#------------------------------------------------------------------------------
#$Date: 2019-11-25 16:12:44 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241290 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/09/4130965.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4130965
loop_
_publ_author_name
'Davis, Holly J.'
'Mihai, Madalina T.'
'Phipps, Robert J.'
_publ_section_title
;
 Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A
 Meta-Selective C-H Borylation of Aromatic Quaternary Ammonium Salts.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12759
_journal_page_last               12762
_journal_paper_doi               10.1021/jacs.6b08164
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety
'C21 H35 B2 F N O4 +, C7 H7 O3 S -, 2(C H2 Cl2)'
_chemical_formula_sum            'C30 H46 B2 Cl4 F N O7 S'
_chemical_formula_weight         747.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.700(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.5416(10)
_cell_length_b                   7.4594(2)
_cell_length_c                   15.8608(5)
_cell_measurement_reflns_used    9438
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.72
_cell_measurement_theta_min      2.75
_cell_volume                     3801.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18136
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.915
_diffrn_reflns_theta_max         66.915
_diffrn_reflns_theta_min         2.751
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    3.740
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.831
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1615P)²+15.3069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2727
_refine_ls_wR_factor_ref         0.2915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2857
_reflns_number_total             3644
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b08164_si_001.cif
_cod_data_source_block           RP_B1_0004
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               4130965
_cambridge_user_name             'Holly Davis'
_cambridge_user_crsid            hd308
_cambridge_supervisor_name       'Robert Phipps'
_cambridge_supervisor_crsid      rjp71
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             HD503A
_cambridge_data_id               RP_B1_0004
_ccdc_publ_extra_info
;
_cambridge_sample_id HD503A
_cambridge_data_id RP_B1_0004
;
_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.
;
_shelx_estimated_absorpt_t_min   0.493
_shelx_estimated_absorpt_t_max   0.896
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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
F1 F 0.25846(9) 0.5000 0.8116(2) 0.0421(8) Uani 1 2 d S T P A .
N1 N 0.26906(13) 0.5000 0.6428(3) 0.0335(10) Uani 1 2 d S T P . .
B1 B 0.32360(17) 0.5000 0.9780(4) 0.0376(14) Uani 1 2 d DS T P . .
O1 O 0.28825(14) 0.4581(10) 0.9979(3) 0.044(3) Uani 0.5 1 d D . P A -1
O2 O 0.35542(15) 0.5499(8) 1.0492(3) 0.050(2) Uani 0.5 1 d D . P A -1
C9 C 0.3000(2) 0.4373(11) 1.0938(4) 0.049(3) Uani 0.5 1 d D . P A -1
C91 C 0.2630(2) 0.494(3) 1.1261(5) 0.073(3) Uani 0.5 1 d D U P A -1
H91A H 0.2704 0.4811 1.1902 0.109 Uiso 0.5 1 calc R U P A -1
H91B H 0.2561 0.6196 1.1102 0.109 Uiso 0.5 1 calc R U P A -1
H91C H 0.2390 0.4182 1.0987 0.109 Uiso 0.5 1 calc R U P A -1
C92 C 0.3086(5) 0.2359(15) 1.1095(10) 0.069(4) Uani 0.5 1 d D U P A -1
H92A H 0.3168 0.2113 1.1728 0.104 Uiso 0.5 1 calc R U P A -1
H92B H 0.2834 0.1679 1.0805 0.104 Uiso 0.5 1 calc R U P A -1
H92C H 0.3312 0.2000 1.0852 0.104 Uiso 0.5 1 calc R U P A -1
C10 C 0.3386(2) 0.5574(12) 1.1244(4) 0.055(3) Uani 0.5 1 d D . P A -1
C101 C 0.3720(2) 0.486(3) 1.2041(5) 0.085(4) Uani 0.5 1 d D U P A -1
H10A H 0.3616 0.4889 1.2559 0.128 Uiso 0.5 1 calc R U P A -1
H10B H 0.3788 0.3617 1.1929 0.128 Uiso 0.5 1 calc R U P A -1
H10C H 0.3970 0.5600 1.2148 0.128 Uiso 0.5 1 calc R U P A -1
C102 C 0.3274(6) 0.7523(17) 1.1356(12) 0.094(6) Uani 0.5 1 d D U P A -1
H10D H 0.3160 0.7623 1.1857 0.141 Uiso 0.5 1 calc R U P A -1
H10E H 0.3525 0.8268 1.1462 0.141 Uiso 0.5 1 calc R U P A -1
H10F H 0.3067 0.7932 1.0820 0.141 Uiso 0.5 1 calc R U P A -1
B2 B 0.42508(19) 0.5000 0.7923(4) 0.0471(16) Uani 1 2 d DS T P . .
