# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_new
_audit_block_doi                 10.5517/ccdc.csd.cc21hbfb
_database_code_depnum_ccdc_archive 'CCDC 1891571'
loop_
_audit_author_name
_audit_author_address
LiMaoFan
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2019-04-25 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;
_audit_creation_date             2019-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br5 Sb, 2(C3 H8 N)'
_chemical_formula_sum            'C6 H16 Br5 N2 Sb'
_chemical_formula_weight         637.51
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P n c a'
_space_group_name_Hall           '-P 2a 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.5314(7)
_cell_length_b                   18.9885(8)
_cell_length_c                   7.8845(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3373.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1984
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.456
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19130
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.797
_diffrn_ambient_temperature      300.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2035
_reflns_number_total             3868
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.970
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+11.2635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1477
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2. Restrained distances
 C1-C2 = C2-C3 = C3-C1
 1.5 with sigma of 0.01
 C1-N1
 1.5 with sigma of 0.01
 C4-C5 = C5-C6 = C6-C4
 1.5 with sigma of 0.01
 C4-N2
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02
C4 \\sim C5 \\sim C6: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02
4.a Ternary CH refined with riding coordinates:
 C4(H4), C1(H1)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C2(H2D,H2E), C5(H5A,H5B)
4.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Sb1 Sb 0.40187(3) 0.13545(3) 0.23831(7) 0.0455(2) Uani 1 1 d . . . . .
Br5 Br 0.38615(6) 0.05159(7) 0.51100(14) 0.0733(4) Uani 1 1 d . . . . .
Br1 Br 0.38218(6) 0.03432(6) 0.02337(15) 0.0738(4) Uani 1 1 d . . . . .
Br4 Br 0.51837(5) 0.09810(7) 0.24132(17) 0.0739(4) Uani 1 1 d . . . . .
Br2 Br 0.27837(5) 0.16805(8) 0.22762(19) 0.0841(4) Uani 1 1 d . . . . .
Br3 Br 0.42150(6) 0.22853(8) -0.04727(17) 0.0862(5) Uani 1 1 d . . . . .
N2 N 0.2960(4) 0.1584(6) 0.7559(14) 0.101(4) Uani 1 1 d D . . . .
H2A H 0.299635 0.204373 0.736530 0.152 Uiso 1 1 calc GR . . . .
H2B H 0.327256 0.135865 0.713583 0.152 Uiso 1 1 calc GR . . . .
H2C H 0.293868 0.150800 0.867144 0.152 Uiso 1 1 calc GR . . . .
N1 N 0.5119(5) 0.0897(7) 0.7538(16) 0.119(5) Uani 1 1 d D . . . .
H1A H 0.518898 0.047069 0.796464 0.178 Uiso 1 1 calc GR . . . .
H1B H 0.486316 0.086169 0.668238 0.178 Uiso 1 1 calc GR . . . .
H1C H 0.496633 0.117178 0.834166 0.178 Uiso 1 1 calc GR . . . .
C6 C 0.1856(8) 0.1525(12) 0.762(3) 0.214(8) Uani 1 1 d D U . . .
H6A H 0.150427 0.160437 0.693395 0.257 Uiso 1 1 calc R . . . .
H6B H 0.189020 0.182047 0.861406 0.257 Uiso 1 1 calc R . . . .
C4 C 0.2409(6) 0.1320(12) 0.673(2) 0.220(8) Uani 1 1 d D U . . .
H4 H 0.240221 0.128246 0.549187 0.264 Uiso 1 1 calc R . . . .
C3 C 0.5973(10) 0.1661(11) 0.820(2) 0.176(6) Uani 1 1 d D U . . .
H3A H 0.640142 0.163467 0.829806 0.211 Uiso 1 1 calc R . . . .
H3B H 0.576355 0.174562 0.925087 0.211 Uiso 1 1 calc R . . . .
C1 C 0.5683(8) 0.1207(9) 0.692(2) 0.173(6) Uani 1 1 d D U . . .
H1 H 0.594059 0.090323 0.623152 0.208 Uiso 1 1 calc R . . . .
C2 C 0.5725(11) 0.1975(9) 0.663(2) 0.171(6) Uani 1 1 d D U . . .
H2D H 0.536405 0.225048 0.672573 0.205 Uiso 1 1 calc R . . . .
H2E H 0.600191 0.213953 0.577293 0.205 Uiso 1 1 calc R . . . .
