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

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

data_160a
_database_code_depnum_ccdc_archive 'CCDC 1524915'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 Cl2 N4 O Zn'
_chemical_formula_sum            'C12 H10 Cl2 N4 O Zn'
_chemical_formula_weight         362.51

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_space_group_name_Hall           -P2ybc

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

_cell_length_a                   7.4184(4)
_cell_length_b                   10.1888(6)
_cell_length_c                   18.1480(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.187(4)
_cell_angle_gamma                90.00
_cell_volume                     1371.42(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    811
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      24.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    2.179
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4210
_exptl_absorpt_correction_T_max  0.7955
_exptl_absorpt_process_details   'Bruker TWINABS, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2408
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2408
_reflns_number_gt                2198
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

 Cell_now output:
 Rotated from first domain by 179.9 degrees about
 reciprocal axis  0.000 -0.001  1.000  and real axis  0.052  0.000  1.000

 Twin law to convert hkl from first to     -1.000   0.001   0.001
 this domain (SHELXL TWIN matrix):         -0.003  -1.000  -0.002
                                            0.103  -0.001   1.000

 The structure has been refined as a non-merohedral twin with a ratio 0.39:0.61
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0519P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2437
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.25781(7) 0.28809(4) 0.03547(2) 0.01860(16) Uani 1 1 d . . .
Cl1 Cl 0.00033(14) 0.21893(9) 0.08649(6) 0.0220(3) Uani 1 1 d . . .
Cl2 Cl 0.51517(14) 0.18677(10) 0.06675(6) 0.0232(3) Uani 1 1 d . . .
O1 O 0.3016(4) 0.4606(3) 0.11633(16) 0.0277(7) Uani 1 1 d . . .
N1 N 0.2208(5) 0.2314(3) -0.07815(18) 0.0196(7) Uani 1 1 d . . .
N2 N 0.2416(5) 0.4667(3) -0.02443(17) 0.0180(7) Uani 1 1 d . . .
N3 N 0.2633(5) 0.5828(3) 0.01287(17) 0.0201(8) Uani 1 1 d . . .
H9 H 0.2589 0.6596 -0.0093 0.024 Uiso 1 1 calc R . .
N4 N 0.3368(5) 0.9154(4) 0.2222(2) 0.0258(9) Uani 1 1 d . . .
C2 C 0.2140(6) 0.1087(4) -0.1039(2) 0.0235(10) Uani 1 1 d . . .
H2 H 0.2355 0.0384 -0.0705 0.028 Uiso 1 1 calc R . .
C3 C 0.1770(6) 0.0792(4) -0.1775(3) 0.0259(10) Uani 1 1 d . . .
H3 H 0.1737 -0.0093 -0.1939 0.031 Uiso 1 1 calc R . .
C4 C 0.1452(6) 0.1809(5) -0.2259(3) 0.0274(11) Uani 1 1 d . . .
H4 H 0.1171 0.1632 -0.2762 0.033 Uiso 1 1 calc R . .
C5 C 0.1543(6) 0.3091(4) -0.2008(2) 0.0238(10) Uani 1 1 d . . .
H5 H 0.1346 0.3806 -0.2335 0.029 Uiso 1 1 calc R . .
C6 C 0.1930(5) 0.3305(4) -0.1264(2) 0.0200(9) Uani 1 1 d . . .
C7 C 0.2108(5) 0.4639(4) -0.0944(2) 0.0202(9) Uani 1 1 d . . .
H7 H 0.2002 0.5413 -0.1233 0.024 Uiso 1 1 calc R . .
C10 C 0.2925(6) 0.5697(4) 0.0882(2) 0.0196(9) Uani 1 1 d . . .
C12 C 0.3107(5) 0.6939(4) 0.1317(2) 0.0193(9) Uani 1 1 d . . .
C13 C 0.3818(5) 0.6844(4) 0.2034(2) 0.0220(10) Uani 1 1 d . . .
H13 H 0.4222 0.6025 0.2225 0.026 Uiso 1 1 calc R . .
C14 C 0.3922(6) 0.7965(4) 0.2458(3) 0.0265(11) Uani 1 1 d . . .
H14 H 0.4413 0.7895 0.2944 0.032 Uiso 1 1 calc R . .
C16 C 0.2712(6) 0.9234(4) 0.1529(2) 0.0239(10) Uani 1 1 d . . .
H16 H 0.2333 1.0068 0.1351 0.029 Uiso 1 1 calc R . .
C17 C 0.2556(6) 0.8164(4) 0.1055(2) 0.0185(9) Uani 1 1 d . . .
H17 H 0.2087 0.8266 0.0567 0.022 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.122(3) . ?
Zn1 N1 2.153(3) . ?
Zn1 Cl2 2.2334(12) . ?
Zn1 Cl1 2.2530(11) . ?
Zn1 O1 2.308(3) . ?
O1 C10 1.225(5) . ?
N1 C2 1.336(5) . ?
N1 C6 1.349(5) . ?
N2 C7 1.285(5) . ?
N2 N3 1.370(4) . ?
N3 C10 1.386(5) . ?
N3 H9 0.8800 . ?
N4 C16 1.343(5) . ?
N4 C14 1.346(6) . ?
C2 C3 1.390(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.483(6) . ?
C7 H7 0.9500 . ?
C10 C12 1.496(6) . ?
C12 C17 1.395(5) . ?
C12 C13 1.397(6) . ?
C13 C14 1.379(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C16 C17 1.391(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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 74.63(12) . . ?
N2 Zn1 Cl2 124.45(10) . . ?
N1 Zn1 Cl2 102.17(10) . . ?
N2 Zn1 Cl1 116.06(10) . . ?
N1 Zn1 Cl1 102.55(10) . . ?
Cl2 Zn1 Cl1 118.59(4) . . ?
N2 Zn1 O1 71.24(11) . . ?
N1 Zn1 O1 145.74(11) . . ?
Cl2 Zn1 O1 94.71(8) . . ?
Cl1 Zn1 O1 94.94(8) . . ?
C10 O1 Zn1 114.8(3) . . ?
C2 N1 C6 118.0(4) . . ?
C2 N1 Zn1 126.1(3) . . ?
C6 N1 Zn1 115.8(3) . . ?
C7 N2 N3 121.6(3) . . ?
C7 N2 Zn1 119.6(3) . . ?
N3 N2 Zn1 118.8(2) . . ?
N2 N3 C10 114.7(3) . . ?
N2 N3 H9 122.6 . . ?
C10 N3 H9 122.6 . . ?
C16 N4 C14 117.0(4) . . ?
N1 C2 C3 122.9(4) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C4 C3 C2 118.6(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 118.4(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 122.5(4) . . ?
N1 C6 C7 114.9(4) . . ?
C5 C6 C7 122.6(4) . . ?
N2 C7 C6 114.8(4) . . ?
N2 C7 H7 122.6 . . ?
C6 C7 H7 122.6 . . ?
O1 C10 N3 120.3(4) . . ?
O1 C10 C12 122.9(4) . . ?
N3 C10 C12 116.8(3) . . ?
C17 C12 C13 118.8(4) . . ?
C17 C12 C10 123.7(4) . . ?
C13 C12 C10 117.5(4) . . ?
C14 C13 C12 118.6(4) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
N4 C14 C13 123.8(4) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C16 C17 123.8(4) . . ?
N4 C16 H16 118.1 . . ?
C17 C16 H16 118.1 . . ?
C16 C17 C12 118.1(4) . . ?
C16 C17 H17 121.0 . . ?
C12 C17 H17 121.0 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.100
####################################################################### 
# 
# 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_s1
_database_code_depnum_ccdc_archive 'CCDC 1524919'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_vrf_PLAT430_I                   
;
PROBLEM: Short Inter D...A Contact  O2W    ..  O2W     ..       2.25 Ang.  
RESPONSE: The H atoms of water molecules could not be located from Fourier map.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C72 H52 I2 N16 O4 Zn4, I4 Zn, 4(O)'
_chemical_formula_sum            'C72 H52 I6 N16 O8 Zn5'
_chemical_formula_weight         2357.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   29.7670(12)
_cell_length_b                   10.3466(4)
_cell_length_c                   25.8735(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.543(2)
_cell_angle_gamma                90
_cell_volume                     7880.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6800
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      28.2

