# 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. 
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data_jane_05072019_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2008416'
loop_
_audit_author_name
_audit_author_address
'Gyeongjin Park'
;Texas AM university
United States of America
;
_audit_update_record             
;
2020-06-06 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_date             2020-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        BrC30Cl2SSb
_chemical_formula_moiety         'C30 H24 Br S Sb, C H2 Cl2'
_chemical_formula_sum            'C31 H26 Br Cl2 S Sb'
_chemical_formula_weight         703.14
_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'
Br Br -0.2901 2.4595 '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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1739(16)
_cell_length_b                   11.503(2)
_cell_length_c                   14.471(3)
_cell_angle_alpha                91.549(4)
_cell_angle_beta                 92.383(4)
_cell_angle_gamma                113.406(4)
_cell_volume                     1398.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9687
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   0.443
_shelx_estimated_absorpt_T_min   0.411
_exptl_absorpt_coefficient_mu    2.700
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1010 before and 0.0754 after correction.
The Ratio of minimum to maximum transmission is 0.7740.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            66623
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.583
_diffrn_reflns_theta_min         2.445
_diffrn_ambient_temperature      109.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5811
_reflns_number_total             6426
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.182
_refine_diff_density_min         -1.150
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         6426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+4.6266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0819
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C18(H18), C17(H17), C16(H16), C15(H15), C24(H24), C23(H23), C22(H22),
  C21(H21), C20(H20), C26(H26), C30(H30), C29(H29), C28(H28), C27(H27)
2.c Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C12(C7,C8,C9,C10,C11), C14(C13,C18,C17,C16,C15), C19(C24,
 C23,C22,C21,C20), C26(C25,C30,C29,C28,C27)
;
_atom_sites_solution_hydrogens   geom
_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
Sb Sb 0.63896(2) 0.83011(2) 0.74271(2) 0.01631(6) Uani 1 1 d . . . . .
Br Br 0.89323(4) 1.09106(3) 0.74645(2) 0.02488(9) Uani 1 1 d . . . . .
S S 0.60062(10) 0.89155(8) 0.96827(6) 0.02211(16) Uani 1 1 d . . . . .
C1 C 0.7899(2) 0.8223(2) 0.85613(11) 0.0191(6) Uani 1 1 d . . . . .
C2 C 0.7596(2) 0.8451(2) 0.94668(13) 0.0193(6) Uani 1 1 d G . . . .
C3 C 0.8571(3) 0.8361(2) 1.01981(10) 0.0235(7) Uani 1 1 d G . . . .
H3 H 0.836418 0.851624 1.081699 0.028 Uiso 1 1 calc R . . . .
C4 C 0.9850(2) 0.8044(2) 1.00241(12) 0.0254(7) Uani 1 1 d G . . . .
H4 H 1.051714 0.798291 1.052390 0.030 Uiso 1 1 calc R . . . .
C5 C 1.0154(2) 0.7817(2) 0.91186(14) 0.0246(7) Uani 1 1 d G . . . .
H5 H 1.102775 0.760037 0.899962 0.030 Uiso 1 1 calc R . . . .
C6 C 0.9178(2) 0.7906(2) 0.83872(10) 0.0232(6) Uani 1 1 d G . . . .
H6 H 0.938538 0.775116 0.776841 0.028 Uiso 1 1 calc R . . . .
C12 C 0.51210(19) 0.54716(19) 0.77184(16) 0.0260(7) Uani 1 1 d . . . . .
H12 H 0.622767 0.565753 0.773220 0.031 Uiso 1 1 calc R . . . .
C7 C 0.4583(2) 0.64230(15) 0.75536(16) 0.0205(6) Uani 1 1 d G . . . .
C8 C 0.2963(2) 0.61509(18) 0.75333(16) 0.0266(7) Uani 1 1 d G . . . .
H8 H 0.259540 0.680111 0.742071 0.032 Uiso 1 1 calc R . . . .
C9 C 0.18824(18) 0.4927(2) 0.76779(18) 0.0348(9) Uani 1 1 d G . . . .
H9 H 0.077565 0.474146 0.766401 0.042 Uiso 1 1 calc R . . . .
C10 C 0.2421(2) 0.39760(16) 0.78426(17) 0.0344(9) Uani 1 1 d G . . . .
H10 H 0.168188 0.313983 0.794141 0.041 Uiso 1 1 calc R . . . .
C11 C 0.4040(3) 0.42481(17) 0.78629(17) 0.0311(8) Uani 1 1 d G . . . .
H11 H 0.440788 0.359785 0.797551 0.037 Uiso 1 1 calc R . . . .
C14 C 0.61986(19) 0.69610(19) 0.55749(14) 0.0218(6) Uani 1 1 d . . . . .
H14 H 0.513512 0.651034 0.574071 0.026 Uiso 1 1 calc R . . . .
C13 C 0.7262(2) 0.79237(19) 0.61666(11) 0.0186(6) Uani 1 1 d G . . . .
C18 C 0.8818(2) 0.85830(18) 0.59240(14) 0.0243(7) Uani 1 1 d G . . . .
H18 H 0.954445 0.924095 0.632843 0.029 Uiso 1 1 calc R . . . .
C17 C 0.9311(2) 0.8280(2) 0.50896(15) 0.0302(8) Uani 1 1 d G . . . .
H17 H 1.037404 0.873023 0.492372 0.036 Uiso 1 1 calc R . . . .
C16 C 0.8247(3) 0.7317(2) 0.44978(12) 0.0308(8) Uani 1 1 d G . . . .
H16 H 0.858419 0.710957 0.392749 0.037 Uiso 1 1 calc R . . . .
C15 C 0.6691(2) 0.66576(19) 0.47404(13) 0.0289(7) Uani 1 1 d G . . . .
H15 H 0.596473 0.599962 0.433597 0.035 Uiso 1 1 calc R . . . .
C19 C 0.4971(2) 0.9350(2) 0.71970(14) 0.0199(6) Uani 1 1 d . . . . .
C24 C 0.5201(3) 1.0047(2) 0.64059(14) 0.0291(7) Uani 1 1 d G . . . .
H24 H 0.600418 1.007045 0.600388 0.035 Uiso 1 1 calc R . . . .
C23 C 0.4256(3) 1.0708(2) 0.62029(14) 0.0366(9) Uani 1 1 d G . . . .
H23 H 0.441262 1.118363 0.566213 0.044 Uiso 1 1 calc R . . . .
C22 C 0.3080(3) 1.0673(2) 0.67910(16) 0.0312(8) Uani 1 1 d G . . . .
H22 H 0.243412 1.112467 0.665224 0.037 Uiso 1 1 calc R . . . .
C21 C 0.2850(2) 0.9976(2) 0.75822(14) 0.0256(7) Uani 1 1 d G . . . .
H21 H 0.204718 0.995255 0.798412 0.031 Uiso 1 1 calc R . . . .
C20 C 0.3796(2) 0.9315(2) 0.77852(12) 0.0233(6) Uani 1 1 d G . . . .
H20 H 0.363874 0.883937 0.832590 0.028 Uiso 1 1 calc R . . . .
C26 C 0.4241(3) 0.63431(19) 0.99250(14) 0.0257(7) Uani 1 1 d . . . . .
H26 H 0.483453 0.616894 0.945822 0.031 Uiso 1 1 calc R . . . .
C25 C 0.4589(2) 0.75889(16) 1.02218(14) 0.0199(6) Uani 1 1 d G . . . .
C30 C 0.3721(3) 0.78437(14) 1.09048(15) 0.0226(6) Uani 1 1 d G . . . .
H30 H 0.395865 0.869518 1.110770 0.027 Uiso 1 1 calc R . . . .
C29 C 0.2505(3) 0.68526(19) 1.12910(15) 0.0284(7) Uani 1 1 d G . . . .
H29 H 0.191186 0.702672 1.175783 0.034 Uiso 1 1 calc R . . . .
C28 C 0.2157(2) 0.56067(17) 1.09942(16) 0.0289(7) Uani 1 1 d G . . . .
H28 H 0.132638 0.492937 1.125815 0.035 Uiso 1 1 calc R . . . .
C27 C 0.3025(3) 0.53520(14) 1.03112(16) 0.0293(7) Uani 1 1 d G . . . .
H27 H 0.278770 0.450046 1.010835 0.035 Uiso 1 1 calc R . . . .
Cl1 Cl 1.23211(19) 0.7090(2) 0.51728(11) 0.0786(5) Uani 1 1 d . . . . .
Cl2 Cl 1.1959(3) 0.5238(2) 0.36740(12) 0.0996(7) Uani 1 1 d . . . . .
C31 C 1.1537(15) 0.6430(8) 0.4091(6) 0.139(5) Uani 1 1 d . . . . .
H31A H 1.036481 0.612319 0.409695 0.167 Uiso 1 1 calc R . . . .
H31B H 1.189311 0.711476 0.364702 0.167 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
Sb Br 2.9785(6) . ?
Sb C1 2.1301(14) . ?
Sb C7 2.1565(15) . ?
Sb C13 2.1237(14) . ?
Sb C19 2.1199(15) . ?
S C2 1.7774(16) . ?
S C25 1.7889(17) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C12 C7 1.3900 . ?
C12 C11 1.3900 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C14 C13 1.3900 . ?
C14 C15 1.3900 . ?
C13 C18 1.3900 . ?
C18 C17 1.3900 . ?
C17 C16 1.3900 . ?
C16 C15 1.3900 . ?
C19 C24 1.3900 . ?
