# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_290K
_database_code_depnum_ccdc_archive 'CCDC 1588041'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;
_audit_creation_date             2017-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl5 Sb, 2(C6 H14 N)'
_chemical_formula_sum            'C12 H28 Cl5 N2 Sb'
_chemical_formula_weight         499.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Sb Br'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.5861(3)
_cell_length_b                   13.2521(5)
_cell_length_c                   20.2623(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2037.00(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4169
_cell_measurement_temperature    290.00(10)
_cell_measurement_theta_max      27.3100
_cell_measurement_theta_min      4.0010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.004
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83986
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8223
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.400
_diffrn_reflns_theta_min         3.386
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   93.00   1.0000   23.4100
omega____ theta____ kappa____ phi______ frames
    -       11.3879   19.0000 -150.0000 128

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00  -14.00   1.0000   23.4100
omega____ theta____ kappa____ phi______ frames
    -      -12.6379   38.0000  120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0099438000
_diffrn_orient_matrix_UB_12      -0.0248445000
_diffrn_orient_matrix_UB_13      0.0307908000
_diffrn_orient_matrix_UB_21      -0.0485315000
_diffrn_orient_matrix_UB_22      0.0389874000
_diffrn_orient_matrix_UB_23      0.0156515000
_diffrn_orient_matrix_UB_31      -0.0793020000
_diffrn_orient_matrix_UB_32      -0.0269506000
_diffrn_orient_matrix_UB_33      -0.0057231000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.734
_reflns_number_gt                3997
_reflns_number_total             4546
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
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_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 1397 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.025(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0267P)²+0.4370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0697
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N1(H1A,H1B), C7(H7A,H7B), C2(H1,H2), C3(H3A,H3B), C6(H6A,H6B),
 C1(H3,H4), C8(H8A,H8B), C4(H4A,H4B), C5(H5A,H5B), C9(H9A,H9B), C10(H10A,H10B),
 C11(H11A,H11B), C12(H12A,H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.55551(5) 0.39308(3) 0.55679(2) 0.04134(11) Uani 1 1 d . . . . .
Cl2 Cl 0.5629(3) 0.27308(11) 0.65384(7) 0.0612(4) Uani 1 1 d . . . . .
Cl5 Cl 0.5183(2) 0.53953(12) 0.46016(8) 0.0604(4) Uani 1 1 d . . . . .
Cl4 Cl 0.3748(2) 0.50278(12) 0.62099(9) 0.0624(4) Uani 1 1 d . . . . .
Cl1 Cl 0.2598(2) 0.30159(12) 0.51611(9) 0.0631(4) Uani 1 1 d . . . . .
Cl3 Cl 0.8371(2) 0.47788(14) 0.60290(9) 0.0693(5) Uani 1 1 d . . . . .
N2 N 0.0931(7) 0.5388(4) 0.4798(3) 0.0638(15) Uani 1 1 d . . . . .
H2A H 0.2114 0.5337 0.4732 0.077 Uiso 1 1 calc R . . . .
H2B H 0.0682 0.5069 0.5184 0.077 Uiso 1 1 calc R . . . .
N1 N 1.0470(12) 0.2776(4) 0.6568(3) 0.098(2) Uani 1 1 d . . . . .
H1A H 0.9334 0.2975 0.6506 0.118 Uiso 1 1 calc R . . . .
H1B H 1.1114 0.3053 0.6235 0.118 Uiso 1 1 calc R . . . .
C7 C 0.0030(9) 0.4835(5) 0.4258(3) 0.0659(19) Uani 1 1 d . . . . .
H7A H -0.1260 0.4917 0.4310 0.079 Uiso 1 1 calc R . . . .
H7B H 0.0303 0.4107 0.4299 0.079 Uiso 1 1 calc R . . . .
C2 C 1.0627(14) 0.1065(5) 0.7070(5) 0.107(3) Uani 1 1 d . . . . .
H1 H 1.1823 0.1135 0.7260 0.128 Uiso 1 1 calc R . . . .
H2 H 1.0499 0.0356 0.6924 0.128 Uiso 1 1 calc R . . . .
C3 C 0.9336(15) 0.1245(6) 0.7604(4) 0.110(3) Uani 1 1 d . . . . .
