# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_matrix_0m_b
_database_code_depnum_ccdc_archive 'CCDC 1035285'
_audit_update_record             
;
2015-06-04 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97


_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 Br N3 O'
_chemical_formula_sum            'C19 H13 Br N3 O'
_chemical_formula_weight         379.23

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc
_symmetry_space_group_name_Hall  C-2yc
_symmetry_Int_Tables_number      ?

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'

_cell_length_a                   37.4840(11)
_cell_length_b                   7.0935(2)
_cell_length_c                   6.2089(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.497(2)
_cell_angle_gamma                90.00
_cell_volume                     1636.79(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2858
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.37

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             764
_exptl_absorpt_coefficient_mu    2.522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_absorpt_correction_T_min  0.3966
_exptl_absorpt_correction_T_max  0.9059
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  multi-scan
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9427
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2858
_reflns_number_gt                2593
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0263P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_number_reflns         2858
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0643
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      0.997
_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
Br Br 0.992401(12) 0.30155(4) 0.02292(4) 0.06338(12) Uani 1 1 d U . .
O O 1.27689(6) 0.1892(3) -0.7354(3) 0.0513(5) Uani 1 1 d U . .
H8 H 1.2950 0.2168 -0.6524 0.077 Uiso 1 1 calc R . .
N2 N 1.15543(6) 0.2885(3) -0.3240(4) 0.0409(5) Uani 1 1 d U . .
C6 C 1.06747(7) 0.3289(3) 0.0056(4) 0.0414(6) Uani 1 1 d U . .
H3 H 1.0684 0.3774 0.1453 0.050 Uiso 1 1 calc R . .
N1 N 1.12715(6) 0.2170(3) -0.4149(4) 0.0423(5) Uani 1 1 d U . .
N3 N 1.31444(6) 0.2746(3) -0.3718(4) 0.0385(5) Uani 1 1 d U . .
C19 C 1.35257(9) 0.1847(3) -0.0353(5) 0.0395(6) Uani 1 1 d U . .
H13 H 1.3327 0.1399 0.0240 0.047 Uiso 1 1 calc R . .
C14 C 1.34821(7) 0.2674(3) -0.2408(4) 0.0342(5) Uani 1 1 d U . .
C13 C 1.28527(7) 0.3025(3) -0.2894(4) 0.0361(5) Uani 1 1 d U . .
C12 C 1.21890(7) 0.3102(3) -0.3279(4) 0.0356(5) Uani 1 1 d U . .
H7 H 1.2203 0.3594 -0.1882 0.043 Uiso 1 1 calc R . .
C3 C 1.06410(9) 0.1780(3) -0.4091(5) 0.0419(7) Uani 1 1 d U . .
H2 H 1.0632 0.1251 -0.5468 0.050 Uiso 1 1 calc R . .
C5 C 1.09834(7) 0.3116(3) -0.0895(4) 0.0400(6) Uani 1 1 d U . .
H4 H 1.1202 0.3501 -0.0145 0.048 Uiso 1 1 calc R . .
C4 C 1.09704(7) 0.2367(3) -0.2981(5) 0.0367(5) Uani 1 1 d U . .
C8 C 1.18325(7) 0.2008(3) -0.6534(4) 0.0396(5) Uani 1 1 d U . .
H5 H 1.1609 0.1725 -0.7300 0.048 Uiso 1 1 calc R . .
C10 C 1.24780(7) 0.2166(3) -0.6363(4) 0.0363(5) Uani 1 1 d U . .
C11 C 1.25039(7) 0.2814(3) -0.4207(4) 0.0347(5) Uani 1 1 d U . .
