# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1461711'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N6 O S2 Zn'
_chemical_formula_sum            'C15 H12 N6 O S2 Zn'
_chemical_formula_weight         421.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_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                   8.5220(2)
_cell_length_b                   15.4590(1)
_cell_length_c                   15.7009(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.1660(10)
_cell_angle_gamma                90.00
_cell_volume                     1750.97(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120.0
_cell_measurement_reflns_used    3660
_cell_measurement_theta_min      4.3834
_cell_measurement_theta_max      70.4976

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.1680
_exptl_crystal_size_mid          0.0846
_exptl_crystal_size_min          0.0758
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    4.324
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41a (release 15-10-2010 CrysAlis171 .NET)
(compiled Oct 15 2010,13:39:29)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120.0
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2673
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6536
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.39
_diffrn_reflns_theta_max         70.63
_reflns_number_total             3267
_reflns_number_gt                2834
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41a (release 15-10-2010 CrysAlis171 .NET)
(compiled Oct 15 2010,13:39:29)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41a (release 15-10-2010 CrysAlis171 .NET)
(compiled Oct 15 2010,13:39:29)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41a (release 15-10-2010 CrysAlis171 .NET)
(compiled Oct 15 2010,13:39:29)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0324P)²+0.2281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3267
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 -0.20604(4) -0.016457(18) -0.21225(2) 0.02288(9) Uani 1 1 d . . .
S2 S -0.27111(8) -0.08020(3) -0.52634(4) 0.02803(13) Uani 1 1 d . . .
S1 S -0.77732(9) 0.04765(5) -0.25086(5) 0.04204(17) Uani 1 1 d . . .
C15 C -0.2672(3) -0.06163(13) -0.42287(16) 0.0235(4) Uani 1 1 d . . .
O1 O -0.1072(2) -0.13765(10) -0.14174(12) 0.0309(3) Uani 1 1 d . . .
N3 N 0.3281(3) -0.36514(13) 0.07205(15) 0.0320(4) Uani 1 1 d . . .
N6 N -0.2618(3) -0.04894(12) -0.34870(14) 0.0280(4) Uani 1 1 d . . .
N4 N -0.1714(2) 0.12308(12) -0.22000(13) 0.0259(4) Uani 1 1 d . . .
N1 N 0.0566(2) 0.00873(11) -0.09284(13) 0.0217(4) Uani 1 1 d . . .
N2 N 0.1637(2) -0.06052(11) -0.03498(13) 0.0234(4) Uani 1 1 d . . .
C13 C 0.3204(3) 0.10775(16) 0.00330(17) 0.0285(5) Uani 1 1 d . . .
C8 C 0.0423(3) 0.23875(15) -0.13815(17) 0.0293(5) Uani 1 1 d . . .
C4 C 0.1548(3) -0.36724(16) -0.00853(19) 0.0326(5) Uani 1 1 d . . .
C2 C 0.1587(3) -0.21287(14) -0.01650(16) 0.0252(4) Uani 1 1 d . . .
C3 C 0.0671(3) -0.29080(15) -0.05432(18) 0.0301(5) Uani 1 1 d . . .
C11 C -0.2940(3) 0.17947(15) -0.28517(18) 0.0334(5) Uani 1 1 d . . .
C5 C 0.4216(4) -0.29086(16) 0.11224(18) 0.0342(5) Uani 1 1 d . . .
C9 C -0.0876(3) 0.29742(16) -0.20622(18) 0.0336(5) Uani 1 1 d . . .
C12 C 0.1270(3) 0.08492(13) -0.07658(14) 0.0215(4) Uani 1 1 d . . .
N5 N -0.4540(3) -0.01528(12) -0.23070(13) 0.0264(4) Uani 1 1 d . . .
C10 C -0.2581(3) 0.26765(16) -0.28128(18) 0.0338(5) Uani 1 1 d . . .
C7 C -0.0032(3) 0.15197(14) -0.14663(15) 0.0223(4) Uani 1 1 d . . .
C14 C -0.5882(3) 0.01156(14) -0.23851(15) 0.0233(4) Uani 1 1 d . . .
C1 C 0.0609(3) -0.13112(14) -0.06946(15) 0.0238(4) Uani 1 1 d . . .
C6 C 0.3392(3) -0.21347(16) 0.06887(17) 0.0291(5) Uani 1 1 d . . .
H13A H 0.378(4) 0.1431(18) -0.0217(19) 0.034(7) Uiso 1 1 d . . .
H3 H -0.056(4) -0.2920(17) -0.113(2) 0.038(7) Uiso 1 1 d . . .
H8 H 0.153(4) 0.2575(17) -0.0911(19) 0.033(7) Uiso 1 1 d . . .
H11 H -0.409(4) 0.1550(19) -0.335(2) 0.040(7) Uiso 1 1 d . . .
H10 H -0.357(4) 0.3048(18) -0.332(2) 0.038(7) Uiso 1 1 d . . .
H9 H -0.061(4) 0.3554(19) -0.2023(19) 0.035(7) Uiso 1 1 d . . .
H5 H 0.546(4) -0.2945(17) 0.172(2) 0.035(7) Uiso 1 1 d . . .
H6 H 0.399(4) -0.1645(19) 0.093(2) 0.036(7) Uiso 1 1 d . . .
H13B H 0.390(5) 0.060(2) 0.031(3) 0.060(10) Uiso 1 1 d . . .
H4 H 0.103(4) -0.4187(19) -0.031(2) 0.040(8) Uiso 1 1 d . . .
H13C H 0.317(4) 0.142(2) 0.054(2) 0.053(9) Uiso 1 1 d . . .
H1 H 0.378(4) -0.413(2) 0.099(2) 0.049(9) 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
Zn1 N5 1.9747(19) . ?
Zn1 N6 1.9960(19) . ?
Zn1 N1 2.0516(18) . ?
Zn1 O1 2.1101(15) . ?
Zn1 N4 2.1894(18) . ?
S2 C15 1.632(2) . ?
S1 C14 1.617(2) . ?
C15 N6 1.158(3) . ?
O1 C1 1.272(3) . ?
N3 C4 1.339(3) . ?
N3 C5 1.348(3) . ?
N3 H1 0.85(3) . ?
N4 C11 1.327(3) . ?
N4 C7 1.350(3) . ?
N1 C12 1.284(3) . ?
N1 N2 1.386(2) . ?
N2 C1 1.322(3) . ?
C13 C12 1.488(3) . ?
C13 H13A 0.94(3) . ?
C13 H13B 0.90(4) . ?
C13 H13C 0.97(3) . ?
C8 C7 1.383(3) . ?
C8 C9 1.389(3) . ?
C8 H8 0.88(3) . ?
C4 C3 1.378(3) . ?
C4 H4 0.89(3) . ?
C2 C3 1.386(3) . ?
C2 C6 1.403(3) . ?
C2 C1 1.498(3) . ?
C3 H3 0.96(3) . ?
C11 C10 1.391(4) . ?
C11 H11 0.95(3) . ?
C5 C6 1.371(3) . ?
C5 H5 0.97(3) . ?
C9 C10 1.374(3) . ?
C9 H9 0.92(3) . ?
C12 C7 1.489(3) . ?
N5 C14 1.160(3) . ?
C10 H10 0.98(3) . ?
C6 H6 0.88(3) . ?

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
N5 Zn1 N6 102.72(8) . . ?
N5 Zn1 N1 133.97(7) . . ?
N6 Zn1 N1 123.31(7) . . ?
N5 Zn1 O1 100.51(7) . . ?
N6 Zn1 O1 98.06(7) . . ?
N1 Zn1 O1 75.66(6) . . ?
N5 Zn1 N4 98.53(7) . . ?
N6 Zn1 N4 98.65(7) . . ?
N1 Zn1 N4 75.52(7) . . ?
O1 Zn1 N4 151.16(6) . . ?
N6 C15 S2 179.0(2) . . ?
C1 O1 Zn1 110.06(14) . . ?
C4 N3 C5 122.9(2) . . ?
C4 N3 H1 117(2) . . ?
C5 N3 H1 120(2) . . ?
C15 N6 Zn1 169.03(18) . . ?
C11 N4 C7 118.89(19) . . ?
C11 N4 Zn1 128.03(15) . . ?
C7 N4 Zn1 113.07(14) . . ?
C12 N1 N2 120.22(17) . . ?
C12 N1 Zn1 121.51(14) . . ?
N2 N1 Zn1 118.01(13) . . ?
C1 N2 N1 107.92(17) . . ?
C12 C13 H13A 111.8(16) . . ?
C12 C13 H13B 111(2) . . ?
H13A C13 H13B 109(3) . . ?
C12 C13 H13C 108.3(19) . . ?
H13A C13 H13C 106(2) . . ?
H13B C13 H13C 111(3) . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H8 121.3(18) . . ?
C9 C8 H8 119.2(18) . . ?
N3 C4 C3 119.4(2) . . ?
N3 C4 H4 117.6(19) . . ?
C3 C4 H4 123.0(19) . . ?
C3 C2 C6 119.0(2) . . ?
C3 C2 C1 118.39(19) . . ?
C6 C2 C1 122.6(2) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 119.8(17) . . ?
C2 C3 H3 120.5(17) . . ?
N4 C11 C10 123.1(2) . . ?
N4 C11 H11 114.7(17) . . ?
C10 C11 H11 122.3(17) . . ?
N3 C5 C6 119.5(2) . . ?
N3 C5 H5 118.1(16) . . ?
C6 C5 H5 122.4(16) . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 119.7(17) . . ?
C8 C9 H9 121.2(17) . . ?
N1 C12 C13 125.1(2) . . ?
N1 C12 C7 113.98(18) . . ?
C13 C12 C7 120.87(19) . . ?
C14 N5 Zn1 159.51(18) . . ?
C9 C10 C11 118.2(2) . . ?
C9 C10 H10 124.0(16) . . ?
C11 C10 H10 117.7(16) . . ?
N4 C7 C8 121.3(2) . . ?
N4 C7 C12 115.79(18) . . ?
C8 C7 C12 122.95(19) . . ?
N5 C14 S1 179.0(2) . . ?
O1 C1 N2 128.1(2) . . ?
O1 C1 C2 117.22(19) . . ?
N2 C1 C2 114.69(18) . . ?
C5 C6 C2 119.4(2) . . ?
C5 C6 H6 120.6(18) . . ?
C2 C6 H6 119.9(18) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        70.63
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.056
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1461712'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 N10 O9 Zn'
_chemical_formula_sum            'C26 H26 N10 O9 Zn'
_chemical_formula_weight         687.96

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   27.2384(10)
_cell_length_b                   12.3781(2)
_cell_length_c                   23.7446(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 133.803(7)
_cell_angle_gamma                90.00
_cell_volume                     5777.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    20808
_cell_measurement_theta_min      2.9384
_cell_measurement_theta_max      29.2582

_exptl_crystal_description       PLATE
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2831
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.72477
_exptl_absorpt_correction_T_max  1.0
_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.
;
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  MIRROR
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33848
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         23.25
_reflns_number_total             4122
_reflns_number_gt                3790
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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 > 2σ(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)+(0.0175P)²+16.7361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4122
_refine_ls_number_parameters     442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.002

