# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1033030'
_audit_update_record             
;
2015-03-27 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H18 N12 O8 Zn3'
_chemical_formula_weight         846.65

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

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

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                   20.861(5)
_cell_length_b                   15.959(5)
_cell_length_c                   13.286(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.789(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     4392(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    12423
_cell_measurement_theta_min      1.611
_cell_measurement_theta_max      24.999

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    1.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6511
_exptl_absorpt_correction_T_max  0.6697
_exptl_absorpt_process_details   'SADABS, Sheldrick (2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART Apex II CCD Detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12423
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3858
_reflns_number_gt                2731
_reflns_threshold_expression     >2sigma(I)

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

_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.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.009 799 46 ' '
2 0.500 0.500 -0.006 799 46 ' '
_platon_squeeze_details          
;
;

_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)+(0.0694P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3858
_refine_ls_number_parameters     225
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 1.0000 0.36265(5) 0.2500 0.0307(2) Uani 1 2 d S . .
Zn2 Zn 0.82918(2) 0.44368(3) 0.01080(4) 0.0331(2) Uani 1 1 d . . .
C1 C 0.8490(3) 0.5813(4) 0.1636(4) 0.0576(16) Uani 1 1 d . . .
H1 H 0.8889 0.5602 0.1906 0.069 Uiso 1 1 calc R . .
C2 C 0.7573(2) 0.5931(3) 0.0723(4) 0.0416(12) Uani 1 1 d . . .
H2 H 0.7215 0.5825 0.0252 0.050 Uiso 1 1 calc R . .
C3 C 0.8237(3) 0.6525(4) 0.1909(5) 0.0644(18) Uani 1 1 d . . .
H3 H 0.8420 0.6895 0.2402 0.077 Uiso 1 1 calc R . .
C4 C 0.7223(2) 0.7321(3) 0.1289(4) 0.0357(11) Uani 1 1 d . . .
C5 C 0.6591(3) 0.7232(4) 0.0871(5) 0.0595(17) Uani 1 1 d . . .
H5 H 0.6444 0.6717 0.0610 0.071 Uiso 1 1 calc R . .
C6 C 0.6174(2) 0.7906(3) 0.0838(5) 0.0518(15) Uani 1 1 d . . .
H6 H 0.5747 0.7841 0.0559 0.062 Uiso 1 1 calc R . .
C7 C 0.6389(2) 0.8679(3) 0.1218(4) 0.0327(11) Uani 1 1 d . . .
C8 C 0.7027(2) 0.8751(3) 0.1633(4) 0.0462(13) Uani 1 1 d . . .
H8 H 0.7181 0.9265 0.1884 0.055 Uiso 1 1 calc R . .
C9 C 0.7437(2) 0.8071(3) 0.1679(4) 0.0458(13) Uani 1 1 d . . .
H9 H 0.7861 0.8126 0.1977 0.055 Uiso 1 1 calc R . .
C10 C 0.5950(2) 0.9391(3) 0.1175(3) 0.0313(11) Uani 1 1 d . . .
C11 C 0.8893(2) 0.3028(3) 0.1401(3) 0.0312(11) Uani 1 1 d . . .
C12 C 0.8370(2) 0.2417(3) 0.1075(4) 0.0408(12) Uani 1 1 d . . .
H12A H 0.8022 0.2605 0.0631 0.049 Uiso 1 1 calc R . .
C13 C 0.8366(2) 0.1645(3) 0.1367(4) 0.0438(13) Uani 1 1 d . . .
H13A H 0.8710 0.1453 0.1815 0.053 Uiso 1 1 calc R . .
C14 C 0.7841(3) 0.1055(4) 0.1024(5) 0.0588(15) Uani 1 1 d U . .
N1 N 0.80784(19) 0.5432(3) 0.0898(3) 0.0407(10) Uani 1 1 d . . .
N2 N 0.76478(19) 0.6617(3) 0.1323(3) 0.0411(10) Uani 1 1 d . . .
N3 N 0.60498(17) 1.0142(2) 0.0765(3) 0.0334(9) Uani 1 1 d . . .
N4 N 0.55173(18) 1.0618(2) 0.0881(3) 0.0363(10) Uani 1 1 d . . .
N5 N 0.51256(18) 1.0169(3) 0.1358(3) 0.0373(10) Uani 1 1 d . . .
N6 N 0.53867(17) 0.9399(2) 0.1549(3) 0.0318(9) Uani 1 1 d . . .
O1 O 0.88412(14) 0.3782(2) 0.1134(2) 0.0363(8) Uani 1 1 d . . .
O2 O 0.93789(14) 0.2771(2) 0.1969(3) 0.0396(8) Uani 1 1 d . . .
O3 O 0.7904(2) 0.0306(3) 0.1226(3) 0.0704(8) Uani 1 1 d U . .
O4 O 0.7357(2) 0.1320(3) 0.0483(3) 0.0704(8) Uani 1 1 d U . .


