# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1485661'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-08-16 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         'C5 H16 N2, Cl5 Sb'
_chemical_formula_sum            'C5 H16 Cl5 N2 Sb'
_chemical_formula_weight         403.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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                   7.662(5)
_cell_length_b                   13.433(9)
_cell_length_c                   13.883(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1428.8(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12903
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    2.832
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.397
_exptl_absorpt_correction_T_max  0.479
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10417
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3252
_reflns_number_gt                2966
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0130P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0143(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1063 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3252
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0516
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
C1 C 0.9342(9) 0.9379(4) 1.0774(4) 0.0545(19) Uani 1 1 d . . . . .
H1A H 0.8098 0.9488 1.0698 0.065 Uiso 1 1 calc R U . . .
H1B H 0.9503 0.8908 1.1296 0.065 Uiso 1 1 calc R U . . .
C5 C 0.9539(7) 0.8091(4) 0.7793(4) 0.0439(15) Uani 1 1 d . . . . .
H5A H 0.8289 0.8161 0.7704 0.053 Uiso 1 1 calc R U . . .
H5B H 1.0033 0.8752 0.7861 0.053 Uiso 1 1 calc R U . . .
C3 C 0.9144(8) 0.7979(4) 0.9606(4) 0.0459(16) Uani 1 1 d . . . . .
H3A H 0.7910 0.8109 0.9511 0.055 Uiso 1 1 calc R U . . .
H3B H 0.9257 0.7513 1.0136 0.055 Uiso 1 1 calc R U . . .
C4 C 0.9886(9) 0.7503(4) 0.8694(3) 0.0459(15) Uani 1 1 d . . . . .
H4A H 1.1137 0.7425 0.8771 0.055 Uiso 1 1 calc R U . . .
H4B H 0.9386 0.6844 0.8620 0.055 Uiso 1 1 calc R U . . .
N2 N 1.0299(6) 0.7603(3) 0.6943(3) 0.0496(13) Uani 1 1 d . . . . .
H2C H 1.1457 0.7600 0.6994 0.074 Uiso 1 1 calc R U . . .
H2D H 0.9988 0.7933 0.6415 0.074 Uiso 1 1 calc R U . . .
H2E H 0.9912 0.6979 0.6907 0.074 Uiso 1 1 calc R U . . .
C2 C 1.0047(8) 0.8937(4) 0.9868(4) 0.0426(14) Uani 1 1 d . . . . .
H2A H 1.1286 0.8812 0.9947 0.051 Uiso 1 1 calc R U . . .
H2B H 0.9906 0.9411 0.9346 0.051 Uiso 1 1 calc R U . . .
Cl5 Cl 0.8034(2) 0.97681(12) 0.32187(12) 0.0540(5) Uani 1 1 d . . . . .
Cl4 Cl 0.9486(2) 0.73099(10) 0.25999(9) 0.0412(4) Uani 1 1 d . . . . .
Cl2 Cl 1.0644(2) 0.98088(12) 0.54731(12) 0.0582(5) Uani 1 1 d . . . . .
Cl3 Cl 1.2595(2) 0.94070(11) 0.30201(12) 0.0501(4) Uani 1 1 d . . . . .
Sb1 Sb 1.01441(4) 0.86648(2) 0.39745(2) 0.02760(11) Uani 1 1 d . . . . .
Cl1 Cl 0.7383(2) 0.78750(11) 0.51026(11) 0.0532(4) Uani 1 1 d . . . . .
N1 N 1.0180(6) 1.0326(3) 1.1035(3) 0.0537(13) Uani 1 1 d . . . . .
H1C H 1.1326 1.0279 1.0943 0.080 Uiso 1 1 calc R U . . .
H1D H 0.9968 1.0461 1.1652 0.080 Uiso 1 1 calc R U . . .
H1E H 0.9752 1.0813 1.0669 0.080 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
C1 N1 1.471(6) . ?
C1 C2 1.491(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 N2 1.470(6) . ?
C5 C4 1.503(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C3 C2 1.507(7) . ?
C3 C4 1.527(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?
N2 H2E 0.8900 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
Cl5 Sb1 2.4314(18) . ?
Cl4 Sb1 2.6849(18) . ?
Cl2 Sb1 2.615(2) . ?
Cl3 Sb1 2.5049(18) . ?
Sb1 Cl1 2.838(2) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 113.2(5) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
N2 C5 C4 111.3(4) . . ?
