# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Sb_1_Et
_database_code_depnum_ccdc_archive 'CCDC 1976847'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-01-10 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;

_audit_creation_date             2017-07-20T11:58:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C6 H11 S3 Sb'
_chemical_formula_weight         301.08

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   7.5797(7)
_cell_length_b                   9.1057(9)
_cell_length_c                   27.371(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.2180(10)
_cell_angle_gamma                90
_cell_volume                     1881.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9868
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.17

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    2.126
_exptl_crystal_F_000             1168

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.4912
_exptl_absorpt_correction_T_min  0.4049
_shelx_estimated_absorpt_T_min   0.479
_shelx_estimated_absorpt_T_max   0.677

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_number            21518
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.494
_diffrn_reflns_theta_max         27.168
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             4176
_reflns_number_gt                3765
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0171P)²+1.5186P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4176
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0429
_refine_ls_wR_factor_gt          0.0412
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.109

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.31283(2) 0.46710(2) 0.29739(2) 0.01001(4) Uani 1 d . .
Sb2 Sb 0.69169(2) 0.45214(2) 0.19996(2) 0.01035(4) Uani 1 d . .
S1 S 0.57150(7) 0.30487(6) 0.30029(2) 0.01142(11) Uani 1 d . .
S2 S 0.50044(7) 0.67722(6) 0.32011(2) 0.01101(11) Uani 1 d . .
S3 S 0.26997(7) 0.41317(6) 0.38323(2) 0.01108(11) Uani 1 d . .
S4 S 0.49928(7) 0.24350(6) 0.17894(2) 0.01119(11) Uani 1 d . .
S5 S 0.43687(7) 0.61782(6) 0.19876(2) 0.01137(11) Uani 1 d . .
S6 S 0.72546(7) 0.50578(6) 0.11349(2) 0.01191(11) Uani 1 d . .
C1 C 0.7254(3) 0.3973(2) 0.34628(8) 0.0106(4) Uani 1 d . .
H1A H 0.8171 0.3252 0.3583 0.013 Uiso 1 calc . .
H1B H 0.7861 0.4763 0.3295 0.013 Uiso 1 calc . .
C2 C 0.5908(3) 0.6266(2) 0.38193(8) 0.0108(4) Uani 1 d . .
H2A H 0.6952 0.6897 0.3908 0.013 Uiso 1 calc . .
H2B H 0.5009 0.651 0.4047 0.013 Uiso 1 calc . .
C3 C 0.4966(3) 0.3695(2) 0.40826(8) 0.0106(4) Uani 1 d . .
H3A H 0.5011 0.3757 0.4445 0.013 Uiso 1 calc . .
H3B H 0.521 0.2662 0.3999 0.013 Uiso 1 calc . .
C4 C 0.6477(3) 0.4654(2) 0.39137(8) 0.0095(4) Uani 1 d . .
C5 C 0.8002(3) 0.4657(2) 0.43334(8) 0.0131(4) Uani 1 d . .
H5A H 0.8241 0.363 0.4438 0.016 Uiso 1 calc . .
H5B H 0.9086 0.5037 0.4201 0.016 Uiso 1 calc . .
C6 C 0.7658(3) 0.5562(3) 0.47845(8) 0.0196(5) Uani 1 d . .
H6A H 0.7595 0.6605 0.4697 0.029 Uiso 1 calc . .
H6B H 0.8624 0.5406 0.5042 0.029 Uiso 1 calc . .
H6C H 0.6535 0.5255 0.4904 0.029 Uiso 1 calc . .
C7 C 0.4025(3) 0.2941(2) 0.11762(8) 0.0107(4) Uani 1 d . .
H7A H 0.4889 0.2684 0.094 0.013 Uiso 1 calc . .
H7B H 0.2964 0.2322 0.1097 0.013 Uiso 1 calc . .
C8 C 0.2775(3) 0.5255(2) 0.15438(8) 0.0106(4) Uani 1 d . .
H8A H 0.2182 0.4475 0.1721 0.013 Uiso 1 calc . .
H8B H 0.1855 0.5981 0.143 0.013 Uiso 1 calc . .
C9 C 0.4970(3) 0.5477(2) 0.08946(8) 0.0112(4) Uani 1 d . .
H9A H 0.4738 0.6521 0.0967 0.013 Uiso 1 calc . .
H9B H 0.4891 0.5372 0.0533 0.013 Uiso 1 calc . .
C10 C 0.3476(3) 0.4554(2) 0.10859(8) 0.0097(4) Uani 1 d . .
C11 C 0.1887(3) 0.4585(2) 0.06854(8) 0.0138(5) Uani 1 d . .
H11A H 0.0817 0.4253 0.0836 0.017 Uiso 1 calc . .
H11B H 0.1684 0.5616 0.058 0.017 Uiso 1 calc . .
C12 C 0.2080(3) 0.3651(3) 0.02289(8) 0.0195(5) Uani 1 d . .
H12A H 0.1043 0.3796 -0.0007 0.029 Uiso 1 calc . .
H12B H 0.2169 0.2613 0.0322 0.029 Uiso 1 calc . .
H12C H 0.3152 0.3946 0.0079 0.029 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 S2 2.4308(6) . ?
Sb1 S1 2.4504(6) . ?
Sb1 S3 2.4505(6) . ?
Sb2 S4 2.4319(6) . ?
Sb2 S5 2.4487(6) . ?
Sb2 S6 2.4525(6) . ?
S1 C1 1.841(2) . ?
S2 C2 1.826(2) . ?
S3 C3 1.834(2) . ?
S4 C7 1.829(2) . ?
S5 C8 1.837(2) . ?
S6 C9 1.836(2) . ?
C1 C4 1.545(3) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C4 1.545(3) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.544(3) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.554(3) . ?
C5 C6 1.526(3) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 C10 1.540(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C10 1.544(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.540(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.553(3) . ?
C11 C12 1.529(3) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?

