# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_HSC280K
_database_code_depnum_ccdc_archive 'CCDC 1859094'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H14 N),  Sb Cl5'
_chemical_formula_sum            'C12 H28 Cl5 N2 Sb'
_chemical_formula_weight         499.36

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'
Sb Sb -0.5866 1.5461 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.576(3)
_cell_length_b                   13.264(4)
_cell_length_c                   20.195(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2029(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    280(2)
_cell_measurement_reflns_used    4345
_cell_measurement_theta_min      3.0830
_cell_measurement_theta_max      28.4080

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.011
_shelx_estimated_absorpt_T_min   0.666
_shelx_estimated_absorpt_T_max   0.780
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      280(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            6640
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.499
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             3557
_reflns_number_gt                3258
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_max     0.869
_reflns_Friedel_fraction_full    0.869

_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       
;
CrysAlisCCD, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 4.0'
_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)+(0.0625P)²+0.4348P] 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_abs_structure_details 
;
 Flack x determined using 1131 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3557
_refine_ls_number_parameters     191
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.096
_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
Sb Sb 0.43898(9) 0.39381(4) 0.55675(3) 0.0402(2) Uani 1 1 d . . . . .
Cl1 Cl 0.6197(4) 0.5031(2) 0.62176(14) 0.0588(7) Uani 1 1 d . . . . .
Cl2 Cl 0.4299(4) 0.27326(19) 0.65363(12) 0.0559(6) Uani 1 1 d . . . . .
Cl3 Cl 0.1570(4) 0.4783(2) 0.60370(15) 0.0643(7) Uani 1 1 d . . . . .
Cl4 Cl 0.7354(4) 0.3020(2) 0.51608(14) 0.0607(7) Uani 1 1 d . . . . .
Cl5 Cl 0.4784(4) 0.5416(2) 0.46016(13) 0.0573(7) Uani 1 1 d . . . . .
N1A N 0.9022(14) 0.5397(7) 0.4801(5) 0.062(2) Uani 1 1 d . U . . .
H1A1 H 0.7864 0.5344 0.4735 0.075 Uiso 1 1 calc R U . . .
H1A2 H 0.9264 0.5085 0.5181 0.075 Uiso 1 1 calc R U . . .
C2A C 0.9942(16) 0.4835(8) 0.4253(5) 0.061(3) Uani 1 1 d . U . . .
H2A1 H 1.1206 0.4929 0.4298 0.073 Uiso 1 1 calc R U . . .
H2A2 H 0.9697 0.4121 0.4298 0.073 Uiso 1 1 calc R U . . .
C3A C 0.938(2) 0.5174(11) 0.3584(6) 0.089(4) Uani 1 1 d . U . . .
H3A1 H 0.9618 0.4633 0.3273 0.107 Uiso 1 1 calc R U . . .
H3A2 H 0.8118 0.5282 0.3590 0.107 Uiso 1 1 calc R U . . .
C4A C 1.023(3) 0.6097(12) 0.3334(7) 0.106(5) Uani 1 1 d . U . . .
H4A1 H 1.1492 0.5970 0.3309 0.127 Uiso 1 1 calc R U . . .
H4A2 H 0.9821 0.6205 0.2884 0.127 Uiso 1 1 calc R U . . .
C5A C 0.998(3) 0.7033(12) 0.3697(9) 0.106(5) Uani 1 1 d . U . . .
H5A1 H 1.1154 0.7300 0.3775 0.127 Uiso 0.68(3) 1 calc R U P A 1
H5A2 H 0.9415 0.7494 0.3390 0.127 Uiso 0.68(3) 1 calc R U P A 1
H5A3 H 1.0678 0.7551 0.3480 0.127 Uiso 0.32(3) 1 calc R U P A 2
H5A4 H 0.8752 0.7227 0.3653 0.127 Uiso 0.32(3) 1 calc R U P A 2
C6A C 0.905(3) 0.7136(15) 0.4308(12) 0.083(6) Uani 0.68(3) 1 d . U P A 1
H6A1 H 0.7808 0.7053 0.4209 0.100 Uiso 0.68(3) 1 calc R U P A 1
H6A2 H 0.9209 0.7828 0.4452 0.100 Uiso 0.68(3) 1 calc R U P A 1
C61A C 1.039(5) 0.705(3) 0.436(2) 0.078(7) Uani 0.32(3) 1 d . U P A 2
H6A3 H 1.0366 0.7749 0.4487 0.094 Uiso 0.32(3) 1 calc R U P A 2
H6A4 H 1.1618 0.6837 0.4384 0.094 Uiso 0.32(3) 1 calc R U P A 2
C7A C 0.945(3) 0.6484(9) 0.4885(7) 0.086(4) Uani 1 1 d . U . . .
H7A1 H 0.8798 0.6737 0.5264 0.104 Uiso 0.68(3) 1 calc R U P A 1
H7A2 H 1.0696 0.6544 0.4986 0.104 Uiso 0.68(3) 1 calc R U P A 1
H7A3 H 0.8345 0.6834 0.4965 0.104 Uiso 0.32(3) 1 calc R U P A 2
H7A4 H 1.0146 0.6546 0.5286 0.104 Uiso 0.32(3) 1 calc R U P A 2
N1B N 0.950(2) 0.2753(8) 0.6567(5) 0.092(4) Uani 1 1 d . . . . .
H1B1 H 0.8883 0.3028 0.6238 0.111 Uiso 1 1 calc R U . . .
H1B2 H 1.0620 0.2930 0.6507 0.111 Uiso 1 1 calc R U . . .
C2B C 0.940(3) 0.1691(10) 0.6492(6) 0.088(4) Uani 1 1 d . . . . .
H2B1 H 1.0420 0.1481 0.6238 0.106 Uiso 1 1 calc R U . . .
H2B2 H 0.8367 0.1547 0.6223 0.106 Uiso 1 1 calc R U . . .
C3B C 0.930(2) 0.1037(8) 0.7082(8) 0.093(5) Uani 1 1 d . . . . .
H3B1 H 0.9408 0.0341 0.6941 0.112 Uiso 1 1 calc R U . . .
H3B2 H 0.8146 0.1116 0.7282 0.112 Uiso 1 1 calc R U . . .
C4B C 1.066(2) 0.1235(10) 0.7596(6) 0.092(5) Uani 1 1 d . . . . .
H4B1 H 1.1769 0.1392 0.7377 0.110 Uiso 1 1 calc R U . . .
H4B2 H 1.0840 0.0624 0.7851 0.110 Uiso 1 1 calc R U . . .
C5B C 1.022(3) 0.2083(12) 0.8066(7) 0.093(5) Uani 1 1 d . . . . .
H5B1 H 0.9087 0.1939 0.8271 0.112 Uiso 1 1 calc R U . . .
H5B2 H 1.1097 0.2099 0.8415 0.112 Uiso 1 1 calc R U . . .
C6B C 1.013(2) 0.3104(10) 0.7752(6) 0.073(4) Uani 1 1 d . . . . .
H6B1 H 0.9799 0.3587 0.8091 0.087 Uiso 1 1 calc R U . . .
H6B2 H 1.1306 0.3281 0.7603 0.087 Uiso 1 1 calc R U . . .
C7B C 0.890(2) 0.3228(9) 0.7185(7) 0.085(5) Uani 1 1 d . . . . .
H7B1 H 0.7766 0.2944 0.7306 0.102 Uiso 1 1 calc R U . . .
H7B2 H 0.8729 0.3942 0.7106 0.102 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
Sb Cl1 2.387(3) . ?
Sb Cl2 2.528(2) . ?
Sb Cl3 2.592(3) . ?
Sb Cl4 2.683(3) . ?
Sb Cl5 2.781(3) . ?
Sb Cl4 3.360(3) 4_456 ?
N1A C7A 1.488(15) . ?
N1A C2A 1.505(14) . ?
N1A H1A1 0.8900 . ?
N1A H1A2 0.8900 . ?
C2A C3A 1.486(16) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A C4A 1.47(2) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A C5A 1.45(2) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A C61A 1.37(5) . ?
C5A C6A 1.43(3) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C5A H5A3 0.9700 . ?
C5A H5A4 0.9700 . ?
C6A C7A 1.48(3) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C61A C7A 1.49(5) . ?
C61A H6A3 0.9700 . ?
C61A H6A4 0.9700 . ?
C7A H7A1 0.9700 . ?
C7A H7A2 0.9700 . ?
C7A H7A3 0.9700 . ?
C7A H7A4 0.9700 . ?
N1B C2B 1.420(15) . ?
N1B C7B 1.469(18) . ?
N1B H1B1 0.8900 . ?
N1B H1B2 0.8900 . ?
C2B C3B 1.476(18) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C3B C4B 1.49(2) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C4B C5B 1.511(18) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B C6B 1.497(18) . ?
C5B H5B1 0.9700 . ?
C5B H5B2 0.9700 . ?
C6B C7B 1.485(18) . ?
C6B H6B1 0.9700 . ?
C6B H6B2 0.9700 . ?
C7B H7B1 0.9700 . ?
C7B H7B2 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
Cl1 Sb Cl2 88.51(10) . . ?
Cl1 Sb Cl3 90.53(11) . . ?
Cl2 Sb Cl3 88.16(10) . . ?
Cl1 Sb Cl4 87.92(10) . . ?
Cl2 Sb Cl4 88.44(10) . . ?
Cl3 Sb Cl4 176.30(10) . . ?
Cl1 Sb Cl5 84.05(9) . . ?
Cl2 Sb Cl5 172.55(9) . . ?
Cl3 Sb Cl5 92.32(9) . . ?
Cl4 Sb Cl5 90.86(9) . . ?
Cl1 Sb Cl4 166.75(9) . 4_456 ?
Cl2 Sb Cl4 80.63(8) . 4_456 ?
Cl3 Sb Cl4 96.66(10) . 4_456 ?
Cl4 Sb Cl4 84.23(4) . 4_456 ?
Cl5 Sb Cl4 106.68(8) . 4_456 ?
C7A N1A C2A 117.5(11) . . ?
C7A N1A H1A1 107.9 . . ?
C2A N1A H1A1 107.9 . . ?
C7A N1A H1A2 107.9 . . ?
C2A N1A H1A2 107.9 . . ?
H1A1 N1A H1A2 107.2 . . ?
C3A C2A N1A 112.8(11) . . ?
C3A C2A H2A1 109.0 . . ?
N1A C2A H2A1 109.0 . . ?
C3A C2A H2A2 109.0 . . ?
N1A C2A H2A2 109.0 . . ?
H2A1 C2A H2A2 107.8 . . ?
C4A C3A C2A 116.1(13) . . ?
C4A C3A H3A1 108.3 . . ?
C2A C3A H3A1 108.3 . . ?
C4A C3A H3A2 108.3 . . ?
C2A C3A H3A2 108.3 . . ?
H3A1 C3A H3A2 107.4 . . ?
C5A C4A C3A 118.7(14) . . ?
C5A C4A H4A1 107.6 . . ?
C3A C4A H4A1 107.6 . . ?
C5A C4A H4A2 107.6 . . ?
C3A C4A H4A2 107.6 . . ?
H4A1 C4A H4A2 107.1 . . ?
C61A C5A C4A 118(2) . . ?
C6A C5A C4A 125.6(16) . . ?
C6A C5A H5A1 105.9 . . ?
C4A C5A H5A1 105.9 . . ?
C6A C5A H5A2 105.9 . . ?
C4A C5A H5A2 105.9 . . ?
H5A1 C5A H5A2 106.2 . . ?
C61A C5A H5A3 107.8 . . ?
C4A C5A H5A3 107.8 . . ?
C61A C5A H5A4 107.8 . . ?
C4A C5A H5A4 107.8 . . ?
H5A3 C5A H5A4 107.1 . . ?
C5A C6A C7A 121.7(19) . . ?
C5A C6A H6A1 106.9 . . ?
C7A C6A H6A1 106.9 . . ?
C5A C6A H6A2 106.9 . . ?
C7A C6A H6A2 106.9 . . ?
H6A1 C6A H6A2 106.7 . . ?
C5A C61A C7A 126(3) . . ?
C5A C61A H6A3 105.9 . . ?
C7A C61A H6A3 105.9 . . ?
C5A C61A H6A4 105.9 . . ?
C7A C61A H6A4 105.9 . . ?
H6A3 C61A H6A4 106.2 . . ?
C6A C7A N1A 115.6(12) . . ?
C61A C7A N1A 121(2) . . ?
C6A C7A H7A1 108.4 . . ?
N1A C7A H7A1 108.4 . . ?
C6A C7A H7A2 108.4 . . ?
N1A C7A H7A2 108.4 . . ?
H7A1 C7A H7A2 107.4 . . ?
C61A C7A H7A3 107.2 . . ?
N1A C7A H7A3 107.2 . . ?
C61A C7A H7A4 107.2 . . ?
N1A C7A H7A4 107.2 . . ?
H7A3 C7A H7A4 106.8 . . ?
C2B N1B C7B 120.0(11) . . ?
C2B N1B H1B1 107.3 . . ?
C7B N1B H1B1 107.3 . . ?
C2B N1B H1B2 107.3 . . ?
C7B N1B H1B2 107.3 . . ?
H1B1 N1B H1B2 106.9 . . ?
N1B C2B C3B 120.0(11) . . ?
N1B C2B H2B1 107.3 . . ?
C3B C2B H2B1 107.3 . . ?
N1B C2B H2B2 107.3 . . ?
C3B C2B H2B2 107.3 . . ?
H2B1 C2B H2B2 106.9 . . ?
C2B C3B C4B 115.2(13) . . ?
C2B C3B H3B1 108.5 . . ?
C4B C3B H3B1 108.5 . . ?
C2B C3B H3B2 108.5 . . ?
C4B C3B H3B2 108.5 . . ?
H3B1 C3B H3B2 107.5 . . ?
C3B C4B C5B 114.5(14) . . ?
C3B C4B H4B1 108.6 . . ?
C5B C4B H4B1 108.6 . . ?
C3B C4B H4B2 108.6 . . ?
C5B C4B H4B2 108.6 . . ?
H4B1 C4B H4B2 107.6 . . ?
C6B C5B C4B 114.7(11) . . ?
C6B C5B H5B1 108.6 . . ?
C4B C5B H5B1 108.6 . . ?
C6B C5B H5B2 108.6 . . ?
C4B C5B H5B2 108.6 . . ?
H5B1 C5B H5B2 107.6 . . ?
C7B C6B C5B 117.1(12) . . ?
C7B C6B H6B1 108.0 . . ?
C5B C6B H6B1 108.0 . . ?
C7B C6B H6B2 108.0 . . ?
C5B C6B H6B2 108.0 . . ?
H6B1 C6B H6B2 107.3 . . ?
N1B C7B C6B 114.5(13) . . ?
N1B C7B H7B1 108.6 . . ?
C6B C7B H7B1 108.6 . . ?
N1B C7B H7B2 108.6 . . ?
C6B C7B H7B2 108.6 . . ?
H7B1 C7B H7B2 107.6 . . ?