C19 C20 1.3900 . ?
C24 C23 1.3900 . ?
C23 C22 1.3900 . ?
C22 C21 1.3900 . ?
C21 C20 1.3900 . ?
C26 C25 1.3900 . ?
C26 C27 1.3900 . ?
C25 C30 1.3900 . ?
C30 C29 1.3900 . ?
C29 C28 1.3900 . ?
C28 C27 1.3900 . ?
Cl1 C31 1.719(7) . ?
Cl2 C31 1.669(9) . ?

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
C1 Sb Br 79.22(6) . . ?
C1 Sb C7 95.91(8) . . ?
C7 Sb Br 174.08(6) . . ?
C13 Sb Br 87.86(6) . . ?
C13 Sb C1 109.56(8) . . ?
C13 Sb C7 97.00(8) . . ?
C19 Sb Br 80.31(6) . . ?
C19 Sb C1 133.58(8) . . ?
C19 Sb C7 100.99(8) . . ?
C19 Sb C13 110.79(8) . . ?
C2 S C25 104.23(11) . . ?
C2 C1 Sb 120.96(10) . . ?
C2 C1 C6 120.0 . . ?
C6 C1 Sb 119.01(10) . . ?
C1 C2 S 119.79(11) . . ?
C3 C2 S 120.16(11) . . ?
C3 C2 C1 120.0 . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C7 C12 C11 120.0 . . ?
C12 C7 Sb 116.22(11) . . ?
C12 C7 C8 120.0 . . ?
C8 C7 Sb 123.66(11) . . ?
C9 C8 C7 120.0 . . ?
C8 C9 C10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C10 C11 C12 120.0 . . ?
C13 C14 C15 120.0 . . ?
C14 C13 Sb 116.91(10) . . ?
C14 C13 C18 120.0 . . ?
C18 C13 Sb 123.09(10) . . ?
C17 C18 C13 120.0 . . ?
C18 C17 C16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C16 C15 C14 120.0 . . ?
C24 C19 Sb 117.74(11) . . ?
C24 C19 C20 120.0 . . ?
C20 C19 Sb 122.20(11) . . ?
C19 C24 C23 120.0 . . ?
C22 C23 C24 120.0 . . ?
C23 C22 C21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C21 C20 C19 120.0 . . ?
C25 C26 C27 120.0 . . ?
C26 C25 S 122.41(12) . . ?
C26 C25 C30 120.0 . . ?
C30 C25 S 117.33(12) . . ?
C25 C30 C29 120.0 . . ?
C28 C29 C30 120.0 . . ?
C27 C28 C29 120.0 . . ?
C28 C27 C26 120.0 . . ?
Cl2 C31 Cl1 118.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Sb C1 C2 S -4.19(16) . . . . ?
Sb C1 C2 C3 178.25(15) . . . . ?
Sb C1 C6 C5 -178.29(15) . . . . ?
Sb C7 C8 C9 -175.96(16) . . . . ?
Sb C13 C18 C17 179.58(16) . . . . ?
Sb C19 C24 C23 177.30(16) . . . . ?
Sb C19 C20 C21 -177.18(16) . . . . ?
S C2 C3 C4 -177.54(17) . . . . ?
S C25 C30 C29 174.30(17) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 S C25 C26 -40.95(16) . . . . ?
C2 S C25 C30 144.90(13) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C6 C1 C2 S 177.55(16) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
C7 C12 C11 C10 0.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C11 C12 C7 Sb 176.25(15) . . . . ?
C11 C12 C7 C8 0.0 . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C13 C18 C17 C16 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C17 C16 C15 C14 0.0 . . . . ?
C15 C14 C13 Sb -179.61(15) . . . . ?
C15 C14 C13 C18 0.0 . . . . ?
C19 C24 C23 C22 0.0 . . . . ?
C24 C19 C20 C21 0.0 . . . . ?
C24 C23 C22 C21 0.0 . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C22 C21 C20 C19 0.0 . . . . ?
C20 C19 C24 C23 0.0 . . . . ?
C26 C25 C30 C29 0.0 . . . . ?
C25 S C2 C1 111.78(13) . . . . ?
C25 S C2 C3 -70.67(14) . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C25 C30 C29 C28 0.0 . . . . ?
C30 C29 C28 C27 0.0 . . . . ?
C29 C28 C27 C26 0.0 . . . . ?
C27 C26 C25 S -174.00(18) . . . . ?
C27 C26 C25 C30 0.0 . . . . ?

_olex2_submission_original_sample_id J
_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_jj_bf4_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2008417'
loop_
_audit_author_name
_audit_author_address
'Gyeongjin Park'
;Texas AM university
United States of America
;
_audit_update_record             
;
2020-06-06 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_date             2020-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        C30H24SBF4Sb
_chemical_formula_moiety         'C30 H24 S Sb, B F4'
_chemical_formula_sum            'C30 H24 B F4 S Sb'
_chemical_formula_weight         625.11
_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'
B B 0.0013 0.0007 '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'
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'

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

_cell_length_a                   7.9877(11)
_cell_length_b                   15.558(2)
_cell_length_c                   21.445(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2665.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.716
_exptl_absorpt_coefficient_mu    1.159
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1791 before and 0.0723 after correction.
The Ratio of minimum to maximum transmission is 0.8847.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.3088
_exptl_crystal_size_mid          0.1806
_exptl_crystal_size_min          0.1395
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            37617
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         2.618
_diffrn_ambient_temperature      110.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5875
_reflns_number_total             6122
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.504
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         6122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.072
_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)+(0.0453P)²+1.2439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0770
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.51(3)
 0.49(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
  C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Sb Sb 0.47451(3) 0.40506(2) 0.68044(2) 0.02621(9) Uani 1 1 d . . . . .
S S 0.76252(17) 0.53993(8) 0.62994(6) 0.0364(3) Uani 1 1 d . . . . .
C1 C 0.6258(6) 0.3827(3) 0.60219(19) 0.0261(9) Uani 1 1 d . . . . .
C2 C 0.7383(6) 0.4466(3) 0.5839(2) 0.0284(9) Uani 1 1 d . . . . .
C3 C 0.8371(7) 0.4327(3) 0.5313(2) 0.0379(11) Uani 1 1 d . . . . .
H3 H 0.914587 0.475344 0.518154 0.045 Uiso 1 1 calc R . . . .
C4 C 0.8223(8) 0.3573(4) 0.4984(2) 0.0447(13) Uani 1 1 d . . . . .
H4 H 0.887251 0.348959 0.461746 0.054 Uiso 1 1 calc R . . . .
C5 C 0.7143(8) 0.2937(3) 0.5179(2) 0.0436(12) Uani 1 1 d . . . . .
H5 H 0.707744 0.241251 0.495358 0.052 Uiso 1 1 calc R . . . .
C6 C 0.6152(6) 0.3059(3) 0.5700(2) 0.0329(10) Uani 1 1 d . . . . .
H6 H 0.540872 0.262051 0.583604 0.039 Uiso 1 1 calc R . . . .
C7 C 0.3078(5) 0.3007(3) 0.6819(2) 0.0275(8) Uani 1 1 d . . . . .
C8 C 0.3478(7) 0.2259(3) 0.7142(2) 0.0394(11) Uani 1 1 d . . . . .
H8 H 0.446064 0.223448 0.739096 0.047 Uiso 1 1 calc R . . . .
C9 C 0.2435(8) 0.1549(3) 0.7098(3) 0.0454(13) Uani 1 1 d . . . . .
H9 H 0.269973 0.103775 0.731906 0.054 Uiso 1 1 calc R . . . .
C10 C 0.1013(7) 0.1585(3) 0.6735(2) 0.0400(11) Uani 1 1 d . . . . .
H10 H 0.031054 0.109477 0.670094 0.048 Uiso 1 1 calc R . . . .
C11 C 0.0604(7) 0.2328(3) 0.6421(2) 0.0411(11) Uani 1 1 d . . . . .
H11 H -0.039099 0.235320 0.617848 0.049 Uiso 1 1 calc R . . . .
C12 C 0.1645(6) 0.3040(3) 0.6458(2) 0.0360(10) Uani 1 1 d . . . . .
H12 H 0.137503 0.354966 0.623536 0.043 Uiso 1 1 calc R . . . .
C13 C 0.3348(6) 0.5183(3) 0.6710(2) 0.0323(10) Uani 1 1 d . . . . .
C14 C 0.2732(7) 0.5382(4) 0.6124(3) 0.0420(12) Uani 1 1 d . . . . .
H14 H 0.287283 0.499660 0.578471 0.050 Uiso 1 1 calc R . . . .
C15 C 0.1902(8) 0.6159(4) 0.6044(3) 0.0549(15) Uani 1 1 d . . . . .
H15 H 0.146957 0.630736 0.564555 0.066 Uiso 1 1 calc R . . . .
C16 C 0.1704(8) 0.6712(4) 0.6535(4) 0.0623(19) Uani 1 1 d . . . . .
H16 H 0.115397 0.724626 0.647163 0.075 Uiso 1 1 calc R . . . .
C17 C 0.2295(8) 0.6501(4) 0.7123(4) 0.0559(16) Uani 1 1 d . . . . .
H17 H 0.212480 0.688257 0.746336 0.067 Uiso 1 1 calc R . . . .
C18 C 0.3137(8) 0.5732(3) 0.7214(3) 0.0441(13) Uani 1 1 d . . . . .
H18 H 0.356117 0.558314 0.761313 0.053 Uiso 1 1 calc R . . . .
