# 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 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_1760
_database_code_depnum_ccdc_archive 'CCDC 1980084'
loop_
_audit_author_name
_audit_author_address
'Vladimir Sharutin'
;South Ural State University
Russia
;
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-07-30 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            'C21 H18 Br3 I4 O3 Sb'
_chemical_formula_weight         1187.43

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'
O O 0.0106 0.0060 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.4322(19)
_cell_length_b                   12.154(2)
_cell_length_c                   13.144(3)
_cell_angle_alpha                87.26(3)
_cell_angle_beta                 80.96(3)
_cell_angle_gamma                82.24(3)
_cell_volume                     1474.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5475
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      25.86

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.675
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    9.212
_shelx_estimated_absorpt_T_min   0.175
_shelx_estimated_absorpt_T_max   0.431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1753
_exptl_absorpt_correction_T_max  0.4306
_exptl_absorpt_process_details   'SADABS (Bruker-AXS, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_reflns_number            22024
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.948
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5461
_reflns_number_gt                4191
_reflns_threshold_expression     >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       'APEX2 (Bruker-AXS, 2004)'
_computing_cell_refinement       'SAINT (Bruker-AXS, 2004)'
_computing_data_reduction        'SAINT (Bruker-AXS, 2004)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0448P)²+4.5122P] 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         5461
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.2382(12) -0.0049(7) 0.4418(8) 0.087(3) Uani 1 1 d . . . . .
H1A H 0.1518 0.0310 0.4818 0.131 Uiso 1 1 calc R U . . .
H1B H 0.3100 -0.0267 0.4858 0.131 Uiso 1 1 calc R U . . .
H1C H 0.2165 -0.0696 0.4111 0.131 Uiso 1 1 calc R U . . .
C2 C 0.2283(8) 0.0845(5) 0.2788(6) 0.0456(16) Uani 1 1 d . . . . .
C3 C 0.1147(9) 0.0391(7) 0.2566(7) 0.062(2) Uani 1 1 d . . . . .
H3 H 0.0714 -0.0108 0.3033 0.075 Uiso 1 1 calc R U . . .
C4 C 0.0631(9) 0.0652(7) 0.1670(8) 0.069(2) Uani 1 1 d . . . . .
H4 H -0.0151 0.0325 0.1530 0.082 Uiso 1 1 calc R U . . .
C5 C 0.1220(8) 0.1373(7) 0.0977(6) 0.0578(19) Uani 1 1 d . . . . .