O3 O 0.45769(14) 0.463(3) 0.8641(3) 0.060(5) Uani 0.5 1 d D . P B -1
O4 O 0.43618(15) 0.515(8) 0.7181(3) 0.055(6) Uani 0.5 1 d D . P B -1
C11 C 0.4960(2) 0.476(3) 0.8386(5) 0.076(5) Uani 0.5 1 d D . P B -1
C111 C 0.5140(9) 0.290(3) 0.8665(18) 0.141(10) Uani 0.5 1 d D U P B -1
H11A H 0.5406 0.2777 0.8532 0.212 Uiso 0.5 1 calc R U P B -1
H11B H 0.5184 0.2749 0.9299 0.212 Uiso 0.5 1 calc R U P B -1
H11C H 0.4945 0.1987 0.8344 0.212 Uiso 0.5 1 calc R U P B -1
C112 C 0.5245(6) 0.623(2) 0.8894(13) 0.101(5) Uani 0.5 1 d D U P B -1
H11D H 0.5499 0.6278 0.8707 0.152 Uiso 0.5 1 calc R U P B -1
H11E H 0.5101 0.7386 0.8777 0.152 Uiso 0.5 1 calc R U P B -1
H11F H 0.5318 0.5969 0.9526 0.152 Uiso 0.5 1 calc R U P B -1
C12 C 0.4810(2) 0.480(3) 0.7380(5) 0.064(4) Uani 0.5 1 d D . P B -1
C121 C 0.4869(7) 0.292(2) 0.7059(17) 0.123(8) Uani 0.5 1 d D U P B -1
H12A H 0.5167 0.2660 0.7188 0.185 Uiso 0.5 1 calc R U P B -1
H12B H 0.4741 0.2040 0.7362 0.185 Uiso 0.5 1 calc R U P B -1
H12C H 0.4737 0.2839 0.6423 0.185 Uiso 0.5 1 calc R U P B -1
C122 C 0.4976(5) 0.621(2) 0.6870(10) 0.093(5) Uani 0.5 1 d D U P B -1
H12D H 0.5276 0.6045 0.6979 0.139 Uiso 0.5 1 calc R U P B -1
H12E H 0.4836 0.6085 0.6240 0.139 Uiso 0.5 1 calc R U P B -1
H12F H 0.4922 0.7412 0.7065 0.139 Uiso 0.5 1 calc R U P B -1
C1 C 0.30520(15) 0.5000 0.7242(3) 0.0295(10) Uani 1 2 d S T P A .
C2 C 0.29828(15) 0.5000 0.8066(3) 0.0297(11) Uani 1 2 d S T P . .
C3 C 0.33035(16) 0.5000 0.8847(3) 0.0337(11) Uani 1 2 d S T P A .
C4 C 0.37067(17) 0.5000 0.8778(4) 0.0398(13) Uani 1 2 d S T P . .
H4A H 0.3933 0.5000 0.9301 0.048 Uiso 1 2 calc R U P A .
C5 C 0.37895(17) 0.5000 0.7969(4) 0.0371(12) Uani 1 2 d S T P A .
C6 C 0.34605(17) 0.5000 0.7209(3) 0.0340(11) Uani 1 2 d S T P . .
H6A H 0.3515 0.5000 0.6654 0.041 Uiso 1 2 calc R U P A .
C7 C 0.28383(19) 0.5000 0.5607(3) 0.0441(14) Uani 1 2 d S T P . .
H7A H 0.2603 0.5000 0.5091 0.066 Uiso 1 2 d R U P . .
H7B H 0.2999 0.3938 0.5601 0.066 Uiso 1 1 d R U . . .
C8 C 0.24259(13) 0.3346(6) 0.6377(3) 0.0471(10) Uani 1 1 d . . . . .
H8A H 0.2324 0.3289 0.6897 0.071 Uiso 1 1 calc R U . . .
H8B H 0.2593 0.2278 0.6358 0.071 Uiso 1 1 calc R U . . .
H8C H 0.2189 0.3396 0.5845 0.071 Uiso 1 1 calc R U . . .
