63(8) 1 d . . P A 1
N6B N 0.4059(17) 0.149(16) 0.0149(14) 0.14(3) Uani 0.37(8) 1 d . . P A 2
O1 O 0.17404(15) 0.0577(5) 0.12729(17) 0.0884(11) Uani 1 1 d . . . . .
O2 O 0.20091(13) -0.0371(4) 0.04365(13) 0.0717(9) Uani 1 1 d . . . . .
C1 C 0.33006(15) 0.1672(4) 0.18175(15) 0.0370(8) Uani 1 1 d . . . . .
C2 C 0.39208(15) -0.0031(5) 0.23909(15) 0.0369(8) Uani 1 1 d . . . . .
C3 C 0.41651(16) -0.2640(5) 0.19152(18) 0.0466(10) Uani 1 1 d . . . . .
H3 H 0.4430 -0.2919 0.2249 0.056 Uiso 1 1 calc R U . . .
C4 C 0.40727(18) -0.3637(5) 0.14305(19) 0.0533(11) Uani 1 1 d . . . . .
C5 C 0.36746(19) -0.3291(5) 0.09260(18) 0.0554(11) Uani 1 1 d . . . . .
H5 H 0.3611 -0.4024 0.0608 0.066 Uiso 1 1 calc R U . . .
C6 C 0.33762(18) -0.1857(5) 0.09014(16) 0.0493(10) Uani 1 1 d . . . . .
H6 H 0.3115 -0.1605 0.0562 0.059 Uiso 1 1 calc R U . . .
C7 C 0.38541(15) -0.1170(4) 0.19080(15) 0.0372(9) Uani 1 1 d . . . . .
C8 C 0.34649(16) -0.0771(4) 0.13872(16) 0.0388(9) Uani 1 1 d . . . . .
C9 C 0.42762(15) -0.0338(5) 0.29842(15) 0.0384(9) Uani 1 1 d . . . . .
C10 C 0.46614(16) 0.0830(5) 0.32291(17) 0.0478(10) Uani 1 1 d . . . . .
H10 H 0.4704 0.1782 0.3018 0.057 Uiso 1 1 calc R U . . .
C11 C 0.49847(19) 0.0583(6) 0.37894(19) 0.0595(12) Uani 1 1 d . . . . .
H11 H 0.5252 0.1357 0.3951 0.071 Uiso 1 1 calc R U . . .
C12 C 0.4909(2) -0.0805(6) 0.41045(19) 0.0623(12) Uani 1 1 d . . . . .
H12 H 0.5123 -0.0963 0.4483 0.075 Uiso 1 1 calc R U . . .
C13 C 0.4523(2) -0.1963(6) 0.38691(18) 0.0599(12) Uani 1 1 d . . . . .
H13 H 0.4474 -0.2896 0.4089 0.072 Uiso 1 1 calc R U . . .
C14 C 0.42048(17) -0.1750(5) 0.33058(17) 0.0519(11) Uani 1 1 d . . . . .
H14 H 0.3946 -0.2542 0.3143 0.062 Uiso 1 1 calc R U . . .
C15 C 0.29973(15) 0.3258(5) 0.17909(15) 0.0391(9) Uani 1 1 d . . . . .
C16 C 0.23270(19) 0.4924(5) 0.12552(19) 0.0589(12) Uani 1 1 d . . . . .
H16 H 0.2069 0.5131 0.0908 0.071 Uiso 1 1 calc R U . . .
C17 C 0.2388(2) 0.6076(5) 0.1706(2) 0.0609(12) Uani 1 1 d . . . . .
H17 H 0.2172 0.7026 0.1666 0.073 Uiso 1 1 calc R U . . .
C18 C 0.27764(18) 0.5785(5) 0.22140(19) 0.0536(11) Uani 1 1 d . . . . .
H18 H 0.2830 0.6541 0.2525 0.064 Uiso 1 1 calc R U . . .
C19 C 0.30862(17) 0.4360(5) 0.22573(17) 0.0453(10) Uani 1 1 d . . . . .
H19 H 0.3352 0.4145 0.2597 0.054 Uiso 1 1 calc R U . . .
C20 C 0.1673(2) -0.0375(6) 0.0850(2) 0.0593(12) Uani 1 1 d . . . . .
C21 C 0.1172(2) -0.1555(6) 0.0799(2) 0.0871(16) Uani 1 1 d . . . . .
H21A H 0.1186 -0.2204 0.0442 0.131 Uiso 1 1 calc R U . . .
H21B H 0.1205 -0.2233 0.1153 0.131 Uiso 1 1 calc R U . . .
H21C H 0.0804 -0.0983 0.0770 0.131 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 2.035(3) . ?