C6 C 0.2386(7) 0.1839(6) 0.1171(5) 0.0466(16) Uani 1 1 d . . . . .
H6 H 0.2822 0.2331 0.0697 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2898(7) 0.1561(5) 0.2083(5) 0.0394(14) Uani 1 1 d . . . . .
C8 C 0.1621(9) 0.4967(6) 0.2986(6) 0.060(2) Uani 1 1 d . . . . .
H8A H 0.0924 0.4918 0.3598 0.090 Uiso 1 1 calc R U . . .
H8B H 0.1159 0.4932 0.2390 0.090 Uiso 1 1 calc R U . . .
H8C H 0.2013 0.5658 0.2970 0.090 Uiso 1 1 calc R U . . .
C9 C 0.4380(7) 0.2936(5) 0.3836(5) 0.0394(14) Uani 1 1 d . . . . .
C10 C 0.3342(7) 0.3856(5) 0.3862(5) 0.0422(15) Uani 1 1 d . . . . .
C11 C 0.2989(8) 0.4461(6) 0.4747(6) 0.0523(18) Uani 1 1 d . . . . .
H11 H 0.2289 0.5080 0.4781 0.063 Uiso 1 1 calc R U . . .
C12 C 0.3674(9) 0.4144(6) 0.5569(6) 0.0564(19) Uani 1 1 d . . . . .
H12 H 0.3437 0.4548 0.6169 0.068 Uiso 1 1 calc R U . . .
C13 C 0.4712(8) 0.3233(6) 0.5519(5) 0.0491(17) Uani 1 1 d . . . . .
C14 C 0.5076(8) 0.2612(6) 0.4652(5) 0.0478(16) Uani 1 1 d . . . . .
H14 H 0.5774 0.1991 0.4622 0.057 Uiso 1 1 calc R U . . .
C15 C 0.5953(15) 0.1187(8) -0.0760(7) 0.103(4) Uani 1 1 d . . . . .
H15A H 0.5607 0.1717 -0.1259 0.155 Uiso 1 1 calc R U . . .
H15B H 0.5484 0.0533 -0.0754 0.155 Uiso 1 1 calc R U . . .
H15C H 0.6981 0.0993 -0.0939 0.155 Uiso 1 1 calc R U . . .
C16 C 0.6013(8) 0.2653(6) 0.0343(5) 0.0480(16) Uani 1 1 d . . . . .
C17 C 0.5626(7) 0.3080(5) 0.1304(5) 0.0394(14) Uani 1 1 d . . . . .
C18 C 0.5988(8) 0.4073(6) 0.1529(5) 0.0478(17) Uani 1 1 d . . . . .
H18 H 0.5735 0.4349 0.2190 0.057 Uiso 1 1 calc R U . . .
C19 C 0.6721(10) 0.4645(7) 0.0774(7) 0.067(2) Uani 1 1 d . . . . .
C20 C 0.7095(12) 0.4237(9) -0.0184(7) 0.085(3) Uani 1 1 d . . . . .
H20 H 0.7606 0.4648 -0.0696 0.102 Uiso 1 1 calc R U . . .
C21 C 0.6744(11) 0.3242(8) -0.0416(6) 0.078(3) Uani 1 1 d . . . . .
H21 H 0.6998 0.2972 -0.1079 0.093 Uiso 1 1 calc R U . . .
O1 O 0.2908(6) 0.0682(4) 0.3648(4) 0.0602(14) Uani 1 1 d . . . . .
O2 O 0.5646(6) 0.1650(4) 0.0217(4) 0.0599(14) Uani 1 1 d . . . . .
O3 O 0.2751(6) 0.4075(4) 0.2989(4) 0.0516(12) Uani 1 1 d . . . . .
Br1 Br 0.05245(14) 0.17129(10) -0.02696(10) 0.1024(4) Uani 1 1 d . . . . .
Br2 Br 0.73076(15) 0.59728(9) 0.10872(10) 0.1022(4) Uani 1 1 d . . . . .
Br3 Br 0.56363(12) 0.28227(10) 0.66692(7) 0.0852(3) Uani 1 1 d . . . . .
Sb1 Sb 0.47281(5) 0.20942(3) 0.24589(3) 0.03681(12) Uani 1 1 d . . . . .
I1 I 0.65765(5) 0.02960(4) 0.26789(4) 0.05228(14) Uani 1 1 d . . . . .
I2 I 0.86300(7) 0.31661(5) 0.30725(5) 0.07412(18) Uani 1 1 d . . . . .
I3 I 0.97807(6) 0.26595(4) 0.49417(5) 0.05924(15) Uani 1 1 d . . . . .
I4 I 1.09084(8) 0.21886(5) 0.69104(5) 0.0815(2) Uani 1 1 d . . . . .