S1 S 0.15567(5) 0.5000 0.38849(11) 0.0525(5) Uani 1 2 d S T P . .
O11 O 0.2009(2) 0.5000 0.4069(4) 0.104(2) Uani 1 2 d S T P . .
O12 O 0.14217(18) 0.3391(6) 0.4169(3) 0.0949(15) Uani 1 1 d . . . . .
C17 C 0.13800(18) 0.5000 0.2729(4) 0.0431(14) Uani 1 2 d S T P . .
C18 C 0.1649(2) 0.5000 0.2217(5) 0.0576(17) Uani 1 2 d S T P . .
H18A H 0.1941 0.5000 0.2495 0.069 Uiso 1 2 calc R U P . .
C19 C 0.1506(2) 0.5000 0.1311(5) 0.0567(17) Uani 1 2 d S T P . .
H19A H 0.1700 0.5000 0.0977 0.068 Uiso 1 2 calc R U P . .
C20 C 0.1094(2) 0.5000 0.0891(5) 0.0624(18) Uani 1 2 d S T P . .
C21 C 0.0822(2) 0.5000 0.1395(6) 0.086(3) Uani 1 2 d S T P . .
H21A H 0.0531 0.5000 0.1111 0.103 Uiso 1 2 calc R U P . .
C22 C 0.0963(2) 0.5000 0.2308(5) 0.072(2) Uani 1 2 d S T P . .
H22A H 0.0768 0.5000 0.2641 0.086 Uiso 1 2 calc R U P . .
C23 C 0.0934(4) 0.5000 -0.0105(6) 0.102(3) Uani 1 2 d S T P . .
H23A H 0.0636 0.5000 -0.0291 0.153 Uiso 1 2 d R U P . .
H23B H 0.1035 0.3949 -0.0327 0.153 Uiso 1 1 d R U . . .
C1S C 0.1171(2) 0.0000 0.5082(5) 0.078(2) Uani 1 2 d DS T P . .
H1S H 0.1158 0.1073 0.4708 0.094 Uiso 1 1 d R U . . .
Cl1S Cl 0.16436(7) 0.0000 0.59286(13) 0.0765(7) Uani 1 2 d DS T P . .
Cl2S Cl 0.07429(8) 0.0000 0.55123(17) 0.1013(9) Uani 1 2 d DS T P . .
C2S C 0.4045(3) 0.0000 0.4430(8) 0.091(6) Uani 0.5 2 d DS TU P . .
H2S H 0.4028 0.1042 0.4774 0.110 Uiso 0.5 1 d R U P . .
C3S C 0.4138(5) 0.0000 0.3234(13) 0.23(2) Uani 0.5 2 d DS TU P . .
H3S H 0.4160 0.1044 0.2896 0.275 Uiso 0.5 1 d R U P . .
Cl3S Cl 0.3654(3) 0.0000 0.3443(4) 0.225(3) Uani 1 2 d DS T P . .
Cl4S Cl 0.4528(3) 0.0000 0.4248(12) 0.507(13) Uani 1 2 d DS T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 N1 C8 111.4(3) . 6_565
C1 N1 C8 111.4(3) . .
C8 N1 C8 109.7(4) 6_565 .
C1 N1 C7 110.9(4) . .
C8 N1 C7 106.6(3) 6_565 .
C8 N1 C7 106.6(3) . .
O1 B1 O2 113.6(5) . .
O1 B1 C3 126.8(5) . .
O2 B1 C3 119.5(4) . .
B1 O1 C9 106.0(5) . .
B1 O2 C10 107.0(5) . .
O1 C9 C91 108.4(5) . .
O1 C9 C10 102.6(5) . .
C91 C9 C10 115.0(8) . .
O1 C9 C92 104.7(8) . .
C91 C9 C92 110.4(7) . .
C10 C9 C92 114.7(8) . .
C9 C91 H91A 109.5 . .
C9 C91 H91B 109.5 . .
H91A C91 H91B 109.5 . .
C9 C91 H91C 109.5 . .
H91A C91 H91C 109.5 . .
H91B C91 H91C 109.5 . .
C9 C92 H92A 109.5 . .
C9 C92 H92B 109.5 . .
H92A C92 H92B 109.5 . .
C9 C92 H92C 109.5 . .
H92A C92 H92C 109.5 . .
H92B C92 H92C 109.5 . .