Zn1 N4 2.054(3) . ?
Zn1 N3 2.106(3) . ?
Zn1 N4 2.190(3) 7 ?
Zn1 N1 2.219(3) . ?
Zn1 O1 2.478(4) . ?
Zn1 C20 2.587(5) . ?
Cl1 C4 1.739(4) . ?
N1 C1 1.314(4) . ?
N1 C8 1.373(4) . ?
N2 C2 1.323(4) . ?
N2 C1 1.357(4) . ?
N3 C16 1.329(5) . ?
N3 C15 1.350(4) . ?
N4 N5 1.176(5) . ?
N4 Zn1 2.190(3) 7 ?
N5 N6A 1.190(13) . ?
N5 N6B 1.22(3) . ?
O1 C20 1.223(5) . ?
O2 C20 1.258(5) . ?
C1 C15 1.488(5) . ?
C2 C7 1.423(5) . ?
C2 C9 1.486(5) . ?
C3 C4 1.353(5) . ?
C3 C7 1.413(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(5) . ?
C5 C6 1.371(5) . ?
C5 H5 0.9300 . ?
C6 C8 1.401(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.413(5) . ?
C9 C10 1.379(5) . ?
C9 C14 1.392(5) . ?
C10 C11 1.385(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C19 1.378(5) . ?
C16 C17 1.378(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.501(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
O2 Zn1 N4 105.64(14) . . ?
O2 Zn1 N3 143.16(12) . . ?
N4 Zn1 N3 111.19(13) . . ?
O2 Zn1 N4 93.05(13) . 7 ?
N4 Zn1 N4 80.52(14) . 7 ?
N3 Zn1 N4 91.97(12) . 7 ?
O2 Zn1 N1 101.23(12) . . ?
N4 Zn1 N1 95.01(11) . . ?
N3 Zn1 N1 76.90(11) . . ?
N4 Zn1 N1 165.71(13) 7 . ?
O2 Zn1 O1 56.23(12) . . ?
N4 Zn1 O1 161.81(14) . . ?
N3 Zn1 O1 86.97(12) . . ?
N4 Zn1 O1 100.50(12) 7 . ?
N1 Zn1 O1 88.00(11) . . ?
O2 Zn1 C20 28.50(13) . . ?
N4 Zn1 C20 134.12(16) . . ?
N3 Zn1 C20 114.65(15) . . ?
N4 Zn1 C20 95.98(13) 7 . ?
N1 Zn1 C20 96.82(12) . . ?
O1 Zn1 C20 27.83(12) . . ?
C1 N1 C8 117.1(3) . . ?
C1 N1 Zn1 112.9(2) . . ?
C8 N1 Zn1 130.0(2) . . ?
C2 N2 C1 116.9(3) . . ?
C16 N3 C15 117.7(3) . . ?
C16 N3 Zn1 125.8(3) . . ?
C15 N3 Zn1 116.4(3) . . ?
N5 N4 Zn1 124.2(3) . . ?
N5 N4 Zn1 121.8(3) . 7 ?
Zn1 N4 Zn1 99.48(14) . 7 ?
N4 N5 N6A 165(2) . . ?
N4 N5 N6B 148(7) . . ?
C20 O1 Zn1 81.1(3) . . ?
C20 O2 Zn1 100.9(3) . . ?
N1 C1 N2 127.2(3) . . ?
N1 C1 C15 117.8(3) . . ?
N2 C1 C15 114.9(3) . . ?
N2 C2 C7 121.3(3) . . ?
N2 C2 C9 115.3(3) . . ?
C7 C2 C9 123.4(3) . . ?
C4 C3 C7 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C7 C3 H3 120.4 . . ?
C3 C4 C5 122.7(4) . . ?
C3 C4 Cl1 118.3(3) . . ?
C5 C4 Cl1 119.0(3) . . ?
C6 C5 C4 119.3(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C8 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C8 C6 H6 119.9 . . ?
C3 C7 C8 118.8(3) . . ?
C3 C7 C2 123.8(3) . . ?
C8 C7 C2 117.4(3) . . ?
N1 C8 C6 120.3(3) . . ?
N1 C8 C7 119.9(3) . . ?
C6 C8 C7 119.8(3) . . ?
C10 C9 C14 119.9(3) . . ?
C10 C9 C2 119.2(3) . . ?
C14 C9 C2 120.9(3) . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 119.3(4) . . ?
C13 C14 H14 120.4 . . ?
C9 C14 H14 120.4 . . ?
N3 C15 C19 122.0(3) . . ?
N3 C15 C1 115.9(3) . . ?
C19 C15 C1 122.1(3) . . ?