C5 C 0.2094(10) 0.0790(11) 0.772(3) 0.225(8) Uani 1 1 d D U . . .
H5A H 0.226954 0.064011 0.878167 0.270 Uiso 1 1 calc R . . . .
H5B H 0.188403 0.042424 0.710334 0.270 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
Sb1 Br5 2.6989(12) . ?
Sb1 Br1 2.5993(12) . ?
Sb1 Br4 2.7190(13) . ?
Sb1 Br2 2.8520(13) . ?
Sb1 Br3 2.8964(13) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C4 1.488(10) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.484(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C4 1.480(10) . ?
C6 C5 1.497(10) . ?
C4 H4 0.9800 . ?
C4 C5 1.456(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C1 1.480(10) . ?
C3 C2 1.482(10) . ?
C1 H1 0.9800 . ?
C1 C2 1.480(9) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 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
Br5 Sb1 Br4 88.04(4) . . ?
Br5 Sb1 Br2 91.35(5) . . ?
Br5 Sb1 Br3 177.99(5) . . ?
Br1 Sb1 Br5 93.50(5) . . ?
Br1 Sb1 Br4 88.73(5) . . ?
Br1 Sb1 Br2 88.54(5) . . ?
Br1 Sb1 Br3 88.28(5) . . ?
Br4 Sb1 Br2 177.16(5) . . ?
Br4 Sb1 Br3 91.07(4) . . ?
Br2 Sb1 Br3 89.63(5) . . ?
Sb1 Br3 Sb1 154.85(6) . 8_565 ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C4 N2 H2A 109.5 . . ?
C4 N2 H2B 109.5 . . ?
C4 N2 H2C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H6A C6 H6B 115.1 . . ?
C4 C6 H6A 117.9 . . ?
C4 C6 H6B 117.9 . . ?
C4 C6 C5 58.6(5) . . ?
C5 C6 H6A 117.9 . . ?
C5 C6 H6B 117.9 . . ?
N2 C4 H4 118.4 . . ?
C6 C4 N2 113.9(15) . . ?
C6 C4 H4 118.4 . . ?
C5 C4 N2 113.9(18) . . ?
C5 C4 C6 61.3(5) . . ?
C5 C4 H4 118.4 . . ?
H3A C3 H3B 114.9 . . ?
C1 C3 H3A 117.8 . . ?
C1 C3 H3B 117.8 . . ?
C1 C3 C2 59.9(5) . . ?
C2 C3 H3A 117.8 . . ?
C2 C3 H3B 117.8 . . ?
N1 C1 H1 117.2 . . ?
C3 C1 N1 112.6(17) . . ?
C3 C1 H1 117.2 . . ?
C2 C1 N1 119.8(19) . . ?
C2 C1 C3 60.1(5) . . ?
C2 C1 H1 117.2 . . ?
C3 C2 H2D 117.8 . . ?
C3 C2 H2E 117.8 . . ?
C1 C2 C3 60.0(5) . . ?
C1 C2 H2D 117.8 . . ?
C1 C2 H2E 117.8 . . ?
H2D C2 H2E 114.9 . . ?
C6 C5 H5A 117.8 . . ?
C6 C5 H5B 117.8 . . ?
C4 C5 C6 60.2(5) . . ?
C4 C5 H5A 117.8 . . ?
C4 C5 H5B 117.8 . . ?
H5A C5 H5B 114.9 . . ?

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
N2 H2A Br2 0.89 2.47 3.326(12) 161.5 8_566 yes
N2 H2B Br5 0.89 2.62 3.460(11) 157.4 . yes
N2 H2C Br2 0.89 2.88 3.745(11) 163.7 1_556 yes
N1 H1A Br1 0.89 3.06 3.785(14) 139.7 5_656 yes
N1 H1A Br4 0.89 2.90 3.630(14) 140.8 5_656 yes
N1 H1B Br5 0.89 2.66 3.495(12) 157.2 . yes
N1 H1C Br3 0.89 2.87 3.682(13) 153.3 1_556 yes
C4 H4 Br2 0.98 2.78 3.677(18) 152.2 . yes
C1 H1 Br5 0.98 2.93 3.782(19) 146.1 5_656 yes
C5 H5B Br5 0.97 2.91 3.87(3) 171.9 2 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1891569'
loop_
_audit_author_name
_audit_author_address
LiMaoFan
;QingDaoUniversity
China
;
_audit_update_record             
;
2019-05-16 deposited with the CCDC.	2019-05-16 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 H16 Br5 N2 Sb'
_chemical_formula_weight         637.51

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'
Br Br -0.2901 2.4595 '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'
Sb Sb -0.5866 1.5461 '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                   11.894(2)
_cell_length_b                   19.099(4)
_cell_length_c                   7.8047(16)
_cell_angle_alpha                90
_cell_angle_beta                 108.91(3)
_cell_angle_gamma                90
_cell_volume                     1677.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    9261
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      27.29

_exptl_crystal_description       bulk
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.525
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    13.532
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0510
_exptl_absorpt_correction_T_max  0.0949
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      270(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31752
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3862
_reflns_number_gt                3310
_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          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+3.2000P] 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       0.00152(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3862
_refine_ls_number_parameters     131
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.026
_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
Sb1 Sb 0.31027(3) 0.36335(2) 0.64024(5) 0.03903(10) Uani 1 1 d . . . . .