_exptl_crystal_description       'block (fragment)'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_F_000             4512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    3.914
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_T_max  0.54
_exptl_absorpt_process_details   'Walker, N. & Stuart, D. (1983)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS-1'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43440
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.384
_diffrn_reflns_theta_max         26.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8113
_reflns_number_gt                5835
_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       'STOE IPDS software'
_computing_cell_refinement       'STOE IPDS software'
_computing_data_reduction        'STOE IPDS software, STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0450P)²+118.6107P] 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         8113
_refine_ls_number_parameters     483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
I1 I -0.33523(2) 1.57858(4) 0.14584(2) 0.02798(13) Uani 1 1 d . . . . .
I2 I 0.03454(2) 0.82050(8) 0.18371(3) 0.0786(3) Uani 1 1 d . . . . .
I3 I 0.06294(2) 0.51612(6) 0.29532(2) 0.04131(16) Uani 1 1 d . . . . .
Zn1 Zn -0.25341(3) 1.57436(7) 0.10521(3) 0.02174(18) Uani 1 1 d . . . . .
Zn2 Zn -0.15526(3) 1.59704(8) 0.00816(3) 0.0262(2) Uani 1 1 d . . . . .
Zn3 Zn 0.0000 0.67115(14) 0.2500 0.0421(3) Uani 1 2 d S T P . .
O1 O -0.19450(16) 1.5208(4) 0.06880(17) 0.0222(10) Uani 1 1 d . . . . .
O1W O -0.4304(3) 1.4055(11) -0.2284(3) 0.114(4) Uani 1 1 d . . . . .
O2 O -0.29071(16) 1.5451(4) 0.02967(16) 0.0229(10) Uani 1 1 d . . . . .
N1 N -0.1058(2) 1.5665(6) -0.0430(3) 0.0380(16) Uani 1 1 d . . . . .
O2W O -0.4909(8) 1.2575(19) -0.2907(9) 0.272(10) Uani 1 1 d . . . . .
N2 N -0.1250(2) 1.4260(5) 0.0333(2) 0.0241(13) Uani 1 1 d . . . . .
N3 N -0.1384(2) 1.3621(5) 0.0750(2) 0.0248(13) Uani 1 1 d . . . . .
N4 N -0.2272(2) 1.4120(5) 0.1495(2) 0.0238(13) Uani 1 1 d . . . . .
N5 N -0.2147(2) 1.7094(6) 0.1588(2) 0.0237(13) Uani 1 1 d . . . . .
N6 N -0.26990(19) 1.7633(5) 0.0737(2) 0.0202(12) Uani 1 1 d . . . . .
N7 N -0.30230(19) 1.7670(5) 0.0300(2) 0.0186(12) Uani 1 1 d . . . . .
N8 N -0.3656(2) 1.7460(6) -0.0540(2) 0.0261(13) Uani 1 1 d . . . . .
C1 C -0.0818(3) 1.4557(8) -0.0346(3) 0.039(2) Uani 1 1 d . . . . .
C3 C -0.0974(3) 1.6438(9) -0.0820(4) 0.056(3) Uani 1 1 d . . . . .
H3A H -0.1142 1.7217 -0.0882 0.067 Uiso 1 1 calc R U . . .
C4 C -0.0651(4) 1.6145(11) -0.1136(4) 0.075(4) Uani 1 1 d . . . . .
H4A H -0.0593 1.6720 -0.1404 0.090 Uiso 1 1 calc R U . . .
C5 C -0.0416(4) 1.5000(11) -0.1050(5) 0.074(4) Uani 1 1 d . . . . .
H5A H -0.0204 1.4751 -0.1272 0.089 Uiso 1 1 calc R U . . .
C6 C -0.0491(3) 1.4216(9) -0.0639(4) 0.051(2) Uani 1 1 d . . . . .
H6A H -0.0318 1.3451 -0.0561 0.061 Uiso 1 1 calc R U . . .
C7 C -0.0940(2) 1.3770(7) 0.0097(3) 0.0290(17) Uani 1 1 d . . . . .
C8 C -0.0716(3) 1.2514(8) 0.0245(3) 0.037(2) Uani 1 1 d . . . . .
C9 C -0.0762(3) 1.1474(8) -0.0109(4) 0.043(2) Uani 1 1 d . . . . .
H9A H -0.0927 1.1574 -0.0451 0.052 Uiso 1 1 calc R U . . .
C10 C -0.0563(3) 1.0305(9) 0.0049(5) 0.059(3) Uani 1 1 d . . . . .
H10A H -0.0601 0.9585 -0.0182 0.071 Uiso 1 1 calc R U . . .
C11 C -0.0311(4) 1.0175(11) 0.0535(5) 0.065(3) Uani 1 1 d . . . . .
H11A H -0.0170 0.9371 0.0634 0.078 Uiso 1 1 calc R U . . .
C12 C -0.0260(3) 1.1183(10) 0.0882(4) 0.056(3) Uani 1 1 d . . . . .
H12A H -0.0079 1.1086 0.1214 0.067 Uiso 1 1 calc R U . . .
C13 C -0.0475(3) 1.2342(9) 0.0743(4) 0.045(2) Uani 1 1 d . . . . .
H13A H -0.0458 1.3027 0.0990 0.055 Uiso 1 1 calc R U . . .
C14 C -0.1729(2) 1.4236(6) 0.0902(2) 0.0227(15) Uani 1 1 d . . . . .
C15 C -0.1870(2) 1.3703(6) 0.1391(2) 0.0209(15) Uani 1 1 d . . . . .
C16 C -0.2413(3) 1.3712(7) 0.1940(3) 0.0308(17) Uani 1 1 d . . . . .
H16A H -0.2704 1.3967 0.2012 0.037 Uiso 1 1 calc R U . . .
C17 C -0.2143(3) 1.2928(7) 0.2295(3) 0.0326(18) Uani 1 1 d . . . . .
H17A H -0.2247 1.2664 0.2609 0.039 Uiso 1 1 calc R U . . .
C18 C -0.1729(3) 1.2542(7) 0.2191(3) 0.0280(17) Uani 1 1 d . . . . .
H18A H -0.1537 1.2025 0.2434 0.034 Uiso 1 1 calc R U . . .
C19 C -0.1593(3) 1.2912(6) 0.1726(3) 0.0254(16) Uani 1 1 d . . . . .
H19A H -0.1310 1.2623 0.1638 0.030 Uiso 1 1 calc R U . . .
C20 C -0.2260(2) 1.8352(6) 0.1502(2) 0.0218(15) Uani 1 1 d . . . . .
C21 C -0.2054(3) 1.9329(7) 0.1813(3) 0.0303(17) Uani 1 1 d . . . . .
H21A H -0.2143 2.0203 0.1750 0.036 Uiso 1 1 calc R U . . .
C22 C -0.1712(3) 1.9011(8) 0.2219(3) 0.0328(18) Uani 1 1 d . . . . .
H22A H -0.1562 1.9670 0.2436 0.039 Uiso 1 1 calc R U . . .
C23 C -0.1594(2) 1.7751(8) 0.2306(3) 0.0300(17) Uani 1 1 d . . . . .
H23A H -0.1362 1.7516 0.2583 0.036 Uiso 1 1 calc R U . . .
C24 C -0.1820(3) 1.6815(7) 0.1980(3) 0.0290(17) Uani 1 1 d . . . . .
H24A H -0.1736 1.5935 0.2041 0.035 Uiso 1 1 calc R U . . .
C25 C -0.2605(2) 1.8627(7) 0.1031(3) 0.0235(15) Uani 1 1 d . . . . .
C26 C -0.2812(2) 1.9948(7) 0.0953(3) 0.0255(16) Uani 1 1 d . . . . .
C27 C -0.3076(3) 2.0417(8) 0.1315(3) 0.042(2) Uani 1 1 d . . . . .
H27A H -0.3133 1.9895 0.1600 0.050 Uiso 1 1 calc R U . . .
C28 C -0.3253(3) 2.1654(9) 0.1251(3) 0.047(2) Uani 1 1 d . . . . .
H28A H -0.3437 2.1981 0.1492 0.056 Uiso 1 1 calc R U . . .
C29 C -0.3164(3) 2.2412(8) 0.0841(3) 0.040(2) Uani 1 1 d . . . . .
H29A H -0.3282 2.3266 0.0803 0.049 Uiso 1 1 calc R U . . .
C30 C -0.2907(3) 2.1941(7) 0.0489(3) 0.0327(18) Uani 1 1 d . . . . .
H30A H -0.2850 2.2469 0.0206 0.039 Uiso 1 1 calc R U . . .
C31 C -0.2730(3) 2.0710(7) 0.0538(3) 0.0283(16) Uani 1 1 d . . . . .
H31A H -0.2554 2.0387 0.0289 0.034 Uiso 1 1 calc R U . . .
C32 C -0.3093(2) 1.6458(7) 0.0106(2) 0.0217(15) Uani 1 1 d . . . . .
C33 C -0.3436(2) 1.6360(7) -0.0388(2) 0.0221(15) Uani 1 1 d . . . . .
C34 C -0.3499(2) 1.5221(7) -0.0663(3) 0.0273(16) Uani 1 1 d . . . . .
H34A H -0.3343 1.4454 -0.0540 0.033 Uiso 1 1 calc R U . . .
C35 C -0.3800(3) 1.5237(9) -0.1129(3) 0.0362(19) Uani 1 1 d . . . . .
H35A H -0.3850 1.4475 -0.1334 0.043 Uiso 1 1 calc R U . . .
C36 C -0.4023(3) 1.6353(9) -0.1289(3) 0.0368(19) Uani 1 1 d . . . . .
H36A H -0.4227 1.6375 -0.1608 0.044 Uiso 1 1 calc R U . . .
C37 C -0.3950(3) 1.7457(8) -0.0980(3) 0.0338(18) Uani 1 1 d . . . . .
H37A H -0.4115 1.8223 -0.1085 0.041 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
I1 Zn1 2.7928(9) . ?
I2 Zn3 2.6288(11) . ?
I3 Zn3 2.6087(10) . ?
Zn1 N4 2.116(6) . ?
Zn1 O2 2.121(5) . ?
Zn1 N6 2.147(5) . ?
Zn1 N5 2.174(6) . ?
Zn1 O1 2.182(4) . ?
Zn2 N7 2.044(5) 7_485 ?
Zn2 N2 2.047(6) . ?
Zn2 N8 2.052(6) 7_485 ?
Zn2 N1 2.146(6) . ?
Zn2 O1 2.235(4) . ?
Zn3 I3 2.6087(10) 2 ?
Zn3 I2 2.6288(11) 2 ?
O1 C14 1.275(8) . ?
O2 C32 1.247(8) . ?
N1 C3 1.340(10) . ?
N1 C1 1.350(10) . ?
N2 C7 1.285(9) . ?
N2 N3 1.376(7) . ?
N3 C14 1.315(9) . ?
N4 C15 1.338(9) . ?
N4 C16 1.350(8) . ?
N5 C24 1.330(9) . ?
N5 C20 1.355(9) . ?
N6 C25 1.285(9) . ?
N6 N7 1.374(7) . ?
N7 C32 1.355(9) . ?
N7 Zn2 2.044(5) 7_485 ?
N8 C37 1.329(9) . ?
N8 C33 1.343(9) . ?
N8 Zn2 2.052(6) 7_485 ?
C1 C6 1.366(11) . ?
C1 C7 1.493(10) . ?
C3 C4 1.383(12) . ?
C4 C5 1.377(14) . ?
C5 C6 1.383(12) . ?
C7 C8 1.483(11) . ?
C8 C13 1.390(12) . ?
C8 C9 1.408(12) . ?
C9 C10 1.382(13) . ?
C10 C11 1.373(15) . ?
C11 C12 1.368(15) . ?
C12 C13 1.381(12) . ?
C14 C15 1.497(9) . ?
C15 C19 1.374(9) . ?
C16 C17 1.388(10) . ?
C17 C18 1.360(11) . ?
C18 C19 1.380(9) . ?
C20 C21 1.378(10) . ?
C20 C25 1.500(10) . ?
C21 C22 1.390(11) . ?
C22 C23 1.360(11) . ?
C23 C24 1.390(10) . ?
C25 C26 1.500(10) . ?
C26 C31 1.380(10) . ?
C26 C27 1.397(10) . ?
C27 C28 1.385(12) . ?
C28 C29 1.377(12) . ?
C29 C30 1.363(11) . ?
C30 C31 1.377(10) . ?
C32 C33 1.515(10) . ?
C33 C34 1.375(10) . ?
C34 C35 1.391(10) . ?
C35 C36 1.366(12) . ?
C36 C37 1.393(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Zn1 O2 119.1(2) . . ?
N4 Zn1 N6 166.8(2) . . ?
O2 Zn1 N6 73.84(19) . . ?
N4 Zn1 N5 92.7(2) . . ?
O2 Zn1 N5 146.58(19) . . ?
N6 Zn1 N5 74.1(2) . . ?
N4 Zn1 O1 77.12(19) . . ?
O2 Zn1 O1 84.85(17) . . ?
N6 Zn1 O1 102.76(18) . . ?
N5 Zn1 O1 93.14(19) . . ?
N4 Zn1 I1 94.60(15) . . ?
O2 Zn1 I1 89.00(13) . . ?
N6 Zn1 I1 88.02(14) . . ?
N5 Zn1 I1 99.16(15) . . ?
O1 Zn1 I1 165.53(12) . . ?
N7 Zn2 N2 163.6(2) 7_485 . ?
N7 Zn2 N8 81.2(2) 7_485 7_485 ?
N2 Zn2 N8 114.8(2) . 7_485 ?
N7 Zn2 N1 103.6(2) 7_485 . ?
N2 Zn2 N1 76.0(2) . . ?
N8 Zn2 N1 107.3(3) 7_485 . ?
N7 Zn2 O1 103.40(19) 7_485 . ?
N2 Zn2 O1 73.91(19) . . ?
N8 Zn2 O1 91.02(19) 7_485 . ?
N1 Zn2 O1 149.3(2) . . ?
I3 Zn3 I3 104.12(6) 2 . ?
I3 Zn3 I2 109.28(2) 2 2 ?
I3 Zn3 I2 113.12(2) . 2 ?
I3 Zn3 I2 113.12(2) 2 . ?
I3 Zn3 I2 109.29(2) . . ?
I2 Zn3 I2 107.99(7) 2 . ?
C14 O1 Zn1 113.5(4) . . ?
C14 O1 Zn2 107.5(4) . . ?
Zn1 O1 Zn2 138.7(2) . . ?
C32 O2 Zn1 112.7(4) . . ?
C3 N1 C1 118.4(7) . . ?
C3 N1 Zn2 126.7(6) . . ?
C1 N1 Zn2 114.8(5) . . ?
C7 N2 N3 119.7(6) . . ?
C7 N2 Zn2 120.3(5) . . ?
N3 N2 Zn2 120.0(4) . . ?
C14 N3 N2 109.4(5) . . ?
C15 N4 C16 118.0(6) . . ?
C15 N4 Zn1 114.6(4) . . ?
C16 N4 Zn1 125.1(5) . . ?
C24 N5 C20 118.0(6) . . ?
C24 N5 Zn1 127.3(5) . . ?
C20 N5 Zn1 114.7(4) . . ?
C25 N6 N7 122.0(6) . . ?
C25 N6 Zn1 119.2(4) . . ?
N7 N6 Zn1 115.5(4) . . ?
C32 N7 N6 109.3(5) . . ?
C32 N7 Zn2 114.1(4) . 7_485 ?
N6 N7 Zn2 136.4(4) . 7_485 ?
C37 N8 C33 118.7(6) . . ?
C37 N8 Zn2 127.0(5) . 7_485 ?
C33 N8 Zn2 114.1(5) . 7_485 ?
N1 C1 C6 122.1(7) . . ?
N1 C1 C7 113.9(7) . . ?
C6 C1 C7 124.0(7) . . ?
N1 C3 C4 122.5(8) . . ?
C5 C4 C3 118.3(8) . . ?
C4 C5 C6 119.5(9) . . ?
C1 C6 C5 119.1(8) . . ?
N2 C7 C8 123.3(6) . . ?
N2 C7 C1 115.0(7) . . ?
C8 C7 C1 121.7(6) . . ?
C13 C8 C9 119.5(8) . . ?
C13 C8 C7 120.1(8) . . ?
C9 C8 C7 120.3(8) . . ?
C10 C9 C8 118.7(9) . . ?
C11 C10 C9 120.6(10) . . ?
C12 C11 C10 121.2(9) . . ?
C11 C12 C13 119.4(10) . . ?
C12 C13 C8 120.5(9) . . ?
O1 C14 N3 128.1(6) . . ?
O1 C14 C15 118.1(6) . . ?
N3 C14 C15 113.8(6) . . ?
N4 C15 C19 122.6(6) . . ?
N4 C15 C14 115.0(6) . . ?
C19 C15 C14 122.3(6) . . ?
N4 C16 C17 121.7(7) . . ?
C18 C17 C16 119.4(6) . . ?
C17 C18 C19 119.0(7) . . ?
C15 C19 C18 119.2(7) . . ?
N5 C20 C21 122.1(7) . . ?
N5 C20 C25 116.0(6) . . ?
C21 C20 C25 121.8(6) . . ?
C20 C21 C22 118.7(7) . . ?
C23 C22 C21 119.6(7) . . ?
C22 C23 C24 118.6(7) . . ?
N5 C24 C23 123.0(7) . . ?
N6 C25 C20 113.1(6) . . ?
N6 C25 C26 126.9(6) . . ?
C20 C25 C26 120.0(6) . . ?
C31 C26 C27 120.3(7) . . ?
C31 C26 C25 120.6(6) . . ?
C27 C26 C25 119.1(6) . . ?
C28 C27 C26 118.9(7) . . ?
C29 C28 C27 120.3(7) . . ?
C30 C29 C28 120.2(8) . . ?
C29 C30 C31 120.9(7) . . ?
C30 C31 C26 119.4(7) . . ?
O2 C32 N7 126.3(6) . . ?
O2 C32 C33 118.8(6) . . ?
N7 C32 C33 114.9(6) . . ?
N8 C33 C34 123.5(7) . . ?
N8 C33 C32 115.4(6) . . ?
C34 C33 C32 121.1(6) . . ?
C33 C34 C35 117.3(7) . . ?
C36 C35 C34 119.7(8) . . ?
C35 C36 C37 119.5(7) . . ?
N8 C37 C36 121.4(7) . . ?

_refine_diff_density_max         2.058
_refine_diff_density_min         -2.637
_refine_diff_density_rms         0.156

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_193a
_database_code_depnum_ccdc_archive 'CCDC 1524914'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 Br2 N4 O Zn'
_chemical_formula_sum            'C12 H10 Br2 N4 O Zn'
_chemical_formula_weight         451.43

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.6877(14)
_cell_length_b                   10.3625(19)
_cell_length_c                   18.182(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.183(2)
_cell_angle_gamma                90.00
_cell_volume                     1448.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2749
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.37

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.071
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    7.214
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.1605
_exptl_absorpt_correction_T_max  0.7143
_exptl_absorpt_process_details   'Bruker SADABS, 2010'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7344
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2540
_reflns_number_gt                2128
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0468P)²+1.9924P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2540
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.48831(6) 0.28346(5) 0.41075(3) 0.02472(16) Uani 1 1 d . . .
Zn1 Zn 0.75387(7) 0.21066(5) 0.46492(3) 0.02115(17) Uani 1 1 d . . .
Br2 Br 1.00942(7) 0.32212(5) 0.43325(3) 0.02860(17) Uani 1 1 d . . .
O1 O 0.7941(5) 0.0418(3) 0.38335(19) 0.0300(9) Uani 1 1 d . . .
N1 N 0.7239(5) 0.2643(4) 0.5779(2) 0.0199(9) Uani 1 1 d . . .
N2 N 0.7466(5) 0.0338(4) 0.5231(2) 0.0224(9) Uani 1 1 d . . .
C17 C 0.7444(6) -0.3063(5) 0.3916(3) 0.0212(11) Uani 1 1 d . . .
H17 H 0.6950 -0.3149 0.4388 0.025 Uiso 1 1 calc R . .
N4 N 0.8281(6) -0.4050(4) 0.2782(2) 0.0284(10) Uani 1 1 d . . .
N3 N 0.7658(5) -0.0782(4) 0.4854(2) 0.0242(10) Uani 1 1 d . . .
H9 H 0.7635 -0.1540 0.5072 0.029 Uiso 1 1 calc R . .
C13 C 0.8775(7) -0.1781(5) 0.2987(3) 0.0272(12) Uani 1 1 d . . .
H13 H 0.9205 -0.0984 0.2807 0.033 Uiso 1 1 calc R . .
C16 C 0.7586(7) -0.4119(5) 0.3455(3) 0.0267(12) Uani 1 1 d . . .
H16 H 0.7174 -0.4931 0.3622 0.032 Uiso 1 1 calc R . .
C6 C 0.7047(6) 0.1650(5) 0.6251(3) 0.0211(11) Uani 1 1 d . . .
C10 C 0.7890(6) -0.0655(5) 0.4111(3) 0.0219(11) Uani 1 1 d . . .
C5 C 0.6743(7) 0.1841(5) 0.6987(3) 0.0284(12) Uani 1 1 d . . .
H5 H 0.6625 0.1126 0.7309 0.034 Uiso 1 1 calc R . .
C2 C 0.7150(7) 0.3843(5) 0.6038(3) 0.0271(12) Uani 1 1 d . . .
H2 H 0.7311 0.4544 0.5710 0.033 Uiso 1 1 calc R . .
C12 C 0.8047(6) -0.1861(5) 0.3672(3) 0.0209(11) Uani 1 1 d . . .
C14 C 0.8862(8) -0.2910(5) 0.2563(3) 0.0302(13) Uani 1 1 d . . .
H14 H 0.9367 -0.2854 0.2092 0.036 Uiso 1 1 calc R . .
C4 C 0.6609(7) 0.3104(5) 0.7253(3) 0.0310(13) Uani 1 1 d . . .
H4 H 0.6372 0.3262 0.7756 0.037 Uiso 1 1 calc R . .
C3 C 0.6829(7) 0.4107(5) 0.6774(3) 0.0297(12) Uani 1 1 d . . .
H3 H 0.6762 0.4973 0.6941 0.036 Uiso 1 1 calc R . .
C7 C 0.7239(7) 0.0362(5) 0.5929(3) 0.0257(12) Uani 1 1 d . . .
H7 H 0.7197 -0.0402 0.6217 0.031 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.3716(8) . ?
Zn1 N2 2.117(4) . ?
Zn1 N1 2.144(4) . ?
Zn1 O1 2.319(4) . ?
Zn1 Br2 2.3605(9) . ?
O1 C10 1.222(6) . ?
N1 C2 1.333(6) . ?
N1 C6 1.350(6) . ?
N2 C7 1.286(6) . ?
N2 N3 1.357(6) . ?
C17 C16 1.384(7) . ?
C17 C12 1.404(7) . ?
C17 H17 0.9500 . ?
N4 C14 1.327(7) . ?
N4 C16 1.348(7) . ?
N3 C10 1.371(6) . ?
N3 H9 0.8800 . ?
C13 C12 1.378(7) . ?
C13 C14 1.403(7) . ?
C13 H13 0.9500 . ?
C16 H16 0.9500 . ?
C6 C5 1.378(7) . ?
C6 C7 1.466(7) . ?
C10 C12 1.490(7) . ?
C5 C4 1.401(7) . ?
C5 H5 0.9500 . ?
C2 C3 1.392(7) . ?
C2 H2 0.9500 . ?
C14 H14 0.9500 . ?
C4 C3 1.369(8) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C7 H7 0.9500 . ?