H3A H 0.9232 0.0623 0.7872 0.132 Uiso 1 1 calc R . . . .
H3B H 0.8170 0.1377 0.7403 0.132 Uiso 1 1 calc R . . . .
C6 C 1.1083(12) 0.3235(5) 0.7188(4) 0.089(3) Uani 1 1 d . . . . .
H6A H 1.2239 0.2938 0.7305 0.106 Uiso 1 1 calc R . . . .
H6B H 1.1263 0.3967 0.7115 0.106 Uiso 1 1 calc R . . . .
C1 C 1.0523(16) 0.1714(6) 0.6484(4) 0.096(3) Uani 1 1 d . . . . .
H3 H 1.1550 0.1555 0.6201 0.115 Uiso 1 1 calc R . . . .
H4 H 0.9455 0.1515 0.6235 0.115 Uiso 1 1 calc R . . . .
C8 C 0.0545(14) 0.5183(7) 0.3588(4) 0.098(3) Uani 1 1 d . . . . .
H8A H 0.1841 0.5267 0.3582 0.117 Uiso 1 1 calc R . . . .
H8B H 0.0256 0.4638 0.3271 0.117 Uiso 1 1 calc R . . . .
C4 C 0.9777(15) 0.2097(7) 0.8051(4) 0.101(3) Uani 1 1 d . . . . .
H4A H 0.8877 0.2123 0.8404 0.121 Uiso 1 1 calc R . . . .
H4B H 1.0924 0.1950 0.8263 0.121 Uiso 1 1 calc R . . . .
C5 C 0.9885(11) 0.3102(6) 0.7743(4) 0.081(2) Uani 1 1 d . . . . .
H5A H 0.8687 0.3289 0.7593 0.097 Uiso 1 1 calc R . . . .
H5B H 1.0226 0.3591 0.8090 0.097 Uiso 1 1 calc R . . . .
C9 C -0.0231(16) 0.6099(8) 0.3348(5) 0.124(4) Uani 1 1 d . . . . .
H9A H -0.1516 0.5983 0.3309 0.149 Uiso 1 1 calc R . . . .
H9B H 0.0222 0.6212 0.2895 0.149 Uiso 1 1 calc R . . . .
C10 C 0.0011(17) 0.7026(8) 0.3709(6) 0.133(4) Uani 1 1 d . . . . .
H10A H 0.0833 0.7439 0.3443 0.159 Uiso 1 1 calc R . . . .
H10B H -0.1140 0.7378 0.3695 0.159 Uiso 1 1 calc R . . . .
C11 C 0.057(3) 0.7102(7) 0.4332(6) 0.210(9) Uani 1 1 d . . . . .
H11A H 0.0035 0.7741 0.4488 0.253 Uiso 1 1 calc R . . . .
H11B H 0.1844 0.7248 0.4286 0.253 Uiso 1 1 calc R . . . .
C12 C 0.0489(15) 0.6480(6) 0.4878(4) 0.095(3) Uani 1 1 d . . . . .
H12A H -0.0722 0.6522 0.5058 0.114 Uiso 1 1 calc R . . . .
H12B H 0.1290 0.6762 0.5217 0.114 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl2 2.5298(15) . ?
Sb1 Cl5 2.7712(16) . ?
Sb1 Cl4 2.3845(15) . ?
Sb1 Cl1 3.3523(16) 3_556 ?
Sb1 Cl1 2.6800(16) . ?
Sb1 Cl3 2.5884(16) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C7 1.483(8) . ?
N2 C12 1.495(8) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C6 1.472(10) . ?
N1 C1 1.419(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.486(10) . ?
C2 H1 0.9900 . ?
C2 H2 0.9900 . ?
C2 C3 1.479(12) . ?
C2 C1 1.468(11) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.484(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.456(10) . ?
C1 H3 0.9900 . ?
C1 H4 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.435(11) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.473(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.442(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.335(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.382(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 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
Cl2 Sb1 Cl5 172.64(5) . . ?
Cl2 Sb1 Cl1 88.47(6) . . ?
Cl2 Sb1 Cl1 81.28(5) . 3_556 ?
Cl2 Sb1 Cl3 88.51(6) . . ?
