# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_D
_database_code_depnum_ccdc_archive 'CCDC 1862415'
_audit_update_record             
;
2018-08-16 deposited with the CCDC.	2019-06-03 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         'C21 H14 Br2 F N3 Zn'
_chemical_formula_sum            'C21 H14 Br2 F N3 Zn'
_chemical_formula_weight         552.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   13.774(3)
_cell_length_b                   14.789(3)
_cell_length_c                   19.060(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.81(3)
_cell_angle_gamma                90
_cell_volume                     3874.0(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13429
_cell_measurement_theta_min      2.874
_cell_measurement_theta_max      29.571

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_F_000             2160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    5.415
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            13429
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.874
_diffrn_reflns_theta_max         29.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4628
_reflns_number_gt                3954
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2016 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2016 and PLATON (Spek, 2009)'
_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)+(0.0417P)²+1.9617P] 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         4628
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.17814(2) 0.08349(2) 0.34007(2) 0.03714(9) Uani 1 1 d . . . . .
Br1 Br 0.10757(2) 0.02155(2) 0.44132(2) 0.04779(10) Uani 1 1 d . . . . .
Br2 Br 0.35256(2) 0.07290(2) 0.34804(2) 0.05495(10) Uani 1 1 d . . . . .
F1 F 0.13863(15) 0.38455(13) -0.15208(8) 0.0625(5) Uani 1 1 d . . . . .
N2 N 0.13290(14) 0.14421(13) 0.24364(10) 0.0339(4) Uani 1 1 d . . . . .
N3 N 0.14888(15) 0.22725(15) 0.36418(10) 0.0403(5) Uani 1 1 d . . . . .
N1 N 0.14355(15) -0.02872(14) 0.26591(10) 0.0382(5) Uani 1 1 d . . . . .
C1 C 0.1457(2) -0.11675(18) 0.28237(14) 0.0453(6) Uani 1 1 d . . . . .
H1A H 0.152311 -0.133151 0.329547 0.054 Uiso 1 1 calc R U . . .
C2 C 0.1385(2) -0.18396(18) 0.23233(15) 0.0460(6) Uani 1 1 d . . . . .
H2A H 0.139548 -0.244552 0.245427 0.055 Uiso 1 1 calc R U . . .
C3 C 0.12985(19) -0.15962(18) 0.16259(14) 0.0434(6) Uani 1 1 d . . . . .
H3A H 0.126719 -0.203691 0.127704 0.052 Uiso 1 1 calc R U . . .
C4 C 0.1258(2) -0.06921(17) 0.14484(13) 0.0401(6) Uani 1 1 d . . . . .
H4A H 0.118700 -0.051630 0.097928 0.048 Uiso 1 1 calc R U . . .
C5 C 0.13257(17) -0.00499(16) 0.19779(12) 0.0343(5) Uani 1 1 d . . . . .
C6 C 0.12754(17) 0.09399(16) 0.18502(12) 0.0338(5) Uani 1 1 d . . . . .
C7 C 0.11936(17) 0.13355(16) 0.11899(12) 0.0359(5) Uani 1 1 d . . . . .
H7A H 0.113373 0.097628 0.078885 0.043 Uiso 1 1 calc R U . . .
C8 C 0.12017(17) 0.22765(17) 0.11299(12) 0.0347(5) Uani 1 1 d . . . . .
C9 C 0.12343(17) 0.27797(17) 0.17491(12) 0.0370(5) Uani 1 1 d . . . . .
H9A H 0.122375 0.340798 0.172930 0.044 Uiso 1 1 calc R U . . .
C10 C 0.12824(16) 0.23466(16) 0.23917(12) 0.0335(5) Uani 1 1 d . . . . .
C11 C 0.12867(17) 0.28119(17) 0.30853(12) 0.0368(5) Uani 1 1 d . . . . .
C12 C 0.1053(2) 0.37150(18) 0.31565(14) 0.0458(6) Uani 1 1 d . . . . .
H12A H 0.093896 0.408226 0.276349 0.055 Uiso 1 1 calc R U . . .
C13 C 0.0992(2) 0.4060(2) 0.38302(16) 0.0565(8) Uani 1 1 d . . . . .
H13A H 0.080342 0.465618 0.389422 0.068 Uiso 1 1 calc R U . . .
C14 C 0.1213(2) 0.3511(2) 0.44031(15) 0.0582(8) Uani 1 1 d . . . . .
H14A H 0.119488 0.373401 0.485822 0.070 Uiso 1 1 calc R U . . .
C15 C 0.1460(2) 0.2625(2) 0.42861(14) 0.0510(7) Uani 1 1 d . . . . .
H15A H 0.161428 0.225452 0.467201 0.061 Uiso 1 1 calc R U . . .
C16 C 0.12077(17) 0.27110(16) 0.04303(12) 0.0355(5) Uani 1 1 d . . . . .
C17 C 0.16980(19) 0.35246(17) 0.03534(13) 0.0409(6) Uani 1 1 d . . . . .
H17A H 0.199010 0.381058 0.074755 0.049 Uiso 1 1 calc R U . . .
C18 C 0.1755(2) 0.39122(19) -0.03032(14) 0.0460(6) Uani 1 1 d . . . . .
H18A H 0.208922 0.445193 -0.035617 0.055 Uiso 1 1 calc R U . . .
C19 C 0.1310(2) 0.34835(19) -0.08711(13) 0.0429(6) Uani 1 1 d . . . . .
C20 C 0.07996(19) 0.26967(19) -0.08180(13) 0.0435(6) Uani 1 1 d . . . . .
H20A H 0.049017 0.243087 -0.121462 0.052 Uiso 1 1 calc R U . . .
C21 C 0.07526(19) 0.23046(18) -0.01639(13) 0.0401(5) Uani 1 1 d . . . . .
H21A H 0.041474 0.176542 -0.011937 0.048 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 2.1024(19) . ?
Zn1 N1 2.211(2) . ?
Zn1 N3 2.218(2) . ?
Zn1 Br1 2.3994(6) . ?
Zn1 Br2 2.4023(7) . ?
F1 C19 1.359(3) . ?
N2 C6 1.340(3) . ?
N2 C10 1.342(3) . ?
N3 C15 1.337(3) . ?
N3 C11 1.341(3) . ?
N1 C1 1.339(3) . ?
N1 C5 1.344(3) . ?
C1 C2 1.377(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.375(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.485(3) . ?
C6 C7 1.386(3) . ?
C7 C8 1.396(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.393(3) . ?
C8 C16 1.481(3) . ?
C9 C10 1.380(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.490(3) . ?
C11 C12 1.383(4) . ?
C12 C13 1.389(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.378(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.376(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.392(4) . ?
C16 C21 1.394(3) . ?
C17 C18 1.384(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.364(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.367(4) . ?
C20 C21 1.380(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 73.92(8) . . ?
N2 Zn1 N3 74.00(8) . . ?
N1 Zn1 N3 144.84(8) . . ?
N2 Zn1 Br1 138.92(6) . . ?
N1 Zn1 Br1 98.40(5) . . ?
N3 Zn1 Br1 96.34(5) . . ?
N2 Zn1 Br2 108.67(6) . . ?
N1 Zn1 Br2 99.41(6) . . ?
N3 Zn1 Br2 104.13(6) . . ?
Br1 Zn1 Br2 112.40(3) . . ?
C6 N2 C10 120.0(2) . . ?
C6 N2 Zn1 119.28(16) . . ?
C10 N2 Zn1 119.44(15) . . ?
C15 N3 C11 118.5(2) . . ?
C15 N3 Zn1 125.49(18) . . ?
C11 N3 Zn1 115.92(16) . . ?
C1 N1 C5 118.7(2) . . ?
C1 N1 Zn1 125.41(17) . . ?
C5 N1 Zn1 115.29(16) . . ?
N1 C1 C2 122.7(2) . . ?
N1 C1 H1A 118.6 . . ?
C2 C1 H1A 118.6 . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
N1 C5 C4 121.5(2) . . ?
N1 C5 C6 114.6(2) . . ?
C4 C5 C6 123.8(2) . . ?
N2 C6 C7 121.3(2) . . ?
N2 C6 C5 114.2(2) . . ?
C7 C6 C5 124.4(2) . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C9 C8 C7 117.6(2) . . ?
C9 C8 C16 121.9(2) . . ?
C7 C8 C16 120.4(2) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
N2 C10 C9 121.2(2) . . ?
N2 C10 C11 114.0(2) . . ?
C9 C10 C11 124.8(2) . . ?
N3 C11 C12 122.3(2) . . ?
N3 C11 C10 114.5(2) . . ?
C12 C11 C10 123.1(2) . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 H12A 120.9 . . ?
C13 C12 H12A 120.9 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?
N3 C15 C14 122.9(3) . . ?
N3 C15 H15A 118.6 . . ?
C14 C15 H15A 118.6 . . ?
C17 C16 C21 118.8(2) . . ?
C17 C16 C8 120.1(2) . . ?
C21 C16 C8 121.0(2) . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C19 C18 C17 118.4(3) . . ?
C19 C18 H18A 120.8 . . ?
C17 C18 H18A 120.8 . . ?
F1 C19 C18 118.8(3) . . ?
F1 C19 C20 118.3(2) . . ?
C18 C19 C20 122.9(2) . . ?
C19 C20 C21 118.7(2) . . ?
C19 C20 H20A 120.7 . . ?
C21 C20 H20A 120.7 . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21A 119.8 . . ?
C16 C21 H21A 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1.0(4) . . . . ?
Zn1 N1 C1 C2 -169.5(2) . . . . ?
N1 C1 C2 C3 0.7(4) . . . . ?
C1 C2 C3 C4 -1.8(4) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C1 N1 C5 C4 -1.5(4) . . . . ?
Zn1 N1 C5 C4 169.84(19) . . . . ?
C1 N1 C5 C6 177.9(2) . . . . ?
Zn1 N1 C5 C6 -10.7(3) . . . . ?
C3 C4 C5 N1 0.5(4) . . . . ?
C3 C4 C5 C6 -179.0(2) . . . . ?
C10 N2 C6 C7 1.5(3) . . . . ?
Zn1 N2 C6 C7 -165.55(18) . . . . ?
C10 N2 C6 C5 -179.4(2) . . . . ?
Zn1 N2 C6 C5 13.6(3) . . . . ?
N1 C5 C6 N2 -1.2(3) . . . . ?
C4 C5 C6 N2 178.3(2) . . . . ?
N1 C5 C6 C7 177.9(2) . . . . ?
C4 C5 C6 C7 -2.6(4) . . . . ?
N2 C6 C7 C8 2.3(4) . . . . ?
C5 C6 C7 C8 -176.8(2) . . . . ?
C6 C7 C8 C9 -3.8(3) . . . . ?
C6 C7 C8 C16 174.3(2) . . . . ?
C7 C8 C9 C10 1.6(3) . . . . ?
C16 C8 C9 C10 -176.4(2) . . . . ?
C6 N2 C10 C9 -3.7(3) . . . . ?
Zn1 N2 C10 C9 163.31(17) . . . . ?
C6 N2 C10 C11 176.2(2) . . . . ?
Zn1 N2 C10 C11 -16.8(3) . . . . ?
C8 C9 C10 N2 2.1(4) . . . . ?
C8 C9 C10 C11 -177.8(2) . . . . ?
C15 N3 C11 C12 0.1(4) . . . . ?
Zn1 N3 C11 C12 177.4(2) . . . . ?
C15 N3 C11 C10 -176.7(2) . . . . ?
Zn1 N3 C11 C10 0.6(3) . . . . ?
N2 C10 C11 N3 10.0(3) . . . . ?
C9 C10 C11 N3 -170.1(2) . . . . ?
N2 C10 C11 C12 -166.8(2) . . . . ?
C9 C10 C11 C12 13.1(4) . . . . ?
N3 C11 C12 C13 -2.4(4) . . . . ?
C10 C11 C12 C13 174.1(2) . . . . ?
C11 C12 C13 C14 3.3(4) . . . . ?
C12 C13 C14 C15 -1.9(5) . . . . ?
C11 N3 C15 C14 1.4(4) . . . . ?
Zn1 N3 C15 C14 -175.7(2) . . . . ?
C13 C14 C15 N3 -0.5(5) . . . . ?
C9 C8 C16 C17 31.4(3) . . . . ?
C7 C8 C16 C17 -146.5(2) . . . . ?
C9 C8 C16 C21 -150.6(2) . . . . ?
C7 C8 C16 C21 31.5(3) . . . . ?
C21 C16 C17 C18 -1.7(4) . . . . ?
C8 C16 C17 C18 176.4(2) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
C17 C18 C19 F1 -178.1(2) . . . . ?
C17 C18 C19 C20 1.0(4) . . . . ?
F1 C19 C20 C21 177.4(2) . . . . ?
C18 C19 C20 C21 -1.7(4) . . . . ?
C19 C20 C21 C16 0.8(4) . . . . ?
C17 C16 C21 C20 0.9(4) . . . . ?
C8 C16 C21 C20 -177.2(2) . . . . ?