C19 C 0.6306(6) 0.4059(3) 0.75868(19) 0.0327(9) Uani 1 1 d . . . . .
C20 C 0.5655(8) 0.4275(3) 0.8173(2) 0.0463(12) Uani 1 1 d . . . . .
H20 H 0.448365 0.434661 0.822955 0.056 Uiso 1 1 calc R . . . .
C21 C 0.6747(10) 0.4381(4) 0.8667(3) 0.0569(17) Uani 1 1 d . . . . .
H21 H 0.632800 0.452343 0.906833 0.068 Uiso 1 1 calc R . . . .
C22 C 0.8458(10) 0.4278(4) 0.8576(3) 0.062(2) Uani 1 1 d . . . . .
H22 H 0.920415 0.436956 0.891481 0.074 Uiso 1 1 calc R . . . .
C23 C 0.9090(7) 0.4046(4) 0.8002(3) 0.0518(13) Uani 1 1 d . . . . .
H23 H 1.025879 0.395966 0.794913 0.062 Uiso 1 1 calc R . . . .
C24 C 0.8003(7) 0.3938(4) 0.7499(2) 0.0396(11) Uani 1 1 d . . . . .
H24 H 0.842477 0.378368 0.710009 0.047 Uiso 1 1 calc R . . . .
C25 C 0.6693(7) 0.6219(3) 0.5839(2) 0.0389(11) Uani 1 1 d . . . . .
C26 C 0.5778(7) 0.6070(3) 0.5300(2) 0.0409(11) Uani 1 1 d . . . . .
H26 H 0.571522 0.550620 0.513127 0.049 Uiso 1 1 calc R . . . .
C27 C 0.4953(9) 0.6744(4) 0.5006(3) 0.0526(15) Uani 1 1 d . . . . .
H27 H 0.430701 0.663599 0.464217 0.063 Uiso 1 1 calc R . . . .
C28 C 0.5066(10) 0.7561(4) 0.5237(3) 0.0630(19) Uani 1 1 d . . . . .
H28 H 0.447511 0.801829 0.504282 0.076 Uiso 1 1 calc R . . . .
C29 C 0.6058(10) 0.7714(4) 0.5760(3) 0.065(2) Uani 1 1 d . . . . .
H29 H 0.618538 0.828611 0.590771 0.079 Uiso 1 1 calc R . . . .
C30 C 0.6860(9) 0.7050(3) 0.6069(3) 0.0528(15) Uani 1 1 d . . . . .
H30 H 0.751271 0.715961 0.643077 0.063 Uiso 1 1 calc R . . . .
F1 F 1.3462(7) 0.6035(3) 0.8991(2) 0.0902(15) Uani 1 1 d . . . . .
F2 F 1.1128(8) 0.5642(3) 0.9528(2) 0.0927(16) Uani 1 1 d . . . . .
F3 F 1.2081(5) 0.4867(3) 0.8726(2) 0.0741(12) Uani 1 1 d . . . . .
F4 F 1.3529(6) 0.4838(3) 0.9598(2) 0.0722(11) Uani 1 1 d . . . . .
B B 1.2559(9) 0.5384(4) 0.9236(3) 0.0486(15) 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
Sb C1 2.097(4) . ?
Sb C7 2.100(4) . ?
Sb C13 2.095(5) . ?
Sb C19 2.090(4) . ?
S C2 1.766(5) . ?
S C25 1.775(6) . ?
C1 C2 1.396(6) . ?
C1 C6 1.382(6) . ?
C2 C3 1.395(6) . ?
C3 C4 1.374(8) . ?
C4 C5 1.378(8) . ?
C5 C6 1.384(7) . ?
C7 C8 1.391(6) . ?
C7 C12 1.383(6) . ?
C8 C9 1.386(8) . ?
C9 C10 1.379(8) . ?
C10 C11 1.377(7) . ?
C11 C12 1.388(7) . ?
C13 C14 1.386(7) . ?
C13 C18 1.386(7) . ?
C14 C15 1.388(8) . ?
C15 C16 1.369(10) . ?
C16 C17 1.387(11) . ?
C17 C18 1.386(9) . ?
C19 C20 1.400(7) . ?
C19 C24 1.382(7) . ?
C20 C21 1.383(8) . ?
C21 C22 1.390(11) . ?
C22 C23 1.379(10) . ?
C23 C24 1.395(7) . ?
C25 C26 1.388(8) . ?
C25 C30 1.390(7) . ?
C26 C27 1.389(7) . ?
C27 C28 1.367(9) . ?
C28 C29 1.395(11) . ?
C29 C30 1.385(10) . ?
F1 B 1.351(8) . ?
F2 B 1.364(9) . ?
F3 B 1.411(8) . ?
F4 B 1.386(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
C1 Sb C7 104.44(17) . . ?
C13 Sb C1 111.68(17) . . ?
C13 Sb C7 108.30(17) . . ?
C19 Sb C1 107.45(17) . . ?
C19 Sb C7 111.77(18) . . ?
C19 Sb C13 112.9(2) . . ?
C2 S C25 103.5(2) . . ?
C2 C1 Sb 118.5(3) . . ?
C6 C1 Sb 120.5(3) . . ?
C6 C1 C2 121.0(4) . . ?
C1 C2 S 120.0(3) . . ?
C3 C2 S 121.2(4) . . ?
C3 C2 C1 118.8(4) . . ?
C4 C3 C2 120.0(5) . . ?
C3 C4 C5 120.7(5) . . ?
C4 C5 C6 120.4(5) . . ?
C1 C6 C5 119.1(5) . . ?
C8 C7 Sb 120.6(3) . . ?
C12 C7 Sb 119.1(3) . . ?
C12 C7 C8 120.0(4) . . ?
C9 C8 C7 119.6(5) . . ?
C10 C9 C8 120.1(5) . . ?
C11 C10 C9 120.4(5) . . ?
C10 C11 C12 120.0(5) . . ?
C7 C12 C11 119.9(4) . . ?
C14 C13 Sb 117.7(4) . . ?
C14 C13 C18 121.7(5) . . ?
C18 C13 Sb 120.5(4) . . ?
C13 C14 C15 118.5(6) . . ?
C16 C15 C14 120.5(6) . . ?
C15 C16 C17 120.8(6) . . ?
C18 C17 C16 119.8(6) . . ?
C13 C18 C17 118.8(6) . . ?
C20 C19 Sb 120.0(4) . . ?
C24 C19 Sb 118.3(3) . . ?
C24 C19 C20 121.3(5) . . ?
C21 C20 C19 118.8(6) . . ?
C20 C21 C22 120.0(6) . . ?
C23 C22 C21 121.0(5) . . ?
C22 C23 C24 119.6(6) . . ?
C19 C24 C23 119.3(5) . . ?
C26 C25 S 124.4(4) . . ?
C26 C25 C30 120.1(5) . . ?
C30 C25 S 115.5(5) . . ?
C25 C26 C27 120.2(5) . . ?
C28 C27 C26 120.4(6) . . ?
C27 C28 C29 119.2(6) . . ?
C30 C29 C28 121.3(6) . . ?
C29 C30 C25 118.7(7) . . ?
F1 B F2 113.9(6) . . ?
F1 B F3 105.7(6) . . ?
F1 B F4 112.3(6) . . ?
F2 B F3 107.3(5) . . ?
F2 B F4 113.1(6) . . ?
F4 B F3 103.7(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Sb C1 C2 S 4.9(5) . . . . ?
Sb C1 C2 C3 -178.9(3) . . . . ?
Sb C1 C6 C5 178.7(4) . . . . ?
Sb C7 C8 C9 -174.0(4) . . . . ?
Sb C7 C12 C11 174.5(4) . . . . ?
Sb C13 C14 C15 -175.6(4) . . . . ?
Sb C13 C18 C17 175.9(4) . . . . ?
Sb C19 C20 C21 -172.0(4) . . . . ?
Sb C19 C24 C23 172.2(4) . . . . ?
S C2 C3 C4 176.3(4) . . . . ?
S C25 C26 C27 173.5(4) . . . . ?
S C25 C30 C29 -175.2(5) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C2 S C25 C26 9.2(5) . . . . ?
C2 S C25 C30 -173.9(4) . . . . ?
C2 C1 C6 C5 -2.1(7) . . . . ?
C2 C3 C4 C5 -2.0(8) . . . . ?
C3 C4 C5 C6 1.9(9) . . . . ?
C4 C5 C6 C1 0.2(8) . . . . ?
C6 C1 C2 S -174.3(4) . . . . ?
C6 C1 C2 C3 1.9(7) . . . . ?
C7 C8 C9 C10 0.2(9) . . . . ?
C8 C7 C12 C11 0.4(7) . . . . ?
C8 C9 C10 C11 -1.0(9) . . . . ?
C9 C10 C11 C12 1.4(8) . . . . ?
C10 C11 C12 C7 -1.1(8) . . . . ?
C12 C7 C8 C9 0.1(8) . . . . ?
C13 C14 C15 C16 0.0(8) . . . . ?
C14 C13 C18 C17 -0.5(8) . . . . ?
C14 C15 C16 C17 -1.3(10) . . . . ?
C15 C16 C17 C18 1.7(10) . . . . ?
C16 C17 C18 C13 -0.8(9) . . . . ?
C18 C13 C14 C15 0.9(8) . . . . ?
C19 C20 C21 C22 0.4(9) . . . . ?
C20 C19 C24 C23 -1.0(8) . . . . ?
C20 C21 C22 C23 -2.0(10) . . . . ?