Cl5 Sb1 Cl1 105.94(5) . 3_556 ?
Cl4 Sb1 Cl2 88.39(6) . . ?
Cl4 Sb1 Cl5 84.26(5) . . ?
Cl4 Sb1 Cl1 167.25(5) . 3_556 ?
Cl4 Sb1 Cl1 87.84(6) . . ?
Cl4 Sb1 Cl3 90.74(6) . . ?
Cl1 Sb1 Cl5 90.82(5) . . ?
Cl1 Sb1 Cl1 84.450(19) . 3_556 ?
Cl3 Sb1 Cl5 92.00(5) . . ?
Cl3 Sb1 Cl1 96.41(6) . 3_556 ?
Cl3 Sb1 Cl1 176.70(6) . . ?
H2A N2 H2B 107.3 . . ?
C7 N2 H2A 108.0 . . ?
C7 N2 H2B 108.0 . . ?
C7 N2 C12 117.1(6) . . ?
C12 N2 H2A 108.0 . . ?
C12 N2 H2B 108.0 . . ?
H1A N1 H1B 106.9 . . ?
C6 N1 H1A 107.3 . . ?
C6 N1 H1B 107.3 . . ?
C1 N1 H1A 107.3 . . ?
C1 N1 H1B 107.3 . . ?
C1 N1 C6 120.2(6) . . ?
N2 C7 H7A 108.9 . . ?
N2 C7 H7B 108.9 . . ?
N2 C7 C8 113.5(6) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H1 C2 H2 107.2 . . ?
C3 C2 H1 107.9 . . ?
C3 C2 H2 107.9 . . ?
C1 C2 H1 107.9 . . ?
C1 C2 H2 107.9 . . ?
C1 C2 C3 117.5(8) . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C2 C3 C4 114.8(8) . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
N1 C6 H6A 108.7 . . ?
N1 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C5 C6 N1 114.3(7) . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
N1 C1 C2 119.1(6) . . ?
N1 C1 H3 107.5 . . ?
N1 C1 H4 107.5 . . ?
C2 C1 H3 107.5 . . ?
C2 C1 H4 107.5 . . ?
H3 C1 H4 107.0 . . ?
C7 C8 H8A 107.9 . . ?
C7 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
C9 C8 C7 117.7(8) . . ?
C9 C8 H8A 107.9 . . ?
C9 C8 H8B 107.9 . . ?
C3 C4 H4A 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 C3 116.3(7) . . ?
C5 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C6 C5 C4 118.1(7) . . ?
C6 C5 H5A 107.8 . . ?
C6 C5 H5B 107.8 . . ?
C4 C5 H5A 107.8 . . ?
C4 C5 H5B 107.8 . . ?
H5A C5 H5B 107.1 . . ?
C8 C9 H9A 107.4 . . ?
C8 C9 H9B 107.4 . . ?
C8 C9 C10 119.8(9) . . ?
H9A C9 H9B 106.9 . . ?
C10 C9 H9A 107.4 . . ?
C10 C9 H9B 107.4 . . ?
C9 C10 H10A 105.9 . . ?
C9 C10 H10B 105.9 . . ?
H10A C10 H10B 106.2 . . ?
C11 C10 C9 125.8(10) . . ?
C11 C10 H10A 105.9 . . ?
C11 C10 H10B 105.9 . . ?
C10 C11 H11A 103.6 . . ?
C10 C11 H11B 103.6 . . ?
C10 C11 C12 134.3(13) . . ?
H11A C11 H11B 105.3 . . ?
C12 C11 H11A 103.6 . . ?
C12 C11 H11B 103.6 . . ?
N2 C12 H12A 107.6 . . ?
N2 C12 H12B 107.6 . . ?
C11 C12 N2 118.7(8) . . ?
C11 C12 H12A 107.6 . . ?
C11 C12 H12B 107.6 . . ?