_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 O2 1.955(3) . ?
Zn1 O2 1.955(3) 2_755 ?
Zn1 N6 2.002(4) 3_545 ?
Zn1 N6 2.002(4) 4_645 ?
Zn2 O4 1.913(4) 7_655 ?
Zn2 O1 1.973(3) . ?
Zn2 N1 1.983(4) . ?
Zn2 N3 2.015(4) 7_665 ?
C1 C3 1.322(7) . ?
C1 N1 1.366(7) . ?
C1 H1 0.9300 . ?
C2 N1 1.320(6) . ?
C2 N2 1.352(6) . ?
C2 H2 0.9300 . ?
C3 N2 1.383(6) . ?
C3 H3 0.9300 . ?
C4 C9 1.358(7) . ?
C4 C5 1.377(7) . ?
C4 N2 1.429(6) . ?
C5 C6 1.380(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(6) . ?
C7 C10 1.455(6) . ?
C8 C9 1.379(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 N6 1.330(5) . ?
C10 N3 1.343(6) . ?
C11 O1 1.256(5) . ?
C11 O2 1.259(5) . ?
C11 C12 1.488(6) . ?
C12 C13 1.291(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.474(7) . ?
C13 H13A 0.9300 . ?
C14 O3 1.229(7) . ?
C14 O4 1.243(6) . ?
N3 N4 1.370(5) . ?
N3 Zn2 2.015(4) 7_665 ?
N4 N5 1.306(5) . ?
N5 N6 1.356(5) . ?
N6 Zn1 2.002(4) 3_455 ?
O4 Zn2 1.913(4) 7_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O2 91.46(19) . 2_755 ?
O2 Zn1 N6 120.10(15) . 3_545 ?
O2 Zn1 N6 111.00(14) 2_755 3_545 ?
O2 Zn1 N6 111.00(14) . 4_645 ?
O2 Zn1 N6 120.10(15) 2_755 4_645 ?
N6 Zn1 N6 104.0(2) 3_545 4_645 ?
O4 Zn2 O1 105.91(15) 7_655 . ?
O4 Zn2 N1 122.07(18) 7_655 . ?
O1 Zn2 N1 101.93(16) . . ?
O4 Zn2 N3 118.17(18) 7_655 7_665 ?
O1 Zn2 N3 101.22(14) . 7_665 ?
N1 Zn2 N3 104.39(16) . 7_665 ?
C3 C1 N1 110.0(5) . . ?
C3 C1 H1 125.0 . . ?
N1 C1 H1 125.0 . . ?
N1 C2 N2 110.5(5) . . ?
N1 C2 H2 124.8 . . ?
N2 C2 H2 124.8 . . ?
C1 C3 N2 107.0(5) . . ?
C1 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
C9 C4 C5 120.1(5) . . ?
C9 C4 N2 120.5(4) . . ?
C5 C4 N2 119.5(5) . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.5(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 118.2(4) . . ?
C8 C7 C10 121.4(4) . . ?
C6 C7 C10 120.4(4) . . ?
C9 C8 C7 121.0(5) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C4 C9 C8 120.1(5) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N6 C10 N3 109.2(4) . . ?
N6 C10 C7 124.9(4) . . ?
N3 C10 C7 125.9(4) . . ?
O1 C11 O2 121.1(4) . . ?
O1 C11 C12 120.7(4) . . ?
O2 C11 C12 118.2(4) . . ?
C13 C12 C11 124.6(4) . . ?
C13 C12 H12A 117.7 . . ?
C11 C12 H12A 117.7 . . ?
C12 C13 C14 123.3(5) . . ?
C12 C13 H13A 118.4 . . ?
C14 C13 H13A 118.4 . . ?
O3 C14 O4 121.2(5) . . ?
O3 C14 C13 119.9(5) . . ?
O4 C14 C13 118.8(5) . . ?
C2 N1 C1 106.2(4) . . ?
C2 N1 Zn2 127.9(4) . . ?
C1 N1 Zn2 125.1(3) . . ?
C2 N2 C3 106.3(4) . . ?
C2 N2 C4 126.2(4) . . ?
C3 N2 C4 127.3(4) . . ?
C10 N3 N4 106.5(4) . . ?
C10 N3 Zn2 132.8(3) . 7_665 ?
N4 N3 Zn2 119.8(3) . 7_665 ?
N5 N4 N3 108.2(4) . . ?
N4 N5 N6 109.1(4) . . ?
C10 N6 N5 107.0(4) . . ?
C10 N6 Zn1 132.0(3) . 3_455 ?
N5 N6 Zn1 119.6(3) . 3_455 ?
C11 O1 Zn2 136.5(3) . . ?
C11 O2 Zn1 116.2(3) . . ?
C14 O4 Zn2 120.6(4) . 7_655 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.107
_refine_diff_density_min         -1.453
_refine_diff_density_rms         0.090
####################################################################### 
# 
# 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 1033032'
_audit_update_record             
;
2015-03-27 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H9 Br N6 O5 Zn2'
_chemical_formula_weight         599.96