O2 C10 C102 107.3(10) . .
O2 C10 C101 107.5(6) . .
C102 C10 C101 112.6(8) . .
O2 C10 C9 102.0(5) . .
C102 C10 C9 112.4(9) . .
C101 C10 C9 114.1(8) . .
C10 C101 H10A 109.5 . .
C10 C101 H10B 109.5 . .
H10A C101 H10B 109.5 . .
C10 C101 H10C 109.5 . .
H10A C101 H10C 109.5 . .
H10B C101 H10C 109.5 . .
C10 C102 H10D 109.5 . .
C10 C102 H10E 109.5 . .
H10D C102 H10E 109.5 . .
C10 C102 H10F 109.5 . .
H10D C102 H10F 109.5 . .
H10E C102 H10F 109.5 . .
O4 B2 O3 113.2(7) . .
O4 B2 C5 124.6(5) . .
O3 B2 C5 121.8(5) . .
B2 O3 C11 108.4(6) . .
B2 O4 C12 108.8(9) . .
O3 C11 C112 111.6(14) . .
O3 C11 C111 99.6(18) . .
C112 C11 C111 111.4(8) . .
O3 C11 C12 103.8(5) . .
C112 C11 C12 120.4(16) . .
C111 C11 C12 107.8(19) . .
C11 C111 H11A 109.5 . .
C11 C111 H11B 109.5 . .
H11A C111 H11B 109.5 . .
C11 C111 H11C 109.5 . .
H11A C111 H11C 109.5 . .
H11B C111 H11C 109.5 . .
C11 C112 H11D 109.5 . .
C11 C112 H11E 109.5 . .
H11D C112 H11E 109.5 . .
C11 C112 H11F 109.5 . .
H11D C112 H11F 109.5 . .
H11E C112 H11F 109.5 . .
O4 C12 C122 105.7(18) . .
O4 C12 C11 103.8(6) . .
C122 C12 C11 120.4(14) . .
O4 C12 C121 108(2) . .
C122 C12 C121 110.8(7) . .
C11 C12 C121 107.0(17) . .
C12 C121 H12A 109.5 . .
C12 C121 H12B 109.5 . .
H12A C121 H12B 109.5 . .
C12 C121 H12C 109.5 . .
H12A C121 H12C 109.5 . .
H12B C121 H12C 109.5 . .
C12 C122 H12D 109.5 . .
C12 C122 H12E 109.5 . .
H12D C122 H12E 109.5 . .
C12 C122 H12F 109.5 . .
H12D C122 H12F 109.5 . .
H12E C122 H12F 109.5 . .
C6 C1 C2 118.0(5) . .
C6 C1 N1 122.1(4) . .
C2 C1 N1 119.9(4) . .
F1 C2 C3 118.0(4) . .
F1 C2 C1 119.1(4) . .
C3 C2 C1 122.9(5) . .
C2 C3 C4 116.9(5) . .
C2 C3 B1 124.1(5) . .
C4 C3 B1 119.0(5) . .
C3 C4 C5 122.0(5) . .
C3 C4 H4A 119.0 . .
C5 C4 H4A 119.0 . .
C6 C5 C4 119.0(5) . .
C6 C5 B2 120.7(5) . .
C4 C5 B2 120.3(5) . .
C5 C6 C1 121.2(5) . .
C5 C6 H6A 119.4 . .
C1 C6 H6A 119.4 . .
N1 C7 H7A 109.8 . .
N1 C7 H7B 109.3 . .
H7A C7 H7B 108.6 . .
N1 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O12 S1 O12 117.7(4) . 6_565
O12 S1 O11 110.4(3) . .
O12 S1 O11 110.4(3) 6_565 .
O12 S1 C17 107.0(2) . .
O12 S1 C17 107.0(2) 6_565 .
O11 S1 C17 103.2(3) . .
C22 C17 C18 117.8(7) . .
C22 C17 S1 120.0(6) . .
C18 C17 S1 122.2(5) . .
C17 C18 C19 121.5(6) . .
C17 C18 H18A 119.2 . .
C19 C18 H18A 119.2 . .
C20 C19 C18 121.1(7) . .
C20 C19 H19A 119.5 . .
C18 C19 H19A 119.5 . .
C19 C20 C21 118.0(7) . .
C19 C20 C23 121.4(8) . .
C21 C20 C23 120.7(8) . .