_refine_diff_density_max         0.657
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_D_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1862421'
_audit_update_record             
;
2018-08-16 deposited with the CCDC.	2019-06-03 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         'C21 H14 I3 N3 Zn'
_chemical_formula_sum            'C21 H14 I3 N3 Zn'
_chemical_formula_weight         754.42

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   14.083(3)
_cell_length_b                   15.755(3)
_cell_length_c                   19.635(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4356.6(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    51899
_cell_measurement_theta_min      2.840
_cell_measurement_theta_max      29.543

_exptl_crystal_description       Prism
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.300
_exptl_crystal_F_000             2800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    5.391
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            51899
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.840
_diffrn_reflns_theta_max         29.543
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5768
_reflns_number_gt                4482
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2016 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2016 and PLATON (Spek, 2009)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²+9.7161P] 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         5768
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.42371(4) -0.67177(4) 0.84233(3) 0.03898(14) Uani 1 1 d . . . . .
I1 I 0.34935(3) -0.73652(3) 0.95155(2) 0.06102(13) Uani 1 1 d . . . . .
I2 I 0.60925(3) -0.68669(3) 0.85020(2) 0.05858(13) Uani 1 1 d . . . . .
I3 I 0.36762(2) -0.36706(2) 0.33002(2) 0.04007(10) Uani 1 1 d . . . . .
N1 N 0.4104(3) -0.5363(3) 0.86900(19) 0.0400(8) Uani 1 1 d . . . . .
N2 N 0.3852(2) -0.6108(2) 0.75170(18) 0.0332(7) Uani 1 1 d . . . . .
N3 N 0.3911(3) -0.7749(3) 0.7688(2) 0.0414(9) Uani 1 1 d . . . . .
C1 C 0.4169(4) -0.5038(4) 0.9315(3) 0.0505(12) Uani 1 1 d . . . . .
H1A H 0.427556 -0.540739 0.967627 0.061 Uiso 1 1 calc R U . . .
C2 C 0.4087(4) -0.4179(4) 0.9453(3) 0.0535(13) Uani 1 1 d . . . . .
H2A H 0.415410 -0.397115 0.989379 0.064 Uiso 1 1 calc R U . . .
C3 C 0.3905(5) -0.3651(4) 0.8919(3) 0.0562(14) Uani 1 1 d . . . . .
H3A H 0.383656 -0.307143 0.899602 0.067 Uiso 1 1 calc R U . . .
C4 C 0.3823(4) -0.3963(3) 0.8269(3) 0.0474(12) Uani 1 1 d . . . . .
H4A H 0.369177 -0.360287 0.790549 0.057 Uiso 1 1 calc R U . . .
C5 C 0.3939(3) -0.4829(3) 0.8166(2) 0.0372(9) Uani 1 1 d . . . . .
C6 C 0.3864(3) -0.5247(3) 0.7489(2) 0.0343(9) Uani 1 1 d . . . . .
C7 C 0.3799(3) -0.4827(3) 0.6877(2) 0.0377(9) Uani 1 1 d . . . . .
H7A H 0.380398 -0.423672 0.686900 0.045 Uiso 1 1 calc R U . . .
C8 C 0.3724(3) -0.5282(3) 0.6265(2) 0.0341(9) Uani 1 1 d . . . . .
C9 C 0.3690(3) -0.6169(3) 0.6315(2) 0.0351(9) Uani 1 1 d . . . . .
H9A H 0.362537 -0.649862 0.592459 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3754(3) -0.6552(3) 0.6950(2) 0.0331(8) Uani 1 1 d . . . . .
C11 C 0.3743(3) -0.7485(3) 0.7046(2) 0.0367(9) Uani 1 1 d . . . . .
C12 C 0.3548(4) -0.8052(3) 0.6519(3) 0.0452(11) Uani 1 1 d . . . . .
H12A H 0.342919 -0.785833 0.607989 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3537(5) -0.8911(4) 0.6668(3) 0.0566(14) Uani 1 1 d . . . . .
H13A H 0.340875 -0.930558 0.632788 0.068 Uiso 1 1 calc R U . . .
C14 C 0.3716(5) -0.9175(4) 0.7319(4) 0.0607(15) Uani 1 1 d . . . . .
H14A H 0.370845 -0.974938 0.742800 0.073 Uiso 1 1 calc R U . . .
C15 C 0.3907(5) -0.8580(3) 0.7809(3) 0.0553(13) Uani 1 1 d . . . . .
H15A H 0.404094 -0.876570 0.824842 0.066 Uiso 1 1 calc R U . . .
C16 C 0.3695(3) -0.4872(3) 0.5591(2) 0.0351(9) Uani 1 1 d . . . . .
C17 C 0.3222(4) -0.5266(3) 0.5057(2) 0.0419(10) Uani 1 1 d . . . . .
H17A H 0.290305 -0.577391 0.513471 0.050 Uiso 1 1 calc R U . . .
C18 C 0.3216(4) -0.4915(3) 0.4409(2) 0.0425(10) Uani 1 1 d . . . . .
H18A H 0.289733 -0.518473 0.405546 0.051 Uiso 1 1 calc R U . . .
C19 C 0.3687(3) -0.4160(3) 0.4295(2) 0.0355(9) Uani 1 1 d . . . . .
C20 C 0.4157(4) -0.3764(3) 0.4813(2) 0.0447(11) Uani 1 1 d . . . . .
H20A H 0.447370 -0.325630 0.473059 0.054 Uiso 1 1 calc R U . . .
C21 C 0.4166(4) -0.4113(3) 0.5461(2) 0.0435(11) Uani 1 1 d . . . . .
H21A H 0.448886 -0.383880 0.581087 0.052 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 2.093(4) . ?
Zn1 N1 2.205(4) . ?
Zn1 N3 2.221(4) . ?
Zn1 I1 2.5954(7) . ?
Zn1 I2 2.6279(8) . ?
I3 C19 2.100(4) . ?
N1 C1 1.332(6) . ?
N1 C5 1.349(6) . ?
N2 C10 1.322(6) . ?
N2 C6 1.359(6) . ?
N3 C15 1.331(7) . ?
N3 C11 1.348(6) . ?
C1 C2 1.385(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.364(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.373(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.390(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.486(6) . ?
C6 C7 1.374(6) . ?
C7 C8 1.404(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.402(6) . ?
C8 C16 1.473(6) . ?
C9 C10 1.390(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.482(6) . ?
C11 C12 1.393(7) . ?
C12 C13 1.385(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.368(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.370(9) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.389(6) . ?
C16 C21 1.391(6) . ?
C17 C18 1.387(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.379(7) . ?
C18 H18A 0.9300 . ?
C19 C20 1.365(7) . ?
C20 C21 1.387(6) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 74.68(14) . . ?
N2 Zn1 N3 74.32(14) . . ?
N1 Zn1 N3 147.61(14) . . ?
N2 Zn1 I1 141.10(10) . . ?
N1 Zn1 I1 98.61(10) . . ?
N3 Zn1 I1 99.57(10) . . ?
N2 Zn1 I2 110.39(10) . . ?
N1 Zn1 I2 99.05(11) . . ?
N3 Zn1 I2 100.27(11) . . ?
I1 Zn1 I2 108.51(2) . . ?
C1 N1 C5 118.4(4) . . ?
C1 N1 Zn1 125.8(3) . . ?
C5 N1 Zn1 115.9(3) . . ?
C10 N2 C6 119.7(4) . . ?
C10 N2 Zn1 120.0(3) . . ?
C6 N2 Zn1 119.3(3) . . ?
C15 N3 C11 118.0(5) . . ?
C15 N3 Zn1 127.2(4) . . ?
C11 N3 Zn1 114.8(3) . . ?
N1 C1 C2 123.4(5) . . ?
N1 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C3 C2 C1 117.5(5) . . ?
C3 C2 H2A 121.3 . . ?
C1 C2 H2A 121.3 . . ?
C2 C3 C4 120.8(5) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 C5 118.5(5) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
N1 C5 C4 121.4(4) . . ?
N1 C5 C6 114.8(4) . . ?
C4 C5 C6 123.8(4) . . ?
N2 C6 C7 121.0(4) . . ?
N2 C6 C5 114.0(4) . . ?
C7 C6 C5 125.0(4) . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C9 C8 C7 116.8(4) . . ?
C9 C8 C16 119.9(4) . . ?
C7 C8 C16 123.3(4) . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
N2 C10 C9 122.2(4) . . ?
N2 C10 C11 114.8(4) . . ?
C9 C10 C11 123.0(4) . . ?
N3 C11 C12 122.1(4) . . ?
N3 C11 C10 114.9(4) . . ?
C12 C11 C10 122.9(4) . . ?
C13 C12 C11 118.1(5) . . ?
C13 C12 H12A 120.9 . . ?
C11 C12 H12A 120.9 . . ?
C14 C13 C12 119.5(6) . . ?
C14 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
C13 C14 C15 119.0(5) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
N3 C15 C14 123.3(5) . . ?
N3 C15 H15A 118.4 . . ?
C14 C15 H15A 118.4 . . ?
C17 C16 C21 118.4(4) . . ?
C17 C16 C8 119.7(4) . . ?
C21 C16 C8 121.8(4) . . ?
C18 C17 C16 121.1(4) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C19 C18 C17 119.4(4) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 I3 121.9(3) . . ?
C18 C19 I3 117.7(3) . . ?
C19 C20 C21 120.5(4) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C20 C21 C16 120.3(4) . . ?
C20 C21 H21A 119.9 . . ?
C16 C21 H21A 119.9 . . ?