N3 C16 C17 123.6(4) . . ?
N3 C16 H16 118.2 . . ?
C17 C16 H16 118.2 . . ?
C18 C17 C16 118.3(4) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C17 C18 C19 119.2(4) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C15 119.2(4) . . ?
C18 C19 H19 120.4 . . ?
C15 C19 H19 120.4 . . ?
O1 C20 O2 121.3(5) . . ?
O1 C20 C21 120.7(5) . . ?
O2 C20 C21 118.0(5) . . ?
O1 C20 Zn1 71.1(3) . . ?
O2 C20 Zn1 50.6(2) . . ?
C21 C20 Zn1 166.3(4) . . ?
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 . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1430171'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Cl3 N3 Zn'
_chemical_formula_sum            'C19 H12 Cl3 N3 Zn'
_chemical_formula_weight         454.06

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.283(5)
_cell_length_b                   7.886(5)
_cell_length_c                   22.684(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.402(5)
_cell_angle_gamma                90
_cell_volume                     1836.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1557
_cell_measurement_theta_min      3.1417
_cell_measurement_theta_max      29.1027

_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.782
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            7456
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.148
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3748
_reflns_number_gt                2402
_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       
;        
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXS-2014 (Sheldrick, 2014)'
_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)+(0.0494P)²+0.6529P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3748
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.35303(5) -0.14824(7) 0.47531(3) 0.0540(2) Uani 1 1 d . . . . .
Cl1 Cl 0.23604(13) -0.91963(16) 0.29302(6) 0.0671(4) Uani 1 1 d . . . . .
Cl2 Cl 0.51914(13) -0.07805(18) 0.42305(7) 0.0752(4) Uani 1 1 d . . . . .
Cl3 Cl 0.34765(13) -0.34472(15) 0.54455(6) 0.0637(4) Uani 1 1 d . . . . .
N1 N 0.2144(3) -0.2592(4) 0.41127(15) 0.0386(8) Uani 1 1 d . . . . .
N2 N -0.0027(3) -0.2187(4) 0.37172(14) 0.0370(8) Uani 1 1 d . . . . .
N3 N 0.2084(3) 0.0358(4) 0.46879(15) 0.0403(8) Uani 1 1 d . . . . .
C1 C 0.1058(4) -0.1742(5) 0.40459(18) 0.0357(9) Uani 1 1 d . . . . .
C2 C 0.0004(4) -0.3617(5) 0.34166(18) 0.0363(9) Uani 1 1 d . . . . .
C3 C 0.1186(4) -0.6286(5) 0.31835(19) 0.0426(10) Uani 1 1 d . . . . .
H3 H 0.0477 -0.6704 0.2954 0.051 Uiso 1 1 calc R U . . .
C4 C 0.2295(5) -0.7211(5) 0.3263(2) 0.0464(11) Uani 1 1 d . . . . .
C5 C 0.3377(5) -0.6659(6) 0.3611(2) 0.0521(12) Uani 1 1 d . . . . .
H5 H 0.4123 -0.7326 0.3655 0.062 Uiso 1 1 calc R U . . .
C6 C 0.3324(4) -0.5123(6) 0.3887(2) 0.0486(11) Uani 1 1 d . . . . .
H6 H 0.4036 -0.4746 0.4123 0.058 Uiso 1 1 calc R U . . .
C7 C 0.1126(4) -0.4675(5) 0.34553(18) 0.0368(10) Uani 1 1 d . . . . .
C8 C 0.2206(4) -0.4113(5) 0.38179(18) 0.0387(10) Uani 1 1 d . . . . .
C9 C -0.1202(4) -0.4040(5) 0.30517(19) 0.0391(10) Uani 1 1 d . . . . .
C10 C -0.2390(4) -0.3957(6) 0.3296(2) 0.0541(12) Uani 1 1 d . . . . .
H10 H -0.2435 -0.3685 0.3693 0.065 Uiso 1 1 calc R U . . .
C11 C -0.3515(5) -0.4274(7) 0.2955(2) 0.0645(14) Uani 1 1 d . . . . .
H11 H -0.4314 -0.4250 0.3126 0.077 Uiso 1 1 calc R U . . .
C12 C -0.3469(5) -0.4626(6) 0.2365(3) 0.0662(15) Uani 1 1 d . . . . .
H12 H -0.4234 -0.4824 0.2136 0.079 Uiso 1 1 calc R U . . .
C13 C -0.2305(5) -0.4682(7) 0.2117(2) 0.0678(15) Uani 1 1 d . . . . .
H13 H -0.2273 -0.4910 0.1716 0.081 Uiso 1 1 calc R U . . .