C20 C21 C22 121.6(7) . .
C20 C21 H21A 119.2 . .
C22 C21 H21A 119.2 . .
C17 C22 C21 120.1(7) . .
C17 C22 H22A 119.9 . .
C21 C22 H22A 119.9 . .
C20 C23 H23A 110.3 . .
C20 C23 H23B 109.0 . .
H23A C23 H23B 109.5 . .
Cl1S C1S Cl2S 111.2(4) . .
Cl1S C1S H1S 109.4 . .
Cl2S C1S H1S 109.4 . .
Cl4S C2S Cl3S 110.6(8) . .
Cl4S C2S C3S 55.5(5) . .
Cl3S C2S C3S 55.1(5) . .
Cl4S C2S H2S 107.8 . .
Cl3S C2S H2S 111.2 . .
C3S C2S H2S 125.9 . .
Cl3S C3S Cl4S 108.3(8) . .
Cl3S C3S C2S 54.2(5) . .
Cl4S C3S C2S 54.1(5) . .
Cl3S C3S H3S 109.3 . .
Cl4S C3S H3S 110.7 . .
C2S C3S H3S 125.8 . .
C2S Cl3S C3S 70.6(7) . .
C2S Cl4S C3S 70.4(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.361(6) .
N1 C1 1.496(6) .
N1 C8 1.509(5) 6_565
N1 C8 1.509(5) .
N1 C7 1.521(6) .
B1 O1 1.349(6) .
B1 O2 1.364(6) .
B1 C3 1.560(7) .
O1 C9 1.465(7) .
O2 C10 1.459(6) .
C9 C91 1.532(7) .
C9 C10 1.534(8) .
C9 C92 1.537(9) .
C91 H91A 0.9800 .
C91 H91B 0.9800 .
C91 H91C 0.9800 .
C92 H92A 0.9800 .
C92 H92B 0.9800 .
C92 H92C 0.9800 .
C10 C102 1.525(9) .
C10 C101 1.525(8) .
C101 H10A 0.9800 .
C101 H10B 0.9800 .
C101 H10C 0.9800 .
C102 H10D 0.9800 .
C102 H10E 0.9800 .
C102 H10F 0.9800 .
B2 O4 1.338(7) .
B2 O3 1.361(7) .
B2 C5 1.570(8) .
O3 C11 1.457(7) .
O4 C12 1.466(9) .
C11 C112 1.523(9) .
C11 C111 1.526(10) .
C11 C12 1.529(8) .
C111 H11A 0.9800 .
C111 H11B 0.9800 .
C111 H11C 0.9800 .
C112 H11D 0.9800 .
C112 H11E 0.9800 .
C112 H11F 0.9800 .
C12 C122 1.526(9) .
C12 C121 1.530(9) .
C121 H12A 0.9800 .
C121 H12B 0.9800 .
C121 H12C 0.9800 .
C122 H12D 0.9800 .
C122 H12E 0.9800 .
C122 H12F 0.9800 .
C1 C6 1.387(7) .
C1 C2 1.390(7) .
C2 C3 1.388(7) .
C3 C4 1.388(8) .
C4 C5 1.389(8) .
C4 H4A 0.9500 .
C5 C6 1.381(8) .
C6 H6A 0.9500 .
C7 H7A 0.9599 .
C7 H7B 0.9605 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
S1 O12 1.402(4) .
S1 O12 1.402(4) 6_565
S1 O11 1.460(7) .
S1 C17 1.757(7) .
C17 C22 1.366(9) .
C17 C18 1.377(10) .
C18 C19 1.378(11) .
C18 H18A 0.9500 .
C19 C20 1.348(10) .
C19 H19A 0.9500 .
C20 C21 1.374(12) .
C20 C23 1.515(12) .
C21 C22 1.389(12) .
C21 H21A 0.9500 .
C22 H22A 0.9500 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C1S Cl1S 1.758(7) .
C1S Cl2S 1.759(6) .
C1S H1S 0.9901 .
C2S Cl4S 1.726(9) .
C2S Cl3S 1.728(9) .
C2S C3S 2.01(2) .
C2S H2S 0.9600 .
C3S Cl3S 1.748(10) .
C3S Cl4S 1.757(10) .
C3S H3S 0.9598 .
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
O2 B1 O1 C9 -14.2(7) .
C3 B1 O1 C9 167.2(4) .
O1 B1 O2 C10 -5.4(7) .