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 75.04(16) . . ?
N2 Zn1 O1 70.80(14) . . ?
N1 Zn1 O1 145.73(14) . . ?
N2 Zn1 Br2 125.17(11) . . ?
N1 Zn1 Br2 102.32(11) . . ?
O1 Zn1 Br2 95.20(10) . . ?
N2 Zn1 Br1 116.84(11) . . ?
N1 Zn1 Br1 101.93(11) . . ?
O1 Zn1 Br1 95.71(9) . . ?
Br2 Zn1 Br1 117.17(3) . . ?
C10 O1 Zn1 114.6(3) . . ?
C2 N1 C6 118.6(4) . . ?
C2 N1 Zn1 126.0(3) . . ?
C6 N1 Zn1 115.3(3) . . ?
C7 N2 N3 122.2(4) . . ?
C7 N2 Zn1 118.8(3) . . ?
N3 N2 Zn1 119.0(3) . . ?
C16 C17 C12 118.7(5) . . ?
C16 C17 H17 120.7 . . ?
C12 C17 H17 120.7 . . ?
C14 N4 C16 117.4(4) . . ?
N2 N3 C10 115.6(4) . . ?
N2 N3 H9 122.2 . . ?
C10 N3 H9 122.2 . . ?
C12 C13 C14 118.1(5) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
N4 C16 C17 123.0(5) . . ?
N4 C16 H16 118.5 . . ?
C17 C16 H16 118.5 . . ?
N1 C6 C5 122.1(5) . . ?
N1 C6 C7 115.3(4) . . ?
C5 C6 C7 122.6(5) . . ?
O1 C10 N3 120.0(4) . . ?
O1 C10 C12 122.5(4) . . ?
N3 C10 C12 117.5(4) . . ?
C6 C5 C4 119.1(5) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
N1 C2 C3 122.4(5) . . ?
N1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C13 C12 C17 118.8(5) . . ?
C13 C12 C10 118.2(5) . . ?
C17 C12 C10 122.9(4) . . ?
N4 C14 C13 124.0(5) . . ?
N4 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
C3 C4 C5 118.5(5) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
N2 C7 C6 115.4(4) . . ?
N2 C7 H7 122.3 . . ?
C6 C7 H7 122.3 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.140
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1524920'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Br2 N4 O Zn'
_chemical_formula_sum            'C18 H14 Br2 N4 O Zn'
_chemical_formula_weight         527.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.1458(6)
_cell_length_b                   11.7060(9)
_cell_length_c                   18.2478(12)
_cell_angle_alpha                80.629(9)
_cell_angle_beta                 77.512(8)
_cell_angle_gamma                88.044(9)
_cell_volume                     1881.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    5.566
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2143
_exptl_absorpt_correction_T_max  0.3048
_exptl_absorpt_process_details   'Walker, N. & Stuart, D. (1983)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18385
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             8410
_reflns_number_gt                5762
_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       'STOE IPDS software'
_computing_cell_refinement       'STOE IPDS software'
_computing_data_reduction        'STOE IPDS software, STOE S-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0272P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8410
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_restrained_S_all      0.826
_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 0.08195(3) 0.26244(3) 0.01210(2) 0.03064(8) Uani 1 1 d . . . . .
Br1 Br 0.19921(3) 0.13434(3) 0.09683(2) 0.03982(8) Uani 1 1 d . . . . .
Br2 Br 0.15254(4) 0.25759(3) -0.11836(2) 0.04559(9) Uani 1 1 d . . . . .
O1 O 0.2315(2) 0.42940(18) 0.00956(12) 0.0374(5) Uani 1 1 d . . . . .
N1 N -0.1419(2) 0.1951(2) 0.04440(14) 0.0308(6) Uani 1 1 d . . . . .
N2 N -0.0380(2) 0.3721(2) 0.08601(13) 0.0274(5) Uani 1 1 d . . . . .
N3 N 0.0359(2) 0.4595(2) 0.10330(13) 0.0303(6) Uani 1 1 d . . . . .
H3 H -0.0042 0.4979 0.1390 0.036 Uiso 1 1 calc R U . . .
N4 N 0.1944(3) 0.6111(2) 0.14958(14) 0.0346(6) Uani 1 1 d . . . . .
C1 C -0.1902(3) 0.1046(3) 0.02088(19) 0.0393(8) Uani 1 1 d . . . . .
H1 H -0.1305 0.0758 -0.0201 0.047 Uiso 1 1 calc R U . . .
C2 C -0.3271(3) 0.0515(3) 0.0555(2) 0.0419(8) Uani 1 1 d . . . . .
H2 H -0.3577 -0.0124 0.0383 0.050 Uiso 1 1 calc R U . . .
C3 C -0.4159(3) 0.0946(3) 0.11516(19) 0.0378(8) Uani 1 1 d . . . . .
H3A H -0.5079 0.0605 0.1390 0.045 Uiso 1 1 calc R U . . .
C4 C -0.3673(3) 0.1896(3) 0.13982(17) 0.0331(7) Uani 1 1 d . . . . .
H4 H -0.4261 0.2202 0.1803 0.040 Uiso 1 1 calc R U . . .
C5 C -0.2296(3) 0.2380(3) 0.10310(16) 0.0286(6) Uani 1 1 d . . . . .
C6 C -0.1666(3) 0.3373(2) 0.12678(16) 0.0272(6) Uani 1 1 d . . . . .
C7 C -0.2430(3) 0.3834(2) 0.19641(17) 0.0303(7) Uani 1 1 d . . . . .
C8 C -0.1944(4) 0.3456(3) 0.26263(18) 0.0411(8) Uani 1 1 d . . . . .
H8 H -0.1136 0.2949 0.2618 0.049 Uiso 1 1 calc R U . . .
C9 C -0.2635(4) 0.3816(3) 0.3303(2) 0.0497(9) Uani 1 1 d . . . . .
H9 H -0.2300 0.3563 0.3749 0.060 Uiso 1 1 calc R U . . .
C10 C -0.3834(4) 0.4562(3) 0.3298(2) 0.0555(11) Uani 1 1 d . . . . .
H10 H -0.4328 0.4801 0.3749 0.067 Uiso 1 1 calc R U . . .
C11 C -0.4306(4) 0.4954(3) 0.2648(2) 0.0577(11) Uani 1 1 d . . . . .
H11 H -0.5109 0.5464 0.2660 0.069 Uiso 1 1 calc R U . . .
C12 C -0.3610(4) 0.4607(3) 0.1960(2) 0.0485(9) Uani 1 1 d . . . . .
H12 H -0.3929 0.4885 0.1514 0.058 Uiso 1 1 calc R U . . .
C13 C 0.1764(3) 0.4832(2) 0.06118(16) 0.0279(6) Uani 1 1 d . . . . .
C14 C 0.2565(3) 0.5759(2) 0.08345(16) 0.0270(6) Uani 1 1 d . . . . .
C15 C 0.3889(3) 0.6202(3) 0.03677(18) 0.0329(7) Uani 1 1 d . . . . .
H15 H 0.4277 0.5932 -0.0087 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4622(3) 0.7052(3) 0.05907(19) 0.0397(8) Uani 1 1 d . . . . .
H16 H 0.5511 0.7372 0.0288 0.048 Uiso 1 1 calc R U . . .
C17 C 0.4011(4) 0.7419(3) 0.1272(2) 0.0436(8) Uani 1 1 d . . . . .
H17 H 0.4487 0.7982 0.1442 0.052 Uiso 1 1 calc R U . . .
C18 C 0.2679(4) 0.6933(3) 0.16988(19) 0.0436(8) Uani 1 1 d . . . . .
H18 H 0.2269 0.7194 0.2154 0.052 Uiso 1 1 calc R U . . .
Zn2 Zn 0.54070(3) 0.21108(3) 0.58518(2) 0.02901(8) Uani 1 1 d . . . . .
Br3 Br 0.68665(4) 0.38183(3) 0.53566(2) 0.04140(9) Uani 1 1 d . . . . .
Br4 Br 0.56743(4) 0.11671(3) 0.70588(2) 0.04402(9) Uani 1 1 d . . . . .
O2 O 0.7052(2) 0.09199(19) 0.51610(12) 0.0361(5) Uani 1 1 d . . . . .
N5 N 0.3129(2) 0.26701(19) 0.60548(13) 0.0257(5) Uani 1 1 d . . . . .
N6 N 0.4542(2) 0.1818(2) 0.48902(13) 0.0266(5) Uani 1 1 d . . . . .
N7 N 0.5537(2) 0.1386(2) 0.43323(13) 0.0288(5) Uani 1 1 d . . . . .
H7 H 0.5365 0.1398 0.3886 0.035 Uiso 1 1 calc R U . . .
N8 N 0.7401(3) 0.0538(2) 0.32409(15) 0.0388(6) Uani 1 1 d . . . . .
C19 C 0.2393(3) 0.2969(3) 0.67098(17) 0.0315(7) Uani 1 1 d . . . . .
H19 H 0.2863 0.2885 0.7119 0.038 Uiso 1 1 calc R U . . .
C20 C 0.0941(3) 0.3404(3) 0.67980(18) 0.0365(7) Uani 1 1 d . . . . .
H20 H 0.0452 0.3620 0.7257 0.044 Uiso 1 1 calc R U . . .
C21 C 0.0246(3) 0.3509(3) 0.61974(19) 0.0401(8) Uani 1 1 d . . . . .
H21 H -0.0720 0.3806 0.6245 0.048 Uiso 1 1 calc R U . . .
C22 C 0.0984(3) 0.3173(3) 0.55173(18) 0.0341(7) Uani 1 1 d . . . . .
H22 H 0.0517 0.3223 0.5108 0.041 Uiso 1 1 calc R U . . .
C23 C 0.2446(3) 0.2758(2) 0.54642(16) 0.0253(6) Uani 1 1 d . . . . .
C24 C 0.3325(3) 0.2335(2) 0.47702(15) 0.0250(6) Uani 1 1 d . . . . .
C25 C 0.2840(3) 0.2524(2) 0.40380(16) 0.0269(6) Uani 1 1 d . . . . .
C26 C 0.2867(3) 0.1622(3) 0.36187(16) 0.0303(6) Uani 1 1 d . . . . .
H26 H 0.3118 0.0876 0.3817 0.036 Uiso 1 1 calc R U . . .
C27 C 0.2520(3) 0.1845(3) 0.29065(17) 0.0340(7) Uani 1 1 d . . . . .
H27 H 0.2556 0.1248 0.2623 0.041 Uiso 1 1 calc R U . . .
C28 C 0.2122(4) 0.2936(3) 0.26155(18) 0.0405(8) Uani 1 1 d . . . . .
H28 H 0.1904 0.3079 0.2134 0.049 Uiso 1 1 calc R U . . .
C29 C 0.2046(4) 0.3823(3) 0.30372(19) 0.0436(8) Uani 1 1 d . . . . .
H29 H 0.1747 0.4557 0.2844 0.052 Uiso 1 1 calc R U . . .
C30 C 0.2408(3) 0.3629(3) 0.37434(18) 0.0361(7) Uani 1 1 d . . . . .
H30 H 0.2365 0.4233 0.4022 0.043 Uiso 1 1 calc R U . . .
C31 C 0.6812(3) 0.0936(2) 0.45230(17) 0.0286(6) Uani 1 1 d . . . . .
C32 C 0.7853(3) 0.0456(2) 0.38980(17) 0.0286(6) Uani 1 1 d . . . . .
C33 C 0.9174(3) -0.0042(3) 0.4019(2) 0.0413(8) Uani 1 1 d . . . . .
H33 H 0.9439 -0.0082 0.4487 0.050 Uiso 1 1 calc R U . . .
C34 C 1.0109(3) -0.0488(3) 0.3426(2) 0.0489(9) Uani 1 1 d . . . . .
H34 H 1.1019 -0.0828 0.3485 0.059 Uiso 1 1 calc R U . . .
C35 C 0.9653(4) -0.0412(3) 0.2751(2) 0.0486(9) Uani 1 1 d . . . . .
H35 H 1.0255 -0.0698 0.2341 0.058 Uiso 1 1 calc R U . . .
C36 C 0.8303(4) 0.0089(3) 0.26880(19) 0.0491(9) Uani 1 1 d . . . . .