C14 C -0.1165(5) -0.4404(6) 0.2456(2) 0.0558(13) Uani 1 1 d . . . . .
H14 H -0.0368 -0.4462 0.2283 0.067 Uiso 1 1 calc R U . . .
C15 C 0.1010(4) -0.0079(5) 0.43454(17) 0.0351(9) Uani 1 1 d . . . . .
C16 C 0.2111(5) 0.1894(5) 0.4929(2) 0.0485(11) Uani 1 1 d . . . . .
H16 H 0.2851 0.2214 0.5157 0.058 Uiso 1 1 calc R U . . .
C17 C 0.1103(5) 0.3035(6) 0.4858(2) 0.0496(12) Uani 1 1 d . . . . .
H17 H 0.1164 0.4102 0.5033 0.059 Uiso 1 1 calc R U . . .
C18 C 0.0008(4) 0.2568(5) 0.45263(19) 0.0466(11) Uani 1 1 d . . . . .
H18 H -0.0693 0.3309 0.4475 0.056 Uiso 1 1 calc R U . . .
C19 C -0.0045(4) 0.0988(5) 0.42682(18) 0.0410(10) Uani 1 1 d . . . . .
H19 H -0.0785 0.0645 0.4044 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N3 2.077(3) . ?
Zn1 N1 2.159(3) . ?
Zn1 Cl2 2.2067(16) . ?
Zn1 Cl3 2.2094(15) . ?
Cl1 C4 1.741(5) . ?
N1 C1 1.304(5) . ?
N1 C8 1.376(5) . ?
N2 C2 1.319(5) . ?
N2 C1 1.351(5) . ?
N3 C16 1.328(5) . ?
N3 C15 1.357(5) . ?
C1 C15 1.480(5) . ?
C2 C7 1.423(5) . ?
C2 C9 1.487(6) . ?
C3 C4 1.357(6) . ?
C3 C7 1.415(5) . ?
C4 C5 1.395(6) . ?
C5 C6 1.366(6) . ?
C6 C8 1.400(5) . ?
C7 C8 1.413(6) . ?
C9 C10 1.372(6) . ?
C9 C14 1.384(6) . ?
C10 C11 1.376(6) . ?
C11 C12 1.371(7) . ?
C12 C13 1.352(7) . ?
C13 C14 1.381(6) . ?
C15 C19 1.375(5) . ?
C16 C17 1.375(6) . ?
C17 C18 1.367(6) . ?
C18 C19 1.377(5) . ?

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 78.11(13) . . ?
N3 Zn1 Cl2 111.12(11) . . ?
N1 Zn1 Cl2 103.97(10) . . ?
N3 Zn1 Cl3 119.52(11) . . ?
N1 Zn1 Cl3 98.66(10) . . ?
Cl2 Zn1 Cl3 127.63(6) . . ?
C1 N1 C8 117.1(3) . . ?
C1 N1 Zn1 113.4(3) . . ?
C8 N1 Zn1 129.2(3) . . ?
C2 N2 C1 117.6(3) . . ?
C16 N3 C15 117.6(4) . . ?
C16 N3 Zn1 127.6(3) . . ?
C15 N3 Zn1 114.7(3) . . ?
N1 C1 N2 127.2(4) . . ?
N1 C1 C15 117.0(3) . . ?
N2 C1 C15 115.7(3) . . ?
N2 C2 C7 120.9(4) . . ?
N2 C2 C9 115.8(4) . . ?
C7 C2 C9 123.3(4) . . ?
C4 C3 C7 118.8(4) . . ?
C3 C4 C5 122.9(4) . . ?
C3 C4 Cl1 118.6(4) . . ?
C5 C4 Cl1 118.4(3) . . ?
C6 C5 C4 118.9(4) . . ?
C5 C6 C8 120.6(4) . . ?
C8 C7 C3 118.8(4) . . ?
C8 C7 C2 117.3(4) . . ?
C3 C7 C2 123.8(4) . . ?
N1 C8 C6 120.2(4) . . ?
N1 C8 C7 119.9(4) . . ?
C6 C8 C7 119.9(4) . . ?
C10 C9 C14 118.8(4) . . ?
C10 C9 C2 119.8(4) . . ?
C14 C9 C2 121.3(4) . . ?
C9 C10 C11 120.2(5) . . ?
C12 C11 C10 120.6(5) . . ?
C13 C12 C11 119.7(5) . . ?
C12 C13 C14 120.4(5) . . ?
C13 C14 C9 120.3(5) . . ?
N3 C15 C19 121.8(4) . . ?
N3 C15 C1 116.1(3) . . ?
C19 C15 C1 122.1(4) . . ?
N3 C16 C17 123.5(4) . . ?