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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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


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

_cell_length_a                   16.279(5)
_cell_length_b                   6.820(5)
_cell_length_c                   23.711(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 103.970(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2555(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13945
_cell_measurement_theta_min      1.3
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    3.478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4101
_exptl_absorpt_correction_T_max  0.4577
_exptl_absorpt_process_details   'SADABS, Sheldrick (2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART Apex II CCD Detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13945
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4489
_reflns_number_gt                3685
_reflns_threshold_expression     >2sigma(I)

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

_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.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 -0.027 0.500 389 15 ' '
2 0.500 -0.009 1.000 389 15 ' '
_platon_squeeze_details          
;
;

_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)+(0.1211P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4489
_refine_ls_number_parameters     278
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1639
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.108
_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 0.17448(3) -0.41947(8) 0.72299(2) 0.0158(2) Uani 1 1 d . . .
Zn2 Zn 0.00321(3) 0.32605(8) 0.75473(2) 0.0126(2) Uani 1 1 d . . .
Br1 Br 0.09178(5) -0.87725(11) 0.57236(3) 0.0487(3) Uani 1 1 d . . .
O3 O 0.0455(2) -0.4065(5) 0.33225(17) 0.0294(9) Uani 1 1 d U . .
O4 O 0.0460(2) -0.7398(5) 0.34115(16) 0.0244(8) Uani 1 1 d U . .
O5 O 0.0817(2) -0.4194(4) 0.76425(15) 0.0128(7) Uani 1 1 d U . .
C8 C 0.2212(3) 0.0747(6) 0.7224(2) 0.0162(10) Uani 1 1 d . . .
O2 O 0.1266(3) -0.4533(6) 0.64027(18) 0.0342(10) Uani 1 1 d U . .
O1 O 0.2527(4) -0.4304(8) 0.6282(3) 0.0651(15) Uani 1 1 d U . .
N1 N 0.1732(2) -0.0876(5) 0.72041(19) 0.0168(9) Uani 1 1 d . A .
C20 C 0.5860(4) 0.0883(12) 0.6588(3) 0.0482(18) Uani 1 1 d U A .
C10 C 0.1792(4) -0.4600(9) 0.6097(3) 0.0330(12) Uani 1 1 d U . .
C17 C 0.0550(4) -0.5640(8) 0.3608(3) 0.0277(13) Uani 1 1 d . . .