H36 H 0.8001 0.0117 0.2231 0.059 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 2.121(2) . ?
Zn1 N1 2.144(2) . ?
Zn1 Br2 2.3374(5) . ?
Zn1 Br1 2.3752(6) . ?
Zn1 O1 2.412(2) . ?
O1 C13 1.226(3) . ?
N1 C1 1.328(4) . ?
N1 C5 1.349(3) . ?
N2 C6 1.288(3) . ?
N2 N3 1.360(3) . ?
N3 C13 1.359(3) . ?
N3 H3 0.8600 . ?
N4 C18 1.336(4) . ?
N4 C14 1.341(3) . ?
C1 C2 1.391(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.478(4) . ?
C6 C7 1.486(4) . ?
C7 C8 1.378(5) . ?
C7 C12 1.385(4) . ?
C8 C9 1.385(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.486(4) . ?
C14 C15 1.383(4) . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
Zn2 N5 2.135(2) . ?
Zn2 N6 2.153(2) . ?
Zn2 O2 2.3249(19) . ?
Zn2 Br4 2.3566(5) . ?
Zn2 Br3 2.3803(5) . ?
O2 C31 1.228(3) . ?
N5 C19 1.333(3) . ?
N5 C23 1.346(4) . ?
N6 C24 1.291(4) . ?
N6 N7 1.363(3) . ?
N7 C31 1.354(4) . ?
N7 H7 0.8600 . ?
N8 C36 1.326(4) . ?
N8 C32 1.339(4) . ?
C19 C20 1.392(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.389(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.395(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.495(3) . ?
C24 C25 1.478(4) . ?
C25 C30 1.396(4) . ?
C25 C26 1.398(4) . ?
C26 C27 1.386(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.370(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.381(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.381(5) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.491(4) . ?
C32 C33 1.369(4) . ?
C33 C34 1.388(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.373(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.368(5) . ?
C35 H35 0.9300 . ?
C36 H36 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 74.92(8) . . ?
N2 Zn1 Br2 138.59(7) . . ?
N1 Zn1 Br2 104.53(7) . . ?
N2 Zn1 Br1 101.14(7) . . ?
N1 Zn1 Br1 100.37(7) . . ?
Br2 Zn1 Br1 119.189(19) . . ?
N2 Zn1 O1 69.86(7) . . ?
N1 Zn1 O1 143.40(8) . . ?
Br2 Zn1 O1 95.55(5) . . ?
Br1 Zn1 O1 95.86(6) . . ?
C13 O1 Zn1 111.26(17) . . ?
C1 N1 C5 118.8(2) . . ?
C1 N1 Zn1 125.64(19) . . ?
C5 N1 Zn1 114.48(18) . . ?
C6 N2 N3 120.8(2) . . ?
C6 N2 Zn1 117.97(18) . . ?
N3 N2 Zn1 119.08(15) . . ?
C13 N3 N2 116.4(2) . . ?
C13 N3 H3 121.8 . . ?
N2 N3 H3 121.8 . . ?
C18 N4 C14 116.4(2) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 115.5(2) . . ?
C4 C5 C6 122.6(2) . . ?
N2 C6 C5 114.5(2) . . ?
N2 C6 C7 124.4(2) . . ?
C5 C6 C7 120.9(2) . . ?
C8 C7 C12 120.3(3) . . ?
C8 C7 C6 117.9(3) . . ?
C12 C7 C6 121.8(3) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 118.0(4) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 121.3(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C11 117.9(4) . . ?
C7 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
O1 C13 N3 121.3(3) . . ?
O1 C13 C14 123.6(2) . . ?
N3 C13 C14 115.1(2) . . ?
N4 C14 C15 123.7(3) . . ?
N4 C14 C13 116.6(2) . . ?
C15 C14 C13 119.7(2) . . ?
C16 C15 C14 118.6(3) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C17 C16 C15 118.6(3) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N4 C18 C17 123.9(3) . . ?
N4 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
N5 Zn2 N6 73.57(8) . . ?
N5 Zn2 O2 142.01(8) . . ?
N6 Zn2 O2 70.98(8) . . ?
N5 Zn2 Br4 103.06(7) . . ?
N6 Zn2 Br4 140.76(7) . . ?
O2 Zn2 Br4 95.87(6) . . ?
N5 Zn2 Br3 105.77(6) . . ?
N6 Zn2 Br3 102.36(6) . . ?
O2 Zn2 Br3 94.80(6) . . ?
Br4 Zn2 Br3 115.762(19) . . ?
C31 O2 Zn2 111.90(18) . . ?
C19 N5 C23 119.6(2) . . ?
C19 N5 Zn2 124.0(2) . . ?
C23 N5 Zn2 116.33(16) . . ?
C24 N6 N7 122.2(2) . . ?
C24 N6 Zn2 119.14(17) . . ?
N7 N6 Zn2 115.72(17) . . ?
C31 N7 N6 116.0(2) . . ?
C31 N7 H7 122.0 . . ?
N6 N7 H7 122.0 . . ?
C36 N8 C32 116.5(3) . . ?
N5 C19 C20 121.8(3) . . ?
N5 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C21 C20 C19 118.8(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 118.2(3) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
N5 C23 C22 121.5(2) . . ?
N5 C23 C24 115.7(2) . . ?
C22 C23 C24 122.7(3) . . ?
N6 C24 C25 125.4(2) . . ?
N6 C24 C23 112.0(2) . . ?
C25 C24 C23 122.6(2) . . ?
C30 C25 C26 119.3(3) . . ?
C30 C25 C24 119.7(2) . . ?
C26 C25 C24 120.9(3) . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C28 C27 C26 120.6(3) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 120.6(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C25 119.7(3) . . ?
C29 C30 H30 120.1 . . ?
C25 C30 H30 120.1 . . ?
O2 C31 N7 121.8(2) . . ?
O2 C31 C32 124.3(3) . . ?
N7 C31 C32 114.0(3) . . ?
N8 C32 C33 124.0(3) . . ?
N8 C32 C31 116.1(3) . . ?
C33 C32 C31 119.9(3) . . ?
C32 C33 C34 118.3(3) . . ?
C32 C33 H33 120.9 . . ?
C34 C33 H33 120.9 . . ?
C35 C34 C33 118.2(3) . . ?
C35 C34 H34 120.9 . . ?
C33 C34 H34 120.9 . . ?
C36 C35 C34 119.2(3) . . ?
C36 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
N8 C36 C35 123.9(4) . . ?
N8 C36 H36 118.1 . . ?
C35 C36 H36 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 N3 C13 174.3(3) . . . . ?
Zn1 N2 N3 C13 11.3(3) . . . . ?
C5 N1 C1 C2 -1.0(5) . . . . ?
Zn1 N1 C1 C2 166.6(3) . . . . ?
N1 C1 C2 C3 0.8(5) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C1 N1 C5 C4 0.7(5) . . . . ?
Zn1 N1 C5 C4 -168.3(2) . . . . ?
C1 N1 C5 C6 178.9(3) . . . . ?
Zn1 N1 C5 C6 9.9(3) . . . . ?
C3 C4 C5 N1 -0.2(5) . . . . ?
C3 C4 C5 C6 -178.2(3) . . . . ?
N3 N2 C6 C5 -177.2(2) . . . . ?
Zn1 N2 C6 C5 -14.1(3) . . . . ?
N3 N2 C6 C7 -2.6(4) . . . . ?
Zn1 N2 C6 C7 160.6(2) . . . . ?
N1 C5 C6 N2 2.4(4) . . . . ?
C4 C5 C6 N2 -179.5(3) . . . . ?
N1 C5 C6 C7 -172.4(3) . . . . ?
C4 C5 C6 C7 5.7(4) . . . . ?
N2 C6 C7 C8 -77.9(4) . . . . ?
C5 C6 C7 C8 96.4(3) . . . . ?
N2 C6 C7 C12 103.0(4) . . . . ?
C5 C6 C7 C12 -82.6(4) . . . . ?
C12 C7 C8 C9 1.3(5) . . . . ?
C6 C7 C8 C9 -177.7(3) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C8 C9 C10 C11 -1.5(5) . . . . ?
C9 C10 C11 C12 0.9(6) . . . . ?
C8 C7 C12 C11 -1.9(5) . . . . ?
C6 C7 C12 C11 177.1(3) . . . . ?
C10 C11 C12 C7 0.9(6) . . . . ?
Zn1 O1 C13 N3 -11.0(3) . . . . ?
Zn1 O1 C13 C14 167.8(2) . . . . ?
N2 N3 C13 O1 1.3(4) . . . . ?
N2 N3 C13 C14 -177.6(3) . . . . ?
C18 N4 C14 C15 -0.3(5) . . . . ?
C18 N4 C14 C13 179.1(3) . . . . ?
O1 C13 C14 N4 -167.4(3) . . . . ?
N3 C13 C14 N4 11.5(4) . . . . ?
O1 C13 C14 C15 12.0(5) . . . . ?
N3 C13 C14 C15 -169.1(3) . . . . ?
N4 C14 C15 C16 0.1(5) . . . . ?
C13 C14 C15 C16 -179.2(3) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C15 C16 C17 C18 -1.0(5) . . . . ?
C14 N4 C18 C17 -0.2(5) . . . . ?
C16 C17 C18 N4 0.9(6) . . . . ?
C24 N6 N7 C31 175.7(2) . . . . ?
Zn2 N6 N7 C31 15.3(3) . . . . ?
C23 N5 C19 C20 -1.8(4) . . . . ?
Zn2 N5 C19 C20 175.5(2) . . . . ?
N5 C19 C20 C21 1.0(5) . . . . ?
C19 C20 C21 C22 0.6(5) . . . . ?
C20 C21 C22 C23 -1.5(5) . . . . ?
C19 N5 C23 C22 0.9(4) . . . . ?
Zn2 N5 C23 C22 -176.6(2) . . . . ?
C19 N5 C23 C24 -176.4(2) . . . . ?
Zn2 N5 C23 C24 6.1(3) . . . . ?
C21 C22 C23 N5 0.8(4) . . . . ?
C21 C22 C23 C24 177.8(3) . . . . ?
N7 N6 C24 C25 0.3(4) . . . . ?
Zn2 N6 C24 C25 160.0(2) . . . . ?
N7 N6 C24 C23 -178.4(2) . . . . ?
Zn2 N6 C24 C23 -18.7(3) . . . . ?
N5 C23 C24 N6 7.9(3) . . . . ?
C22 C23 C24 N6 -169.3(3) . . . . ?
N5 C23 C24 C25 -170.8(2) . . . . ?
C22 C23 C24 C25 12.0(4) . . . . ?
N6 C24 C25 C30 -129.6(3) . . . . ?
C23 C24 C25 C30 49.0(4) . . . . ?
N6 C24 C25 C26 47.7(4) . . . . ?
C23 C24 C25 C26 -133.8(3) . . . . ?
C30 C25 C26 C27 2.3(4) . . . . ?
C24 C25 C26 C27 -174.9(3) . . . . ?
C25 C26 C27 C28 -1.2(4) . . . . ?
C26 C27 C28 C29 -0.9(5) . . . . ?
C27 C28 C29 C30 1.9(5) . . . . ?
C28 C29 C30 C25 -0.7(5) . . . . ?
C26 C25 C30 C29 -1.3(4) . . . . ?
C24 C25 C30 C29 175.9(3) . . . . ?
Zn2 O2 C31 N7 -13.8(3) . . . . ?
Zn2 O2 C31 C32 167.3(2) . . . . ?
N6 N7 C31 O2 0.0(4) . . . . ?
N6 N7 C31 C32 179.1(2) . . . . ?
C36 N8 C32 C33 0.8(5) . . . . ?
C36 N8 C32 C31 -178.4(3) . . . . ?
O2 C31 C32 N8 179.3(3) . . . . ?
N7 C31 C32 N8 0.3(4) . . . . ?
O2 C31 C32 C33 0.1(4) . . . . ?
N7 C31 C32 C33 -179.0(3) . . . . ?
N8 C32 C33 C34 0.3(5) . . . . ?
C31 C32 C33 C34 179.5(3) . . . . ?
C32 C33 C34 C35 -0.5(5) . . . . ?
C33 C34 C35 C36 -0.3(5) . . . . ?
C32 N8 C36 C35 -1.7(5) . . . . ?
C34 C35 C36 N8 1.5(6) . . . . ?