_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 O1 1.392(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.346(10) . ?
C2 O1 1.349(9) . ?
C2 C7 1.357(9) . ?
C3 C4 1.352(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.342(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(10) . ?
C5 Br1 1.867(8) . ?
C6 C7 1.372(9) . ?
C6 H6 0.9300 . ?
C7 Sb1 2.060(6) . ?
C8 O3 1.415(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.359(9) . ?
C9 C10 1.381(9) . ?
C9 Sb1 2.081(6) . ?
C10 O3 1.354(8) . ?
C10 C11 1.377(9) . ?
C11 C12 1.358(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(10) . ?
C13 Br3 1.876(7) . ?
C14 H14 0.9300 . ?
C15 O2 1.399(9) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O2 1.337(8) . ?
C16 C21 1.354(11) . ?
C16 C17 1.365(9) . ?
C17 C18 1.356(9) . ?
C17 Sb1 2.038(6) . ?
C18 C19 1.340(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.354(13) . ?
C19 Br2 1.858(8) . ?
C20 C21 1.356(13) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
Sb1 I1 2.6399(11) . ?
I2 I3 2.8472(11) . ?
I3 I4 2.9520(11) . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 127.8(7) . . ?
C3 C2 C7 118.0(7) . . ?
O1 C2 C7 114.2(6) . . ?
C2 C3 C4 120.7(8) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 121.5(7) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 119.4(8) . . ?
C4 C5 Br1 121.4(6) . . ?
C6 C5 Br1 119.2(6) . . ?
C5 C6 C7 118.2(7) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C2 C7 C6 122.1(6) . . ?
C2 C7 Sb1 114.2(5) . . ?
C6 C7 Sb1 123.5(5) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 122.2(6) . . ?
C14 C9 Sb1 124.0(5) . . ?
C10 C9 Sb1 113.9(5) . . ?
O3 C10 C11 125.8(6) . . ?
O3 C10 C9 115.2(6) . . ?
C11 C10 C9 119.0(6) . . ?
C12 C11 C10 119.4(7) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.4(7) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 121.4(7) . . ?
C14 C13 Br3 119.4(6) . . ?
C12 C13 Br3 119.2(5) . . ?
C9 C14 C13 117.6(7) . . ?
C9 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 C21 123.7(7) . . ?
O2 C16 C17 116.6(6) . . ?
C21 C16 C17 119.7(7) . . ?
C18 C17 C16 121.6(6) . . ?
C18 C17 Sb1 119.6(5) . . ?
C16 C17 Sb1 118.2(5) . . ?
C19 C18 C17 118.2(7) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C18 C19 C20 120.7(8) . . ?
C18 C19 Br2 118.7(7) . . ?
C20 C19 Br2 120.5(6) . . ?
C19 C20 C21 121.6(8) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C16 C21 C20 118.2(8) . . ?
C16 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C2 O1 C1 119.3(7) . . ?
C16 O2 C15 119.5(6) . . ?
C10 O3 C8 118.0(5) . . ?
C17 Sb1 C7 110.6(3) . . ?
C17 Sb1 C9 109.1(2) . . ?
C7 Sb1 C9 114.0(3) . . ?
C17 Sb1 I1 108.99(19) . . ?
C7 Sb1 I1 106.56(18) . . ?
C9 Sb1 I1 107.39(18) . . ?
I2 I3 I4 178.25(3) . . ?