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
C7A N1A C2A C3A -67.9(15) . . . . ?
N1A C2A C3A C4A 81.2(16) . . . . ?
C2A C3A C4A C5A -62(2) . . . . ?
C3A C4A C5A C61A 54(3) . . . . ?
C3A C4A C5A C6A 4(3) . . . . ?
C4A C5A C6A C7A 51(3) . . . . ?
C4A C5A C61A C7A -67(5) . . . . ?
C5A C6A C7A N1A -66(3) . . . . ?
C5A C61A C7A N1A 48(4) . . . . ?
C2A N1A C7A C6A 60(2) . . . . ?
C2A N1A C7A C61A 14(3) . . . . ?
C7B N1B C2B C3B -21(3) . . . . ?
N1B C2B C3B C4B -50(2) . . . . ?
C2B C3B C4B C5B 83.3(17) . . . . ?
C3B C4B C5B C6B -66(2) . . . . ?
C4B C5B C6B C7B 56(2) . . . . ?
C2B N1B C7B C6B 75(2) . . . . ?
C5B C6B C7B N1B -73.5(17) . . . . ?

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
N1A H1A1 Cl5 0.89 2.35 3.236(11) 172.9 .
N1A H1A2 Cl3 0.89 2.49 3.259(10) 144.8 1_655
N1A H1A1 Cl5 0.89 2.35 3.236(11) 172.9 .
C2A H2A2 Cl4 0.97 2.88 3.606(11) 132.0 .
C2A H2A1 Cl5 0.97 2.85 3.814(13) 170.8 1_655
N1B H1B1 Cl4 0.89 2.46 3.291(10) 154.7 .
N1B H1B2 Cl2 0.89 2.80 3.637(17) 157.4 1_655
N1B H1B2 Cl3 0.89 2.73 3.295(11) 122.4 1_655
C2B H2B1 Cl5 0.97 3.07 3.573(13) 113.6 4_556
C7B H7B2 Cl1 0.97 3.00 3.706(13) 130.9 .

_refine_diff_density_max         0.695
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.117

####################################################################### 
# 
# 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_HBB280K
_database_code_depnum_ccdc_archive 'CCDC 1859099'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H14 N), Bi Br5'
_chemical_formula_sum            'C12 H28 Bi Br5 N2'
_chemical_formula_weight         808.89

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'
Bi Bi -4.1077 10.2566 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.205(4)
_cell_length_b                   8.005(3)
_cell_length_c                   20.946(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.28(3)
_cell_angle_gamma                90
_cell_volume                     2213(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    280(2)
_cell_measurement_reflns_used    5759
_cell_measurement_theta_min      2.9610
_cell_measurement_theta_max      27.7310