C18 C17 C16 118.5(4) . . ?
C17 C18 C19 119.3(4) . . ?
C15 C19 C18 119.2(4) . . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.078

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1430172'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H24 Cl2 N18 Zn2'
_chemical_formula_sum            'C38 H24 Cl2 N18 Zn2'
_chemical_formula_weight         934.43

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.360(5)
_cell_length_b                   7.813(5)
_cell_length_c                   19.833(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.586(5)
_cell_angle_gamma                90
_cell_volume                     1902.6(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1288
_cell_measurement_theta_min      3.1914
_cell_measurement_theta_max      29.1837

_exptl_crystal_description       'block shaped'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.459
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            7576
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.198
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3887
_reflns_number_gt                2582
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXS-2014 (Sheldrick, 2014)'
_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)+(0.0398P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3887
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.12010(3) 0.02661(7) 0.97836(2) 0.03790(17) Uani 1 1 d . . . . .
Cl1 Cl 0.59629(9) -0.57711(18) 0.82018(6) 0.0625(4) Uani 1 1 d . . . . .
N1 N 0.4475(2) -0.1575(4) 1.03613(15) 0.0363(8) Uani 1 1 d . . . . .
N2 N 0.2715(2) -0.1330(4) 0.97381(14) 0.0320(8) Uani 1 1 d . . . . .
N3 N 0.2100(2) 0.0707(5) 1.07109(14) 0.0360(8) Uani 1 1 d . . . . .
N4 N 0.1343(3) 0.1600(6) 0.89734(17) 0.0598(12) Uani 1 1 d . . . . .
N5 N 0.2133(3) 0.1858(5) 0.87145(16) 0.0526(10) Uani 1 1 d . . . . .
N6 N 0.2898(4) 0.2144(7) 0.84427(18) 0.0822(16) Uani 1 1 d . . . . .
N7 N 0.0218(2) -0.1701(5) 0.99766(15) 0.0397(9) Uani 1 1 d . . . . .
N8 N 0.0618(3) -0.2906(6) 1.03047(19) 0.0470(9) Uani 1 1 d . . . . .
N9 N 0.1001(4) -0.4081(7) 1.0589(2) 0.0843(15) Uani 1 1 d . . . . .
C1 C 0.3461(3) -0.1038(5) 1.02834(17) 0.0320(9) Uani 1 1 d . . . . .
C2 C 0.3019(3) -0.2239(5) 0.92319(17) 0.0330(9) Uani 1 1 d . . . . .
C3 C 0.4461(3) -0.3915(6) 0.87467(18) 0.0394(10) Uani 1 1 d . . . . .
H3 H 0.3999 -0.4188 0.8358 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5495(3) -0.4515(6) 0.8830(2) 0.0397(10) Uani 1 1 d . . . . .
C5 C 0.6213(3) -0.4173(6) 0.9409(2) 0.0426(11) Uani 1 1 d . . . . .
H5 H 0.6918 -0.4609 0.9451 0.051 Uiso 1 1 calc R U . . .
C6 C 0.5873(3) -0.3193(6) 0.99103(19) 0.0409(11) Uani 1 1 d . . . . .
H6 H 0.6347 -0.2954 1.0297 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4091(3) -0.2877(5) 0.92510(17) 0.0321(9) Uani 1 1 d . . . . .
C8 C 0.4798(3) -0.2533(6) 0.98454(18) 0.0353(10) Uani 1 1 d . . . . .
C9 C 0.2200(3) -0.2622(5) 0.86369(18) 0.0340(10) Uani 1 1 d . . . . .
C10 C 0.1358(3) -0.3728(6) 0.8715(2) 0.0506(12) Uani 1 1 d . . . . .
H10 H 0.1287 -0.4187 0.9140 0.061 Uiso 1 1 calc R U . . .
C11 C 0.0617(4) -0.4166(7) 0.8165(2) 0.0629(15) Uani 1 1 d . . . . .
H11 H 0.0056 -0.4929 0.8218 0.076 Uiso 1 1 calc R U . . .
C12 C 0.0716(4) -0.3463(7) 0.7540(2) 0.0644(15) Uani 1 1 d . . . . .
H12 H 0.0212 -0.3739 0.7171 0.077 Uiso 1 1 calc R U . . .
C13 C 0.1550(4) -0.2360(7) 0.7456(2) 0.0589(14) Uani 1 1 d . . . . .
H13 H 0.1615 -0.1892 0.7031 0.071 Uiso 1 1 calc R U . . .
C14 C 0.2293(3) -0.1947(6) 0.80019(19) 0.0485(12) Uani 1 1 d . . . . .