_refine_diff_density_max         1.263
_refine_diff_density_min         -1.208
_refine_diff_density_rms         0.140

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

####################################################################### 
# 
# 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_1824
_database_code_depnum_ccdc_archive 'CCDC 1989015'
loop_
_audit_author_name
_audit_author_address
'Vladimir Sharutin'
;South Ural State University
Russia
;
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-07-30 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            'C21 H21 I2 Sb'
_chemical_formula_weight         648.93

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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.213(3)
_cell_length_b                   15.643(3)
_cell_length_c                   9.2291(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.34(3)
_cell_angle_gamma                90
_cell_volume                     2192.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    18440
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      34.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.966
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    4.074
_shelx_estimated_absorpt_T_min   0.240
_shelx_estimated_absorpt_T_max   0.482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4097
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_process_details   'SADABS (Bruker-AXS, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_reflns_number            56515
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.835
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_full        25.500
_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             4162
_reflns_number_gt                3626
_reflns_threshold_expression     >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       'APEX2 (Bruker-AXS, 2004)'
_computing_cell_refinement       'SAINT (Bruker-AXS, 2004)'
_computing_data_reduction        'SAINT (Bruker-AXS, 2004)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0115P)²+8.3516P] 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         4162
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.176
_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
C1 C 0.2510(4) 0.5672(3) 0.5437(5) 0.0459(12) Uani 1 1 d . . . . .
C2 C 0.3273(4) 0.6141(4) 0.5593(7) 0.0681(17) Uani 1 1 d . . . . .
H2 H 0.3722 0.5982 0.6266 0.082 Uiso 1 1 calc R U . . .
C3 C 0.3360(6) 0.6865(5) 0.4716(9) 0.084(2) Uani 1 1 d . . . . .
H3 H 0.3865 0.7200 0.4819 0.101 Uiso 1 1 calc R U . . .
C4 C 0.2708(6) 0.7076(4) 0.3717(8) 0.079(2) Uani 1 1 d . . . . .
H4 H 0.2773 0.7559 0.3144 0.094 Uiso 1 1 calc R U . . .
C5 C 0.1955(5) 0.6598(4) 0.3528(7) 0.0676(17) Uani 1 1 d . . . . .
C6 C 0.1856(4) 0.5898(4) 0.4428(6) 0.0546(14) Uani 1 1 d . . . . .
H6 H 0.1339 0.5580 0.4346 0.065 Uiso 1 1 calc R U . . .
C7 C 0.1255(6) 0.6819(6) 0.2354(9) 0.112(3) Uani 1 1 d . . . . .
H7A H 0.1410 0.7344 0.1893 0.168 Uiso 1 1 calc R U . . .
H7B H 0.0698 0.6886 0.2779 0.168 Uiso 1 1 calc R U . . .
H7C H 0.1214 0.6369 0.1647 0.168 Uiso 1 1 calc R U . . .
C8 C 0.3092(3) 0.4775(3) 0.8870(5) 0.0467(12) Uani 1 1 d . . . . .
C9 C 0.2998(5) 0.5527(4) 0.9586(7) 0.0645(16) Uani 1 1 d . . . . .
H9 H 0.2612 0.5943 0.9211 0.077 Uiso 1 1 calc R U . . .
C10 C 0.3488(5) 0.5665(5) 1.0894(7) 0.078(2) Uani 1 1 d . . . . .
H10 H 0.3450 0.6186 1.1374 0.093 Uiso 1 1 calc R U . . .
C11 C 0.4022(5) 0.5036(5) 1.1462(7) 0.0721(19) Uani 1 1 d . . . . .
H11 H 0.4332 0.5130 1.2345 0.087 Uiso 1 1 calc R U . . .
C12 C 0.4116(4) 0.4265(4) 1.0772(6) 0.0573(15) Uani 1 1 d . . . . .
C13 C 0.3646(3) 0.4144(4) 0.9440(6) 0.0502(13) Uani 1 1 d . . . . .
H13 H 0.3707 0.3635 0.8934 0.060 Uiso 1 1 calc R U . . .
C14 C 0.4705(5) 0.3581(6) 1.1403(8) 0.090(2) Uani 1 1 d . . . . .
H14A H 0.5103 0.3823 1.2138 0.134 Uiso 1 1 calc R U . . .
H14B H 0.5035 0.3335 1.0652 0.134 Uiso 1 1 calc R U . . .
H14C H 0.4356 0.3146 1.1826 0.134 Uiso 1 1 calc R U . . .
C15 C 0.1682(3) 0.3479(3) 0.6243(5) 0.0447(11) Uani 1 1 d . . . . .
C16 C 0.0925(4) 0.3552(4) 0.5338(7) 0.0634(16) Uani 1 1 d . . . . .
H16 H 0.0715 0.4085 0.5038 0.076 Uiso 1 1 calc R U . . .
C17 C 0.0492(5) 0.2817(5) 0.4895(8) 0.079(2) Uani 1 1 d . . . . .
H17 H -0.0006 0.2851 0.4264 0.095 Uiso 1 1 calc R U . . .
C18 C 0.0786(4) 0.2038(5) 0.5373(7) 0.0667(17) Uani 1 1 d . . . . .
H18 H 0.0481 0.1551 0.5057 0.080 Uiso 1 1 calc R U . . .
C19 C 0.1518(4) 0.1946(4) 0.6307(6) 0.0516(13) Uani 1 1 d . . . . .
C20 C 0.1982(4) 0.2695(4) 0.6730(6) 0.0497(13) Uani 1 1 d . . . . .
H20 H 0.2490 0.2658 0.7337 0.060 Uiso 1 1 calc R U . . .
C21 C 0.1816(5) 0.1093(4) 0.6872(8) 0.0716(18) Uani 1 1 d . . . . .
H21A H 0.1320 0.0781 0.7193 0.107 Uiso 1 1 calc R U . . .
H21B H 0.2241 0.1170 0.7672 0.107 Uiso 1 1 calc R U . . .
H21C H 0.2079 0.0779 0.6115 0.107 Uiso 1 1 calc R U . . .
Sb1 Sb 0.23956(2) 0.46026(2) 0.68267(3) 0.04004(9) Uani 1 1 d . . . . .
I1 I 0.08150(3) 0.53241(3) 0.78787(5) 0.06918(14) Uani 1 1 d . . . . .
I2 I 0.39220(3) 0.38833(3) 0.55988(5) 0.06305(13) Uani 1 1 d . . . . .