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(8) . . . . ?
Zn1 N1 C1 C2 179.4(4) . . . . ?
N1 C1 C2 C3 1.8(9) . . . . ?
C1 C2 C3 C4 -1.0(10) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C1 N1 C5 C4 -1.2(7) . . . . ?
Zn1 N1 C5 C4 178.7(4) . . . . ?
C1 N1 C5 C6 -179.2(5) . . . . ?
Zn1 N1 C5 C6 0.7(5) . . . . ?
C3 C4 C5 N1 1.9(8) . . . . ?
C3 C4 C5 C6 179.7(5) . . . . ?
C10 N2 C6 C7 -1.7(6) . . . . ?
Zn1 N2 C6 C7 167.2(3) . . . . ?
C10 N2 C6 C5 177.7(4) . . . . ?
Zn1 N2 C6 C5 -13.5(5) . . . . ?
N1 C5 C6 N2 7.9(6) . . . . ?
C4 C5 C6 N2 -170.1(5) . . . . ?
N1 C5 C6 C7 -172.8(4) . . . . ?
C4 C5 C6 C7 9.2(7) . . . . ?
N2 C6 C7 C8 -0.4(7) . . . . ?
C5 C6 C7 C8 -179.6(4) . . . . ?
C6 C7 C8 C9 2.0(7) . . . . ?
C6 C7 C8 C16 -177.2(4) . . . . ?
C7 C8 C9 C10 -1.6(6) . . . . ?
C16 C8 C9 C10 177.6(4) . . . . ?
C6 N2 C10 C9 2.1(6) . . . . ?
Zn1 N2 C10 C9 -166.7(3) . . . . ?
C6 N2 C10 C11 -179.5(4) . . . . ?
Zn1 N2 C10 C11 11.7(5) . . . . ?
C8 C9 C10 N2 -0.4(7) . . . . ?
C8 C9 C10 C11 -178.7(4) . . . . ?
C15 N3 C11 C12 1.4(8) . . . . ?
Zn1 N3 C11 C12 178.6(4) . . . . ?
C15 N3 C11 C10 179.7(5) . . . . ?
Zn1 N3 C11 C10 -3.2(5) . . . . ?
N2 C10 C11 N3 -5.1(6) . . . . ?
C9 C10 C11 N3 173.4(4) . . . . ?
N2 C10 C11 C12 173.2(5) . . . . ?
C9 C10 C11 C12 -8.4(7) . . . . ?
N3 C11 C12 C13 -0.5(8) . . . . ?
C10 C11 C12 C13 -178.6(5) . . . . ?
C11 C12 C13 C14 -0.1(9) . . . . ?
C12 C13 C14 C15 -0.3(10) . . . . ?
C11 N3 C15 C14 -1.8(9) . . . . ?
Zn1 N3 C15 C14 -178.6(5) . . . . ?
C13 C14 C15 N3 1.3(10) . . . . ?
C9 C8 C16 C17 29.3(6) . . . . ?
C7 C8 C16 C17 -151.6(5) . . . . ?
C9 C8 C16 C21 -147.8(5) . . . . ?
C7 C8 C16 C21 31.3(7) . . . . ?
C21 C16 C17 C18 0.0(7) . . . . ?
C8 C16 C17 C18 -177.2(5) . . . . ?
C16 C17 C18 C19 -0.1(8) . . . . ?
C17 C18 C19 C20 0.2(8) . . . . ?
C17 C18 C19 I3 178.8(4) . . . . ?
C18 C19 C20 C21 -0.1(8) . . . . ?
I3 C19 C20 C21 -178.7(4) . . . . ?
C19 C20 C21 C16 0.0(8) . . . . ?
C17 C16 C21 C20 0.1(8) . . . . ?
C8 C16 C21 C20 177.3(5) . . . . ?

_refine_diff_density_max         1.066
_refine_diff_density_min         -1.819
_refine_diff_density_rms         0.134

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

data_D_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1862417'
_audit_update_record             
;
2018-08-16 deposited with the CCDC.	2019-06-03 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         'C21 H14 Cl I2 N3 Zn'
_chemical_formula_sum            'C21 H14 Cl I2 N3 Zn'
_chemical_formula_weight         662.97

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   14.040(3)
_cell_length_b                   15.296(3)
_cell_length_c                   19.559(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4200.4(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    61042
_cell_measurement_theta_min      2.860
_cell_measurement_theta_max      29.497

_exptl_crystal_description       Prism
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.097
_exptl_crystal_F_000             2512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    4.249
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            61042
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         29.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5459
_reflns_number_gt                4120
_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_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2016 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2016 and PLATON (Spek, 2009)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+10.4887P] 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         5459
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.92701(4) 0.16952(3) 0.33947(2) 0.03710(13) Uani 1 1 d . . . . .
I1 I 0.84774(3) 0.23072(2) 0.44917(2) 0.05421(11) Uani 1 1 d . . . . .
I2 I 1.11243(2) 0.18499(2) 0.34530(2) 0.05573(11) Uani 1 1 d . . . . .
Cl1 Cl 0.87550(10) -0.12458(8) -0.15997(5) 0.0510(3) Uani 1 1 d . . . . .
N1 N 0.9139(3) 0.0284(2) 0.36394(17) 0.0370(7) Uani 1 1 d . . . . .
N2 N 0.8862(2) 0.1090(2) 0.24829(16) 0.0322(7) Uani 1 1 d . . . . .
N3 N 0.8926(3) 0.2774(2) 0.26798(18) 0.0385(8) Uani 1 1 d . . . . .
C1 C 0.9219(4) -0.0061(3) 0.4259(2) 0.0470(11) Uani 1 1 d . . . . .
H1A H 0.935481 0.030659 0.462537 0.056 Uiso 1 1 calc R U . . .
C2 C 0.9108(4) -0.0943(3) 0.4383(2) 0.0510(12) Uani 1 1 d . . . . .
H2A H 0.918860 -0.116901 0.482010 0.061 Uiso 1 1 calc R U . . .
C3 C 0.8878(4) -0.1473(3) 0.3851(3) 0.0513(12) Uani 1 1 d . . . . .
H3A H 0.877078 -0.206508 0.392520 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8803(4) -0.1133(3) 0.3201(2) 0.0461(10) Uani 1 1 d . . . . .
H4A H 0.866540 -0.149128 0.283008 0.055 Uiso 1 1 calc R U . . .
C5 C 0.8940(3) -0.0235(3) 0.3113(2) 0.0347(8) Uani 1 1 d . . . . .
C6 C 0.8863(3) 0.0207(3) 0.2441(2) 0.0337(8) Uani 1 1 d . . . . .
C7 C 0.8800(3) -0.0212(3) 0.1818(2) 0.0382(9) Uani 1 1 d . . . . .
H7A H 0.880816 -0.081912 0.179751 0.046 Uiso 1 1 calc R U . . .
C8 C 0.8724(3) 0.0277(3) 0.1219(2) 0.0349(8) Uani 1 1 d . . . . .
C9 C 0.8689(3) 0.1186(3) 0.1277(2) 0.0373(9) Uani 1 1 d . . . . .
H9A H 0.861758 0.153289 0.088959 0.045 Uiso 1 1 calc R U . . .
C10 C 0.8761(3) 0.1566(3) 0.19179(19) 0.0336(8) Uani 1 1 d . . . . .
C11 C 0.8755(3) 0.2527(3) 0.2034(2) 0.0342(8) Uani 1 1 d . . . . .
C12 C 0.8562(4) 0.3124(3) 0.1520(2) 0.0444(10) Uani 1 1 d . . . . .
H12A H 0.843684 0.293949 0.107618 0.053 Uiso 1 1 calc R U . . .
C13 C 0.8560(4) 0.4008(3) 0.1686(3) 0.0495(11) Uani 1 1 d . . . . .
H13A H 0.843906 0.442475 0.135088 0.059 Uiso 1 1 calc R U . . .
C14 C 0.8736(4) 0.4258(3) 0.2339(3) 0.0528(12) Uani 1 1 d . . . . .
H14A H 0.873378 0.484748 0.245632 0.063 Uiso 1 1 calc R U . . .