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.427
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    16.985
_shelx_estimated_absorpt_T_min   0.235
_shelx_estimated_absorpt_T_max   0.429
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.219
_exptl_absorpt_correction_T_max  0.394
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      280(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            16470
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.976
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.499
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4112
_reflns_number_gt                3148
_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       
;
CrysAlisCCD, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 4.0'
_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)+(0.0507P)²+0.4231P] 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         4112
_refine_ls_number_parameters     209
_refine_ls_number_restraints     169
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.062
_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
Bi Bi 0.60866(2) 1.04806(4) 0.69171(2) 0.03770(14) Uani 1 1 d . . . . .
Br1 Br 0.47513(7) 0.84206(14) 0.63323(5) 0.0556(3) Uani 1 1 d . . . . .
Br2 Br 0.51408(9) 1.33852(13) 0.64801(5) 0.0621(3) Uani 1 1 d . . . . .
Br3 Br 0.72702(9) 1.02925(14) 0.58170(5) 0.0584(3) Uani 1 1 d . . . . .
Br4 Br 0.47801(8) 1.03743(13) 0.80002(5) 0.0553(3) Uani 1 1 d . . . . .
Br5 Br 0.71855(8) 0.75348(14) 0.74071(5) 0.0562(3) Uani 1 1 d . . . . .
N1A N 0.4616(7) 0.6035(14) 0.7767(5) 0.074(3) Uani 1 1 d . U . . .
H1A1 H 0.4644 0.7133 0.7831 0.088 Uiso 1 1 calc R U . . .
H1A2 H 0.4951 0.5824 0.7412 0.088 Uiso 1 1 calc R U . . .
C2A C 0.3563(10) 0.559(2) 0.7649(7) 0.098(5) Uani 1 1 d D U . . .
H2A1 H 0.3503 0.4384 0.7644 0.117 Uiso 0.57(2) 1 calc R U P A 1
H2A2 H 0.3355 0.5999 0.7230 0.117 Uiso 0.57(2) 1 calc R U P A 1
H2A3 H 0.3237 0.6567 0.7461 0.117 Uiso 0.43(2) 1 calc R U P A 2
H2A4 H 0.3556 0.4735 0.7321 0.117 Uiso 0.43(2) 1 calc R U P A 2
C3A C 0.2855(17) 0.629(4) 0.8140(12) 0.082(7) Uani 0.57(2) 1 d D U P A 1
H3A1 H 0.2164 0.6169 0.7979 0.098 Uiso 0.57(2) 1 calc R U P A 1
H3A2 H 0.2988 0.7478 0.8186 0.098 Uiso 0.57(2) 1 calc R U P A 1
C31A C 0.297(3) 0.506(4) 0.8103(19) 0.116(10) Uani 0.43(2) 1 d D U P A 2
H3A3 H 0.3043 0.3855 0.8095 0.139 Uiso 0.43(2) 1 calc R U P A 2
H3A4 H 0.2290 0.5284 0.7940 0.139 Uiso 0.43(2) 1 calc R U P A 2
C4A C 0.2933(12) 0.549(2) 0.8797(8) 0.110(5) Uani 1 1 d D U . . .
H4A1 H 0.2497 0.6149 0.9065 0.132 Uiso 0.57(2) 1 calc R U P A 1
H4A2 H 0.2604 0.4410 0.8749 0.132 Uiso 0.57(2) 1 calc R U P A 1
H4A3 H 0.2517 0.6477 0.8839 0.132 Uiso 0.43(2) 1 calc R U P A 2
H4A4 H 0.2589 0.4583 0.9012 0.132 Uiso 0.43(2) 1 calc R U P A 2
C5A C 0.383(3) 0.517(4) 0.919(2) 0.103(8) Uani 0.57(2) 1 d D U P A 1
H5A1 H 0.3932 0.3970 0.9223 0.123 Uiso 0.57(2) 1 calc R U P A 1
H5A2 H 0.3733 0.5604 0.9612 0.123 Uiso 0.57(2) 1 calc R U P A 1
C51A C 0.386(4) 0.578(4) 0.913(3) 0.084(8) Uani 0.43(2) 1 d D U P A 2
H5A3 H 0.3779 0.5566 0.9580 0.100 Uiso 0.43(2) 1 calc R U P A 2
H5A4 H 0.4057 0.6939 0.9078 0.100 Uiso 0.43(2) 1 calc R U P A 2
C6A C 0.475(2) 0.592(4) 0.8925(11) 0.094(7) Uani 0.57(2) 1 d D U P A 1
H6A1 H 0.5288 0.5837 0.9248 0.113 Uiso 0.57(2) 1 calc R U P A 1
H6A2 H 0.4621 0.7104 0.8860 0.113 Uiso 0.57(2) 1 calc R U P A 1
C61A C 0.466(3) 0.469(4) 0.8881(15) 0.078(8) Uani 0.43(2) 1 d D U P A 2
H6A3 H 0.5173 0.4552 0.9216 0.093 Uiso 0.43(2) 1 calc R U P A 2
H6A4 H 0.4364 0.3596 0.8801 0.093 Uiso 0.43(2) 1 calc R U P A 2
C7A C 0.5166(9) 0.5222(18) 0.8299(6) 0.083(4) Uani 1 1 d D U . . .
H7A1 H 0.5886 0.5449 0.8274 0.100 Uiso 0.57(2) 1 calc R U P A 1
H7A2 H 0.5066 0.4023 0.8282 0.100 Uiso 0.57(2) 1 calc R U P A 1
H7A3 H 0.5490 0.4240 0.8126 0.100 Uiso 0.43(2) 1 calc R U P A 2
H7A4 H 0.5705 0.5979 0.8432 0.100 Uiso 0.43(2) 1 calc R U P A 2
N1B N 0.6873(7) 0.6049(13) 0.5796(4) 0.067(3) Uani 1 1 d . U . . .
H1B1 H 0.6450 0.5541 0.6057 0.080 Uiso 1 1 calc R U . . .
H1B2 H 0.6918 0.7110 0.5920 0.080 Uiso 1 1 calc R U . . .
C2B C 0.7901(10) 0.5266(19) 0.5891(6) 0.091(4) Uani 1 1 d . U . . .
H2B1 H 0.8201 0.5703 0.6284 0.109 Uiso 1 1 calc R U . . .
H2B2 H 0.7810 0.4074 0.5949 0.109 Uiso 1 1 calc R U . . .
C3B C 0.8602(10) 0.551(2) 0.5392(7) 0.100(5) Uani 1 1 d . U . . .
H3B1 H 0.9283 0.5395 0.5570 0.120 Uiso 1 1 calc R U . . .
H3B2 H 0.8532 0.6650 0.5237 0.120 Uiso 1 1 calc R U . . .
C4B C 0.8485(10) 0.4311(19) 0.4815(7) 0.095(5) Uani 1 1 d . U . . .
H4B1 H 0.9065 0.4464 0.4545 0.114 Uiso 1 1 calc R U . . .
H4B2 H 0.8514 0.3175 0.4976 0.114 Uiso 1 1 calc R U . . .
C5B C 0.7544(10) 0.4475(17) 0.4402(6) 0.076(4) Uani 1 1 d . U . . .
H5B1 H 0.7514 0.3541 0.4107 0.091 Uiso 1 1 calc R U . . .
H5B2 H 0.7593 0.5489 0.4152 0.091 Uiso 1 1 calc R U . . .
C6B C 0.6574(10) 0.4524(14) 0.4768(6) 0.070(3) Uani 1 1 d . U . . .
H6B1 H 0.6011 0.4391 0.4467 0.084 Uiso 1 1 calc R U . . .
H6B2 H 0.6567 0.3572 0.5055 0.084 Uiso 1 1 calc R U . . .
C7B C 0.6402(9) 0.6023(16) 0.5140(5) 0.073(3) Uani 1 1 d . U . . .
H7B1 H 0.5677 0.6174 0.5179 0.087 Uiso 1 1 calc R U . . .
H7B2 H 0.6657 0.6971 0.4905 0.087 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
Bi Br1 2.6893(12) . ?
Bi Br2 2.7844(13) . ?
Bi Br3 2.8171(14) . ?
Bi Br4 2.8819(14) . ?
Bi Br5 2.9416(13) . ?
Bi Br5 3.1256(13) 2_656 ?
Br5 Bi 3.1256(13) 2_646 ?
N1A C2A 1.450(15) . ?
N1A C7A 1.470(15) . ?
N1A H1A1 0.8900 . ?
N1A H1A2 0.8900 . ?
C2A C31A 1.32(4) . ?
C2A C3A 1.51(3) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C2A H2A3 0.9700 . ?
C2A H2A4 0.9700 . ?
C3A C4A 1.52(3) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C31A C4A 1.50(4) . ?
C31A H3A3 0.9700 . ?
C31A H3A4 0.9700 . ?
C4A C51A 1.41(5) . ?
C4A C5A 1.45(5) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C4A H4A3 0.9700 . ?
C4A H4A4 0.9700 . ?
C5A C6A 1.47(5) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C51A C61A 1.47(5) . ?
C51A H5A3 0.9700 . ?
C51A H5A4 0.9700 . ?
C6A C7A 1.54(3) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C61A C7A 1.47(3) . ?
C61A H6A3 0.9700 . ?
C61A H6A4 0.9700 . ?
C7A H7A1 0.9700 . ?
C7A H7A2 0.9700 . ?
C7A H7A3 0.9700 . ?
C7A H7A4 0.9700 . ?
N1B C7B 1.495(13) . ?
N1B C2B 1.504(15) . ?
N1B H1B1 0.8900 . ?
N1B H1B2 0.8900 . ?
C2B C3B 1.427(17) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C3B C4B 1.549(18) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C4B C5B 1.503(18) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B C6B 1.509(17) . ?
C5B H5B1 0.9700 . ?
C5B H5B2 0.9700 . ?
C6B C7B 1.452(15) . ?
C6B H6B1 0.9700 . ?
C6B H6B2 0.9700 . ?
C7B H7B1 0.9700 . ?
C7B H7B2 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 Bi Br2 94.45(4) . . ?
Br1 Bi Br3 87.98(4) . . ?
Br2 Bi Br3 91.64(4) . . ?
Br1 Bi Br4 86.71(4) . . ?
Br2 Bi Br4 90.66(4) . . ?
Br3 Bi Br4 174.36(3) . . ?
Br1 Bi Br5 88.89(4) . . ?
Br2 Bi Br5 176.62(3) . . ?
Br3 Bi Br5 87.95(4) . . ?
Br4 Bi Br5 90.06(3) . . ?
Br1 Bi Br5 173.43(3) . 2_656 ?
Br2 Bi Br5 91.55(4) . 2_656 ?
Br3 Bi Br5 89.19(4) . 2_656 ?
Br4 Bi Br5 95.90(4) . 2_656 ?
Br5 Bi Br5 85.08(3) . 2_656 ?
Bi Br5 Bi 158.31(4) . 2_646 ?
C2A N1A C7A 118.5(11) . . ?
C2A N1A H1A1 107.7 . . ?
C7A N1A H1A1 107.7 . . ?
C2A N1A H1A2 107.7 . . ?
C7A N1A H1A2 107.7 . . ?
H1A1 N1A H1A2 107.1 . . ?
C31A C2A N1A 123(2) . . ?
N1A C2A C3A 113.4(15) . . ?
N1A C2A H2A1 108.9 . . ?
C3A C2A H2A1 108.9 . . ?
N1A C2A H2A2 108.9 . . ?
C3A C2A H2A2 108.9 . . ?
H2A1 C2A H2A2 107.7 . . ?
C31A C2A H2A3 106.7 . . ?
N1A C2A H2A3 106.7 . . ?
C31A C2A H2A4 106.7 . . ?
N1A C2A H2A4 106.7 . . ?
H2A3 C2A H2A4 106.6 . . ?
C2A C3A C4A 115.3(19) . . ?
C2A C3A H3A1 108.4 . . ?
C4A C3A H3A1 108.4 . . ?
C2A C3A H3A2 108.4 . . ?
C4A C3A H3A2 108.4 . . ?
H3A1 C3A H3A2 107.5 . . ?
C2A C31A C4A 131(3) . . ?
C2A C31A H3A3 104.4 . . ?
C4A C31A H3A3 104.4 . . ?
C2A C31A H3A4 104.4 . . ?
C4A C31A H3A4 104.4 . . ?
H3A3 C31A H3A4 105.6 . . ?
C51A C4A C31A 118(3) . . ?
C5A C4A C3A 128(2) . . ?
C5A C4A H4A1 105.2 . . ?
C3A C4A H4A1 105.2 . . ?
C5A C4A H4A2 105.2 . . ?
C3A C4A H4A2 105.2 . . ?
H4A1 C4A H4A2 105.9 . . ?
C51A C4A H4A3 107.8 . . ?
C31A C4A H4A3 107.8 . . ?
C51A C4A H4A4 107.8 . . ?
C31A C4A H4A4 107.8 . . ?
H4A3 C4A H4A4 107.2 . . ?
C4A C5A C6A 113(3) . . ?
C4A C5A H5A1 109.0 . . ?
C6A C5A H5A1 109.0 . . ?
C4A C5A H5A2 109.0 . . ?
C6A C5A H5A2 109.0 . . ?
H5A1 C5A H5A2 107.8 . . ?
C4A C51A C61A 110(4) . . ?
C4A C51A H5A3 109.6 . . ?
C61A C51A H5A3 109.6 . . ?
C4A C51A H5A4 109.6 . . ?
C61A C51A H5A4 109.6 . . ?
H5A3 C51A H5A4 108.1 . . ?
C5A C6A C7A 119(3) . . ?
C5A C6A H6A1 107.7 . . ?
C7A C6A H6A1 107.7 . . ?
C5A C6A H6A2 107.7 . . ?
C7A C6A H6A2 107.7 . . ?
H6A1 C6A H6A2 107.1 . . ?
C7A C61A C51A 118(3) . . ?
C7A C61A H6A3 107.9 . . ?
C51A C61A H6A3 107.9 . . ?
C7A C61A H6A4 107.9 . . ?
C51A C61A H6A4 107.9 . . ?
H6A3 C61A H6A4 107.2 . . ?
C61A C7A N1A 122.2(16) . . ?
N1A C7A C6A 107.9(16) . . ?
N1A C7A H7A1 110.1 . . ?
C6A C7A H7A1 110.1 . . ?
N1A C7A H7A2 110.1 . . ?
C6A C7A H7A2 110.1 . . ?
H7A1 C7A H7A2 108.4 . . ?
C61A C7A H7A3 106.8 . . ?
N1A C7A H7A3 106.8 . . ?
C61A C7A H7A4 106.8 . . ?
N1A C7A H7A4 106.8 . . ?
H7A3 C7A H7A4 106.6 . . ?
C7B N1B C2B 118.2(9) . . ?
C7B N1B H1B1 107.8 . . ?
C2B N1B H1B1 107.8 . . ?
C7B N1B H1B2 107.8 . . ?
C2B N1B H1B2 107.8 . . ?
H1B1 N1B H1B2 107.1 . . ?
C3B C2B N1B 116.3(12) . . ?
C3B C2B H2B1 108.2 . . ?
N1B C2B H2B1 108.2 . . ?
C3B C2B H2B2 108.2 . . ?
N1B C2B H2B2 108.2 . . ?
H2B1 C2B H2B2 107.4 . . ?
C2B C3B C4B 115.5(13) . . ?
C2B C3B H3B1 108.4 . . ?
C4B C3B H3B1 108.4 . . ?
C2B C3B H3B2 108.4 . . ?
C4B C3B H3B2 108.4 . . ?
H3B1 C3B H3B2 107.5 . . ?
C5B C4B C3B 117.5(11) . . ?
C5B C4B H4B1 107.9 . . ?
C3B C4B H4B1 107.9 . . ?
C5B C4B H4B2 107.9 . . ?
C3B C4B H4B2 107.9 . . ?
H4B1 C4B H4B2 107.2 . . ?
C4B C5B C6B 114.3(10) . . ?
C4B C5B H5B1 108.7 . . ?
C6B C5B H5B1 108.7 . . ?
C4B C5B H5B2 108.7 . . ?
C6B C5B H5B2 108.7 . . ?
H5B1 C5B H5B2 107.6 . . ?
C7B C6B C5B 116.0(11) . . ?
C7B C6B H6B1 108.3 . . ?
C5B C6B H6B1 108.3 . . ?
C7B C6B H6B2 108.3 . . ?
C5B C6B H6B2 108.3 . . ?
H6B1 C6B H6B2 107.4 . . ?
C6B C7B N1B 116.0(10) . . ?
C6B C7B H7B1 108.3 . . ?
N1B C7B H7B1 108.3 . . ?
C6B C7B H7B2 108.3 . . ?
N1B C7B H7B2 108.3 . . ?
H7B1 C7B H7B2 107.4 . . ?

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
C7A N1A C2A C31A 27(3) . . . . ?
C7A N1A C2A C3A 73(2) . . . . ?
N1A C2A C3A C4A -71(3) . . . . ?
N1A C2A C31A C4A 33(5) . . . . ?
C2A C31A C4A C51A -37(5) . . . . ?
C2A C3A C4A C5A 49(4) . . . . ?
C3A C4A C5A C6A 8(5) . . . . ?
C31A C4A C51A C61A -35(4) . . . . ?
C4A C5A C6A C7A -68(5) . . . . ?
C4A C51A C61A C7A 82(4) . . . . ?
C51A C61A C7A N1A -38(5) . . . . ?
C2A N1A C7A C61A -31(3) . . . . ?
C2A N1A C7A C6A -71.3(19) . . . . ?
C5A C6A C7A N1A 84(3) . . . . ?
C7B N1B C2B C3B 38.6(18) . . . . ?
N1B C2B C3B C4B -82.2(17) . . . . ?
C2B C3B C4B C5B 67.5(19) . . . . ?
C3B C4B C5B C6B -49.1(18) . . . . ?
C4B C5B C6B C7B 70.0(15) . . . . ?
C5B C6B C7B N1B -85.3(14) . . . . ?
C2B N1B C7B C6B 37.2(17) . . . . ?

