# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2141834'
loop_
_audit_author_name
_audit_author_address
'Tingting ying'
;Jiangxi University of Science and Technology
China
;
_audit_update_record             
;
2022-01-13 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-06-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl5 Sb, 2(C4 H10 N O)'
_chemical_formula_sum            'C8 H20 Cl5 N2 O2 Sb'
_chemical_formula_weight         475.26
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.7467(4)
_cell_length_b                   11.3654(5)
_cell_length_c                   17.6409(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1753.68(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9716
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      27.369
_cell_measurement_theta_min      2.924
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    2.331
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0935 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.6334.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21133
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.939
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2565
_reflns_number_total             3074
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.613
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.241
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     179
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0877
_refine_ls_restrained_S_all      5.708
_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)+(0.1981P)²+2.3757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2589
_refine_ls_wR_factor_ref         0.2891
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(2)
 0.2(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Restrained distances
 O1-C3 = O2-C6
 1.431 with sigma of 0.001
 O2-C5 = O2-C7 = O1-C2 = O1-C4
 2.344 with sigma of 0.001
 C7-C5 = C4-C2
 2.34 with sigma of 0.001
 C6-C5 = C7-C6 = C3-C2 = C4-C3
 1.485 with sigma of 0.001
 Cl1_$2-H1
 2.271 with sigma of 0.001
 C2-C1 = C8-C7
 1.501 with sigma of 0.001
 Cl4_$1-H2
 2.04 with sigma of 0.001
 N2-C5 = N2-C8 = N1A-C1 = N1A-C4
 1.485 with sigma of 0.001
 N2-C6 = C8-C6 = C3-C1 = N1A-C3
 2.352 with sigma of 0.001
 H2-O2
 0.85 with sigma of 0.001
 H1-Cl1_$2
 2.322 with sigma of 0.001
 H1b-H7b
 2.1 with sigma of 0.01
 H1b-H6
 2.1 with sigma of 0.01
 H3_$3-H1Ab
 2.1 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C4) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(N1A) \\sim Ueq: with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C3) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(N1A) \\sim Ueq: with sigma of 0.001 and sigma
for terminal atoms of 0.002
Uanis(C5) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C8) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.001 and sigma
for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 N2, O2, C7, C6, C5, C8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N1A, O1, C3, C4, C2, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6.a Everything fixed:
 O1, O2, H2, C8
6.b Riding coordinates:
 O1(H1)
6.c Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
6.d Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b), C4(H4a,H4b), N1A(H1Aa,H1Ab), C8(H8a,H8b), C7(H7a,
 H7b), C5(H5a,H5b), N2(H2c,H2d)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb -0.01392(15) -0.10966(10) 0.56829(7) 0.0764(6) Uani 1 1 d . . . . .
Cl2 Cl -0.2676(10) -0.2468(9) 0.5004(5) 0.132(2) Uani 1 1 d . . . . .
Cl5 Cl -0.0097(10) -0.2507(7) 0.6803(4) 0.131(2) Uani 1 1 d . . . . .
Cl4 Cl 0.1798(7) 0.0108(5) 0.6281(4) 0.134(3) Uani 1 1 d . . . . .
Cl3 Cl -0.2115(11) 0.0085(8) 0.6282(6) 0.154(4) Uani 1 1 d . . . . .
Cl1 Cl -0.0248(9) 0.0343(9) 0.4470(6) 0.176(4) Uani 1 1 d . . . . .
O1 O 0.128230 0.450920 0.576840 0.398 Uani 1 1 d D U . . .
H1 H 0.215440 0.439400 0.561480 0.598 Uiso 1 1 d DR U . . .
C1 C -0.0662(10) 0.1922(7) 0.6360(6) 0.276(6) Uani 1 1 d D U . . .
H1A H -0.023010 0.115780 0.624100 0.331 Uiso 1 1 calc R U . . .
H1B H -0.126387 0.185635 0.681948 0.331 Uiso 1 1 calc DR U . . .
C2 C 0.058(2) 0.2825(11) 0.6451(7) 0.273(5) Uani 1 1 d D U . . .
H2A H 0.027521 0.342916 0.680964 0.328 Uiso 1 1 calc R U . . .
H2B H 0.151899 0.246410 0.662408 0.328 Uiso 1 1 calc R U . . .
C3 C 0.0761(10) 0.3324(4) 0.5678(5) 0.265(4) Uani 1 1 d D U . . .
H3 H 0.143925 0.285164 0.535750 0.318 Uiso 1 1 calc R U . . .
C4 C -0.082(2) 0.3386(14) 0.5381(12) 0.276(5) Uani 1 1 d D U . . .
H4A H -0.083075 0.333478 0.483176 0.331 Uiso 1 1 calc R U . . .
H4B H -0.131383 0.411526 0.553179 0.331 Uiso 1 1 calc R U . . .
N1A N -0.1615(17) 0.236(2) 0.5722(12) 0.277(6) Uani 1 1 d D U . . .
H1AA H -0.253400 0.256945 0.589092 0.332 Uiso 1 1 calc R U . . .
H1AB H -0.173540 0.179443 0.537717 0.332 Uiso 1 1 calc DR U . . .
O2 O -0.399040 0.335720 0.831750 0.333 Uani 1 1 d D U . . .
H2 H -0.336290 0.412260 0.814240 0.499 Uiso 1 1 d D U . . .
C8 C -0.485080 0.076520 0.783200 0.271 Uani 1 1 d D U . . .
H8A H -0.476891 0.028384 0.737976 0.325 Uiso 1 1 calc R U . . .
H8B H -0.507127 0.025601 0.825952 0.325 Uiso 1 1 calc R U . . .
