# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_6
_audit_block_doi                 10.5517/ccdc.csd.cc13n463
_database_code_depnum_ccdc_archive 'CCDC 1032244'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 N20 Zn2'
_chemical_formula_sum            'C36 H26 N20 Zn2'
_chemical_formula_weight         869.51

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

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

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

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

_cell_length_a                   8.0218(8)
_cell_length_b                   10.0798(10)
_cell_length_c                   11.6154(12)
_cell_angle_alpha                83.9840(10)
_cell_angle_beta                 83.1740(10)
_cell_angle_gamma                76.6970(10)
_cell_volume                     904.60(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1666
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      23.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_F_000             442
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.386
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4120
_exptl_absorpt_correction_T_max  0.6147
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4739
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.771
_diffrn_reflns_theta_max         25.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3259
_reflns_number_gt                2533
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3259
_refine_ls_number_parameters     262
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.036
_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 0.86875(6) 0.22685(5) 0.21406(4) 0.0534(2) Uani 1 1 d . . . . .
N1 N 0.7392(5) 0.1436(4) 0.3947(3) 0.0600(9) Uani 1 1 d . . . . .
N2 N 0.9523(4) 0.0205(3) 0.2312(3) 0.0469(7) Uani 1 1 d . . . . .
N3 N 1.0734(4) 0.2264(3) 0.0679(3) 0.0487(8) Uani 1 1 d . . . . .
N4 N 1.1048(5) -0.1895(4) 0.2091(3) 0.0608(8) Uani 1 1 d . U . . .
N9 N 0.6581(5) 0.2883(4) 0.1310(3) 0.0675(10) Uani 1 1 d . . . . .
N10 N 0.9251(6) 0.3720(4) 0.2948(3) 0.0706(11) Uani 1 1 d . . . . .
N11 N 0.5361(6) 0.2507(4) 0.1711(4) 0.0678(10) Uani 1 1 d . . . . .
N12 N 0.8177(6) 0.4672(5) 0.3250(3) 0.0715(11) Uani 1 1 d . . . . .
N13 N 0.7196(8) 0.5592(6) 0.3570(5) 0.115(2) Uani 1 1 d . . . . .
N18 N 0.4098(8) 0.2187(7) 0.2108(6) 0.131(3) Uani 1 1 d . . . . .
C1 C 0.6251(7) 0.2138(6) 0.4699(4) 0.0749(14) Uani 1 1 d . . . . .
H1 H 0.575055 0.304168 0.447544 0.090 Uiso 1 1 calc R U . . .
C2 C 0.5756(7) 0.1608(7) 0.5800(4) 0.0812(15) Uani 1 1 d . . . . .
H2 H 0.494216 0.213780 0.630111 0.097 Uiso 1 1 calc R U . . .
C3 C 0.6491(8) 0.0292(7) 0.6128(4) 0.0812(16) Uani 1 1 d . . . . .
H3 H 0.618284 -0.009004 0.686451 0.097 Uiso 1 1 calc R U . . .
C4 C 0.7697(7) -0.0484(6) 0.5373(4) 0.0742(13) Uani 1 1 d . . . . .
H4 H 0.822025 -0.138225 0.559695 0.089 Uiso 1 1 calc R U . . .
C5 C 0.8116(5) 0.0117(5) 0.4257(3) 0.0540(10) Uani 1 1 d . . . . .
C6 C 0.9295(5) -0.0523(4) 0.3326(3) 0.0484(8) Uani 1 1 d . U . . .
C7 C 1.0236(5) -0.1831(4) 0.3224(3) 0.0423(7) Uani 1 1 d . U . . .
C8 C 1.0526(7) -0.2980(5) 0.4022(4) 0.0698(13) Uani 1 1 d . . . . .
H8 H 1.001475 -0.293595 0.478238 0.084 Uiso 1 1 calc R U . . .
C9 C 1.1557(8) -0.4148(6) 0.3672(5) 0.0826(16) Uani 1 1 d . . . . .
H9 H 1.176074 -0.491003 0.420421 0.099 Uiso 1 1 calc R U . . .
C10 C 1.2322(8) -0.4251(5) 0.2544(5) 0.0801(15) Uani 1 1 d . . . . .
H10 H 1.301084 -0.507934 0.232795 0.096 Uiso 1 1 calc R U . . .
C11 C 1.2080(6) -0.3159(5) 0.1754(4) 0.0627(11) Uani 1 1 d . U . . .
H11 H 1.258595 -0.323641 0.099374 0.075 Uiso 1 1 calc R U . . .
C12 C 1.0572(5) -0.0604(4) 0.1556(3) 0.0476(8) Uani 1 1 d . U . . .
C13 C 1.0872(5) -0.0120(4) 0.0295(3) 0.0463(9) Uani 1 1 d . . . . .
H13 H 1.171106 -0.084710 -0.009016 0.056 Uiso 1 1 calc R U . . .
C14 C 1.1577(5) 0.1182(4) 0.0095(3) 0.0451(8) Uani 1 1 d . . . . .
C15 C 1.2948(6) 0.1260(5) -0.0706(4) 0.0605(11) Uani 1 1 d . . . . .
H15 H 1.352580 0.049075 -0.108153 0.073 Uiso 1 1 calc R U . . .
C16 C 1.3476(6) 0.2464(5) -0.0959(4) 0.0655(12) Uani 1 1 d . . . . .
H16 H 1.439376 0.252485 -0.151676 0.079 Uiso 1 1 calc R U . . .
C17 C 1.2626(6) 0.3582(5) -0.0375(4) 0.0666(12) Uani 1 1 d . . . . .
H17 H 1.294022 0.441948 -0.053739 0.080 Uiso 1 1 calc R U . . .
C18 C 1.1308(6) 0.3427(4) 0.0449(4) 0.0592(11) Uani 1 1 d . . . . .
H18 H 1.077620 0.416675 0.087644 0.071 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N10 1.979(4) . ?
Zn1 N2 2.029(3) . ?
Zn1 N9 1.988(4) . ?
Zn1 N3 2.216(3) . ?
Zn1 N1 2.388(3) . ?
N1 C1 1.320(6) . ?