_refine_diff_density_max         0.550
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-4

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1524918'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.939 Note
RESPONSE: The reason for the low fraction of measured reflections is 
the data collection on a STOE IPDS-I diffractometer (rotation of the
crystal around the vertical omega axis only).
;
# end Validation Reply Formend Validation Reply Form


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl2 N4 O Zn '
_chemical_formula_sum            'C18 H14 Cl2 N4 O Zn'
_chemical_formula_weight         438.60

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

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

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

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

_cell_length_a                   9.0285(6)
_cell_length_b                   11.7143(8)
_cell_length_c                   17.5898(11)
_cell_angle_alpha                82.781(8)
_cell_angle_beta                 78.436(5)
_cell_angle_gamma                88.107(8)
_cell_volume                     1808.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    6613
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      28.0

_exptl_crystal_description       'block (fragment)'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.669
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4605
_exptl_absorpt_correction_T_max  0.5928
_exptl_absorpt_process_details   'Walker, N. & Stuart, D. (1983)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS-1'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21321
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.780
_diffrn_reflns_theta_max         28.133
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.939
_reflns_number_total             8108
_reflns_number_gt                6437
_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       'STOE IPDS software'
_computing_cell_refinement       'STOE IPDS software'
_computing_data_reduction        'STOE IPDS software, STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0491P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8108
_refine_ls_number_parameters     477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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
C1 C -0.1923(2) 0.1049(2) 0.02202(12) 0.0383(5) Uani 1 1 d . . . . .
H1 H -0.1327 0.0737 -0.0200 0.046 Uiso 1 1 calc R U . . .
C2 C -0.3301(3) 0.0548(2) 0.05602(13) 0.0427(5) Uani 1 1 d . . . . .
H2 H -0.3620 -0.0094 0.0377 0.051 Uiso 1 1 calc R U . . .
C3 C -0.4187(2) 0.1018(2) 0.11758(13) 0.0400(5) Uani 1 1 d . . . . .
H3 H -0.5120 0.0699 0.1413 0.048 Uiso 1 1 calc R U . . .
C4 C -0.3685(2) 0.1968(2) 0.14409(11) 0.0339(4) Uani 1 1 d . . . . .
H4 H -0.4273 0.2296 0.1856 0.041 Uiso 1 1 calc R U . . .
C5 C -0.2287(2) 0.24209(18) 0.10742(10) 0.0284(4) Uani 1 1 d . . . . .
C6 C -0.1640(2) 0.34156(18) 0.13231(10) 0.0282(4) Uani 1 1 d . . . . .
C7 C -0.2375(2) 0.38977(19) 0.20530(11) 0.0317(4) Uani 1 1 d . . . . .
C8 C -0.1898(3) 0.3478(2) 0.27342(12) 0.0411(5) Uani 1 1 d . . . . .
H8 H -0.1111 0.2943 0.2721 0.049 Uiso 1 1 calc R U . . .
C9 C -0.2592(3) 0.3852(2) 0.34380(13) 0.0504(6) Uani 1 1 d . . . . .
H9 H -0.2262 0.3578 0.3896 0.060 Uiso 1 1 calc R U . . .
C10 C -0.3762(3) 0.4625(3) 0.34551(14) 0.0543(7) Uani 1 1 d . . . . .
H10 H -0.4250 0.4858 0.3929 0.065 Uiso 1 1 calc R U . . .
C11 C -0.4221(3) 0.5058(3) 0.27795(16) 0.0550(7) Uani 1 1 d . . . . .
H11 H -0.5005 0.5595 0.2797 0.066 Uiso 1 1 calc R U . . .
C12 C -0.3528(3) 0.4704(2) 0.20656(14) 0.0444(5) Uani 1 1 d . . . . .
H12 H -0.3836 0.5004 0.1607 0.053 Uiso 1 1 calc R U . . .
C13 C 0.1788(2) 0.48702(18) 0.06387(10) 0.0288(4) Uani 1 1 d . . . . .
C14 C 0.2605(2) 0.58077(18) 0.08629(10) 0.0281(4) Uani 1 1 d . . . . .
C15 C 0.3923(2) 0.62366(19) 0.03801(11) 0.0325(4) Uani 1 1 d . . . . .
H15 H 0.4289 0.5953 -0.0093 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4683(2) 0.7089(2) 0.06122(13) 0.0409(5) Uani 1 1 d . . . . .
H16 H 0.5568 0.7396 0.0297 0.049 Uiso 1 1 calc R U . . .
C17 C 0.4110(3) 0.7480(2) 0.13188(13) 0.0443(5) Uani 1 1 d . . . . .
H17 H 0.4601 0.8053 0.1492 0.053 Uiso 1 1 calc R U . . .
C18 C 0.2785(3) 0.7002(2) 0.17673(12) 0.0430(5) Uani 1 1 d . . . . .
H18 H 0.2408 0.7267 0.2246 0.052 Uiso 1 1 calc R U . . .
C19 C 0.2377(2) 0.2825(2) 0.68010(11) 0.0332(4) Uani 1 1 d . . . . .
H19 H 0.2806 0.2674 0.7242 0.040 Uiso 1 1 calc R U . . .
C20 C 0.0946(2) 0.3320(2) 0.68776(11) 0.0371(5) Uani 1 1 d . . . . .
H20 H 0.0434 0.3513 0.7359 0.045 Uiso 1 1 calc R U . . .
C21 C 0.0302(2) 0.3520(2) 0.62299(12) 0.0415(5) Uani 1 1 d . . . . .
H21 H -0.0652 0.3858 0.6265 0.050 Uiso 1 1 calc R U . . .
C22 C 0.1087(2) 0.3210(2) 0.55197(11) 0.0361(5) Uani 1 1 d . . . . .
H22 H 0.0658 0.3321 0.5077 0.043 Uiso 1 1 calc R U . . .
C23 C 0.2515(2) 0.27352(18) 0.54851(10) 0.0278(4) Uani 1 1 d . . . . .
C24 C 0.3431(2) 0.23201(17) 0.47678(10) 0.0268(4) Uani 1 1 d . . . . .
C25 C 0.2951(2) 0.25436(18) 0.40035(10) 0.0274(4) Uani 1 1 d . . . . .
C26 C 0.2895(2) 0.16434(19) 0.35619(10) 0.0316(4) Uani 1 1 d . . . . .
H26 H 0.3100 0.0893 0.3758 0.038 Uiso 1 1 calc R U . . .
C27 C 0.2534(2) 0.1872(2) 0.28312(11) 0.0372(5) Uani 1 1 d . . . . .
H27 H 0.2507 0.1276 0.2532 0.045 Uiso 1 1 calc R U . . .
C28 C 0.2216(3) 0.2976(2) 0.25458(11) 0.0420(5) Uani 1 1 d . . . . .
H28 H 0.1993 0.3127 0.2049 0.050 Uiso 1 1 calc R U . . .
C29 C 0.2224(3) 0.3864(2) 0.29901(12) 0.0454(6) Uani 1 1 d . . . . .
H29 H 0.1975 0.4606 0.2799 0.054 Uiso 1 1 calc R U . . .
C30 C 0.2600(3) 0.3654(2) 0.37194(12) 0.0386(5) Uani 1 1 d . . . . .
H30 H 0.2617 0.4254 0.4017 0.046 Uiso 1 1 calc R U . . .
C31 C 0.6911(2) 0.08685(18) 0.45035(10) 0.0285(4) Uani 1 1 d . . . . .
C32 C 0.7985(2) 0.04087(18) 0.38527(10) 0.0297(4) Uani 1 1 d . . . . .
C33 C 0.9276(2) -0.0156(2) 0.39936(13) 0.0407(5) Uani 1 1 d . . . . .
H33 H 0.9493 -0.0258 0.4493 0.049 Uiso 1 1 calc R U . . .
C34 C 1.0250(2) -0.0569(2) 0.33719(15) 0.0472(6) Uani 1 1 d . . . . .
H34 H 1.1141 -0.0950 0.3443 0.057 Uiso 1 1 calc R U . . .
C35 C 0.9869(3) -0.0405(2) 0.26518(14) 0.0509(6) Uani 1 1 d . . . . .
H35 H 1.0504 -0.0667 0.2223 0.061 Uiso 1 1 calc R U . . .
C36 C 0.8538(3) 0.0152(2) 0.25695(13) 0.0514(7) Uani 1 1 d . . . . .
H36 H 0.8283 0.0242 0.2079 0.062 Uiso 1 1 calc R U . . .
N1 N -0.14150(18) 0.19589(16) 0.04679(9) 0.0316(4) Uani 1 1 d . . . . .
N2 N -0.03618(17) 0.37574(15) 0.09013(9) 0.0282(3) Uani 1 1 d . . . . .
N3 N 0.03846(19) 0.46424(16) 0.10786(10) 0.0310(4) Uani 1 1 d . . . . .
N4 N 0.20234(19) 0.61852(16) 0.15525(9) 0.0344(4) Uani 1 1 d . . . . .
N5 N 0.31566(18) 0.25584(15) 0.61204(8) 0.0284(3) Uani 1 1 d . . . . .
N6 N 0.46330(18) 0.17757(15) 0.48868(8) 0.0281(3) Uani 1 1 d . . . . .
N7 N 0.56357(18) 0.13431(16) 0.43036(9) 0.0302(4) Uani 1 1 d . . . . .
N8 N 0.7591(2) 0.05718(17) 0.31540(9) 0.0395(4) Uani 1 1 d . . . . .
O1 O 0.23137(16) 0.43073(14) 0.01019(8) 0.0392(3) Uani 1 1 d . . . . .
O2 O 0.71358(17) 0.08194(14) 0.51715(8) 0.0377(3) Uani 1 1 d . . . . .
Cl1 Cl 0.20412(6) 0.14415(5) 0.08740(3) 0.03802(12) Uani 1 1 d . . . . .
Cl2 Cl 0.13822(7) 0.26253(6) -0.11497(3) 0.04829(15) Uani 1 1 d . . . . .
Cl3 Cl 0.68473(6) 0.35651(5) 0.55625(3) 0.04436(13) Uani 1 1 d . . . . .
Cl4 Cl 0.55913(6) 0.09899(5) 0.70630(3) 0.04331(14) Uani 1 1 d . . . . .
Zn1 Zn 0.08228(2) 0.26405(2) 0.01209(2) 0.02938(7) Uani 1 1 d . . . . .
Zn2 Zn 0.54457(2) 0.19725(2) 0.59246(2) 0.02941(7) Uani 1 1 d . . . . .
H3A H 0.006(3) 0.503(2) 0.1380(13) 0.032(6) Uiso 1 1 d . . . . .
H7 H 0.545(3) 0.135(2) 0.3856(15) 0.045(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.328(3) . ?
C1 C2 1.383(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.353(2) . ?
C5 C6 1.472(3) . ?
C6 N2 1.287(2) . ?
C6 C7 1.491(2) . ?
C7 C12 1.381(3) . ?
C7 C8 1.381(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O1 1.228(2) . ?
C13 N3 1.361(2) . ?
C13 C14 1.478(3) . ?
C14 N4 1.344(2) . ?
C14 C15 1.384(3) . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9300 . ?
C18 N4 1.330(3) . ?
C18 H18 0.9300 . ?
C19 N5 1.330(2) . ?
C19 C20 1.387(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.391(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9300 . ?
C23 N5 1.349(2) . ?
C23 C24 1.490(2) . ?
C24 N6 1.281(2) . ?
C24 C25 1.484(2) . ?
C25 C30 1.384(3) . ?
C25 C26 1.394(3) . ?
C26 C27 1.380(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.370(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.378(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.382(3) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 O2 1.226(2) . ?
C31 N7 1.353(2) . ?
C31 C32 1.488(2) . ?
C32 N8 1.336(2) . ?
C32 C33 1.371(3) . ?
C33 C34 1.387(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.367(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.373(4) . ?
C35 H35 0.9300 . ?
C36 N8 1.333(3) . ?
C36 H36 0.9300 . ?
N1 Zn1 2.1405(17) . ?
N2 N3 1.356(2) . ?
N2 Zn1 2.1237(15) . ?
N3 H3A 0.75(2) . ?
N5 Zn2 2.1310(16) . ?
N6 N7 1.363(2) . ?
N6 Zn2 2.1395(15) . ?
N7 H7 0.83(3) . ?
O1 Zn1 2.4010(16) . ?
O2 Zn2 2.3262(14) . ?
Cl1 Zn1 2.2252(6) . ?
Cl2 Zn1 2.1926(5) . ?
Cl3 Zn2 2.2410(7) . ?
Cl4 Zn2 2.2066(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.80(19) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 118.57(18) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.74(19) . . ?
N1 C5 C6 115.56(16) . . ?
C4 C5 C6 122.69(17) . . ?
N2 C6 C5 114.85(16) . . ?
N2 C6 C7 123.95(19) . . ?
C5 C6 C7 120.97(16) . . ?
C12 C7 C8 120.32(19) . . ?
C12 C7 C6 122.13(19) . . ?
C8 C7 C6 117.51(18) . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 118.7(2) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
O1 C13 N3 120.6(2) . . ?
O1 C13 C14 123.80(17) . . ?
N3 C13 C14 115.55(16) . . ?
N4 C14 C15 123.1(2) . . ?
N4 C14 C13 116.77(17) . . ?
C15 C14 C13 120.11(17) . . ?
C16 C15 C14 118.93(18) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C15 118.7(2) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 118.6(2) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
N4 C18 C17 123.7(2) . . ?
N4 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
N5 C19 C20 122.43(18) . . ?
N5 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C21 C20 C19 118.67(17) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C22 119.42(19) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 118.68(18) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
N5 C23 C22 121.73(16) . . ?
N5 C23 C24 114.77(16) . . ?
C22 C23 C24 123.41(16) . . ?
N6 C24 C25 125.22(15) . . ?
N6 C24 C23 113.36(15) . . ?
C25 C24 C23 121.42(16) . . ?
C30 C25 C26 120.01(17) . . ?
C30 C25 C24 119.83(17) . . ?
C26 C25 C24 120.14(18) . . ?
C27 C26 C25 119.6(2) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 120.42(19) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C30 120.3(2) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 119.5(2) . . ?
C29 C30 H30 120.3 . . ?
C25 C30 H30 120.3 . . ?
O2 C31 N7 121.78(16) . . ?
O2 C31 C32 123.70(17) . . ?
N7 C31 C32 114.51(15) . . ?
N8 C32 C33 124.09(18) . . ?
N8 C32 C31 115.94(17) . . ?
C33 C32 C31 119.96(17) . . ?
C32 C33 C34 118.3(2) . . ?
C32 C33 H33 120.9 . . ?
C34 C33 H33 120.9 . . ?
C35 C34 C33 118.5(2) . . ?
C35 C34 H34 120.8 . . ?
C33 C34 H34 120.8 . . ?
C34 C35 C36 119.2(2) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
N8 C36 C35 123.7(2) . . ?
N8 C36 H36 118.2 . . ?
C35 C36 H36 118.2 . . ?
C1 N1 C5 118.66(18) . . ?
C1 N1 Zn1 126.16(13) . . ?
C5 N1 Zn1 114.50(13) . . ?
C6 N2 N3 121.10(16) . . ?
C6 N2 Zn1 117.68(14) . . ?
N3 N2 Zn1 119.21(12) . . ?
N2 N3 C13 116.48(16) . . ?
N2 N3 H3A 124.7(19) . . ?
C13 N3 H3A 118.7(19) . . ?
C18 N4 C14 116.85(18) . . ?
C19 N5 C23 119.02(16) . . ?
C19 N5 Zn2 124.80(13) . . ?
C23 N5 Zn2 116.03(11) . . ?
C24 N6 N7 122.49(15) . . ?
C24 N6 Zn2 118.61(11) . . ?
N7 N6 Zn2 116.40(11) . . ?
C31 N7 N6 115.86(15) . . ?
C31 N7 H7 122.6(18) . . ?
N6 N7 H7 121.5(18) . . ?
C36 N8 C32 116.35(19) . . ?
C13 O1 Zn1 111.95(13) . . ?
C31 O2 Zn2 111.95(12) . . ?
N2 Zn1 N1 75.08(6) . . ?
N2 Zn1 Cl2 136.20(5) . . ?
N1 Zn1 Cl2 104.72(5) . . ?
N2 Zn1 Cl1 103.52(4) . . ?
N1 Zn1 Cl1 100.53(5) . . ?
Cl2 Zn1 Cl1 119.08(2) . . ?
N2 Zn1 O1 69.72(6) . . ?
N1 Zn1 O1 143.54(6) . . ?
Cl2 Zn1 O1 94.39(4) . . ?
Cl1 Zn1 O1 96.63(4) . . ?
N5 Zn2 N6 73.87(6) . . ?
N5 Zn2 Cl4 102.13(4) . . ?
N6 Zn2 Cl4 139.62(5) . . ?
N5 Zn2 Cl3 105.50(5) . . ?
N6 Zn2 Cl3 102.40(5) . . ?
Cl4 Zn2 Cl3 116.99(3) . . ?
N5 Zn2 O2 142.42(6) . . ?
N6 Zn2 O2 71.06(5) . . ?
Cl4 Zn2 O2 95.95(4) . . ?
Cl3 Zn2 O2 94.86(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
N1 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C3 C4 C5 C6 -178.75(18) . . . . ?
N1 C5 C6 N2 3.8(2) . . . . ?
C4 C5 C6 N2 -177.30(18) . . . . ?
N1 C5 C6 C7 -170.97(17) . . . . ?
C4 C5 C6 C7 7.9(3) . . . . ?
N2 C6 C7 C12 100.0(3) . . . . ?
C5 C6 C7 C12 -85.7(3) . . . . ?
N2 C6 C7 C8 -82.3(3) . . . . ?
C5 C6 C7 C8 92.0(2) . . . . ?
C12 C7 C8 C9 0.9(4) . . . . ?
C6 C7 C8 C9 -176.8(2) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C8 C9 C10 C11 -2.1(4) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C8 C7 C12 C11 -1.7(4) . . . . ?
C6 C7 C12 C11 176.0(2) . . . . ?
C10 C11 C12 C7 0.5(4) . . . . ?
O1 C13 C14 N4 -166.85(19) . . . . ?
N3 C13 C14 N4 12.2(3) . . . . ?
O1 C13 C14 C15 11.7(3) . . . . ?
N3 C13 C14 C15 -169.29(17) . . . . ?
N4 C14 C15 C16 0.1(3) . . . . ?
C13 C14 C15 C16 -178.36(18) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 N4 -0.4(4) . . . . ?
N5 C19 C20 C21 1.4(4) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C20 C21 C22 C23 -1.6(4) . . . . ?
C21 C22 C23 N5 0.5(3) . . . . ?
C21 C22 C23 C24 177.0(2) . . . . ?
N5 C23 C24 N6 5.3(3) . . . . ?
C22 C23 C24 N6 -171.4(2) . . . . ?
N5 C23 C24 C25 -174.38(18) . . . . ?
C22 C23 C24 C25 8.9(3) . . . . ?
N6 C24 C25 C30 -127.5(2) . . . . ?
C23 C24 C25 C30 52.2(3) . . . . ?
N6 C24 C25 C26 50.7(3) . . . . ?
C23 C24 C25 C26 -129.6(2) . . . . ?
C30 C25 C26 C27 2.0(3) . . . . ?
C24 C25 C26 C27 -176.18(18) . . . . ?
C25 C26 C27 C28 -0.7(3) . . . . ?
C26 C27 C28 C29 -1.3(4) . . . . ?
C27 C28 C29 C30 2.0(4) . . . . ?
C28 C29 C30 C25 -0.7(4) . . . . ?
C26 C25 C30 C29 -1.3(3) . . . . ?
C24 C25 C30 C29 176.9(2) . . . . ?
O2 C31 C32 N8 -177.6(2) . . . . ?
N7 C31 C32 N8 3.1(3) . . . . ?
O2 C31 C32 C33 3.2(3) . . . . ?
N7 C31 C32 C33 -176.0(2) . . . . ?
N8 C32 C33 C34 1.0(4) . . . . ?
C31 C32 C33 C34 -179.9(2) . . . . ?
C32 C33 C34 C35 -0.6(4) . . . . ?
C33 C34 C35 C36 -0.5(4) . . . . ?
C34 C35 C36 N8 1.5(4) . . . . ?
C2 C1 N1 C5 -0.6(3) . . . . ?
C2 C1 N1 Zn1 169.31(17) . . . . ?
C4 C5 N1 C1 0.2(3) . . . . ?
C6 C5 N1 C1 179.15(18) . . . . ?
C4 C5 N1 Zn1 -170.85(15) . . . . ?
C6 C5 N1 Zn1 8.1(2) . . . . ?
C5 C6 N2 N3 -177.93(16) . . . . ?
C7 C6 N2 N3 -3.4(3) . . . . ?
C5 C6 N2 Zn1 -14.2(2) . . . . ?
C7 C6 N2 Zn1 160.38(15) . . . . ?
C6 N2 N3 C13 174.30(17) . . . . ?
Zn1 N2 N3 C13 10.8(2) . . . . ?
O1 C13 N3 N2 1.4(3) . . . . ?
C14 C13 N3 N2 -177.62(16) . . . . ?
C17 C18 N4 C14 0.8(3) . . . . ?
C15 C14 N4 C18 -0.7(3) . . . . ?
C13 C14 N4 C18 177.81(19) . . . . ?
C20 C19 N5 C23 -2.5(3) . . . . ?
C20 C19 N5 Zn2 172.82(17) . . . . ?
C22 C23 N5 C19 1.5(3) . . . . ?
C24 C23 N5 C19 -175.23(19) . . . . ?
C22 C23 N5 Zn2 -174.18(17) . . . . ?
C24 C23 N5 Zn2 9.1(2) . . . . ?
C25 C24 N6 N7 0.8(3) . . . . ?
C23 C24 N6 N7 -178.91(18) . . . . ?
C25 C24 N6 Zn2 162.16(16) . . . . ?
C23 C24 N6 Zn2 -17.5(2) . . . . ?
O2 C31 N7 N6 0.9(3) . . . . ?
C32 C31 N7 N6 -179.76(17) . . . . ?
C24 N6 N7 C31 174.99(19) . . . . ?
Zn2 N6 N7 C31 13.2(2) . . . . ?
C35 C36 N8 C32 -1.1(4) . . . . ?
C33 C32 N8 C36 -0.2(3) . . . . ?
C31 C32 N8 C36 -179.3(2) . . . . ?
N3 C13 O1 Zn1 -10.9(2) . . . . ?
C14 C13 O1 Zn1 168.06(14) . . . . ?
N7 C31 O2 Zn2 -13.0(3) . . . . ?
C32 C31 O2 Zn2 167.76(16) . . . . ?