H12A C12 H12B 107.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_350K
_database_code_depnum_ccdc_archive 'CCDC 1588042'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;
_audit_creation_date             2017-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Sb, Cl, C12 H28 N2'
_chemical_formula_sum            'C12 H28 Cl5 N2 Sb'
_chemical_formula_weight         499.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Sb Cl'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   13.0708(7)
_cell_length_b                   7.9573(5)
_cell_length_c                   20.1605(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2096.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2301
_cell_measurement_temperature    350.00(10)
_cell_measurement_theta_max      22.8910
_cell_measurement_theta_min      4.0320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.947
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7734
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.493
_diffrn_reflns_theta_min         3.409
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      350.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  38.00   1.00   25.25    --   11.39 -38.00  90.00  103
  2  ω     -1.00  42.00   1.00   25.25    --   11.39  57.00 -90.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0222630000
_diffrn_orient_matrix_UB_12      -0.0788264000
_diffrn_orient_matrix_UB_13      0.0078340000
_diffrn_orient_matrix_UB_21      0.0388615000
_diffrn_orient_matrix_UB_22      0.0413337000
_diffrn_orient_matrix_UB_23      0.0183478000
_diffrn_orient_matrix_UB_31      -0.0306364000
_diffrn_orient_matrix_UB_32      -0.0048862000
_diffrn_orient_matrix_UB_33      0.0289813000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1547
_reflns_number_total             2718
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0818P)²+3.0427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1954
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 C1-C2 \\sim C2-C3 \\sim C3-C4 \\sim C4-C5 \\sim C5-C6
 with sigma of 0.02
 C7-C8 \\sim C8-C9 \\sim C9-C10 \\sim C10-C11 \\sim C11-C12
 with sigma of 0.02
3. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H4A(0.5) H4B(0.5) H1C(0.5) H1D(0.5) H2A(0.5)
 H2B(0.5) H5A(0.5) H5B(0.5) H3A(0.5) H3B(0.5) H6A(0.5) H6B(0.5) H9A(0.5)
 H9B(0.5) H7A(0.5) H7B(0.5) H12A(0.5) H12B(0.5) H2C(0.5) H2D(0.5) H11A(0.5)
 H11B(0.5) H10A(0.5) H10B(0.5) H8A(0.5) H8B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C4(H4A,H4B), C1(H1C,H1D), C2(H2A,H2B), C5(H5A,H5B), C3(H3A,H3B),
 C6(H6A,H6B), C9(H9A,H9B), C7(H7A,H7B), C12(H12A,H12B), N2(H2C,H2D), C11(H11A,
 H11B), C10(H10A,H10B), C8(H8A,H8B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.13910(5) 0.2500 0.44098(3) 0.0898(3) Uani 1 2 d S T P . .
Cl1 Cl 0.2763(3) 0.2500 0.54331(18) 0.1400(12) Uani 1 2 d S T P . .
Cl2 Cl 0.0202(3) 0.2500 0.34025(15) 0.1326(11) Uani 1 2 d S T P . .
Cl3 Cl 0.2429(2) 0.0317(6) 0.38891(17) 0.230(2) Uani 1 1 d . . . . .
Cl4 Cl 0.0000 0.0000 0.5000 0.255(3) Uani 1 2 d S T P . .
N1 N 0.0276(12) -0.2500 0.3428(6) 0.195(6) Uani 1 2 d S T P . .
H1A H 0.0498 -0.3416 0.3657 0.234 Uiso 0.5 1 calc R . . . .
H1B H 0.0498 -0.1584 0.3657 0.234 Uiso 0.5 1 calc R . . . .
C4 C -0.041(2) -0.2500 0.1949(8) 0.237(13) Uani 1 2 d DS T P . .
H4A H -0.0476 -0.1501 0.1659 0.284 Uiso 0.5 1 calc R . . . .
H4B H -0.0476 -0.3499 0.1659 0.284 Uiso 0.5 1 calc R . . . .
C1 C -0.0695(14) -0.2500 0.3473(7) 0.30(2) Uani 1 2 d DS T P . .
H1C H -0.0875 -0.1504 0.3743 0.360 Uiso 0.5 1 calc R . . . .
H1D H -0.0875 -0.3496 0.3743 0.360 Uiso 0.5 1 calc R . . . .
C2 C -0.1318(14) -0.2500 0.2977(11) 0.38(3) Uani 1 2 d DS T P . .
H2A H -0.1759 -0.3489 0.3061 0.459 Uiso 0.5 1 calc R . . . .
H2B H -0.1759 -0.1511 0.3061 0.459 Uiso 0.5 1 calc R . . . .