C14 C 0.0834(4) -0.5386(9) 0.4257(3) 0.0320(13) Uani 1 1 d . . .
N9 N 0.0979(2) -0.0167(6) 0.72527(18) 0.0166(9) Uani 1 1 d . . .
N2 N 0.1017(2) 0.1703(5) 0.73067(18) 0.0144(8) Uani 1 1 d . . .
N12 N 0.7026(3) 0.0848(6) 0.7319(2) 0.0197(10) Uani 1 1 d . . .
C16 C 0.1027(3) -0.6666(8) 0.5236(3) 0.0273(12) Uani 1 1 d . . .
C18 C 0.6350(3) 0.0818(7) 0.7530(2) 0.0219(12) Uani 1 1 d . A .
H18 H 0.6360 0.0790 0.7924 0.026 Uiso 1 1 calc R . .
C12 C 0.1490(4) -0.3465(10) 0.5069(3) 0.0412(16) Uani 1 1 d . . .
H12 H 0.1745 -0.2290 0.5214 0.049 Uiso 1 1 calc R . .
N3 N 0.1787(2) 0.2341(6) 0.72991(19) 0.0172(9) Uani 1 1 d . . .
C11 C 0.1444(4) -0.4968(9) 0.5458(3) 0.0324(13) Uani 1 1 d . . .
C13 C 0.1182(4) -0.3644(9) 0.4490(3) 0.0399(15) Uani 1 1 d . . .
H13 H 0.1205 -0.2583 0.4248 0.048 Uiso 1 1 calc R . .
C15 C 0.0741(4) -0.6967(9) 0.4644(3) 0.0327(13) Uani 1 1 d . . .
H15 H 0.0495 -0.8152 0.4499 0.039 Uiso 1 1 calc R . .
C19 C 0.6688(4) 0.0852(14) 0.6740(3) 0.063(3) Uani 1 1 d . . .
H19 H 0.7018 0.0834 0.6470 0.076 Uiso 1 1 calc R . .
N10 N 0.5661(2) 0.0833(6) 0.7111(2) 0.0237(10) Uani 1 1 d . . .
C1 C 0.3115(2) 0.0580(5) 0.71940(15) 0.0152(10) Uani 0.50 1 d PGU A 1
C2A C 0.3740(2) 0.0892(6) 0.76876(14) 0.0307(13) Uani 0.50 1 d PGU A 1
H2A H 0.3601 0.1102 0.8041 0.037 Uiso 0.50 1 calc PR A 1
C3A C 0.45719(19) 0.0894(6) 0.76612(14) 0.0274(12) Uani 0.50 1 d PGU A 1
H3A H 0.4997 0.1106 0.7996 0.033 Uiso 0.50 1 calc PR A 1
C4A C 0.4778(2) 0.0585(6) 0.71411(15) 0.0159(11) Uani 0.50 1 d PGU A 1
C5A C 0.4152(2) 0.0272(7) 0.66476(16) 0.032(2) Uani 0.50 1 d PGU A 1
H5A H 0.4292 0.0062 0.6295 0.039 Uiso 0.50 1 calc PR A 1
C6A C 0.3321(2) 0.0270(7) 0.66739(16) 0.0297(19) Uani 0.50 1 d PGU A 1
H6A H 0.2896 0.0058 0.6339 0.036 Uiso 0.50 1 calc PR A 1
C1B C 0.3113(2) 0.0862(5) 0.71949(15) 0.0152(10) Uani 0.50 1 d PGU A 2
C2B C 0.3748(2) 0.0904(6) 0.76989(15) 0.0307(13) Uani 0.50 1 d PGU A 2
H2B H 0.3612 0.0895 0.8058 0.037 Uiso 0.50 1 calc PR A 2
C3B C 0.4583(2) 0.0960(6) 0.76705(15) 0.0274(12) Uani 0.50 1 d PGU A 2
H3B H 0.5011 0.0989 0.8011 0.033 Uiso 0.50 1 calc PR A 2
C4B C 0.4784(2) 0.0974(6) 0.71379(15) 0.0159(11) Uani 0.50 1 d PGU A 2
C5B C 0.4149(2) 0.0931(7) 0.66338(15) 0.032(2) Uani 0.50 1 d PGU A 2
H5B H 0.4285 0.0940 0.6275 0.039 Uiso 0.50 1 calc PR A 2
C6B C 0.3314(2) 0.0875(7) 0.66623(15) 0.0297(19) Uani 0.50 1 d PGU A 2
H6B H 0.2885 0.0847 0.6322 0.036 Uiso 0.50 1 calc PR A 2