_refine_diff_density_max         0.472
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1524917'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 Cd N9 O6, N O3'
_chemical_formula_sum            'C24 H22 Cd N10 O9'
_chemical_formula_weight         706.91

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.2443(18)
_cell_length_b                   10.2822(13)
_cell_length_c                   14.4976(16)
_cell_angle_alpha                82.264(10)
_cell_angle_beta                 86.277(13)
_cell_angle_gamma                88.430(13)
_cell_volume                     1362.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.80


_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.875
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   'Walker, N. & Stuart, D. (1983)'

_exptl_special_details           
; 
A crystal was mounted at 173K on a Stoe Image Plate Diffraction
System (Stoe & Cie, 2000) using MoKα graphite monochromated
radiation.  Image plate distance 70mm, φ oscillation scans
0 - 200°, step Δφ = 1.5°, 5 minutes per frame.
;


_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'phi oscillation'
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            25804
_diffrn_reflns_av_unetI/netI     0.1019
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.999
_diffrn_reflns_theta_max         29.184
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7336
_reflns_number_gt                5321
_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       'EXPOSE (Stoe & Cie, 2000)'
_computing_cell_refinement       'CELL (Stoe & Cie, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe & Cie, 2000)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'


_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)+(0.0205P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7336
_refine_ls_number_parameters     411
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
C1 C 0.2107(4) 0.4530(3) 0.1441(2) 0.0186(7) Uani 1 1 d . . . . .
C2 C 0.1168(4) 0.3781(3) 0.0901(2) 0.0198(7) Uani 1 1 d . . . . .
C3 C 0.0008(4) 0.3015(4) 0.1299(3) 0.0257(9) Uani 1 1 d . . . . .
H3 H -0.0208 0.2908 0.1940 0.031 Uiso 1 1 calc R U . . .
C4 C -0.0819(4) 0.2414(4) 0.0714(3) 0.0325(9) Uani 1 1 d . . . . .
H4 H -0.1599 0.1915 0.0982 0.039 Uiso 1 1 calc R U . . .
C5 C 0.0574(4) 0.3236(3) -0.0574(3) 0.0260(8) Uani 1 1 d . . . . .
H5 H 0.0781 0.3303 -0.1215 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1451(4) 0.3888(3) -0.0058(2) 0.0240(8) Uani 1 1 d . . . . .
H6 H 0.2216 0.4388 -0.0348 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2581(4) 0.4792(3) 0.3777(2) 0.0228(8) Uani 1 1 d . . . . .
H7 H 0.3218 0.5234 0.4091 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1545(4) 0.3967(4) 0.4374(3) 0.0218(8) Uani 1 1 d . . . . .
C9 C 0.1495(4) 0.3966(3) 0.5336(3) 0.0260(8) Uani 1 1 d . . . . .
H9 H 0.2134 0.4471 0.5600 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0485(4) 0.3203(4) 0.5892(3) 0.0328(9) Uani 1 1 d . . . . .
H10 H 0.0425 0.3194 0.6536 0.039 Uiso 1 1 calc R U . . .
C11 C -0.0445(4) 0.2447(4) 0.5469(3) 0.0333(9) Uani 1 1 d . . . . .
H11 H -0.1135 0.1925 0.5826 0.040 Uiso 1 1 calc R U . . .
C12 C -0.0319(4) 0.2490(4) 0.4510(3) 0.0304(9) Uani 1 1 d . . . . .
H12 H -0.0935 0.1978 0.4234 0.036 Uiso 1 1 calc R U . . .
C13 C 0.5081(4) 0.8166(3) 0.3651(2) 0.0195(7) Uani 1 1 d . . . . .
C14 C 0.5415(4) 0.8332(3) 0.4626(2) 0.0192(7) Uani 1 1 d . . . . .
C15 C 0.4467(4) 0.7781(3) 0.5349(3) 0.0272(8) Uani 1 1 d . . . . .
H15 H 0.3662 0.7326 0.5225 0.033 Uiso 1 1 calc R U . . .
C16 C 0.4745(4) 0.7924(4) 0.6257(3) 0.0302(9) Uani 1 1 d . . . . .
H16 H 0.4097 0.7567 0.6736 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6813(4) 0.9053(3) 0.5787(3) 0.0261(8) Uani 1 1 d . . . . .
H17 H 0.7629 0.9471 0.5935 0.031 Uiso 1 1 calc R U . . .
C18 C 0.6622(4) 0.8991(3) 0.4855(2) 0.0204(7) Uani 1 1 d . . . . .
H18 H 0.7279 0.9377 0.4393 0.025 Uiso 1 1 calc R U . . .
C19 C 0.6428(4) 0.8961(3) 0.1357(2) 0.0229(8) Uani 1 1 d . . . . .
H19 H 0.7091 0.9610 0.1401 0.028 Uiso 1 1 calc R U . . .
C20 C 0.6131(4) 0.8580(3) 0.0453(2) 0.0204(7) Uani 1 1 d . . . . .
C21 C 0.6766(4) 0.9238(4) -0.0367(3) 0.0263(9) Uani 1 1 d . . . . .
H21 H 0.7402 0.9919 -0.0351 0.032 Uiso 1 1 calc R U . . .
C22 C 0.6434(4) 0.8860(3) -0.1213(2) 0.0272(8) Uani 1 1 d . . . . .
H22 H 0.6847 0.9278 -0.1773 0.033 Uiso 1 1 calc R U . . .
C23 C 0.5474(4) 0.7846(4) -0.1201(2) 0.0277(8) Uani 1 1 d . . . . .
H23 H 0.5224 0.7580 -0.1757 0.033 Uiso 1 1 calc R U . . .
C24 C 0.4885(4) 0.7228(4) -0.0353(2) 0.0245(8) Uani 1 1 d . . . . .
H24 H 0.4250 0.6543 -0.0355 0.029 Uiso 1 1 calc R U . . .
Cd1 Cd 0.42380(3) 0.66036(3) 0.19781(2) 0.01817(7) Uani 1 1 d . . . . .
N1 N -0.0559(3) 0.2510(3) -0.0205(2) 0.0309(7) Uani 1 1 d . . . . .
N2 N 0.1877(3) 0.4328(3) 0.2377(2) 0.0229(7) Uani 1 1 d . . . . .
N3 N 0.2748(3) 0.5002(3) 0.2886(2) 0.0229(6) Uani 1 1 d . . . . .
N4 N 0.0640(3) 0.3228(3) 0.3962(2) 0.0239(7) Uani 1 1 d . . . . .
N5 N 0.5902(4) 0.8552(3) 0.6484(2) 0.0306(7) Uani 1 1 d . . . . .
N6 N 0.6009(3) 0.8677(3) 0.2950(2) 0.0198(6) Uani 1 1 d . . . . .
N7 N 0.5753(3) 0.8379(3) 0.20820(18) 0.0189(6) Uani 1 1 d . . . . .
N8 N 0.5196(3) 0.7581(3) 0.04631(19) 0.0203(6) Uani 1 1 d . . . . .
N9 N 0.6734(3) 0.4969(3) 0.2571(2) 0.0311(8) Uani 1 1 d . . . . .
N10 N 0.9516(3) 0.9868(3) 0.2659(2) 0.0331(8) Uani 1 1 d . . . . .
O1 O 0.3029(3) 0.5284(2) 0.10335(16) 0.0253(6) Uani 1 1 d . . . . .
O2 O 0.3995(2) 0.7562(2) 0.35128(16) 0.0245(5) Uani 1 1 d . . . . .
O7 O 0.6194(3) 0.4982(3) 0.1786(2) 0.0455(8) Uani 1 1 d . . . . .
O8 O 0.6058(3) 0.5588(3) 0.3149(2) 0.0442(7) Uani 1 1 d . . . . .
O9 O 0.7854(3) 0.4349(4) 0.2762(2) 0.0626(10) Uani 1 1 d . . . . .
O3 O 0.9376(3) 0.8905(3) 0.2239(2) 0.0550(9) Uani 1 1 d . . . . .
O4 O 0.8396(3) 1.0459(3) 0.2932(2) 0.0362(7) Uani 1 1 d . . . . .
O5 O 1.0735(3) 1.0223(4) 0.2805(2) 0.0655(11) Uani 1 1 d . . . . .
H2A H 0.126(4) 0.380(4) 0.276(3) 0.031(11) Uiso 1 1 d . . . . .
H6A H 0.668(4) 0.914(4) 0.297(3) 0.029(11) Uiso 1 1 d . . . . .
O6 O 0.2221(3) 0.7927(3) 0.16819(19) 0.0315(6) Uani 1 1 d D . . . .
H5A H 0.170(4) 0.830(4) 0.205(2) 0.047 Uiso 1 1 d D U . . .
H5B H 0.169(4) 0.783(4) 0.126(2) 0.047 Uiso 1 1 d D 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
C1 O1 1.234(4) . ?
C1 N2 1.349(4) . ?
C1 C2 1.499(4) . ?
C2 C6 1.388(5) . ?
C2 C3 1.396(5) . ?
C3 C4 1.392(5) . ?
C3 H3 0.9300 . ?
C4 N1 1.328(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.343(5) . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N3 1.281(4) . ?
C7 C8 1.458(5) . ?
C7 H7 0.9300 . ?
C8 N4 1.363(4) . ?
C8 C9 1.391(5) . ?
C9 C10 1.382(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.397(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9300 . ?
C12 N4 1.332(5) . ?
C12 H12 0.9300 . ?
C13 O2 1.236(4) . ?
C13 N6 1.346(5) . ?
C13 C14 1.499(4) . ?
C14 C15 1.391(5) . ?
C14 C18 1.402(4) . ?
C15 C16 1.386(5) . ?
C15 H15 0.9300 . ?
C16 N5 1.345(5) . ?
C16 H16 0.9300 . ?
C17 N5 1.330(5) . ?
C17 C18 1.384(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N7 1.272(4) . ?
C19 C20 1.461(5) . ?
C19 H19 0.9300 . ?
C20 N8 1.359(4) . ?
C20 C21 1.390(5) . ?
C21 C22 1.390(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.390(5) . ?
C23 H23 0.9300 . ?
C24 N8 1.334(4) . ?
C24 H24 0.9300 . ?
Cd1 O6 2.306(3) . ?
Cd1 N7 2.358(3) . ?
Cd1 N3 2.377(3) . ?
Cd1 O1 2.398(2) . ?
Cd1 N8 2.412(3) . ?
Cd1 O7 2.454(3) . ?
Cd1 O2 2.547(2) . ?
Cd1 O8 2.570(3) . ?
N2 N3 1.385(4) . ?
N2 H2A 0.91(4) . ?
N6 N7 1.371(4) . ?
N6 H6A 0.80(4) . ?
N9 O9 1.228(4) . ?
N9 O8 1.246(4) . ?
N9 O7 1.269(4) . ?
N10 O5 1.233(4) . ?
N10 O3 1.246(4) . ?
N10 O4 1.255(4) . ?
O6 H5A 0.819(18) . ?
O6 H5B 0.828(18) . ?