N1 C5 1.352(6) . ?
N2 C6 1.337(5) . ?
N2 C12 1.343(5) . ?
N3 C14 1.347(5) . ?
N3 C18 1.345(5) . ?
N4 C7 1.398(5) . ?
N4 C11 1.415(6) . ?
N4 C12 1.372(5) . ?
N9 N11 1.159(6) . ?
N10 N12 1.185(6) . ?
N11 N18 1.162(7) . ?
N12 N13 1.134(6) . ?
C1 C2 1.383(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.357(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.450(6) . ?
C6 C7 1.369(6) . ?
C7 C8 1.398(6) . ?
C8 C9 1.345(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.351(7) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.504(5) . ?
C13 C14 1.531(5) . ?
C13 C13 1.588(7) 2_755 ?
C13 H13 0.9800 . ?
C14 C15 1.364(6) . ?
C15 C16 1.367(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(6) . ?
C17 H17 0.9300 . ?
C18 H18 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
N10 Zn1 N2 130.94(16) . . ?
N10 Zn1 N9 113.91(18) . . ?
N2 Zn1 N9 113.42(16) . . ?
N10 Zn1 N3 96.21(14) . . ?
N2 Zn1 N3 86.71(12) . . ?
N9 Zn1 N3 101.25(14) . . ?
N10 Zn1 N1 89.15(15) . . ?
N2 Zn1 N1 71.93(13) . . ?
N9 Zn1 N1 98.38(15) . . ?
N3 Zn1 N1 155.43(14) . . ?
C1 N1 C5 118.7(4) . . ?
C1 N1 Zn1 128.0(3) . . ?
C5 N1 Zn1 112.8(3) . . ?
C6 N2 C12 109.3(3) . . ?
C6 N2 Zn1 121.8(3) . . ?
C12 N2 Zn1 128.1(3) . . ?
C14 N3 C18 117.3(3) . . ?
C14 N3 Zn1 126.6(3) . . ?
C18 N3 Zn1 115.7(3) . . ?
C7 N4 C11 118.8(3) . . ?
C7 N4 C12 105.8(3) . . ?
C11 N4 C12 135.4(4) . . ?
N11 N9 Zn1 117.5(3) . . ?
N12 N10 Zn1 121.5(4) . . ?
N9 N11 N18 177.1(5) . . ?
N13 N12 N10 177.1(6) . . ?
N1 C1 C2 123.8(5) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 118.1(5) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 120.6(4) . . ?
N1 C5 C6 112.0(3) . . ?
C4 C5 C6 127.4(4) . . ?
N2 C6 C7 108.2(3) . . ?
N2 C6 C5 119.2(4) . . ?
C7 C6 C5 132.4(4) . . ?
C6 C7 N4 107.6(3) . . ?
C6 C7 C8 132.2(4) . . ?
N4 C7 C8 120.1(4) . . ?
C7 C8 C9 119.0(5) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 121.9(5) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 N4 119.5(4) . . ?
C10 C11 H11 120.3 . . ?
N4 C11 H11 120.3 . . ?
N2 C12 N4 109.1(3) . . ?
N2 C12 C13 121.3(4) . . ?
N4 C12 C13 129.0(4) . . ?
C12 C13 C14 113.9(3) . . ?
C12 C13 C13 109.4(4) . 2_755 ?
C14 C13 C13 109.6(4) . 2_755 ?
C12 C13 H13 107.9 . . ?
C14 C13 H13 107.9 . . ?
C13 C13 H13 107.9 2_755 . ?
N3 C14 C15 121.6(4) . . ?
N3 C14 C13 117.8(3) . . ?
C15 C14 C13 120.5(4) . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 118.9(4) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 118.1(4) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C17 C18 N3 123.7(4) . . ?
C17 C18 H18 118.1 . . ?
N3 C18 H18 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.6(7) . . . . ?
Zn1 N1 C1 C2 -170.3(4) . . . . ?
N1 C1 C2 C3 0.3(8) . . . . ?
C1 C2 C3 C4 -0.1(8) . . . . ?
C2 C3 C4 C5 -1.0(8) . . . . ?
C1 N1 C5 C4 -1.8(6) . . . . ?
Zn1 N1 C5 C4 170.4(3) . . . . ?
C1 N1 C5 C6 178.1(4) . . . . ?
Zn1 N1 C5 C6 -9.6(4) . . . . ?
C3 C4 C5 N1 2.0(7) . . . . ?
C3 C4 C5 C6 -177.9(4) . . . . ?
C12 N2 C6 C7 0.7(4) . . . . ?
Zn1 N2 C6 C7 -169.9(2) . . . . ?
C12 N2 C6 C5 -176.1(3) . . . . ?
Zn1 N2 C6 C5 13.4(5) . . . . ?
N1 C5 C6 N2 -0.6(5) . . . . ?
C4 C5 C6 N2 179.3(4) . . . . ?
N1 C5 C6 C7 -176.4(4) . . . . ?
C4 C5 C6 C7 3.5(7) . . . . ?
N2 C6 C7 N4 -0.8(4) . . . . ?
C5 C6 C7 N4 175.3(4) . . . . ?
N2 C6 C7 C8 176.5(4) . . . . ?
C5 C6 C7 C8 -7.4(7) . . . . ?
C11 N4 C7 C6 -178.6(3) . . . . ?
C12 N4 C7 C6 0.7(4) . . . . ?
C11 N4 C7 C8 3.7(6) . . . . ?
C12 N4 C7 C8 -177.0(4) . . . . ?
C6 C7 C8 C9 -178.8(4) . . . . ?
N4 C7 C8 C9 -1.8(7) . . . . ?
C7 C8 C9 C10 -0.7(8) . . . . ?
C8 C9 C10 C11 1.2(9) . . . . ?
C9 C10 C11 N4 0.8(8) . . . . ?
C7 N4 C11 C10 -3.2(6) . . . . ?
C12 N4 C11 C10 177.8(5) . . . . ?
C6 N2 C12 N4 -0.2(4) . . . . ?
Zn1 N2 C12 N4 169.6(3) . . . . ?
C6 N2 C12 C13 171.5(3) . . . . ?
Zn1 N2 C12 C13 -18.7(5) . . . . ?
C7 N4 C12 N2 -0.3(4) . . . . ?
C11 N4 C12 N2 178.9(4) . . . . ?
C7 N4 C12 C13 -171.2(4) . . . . ?
C11 N4 C12 C13 7.9(8) . . . . ?
N2 C12 C13 C14 57.7(5) . . . . ?
N4 C12 C13 C14 -132.4(4) . . . . ?
N2 C12 C13 C13 -65.3(5) . . . 2_755 ?
N4 C12 C13 C13 104.6(5) . . . 2_755 ?
C18 N3 C14 C15 -0.7(6) . . . . ?
Zn1 N3 C14 C15 -172.6(3) . . . . ?
C18 N3 C14 C13 -176.4(3) . . . . ?
Zn1 N3 C14 C13 11.6(5) . . . . ?
C12 C13 C14 N3 -51.6(5) . . . . ?
C13 C13 C14 N3 71.3(5) 2_755 . . . ?
C12 C13 C14 C15 132.6(4) . . . . ?
C13 C13 C14 C15 -104.5(5) 2_755 . . . ?
N3 C14 C15 C16 -1.7(7) . . . . ?
C13 C14 C15 C16 174.0(4) . . . . ?
C14 C15 C16 C17 1.4(7) . . . . ?
C15 C16 C17 C18 1.2(7) . . . . ?
C16 C17 C18 N3 -3.7(7) . . . . ?
C14 N3 C18 C17 3.4(6) . . . . ?
Zn1 N3 C18 C17 176.3(4) . . . . ?