C1 C 1.03514(7) 0.2738(3) -0.1074(5) 0.0407(6) Uani 1 1 d U . .
C9 C 1.21394(8) 0.1775(3) -0.7504(4) 0.0402(6) Uani 1 1 d U . .
H6 H 1.2121 0.1354 -0.8933 0.048 Uiso 1 1 calc R . .
C7 C 1.18561(7) 0.2669(3) -0.4397(4) 0.0366(5) Uani 1 1 d U . .
C18 C 1.38666(8) 0.1697(3) 0.0801(5) 0.0484(6) Uani 1 1 d U . .
H12 H 1.3897 0.1127 0.2162 0.058 Uiso 1 1 calc R . .
C2 C 1.03307(7) 0.1982(4) -0.3160(5) 0.0437(6) Uani 1 1 d U . .
H1 H 1.0110 0.1620 -0.3907 0.052 Uiso 1 1 calc R . .
C16 C 1.41195(8) 0.3218(4) -0.2087(6) 0.0511(7) Uani 1 1 d U . .
H10 H 1.4318 0.3690 -0.2662 0.061 Uiso 1 1 calc R . .
C15 C 1.37810(7) 0.3344(3) -0.3264(5) 0.0417(6) Uani 1 1 d U . .
H9 H 1.3754 0.3882 -0.4641 0.050 Uiso 1 1 calc R . .
C17 C 1.41619(9) 0.2395(5) -0.0069(6) 0.0524(7) Uani 1 1 d U . .
H11 H 1.4390 0.2306 0.0717 0.063 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br C1 1.897(3) . ?
O C10 1.334(3) . ?
N2 N1 1.243(3) . ?
N2 C7 1.425(3) . ?
C6 C5 1.371(4) . ?
C6 C1 1.375(4) . ?
N1 C4 1.426(3) . ?
N3 C13 1.282(3) . ?
N3 C14 1.413(3) . ?
C19 C18 1.386(4) . ?
C19 C14 1.394(4) . ?
C14 C15 1.385(3) . ?
C13 C11 1.455(4) . ?
C12 C7 1.381(4) . ?
C12 C11 1.395(3) . ?
C3 C2 1.373(4) . ?
C3 C4 1.397(4) . ?
C5 C4 1.395(4) . ?
C8 C9 1.376(4) . ?
C8 C7 1.399(4) . ?
C10 C9 1.398(4) . ?
C10 C11 1.407(4) . ?
C1 C2 1.394(4) . ?
C18 C17 1.385(5) . ?
C16 C17 1.372(5) . ?
C16 C15 1.382(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 C7 114.4(2) . . ?
C5 C6 C1 119.5(2) . . ?
N2 N1 C4 114.5(2) . . ?
C13 N3 C14 121.5(2) . . ?
C18 C19 C14 119.7(3) . . ?
C15 C14 C19 119.4(3) . . ?
C15 C14 N3 118.4(2) . . ?
C19 C14 N3 122.1(2) . . ?
N3 C13 C11 120.8(2) . . ?
C7 C12 C11 121.2(2) . . ?
C2 C3 C4 120.3(3) . . ?
C6 C5 C4 120.3(2) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 N1 125.1(2) . . ?
C3 C4 N1 115.3(2) . . ?
C9 C8 C7 120.2(2) . . ?
O C10 C9 118.7(2) . . ?
O C10 C11 121.8(2) . . ?
C9 C10 C11 119.5(2) . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 C13 120.0(2) . . ?
C10 C11 C13 120.8(2) . . ?
C6 C1 C2 121.4(2) . . ?
C6 C1 Br 119.3(2) . . ?
C2 C1 Br 119.2(2) . . ?
C8 C9 C10 120.7(2) . . ?
C12 C7 C8 119.5(2) . . ?
C12 C7 N2 116.6(2) . . ?
C8 C7 N2 123.9(2) . . ?
C17 C18 C19 120.0(3) . . ?
C3 C2 C1 118.9(3) . . ?
C17 C16 C15 120.0(3) . . ?
C16 C15 C14 120.5(3) . . ?
C16 C17 C18 120.3(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
#
#D   H   A   D - H   H...A    D...A      D - H...A  symm(A)
#
C4 H4 O2 0.93 2.33 2.860(2) 116 1_555
O1 H2 O2 0.82 2.14 2.7194(15) 128 1_655C13
C13 H13 Cg1 0.93 2.94 3.6903(18) 139 2_545
C16 H16A Cg4 0.99(2) 2.86(2) 3.692(2) 143.4(15) 2_555

_iucr_geom_hbonds_special_details 
;
Cg1 and Cg4 are the centroids of rings N1/C8-C11 and C2-C7, 
respectively.
;

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_matrix_0m
_database_code_depnum_ccdc_archive 'CCDC 1035286'
_audit_update_record             
;
2015-06-04 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H26 Br2 N6 O2 Zn'
_chemical_formula_sum            'C38 H26 Br2 N6 O2 Zn'
_chemical_formula_weight         823.34

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

_symmetry_Int_Tables_number      ?