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
O1 C1 N2 123.2(3) . . ?
O1 C1 C2 120.6(3) . . ?
N2 C1 C2 116.2(3) . . ?
C6 C2 C3 118.2(3) . . ?
C6 C2 C1 117.7(3) . . ?
C3 C2 C1 124.1(3) . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
N1 C4 C3 123.9(4) . . ?
N1 C4 H4 118.0 . . ?
C3 C4 H4 118.0 . . ?
N1 C5 C6 123.9(3) . . ?
N1 C5 H5 118.1 . . ?
C6 C5 H5 118.1 . . ?
C5 C6 C2 118.7(3) . . ?
C5 C6 H6 120.6 . . ?
C2 C6 H6 120.6 . . ?
N3 C7 C8 129.8(3) . . ?
N3 C7 H7 115.1 . . ?
C8 C7 H7 115.1 . . ?
N4 C8 C9 122.1(3) . . ?
N4 C8 C7 118.2(3) . . ?
C9 C8 C7 119.7(3) . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 118.8(4) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 118.7(4) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
N4 C12 C11 123.3(4) . . ?
N4 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
O2 C13 N6 122.2(3) . . ?
O2 C13 C14 120.1(3) . . ?
N6 C13 C14 117.7(3) . . ?
C15 C14 C18 118.1(3) . . ?
C15 C14 C13 117.5(3) . . ?
C18 C14 C13 124.4(3) . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N5 C16 C15 123.5(4) . . ?
N5 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
N5 C17 C18 124.1(3) . . ?
N5 C17 H17 117.9 . . ?
C18 C17 H17 117.9 . . ?
C17 C18 C14 118.4(3) . . ?
C17 C18 H18 120.8 . . ?
C14 C18 H18 120.8 . . ?
N7 C19 C20 118.1(3) . . ?
N7 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
N8 C20 C21 122.7(3) . . ?
N8 C20 C19 116.7(3) . . ?
C21 C20 C19 120.7(3) . . ?
C20 C21 C22 118.8(4) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C23 C22 C21 118.4(3) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C22 C23 C24 119.6(3) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
N8 C24 C23 122.5(3) . . ?
N8 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
O6 Cd1 N7 93.89(10) . . ?
O6 Cd1 N3 89.89(10) . . ?
N7 Cd1 N3 142.98(9) . . ?
O6 Cd1 O1 80.86(9) . . ?
N7 Cd1 O1 149.23(9) . . ?
N3 Cd1 O1 67.68(9) . . ?
O6 Cd1 N8 85.66(10) . . ?
N7 Cd1 N8 68.16(9) . . ?
N3 Cd1 N8 148.85(9) . . ?
O1 Cd1 N8 81.18(9) . . ?
O6 Cd1 O7 160.63(9) . . ?
N7 Cd1 O7 96.31(10) . . ?
N3 Cd1 O7 91.81(10) . . ?
O1 Cd1 O7 81.96(9) . . ?
N8 Cd1 O7 82.94(10) . . ?
O6 Cd1 O2 81.85(9) . . ?
N7 Cd1 O2 64.21(8) . . ?
N3 Cd1 O2 79.99(9) . . ?
O1 Cd1 O2 143.12(8) . . ?
N8 Cd1 O2 129.51(9) . . ?
O7 Cd1 O2 117.44(9) . . ?
O6 Cd1 O8 148.49(10) . . ?
N7 Cd1 O8 77.44(9) . . ?
N3 Cd1 O8 80.28(10) . . ?
O1 Cd1 O8 121.40(9) . . ?
N8 Cd1 O8 117.60(10) . . ?
O7 Cd1 O8 50.50(9) . . ?
O2 Cd1 O8 67.04(8) . . ?
C4 N1 C5 116.9(3) . . ?
C1 N2 N3 116.9(3) . . ?
C1 N2 H2A 133(2) . . ?
N3 N2 H2A 111(2) . . ?
C7 N3 N2 118.0(3) . . ?
C7 N3 Cd1 126.9(2) . . ?
N2 N3 Cd1 114.8(2) . . ?
C12 N4 C8 117.9(3) . . ?
C17 N5 C16 117.0(3) . . ?
C13 N6 N7 115.8(3) . . ?
C13 N6 H6A 129(3) . . ?
N7 N6 H6A 115(3) . . ?
C19 N7 N6 120.7(3) . . ?
C19 N7 Cd1 120.6(2) . . ?
N6 N7 Cd1 118.4(2) . . ?
C24 N8 C20 117.9(3) . . ?
C24 N8 Cd1 125.8(2) . . ?
C20 N8 Cd1 116.2(2) . . ?
O9 N9 O8 121.2(3) . . ?
O9 N9 O7 121.7(4) . . ?
O8 N9 O7 117.0(3) . . ?
O5 N10 O3 120.2(4) . . ?
O5 N10 O4 121.2(4) . . ?
O3 N10 O4 118.6(3) . . ?
C1 O1 Cd1 116.5(2) . . ?
C13 O2 Cd1 112.6(2) . . ?
N9 O7 Cd1 98.4(2) . . ?
N9 O8 Cd1 93.5(2) . . ?
Cd1 O6 H5A 129(3) . . ?
Cd1 O6 H5B 122(3) . . ?
H5A O6 H5B 104(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
O1 C1 C2 C6 5.0(5) . . . . ?
N2 C1 C2 C6 -175.2(3) . . . . ?
O1 C1 C2 C3 -173.2(3) . . . . ?
N2 C1 C2 C3 6.6(5) . . . . ?
C6 C2 C3 C4 -0.9(5) . . . . ?
C1 C2 C3 C4 177.3(3) . . . . ?
C2 C3 C4 N1 0.9(6) . . . . ?
N1 C5 C6 C2 0.9(5) . . . . ?
C3 C2 C6 C5 0.1(5) . . . . ?
C1 C2 C6 C5 -178.2(3) . . . . ?
N3 C7 C8 N4 4.1(6) . . . . ?
N3 C7 C8 C9 -175.2(4) . . . . ?
N4 C8 C9 C10 -0.8(6) . . . . ?
C7 C8 C9 C10 178.4(3) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C10 C11 C12 N4 -0.6(6) . . . . ?
O2 C13 C14 C15 0.1(5) . . . . ?
N6 C13 C14 C15 -178.9(3) . . . . ?
O2 C13 C14 C18 179.5(3) . . . . ?
N6 C13 C14 C18 0.5(5) . . . . ?
C18 C14 C15 C16 0.9(5) . . . . ?
C13 C14 C15 C16 -179.7(3) . . . . ?
C14 C15 C16 N5 -1.1(6) . . . . ?
N5 C17 C18 C14 -1.7(5) . . . . ?
C15 C14 C18 C17 0.4(5) . . . . ?
C13 C14 C18 C17 -179.0(3) . . . . ?
N7 C19 C20 N8 -3.0(5) . . . . ?
N7 C19 C20 C21 175.9(3) . . . . ?
N8 C20 C21 C22 0.0(5) . . . . ?
C19 C20 C21 C22 -178.9(3) . . . . ?
C20 C21 C22 C23 0.4(5) . . . . ?
C21 C22 C23 C24 -0.8(5) . . . . ?
C22 C23 C24 N8 0.7(5) . . . . ?
C3 C4 N1 C5 0.0(6) . . . . ?
C6 C5 N1 C4 -0.9(5) . . . . ?
O1 C1 N2 N3 -0.8(5) . . . . ?
C2 C1 N2 N3 179.3(3) . . . . ?
C8 C7 N3 N2 -2.9(6) . . . . ?
C8 C7 N3 Cd1 170.3(3) . . . . ?
C1 N2 N3 C7 -177.7(3) . . . . ?
C1 N2 N3 Cd1 8.3(4) . . . . ?
C11 C12 N4 C8 0.5(5) . . . . ?
C9 C8 N4 C12 0.2(5) . . . . ?
C7 C8 N4 C12 -179.1(3) . . . . ?
C18 C17 N5 C16 1.5(5) . . . . ?
C15 C16 N5 C17 -0.1(6) . . . . ?
O2 C13 N6 N7 -6.0(5) . . . . ?
C14 C13 N6 N7 173.0(3) . . . . ?
C20 C19 N7 N6 178.7(3) . . . . ?
C20 C19 N7 Cd1 5.7(4) . . . . ?
C13 N6 N7 C19 169.7(3) . . . . ?
C13 N6 N7 Cd1 -17.1(4) . . . . ?
C23 C24 N8 C20 -0.3(5) . . . . ?
C23 C24 N8 Cd1 179.5(3) . . . . ?
C21 C20 N8 C24 -0.1(5) . . . . ?
C19 C20 N8 C24 178.8(3) . . . . ?
C21 C20 N8 Cd1 -179.9(3) . . . . ?
C19 C20 N8 Cd1 -1.0(4) . . . . ?
N2 C1 O1 Cd1 -7.1(4) . . . . ?
C2 C1 O1 Cd1 172.7(2) . . . . ?
N6 C13 O2 Cd1 23.3(4) . . . . ?
C14 C13 O2 Cd1 -155.6(2) . . . . ?
O9 N9 O7 Cd1 -173.9(3) . . . . ?
O8 N9 O7 Cd1 7.8(3) . . . . ?
O9 N9 O8 Cd1 174.4(3) . . . . ?
O7 N9 O8 Cd1 -7.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O7 0.93 2.49 3.319(5) 147.9 2_665
C7 H7 O2 0.93 2.53 3.132(4) 122.3 .
C9 H9 O8 0.93 2.54 3.335(5) 143.9 2_666
C17 H17 O5 0.93 2.50 3.311(4) 145.6 2_776
C18 H18 O4 0.93 2.44 3.339(4) 163.9 .
C19 H19 O3 0.93 2.54 3.080(5) 117.0 .
C24 H24 O1 0.93 2.47 3.106(4) 125.9 .
N2 H2A N4 0.91(4) 1.82(4) 2.627(4) 147(3) .
N6 H6A O4 0.80(4) 2.11(4) 2.902(4) 176(4) .
O6 H5A O3 0.819(18) 2.23(3) 2.895(4) 138(3) 1_455
O6 H5A O5 0.819(18) 2.50(2) 3.269(5) 156(4) 1_455
O6 H5B N1 0.828(18) 1.982(18) 2.806(4) 174(4) 2_565

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.110

_shelxl_version_number           2013-4

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1524916'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Br2 Cd N4 O'
_chemical_formula_sum            'C18 H14 Br2 Cd N4 O'
_chemical_formula_weight         574.55

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.3470(14)
_cell_length_b                   11.4750(12)
_cell_length_c                   18.590(2)
_cell_angle_alpha                78.554(5)
_cell_angle_beta                 76.342(6)
_cell_angle_gamma                87.434(4)
_cell_volume                     1899.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    13978
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      29.17

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.010
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    5.373
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5502
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  Supernova
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            28816
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.037
_diffrn_reflns_theta_max         29.226
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9056
_reflns_number_gt                7818
_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       Supernova
_computing_cell_refinement       Supernova
_computing_data_reduction        Supernova
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0181P)²+1.1011P] 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         9056
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0566
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
C13 C 0.6761(3) 0.4866(3) 0.06033(16) 0.0133(6) Uani 1 1 d . . . . .
C6 C 0.3348(3) 0.3394(3) 0.12646(15) 0.0127(6) Uani 1 1 d . . . . .
C5 C 0.2688(3) 0.2404(3) 0.10393(15) 0.0123(6) Uani 1 1 d . . . . .
C1 C 0.2985(3) 0.1076(3) 0.02278(17) 0.0189(7) Uani 1 1 d . . . . .
H1 H 0.3546 0.0784 -0.0182 0.023 Uiso 1 1 calc R U . . .
C2 C 0.1618(3) 0.0559(3) 0.05914(18) 0.0201(7) Uani 1 1 d . . . . .
H2 H 0.1275 -0.0064 0.0426 0.024 Uiso 1 1 calc R U . . .
C3 C 0.0786(3) 0.0983(3) 0.11974(17) 0.0197(7) Uani 1 1 d . . . . .
H3 H -0.0123 0.0644 0.1452 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1318(3) 0.1926(3) 0.14277(16) 0.0163(6) Uani 1 1 d . . . . .
H4 H 0.0766 0.2232 0.1834 0.020 Uiso 1 1 calc R U . . .
C7 C 0.2577(3) 0.3837(3) 0.19536(16) 0.0134(6) Uani 1 1 d . . . . .
C12 C 0.3085(3) 0.3469(3) 0.26053(16) 0.0176(6) Uani 1 1 d . . . . .
H12 H 0.3914 0.2988 0.2596 0.021 Uiso 1 1 calc R U . . .
C11 C 0.2361(4) 0.3813(3) 0.32676(17) 0.0218(7) Uani 1 1 d . . . . .
H11 H 0.2705 0.3567 0.3704 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1124(4) 0.4525(3) 0.32833(18) 0.0239(7) Uani 1 1 d . . . . .
H10 H 0.0624 0.4741 0.3732 0.029 Uiso 1 1 calc R U . . .
C9 C 0.0632(3) 0.4915(3) 0.26302(19) 0.0246(7) Uani 1 1 d . . . . .
H9 H -0.0188 0.5408 0.2639 0.030 Uiso 1 1 calc R U . . .
C8 C 0.1353(3) 0.4576(3) 0.19662(17) 0.0205(7) Uani 1 1 d . . . . .
H8 H 0.1022 0.4841 0.1528 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7563(3) 0.5789(2) 0.08232(16) 0.0127(6) Uani 1 1 d . . . . .
C15 C 0.8893(3) 0.6217(3) 0.03603(17) 0.0157(6) Uani 1 1 d . . . . .
H15 H 0.9288 0.5940 -0.0083 0.019 Uiso 1 1 calc R U . . .
C16 C 0.9625(3) 0.7075(3) 0.05751(17) 0.0189(7) Uani 1 1 d . . . . .
H16 H 1.0518 0.7392 0.0277 0.023 Uiso 1 1 calc R U . . .
C17 C 0.8986(3) 0.7440(3) 0.12427(17) 0.0205(7) Uani 1 1 d . . . . .
H17 H 0.9453 0.8003 0.1406 0.025 Uiso 1 1 calc R U . . .
C18 C 0.7640(3) 0.6959(3) 0.16686(18) 0.0220(7) Uani 1 1 d . . . . .
H18 H 0.7220 0.7219 0.2115 0.026 Uiso 1 1 calc R U . . .
C31 C 1.1705(3) 0.0960(2) 0.44538(16) 0.0136(6) Uani 1 1 d . . . . .
C24 C 0.8197(3) 0.2292(2) 0.47508(15) 0.0121(6) Uani 1 1 d . . . . .
C23 C 0.7294(3) 0.2729(2) 0.54201(15) 0.0116(6) Uani 1 1 d . . . . .
C19 C 0.7212(3) 0.3096(3) 0.66103(16) 0.0158(6) Uani 1 1 d . . . . .
H19 H 0.7676 0.3087 0.7002 0.019 Uiso 1 1 calc R U . . .
C20 C 0.5766(3) 0.3464(3) 0.67012(17) 0.0178(6) Uani 1 1 d . . . . .
H20 H 0.5275 0.3719 0.7139 0.021 Uiso 1 1 calc R U . . .
C21 C 0.5061(3) 0.3447(3) 0.61302(17) 0.0179(6) Uani 1 1 d . . . . .
H21 H 0.4085 0.3687 0.6177 0.021 Uiso 1 1 calc R U . . .
C22 C 0.5836(3) 0.3065(3) 0.54800(17) 0.0168(6) Uani 1 1 d . . . . .
H22 H 0.5378 0.3036 0.5091 0.020 Uiso 1 1 calc R U . . .
C25 C 0.7732(3) 0.2468(3) 0.40244(15) 0.0123(6) Uani 1 1 d . . . . .
C26 C 0.7817(3) 0.1552(3) 0.36222(16) 0.0142(6) Uani 1 1 d . . . . .
H26 H 0.8071 0.0789 0.3832 0.017 Uiso 1 1 calc R U . . .
C27 C 0.7521(3) 0.1778(3) 0.29121(16) 0.0162(6) Uani 1 1 d . . . . .
H27 H 0.7602 0.1170 0.2640 0.019 Uiso 1 1 calc R U . . .
C28 C 0.7106(3) 0.2907(3) 0.26040(17) 0.0180(6) Uani 1 1 d . . . . .
H28 H 0.6919 0.3058 0.2124 0.022 Uiso 1 1 calc R U . . .
C29 C 0.6969(3) 0.3809(3) 0.30120(17) 0.0199(7) Uani 1 1 d . . . . .
H29 H 0.6667 0.4561 0.2811 0.024 Uiso 1 1 calc R U . . .
C30 C 0.7281(3) 0.3595(3) 0.37175(16) 0.0169(6) Uani 1 1 d . . . . .
H30 H 0.7190 0.4205 0.3988 0.020 Uiso 1 1 calc R U . . .
C32 C 1.2689(3) 0.0474(2) 0.38281(16) 0.0139(6) Uani 1 1 d . . . . .
C33 C 1.4096(3) 0.0106(3) 0.38731(18) 0.0202(7) Uani 1 1 d . . . . .
H33 H 1.4457 0.0170 0.4289 0.024 Uiso 1 1 calc R U . . .
C34 C 1.4959(3) -0.0363(3) 0.32817(18) 0.0227(7) Uani 1 1 d . . . . .
H34 H 1.5912 -0.0624 0.3291 0.027 Uiso 1 1 calc R U . . .
C35 C 1.4365(4) -0.0432(3) 0.26800(18) 0.0239(7) Uani 1 1 d . . . . .
H36 H 1.4920 -0.0733 0.2272 0.029 Uiso 1 1 calc R U . . .
C36 C 1.2940(4) -0.0050(3) 0.26863(18) 0.0220(7) Uani 1 1 d . . . . .
H35 H 1.2549 -0.0121 0.2281 0.026 Uiso 1 1 calc R U . . .
Br1 Br 0.70791(3) 0.11406(3) 0.10015(2) 0.02024(7) Uani 1 1 d . . . . .
Br2 Br 0.66581(4) 0.25192(3) -0.13410(2) 0.02367(8) Uani 1 1 d . . . . .
Br3 Br 1.19514(3) 0.41387(3) 0.52025(2) 0.01871(7) Uani 1 1 d . . . . .
Br4 Br 1.08887(3) 0.13143(3) 0.71042(2) 0.01969(7) Uani 1 1 d . . . . .
Cd1 Cd 0.59900(2) 0.25826(2) 0.00365(2) 0.01412(5) Uani 1 1 d . . . . .
Cd2 Cd 1.04605(2) 0.22434(2) 0.58206(2) 0.01346(5) Uani 1 1 d . . . . .
N3 N 0.5362(3) 0.4627(2) 0.10256(13) 0.0132(5) Uani 1 1 d . . . . .
H3A H 0.4965 0.5010 0.1376 0.016 Uiso 1 1 calc R U . . .
N2 N 0.4624(3) 0.3745(2) 0.08604(13) 0.0142(5) Uani 1 1 d . . . . .
N1 N 0.3522(3) 0.1974(2) 0.04455(13) 0.0150(5) Uani 1 1 d . . . . .
N4 N 0.6917(3) 0.6138(2) 0.14681(13) 0.0158(5) Uani 1 1 d . . . . .
N7 N 1.0397(3) 0.1369(2) 0.43073(13) 0.0130(5) Uani 1 1 d . . . . .
H7 H 1.0194 0.1357 0.3881 0.016 Uiso 1 1 calc R U . . .
N6 N 0.9420(3) 0.1797(2) 0.48606(13) 0.0118(5) Uani 1 1 d . . . . .
N5 N 0.7974(3) 0.2751(2) 0.59865(13) 0.0127(5) Uani 1 1 d . . . . .
N8 N 1.2098(3) 0.0415(2) 0.32429(14) 0.0175(5) Uani 1 1 d . . . . .
O1 O 0.7324(2) 0.43578(18) 0.00828(11) 0.0179(5) Uani 1 1 d . . . . .
O2 O 1.2040(2) 0.09800(18) 0.50552(11) 0.0168(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C13 O1 1.228(3) . ?
C13 N3 1.365(3) . ?
C13 C14 1.497(4) . ?
C6 N2 1.285(4) . ?
C6 C7 1.486(4) . ?
C6 C5 1.490(4) . ?
C5 N1 1.358(4) . ?
C5 C4 1.390(4) . ?
C1 N1 1.336(4) . ?
C1 C2 1.394(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C7 C12 1.386(4) . ?
C7 C8 1.391(4) . ?
C12 C11 1.381(4) . ?
C12 H12 0.9300 . ?
C11 C10 1.383(5) . ?
C11 H11 0.9300 . ?
C10 C9 1.384(5) . ?
C10 H10 0.9300 . ?
C9 C8 1.380(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C14 N4 1.338(4) . ?
C14 C15 1.381(4) . ?
C15 C16 1.394(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(4) . ?
C17 H17 0.9300 . ?
C18 N4 1.341(4) . ?
C18 H18 0.9300 . ?
C31 O2 1.235(3) . ?
C31 N7 1.358(4) . ?
C31 C32 1.489(4) . ?
C24 N6 1.295(4) . ?
C24 C25 1.488(4) . ?
C24 C23 1.492(4) . ?
C23 N5 1.357(3) . ?
C23 C22 1.385(4) . ?
C19 N5 1.332(4) . ?
C19 C20 1.380(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.395(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C25 C30 1.395(4) . ?
C25 C26 1.396(4) . ?
C26 C27 1.384(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.387(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.384(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C32 N8 1.345(4) . ?
C32 C33 1.379(4) . ?
C33 C34 1.388(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.377(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.382(5) . ?
C35 H36 0.9300 . ?
C36 N8 1.331(4) . ?
C36 H35 0.9300 . ?
Br1 Cd1 2.5547(4) . ?
Br2 Cd1 2.5035(5) . ?
Br3 Cd2 2.5526(4) . ?
Br4 Cd2 2.5288(4) . ?
Cd1 N2 2.343(2) . ?
Cd1 N1 2.344(2) . ?
Cd1 O1 2.4614(19) . ?
Cd2 N5 2.334(2) . ?
Cd2 N6 2.371(2) . ?
Cd2 O2 2.437(2) . ?
N3 N2 1.372(3) . ?
N3 H3A 0.8600 . ?
N7 N6 1.361(3) . ?
N7 H7 0.8600 . ?