C21 C22 C23 C24 2.1(9) . . . . ?
C22 C23 C24 C19 -0.6(9) . . . . ?
C24 C19 C20 C21 1.1(8) . . . . ?
C25 S C2 C1 -109.4(4) . . . . ?
C25 S C2 C3 74.5(4) . . . . ?
C25 C26 C27 C28 1.5(9) . . . . ?
C26 C25 C30 C29 1.9(8) . . . . ?
C26 C27 C28 C29 1.9(9) . . . . ?
C27 C28 C29 C30 -3.4(10) . . . . ?
C28 C29 C30 C25 1.4(9) . . . . ?
C30 C25 C26 C27 -3.4(8) . . . . ?

_olex2_submission_original_sample_id JJ_BF4
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.51(3)
2 0.49(3)

####################################################################### 
# 
# 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_phssb(ptol)3br
_database_code_depnum_ccdc_archive 'CCDC 2021695'
loop_
_audit_author_name
_audit_author_address
'Gyeongjin Park'
;Texas AM university
United States of America
;
_audit_update_record             
;
2020-08-05 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_date             2020-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H30 Br S Sb'
_chemical_formula_sum            'C33 H30 Br S Sb'
_chemical_formula_weight         660.29
_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'
Br Br -0.2901 2.4595 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   16.7041(12)
_cell_length_b                   10.2829(7)
_cell_length_c                   17.9121(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.860(2)
_cell_angle_gamma                90
_cell_volume                     2928.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9322
_cell_measurement_temperature    110
_cell_measurement_theta_max      30.657
_cell_measurement_theta_min      2.313
_shelx_estimated_absorpt_T_max   0.702
_shelx_estimated_absorpt_T_min   0.511
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1042 before and 0.0673 after correction. The Ratio of minimum to maximum transmission is 0.7749. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.2515
_exptl_crystal_size_min          0.1585
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            110270
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.063
_diffrn_reflns_theta_min         2.002
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7431
_reflns_number_total             9366
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.672
_refine_diff_density_min         -1.284
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         9366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.160
_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)+(0.0288P)²+16.4567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15), C18(H18), C6(H6), C9(H9), C19(H19), C8(H8), C16(H16),
 C22(H22), C4(H4), C26(H26), C12(H12), C25(H25), C11(H11), C3(H3), C23(H23),
 C29(H29), C33(H33), C32(H32), C30(H30), C31(H31)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C27(H27A,H27B,H27C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Sb Sb 0.49967(2) 0.38634(3) 0.68730(2) 0.01469(7) Uani 1 1 d . . . . .
Br Br 0.63702(3) 0.37335(4) 0.83251(2) 0.02132(9) Uani 1 1 d . . . . .
S S 0.41892(7) 0.64805(12) 0.74701(7) 0.0254(2) Uani 1 1 d . . . . .
C5 C 0.6472(3) 0.7267(5) 0.6666(3) 0.0258(9) Uani 1 1 d . . . . .
H5 H 0.694429 0.742866 0.648929 0.031 Uiso 1 1 calc R . . . .
C1 C 0.5496(2) 0.5771(4) 0.6946(2) 0.0166(7) Uani 1 1 d . . . . .
C14 C 0.5643(3) 0.2606(4) 0.6315(2) 0.0166(7) Uani 1 1 d . . . . .
C21 C 0.4393(2) 0.2731(4) 0.7526(2) 0.0175(7) Uani 1 1 d . . . . .
C15 C 0.5226(3) 0.2252(4) 0.5532(2) 0.0204(8) Uani 1 1 d . . . . .
H15 H 0.467593 0.257241 0.527831 0.024 Uiso 1 1 calc R . . . .
C18 C 0.6829(3) 0.1324(4) 0.6256(3) 0.0230(8) Uani 1 1 d . . . . .
H18 H 0.737983 0.100368 0.650589 0.028 Uiso 1 1 calc R . . . .
C10 C 0.2512(3) 0.4730(4) 0.4574(2) 0.0213(8) Uani 1 1 d . . . . .
C7 C 0.3909(2) 0.4241(4) 0.5894(2) 0.0156(7) Uani 1 1 d . . . . .
C6 C 0.6182(3) 0.6000(4) 0.6679(2) 0.0217(8) Uani 1 1 d . . . . .
H6 H 0.645031 0.529812 0.650658 0.026 Uiso 1 1 calc R . . . .
C9 C 0.3148(3) 0.5637(4) 0.4829(2) 0.0241(9) Uani 1 1 d . . . . .
H9 H 0.310907 0.643792 0.455544 0.029 Uiso 1 1 calc R . . . .
C19 C 0.6453(3) 0.2129(4) 0.6669(2) 0.0187(7) Uani 1 1 d . . . . .
H19 H 0.674704 0.235847 0.719513 0.022 Uiso 1 1 calc R . . . .
C8 C 0.3844(3) 0.5400(4) 0.5477(2) 0.0207(8) Uani 1 1 d . . . . .
H8 H 0.427795 0.603184 0.563721 0.025 Uiso 1 1 calc R . . . .
C16 C 0.5611(3) 0.1445(4) 0.5133(2) 0.0231(8) Uani 1 1 d . . . . .
H16 H 0.531704 0.120533 0.460842 0.028 Uiso 1 1 calc R . . . .
C22 C 0.4733(3) 0.1524(4) 0.7784(3) 0.0231(8) Uani 1 1 d . . . . .
H22 H 0.523759 0.125492 0.769023 0.028 Uiso 1 1 calc R . . . .
C4 C 0.6078(3) 0.8286(5) 0.6909(3) 0.0290(10) Uani 1 1 d . . . . .
H4 H 0.628081 0.914691 0.690038 0.035 Uiso 1 1 calc R . . . .
C17 C 0.6420(3) 0.0971(4) 0.5481(3) 0.0241(8) Uani 1 1 d . . . . .
C24 C 0.3602(3) 0.1077(5) 0.8323(3) 0.0259(9) Uani 1 1 d . . . . .
C26 C 0.3646(3) 0.3111(4) 0.7645(3) 0.0227(8) Uani 1 1 d . . . . .
H26 H 0.339848 0.392349 0.745062 0.027 Uiso 1 1 calc R . . . .
C12 C 0.3261(2) 0.3326(4) 0.5644(2) 0.0182(7) Uani 1 1 d . . . . .
H12 H 0.329028 0.253727 0.592664 0.022 Uiso 1 1 calc R . . . .
C25 C 0.3263(3) 0.2297(5) 0.8050(3) 0.0269(9) Uani 1 1 d . . . . .
H25 H 0.275930 0.257186 0.814408 0.032 Uiso 1 1 calc R . . . .
C2 C 0.5097(3) 0.6799(4) 0.7190(2) 0.0192(8) Uani 1 1 d . . . . .
C13 C 0.1760(3) 0.5002(5) 0.3867(3) 0.0300(10) Uani 1 1 d . . . . .
H13A H 0.124888 0.501856 0.402650 0.045 Uiso 1 1 calc GR . . . .
H13B H 0.171070 0.431762 0.347428 0.045 Uiso 1 1 calc GR . . . .
H13C H 0.183207 0.584535 0.364105 0.045 Uiso 1 1 calc GR . . . .
C11 C 0.2580(3) 0.3560(4) 0.4988(2) 0.0206(8) Uani 1 1 d . . . . .
H11 H 0.215280 0.291950 0.481641 0.025 Uiso 1 1 calc R . . . .
C3 C 0.5389(3) 0.8068(5) 0.7165(3) 0.0277(10) Uani 1 1 d . . . . .
H3 H 0.511538 0.877688 0.732420 0.033 Uiso 1 1 calc R . . . .
C23 C 0.4339(3) 0.0704(5) 0.8179(3) 0.0266(9) Uani 1 1 d . . . . .
H23 H 0.457775 -0.012238 0.835260 0.032 Uiso 1 1 calc R . . . .
C28 C 0.4535(3) 0.6600(5) 0.8513(3) 0.0272(9) Uani 1 1 d . . . . .
C29 C 0.3923(3) 0.6377(5) 0.8880(3) 0.0345(11) Uani 1 1 d . . . . .
H29 H 0.336129 0.618253 0.857777 0.041 Uiso 1 1 calc R . . . .
C33 C 0.5358(4) 0.6868(5) 0.8953(3) 0.0346(11) Uani 1 1 d . . . . .
H33 H 0.578146 0.698173 0.870627 0.042 Uiso 1 1 calc R . . . .
C27 C 0.3205(3) 0.0217(6) 0.8788(3) 0.0376(12) Uani 1 1 d . . . . .
H27A H 0.354818 0.022536 0.934010 0.056 Uiso 1 1 calc GR . . . .
H27B H 0.316834 -0.067386 0.858487 0.056 Uiso 1 1 calc GR . . . .
H27C H 0.263901 0.053671 0.874090 0.056 Uiso 1 1 calc GR . . . .
C20 C 0.6842(4) 0.0117(5) 0.5026(3) 0.0378(12) Uani 1 1 d . . . . .
H20A H 0.731041 0.059219 0.493102 0.057 Uiso 1 1 calc GR . . . .
H20B H 0.643400 -0.012260 0.452322 0.057 Uiso 1 1 calc GR . . . .
H20C H 0.705640 -0.067131 0.532876 0.057 Uiso 1 1 calc GR . . . .
C32 C 0.5551(4) 0.6966(6) 0.9768(3) 0.0439(14) Uani 1 1 d . . . . .
