# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1919003'
loop_
_audit_author_name
_audit_author_address
'Houcine Naili'
;University of Sfax
Tunisia
;
#Added by publCIF



_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2020-01-17 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  'multilayer monochromator'
#Added by publCIF




_cell_special_details            ?

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 Cl2 N2  O'
_chemical_formula_weight         199.08

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   16.678(5)
_cell_length_b                   7.107(5)
_cell_length_c                   15.865(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 97.397(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1864.8(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8571
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.645
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35787
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.231
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4666
_reflns_number_gt                4319
_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0457P)²+0.8252P] 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         4666
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.191
_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
N1 N 0.88323(6) 0.22103(16) 0.02864(7) 0.0138(2) Uani 1 1 d . . . . .
H3 H 0.837461 0.214713 0.048011 0.017 Uiso 1 1 calc R U . . .
N3 N 0.38221(7) 0.31321(16) 0.02606(7) 0.0152(2) Uani 1 1 d . . . . .
H4 H 0.337671 0.337710 0.045762 0.018 Uiso 1 1 calc R U . . .
N4 N 0.29123(7) 0.22438(17) -0.19281(7) 0.0176(2) Uani 1 1 d . . . . .
H5A H 0.242230 0.245488 -0.220611 0.026 Uiso 1 1 calc R U . . .
H5B H 0.328477 0.268947 -0.222992 0.026 Uiso 1 1 calc R U . . .
H5C H 0.298433 0.101203 -0.185052 0.026 Uiso 1 1 calc R U . . .
N2 N 0.79126(7) 0.21444(19) -0.18543(7) 0.0198(2) Uani 1 1 d . . . . .
H6A H 0.744831 0.173969 -0.213516 0.030 Uiso 1 1 calc R U . . .
H6B H 0.787805 0.337258 -0.175539 0.030 Uiso 1 1 calc R U . . .
H6C H 0.831187 0.193252 -0.216413 0.030 Uiso 1 1 calc R U . . .
C5 C 0.88607(7) 0.17639(17) -0.05344(8) 0.0126(2) Uani 1 1 d . . . . .
C11 C 0.38034(7) 0.29045(18) -0.05854(8) 0.0126(2) Uani 1 1 d . . . . .
C4 C 0.95978(8) 0.18533(19) -0.08479(8) 0.0151(2) Uani 1 1 d . . . . .
H31 H 0.963363 0.153327 -0.141019 0.018 Uiso 1 1 calc R U . . .
C10 C 0.45174(8) 0.2506(2) -0.09026(8) 0.0170(3) Uani 1 1 d . . . . .
H41 H 0.452123 0.234973 -0.148410 0.020 Uiso 1 1 calc R U . . .
C3 C 1.02840(8) 0.24244(19) -0.03168(8) 0.0158(3) Uani 1 1 d . . . . .
H5 H 1.077898 0.250501 -0.052557 0.019 Uiso 1 1 calc R U . . .
C8 C 0.52270(8) 0.2591(2) 0.05217(8) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.570074 0.249110 0.089832 0.022 Uiso 1 1 calc R U . . .
C1 C 0.94851(8) 0.2749(2) 0.08167(8) 0.0173(3) Uani 1 1 d . . . . .
H7 H 0.943568 0.303792 0.137943 0.021 Uiso 1 1 calc R U . . .
C2 C 1.02280(8) 0.2875(2) 0.05281(8) 0.0172(3) Uani 1 1 d . . . . .
H8 H 1.068274 0.325303 0.089005 0.021 Uiso 1 1 calc R U . . .
C9 C 0.52340(8) 0.2337(2) -0.03459(9) 0.0177(3) Uani 1 1 d . . . . .
H9 H 0.571555 0.205523 -0.055570 0.021 Uiso 1 1 calc R U . . .
C12 C 0.29877(8) 0.3196(2) -0.10960(8) 0.0178(3) Uani 1 1 d . . . . .
H10A H 0.257273 0.272451 -0.077530 0.021 Uiso 1 1 calc R U . . .
H10B H 0.289680 0.453388 -0.118455 0.021 Uiso 1 1 calc R U . . .
C7 C 0.45026(8) 0.2995(2) 0.08106(8) 0.0192(3) Uani 1 1 d . . . . .
H11 H 0.448426 0.317256 0.138856 0.023 Uiso 1 1 calc R U . . .
C6 C 0.80779(8) 0.1129(2) -0.10375(9) 0.0180(3) Uani 1 1 d . . . . .
H12A H 0.810543 -0.021062 -0.114680 0.022 Uiso 1 1 calc R U . . .
H12B H 0.763709 0.134404 -0.070554 0.022 Uiso 1 1 calc R U . . .
Cl2 Cl 0.72908(2) 0.17066(5) 0.10844(2) 0.01835(9) Uani 1 1 d . . . . .
Cl3 Cl 0.22863(2) 0.39359(5) 0.10225(2) 0.01857(9) Uani 1 1 d . . . . .
Cl4 Cl 0.38568(2) 0.53603(5) -0.28371(2) 0.01969(9) Uani 1 1 d . . . . .
Cl1 Cl 0.88853(2) -0.11766(5) -0.27423(2) 0.01730(9) Uani 1 1 d . . . . .
O2 O 0.42272(7) -0.02814(18) -0.24999(7) 0.0247(2) Uani 1 1 d . . . . .
O1 O 0.91959(7) 0.43910(18) -0.24727(8) 0.0265(2) Uani 1 1 d . . . . .
H118 H 0.9647(15) 0.433(4) -0.2393(15) 0.045(7) Uiso 1 1 d . . . . .
H120 H 0.4675(16) -0.034(4) -0.2375(16) 0.056(8) Uiso 1 1 d . . . . .
H119 H 0.9040(15) 0.550(4) -0.2540(16) 0.047(7) Uiso 1 1 d . . . . .
H121 H 0.4046(17) -0.141(5) -0.2565(18) 0.069(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
N1 C1 1.3431(17) . ?
N1 C5 1.3471(16) . ?
N3 C7 1.3431(17) . ?
N3 C11 1.3483(16) . ?
N4 C12 1.4745(17) . ?
N2 C6 1.4777(18) . ?
C5 C4 1.3856(18) . ?
C5 C6 1.5089(17) . ?
C11 C10 1.3805(18) . ?
C11 C12 1.5054(17) . ?
C4 C3 1.3914(18) . ?
C10 C9 1.3967(18) . ?
C3 C2 1.3930(19) . ?
C8 C7 1.376(2) . ?
C8 C9 1.3898(19) . ?
C1 C2 1.3780(19) . ?