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                   34.9897(7)
_cell_length_b                   8.3586(2)
_cell_length_c                   11.8489(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.3030(10)
_cell_angle_gamma                90.00
_cell_volume                     3342.52(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4951
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      30.3

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    3.171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_absorpt_correction_T_min  0.3295
_exptl_absorpt_correction_T_max  0.7422
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  multi-scan
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19157
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         30.27
_reflns_number_total             4951
_reflns_number_gt                3284
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_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)+(0.0416P)²+1.8792P] 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         4951
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.305
_refine_ls_shift/su_mean         0.026

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.340365(9) 0.12233(5) 0.11075(3) 0.09078(15) Uani 1 1 d . . .
Zn1 Zn 0.0000 -0.03329(4) -0.7500 0.03798(10) Uani 1 2 d S . .
O1 O 0.04911(4) 0.08121(17) -0.73022(12) 0.0416(3) Uani 1 1 d . . .
N1 N 0.20719(6) 0.1340(2) -0.33594(18) 0.0538(5) Uani 1 1 d . . .
N2 N 0.17579(5) 0.0663(2) -0.33241(17) 0.0514(5) Uani 1 1 d . . .
N3 N 0.01331(5) -0.14829(19) -0.59609(13) 0.0341(4) Uani 1 1 d . . .
C3 C 0.29856(7) 0.1150(3) -0.0281(2) 0.0566(7) Uani 1 1 d . . .
C2 C 0.30495(7) 0.1749(4) -0.1290(3) 0.0658(7) Uani 1 1 d . . .
H2 H 0.3299 0.2126 -0.1303 0.079 Uiso 1 1 calc R . .
C1 C 0.27388(7) 0.1787(3) -0.2290(2) 0.0642(7) Uani 1 1 d . . .
H1 H 0.2779 0.2198 -0.2979 0.077 Uiso 1 1 calc R . .
C6 C 0.23717(7) 0.1222(3) -0.2274(2) 0.0499(6) Uani 1 1 d . . .
C7 C 0.14485(6) 0.0766(3) -0.43810(19) 0.0445(5) Uani 1 1 d . . .
C12 C 0.11185(6) -0.0116(3) -0.43872(18) 0.0429(5) Uani 1 1 d . . .
H12 H 0.1114 -0.0696 -0.3721 0.051 Uiso 1 1 calc R . .
C11 C 0.07855(6) -0.0183(2) -0.53597(16) 0.0357(4) Uani 1 1 d . . .
C10 C 0.07862(6) 0.0744(2) -0.63651(17) 0.0355(4) Uani 1 1 d . . .
C14 C -0.01442(5) -0.2547(2) -0.56550(17) 0.0351(4) Uani 1 1 d . . .
C19 C -0.01172(6) -0.3046(3) -0.45179(18) 0.0411(5) Uani 1 1 d . . .
H19 H 0.0090 -0.2689 -0.3904 0.049 Uiso 1 1 calc R . .
C18 C -0.03978(7) -0.4072(3) -0.4302(2) 0.0506(6) Uani 1 1 d . . .
H18 H -0.0377 -0.4403 -0.3539 0.061 Uiso 1 1 calc R . .
C17 C -0.07060(7) -0.4614(3) -0.5189(3) 0.0582(6) Uani 1 1 d . . .
H17 H -0.0893 -0.5307 -0.5030 0.070 Uiso 1 1 calc R . .