H32 H 0.610556 0.719307 1.007544 0.053 Uiso 1 1 calc R . . . .
C30 C 0.4142(4) 0.6440(6) 0.9688(3) 0.0426(14) Uani 1 1 d . . . . .
H30 H 0.372715 0.627340 0.993957 0.051 Uiso 1 1 calc R . . . .
C31 C 0.4946(4) 0.6738(6) 1.0132(3) 0.0441(14) Uani 1 1 d . . . . .
H31 H 0.508599 0.678663 1.068737 0.053 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
Sb Br 2.8960(5) . ?
Sb C1 2.120(4) . ?
Sb C14 2.121(4) . ?
Sb C21 2.114(4) . ?
Sb C7 2.139(4) . ?
S C2 1.768(4) . ?
S C28 1.782(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(6) . ?
C5 C4 1.378(7) . ?
C1 C6 1.390(6) . ?
C1 C2 1.390(6) . ?
C14 C15 1.409(6) . ?
C14 C19 1.394(5) . ?
C21 C22 1.384(6) . ?
C21 C26 1.383(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(6) . ?
C18 C17 1.393(6) . ?
C10 C9 1.382(6) . ?
C10 C13 1.511(6) . ?
C10 C11 1.399(6) . ?
C7 C8 1.392(6) . ?
C7 C12 1.399(5) . ?
C6 H6 0.9500 . ?
C9 H9 0.9500 . ?
C9 C8 1.390(6) . ?
C19 H19 0.9500 . ?
C8 H8 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.392(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.380(7) . ?
C17 C20 1.512(6) . ?
C24 C25 1.401(7) . ?
C24 C23 1.387(7) . ?
C24 C27 1.501(6) . ?
C26 H26 0.9500 . ?
C26 C25 1.386(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.384(6) . ?
C25 H25 0.9500 . ?
C2 C3 1.398(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
C23 H23 0.9500 . ?
C28 C29 1.394(7) . ?
C28 C33 1.386(7) . ?
C29 H29 0.9500 . ?
C29 C30 1.381(8) . ?
C33 H33 0.9500 . ?
C33 C32 1.400(7) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C32 H32 0.9500 . ?
C32 C31 1.381(8) . ?
C30 H30 0.9500 . ?
C30 C31 1.370(9) . ?
C31 H31 0.9500 . ?

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
C1 Sb Br 78.40(10) . . ?
C1 Sb C14 110.21(15) . . ?
C1 Sb C7 95.84(15) . . ?
C14 Sb Br 91.00(11) . . ?
C14 Sb C7 98.72(15) . . ?
C21 Sb Br 81.86(10) . . ?
C21 Sb C1 136.16(15) . . ?
C21 Sb C14 108.88(15) . . ?
C21 Sb C7 97.14(15) . . ?
C7 Sb Br 169.98(11) . . ?
C2 S C28 104.7(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(4) . . ?
C6 C1 Sb 119.1(3) . . ?
C6 C1 C2 120.3(4) . . ?
C2 C1 Sb 120.3(3) . . ?
C15 C14 Sb 117.3(3) . . ?
C19 C14 Sb 124.3(3) . . ?
C19 C14 C15 118.5(4) . . ?
C22 C21 Sb 117.5(3) . . ?
C26 C21 Sb 122.4(3) . . ?
C26 C21 C22 119.9(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.8 . . ?
C19 C18 H18 119.2 . . ?
C19 C18 C17 121.6(4) . . ?
C17 C18 H18 119.2 . . ?
C9 C10 C13 120.6(4) . . ?
C9 C10 C11 118.4(4) . . ?
C11 C10 C13 120.9(4) . . ?
C8 C7 Sb 120.1(3) . . ?
C8 C7 C12 118.6(4) . . ?
C12 C7 Sb 121.3(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 C5 119.5(4) . . ?
C1 C6 H6 120.2 . . ?
C10 C9 H9 119.4 . . ?
C10 C9 C8 121.3(4) . . ?
C8 C9 H9 119.4 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.3(4) . . ?
C18 C19 H19 119.9 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(4) . . ?
C23 C22 H22 119.9 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C18 C17 C20 121.4(4) . . ?
C16 C17 C18 117.8(4) . . ?
C16 C17 C20 120.8(4) . . ?
C25 C24 C27 121.4(4) . . ?
C23 C24 C25 118.0(4) . . ?
C23 C24 C27 120.6(5) . . ?
C21 C26 H26 120.2 . . ?
C21 C26 C25 119.5(4) . . ?
C25 C26 H26 120.2 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C24 C25 H25 119.3 . . ?
C26 C25 C24 121.4(4) . . ?
C26 C25 H25 119.3 . . ?
C1 C2 S 119.0(3) . . ?
C1 C2 C3 119.6(4) . . ?
C3 C2 S 121.3(3) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.9(4) . . ?
C24 C23 H23 119.6 . . ?
C29 C28 S 115.8(4) . . ?
C33 C28 S 123.8(4) . . ?
C33 C28 C29 120.4(5) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 C28 119.4(5) . . ?
C30 C29 H29 120.3 . . ?
C28 C33 H33 120.7 . . ?
C28 C33 C32 118.6(5) . . ?
C32 C33 H33 120.7 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C33 C32 H32 119.6 . . ?
C31 C32 C33 120.8(6) . . ?
C31 C32 H32 119.6 . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 121.1(5) . . ?
C31 C30 H30 119.5 . . ?
C32 C31 H31 120.2 . . ?
C30 C31 C32 119.6(5) . . ?
C30 C31 H31 120.2 . . ?

_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_phssb(ptol)3bf4
_database_code_depnum_ccdc_archive 'CCDC 2021710'
loop_
_audit_author_name
_audit_author_address
'Gyeongjin Park'
;Texas AM university
United States of America
;
_audit_update_record             
;
2020-08-05 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_date             2020-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H30 S Sb, B F4'
_chemical_formula_sum            'C33 H30 B F4 S Sb'
_chemical_formula_weight         667.19
_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'
B B 0.0013 0.0007 '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'
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'

_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.555
_cell_length_b                   12.162
_cell_length_c                   24.558
_cell_angle_alpha                90
_cell_angle_beta                 101.94
_cell_angle_gamma                90
_cell_volume                     6006.3
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9274
_cell_measurement_temperature    110
_cell_measurement_theta_max      30.493
_cell_measurement_theta_min      2.213
_shelx_estimated_absorpt_T_max   0.848
_shelx_estimated_absorpt_T_min   0.766
_exptl_absorpt_coefficient_mu    1.034
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0931 before and 0.0526 after correction. The Ratio of minimum to maximum transmission is 0.8956. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.1781
_exptl_crystal_size_min          0.1649
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            113069
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.549
_diffrn_reflns_theta_min         1.957
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7998
_reflns_number_total             9135
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         9135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0219
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0182P)²+6.4468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0465
_refine_ls_wR_factor_ref         0.0499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C4(H4), C22(H22), C12(H12), C8(H8), C11(H11),
 C26(H26), C9(H9), C25(H25), C19(H19), C15(H15), C23(H23), C16(H16), C33(H33),
 C18(H18), C29(H29), C32(H32), C31(H31), C30(H30)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Sb Sb 0.56243(2) 0.61126(2) 0.61790(2) 0.01606(3) Uani 1 1 d . . . . .
S S 0.71321(2) 0.50650(3) 0.65492(2) 0.02250(7) Uani 1 1 d . . . . .
F4 F 0.62389(4) 0.82161(7) 0.60513(4) 0.02588(18) Uani 1 1 d . . . . .
F1 F 0.63117(5) 0.93155(9) 0.53231(4) 0.0356(2) Uani 1 1 d . . . . .
F3 F 0.59174(5) 1.00035(8) 0.60487(4) 0.0333(2) Uani 1 1 d . . . . .
F2 F 0.70185(5) 0.95640(9) 0.61583(5) 0.0397(2) Uani 1 1 d . . . . .
C1 C 0.63216(7) 0.60440(11) 0.56607(6) 0.0179(2) Uani 1 1 d . . . . .
C3 C 0.74360(7) 0.56816(13) 0.55432(7) 0.0257(3) Uani 1 1 d . . . . .
H3 H 0.787260 0.541470 0.568500 0.031 Uiso 1 1 calc R . . . .
C21 C 0.58591(7) 0.68541(12) 0.69669(6) 0.0190(3) Uani 1 1 d . . . . .
C7 C 0.47689(7) 0.68155(11) 0.56809(6) 0.0179(2) Uani 1 1 d . . . . .
C14 C 0.53082(7) 0.45169(11) 0.63207(6) 0.0178(2) Uani 1 1 d . . . . .
C2 C 0.69596(7) 0.56492(11) 0.58731(6) 0.0197(3) Uani 1 1 d . . . . .
C5 C 0.66319(8) 0.64827(13) 0.47958(6) 0.0264(3) Uani 1 1 d . . . . .
H5 H 0.652124 0.676006 0.442651 0.032 Uiso 1 1 calc R . . . .
C24 C 0.61669(7) 0.78314(13) 0.80163(6) 0.0241(3) Uani 1 1 d . . . . .
C6 C 0.61525(7) 0.64587(12) 0.51198(6) 0.0218(3) Uani 1 1 d . . . . .
H6 H 0.571557 0.672107 0.497533 0.026 Uiso 1 1 calc R . . . .
C4 C 0.72710(8) 0.61046(13) 0.50073(7) 0.0289(3) Uani 1 1 d . . . . .