C15 C 0.8917(4) 0.3630(3) 0.2824(3) 0.0487(11) Uani 1 1 d . . . . .
H15A H 0.903720 0.380583 0.327117 0.058 Uiso 1 1 calc R U . . .
C16 C 0.8692(3) -0.0134(3) 0.0533(2) 0.0360(9) Uani 1 1 d . . . . .
C17 C 0.8196(3) 0.0258(3) 0.0006(2) 0.0420(10) Uani 1 1 d . . . . .
H17A H 0.784263 0.076045 0.009346 0.050 Uiso 1 1 calc R U . . .
C18 C 0.8213(3) -0.0078(3) -0.0647(2) 0.0423(10) Uani 1 1 d . . . . .
H18A H 0.788374 0.019756 -0.099870 0.051 Uiso 1 1 calc R U . . .
C19 C 0.8728(3) -0.0830(3) -0.0770(2) 0.0394(9) Uani 1 1 d . . . . .
C20 C 0.9218(4) -0.1246(3) -0.0255(2) 0.0433(10) Uani 1 1 d . . . . .
H20A H 0.955691 -0.175575 -0.034477 0.052 Uiso 1 1 calc R U . . .
C21 C 0.9199(3) -0.0901(3) 0.0392(2) 0.0400(9) Uani 1 1 d . . . . .
H21A H 0.952889 -0.117993 0.074152 0.048 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 2.090(3) . ?
Zn1 N3 2.216(4) . ?
Zn1 N1 2.218(3) . ?
Zn1 I1 2.5920(7) . ?
Zn1 I2 2.6166(8) . ?
Cl1 C19 1.742(4) . ?
N1 C1 1.327(5) . ?
N1 C5 1.330(5) . ?
N2 C10 1.331(5) . ?
N2 C6 1.353(5) . ?
N3 C15 1.339(6) . ?
N3 C11 1.340(5) . ?
C1 C2 1.379(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.358(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.483(5) . ?
C6 C7 1.379(5) . ?
C7 C8 1.394(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.396(6) . ?
C8 C16 1.482(5) . ?
C9 C10 1.386(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.487(5) . ?
C11 C12 1.385(6) . ?
C12 C13 1.389(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.355(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.376(7) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.382(6) . ?
C16 C21 1.400(6) . ?
C17 C18 1.376(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.381(6) . ?
C18 H18A 0.9300 . ?
C19 C20 1.375(6) . ?
C20 C21 1.372(6) . ?
C20 H20A 0.9300 . ?
C21 H21A 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 N3 74.44(12) . . ?
N2 Zn1 N1 74.35(12) . . ?
N3 Zn1 N1 147.40(13) . . ?
N2 Zn1 I1 138.48(9) . . ?
N3 Zn1 I1 99.19(9) . . ?
N1 Zn1 I1 97.88(9) . . ?
N2 Zn1 I2 110.50(9) . . ?
N3 Zn1 I2 100.20(10) . . ?
N1 Zn1 I2 99.28(10) . . ?
I1 Zn1 I2 111.01(2) . . ?
C1 N1 C5 119.2(4) . . ?
C1 N1 Zn1 125.2(3) . . ?
C5 N1 Zn1 115.6(3) . . ?
C10 N2 C6 119.7(3) . . ?
C10 N2 Zn1 119.7(3) . . ?
C6 N2 Zn1 119.6(3) . . ?
C15 N3 C11 118.2(4) . . ?
C15 N3 Zn1 126.6(3) . . ?
C11 N3 Zn1 115.1(3) . . ?
N1 C1 C2 122.6(4) . . ?
N1 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 118.3(4) . . ?
C3 C4 H4A 120.8 . . ?
C5 C4 H4A 120.8 . . ?
N1 C5 C4 121.4(4) . . ?
N1 C5 C6 115.4(3) . . ?
C4 C5 C6 123.2(4) . . ?
N2 C6 C7 121.1(4) . . ?
N2 C6 C5 113.6(3) . . ?
C7 C6 C5 125.2(4) . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C7 C8 C9 118.0(4) . . ?
C7 C8 C16 122.4(4) . . ?
C9 C8 C16 119.7(4) . . ?
C10 C9 C8 119.2(4) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
N2 C10 C9 122.0(4) . . ?
N2 C10 C11 114.5(3) . . ?
C9 C10 C11 123.5(4) . . ?
N3 C11 C12 122.2(4) . . ?
N3 C11 C10 114.9(3) . . ?
C12 C11 C10 122.9(4) . . ?
C11 C12 C13 118.2(4) . . ?
C11 C12 H12A 120.9 . . ?
C13 C12 H12A 120.9 . . ?
C14 C13 C12 119.6(4) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H14A 120.4 . . ?
C15 C14 H14A 120.4 . . ?
N3 C15 C14 122.6(4) . . ?
N3 C15 H15A 118.7 . . ?
C14 C15 H15A 118.7 . . ?
C17 C16 C21 118.2(4) . . ?
C17 C16 C8 120.4(4) . . ?
C21 C16 C8 121.3(4) . . ?
C18 C17 C16 121.4(4) . . ?
C18 C17 H17A 119.3 . . ?
C16 C17 H17A 119.3 . . ?
C17 C18 C19 118.9(4) . . ?
C17 C18 H18A 120.6 . . ?
C19 C18 H18A 120.6 . . ?
C20 C19 C18 121.3(4) . . ?
C20 C19 Cl1 120.2(3) . . ?
C18 C19 Cl1 118.6(3) . . ?
C21 C20 C19 119.2(4) . . ?
C21 C20 H20A 120.4 . . ?
C19 C20 H20A 120.4 . . ?
C20 C21 C16 121.0(4) . . ?
C20 C21 H21A 119.5 . . ?
C16 C21 H21A 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.3(7) . . . . ?
Zn1 N1 C1 C2 178.4(4) . . . . ?
N1 C1 C2 C3 -2.2(8) . . . . ?
C1 C2 C3 C4 2.9(8) . . . . ?
C2 C3 C4 C5 -2.0(8) . . . . ?
C1 N1 C5 C4 0.8(7) . . . . ?
Zn1 N1 C5 C4 -177.6(3) . . . . ?
C1 N1 C5 C6 179.9(4) . . . . ?
Zn1 N1 C5 C6 1.6(5) . . . . ?
C3 C4 C5 N1 0.1(7) . . . . ?
C3 C4 C5 C6 -179.0(4) . . . . ?
C10 N2 C6 C7 2.6(6) . . . . ?
Zn1 N2 C6 C7 -165.9(3) . . . . ?
C10 N2 C6 C5 -177.6(4) . . . . ?
Zn1 N2 C6 C5 13.9(5) . . . . ?
N1 C5 C6 N2 -9.7(5) . . . . ?
C4 C5 C6 N2 169.5(4) . . . . ?
N1 C5 C6 C7 170.2(4) . . . . ?
C4 C5 C6 C7 -10.7(7) . . . . ?
N2 C6 C7 C8 -0.6(6) . . . . ?
C5 C6 C7 C8 179.5(4) . . . . ?
C6 C7 C8 C9 -1.7(6) . . . . ?
C6 C7 C8 C16 177.5(4) . . . . ?
C7 C8 C9 C10 2.0(6) . . . . ?
C16 C8 C9 C10 -177.2(4) . . . . ?
C6 N2 C10 C9 -2.2(6) . . . . ?
Zn1 N2 C10 C9 166.3(3) . . . . ?
C6 N2 C10 C11 179.0(4) . . . . ?
Zn1 N2 C10 C11 -12.5(5) . . . . ?
C8 C9 C10 N2 -0.1(6) . . . . ?
C8 C9 C10 C11 178.5(4) . . . . ?
C15 N3 C11 C12 -0.7(7) . . . . ?
Zn1 N3 C11 C12 -177.7(4) . . . . ?
C15 N3 C11 C10 -179.0(4) . . . . ?
Zn1 N3 C11 C10 3.9(5) . . . . ?
N2 C10 C11 N3 5.0(5) . . . . ?
C9 C10 C11 N3 -173.7(4) . . . . ?
N2 C10 C11 C12 -173.3(4) . . . . ?
C9 C10 C11 C12 8.0(7) . . . . ?
N3 C11 C12 C13 0.9(7) . . . . ?
C10 C11 C12 C13 179.0(4) . . . . ?
C11 C12 C13 C14 -0.6(8) . . . . ?
C12 C13 C14 C15 0.3(8) . . . . ?
C11 N3 C15 C14 0.3(7) . . . . ?
Zn1 N3 C15 C14 177.0(4) . . . . ?
C13 C14 C15 N3 -0.1(8) . . . . ?
C7 C8 C16 C17 149.6(4) . . . . ?
C9 C8 C16 C17 -31.2(6) . . . . ?
C7 C8 C16 C21 -33.8(6) . . . . ?
C9 C8 C16 C21 145.4(4) . . . . ?
C21 C16 C17 C18 -1.5(7) . . . . ?
C8 C16 C17 C18 175.2(4) . . . . ?
C16 C17 C18 C19 0.9(7) . . . . ?
C17 C18 C19 C20 0.2(7) . . . . ?
C17 C18 C19 Cl1 -179.4(4) . . . . ?
C18 C19 C20 C21 -0.6(7) . . . . ?
Cl1 C19 C20 C21 179.0(4) . . . . ?
C19 C20 C21 C16 0.0(7) . . . . ?
C17 C16 C21 C20 1.1(7) . . . . ?
C8 C16 C21 C20 -175.7(4) . . . . ?