C16 C -0.07362(7) -0.4125(3) -0.6313(3) 0.0653(7) Uani 1 1 d . . .
H16 H -0.0945 -0.4485 -0.6920 0.078 Uiso 1 1 calc R . .
C15 C -0.04559(6) -0.3096(3) -0.6547(2) 0.0521(6) Uani 1 1 d . . .
H15 H -0.0478 -0.2772 -0.7312 0.063 Uiso 1 1 calc R . .
C13 C 0.04713(6) -0.1198(2) -0.52184(17) 0.0364(4) Uani 1 1 d . . .
H13 H 0.0516 -0.1720 -0.4502 0.044 Uiso 1 1 calc R . .
C9 C 0.11296(6) 0.1664(3) -0.63233(19) 0.0435(5) Uani 1 1 d . . .
H10 H 0.1137 0.2287 -0.6968 0.052 Uiso 1 1 calc R . .
C8 C 0.14513(6) 0.1672(3) -0.5370(2) 0.0465(5) Uani 1 1 d . . .
H11 H 0.1673 0.2281 -0.5381 0.056 Uiso 1 1 calc R . .
C4 C 0.26213(7) 0.0581(4) -0.0242(2) 0.0624(7) Uani 1 1 d . . .
H4 H 0.2583 0.0184 0.0453 0.075 Uiso 1 1 calc R . .
C5 C 0.23118(7) 0.0607(3) -0.1249(2) 0.0581(6) Uani 1 1 d . . .
H5 H 0.2064 0.0212 -0.1237 0.070 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.892(2) . ?
Zn1 O1 1.9265(14) . ?
Zn1 O1 1.9265(14) 2_553 ?
Zn1 N3 2.0045(16) 2_553 ?
Zn1 N3 2.0045(16) . ?
O1 C10 1.303(2) . ?
N1 N2 1.246(3) . ?
N1 C6 1.432(3) . ?
N2 C7 1.426(3) . ?
N3 C13 1.297(2) . ?
N3 C14 1.432(3) . ?
C3 C2 1.368(4) . ?
C3 C4 1.373(4) . ?
C2 C1 1.380(4) . ?
C2 H2 0.9300 . ?
C1 C6 1.373(3) . ?
C1 H1 0.9300 . ?
C6 C5 1.386(4) . ?
C7 C12 1.369(3) . ?
C7 C8 1.397(3) . ?
C12 C11 1.407(3) . ?
C12 H12 0.9300 . ?
C11 C10 1.422(3) . ?
C11 C13 1.433(3) . ?
C10 C9 1.417(3) . ?
C14 C15 1.382(3) . ?
C14 C19 1.390(3) . ?
C19 C18 1.378(3) . ?
C19 H19 0.9300 . ?
C18 C17 1.369(4) . ?
C18 H18 0.9300 . ?
C17 C16 1.370(4) . ?
C17 H17 0.9300 . ?
C16 C15 1.387(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C9 C8 1.368(3) . ?
C9 H10 0.9300 . ?
C8 H11 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 120.42(9) . 2_553 ?
O1 Zn1 N3 109.55(6) . 2_553 ?
O1 Zn1 N3 98.16(6) 2_553 2_553 ?
O1 Zn1 N3 98.16(6) . . ?
O1 Zn1 N3 109.55(6) 2_553 . ?
N3 Zn1 N3 122.69(9) 2_553 . ?
C10 O1 Zn1 124.25(13) . . ?
N2 N1 C6 112.5(2) . . ?
N1 N2 C7 114.5(2) . . ?
C13 N3 C14 120.01(16) . . ?
C13 N3 Zn1 118.73(14) . . ?
C14 N3 Zn1 121.20(12) . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 Br1 118.76(19) . . ?
C4 C3 Br1 119.5(2) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 N1 115.5(2) . . ?
C5 C6 N1 124.6(2) . . ?
C12 C7 C8 118.69(19) . . ?
C12 C7 N2 114.6(2) . . ?
C8 C7 N2 126.7(2) . . ?
C7 C12 C11 122.7(2) . . ?
C7 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C12 C11 C10 118.70(19) . . ?
C12 C11 C13 115.01(18) . . ?
C10 C11 C13 126.29(17) . . ?
O1 C10 C9 118.69(18) . . ?
O1 C10 C11 124.17(18) . . ?
C9 C10 C11 117.13(18) . . ?
C15 C14 C19 118.66(19) . . ?
C15 C14 N3 117.63(18) . . ?
C19 C14 N3 123.71(17) . . ?
C18 C19 C14 119.9(2) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C17 C18 C19 121.2(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.7 . . ?
