# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_EE15_RB1
_database_code_depnum_ccdc_archive 'CCDC 2026029'
loop_
_audit_author_name
_audit_author_address
'Carmen Ramirez de Arellano'
;Universidad de Valencia
Spain
;
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Br N5'
_chemical_formula_weight         290.13

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.4811(3)
_cell_length_b                   7.2879(3)
_cell_length_c                   19.9293(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.283(5)
_cell_angle_gamma                90
_cell_volume                     1075.25(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7945
_cell_measurement_theta_min      3.3252
_cell_measurement_theta_max      37.3289

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    3.805
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro (Agilent Technologies,2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford diffraction-Supernova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0267
_diffrn_reflns_number            13996
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.476
_diffrn_reflns_theta_max         31.963
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3494
_reflns_number_gt                2296
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro (Agilent Technologies,2011)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies,2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies,2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'CrystalMaker 2.1.5 (1994-2009)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
; 
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. 

Least-squares planes (x,y,z in crystal coordinates) 
and deviations from them
 (* indicates atom used to define plane)

6.9108(25) x +  2.3048(46) y +  1.6069(212) z =  3.6366 (0.0116) 

 * -0.0259 (0.0023)  N1
 * -0.0168 (0.0023)  N2
 *  0.0125 (0.0025)  C3
 *  0.0242 (0.0028)  C3A
 *  0.0000 (0.0026)  C4
 * -0.0280 (0.0026)  C5
 * -0.0073 (0.0025)  C6
 *  0.0286 (0.0025)  C7
 *  0.0127 (0.0025)  N8

 Rms deviation of fitted atoms =   0.0197


1.4108(108) x +  7.1549(21) y -  0.0510(270) z =  4.6500 (0.0204) 

Angle to previous plane (with approximate esd) = 60.657 (0.097)

 * -0.0091 (0.0023)  N11
 *  0.0174 (0.0025)  C12
 * -0.0084 (0.0024)  N13
 * -0.0075 (0.0024)  C14
 *  0.0145 (0.0024)  C15
 * -0.0069 (0.0024)  C16