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
C1 N1 C5 123.10(11) . . ?
C7 N3 C11 123.18(11) . . ?
N1 C5 C4 118.64(11) . . ?
N1 C5 C6 116.49(11) . . ?
C4 C5 C6 124.82(12) . . ?
N3 C11 C10 118.49(11) . . ?
N3 C11 C12 115.00(11) . . ?
C10 C11 C12 126.46(12) . . ?
C5 C4 C3 119.65(12) . . ?
C11 C10 C9 119.67(12) . . ?
C4 C3 C2 119.86(12) . . ?
C7 C8 C9 118.46(12) . . ?
N1 C1 C2 120.09(12) . . ?
C1 C2 C3 118.64(12) . . ?
C8 C9 C10 119.97(12) . . ?
N4 C12 C11 112.67(11) . . ?
N3 C7 C8 120.22(12) . . ?
N2 C6 C5 111.65(11) . . ?

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
N1 H3 Cl2 0.86 2.17 3.0296(13) 172.4 .
N3 H4 Cl3 0.86 2.17 3.0241(13) 176.8 .
N4 H5A Cl1 0.89 2.38 3.1809(15) 149.9 2_654
N4 H5A Cl3 0.89 2.96 3.3897(15) 111.6 4_565
N4 H5C Cl2 0.89 2.36 3.147(2) 147.7 3_655
N4 H5C O2 0.89 2.60 3.0603(19) 113.2 .
N4 H5B Cl4 0.89 2.38 3.1705(17) 147.6 .
N2 H6A Cl4 0.89 2.38 3.1913(15) 151.2 2_644
N2 H6C O1 0.89 2.38 2.9383(18) 121.2 .
N2 H6C Cl1 0.89 2.62 3.2826(18) 132.0 .
N2 H6B Cl3 0.89 2.27 3.118(2) 158.5 3_665
O1 H118 Cl1 0.75(2) 2.46(2) 3.1999(15) 173(3) 2_754
O2 H120 Cl4 0.75(3) 2.48(3) 3.2039(15) 163(3) 2_644
O1 H119 Cl1 0.84(3) 2.39(3) 3.212(3) 168(2) 1_565
O2 H121 Cl4 0.86(3) 2.35(3) 3.190(2) 166(3) 1_545

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1919004'
loop_
_audit_author_name
_audit_author_address
'Houcine Naili'
;University of Sfax
Tunisia
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2020-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H10 Br2 N2'
_chemical_formula_weight         269.98