N2 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C2 C3 C4 112.8(5) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 113.8(5) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C5 N2 H2C 109.5 . . ?
C5 N2 H2D 109.5 . . ?
H2C N2 H2D 109.5 . . ?
C5 N2 H2E 109.5 . . ?
H2C N2 H2E 109.5 . . ?
H2D N2 H2E 109.5 . . ?
C1 C2 C3 112.2(5) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
Cl5 Sb1 Cl3 91.58(7) . . ?
Cl5 Sb1 Cl2 94.74(7) . . ?
Cl3 Sb1 Cl2 94.43(7) . . ?
Cl5 Sb1 Cl4 88.95(7) . . ?
Cl3 Sb1 Cl4 91.98(6) . . ?
Cl2 Sb1 Cl4 172.51(5) . . ?
Cl5 Sb1 Cl1 88.30(7) . . ?
Cl3 Sb1 Cl1 178.08(5) . . ?
Cl2 Sb1 Cl1 83.67(6) . . ?
Cl4 Sb1 Cl1 89.93(6) . . ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
H1C N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?

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
N2 C5 C4 C3 179.4(5) . . . . ?
C2 C3 C4 C5 -67.5(7) . . . . ?
N1 C1 C2 C3 -178.9(5) . . . . ?
C4 C3 C2 C1 -178.5(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
N2 H2C Cl4 0.89 2.39 3.272(5) 170.3 4_566
N2 H2D Cl2 0.89 2.88 3.608(5) 139.8 .
N2 H2D Cl1 0.89 2.70 3.414(5) 137.6 .
N2 H2E Cl3 0.89 2.57 3.403(5) 155.3 4_466
N1 H1C Cl2 0.89 2.41 3.299(5) 172.5 2_775
N1 H1D Cl5 0.89 2.79 3.529(5) 141.2 1_556
N1 H1D Cl4 0.89 2.72 3.279(4) 121.6 3_756
N1 H1E Cl1 0.89 2.53 3.372(5) 157.9 2_675

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.106



####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1485662'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;
_vrf_PLAT_242_2                  
;
PROBLEM:  Low    'MainMol' Ueq as Compared to Neighbors of        Sb1 Check    
RESPONSE: The structure was determined at 393 K. The Sb1 atom is the 
center atom of SbCl6 octahedra, in which the Cl atoms show large 
anisotropic displacement parameters.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H16 N2, Cl5 Sb'
_chemical_formula_sum            'C5 H16 Cl5 N2 Sb'
_chemical_formula_weight         403.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   13.514(10)
_cell_length_b                   7.818(12)
_cell_length_c                   13.80(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1458(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    393(2)
_cell_measurement_reflns_used    12903
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    2.776
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_T_max  0.486
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      393(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10124
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.952
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1792
_reflns_number_gt                1429
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0569P)²+3.3323P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0127(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1792
_refine_ls_number_parameters     83
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.045
_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
N2 N 0.0154(10) 0.7500 0.8026(7) 0.216(7) Uani 1 2 d DS T P . .
H2C H 0.0701 0.7500 0.8397 0.325 Uiso 1 2 d R U P . .
H2D H -0.0208 0.8440 0.8155 0.325 Uiso 0.5 1 d R U P . .
H2E H -0.0208 0.6560 0.8155 0.325 Uiso 0.5 1 d R U P . .
Cl2 Cl 0.7373(2) 0.7500 0.5519(2) 0.1469(12) Uani 1 2 d S T P . .
Cl3 Cl 0.70336(15) 0.9787(3) 0.30814(14) 0.1280(7) Uani 1 1 d . . . . .
Cl4 Cl 0.47902(18) 0.7500 0.26402(18) 0.1105(9) Uani 1 2 d S T P . .
Sb1 Sb 0.61583(4) 0.7500 0.39779(4) 0.06937(15) Uani 1 2 d S T P . .
C1 C 0.2071(12) 0.7500 0.4461(12) 0.205(6) Uani 1 2 d S TU P . .
H1A H 0.1790 0.6799 0.3960 0.246 Uiso 0.5 1 d R U P . .
H1B H 0.2359 0.6711 0.4913 0.246 Uiso 0.5 1 d R U P . .
C2 C 0.1345(10) 0.798(4) 0.4919(15) 0.201(8) Uani 0.5 1 d . U P . .