Br1 Br 0.26876(7) 0.46675(3) 0.41265(8) 0.05968(19) Uani 1 1 d . . . . .
Br2 Br 0.35462(7) 0.27739(4) 0.36322(9) 0.0641(2) Uani 1 1 d . . . . .
Br3 Br 0.06047(6) 0.32972(4) 0.49852(10) 0.06423(19) Uani 1 1 d . . . . .
Br4 Br 0.27621(7) 0.44388(3) 0.90388(8) 0.05763(17) Uani 1 1 d . . . . .
Br5 Br 0.54048(6) 0.40179(4) 0.76217(10) 0.06231(18) Uani 1 1 d . . . . .
N1 N 0.0932(4) 0.1577(3) 0.5624(8) 0.0657(15) Uani 1 1 d . . . . .
H1A H 0.102914 0.200740 0.525610 0.079 Uiso 1 1 calc R U . . .
H1B H 0.152932 0.130635 0.557173 0.079 Uiso 1 1 calc R U . . .
H1C H 0.092266 0.159343 0.675849 0.079 Uiso 1 1 calc R U . . .
C1 C -0.0192(7) 0.1289(5) 0.4449(13) 0.091(2) Uani 1 1 d . U . . .
H1 H -0.022744 0.119572 0.319733 0.109 Uiso 1 1 calc R U . . .
C2 C -0.0838(9) 0.0824(6) 0.5162(16) 0.113(3) Uani 1 1 d . U . . .
H2D H -0.051836 0.071254 0.644101 0.136 Uiso 1 1 calc R U . . .
H2E H -0.125274 0.044272 0.439589 0.136 Uiso 1 1 calc R U . . .
C3 C -0.1278(8) 0.1524(6) 0.4672(16) 0.109(3) Uani 1 1 d . U . . .
H3A H -0.196268 0.158272 0.359291 0.131 Uiso 1 1 calc R U . . .
H3B H -0.122734 0.185289 0.564072 0.131 Uiso 1 1 calc R U . . .
N2 N 0.5335(5) 0.4114(3) 0.2650(10) 0.086(2) Uani 1 1 d . . . . .
H2A H 0.493286 0.423569 0.151562 0.103 Uiso 1 1 calc R U . . .
H2B H 0.547920 0.449281 0.335111 0.103 Uiso 1 1 calc R U . . .
H2C H 0.490896 0.381006 0.304707 0.103 Uiso 1 1 calc R U . . .
C4 C 0.6467(10) 0.3789(4) 0.2708(13) 0.094(2) Uani 1 1 d . U . . .
H4 H 0.696936 0.407115 0.219824 0.113 Uiso 1 1 calc R U . . .
C5 C 0.7070(10) 0.3365(5) 0.4143(15) 0.113(3) Uani 1 1 d . U . . .
H5A H 0.671508 0.329036 0.508540 0.135 Uiso 1 1 calc R U . . .
H5B H 0.793067 0.338919 0.456707 0.135 Uiso 1 1 calc R U . . .
C6 C 0.6511(9) 0.3051(4) 0.2439(13) 0.098(2) Uani 1 1 d . U . . .
H6A H 0.579353 0.278130 0.228410 0.117 Uiso 1 1 calc R U . . .
H6B H 0.701196 0.288037 0.176457 0.117 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
Sb1 Br1 2.5943(8) . ?
Sb1 Br5 2.6931(10) . ?
Sb1 Br4 2.7025(8) . ?