_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 C6 1.369(7) . ?
C1 C2 1.373(8) . ?
C1 Sb1 2.122(5) . ?
C2 C3 1.404(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(8) . ?
C5 C7 1.513(10) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.360(8) . ?
C8 C13 1.382(7) . ?
C8 Sb1 2.126(5) . ?
C9 C10 1.398(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(7) . ?
C12 C14 1.492(9) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.375(7) . ?
C15 C16 1.387(7) . ?
C15 Sb1 2.119(5) . ?
C16 C17 1.375(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.362(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.411(8) . ?
C19 C21 1.494(8) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
Sb1 I2 2.8722(8) . ?
Sb1 I1 2.8759(8) . ?

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
C6 C1 C2 120.7(5) . . ?
C6 C1 Sb1 122.2(4) . . ?
C2 C1 Sb1 117.1(4) . . ?
C1 C2 C3 118.6(6) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.9(7) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.8(6) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 118.3(6) . . ?
C4 C5 C7 120.9(7) . . ?
C6 C5 C7 120.8(7) . . ?
C1 C6 C5 120.7(6) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 120.8(5) . . ?
C9 C8 Sb1 118.7(4) . . ?
C13 C8 Sb1 120.5(4) . . ?
C8 C9 C10 119.2(6) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 119.8(6) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 122.1(6) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C13 117.6(6) . . ?
C11 C12 C14 121.6(6) . . ?
C13 C12 C14 120.8(6) . . ?
C8 C13 C12 120.5(5) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 121.2(5) . . ?
C20 C15 Sb1 120.1(4) . . ?
C16 C15 Sb1 118.7(4) . . ?
C17 C16 C15 118.5(6) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C18 C17 C16 120.6(6) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 122.4(6) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C20 117.4(5) . . ?
C18 C19 C21 122.1(6) . . ?
C20 C19 C21 120.5(5) . . ?
C15 C20 C19 119.9(5) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15 Sb1 C1 124.0(2) . . ?
C15 Sb1 C8 123.6(2) . . ?
C1 Sb1 C8 112.4(2) . . ?
C15 Sb1 I2 89.36(14) . . ?
C1 Sb1 I2 88.51(14) . . ?
C8 Sb1 I2 91.55(14) . . ?
C15 Sb1 I1 89.15(14) . . ?
C1 Sb1 I1 89.65(14) . . ?
C8 Sb1 I1 91.95(14) . . ?
I2 Sb1 I1 176.456(18) . . ?

_refine_diff_density_max         1.163
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.098

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

####################################################################### 
# 
# 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_1811
_database_code_depnum_ccdc_archive 'CCDC 1987109'
loop_
_audit_author_name
_audit_author_address
'Vladimir Sharutin'
;South Ural State University
Russia
;
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-07-30 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            'C18 H12 F3 I2 Sb'
_chemical_formula_weight         660.83

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'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.6690(17)
_cell_length_b                   9.4881(19)
_cell_length_c                   13.136(3)
_cell_angle_alpha                85.17(3)
_cell_angle_beta                 84.75(3)
_cell_angle_gamma                73.62(3)
_cell_volume                     1030.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4867
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.9