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
N1A H1A1 Br4 0.89 2.62 3.514(11) 178.2 .
N1A H1A2 Br2 0.89 2.78 3.511(10) 140.8 1_545
C2A H2A4 Br2 0.97 2.97 3.698(16) 133.0 1_545
C7A H7A1 Br5 0.97 3.03 3.776(12) 134.8 .
C7A H7A2 Br4 0.97 3.00 3.962(15) 170.9 1_545
N1B H1B1 Br2 0.89 2.61 3.461(10) 160.1 1_545
N1B H1B2 Br3 0.89 2.60 3.438(10) 157.2 .
C2B H2B1 Br4 0.97 3.04 3.803(13) 136.3 2_646
C6B H6B1 Br1 0.97 2.97 3.708(11) 134.1 3_666

_refine_diff_density_max         1.293
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.189

####################################################################### 
# 
# 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_HBC200K
_database_code_depnum_ccdc_archive 'CCDC 1859098'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_HBC200K             
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern along the b* axis: reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted.
;
_vrf_PLAT112_HBC200K             
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       c/2        100 %Fit
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern along the b* axis: reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted.
;
_vrf_PLAT113_HBC200K             
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       C2/m Check
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern along the b* axis: reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted.
;
# Added during the CSD deposition process: Monday 30 July 2018 09:49 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H14 N), Bi Cl6, H3 O'
_chemical_formula_sum            'C12 H31 Bi Cl6 N2 O'
_chemical_formula_weight         641.07

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'
Bi Bi -4.1077 10.2566 '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'
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           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                   18.212(4)
_cell_length_b                   7.863(2)
_cell_length_c                   15.828(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.33(2)
_cell_angle_gamma                90
_cell_volume                     2266(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4015
_cell_measurement_theta_min      3.7870
_cell_measurement_theta_max      28.7270

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    8.490
_shelx_estimated_absorpt_T_min   0.429
_shelx_estimated_absorpt_T_max   0.676
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.458
_exptl_absorpt_correction_T_max  0.721
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            6652
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.822
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2289
_reflns_number_gt                1823
_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       
;
CrysAlisCCD, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 4.0'
_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)+(0.0617P)²+1.8821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2289
_refine_ls_number_parameters     112
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Bi Bi 0.5000 0.5000 0.5000 0.02873(17) Uani 1 2 d S . P . .
Cl1 Cl 0.56400(10) 0.2809(3) 0.39317(12) 0.0501(5) Uani 1 1 d . . . . .
Cl2 Cl 0.37938(12) 0.5268(2) 0.39719(14) 0.0426(4) Uani 1 1 d . . . . .
Cl3 Cl 0.55501(9) 0.7704(2) 0.41641(11) 0.0420(4) Uani 1 1 d . . . . .
O1H O 0.5000 0.5396(12) 0.2500 0.089(4) Uani 1 2 d S T P . .
H1H H 0.4783 0.5989 0.2858 0.133 Uiso 0.5 1 d R U P . .
H2H H 0.5182 0.4508 0.2713 0.133 Uiso 1 1 d R U . . .
N1A N 0.6182(5) 1.0348(9) 0.5628(6) 0.067(2) Uani 1 1 d . U . . .
H1A1 H 0.5904 0.9832 0.5217 0.080 Uiso 1 1 calc R U . . .
H1A2 H 0.6055 1.1467 0.5626 0.080 Uiso 1 1 calc R U . . .
C2A C 0.6950(8) 1.0239(11) 0.5377(9) 0.074(3) Uani 1 1 d . U . . .
H2A1 H 0.7158 1.1401 0.5409 0.089 Uiso 0.66(2) 1 calc R U P A 1
H2A2 H 0.6950 0.9896 0.4775 0.089 Uiso 0.66(2) 1 calc R U P A 1
H2A3 H 0.7012 0.9108 0.5112 0.089 Uiso 0.34(2) 1 calc R U P A 2
H2A4 H 0.7014 1.1091 0.4924 0.089 Uiso 0.34(2) 1 calc R U P A 2
C3A C 0.7466(6) 0.9092(19) 0.5843(8) 0.048(4) Uani 0.66(2) 1 d . U P A 1
H3A1 H 0.7244 0.7942 0.5849 0.058 Uiso 0.66(2) 1 calc R U P A 1
H3A2 H 0.7922 0.9014 0.5517 0.058 Uiso 0.66(2) 1 calc R U P A 1
C31A C 0.7520(17) 1.044(6) 0.593(2) 0.070(8) Uani 0.34(2) 1 d . U P A 2
H3A3 H 0.7515 1.1662 0.6079 0.084 Uiso 0.34(2) 1 calc R U P A 2
H3A4 H 0.7964 1.0272 0.5587 0.084 Uiso 0.34(2) 1 calc R U P A 2
C4A C 0.7673(6) 0.9546(13) 0.6720(8) 0.072(3) Uani 1 1 d . U . . .
H4A1 H 0.7860 1.0728 0.6714 0.087 Uiso 0.66(2) 1 calc R U P A 1
H4A2 H 0.8089 0.8807 0.6896 0.087 Uiso 0.66(2) 1 calc R U P A 1
H4A3 H 0.8116 1.0076 0.6980 0.087 Uiso 0.34(2) 1 calc R U P A 2
H4A4 H 0.7807 0.8365 0.6573 0.087 Uiso 0.34(2) 1 calc R U P A 2
C5A C 0.7111(6) 0.9441(14) 0.7391(6) 0.074(3) Uani 1 1 d . U . . .
H5A1 H 0.7020 0.8225 0.7512 0.089 Uiso 1 1 calc R U . . .
H5A2 H 0.7322 0.9958 0.7913 0.089 Uiso 1 1 calc R U . . .
C6A C 0.6402(8) 1.0259(11) 0.7203(7) 0.069(3) Uani 1 1 d . U . . .
H6A1 H 0.6491 1.1490 0.7124 0.083 Uiso 1 1 calc R U . . .
H6A2 H 0.6093 1.0136 0.7706 0.083 Uiso 1 1 calc R U . . .
C7A C 0.5965(5) 0.9628(12) 0.6448(10) 0.076(3) Uani 1 1 d . U . . .
H7A1 H 0.6012 0.8375 0.6421 0.091 Uiso 1 1 calc R U . . .
H7A2 H 0.5440 0.9894 0.6532 0.091 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
Bi Cl1 2.6976(18) 5_666 ?
Bi Cl1 2.6976(18) . ?
Bi Cl3 2.7086(18) . ?
Bi Cl3 2.7086(18) 5_666 ?
Bi Cl2 2.712(2) 5_666 ?
Bi Cl2 2.712(2) . ?
O1H H1H 0.8400 . ?
O1H H2H 0.8400 . ?
N1A C2A 1.465(16) . ?
N1A C7A 1.478(16) . ?
N1A H1A1 0.9100 . ?
N1A H1A2 0.9100 . ?
C2A C31A 1.35(4) . ?
C2A C3A 1.485(18) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C2A H2A3 0.9900 . ?
C2A H2A4 0.9900 . ?
C3A C4A 1.474(17) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C31A C4A 1.46(4) . ?
C31A H3A3 0.9900 . ?
C31A H3A4 0.9900 . ?
C4A C5A 1.494(15) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C4A H4A3 0.9900 . ?
C4A H4A4 0.9900 . ?
C5A C6A 1.467(16) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A C7A 1.505(18) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?

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
Cl1 Bi Cl1 180.0 5_666 . ?
Cl1 Bi Cl3 88.57(6) 5_666 . ?
Cl1 Bi Cl3 91.43(6) . . ?
Cl1 Bi Cl3 91.43(6) 5_666 5_666 ?
Cl1 Bi Cl3 88.57(6) . 5_666 ?
Cl3 Bi Cl3 180.0 . 5_666 ?
Cl1 Bi Cl2 91.68(6) 5_666 5_666 ?
Cl1 Bi Cl2 88.32(6) . 5_666 ?
Cl3 Bi Cl2 92.90(6) . 5_666 ?
Cl3 Bi Cl2 87.10(6) 5_666 5_666 ?
Cl1 Bi Cl2 88.32(6) 5_666 . ?
Cl1 Bi Cl2 91.68(6) . . ?
Cl3 Bi Cl2 87.10(6) . . ?
Cl3 Bi Cl2 92.90(6) 5_666 . ?
Cl2 Bi Cl2 180.0 5_666 . ?
H1H O1H H2H 112.3 . . ?
C2A N1A C7A 119.5(8) . . ?
C2A N1A H1A1 107.4 . . ?
C7A N1A H1A1 107.4 . . ?
C2A N1A H1A2 107.4 . . ?
C7A N1A H1A2 107.4 . . ?
H1A1 N1A H1A2 107.0 . . ?
C31A C2A N1A 122.9(17) . . ?
N1A C2A C3A 119.8(10) . . ?
N1A C2A H2A1 107.4 . . ?
C3A C2A H2A1 107.4 . . ?
N1A C2A H2A2 107.4 . . ?
C3A C2A H2A2 107.4 . . ?
H2A1 C2A H2A2 106.9 . . ?
C31A C2A H2A3 106.6 . . ?
N1A C2A H2A3 106.6 . . ?
C31A C2A H2A4 106.6 . . ?
N1A C2A H2A4 106.6 . . ?
H2A3 C2A H2A4 106.6 . . ?
C4A C3A C2A 117.7(11) . . ?
C4A C3A H3A1 107.9 . . ?
C2A C3A H3A1 107.9 . . ?
C4A C3A H3A2 107.9 . . ?
C2A C3A H3A2 107.9 . . ?
H3A1 C3A H3A2 107.2 . . ?
C2A C31A C4A 129(3) . . ?
C2A C31A H3A3 105.1 . . ?
C4A C31A H3A3 105.1 . . ?
C2A C31A H3A4 105.1 . . ?
C4A C31A H3A4 105.1 . . ?
H3A3 C31A H3A4 105.9 . . ?
C31A C4A C5A 121.2(15) . . ?
C3A C4A C5A 119.5(10) . . ?
C3A C4A H4A1 107.5 . . ?
C5A C4A H4A1 107.5 . . ?
C3A C4A H4A2 107.5 . . ?
C5A C4A H4A2 107.5 . . ?
H4A1 C4A H4A2 107.0 . . ?
C31A C4A H4A3 107.0 . . ?
C5A C4A H4A3 107.0 . . ?
C31A C4A H4A4 107.0 . . ?
C5A C4A H4A4 107.0 . . ?
H4A3 C4A H4A4 106.8 . . ?
C6A C5A C4A 116.5(9) . . ?
C6A C5A H5A1 108.2 . . ?
C4A C5A H5A1 108.2 . . ?
C6A C5A H5A2 108.2 . . ?
C4A C5A H5A2 108.2 . . ?
H5A1 C5A H5A2 107.3 . . ?
C5A C6A C7A 117.6(9) . . ?
C5A C6A H6A1 107.9 . . ?
C7A C6A H6A1 107.9 . . ?
C5A C6A H6A2 107.9 . . ?
C7A C6A H6A2 107.9 . . ?
H6A1 C6A H6A2 107.2 . . ?
N1A C7A C6A 115.1(8) . . ?
N1A C7A H7A1 108.5 . . ?
C6A C7A H7A1 108.5 . . ?
N1A C7A H7A2 108.5 . . ?
C6A C7A H7A2 108.5 . . ?
H7A1 C7A H7A2 107.5 . . ?

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
C7A N1A C2A C31A -39(3) . . . . ?
C7A N1A C2A C3A 13.6(15) . . . . ?
N1A C2A C3A C4A -68.9(15) . . . . ?
N1A C2A C31A C4A 54(5) . . . . ?
C2A C31A C4A C5A -53(5) . . . . ?
C2A C3A C4A C5A 68.9(16) . . . . ?
C31A C4A C5A C6A 1(3) . . . . ?
C3A C4A C5A C6A -49.3(16) . . . . ?
C4A C5A C6A C7A 60.1(15) . . . . ?
C2A N1A C7A C6A 53.9(13) . . . . ?
C5A C6A C7A N1A -82.6(12) . . . . ?