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 0.255127(13) 0.07574(2) 0.106507(14) 0.01766(9) Uani 1 1 d . . .
O1 O 0.34547(8) 0.11062(12) 0.13044(9) 0.0205(4) Uani 1 1 d . . .
O2 O 0.20946(8) -0.01922(12) 0.00649(9) 0.0246(4) Uani 1 1 d . . .
N3 N 0.15996(9) 0.13134(15) 0.07199(10) 0.0182(4) Uani 1 1 d . . .
N5 N 0.26246(9) -0.08258(15) 0.14088(10) 0.0176(4) Uani 1 1 d . . .
N1 N 0.30073(9) 0.28548(15) 0.09498(10) 0.0182(4) Uani 1 1 d . . .
N6 N 0.30811(9) 0.08733(15) 0.22908(10) 0.0184(4) Uani 1 1 d . . .
N4 N 0.23162(9) -0.16317(15) 0.08483(11) 0.0193(4) Uani 1 1 d . . .
N2 N 0.24774(9) 0.23780(15) 0.08136(10) 0.0167(4) Uani 1 1 d . . .
N12 N 0.51523(10) 0.32822(16) 0.15994(11) 0.0231(5) Uani 1 1 d . . .
H12 H 0.5543(16) 0.357(2) 0.1691(17) 0.050(9) Uiso 1 1 d . . .
C19 C 0.36432(12) 0.1750(2) 0.35029(14) 0.0253(6) Uani 1 1 d . . .
H19 H 0.3770 0.2403 0.3785 0.030 Uiso 1 1 calc R . .
C20 C 0.38138(13) 0.0763(2) 0.38648(14) 0.0284(6) Uani 1 1 d . . .
H20 H 0.4074 0.0722 0.4408 0.034 Uiso 1 1 calc R . .
C21 C 0.36014(12) -0.0168(2) 0.34282(13) 0.0248(6) Uani 1 1 d . . .
H21 H 0.3712 -0.0856 0.3668 0.030 Uiso 1 1 calc R . .
N26 N 0.10440(10) -0.32953(16) -0.17428(12) 0.0211(4) Uani 1 1 d . . .
H26 H 0.0818(16) -0.374(3) -0.2165(19) 0.052(9) Uiso 1 1 d . . .
C10 C 0.41021(12) 0.36149(19) 0.12111(13) 0.0225(5) Uani 1 1 d . . .
H10 H 0.3749 0.4103 0.1032 0.027 Uiso 1 1 calc R . .
C1 C 0.34680(11) 0.21057(18) 0.11906(12) 0.0176(5) Uani 1 1 d . . .
C9 C 0.40630(11) 0.25292(18) 0.13373(12) 0.0174(5) Uani 1 1 d . . .
C23 C 0.17051(11) -0.19443(18) -0.04887(13) 0.0198(5) Uani 1 1 d . . .
C24 C 0.16377(12) -0.30435(18) -0.04228(13) 0.0222(5) Uani 1 1 d . . .
H24 H 0.1818 -0.3331 0.0060 0.027 Uiso 1 1 calc R . .
C6 C 0.04381(12) 0.2246(2) 0.02428(13) 0.0248(6) Uani 1 1 d . . .
H6 H 0.0037 0.2564 0.0075 0.030 Uiso 1 1 calc R . .
C11 C 0.46553(12) 0.3971(2) 0.13489(14) 0.0254(6) Uani 1 1 d . . .
H11 H 0.4686 0.4709 0.1266 0.031 Uiso 1 1 calc R . .
C22 C 0.30485(15) -0.2160(2) 0.24335(16) 0.0268(6) Uani 1 1 d . . .
H22A H 0.2832(14) -0.268(2) 0.2042(17) 0.035 Uiso 1 1 d . . .
H22B H 0.2858(14) -0.218(2) 0.2650(16) 0.035 Uiso 1 1 d . . .
H22C H 0.3507(15) -0.233(2) 0.2816(17) 0.035 Uiso 1 1 d . . .
C8 C 0.19237(14) 0.41518(19) 0.04335(15) 0.0214(5) Uani 1 1 d . . .
H8A H 0.2190(13) 0.435(2) 0.0315(15) 0.028 Uiso 1 1 d . . .
H8B H 0.2115(13) 0.452(2) 0.0871(16) 0.028 Uiso 1 1 d . . .
H8C H 0.1459(14) 0.437(2) 0.0020(16) 0.028 Uiso 1 1 d . . .
C14 C 0.45838(11) 0.18399(19) 0.15899(13) 0.0204(5) Uani 1 1 d . . .
H14 H 0.4566 0.1097 0.1675 0.025 Uiso 1 1 calc R . .
C27 C 0.11010(12) -0.22447(19) -0.18282(14) 0.0233(5) Uani 1 1 d . . .
H27 H 0.0908 -0.1978 -0.2321 0.028 Uiso 1 1 calc R . .
C28 C 0.14379(12) -0.15552(19) -0.12051(13) 0.0226(5) Uani 1 1 d . . .
H28 H 0.1489 -0.0815 -0.1262 0.027 Uiso 1 1 calc R . .
C7 C 0.08635(11) 0.28403(19) 0.02311(13) 0.0205(5) Uani 1 1 d . . .
H7 H 0.0752 0.3563 0.0045 0.025 Uiso 1 1 calc R . .
C17 C 0.32284(11) -0.00942(19) 0.26416(13) 0.0189(5) Uani 1 1 d . . .
C13 C 0.51248(12) 0.22334(19) 0.17165(13) 0.0230(5) Uani 1 1 d . . .
H13 H 0.5481 0.1761 0.1888 0.028 Uiso 1 1 calc R . .
C3 C 0.14519(11) 0.23648(18) 0.04943(12) 0.0170(5) Uani 1 1 d . . .
C5 C 0.06024(12) 0.1192(2) 0.05002(13) 0.0253(6) Uani 1 1 d . . .
H5 H 0.0325 0.0775 0.0525 0.030 Uiso 1 1 calc R . .
C18 C 0.32813(11) 0.17634(19) 0.27157(13) 0.0211(5) Uani 1 1 d . . .
H18 H 0.3170 0.2443 0.2466 0.025 Uiso 1 1 calc R . .
C15 C 0.20644(11) -0.11795(18) 0.01865(13) 0.0193(5) Uani 1 1 d . . .
C2 C 0.19730(11) 0.29637(18) 0.05765(12) 0.0173(5) Uani 1 1 d . . .
C4 C 0.11841(12) 0.07531(19) 0.07225(13) 0.0222(5) Uani 1 1 d . . .
H4 H 0.1291 0.0019 0.0884 0.027 Uiso 1 1 calc R . .
C16 C 0.29501(11) -0.10553(18) 0.21229(13) 0.0186(5) Uani 1 1 d . . .
C25 C 0.13097(12) -0.37076(19) -0.10582(13) 0.0230(5) Uani 1 1 d . . .
H25 H 0.1271 -0.4459 -0.1013 0.028 Uiso 1 1 calc R . .
O3 O 0.38430(9) 0.40766(13) 0.32211(10) 0.0297(4) Uani 1 1 d . . .
O4 O 0.39106(11) 0.52878(16) 0.26260(13) 0.0487(6) Uani 1 1 d . . .
O5 O 0.29866(10) 0.51324(17) 0.23808(12) 0.0471(5) Uani 1 1 d . . .
N7 N 0.35690(11) 0.48492(16) 0.27267(12) 0.0275(5) Uani 1 1 d . . .
O6 O 0.03667(9) 0.46505(13) 0.20209(9) 0.0298(4) Uani 1 1 d . . .
O7 O -0.03091(9) 0.46155(15) 0.07655(10) 0.0376(5) Uani 1 1 d . . .
O8 O 0.01613(10) 0.31372(15) 0.14401(11) 0.0429(5) Uani 1 1 d . . .
N8 N 0.00690(10) 0.41328(17) 0.13982(11) 0.0252(5) Uani 1 1 d . . .
O29 O 0.4254(2) 0.3321(3) 0.5150(2) 0.050 Uiso 0.596(6) 1 d P . .
H3W H 0.451(3) 0.292(5) 0.551(3) 0.050 Uiso 0.596(6) 1 d P . .
H4W H 0.381(3) 0.333(5) 0.487(3) 0.050 Uiso 0.596(6) 1 d P . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 2.0627(18) . ?
Zn1 N5 2.0787(18) . ?
Zn1 O2 2.1166(15) . ?
Zn1 O1 2.1514(16) . ?
Zn1 N6 2.1815(18) . ?
Zn1 N3 2.2189(19) . ?
O1 C1 1.272(3) . ?
O2 C15 1.271(3) . ?
N3 C4 1.331(3) . ?
N3 C3 1.358(3) . ?
N5 C16 1.289(3) . ?
N5 N4 1.387(3) . ?
N1 C1 1.330(3) . ?
N1 N2 1.375(3) . ?
N6 C18 1.330(3) . ?
N6 C17 1.351(3) . ?
N4 C15 1.327(3) . ?
N2 C2 1.288(3) . ?
N12 C13 1.341(3) . ?
N12 C11 1.341(3) . ?
N12 H12 0.99(3) . ?
C19 C20 1.377(4) . ?
C19 C18 1.384(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(4) . ?
C20 H20 0.9500 . ?
C21 C17 1.379(3) . ?
C21 H21 0.9500 . ?
N26 C25 1.341(3) . ?
N26 C27 1.342(3) . ?
N26 H26 0.91(3) . ?
C10 C11 1.374(3) . ?
C10 C9 1.397(3) . ?
C10 H10 0.9500 . ?
C1 C9 1.497(3) . ?
C9 C14 1.386(3) . ?
C23 C28 1.393(3) . ?
C23 C24 1.396(3) . ?
C23 C15 1.501(3) . ?
C24 C25 1.373(3) . ?
C24 H24 0.9500 . ?
C6 C5 1.378(4) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C11 H11 0.9500 . ?
C22 C16 1.487(3) . ?
C22 H22A 0.94(3) . ?
C22 H22B 0.95(3) . ?
C22 H22C 0.93(3) . ?
C8 C2 1.494(3) . ?
C8 H8A 0.97(3) . ?
C8 H8B 0.90(3) . ?
C8 H8C 0.96(3) . ?
C14 C13 1.373(3) . ?
C14 H14 0.9500 . ?
C27 C28 1.371(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C7 C3 1.385(3) . ?
C7 H7 0.9500 . ?
C17 C16 1.488(3) . ?
C13 H13 0.9500 . ?
C3 C2 1.489(3) . ?
C5 C4 1.388(3) . ?
C5 H5 0.9500 . ?
C18 H18 0.9500 . ?
C4 H4 0.9500 . ?
C25 H25 0.9500 . ?
O3 N7 1.279(3) . ?
O4 N7 1.235(3) . ?
O5 N7 1.229(3) . ?
O6 N8 1.263(3) . ?
O7 N8 1.238(3) . ?
O8 N8 1.248(3) . ?