H4 H 0.759723 0.613523 0.478435 0.035 Uiso 1 1 calc R . . . .
C22 C 0.61695(8) 0.62413(12) 0.74267(6) 0.0236(3) Uani 1 1 d . . . . .
H22 H 0.627626 0.549024 0.738472 0.028 Uiso 1 1 calc R . . . .
C12 C 0.47572(7) 0.78745(12) 0.54602(6) 0.0221(3) Uani 1 1 d . . . . .
H12 H 0.513422 0.833998 0.556024 0.026 Uiso 1 1 calc R . . . .
C8 C 0.42087(7) 0.61494(12) 0.55397(6) 0.0196(3) Uani 1 1 d . . . . .
H8 H 0.420914 0.543386 0.569495 0.023 Uiso 1 1 calc R . . . .
C11 C 0.41924(7) 0.82452(13) 0.50939(6) 0.0232(3) Uani 1 1 d . . . . .
H11 H 0.418560 0.896942 0.494795 0.028 Uiso 1 1 calc R . . . .
C26 C 0.56919(7) 0.79466(12) 0.70292(6) 0.0235(3) Uani 1 1 d . . . . .
H26 H 0.547303 0.836203 0.671709 0.028 Uiso 1 1 calc R . . . .
C9 C 0.36464(7) 0.65347(12) 0.51696(6) 0.0214(3) Uani 1 1 d . . . . .
H9 H 0.326493 0.607733 0.507575 0.026 Uiso 1 1 calc R . . . .
C25 C 0.58484(8) 0.84230(13) 0.75528(6) 0.0255(3) Uani 1 1 d . . . . .
H25 H 0.573553 0.917091 0.759591 0.031 Uiso 1 1 calc R . . . .
C19 C 0.49069(8) 0.43637(13) 0.67077(6) 0.0259(3) Uani 1 1 d . . . . .
H19 H 0.480084 0.496915 0.691782 0.031 Uiso 1 1 calc R . . . .
C17 C 0.48151(8) 0.24243(13) 0.64869(7) 0.0275(3) Uani 1 1 d . . . . .
C28 C 0.76261(7) 0.60871(12) 0.69600(6) 0.0212(3) Uani 1 1 d . . . . .
C15 C 0.54621(7) 0.36228(12) 0.60177(6) 0.0203(3) Uani 1 1 d . . . . .
H15 H 0.573315 0.372129 0.575154 0.024 Uiso 1 1 calc R . . . .
C23 C 0.63218(8) 0.67370(14) 0.79472(6) 0.0265(3) Uani 1 1 d . . . . .
H23 H 0.653532 0.632002 0.826064 0.032 Uiso 1 1 calc R . . . .
C16 C 0.52191(8) 0.25848(12) 0.61045(6) 0.0246(3) Uani 1 1 d . . . . .
H16 H 0.533083 0.197602 0.589938 0.030 Uiso 1 1 calc R . . . .
C33 C 0.76120(7) 0.71875(13) 0.68080(6) 0.0246(3) Uani 1 1 d . . . . .
H33 H 0.735144 0.742208 0.646188 0.030 Uiso 1 1 calc R . . . .
C10 C 0.36358(7) 0.75755(13) 0.49365(6) 0.0216(3) Uani 1 1 d . . . . .
C27 C 0.63447(9) 0.83768(15) 0.85774(7) 0.0337(4) Uani 1 1 d . . . . .
H27A H 0.675517 0.880129 0.860282 0.051 Uiso 1 1 calc GR . . . .
H27B H 0.641113 0.781445 0.886951 0.051 Uiso 1 1 calc GR . . . .
H27C H 0.598370 0.886994 0.862541 0.051 Uiso 1 1 calc GR . . . .
C18 C 0.46623(8) 0.33223(14) 0.67855(7) 0.0307(3) Uani 1 1 d . . . . .
H18 H 0.438588 0.322406 0.704746 0.037 Uiso 1 1 calc R . . . .
C29 C 0.80056(8) 0.57384(14) 0.74693(6) 0.0263(3) Uani 1 1 d . . . . .
H29 H 0.801254 0.498432 0.757123 0.032 Uiso 1 1 calc R . . . .
C13 C 0.30437(8) 0.79621(15) 0.45092(7) 0.0315(3) Uani 1 1 d . . . . .
H13A H 0.292056 0.870574 0.460387 0.047 Uiso 1 1 calc GR . . . .
H13B H 0.266865 0.746247 0.450531 0.047 Uiso 1 1 calc GR . . . .
H13C H 0.315704 0.796919 0.414074 0.047 Uiso 1 1 calc GR . . . .
C32 C 0.79844(8) 0.79421(13) 0.71693(7) 0.0281(3) Uani 1 1 d . . . . .
H32 H 0.797777 0.869709 0.706914 0.034 Uiso 1 1 calc R . . . .
C31 C 0.83659(8) 0.76005(14) 0.76756(7) 0.0299(3) Uani 1 1 d . . . . .
H31 H 0.862200 0.811934 0.791904 0.036 Uiso 1 1 calc R . . . .
C30 C 0.83719(8) 0.65016(15) 0.78246(7) 0.0307(3) Uani 1 1 d . . . . .
H30 H 0.862897 0.626986 0.817266 0.037 Uiso 1 1 calc R . . . .
B B 0.63779(8) 0.92901(14) 0.58969(7) 0.0226(3) Uani 1 1 d . . . . .
C20 C 0.45545(11) 0.12937(15) 0.65753(10) 0.0459(5) Uani 1 1 d . . . . .
H20A H 0.436435 0.096087 0.621406 0.069 Uiso 1 1 calc GR . . . .
H20B H 0.421025 0.135156 0.679670 0.069 Uiso 1 1 calc GR . . . .
H20C H 0.491957 0.083382 0.677278 0.069 Uiso 1 1 calc GR . . . .


_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
Sb C1 2.1060(13) . ?
Sb C21 2.0986(14) . ?
Sb C7 2.1044(13) . ?
Sb C14 2.0983(14) . ?
S C2 1.7731(15) . ?
S C28 1.7805(15) . ?
F4 B 1.4058(19) . ?
F1 B 1.388(2) . ?
F3 B 1.3905(19) . ?
F2 B 1.3811(19) . ?
C1 C2 1.3926(19) . ?
C1 C6 1.3960(19) . ?
C3 H3 0.9500 . ?
C3 C2 1.395(2) . ?
C3 C4 1.388(2) . ?
C21 C22 1.393(2) . ?
C21 C26 1.389(2) . ?
C7 C12 1.396(2) . ?
C7 C8 1.3920(19) . ?
C14 C19 1.394(2) . ?
C14 C15 1.3906(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(2) . ?
C5 C4 1.387(2) . ?
C24 C25 1.391(2) . ?
C24 C23 1.387(2) . ?
C24 C27 1.505(2) . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.389(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.389(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.3952(19) . ?
C11 H11 0.9500 . ?
C11 C10 1.392(2) . ?
C26 H26 0.9500 . ?
C26 C25 1.386(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(2) . ?
C25 H25 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.390(2) . ?
C17 C16 1.390(2) . ?
C17 C18 1.387(2) . ?
C17 C20 1.508(2) . ?
C28 C33 1.388(2) . ?
C28 C29 1.396(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C23 H23 0.9500 . ?
C16 H16 0.9500 . ?
C33 H33 0.9500 . ?
C33 C32 1.391(2) . ?
C10 C13 1.508(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C18 H18 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.385(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C32 H32 0.9500 . ?
C32 C31 1.389(2) . ?
C31 H31 0.9500 . ?
C31 C30 1.385(2) . ?
C30 H30 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C21 Sb C1 121.25(5) . . ?
C21 Sb C7 111.50(5) . . ?
C7 Sb C1 104.83(5) . . ?
C14 Sb C1 109.66(5) . . ?
C14 Sb C21 105.34(5) . . ?
C14 Sb C7 102.83(5) . . ?
C2 S C28 103.36(7) . . ?
C2 C1 Sb 119.55(10) . . ?
C2 C1 C6 120.70(13) . . ?
C6 C1 Sb 119.62(10) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.87(14) . . ?
C22 C21 Sb 119.80(10) . . ?
C26 C21 Sb 119.86(10) . . ?
C26 C21 C22 120.32(13) . . ?
C12 C7 Sb 123.08(10) . . ?
C8 C7 Sb 117.20(10) . . ?
C8 C7 C12 119.57(13) . . ?
C19 C14 Sb 118.95(11) . . ?
C15 C14 Sb 121.45(10) . . ?
C15 C14 C19 119.51(13) . . ?
C1 C2 S 118.63(11) . . ?
C1 C2 C3 119.53(14) . . ?
C3 C2 S 121.79(11) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.50(15) . . ?
C25 C24 C27 120.38(15) . . ?
C23 C24 C25 118.51(14) . . ?
C23 C24 C27 121.11(15) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.10(14) . . ?
C5 C6 H6 120.4 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.29(14) . . ?
C5 C4 H4 119.9 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.48(14) . . ?
C23 C22 H22 120.3 . . ?
C7 C12 H12 120.1 . . ?
C11 C12 C7 119.74(13) . . ?
C11 C12 H12 120.1 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.86(13) . . ?
C9 C8 H8 120.1 . . ?
C12 C11 H11 119.4 . . ?
C12 C11 C10 121.25(14) . . ?
C10 C11 H11 119.4 . . ?
C21 C26 H26 120.4 . . ?
C25 C26 C21 119.14(14) . . ?