_refine_diff_density_max         0.857
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_2
_audit_block_doi                 10.5517/ccdc.csd.cc1mn1p0
_database_code_depnum_ccdc_archive 'CCDC 1508822'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N10 Zn'
_chemical_formula_sum            'C18 H14 N10 Zn'
_chemical_formula_weight         435.76

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'

_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                   18.130(3)
_cell_length_b                   18.615(3)
_cell_length_c                   13.827(2)
_cell_angle_alpha                90
_cell_angle_beta                 128.341(2)
_cell_angle_gamma                90
_cell_volume                     3660.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1939
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      21.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.371
_shelx_estimated_absorpt_T_min   0.752
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7524
_exptl_absorpt_correction_T_max  0.8751
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9356
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.802
_diffrn_reflns_theta_max         25.249
_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             3315
_reflns_number_gt                2073
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0691P)²+0.4138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3315
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.25594(3) 0.08885(2) 0.17125(5) 0.0714(2) Uani 1 1 d . . . . .
N1 N 0.1722(2) -0.01016(18) 0.0830(3) 0.0703(9) Uani 1 1 d . . . . .
N2 N 0.3685(2) 0.02324(16) 0.2791(3) 0.0573(7) Uani 1 1 d . . . . .
N3 N 0.5186(2) -0.00340(16) 0.3885(3) 0.0571(7) Uani 1 1 d . . . . .
N4 N 0.3829(2) 0.16344(17) 0.2850(3) 0.0697(9) Uani 1 1 d . . . . .
N5 N 0.2298(3) 0.1286(2) 0.0178(4) 0.0931(12) Uani 1 1 d . . . . .
N6 N 0.1924(3) 0.1030(2) -0.0770(5) 0.0867(11) Uani 1 1 d . . . . .
N7 N 0.1546(5) 0.0792(3) -0.1747(6) 0.141(2) Uani 1 1 d . . . . .
N8 N 0.1763(3) 0.1301(3) 0.2070(5) 0.1190(17) Uani 1 1 d . . . . .
N9 N 0.1734(2) 0.1803(2) 0.2515(4) 0.0798(10) Uani 1 1 d . . . . .
N10 N 0.1660(4) 0.2245(3) 0.2997(5) 0.1273(17) Uani 1 1 d . . . . .
C1 C 0.0853(3) 0.0025(2) -0.0237(4) 0.0784(12) Uani 1 1 d . . . . .
H1 H 0.063797 0.049688 -0.042959 0.094 Uiso 1 1 calc R U . . .
C2 C 0.0273(3) -0.0505(3) -0.1047(4) 0.0910(14) Uani 1 1 d . . . . .
H2 H -0.032955 -0.039697 -0.175379 0.109 Uiso 1 1 calc R U . . .
C3 C 0.0598(3) -0.1194(3) -0.0798(5) 0.0963(15) Uani 1 1 d . . . . .
H3 H 0.022698 -0.156368 -0.134407 0.116 Uiso 1 1 calc R U . . .
C4 C 0.1474(3) -0.1331(2) 0.0265(4) 0.0817(12) Uani 1 1 d . . . . .
H4 H 0.170842 -0.179733 0.043902 0.098 Uiso 1 1 calc R U . . .
C5 C 0.2020(3) -0.0786(2) 0.1090(4) 0.0664(10) Uani 1 1 d . . . . .
C6 C 0.2927(3) -0.0965(2) 0.2328(4) 0.0759(12) Uani 1 1 d . . . . .
H6A H 0.279969 -0.098440 0.291303 0.091 Uiso 1 1 calc R U . . .
H6B H 0.310746 -0.144486 0.227576 0.091 Uiso 1 1 calc R U . . .
C7 C 0.3746(3) -0.0493(2) 0.2851(3) 0.0609(10) Uani 1 1 d . . . . .
C8 C 0.4677(3) -0.0680(2) 0.3520(3) 0.0596(9) Uani 1 1 d . . . . .
C9 C 0.5174(3) -0.1340(2) 0.3874(4) 0.0734(11) Uani 1 1 d . . . . .
H9 H 0.485373 -0.177430 0.364420 0.088 Uiso 1 1 calc R U . . .
C10 C 0.6125(3) -0.1328(2) 0.4551(4) 0.0789(12) Uani 1 1 d . . . . .
H10 H 0.645698 -0.175691 0.477216 0.095 Uiso 1 1 calc R U . . .
C11 C 0.6604(3) -0.0674(3) 0.4916(4) 0.0811(13) Uani 1 1 d . . . . .
H11 H 0.725629 -0.067842 0.540562 0.097 Uiso 1 1 calc R U . . .
C12 C 0.6163(3) -0.0043(2) 0.4592(4) 0.0721(11) Uani 1 1 d . . . . .
H12 H 0.650040 0.038404 0.483305 0.087 Uiso 1 1 calc R U . . .
C13 C 0.4546(2) 0.0508(2) 0.3411(3) 0.0565(9) Uani 1 1 d . . . . .
C14 C 0.4674(3) 0.1293(2) 0.3511(3) 0.0605(9) Uani 1 1 d . . . . .
C15 C 0.5510(3) 0.1667(2) 0.4177(4) 0.0757(12) Uani 1 1 d . . . . .
H15 H 0.608200 0.142637 0.460887 0.091 Uiso 1 1 calc R U . . .
C16 C 0.5476(4) 0.2408(3) 0.4188(5) 0.0911(14) Uani 1 1 d . . . . .
H16 H 0.603145 0.267150 0.464172 0.109 Uiso 1 1 calc R U . . .
C17 C 0.4635(4) 0.2754(3) 0.3540(5) 0.0965(15) Uani 1 1 d . . . . .
H17 H 0.460965 0.325258 0.355488 0.116 Uiso 1 1 calc R U . . .
C18 C 0.3813(3) 0.2351(2) 0.2854(5) 0.0869(13) Uani 1 1 d . . . . .
H18 H 0.323608 0.258605 0.238579 0.104 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 N8 1.950(4) . ?
Zn1 N5 2.007(5) . ?
Zn1 N2 2.026(3) . ?
Zn1 N1 2.212(3) . ?
Zn1 N4 2.283(3) . ?
N1 C5 1.343(5) . ?
N1 C1 1.353(5) . ?
N2 C13 1.333(4) . ?
N2 C7 1.354(4) . ?
N3 C13 1.359(4) . ?
N3 C12 1.395(5) . ?
N3 C8 1.405(5) . ?
N4 C18 1.333(5) . ?
N4 C14 1.358(5) . ?
N5 N6 1.141(6) . ?
N6 N7 1.159(7) . ?
N8 N9 1.139(5) . ?
N9 N10 1.118(5) . ?
C1 C2 1.368(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.500(6) . ?
C6 C7 1.472(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.374(5) . ?
C8 C9 1.418(5) . ?
C9 C10 1.358(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.396(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.332(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.474(5) . ?
C14 C15 1.377(5) . ?
C15 C16 1.381(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(6) . ?
C17 H17 0.9300 . ?
C18 H18 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
N8 Zn1 N5 113.4(2) . . ?
N8 Zn1 N2 128.08(18) . . ?
N5 Zn1 N2 118.04(15) . . ?
N8 Zn1 N1 96.03(16) . . ?
N5 Zn1 N1 95.31(15) . . ?
N2 Zn1 N1 86.39(12) . . ?
N8 Zn1 N4 100.08(15) . . ?
N5 Zn1 N4 88.86(15) . . ?
N2 Zn1 N4 74.61(12) . . ?
N1 Zn1 N4 160.18(12) . . ?
C5 N1 C1 117.4(4) . . ?
C5 N1 Zn1 128.2(3) . . ?
C1 N1 Zn1 113.1(3) . . ?
C13 N2 C7 109.0(3) . . ?
C13 N2 Zn1 119.0(2) . . ?
C7 N2 Zn1 130.8(2) . . ?
C13 N3 C12 132.8(3) . . ?
C13 N3 C8 106.8(3) . . ?
C12 N3 C8 120.4(3) . . ?
C18 N4 C14 118.9(4) . . ?
C18 N4 Zn1 126.5(3) . . ?
C14 N4 Zn1 114.4(2) . . ?
N6 N5 Zn1 130.0(4) . . ?
N5 N6 N7 177.7(6) . . ?
N9 N8 Zn1 138.6(4) . . ?
N10 N9 N8 171.7(5) . . ?
N1 C1 C2 123.4(4) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 118.7(5) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C4 120.8(4) . . ?
N1 C5 C6 119.4(3) . . ?
C4 C5 C6 119.7(4) . . ?
C7 C6 C5 119.1(3) . . ?
C7 C6 H6A 107.5 . . ?
C5 C6 H6A 107.5 . . ?
C7 C6 H6B 107.5 . . ?
C5 C6 H6B 107.5 . . ?
H6A C6 H6B 107.0 . . ?
N2 C7 C8 108.3(3) . . ?
N2 C7 C6 123.0(3) . . ?
C8 C7 C6 128.6(4) . . ?
C7 C8 N3 106.5(3) . . ?
C7 C8 C9 134.8(4) . . ?
N3 C8 C9 118.8(4) . . ?
C10 C9 C8 119.2(4) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 122.6(4) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 N3 118.9(4) . . ?
C11 C12 H12 120.6 . . ?
N3 C12 H12 120.6 . . ?
N2 C13 N3 109.5(3) . . ?
N2 C13 C14 119.7(3) . . ?
N3 C13 C14 130.9(3) . . ?
N4 C14 C15 121.8(4) . . ?
N4 C14 C13 110.8(3) . . ?
C15 C14 C13 127.4(4) . . ?
C14 C15 C16 118.3(4) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 118.9(5) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N4 C18 C17 121.7(4) . . ?
N4 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.2(6) . . . . ?
Zn1 N1 C1 C2 168.4(3) . . . . ?
N1 C1 C2 C3 -2.7(7) . . . . ?
C1 C2 C3 C4 2.0(7) . . . . ?
C2 C3 C4 C5 1.2(7) . . . . ?
C1 N1 C5 C4 3.1(6) . . . . ?
Zn1 N1 C5 C4 -163.1(3) . . . . ?
C1 N1 C5 C6 -172.6(4) . . . . ?
Zn1 N1 C5 C6 21.3(5) . . . . ?
C3 C4 C5 N1 -3.8(6) . . . . ?
C3 C4 C5 C6 171.8(4) . . . . ?
N1 C5 C6 C7 -43.1(6) . . . . ?
C4 C5 C6 C7 141.1(4) . . . . ?
C13 N2 C7 C8 -0.7(4) . . . . ?
Zn1 N2 C7 C8 166.5(2) . . . . ?
C13 N2 C7 C6 176.1(4) . . . . ?
Zn1 N2 C7 C6 -16.7(5) . . . . ?
C5 C6 C7 N2 41.7(6) . . . . ?
C5 C6 C7 C8 -142.2(4) . . . . ?
N2 C7 C8 N3 1.0(4) . . . . ?
C6 C7 C8 N3 -175.6(4) . . . . ?
N2 C7 C8 C9 -178.7(4) . . . . ?
C6 C7 C8 C9 4.8(7) . . . . ?
C13 N3 C8 C7 -0.9(4) . . . . ?
C12 N3 C8 C7 179.7(3) . . . . ?
C13 N3 C8 C9 178.8(3) . . . . ?
C12 N3 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 C10 179.5(4) . . . . ?
N3 C8 C9 C10 -0.1(6) . . . . ?
C8 C9 C10 C11 1.5(6) . . . . ?
C9 C10 C11 C12 -2.3(7) . . . . ?
C10 C11 C12 N3 1.6(6) . . . . ?
C13 N3 C12 C11 -179.4(4) . . . . ?
C8 N3 C12 C11 -0.1(5) . . . . ?
C7 N2 C13 N3 0.1(4) . . . . ?
Zn1 N2 C13 N3 -168.8(2) . . . . ?
C7 N2 C13 C14 -178.5(3) . . . . ?
Zn1 N2 C13 C14 12.5(4) . . . . ?
C12 N3 C13 N2 179.8(4) . . . . ?
C8 N3 C13 N2 0.5(4) . . . . ?
C12 N3 C13 C14 -1.7(6) . . . . ?
C8 N3 C13 C14 178.9(4) . . . . ?
C18 N4 C14 C15 -0.3(6) . . . . ?
Zn1 N4 C14 C15 175.4(3) . . . . ?
C18 N4 C14 C13 178.8(3) . . . . ?
Zn1 N4 C14 C13 -5.5(4) . . . . ?
N2 C13 C14 N4 -3.7(5) . . . . ?
N3 C13 C14 N4 178.0(3) . . . . ?
N2 C13 C14 C15 175.4(4) . . . . ?
N3 C13 C14 C15 -2.9(6) . . . . ?
N4 C14 C15 C16 1.6(6) . . . . ?
C13 C14 C15 C16 -177.4(4) . . . . ?
C14 C15 C16 C17 -0.9(7) . . . . ?
C15 C16 C17 C18 -0.9(7) . . . . ?
C14 N4 C18 C17 -1.7(7) . . . . ?
Zn1 N4 C18 C17 -176.8(4) . . . . ?
C16 C17 C18 N4 2.3(8) . . . . ?

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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/ccdc.csd.cc1mn1cp
_database_code_depnum_ccdc_archive 'CCDC 1508812'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Cl4 N8 Zn2'
_chemical_formula_sum            'C36 H26 Cl4 N8 Zn2'
_chemical_formula_weight         843.19