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 N5 173.79(7) . . ?
N2 Zn1 O2 110.58(6) . . ?
N5 Zn1 O2 74.88(6) . . ?
N2 Zn1 O1 75.28(6) . . ?
N5 Zn1 O1 107.70(6) . . ?
O2 Zn1 O1 94.83(6) . . ?
N2 Zn1 N6 99.45(7) . . ?
N5 Zn1 N6 75.11(7) . . ?
O2 Zn1 N6 149.97(6) . . ?
O1 Zn1 N6 93.15(6) . . ?
N2 Zn1 N3 74.72(7) . . ?
N5 Zn1 N3 101.98(7) . . ?
O2 Zn1 N3 97.40(7) . . ?
O1 Zn1 N3 149.94(6) . . ?
N6 Zn1 N3 89.85(7) . . ?
C1 O1 Zn1 109.55(14) . . ?
C15 O2 Zn1 111.04(14) . . ?
C4 N3 C3 118.7(2) . . ?
C4 N3 Zn1 128.06(16) . . ?
C3 N3 Zn1 113.22(14) . . ?
C16 N5 N4 120.81(19) . . ?
C16 N5 Zn1 121.07(15) . . ?
N4 N5 Zn1 118.12(13) . . ?
C1 N1 N2 109.05(18) . . ?
C18 N6 C17 118.40(19) . . ?
C18 N6 Zn1 127.74(15) . . ?
C17 N6 Zn1 113.83(14) . . ?
C15 N4 N5 107.84(18) . . ?
C2 N2 N1 119.32(18) . . ?
C2 N2 Zn1 122.32(15) . . ?
N1 N2 Zn1 118.24(13) . . ?
C13 N12 C11 121.6(2) . . ?
C13 N12 H12 120.8(17) . . ?
C11 N12 H12 117.7(17) . . ?
C20 C19 C18 118.1(2) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C21 C20 C19 119.2(2) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C17 C21 C20 119.6(2) . . ?
C17 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C25 N26 C27 122.0(2) . . ?
C25 N26 H26 119(2) . . ?
C27 N26 H26 119(2) . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
O1 C1 N1 127.8(2) . . ?
O1 C1 C9 118.5(2) . . ?
N1 C1 C9 113.78(19) . . ?
C14 C9 C10 118.5(2) . . ?
C14 C9 C1 120.3(2) . . ?
C10 C9 C1 121.2(2) . . ?
C28 C23 C24 118.4(2) . . ?
C28 C23 C15 119.3(2) . . ?
C24 C23 C15 122.3(2) . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C5 C6 C7 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
N12 C11 C10 120.3(2) . . ?
N12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C16 C22 H22A 111.8(17) . . ?
C16 C22 H22B 108.6(17) . . ?
H22A C22 H22B 108(2) . . ?
C16 C22 H22C 110.5(17) . . ?
H22A C22 H22C 108(2) . . ?
H22B C22 H22C 110(2) . . ?
C2 C8 H8A 110.1(15) . . ?
C2 C8 H8B 110.3(16) . . ?
H8A C8 H8B 105(2) . . ?
C2 C8 H8C 111.3(15) . . ?
H8A C8 H8C 111(2) . . ?
H8B C8 H8C 110(2) . . ?
C13 C14 C9 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
N26 C27 C28 120.1(2) . . ?
N26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C23 119.7(2) . . ?
C27 C28 H28 120.1 . . ?
C23 C28 H28 120.1 . . ?
C3 C7 C6 119.1(2) . . ?
C3 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
N6 C17 C21 121.3(2) . . ?
N6 C17 C16 115.75(19) . . ?
C21 C17 C16 122.9(2) . . ?
N12 C13 C14 120.2(2) . . ?
N12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
N3 C3 C7 121.3(2) . . ?
N3 C3 C2 115.47(19) . . ?
C7 C3 C2 123.2(2) . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
N6 C18 C19 123.3(2) . . ?
N6 C18 H18 118.3 . . ?
C19 C18 H18 118.3 . . ?
O2 C15 N4 127.8(2) . . ?
O2 C15 C23 117.4(2) . . ?
N4 C15 C23 114.8(2) . . ?
N2 C2 C3 114.11(19) . . ?
N2 C2 C8 123.6(2) . . ?
C3 C2 C8 122.2(2) . . ?
N3 C4 C5 123.0(2) . . ?
N3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
N5 C16 C17 113.9(2) . . ?
N5 C16 C22 125.4(2) . . ?
C17 C16 C22 120.7(2) . . ?
N26 C25 C24 119.9(2) . . ?
N26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
O5 N7 O4 122.8(2) . . ?
O5 N7 O3 119.3(2) . . ?
O4 N7 O3 117.8(2) . . ?
O7 N8 O8 121.7(2) . . ?
O7 N8 O6 119.8(2) . . ?
O8 N8 O6 118.51(19) . . ?

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 Zn1 O1 C1 2.16(14) . . . . ?
N5 Zn1 O1 C1 -172.16(14) . . . . ?
O2 Zn1 O1 C1 112.19(14) . . . . ?
N6 Zn1 O1 C1 -96.79(14) . . . . ?
N3 Zn1 O1 C1 -1.6(2) . . . . ?
N2 Zn1 O2 C15 -172.17(15) . . . . ?
N5 Zn1 O2 C15 4.71(15) . . . . ?
O1 Zn1 O2 C15 111.76(15) . . . . ?
N6 Zn1 O2 C15 6.9(2) . . . . ?
N3 Zn1 O2 C15 -95.76(16) . . . . ?
N2 Zn1 N3 C4 -175.81(19) . . . . ?
N5 Zn1 N3 C4 -1.23(19) . . . . ?
O2 Zn1 N3 C4 74.81(18) . . . . ?
O1 Zn1 N3 C4 -171.99(16) . . . . ?
N6 Zn1 N3 C4 -75.97(19) . . . . ?
N2 Zn1 N3 C3 3.12(14) . . . . ?
N5 Zn1 N3 C3 177.70(14) . . . . ?
O2 Zn1 N3 C3 -106.27(14) . . . . ?
O1 Zn1 N3 C3 6.9(2) . . . . ?
N6 Zn1 N3 C3 102.96(15) . . . . ?
N2 Zn1 N5 C16 -33.4(8) . . . . ?
O2 Zn1 N5 C16 174.70(18) . . . . ?
O1 Zn1 N5 C16 84.39(18) . . . . ?
N6 Zn1 N5 C16 -4.16(17) . . . . ?
N3 Zn1 N5 C16 -90.77(18) . . . . ?
N2 Zn1 N5 N4 146.9(6) . . . . ?
O2 Zn1 N5 N4 -4.94(14) . . . . ?
O1 Zn1 N5 N4 -95.24(15) . . . . ?
N6 Zn1 N5 N4 176.21(16) . . . . ?
N3 Zn1 N5 N4 89.60(15) . . . . ?
N2 Zn1 N6 C18 0.2(2) . . . . ?
N5 Zn1 N6 C18 -176.7(2) . . . . ?
O2 Zn1 N6 C18 -178.91(17) . . . . ?
O1 Zn1 N6 C18 75.82(19) . . . . ?
N3 Zn1 N6 C18 -74.26(19) . . . . ?
N2 Zn1 N6 C17 -177.95(15) . . . . ?
N5 Zn1 N6 C17 5.12(15) . . . . ?
O2 Zn1 N6 C17 2.9(2) . . . . ?
O1 Zn1 N6 C17 -102.36(15) . . . . ?
N3 Zn1 N6 C17 107.57(15) . . . . ?
C16 N5 N4 C15 -175.5(2) . . . . ?
Zn1 N5 N4 C15 4.1(2) . . . . ?
C1 N1 N2 C2 179.80(19) . . . . ?
C1 N1 N2 Zn1 3.6(2) . . . . ?
N5 Zn1 N2 C2 -59.9(7) . . . . ?
O2 Zn1 N2 C2 90.99(17) . . . . ?
O1 Zn1 N2 C2 -179.34(18) . . . . ?
N6 Zn1 N2 C2 -88.55(17) . . . . ?
N3 Zn1 N2 C2 -1.31(16) . . . . ?
N5 Zn1 N2 N1 116.2(7) . . . . ?
O2 Zn1 N2 N1 -92.91(15) . . . . ?
O1 Zn1 N2 N1 -3.24(14) . . . . ?
N6 Zn1 N2 N1 87.55(15) . . . . ?
N3 Zn1 N2 N1 174.79(16) . . . . ?
C18 C19 C20 C21 -2.0(4) . . . . ?
C19 C20 C21 C17 0.5(4) . . . . ?
Zn1 O1 C1 N1 -1.0(3) . . . . ?
Zn1 O1 C1 C9 178.96(14) . . . . ?
N2 N1 C1 O1 -1.6(3) . . . . ?
N2 N1 C1 C9 178.45(17) . . . . ?
C11 C10 C9 C14 -0.8(3) . . . . ?
C11 C10 C9 C1 -179.7(2) . . . . ?
O1 C1 C9 C14 0.1(3) . . . . ?
N1 C1 C9 C14 -179.9(2) . . . . ?
O1 C1 C9 C10 179.0(2) . . . . ?
N1 C1 C9 C10 -1.1(3) . . . . ?
C28 C23 C24 C25 -0.5(3) . . . . ?
C15 C23 C24 C25 -179.3(2) . . . . ?
C13 N12 C11 C10 0.6(3) . . . . ?
C9 C10 C11 N12 0.3(3) . . . . ?
C10 C9 C14 C13 0.6(3) . . . . ?
C1 C9 C14 C13 179.4(2) . . . . ?
C25 N26 C27 C28 -0.1(4) . . . . ?
N26 C27 C28 C23 -1.7(4) . . . . ?
C24 C23 C28 C27 1.9(3) . . . . ?
C15 C23 C28 C27 -179.2(2) . . . . ?
C5 C6 C7 C3 -1.3(3) . . . . ?
C18 N6 C17 C21 -2.7(3) . . . . ?
Zn1 N6 C17 C21 175.70(17) . . . . ?
C18 N6 C17 C16 176.00(19) . . . . ?
Zn1 N6 C17 C16 -5.6(2) . . . . ?
C20 C21 C17 N6 1.8(4) . . . . ?
C20 C21 C17 C16 -176.7(2) . . . . ?
C11 N12 C13 C14 -0.8(3) . . . . ?
C9 C14 C13 N12 0.2(3) . . . . ?
C4 N3 C3 C7 -3.4(3) . . . . ?
Zn1 N3 C3 C7 177.56(16) . . . . ?
C4 N3 C3 C2 174.60(19) . . . . ?
Zn1 N3 C3 C2 -4.4(2) . . . . ?
C6 C7 C3 N3 3.9(3) . . . . ?
C6 C7 C3 C2 -174.0(2) . . . . ?
C7 C6 C5 C4 -1.5(3) . . . . ?
C17 N6 C18 C19 1.1(3) . . . . ?
Zn1 N6 C18 C19 -176.96(17) . . . . ?
C20 C19 C18 N6 1.2(4) . . . . ?
Zn1 O2 C15 N4 -4.7(3) . . . . ?
Zn1 O2 C15 C23 175.47(15) . . . . ?
N5 N4 C15 O2 0.6(3) . . . . ?
N5 N4 C15 C23 -179.53(18) . . . . ?
C28 C23 C15 O2 1.6(3) . . . . ?
C24 C23 C15 O2 -179.6(2) . . . . ?
C28 C23 C15 N4 -178.3(2) . . . . ?
C24 C23 C15 N4 0.6(3) . . . . ?
N1 N2 C2 C3 -176.68(17) . . . . ?
Zn1 N2 C2 C3 -0.6(3) . . . . ?
N1 N2 C2 C8 0.3(3) . . . . ?
Zn1 N2 C2 C8 176.35(17) . . . . ?
N3 C3 C2 N2 3.5(3) . . . . ?
C7 C3 C2 N2 -178.5(2) . . . . ?
N3 C3 C2 C8 -173.5(2) . . . . ?
C7 C3 C2 C8 4.4(3) . . . . ?
C3 N3 C4 C5 0.4(3) . . . . ?
Zn1 N3 C4 C5 179.30(16) . . . . ?
C6 C5 C4 N3 2.0(3) . . . . ?
N4 N5 C16 C17 -177.92(18) . . . . ?
Zn1 N5 C16 C17 2.5(3) . . . . ?
N4 N5 C16 C22 1.3(3) . . . . ?
Zn1 N5 C16 C22 -178.29(19) . . . . ?
N6 C17 C16 N5 2.4(3) . . . . ?
C21 C17 C16 N5 -179.0(2) . . . . ?
N6 C17 C16 C22 -176.9(2) . . . . ?
C21 C17 C16 C22 1.7(3) . . . . ?
C27 N26 C25 C24 1.6(4) . . . . ?
C23 C24 C25 N26 -1.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.046
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1461713'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Cd N8 O2'
_chemical_formula_weight         590.91
_chemical_oxdiff_usercomment     'Farhad sample 501-A'