_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 O2 1.942(4) . ?
Zn1 O5 1.988(3) . ?
Zn1 N12 2.028(4) 2_646 ?
Zn1 N1 2.264(4) . ?
Zn1 N3 2.368(4) 1_545 ?
Zn2 O4 2.083(4) 4_556 ?
Zn2 O3 2.096(4) 3_556 ?
Zn2 N9 2.112(4) 2_556 ?
Zn2 N2 2.113(4) . ?
Zn2 O5 2.135(3) 1_565 ?
Zn2 O5 2.148(3) 2_556 ?
Br1 C16 1.880(6) . ?
O3 C17 1.259(7) . ?
O3 Zn2 2.096(4) 3_556 ?
O4 C17 1.283(6) . ?
O4 Zn2 2.083(4) 4 ?
O5 Zn2 2.135(3) 1_545 ?
O5 Zn2 2.148(3) 2_546 ?
C8 N3 1.324(6) . ?
C8 N1 1.349(6) . ?
C8 C1B 1.486(5) . ?
C8 C1 1.492(5) . ?
O2 C10 1.250(7) . ?
O1 C10 1.188(8) . ?
N1 N9 1.348(5) . ?
C20 C19 1.310(9) . ?
C20 N10 1.355(8) . ?
C10 C11 1.504(8) . ?
C17 C14 1.505(8) . ?
C14 C13 1.374(9) . ?
C14 C15 1.448(8) . ?
N9 N2 1.282(6) . ?
N9 Zn2 2.112(4) 2_546 ?
N2 N3 1.332(5) . ?
N12 C18 1.314(6) . ?
N12 C19 1.352(9) . ?
N12 Zn1 2.028(4) 2_656 ?
C16 C11 1.381(8) . ?
C16 C15 1.382(8) . ?
C18 N10 1.306(7) . ?
C12 C13 1.347(9) . ?
C12 C11 1.394(9) . ?
N3 Zn1 2.368(4) 1_565 ?
N10 C4B 1.448(5) . ?
N10 C4A 1.467(5) . ?
C1 C2A 1.370(2) . ?
C1 C6A 1.370(2) . ?
C2A C3A 1.370(2) . ?
C3A C4A 1.370(2) . ?
C4A C5A 1.370(2) . ?
C5A C6A 1.370(2) . ?
C1B C2B 1.379(2) . ?
C1B C6B 1.379(2) . ?
C2B C3B 1.379(2) . ?
C3B C4B 1.379(2) . ?
C4B C5B 1.379(2) . ?
C5B C6B 1.379(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
O2 Zn1 O5 109.24(17) . . ?
O2 Zn1 N12 129.69(18) . 2_646 ?
O5 Zn1 N12 120.71(16) . 2_646 ?
O2 Zn1 N1 95.31(17) . . ?
O5 Zn1 N1 90.57(13) . . ?
N12 Zn1 N1 90.07(15) 2_646 . ?
O2 Zn1 N3 87.10(16) . 1_545 ?
O5 Zn1 N3 88.81(12) . 1_545 ?
N12 Zn1 N3 88.24(15) 2_646 1_545 ?
N1 Zn1 N3 177.58(16) . 1_545 ?
O4 Zn2 O3 177.24(14) 4_556 3_556 ?
O4 Zn2 N9 90.93(15) 4_556 2_556 ?
O3 Zn2 N9 87.58(16) 3_556 2_556 ?
O4 Zn2 N2 91.61(15) 4_556 . ?
O3 Zn2 N2 89.86(16) 3_556 . ?
N9 Zn2 N2 177.40(16) 2_556 . ?
O4 Zn2 O5 94.35(14) 4_556 1_565 ?
O3 Zn2 O5 88.04(14) 3_556 1_565 ?
N9 Zn2 O5 92.42(14) 2_556 1_565 ?
N2 Zn2 O5 87.92(14) . 1_565 ?
O4 Zn2 O5 91.82(14) 4_556 2_556 ?
O3 Zn2 O5 85.79(14) 3_556 2_556 ?
N9 Zn2 O5 86.89(14) 2_556 2_556 ?
N2 Zn2 O5 92.49(14) . 2_556 ?