C5 C 0.0525(19) -0.2500 0.2195(10) 0.268(15) Uani 1 2 d DS T P . .
H5A H 0.0858 -0.3492 0.1992 0.321 Uiso 0.5 1 calc R . . . .
H5B H 0.0858 -0.1508 0.1992 0.321 Uiso 0.5 1 calc R . . . .
C3 C -0.1210(15) -0.2500 0.2345(12) 0.37(3) Uani 1 2 d DS T P . .
H3A H -0.1610 -0.1511 0.2199 0.446 Uiso 0.5 1 calc R . . . .
H3B H -0.1610 -0.3489 0.2199 0.446 Uiso 0.5 1 calc R . . . .
C6 C 0.0834(14) -0.2500 0.2799(12) 0.32(2) Uani 1 2 d DS T P . .
H6A H 0.1290 -0.1509 0.2829 0.383 Uiso 0.5 1 calc R . . . .
H6B H 0.1290 -0.3491 0.2829 0.383 Uiso 0.5 1 calc R . . . .
C9 C 0.1354(18) 0.2500 0.1593(11) 0.246(14) Uani 1 2 d DS T P . .
H9A H 0.1297 0.3493 0.1887 0.296 Uiso 0.5 1 calc R . . . .
H9B H 0.1297 0.1507 0.1887 0.296 Uiso 0.5 1 calc R . . . .
C7 C 0.2671(12) 0.2500 0.0764(10) 0.209(11) Uani 1 2 d DS T P . .
H7A H 0.3127 0.3492 0.0743 0.250 Uiso 0.5 1 calc R . . . .
H7B H 0.3127 0.1508 0.0743 0.250 Uiso 0.5 1 calc R . . . .
C12 C 0.107(2) 0.2500 0.0087(9) 0.194(8) Uani 1 2 d DS T P . .
H12A H 0.0928 0.3498 -0.0191 0.233 Uiso 0.5 1 calc R . . . .
H12B H 0.0928 0.1502 -0.0191 0.233 Uiso 0.5 1 calc R . . . .
N2 N 0.2210(14) 0.2500 0.0219(8) 0.278(13) Uani 1 2 d S T P . .
H2C H 0.2455 0.1587 -0.0002 0.334 Uiso 0.5 1 calc R . . . .
H2D H 0.2455 0.3413 -0.0002 0.334 Uiso 0.5 1 calc R . . . .
C11 C 0.0401(18) 0.2500 0.0570(13) 0.33(3) Uani 1 2 d DS T P . .
H11A H -0.0034 0.1510 0.0474 0.400 Uiso 0.5 1 calc R . . . .
H11B H -0.0034 0.3490 0.0474 0.400 Uiso 0.5 1 calc R . . . .
C10 C 0.0484(15) 0.2500 0.1228(13) 0.247(15) Uani 1 2 d DS T P . .
H10A H 0.0093 0.1506 0.1380 0.296 Uiso 0.5 1 calc R . . . .
H10B H 0.0093 0.3494 0.1380 0.296 Uiso 0.5 1 calc R . . . .
C8 C 0.2307(17) 0.2500 0.1387(9) 0.221(10) Uani 1 2 d DS T P . .
H8A H 0.2624 0.1507 0.1601 0.265 Uiso 0.5 1 calc R . . . .
H8B H 0.2624 0.3493 0.1601 0.265 Uiso 0.5 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl1 2.734(3) . ?
Sb1 Cl2 2.557(3) . ?
Sb1 Cl3 2.441(3) 8_565 ?
Sb1 Cl3 2.441(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C1 1.272(18) . ?
N1 C6 1.46(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.324(13) . ?
C4 C3 1.310(13) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.290(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.282(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.283(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.355(13) . ?
C9 C8 1.313(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N2 1.25(2) . ?
C7 C8 1.344(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 N2 1.51(2) . ?
C12 C11 1.313(15) . ?
N2 H2C 0.9100 . ?
N2 H2D 0.9100 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.331(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 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
Cl2 Sb1 Cl1 176.43(11) . . ?
Cl3 Sb1 Cl1 87.70(10) 8_565 . ?
Cl3 Sb1 Cl1 87.70(10) . . ?