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   12.4748(3)
_cell_length_b                   19.5344(3)
_cell_length_c                   10.0185(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2441.39(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.0(1)
_cell_measurement_reflns_used    10148
_cell_measurement_theta_min      3.2550
_cell_measurement_theta_max      34.0290

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3933
_exptl_crystal_size_mid          0.3015
_exptl_crystal_size_min          0.1158
_exptl_absorpt_coefficient_mu    0.936
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.78811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.0(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22337
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.128
_diffrn_reflns_theta_max         34.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_point_group_measured_fraction_full 0.858
_reflns_number_total             7997
_reflns_number_gt                6584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.554
_reflns_Friedel_fraction_max     0.578
_reflns_Friedel_fraction_full    0.699

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_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)+(0.0313P)²+0.2397P]
 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_abs_structure_details 
;
 Flack x determined using 2139 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.046(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7997
_refine_ls_number_parameters     336
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.6239(2) 0.13991(13) 0.3045(3) 0.0202(5) Uani 1 1 d . . . . .
C2 C 0.6531(2) 0.08891(13) 0.4089(3) 0.0231(5) Uani 1 1 d . . . . .
C3 C 0.5740(2) 0.05820(15) 0.4861(3) 0.0328(7) Uani 1 1 d . . . . .
H3 H 0.5019 0.0677 0.4712 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6047(3) 0.01297(16) 0.5860(4) 0.0399(8) Uani 1 1 d . . . . .
H4 H 0.5511 -0.0072 0.6370 0.048 Uiso 1 1 calc R U . . .
C6 C 0.7796(3) 0.02600(16) 0.5381(4) 0.0362(7) Uani 1 1 d . . . . .
H6 H 0.8509 0.0152 0.5551 0.043 Uiso 1 1 calc R U . . .
C7 C 0.7586(2) 0.07159(14) 0.4358(3) 0.0287(6) Uani 1 1 d . . . . .
H7 H 0.8143 0.0903 0.3860 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7428(2) 0.24780(12) 0.0812(3) 0.0181(5) Uani 1 1 d . . . . .
C9 C 0.69940(19) 0.29811(12) -0.0165(3) 0.0190(5) Uani 1 1 d . . . . .
C10 C 0.7653(2) 0.33521(12) -0.1013(3) 0.0247(6) Uani 1 1 d . . . . .
H10 H 0.8391 0.3289 -0.0987 0.030 Uiso 1 1 calc R U . . .
C11 C 0.7212(2) 0.38155(14) -0.1895(3) 0.0311(7) Uani 1 1 d . . . . .
H11 H 0.7649 0.4069 -0.2463 0.037 Uiso 1 1 calc R U . . .
C12 C 0.6108(3) 0.38978(15) -0.1923(3) 0.0321(7) Uani 1 1 d . . . . .
H12 H 0.5785 0.4206 -0.2507 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5505(2) 0.35083(14) -0.1057(3) 0.0250(5) Uani 1 1 d . . . . .
H13 H 0.4763 0.3558 -0.1078 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8612(2) 0.23776(15) 0.0937(3) 0.0265(6) Uani 1 1 d . . . . .
H15A H 0.8931 0.2783 0.1306 0.040 Uiso 1 1 calc R U . . .
H15B H 0.8912 0.2290 0.0072 0.040 Uiso 1 1 calc R U . . .
H15C H 0.8753 0.1996 0.1514 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3974(2) 0.35655(13) 0.3167(3) 0.0195(5) Uani 1 1 d . . . . .
C17 C 0.3838(2) 0.41348(13) 0.4150(3) 0.0215(5) Uani 1 1 d . . . . .
C18 C 0.2846(2) 0.43124(16) 0.4664(4) 0.0357(8) Uani 1 1 d . . . . .
H18 H 0.2227 0.4098 0.4357 0.043 Uiso 1 1 calc R U . . .
C19 C 0.2788(3) 0.48129(18) 0.5639(4) 0.0461(10) Uani 1 1 d . . . . .
H19 H 0.2117 0.4916 0.5990 0.055 Uiso 1 1 calc R U . . .
C21 C 0.4575(2) 0.49952(14) 0.5581(3) 0.0305(6) Uani 1 1 d . . . . .
H21 H 0.5174 0.5235 0.5874 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4721(2) 0.44950(15) 0.4626(3) 0.0268(6) Uani 1 1 d . . . . .
H22 H 0.5404 0.4399 0.4303 0.032 Uiso 1 1 calc R U . . .
C23 C 0.2493(2) 0.25681(12) 0.1057(3) 0.0194(5) Uani 1 1 d . . . . .
C24 C 0.27753(19) 0.20338(13) 0.0074(3) 0.0192(5) Uani 1 1 d . . . . .
C25 C 0.2010(2) 0.17217(14) -0.0723(3) 0.0244(6) Uani 1 1 d . . . . .
H25 H 0.1291 0.1841 -0.0640 0.029 Uiso 1 1 calc R U . . .
C26 C 0.2320(2) 0.12322(14) -0.1643(3) 0.0286(6) Uani 1 1 d . . . . .
H26 H 0.1813 0.1021 -0.2186 0.034 Uiso 1 1 calc R U . . .
C27 C 0.3383(2) 0.10623(16) -0.1746(3) 0.0315(7) Uani 1 1 d . . . . .
H27 H 0.3611 0.0735 -0.2357 0.038 Uiso 1 1 calc R U . . .
C28 C 0.4113(2) 0.13900(14) -0.0915(3) 0.0273(6) Uani 1 1 d . . . . .
H28 H 0.4834 0.1273 -0.0981 0.033 Uiso 1 1 calc R U . . .
C29 C 0.13418(19) 0.27397(15) 0.1327(4) 0.0289(6) Uani 1 1 d . . . . .
H29A H 0.1007 0.2366 0.1789 0.043 Uiso 1 1 calc R U . . .
H29B H 0.0978 0.2818 0.0497 0.043 Uiso 1 1 calc R U . . .
H29C H 0.1304 0.3145 0.1867 0.043 Uiso 1 1 calc R U . . .
N1 N 0.70748(16) 0.16893(11) 0.2442(2) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.67319(14) 0.21585(9) 0.1511(3) 0.0176(4) Uani 1 1 d . . . . .
N3 N 0.59210(16) 0.30647(10) -0.0192(2) 0.0192(4) Uani 1 1 d . . . . .
N4 N 0.30666(17) 0.33626(11) 0.2586(2) 0.0219(5) Uani 1 1 d . . . . .
N5 N 0.32793(15) 0.28548(10) 0.1668(2) 0.0197(5) Uani 1 1 d . . . . .
N6 N 0.38260(16) 0.18642(11) -0.0029(2) 0.0208(4) Uani 1 1 d . . . . .
N7 N 0.7056(2) -0.00335(13) 0.6136(3) 0.0386(7) Uani 1 1 d . . . . .
N8 N 0.3627(2) 0.51568(12) 0.6110(3) 0.0354(7) Uani 1 1 d . . . . .
Cd Cd 0.49757(2) 0.24457(2) 0.14600(7) 0.01628(5) Uani 1 1 d . . . . .
O1 O 0.52502(16) 0.15170(11) 0.2839(2) 0.0289(5) Uani 1 1 d . . . . .
O2 O 0.49055(13) 0.33265(13) 0.3000(3) 0.0304(5) 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
C1 O1 1.272(3) . ?
C1 N1 1.331(3) . ?
C1 C2 1.490(4) . ?
C2 C7 1.386(4) . ?
C2 C3 1.390(4) . ?
C3 C4 1.389(4) . ?
C4 N7 1.327(4) . ?
C6 N7 1.323(4) . ?
C6 C7 1.383(4) . ?
C8 N2 1.278(3) . ?
C8 C9 1.489(4) . ?
C8 C15 1.495(4) . ?
C9 N3 1.349(3) . ?
C9 C10 1.386(4) . ?
C10 C11 1.379(4) . ?
C11 C12 1.388(4) . ?
C12 C13 1.378(4) . ?
C13 N3 1.331(3) . ?
C16 O2 1.264(3) . ?
C16 N4 1.333(3) . ?
C16 C17 1.495(4) . ?
C17 C18 1.385(4) . ?
C17 C22 1.391(4) . ?
C18 C19 1.384(4) . ?
C19 N8 1.330(4) . ?
C21 N8 1.333(4) . ?
C21 C22 1.379(4) . ?
C23 N5 1.284(3) . ?
C23 C24 1.478(4) . ?
C23 C29 1.499(4) . ?
C24 N6 1.356(3) . ?
C24 C25 1.386(3) . ?
C25 C26 1.383(4) . ?
C26 C27 1.371(4) . ?
C27 C28 1.390(4) . ?
C28 N6 1.332(3) . ?
N1 N2 1.376(3) . ?
N2 Cd 2.2621(17) . ?
N3 Cd 2.365(2) . ?
N4 N5 1.379(3) . ?
N5 Cd 2.2716(19) . ?
N6 Cd 2.361(2) . ?
Cd O1 2.306(2) . ?
Cd O2 2.313(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 127.5(2) . . ?
O1 C1 C2 118.1(2) . . ?
N1 C1 C2 114.4(2) . . ?
C7 C2 C3 117.4(3) . . ?
C7 C2 C1 122.1(2) . . ?
C3 C2 C1 120.4(2) . . ?
C4 C3 C2 118.7(3) . . ?
N7 C4 C3 124.4(3) . . ?
N7 C6 C7 124.8(3) . . ?
C6 C7 C2 118.8(3) . . ?
N2 C8 C9 115.8(2) . . ?
N2 C8 C15 124.1(3) . . ?
C9 C8 C15 120.0(2) . . ?
N3 C9 C10 120.9(3) . . ?
N3 C9 C8 117.0(2) . . ?
C10 C9 C8 122.2(2) . . ?
C11 C10 C9 120.0(3) . . ?
C10 C11 C12 119.0(3) . . ?
C13 C12 C11 117.8(3) . . ?
N3 C13 C12 123.8(3) . . ?
O2 C16 N4 127.8(2) . . ?
O2 C16 C17 117.8(2) . . ?
N4 C16 C17 114.4(2) . . ?
C18 C17 C22 117.0(3) . . ?
C18 C17 C16 122.2(2) . . ?
C22 C17 C16 120.8(2) . . ?
C19 C18 C17 119.1(3) . . ?
N8 C19 C18 124.5(3) . . ?
N8 C21 C22 124.1(3) . . ?
C21 C22 C17 119.4(3) . . ?
N5 C23 C24 116.3(2) . . ?
N5 C23 C29 123.3(3) . . ?
C24 C23 C29 120.4(2) . . ?
N6 C24 C25 121.0(2) . . ?
N6 C24 C23 117.0(2) . . ?
C25 C24 C23 122.0(2) . . ?
C26 C25 C24 119.7(2) . . ?
C27 C26 C25 119.2(3) . . ?
C26 C27 C28 118.5(3) . . ?
N6 C28 C27 122.9(3) . . ?
C1 N1 N2 110.36(19) . . ?
C8 N2 N1 119.0(2) . . ?
C8 N2 Cd 121.63(18) . . ?
N1 N2 Cd 118.80(15) . . ?
C13 N3 C9 118.6(2) . . ?
C13 N3 Cd 126.44(17) . . ?
C9 N3 Cd 114.78(18) . . ?
C16 N4 N5 110.0(2) . . ?
C23 N5 N4 119.0(2) . . ?
C23 N5 Cd 120.96(18) . . ?
N4 N5 Cd 119.57(15) . . ?
C28 N6 C24 118.7(2) . . ?
C28 N6 Cd 126.34(17) . . ?
C24 N6 Cd 114.93(17) . . ?
C6 N7 C4 116.0(3) . . ?
C19 N8 C21 115.9(3) . . ?
N2 Cd N5 170.90(9) . . ?
N2 Cd O1 69.36(8) . . ?
N5 Cd O1 111.11(8) . . ?
N2 Cd O2 101.89(7) . . ?
N5 Cd O2 69.02(7) . . ?
O1 Cd O2 101.03(11) . . ?
N2 Cd N6 118.90(8) . . ?
N5 Cd N6 70.20(7) . . ?
O1 Cd N6 95.18(8) . . ?
O2 Cd N6 139.17(7) . . ?
N2 Cd N3 70.10(8) . . ?
N5 Cd N3 110.42(8) . . ?
O1 Cd N3 138.38(7) . . ?
O2 Cd N3 96.06(9) . . ?
N6 Cd N3 96.12(9) . . ?
C1 O1 Cd 112.56(17) . . ?
C16 O2 Cd 113.45(17) . . ?