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
S2 Sb1 S1 91.061(19) . . ?
S2 Sb1 S3 92.175(19) . . ?
S1 Sb1 S3 91.358(18) . . ?
S4 Sb2 S5 91.30(2) . . ?
S4 Sb2 S6 92.315(19) . . ?
S5 Sb2 S6 90.904(18) . . ?
C1 S1 Sb1 101.65(7) . . ?
C2 S2 Sb1 101.52(7) . . ?
C3 S3 Sb1 101.56(7) . . ?
C7 S4 Sb2 101.65(7) . . ?
C8 S5 Sb2 101.39(7) . . ?
C9 S6 Sb2 102.08(7) . . ?
C4 C1 S1 117.76(14) . . ?
C4 C1 H1A 107.9 . . ?
S1 C1 H1A 107.9 . . ?
C4 C1 H1B 107.9 . . ?
S1 C1 H1B 107.9 . . ?
H1A C1 H1B 107.2 . . ?
C4 C2 S2 118.07(15) . . ?
C4 C2 H2A 107.8 . . ?
S2 C2 H2A 107.8 . . ?
C4 C2 H2B 107.8 . . ?
S2 C2 H2B 107.8 . . ?
H2A C2 H2B 107.1 . . ?
C4 C3 S3 117.43(15) . . ?
C4 C3 H3A 107.9 . . ?
S3 C3 H3A 107.9 . . ?
C4 C3 H3B 107.9 . . ?
S3 C3 H3B 107.9 . . ?
H3A C3 H3B 107.2 . . ?
C3 C4 C2 112.58(17) . . ?
C3 C4 C1 111.07(17) . . ?
C2 C4 C1 111.62(17) . . ?
C3 C4 C5 107.58(17) . . ?
C2 C4 C5 107.44(17) . . ?
C1 C4 C5 106.19(17) . . ?
C6 C5 C4 115.38(18) . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C10 C7 S4 117.89(15) . . ?
C10 C7 H7A 107.8 . . ?
S4 C7 H7A 107.8 . . ?
C10 C7 H7B 107.8 . . ?
S4 C7 H7B 107.8 . . ?
H7A C7 H7B 107.2 . . ?
C10 C8 S5 118.16(15) . . ?
C10 C8 H8A 107.8 . . ?
S5 C8 H8A 107.8 . . ?
C10 C8 H8B 107.8 . . ?
S5 C8 H8B 107.8 . . ?
H8A C8 H8B 107.1 . . ?
C10 C9 S6 117.63(15) . . ?
C10 C9 H9A 107.9 . . ?
S6 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
S6 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?
C7 C10 C9 112.25(17) . . ?
C7 C10 C8 111.86(17) . . ?
C9 C10 C8 111.60(17) . . ?
C7 C10 C11 108.16(17) . . ?
C9 C10 C11 107.29(17) . . ?
C8 C10 C11 105.26(17) . . ?
C12 C11 C10 116.15(18) . . ?
C12 C11 H11A 108.2 . . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C10 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