C25 C26 H26 120.4 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.02(13) . . ?
C10 C9 H9 119.5 . . ?
C24 C25 H25 119.2 . . ?
C26 C25 C24 121.52(14) . . ?
C26 C25 H25 119.2 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.82(14) . . ?
C18 C19 H19 120.1 . . ?
C16 C17 C20 120.34(16) . . ?
C18 C17 C16 118.60(14) . . ?
C18 C17 C20 121.05(15) . . ?
C33 C28 S 122.89(11) . . ?
C33 C28 C29 120.70(14) . . ?
C29 C28 S 116.30(12) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.95(13) . . ?
C16 C15 H15 120.0 . . ?
C24 C23 C22 121.01(14) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C17 C16 C15 120.99(14) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C28 C33 H33 120.4 . . ?
C28 C33 C32 119.11(14) . . ?
C32 C33 H33 120.4 . . ?
C11 C10 C13 120.61(14) . . ?
C9 C10 C11 118.51(13) . . ?
C9 C10 C13 120.86(14) . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C19 C18 H18 119.4 . . ?
C17 C18 C19 121.12(14) . . ?
C17 C18 H18 119.4 . . ?
C28 C29 H29 120.3 . . ?
C30 C29 C28 119.41(15) . . ?
C30 C29 H29 120.3 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C33 C32 H32 119.7 . . ?
C31 C32 C33 120.52(15) . . ?
C31 C32 H32 119.7 . . ?
C32 C31 H31 120.1 . . ?
C30 C31 C32 119.83(15) . . ?
C30 C31 H31 120.1 . . ?
C29 C30 C31 120.42(15) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
F1 B F4 108.17(13) . . ?
F1 B F3 109.22(13) . . ?
F3 B F4 108.65(13) . . ?
F2 B F4 109.04(12) . . ?
F2 B F1 110.51(13) . . ?
F2 B F3 111.18(14) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_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_me_2_bf4_0ma
_database_code_depnum_ccdc_archive 'CCDC 2008418'
loop_
_audit_author_name
_audit_author_address
'Gyeongjin Park'
;Texas AM university
United States of America
;
_audit_update_record             
;
2020-06-06 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_date             2020-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        J_Me_BF4
_chemical_formula_moiety         'C62 H54 F S2 Sb2, 2(C H2 Cl2), 3(B F4)'
_chemical_formula_sum            'C64 H58 B3 Cl4 F13 S2 Sb2'
_chemical_formula_weight         1555.95
_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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'

_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      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   15.494(2)
_cell_length_b                   10.9891(16)
_cell_length_c                   19.761(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.566(7)
_cell_angle_gamma                90
_cell_volume                     3150.3(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9203
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.758
_exptl_absorpt_coefficient_mu    1.173
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1184 before and 0.0631 after correction. The Ratio of minimum to maximum transmission is 0.8648. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_preparation       'In DCM and pentane mixture'
_exptl_crystal_recrystallization_method 'In air and at room temperature'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1577
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            84174
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.156
_diffrn_ambient_temperature      109.98
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6476
_reflns_number_total             7231
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.164
_refine_diff_density_min         -1.329
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         7231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+8.5472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1100
_refine_special_details          
'the boron (B1) is located in the other side of the inversion center.The other boron should be in the opposit from the inversion center.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F6(0.5) F7(0.5) F8(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
  C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
3.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_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 0.78180(2) 0.43485(2) 0.36890(2) 0.01281(8) Uani 1 1 d . . . . .
S1 S 0.70978(5) 0.26133(7) 0.48371(4) 0.01460(15) Uani 1 1 d . . . . .
Cl2 Cl 1.12727(9) 0.05294(11) 0.30608(6) 0.0457(3) Uani 1 1 d . . . . .
Cl1 Cl 1.11578(10) 0.10582(12) 0.15823(6) 0.0530(3) Uani 1 1 d . . . . .
F1 F 0.750000 0.3875(2) 0.250000 0.0162(5) Uani 1 2 d S T P . .
F4 F 0.63744(17) 0.0389(2) 0.40936(14) 0.0370(5) Uani 1 1 d . . . . .
F5 F 0.6454(2) -0.1458(2) 0.36108(17) 0.0535(8) Uani 1 1 d . . . . .
F2 F 0.6883(2) 0.0213(3) 0.31529(14) 0.0553(8) Uani 1 1 d . . . . .
F3 F 0.7765(2) -0.0437(3) 0.42616(17) 0.0620(9) Uani 1 1 d . . . . .
C19 C 0.8679(2) 0.2799(3) 0.39164(16) 0.0155(6) Uani 1 1 d . . . . .
C13 C 0.6371(2) 0.4451(3) 0.33147(16) 0.0170(6) Uani 1 1 d . . . . .
C1 C 0.7921(2) 0.4803(3) 0.47894(15) 0.0150(5) Uani 1 1 d . . . . .
C7 C 0.8560(2) 0.5815(3) 0.34884(16) 0.0149(5) Uani 1 1 d . . . . .
C2 C 0.7543(2) 0.4074(3) 0.51973(15) 0.0142(5) Uani 1 1 d . . . . .
C12 C 0.9454(2) 0.5597(3) 0.35088(17) 0.0177(6) Uani 1 1 d . . . . .
H12 H 0.971638 0.480720 0.361637 0.021 Uiso 1 1 calc R . . . .
C24 C 0.9350(2) 0.2752(3) 0.46060(16) 0.0187(6) Uani 1 1 d . . . . .
H24 H 0.935832 0.334613 0.495742 0.022 Uiso 1 1 calc R . . . .
C11 C 0.9959(2) 0.6551(3) 0.33693(17) 0.0211(6) Uani 1 1 d . . . . .
H11 H 1.057142 0.641341 0.338596 0.025 Uiso 1 1 calc R . . . .
C18 C 0.5992(2) 0.5538(3) 0.34498(17) 0.0202(6) Uani 1 1 d . . . . .
H18 H 0.638332 0.619732 0.367637 0.024 Uiso 1 1 calc R . . . .
C20 C 0.8667(2) 0.1941(3) 0.33970(17) 0.0185(6) Uani 1 1 d . . . . .
H20 H 0.820651 0.197247 0.292862 0.022 Uiso 1 1 calc R . . . .
C25 C 0.6028(2) 0.2531(3) 0.49831(16) 0.0175(6) Uani 1 1 d . . . . .
C8 C 0.8177(2) 0.6975(3) 0.33378(17) 0.0192(6) Uani 1 1 d . . . . .
H8 H 0.757197 0.712323 0.333612 0.023 Uiso 1 1 calc R . . . .
C3 C 0.7511(2) 0.4446(3) 0.58620(17) 0.0186(6) Uani 1 1 d . . . . .
H3 H 0.725293 0.392998 0.612724 0.022 Uiso 1 1 calc R . . . .
C14 C 0.5815(2) 0.3481(3) 0.29883(17) 0.0230(7) Uani 1 1 d . . . . .
H14 H 0.607560 0.274456 0.289740 0.028 Uiso 1 1 calc R . . . .
C16 C 0.4486(2) 0.4682(4) 0.29263(19) 0.0314(8) Uani 1 1 d . . . . .
H16 H 0.383593 0.475641 0.279101 0.038 Uiso 1 1 calc R . . . .
C23 C 1.0006(2) 0.1828(3) 0.47763(18) 0.0223(6) Uani 1 1 d . . . . .
H23 H 1.045750 0.177944 0.524799 0.027 Uiso 1 1 calc R . . . .
C17 C 0.5045(3) 0.5650(3) 0.32524(19) 0.0277(8) Uani 1 1 d . . . . .
H17 H 0.478292 0.638768 0.334075 0.033 Uiso 1 1 calc R . . . .
C10 C 0.9574(2) 0.7700(3) 0.32064(18) 0.0227(7) Uani 1 1 d . . . . .
H10 H 0.991891 0.834496 0.310560 0.027 Uiso 1 1 calc R . . . .
C22 C 1.0000(2) 0.0982(3) 0.42568(19) 0.0244(7) Uani 1 1 d . . . . .
H22 H 1.045431 0.036006 0.437058 0.029 Uiso 1 1 calc R . . . .
C4 C 0.7859(2) 0.5573(3) 0.61304(17) 0.0199(6) Uani 1 1 d . . . . .
H4 H 0.782665 0.584681 0.657703 0.024 Uiso 1 1 calc R . . . .
C30 C 0.5402(2) 0.3456(3) 0.46807(18) 0.0216(6) Uani 1 1 d . . . . .
H30 H 0.555857 0.410991 0.443096 0.026 Uiso 1 1 calc R . . . .
C9 C 0.8684(2) 0.7909(3) 0.31906(19) 0.0251(7) Uani 1 1 d . . . . .
H9 H 0.842107 0.869775 0.307818 0.030 Uiso 1 1 calc R . . . .
C21 C 0.9334(2) 0.1037(3) 0.35702(19) 0.0235(7) Uani 1 1 d . . . . .
H21 H 0.933588 0.045178 0.321657 0.028 Uiso 1 1 calc R . . . .
C5 C 0.8256(2) 0.6308(3) 0.57481(17) 0.0225(6) Uani 1 1 d . . . . .
H5 H 0.850538 0.707663 0.593784 0.027 Uiso 1 1 calc R . . . .
C6 C 0.8288(2) 0.5918(3) 0.50855(17) 0.0196(6) Uani 1 1 d . . . . .
H6 H 0.856662 0.642565 0.483118 0.024 Uiso 1 1 calc R . . . .