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      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                   6.6560(9)
_cell_length_b                   7.7563(10)
_cell_length_c                   9.1524(12)
_cell_angle_alpha                76.320(4)
_cell_angle_beta                 80.652(4)
_cell_angle_gamma                82.187(5)
_cell_volume                     450.65(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8571
_cell_measurement_theta_min      1.2
_cell_measurement_theta_max      28.4

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.990
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    8.927
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.130
_exptl_absorpt_correction_T_max  0.240
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10622
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.118
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2065
_reflns_number_gt                1928
_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0234P)²+0.2778P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.073(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2065
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0515
_refine_ls_wR_factor_gt          0.0506
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.62812(3) -0.08766(3) 0.76796(2) 0.01704(9) Uani 1 1 d . . . . .
Br2 Br 1.25218(3) 0.60915(2) 0.62284(2) 0.01308(9) Uani 1 1 d . . . . .
N1 N 0.8458(2) 0.3137(2) 0.72342(18) 0.0126(3) Uani 1 1 d . . . . .
H1A H 0.806539 0.326461 0.636153 0.015 Uiso 1 1 calc R U . . .
N2 N 1.3263(3) 0.1958(2) 0.56231(19) 0.0149(3) Uani 1 1 d . . . . .
H2A H 1.388432 0.142494 0.488583 0.022 Uiso 1 1 calc R U . . .
H2B H 1.302714 0.312367 0.524809 0.022 Uiso 1 1 calc R U . . .
H2C H 1.405892 0.177510 0.634919 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7900(3) 0.3810(3) 0.9644(2) 0.0195(4) Uani 1 1 d . . . . .
H2 H 0.711584 0.438868 1.035732 0.023 Uiso 1 1 calc R U . . .
C5 C 1.0180(3) 0.2072(2) 0.7524(2) 0.0114(4) Uani 1 1 d . . . . .
C4 C 1.0826(3) 0.1858(3) 0.8924(2) 0.0147(4) Uani 1 1 d . . . . .
H4 H 1.202170 0.113944 0.914899 0.018 Uiso 1 1 calc R U . . .
C3 C 0.9668(3) 0.2730(3) 0.9987(2) 0.0169(4) Uani 1 1 d . . . . .
H3 H 1.008204 0.258715 1.093494 0.020 Uiso 1 1 calc R U . . .
C1 C 0.7315(3) 0.4016(3) 0.8233(2) 0.0184(4) Uani 1 1 d . . . . .
H1 H 0.614533 0.475353 0.797324 0.022 Uiso 1 1 calc R U . . .
C6 C 1.1280(3) 0.1203(3) 0.6270(2) 0.0156(4) Uani 1 1 d . . . . .
H6A H 1.153626 -0.007052 0.666400 0.019 Uiso 1 1 calc R U . . .
H6B H 1.042188 0.138601 0.547475 0.019 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
N1 C5 1.343(3) . ?
N1 C1 1.344(3) . ?
N1 H1A 0.8600 . ?
N2 C6 1.492(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C2 C1 1.376(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C5 C4 1.383(3) . ?
C5 C6 1.505(3) . ?
C4 C3 1.387(3) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C1 H1 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

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
C5 N1 C1 123.64(17) . . ?
C5 N1 H1A 118.2 . . ?
C1 N1 H1A 118.2 . . ?
C6 N2 H2A 109.5 . . ?
C6 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C6 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C1 C2 C3 119.14(19) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
N1 C5 C4 118.67(17) . . ?
N1 C5 C6 116.61(17) . . ?
C4 C5 C6 124.72(18) . . ?
C5 C4 C3 119.14(19) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C2 C3 C4 120.28(19) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
N1 C1 C2 119.11(19) . . ?
N1 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
N2 C6 C5 111.10(16) . . ?
N2 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?

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
N1 H1A Br2 0.86 2.39 3.2397(17) 170.0 2_766
N2 H2A Br1 0.89 2.50 3.2808(17) 146.0 2_756
N2 H2C Br1 0.89 2.54 3.2378(18) 135.3 1_655
N2 H2B Br2 0.89 2.62 3.3393(17) 138.0 .
C2 H2 Br2 0.93 3.10 3.761(2) 129.2 2_767
C1 H1 Br2 0.93 3.04 3.904(2) 155.7 1_455
C6 H6A Br2 0.97 3.07 3.947(2) 151.8 1_545
C6 H6B Br2 0.97 2.93 3.769(2) 144.9 2_766

_refine_diff_density_max         0.650
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.131