 Rms deviation of fitted atoms =   0.0113
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0264P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3494
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.56208(4) 0.57165(5) 0.71346(2) 0.02137(12) Uani 1 1 d . . . . .
N1 N 0.2766(4) 0.3072(4) 0.61679(15) 0.0185(7) Uani 1 1 d . . . . .
N2 N 0.3254(4) 0.1983(4) 0.56865(16) 0.0191(7) Uani 1 1 d . . . . .
C3 C 0.3136(4) 0.2883(5) 0.50876(18) 0.0176(8) Uani 1 1 d . . . . .
C3A C 0.2537(4) 0.4663(5) 0.51841(18) 0.0152(7) Uani 1 1 d . . . . .
C4 C 0.2072(4) 0.6235(5) 0.4779(2) 0.0206(8) Uani 1 1 d . . . . .
H4 H 0.218499 0.623647 0.431043 0.025 Uiso 1 1 calc R U . . .
C5 C 0.1460(4) 0.7741(5) 0.50769(19) 0.0194(8) Uani 1 1 d . . . . .
H5 H 0.111919 0.880063 0.481162 0.023 Uiso 1 1 calc R U . . .
C6 C 0.1322(4) 0.7749(5) 0.57842(19) 0.0183(8) Uani 1 1 d . . . . .
H6 H 0.090179 0.882048 0.598347 0.022 Uiso 1 1 calc R U . . .
C7 C 0.1781(4) 0.6255(5) 0.61761(19) 0.0166(8) Uani 1 1 d . . . . .
N8 N 0.2346(4) 0.4713(4) 0.58595(15) 0.0145(6) Uani 1 1 d . . . . .
N11 N 0.1553(4) 0.6239(4) 0.82900(16) 0.0206(7) Uani 1 1 d . . . . .
C12 C 0.0154(5) 0.6549(5) 0.78025(19) 0.0206(8) Uani 1 1 d . . . . .
H12 H -0.096669 0.682911 0.795001 0.025 Uiso 1 1 calc R U . . .
N13 N 0.0159(4) 0.6507(4) 0.71328(16) 0.0195(7) Uani 1 1 d . . . . .
C14 C 0.1767(5) 0.6189(5) 0.69211(19) 0.0163(7) Uani 1 1 d . . . . .
C15 C 0.3295(4) 0.5922(5) 0.73895(19) 0.0166(7) Uani 1 1 d . . . . .
C16 C 0.3133(5) 0.5929(5) 0.80712(19) 0.0173(7) Uani 1 1 d . . . . .
H16 H 0.417520 0.570714 0.839374 0.021 Uiso 1 1 calc R U . . .
C21 C 0.3565(5) 0.1996(5) 0.44576(19) 0.0221(8) Uani 1 1 d . . . . .
H21A H 0.466017 0.254814 0.432846 0.029 Uiso 1 1 calc R U . . .
H21B H 0.255569 0.217558 0.409163 0.029 Uiso 1 1 calc R U . . .
H21C H 0.376129 0.067966 0.453762 0.029 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.888(3) . ?
N1 N2 1.336(4) . ?
N1 N8 1.361(4) . ?
N2 C3 1.354(4) . ?
C3 C3A 1.395(5) . ?
C3 C21 1.488(5) . ?
C3A N8 1.374(4) . ?
C3A C4 1.416(5) . ?
C4 C5 1.358(5) . ?
C5 C6 1.428(5) . ?
C6 C7 1.355(5) . ?
C7 N8 1.384(4) . ?
C7 C14 1.487(5) . ?
N11 C16 1.337(4) . ?
N11 C12 1.341(5) . ?
C12 N13 1.336(5) . ?
N13 C14 1.351(4) . ?
C14 C15 1.381(5) . ?
C15 C16 1.381(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 N8 105.5(3) . . ?
N1 N2 C3 110.8(3) . . ?
N2 C3 C3A 108.1(3) . . ?
N2 C3 C21 122.6(3) . . ?
C3A C3 C21 129.3(3) . . ?
N8 C3A C3 103.9(3) . . ?
N8 C3A C4 119.0(3) . . ?
C3 C3A C4 137.0(3) . . ?
C5 C4 C3A 118.4(4) . . ?
C4 C5 C6 120.8(3) . . ?
C7 C6 C5 121.1(3) . . ?
C6 C7 N8 117.3(3) . . ?
C6 C7 C14 124.3(3) . . ?
N8 C7 C14 118.4(3) . . ?
N1 N8 C3A 111.7(3) . . ?
N1 N8 C7 125.0(3) . . ?
C3A N8 C7 123.3(3) . . ?
C16 N11 C12 115.3(3) . . ?
N13 C12 N11 127.3(3) . . ?
C12 N13 C14 116.5(3) . . ?
N13 C14 C15 120.0(3) . . ?
N13 C14 C7 116.2(3) . . ?
C15 C14 C7 123.7(3) . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 Br1 118.7(3) . . ?
C14 C15 Br1 122.3(3) . . ?
N11 C16 C15 121.9(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
_geom_hbond_publ_flag
C12 H12 Br1 0.95 2.94 3.513(4) 120.3 1_455 yes
C12 H12 N1 0.95 2.53 3.392(5) 150.9 2_556 yes
C16 H16 N2 0.95 2.63 3.478(5) 149.1 2_656 yes

_refine_diff_density_max         0.967
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.152

####################################################################### 
# 
# 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_ra4a250
_database_code_depnum_ccdc_archive 'CCDC 2026030'
loop_
_audit_author_name
_audit_author_address
'Carmen Ramirez de Arellano'
;Universidad de Valencia
Spain
;
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 Br2 Cl4 N10 Zn2'
_chemical_formula_weight         852.81

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.3058(5)
_cell_length_b                   12.5506(3)
_cell_length_c                   15.1113(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.054(3)
_cell_angle_gamma                90
_cell_volume                     2866.67(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    25570
_cell_measurement_theta_min      2.3866
_cell_measurement_theta_max      32.5875