O5 Zn2 O5 173.81(6) 1_565 2_556 ?
C17 O3 Zn2 136.2(4) . 3_556 ?
C17 O4 Zn2 127.1(4) . 4 ?
Zn1 O5 Zn2 117.00(14) . 1_545 ?
Zn1 O5 Zn2 115.09(14) . 2_546 ?
Zn2 O5 Zn2 105.85(14) 1_545 2_546 ?
N3 C8 N1 111.2(4) . . ?
N3 C8 C1B 121.1(4) . . ?
N1 C8 C1B 127.7(4) . . ?
N3 C8 C1 128.4(4) . . ?
N1 C8 C1 120.3(4) . . ?
C1B C8 C1 7.4 . . ?
C10 O2 Zn1 115.2(4) . . ?
N9 N1 C8 103.5(4) . . ?
N9 N1 Zn1 111.0(3) . . ?
C8 N1 Zn1 144.8(3) . . ?
C19 C20 N10 101.9(6) . . ?
O1 C10 O2 123.4(6) . . ?
O1 C10 C11 120.1(6) . . ?
O2 C10 C11 116.4(6) . . ?
O3 C17 O4 127.8(5) . . ?
O3 C17 C14 114.8(5) . . ?
O4 C17 C14 117.4(5) . . ?
C13 C14 C15 119.0(6) . . ?
C13 C14 C17 120.4(5) . . ?
C15 C14 C17 120.6(5) . . ?
N2 N9 N1 110.0(3) . . ?
N2 N9 Zn2 120.3(3) . 2_546 ?
N1 N9 Zn2 127.7(3) . 2_546 ?
N9 N2 N3 110.3(3) . . ?
N9 N2 Zn2 120.4(3) . . ?
N3 N2 Zn2 128.1(3) . . ?
C18 N12 C19 102.3(5) . . ?
C18 N12 Zn1 127.6(4) . 2_656 ?
C19 N12 Zn1 130.1(4) . 2_656 ?
C11 C16 C15 121.8(5) . . ?
C11 C16 Br1 121.1(5) . . ?
C15 C16 Br1 116.9(4) . . ?
N10 C18 N12 110.8(5) . . ?
C13 C12 C11 122.8(6) . . ?
C8 N3 N2 104.9(4) . . ?
C8 N3 Zn1 144.9(3) . 1_565 ?
N2 N3 Zn1 108.4(3) . 1_565 ?
C16 C11 C12 117.6(6) . . ?
C16 C11 C10 123.7(5) . . ?
C12 C11 C10 118.5(5) . . ?
C12 C13 C14 120.3(6) . . ?
C16 C15 C14 118.1(5) . . ?
C20 C19 N12 114.7(6) . . ?
C18 N10 C20 110.2(5) . . ?
C18 N10 C4B 129.9(4) . . ?
C20 N10 C4B 119.6(5) . . ?
C18 N10 C4A 129.3(4) . . ?
C20 N10 C4A 120.1(5) . . ?
C4B N10 C4A 10.4 . . ?
C2A C1 C6A 120.0 . . ?
C2A C1 C8 119.0(3) . . ?
C6A C1 C8 120.8(3) . . ?
C1 C2A C3A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A N10 120.8(3) . . ?
C3A C4A N10 118.8(3) . . ?
C4A C5A C6A 120.0 . . ?
C5A C6A C1 120.0 . . ?
C2B C1B C6B 120.0 . . ?
C2B C1B C8 120.1(3) . . ?
C6B C1B C8 119.9(3) . . ?
C3B C2B C1B 120.0 . . ?
C2B C3B C4B 120.0 . . ?
C5B C4B C3B 120.0 . . ?
C5B C4B N10 120.1(3) . . ?
C3B C4B N10 119.6(3) . . ?
C4B C5B C6B 120.0 . . ?
C5B C6B C1B 120.0 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.528
_refine_diff_density_min         -1.790
_refine_diff_density_rms         0.198