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/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                   8.730(2)
_cell_length_b                   13.047(4)
_cell_length_c                   15.560(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.344(3)
_cell_angle_gamma                90
_cell_volume                     1761.5(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1665
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      20.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.705
_shelx_estimated_absorpt_T_min   0.695
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4120
_exptl_absorpt_correction_T_max  0.6147
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6438
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.042
_diffrn_reflns_theta_max         25.669
_diffrn_reflns_theta_full        25.669
_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             2071
_reflns_number_gt                1568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+1.6398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2071
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.86662(7) 0.25717(5) 0.94919(4) 0.0643(3) Uani 1 1 d . . . . .
Cl1 Cl 0.72397(18) 0.33481(12) 0.83801(10) 0.0829(5) Uani 1 1 d . . . . .
Cl2 Cl 1.10233(18) 0.31357(13) 0.99749(12) 0.0922(6) Uani 1 1 d . . . . .
N2 N 0.7789(5) 0.1437(3) 1.0171(3) 0.0584(11) Uani 1 1 d . . . . .
N1 N 0.9375(5) 0.1248(3) 0.8634(3) 0.0578(11) Uani 1 1 d . . . . .
N3 N 0.7221(6) 0.3364(4) 1.0456(3) 0.0810(14) Uani 1 1 d . . . . .
N4 N 0.6098(5) 0.0793(4) 1.0968(3) 0.0672(13) Uani 1 1 d . . . . .
C5 C 0.9326(5) 0.0247(4) 0.8798(3) 0.0511(13) Uani 1 1 d . . . . .
C7 C 0.7949(5) 0.0421(4) 1.0142(3) 0.0506(13) Uani 1 1 d . . . . .
C4 C 0.9481(6) -0.0484(5) 0.8175(4) 0.0719(16) Uani 1 1 d . . . . .
H4 H 0.940506 -0.117770 0.830168 0.086 Uiso 1 1 calc R U . . .
C6 C 0.9201(5) -0.0086(4) 0.9724(3) 0.0498(12) Uani 1 1 d . . . . .
H6 H 0.899378 -0.082487 0.971477 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6257(7) 0.2730(5) 1.0788(4) 0.0736(17) Uani 1 1 d . . . . .
C13 C 0.6663(6) 0.1677(5) 1.0670(3) 0.0594(14) Uani 1 1 d . . . . .
C1 C 0.9641(7) 0.1531(5) 0.7839(4) 0.0770(17) Uani 1 1 d . . . . .
H1 H 0.967360 0.222795 0.771744 0.092 Uiso 1 1 calc R U . . .
C8 C 0.6901(6) -0.0024(5) 1.0640(3) 0.0602(14) Uani 1 1 d . . . . .
C2 C 0.9868(7) 0.0855(6) 0.7193(4) 0.088(2) Uani 1 1 d . . . . .
H2 H 1.009447 0.108828 0.665632 0.105 Uiso 1 1 calc R U . . .
C3 C 0.9754(7) -0.0168(6) 0.7354(4) 0.088(2) Uani 1 1 d . . . . .
H3 H 0.985664 -0.064545 0.692067 0.105 Uiso 1 1 calc R U . . .
C15 C 0.4983(8) 0.3089(6) 1.1177(4) 0.101(2) Uani 1 1 d . . . . .
H15 H 0.428940 0.263422 1.138456 0.121 Uiso 1 1 calc R U . . .
C16 C 0.4790(11) 0.4130(8) 1.1244(5) 0.122(3) Uani 1 1 d . . . . .
H16 H 0.394252 0.438552 1.148817 0.146 Uiso 1 1 calc R U . . .
C18 C 0.7029(9) 0.4384(6) 1.0532(4) 0.101(2) Uani 1 1 d . . . . .
H18 H 0.771183 0.482359 1.029763 0.121 Uiso 1 1 calc R U . . .
C17 C 0.5841(11) 0.4803(7) 1.0951(5) 0.115(3) Uani 1 1 d . . . . .
H17 H 0.575876 0.550675 1.102953 0.138 Uiso 1 1 calc R U . . .
C9 C 0.6549(6) -0.1059(5) 1.0840(4) 0.0750(17) Uani 1 1 d . . . . .
H9 H 0.707955 -0.160155 1.062358 0.090 Uiso 1 1 calc R U . . .
C12 C 0.4970(7) 0.0617(7) 1.1515(4) 0.086(2) Uani 1 1 d . . . . .
H12 H 0.446279 0.115628 1.175417 0.104 Uiso 1 1 calc R U . . .
C10 C 0.5419(8) -0.1229(6) 1.1355(4) 0.094(2) Uani 1 1 d . . . . .
H10 H 0.515426 -0.189518 1.149149 0.112 Uiso 1 1 calc R U . . .
C11 C 0.4638(8) -0.0377(8) 1.1686(4) 0.098(2) Uani 1 1 d . . . . .
H11 H 0.386382 -0.050921 1.203577 0.118 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.019(4) . ?
Zn1 Cl2 2.2359(17) . ?
Zn1 Cl1 2.2570(16) . ?
Zn1 N1 2.308(4) . ?
Zn1 N3 2.308(5) . ?
N2 C7 1.334(6) . ?
N2 C13 1.355(6) . ?
N1 C5 1.333(6) . ?
N1 C1 1.336(6) . ?
N3 C14 1.324(7) . ?
N3 C18 1.348(8) . ?
N4 C13 1.357(7) . ?
N4 C12 1.390(7) . ?
N4 C8 1.402(7) . ?
C5 C4 1.378(7) . ?
C5 C6 1.520(6) . ?
C7 C8 1.389(7) . ?
C7 C6 1.488(7) . ?
C4 C3 1.387(8) . ?
C6 C6 1.572(9) 3_757 ?
C14 C15 1.405(9) . ?
C14 C13 1.435(8) . ?
C1 C2 1.368(8) . ?
C8 C9 1.426(8) . ?
C2 C3 1.364(9) . ?
C15 C16 1.375(11) . ?
C16 C17 1.383(11) . ?
C18 C17 1.396(10) . ?
C9 C10 1.356(8) . ?
C12 C11 1.362(10) . ?
C10 C11 1.429(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
N2 Zn1 Cl2 117.00(13) . . ?
N2 Zn1 Cl1 121.41(12) . . ?
Cl2 Zn1 Cl1 121.29(7) . . ?
N2 Zn1 N1 83.99(17) . . ?
Cl2 Zn1 N1 98.33(11) . . ?
Cl1 Zn1 N1 93.05(11) . . ?
N2 Zn1 N3 73.9(2) . . ?
Cl2 Zn1 N3 100.55(14) . . ?
Cl1 Zn1 N3 90.13(13) . . ?
N1 Zn1 N3 155.69(19) . . ?
C7 N2 C13 109.5(5) . . ?
C7 N2 Zn1 131.6(4) . . ?
C13 N2 Zn1 118.1(4) . . ?
C5 N1 C1 117.4(5) . . ?
C5 N1 Zn1 127.3(3) . . ?
C1 N1 Zn1 114.5(4) . . ?
C14 N3 C18 119.5(6) . . ?
C14 N3 Zn1 113.0(4) . . ?
C18 N3 Zn1 125.5(5) . . ?
C13 N4 C12 131.2(6) . . ?
C13 N4 C8 107.9(4) . . ?
C12 N4 C8 120.9(6) . . ?
N1 C5 C4 122.4(5) . . ?
N1 C5 C6 118.0(4) . . ?
C4 C5 C6 119.5(5) . . ?
N2 C7 C8 108.6(5) . . ?
N2 C7 C6 122.7(5) . . ?
C8 C7 C6 128.2(5) . . ?
C5 C4 C3 118.8(6) . . ?
C7 C6 C5 114.9(4) . . ?
C7 C6 C6 110.3(5) . 3_757 ?
C5 C6 C6 108.9(5) . 3_757 ?
N3 C14 C15 121.9(7) . . ?
N3 C14 C13 111.8(6) . . ?
C15 C14 C13 126.3(7) . . ?
N2 C13 N4 108.2(5) . . ?
N2 C13 C14 120.0(6) . . ?
N4 C13 C14 131.8(6) . . ?
N1 C1 C2 123.9(6) . . ?
C7 C8 N4 105.7(5) . . ?
C7 C8 C9 133.5(6) . . ?
N4 C8 C9 120.7(5) . . ?
C3 C2 C1 118.4(6) . . ?
C2 C3 C4 119.0(6) . . ?
C16 C15 C14 118.1(8) . . ?
C15 C16 C17 120.8(8) . . ?
N3 C18 C17 122.2(8) . . ?
C16 C17 C18 117.4(8) . . ?
C10 C9 C8 118.2(6) . . ?
C11 C12 N4 117.1(7) . . ?
C9 C10 C11 119.5(7) . . ?
C12 C11 C10 123.4(7) . . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_3
_audit_block_doi                 10.5517/ccdc.csd.cc13n430
_database_code_depnum_ccdc_archive 'CCDC 1032241'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H28 Cl4 N8 Zn2'
_chemical_formula_sum            'C36 H28 Cl4 N8 O Zn2'
_chemical_formula_weight         861.20

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'
O O 0.0106 0.0060 '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                   22.85(3)
_cell_length_b                   14.997(18)
_cell_length_c                   14.976(19)
_cell_angle_alpha                90
_cell_angle_beta                 127.339(14)
_cell_angle_gamma                90
_cell_volume                     4080(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    804
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      16.74