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
O1H H2H Cl1 0.84 2.48 3.242(6) 152.1 .
O1H H1H Cl2 0.84 2.61 3.241(2) 132.7 .
O1H H1H Cl3 0.84 2.81 3.334(5) 121.9 .
N1A H1A2 Cl2 0.91 2.66 3.505(7) 155.3 5_676
N1A H1A1 Cl3 0.91 2.44 3.300(8) 158.1 .
C7A H7A2 Cl3 0.99 2.82 3.581(10) 134.4 5_676

_refine_diff_density_max         0.856
_refine_diff_density_min         -2.049
_refine_diff_density_rms         0.215

####################################################################### 
# 
# 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_HSC200K
_database_code_depnum_ccdc_archive 'CCDC 1859095'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H14 N), Sb Cl5'
_chemical_formula_sum            'C12 H28 Cl5 N2 Sb'
_chemical_formula_weight         499.36

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'
Sb Sb -0.5866 1.5461 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.478(4)
_cell_length_b                   13.246(2)
_cell_length_c                   19.854(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1966(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    22268
_cell_measurement_theta_min      3.1010
_cell_measurement_theta_max      36.8100

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.076
_shelx_estimated_absorpt_T_min   0.658
_shelx_estimated_absorpt_T_max   0.789
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            20589
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.911
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.499
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3653
_reflns_number_gt                3593
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       
;
CrysAlisCCD, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 4.0'
_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)+(0.0426P)²+0.5280P] 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_abs_structure_details 
;
 Flack x determined using 1514 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.055(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3653
_refine_ls_number_parameters     200
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Sb Sb 0.42566(4) 0.39756(2) 0.55621(2) 0.01682(11) Uani 1 1 d . . . . .
Cl1 Cl 0.60745(15) 0.50518(8) 0.62391(6) 0.0272(3) Uani 1 1 d . . . . .
Cl2 Cl 0.41213(17) 0.27357(8) 0.65206(6) 0.0249(2) Uani 1 1 d . . . . .
Cl3 Cl 0.14318(15) 0.48056(9) 0.60634(6) 0.0268(3) Uani 1 1 d . . . . .
Cl4 Cl 0.72581(16) 0.30593(9) 0.51625(6) 0.0273(3) Uani 1 1 d . . . . .
Cl5 Cl 0.47191(15) 0.55001(9) 0.45970(6) 0.0257(3) Uani 1 1 d . . . . .
N1A N 0.8952(6) 0.5436(3) 0.4799(2) 0.0268(9) Uani 1 1 d . . . . .
H1A2 H 0.9165 0.5136 0.5203 0.032 Uiso 1 1 calc R U . . .
H1A1 H 0.7757 0.5391 0.4719 0.032 Uiso 1 1 calc R U . . .
C2A C 0.9901(7) 0.4844(4) 0.4269(3) 0.0301(12) Uani 1 1 d . . . . .
H2A2 H 0.9669 0.4116 0.4342 0.036 Uiso 1 1 calc R U . . .
H2A1 H 1.1205 0.4956 0.4314 0.036 Uiso 1 1 calc R U . . .
C3A C 0.9338(9) 0.5121(5) 0.3571(3) 0.0413(13) Uani 1 1 d . . . . .
H3A2 H 0.8024 0.5216 0.3568 0.050 Uiso 1 1 calc R U . . .
H3A1 H 0.9613 0.4548 0.3268 0.050 Uiso 1 1 calc R U . . .
C4A C 1.0192(12) 0.6053(5) 0.3288(3) 0.0567(19) Uani 1 1 d . . . . .
H4A2 H 0.9915 0.6088 0.2801 0.068 Uiso 0.600(19) 1 calc R U P A 1
H4A1 H 1.1505 0.5985 0.3333 0.068 Uiso 0.600(19) 1 calc R U P A 1
H4A3 H 1.1440 0.5876 0.3171 0.068 Uiso 0.400(19) 1 calc R U P A 2
H4A4 H 0.9571 0.6212 0.2861 0.068 Uiso 0.400(19) 1 calc R U P A 2
C5A C 0.962(2) 0.7066(15) 0.3619(10) 0.050(5) Uani 0.600(19) 1 d . U P A 1
H5A1 H 1.0696 0.7502 0.3615 0.060 Uiso 0.600(19) 1 calc R U P A 1
H5A2 H 0.8756 0.7380 0.3305 0.060 Uiso 0.600(19) 1 calc R U P A 1
C51A C 1.025(4) 0.696(2) 0.3671(17) 0.055(7) Uani 0.400(19) 1 d . U P A 2
H5A3 H 1.1261 0.7348 0.3481 0.066 Uiso 0.400(19) 1 calc R U P A 2
H5A4 H 0.9155 0.7329 0.3548 0.066 Uiso 0.400(19) 1 calc R U P A 2
C6A C 0.8884(15) 0.7162(7) 0.4257(6) 0.044(4) Uani 0.600(19) 1 d . . P A 1
H6A1 H 0.7580 0.7060 0.4203 0.053 Uiso 0.600(19) 1 calc R U P A 1
H6A2 H 0.9048 0.7877 0.4388 0.053 Uiso 0.600(19) 1 calc R U P A 1
C61A C 1.0395(16) 0.7050(9) 0.4306(7) 0.027(4) Uani 0.400(19) 1 d . . P A 2
H6A3 H 1.0214 0.7779 0.4390 0.032 Uiso 0.400(19) 1 calc R U P A 2
H6A4 H 1.1674 0.6920 0.4401 0.032 Uiso 0.400(19) 1 calc R U P A 2
C7A C 0.9427(10) 0.6542(4) 0.4863(3) 0.0418(14) Uani 1 1 d . . . . .
H7A1 H 0.8835 0.6820 0.5268 0.050 Uiso 0.600(19) 1 calc R U P A 1
H7A2 H 1.0735 0.6604 0.4928 0.050 Uiso 0.600(19) 1 calc R U P A 1
H7A3 H 0.8300 0.6918 0.4938 0.050 Uiso 0.400(19) 1 calc R U P A 2
H7A4 H 1.0157 0.6620 0.5275 0.050 Uiso 0.400(19) 1 calc R U P A 2
N1B N 0.9520(7) 0.2703(3) 0.6541(2) 0.0349(11) Uani 1 1 d . . . . .
H1B1 H 0.9046 0.3026 0.6177 0.042 Uiso 1 1 calc R U . . .
H1B2 H 1.0718 0.2821 0.6537 0.042 Uiso 1 1 calc R U . . .
C2B C 0.9234(10) 0.1601(4) 0.6450(3) 0.0381(13) Uani 1 1 d . . . . .
H2B1 H 1.0180 0.1336 0.6149 0.046 Uiso 1 1 calc R U . . .
H2B2 H 0.8072 0.1497 0.6221 0.046 Uiso 1 1 calc R U . . .
C3B C 0.9242(9) 0.0992(4) 0.7093(3) 0.0381(13) Uani 1 1 d . . . . .
H3B1 H 0.8081 0.1094 0.7322 0.046 Uiso 1 1 calc R U . . .
H3B2 H 0.9324 0.0268 0.6972 0.046 Uiso 1 1 calc R U . . .
C4B C 1.0714(8) 0.1228(4) 0.7585(3) 0.0338(12) Uani 1 1 d . . . . .
H4B1 H 1.1801 0.1419 0.7331 0.041 Uiso 1 1 calc R U . . .
H4B2 H 1.0994 0.0610 0.7846 0.041 Uiso 1 1 calc R U . . .
C5B C 1.0255(8) 0.2072(5) 0.8073(3) 0.0353(13) Uani 1 1 d . . . . .
H5B1 H 1.1204 0.2109 0.8420 0.042 Uiso 1 1 calc R U . . .
H5B2 H 0.9123 0.1899 0.8304 0.042 Uiso 1 1 calc R U . . .
C6B C 1.0054(8) 0.3106(4) 0.7750(3) 0.0317(12) Uani 1 1 d . . . . .
H6B1 H 0.9667 0.3588 0.8102 0.038 Uiso 1 1 calc R U . . .
H6B2 H 1.1245 0.3327 0.7590 0.038 Uiso 1 1 calc R U . . .
C7B C 0.8753(7) 0.3176(4) 0.7166(3) 0.0328(12) Uani 1 1 d . . . . .
H7B1 H 0.7625 0.2829 0.7287 0.039 Uiso 1 1 calc R U . . .
H7B2 H 0.8473 0.3894 0.7076 0.039 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
Sb Cl1 2.3846(12) . ?
Sb Cl2 2.5158(11) . ?
Sb Cl3 2.5809(15) . ?
Sb Cl4 2.6721(16) . ?
Sb Cl5 2.8052(12) . ?
Sb Cl4 3.4012(13) 4_456 ?
N1A C2A 1.493(7) . ?
N1A C7A 1.512(7) . ?
N1A H1A2 0.9100 . ?
N1A H1A1 0.9100 . ?
C2A C3A 1.494(8) . ?
C2A H2A2 0.9900 . ?
C2A H2A1 0.9900 . ?
C3A C4A 1.499(9) . ?
C3A H3A2 0.9900 . ?
C3A H3A1 0.9900 . ?
C4A C51A 1.42(3) . ?
C4A C5A 1.55(2) . ?
C4A H4A2 0.9900 . ?
C4A H4A1 0.9900 . ?
C4A H4A3 0.9900 . ?
C4A H4A4 0.9900 . ?
C5A C6A 1.39(2) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C51A C61A 1.27(4) . ?
C51A H5A3 0.9900 . ?
C51A H5A4 0.9900 . ?
C6A C7A 1.511(13) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C61A C7A 1.483(14) . ?
C61A H6A3 0.9900 . ?
C61A H6A4 0.9900 . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C7A H7A3 0.9900 . ?
C7A H7A4 0.9900 . ?
N1B C2B 1.487(6) . ?
N1B C7B 1.505(7) . ?
N1B H1B1 0.9100 . ?
N1B H1B2 0.9100 . ?
C2B C3B 1.510(8) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B C4B 1.505(8) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C4B C5B 1.518(8) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5B C6B 1.520(8) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B C7B 1.517(8) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?

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
Cl1 Sb Cl2 89.25(4) . . ?
Cl1 Sb Cl3 89.69(5) . . ?
Cl2 Sb Cl3 87.33(4) . . ?
Cl1 Sb Cl4 87.71(5) . . ?
Cl2 Sb Cl4 87.81(4) . . ?
Cl3 Sb Cl4 174.52(4) . . ?
Cl1 Sb Cl5 83.36(4) . . ?
Cl2 Sb Cl5 172.57(4) . . ?
Cl3 Sb Cl5 93.30(4) . . ?
Cl4 Sb Cl5 91.18(4) . . ?
Cl1 Sb Cl4 164.29(4) . 4_456 ?
Cl2 Sb Cl4 77.58(3) . 4_456 ?
Cl3 Sb Cl4 98.11(5) . 4_456 ?
Cl4 Sb Cl4 83.31(3) . 4_456 ?
Cl5 Sb Cl4 109.62(3) . 4_456 ?
C2A N1A C7A 117.1(4) . . ?
C2A N1A H1A2 108.0 . . ?
C7A N1A H1A2 108.0 . . ?
C2A N1A H1A1 108.0 . . ?
C7A N1A H1A1 108.0 . . ?
H1A2 N1A H1A1 107.3 . . ?
N1A C2A C3A 113.0(4) . . ?
N1A C2A H2A2 109.0 . . ?
C3A C2A H2A2 109.0 . . ?
N1A C2A H2A1 109.0 . . ?
C3A C2A H2A1 109.0 . . ?
H2A2 C2A H2A1 107.8 . . ?
C2A C3A C4A 115.4(5) . . ?
C2A C3A H3A2 108.4 . . ?
C4A C3A H3A2 108.4 . . ?
C2A C3A H3A1 108.4 . . ?
C4A C3A H3A1 108.4 . . ?
H3A2 C3A H3A1 107.5 . . ?
C51A C4A C3A 120.6(11) . . ?
C3A C4A C5A 115.9(10) . . ?
C3A C4A H4A2 108.3 . . ?
C5A C4A H4A2 108.3 . . ?
C3A C4A H4A1 108.3 . . ?
C5A C4A H4A1 108.3 . . ?
H4A2 C4A H4A1 107.4 . . ?
C51A C4A H4A3 107.2 . . ?
C3A C4A H4A3 107.2 . . ?
C51A C4A H4A4 107.2 . . ?
C3A C4A H4A4 107.2 . . ?
H4A3 C4A H4A4 106.8 . . ?
C6A C5A C4A 125.0(15) . . ?
C6A C5A H5A1 106.1 . . ?
C4A C5A H5A1 106.1 . . ?
C6A C5A H5A2 106.1 . . ?
C4A C5A H5A2 106.1 . . ?
H5A1 C5A H5A2 106.3 . . ?
C61A C51A C4A 128(2) . . ?
C61A C51A H5A3 105.3 . . ?
C4A C51A H5A3 105.3 . . ?
C61A C51A H5A4 105.3 . . ?
C4A C51A H5A4 105.3 . . ?
H5A3 C51A H5A4 106.0 . . ?
C5A C6A C7A 124.7(10) . . ?
C5A C6A H6A1 106.2 . . ?
C7A C6A H6A1 106.2 . . ?
C5A C6A H6A2 106.2 . . ?
C7A C6A H6A2 106.2 . . ?
H6A1 C6A H6A2 106.3 . . ?
C51A C61A C7A 130.9(13) . . ?
C51A C61A H6A3 104.6 . . ?
C7A C61A H6A3 104.6 . . ?
C51A C61A H6A4 104.6 . . ?
C7A C61A H6A4 104.6 . . ?
H6A3 C61A H6A4 105.7 . . ?
C61A C7A N1A 119.5(6) . . ?
C6A C7A N1A 113.4(6) . . ?
C6A C7A H7A1 108.9 . . ?
N1A C7A H7A1 108.9 . . ?
C6A C7A H7A2 108.9 . . ?
N1A C7A H7A2 108.9 . . ?
H7A1 C7A H7A2 107.7 . . ?
C61A C7A H7A3 107.4 . . ?
N1A C7A H7A3 107.4 . . ?
C61A C7A H7A4 107.4 . . ?
N1A C7A H7A4 107.4 . . ?
H7A3 C7A H7A4 107.0 . . ?
C2B N1B C7B 117.0(4) . . ?
C2B N1B H1B1 108.0 . . ?
C7B N1B H1B1 108.0 . . ?
C2B N1B H1B2 108.0 . . ?
C7B N1B H1B2 108.0 . . ?
H1B1 N1B H1B2 107.3 . . ?
N1B C2B C3B 114.9(4) . . ?
N1B C2B H2B1 108.5 . . ?
C3B C2B H2B1 108.5 . . ?
N1B C2B H2B2 108.5 . . ?
C3B C2B H2B2 108.5 . . ?
H2B1 C2B H2B2 107.5 . . ?
C4B C3B C2B 116.2(5) . . ?
C4B C3B H3B1 108.2 . . ?
C2B C3B H3B1 108.2 . . ?
C4B C3B H3B2 108.2 . . ?
C2B C3B H3B2 108.2 . . ?
H3B1 C3B H3B2 107.4 . . ?
C3B C4B C5B 113.7(5) . . ?
C3B C4B H4B1 108.8 . . ?
C5B C4B H4B1 108.8 . . ?
C3B C4B H4B2 108.8 . . ?
C5B C4B H4B2 108.8 . . ?
H4B1 C4B H4B2 107.7 . . ?
C4B C5B C6B 114.6(4) . . ?
C4B C5B H5B1 108.6 . . ?
C6B C5B H5B1 108.6 . . ?
C4B C5B H5B2 108.6 . . ?
C6B C5B H5B2 108.6 . . ?
H5B1 C5B H5B2 107.6 . . ?
C7B C6B C5B 116.2(5) . . ?
C7B C6B H6B1 108.2 . . ?
C5B C6B H6B1 108.2 . . ?
C7B C6B H6B2 108.2 . . ?
C5B C6B H6B2 108.2 . . ?
H6B1 C6B H6B2 107.4 . . ?
N1B C7B C6B 111.2(4) . . ?
N1B C7B H7B1 109.4 . . ?
C6B C7B H7B1 109.4 . . ?
N1B C7B H7B2 109.4 . . ?
C6B C7B H7B2 109.4 . . ?
H7B1 C7B H7B2 108.0 . . ?