N3 C13 C11 128.32(18) . . ?
N3 C13 H13 115.8 . . ?
C11 C13 H13 115.8 . . ?
C8 C9 C10 122.5(2) . . ?
C8 C9 H10 118.8 . . ?
C10 C9 H10 118.8 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H11 119.9 . . ?
C7 C8 H11 119.9 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Zn1 O1 C10 116.80(16) 2_553 . . . ?
N3 Zn1 O1 C10 -130.67(15) 2_553 . . . ?
N3 Zn1 O1 C10 -1.63(16) . . . . ?
C6 N1 N2 C7 179.20(19) . . . . ?
O1 Zn1 N3 C13 2.96(15) . . . . ?
O1 Zn1 N3 C13 -123.46(14) 2_553 . . . ?
N3 Zn1 N3 C13 122.54(15) 2_553 . . . ?
O1 Zn1 N3 C14 -179.80(14) . . . . ?
O1 Zn1 N3 C14 53.78(15) 2_553 . . . ?
N3 Zn1 N3 C14 -60.22(13) 2_553 . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?
Br1 C3 C2 C1 -176.2(2) . . . . ?
C3 C2 C1 C6 -0.4(4) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C1 C6 N1 179.3(3) . . . . ?
N2 N1 C6 C1 173.1(2) . . . . ?
N2 N1 C6 C5 -7.5(3) . . . . ?
N1 N2 C7 C12 173.4(2) . . . . ?
N1 N2 C7 C8 -7.3(3) . . . . ?
C8 C7 C12 C11 1.7(3) . . . . ?
N2 C7 C12 C11 -179.0(2) . . . . ?
C7 C12 C11 C10 -2.1(3) . . . . ?
C7 C12 C11 C13 178.6(2) . . . . ?
Zn1 O1 C10 C9 -179.08(14) . . . . ?
Zn1 O1 C10 C11 -0.1(3) . . . . ?
C12 C11 C10 O1 -178.01(19) . . . . ?
C13 C11 C10 O1 1.3(3) . . . . ?
C12 C11 C10 C9 0.9(3) . . . . ?
C13 C11 C10 C9 -179.7(2) . . . . ?
C13 N3 C14 C15 -165.53(19) . . . . ?
Zn1 N3 C14 C15 17.3(2) . . . . ?
C13 N3 C14 C19 14.7(3) . . . . ?
Zn1 N3 C14 C19 -162.49(15) . . . . ?
C15 C14 C19 C18 0.2(3) . . . . ?
N3 C14 C19 C18 179.93(19) . . . . ?
C14 C19 C18 C17 -0.1(3) . . . . ?
C19 C18 C17 C16 -0.1(4) . . . . ?
C18 C17 C16 C15 0.2(4) . . . . ?
C19 C14 C15 C16 0.0(4) . . . . ?
N3 C14 C15 C16 -179.8(2) . . . . ?
C17 C16 C15 C14 -0.2(4) . . . . ?
C14 N3 C13 C11 179.88(19) . . . . ?
Zn1 N3 C13 C11 -2.8(3) . . . . ?
C12 C11 C13 N3 179.9(2) . . . . ?
C10 C11 C13 N3 0.5(3) . . . . ?
O1 C10 C9 C8 179.5(2) . . . . ?
C11 C10 C9 C8 0.5(3) . . . . ?
C10 C9 C8 C7 -0.9(3) . . . . ?
C12 C7 C8 C9 -0.2(3) . . . . ?
N2 C7 C8 C9 -179.5(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
Br1 C3 C4 C5 176.8(2) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C1 C6 C5 C4 0.8(4) . . . . ?
N1 C6 C5 C4 -178.6(2) . . . . ?

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
#
#D   H   A   D - H   H...A    D...A      D - H...A  symm(A)
#
C4 H4 O2 0.93 2.33 2.860(2) 116 1_555
O1 H2 O2 0.82 2.14 2.7194(15) 128 1_655C13
C13 H13 Cg1 0.93 2.94 3.6903(18) 139 2_545
C16 H16A Cg4 0.99(2) 2.86(2) 3.692(2) 143.4(15) 2_555

_iucr_geom_hbonds_special_details 
;
Cg1 and Cg4 are the centroids of rings N1/C8-C11 and C2-C7, 
respectively.
;


_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.27
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.058