Sb1 Br3 2.8867(11) . ?
Sb1 Br2 2.8960(8) . ?
N1 C1 1.462(9) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C1 C2 1.402(12) . ?
C1 C3 1.430(12) . ?
C1 H1 0.9800 . ?
C2 C3 1.440(13) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N2 C4 1.470(11) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C4 C5 1.379(13) . ?
C4 C6 1.428(11) . ?
C4 H4 0.9800 . ?
C5 C6 1.414(13) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
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
Br1 Sb1 Br5 88.88(3) . . ?
Br1 Sb1 Br4 92.63(3) . . ?
Br5 Sb1 Br4 87.82(3) . . ?
Br1 Sb1 Br3 87.89(3) . . ?
Br5 Sb1 Br3 176.70(2) . . ?
Br4 Sb1 Br3 91.65(3) . . ?
Br1 Sb1 Br2 87.74(3) . . ?
Br5 Sb1 Br2 90.46(3) . . ?
Br4 Sb1 Br2 178.23(3) . . ?
Br3 Sb1 Br2 90.10(3) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 C1 C3 61.1(7) . . ?
C2 C1 N1 119.8(9) . . ?
C3 C1 N1 118.9(8) . . ?
C2 C1 H1 115.4 . . ?
C3 C1 H1 115.4 . . ?
N1 C1 H1 115.4 . . ?
C1 C2 C3 60.4(7) . . ?
C1 C2 H2D 117.7 . . ?
C3 C2 H2D 117.7 . . ?
C1 C2 H2E 117.7 . . ?
C3 C2 H2E 117.7 . . ?
H2D C2 H2E 114.9 . . ?
C1 C3 C2 58.5(7) . . ?
C1 C3 H3A 117.9 . . ?
C2 C3 H3A 117.9 . . ?
C1 C3 H3B 117.9 . . ?
C2 C3 H3B 117.9 . . ?
H3A C3 H3B 115.1 . . ?
C4 N2 H2A 109.5 . . ?
C4 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C4 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C5 C4 C6 60.4(7) . . ?
C5 C4 N2 120.2(9) . . ?
C6 C4 N2 119.3(8) . . ?
C5 C4 H4 115.3 . . ?
C6 C4 H4 115.3 . . ?
N2 C4 H4 115.3 . . ?
C4 C5 C6 61.5(7) . . ?
C4 C5 H5A 117.6 . . ?
C6 C5 H5A 117.6 . . ?
C4 C5 H5B 117.6 . . ?
C6 C5 H5B 117.6 . . ?
H5A C5 H5B 114.7 . . ?
C5 C6 C4 58.0(6) . . ?
C5 C6 H6A 118.0 . . ?
C4 C6 H6A 118.0 . . ?
C5 C6 H6B 118.0 . . ?
C4 C6 H6B 118.0 . . ?
H6A C6 H6B 115.1 . . ?

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
N1 C1 C2 C3 108.7(10) . . . . ?
N1 C1 C3 C2 -110.1(10) . . . . ?
N2 C4 C5 C6 108.7(10) . . . . ?
N2 C4 C6 C5 -110.1(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 H1A Br3 0.89 2.51 3.327(6) 152.8 .
N1 H1B Br4 0.89 2.60 3.432(6) 156.6 4_565
N1 H1C Br3 0.89 2.67 3.558(7) 172.6 4_566
C1 H1 Br3 0.98 3.13 3.975(10) 145.0 4_565
C2 H2E Br1 0.97 3.10 4.019(10) 158.2 2_545
C2 H2E Br4 0.97 3.13 3.681(10) 117.4 2_546
N2 H2A Br4 0.89 2.71 3.479(6) 146.0 1_554
N2 H2B Br1 0.89 2.90 3.666(7) 145.0 3_666
N2 H2B Br5 0.89 3.04 3.665(6) 128.7 3_666
N2 H2C Br2 0.89 2.69 3.567(7) 169.1 .
C4 H4 Br4 0.98 3.05 3.869(9) 141.4 3_666
C5 H5B Br3 0.97 3.10 4.042(11) 165.6 1_655

_refine_diff_density_max         0.988
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_new_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc21hbhd
_database_code_depnum_ccdc_archive 'CCDC 1891573'
loop_
_audit_author_name
_audit_author_address
LiMaoFan
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2019-04-25 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;
_audit_creation_date             2019-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(Br10 Sb2), C6 H16 N2'
_chemical_formula_sum            'C6 H16 Br5 N2 Sb'
_chemical_formula_weight         637.51
_chemical_melting_point          ?