C3 B1 O2 C10 173.3(4) .
B1 O1 C9 C91 148.6(9) .
B1 O1 C9 C10 26.5(7) .
B1 O1 C9 C92 -93.6(8) .
B1 O2 C10 C102 -96.9(9) .
B1 O2 C10 C101 141.7(9) .
B1 O2 C10 C9 21.4(7) .
O1 C9 C10 O2 -28.7(7) .
C91 C9 C10 O2 -146.2(7) .
C92 C9 C10 O2 84.1(10) .
O1 C9 C10 C102 85.9(9) .
C91 C9 C10 C102 -31.6(10) .
C92 C9 C10 C102 -161.3(7) .
O1 C9 C10 C101 -144.3(7) .
C91 C9 C10 C101 98.2(8) .
C92 C9 C10 C101 -31.5(10) .
O4 B2 O3 C11 8(3) .
C5 B2 O3 C11 -179.4(12) .
O3 B2 O4 C12 2(4) .
C5 B2 O4 C12 -170.8(15) .
B2 O3 C11 C112 117.9(14) .
B2 O3 C11 C111 -124.4(14) .
B2 O3 C11 C12 -13(2) .
B2 O4 C12 C122 -138(3) .
B2 O4 C12 C11 -10(4) .
B2 O4 C12 C121 103(3) .
O3 C11 C12 O4 14(3) .
C112 C11 C12 O4 -112(3) .
C111 C11 C12 O4 119(3) .
O3 C11 C12 C122 131.7(15) .
C112 C11 C12 C122 6(2) .
C111 C11 C12 C122 -123.2(18) .
O3 C11 C12 C121 -100.7(16) .
C112 C11 C12 C121 133.6(16) .
C111 C11 C12 C121 4.3(16) .
C8 N1 C1 C6 -118.6(3) 6_565
C8 N1 C1 C6 118.6(3) .
C7 N1 C1 C6 0.000(1) .
C8 N1 C1 C2 61.4(3) 6_565
C8 N1 C1 C2 -61.4(3) .
C7 N1 C1 C2 180.000(1) .
C6 C1 C2 F1 180.000(1) .
N1 C1 C2 F1 0.000(1) .
C6 C1 C2 C3 0.000(2) .
N1 C1 C2 C3 180.000(1) .
F1 C2 C3 C4 180.000(1) .
C1 C2 C3 C4 0.000(2) .
F1 C2 C3 B1 0.000(2) .
C1 C2 C3 B1 180.000(2) .
O1 B1 C3 C2 16.8(4) .
O2 B1 C3 C2 -161.7(3) .
O1 B1 C3 C4 -163.2(4) .
O2 B1 C3 C4 18.3(3) .
C2 C3 C4 C5 0.000(2) .
B1 C3 C4 C5 180.000(2) .
C3 C4 C5 C6 0.000(2) .
C3 C4 C5 B2 180.000(2) .
O4 B2 C5 C6 6(3) .
O3 B2 C5 C6 -166.3(9) .
O4 B2 C5 C4 -174(3) .
O3 B2 C5 C4 13.7(9) .
C4 C5 C6 C1 0.000(2) .
B2 C5 C6 C1 180.000(1) .
C2 C1 C6 C5 0.000(2) .
N1 C1 C6 C5 180.000(1) .
O12 S1 C17 C22 63.5(3) .
O12 S1 C17 C22 -63.5(3) 6_565
O11 S1 C17 C22 180.000(1) .
O12 S1 C17 C18 -116.5(3) .
O12 S1 C17 C18 116.5(3) 6_565
O11 S1 C17 C18 0.000(1) .
C22 C17 C18 C19 0.000(1) .
S1 C17 C18 C19 180.000(1) .
C17 C18 C19 C20 0.000(1) .
C18 C19 C20 C21 0.000(1) .
C18 C19 C20 C23 180.000(0) .
C19 C20 C21 C22 0.000(1) .
C23 C20 C21 C22 180.000(1) .
C18 C17 C22 C21 0.000(1) .
S1 C17 C22 C21 180.000(1) .
C20 C21 C22 C17 0.000(1) .
Cl4S C2S Cl3S C3S 0.000(2) .
Cl4S C3S Cl3S C2S 0.000(2) .
Cl3S C2S Cl4S C3S 0.000(1) .
Cl3S C3S Cl4S C2S 0.000(2) .