_refine_diff_density_max         0.640
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_D_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1862418'
_audit_update_record             
;
2018-08-16 deposited with the CCDC.	2019-06-03 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         'C21 H14 Br3 N3 Zn'
_chemical_formula_sum            'C21 H14 Br3 N3 Zn'
_chemical_formula_weight         613.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.0757(18)
_cell_length_b                   15.534(3)
_cell_length_c                   14.621(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.49(3)
_cell_angle_gamma                90
_cell_volume                     2004.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    12723
_cell_measurement_theta_min      2.865
_cell_measurement_theta_max      29.514

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    7.218
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.26762
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            12723
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.865
_diffrn_reflns_theta_max         29.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4800
_reflns_number_gt                3288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2016 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2016 and PLATON (Spek, 2009)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+1.2552P] 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         4800
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.24726(5) 0.16917(3) 0.10592(3) 0.03741(13) Uani 1 1 d . . . . .
Br1 Br 0.24529(6) 0.23132(3) -0.04406(3) 0.05472(15) Uani 1 1 d . . . . .
Br2 Br 0.49428(5) 0.17323(4) 0.21018(3) 0.05501(15) Uani 1 1 d . . . . .
Br3 Br -0.34733(5) -0.14245(3) 0.58807(3) 0.04551(13) Uani 1 1 d . . . . .
N1 N 0.1364(4) 0.2741(2) 0.1670(2) 0.0392(8) Uani 1 1 d . . . . .
N2 N 0.0895(3) 0.1087(2) 0.1708(2) 0.0328(7) Uani 1 1 d . . . . .
N3 N 0.2331(4) 0.0339(2) 0.0595(2) 0.0392(8) Uani 1 1 d . . . . .
C1 C 0.1611(5) 0.3583(3) 0.1578(3) 0.0453(10) Uani 1 1 d . . . . .
H1A H 0.225663 0.375466 0.120257 0.054 Uiso 1 1 calc R U . . .
C2 C 0.0943(5) 0.4204(3) 0.2018(3) 0.0474(11) Uani 1 1 d . . . . .
H2A H 0.113611 0.478404 0.194159 0.057 Uiso 1 1 calc R U . . .
C3 C -0.0010(5) 0.3955(3) 0.2570(3) 0.0474(11) Uani 1 1 d . . . . .
H3A H -0.047464 0.436422 0.287278 0.057 Uiso 1 1 calc R U . . .
C4 C -0.0271(5) 0.3091(3) 0.2673(3) 0.0455(10) Uani 1 1 d . . . . .
H4A H -0.091843 0.290771 0.304165 0.055 Uiso 1 1 calc R U . . .
C5 C 0.0448(4) 0.2500(2) 0.2216(2) 0.0333(9) Uani 1 1 d . . . . .
C6 C 0.0237(4) 0.1556(2) 0.2275(3) 0.0336(9) Uani 1 1 d . . . . .
C7 C -0.0527(4) 0.1159(3) 0.2878(3) 0.0357(9) Uani 1 1 d . . . . .
H7A H -0.097800 0.149092 0.326689 0.043 Uiso 1 1 calc R U . . .
C8 C -0.0622(4) 0.0267(2) 0.2903(3) 0.0350(9) Uani 1 1 d . . . . .
C9 C 0.0009(4) -0.0199(3) 0.2270(3) 0.0355(9) Uani 1 1 d . . . . .
H9A H -0.007436 -0.079520 0.224260 0.043 Uiso 1 1 calc R U . . .
C10 C 0.0758(4) 0.0231(3) 0.1685(2) 0.0338(9) Uani 1 1 d . . . . .
C11 C 0.1484(4) -0.0193(3) 0.0992(2) 0.0337(9) Uani 1 1 d . . . . .
C12 C 0.1306(5) -0.1050(3) 0.0748(3) 0.0416(10) Uani 1 1 d . . . . .
H12A H 0.071267 -0.140721 0.102645 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2016(5) -0.1370(3) 0.0087(3) 0.0506(11) Uani 1 1 d . . . . .
H13A H 0.191195 -0.194675 -0.008546 0.061 Uiso 1 1 calc R U . . .
C14 C 0.2885(5) -0.0827(3) -0.0320(3) 0.0521(12) Uani 1 1 d . . . . .
H14A H 0.337272 -0.103048 -0.077102 0.062 Uiso 1 1 calc R U . . .
C15 C 0.3012(5) 0.0014(3) -0.0045(3) 0.0464(11) Uani 1 1 d . . . . .
H15A H 0.360175 0.037948 -0.031672 0.056 Uiso 1 1 calc R U . . .
C16 C -0.1316(4) -0.0159(2) 0.3607(3) 0.0345(9) Uani 1 1 d . . . . .
C17 C -0.0897(5) -0.0983(3) 0.3927(3) 0.0452(11) Uani 1 1 d . . . . .
H17A H -0.019664 -0.128260 0.367538 0.054 Uiso 1 1 calc R U . . .
C18 C -0.1496(5) -0.1369(3) 0.4609(3) 0.0438(10) Uani 1 1 d . . . . .
H18A H -0.118763 -0.191723 0.482799 0.053 Uiso 1 1 calc R U . . .
C19 C -0.2564(4) -0.0924(2) 0.4964(3) 0.0340(9) Uani 1 1 d . . . . .
C20 C -0.2997(4) -0.0102(2) 0.4654(3) 0.0360(9) Uani 1 1 d . . . . .
H20A H -0.370468 0.019504 0.490138 0.043 Uiso 1 1 calc R U . . .
C21 C -0.2379(4) 0.0277(2) 0.3979(3) 0.0350(9) Uani 1 1 d . . . . .
H21A H -0.267660 0.082907 0.376883 0.042 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 2.113(3) . ?
Zn1 N3 2.203(3) . ?
Zn1 N1 2.210(3) . ?
Zn1 Br1 2.3923(7) . ?
Zn1 Br2 2.3997(10) . ?
Br3 C19 1.898(3) . ?
N1 C5 1.334(5) . ?
N1 C1 1.340(5) . ?
N2 C10 1.335(5) . ?
N2 C6 1.343(5) . ?
N3 C15 1.334(5) . ?
N3 C11 1.349(5) . ?
C1 C2 1.376(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.370(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.484(5) . ?
C6 C7 1.387(5) . ?
C7 C8 1.389(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.399(5) . ?
C8 C16 1.482(5) . ?
C9 C10 1.382(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.486(5) . ?
C11 C12 1.378(6) . ?
C12 C13 1.374(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.380(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.365(6) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.384(5) . ?
C16 C21 1.389(5) . ?
C17 C18 1.380(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.385(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.381(5) . ?
C20 C21 1.376(5) . ?
C20 H20A 0.9300 . ?
C21 H21A 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 N3 73.61(12) . . ?
N2 Zn1 N1 74.11(12) . . ?
N3 Zn1 N1 145.97(12) . . ?
N2 Zn1 Br1 136.86(9) . . ?
N3 Zn1 Br1 96.60(8) . . ?
N1 Zn1 Br1 99.56(8) . . ?
N2 Zn1 Br2 110.93(9) . . ?
N3 Zn1 Br2 101.50(9) . . ?
N1 Zn1 Br2 99.77(9) . . ?
Br1 Zn1 Br2 112.19(3) . . ?
C5 N1 C1 118.5(4) . . ?
C5 N1 Zn1 116.2(3) . . ?
C1 N1 Zn1 125.2(3) . . ?
C10 N2 C6 120.2(3) . . ?
C10 N2 Zn1 120.0(2) . . ?
C6 N2 Zn1 118.8(2) . . ?
C15 N3 C11 118.3(4) . . ?
C15 N3 Zn1 125.0(3) . . ?
C11 N3 Zn1 116.7(2) . . ?
N1 C1 C2 122.3(4) . . ?
N1 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
N1 C5 C4 122.1(4) . . ?
N1 C5 C6 114.8(3) . . ?
C4 C5 C6 123.1(3) . . ?
N2 C6 C7 120.8(3) . . ?
N2 C6 C5 114.7(3) . . ?
C7 C6 C5 124.5(3) . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C7 C8 C9 117.4(3) . . ?
C7 C8 C16 120.2(3) . . ?
C9 C8 C16 122.3(3) . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
N2 C10 C9 121.5(3) . . ?
N2 C10 C11 113.9(3) . . ?
C9 C10 C11 124.6(3) . . ?
N3 C11 C12 121.6(3) . . ?
N3 C11 C10 114.2(3) . . ?
C12 C11 C10 124.2(3) . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C12 C13 C14 119.5(4) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C15 C14 C13 118.3(4) . . ?
C15 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?
N3 C15 C14 123.2(4) . . ?
N3 C15 H15A 118.4 . . ?
C14 C15 H15A 118.4 . . ?
C17 C16 C21 118.7(3) . . ?
C17 C16 C8 121.3(3) . . ?
C21 C16 C8 120.0(3) . . ?
C18 C17 C16 121.5(4) . . ?
C18 C17 H17A 119.3 . . ?
C16 C17 H17A 119.3 . . ?
C17 C18 C19 118.8(4) . . ?
C17 C18 H18A 120.6 . . ?
C19 C18 H18A 120.6 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 Br3 118.2(3) . . ?
C18 C19 Br3 121.2(3) . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20A 120.1 . . ?
C19 C20 H20A 120.1 . . ?
C20 C21 C16 120.6(4) . . ?
C20 C21 H21A 119.7 . . ?
C16 C21 H21A 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.6(6) . . . . ?
Zn1 N1 C1 C2 -176.5(3) . . . . ?
N1 C1 C2 C3 -0.1(7) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C1 N1 C5 C4 1.2(6) . . . . ?
Zn1 N1 C5 C4 177.4(3) . . . . ?
C1 N1 C5 C6 179.8(4) . . . . ?
Zn1 N1 C5 C6 -4.0(4) . . . . ?
C3 C4 C5 N1 -1.1(6) . . . . ?
C3 C4 C5 C6 -179.6(4) . . . . ?
C10 N2 C6 C7 3.2(6) . . . . ?
Zn1 N2 C6 C7 -165.2(3) . . . . ?
C10 N2 C6 C5 -178.7(3) . . . . ?
Zn1 N2 C6 C5 12.9(4) . . . . ?
N1 C5 C6 N2 -5.4(5) . . . . ?
C4 C5 C6 N2 173.2(4) . . . . ?
N1 C5 C6 C7 172.6(4) . . . . ?
C4 C5 C6 C7 -8.8(6) . . . . ?
N2 C6 C7 C8 0.1(6) . . . . ?
C5 C6 C7 C8 -177.9(4) . . . . ?
C6 C7 C8 C9 -3.2(6) . . . . ?
C6 C7 C8 C16 174.4(4) . . . . ?
C7 C8 C9 C10 3.2(6) . . . . ?
C16 C8 C9 C10 -174.4(4) . . . . ?
C6 N2 C10 C9 -3.2(6) . . . . ?
Zn1 N2 C10 C9 165.1(3) . . . . ?
C6 N2 C10 C11 177.3(3) . . . . ?
Zn1 N2 C10 C11 -14.4(4) . . . . ?
C8 C9 C10 N2 -0.1(6) . . . . ?
C8 C9 C10 C11 179.4(4) . . . . ?
C15 N3 C11 C12 -0.4(6) . . . . ?
Zn1 N3 C11 C12 179.4(3) . . . . ?
C15 N3 C11 C10 -179.2(4) . . . . ?
Zn1 N3 C11 C10 0.6(4) . . . . ?
N2 C10 C11 N3 8.5(5) . . . . ?
C9 C10 C11 N3 -171.0(4) . . . . ?
N2 C10 C11 C12 -170.2(4) . . . . ?
C9 C10 C11 C12 10.3(6) . . . . ?
N3 C11 C12 C13 0.4(6) . . . . ?
C10 C11 C12 C13 179.0(4) . . . . ?
C11 C12 C13 C14 -0.3(7) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C11 N3 C15 C14 0.4(6) . . . . ?
Zn1 N3 C15 C14 -179.4(3) . . . . ?
C13 C14 C15 N3 -0.3(7) . . . . ?
C7 C8 C16 C17 -152.6(4) . . . . ?
C9 C8 C16 C17 24.9(6) . . . . ?
C7 C8 C16 C21 25.7(6) . . . . ?
C9 C8 C16 C21 -156.8(4) . . . . ?
C21 C16 C17 C18 -0.9(6) . . . . ?
C8 C16 C17 C18 177.4(4) . . . . ?
C16 C17 C18 C19 1.5(7) . . . . ?
C17 C18 C19 C20 -1.4(6) . . . . ?
C17 C18 C19 Br3 178.4(3) . . . . ?
C18 C19 C20 C21 0.9(6) . . . . ?
Br3 C19 C20 C21 -179.0(3) . . . . ?
C19 C20 C21 C16 -0.3(6) . . . . ?
C17 C16 C21 C20 0.3(6) . . . . ?
C8 C16 C21 C20 -178.0(4) . . . . ?