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.130
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    4.358
_shelx_estimated_absorpt_T_min   0.375
_shelx_estimated_absorpt_T_max   0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5315
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker-AXS, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_reflns_number            27698
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.808
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.500
_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             3907
_reflns_number_gt                3003
_reflns_threshold_expression     >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       'APEX2 (Bruker-AXS, 2004)'
_computing_cell_refinement       'SAINT (Bruker-AXS, 2004)'
_computing_data_reduction        'SAINT (Bruker-AXS, 2004)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0778P)²+3.0161P] 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         3907
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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
C1 C 0.1708(9) 0.7086(8) 0.3931(5) 0.0613(17) Uani 1 1 d . . . . .
C2 C 0.2067(11) 0.6097(9) 0.4777(6) 0.076(2) Uani 1 1 d . . . . .
H2 H 0.3037 0.5359 0.4776 0.092 Uiso 1 1 calc R U . . .
C3 C 0.0971(13) 0.6220(11) 0.5619(7) 0.087(3) Uani 1 1 d . . . . .
H3 H 0.1173 0.5557 0.6187 0.104 Uiso 1 1 calc R U . . .
C4 C -0.0428(12) 0.7350(12) 0.5592(7) 0.084(3) Uani 1 1 d . . . . .
C5 C -0.0806(11) 0.8342(12) 0.4789(8) 0.090(3) Uani 1 1 d . . . . .
H5 H -0.1760 0.9099 0.4814 0.108 Uiso 1 1 calc R U . . .
C6 C 0.0270(11) 0.8203(11) 0.3920(7) 0.088(3) Uani 1 1 d . . . . .
H6 H 0.0029 0.8845 0.3346 0.106 Uiso 1 1 calc R U . . .
C7 C 0.3133(8) 0.8774(7) 0.1561(5) 0.0573(16) Uani 1 1 d . . . . .
C8 C 0.3129(13) 0.8661(11) 0.0514(7) 0.088(3) Uani 1 1 d . . . . .
H8 H 0.3243 0.7755 0.0250 0.106 Uiso 1 1 calc R U . . .
C9 C 0.2948(15) 0.9944(13) -0.0140(7) 0.104(4) Uani 1 1 d . . . . .
H9 H 0.2962 0.9892 -0.0845 0.124 Uiso 1 1 calc R U . . .
C10 C 0.2756(12) 1.1237(10) 0.0261(8) 0.086(3) Uani 1 1 d . . . . .
C11 C 0.2739(12) 1.1374(9) 0.1269(8) 0.088(3) Uani 1 1 d . . . . .
H11 H 0.2587 1.2296 0.1518 0.106 Uiso 1 1 calc R U . . .
C12 C 0.2949(11) 1.0135(8) 0.1942(6) 0.073(2) Uani 1 1 d . . . . .
H12 H 0.2967 1.0218 0.2641 0.088 Uiso 1 1 calc R U . . .
C13 C 0.5195(9) 0.4843(7) 0.2437(5) 0.0577(16) Uani 1 1 d . . . . .
C14 C 0.6646(11) 0.4832(9) 0.1887(7) 0.077(2) Uani 1 1 d . . . . .
H14 H 0.6818 0.5708 0.1597 0.092 Uiso 1 1 calc R U . . .
C15 C 0.7841(12) 0.3513(10) 0.1770(7) 0.085(2) Uani 1 1 d . . . . .
H15 H 0.8796 0.3484 0.1377 0.103 Uiso 1 1 calc R U . . .
C16 C 0.7572(11) 0.2262(9) 0.2250(7) 0.076(2) Uani 1 1 d . . . . .
C17 C 0.6178(12) 0.2237(9) 0.2822(8) 0.086(3) Uani 1 1 d . . . . .
H17 H 0.6051 0.1368 0.3154 0.104 Uiso 1 1 calc R U . . .
C18 C 0.4949(10) 0.3551(8) 0.2895(7) 0.073(2) Uani 1 1 d . . . . .
H18 H 0.3969 0.3556 0.3250 0.088 Uiso 1 1 calc R U . . .
F1 F -0.1531(9) 0.7491(8) 0.6419(5) 0.126(2) Uani 1 1 d . . . . .
F2 F 0.2600(9) 1.2459(7) -0.0405(5) 0.131(3) Uani 1 1 d . . . . .
F3 F 0.8754(8) 0.0949(6) 0.2157(6) 0.116(2) Uani 1 1 d . . . . .
Sb1 Sb 0.33463(6) 0.68844(5) 0.26157(4) 0.05596(19) Uani 1 1 d . . . . .
I1 I 0.55137(8) 0.78178(7) 0.37897(5) 0.0889(3) Uani 1 1 d . . . . .
I2 I 0.11899(8) 0.58938(7) 0.15315(6) 0.0899(3) Uani 1 1 d . . . . .


_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 C6 1.390(12) . ?
C1 C2 1.391(10) . ?
C1 Sb1 2.120(8) . ?
C2 C3 1.381(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.352(13) . ?
C4 F1 1.370(10) . ?
C5 C6 1.396(13) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.386(11) . ?
C7 C8 1.388(11) . ?
C7 Sb1 2.147(6) . ?
C8 C9 1.410(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.336(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.341(14) . ?
C10 F2 1.375(8) . ?
C11 C12 1.389(10) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.382(9) . ?
C13 C14 1.390(11) . ?
C13 Sb1 2.152(7) . ?
C14 C15 1.391(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(13) . ?
C16 F3 1.378(10) . ?
C17 C18 1.396(12) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
Sb1 I2 2.8478(10) . ?
Sb1 I1 2.8967(10) . ?