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
C7A N1A C2A C3A -70.6(6) . . . . ?
N1A C2A C3A C4A 80.7(6) . . . . ?
C2A C3A C4A C51A -48.4(18) . . . . ?
C2A C3A C4A C5A -69.2(10) . . . . ?
C3A C4A C5A C6A 21.5(19) . . . . ?
C3A C4A C51A C61A 33(4) . . . . ?
C4A C5A C6A C7A 37(2) . . . . ?
C4A C51A C61A C7A -47(4) . . . . ?
C51A C61A C7A N1A 38(2) . . . . ?
C5A C6A C7A N1A -66.7(16) . . . . ?
C2A N1A C7A C61A 16.2(9) . . . . ?
C2A N1A C7A C6A 66.3(8) . . . . ?
C7B N1B C2B C3B -34.5(8) . . . . ?
N1B C2B C3B C4B -45.1(8) . . . . ?
C2B C3B C4B C5B 87.7(6) . . . . ?
C3B C4B C5B C6B -66.9(6) . . . . ?
C4B C5B C6B C7B 53.8(7) . . . . ?
C2B N1B C7B C6B 87.3(6) . . . . ?
C5B C6B C7B N1B -74.4(6) . . . . ?

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
N1A H1A2 Cl3 0.91 2.45 3.230(5) 144.6 1_655
N1A H1A1 Cl5 0.91 2.29 3.192(5) 171.6 .
C2A H2A2 Cl4 0.99 2.80 3.556(5) 133.1 .
C2A H2A1 Cl5 0.99 2.78 3.763(6) 170.8 1_655
N1B H1B1 Cl4 0.91 2.42 3.251(5) 152.1 .
N1B H1B2 Cl2 0.91 2.55 3.442(6) 167.5 1_655
N1B H1B2 Cl3 0.91 2.84 3.271(4) 110.3 1_655
C2B H2B1 Cl5 0.99 2.87 3.492(5) 121.7 4_556
C7B H7B2 Cl1 0.99 2.89 3.684(5) 138.2 .

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_HBC260K
_database_code_depnum_ccdc_archive 'CCDC 1859097'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H14 N), Bi Cl6, H3 O'
_chemical_formula_sum            'C12 H31 Bi Cl6 N2 O'
_chemical_formula_weight         641.07

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'
Bi Bi -4.1077 10.2566 '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'
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           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   18.338(2)
_cell_length_b                   7.905(2)
_cell_length_c                   7.933(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.32(3)
_cell_angle_gamma                90
_cell_volume                     1149(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    2077
_cell_measurement_theta_min      3.7710
_cell_measurement_theta_max      27.5160

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    8.367
_shelx_estimated_absorpt_T_min   0.433
_shelx_estimated_absorpt_T_max   0.680
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.443
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            2498
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.806
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             1348
_reflns_number_gt                1348
_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       
;
CrysAlisCCD, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 4.0'
_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)+(0.0748P)²+0.7387P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1348
_refine_ls_number_parameters     87
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1256
_refine_ls_wR_factor_gt          0.1256
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Bi Bi 0.5000 0.5000 0.5000 0.0396(2) Uani 1 4 d S T P . .
Cl1 Cl 0.55785(16) 0.2537(5) 0.3095(4) 0.0833(9) Uani 1 1 d . . . . .
Cl2 Cl 0.37960(18) 0.5000 0.2963(4) 0.0678(10) Uani 1 2 d S T P . .
O1H O 0.5000 0.5000 0.0000 0.162(14) Uani 1 4 d S T P . .
H1H H 0.4827 0.5888 -0.0419 0.243 Uiso 0.25 1 d R U P . .
H2H H 0.5028 0.5000 0.1056 0.243 Uiso 1 2 d R U P . .
N1A N 0.6154(10) 1.018(10) 0.635(2) 0.118(10) Uani 0.5 1 d D U P A -1
H1A1 H 0.6097 1.1298 0.6263 0.141 Uiso 0.5 1 calc R U P A -1
H1A2 H 0.5837 0.9707 0.5630 0.141 Uiso 0.5 1 calc R U P A -1
C2A C 0.6902(15) 0.976(11) 0.579(3) 0.111(11) Uani 0.5 1 d . U P A -1
H2A1 H 0.6839 0.8876 0.4952 0.133 Uiso 0.5 1 calc R U P A -1
H2A2 H 0.7068 1.0751 0.5184 0.133 Uiso 0.5 1 calc R U P A -1
C3A C 0.7470(13) 0.928(4) 0.677(3) 0.088(6) Uani 0.5 1 d . U P A -1
H3A1 H 0.7899 0.9608 0.6157 0.105 Uiso 0.5 1 calc R U P A -1
H3A2 H 0.7461 0.8049 0.6742 0.105 Uiso 0.5 1 calc R U P A -1
C4A C 0.7626(13) 0.969(8) 0.844(3) 0.103(11) Uani 0.5 1 d . U P A -1
H4A1 H 0.7798 1.0853 0.8435 0.123 Uiso 0.5 1 calc R U P A -1
H4A2 H 0.8040 0.9001 0.8787 0.123 Uiso 0.5 1 calc R U P A -1
C5A C 0.7121(15) 0.958(6) 0.975(3) 0.107(12) Uani 0.5 1 d . U P A -1
H5A1 H 0.7340 1.0082 1.0757 0.128 Uiso 0.5 1 calc R U P A -1
H5A2 H 0.7035 0.8397 0.9988 0.128 Uiso 0.5 1 calc R U P A -1
C6A C 0.6407(14) 1.041(6) 0.942(3) 0.103(12) Uani 0.5 1 d . U P A -1
H6A1 H 0.6132 1.0373 1.0450 0.123 Uiso 0.5 1 calc R U P A -1
H6A2 H 0.6495 1.1590 0.9161 0.123 Uiso 0.5 1 calc R U P A -1
C7A C 0.5954(12) 0.969(8) 0.806(4) 0.121(12) Uani 0.5 1 d D U P A -1
H7A1 H 0.5452 1.0015 0.8230 0.145 Uiso 0.5 1 calc R U P A -1
H7A2 H 0.5979 0.8463 0.8139 0.145 Uiso 0.5 1 calc R U P A -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
Bi Cl1 2.697(3) 5_666 ?
Bi Cl1 2.697(3) 2_656 ?
Bi Cl1 2.697(3) . ?
Bi Cl1 2.697(3) 6_565 ?
Bi Cl2 2.706(3) . ?
Bi Cl2 2.706(3) 5_666 ?
O1H H1H 0.8363 . ?
O1H H2H 0.8382 . ?
N1A C7A 1.465(19) . ?
N1A C2A 1.49(4) . ?
N1A H1A1 0.8900 . ?
N1A H1A2 0.8900 . ?
C2A C3A 1.34(4) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A C4A 1.39(3) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A C5A 1.41(3) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A C6A 1.48(4) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A C7A 1.46(5) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C7A H7A1 0.9700 . ?
C7A H7A2 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
Cl1 Bi Cl1 92.44(18) 5_666 2_656 ?
Cl1 Bi Cl1 180.00(11) 5_666 . ?
Cl1 Bi Cl1 87.56(18) 2_656 . ?
Cl1 Bi Cl1 87.56(18) 5_666 6_565 ?
Cl1 Bi Cl1 180.0 2_656 6_565 ?
Cl1 Bi Cl1 92.44(18) . 6_565 ?
Cl1 Bi Cl2 90.49(8) 5_666 . ?
Cl1 Bi Cl2 90.49(8) 2_656 . ?
Cl1 Bi Cl2 89.51(8) . . ?
Cl1 Bi Cl2 89.51(8) 6_565 . ?
Cl1 Bi Cl2 89.51(8) 5_666 5_666 ?
Cl1 Bi Cl2 89.51(8) 2_656 5_666 ?
Cl1 Bi Cl2 90.49(8) . 5_666 ?
Cl1 Bi Cl2 90.49(8) 6_565 5_666 ?
Cl2 Bi Cl2 180.0 . 5_666 ?
H1H O1H H2H 114.3 . . ?
C7A N1A C2A 118(4) . . ?
C7A N1A H1A1 107.8 . . ?
C2A N1A H1A1 107.8 . . ?
C7A N1A H1A2 107.8 . . ?
C2A N1A H1A2 107.8 . . ?
H1A1 N1A H1A2 107.2 . . ?
C3A C2A N1A 127(2) . . ?
C3A C2A H2A1 105.6 . . ?
N1A C2A H2A1 105.6 . . ?
C3A C2A H2A2 105.6 . . ?
N1A C2A H2A2 105.6 . . ?
H2A1 C2A H2A2 106.1 . . ?
C2A C3A C4A 129(3) . . ?
C2A C3A H3A1 105.1 . . ?
C4A C3A H3A1 105.1 . . ?
C2A C3A H3A2 105.1 . . ?
C4A C3A H3A2 105.1 . . ?
H3A1 C3A H3A2 105.9 . . ?
C3A C4A C5A 124(3) . . ?
C3A C4A H4A1 106.3 . . ?
C5A C4A H4A1 106.3 . . ?
C3A C4A H4A2 106.3 . . ?
C5A C4A H4A2 106.3 . . ?
H4A1 C4A H4A2 106.4 . . ?
C4A C5A C6A 116(3) . . ?
C4A C5A H5A1 108.3 . . ?
C6A C5A H5A1 108.3 . . ?
C4A C5A H5A2 108.3 . . ?
C6A C5A H5A2 108.3 . . ?
H5A1 C5A H5A2 107.4 . . ?
C7A C6A C5A 116(4) . . ?
C7A C6A H6A1 108.2 . . ?
C5A C6A H6A1 108.2 . . ?
C7A C6A H6A2 108.2 . . ?
C5A C6A H6A2 108.2 . . ?
H6A1 C6A H6A2 107.4 . . ?
C6A C7A N1A 115(3) . . ?
C6A C7A H7A1 108.4 . . ?
N1A C7A H7A1 108.4 . . ?
C6A C7A H7A2 108.4 . . ?
N1A C7A H7A2 108.4 . . ?
H7A1 C7A H7A2 107.5 . . ?