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.476
_shelx_estimated_absorpt_T_min   0.728
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7277
_exptl_absorpt_correction_T_max  0.8786
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6388
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.761
_diffrn_reflns_theta_max         25.304
_diffrn_reflns_theta_full        25.304
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1972
_reflns_number_gt                1258
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.4360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1972
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.82907(5) 0.02211(6) -0.02440(7) 0.0677(4) Uani 1 1 d . . . . .
Cl1 Cl 0.88605(13) -0.01858(15) -0.09627(19) 0.0943(8) Uani 1 1 d . . . . .
Cl2 Cl 0.70999(13) -0.02090(16) -0.1138(2) 0.1140(10) Uani 1 1 d . . . . .
N1 N 0.8746(3) -0.0874(4) 0.1075(5) 0.0630(18) Uani 1 1 d . . . . .
N2 N 0.8805(3) 0.1071(4) 0.1080(5) 0.0527(16) Uani 1 1 d . . . . .
N3 N 0.9006(4) 0.2353(5) 0.1930(6) 0.0650(18) Uani 1 1 d . . . . .
N4 N 0.7937(4) 0.1639(5) -0.0983(7) 0.079(2) Uani 1 1 d . . . . .
C1 C 0.8411(4) -0.1692(7) 0.0699(7) 0.080(3) Uani 1 1 d . . . . .
H1 H 0.804897 -0.176582 -0.006910 0.096 Uiso 1 1 calc R U . . .
C2 C 0.8574(5) -0.2397(6) 0.1378(10) 0.095(3) Uani 1 1 d . . . . .
H2 H 0.834633 -0.294515 0.108118 0.114 Uiso 1 1 calc R U . . .
C3 C 0.9093(5) -0.2279(7) 0.2530(9) 0.091(3) Uani 1 1 d . . . . .
H3 H 0.920524 -0.274171 0.302473 0.110 Uiso 1 1 calc R U . . .
C4 C 0.9433(4) -0.1471(6) 0.2921(7) 0.071(2) Uani 1 1 d . . . . .
H4 H 0.978454 -0.138022 0.368831 0.085 Uiso 1 1 calc R U . . .
C5 C 0.9259(4) -0.0794(5) 0.2185(7) 0.055(2) Uani 1 1 d . . . . .
C6 C 0.9704(4) 0.0055(4) 0.2621(6) 0.051(2) Uani 1 1 d . . . . .
H6 H 0.998039 0.005268 0.343817 0.061 Uiso 1 1 calc R U . . .
C7 C 0.9283(4) 0.0916(5) 0.2198(6) 0.050(2) Uani 1 1 d . . . . .
C8 C 0.9401(4) 0.1710(6) 0.2752(7) 0.055(2) Uani 1 1 d . . . . .
C9 C 0.9870(4) 0.1943(6) 0.3907(7) 0.073(2) Uani 1 1 d . . . . .
H9 H 1.015093 0.151360 0.445745 0.087 Uiso 1 1 calc R U . . .
C10 C 0.9897(5) 0.2798(8) 0.4181(8) 0.096(3) Uani 1 1 d . . . . .
H10 H 1.019270 0.296469 0.493293 0.115 Uiso 1 1 calc R U . . .
C11 C 0.9482(6) 0.3451(7) 0.3344(11) 0.108(3) Uani 1 1 d . . . . .
H11 H 0.952096 0.404396 0.355752 0.130 Uiso 1 1 calc R U . . .
C12 C 0.9025(5) 0.3239(7) 0.2232(9) 0.089(3) Uani 1 1 d . . . . .
H12 H 0.873470 0.367164 0.169019 0.107 Uiso 1 1 calc R U . . .
C13 C 0.8629(4) 0.1936(6) 0.0904(7) 0.056(2) Uani 1 1 d . . . . .
C14 C 0.8174(4) 0.2281(7) -0.0231(9) 0.070(2) Uani 1 1 d . . . . .
C15 C 0.7986(5) 0.3179(8) -0.0524(9) 0.098(3) Uani 1 1 d . . . . .
H15 H 0.815301 0.361703 0.002041 0.118 Uiso 1 1 calc R U . . .
C16 C 0.7550(6) 0.3387(8) -0.1640(12) 0.120(4) Uani 1 1 d . . . . .
H16 H 0.741445 0.397757 -0.185789 0.144 Uiso 1 1 calc R U . . .
C17 C 0.7518(5) 0.1886(8) -0.2076(9) 0.111(4) Uani 1 1 d . . . . .
H17 H 0.736041 0.144903 -0.261834 0.133 Uiso 1 1 calc R U . . .
C18 C 0.7313(6) 0.2765(10) -0.2423(10) 0.119(4) Uani 1 1 d . . . . .
H18 H 0.701886 0.291398 -0.318080 0.143 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.027(6) . ?
Zn1 Cl1 2.219(3) . ?
Zn1 N1 2.279(6) . ?
Zn1 Cl2 2.279(4) . ?
Zn1 N4 2.305(7) . ?
N1 C5 1.337(8) . ?
N1 C1 1.373(9) . ?
N2 C13 1.336(8) . ?
N2 C7 1.354(8) . ?
N3 C13 1.374(9) . ?
N3 C8 1.382(8) . ?
N3 C12 1.396(10) . ?
N4 C14 1.321(10) . ?
N4 C17 1.354(11) . ?
C1 C2 1.352(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.390(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.508(9) . ?
C6 C7 1.502(9) . ?
C6 C6 1.596(13) 2_755 ?
C6 H6 0.9800 . ?
C7 C8 1.381(9) . ?
C8 C9 1.419(10) . ?
C9 C10 1.336(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.410(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(11) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.447(11) . ?
C14 C15 1.401(11) . ?
C15 C16 1.364(13) . ?
C15 H15 0.9300 . ?
C16 C18 1.329(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(13) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 Cl1 118.98(18) . . ?
N2 Zn1 N1 85.2(3) . . ?
Cl1 Zn1 N1 97.40(18) . . ?
N2 Zn1 Cl2 122.01(17) . . ?
Cl1 Zn1 Cl2 118.66(13) . . ?
N1 Zn1 Cl2 93.44(18) . . ?
N2 Zn1 N4 73.5(3) . . ?
Cl1 Zn1 N4 99.2(2) . . ?
N1 Zn1 N4 157.5(3) . . ?
Cl2 Zn1 N4 91.87(18) . . ?
C5 N1 C1 116.2(7) . . ?
C5 N1 Zn1 127.4(6) . . ?
C1 N1 Zn1 116.1(6) . . ?
C13 N2 C7 109.3(6) . . ?
C13 N2 Zn1 119.5(5) . . ?
C7 N2 Zn1 131.0(6) . . ?
C13 N3 C8 107.9(7) . . ?
C13 N3 C12 132.1(8) . . ?
C8 N3 C12 120.0(8) . . ?
C14 N4 C17 117.0(9) . . ?
C14 N4 Zn1 114.8(6) . . ?
C17 N4 Zn1 128.2(8) . . ?
C2 C1 N1 123.9(8) . . ?
C2 C1 H1 118.0 . . ?
N1 C1 H1 118.0 . . ?
C1 C2 C3 118.3(9) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 118.6(8) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 120.1(8) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 122.8(7) . . ?
N1 C5 C6 117.8(7) . . ?
C4 C5 C6 119.2(8) . . ?
C7 C6 C5 116.8(6) . . ?
C7 C6 C6 108.6(4) . 2_755 ?
C5 C6 C6 110.1(4) . 2_755 ?
C7 C6 H6 106.9 . . ?
C5 C6 H6 106.9 . . ?
C6 C6 H6 106.9 2_755 . ?
N2 C7 C8 108.2(6) . . ?
N2 C7 C6 119.9(7) . . ?
C8 C7 C6 130.3(7) . . ?
N3 C8 C7 106.4(7) . . ?
N3 C8 C9 121.1(8) . . ?
C7 C8 C9 132.2(9) . . ?
C10 C9 C8 118.0(8) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 120.9(9) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 121.9(9) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 N3 117.9(8) . . ?
C11 C12 H12 121.0 . . ?
N3 C12 H12 121.0 . . ?
N2 C13 N3 108.2(7) . . ?
N2 C13 C14 119.6(9) . . ?
N3 C13 C14 131.9(9) . . ?
N4 C14 C15 122.9(9) . . ?
N4 C14 C13 111.8(9) . . ?
C15 C14 C13 125.2(11) . . ?
C16 C15 C14 117.4(10) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C18 C16 C15 121.6(12) . . ?
C18 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
N4 C17 C18 122.9(10) . . ?
N4 C17 H17 118.6 . . ?
C18 C17 H17 118.6 . . ?
C16 C18 C17 118.1(11) . . ?
C16 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.4(12) . . . . ?
Zn1 N1 C1 C2 -175.0(7) . . . . ?
N1 C1 C2 C3 2.6(14) . . . . ?
C1 C2 C3 C4 -2.6(14) . . . . ?
C2 C3 C4 C5 0.5(13) . . . . ?
C1 N1 C5 C4 -1.9(10) . . . . ?
Zn1 N1 C5 C4 172.1(5) . . . . ?
C1 N1 C5 C6 172.8(6) . . . . ?
Zn1 N1 C5 C6 -13.3(9) . . . . ?
C3 C4 C5 N1 1.8(12) . . . . ?
C3 C4 C5 C6 -172.8(7) . . . . ?
N1 C5 C6 C7 49.6(8) . . . . ?
C4 C5 C6 C7 -135.5(7) . . . . ?
N1 C5 C6 C6 -74.9(8) . . . 2_755 ?
C4 C5 C6 C6 100.0(8) . . . 2_755 ?
C13 N2 C7 C8 1.3(8) . . . . ?
Zn1 N2 C7 C8 -172.5(5) . . . . ?
C13 N2 C7 C6 -165.5(6) . . . . ?
Zn1 N2 C7 C6 20.6(9) . . . . ?
C5 C6 C7 N2 -55.3(8) . . . . ?
C6 C6 C7 N2 70.0(8) 2_755 . . . ?
C5 C6 C7 C8 141.2(7) . . . . ?
C6 C6 C7 C8 -93.6(9) 2_755 . . . ?
C13 N3 C8 C7 2.9(8) . . . . ?
C12 N3 C8 C7 -179.0(6) . . . . ?
C13 N3 C8 C9 177.6(7) . . . . ?
C12 N3 C8 C9 -4.3(10) . . . . ?
N2 C7 C8 N3 -2.6(8) . . . . ?
C6 C7 C8 N3 162.4(6) . . . . ?
N2 C7 C8 C9 -176.5(7) . . . . ?
C6 C7 C8 C9 -11.4(13) . . . . ?
N3 C8 C9 C10 2.6(11) . . . . ?
C7 C8 C9 C10 175.7(8) . . . . ?
C8 C9 C10 C11 -1.3(13) . . . . ?
C9 C10 C11 C12 1.8(16) . . . . ?
C10 C11 C12 N3 -3.4(15) . . . . ?
C13 N3 C12 C11 -177.8(9) . . . . ?
C8 N3 C12 C11 4.6(12) . . . . ?
C7 N2 C13 N3 0.5(8) . . . . ?
Zn1 N2 C13 N3 175.2(4) . . . . ?
C7 N2 C13 C14 174.7(6) . . . . ?
Zn1 N2 C13 C14 -10.6(9) . . . . ?
C8 N3 C13 N2 -2.1(8) . . . . ?
C12 N3 C13 N2 -179.9(7) . . . . ?
C8 N3 C13 C14 -175.4(7) . . . . ?
C12 N3 C13 C14 6.8(14) . . . . ?
C17 N4 C14 C15 2.6(12) . . . . ?
Zn1 N4 C14 C15 -177.0(6) . . . . ?
C17 N4 C14 C13 -178.5(7) . . . . ?
Zn1 N4 C14 C13 1.9(8) . . . . ?
N2 C13 C14 N4 5.1(10) . . . . ?
N3 C13 C14 N4 177.7(7) . . . . ?
N2 C13 C14 C15 -176.1(7) . . . . ?
N3 C13 C14 C15 -3.5(13) . . . . ?
N4 C14 C15 C16 -1.2(13) . . . . ?
C13 C14 C15 C16 -180.0(9) . . . . ?
C14 C15 C16 C18 -0.4(16) . . . . ?
C14 N4 C17 C18 -2.5(13) . . . . ?
Zn1 N4 C17 C18 177.1(7) . . . . ?
C15 C16 C18 C17 0.5(18) . . . . ?
N4 C17 C18 C16 1.0(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 Cl2 0.93 2.92 3.390(10) 113.0 .
C2 H2 Cl2 0.93 2.97 3.838(10) 156.0 7_645
C12 H12 Cl2 0.93 2.78 3.592(10) 146.6 7_655
C1 H1 Cl2 0.93 2.92 3.390(10) 113.0 .
C2 H2 Cl2 0.93 2.97 3.838(10) 156.0 7_645
C12 H12 Cl2 0.93 2.78 3.592(10) 146.6 7_655

_refine_diff_density_max         0.587
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.063



####################################################################### 
# 
# 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_5
_audit_block_doi                 10.5517/ccdc.csd.cc13n452
_database_code_depnum_ccdc_archive 'CCDC 1032243'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 N20 Zn2'
_chemical_formula_sum            'C36 H26 N20 Zn2'
_chemical_formula_weight         869.51

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'

_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                   8.884(2)
_cell_length_b                   19.730(5)
_cell_length_c                   21.404(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.623(4)
_cell_angle_gamma                90
_cell_volume                     3744.1(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2292
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      20.27