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    4.869
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77337
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro (Agilent Technologies,2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford diffraction-Supernova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0267
_diffrn_reflns_number            61348
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.394
_diffrn_reflns_theta_max         32.652
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5055
_reflns_number_gt                3960
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro (Agilent Technologies,2011)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies,2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies,2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'CrystalMaker 2.1.5 (1994-2009)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
; 
 Distance CONT1 
    8.8887 (0.0004)  Zn1 - Zn1_$1 

 Distance CONT2 
   10.0914 (0.0005)  Zn1 - Zn1_$2 

 Distance CONT3 
    3.4215 (0.0013)  C15 - Cl1_$3 
    88.97 ( 0.04)  Br1 - C15 - Cl1_$3 
   109.55 ( 0.03)  C15 - Cl1_$3 - Zn1_$3 
  -171.06 ( 0.03)  Br1 - C15 - Cl1_$3 - Zn1_$3 

 Distance CONT5 
    3.2329 (0.0004)  Br1 - Cl2_$4 
   172.75 ( 0.04)  C15 - Br1 - Cl2_$4 
   152.64 ( 0.02)  Br1 - Cl2_$4 - Zn1_$4 
    74.48 ( 0.32)  C15 - Br1 - Cl2_$4 - Zn1_$4  

Least-squares planes (x,y,z in crystal coordinates) and deviations 
from the (* indicates atom used to define plane)

3.6454(0.0046)x + 12.0352(0.0016)y - 2.8647(0.0063)z = 0.7514 (0.0035) 

 * -0.0123 (0.0009)  N1
 * -0.0127 (0.0009)  N2
 * -0.0006 (0.0010)  C3
 *  0.0137 (0.0012)  C3A
 *  0.0060 (0.0010)  C4
 * -0.0143 (0.0011)  C5
 * -0.0139 (0.0010)  C6
 *  0.0149 (0.0010)  C7
 *  0.0192 (0.0010)  N8

Rms deviation of fitted atoms =   0.0130


12.5956(0.0045)x + 6.0513(0.0060)y + 2.5277(0.0079)z = 5.3956(0.0062) 

Angle to previous plane (with approximate esd) = 52.261 ( 0.039 )

 * -0.0212 (0.0009)  N11
 *  0.0239 (0.0009)  C12
 * -0.0025 (0.0009)  N13
 * -0.0199 (0.0009)  C14
 *  0.0208 (0.0009)  C15
 * -0.0012 (0.0009)  C16