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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'B b c m'
_space_group_name_Hall           '-B 2 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x, -y+1/2, -z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, y, -z'
'-x, y-1/2, z-1/2'
'x, -y-1/2, z-1/2'
'-x+1/2, -y, -z+1/2'
'x+1/2, y, -z+1/2'
'-x+1/2, y-1/2, z'
'x+1/2, -y-1/2, z'

_cell_length_a                   22.4485(6)
_cell_length_b                   18.9653(5)
_cell_length_c                   7.9488(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3384.14(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2766
_cell_measurement_temperature    325(2)
_cell_measurement_theta_max      24.45
_cell_measurement_theta_min      2.812
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.413
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13466
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         2.148
_diffrn_ambient_temperature      325.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1428
_reflns_number_total             2093
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.127
_refine_diff_density_min         -1.110
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         2093
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+18.3235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1290
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2. Restrained distances
 C1-N1
 1.46 with sigma of 0.01
 C1-C2
 1.49 with sigma of 0.01
 N2-C4
 1.46 with sigma of 0.02
 C1-C3
 1.49 with sigma of 0.01
 C4-C5
 1.49 with sigma of 0.01
 C1-C2 \\sim C2-C3 \\sim C3-C1 \\sim C4-C5 \\sim C5-C6 \\sim C6-C4
 with sigma of 0.01
3. Rigid bond restraints
 C4, C5, C6, N2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim C6 \\sim N2: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C1 \\sim C2 \\sim C3 \\sim N1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
5. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H6A(0.5) H6B(0.5) H1(0.5) H2A(0.5)
 H2B(0.5) H2C(0.5) H2D(0.5) H2E(0.5) C5(0.5) H5A(0.5) H5B(0.5) H4(0.5) C3(0.5)
 H3A(0.5) H3B(0.5)
6.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
6.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B), C5(H5A,H5B), C3(H3A,H3B)
6.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2C,H2D,H2E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Sb1 Sb 0.35023(3) 0.63449(3) 0.500000 0.0507(2) Uani 1 2 d S T P . .
Br2 Br 0.23225(6) 0.59890(8) 0.500000 0.0859(4) Uani 1 2 d S T P . .
Br1 Br 0.36645(5) 0.54191(5) 0.25557(12) 0.0900(4) Uani 1 1 d . . . . .
Br4 Br 0.47348(6) 0.66508(8) 0.500000 0.0959(5) Uani 1 2 d S T P . .
Br3 Br 0.33397(8) 0.750000 0.750000 0.1337(8) Uani 1 2 d S T P . .
N1 N 0.7413(7) 0.5885(8) 0.500000 0.158(7) Uani 1 2 d DS TU P D .
H1A H 0.753473 0.581980 0.394537 0.190 Uiso 0.5 1 calc GR . . A -1
H1B H 0.735363 0.546825 0.548744 0.190 Uiso 0.5 1 calc GR . . A -1
H1C H 0.769036 0.612192 0.556718 0.190 Uiso 0.5 1 calc GR . . A -1
C6 C 0.5650(7) 0.8450(10) 0.500000 0.173(8) Uani 1 2 d DS TU P . .
H6A H 0.587501 0.847711 0.396073 0.207 Uiso 0.5 1 calc R . . C .
H6B H 0.572678 0.803301 0.567303 0.207 Uiso 0.5 1 calc R . . . .
C1 C 0.6867(9) 0.6279(9) 0.500000 0.196(10) Uani 1 2 d DS TU P . .
H1 H 0.663342 0.611381 0.596440 0.235 Uiso 0.5 1 calc R . . D .
C2 C 0.6830(14) 0.7042(9) 0.500000 0.219(11) Uani 1 2 d DS TU P D .
H2A H 0.664297 0.726803 0.595909 0.263 Uiso 0.5 1 calc R . . . .
H2B H 0.715829 0.730281 0.450778 0.263 Uiso 0.5 1 calc R . . . .
N2 N 0.4530(5) 0.8391(6) 0.500000 0.107(4) Uani 1 2 d DS TU P . .