C7 C -0.33872(18) 0.1424(3) 0.7964(6) 0.274(3) Uani 1 1 d D U . . .
H7A H -0.313467 0.144531 0.849955 0.329 Uiso 1 1 calc R U . . .
H7B H -0.254776 0.106507 0.768921 0.329 Uiso 1 1 calc DR U . . .
C6 C -0.3713(10) 0.2624(3) 0.7673(3) 0.268(3) Uani 1 1 d D U . . .
H6 H -0.289794 0.292672 0.734520 0.322 Uiso 1 1 calc DR U . . .
C5 C -0.5193(17) 0.2492(4) 0.7269(5) 0.270(4) Uani 1 1 d D U . . .
H5A H -0.503728 0.218236 0.676260 0.324 Uiso 1 1 calc R U . . .
H5B H -0.571688 0.324236 0.723202 0.324 Uiso 1 1 calc R U . . .
N2 N -0.6083(5) 0.1652(3) 0.7740(9) 0.270(3) Uani 1 1 d D U . . .
H2C H -0.689177 0.136542 0.749517 0.324 Uiso 1 1 calc R U . . .
H2D H -0.637359 0.196371 0.817948 0.324 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl2 2.964(9) . ?
Sb1 Cl5 2.544(7) . ?
Sb1 Cl4 2.421(6) . ?
Sb1 Cl3 2.431(7) . ?
Sb1 Cl1 2.696(8) . ?
O1 H1 0.8200 . ?
O1 C3 1.4309(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.5011(14) . ?
C1 N1A 1.4849(14) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.4850(14) . ?
C3 H3 0.9800 . ?
C3 C4 1.4851(14) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1A 1.4852(14) . ?
N1A H1AA 0.8900 . ?
N1A H1AB 0.8900 . ?
O2 H2 1.0740 . ?
O2 C6 1.4311(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.5013(14) . ?
C8 N2 1.4851(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.4852(14) . ?
C6 H6 0.9800 . ?
C6 C5 1.4852(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 N2 1.4851(14) . ?
N2 H2C 0.8900 . ?
N2 H2D 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
Cl5 Sb1 Cl2 89.6(3) . . ?
Cl5 Sb1 Cl1 177.9(3) . . ?
Cl4 Sb1 Cl2 176.0(3) . . ?
Cl4 Sb1 Cl5 90.4(2) . . ?
Cl4 Sb1 Cl1 91.6(3) . . ?
Cl3 Sb1 Cl2 86.2(3) . . ?
Cl3 Sb1 Cl5 91.2(3) . . ?
Cl3 Sb1 Cl4 89.7(3) . . ?
Cl3 Sb1 Cl1 89.1(4) . . ?
Cl1 Sb1 Cl2 88.4(3) . . ?
C3 O1 H1 96.3 . . ?
H1A C1 H1B 108.8 . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
N1A C1 H1A 110.8 . . ?
N1A C1 H1B 110.8 . . ?
N1A C1 C2 105.0(8) . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 C1 103.93(13) . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
O1 C3 C2 106.99(14) . . ?
O1 C3 H3 112.8 . . ?
O1 C3 C4 106.98(14) . . ?
C2 C3 H3 112.8 . . ?
C2 C3 C4 103.96(13) . . ?
C4 C3 H3 112.8 . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C3 C4 N1A 104.71(13) . . ?
H4A C4 H4B 108.9 . . ?
N1A C4 H4A 110.8 . . ?
N1A C4 H4B 110.8 . . ?
C1 N1A C4 108.0(5) . . ?
C1 N1A H1AA 110.1 . . ?
C1 N1A H1AB 110.1 . . ?
C4 N1A H1AA 110.1 . . ?
C4 N1A H1AB 110.1 . . ?
H1AA N1A H1AB 108.4 . . ?
C6 O2 H2 99.0 . . ?
H8A C8 H8B 108.5 . . ?
C7 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
N2 C8 H8A 110.3 . . ?
N2 C8 H8B 110.3 . . ?
N2 C8 C7 107.31(13) . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
C6 C7 C8 103.91(12) . . ?
C6 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
O2 C6 C7 106.97(14) . . ?
O2 C6 H6 112.8 . . ?
O2 C6 C5 106.97(14) . . ?
C7 C6 H6 112.8 . . ?
C7 C6 C5 103.94(13) . . ?
C5 C6 H6 112.8 . . ?
C6 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
C6 C5 N2 104.71(13) . . ?
H5A C5 H5B 108.9 . . ?
N2 C5 H5A 110.8 . . ?
N2 C5 H5B 110.8 . . ?
C8 N2 H2C 112.4 . . ?
C8 N2 H2D 112.4 . . ?
C5 N2 C8 96.7(3) . . ?
C5 N2 H2C 112.4 . . ?
C5 N2 H2D 112.4 . . ?
H2C N2 H2D 110.0 . . ?

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
O1 C3 C4 N1A -146.3(15) . . . . ?
C1 C2 C3 O1 151.4(8) . . . . ?
C1 C2 C3 C4 38.4(9) . . . . ?
C2 C1 N1A C4 8(3) . . . . ?
C2 C3 C4 N1A -33.3(15) . . . . ?
C3 C4 N1A C1 16(3) . . . . ?
N1A C1 C2 C3 -29(2) . . . . ?
O2 C6 C5 N2 -75.4(3) . . . . ?
C8 C7 C6 O2 102.40(18) . . . . ?
C8 C7 C6 C5 -10.6(3) . . . . ?
C7 C8 N2 C5 41.0(6) . . . . ?
C7 C6 C5 N2 37.5(3) . . . . ?
C6 C5 N2 C8 -47.7(5) . . . . ?
N2 C8 C7 C6 -19.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(2)
2 0.2(2)