H14 H 0.2864 -0.1207 0.7943 0.058 Uiso 1 1 calc R U . . .
C15 C 0.3089(3) -0.0002(5) 1.08377(17) 0.0330(9) Uani 1 1 d . . . . .
C16 C 0.1724(3) 0.1659(6) 1.1199(2) 0.0486(12) Uani 1 1 d . . . . .
H16 H 0.1039 0.2158 1.1113 0.058 Uiso 1 1 calc R U . . .
C17 C 0.2316(4) 0.1919(6) 1.1818(2) 0.0528(13) Uani 1 1 d . . . . .
H17 H 0.2036 0.2588 1.2145 0.063 Uiso 1 1 calc R U . . .
C18 C 0.3320(3) 0.1186(6) 1.19490(19) 0.0466(11) Uani 1 1 d . . . . .
H18 H 0.3726 0.1341 1.2369 0.056 Uiso 1 1 calc R U . . .
C19 C 0.3732(3) 0.0211(6) 1.14548(18) 0.0410(10) Uani 1 1 d . . . . .
H19 H 0.4418 -0.0287 1.1533 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N4 1.940(3) . ?
Zn1 N7 2.023(4) . ?
Zn1 N3 2.065(3) . ?
Zn1 N7 2.180(3) 3_557 ?
Zn1 N2 2.259(3) . ?
Cl1 C4 1.737(4) . ?
N1 C1 1.314(5) . ?
N1 C8 1.364(5) . ?
N2 C2 1.319(4) . ?
N2 C1 1.357(4) . ?
N3 C15 1.340(5) . ?
N3 C16 1.345(5) . ?
N4 N5 1.171(4) . ?
N5 N6 1.163(5) . ?
N7 N8 1.216(5) . ?
N7 Zn1 2.180(3) 3_557 ?
N8 N9 1.151(5) . ?
C1 C15 1.480(5) . ?
C2 C7 1.412(5) . ?
C2 C9 1.494(5) . ?
C3 C4 1.354(5) . ?
C3 C7 1.405(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(6) . ?
C5 C6 1.360(5) . ?
C5 H5 0.9300 . ?
C6 C8 1.417(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.410(5) . ?
C9 C10 1.375(5) . ?
C9 C14 1.382(5) . ?
C10 C11 1.384(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C19 1.391(5) . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(5) . ?
C18 H18 0.9300 . ?
C19 H19 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
N4 Zn1 N7 132.71(16) . . ?
N4 Zn1 N3 123.88(16) . . ?
N7 Zn1 N3 103.38(12) . . ?
N4 Zn1 N7 93.22(14) . 3_557 ?
N7 Zn1 N7 80.43(16) . 3_557 ?
N3 Zn1 N7 94.81(12) . 3_557 ?
N4 Zn1 N2 96.27(13) . . ?
N7 Zn1 N2 96.10(13) . . ?
N3 Zn1 N2 76.37(12) . . ?
N7 Zn1 N2 169.61(11) 3_557 . ?
C1 N1 C8 116.4(3) . . ?
C2 N2 C1 118.1(3) . . ?
C2 N2 Zn1 129.6(2) . . ?
C1 N2 Zn1 111.4(2) . . ?
C15 N3 C16 118.5(3) . . ?
C15 N3 Zn1 119.0(2) . . ?
C16 N3 Zn1 122.5(3) . . ?
N5 N4 Zn1 128.0(3) . . ?
N6 N5 N4 178.0(5) . . ?
N8 N7 Zn1 118.3(3) . . ?
N8 N7 Zn1 124.7(3) . 3_557 ?
Zn1 N7 Zn1 99.56(16) . 3_557 ?
N9 N8 N7 177.0(5) . . ?
N1 C1 N2 126.3(3) . . ?
N1 C1 C15 117.4(3) . . ?
N2 C1 C15 116.3(3) . . ?
N2 C2 C7 121.2(3) . . ?
N2 C2 C9 118.9(3) . . ?
C7 C2 C9 120.0(3) . . ?
C4 C3 C7 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C7 C3 H3 120.2 . . ?
C3 C4 C5 122.5(4) . . ?
C3 C4 Cl1 119.7(3) . . ?
C5 C4 Cl1 117.8(3) . . ?
C6 C5 C4 119.3(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C8 120.3(4) . . ?
C5 C6 H6 119.9 . . ?
C8 C6 H6 119.9 . . ?
C3 C7 C8 118.9(3) . . ?
C3 C7 C2 124.5(3) . . ?
C8 C7 C2 116.4(3) . . ?
N1 C8 C7 121.6(3) . . ?
N1 C8 C6 118.9(3) . . ?
C7 C8 C6 119.5(4) . . ?