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             1768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.340
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4120
_exptl_absorpt_correction_T_max  0.6147
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18710
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.405
_diffrn_reflns_theta_max         25.032
_diffrn_reflns_theta_full        25.032
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6588
_reflns_number_gt                3609
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0879P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6588
_refine_ls_number_parameters     524
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1849
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.91335(8) 0.80017(4) 0.00990(3) 0.0552(3) Uani 1 1 d . . . . .
Zn2 Zn 0.42068(9) 0.92398(4) 0.23029(3) 0.0617(3) Uani 1 1 d . . . . .
N13 N 0.5345(5) 0.9840(2) 0.1552(2) 0.0523(13) Uani 1 1 d . . . . .
N12 N 0.3974(5) 0.8519(2) 0.1622(2) 0.0497(12) Uani 1 1 d . . . . .
N11 N 0.2216(6) 0.8578(3) 0.2541(3) 0.0691(15) Uani 1 1 d . . . . .
N2 N 0.8254(5) 0.7544(2) 0.0843(2) 0.0470(12) Uani 1 1 d . . . . .
N3 N 0.9566(5) 0.8882(2) 0.0768(2) 0.0559(13) Uani 1 1 d . . . . .
N1 N 0.8863(6) 0.6853(3) -0.0158(2) 0.0605(14) Uani 1 1 d . . . . .
N16 N 0.3093(5) 0.7592(2) 0.1166(2) 0.0525(13) Uani 1 1 d . . . . .
C7 C 0.7291(6) 0.6714(3) 0.1372(2) 0.0437(10) Uani 1 1 d . U . . .
C30 C 0.4766(6) 0.8421(3) 0.1099(3) 0.0468(14) Uani 1 1 d . . . . .
C31 C 0.6137(6) 0.8830(3) 0.0984(3) 0.0458(14) Uani 1 1 d . . . . .
H31 H 0.639249 0.873729 0.055350 0.055 Uiso 1 1 calc R U . . .
C33 C 0.6426(7) 1.0009(3) 0.0576(3) 0.0555(16) Uani 1 1 d . . . . .
H33 H 0.683012 0.982112 0.022512 0.067 Uiso 1 1 calc R U . . .
C32 C 0.5932(6) 0.9593(3) 0.1040(3) 0.0455(14) Uani 1 1 d . . . . .
C24 C 0.2975(7) 0.8022(3) 0.1664(3) 0.0523(15) Uani 1 1 d . . . . .
C25 C 0.2356(8) 0.6989(3) 0.1000(4) 0.0700(19) Uani 1 1 d . . . . .
H25 H 0.159081 0.682369 0.123479 0.084 Uiso 1 1 calc R U . . .
C29 C 0.4242(7) 0.7841(3) 0.0800(3) 0.0491(15) Uani 1 1 d . . . . .
C23 C 0.1986(7) 0.8021(3) 0.2179(3) 0.0567(16) Uani 1 1 d . . . . .
C34 C 0.6321(7) 1.0699(3) 0.0633(3) 0.0649(18) Uani 1 1 d . . . . .
H34 H 0.664966 1.098189 0.032182 0.078 Uiso 1 1 calc R U . . .
C36 C 0.5246(7) 1.0520(3) 0.1603(3) 0.0649(18) Uani 1 1 d . . . . .
H36 H 0.483579 1.069944 0.195611 0.078 Uiso 1 1 calc R U . . .
C28 C 0.4651(7) 0.7479(3) 0.0268(3) 0.0590(17) Uani 1 1 d . . . . .
H28 H 0.540278 0.764261 0.002500 0.071 Uiso 1 1 calc R U . . .
C26 C 0.2766(9) 0.6654(3) 0.0499(4) 0.082(2) Uani 1 1 d . . . . .
H26 H 0.227845 0.625007 0.039005 0.098 Uiso 1 1 calc R U . . .
C20 C 0.0219(9) 0.8200(5) 0.3154(4) 0.090(3) Uani 1 1 d . . . . .
H20 H -0.040013 0.827773 0.348117 0.108 Uiso 1 1 calc R U . . .
C22 C 0.0927(8) 0.7549(4) 0.2312(4) 0.075(2) Uani 1 1 d . . . . .
H22 H 0.079421 0.716449 0.206262 0.091 Uiso 1 1 calc R U . . .
C19 C 0.1323(9) 0.8672(4) 0.3016(4) 0.088(2) Uani 1 1 d . . . . .
H19 H 0.144252 0.906090 0.325911 0.106 Uiso 1 1 calc R U . . .
C35 C 0.5726(8) 1.0966(3) 0.1152(3) 0.0704(19) Uani 1 1 d . . . . .
H35 H 0.564524 1.143278 0.120368 0.084 Uiso 1 1 calc R U . . .
C27 C 0.3940(8) 0.6894(4) 0.0117(3) 0.075(2) Uani 1 1 d . . . . .
H27 H 0.420119 0.664612 -0.022988 0.090 Uiso 1 1 calc R U . . .
C21 C 0.0064(9) 0.7641(4) 0.2812(4) 0.082(2) Uani 1 1 d . . . . .
H21 H -0.063063 0.731216 0.291248 0.099 Uiso 1 1 calc R U . . .
C6 C 0.8023(6) 0.6874(3) 0.0852(3) 0.0464(12) Uani 1 1 d . U . . .
C5 C 0.8385(7) 0.6466(3) 0.0312(3) 0.0585(17) Uani 1 1 d . . . . .
C1 C 0.9187(8) 0.6544(4) -0.0680(3) 0.080(2) Uani 1 1 d . . . . .
H1 H 0.951747 0.680670 -0.100504 0.096 Uiso 1 1 calc R U . . .
C4 C 0.8264(12) 0.5784(4) 0.0246(4) 0.118(4) Uani 1 1 d . . . . .
H4 H 0.796229 0.552060 0.057586 0.142 Uiso 1 1 calc R U . . .
C8 C 0.6754(9) 0.6105(4) 0.1587(3) 0.082(2) Uani 1 1 d . . . . .
H8 H 0.692371 0.570675 0.137073 0.099 Uiso 1 1 calc R U . . .
C3 C 0.8587(14) 0.5481(4) -0.0308(4) 0.139(4) Uani 1 1 d . . . . .
H3 H 0.847275 0.501533 -0.035892 0.166 Uiso 1 1 calc R U . . .
C2 C 0.9063(10) 0.5860(4) -0.0770(4) 0.098(3) Uani 1 1 d . . . . .
H2 H 0.930712 0.566326 -0.114514 0.117 Uiso 1 1 calc R U . . .
N14 N 0.5977(8) 0.8925(3) 0.2845(3) 0.0768(18) Uani 1 1 d . . . . .
N15 N 0.3258(7) 1.0028(3) 0.2714(3) 0.0756(17) Uani 1 1 d . . . . .
N4 N 1.1127(6) 0.8083(3) -0.0231(3) 0.0704(16) Uani 1 1 d . . . . .
N5 N 0.7508(7) 0.8385(3) -0.0464(3) 0.0758(17) Uani 1 1 d . . . . .
C11 C 0.6293(7) 0.7291(3) 0.2270(3) 0.0644(18) Uani 1 1 d . . . . .
H11 H 0.615729 0.768080 0.250396 0.077 Uiso 1 1 calc R U . . .
N17 N 0.6819(9) 0.9199(3) 0.3198(4) 0.0802(19) Uani 1 1 d . . . . .
N19 N 0.3912(8) 1.0427(3) 0.3038(3) 0.0724(17) Uani 1 1 d . . . . .
N7 N 1.1586(6) 0.7818(3) -0.0677(3) 0.0664(15) Uani 1 1 d . . . . .
N9 N 0.7656(6) 0.8414(3) -0.1016(3) 0.0657(15) Uani 1 1 d . . . . .
C14 C 0.8899(7) 0.8984(3) 0.1304(3) 0.0464(14) Uani 1 1 d . . . . .
C17 C 1.1187(8) 0.9831(4) 0.1011(4) 0.077(2) Uani 1 1 d . . . . .
H17 H 1.195313 1.011749 0.089581 0.092 Uiso 1 1 calc R U . . .
C15 C 0.9381(7) 0.9502(3) 0.1708(3) 0.0606(17) Uani 1 1 d . . . . .
H15 H 0.891866 0.956529 0.208140 0.073 Uiso 1 1 calc R U . . .
C16 C 1.0546(8) 0.9925(3) 0.1556(3) 0.073(2) Uani 1 1 d . . . . .
H16 H 1.088089 1.026865 0.182770 0.088 Uiso 1 1 calc R U . . .
C18 C 1.0692(7) 0.9297(3) 0.0619(3) 0.0697(19) Uani 1 1 d . . . . .
H18 H 1.115327 0.922782 0.024633 0.084 Uiso 1 1 calc R U . . .
C13 C 0.7522(6) 0.8583(3) 0.1432(3) 0.0441(14) Uani 1 1 d . . . . .
H13 H 0.728112 0.867389 0.186427 0.053 Uiso 1 1 calc R U . . .
C12 C 0.7689(6) 0.7834(3) 0.1360(3) 0.0491(12) Uani 1 1 d . U . . .
C10 C 0.5756(9) 0.6686(4) 0.2459(3) 0.087(2) Uani 1 1 d . . . . .
H10 H 0.523025 0.666148 0.282002 0.105 Uiso 1 1 calc R U . . .
C9 C 0.5995(11) 0.6088(4) 0.2105(4) 0.101(3) Uani 1 1 d . . . . .
H9 H 0.561281 0.567674 0.223717 0.121 Uiso 1 1 calc R U . . .
N6 N 0.7060(6) 0.7318(2) 0.1713(2) 0.0571(10) Uani 1 1 d . U . . .
N20 N 0.4513(9) 1.0828(4) 0.3354(4) 0.108(3) Uani 1 1 d . . . . .
N18 N 0.7661(10) 0.9426(4) 0.3574(5) 0.145(4) Uani 1 1 d . . . . .
N10 N 0.7758(8) 0.8466(4) -0.1547(3) 0.107(2) Uani 1 1 d . . . . .
N8 N 1.2115(8) 0.7571(3) -0.1105(3) 0.091(2) Uani 1 1 d . . . . .