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
C6 C1 C2 121.2(8) . . ?
C6 C1 Sb1 118.7(6) . . ?
C2 C1 Sb1 120.1(6) . . ?
C3 C2 C1 119.4(8) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 118.0(8) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C5 C4 F1 116.9(10) . . ?
C5 C4 C3 124.2(9) . . ?
F1 C4 C3 118.9(9) . . ?
C4 C5 C6 118.4(9) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 118.8(8) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C12 C7 C8 119.8(7) . . ?
C12 C7 Sb1 119.0(5) . . ?
C8 C7 Sb1 121.2(6) . . ?
C7 C8 C9 118.7(9) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 119.5(9) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 122.8(8) . . ?
C9 C10 F2 117.6(10) . . ?
C11 C10 F2 119.7(9) . . ?
C10 C11 C12 119.8(9) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 119.4(8) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C18 C13 C14 120.2(7) . . ?
C18 C13 Sb1 119.7(6) . . ?
C14 C13 Sb1 120.1(5) . . ?
C13 C14 C15 120.2(7) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 118.1(8) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C17 123.4(8) . . ?
C15 C16 F3 118.9(9) . . ?
C17 C16 F3 117.7(8) . . ?
C16 C17 C18 118.3(7) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C13 C18 C17 119.8(8) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C1 Sb1 C7 117.9(3) . . ?
C1 Sb1 C13 118.7(3) . . ?
C7 Sb1 C13 123.4(3) . . ?
C1 Sb1 I2 89.82(19) . . ?
C7 Sb1 I2 91.01(19) . . ?
C13 Sb1 I2 91.53(19) . . ?
C1 Sb1 I1 88.48(19) . . ?
C7 Sb1 I1 91.16(19) . . ?
C13 Sb1 I1 87.93(19) . . ?
I2 Sb1 I1 177.69(2) . . ?

_refine_diff_density_max         0.701
_refine_diff_density_min         -1.581
_refine_diff_density_rms         0.195

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

####################################################################### 
# 
# 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_1827
_database_code_depnum_ccdc_archive 'CCDC 1989078'
loop_
_audit_author_name
_audit_author_address
'Vladimir Sharutin'
;South Ural State University
Russia
;
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 Br0.60 I1.40 Sb'
_chemical_formula_weight         620.73

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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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      cubic
_space_group_IT_number           212
_space_group_name_H-M_alt        'P 43 3 2'
_space_group_name_Hall           'P 4acd 2ab 3'

_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'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+1/2'
'y+1/4, x+3/4, -z+3/4'
'-y+1/4, -x+1/4, -z+1/4'
'y+3/4, -x+3/4, z+1/4'
'-y+3/4, x+1/4, z+3/4'
'x+1/4, z+3/4, -y+3/4'
'-x+3/4, z+1/4, y+3/4'
'-x+1/4, -z+1/4, -y+1/4'
'x+3/4, -z+3/4, y+1/4'
'z+1/4, y+3/4, -x+3/4'
'z+3/4, -y+3/4, x+1/4'
'-z+3/4, y+1/4, x+3/4'
'-z+1/4, -y+1/4, -x+1/4'