C10 C9 C14 119.0(4) . . ?
C10 C9 C2 119.3(3) . . ?
C14 C9 C2 121.6(4) . . ?
C9 C10 C11 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.5(5) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 120.7(4) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
N3 C15 C19 122.2(3) . . ?
N3 C15 C1 116.2(3) . . ?
C19 C15 C1 121.6(3) . . ?
N3 C16 C17 122.3(4) . . ?
N3 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C18 C17 C16 119.2(4) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 119.8(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C15 118.0(4) . . ?
C18 C19 H19 121.0 . . ?
C15 C19 H19 121.0 . . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1430174'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Cl3 N3 Zn'
_chemical_formula_sum            'C19 H12 Cl3 N3 Zn'
_chemical_formula_weight         454.06

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.935(5)
_cell_length_b                   11.989(5)
_cell_length_c                   17.442(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1868.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1211
_cell_measurement_theta_min      3.0677
_cell_measurement_theta_max      28.8960

_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.751
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            5736
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.074
_diffrn_reflns_theta_max         28.959
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.752
_diffrn_reflns_point_group_measured_fraction_full 0.906
_reflns_number_total             3731
_reflns_number_gt                2655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.528
_reflns_Friedel_fraction_max     0.600
_reflns_Friedel_fraction_full    0.781

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXS-2014 (Sheldrick, 2014)'
_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)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3731
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.035
_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
Zn Zn 0.64307(10) 0.52526(8) 0.79522(5) 0.0402(3) Uani 1 1 d . . . . .
Cl1 Cl -0.1658(3) 0.7819(2) 0.65228(12) 0.0587(6) Uani 1 1 d . . . . .
Cl2 Cl 0.8004(2) 0.6345(3) 0.85662(12) 0.0661(7) Uani 1 1 d . . . . .
Cl3 Cl 0.5418(3) 0.3824(2) 0.85569(13) 0.0652(7) Uani 1 1 d . . . . .
N1 N 0.4228(7) 0.5881(6) 0.5868(3) 0.0389(17) Uani 1 1 d . . . . .
N2 N 0.4822(6) 0.5881(5) 0.7204(3) 0.0320(15) Uani 1 1 d . . . . .
N3 N 0.7405(7) 0.4870(6) 0.6915(3) 0.0416(16) Uani 1 1 d . . . . .
C1 C 0.5141(8) 0.5697(6) 0.6438(4) 0.0354(18) Uani 1 1 d . . . . .
C2 C 0.3457(9) 0.6261(6) 0.7390(4) 0.0313(16) Uani 1 1 d . . . . .
C3 C 0.0991(8) 0.6950(6) 0.6962(5) 0.0407(19) Uani 1 1 d . . . . .
H3 H 0.0683 0.7075 0.7464 0.049 Uiso 1 1 calc R U . . .
C4 C 0.0079(9) 0.7219(7) 0.6346(4) 0.043(2) Uani 1 1 d . . . . .
C5 C 0.0516(10) 0.7038(8) 0.5588(5) 0.049(2) Uani 1 1 d . . . . .
H5 H -0.0109 0.7244 0.5187 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1885(10) 0.6550(7) 0.5440(4) 0.046(2) Uani 1 1 d . . . . .
H6 H 0.2159 0.6388 0.4938 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2403(8) 0.6481(7) 0.6801(4) 0.0342(18) Uani 1 1 d . . . . .
C8 C 0.2860(9) 0.6298(7) 0.6040(4) 0.0344(19) Uani 1 1 d . . . . .
C9 C 0.3147(8) 0.6422(6) 0.8214(4) 0.0323(18) Uani 1 1 d . . . . .
C10 C 0.4062(8) 0.7111(8) 0.8649(4) 0.045(2) Uani 1 1 d . . . . .
H10 H 0.4852 0.7489 0.8419 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3795(11) 0.7235(8) 0.9432(4) 0.055(3) Uani 1 1 d . . . . .
H11 H 0.4396 0.7697 0.9729 0.067 Uiso 1 1 calc R U . . .
C12 C 0.2613(11) 0.6653(9) 0.9757(5) 0.057(3) Uani 1 1 d . . . . .
H12 H 0.2436 0.6726 1.0280 0.068 Uiso 1 1 calc R U . . .
C13 C 0.1715(10) 0.5988(8) 0.9340(4) 0.051(2) Uani 1 1 d . . . . .
H13 H 0.0933 0.5609 0.9577 0.061 Uiso 1 1 calc R U . . .
C14 C 0.1949(9) 0.5862(7) 0.8555(4) 0.044(2) Uani 1 1 d . . . . .
H14 H 0.1319 0.5413 0.8264 0.053 Uiso 1 1 calc R U . . .