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 C7 178.4(3) . . . . ?
N1 C1 C2 C7 -2.6(4) . . . . ?
O1 C1 C2 C3 -3.5(4) . . . . ?
N1 C1 C2 C3 175.5(3) . . . . ?
C7 C2 C3 C4 0.8(5) . . . . ?
C1 C2 C3 C4 -177.5(3) . . . . ?
C2 C3 C4 N7 0.0(5) . . . . ?
N7 C6 C7 C2 0.4(5) . . . . ?
C3 C2 C7 C6 -0.9(4) . . . . ?
C1 C2 C7 C6 177.3(3) . . . . ?
N2 C8 C9 N3 1.8(4) . . . . ?
C15 C8 C9 N3 -177.6(2) . . . . ?
N2 C8 C9 C10 -178.4(3) . . . . ?
C15 C8 C9 C10 2.2(4) . . . . ?
N3 C9 C10 C11 0.2(4) . . . . ?
C8 C9 C10 C11 -179.6(3) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 N3 0.7(5) . . . . ?
O2 C16 C17 C18 -162.9(3) . . . . ?
N4 C16 C17 C18 15.8(4) . . . . ?
O2 C16 C17 C22 14.8(4) . . . . ?
N4 C16 C17 C22 -166.6(3) . . . . ?
C22 C17 C18 C19 -2.2(5) . . . . ?
C16 C17 C18 C19 175.5(3) . . . . ?
C17 C18 C19 N8 1.8(6) . . . . ?
N8 C21 C22 C17 1.0(5) . . . . ?
C18 C17 C22 C21 0.9(4) . . . . ?
C16 C17 C22 C21 -176.9(3) . . . . ?
N5 C23 C24 N6 4.2(4) . . . . ?
C29 C23 C24 N6 -174.3(3) . . . . ?
N5 C23 C24 C25 -175.1(3) . . . . ?
C29 C23 C24 C25 6.4(4) . . . . ?
N6 C24 C25 C26 -0.3(4) . . . . ?
C23 C24 C25 C26 179.0(3) . . . . ?
C24 C25 C26 C27 0.3(4) . . . . ?
C25 C26 C27 C28 0.0(5) . . . . ?
C26 C27 C28 N6 -0.4(5) . . . . ?
O1 C1 N1 N2 -0.2(4) . . . . ?
C2 C1 N1 N2 -179.1(2) . . . . ?
C9 C8 N2 N1 -179.5(2) . . . . ?
C15 C8 N2 N1 -0.1(4) . . . . ?
C9 C8 N2 Cd -8.0(3) . . . . ?
C15 C8 N2 Cd 171.4(2) . . . . ?
C1 N1 N2 C8 -178.5(2) . . . . ?
C1 N1 N2 Cd 9.7(3) . . . . ?
C12 C13 N3 C9 -0.9(4) . . . . ?
C12 C13 N3 Cd 174.2(2) . . . . ?
C10 C9 N3 C13 0.5(4) . . . . ?
C8 C9 N3 C13 -179.7(2) . . . . ?
C10 C9 N3 Cd -175.2(2) . . . . ?
C8 C9 N3 Cd 4.6(3) . . . . ?
O2 C16 N4 N5 -3.5(4) . . . . ?
C17 C16 N4 N5 177.9(2) . . . . ?
C24 C23 N5 N4 179.3(2) . . . . ?
C29 C23 N5 N4 -2.3(4) . . . . ?
C24 C23 N5 Cd -8.8(3) . . . . ?
C29 C23 N5 Cd 169.7(2) . . . . ?
C16 N4 N5 C23 176.3(2) . . . . ?
C16 N4 N5 Cd 4.2(3) . . . . ?
C27 C28 N6 C24 0.3(4) . . . . ?
C27 C28 N6 Cd 179.0(2) . . . . ?
C25 C24 N6 C28 0.0(4) . . . . ?
C23 C24 N6 C28 -179.3(2) . . . . ?
C25 C24 N6 Cd -178.8(2) . . . . ?
C23 C24 N6 Cd 1.9(3) . . . . ?
C7 C6 N7 C4 0.4(5) . . . . ?
C3 C4 N7 C6 -0.5(5) . . . . ?
C18 C19 N8 C21 0.1(6) . . . . ?
C22 C21 N8 C19 -1.5(5) . . . . ?
N1 C1 O1 Cd -8.8(4) . . . . ?
C2 C1 O1 Cd 170.10(19) . . . . ?
N4 C16 O2 Cd 1.1(4) . . . . ?
C17 C16 O2 Cd 179.61(19) . . . . ?

_refine_diff_density_max         0.759
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.078

_shelxl_version_number           2012-9

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1461714'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 I2 N4 O Zn'
_chemical_formula_weight         559.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   7.5604(3)
_cell_length_b                   8.0042(3)
_cell_length_c                   15.2219(6)
_cell_angle_alpha                93.114(2)
_cell_angle_beta                 103.265(2)
_cell_angle_gamma                115.536(2)
_cell_volume                     796.58(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8546
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      34.93

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.332
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    5.420
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6201
_exptl_absorpt_correction_T_max  0.6201
_exptl_absorpt_process_details   'Bruker AXScale'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26749
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.396
_diffrn_reflns_theta_max         35.062
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6965
_reflns_number_gt                5802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+0.0269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6965
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0649
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
O1 O 0.1911(3) 0.8540(2) 0.63948(12) 0.0213(3) Uani 1 1 d . . . . .
Zn1 Zn 0.21133(4) 0.71941(4) 0.75833(2) 0.01568(5) Uani 1 1 d . . . . .
I1 I -0.12511(2) 0.68048(2) 0.79277(2) 0.01722(4) Uani 1 1 d . . . . .
I2 I 0.19855(2) 0.40666(2) 0.68674(2) 0.01929(4) Uani 1 1 d . . . . .
C1 C 0.5733(3) 0.8729(3) 0.92822(14) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.3121(4) 0.6241(3) 0.96168(17) 0.0196(4) Uani 1 1 d . . . . .
H2A H 0.1760 0.5258 0.9431 0.024 Uiso 1 1 calc R U . . .
C3 C 0.4317(4) 0.6475(4) 1.05039(17) 0.0215(4) Uani 1 1 d . . . . .
H3A H 0.3783 0.5671 1.0914 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6292(4) 0.7901(4) 1.07724(16) 0.0206(4) Uani 1 1 d . . . . .
H4A H 0.7143 0.8102 1.1374 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7022(3) 0.9043(3) 1.01505(15) 0.0181(4) Uani 1 1 d . . . . .
H5A H 0.8384 1.0023 1.0318 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6351(3) 0.9931(3) 0.85863(15) 0.0149(3) Uani 1 1 d . . . . .
C7 C 0.8425(3) 1.1536(3) 0.87566(17) 0.0203(4) Uani 1 1 d . . . . .
H7A H 0.8319 1.2556 0.8458 0.030 Uiso 1 1 calc R U . . .
H7B H 0.9282 1.1121 0.8506 0.030 Uiso 1 1 calc R U . . .
H7C H 0.9040 1.1986 0.9418 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3646(3) 0.9918(3) 0.64685(15) 0.0158(4) Uani 1 1 d . . . . .
C9 C 0.3915(3) 1.0960(3) 0.56827(15) 0.0162(4) Uani 1 1 d . . . . .
C10 C 0.5766(4) 1.2536(3) 0.57393(16) 0.0192(4) Uani 1 1 d . . . . .
H10A H 0.6855 1.3006 0.6289 0.023 Uiso 1 1 calc R U . . .
C11 C 0.5971(4) 1.3393(3) 0.49773(18) 0.0227(4) Uani 1 1 d . . . . .
H11A H 0.7223 1.4440 0.4993 0.027 Uiso 1 1 calc R U . . .
C12 C 0.2597(4) 1.1241(4) 0.41409(16) 0.0229(5) Uani 1 1 d . . . . .
H12A H 0.1519 1.0820 0.3589 0.027 Uiso 1 1 calc R U . . .
C13 C 0.2338(4) 1.0321(3) 0.48777(16) 0.0192(4) Uani 1 1 d . . . . .
H13A H 0.1081 0.9253 0.4833 0.023 Uiso 1 1 calc R U . . .
N1 N 0.3802(3) 0.7336(3) 0.90171(13) 0.0160(3) Uani 1 1 d . . . . .
N2 N 0.4913(3) 0.9488(3) 0.78348(13) 0.0143(3) Uani 1 1 d . . . . .
N3 N 0.5328(3) 1.0556(3) 0.71574(13) 0.0159(3) Uani 1 1 d . . . . .
N4 N 0.4386(4) 1.2732(3) 0.42136(15) 0.0230(4) Uani 1 1 d . . . . .
H4B H 0.448(5) 1.321(5) 0.376(2) 0.028 Uiso 1 1 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
O1 C8 1.273(3) . ?
O1 Zn1 2.1643(17) . ?
Zn1 N2 2.0495(19) . ?
Zn1 N1 2.2307(18) . ?
Zn1 I1 2.6055(3) . ?
Zn1 I2 2.6287(3) . ?
C1 N1 1.347(3) . ?
C1 C5 1.386(3) . ?
C1 C6 1.489(3) . ?
C2 N1 1.334(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.378(4) . ?
C4 C5 1.391(3) . ?
C6 N2 1.292(3) . ?
C6 C7 1.489(3) . ?
C8 N3 1.322(3) . ?
C8 C9 1.497(3) . ?
C9 C13 1.386(3) . ?
C9 C10 1.403(3) . ?
C10 C11 1.384(3) . ?
C11 N4 1.347(4) . ?
C12 N4 1.339(4) . ?
C12 C13 1.380(3) . ?
N2 N3 1.380(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 Zn1 109.02(14) . . ?
N2 Zn1 O1 74.97(7) . . ?
N2 Zn1 N1 74.26(7) . . ?
O1 Zn1 N1 148.52(7) . . ?
N2 Zn1 I1 131.45(5) . . ?
O1 Zn1 I1 98.49(5) . . ?
N1 Zn1 I1 96.80(5) . . ?
N2 Zn1 I2 113.63(5) . . ?
O1 Zn1 I2 101.07(5) . . ?
N1 Zn1 I2 97.17(5) . . ?
I1 Zn1 I2 114.821(11) . . ?
N1 C1 C5 122.0(2) . . ?
N1 C1 C6 115.13(18) . . ?
C5 C1 C6 122.8(2) . . ?
N1 C2 C3 123.0(2) . . ?
C4 C3 C2 118.4(2) . . ?
C3 C4 C5 119.1(2) . . ?
C1 C5 C4 119.0(2) . . ?
N2 C6 C1 114.04(19) . . ?
N2 C6 C7 123.2(2) . . ?
C1 C6 C7 122.72(19) . . ?
O1 C8 N3 128.2(2) . . ?
O1 C8 C9 118.4(2) . . ?
N3 C8 C9 113.4(2) . . ?
C13 C9 C10 119.5(2) . . ?
C13 C9 C8 119.5(2) . . ?
C10 C9 C8 120.9(2) . . ?
C11 C10 C9 118.6(2) . . ?
N4 C11 C10 119.6(2) . . ?
N4 C12 C13 119.2(2) . . ?
C12 C13 C9 119.9(2) . . ?
C2 N1 C1 118.42(19) . . ?
C2 N1 Zn1 127.99(16) . . ?
C1 N1 Zn1 113.58(14) . . ?
C6 N2 N3 118.21(18) . . ?
C6 N2 Zn1 122.77(15) . . ?
N3 N2 Zn1 118.93(14) . . ?
C8 N3 N2 108.47(18) . . ?
C12 N4 C11 123.1(2) . . ?