_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 1.954(5) . ?
Zn1 N5 1.972(6) . ?
Zn1 N2 2.029(4) . ?
Zn1 N3 2.268(5) . ?
Zn1 N1 2.342(5) . ?
Zn2 N14 1.994(6) . ?
Zn2 N15 2.000(6) . ?
Zn2 N12 2.038(5) . ?
Zn2 N13 2.284(5) . ?
Zn2 N11 2.282(5) . ?
N13 C32 1.335(7) . ?
N13 C36 1.349(7) . ?
N12 C24 1.329(7) . ?
N12 C30 1.372(7) . ?
N11 C19 1.341(8) . ?
N11 C23 1.352(8) . ?
N2 C6 1.337(6) . ?
N2 C12 1.369(7) . ?
N3 C14 1.339(7) . ?
N3 C18 1.347(7) . ?
N1 C1 1.320(8) . ?
N1 C5 1.353(7) . ?
N16 C24 1.371(7) . ?
N16 C25 1.393(7) . ?
N16 C29 1.414(7) . ?
C7 C6 1.361(7) . ?
C7 C8 1.382(8) . ?
C7 N6 1.420(7) . ?
C30 C29 1.379(8) . ?
C30 C31 1.495(7) . ?
C31 C32 1.523(7) . ?
C31 C13 1.587(8) . ?
C33 C34 1.370(8) . ?
C33 C32 1.381(7) . ?
C24 C23 1.453(8) . ?
C25 C26 1.330(10) . ?
C29 C28 1.411(8) . ?
C23 C22 1.367(8) . ?
C34 C35 1.367(9) . ?
C36 C35 1.393(9) . ?
C28 C27 1.346(9) . ?
C26 C27 1.444(10) . ?
C20 C21 1.326(10) . ?
C20 C19 1.398(10) . ?
C22 C21 1.368(10) . ?
C6 C5 1.462(8) . ?
C5 C4 1.356(9) . ?
C1 C2 1.368(9) . ?
C4 C3 1.373(10) . ?
C8 C9 1.333(9) . ?
C3 C2 1.330(11) . ?
N14 N17 1.162(8) . ?
N15 N19 1.178(8) . ?
N4 N7 1.184(7) . ?
N5 N9 1.198(7) . ?
C11 C10 1.355(9) . ?
C11 N6 1.411(7) . ?
N17 N18 1.154(9) . ?
N19 N20 1.149(9) . ?
N7 N8 1.162(7) . ?
N9 N10 1.150(8) . ?
C14 C15 1.390(8) . ?
C14 C13 1.496(8) . ?
C17 C16 1.342(9) . ?
C17 C18 1.400(9) . ?
C15 C16 1.384(8) . ?
C13 C12 1.495(7) . ?
C12 N6 1.405(7) . ?
C10 C9 1.426(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
N4 Zn1 N5 113.1(2) . . ?
N4 Zn1 N2 136.3(2) . . ?
N5 Zn1 N2 110.3(2) . . ?
N4 Zn1 N3 92.5(2) . . ?
N5 Zn1 N3 100.4(2) . . ?
N2 Zn1 N3 84.50(18) . . ?
N4 Zn1 N1 94.4(2) . . ?
N5 Zn1 N1 99.6(2) . . ?
N2 Zn1 N1 73.42(17) . . ?
N3 Zn1 N1 154.26(18) . . ?
N14 Zn2 N15 109.0(3) . . ?
N14 Zn2 N12 103.9(2) . . ?
N15 Zn2 N12 146.2(2) . . ?
N14 Zn2 N13 101.7(2) . . ?
N15 Zn2 N13 97.1(2) . . ?
N12 Zn2 N13 83.58(18) . . ?
N14 Zn2 N11 106.6(2) . . ?
N15 Zn2 N11 89.6(2) . . ?
N12 Zn2 N11 73.43(19) . . ?
N13 Zn2 N11 146.93(19) . . ?
C32 N13 C36 117.4(5) . . ?
C32 N13 Zn2 127.0(4) . . ?
C36 N13 Zn2 115.1(4) . . ?
C24 N12 C30 109.3(5) . . ?
C24 N12 Zn2 120.3(4) . . ?
C30 N12 Zn2 130.3(4) . . ?
C19 N11 C23 118.1(6) . . ?
C19 N11 Zn2 126.4(5) . . ?
C23 N11 Zn2 115.4(4) . . ?
C6 N2 C12 109.6(5) . . ?
C6 N2 Zn1 121.3(4) . . ?
C12 N2 Zn1 128.8(4) . . ?
C14 N3 C18 119.1(5) . . ?
C14 N3 Zn1 126.1(4) . . ?
C18 N3 Zn1 114.6(4) . . ?
C1 N1 C5 117.7(6) . . ?
C1 N1 Zn1 128.4(5) . . ?
C5 N1 Zn1 113.8(4) . . ?
C24 N16 C25 132.0(6) . . ?
C24 N16 C29 108.0(5) . . ?
C25 N16 C29 119.9(5) . . ?
C6 C7 C8 131.9(6) . . ?
C6 C7 N6 108.5(5) . . ?
C8 C7 N6 119.6(6) . . ?
N12 C30 C29 108.7(5) . . ?
N12 C30 C31 121.6(5) . . ?
C29 C30 C31 128.8(5) . . ?
C30 C31 C32 114.7(5) . . ?
C30 C31 C13 110.1(4) . . ?
C32 C31 C13 110.4(4) . . ?
C34 C33 C32 120.0(6) . . ?
N13 C32 C33 122.1(5) . . ?
N13 C32 C31 118.7(5) . . ?
C33 C32 C31 119.1(5) . . ?
N12 C24 N16 108.7(5) . . ?
N12 C24 C23 119.4(6) . . ?
N16 C24 C23 131.9(6) . . ?
C26 C25 N16 118.8(7) . . ?
C30 C29 C28 134.3(6) . . ?
C30 C29 N16 105.4(5) . . ?
C28 C29 N16 120.2(5) . . ?
N11 C23 C22 121.1(7) . . ?
N11 C23 C24 110.9(5) . . ?
C22 C23 C24 128.0(7) . . ?
C33 C34 C35 119.2(6) . . ?
N13 C36 C35 123.3(6) . . ?
C27 C28 C29 119.2(6) . . ?
C25 C26 C27 122.6(7) . . ?
C21 C20 C19 119.1(8) . . ?
C23 C22 C21 119.9(7) . . ?
N11 C19 C20 121.7(8) . . ?
C34 C35 C36 118.0(6) . . ?
C28 C27 C26 119.3(7) . . ?
C20 C21 C22 119.9(7) . . ?
N2 C6 C7 108.9(5) . . ?
N2 C6 C5 119.4(5) . . ?
C7 C6 C5 131.2(6) . . ?
N1 C5 C4 120.6(6) . . ?
N1 C5 C6 111.9(5) . . ?
C4 C5 C6 127.6(6) . . ?
N1 C1 C2 123.7(7) . . ?
C5 C4 C3 120.2(7) . . ?
C9 C8 C7 120.2(7) . . ?
C2 C3 C4 119.4(8) . . ?
C3 C2 C1 118.5(7) . . ?
N17 N14 Zn2 133.2(6) . . ?
N19 N15 Zn2 125.0(5) . . ?
N7 N4 Zn1 128.4(5) . . ?
N9 N5 Zn1 119.9(5) . . ?
C10 C11 N6 118.9(6) . . ?
N18 N17 N14 174.8(9) . . ?
N20 N19 N15 178.0(8) . . ?
N8 N7 N4 176.2(7) . . ?
N10 N9 N5 177.0(8) . . ?
N3 C14 C15 120.5(5) . . ?
N3 C14 C13 119.3(5) . . ?
C15 C14 C13 119.9(5) . . ?
C16 C17 C18 119.3(6) . . ?
C16 C15 C14 120.2(6) . . ?
C17 C16 C15 119.0(6) . . ?
N3 C18 C17 121.7(6) . . ?
C14 C13 C12 114.6(5) . . ?
C14 C13 C31 109.8(4) . . ?
C12 C13 C31 108.6(4) . . ?
N2 C12 N6 108.2(5) . . ?
N2 C12 C13 122.7(5) . . ?
N6 C12 C13 128.0(5) . . ?
C11 C10 C9 120.3(7) . . ?
C8 C9 C10 121.3(7) . . ?
C12 N6 C7 104.8(5) . . ?
C12 N6 C11 135.5(5) . . ?
C7 N6 C11 119.7(5) . . ?

_refine_diff_density_max         0.880
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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/ccdc.csd.cc13n41y
_database_code_depnum_ccdc_archive 'CCDC 1032239'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl2 N4 Zn'
_chemical_formula_sum            'C18 H14 Cl2 N4 Zn'
_chemical_formula_weight         422.60