C15 C 0.4862(2) 0.3603(4) 0.27943(19) 0.0308(8) Uani 1 1 d . . . . .
H15 H 0.446973 0.294271 0.257059 0.037 Uiso 1 1 calc R . . . .
C26 C 0.5807(2) 0.1550(3) 0.53343(18) 0.0222(6) Uani 1 1 d . . . . .
H26 H 0.623877 0.091526 0.553046 0.027 Uiso 1 1 calc R . . . .
C28 C 0.4311(2) 0.2443(4) 0.5102(2) 0.0279(7) Uani 1 1 d . . . . .
H28 H 0.371913 0.241203 0.514455 0.034 Uiso 1 1 calc R . . . .
C29 C 0.4539(2) 0.3408(4) 0.4751(2) 0.0280(7) Uani 1 1 d . . . . .
H29 H 0.410552 0.404177 0.455584 0.034 Uiso 1 1 calc R . . . .
C27 C 0.4939(3) 0.1519(3) 0.53921(19) 0.0271(7) Uani 1 1 d . . . . .
H27 H 0.477609 0.085780 0.563280 0.033 Uiso 1 1 calc R . . . .
C31 C 0.7840(2) 0.1586(3) 0.54932(17) 0.0201(6) Uani 1 1 d . . . . .
H31A H 0.779140 0.174457 0.596668 0.030 Uiso 1 1 calc GR . . . .
H31B H 0.847835 0.170841 0.552256 0.030 Uiso 1 1 calc GR . . . .
H31C H 0.765381 0.074562 0.534823 0.030 Uiso 1 1 calc GR . . . .
C32 C 1.0835(5) 0.0049(6) 0.2151(3) 0.0656(16) Uani 1 1 d . . . . .
H32A H 1.015461 0.000238 0.198796 0.079 Uiso 1 1 calc R . . . .
H32B H 1.107173 -0.077607 0.211331 0.079 Uiso 1 1 calc R . . . .
B1 B 0.6873(3) -0.0327(4) 0.3776(2) 0.0277(8) Uani 1 1 d . . . . .
F9 F 0.750000 0.4023(3) 0.750000 0.0368(8) Uani 1 2 d S T P . .
B2 B 0.750000 0.2771(6) 0.750000 0.0408(17) Uani 1 2 d S T P . .
F6 F 0.8363(3) 0.2525(4) 0.7255(3) 0.0339(10) Uani 0.5 1 d . . . . .
F7 F 0.7360(4) 0.2114(4) 0.6945(2) 0.0357(11) Uani 0.5 1 d . . . . .
F8 F 0.6810(4) 0.2472(5) 0.6861(2) 0.0368(11) Uani 0.5 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
Sb1 F1 2.2849(7) . ?
Sb1 C19 2.112(3) . ?
Sb1 C13 2.103(3) . ?
Sb1 C1 2.182(3) . ?
Sb1 C7 2.097(3) . ?
S1 C2 1.793(3) . ?
S1 C25 1.782(3) . ?
S1 C31 1.797(3) . ?
Cl2 C32 1.765(5) . ?
Cl1 C32 1.772(6) . ?
F4 B1 1.397(5) . ?
F5 B1 1.387(5) . ?
F2 B1 1.372(5) . ?
F3 B1 1.384(5) . ?
C19 C24 1.395(4) . ?
C19 C20 1.389(4) . ?
C13 C18 1.396(4) . ?
C13 C14 1.380(5) . ?
C1 C2 1.403(4) . ?
C1 C6 1.390(4) . ?
C7 C12 1.393(4) . ?
C7 C8 1.393(4) . ?
C2 C3 1.393(4) . ?
C12 C11 1.392(4) . ?
C24 C23 1.392(5) . ?
C11 C10 1.385(5) . ?
C18 C17 1.385(5) . ?
C20 C21 1.388(5) . ?
C25 C30 1.387(5) . ?
C25 C26 1.389(4) . ?
C8 C9 1.385(5) . ?
C3 C4 1.381(5) . ?
C14 C15 1.394(5) . ?
C16 C17 1.381(6) . ?
C16 C15 1.387(6) . ?
C23 C22 1.382(5) . ?
C10 C9 1.387(5) . ?
C22 C21 1.387(5) . ?
C4 C5 1.388(5) . ?
C30 C29 1.393(5) . ?
C5 C6 1.395(4) . ?
C26 C27 1.389(5) . ?
C28 C29 1.380(5) . ?
C28 C27 1.384(6) . ?
F9 B2 1.376(7) . ?
B2 F6 1.597(4) . ?
B2 F6 1.597(4) 2_656 ?
B2 F7 1.266(6) 2_656 ?
B2 F7 1.267(6) . ?
B2 F8 1.378(5) . ?
B2 F8 1.378(5) 2_656 ?
F6 F7 1.525(7) . ?
F7 F8 0.900(6) . ?

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
C19 Sb1 F1 85.82(9) . . ?
C19 Sb1 C1 98.81(11) . . ?
C13 Sb1 F1 80.36(8) . . ?
C13 Sb1 C19 129.34(12) . . ?
C13 Sb1 C1 91.93(11) . . ?
C1 Sb1 F1 172.27(8) . . ?
C7 Sb1 F1 85.14(9) . . ?
C7 Sb1 C19 108.23(12) . . ?
C7 Sb1 C13 118.67(12) . . ?
C7 Sb1 C1 99.17(11) . . ?
C2 S1 C31 102.51(15) . . ?
C25 S1 C2 103.35(14) . . ?
C25 S1 C31 104.30(15) . . ?
Sb1 F1 Sb1 153.66(12) 2_655 . ?
C24 C19 Sb1 115.9(2) . . ?
C20 C19 Sb1 123.1(2) . . ?
C20 C19 C24 120.6(3) . . ?
C18 C13 Sb1 116.5(2) . . ?
C14 C13 Sb1 122.4(2) . . ?
C14 C13 C18 121.0(3) . . ?
C2 C1 Sb1 122.9(2) . . ?
C6 C1 Sb1 119.8(2) . . ?
C6 C1 C2 117.0(3) . . ?
C12 C7 Sb1 117.9(2) . . ?
C8 C7 Sb1 121.5(2) . . ?
C8 C7 C12 120.6(3) . . ?
C1 C2 S1 117.6(2) . . ?
C3 C2 S1 120.1(2) . . ?
C3 C2 C1 122.3(3) . . ?
C11 C12 C7 119.1(3) . . ?
C23 C24 C19 119.6(3) . . ?
C10 C11 C12 120.4(3) . . ?
C17 C18 C13 119.8(3) . . ?
C21 C20 C19 119.2(3) . . ?
C30 C25 S1 116.3(2) . . ?
C30 C25 C26 121.8(3) . . ?
C26 C25 S1 121.8(3) . . ?
C9 C8 C7 119.5(3) . . ?
C4 C3 C2 119.1(3) . . ?
C13 C14 C15 118.8(3) . . ?
C17 C16 C15 120.7(3) . . ?
C22 C23 C24 119.8(3) . . ?
C16 C17 C18 119.5(3) . . ?
C11 C10 C9 120.0(3) . . ?
C23 C22 C21 120.4(3) . . ?
C3 C4 C5 120.0(3) . . ?
C25 C30 C29 118.7(3) . . ?
C8 C9 C10 120.4(3) . . ?
C22 C21 C20 120.4(3) . . ?
C4 C5 C6 120.1(3) . . ?
C1 C6 C5 121.4(3) . . ?
C16 C15 C14 120.3(4) . . ?
C25 C26 C27 118.4(3) . . ?
C29 C28 C27 120.3(3) . . ?
C28 C29 C30 120.3(3) . . ?
C28 C27 C26 120.6(3) . . ?
Cl2 C32 Cl1 111.5(4) . . ?
F5 B1 F4 108.9(3) . . ?
F2 B1 F4 110.0(4) . . ?
F2 B1 F5 109.2(3) . . ?
F2 B1 F3 109.7(3) . . ?
F3 B1 F4 108.2(3) . . ?
F3 B1 F5 110.9(4) . . ?
F9 B2 F6 99.8(3) . 2_656 ?
F9 B2 F6 99.8(3) . . ?
F9 B2 F8 103.8(3) . 2_656 ?
F9 B2 F8 103.8(3) . . ?
F6 B2 F6 160.5(6) . 2_656 ?
F7 B2 F9 124.8(3) 2_656 . ?
F7 B2 F9 124.8(3) . . ?
F7 B2 F6 105.0(4) . 2_656 ?
F7 B2 F6 63.1(3) . . ?
F7 B2 F6 63.1(3) 2_656 2_656 ?
F7 B2 F6 105.0(4) 2_656 . ?
F7 B2 F7 110.5(7) 2_656 . ?
F7 B2 F8 39.5(3) . . ?
F7 B2 F8 120.0(5) 2_656 . ?
F7 B2 F8 39.5(3) 2_656 2_656 ?
F7 B2 F8 120.0(5) . 2_656 ?
F8 B2 F6 98.3(3) . . ?
F8 B2 F6 77.0(3) . 2_656 ?
F8 B2 F6 77.0(3) 2_656 . ?
F8 B2 F6 98.3(3) 2_656 2_656 ?
F8 B2 F8 152.4(7) . 2_656 ?
F7 F6 B2 47.8(3) . . ?
B2 F7 F6 69.1(3) . . ?
F8 F7 B2 76.9(5) . . ?
F8 F7 F6 135.3(6) . . ?
F7 F8 B2 63.6(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