_refine_diff_density_max         1.509
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.158

_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_2
_database_code_depnum_ccdc_archive 'CCDC 1461715'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 Br2 N4 O Zn'
_chemical_formula_weight         465.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5331(9)
_cell_length_b                   7.8320(10)
_cell_length_c                   14.7352(18)
_cell_angle_alpha                93.2690(10)
_cell_angle_beta                 103.0100(10)
_cell_angle_gamma                116.0050(10)
_cell_volume                     749.16(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    132(2)
_cell_measurement_reflns_used    5566
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.38

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.063
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    6.975
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3870
_exptl_absorpt_correction_T_max  0.6336
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      132(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8661
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         27.10
_reflns_number_total             3282
_reflns_number_gt                2856
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (Bruker, 2007)'
_computing_cell_refinement       'Bruker SAINT  (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT  (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL  (Bruker, 2007)'
_computing_publication_material  'Bruker SHELXTL  (Bruker, 2007)'

_refine_special_details          
; 
A suitable crystal was mounted in a nylon loop with Paratone-N
 cryoprotectant oil and data collected on a Bruker APEX 2 CCD 
platform diffractometer. The structure was solved using 
direct methods and standard difference map techniques, 
and was refined by full-matrix least-squares procedures 
on F2 with SHELXTL Version 6.14 (Sheldrick, 2008).  

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)+(0.0231P)²+0.5360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3282
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0508
_refine_ls_wR_factor_gt          0.0488
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Zn Zn -0.80148(4) 0.70952(4) 0.75779(2) 0.01652(8) Uani 1 1 d . . .
Br1 Br -1.11044(4) 0.67684(4) 0.793552(18) 0.02020(7) Uani 1 1 d . . .
Br2 Br -0.80933(4) 0.41700(4) 0.687738(18) 0.02268(7) Uani 1 1 d . . .
N2 N -0.5156(3) 0.9418(3) 0.78270(14) 0.0152(4) Uani 1 1 d . . .
C33 C -0.7373(5) 1.1339(4) 0.40364(19) 0.0262(6) Uani 1 1 d . . .
H33A H -0.8434 1.0925 0.3459 0.031 Uiso 1 1 calc R . .
O O -0.8201(3) 0.8521(3) 0.63584(12) 0.0215(4) Uani 1 1 d . . .
N1 N -0.6299(3) 0.7241(3) 0.90566(14) 0.0162(4) Uani 1 1 d . . .
N4 N -0.5547(4) 1.2856(4) 0.41292(17) 0.0272(5) Uani 1 1 d . . .
C11 C -0.4311(4) 0.8625(3) 0.93086(17) 0.0145(5) Uani 1 1 d . . .
C16 C -0.3006(4) 0.8923(4) 1.02013(17) 0.0183(5) Uani 1 1 d . . .
H16A H -0.1616 0.9900 1.0366 0.022 Uiso 1 1 calc R . .
C3 C -0.6440(4) 0.9914(4) 0.64310(17) 0.0167(5) Uani 1 1 d . . .
C36 C -0.4236(4) 1.2608(4) 0.56968(19) 0.0222(6) Uani 1 1 d . . .
H36A H -0.3153 1.3066 0.6268 0.027 Uiso 1 1 calc R . .
C31 C -0.6131(4) 1.1007(4) 0.56267(17) 0.0173(5) Uani 1 1 d . . .
C13 C -0.6995(4) 0.6155(4) 0.96910(18) 0.0200(5) Uani 1 1 d . . .
H13A H -0.8391 0.5191 0.9517 0.024 Uiso 1 1 calc R . .
C15 C -0.3748(4) 0.7784(4) 1.08502(18) 0.0211(5) Uani 1 1 d . . .
H15A H -0.2876 0.7974 1.1464 0.025 Uiso 1 1 calc R . .
C32 C -0.7699(4) 1.0382(4) 0.47867(18) 0.0211(5) Uani 1 1 d . . .
H32A H -0.8989 0.9300 0.4730 0.025 Uiso 1 1 calc R . .
C2 C -0.1564(4) 1.1408(4) 0.87332(19) 0.0207(5) Uani 1 1 d . . .
H2A H -0.1485 1.2025 0.8173 0.031 Uiso 1 1 calc R . .
H2B H -0.0598 1.0866 0.8835 0.031 Uiso 1 1 calc R . .
H2C H -0.1208 1.2367 0.9288 0.031 Uiso 1 1 calc R . .
C14 C -0.5769(4) 0.6373(4) 1.05912(18) 0.0214(5) Uani 1 1 d . . .
H14A H -0.6312 0.5566 1.1021 0.026 Uiso 1 1 calc R . .
C1 C -0.3697(4) 0.9830(3) 0.85847(17) 0.0153(5) Uani 1 1 d . . .
C35 C -0.3972(5) 1.3503(4) 0.49261(19) 0.0250(6) Uani 1 1 d . . .
H35A H -0.2690 1.4569 0.4954 0.030 Uiso 1 1 calc R . .
N3 N -0.4737(3) 1.0531(3) 0.71337(14) 0.0164(4) Uani 1 1 d . . .
H1 H -0.534(5) 1.339(5) 0.367(2) 0.035(9) 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
Zn N2 2.053(2) . ?
Zn O 2.1791(17) . ?
Zn N1 2.237(2) . ?
Zn Br1 2.4094(5) . ?
Zn Br2 2.4293(5) . ?
N2 C1 1.286(3) . ?
N2 N3 1.382(3) . ?
C33 N4 1.336(4) . ?
C33 C32 1.378(4) . ?
C33 H33A 0.9500 . ?
O C3 1.271(3) . ?
N1 C13 1.339(3) . ?
N1 C11 1.355(3) . ?
N4 C35 1.349(4) . ?
N4 H1 0.82(3) . ?
C11 C16 1.390(3) . ?
C11 C1 1.482(3) . ?
C16 C15 1.387(4) . ?
C16 H16A 0.9500 . ?
C3 N3 1.324(3) . ?
C3 C31 1.502(3) . ?
C36 C35 1.375(4) . ?
C36 C31 1.403(4) . ?
C36 H36A 0.9500 . ?
C31 C32 1.390(4) . ?
C13 C14 1.388(4) . ?
C13 H13A 0.9500 . ?
C15 C14 1.378(4) . ?
C15 H15A 0.9500 . ?
C32 H32A 0.9500 . ?
C2 C1 1.492(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C14 H14A 0.9500 . ?
C35 H35A 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 Zn O 74.80(7) . . ?
N2 Zn N1 74.06(8) . . ?
O Zn N1 147.90(7) . . ?
N2 Zn Br1 131.83(6) . . ?
O Zn Br1 98.40(5) . . ?
N1 Zn Br1 96.50(5) . . ?
N2 Zn Br2 111.19(6) . . ?
O Zn Br2 101.26(5) . . ?
N1 Zn Br2 97.04(5) . . ?
Br1 Zn Br2 116.858(14) . . ?
C1 N2 N3 118.2(2) . . ?
C1 N2 Zn 122.76(17) . . ?
N3 N2 Zn 118.96(15) . . ?
N4 C33 C32 119.3(3) . . ?
N4 C33 H33A 120.4 . . ?
C32 C33 H33A 120.4 . . ?
C3 O Zn 109.02(15) . . ?
C13 N1 C11 118.4(2) . . ?
C13 N1 Zn 128.27(17) . . ?
C11 N1 Zn 113.32(15) . . ?
C33 N4 C35 123.2(2) . . ?
C33 N4 H1 119(2) . . ?
C35 N4 H1 118(2) . . ?
N1 C11 C16 121.4(2) . . ?
N1 C11 C1 114.9(2) . . ?
C16 C11 C1 123.6(2) . . ?
C15 C16 C11 119.5(2) . . ?
C15 C16 H16A 120.2 . . ?
C11 C16 H16A 120.2 . . ?
O C3 N3 128.1(2) . . ?
O C3 C31 118.9(2) . . ?
N3 C3 C31 113.0(2) . . ?
C35 C36 C31 119.0(3) . . ?
C35 C36 H36A 120.5 . . ?
C31 C36 H36A 120.5 . . ?
C32 C31 C36 119.3(2) . . ?
C32 C31 C3 120.0(2) . . ?
C36 C31 C3 120.7(2) . . ?
N1 C13 C14 123.0(2) . . ?
N1 C13 H13A 118.5 . . ?
C14 C13 H13A 118.5 . . ?
C14 C15 C16 119.0(2) . . ?
C14 C15 H15A 120.5 . . ?
C16 C15 H15A 120.5 . . ?
C33 C32 C31 119.7(3) . . ?
C33 C32 H32A 120.2 . . ?
C31 C32 H32A 120.2 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C15 C14 C13 118.7(2) . . ?
C15 C14 H14A 120.7 . . ?
C13 C14 H14A 120.7 . . ?
N2 C1 C11 114.5(2) . . ?
N2 C1 C2 123.0(2) . . ?
C11 C1 C2 122.5(2) . . ?
N4 C35 C36 119.5(3) . . ?
N4 C35 H35A 120.2 . . ?
C36 C35 H35A 120.2 . . ?
C3 N3 N2 108.83(19) . . ?