_cell_length_a                   13.0818(15)
_cell_length_b                   13.0818(15)
_cell_length_c                   13.0818(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2238.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2719
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      32.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_F_000             1173
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    4.234
_shelx_estimated_absorpt_T_min   0.406
_shelx_estimated_absorpt_T_max   0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5791
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   'SADABS (Bruker-AXS, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 25
_diffrn_reflns_number            26013
_diffrn_reflns_av_unetI/netI     0.0068
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.482
_diffrn_reflns_theta_max         25.654
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             720
_reflns_number_gt                685
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.522
_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       'APEX2 (Bruker-AXS, 2004)'
_computing_cell_refinement       'SAINT (Bruker-AXS, 2004)'
_computing_data_reduction        'SAINT (Bruker-AXS, 2004)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0288P)²+1.9858P] 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 227 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         720
_refine_ls_number_parameters     42
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0647
_refine_ls_wR_factor_gt          0.0622
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_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 0.375000 0.7606(4) 0.5106(4) 0.0506(14) Uani 1 2 d S T P . .
C2 C 0.4652(4) 0.7243(5) 0.4714(5) 0.0679(13) Uani 1 1 d . . . . .
H2 H 0.526950 0.751169 0.494260 0.082 Uiso 1 1 calc R U . . .
C3 C 0.4653(5) 0.6487(5) 0.3987(5) 0.0729(16) Uani 1 1 d . . . . .
H3 H 0.527296 0.623184 0.375219 0.087 Uiso 1 1 calc R U . . .
C4 C 0.375000 0.6096(4) 0.3596(4) 0.0655(18) Uani 1 2 d S T P . .
C5 C 0.375000 0.5284(5) 0.2784(5) 0.097(3) Uani 1 2 d S T P . .
H5A H 0.314665 0.535055 0.237168 0.145 Uiso 0.5 1 calc R U P . .
H5B H 0.375843 0.462192 0.310031 0.145 Uiso 0.5 1 calc R U P . .
H5C H 0.434492 0.536088 0.236135 0.145 Uiso 0.5 1 calc R U P . .
Sb1 Sb 0.375000 0.875000 0.625000 0.0492(2) Uani 1 6 d S T P . .
I1 I 0.5004(5) 1.0004(5) 0.4996(5) 0.0766(13) Uani 0.7 3 d S T P . .
Br1 Br 0.4953(19) 0.9953(19) 0.5047(19) 0.084(7) Uani 0.3 3 d S T 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
C1 C2 1.372(6) . ?
C1 C2 1.372(6) 18_554 ?
C1 Sb1 2.117(7) . ?
C2 C3 1.371(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.502(11) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 H5A 0.9600 18_554 ?
C5 H5B 0.9600 18_554 ?
C5 H5C 0.9600 18_554 ?
Sb1 Br1 2.73(4) . ?
Sb1 Br1 2.73(4) 14_666 ?
Sb1 I1 2.841(12) 14_666 ?
Sb1 I1 2.841(12) . ?

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
C2 C1 C2 118.8(7) . 18_554 ?
C2 C1 Sb1 120.6(3) . . ?
C2 C1 Sb1 120.6(3) 18_554 . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.5(6) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C3 117.0(7) 18_554 . ?
C3 C4 C5 121.5(4) 18_554 . ?
C3 C4 C5 121.5(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C5 H5A 109.469(1) . 18_554 ?
H5A C5 H5A 141.1 . 18_554 ?
H5B C5 H5A 56.3 . 18_554 ?
H5C C5 H5A 56.3 . 18_554 ?
C4 C5 H5B 109.473(1) . 18_554 ?
H5A C5 H5B 56.3 . 18_554 ?
H5B C5 H5B 141.1 . 18_554 ?
H5C C5 H5B 56.2 . 18_554 ?
H5A C5 H5B 109.5 18_554 18_554 ?
C4 C5 H5C 109.5 . 18_554 ?
H5A C5 H5C 56.3 . 18_554 ?
H5B C5 H5C 56.3 . 18_554 ?
H5C C5 H5C 141.1 . 18_554 ?
H5A C5 H5C 109.5 18_554 18_554 ?
H5B C5 H5C 109.5 18_554 18_554 ?
C1 Sb1 C1 120.0 . 8_656 ?
C1 Sb1 C1 120.0 . 11_466 ?
C1 Sb1 C1 120.0 8_656 11_466 ?
C1 Sb1 Br1 90.000(1) . . ?
C1 Sb1 Br1 90.000(5) 8_656 . ?
C1 Sb1 Br1 90.000(2) 11_466 . ?
C1 Sb1 Br1 90.000(4) . 14_666 ?
C1 Sb1 Br1 90.000(1) 8_656 14_666 ?
C1 Sb1 Br1 90.000(3) 11_466 14_666 ?
Br1 Sb1 Br1 180.0 . 14_666 ?
C1 Sb1 I1 90.000(1) . 14_666 ?
C1 Sb1 I1 90.0 8_656 14_666 ?
C1 Sb1 I1 90.000(1) 11_466 14_666 ?
Br1 Sb1 I1 180.0(3) . 14_666 ?
Br1 Sb1 I1 0.0(3) 14_666 14_666 ?
C1 Sb1 I1 90.0 . . ?
C1 Sb1 I1 90.000(1) 8_656 . ?
C1 Sb1 I1 90.000(1) 11_466 . ?
Br1 Sb1 I1 0.0(5) . . ?
Br1 Sb1 I1 180.0(5) 14_666 . ?
I1 Sb1 I1 180.0 14_666 . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.081

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