H2A H 0.1048 0.8709 0.4441 0.241 Uiso 0.5 1 d R U P . .
H2B H 0.1639 0.8751 0.5377 0.241 Uiso 0.5 1 d R U P . .
C3 C 0.0590(11) 0.7500 0.5419(11) 0.219(7) Uani 1 2 d S TU P . .
H3A H 0.0547 0.6316 0.5240 0.262 Uiso 0.5 1 d R U P . .
H3B H 0.0050 0.8047 0.5090 0.262 Uiso 0.5 1 d R U P . .
C4 C 0.0217(15) 0.7500 0.6304(8) 0.236(10) Uani 1 2 d DS T P . .
H4A H -0.0220 0.6533 0.6286 0.283 Uiso 0.5 1 d R U P . .
H4B H -0.0220 0.8467 0.6286 0.283 Uiso 0.5 1 d R U P . .
C5 C 0.0519(13) 0.7500 0.7144(7) 0.224(9) Uani 1 2 d DS T P . .
H5A H 0.0957 0.6534 0.7155 0.269 Uiso 0.5 1 d R U P . .
H5B H 0.0957 0.8466 0.7155 0.269 Uiso 0.5 1 d R U P . .
N1 N 0.2826(8) 0.8193(19) 0.4029(9) 0.152(7) Uani 0.5 1 d . U P . .
H1C H 0.3211 0.7359 0.3783 0.228 Uiso 0.5 1 d R U P . .
H1D H 0.2625 0.8887 0.3547 0.228 Uiso 0.5 1 d R U P . .
H1E H 0.3173 0.8801 0.4465 0.228 Uiso 0.5 1 d R U P . .
Cl1 Cl 0.5000 1.0000 0.5000 0.1922(16) Uani 1 2 d S . P . .


_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
N2 C5 1.313(12) . ?
N2 H2C 0.9000 . ?
N2 H2D 0.9000 . ?
N2 H2E 0.9000 . ?
Cl2 Sb1 2.686(4) . ?
Cl3 Sb1 2.475(3) . ?
Cl4 Sb1 2.613(4) . ?
Sb1 Cl3 2.475(3) 7_575 ?
Sb1 Cl1 2.874(3) 3_646 ?
Sb1 Cl1 2.874(3) . ?
C1 C2 1.225(19) 7_575 ?
C1 C2 1.225(19) . ?
C1 N1 1.300(16) . ?
C1 N1 1.300(16) 7_575 ?
C1 H1A 0.9601 . ?
C1 H1B 0.9600 . ?
C2 C2 0.75(6) 7_575 ?
C2 C3 1.288(19) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C3 C2 1.288(19) 7_575 ?
C3 C4 1.321(19) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9601 . ?
C4 C5 1.228(13) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C5 H5A 0.9599 . ?
C5 H5B 0.9599 . ?
N1 N1 1.08(3) 7_575 ?
N1 H1C 0.9001 . ?
N1 H1D 0.9000 . ?
N1 H1E 0.9000 . ?
Cl1 Sb1 2.874(3) 5_676 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N2 H2C 102.6 . . ?
C5 N2 H2D 112.8 . . ?
H2C N2 H2D 109.5 . . ?
C5 N2 H2E 112.8 . . ?
H2C N2 H2E 109.5 . . ?
H2D N2 H2E 109.5 . . ?
Cl3 Sb1 Cl3 92.50(15) 7_575 . ?
Cl3 Sb1 Cl4 89.14(10) 7_575 . ?
Cl3 Sb1 Cl4 89.14(10) . . ?
Cl3 Sb1 Cl2 95.96(11) 7_575 . ?
Cl3 Sb1 Cl2 95.95(11) . . ?
Cl4 Sb1 Cl2 172.61(10) . . ?
Cl3 Sb1 Cl1 90.82(11) 7_575 3_646 ?
Cl3 Sb1 Cl1 175.44(5) . 3_646 ?
Cl4 Sb1 Cl1 87.78(9) . 3_646 ?
Cl2 Sb1 Cl1 86.80(10) . 3_646 ?
Cl3 Sb1 Cl1 175.44(5) 7_575 . ?
Cl3 Sb1 Cl1 90.82(11) . . ?
Cl4 Sb1 Cl1 87.78(9) . . ?
Cl2 Sb1 Cl1 86.80(10) . . ?