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                   7.229(3)
_cell_length_b                   14.023(6)
_cell_length_c                   19.027(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.403(5)
_cell_angle_gamma                90
_cell_volume                     1920.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1590
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      20.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.564
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7139
_exptl_absorpt_correction_T_max  0.8587
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            6304
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.807
_diffrn_reflns_theta_max         24.672
_diffrn_reflns_theta_full        24.672
_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             1958
_reflns_number_gt                1606
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+0.7731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1958
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0748
_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 0.15741(7) 0.86753(4) 0.86280(3) 0.0482(2) Uani 1 1 d . . . . .
Cl1 Cl -0.0287(2) 0.74064(10) 0.87704(7) 0.0802(4) Uani 1 1 d . . . . .
Cl2 Cl 0.42534(16) 0.80987(9) 0.82729(6) 0.0606(4) Uani 1 1 d . . . . .
N1 N -0.0116(5) 0.9263(3) 0.76547(17) 0.0459(9) Uani 1 1 d . . . . .
N2 N 0.2173(4) 1.0070(2) 0.88213(18) 0.0413(9) Uani 1 1 d . . . . .
N3 N 0.1941(5) 0.8904(3) 0.98752(18) 0.0506(10) Uani 1 1 d . . . . .
N4 N 0.2915(4) 1.1381(3) 0.94280(18) 0.0422(9) Uani 1 1 d . . . . .
C1 C -0.1734(7) 0.8837(3) 0.7451(2) 0.0557(13) Uani 1 1 d . . . . .
H1 H -0.198846 0.825364 0.765321 0.067 Uiso 1 1 calc R U . . .
C2 C -0.3051(7) 0.9221(4) 0.6954(3) 0.0640(14) Uani 1 1 d . . . . .
H2 H -0.416164 0.890346 0.682663 0.077 Uiso 1 1 calc R U . . .
C3 C -0.2677(8) 1.0074(4) 0.6657(3) 0.0730(16) Uani 1 1 d . . . . .
H3 H -0.353203 1.035002 0.632107 0.088 Uiso 1 1 calc R U . . .
C4 C -0.1022(7) 1.0525(4) 0.6858(2) 0.0620(14) Uani 1 1 d . . . . .
H4 H -0.075751 1.111067 0.666133 0.074 Uiso 1 1 calc R U . . .
C5 C 0.0253(6) 1.0104(3) 0.7354(2) 0.0464(12) Uani 1 1 d . . . . .
C6 C 0.2068(6) 1.0576(3) 0.7574(2) 0.0520(12) Uani 1 1 d . . . . .
H6A H 0.213836 1.116911 0.731600 0.062 Uiso 1 1 calc R U . . .
H6B H 0.306736 1.016731 0.744683 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2350(5) 1.0782(3) 0.8350(2) 0.0421(11) Uani 1 1 d . . . . .
C8 C 0.2790(6) 1.1615(3) 0.8705(2) 0.0429(11) Uani 1 1 d . . . . .
C9 C 0.3101(6) 1.2565(4) 0.8508(2) 0.0570(13) Uani 1 1 d . . . . .
H9 H 0.301103 1.273366 0.803318 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3529(7) 1.3229(4) 0.9007(3) 0.0723(15) Uani 1 1 d . . . . .
H10 H 0.374073 1.385736 0.887896 0.087 Uiso 1 1 calc R U . . .
C11 C 0.3654(8) 1.2965(4) 0.9726(3) 0.0741(16) Uani 1 1 d . . . . .
H11 H 0.395928 1.342899 1.006727 0.089 Uiso 1 1 calc R U . . .
C12 C 0.3349(6) 1.2073(4) 0.9935(2) 0.0560(13) Uani 1 1 d . . . . .
H12 H 0.342712 1.192042 1.041277 0.067 Uiso 1 1 calc R U . . .
C13 C 0.2525(5) 1.0428(3) 0.9470(2) 0.0394(11) Uani 1 1 d . . . . .
C14 C 0.2466(5) 0.9793(3) 1.0080(2) 0.0389(11) Uani 1 1 d . . . . .
C15 C 0.2900(6) 1.0018(3) 1.0787(2) 0.0468(12) Uani 1 1 d . . . . .
H15 H 0.327544 1.063036 1.092223 0.056 Uiso 1 1 calc R U . . .
C16 C 0.2760(6) 0.9307(4) 1.1286(2) 0.0549(13) Uani 1 1 d . . . . .
H16 H 0.305713 0.944032 1.176255 0.066 Uiso 1 1 calc R U . . .
C17 C 0.2190(7) 0.8418(4) 1.1083(3) 0.0608(14) Uani 1 1 d . . . . .
H17 H 0.206596 0.793816 1.141256 0.073 Uiso 1 1 calc R U . . .
C18 C 0.1804(7) 0.8251(4) 1.0372(3) 0.0605(13) Uani 1 1 d . . . . .
H18 H 0.142359 0.764130 1.023029 0.073 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.030(4) . ?
Zn1 Cl2 2.2602(14) . ?
Zn1 Cl1 2.2626(16) . ?
Zn1 N1 2.275(3) . ?
Zn1 N3 2.385(4) . ?
N1 C1 1.338(5) . ?
N1 C5 1.349(5) . ?
N2 C13 1.334(5) . ?
N2 C7 1.356(5) . ?
N3 C18 1.327(5) . ?
N3 C14 1.349(5) . ?
N4 C13 1.368(5) . ?
N4 C12 1.384(5) . ?
N4 C8 1.410(5) . ?
C1 C2 1.386(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.494(6) . ?
C6 C7 1.499(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.372(6) . ?
C8 C9 1.408(6) . ?
C9 C10 1.345(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.413(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.338(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.468(6) . ?
C14 C15 1.388(6) . ?
C15 C16 1.387(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.359(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 Cl2 102.98(10) . . ?
N2 Zn1 Cl1 148.81(10) . . ?
Cl2 Zn1 Cl1 106.89(6) . . ?
N2 Zn1 N1 83.55(14) . . ?
Cl2 Zn1 N1 107.21(10) . . ?
Cl1 Zn1 N1 95.87(11) . . ?
N2 Zn1 N3 71.82(14) . . ?
Cl2 Zn1 N3 109.13(9) . . ?
Cl1 Zn1 N3 89.91(10) . . ?
N1 Zn1 N3 139.66(13) . . ?
C1 N1 C5 118.0(4) . . ?
C1 N1 Zn1 117.6(3) . . ?
C5 N1 Zn1 123.3(3) . . ?
C13 N2 C7 108.2(4) . . ?
C13 N2 Zn1 123.3(3) . . ?
C7 N2 Zn1 128.4(3) . . ?
C18 N3 C14 118.0(4) . . ?
C18 N3 Zn1 127.4(3) . . ?
C14 N3 Zn1 114.5(3) . . ?
C13 N4 C12 132.7(4) . . ?
C13 N4 C8 106.8(3) . . ?
C12 N4 C8 120.4(4) . . ?
N1 C1 C2 123.4(5) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 118.3(5) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.3(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.9(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 121.0(4) . . ?
N1 C5 C6 118.1(4) . . ?
C4 C5 C6 120.8(5) . . ?
C5 C6 C7 113.3(4) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N2 C7 C8 109.5(3) . . ?
N2 C7 C6 119.8(4) . . ?
C8 C7 C6 130.7(4) . . ?
C7 C8 C9 135.3(4) . . ?
C7 C8 N4 105.8(4) . . ?
C9 C8 N4 118.9(4) . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.5(5) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 122.4(5) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 N4 118.8(4) . . ?
C11 C12 H12 120.6 . . ?
N4 C12 H12 120.6 . . ?
N2 C13 N4 109.6(4) . . ?
N2 C13 C14 119.1(4) . . ?
N4 C13 C14 131.3(4) . . ?
N3 C14 C15 121.5(4) . . ?
N3 C14 C13 111.1(4) . . ?
C15 C14 C13 127.4(4) . . ?
C16 C15 C14 118.4(4) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C17 C16 C15 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 117.7(5) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
N3 C18 C17 124.1(5) . . ?
N3 C18 H18 117.9 . . ?
C17 C18 H18 117.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.7(6) . . . . ?
Zn1 N1 C1 C2 167.7(3) . . . . ?
N1 C1 C2 C3 0.1(7) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C1 N1 C5 C4 1.2(6) . . . . ?
Zn1 N1 C5 C4 -166.5(3) . . . . ?
C1 N1 C5 C6 -179.3(4) . . . . ?
Zn1 N1 C5 C6 13.0(5) . . . . ?
C3 C4 C5 N1 -1.2(7) . . . . ?
C3 C4 C5 C6 179.3(4) . . . . ?
N1 C5 C6 C7 -58.6(5) . . . . ?
C4 C5 C6 C7 120.9(5) . . . . ?
C13 N2 C7 C8 -1.1(5) . . . . ?
Zn1 N2 C7 C8 -179.1(3) . . . . ?
C13 N2 C7 C6 178.8(4) . . . . ?
Zn1 N2 C7 C6 0.7(6) . . . . ?
C5 C6 C7 N2 53.7(5) . . . . ?
C5 C6 C7 C8 -126.4(5) . . . . ?
N2 C7 C8 C9 -178.6(5) . . . . ?
C6 C7 C8 C9 1.6(8) . . . . ?
N2 C7 C8 N4 1.1(5) . . . . ?
C6 C7 C8 N4 -178.7(4) . . . . ?
C13 N4 C8 C7 -0.7(4) . . . . ?
C12 N4 C8 C7 179.9(4) . . . . ?
C13 N4 C8 C9 179.0(4) . . . . ?
C12 N4 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 C10 -179.7(5) . . . . ?
N4 C8 C9 C10 0.7(7) . . . . ?
C8 C9 C10 C11 -0.3(8) . . . . ?
C9 C10 C11 C12 -0.5(9) . . . . ?
C10 C11 C12 N4 0.7(8) . . . . ?
C13 N4 C12 C11 -179.5(5) . . . . ?
C8 N4 C12 C11 -0.3(6) . . . . ?
C7 N2 C13 N4 0.6(4) . . . . ?
Zn1 N2 C13 N4 178.8(2) . . . . ?
C7 N2 C13 C14 -178.7(3) . . . . ?
Zn1 N2 C13 C14 -0.5(5) . . . . ?
C12 N4 C13 N2 179.4(4) . . . . ?
C8 N4 C13 N2 0.1(4) . . . . ?
C12 N4 C13 C14 -1.4(7) . . . . ?
C8 N4 C13 C14 179.3(4) . . . . ?
C18 N3 C14 C15 1.6(6) . . . . ?
Zn1 N3 C14 C15 -174.1(3) . . . . ?
C18 N3 C14 C13 -179.3(4) . . . . ?
Zn1 N3 C14 C13 5.0(4) . . . . ?
N2 C13 C14 N3 -3.3(5) . . . . ?
N4 C13 C14 N3 177.5(4) . . . . ?
N2 C13 C14 C15 175.7(4) . . . . ?
N4 C13 C14 C15 -3.4(7) . . . . ?
N3 C14 C15 C16 -0.8(6) . . . . ?
C13 C14 C15 C16 -179.7(4) . . . . ?
C14 C15 C16 C17 -0.7(7) . . . . ?
C15 C16 C17 C18 1.3(7) . . . . ?
C14 N3 C18 C17 -1.0(7) . . . . ?
Zn1 N3 C18 C17 174.2(3) . . . . ?
C16 C17 C18 N3 -0.5(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 Cl1 0.93 2.64 3.306(5) 129.4 .
C9 H9 Cl2 0.93 2.89 3.722(5) 149.6 2_556
C12 H12 Cl2 0.93 2.88 3.684(5) 145.9 3_677
C15 H15 Cl2 0.93 2.86 3.704(5) 151.0 3_677
C18 H18 Cl1 0.93 2.95 3.479(5) 117.5 .

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.048