Rms deviation of fitted atoms =   0.0176
 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²] 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         5055
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0186
_refine_ls_wR_factor_ref         0.0441
_refine_ls_wR_factor_gt          0.0434
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn -0.08305(2) 0.22435(2) 0.45463(2) 0.01246(4) Uani 1 1 d . . . . .
Br1 Br 0.11845(2) 0.39488(2) 0.69818(2) 0.01547(4) Uani 1 1 d . . . . .
Cl1 Cl -0.15977(2) 0.11087(3) 0.36187(2) 0.01925(7) Uani 1 1 d . . . . .
Cl2 Cl -0.06908(2) 0.39535(3) 0.42361(3) 0.02229(8) Uani 1 1 d . . . . .
N1 N 0.07092(7) 0.18026(9) 0.58955(7) 0.0134(2) Uani 1 1 d . . . . .
N2 N 0.04113(7) 0.16841(9) 0.50196(7) 0.0133(2) Uani 1 1 d . . . . .
C3 C 0.10582(9) 0.13892(11) 0.45619(9) 0.0136(3) Uani 1 1 d . . . . .
C3A C 0.18329(9) 0.13131(10) 0.51780(8) 0.0127(2) Uani 1 1 d . . . . .
C4 C 0.27247(9) 0.10331(11) 0.51636(9) 0.0159(3) Uani 1 1 d . . . . .
H4 H 0.291841 0.085134 0.461580 0.019 Uiso 1 1 calc R U . . .
C5 C 0.33015(9) 0.10279(11) 0.59464(10) 0.0170(3) Uani 1 1 d . . . . .
H5 H 0.390167 0.083440 0.594737 0.020 Uiso 1 1 calc R U . . .
C6 C 0.30102(9) 0.13110(11) 0.67638(9) 0.0153(3) Uani 1 1 d . . . . .
H6 H 0.341983 0.129903 0.730577 0.018 Uiso 1 1 calc R U . . .
C7 C 0.21562(8) 0.15986(10) 0.67847(8) 0.0118(2) Uani 1 1 d . . . . .
N8 N 0.15772(7) 0.15869(8) 0.59835(7) 0.0108(2) Uani 1 1 d . . . . .
N11 N 0.13459(7) 0.22078(9) 0.92697(7) 0.0133(2) Uani 1 1 d . . . . .
C12 C 0.18243(9) 0.13674(11) 0.90762(9) 0.0161(3) Uani 1 1 d . . . . .
H12 H 0.200970 0.087717 0.954742 0.019 Uiso 1 1 calc R U . . .
N13 N 0.20602(8) 0.11604(9) 0.82919(8) 0.0151(2) Uani 1 1 d . . . . .
C14 C 0.18359(8) 0.18750(10) 0.76302(8) 0.0119(2) Uani 1 1 d . . . . .
C15 C 0.13876(8) 0.28075(10) 0.77924(8) 0.0119(2) Uani 1 1 d . . . . .
C16 C 0.11403(9) 0.29369(11) 0.86277(9) 0.0135(3) Uani 1 1 d . . . . .
H16 H 0.081903 0.355451 0.874633 0.016 Uiso 1 1 calc R U . . .
C21 C 0.09020(10) 0.12070(12) 0.35733(9) 0.0201(3) Uani 1 1 d . . . . .
H21A H 0.047958 0.062193 0.342916 0.030 Uiso 1 1 calc R U . . .
H21B H 0.146219 0.102267 0.337420 0.030 Uiso 1 1 calc R U . . .
H21C H 0.066173 0.185689 0.326763 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.0467(11) . ?
Zn1 N11 2.0663(11) 2_556 ?
Zn1 Cl1 2.2032(4) . ?
Zn1 Cl2 2.2142(4) . ?
Br1 C15 1.8785(13) . ?
N1 N2 1.3386(15) . ?
N1 N8 1.3418(15) . ?
N2 C3 1.3459(17) . ?
C3 C3A 1.3909(18) . ?
C3 C21 1.4928(18) . ?
C3A N8 1.3795(16) . ?
C3A C4 1.4129(19) . ?
C4 C5 1.360(2) . ?
C5 C6 1.4226(19) . ?
C6 C7 1.3612(18) . ?
C7 N8 1.3833(16) . ?
C7 C14 1.4799(17) . ?
N11 C16 1.3347(16) . ?
N11 C12 1.3422(17) . ?
C12 N13 1.3180(17) . ?
N13 C14 1.3470(16) . ?
C14 C15 1.3977(18) . ?
C15 C16 1.3832(17) . ?