Cl1 Sb1 Cl1 85.70(10) 3_646 . ?
C2 C1 C2 36(3) 7_575 . ?
C2 C1 N1 172.8(16) 7_575 . ?
C2 C1 N1 137.5(15) . . ?
C2 C1 N1 137.5(15) 7_575 7_575 ?
C2 C1 N1 172.8(16) . 7_575 ?
N1 C1 N1 49.2(14) . 7_575 ?
C2 C1 H1A 83.1 7_575 . ?
C2 C1 H1A 103.3 . . ?
N1 C1 H1A 102.6 . . ?
N1 C1 H1A 75.1 7_575 . ?
C2 C1 H1B 78.0 7_575 . ?
C2 C1 H1B 100.7 . . ?
N1 C1 H1B 104.3 . . ?
N1 C1 H1B 73.2 7_575 . ?
H1A C1 H1B 105.1 . . ?
C2 C2 C1 72.2(13) 7_575 . ?
C2 C2 C3 73.1(12) 7_575 . ?
C1 C2 C3 145(3) . . ?
C2 C2 H2A 126.4 7_575 . ?
C1 C2 H2A 99.3 . . ?
C3 C2 H2A 102.2 . . ?
C2 C2 H2B 128.9 7_575 . ?
C1 C2 H2B 101.6 . . ?
C3 C2 H2B 99.1 . . ?
H2A C2 H2B 104.6 . . ?
C2 C3 C2 34(2) . 7_575 ?
C2 C3 C4 142.9(17) . . ?
C2 C3 C4 142.9(17) 7_575 . ?
C2 C3 H3A 101.0 . . ?
C2 C3 H3A 68.2 7_575 . ?
C4 C3 H3A 102.4 . . ?
C2 C3 H3B 102.6 . . ?
C2 C3 H3B 118.6 7_575 . ?
C4 C3 H3B 98.5 . . ?
H3A C3 H3B 105.2 . . ?
C5 C4 C3 138(2) . . ?
C5 C4 H4A 103.2 . . ?
C3 C4 H4A 102.2 . . ?
C5 C4 H4B 103.2 . . ?
C3 C4 H4B 102.2 . . ?
H4A C4 H4B 103.9 . . ?
C4 C5 N2 138.6(19) . . ?
C4 C5 H5A 102.7 . . ?
N2 C5 H5A 102.6 . . ?
C4 C5 H5B 102.7 . . ?
N2 C5 H5B 102.6 . . ?
H5A C5 H5B 103.8 . . ?
N1 N1 C1 65.4(7) 7_575 . ?
N1 N1 H1C 43.6 7_575 . ?
C1 N1 H1C 108.9 . . ?
N1 N1 H1D 127.1 7_575 . ?
C1 N1 H1D 110.7 . . ?
H1C N1 H1D 109.5 . . ?
N1 N1 H1E 121.9 7_575 . ?
C1 N1 H1E 108.8 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
Sb1 Cl1 Sb1 180.0 5_676 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C2 -177(3) . . . 7_575 ?
C2 C1 C2 C3 2(4) 7_575 . . . ?
N1 C1 C2 C3 -174(3) . . . . ?
C1 C2 C3 C2 -2(4) . . . 7_575 ?
C2 C2 C3 C4 114(2) 7_575 . . . ?
C1 C2 C3 C4 112(3) . . . . ?
C2 C3 C4 C5 -29(2) . . . . ?
C2 C3 C4 C5 29(2) 7_575 . . . ?
C3 C4 C5 N2 180.000(4) . . . . ?
C2 C1 N1 N1 176(3) . . . 7_575 ?

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
N2 H2C Cl2 0.90 2.71 3.609(14) 178.8 6_557
N2 H2D Cl3 0.90 2.83 3.639(12) 149.9 2_575
N2 H2D Cl1 0.90 2.84 3.359(8) 118.4 2_575
N2 H2E Cl3 0.90 2.83 3.639(12) 149.9 8_656
N2 H2E Cl1 0.90 2.84 3.359(8) 118.4 4_466
N1 H1C Cl4 0.90 2.66 3.318(12) 131.1 .
N1 H1D Cl3 0.90 2.49 3.343(13) 159.2 6_556
N1 H1E Cl2 0.90 2.98 3.435(16) 112.8 5_676
N1 H1E Cl1 0.90 2.74 3.525(13) 146.2 .

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.093