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
O Zn N2 C1 178.3(2) . . . . ?
N1 Zn N2 C1 6.20(19) . . . . ?
Br1 Zn N2 C1 90.6(2) . . . . ?
Br2 Zn N2 C1 -85.29(19) . . . . ?
O Zn N2 N3 -5.23(16) . . . . ?
N1 Zn N2 N3 -177.34(18) . . . . ?
Br1 Zn N2 N3 -92.93(17) . . . . ?
Br2 Zn N2 N3 91.18(16) . . . . ?
N2 Zn O C3 4.11(16) . . . . ?
N1 Zn O C3 18.5(2) . . . . ?
Br1 Zn O C3 135.30(15) . . . . ?
Br2 Zn O C3 -105.03(15) . . . . ?
N2 Zn N1 C13 175.4(2) . . . . ?
O Zn N1 C13 160.94(19) . . . . ?
Br1 Zn N1 C13 43.7(2) . . . . ?
Br2 Zn N1 C13 -74.5(2) . . . . ?
N2 Zn N1 C11 -4.70(16) . . . . ?
O Zn N1 C11 -19.1(2) . . . . ?
Br1 Zn N1 C11 -136.43(15) . . . . ?
Br2 Zn N1 C11 105.39(15) . . . . ?
C32 C33 N4 C35 0.7(4) . . . . ?
C13 N1 C11 C16 0.1(3) . . . . ?
Zn N1 C11 C16 -179.82(18) . . . . ?
C13 N1 C11 C1 -176.8(2) . . . . ?
Zn N1 C11 C1 3.2(2) . . . . ?
N1 C11 C16 C15 0.0(4) . . . . ?
C1 C11 C16 C15 176.7(2) . . . . ?
Zn O C3 N3 -3.1(3) . . . . ?
Zn O C3 C31 174.33(17) . . . . ?
C35 C36 C31 C32 -0.8(4) . . . . ?
C35 C36 C31 C3 176.2(2) . . . . ?
O C3 C31 C32 -5.8(3) . . . . ?
N3 C3 C31 C32 171.9(2) . . . . ?
O C3 C31 C36 177.1(2) . . . . ?
N3 C3 C31 C36 -5.1(3) . . . . ?
C11 N1 C13 C14 -0.5(4) . . . . ?
Zn N1 C13 C14 179.45(18) . . . . ?
C11 C16 C15 C14 0.2(4) . . . . ?
N4 C33 C32 C31 0.1(4) . . . . ?
C36 C31 C32 C33 0.1(4) . . . . ?
C3 C31 C32 C33 -177.1(2) . . . . ?
C16 C15 C14 C13 -0.6(4) . . . . ?
N1 C13 C14 C15 0.7(4) . . . . ?
N3 N2 C1 C11 177.14(19) . . . . ?
Zn N2 C1 C11 -6.4(3) . . . . ?
N3 N2 C1 C2 -2.1(4) . . . . ?
Zn N2 C1 C2 174.38(18) . . . . ?
N1 C11 C1 N2 1.5(3) . . . . ?
C16 C11 C1 N2 -175.4(2) . . . . ?
N1 C11 C1 C2 -179.3(2) . . . . ?
C16 C11 C1 C2 3.9(4) . . . . ?
C33 N4 C35 C36 -1.5(4) . . . . ?
C31 C36 C35 N4 1.5(4) . . . . ?
O C3 N3 N2 -1.1(4) . . . . ?
C31 C3 N3 N2 -178.60(19) . . . . ?
C1 N2 N3 C3 -178.2(2) . . . . ?
Zn N2 N3 C3 5.2(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
N4 H1 Br2 0.82(3) 2.79(3) 3.431(3) 136(3) 2_476
N4 H1 Br1 0.82(3) 3.10(3) 3.606(3) 122(3) 2_376

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.080
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 1461716'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 Cd I2 N4 O3'
_chemical_formula_sum            'C15 H20 Cd I2 N4 O3'
_chemical_formula_weight         670.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.874(3)
_cell_length_b                   15.738(5)
_cell_length_c                   15.117(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.40(2)
_cell_angle_gamma                90.00
_cell_volume                     2101.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    896
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      15.0

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          .29
_exptl_crystal_size_mid          .21
_exptl_crystal_size_min          .19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1260
_exptl_absorpt_coefficient_mu    3.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_T_max  0.31
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_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
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8349
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4268
_reflns_number_gt                4172
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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 > 2σ(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)+(0.0216P)²+3.2168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4268
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_ref         0.0510
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_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
I1 I 0.347251(18) 0.193761(11) 0.009465(11) 0.01535(6) Uani 1 1 d . . .
I2 I 0.337449(19) 0.073497(12) 0.290150(12) 0.01993(6) Uani 1 1 d . . .
Cd1 Cd 0.18902(2) 0.106393(12) 0.126078(13) 0.01327(6) Uani 1 1 d . . .
O1 O 0.1905(2) -0.03798(12) 0.07607(13) 0.0175(4) Uani 1 1 d . . .
N1 N -0.0380(3) -0.05128(15) 0.13090(15) 0.0138(4) Uani 1 1 d . . .
N2 N -0.0434(2) 0.03635(14) 0.13281(15) 0.0139(4) Uani 1 1 d . . .
N3 N -0.0167(2) 0.20263(14) 0.12264(15) 0.0144(4) Uani 1 1 d . . .
N4 N 0.1809(3) -0.35176(16) 0.12336(16) 0.0189(5) Uani 1 1 d . . .
C1 C 0.0935(3) -0.08392(17) 0.10552(18) 0.0140(5) Uani 1 1 d . . .
C9 C 0.1169(3) -0.17768(17) 0.11300(17) 0.0133(5) Uani 1 1 d . . .
C10 C 0.0100(3) -0.23483(17) 0.13944(18) 0.0150(5) Uani 1 1 d . . .
H10 H -0.0856 -0.2156 0.1548 0.018 Uiso 1 1 calc R . .
C2 C -0.1701(3) 0.07622(17) 0.13461(17) 0.0137(5) Uani 1 1 d . . .
C3 C -0.1543(3) 0.17030(17) 0.13721(17) 0.0131(5) Uani 1 1 d . . .
C7 C -0.2753(3) 0.22348(18) 0.15274(18) 0.0166(5) Uani 1 1 d . . .
H7 H -0.3701 0.2002 0.1646 0.020 Uiso 1 1 calc R . .
C13 C 0.2564(3) -0.20958(18) 0.09231(18) 0.0167(5) Uani 1 1 d . . .
H13 H 0.3318 -0.1724 0.0739 0.020 Uiso 1 1 calc R . .
C12 C 0.2831(3) -0.29563(19) 0.0989(2) 0.0197(6) Uani 1 1 d . . .
H12 H 0.3789 -0.3164 0.0855 0.024 Uiso 1 1 calc R . .
C8 C -0.3242(3) 0.03754(18) 0.12947(19) 0.0186(6) Uani 1 1 d . . .
H8A H -0.3185 -0.0219 0.1109 0.028 Uiso 1 1 calc . . .
H8B H -0.3922 0.0688 0.0862 0.028 Uiso 1 1 calc . . .
H8C H -0.3631 0.0403 0.1880 0.028 Uiso 1 1 calc . . .
C4 C 0.0001(3) 0.28665(18) 0.11863(18) 0.0172(5) Uani 1 1 d . . .
H4 H 0.0955 0.3087 0.1060 0.021 Uiso 1 1 calc R . .
C5 C -0.1159(3) 0.34375(18) 0.13207(19) 0.0195(6) Uani 1 1 d . . .
H5 H -0.1004 0.4033 0.1287 0.023 Uiso 1 1 calc R . .
C6 C -0.2546(3) 0.31092(19) 0.1505(2) 0.0203(6) Uani 1 1 d . . .
H6 H -0.3351 0.3481 0.1615 0.024 Uiso 1 1 calc R . .
C11 C 0.0470(3) -0.32109(18) 0.14272(18) 0.0174(5) Uani 1 1 d . . .
H11 H -0.0267 -0.3602 0.1596 0.021 Uiso 1 1 calc R . .
O2 O 0.2338(2) 0.37548(14) 0.25634(14) 0.0194(4) Uani 1 1 d . . .
C14 C 0.3822(3) 0.3395(2) 0.2582(2) 0.0241(6) Uani 1 1 d . . .
H14A H 0.4580 0.3843 0.2709 0.036 Uiso 1 1 calc . . .
H14B H 0.3956 0.3138 0.2005 0.036 Uiso 1 1 calc . . .
H14C H 0.3948 0.2959 0.3046 0.036 Uiso 1 1 calc . . .
O3 O 0.1946(3) 0.47436(15) 0.11311(15) 0.0271(5) Uani 1 1 d . . .
C15 C 0.2582(7) 0.4590(2) 0.0333(3) 0.0618(15) Uani 1 1 d . . .
H15A H 0.2145 0.4983 -0.0124 0.093 Uiso 1 1 calc . . .
H15B H 0.2366 0.4004 0.0142 0.093 Uiso 1 1 calc . . .
H15C H 0.3680 0.4675 0.0422 0.093 Uiso 1 1 calc . . .
H1Q1 H 0.200(4) 0.520(3) 0.120(3) 0.030(11) Uiso 1 1 d . . .
H1Q4 H -0.102(5) -0.079(2) 0.161(3) 0.030(10) Uiso 1 1 d . . .
H1Q2 H 0.223(4) 0.407(2) 0.214(3) 0.025(10) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 Cd1 2.7268(8) . ?
I2 Cd1 2.7459(11) . ?
Cd1 N2 2.349(2) . ?
Cd1 N3 2.369(2) . ?
Cd1 O1 2.395(2) . ?
O1 C1 1.238(3) . ?
N1 C1 1.363(3) . ?
N1 N2 1.380(3) . ?
N1 H1Q4 0.87(4) . ?
N2 C2 1.290(3) . ?
N3 C4 1.333(4) . ?
N3 C3 1.359(3) . ?
N4 C11 1.340(4) . ?
N4 C12 1.342(4) . ?
C1 C9 1.493(4) . ?
C9 C10 1.393(4) . ?
C9 C13 1.398(4) . ?
C10 C11 1.397(4) . ?
C10 H10 0.9500 . ?
C2 C3 1.487(4) . ?
C2 C8 1.492(4) . ?
C3 C7 1.399(4) . ?
C7 C6 1.389(4) . ?
C7 H7 0.9500 . ?
C13 C12 1.377(4) . ?
C13 H13 0.9500 . ?
C12 H12 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C11 H11 0.9500 . ?
O2 C14 1.432(3) . ?
O2 H1Q2 0.80(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O3 C15 1.401(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 Cd1 N3 67.85(8) . . ?
N2 Cd1 O1 66.39(7) . . ?
N3 Cd1 O1 128.81(7) . . ?
N2 Cd1 I1 140.55(6) . . ?
N3 Cd1 I1 96.09(6) . . ?
O1 Cd1 I1 104.82(5) . . ?
N2 Cd1 I2 102.77(6) . . ?
N3 Cd1 I2 116.33(6) . . ?
O1 Cd1 I2 95.16(5) . . ?
I1 Cd1 I2 116.52(3) . . ?
C1 O1 Cd1 114.57(17) . . ?
C1 N1 N2 114.5(2) . . ?
C1 N1 H1Q4 125(3) . . ?
N2 N1 H1Q4 117(3) . . ?
C2 N2 N1 121.2(2) . . ?
C2 N2 Cd1 122.90(19) . . ?
N1 N2 Cd1 115.81(16) . . ?
C4 N3 C3 119.0(2) . . ?
C4 N3 Cd1 123.07(18) . . ?
C3 N3 Cd1 117.33(18) . . ?
C11 N4 C12 117.3(2) . . ?
O1 C1 N1 121.6(3) . . ?
O1 C1 C9 120.5(2) . . ?
N1 C1 C9 117.9(2) . . ?
C10 C9 C13 118.3(3) . . ?
C10 C9 C1 124.5(2) . . ?
C13 C9 C1 117.2(2) . . ?
C9 C10 C11 118.3(2) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
N2 C2 C3 113.9(2) . . ?
N2 C2 C8 126.6(3) . . ?
C3 C2 C8 119.4(2) . . ?
N3 C3 C7 121.2(3) . . ?
N3 C3 C2 116.9(2) . . ?
C7 C3 C2 121.9(2) . . ?
C6 C7 C3 118.9(3) . . ?
C6 C7 H7 120.5 . . ?
C3 C7 H7 120.5 . . ?
C12 C13 C9 119.1(3) . . ?
C12 C13 H13 120.4 . . ?
C9 C13 H13 120.4 . . ?
N4 C12 C13 123.5(3) . . ?
N4 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C4 C5 123.0(3) . . ?
N3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
N4 C11 C10 123.6(3) . . ?
N4 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C14 O2 H1Q2 107(3) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
N2 Cd1 O1 C1 -23.26(18) . . . . ?
N3 Cd1 O1 C1 -51.7(2) . . . . ?
I1 Cd1 O1 C1 -162.38(18) . . . . ?
I2 Cd1 O1 C1 78.43(19) . . . . ?
C1 N1 N2 C2 163.3(2) . . . . ?
C1 N1 N2 Cd1 -14.1(3) . . . . ?
N3 Cd1 N2 C2 -2.2(2) . . . . ?
O1 Cd1 N2 C2 -158.6(2) . . . . ?
I1 Cd1 N2 C2 -73.9(2) . . . . ?
I2 Cd1 N2 C2 111.3(2) . . . . ?
N3 Cd1 N2 N1 175.1(2) . . . . ?
O1 Cd1 N2 N1 18.71(16) . . . . ?
I1 Cd1 N2 N1 103.45(17) . . . . ?
I2 Cd1 N2 N1 -71.38(18) . . . . ?
N2 Cd1 N3 C4 179.1(2) . . . . ?
O1 Cd1 N3 C4 -152.8(2) . . . . ?
I1 Cd1 N3 C4 -38.2(2) . . . . ?
I2 Cd1 N3 C4 85.4(2) . . . . ?
N2 Cd1 N3 C3 7.94(18) . . . . ?
O1 Cd1 N3 C3 36.0(2) . . . . ?
I1 Cd1 N3 C3 150.60(18) . . . . ?
I2 Cd1 N3 C3 -85.77(19) . . . . ?
Cd1 O1 C1 N1 26.3(3) . . . . ?
Cd1 O1 C1 C9 -154.56(19) . . . . ?
N2 N1 C1 O1 -8.7(4) . . . . ?
N2 N1 C1 C9 172.2(2) . . . . ?
O1 C1 C9 C10 -175.4(3) . . . . ?
N1 C1 C9 C10 3.8(4) . . . . ?
O1 C1 C9 C13 5.0(4) . . . . ?
N1 C1 C9 C13 -175.9(2) . . . . ?
C13 C9 C10 C11 -0.9(4) . . . . ?
C1 C9 C10 C11 179.5(3) . . . . ?
N1 N2 C2 C3 179.6(2) . . . . ?
Cd1 N2 C2 C3 -3.3(3) . . . . ?
N1 N2 C2 C8 -3.9(4) . . . . ?
Cd1 N2 C2 C8 173.2(2) . . . . ?
C4 N3 C3 C7 -3.5(4) . . . . ?
Cd1 N3 C3 C7 168.0(2) . . . . ?
C4 N3 C3 C2 175.7(2) . . . . ?
Cd1 N3 C3 C2 -12.7(3) . . . . ?
N2 C2 C3 N3 10.5(4) . . . . ?
C8 C2 C3 N3 -166.2(2) . . . . ?
N2 C2 C3 C7 -170.3(2) . . . . ?
C8 C2 C3 C7 13.0(4) . . . . ?
N3 C3 C7 C6 1.9(4) . . . . ?
C2 C3 C7 C6 -177.2(3) . . . . ?
C10 C9 C13 C12 -0.1(4) . . . . ?
C1 C9 C13 C12 179.5(3) . . . . ?
C11 N4 C12 C13 -0.5(4) . . . . ?
C9 C13 C12 N4 0.9(4) . . . . ?
C3 N3 C4 C5 2.5(4) . . . . ?
Cd1 N3 C4 C5 -168.5(2) . . . . ?
N3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 -1.6(4) . . . . ?
C3 C7 C6 C5 0.7(4) . . . . ?
C12 N4 C11 C10 -0.6(4) . . . . ?
C9 C10 C11 N4 1.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.117
####################################################################### 
# 
# 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 1461717'
_audit_update_record             
;
2016-04-16 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Br2 Cd N4 O2'
_chemical_formula_weight         544.53