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 N11 98.63(4) . 2_556 ?
N2 Zn1 Cl1 111.91(3) . . ?
N11 Zn1 Cl1 107.40(3) 2_556 . ?
N2 Zn1 Cl2 106.93(3) . . ?
N11 Zn1 Cl2 105.49(3) 2_556 . ?
Cl1 Zn1 Cl2 123.465(15) . . ?
N2 N1 N8 104.69(10) . . ?
N1 N2 C3 112.03(11) . . ?
N1 N2 Zn1 117.42(8) . . ?
C3 N2 Zn1 129.24(9) . . ?
N2 C3 C3A 107.07(11) . . ?
N2 C3 C21 122.79(12) . . ?
C3A C3 C21 130.15(12) . . ?
N8 C3A C3 104.07(11) . . ?
N8 C3A C4 118.98(12) . . ?
C3 C3A C4 136.94(12) . . ?
C5 C4 C3A 118.96(12) . . ?
C4 C5 C6 120.31(13) . . ?
C7 C6 C5 121.31(13) . . ?
C6 C7 N8 117.53(12) . . ?
C6 C7 C14 122.14(12) . . ?
N8 C7 C14 120.29(11) . . ?
N1 N8 C3A 112.13(10) . . ?
N1 N8 C7 124.93(10) . . ?
C3A N8 C7 122.90(11) . . ?
C16 N11 C12 117.05(11) . . ?
C16 N11 Zn1 122.41(9) . 2_556 ?
C12 N11 Zn1 120.09(9) . 2_556 ?
N13 C12 N11 125.94(12) . . ?
C12 N13 C14 117.54(12) . . ?
N13 C14 C15 120.15(11) . . ?
N13 C14 C7 113.86(11) . . ?
C15 C14 C7 125.89(11) . . ?
C16 C15 C14 118.08(12) . . ?
C16 C15 Br1 117.68(10) . . ?
C14 C15 Br1 124.02(10) . . ?
N11 C16 C15 121.05(12) . . ?

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
N8 N1 N2 C3 0.82(14) . . . . ?
N8 N1 N2 Zn1 -167.30(8) . . . . ?
N1 N2 C3 C3A -0.23(15) . . . . ?
Zn1 N2 C3 C3A 166.12(9) . . . . ?
N1 N2 C3 C21 -179.78(12) . . . . ?
Zn1 N2 C3 C21 -13.43(19) . . . . ?
N2 C3 C3A N8 -0.44(14) . . . . ?
C21 C3 C3A N8 179.06(14) . . . . ?
N2 C3 C3A C4 178.55(15) . . . . ?
C21 C3 C3A C4 -1.9(3) . . . . ?
N8 C3A C4 C5 0.89(19) . . . . ?
C3 C3A C4 C5 -178.00(15) . . . . ?
C3A C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 N8 1.2(2) . . . . ?
C5 C6 C7 C14 178.76(12) . . . . ?
N2 N1 N8 C3A -1.13(14) . . . . ?
N2 N1 N8 C7 -179.18(12) . . . . ?
C3 C3A N8 N1 0.99(14) . . . . ?
C4 C3A N8 N1 -178.22(11) . . . . ?
C3 C3A N8 C7 179.09(12) . . . . ?
C4 C3A N8 C7 -0.13(19) . . . . ?
C6 C7 N8 N1 176.96(12) . . . . ?
C14 C7 N8 N1 -0.69(19) . . . . ?
C6 C7 N8 C3A -0.89(19) . . . . ?
C14 C7 N8 C3A -178.54(12) . . . . ?
C16 N11 C12 N13 -4.8(2) . . . . ?
Zn1 N11 C12 N13 167.73(11) 2_556 . . . ?
N11 C12 N13 C14 3.0(2) . . . . ?
C12 N13 C14 C15 1.45(19) . . . . ?
C12 N13 C14 C7 177.82(12) . . . . ?
C6 C7 C14 N13 -49.00(17) . . . . ?
N8 C7 C14 N13 128.54(13) . . . . ?
C6 C7 C14 C15 127.12(15) . . . . ?
N8 C7 C14 C15 -55.34(18) . . . . ?
N13 C14 C15 C16 -3.75(19) . . . . ?
C7 C14 C15 C16 -179.65(12) . . . . ?
N13 C14 C15 Br1 170.81(10) . . . . ?
C7 C14 C15 Br1 -5.08(19) . . . . ?
C12 N11 C16 C15 2.05(19) . . . . ?
Zn1 N11 C16 C15 -170.25(9) 2_556 . . . ?
C14 C15 C16 N11 1.93(19) . . . . ?
Br1 C15 C16 N11 -172.99(10) . . . . ?

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
_geom_hbond_publ_flag
C4 H4 Br1 0.95 2.97 3.8732(13) 159.3 7_556 yes
C5 H5 Cl2 0.95 2.81 3.7106(14) 159.0 7_556 yes

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.076