H2C H 0.437476 0.840239 0.396988 0.128 Uiso 0.5 1 calc GR . . B -1
H2D H 0.428392 0.860445 0.571482 0.128 Uiso 0.5 1 calc GR . . B -1
H2E H 0.458070 0.794429 0.531530 0.128 Uiso 0.5 1 calc GR . . B -1
C5 C 0.5526(9) 0.9101(10) 0.588(3) 0.171(10) Uani 0.5 1 d D U . C -1
H5A H 0.552202 0.909126 0.709523 0.206 Uiso 0.5 1 calc R . . C -1
H5B H 0.567040 0.953578 0.538129 0.206 Uiso 0.5 1 calc R . . C -1
C4 C 0.5061(6) 0.8725(10) 0.500000 0.160(7) Uani 1 2 d DS TU P C .
H4 H 0.504910 0.897495 0.392132 0.191 Uiso 0.5 1 calc R . . . .
C3 C 0.6457(11) 0.6641(12) 0.389(4) 0.192(12) Uani 0.5 1 d D U . D -1
H3A H 0.655106 0.664876 0.269907 0.231 Uiso 0.5 1 calc R . . D -1
H3B H 0.603581 0.661398 0.415019 0.231 Uiso 0.5 1 calc R . . D -1


_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
Sb1 Br2 2.7332(14) . ?
Sb1 Br1 2.6440(9) . ?
Sb1 Br1 2.6440(9) 10_556 ?
Sb1 Br4 2.8269(14) . ?
Sb1 Br3 2.9801(5) . ?
Sb1 Br3 2.9801(5) 10_556 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.437(10) . ?
C6 H6A 0.9700 10_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6B 0.9700 10_556 ?
C6 C5 1.444(10) . ?
C6 C4 1.421(9) . ?
C1 H1 0.9800 10_556 ?
C1 H1 0.9800 . ?
C1 C2 1.449(7) . ?
C1 C3 1.446(7) . ?
C2 H2A 0.9700 10_556 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9699 10_556 ?
C2 H2B 0.9700 . ?
C2 C3 1.434(10) . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?
N2 H2E 0.8900 . ?
N2 C4 1.351(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.442(7) . ?
C5 H4 1.108(17) 10_556 ?
C4 H4 0.9800 10_556 ?
C4 H4 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 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
Br2 Sb1 Br4 177.54(5) . . ?
Br2 Sb1 Br3 93.60(5) . . ?
Br2 Sb1 Br3 93.60(5) . 10_556 ?
Br1 Sb1 Br2 88.25(3) . . ?
Br1 Sb1 Br2 88.25(3) 10_556 . ?
Br1 Sb1 Br1 94.59(5) . 10_556 ?
Br1 Sb1 Br4 90.09(3) 10_556 . ?
Br1 Sb1 Br4 90.09(3) . . ?
Br1 Sb1 Br3 90.86(2) . 10_556 ?
Br1 Sb1 Br3 174.30(3) 10_556 10_556 ?
Br1 Sb1 Br3 90.86(2) 10_556 . ?
Br1 Sb1 Br3 174.30(3) . . ?
Br4 Sb1 Br3 88.23(4) . 10_556 ?
Br4 Sb1 Br3 88.23(4) . . ?
Br3 Sb1 Br3 83.644(17) . 10_556 ?
Sb1 Br3 Sb1 165.93(7) 3_566 . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H6A C6 H6A 116.8 . 10_556 ?
H6A C6 H6B 58.7 . 10_556 ?
H6A C6 H6B 114.9 10_556 10_556 ?
H6A C6 H6B 114.9 . . ?
H6B C6 H6A 58.7 . 10_556 ?
H6B C6 H6B 66.9 . 10_556 ?
C5 C6 H6A 117.7 . . ?
C5 C6 H6A 69.2(9) . 10_556 ?
C5 C6 H6B 175.3(11) . 10_556 ?
C5 C6 H6B 117.7 . . ?
C4 C6 H6A 117.7(3) . 10_556 ?
C4 C6 H6A 117.7 . . ?
C4 C6 H6B 117.7 . . ?
C4 C6 H6B 117.7(9) . 10_556 ?
C4 C6 C5 60.4(4) . . ?
N1 C1 H1 106.8 . . ?
N1 C1 H1 106.8(7) . 10_556 ?
N1 C1 C2 125(2) . . ?
N1 C1 C3 142.1(15) . . ?
H1 C1 H1 102.9 . 10_556 ?
C2 C1 H1 106.8 . . ?
C2 C1 H1 106.8(9) . 10_556 ?
C3 C1 H1 106.8 . . ?
C3 C1 H1 48.3(11) . 10_556 ?