_refine_diff_density_max         0.859
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_D_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1862416'
_audit_update_record             
;
2018-08-16 deposited with the CCDC.	2019-06-03 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         'C84 H56 F4 I8 N12 Zn4'
_chemical_formula_sum            'C84 H56 F4 I8 N12 Zn4'
_chemical_formula_weight         2586.08

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'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   14.0571(4)
_cell_length_b                   14.9076(3)
_cell_length_c                   19.6740(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4122.84(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    29460
_cell_measurement_theta_min      2.898
_cell_measurement_theta_max      29.632

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.083
_exptl_crystal_F_000             2448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.45
_exptl_absorpt_coefficient_mu    4.207
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            29460
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.898
_diffrn_reflns_theta_max         29.632
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5231
_reflns_number_gt                4410
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2016 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2016 and PLATON (Spek, 2009)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+5.1739P] 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         5231
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.003
_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 0.92900(3) 0.16460(3) 0.34119(2) 0.03028(10) Uani 1 1 d . . . . .
I1 I 0.84841(2) 0.22181(2) 0.45188(2) 0.04445(9) Uani 1 1 d . . . . .
I2 I 1.11356(2) 0.18187(2) 0.34463(2) 0.04783(9) Uani 1 1 d . . . . .
F1 F 0.8817(2) -0.11180(18) -0.14120(11) 0.0586(7) Uani 1 1 d . . . . .
N1 N 0.9149(2) 0.01914(18) 0.36236(13) 0.0307(6) Uani 1 1 d . . . . .
N2 N 0.88672(18) 0.10663(17) 0.24928(13) 0.0263(5) Uani 1 1 d . . . . .
N3 N 0.8941(2) 0.27832(18) 0.27321(14) 0.0309(6) Uani 1 1 d . . . . .
C1 C 0.9233(3) -0.0197(3) 0.42324(18) 0.0410(8) Uani 1 1 d . . . . .
H1A H 0.938415 0.015783 0.460591 0.049 Uiso 1 1 calc R U . . .
C2 C 0.9103(3) -0.1104(3) 0.43265(19) 0.0464(9) Uani 1 1 d . . . . .
H2A H 0.917372 -0.135979 0.475476 0.056 Uiso 1 1 calc R U . . .
C3 C 0.8865(3) -0.1627(3) 0.3773(2) 0.0453(9) Uani 1 1 d . . . . .
H3A H 0.875757 -0.223883 0.382712 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8787(3) -0.1236(2) 0.31398(19) 0.0376(8) Uani 1 1 d . . . . .
H4A H 0.863795 -0.158000 0.276004 0.045 Uiso 1 1 calc R U . . .
C5 C 0.8936(2) -0.0323(2) 0.30819(16) 0.0278(6) Uani 1 1 d . . . . .
C6 C 0.8860(2) 0.0172(2) 0.24314(16) 0.0266(6) Uani 1 1 d . . . . .
C7 C 0.8789(2) -0.0241(2) 0.18029(16) 0.0302(7) Uani 1 1 d . . . . .
H7A H 0.878911 -0.086348 0.177029 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8715(2) 0.0287(2) 0.12180(16) 0.0283(6) Uani 1 1 d . . . . .
C9 C 0.8682(2) 0.1213(2) 0.12992(16) 0.0296(6) Uani 1 1 d . . . . .
H9A H 0.860371 0.158348 0.092301 0.036 Uiso 1 1 calc R U . . .
C10 C 0.8766(2) 0.1581(2) 0.19414(15) 0.0259(6) Uani 1 1 d . . . . .
C11 C 0.8760(2) 0.2561(2) 0.20834(16) 0.0270(6) Uani 1 1 d . . . . .
C12 C 0.8568(3) 0.3205(2) 0.15931(18) 0.0357(7) Uani 1 1 d . . . . .
H12A H 0.843916 0.303689 0.114741 0.043 Uiso 1 1 calc R U . . .
C13 C 0.8571(3) 0.4099(2) 0.1776(2) 0.0398(8) Uani 1 1 d . . . . .
H13A H 0.845037 0.454108 0.145346 0.048 Uiso 1 1 calc R U . . .
C14 C 0.8757(3) 0.4329(2) 0.2444(2) 0.0407(8) Uani 1 1 d . . . . .
H14A H 0.876207 0.492584 0.257994 0.049 Uiso 1 1 calc R U . . .
C15 C 0.8933(3) 0.3652(2) 0.29010(19) 0.0379(8) Uani 1 1 d . . . . .
H15A H 0.905236 0.380649 0.335093 0.045 Uiso 1 1 calc R U . . .
C16 C 0.8693(2) -0.0119(2) 0.05291(15) 0.0302(7) Uani 1 1 d . . . . .
C17 C 0.8186(3) 0.0290(2) 0.00074(17) 0.0345(7) Uani 1 1 d . . . . .
H17A H 0.782022 0.079548 0.009894 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8220(3) -0.0050(2) -0.06479(17) 0.0386(8) Uani 1 1 d . . . . .
H18A H 0.788137 0.021883 -0.099883 0.046 Uiso 1 1 calc R U . . .
C19 C 0.8768(3) -0.0794(2) -0.07631(17) 0.0394(8) Uani 1 1 d . . . . .
C20 C 0.9263(3) -0.1229(2) -0.02647(18) 0.0387(8) Uani 1 1 d . . . . .
H20A H 0.962035 -0.173782 -0.036201 0.046 Uiso 1 1 calc R U . . .
C21 C 0.9216(3) -0.0893(2) 0.03838(17) 0.0353(7) Uani 1 1 d . . . . .
H21A H 0.953789 -0.118587 0.073245 0.042 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 2.090(3) . ?
Zn1 N3 2.214(3) . ?
Zn1 N1 2.217(3) . ?
Zn1 I1 2.5985(4) . ?
Zn1 I2 2.6081(5) . ?
F1 C19 1.366(4) . ?
N1 C1 1.335(4) . ?
N1 C5 1.346(4) . ?
N2 C10 1.336(4) . ?
N2 C6 1.338(4) . ?
N3 C15 1.337(4) . ?
N3 C11 1.343(4) . ?
C1 C2 1.378(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.379(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.380(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.481(4) . ?
C6 C7 1.385(4) . ?
C7 C8 1.398(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.390(4) . ?
C8 C16 1.485(4) . ?
C9 C10 1.382(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.487(4) . ?
C11 C12 1.388(5) . ?
C12 C13 1.380(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.383(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(5) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.391(5) . ?
C16 C21 1.398(5) . ?
C17 C18 1.386(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.369(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.365(5) . ?
C20 C21 1.372(5) . ?
C20 H20A 0.9300 . ?
C21 H21A 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 N3 74.40(10) . . ?
N2 Zn1 N1 74.50(10) . . ?
N3 Zn1 N1 147.40(10) . . ?
N2 Zn1 I1 137.45(7) . . ?
N3 Zn1 I1 99.11(7) . . ?
N1 Zn1 I1 97.16(7) . . ?
N2 Zn1 I2 110.25(7) . . ?
N3 Zn1 I2 99.23(8) . . ?
N1 Zn1 I2 100.41(8) . . ?
I1 Zn1 I2 112.302(16) . . ?
C1 N1 C5 118.9(3) . . ?
C1 N1 Zn1 125.8(2) . . ?
C5 N1 Zn1 115.3(2) . . ?
C10 N2 C6 119.9(3) . . ?
C10 N2 Zn1 119.7(2) . . ?
C6 N2 Zn1 119.5(2) . . ?
C15 N3 C11 118.3(3) . . ?
C15 N3 Zn1 126.4(2) . . ?
C11 N3 Zn1 115.3(2) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C5 118.6(4) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
N1 C5 C4 121.9(3) . . ?
N1 C5 C6 114.6(3) . . ?
C4 C5 C6 123.4(3) . . ?
N2 C6 C7 121.6(3) . . ?
N2 C6 C5 114.7(3) . . ?
C7 C6 C5 123.7(3) . . ?
C6 C7 C8 119.3(3) . . ?
C6 C7 H7A 120.3 . . ?
C8 C7 H7A 120.3 . . ?
C9 C8 C7 117.8(3) . . ?
C9 C8 C16 120.6(3) . . ?
C7 C8 C16 121.5(3) . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
N2 C10 C9 121.5(3) . . ?
N2 C10 C11 114.3(3) . . ?
C9 C10 C11 124.1(3) . . ?
N3 C11 C12 121.8(3) . . ?
N3 C11 C10 114.8(3) . . ?
C12 C11 C10 123.4(3) . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
C12 C13 C14 119.1(3) . . ?
C12 C13 H13A 120.4 . . ?
C14 C13 H13A 120.4 . . ?
C15 C14 C13 118.3(3) . . ?
C15 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?
N3 C15 C14 123.4(3) . . ?
N3 C15 H15A 118.3 . . ?
C14 C15 H15A 118.3 . . ?
C17 C16 C21 118.7(3) . . ?
C17 C16 C8 120.4(3) . . ?
C21 C16 C8 120.8(3) . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C19 C18 C17 118.0(3) . . ?
C19 C18 H18A 121.0 . . ?
C17 C18 H18A 121.0 . . ?
C20 C19 F1 118.5(3) . . ?
C20 C19 C18 123.5(3) . . ?
F1 C19 C18 118.0(3) . . ?
C19 C20 C21 118.1(3) . . ?
C19 C20 H20A 121.0 . . ?
C21 C20 H20A 121.0 . . ?
C20 C21 C16 121.1(3) . . ?
C20 C21 H21A 119.5 . . ?
C16 C21 H21A 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.5(6) . . . . ?
Zn1 N1 C1 C2 177.7(3) . . . . ?
N1 C1 C2 C3 -0.9(7) . . . . ?
C1 C2 C3 C4 1.7(7) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C1 N1 C5 C4 1.1(5) . . . . ?
Zn1 N1 C5 C4 -177.3(3) . . . . ?
C1 N1 C5 C6 -180.0(3) . . . . ?
Zn1 N1 C5 C6 1.7(4) . . . . ?
C3 C4 C5 N1 -0.3(6) . . . . ?
C3 C4 C5 C6 -179.2(3) . . . . ?
C10 N2 C6 C7 2.6(5) . . . . ?
Zn1 N2 C6 C7 -165.8(2) . . . . ?
C10 N2 C6 C5 -177.4(3) . . . . ?
Zn1 N2 C6 C5 14.1(4) . . . . ?
N1 C5 C6 N2 -9.9(4) . . . . ?
C4 C5 C6 N2 169.1(3) . . . . ?
N1 C5 C6 C7 170.1(3) . . . . ?
C4 C5 C6 C7 -11.0(5) . . . . ?
N2 C6 C7 C8 -0.4(5) . . . . ?
C5 C6 C7 C8 179.7(3) . . . . ?
C6 C7 C8 C9 -2.4(5) . . . . ?
C6 C7 C8 C16 176.4(3) . . . . ?
C7 C8 C9 C10 3.0(5) . . . . ?
C16 C8 C9 C10 -175.8(3) . . . . ?
C6 N2 C10 C9 -2.0(5) . . . . ?
Zn1 N2 C10 C9 166.5(2) . . . . ?
C6 N2 C10 C11 178.4(3) . . . . ?
Zn1 N2 C10 C11 -13.1(4) . . . . ?
C8 C9 C10 N2 -0.8(5) . . . . ?
C8 C9 C10 C11 178.7(3) . . . . ?
C15 N3 C11 C12 0.0(5) . . . . ?
Zn1 N3 C11 C12 -177.4(3) . . . . ?
C15 N3 C11 C10 -178.9(3) . . . . ?
Zn1 N3 C11 C10 3.7(4) . . . . ?
N2 C10 C11 N3 5.6(4) . . . . ?
C9 C10 C11 N3 -173.9(3) . . . . ?
N2 C10 C11 C12 -173.3(3) . . . . ?
C9 C10 C11 C12 7.1(5) . . . . ?
N3 C11 C12 C13 0.6(6) . . . . ?
C10 C11 C12 C13 179.4(3) . . . . ?
C11 C12 C13 C14 -0.6(6) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C11 N3 C15 C14 -0.6(6) . . . . ?
Zn1 N3 C15 C14 176.5(3) . . . . ?
C13 C14 C15 N3 0.5(6) . . . . ?
C9 C8 C16 C17 -32.7(5) . . . . ?
C7 C8 C16 C17 148.6(3) . . . . ?
C9 C8 C16 C21 144.3(3) . . . . ?
C7 C8 C16 C21 -34.4(5) . . . . ?
C21 C16 C17 C18 -1.8(5) . . . . ?
C8 C16 C17 C18 175.2(3) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 1.6(6) . . . . ?
C17 C18 C19 F1 -178.7(3) . . . . ?
F1 C19 C20 C21 179.4(3) . . . . ?
C18 C19 C20 C21 -0.9(6) . . . . ?
C19 C20 C21 C16 -1.2(6) . . . . ?
C17 C16 C21 C20 2.5(5) . . . . ?
C8 C16 C21 C20 -174.5(3) . . . . ?

_refine_diff_density_max         0.657
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_M
_database_code_depnum_ccdc_archive 'CCDC 1862420'
_audit_update_record             
;
2018-08-16 deposited with the CCDC.	2019-06-03 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         'C21 H14 Br2 I N3 Zn'
_chemical_formula_sum            'C21 H14 Br2 I N3 Zn'
_chemical_formula_weight         660.44

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   9.3250(19)
_cell_length_b                   15.850(3)
_cell_length_c                   14.480(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.45(3)
_cell_angle_gamma                90
_cell_volume                     2081.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13368
_cell_measurement_theta_min      2.893
_cell_measurement_theta_max      29.531