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
O1 C13 N3 122.6(3) . . ?
O1 C13 C14 122.4(3) . . ?
N3 C13 C14 115.1(2) . . ?
N2 C6 C7 124.7(2) . . ?
N2 C6 C5 115.5(3) . . ?
C7 C6 C5 119.6(2) . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 C6 116.1(2) . . ?
C4 C5 C6 121.9(3) . . ?
N1 C1 C2 122.6(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C12 C7 C8 119.7(3) . . ?
C12 C7 C6 118.1(3) . . ?
C8 C7 C6 122.1(3) . . ?
C11 C12 C7 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
N4 C14 C15 124.8(3) . . ?
N4 C14 C13 116.2(2) . . ?
C15 C14 C13 119.0(3) . . ?
C14 C15 C16 118.2(3) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C17 C16 C15 118.1(3) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
N4 C18 C17 123.3(3) . . ?
N4 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
O2 C31 N7 122.9(3) . . ?
O2 C31 C32 123.1(3) . . ?
N7 C31 C32 114.0(2) . . ?
N6 C24 C25 124.5(3) . . ?
N6 C24 C23 113.6(2) . . ?
C25 C24 C23 121.9(2) . . ?
N5 C23 C22 121.1(3) . . ?
N5 C23 C24 116.0(2) . . ?
C22 C23 C24 122.9(2) . . ?
N5 C19 C20 123.0(3) . . ?
N5 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C21 C20 C19 118.7(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 118.9(3) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 119.3(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C30 C25 C26 119.2(3) . . ?
C30 C25 C24 119.1(3) . . ?
C26 C25 C24 121.6(3) . . ?
C27 C26 C25 120.1(3) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.3(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 119.9(3) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C30 C29 C28 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C25 120.3(3) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
N8 C32 C33 124.1(3) . . ?
N8 C32 C31 115.3(2) . . ?
C33 C32 C31 120.5(3) . . ?
C32 C33 C34 118.3(3) . . ?
C32 C33 H33 120.9 . . ?
C34 C33 H33 120.9 . . ?
C35 C34 C33 118.2(3) . . ?
C35 C34 H34 120.9 . . ?
C33 C34 H34 120.9 . . ?
C34 C35 C36 119.5(3) . . ?
C34 C35 H36 120.2 . . ?
C36 C35 H36 120.2 . . ?
N8 C36 C35 123.3(3) . . ?
N8 C36 H35 118.3 . . ?
C35 C36 H35 118.3 . . ?
N2 Cd1 N1 68.57(8) . . ?
N2 Cd1 O1 66.69(7) . . ?
N1 Cd1 O1 134.03(8) . . ?
N2 Cd1 Br2 139.75(6) . . ?
N1 Cd1 Br2 104.79(6) . . ?
O1 Cd1 Br2 102.32(5) . . ?
N2 Cd1 Br1 97.72(6) . . ?
N1 Cd1 Br1 99.45(6) . . ?
O1 Cd1 Br1 96.40(5) . . ?
Br2 Cd1 Br1 122.364(15) . . ?
N5 Cd2 N6 67.58(8) . . ?
N5 Cd2 O2 133.14(7) . . ?
N6 Cd2 O2 67.21(7) . . ?
N5 Cd2 Br4 107.39(6) . . ?
N6 Cd2 Br4 140.81(6) . . ?
O2 Cd2 Br4 99.75(5) . . ?
N5 Cd2 Br3 107.42(6) . . ?
N6 Cd2 Br3 104.57(6) . . ?
O2 Cd2 Br3 95.16(5) . . ?
Br4 Cd2 Br3 113.564(13) . . ?
C13 N3 N2 116.4(2) . . ?
C13 N3 H3A 121.8 . . ?
N2 N3 H3A 121.8 . . ?
C6 N2 N3 120.9(2) . . ?
C6 N2 Cd1 120.04(19) . . ?
N3 N2 Cd1 117.22(17) . . ?
C1 N1 C5 118.3(2) . . ?
C1 N1 Cd1 123.4(2) . . ?
C5 N1 Cd1 117.04(17) . . ?
C14 N4 C18 116.3(2) . . ?
C31 N7 N6 117.5(2) . . ?
C31 N7 H7 121.3 . . ?
N6 N7 H7 121.3 . . ?
C24 N6 N7 121.8(2) . . ?
C24 N6 Cd2 119.99(18) . . ?
N7 N6 Cd2 114.35(16) . . ?
C19 N5 C23 118.9(2) . . ?
C19 N5 Cd2 122.13(18) . . ?
C23 N5 Cd2 118.91(18) . . ?
C36 N8 C32 116.5(3) . . ?
C13 O1 Cd1 114.94(18) . . ?
C31 O2 Cd2 114.01(18) . . ?

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
N2 C6 C5 N1 1.3(4) . . . . ?
C7 C6 C5 N1 -174.0(2) . . . . ?
N2 C6 C5 C4 179.5(3) . . . . ?
C7 C6 C5 C4 4.2(4) . . . . ?
N1 C1 C2 C3 -0.1(5) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
N1 C5 C4 C3 -0.3(4) . . . . ?
C6 C5 C4 C3 -178.4(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
N2 C6 C7 C12 -73.5(4) . . . . ?
C5 C6 C7 C12 101.4(3) . . . . ?
N2 C6 C7 C8 108.2(3) . . . . ?
C5 C6 C7 C8 -76.9(4) . . . . ?
C8 C7 C12 C11 1.3(4) . . . . ?
C6 C7 C12 C11 -177.0(3) . . . . ?
C7 C12 C11 C10 0.2(4) . . . . ?
C12 C11 C10 C9 -1.5(5) . . . . ?
C11 C10 C9 C8 1.4(5) . . . . ?
C10 C9 C8 C7 0.1(5) . . . . ?
C12 C7 C8 C9 -1.5(4) . . . . ?
C6 C7 C8 C9 176.7(3) . . . . ?
O1 C13 C14 N4 -170.0(3) . . . . ?
N3 C13 C14 N4 9.7(4) . . . . ?
O1 C13 C14 C15 10.0(4) . . . . ?
N3 C13 C14 C15 -170.3(3) . . . . ?
N4 C14 C15 C16 0.1(4) . . . . ?
C13 C14 C15 C16 -179.9(3) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C18 -0.9(5) . . . . ?
C16 C17 C18 N4 0.5(5) . . . . ?
N6 C24 C23 N5 11.7(3) . . . . ?
C25 C24 C23 N5 -166.0(2) . . . . ?
N6 C24 C23 C22 -166.7(3) . . . . ?
C25 C24 C23 C22 15.6(4) . . . . ?
N5 C19 C20 C21 1.7(4) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
N5 C23 C22 C21 0.8(4) . . . . ?
C24 C23 C22 C21 179.1(3) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
N6 C24 C25 C30 -128.9(3) . . . . ?
C23 C24 C25 C30 48.6(4) . . . . ?
N6 C24 C25 C26 47.4(4) . . . . ?
C23 C24 C25 C26 -135.2(3) . . . . ?
C30 C25 C26 C27 3.0(4) . . . . ?
C24 C25 C26 C27 -173.3(3) . . . . ?
C25 C26 C27 C28 -1.6(4) . . . . ?
C26 C27 C28 C29 -0.7(4) . . . . ?
C27 C28 C29 C30 1.6(4) . . . . ?
C28 C29 C30 C25 -0.2(5) . . . . ?
C26 C25 C30 C29 -2.1(4) . . . . ?
C24 C25 C30 C29 174.2(3) . . . . ?
O2 C31 C32 N8 173.9(3) . . . . ?
N7 C31 C32 N8 -5.5(4) . . . . ?
O2 C31 C32 C33 -5.3(4) . . . . ?
N7 C31 C32 C33 175.3(3) . . . . ?
N8 C32 C33 C34 -0.5(4) . . . . ?
C31 C32 C33 C34 178.7(3) . . . . ?
C32 C33 C34 C35 0.2(4) . . . . ?
C33 C34 C35 C36 -0.8(5) . . . . ?
C34 C35 C36 N8 1.6(5) . . . . ?
O1 C13 N3 N2 2.7(4) . . . . ?
C14 C13 N3 N2 -177.0(2) . . . . ?
C7 C6 N2 N3 -3.1(4) . . . . ?
C5 C6 N2 N3 -178.1(2) . . . . ?
C7 C6 N2 Cd1 161.0(2) . . . . ?
C5 C6 N2 Cd1 -14.1(3) . . . . ?
C13 N3 N2 C6 174.5(3) . . . . ?
C13 N3 N2 Cd1 10.0(3) . . . . ?
C2 C1 N1 C5 -0.8(4) . . . . ?
C2 C1 N1 Cd1 165.9(2) . . . . ?
C4 C5 N1 C1 0.9(4) . . . . ?
C6 C5 N1 C1 179.2(2) . . . . ?
C4 C5 N1 Cd1 -166.5(2) . . . . ?
C6 C5 N1 Cd1 11.7(3) . . . . ?
C15 C14 N4 C18 -0.4(4) . . . . ?
C13 C14 N4 C18 179.5(3) . . . . ?
C17 C18 N4 C14 0.1(5) . . . . ?
O2 C31 N7 N6 -1.1(4) . . . . ?
C32 C31 N7 N6 178.3(2) . . . . ?
C25 C24 N6 N7 -1.0(4) . . . . ?
C23 C24 N6 N7 -178.7(2) . . . . ?
C25 C24 N6 Cd2 155.5(2) . . . . ?
C23 C24 N6 Cd2 -22.2(3) . . . . ?
C31 N7 N6 C24 174.3(2) . . . . ?
C31 N7 N6 Cd2 16.6(3) . . . . ?
C20 C19 N5 C23 -1.8(4) . . . . ?
C20 C19 N5 Cd2 176.2(2) . . . . ?
C22 C23 N5 C19 0.5(4) . . . . ?
C24 C23 N5 C19 -177.9(2) . . . . ?
C22 C23 N5 Cd2 -177.6(2) . . . . ?
C24 C23 N5 Cd2 4.1(3) . . . . ?
C35 C36 N8 C32 -1.7(4) . . . . ?
C33 C32 N8 C36 1.2(4) . . . . ?
C31 C32 N8 C36 -178.0(3) . . . . ?
N3 C13 O1 Cd1 -13.2(3) . . . . ?
C14 C13 O1 Cd1 166.5(2) . . . . ?
N7 C31 O2 Cd2 -14.5(3) . . . . ?
C32 C31 O2 Cd2 166.2(2) . . . . ?

_refine_diff_density_max         0.627
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.111

_shelxl_version_number           2013-4