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.85990(10)
_cell_length_b                   14.8149(2)
_cell_length_c                   15.7341(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.3830(10)
_cell_angle_gamma                90
_cell_volume                     1828.94(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    14297
_cell_measurement_theta_min      2.9298
_cell_measurement_theta_max      29.0098

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    5.576
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51553
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28485
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.936
_diffrn_reflns_theta_max         29.074
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4540
_reflns_number_gt                4040
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0116P)²+1.7235P] 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         4540
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0427
_refine_ls_wR_factor_gt          0.0410
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
Br1 Br -0.20303(3) 0.28566(2) -0.18612(2) 0.02795(6) Uani 1 1 d . . . . .
Br2 Br 0.26310(3) 0.15019(2) -0.11878(2) 0.01999(6) Uani 1 1 d . . . . .
Cd1 Cd 0.06223(2) 0.28298(2) -0.08332(2) 0.01398(4) Uani 1 1 d . . . . .
N1 N -0.0548(2) 0.21640(12) 0.03820(11) 0.0163(4) Uani 1 1 d . . . . .
N2 N 0.1112(2) 0.37212(11) 0.03383(10) 0.0117(3) Uani 1 1 d . . . . .
N3 N 0.1973(2) 0.45224(11) 0.02516(10) 0.0131(3) Uani 1 1 d . . . . .
N4 N 0.5042(2) 0.70504(13) -0.09841(14) 0.0229(4) Uani 1 1 d . . . . .
H2N H 0.551(3) 0.7530(19) -0.1055(17) 0.027 Uiso 1 1 d . U . . .
O1 O 0.2141(2) 0.40956(10) -0.11760(9) 0.0183(3) Uani 1 1 d . . . . .
C5 C -0.2015(3) 0.10153(15) 0.11203(15) 0.0249(5) Uani 1 1 d . . . . .
H5 H -0.2575 0.0462 0.1105 0.030 Uiso 1 1 calc R U . . .
C4 C -0.1355(3) 0.13698(15) 0.03928(14) 0.0229(5) Uani 1 1 d . . . . .
H4 H -0.1479 0.1040 -0.0110 0.027 Uiso 1 1 calc R U . . .
C6 C -0.1824(3) 0.15010(15) 0.18663(15) 0.0225(5) Uani 1 1 d . . . . .
H6 H -0.2258 0.1280 0.2363 0.027 Uiso 1 1 calc R U . . .
C7 C -0.0975(3) 0.23247(14) 0.18697(13) 0.0168(4) Uani 1 1 d . . . . .
H7 H -0.0826 0.2659 0.2369 0.020 Uiso 1 1 calc R U . . .
C3 C -0.0353(2) 0.26416(13) 0.11152(12) 0.0122(4) Uani 1 1 d . . . . .
C2 C 0.0551(2) 0.35218(14) 0.10720(12) 0.0120(4) Uani 1 1 d . . . . .
C8 C 0.0771(3) 0.41107(15) 0.18444(12) 0.0173(4) Uani 1 1 d . . . . .
H8A H 0.1474 0.3807 0.2275 0.026 Uiso 1 1 calc R U . . .
H8B H -0.0323 0.4235 0.2058 0.026 Uiso 1 1 calc R U . . .
H8C H 0.1304 0.4667 0.1695 0.026 Uiso 1 1 calc R U . . .
C1 C 0.2410(2) 0.46174(13) -0.05447(12) 0.0125(4) Uani 1 1 d . . . . .
C9 C 0.3361(2) 0.54790(13) -0.06861(13) 0.0135(4) Uani 1 1 d . . . . .
C10 C 0.3942(3) 0.56677(15) -0.14898(14) 0.0187(4) Uani 1 1 d . . . . .
H10 H 0.3760 0.5256 -0.1932 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3674(3) 0.61054(14) -0.00373(14) 0.0169(4) Uani 1 1 d . . . . .
H14 H 0.3314 0.5991 0.0505 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4783(3) 0.64647(16) -0.16240(15) 0.0226(5) Uani 1 1 d . . . . .
H11 H 0.5171 0.6595 -0.2158 0.027 Uiso 1 1 calc R U . . .
C13 C 0.4519(3) 0.68951(15) -0.02001(15) 0.0216(5) Uani 1 1 d . . . . .
H13 H 0.4727 0.7318 0.0230 0.026 Uiso 1 1 calc R U . . .
O2 O 0.3449(4) 0.13246(16) 0.0861(2) 0.0343(10) Uani 0.724(9) 1 d . . P A 1
H2 H 0.3136 0.1287 0.0356 0.051 Uiso 1 1 calc R U . A 1
C15 C 0.3213(4) 0.04936(18) 0.12584(19) 0.0435(7) Uani 1 1 d . . . A 1
H15A H 0.3676 0.0521 0.1836 0.065 Uiso 1 1 calc R U . A 1
H15B H 0.3784 0.0029 0.0959 0.065 Uiso 1 1 calc R U . A 1
H15C H 0.2018 0.0360 0.1253 0.065 Uiso 1 1 calc R U . A 1
O2B O 0.3492(10) 0.1374(5) 0.1364(8) 0.043(3) Uiso 0.276(9) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cd1 2.5625(3) . ?
Br2 Cd1 2.6035(3) . ?
Cd1 N2 2.2816(16) . ?
Cd1 O1 2.3041(14) . ?
Cd1 N1 2.3838(17) . ?
N1 C4 1.337(3) . ?
N1 C3 1.354(3) . ?
N2 C2 1.294(2) . ?
N2 N3 1.377(2) . ?
N3 C1 1.326(3) . ?
N4 C11 1.336(3) . ?
N4 C13 1.343(3) . ?
N4 H2N 0.81(3) . ?
O1 C1 1.267(2) . ?
C5 C6 1.377(3) . ?
C5 C4 1.388(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C6 C7 1.391(3) . ?
C6 H6 0.9300 . ?
C7 C3 1.392(3) . ?
C7 H7 0.9300 . ?
C3 C2 1.489(3) . ?
C2 C8 1.498(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C1 C9 1.502(3) . ?
C9 C14 1.391(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C14 C13 1.377(3) . ?
C14 H14 0.9300 . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
O2 C15 1.398(3) . ?
O2 H2 0.8200 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cd1 O1 69.70(5) . . ?
N2 Cd1 N1 69.28(6) . . ?
O1 Cd1 N1 138.97(5) . . ?
N2 Cd1 Br1 126.38(4) . . ?
O1 Cd1 Br1 104.66(4) . . ?
N1 Cd1 Br1 100.05(4) . . ?
N2 Cd1 Br2 122.35(4) . . ?
O1 Cd1 Br2 103.63(4) . . ?
N1 Cd1 Br2 97.28(4) . . ?
Br1 Cd1 Br2 110.946(9) . . ?
C4 N1 C3 118.61(18) . . ?
C4 N1 Cd1 125.45(14) . . ?
C3 N1 Cd1 115.93(13) . . ?
C2 N2 N3 118.71(16) . . ?
C2 N2 Cd1 122.59(13) . . ?
N3 N2 Cd1 118.63(12) . . ?
C1 N3 N2 109.96(16) . . ?
C11 N4 C13 122.7(2) . . ?
C11 N4 H2N 121.0(19) . . ?
C13 N4 H2N 116.3(19) . . ?
C1 O1 Cd1 112.20(12) . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
N1 C4 C5 123.0(2) . . ?
N1 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C5 C6 C7 119.3(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C3 119.0(2) . . ?
C6 C7 H7 120.5 . . ?
C3 C7 H7 120.5 . . ?
N1 C3 C7 121.50(19) . . ?
N1 C3 C2 116.69(17) . . ?
C7 C3 C2 121.81(18) . . ?
N2 C2 C3 115.42(17) . . ?
N2 C2 C8 124.19(18) . . ?
C3 C2 C8 120.38(17) . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C1 N3 129.47(19) . . ?
O1 C1 C9 117.63(17) . . ?
N3 C1 C9 112.89(17) . . ?
C14 C9 C10 118.51(19) . . ?
C14 C9 C1 121.76(18) . . ?
C10 C9 C1 119.73(18) . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C13 C14 C9 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
N4 C11 C10 119.7(2) . . ?
N4 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
N4 C13 C14 119.6(2) . . ?
N4 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 O2 H2 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.536
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.082