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    6.514
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            13366
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.893
_diffrn_reflns_theta_max         29.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5079
_reflns_number_gt                3544
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2016 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2016 and PLATON (Spek, 2009)'
_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)+(0.0562P)²+4.2761P] 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         5079
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.74287(7) 0.17030(5) 0.09878(4) 0.04848(19) Uani 1 1 d . . . . .
I1 I 0.14682(4) -0.14559(2) 0.58934(3) 0.05479(15) Uani 1 1 d . . . . .
Br1 Br 0.98684(8) 0.17710(6) 0.20226(5) 0.0746(2) Uani 1 1 d . . . . .
Br2 Br 0.73863(10) 0.22978(5) -0.05405(5) 0.0788(3) Uani 1 1 d . . . . .
N1 N 0.6363(5) 0.2725(3) 0.1616(3) 0.0483(11) Uani 1 1 d . . . . .
N2 N 0.5904(5) 0.1103(3) 0.1642(3) 0.0409(10) Uani 1 1 d . . . . .
N3 N 0.7356(5) 0.0376(3) 0.0538(3) 0.0504(11) Uani 1 1 d . . . . .
C1 C 0.6614(7) 0.3548(4) 0.1546(5) 0.0601(16) Uani 1 1 d . . . . .
H1A H 0.724567 0.371943 0.117088 0.072 Uiso 1 1 calc R U . . .
C2 C 0.5984(8) 0.4150(4) 0.1999(4) 0.0616(16) Uani 1 1 d . . . . .
H2A H 0.619391 0.471768 0.193637 0.074 Uiso 1 1 calc R U . . .
C3 C 0.5042(8) 0.3910(4) 0.2546(4) 0.0623(16) Uani 1 1 d . . . . .
H3A H 0.459957 0.431122 0.285785 0.075 Uiso 1 1 calc R U . . .
C4 C 0.4755(7) 0.3058(4) 0.2629(4) 0.0568(15) Uani 1 1 d . . . . .
H4A H 0.410997 0.287672 0.299099 0.068 Uiso 1 1 calc R U . . .
C5 C 0.5454(6) 0.2482(3) 0.2160(4) 0.0431(12) Uani 1 1 d . . . . .
C6 C 0.5250(6) 0.1551(3) 0.2207(4) 0.0421(12) Uani 1 1 d . . . . .
C7 C 0.4492(6) 0.1165(3) 0.2810(4) 0.0447(12) Uani 1 1 d . . . . .
H7A H 0.403528 0.149017 0.319348 0.054 Uiso 1 1 calc R U . . .
C8 C 0.4418(6) 0.0294(3) 0.2839(4) 0.0443(12) Uani 1 1 d . . . . .
C9 C 0.5046(6) -0.0162(4) 0.2209(4) 0.0476(13) Uani 1 1 d . . . . .
H9A H 0.496338 -0.074622 0.217968 0.057 Uiso 1 1 calc R U . . .
C10 C 0.5795(6) 0.0260(3) 0.1626(4) 0.0422(12) Uani 1 1 d . . . . .
C11 C 0.6547(6) -0.0153(4) 0.0943(4) 0.0431(12) Uani 1 1 d . . . . .
C12 C 0.6424(7) -0.0996(4) 0.0721(4) 0.0551(14) Uani 1 1 d . . . . .
H12A H 0.586669 -0.135088 0.101042 0.066 Uiso 1 1 calc R U . . .
C13 C 0.7142(9) -0.1307(5) 0.0060(5) 0.0676(18) Uani 1 1 d . . . . .
H13A H 0.705731 -0.187437 -0.010866 0.081 Uiso 1 1 calc R U . . .
C14 C 0.7985(8) -0.0775(5) -0.0348(5) 0.0685(19) Uani 1 1 d . . . . .
H14A H 0.849756 -0.097465 -0.078202 0.082 Uiso 1 1 calc R U . . .
C15 C 0.8044(7) 0.0058(5) -0.0093(4) 0.0651(18) Uani 1 1 d . . . . .
H15A H 0.859504 0.042252 -0.037736 0.078 Uiso 1 1 calc R U . . .
C16 C 0.3730(6) -0.0134(3) 0.3539(4) 0.0435(12) Uani 1 1 d . . . . .
C17 C 0.4147(7) -0.0943(4) 0.3870(5) 0.0563(15) Uani 1 1 d . . . . .
H17A H 0.485438 -0.122961 0.363222 0.068 Uiso 1 1 calc R U . . .
C18 C 0.3537(7) -0.1331(4) 0.4541(5) 0.0554(15) Uani 1 1 d . . . . .
H18A H 0.383369 -0.187062 0.475638 0.066 Uiso 1 1 calc R U . . .
C19 C 0.2477(6) -0.0906(3) 0.4889(4) 0.0444(12) Uani 1 1 d . . . . .
C20 C 0.2041(6) -0.0105(3) 0.4580(4) 0.0467(13) Uani 1 1 d . . . . .
H20A H 0.133935 0.017919 0.482510 0.056 Uiso 1 1 calc R U . . .
C21 C 0.2654(6) 0.0272(3) 0.3903(4) 0.0455(12) Uani 1 1 d . . . . .
H21A H 0.234327 0.080868 0.368464 0.055 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 2.110(4) . ?
Zn1 N3 2.198(5) . ?
Zn1 N1 2.204(5) . ?
Zn1 Br2 2.3973(10) . ?
Zn1 Br1 2.4180(13) . ?
I1 C19 2.098(5) . ?
N1 C1 1.333(8) . ?
N1 C5 1.340(7) . ?
N2 C6 1.333(7) . ?
N2 C10 1.339(7) . ?
N3 C15 1.333(7) . ?
N3 C11 1.349(7) . ?
C1 C2 1.367(10) . ?
C1 H1A 0.9300 . ?
C2 C3 1.367(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.387(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.492(7) . ?
C6 C7 1.387(7) . ?
C7 C8 1.383(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.396(7) . ?
C8 C16 1.484(7) . ?
C9 C10 1.386(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.490(7) . ?
C11 C12 1.373(9) . ?
C12 C13 1.380(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(10) . ?
C13 H13A 0.9300 . ?
C14 C15 1.368(10) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C21 1.394(7) . ?
C16 C17 1.392(8) . ?
C17 C18 1.379(8) . ?
C17 H17A 0.9300 . ?
C18 C19 1.384(8) . ?
C18 H18A 0.9300 . ?
C19 C20 1.375(8) . ?
C20 C21 1.381(7) . ?
C20 H20A 0.9300 . ?
C21 H21A 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 N3 73.97(17) . . ?
N2 Zn1 N1 74.34(17) . . ?
N3 Zn1 N1 147.07(17) . . ?
N2 Zn1 Br2 136.38(12) . . ?
N3 Zn1 Br2 96.33(12) . . ?
N1 Zn1 Br2 100.37(12) . . ?
N2 Zn1 Br1 112.14(12) . . ?
N3 Zn1 Br1 100.72(13) . . ?
N1 Zn1 Br1 99.27(13) . . ?
Br2 Zn1 Br1 111.45(4) . . ?
C1 N1 C5 118.1(5) . . ?
C1 N1 Zn1 125.7(4) . . ?
C5 N1 Zn1 116.1(4) . . ?
C6 N2 C10 119.9(4) . . ?
C6 N2 Zn1 119.2(3) . . ?
C10 N2 Zn1 119.9(3) . . ?
C15 N3 C11 118.1(6) . . ?
C15 N3 Zn1 125.3(4) . . ?
C11 N3 Zn1 116.6(3) . . ?
N1 C1 C2 123.0(6) . . ?
N1 C1 H1A 118.5 . . ?
C2 C1 H1A 118.5 . . ?
C1 C2 C3 119.3(6) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C2 C3 C4 119.0(6) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C3 C4 C5 118.4(6) . . ?
C3 C4 H4A 120.8 . . ?
C5 C4 H4A 120.8 . . ?
N1 C5 C4 122.2(5) . . ?
N1 C5 C6 114.5(5) . . ?
C4 C5 C6 123.3(5) . . ?
N2 C6 C7 121.6(5) . . ?
N2 C6 C5 114.7(4) . . ?
C7 C6 C5 123.7(5) . . ?
C8 C7 C6 119.7(5) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C7 C8 C9 117.7(5) . . ?
C7 C8 C16 120.7(5) . . ?
C9 C8 C16 121.6(5) . . ?
C10 C9 C8 119.8(5) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
N2 C10 C9 121.2(5) . . ?
N2 C10 C11 113.8(4) . . ?
C9 C10 C11 125.0(5) . . ?
N3 C11 C12 121.8(5) . . ?
N3 C11 C10 114.3(5) . . ?
C12 C11 C10 123.8(5) . . ?
C11 C12 C13 118.9(6) . . ?
C11 C12 H12A 120.5 . . ?
C13 C12 H12A 120.5 . . ?
C14 C13 C12 119.7(7) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C15 C14 C13 117.9(6) . . ?
C15 C14 H14A 121.0 . . ?
C13 C14 H14A 121.0 . . ?
N3 C15 C14 123.6(6) . . ?
N3 C15 H15A 118.2 . . ?
C14 C15 H15A 118.2 . . ?
C21 C16 C17 117.6(5) . . ?
C21 C16 C8 120.7(5) . . ?
C17 C16 C8 121.7(5) . . ?
C18 C17 C16 121.7(5) . . ?
C18 C17 H17A 119.2 . . ?
C16 C17 H17A 119.2 . . ?
C19 C18 C17 119.0(5) . . ?
C19 C18 H18A 120.5 . . ?
C17 C18 H18A 120.5 . . ?
C20 C19 C18 120.9(5) . . ?
C20 C19 I1 117.5(4) . . ?
C18 C19 I1 121.6(4) . . ?
C19 C20 C21 119.3(5) . . ?
C19 C20 H20A 120.3 . . ?
C21 C20 H20A 120.3 . . ?
C20 C21 C16 121.4(5) . . ?
C20 C21 H21A 119.3 . . ?
C16 C21 H21A 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.2(9) . . . . ?
Zn1 N1 C1 C2 -175.9(5) . . . . ?
N1 C1 C2 C3 -0.6(10) . . . . ?
C1 C2 C3 C4 0.3(10) . . . . ?
C2 C3 C4 C5 0.8(10) . . . . ?
C1 N1 C5 C4 1.3(8) . . . . ?
Zn1 N1 C5 C4 177.5(5) . . . . ?
C1 N1 C5 C6 -179.4(5) . . . . ?
Zn1 N1 C5 C6 -3.3(6) . . . . ?
C3 C4 C5 N1 -1.6(9) . . . . ?
C3 C4 C5 C6 179.2(6) . . . . ?
C10 N2 C6 C7 2.3(8) . . . . ?
Zn1 N2 C6 C7 -166.0(4) . . . . ?
C10 N2 C6 C5 180.0(5) . . . . ?
Zn1 N2 C6 C5 11.6(6) . . . . ?
N1 C5 C6 N2 -5.1(7) . . . . ?
C4 C5 C6 N2 174.2(5) . . . . ?
N1 C5 C6 C7 172.5(5) . . . . ?
C4 C5 C6 C7 -8.2(9) . . . . ?
N2 C6 C7 C8 0.6(9) . . . . ?
C5 C6 C7 C8 -176.8(5) . . . . ?
C6 C7 C8 C9 -3.7(8) . . . . ?
C6 C7 C8 C16 174.5(5) . . . . ?
C7 C8 C9 C10 4.1(8) . . . . ?
C16 C8 C9 C10 -174.1(5) . . . . ?
C6 N2 C10 C9 -1.9(8) . . . . ?
Zn1 N2 C10 C9 166.3(4) . . . . ?
C6 N2 C10 C11 178.4(5) . . . . ?
Zn1 N2 C10 C11 -13.3(6) . . . . ?
C8 C9 C10 N2 -1.3(8) . . . . ?
C8 C9 C10 C11 178.3(5) . . . . ?
C15 N3 C11 C12 0.0(8) . . . . ?
Zn1 N3 C11 C12 -179.8(4) . . . . ?
C15 N3 C11 C10 -178.9(5) . . . . ?
Zn1 N3 C11 C10 1.3(6) . . . . ?
N2 C10 C11 N3 7.4(7) . . . . ?
C9 C10 C11 N3 -172.2(5) . . . . ?
N2 C10 C11 C12 -171.5(5) . . . . ?
C9 C10 C11 C12 8.9(9) . . . . ?
N3 C11 C12 C13 -0.4(9) . . . . ?
C10 C11 C12 C13 178.4(6) . . . . ?
C11 C12 C13 C14 1.2(10) . . . . ?
C12 C13 C14 C15 -1.6(11) . . . . ?
C11 N3 C15 C14 -0.5(10) . . . . ?
Zn1 N3 C15 C14 179.3(5) . . . . ?
C13 C14 C15 N3 1.3(11) . . . . ?
C7 C8 C16 C21 26.2(8) . . . . ?
C9 C8 C16 C21 -155.7(6) . . . . ?
C7 C8 C16 C17 -152.6(6) . . . . ?
C9 C8 C16 C17 25.6(9) . . . . ?
C21 C16 C17 C18 -0.7(9) . . . . ?
C8 C16 C17 C18 178.1(6) . . . . ?
C16 C17 C18 C19 0.4(10) . . . . ?
C17 C18 C19 C20 -0.6(10) . . . . ?
C17 C18 C19 I1 179.0(5) . . . . ?
C18 C19 C20 C21 1.0(9) . . . . ?
I1 C19 C20 C21 -178.6(4) . . . . ?
C19 C20 C21 C16 -1.4(9) . . . . ?
C17 C16 C21 C20 1.2(9) . . . . ?
C8 C16 C21 C20 -177.6(5) . . . . ?