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
O1H H2H Cl1 0.84 2.71 3.290(4) 127.5 .
O1H H1H Cl1 0.84 2.56 3.290(4) 147.1 5_665
O1H H2H Cl1 0.84 2.71 3.290(4) 127.5 6_565
O1H H2H Cl2 0.84 2.75 3.262(4) 121.2 .
N1A H1A2 Cl1 0.89 2.71 3.50(5) 148.5 6_565
N1A H1A1 Cl1 0.89 2.84 3.33(5) 116.5 1_565
C7A H7A1 Cl1 0.97 2.93 3.70(4) 137.7 2_666

_refine_diff_density_max         0.884
_refine_diff_density_min         -2.574
_refine_diff_density_rms         0.239

####################################################################### 
# 
# 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_HBB200K
_database_code_depnum_ccdc_archive 'CCDC 1859100'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H28 Bi Br5 N2'
_chemical_formula_weight         808.89

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'
Bi Bi -4.1077 10.2566 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.993(4)
_cell_length_b                   7.845(2)
_cell_length_c                   21.164(4)
_cell_angle_alpha                90
_cell_angle_beta                 89.42(2)
_cell_angle_gamma                90
_cell_volume                     2157(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6787
_cell_measurement_theta_min      3.0190
_cell_measurement_theta_max      32.3560

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.491
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    17.430
_shelx_estimated_absorpt_T_min   0.210
_shelx_estimated_absorpt_T_max   0.421
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.211
_exptl_absorpt_correction_T_max  0.385
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            14584
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.769
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4368
_reflns_number_gt                3573
_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       
;
CrysAlisCCD, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 4.0'
_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)+(0.0675P)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         4368
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.002
_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
Bi Bi 0.60920(2) 1.05002(3) 0.69467(2) 0.01870(12) Uani 1 1 d . . . . .
Br1 Br 0.51515(7) 0.75262(10) 0.65692(4) 0.0293(2) Uani 1 1 d . . . . .
Br2 Br 0.47126(6) 1.25803(11) 0.63781(4) 0.0297(2) Uani 1 1 d . . . . .
Br3 Br 0.73082(7) 1.06177(11) 0.58345(4) 0.0309(2) Uani 1 1 d . . . . .
Br4 Br 0.47694(7) 1.05655(10) 0.80442(4) 0.0278(2) Uani 1 1 d . . . . .
Br5 Br 0.78302(6) 0.86099(11) 0.76217(4) 0.0286(2) Uani 1 1 d . . . . .
N1A N 0.4569(6) 0.4895(10) 0.7819(3) 0.0302(17) Uani 1 1 d . . . . .
H1A1 H 0.4918 0.5082 0.7451 0.036 Uiso 1 1 calc R U . . .
H1A2 H 0.4545 0.3748 0.7880 0.036 Uiso 1 1 calc R U . . .
C2A C 0.3492(7) 0.5518(12) 0.7739(5) 0.039(2) Uani 1 1 d . . . . .
H2A1 H 0.3295 0.5409 0.7290 0.047 Uiso 1 1 calc R U . . .
H2A2 H 0.3453 0.6739 0.7855 0.047 Uiso 1 1 calc R U . . .
C3A C 0.2738(7) 0.4499(13) 0.8152(5) 0.044(3) Uani 1 1 d . . . . .
H3A1 H 0.2031 0.4756 0.8011 0.052 Uiso 1 1 calc R U . . .
H3A2 H 0.2862 0.3271 0.8075 0.052 Uiso 1 1 calc R U . . .
C4A C 0.2784(7) 0.4805(12) 0.8849(5) 0.038(2) Uani 1 1 d . . . . .
H4A1 H 0.2304 0.4002 0.9060 0.046 Uiso 1 1 calc R U . . .
H4A2 H 0.2528 0.5973 0.8934 0.046 Uiso 1 1 calc R U . . .
C5A C 0.3828(8) 0.4622(12) 0.9153(5) 0.038(2) Uani 1 1 d . . . . .
H5A1 H 0.4120 0.3496 0.9040 0.046 Uiso 1 1 calc R U . . .
H5A2 H 0.3740 0.4657 0.9618 0.046 Uiso 1 1 calc R U . . .
C6A C 0.4591(8) 0.6020(13) 0.8951(5) 0.041(2) Uani 1 1 d . . . . .
H6A1 H 0.4206 0.7100 0.8898 0.050 Uiso 1 1 calc R U . . .
H6A2 H 0.5090 0.6192 0.9296 0.050 Uiso 1 1 calc R U . . .
C7A C 0.5183(7) 0.5661(12) 0.8347(4) 0.033(2) Uani 1 1 d . . . . .
H7A1 H 0.5489 0.6743 0.8194 0.040 Uiso 1 1 calc R U . . .
H7A2 H 0.5757 0.4878 0.8445 0.040 Uiso 1 1 calc R U . . .
N1B N 0.6932(5) 0.4978(10) 0.5827(3) 0.0296(16) Uani 1 1 d . . . . .
H1B1 H 0.7040 0.3832 0.5818 0.036 Uiso 1 1 calc R U . . .
H1B2 H 0.6528 0.5203 0.6171 0.036 Uiso 1 1 calc R U . . .
C2B C 0.7968(7) 0.5851(13) 0.5922(4) 0.034(2) Uani 1 1 d . . . . .
H2B1 H 0.7855 0.6901 0.6173 0.041 Uiso 1 1 calc R U . . .
H2B2 H 0.8412 0.5086 0.6173 0.041 Uiso 1 1 calc R U . . .
C3B C 0.8537(7) 0.6323(12) 0.5320(4) 0.034(2) Uani 1 1 d . . . . .
H3B1 H 0.8187 0.7315 0.5129 0.041 Uiso 1 1 calc R U . . .
H3B2 H 0.9241 0.6689 0.5432 0.041 Uiso 1 1 calc R U . . .
C4B C 0.8620(7) 0.4936(12) 0.4828(5) 0.034(2) Uani 1 1 d . . . . .
H4B1 H 0.8680 0.3820 0.5043 0.041 Uiso 1 1 calc R U . . .
H4B2 H 0.9255 0.5114 0.4574 0.041 Uiso 1 1 calc R U . . .
C5B C 0.7691(7) 0.4888(12) 0.4383(4) 0.032(2) Uani 1 1 d . . . . .
H5B1 H 0.7609 0.6033 0.4194 0.038 Uiso 1 1 calc R U . . .
H5B2 H 0.7847 0.4083 0.4035 0.038 Uiso 1 1 calc R U . . .
C6B C 0.6697(7) 0.4386(11) 0.4679(4) 0.031(2) Uani 1 1 d . . . . .
H6B1 H 0.6748 0.3180 0.4812 0.038 Uiso 1 1 calc R U . . .
H6B2 H 0.6156 0.4453 0.4354 0.038 Uiso 1 1 calc R U . . .
C7B C 0.6346(7) 0.5453(11) 0.5253(4) 0.034(2) Uani 1 1 d . . . . .
H7B1 H 0.6452 0.6678 0.5161 0.041 Uiso 1 1 calc R U . . .
H7B2 H 0.5602 0.5267 0.5332 0.041 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
Bi Br2 2.7142(10) . ?
Bi Br1 2.7559(10) . ?
Bi Br3 2.8234(11) . ?
Bi Br4 2.8758(11) . ?
Bi Br5 2.9619(10) 2_656 ?
Bi Br5 3.0669(11) . ?
Br5 Bi 2.9619(10) 2_646 ?
N1A C2A 1.495(11) . ?
N1A C7A 1.503(11) . ?
N1A H1A1 0.9100 . ?
N1A H1A2 0.9100 . ?
C2A C3A 1.532(14) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A C4A 1.495(15) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A C5A 1.515(13) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A C6A 1.536(14) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A C7A 1.513(12) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
N1B C7B 1.487(11) . ?
N1B C2B 1.526(11) . ?
N1B H1B1 0.9100 . ?
N1B H1B2 0.9100 . ?
C2B C3B 1.513(12) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B C4B 1.509(13) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C4B C5B 1.538(12) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5B C6B 1.483(12) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B C7B 1.541(12) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?

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 Bi Br1 94.80(3) . . ?
Br2 Bi Br3 88.70(3) . . ?
Br1 Bi Br3 91.83(3) . . ?
Br2 Bi Br4 87.45(3) . . ?
Br1 Bi Br4 89.21(3) . . ?
Br3 Bi Br4 176.08(2) . . ?
Br2 Bi Br5 87.59(3) . 2_656 ?
Br1 Bi Br5 177.61(3) . 2_656 ?
Br3 Bi Br5 88.16(3) . 2_656 ?
Br4 Bi Br5 90.96(3) . 2_656 ?
Br2 Bi Br5 171.86(3) . . ?
Br1 Bi Br5 93.24(3) . . ?
Br3 Bi Br5 89.74(3) . . ?
Br4 Bi Br5 93.97(3) . . ?
Br5 Bi Br5 84.37(2) 2_656 . ?
Bi Br5 Bi 153.46(3) 2_646 . ?
C2A N1A C7A 117.3(7) . . ?
C2A N1A H1A1 108.0 . . ?
C7A N1A H1A1 108.0 . . ?
C2A N1A H1A2 108.0 . . ?
C7A N1A H1A2 108.0 . . ?
H1A1 N1A H1A2 107.2 . . ?
N1A C2A C3A 111.0(8) . . ?
N1A C2A H2A1 109.4 . . ?
C3A C2A H2A1 109.4 . . ?
N1A C2A H2A2 109.4 . . ?
C3A C2A H2A2 109.4 . . ?
H2A1 C2A H2A2 108.0 . . ?
C4A C3A C2A 116.6(8) . . ?
C4A C3A H3A1 108.1 . . ?
C2A C3A H3A1 108.1 . . ?
C4A C3A H3A2 108.1 . . ?
C2A C3A H3A2 108.1 . . ?
H3A1 C3A H3A2 107.3 . . ?
C3A C4A C5A 116.7(8) . . ?
C3A C4A H4A1 108.1 . . ?
C5A C4A H4A1 108.1 . . ?
C3A C4A H4A2 108.1 . . ?
C5A C4A H4A2 108.1 . . ?
H4A1 C4A H4A2 107.3 . . ?
C4A C5A C6A 113.1(8) . . ?
C4A C5A H5A1 109.0 . . ?
C6A C5A H5A1 109.0 . . ?
C4A C5A H5A2 109.0 . . ?
C6A C5A H5A2 109.0 . . ?
H5A1 C5A H5A2 107.8 . . ?
C7A C6A C5A 115.1(8) . . ?
C7A C6A H6A1 108.5 . . ?
C5A C6A H6A1 108.5 . . ?
C7A C6A H6A2 108.5 . . ?
C5A C6A H6A2 108.5 . . ?
H6A1 C6A H6A2 107.5 . . ?
N1A C7A C6A 115.7(7) . . ?
N1A C7A H7A1 108.4 . . ?
C6A C7A H7A1 108.4 . . ?
N1A C7A H7A2 108.4 . . ?
C6A C7A H7A2 108.4 . . ?
H7A1 C7A H7A2 107.4 . . ?
C7B N1B C2B 117.0(7) . . ?
C7B N1B H1B1 108.0 . . ?
C2B N1B H1B1 108.0 . . ?
C7B N1B H1B2 108.0 . . ?
C2B N1B H1B2 108.0 . . ?
H1B1 N1B H1B2 107.3 . . ?
C3B C2B N1B 115.0(7) . . ?
C3B C2B H2B1 108.5 . . ?
N1B C2B H2B1 108.5 . . ?
C3B C2B H2B2 108.5 . . ?
N1B C2B H2B2 108.5 . . ?
H2B1 C2B H2B2 107.5 . . ?
C4B C3B C2B 115.8(8) . . ?
C4B C3B H3B1 108.3 . . ?
C2B C3B H3B1 108.3 . . ?
C4B C3B H3B2 108.3 . . ?
C2B C3B H3B2 108.3 . . ?
H3B1 C3B H3B2 107.4 . . ?
C3B C4B C5B 112.9(8) . . ?
C3B C4B H4B1 109.0 . . ?
C5B C4B H4B1 109.0 . . ?
C3B C4B H4B2 109.0 . . ?
C5B C4B H4B2 109.0 . . ?
H4B1 C4B H4B2 107.8 . . ?
C6B C5B C4B 115.7(7) . . ?
C6B C5B H5B1 108.4 . . ?
C4B C5B H5B1 108.4 . . ?
C6B C5B H5B2 108.4 . . ?
C4B C5B H5B2 108.4 . . ?
H5B1 C5B H5B2 107.4 . . ?
C5B C6B C7B 116.0(8) . . ?
C5B C6B H6B1 108.3 . . ?
C7B C6B H6B1 108.3 . . ?
C5B C6B H6B2 108.3 . . ?
C7B C6B H6B2 108.3 . . ?
H6B1 C6B H6B2 107.4 . . ?
N1B C7B C6B 111.0(7) . . ?
N1B C7B H7B1 109.4 . . ?
C6B C7B H7B1 109.4 . . ?
N1B C7B H7B2 109.4 . . ?
C6B C7B H7B2 109.4 . . ?
H7B1 C7B H7B2 108.0 . . ?