Cl3 Sb1 Cl2 89.79(9) . . ?
Cl3 Sb1 Cl2 89.79(9) 8_565 . ?
Cl3 Sb1 Cl3 90.7(2) 8_565 . ?
H1A N1 H1B 106.4 . . ?
C1 N1 H1A 106.3 . . ?
C1 N1 H1B 106.3 . . ?
C1 N1 C6 124.0(13) . . ?
C6 N1 H1A 106.3 . . ?
C6 N1 H1B 106.3 . . ?
H4A C4 H4B 106.8 . . ?
C5 C4 H4A 107.2 . . ?
C5 C4 H4B 107.2 . . ?
C3 C4 H4A 107.2 . . ?
C3 C4 H4B 107.2 . . ?
C3 C4 C5 120.5(18) . . ?
N1 C1 H1C 106.1 . . ?
N1 C1 H1D 106.1 . . ?
N1 C1 C2 125.1(16) . . ?
H1C C1 H1D 106.3 . . ?
C2 C1 H1C 106.1 . . ?
C2 C1 H1D 106.1 . . ?
C1 C2 H2A 103.6 . . ?
C1 C2 H2B 103.6 . . ?
H2A C2 H2B 105.3 . . ?
C3 C2 C1 134(2) . . ?
C3 C2 H2A 103.6 . . ?
C3 C2 H2B 103.6 . . ?
C4 C5 H5A 104.7 . . ?
C4 C5 H5B 104.7 . . ?
H5A C5 H5B 105.7 . . ?
C6 C5 C4 130.3(18) . . ?
C6 C5 H5A 104.7 . . ?
C6 C5 H5B 104.7 . . ?
C4 C3 H3A 103.7 . . ?
C4 C3 H3B 103.7 . . ?
C2 C3 C4 134(2) . . ?
C2 C3 H3A 103.7 . . ?
C2 C3 H3B 103.7 . . ?
H3A C3 H3B 105.4 . . ?
N1 C6 H6A 104.3 . . ?
N1 C6 H6B 104.3 . . ?
C5 C6 N1 131.7(16) . . ?
C5 C6 H6A 104.3 . . ?
C5 C6 H6B 104.3 . . ?
H6A C6 H6B 105.6 . . ?
H9A C9 H9B 105.9 . . ?
C10 C9 H9A 105.1 . . ?
C10 C9 H9B 105.1 . . ?
C8 C9 H9A 105.1 . . ?
C8 C9 H9B 105.1 . . ?
C8 C9 C10 129(2) . . ?
H7A C7 H7B 105.7 . . ?
N2 C7 H7A 104.6 . . ?
N2 C7 H7B 104.6 . . ?
N2 C7 C8 130.6(17) . . ?
C8 C7 H7A 104.6 . . ?
C8 C7 H7B 104.6 . . ?
H12A C12 H12B 106.7 . . ?
N2 C12 H12A 106.8 . . ?
N2 C12 H12B 106.8 . . ?
C11 C12 H12A 106.8 . . ?
C11 C12 H12B 106.8 . . ?
C11 C12 N2 122.0(18) . . ?
C7 N2 C12 128.9(14) . . ?
C7 N2 H2C 105.1 . . ?
C7 N2 H2D 105.1 . . ?
C12 N2 H2C 105.1 . . ?
C12 N2 H2D 105.1 . . ?
H2C N2 H2D 105.9 . . ?
C12 C11 H11A 103.9 . . ?
C12 C11 H11B 103.9 . . ?
C12 C11 C10 133(2) . . ?
H11A C11 H11B 105.4 . . ?
C10 C11 H11A 103.9 . . ?
C10 C11 H11B 103.9 . . ?
C9 C10 H10A 105.4 . . ?
C9 C10 H10B 105.4 . . ?
C11 C10 C9 128(2) . . ?
C11 C10 H10A 105.4 . . ?
C11 C10 H10B 105.4 . . ?
H10A C10 H10B 106.0 . . ?
C9 C8 C7 129.1(19) . . ?
C9 C8 H8A 105.0 . . ?
C9 C8 H8B 105.0 . . ?
C7 C8 H8A 105.0 . . ?
C7 C8 H8B 105.0 . . ?
H8A C8 H8B 105.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.838