C3 C1 C2 59.4(4) . . ?
C1 C2 H2A 117.8 . . ?
C1 C2 H2A 117.7(7) . 10_556 ?
C1 C2 H2B 117.8 . . ?
C1 C2 H2B 117.8(14) . 10_556 ?
H2A C2 H2A 103.6 . 10_556 ?
H2A C2 H2B 114.9 . . ?
H2A C2 H2B 77.7 . 10_556 ?
H2A C2 H2B 114.9 10_556 10_556 ?
H2B C2 H2A 77.7 . 10_556 ?
H2B C2 H2B 47.6 . 10_556 ?
C3 C2 C1 60.2(3) . . ?
C3 C2 H2A 117.8 . . ?
C3 C2 H2A 59.9(9) . 10_556 ?
C3 C2 H2B 164.1(18) . 10_556 ?
C3 C2 H2B 117.8 . . ?
H2C N2 H2D 109.5 . . ?
H2C N2 H2E 109.5 . . ?
H2D N2 H2E 109.5 . . ?
C4 N2 H2C 109.5 . . ?
C4 N2 H2D 109.5 . . ?
C4 N2 H2E 109.5 . . ?
C6 C5 H6A 39.5(3) . 10_556 ?
C6 C5 H5A 117.9 . . ?
C6 C5 H5B 117.9 . . ?
C6 C5 H4 94.2(7) . 10_556 ?
H6A C5 H4 109.9 10_556 10_556 ?
H5A C5 H6A 84.1 . 10_556 ?
H5A C5 H5B 115.0 . . ?
H5A C5 H4 80.9 . 10_556 ?
H5B C5 H6A 123.9 . 10_556 ?
H5B C5 H4 124.5 . 10_556 ?
C4 C5 C6 59.0(4) . . ?
C4 C5 H6A 91.9(7) . 10_556 ?
C4 C5 H5A 117.9 . . ?
C4 C5 H5B 117.9 . . ?
C4 C5 H4 42.8(3) . 10_556 ?
C6 C4 C5 60.6(4) . . ?
C6 C4 H4 101.7 . . ?
C6 C4 H4 101.7(5) . 10_556 ?
N2 C4 C6 130.4(18) . . ?
N2 C4 C5 150.5(10) . . ?
N2 C4 H4 101.7 . . ?
N2 C4 H4 101.7(4) . 10_556 ?
C5 C4 H4 50.1(9) . 10_556 ?
C5 C4 H4 101.7 . . ?
H4 C4 H4 122.1 . 10_556 ?
C1 C3 H1 42.7(3) . 10_556 ?
C1 C3 H2A 100.3(7) . 10_556 ?
C1 C3 H3A 117.7 . . ?
C1 C3 H3B 117.7 . . ?
H1 C3 H2A 137.6 10_556 10_556 ?
C2 C3 C1 60.4(3) . . ?
C2 C3 H1 102.2(6) . 10_556 ?
C2 C3 H2A 41.5(3) . 10_556 ?
C2 C3 H3A 117.7 . . ?
C2 C3 H3B 117.7 . . ?
H3A C3 H1 92.3 . 10_556 ?
H3A C3 H2A 90.3 . 10_556 ?
H3A C3 H3B 114.9 . . ?
H3B C3 H1 106.6 . 10_556 ?
H3B C3 H2A 110.5 . 10_556 ?

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
N1 H1A Br1 0.89 2.90 3.577(11) 133.7 14 yes
N1 H1B Br2 0.89 2.88 3.603(15) 138.9 9_666 yes
N1 H1C Br1 0.89 3.01 3.577(11) 123.4 5 yes
C2 H2B Br3 0.97 3.12 4.02(3) 156.1 5_554 yes
N2 H2C Br1 0.89 3.00 3.605(9) 126.7 3_565 yes
N2 H2C Br3 0.89 3.11 3.734(9) 128.6 10_556 yes
N2 H2D Br1 0.89 2.74 3.605(9) 164.6 12_576 yes
N2 H2E Br4 0.89 2.49 3.331(12) 157.9 . yes
C5 H5B Br1 0.97 2.83 3.368(12) 115.7 11_666 yes
C3 H3A Br2 0.97 3.03 3.85(3) 144.0 5_554 yes
C3 H3B Br4 0.97 3.00 3.97(3) 175.6 . yes

_olex2_submission_special_instructions 'No special instructions were received'