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
C7A N1A C2A C3A -87.3(10) . . . . ?
N1A C2A C3A C4A 71.3(11) . . . . ?
C2A C3A C4A C5A -53.2(12) . . . . ?
C3A C4A C5A C6A 68.3(11) . . . . ?
C4A C5A C6A C7A -86.0(11) . . . . ?
C2A N1A C7A C6A 37.9(12) . . . . ?
C5A C6A C7A N1A 41.9(12) . . . . ?
C7B N1B C2B C3B -30.9(11) . . . . ?
N1B C2B C3B C4B -48.3(11) . . . . ?
C2B C3B C4B C5B 87.3(10) . . . . ?
C3B C4B C5B C6B -67.1(11) . . . . ?
C4B C5B C6B C7B 55.6(11) . . . . ?
C2B N1B C7B C6B 85.2(9) . . . . ?
C5B C6B C7B N1B -76.5(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
N1A H1A1 Br1 0.91 2.69 3.434(8) 139.5 .
N1A H1A1 Br2 0.91 3.02 3.553(7) 119.6 1_545
N1A H1A2 Br4 0.91 2.54 3.440(8) 171.4 1_545
C7A H7A2 Br3 0.99 3.01 3.707(9) 128.5 2_646
N1B H1B1 Br3 0.91 2.55 3.456(8) 177.7 1_545
N1B H1B2 Br1 0.91 2.68 3.426(8) 139.4 .
N1B H1B2 Br5 0.91 2.97 3.470(7) 116.2 2_646
C2B H2B2 Br4 0.99 2.92 3.688(8) 134.7 2_646
C6B H6B2 Br1 0.99 3.03 3.889(9) 145.9 3_666
C6B H6B2 Br2 0.99 3.02 3.755(8) 132.0 3_676

_refine_diff_density_max         1.584
_refine_diff_density_min         -1.832
_refine_diff_density_rms         0.266

####################################################################### 
# 
# 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_HBC300K
_database_code_depnum_ccdc_archive 'CCDC 1859096'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT974_HBC300K             
;
PROBLEM: Check Calcd Negative Resid. Density on        Bi      -2.08 eA-3
RESPONSE: Bismuth is the heaviest element (83 electrons), the precise analytical absorption correction was applied, it happens that the residual density is -2.08 eV-3
;
# Added during the CSD deposition process: Monday 30 July 2018 09:49 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H14 N), Bi Cl6, H3 O'
_chemical_formula_sum            'C12 H31 Bi Cl6 N2 O'
_chemical_formula_weight         641.07

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'
Bi Bi -4.1077 10.2566 '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'
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           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   18.449(3)
_cell_length_b                   7.942(5)
_cell_length_c                   7.949(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.22(4)
_cell_angle_gamma                90
_cell_volume                     1164(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    3014
_cell_measurement_theta_min      3.7450
_cell_measurement_theta_max      25.7430

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    8.261
_shelx_estimated_absorpt_T_min   0.437
_shelx_estimated_absorpt_T_max   0.683
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_T_max  0.739
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            4641
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.792
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1266
_reflns_number_gt                1249
_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       
;
CrysAlisCCD, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 4.0'
_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)+(0.0645P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1266
_refine_ls_number_parameters     87
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Bi Bi 0.5000 0.5000 0.5000 0.0515(2) Uani 1 4 d S T P . .
Cl1 Cl 0.55660(14) 0.2541(4) 0.3081(3) 0.0871(7) Uani 1 1 d . . . . .
Cl2 Cl 0.37996(16) 0.5000 0.2973(4) 0.0751(8) Uani 1 2 d S T P . .
O1H O 0.5000 0.5000 0.0000 0.153(9) Uani 1 4 d S T P . .
H1H H 0.4827 0.5888 -0.0419 0.229 Uiso 0.25 1 d R U P . .
H2H H 0.5028 0.5000 0.1056 0.229 Uiso 1 2 d R U P . .
N1A N 0.6141(11) 1.020(8) 0.638(3) 0.142(10) Uani 0.5 1 d D U P A -1
H1A1 H 0.6053 1.1297 0.6258 0.171 Uiso 0.5 1 calc R U P A -1
H1A2 H 0.5828 0.9652 0.5716 0.171 Uiso 0.5 1 calc R U P A -1
C2A C 0.6886(15) 0.985(15) 0.579(3) 0.134(10) Uani 0.5 1 d . U P A -1
H2A1 H 0.6834 0.9050 0.4876 0.161 Uiso 0.5 1 calc R U P A -1
H2A2 H 0.7056 1.0893 0.5292 0.161 Uiso 0.5 1 calc R U P A -1
C3A C 0.7458(13) 0.926(4) 0.683(4) 0.119(7) Uani 0.5 1 d . U P A -1
H3A1 H 0.7402 0.8045 0.6838 0.143 Uiso 0.5 1 calc R U P A -1
H3A2 H 0.7894 0.9481 0.6207 0.143 Uiso 0.5 1 calc R U P A -1
C4A C 0.7625(11) 0.967(7) 0.841(3) 0.123(10) Uani 0.5 1 d . U P A -1
H4A1 H 0.7848 1.0776 0.8373 0.147 Uiso 0.5 1 calc R U P A -1
H4A2 H 0.8001 0.8895 0.8784 0.147 Uiso 0.5 1 calc R U P A -1
C5A C 0.7116(14) 0.973(8) 0.972(3) 0.120(11) Uani 0.5 1 d . U P A -1
H5A1 H 0.7349 1.0298 1.0674 0.144 Uiso 0.5 1 calc R U P A -1
H5A2 H 0.7023 0.8585 1.0071 0.144 Uiso 0.5 1 calc R U P A -1
C6A C 0.6419(14) 1.054(3) 0.943(3) 0.109(8) Uani 0.5 1 d . U P A -1
H6A1 H 0.6153 1.0534 1.0471 0.131 Uiso 0.5 1 calc R U P A -1
H6A2 H 0.6497 1.1702 0.9114 0.131 Uiso 0.5 1 calc R U P A -1
C7A C 0.5993(12) 0.974(9) 0.815(4) 0.141(11) Uani 0.5 1 d D U P A -1
H7A1 H 0.5487 0.9977 0.8362 0.169 Uiso 0.5 1 calc R U P A -1
H7A2 H 0.6058 0.8529 0.8268 0.169 Uiso 0.5 1 calc R U P A -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
Bi Cl1 2.702(2) 5_666 ?
Bi Cl1 2.702(2) 2_656 ?
Bi Cl1 2.702(2) . ?
Bi Cl1 2.702(2) 6_565 ?
Bi Cl2 2.711(3) . ?
Bi Cl2 2.711(3) 5_666 ?
O1H H1H 0.8403 . ?
O1H H2H 0.8400 . ?
N1A C7A 1.486(19) . ?
N1A C2A 1.49(4) . ?
N1A H1A1 0.8900 . ?
N1A H1A2 0.8900 . ?
C2A C3A 1.41(5) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A C4A 1.33(3) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A C5A 1.42(3) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A C6A 1.45(4) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A C7A 1.42(5) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C7A H7A1 0.9700 . ?
C7A H7A2 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
Cl1 Bi Cl1 92.57(14) 5_666 2_656 ?
Cl1 Bi Cl1 180.0 5_666 . ?
Cl1 Bi Cl1 87.43(14) 2_656 . ?
Cl1 Bi Cl1 87.43(14) 5_666 6_565 ?
Cl1 Bi Cl1 180.0 2_656 6_565 ?
Cl1 Bi Cl1 92.57(14) . 6_565 ?
Cl1 Bi Cl2 90.86(7) 5_666 . ?
Cl1 Bi Cl2 90.86(8) 2_656 . ?
Cl1 Bi Cl2 89.14(7) . . ?
Cl1 Bi Cl2 89.14(7) 6_565 . ?
Cl1 Bi Cl2 89.14(7) 5_666 5_666 ?
Cl1 Bi Cl2 89.14(7) 2_656 5_666 ?
Cl1 Bi Cl2 90.86(7) . 5_666 ?
Cl1 Bi Cl2 90.86(7) 6_565 5_666 ?
Cl2 Bi Cl2 180.0 . 5_666 ?
H1H O1H H2H 114.3 . . ?
C7A N1A C2A 116(3) . . ?
C7A N1A H1A1 108.2 . . ?
C2A N1A H1A1 108.2 . . ?
C7A N1A H1A2 108.2 . . ?
C2A N1A H1A2 108.2 . . ?
H1A1 N1A H1A2 107.3 . . ?
C3A C2A N1A 124(3) . . ?
C3A C2A H2A1 106.3 . . ?
N1A C2A H2A1 106.3 . . ?
C3A C2A H2A2 106.3 . . ?
N1A C2A H2A2 106.3 . . ?
H2A1 C2A H2A2 106.4 . . ?
C4A C3A C2A 129(4) . . ?
C4A C3A H3A1 105.0 . . ?
C2A C3A H3A1 105.0 . . ?
C4A C3A H3A2 105.0 . . ?
C2A C3A H3A2 105.0 . . ?
H3A1 C3A H3A2 105.9 . . ?
C3A C4A C5A 124(2) . . ?
C3A C4A H4A1 106.3 . . ?
C5A C4A H4A1 106.3 . . ?
C3A C4A H4A2 106.3 . . ?
C5A C4A H4A2 106.3 . . ?
H4A1 C4A H4A2 106.4 . . ?
C4A C5A C6A 120(2) . . ?
C4A C5A H5A1 107.4 . . ?
C6A C5A H5A1 107.4 . . ?
C4A C5A H5A2 107.4 . . ?
C6A C5A H5A2 107.4 . . ?
H5A1 C5A H5A2 106.9 . . ?
C7A C6A C5A 113(3) . . ?
C7A C6A H6A1 108.9 . . ?
C5A C6A H6A1 108.9 . . ?
C7A C6A H6A2 108.9 . . ?
C5A C6A H6A2 108.9 . . ?
H6A1 C6A H6A2 107.8 . . ?
C6A C7A N1A 117(4) . . ?
C6A C7A H7A1 108.0 . . ?
N1A C7A H7A1 108.0 . . ?
C6A C7A H7A2 108.0 . . ?
N1A C7A H7A2 108.0 . . ?
H7A1 C7A H7A2 107.3 . . ?

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
O1H H2H Cl1 0.84 2.71 3.285(3) 127.5 .
O1H H1H Cl1 0.84 2.55 3.285(3) 147.1 5_665
O1H H2H Cl1 0.84 2.71 3.285(3) 127.5 6_565
O1H H2H Cl2 0.84 2.76 3.273(3) 121.3 .
N1A H1A2 Cl1 0.89 2.76 3.56(4) 149.6 6_565
N1A H1A1 Cl1 0.89 2.84 3.37(4) 119.5 1_565
C7A H7A1 Cl1 0.97 3.02 3.75(5) 132.9 2_666

_refine_diff_density_max         1.323
_refine_diff_density_min         -1.996
_refine_diff_density_rms         0.191