C15 C 0.6627(8) 0.5212(7) 0.6280(4) 0.0345(17) Uani 1 1 d . . . . .
C16 C 0.8775(9) 0.4404(7) 0.6816(4) 0.043(2) Uani 1 1 d . . . . .
H16 H 0.9318 0.4178 0.7244 0.051 Uiso 1 1 calc R U . . .
C17 C 0.9382(10) 0.4257(8) 0.6097(5) 0.053(2) Uani 1 1 d . . . . .
H17 H 1.0316 0.3926 0.6040 0.064 Uiso 1 1 calc R U . . .
C18 C 0.8591(10) 0.4605(8) 0.5462(4) 0.055(2) Uani 1 1 d . . . . .
H18 H 0.8992 0.4514 0.4974 0.066 Uiso 1 1 calc R U . . .
C19 C 0.7214(9) 0.5086(8) 0.5553(4) 0.048(2) Uani 1 1 d . . . . .
H19 H 0.6676 0.5327 0.5127 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn N3 2.060(6) . ?
Zn N2 2.083(6) . ?
Zn Cl2 2.200(3) . ?
Zn Cl3 2.205(3) . ?
Cl1 C4 1.738(8) . ?
N1 C1 1.304(8) . ?
N1 C8 1.354(9) . ?
N2 C2 1.342(9) . ?
N2 C1 1.383(8) . ?
N3 C16 1.357(9) . ?
N3 C15 1.369(9) . ?
C1 C15 1.475(10) . ?
C2 C7 1.419(9) . ?
C2 C9 1.476(9) . ?
C3 C4 1.388(10) . ?
C3 C7 1.410(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(10) . ?
C5 C6 1.381(11) . ?
C5 H5 0.9300 . ?
C6 C8 1.394(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(9) . ?
C9 C10 1.388(10) . ?
C9 C14 1.397(11) . ?
C10 C11 1.394(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.346(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(10) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C19 1.381(9) . ?
C16 C17 1.378(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(11) . ?
C18 H18 0.9300 . ?
C19 H19 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
N3 Zn N2 79.7(2) . . ?
N3 Zn Cl2 106.87(19) . . ?
N2 Zn Cl2 122.06(19) . . ?
N3 Zn Cl3 114.9(2) . . ?
N2 Zn Cl3 107.32(19) . . ?
Cl2 Zn Cl3 119.46(10) . . ?
C1 N1 C8 117.3(6) . . ?
C2 N2 C1 118.4(6) . . ?
C2 N2 Zn 126.7(5) . . ?
C1 N2 Zn 113.9(5) . . ?
C16 N3 C15 118.6(6) . . ?
C16 N3 Zn 125.8(5) . . ?
C15 N3 Zn 115.4(5) . . ?
N1 C1 N2 125.5(7) . . ?
N1 C1 C15 119.2(6) . . ?
N2 C1 C15 115.3(6) . . ?
N2 C2 C7 119.4(6) . . ?
N2 C2 C9 116.8(7) . . ?
C7 C2 C9 123.8(7) . . ?
C4 C3 C7 117.6(7) . . ?
C4 C3 H3 121.2 . . ?
C7 C3 H3 121.2 . . ?
C3 C4 C5 122.2(8) . . ?
C3 C4 Cl1 118.9(6) . . ?
C5 C4 Cl1 118.9(6) . . ?
C6 C5 C4 119.5(8) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C8 120.3(7) . . ?
C5 C6 H6 119.8 . . ?
C8 C6 H6 119.8 . . ?
C8 C7 C3 120.7(7) . . ?
C8 C7 C2 117.5(7) . . ?
C3 C7 C2 121.6(7) . . ?
N1 C8 C6 118.5(7) . . ?
N1 C8 C7 121.9(7) . . ?
C6 C8 C7 119.6(7) . . ?
C10 C9 C14 120.3(7) . . ?
C10 C9 C2 120.0(7) . . ?
C14 C9 C2 119.7(7) . . ?
C9 C10 C11 119.9(8) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 118.5(8) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 122.1(8) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 120.4(9) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 118.8(8) . . ?
C13 C14 H14 120.6 . . ?
C9 C14 H14 120.6 . . ?
N3 C15 C19 121.1(7) . . ?
N3 C15 C1 115.1(6) . . ?
C19 C15 C1 123.8(7) . . ?
N3 C16 C17 121.5(7) . . ?
N3 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 119.4(8) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C19 C18 C17 119.7(7) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C15 119.6(8) . . ?
C18 C19 H19 120.2 . . ?
C15 C19 H19 120.2 . . ?

_refine_diff_density_max         0.739
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.088