_refine_diff_density_max         0.800
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_D_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1862419'
_audit_update_record             
;
2018-08-16 deposited with the CCDC.	2019-06-03 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         'C21 H14 Br I2 N3 Zn'
_chemical_formula_sum            'C21 H14 Br I2 N3 Zn'
_chemical_formula_weight         707.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.0871(18)
_cell_length_b                   15.805(3)
_cell_length_c                   15.288(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.77(3)
_cell_angle_gamma                90
_cell_volume                     2141.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13851
_cell_measurement_theta_min      2.917
_cell_measurement_theta_max      29.340

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    5.908
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            13851
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.917
_diffrn_reflns_theta_max         29.340
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5086
_reflns_number_gt                3911
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2016 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2016 and PLATON (Spek, 2009)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²+1.9193P] 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         5086
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.23880(5) 0.16135(3) 0.10568(3) 0.04262(12) Uani 1 1 d . . . . .
Br1 Br -0.33602(5) -0.13243(3) 0.58651(3) 0.05371(12) Uani 1 1 d . . . . .
I1 I 0.24780(3) 0.22674(2) -0.04822(2) 0.06252(11) Uani 1 1 d . . . . .
I2 I 0.50250(3) 0.16910(2) 0.21383(2) 0.06240(11) Uani 1 1 d . . . . .
N1 N 0.2268(3) 0.0275(2) 0.0640(2) 0.0449(7) Uani 1 1 d . . . . .
N2 N 0.0850(3) 0.10381(19) 0.1712(2) 0.0385(7) Uani 1 1 d . . . . .
N3 N 0.1285(4) 0.2665(2) 0.1617(2) 0.0459(8) Uani 1 1 d . . . . .
C1 C 0.2940(5) -0.0057(3) 0.0033(3) 0.0589(11) Uani 1 1 d . . . . .
H1A H 0.349674 0.029915 -0.025513 0.071 Uiso 1 1 calc R U . . .
C2 C 0.2853(6) -0.0901(3) -0.0191(3) 0.0672(13) Uani 1 1 d . . . . .
H2A H 0.334443 -0.111436 -0.061685 0.081 Uiso 1 1 calc R U . . .
C3 C 0.2023(6) -0.1417(3) 0.0231(3) 0.0679(13) Uani 1 1 d . . . . .
H3A H 0.191366 -0.198785 0.008144 0.082 Uiso 1 1 calc R U . . .
C4 C 0.1348(5) -0.1088(3) 0.0879(3) 0.0523(10) Uani 1 1 d . . . . .
H4A H 0.080902 -0.143849 0.118412 0.063 Uiso 1 1 calc R U . . .
C5 C 0.1477(4) -0.0240(3) 0.1070(2) 0.0418(8) Uani 1 1 d . . . . .
C6 C 0.0748(4) 0.0195(2) 0.1723(2) 0.0392(8) Uani 1 1 d . . . . .
C7 C 0.0027(4) -0.0215(2) 0.2308(2) 0.0410(8) Uani 1 1 d . . . . .
H7A H -0.004037 -0.080251 0.230301 0.049 Uiso 1 1 calc R U . . .
C8 C -0.0605(4) 0.0258(2) 0.2912(3) 0.0401(8) Uani 1 1 d . . . . .
C9 C -0.0528(4) 0.1131(2) 0.2856(3) 0.0423(8) Uani 1 1 d . . . . .
H9A H -0.096844 0.146670 0.322734 0.051 Uiso 1 1 calc R U . . .
C10 C 0.0203(4) 0.1508(2) 0.2249(2) 0.0391(8) Uani 1 1 d . . . . .
C11 C 0.0381(4) 0.2431(2) 0.2161(2) 0.0421(8) Uani 1 1 d . . . . .
C12 C -0.0312(5) 0.3029(3) 0.2599(3) 0.0580(11) Uani 1 1 d . . . . .
H12A H -0.095250 0.286066 0.296500 0.070 Uiso 1 1 calc R U . . .
C13 C -0.0039(5) 0.3877(3) 0.2485(3) 0.0606(11) Uani 1 1 d . . . . .
H13A H -0.048266 0.428596 0.277929 0.073 Uiso 1 1 calc R U . . .
C14 C 0.0886(5) 0.4109(3) 0.1937(3) 0.0573(11) Uani 1 1 d . . . . .
H14A H 0.108420 0.467644 0.185216 0.069 Uiso 1 1 calc R U . . .
C15 C 0.1519(5) 0.3490(3) 0.1513(3) 0.0566(11) Uani 1 1 d . . . . .
H15A H 0.214271 0.365090 0.113512 0.068 Uiso 1 1 calc R U . . .
C16 C -0.1276(4) -0.0150(2) 0.3608(2) 0.0397(8) Uani 1 1 d . . . . .
C17 C -0.2324(4) 0.0286(2) 0.3973(3) 0.0432(9) Uani 1 1 d . . . . .
H17A H -0.262268 0.082545 0.376341 0.052 Uiso 1 1 calc R U . . .
C18 C -0.2930(4) -0.0066(2) 0.4638(3) 0.0436(9) Uani 1 1 d . . . . .
H18A H -0.363748 0.023201 0.487226 0.052 Uiso 1 1 calc R U . . .
C19 C -0.2485(4) -0.0855(2) 0.4951(3) 0.0409(8) Uani 1 1 d . . . . .
C20 C -0.1449(5) -0.1312(3) 0.4604(3) 0.0527(10) Uani 1 1 d . . . . .
H20A H -0.115749 -0.185134 0.481696 0.063 Uiso 1 1 calc R U . . .
C21 C -0.0858(5) -0.0954(3) 0.3936(3) 0.0540(11) Uani 1 1 d . . . . .
H21A H -0.016180 -0.125824 0.369883 0.065 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 2.098(3) . ?
Zn1 N1 2.205(3) . ?
Zn1 N3 2.209(3) . ?
Zn1 I1 2.5876(7) . ?
Zn1 I2 2.5960(10) . ?
Br1 C19 1.904(4) . ?
N1 C1 1.327(5) . ?
N1 C5 1.348(5) . ?
N2 C6 1.336(5) . ?
N2 C10 1.337(5) . ?
N3 C15 1.335(5) . ?
N3 C11 1.344(5) . ?
C1 C2 1.376(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.366(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.484(5) . ?
C6 C7 1.382(5) . ?
C7 C8 1.405(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.384(5) . ?
C8 C16 1.486(5) . ?
C9 C10 1.389(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.477(5) . ?
C11 C12 1.387(6) . ?
C12 C13 1.382(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.361(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.368(6) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C21 1.388(5) . ?
C16 C17 1.389(5) . ?
C17 C18 1.376(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.365(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.382(5) . ?
C20 C21 1.376(6) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 74.10(12) . . ?
N2 Zn1 N3 74.58(12) . . ?
N1 Zn1 N3 146.72(11) . . ?
N2 Zn1 I1 139.94(8) . . ?
N1 Zn1 I1 97.49(8) . . ?
N3 Zn1 I1 99.21(9) . . ?
N2 Zn1 I2 109.57(8) . . ?
N1 Zn1 I2 102.06(8) . . ?
N3 Zn1 I2 98.73(9) . . ?
I1 Zn1 I2 110.49(3) . . ?
C1 N1 C5 118.7(4) . . ?
C1 N1 Zn1 125.4(3) . . ?
C5 N1 Zn1 115.8(2) . . ?
C6 N2 C10 120.3(3) . . ?
C6 N2 Zn1 119.6(2) . . ?
C10 N2 Zn1 118.9(2) . . ?
C15 N3 C11 118.5(4) . . ?
C15 N3 Zn1 126.2(3) . . ?
C11 N3 Zn1 115.1(3) . . ?
N1 C1 C2 123.2(4) . . ?
N1 C1 H1A 118.4 . . ?
C2 C1 H1A 118.4 . . ?
C3 C2 C1 118.0(4) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C2 C3 C4 119.6(5) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
N1 C5 C4 121.0(4) . . ?
N1 C5 C6 114.5(3) . . ?
C4 C5 C6 124.5(4) . . ?
N2 C6 C7 121.4(3) . . ?
N2 C6 C5 114.2(3) . . ?
C7 C6 C5 124.4(4) . . ?
C6 C7 C8 119.7(4) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C9 C8 C7 117.2(3) . . ?
C9 C8 C16 120.8(3) . . ?
C7 C8 C16 122.0(3) . . ?
C8 C9 C10 120.5(4) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
N2 C10 C9 120.8(4) . . ?
N2 C10 C11 114.9(3) . . ?
C9 C10 C11 124.3(3) . . ?
N3 C11 C12 121.1(4) . . ?
N3 C11 C10 115.0(3) . . ?
C12 C11 C10 123.9(3) . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C13 C14 C15 118.7(4) . . ?
C13 C14 H14A 120.7 . . ?
C15 C14 H14A 120.7 . . ?
N3 C15 C14 123.1(4) . . ?
N3 C15 H15A 118.4 . . ?
C14 C15 H15A 118.4 . . ?
C21 C16 C17 117.8(3) . . ?
C21 C16 C8 122.3(3) . . ?
C17 C16 C8 119.9(3) . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17A 119.4 . . ?
C16 C17 H17A 119.4 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C18 C19 C20 121.1(3) . . ?
C18 C19 Br1 118.3(3) . . ?
C20 C19 Br1 120.6(3) . . ?
C21 C20 C19 118.7(4) . . ?
C21 C20 H20A 120.6 . . ?
C19 C20 H20A 120.6 . . ?
C20 C21 C16 121.7(4) . . ?
C20 C21 H21A 119.2 . . ?
C16 C21 H21A 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1.0(7) . . . . ?
Zn1 N1 C1 C2 178.7(4) . . . . ?
N1 C1 C2 C3 0.5(8) . . . . ?
C1 C2 C3 C4 -2.1(8) . . . . ?
C2 C3 C4 C5 2.2(7) . . . . ?
C1 N1 C5 C4 -0.9(6) . . . . ?
Zn1 N1 C5 C4 -178.8(3) . . . . ?
C1 N1 C5 C6 -178.9(4) . . . . ?
Zn1 N1 C5 C6 3.1(4) . . . . ?
C3 C4 C5 N1 -0.7(6) . . . . ?
C3 C4 C5 C6 177.2(4) . . . . ?
C10 N2 C6 C7 -2.5(5) . . . . ?
Zn1 N2 C6 C7 164.8(3) . . . . ?
C10 N2 C6 C5 178.1(3) . . . . ?
Zn1 N2 C6 C5 -14.6(4) . . . . ?
N1 C5 C6 N2 6.9(5) . . . . ?
C4 C5 C6 N2 -171.0(4) . . . . ?
N1 C5 C6 C7 -172.5(3) . . . . ?
C4 C5 C6 C7 9.5(6) . . . . ?
N2 C6 C7 C8 -0.5(5) . . . . ?
C5 C6 C7 C8 178.8(3) . . . . ?
C6 C7 C8 C9 3.0(5) . . . . ?
C6 C7 C8 C16 -174.6(3) . . . . ?
C7 C8 C9 C10 -2.6(5) . . . . ?
C16 C8 C9 C10 175.1(3) . . . . ?
C6 N2 C10 C9 2.9(5) . . . . ?
Zn1 N2 C10 C9 -164.5(3) . . . . ?
C6 N2 C10 C11 -179.1(3) . . . . ?
Zn1 N2 C10 C11 13.5(4) . . . . ?
C8 C9 C10 N2 -0.3(6) . . . . ?
C8 C9 C10 C11 -178.1(4) . . . . ?
C15 N3 C11 C12 0.8(6) . . . . ?
Zn1 N3 C11 C12 176.2(3) . . . . ?
C15 N3 C11 C10 -179.0(4) . . . . ?
Zn1 N3 C11 C10 -3.6(4) . . . . ?
N2 C10 C11 N3 -6.0(5) . . . . ?
C9 C10 C11 N3 171.9(4) . . . . ?
N2 C10 C11 C12 174.2(4) . . . . ?
C9 C10 C11 C12 -7.9(6) . . . . ?
N3 C11 C12 C13 -1.3(7) . . . . ?
C10 C11 C12 C13 178.5(4) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C11 N3 C15 C14 0.2(7) . . . . ?
Zn1 N3 C15 C14 -174.7(3) . . . . ?
C13 C14 C15 N3 -0.6(7) . . . . ?
C9 C8 C16 C21 -153.1(4) . . . . ?
C7 C8 C16 C21 24.5(6) . . . . ?
C9 C8 C16 C17 24.9(5) . . . . ?
C7 C8 C16 C17 -157.6(4) . . . . ?
C21 C16 C17 C18 0.1(6) . . . . ?
C8 C16 C17 C18 -178.0(4) . . . . ?
C16 C17 C18 C19 0.5(6) . . . . ?
C17 C18 C19 C20 -0.8(6) . . . . ?
C17 C18 C19 Br1 -179.5(3) . . . . ?
C18 C19 C20 C21 0.5(7) . . . . ?
Br1 C19 C20 C21 179.2(3) . . . . ?
C19 C20 C21 C16 0.1(7) . . . . ?
C17 C16 C21 C20 -0.3(6) . . . . ?
C8 C16 C21 C20 177.6(4) . . . . ?

_refine_diff_density_max         0.734
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.091

