#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/98/4329858.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_4329858
loop_
_publ_author_name
'Alasdair P. M. Robertson'
'Mairi F. Haddow'
'Ian Manners'
_publ_section_title
;
 Synthesis and the Thermal and Catalytic Dehydrogenation Reactions of
 Amine-Thioboranes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8254
_journal_page_last               8264
_journal_paper_doi               10.1021/ic3008188
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C9 H11 B F5 N S'
_chemical_formula_sum            'C9 H11 B F5 N S'
_chemical_formula_weight         271.06
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.6790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6164(2)
_cell_length_b                   11.1326(2)
_cell_length_c                   10.9813(3)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.77
_cell_volume                     1159.68(4)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker ShelXTL'
_computing_publication_material  'Bruker ShelXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex II kappa with CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21386
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       lath
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0313P)²+0.4959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0686
_reflns_number_gt                2465
_reflns_number_total             2696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic3008188_si_002_03.cif
_cod_data_source_block           Me3NBH2SC6F5
_cod_database_code               4329858
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.72258(3) 0.18386(3) 0.01378(3) 0.02432(9) Uani 1 1 d .
B1 B 0.89277(14) 0.20855(11) 0.17812(15) 0.0228(3) Uani 1 1 d .
H1A H 0.8820(15) 0.1739(13) 0.2665(15) 0.027 Uiso 1 1 d .
H1B H 0.9767(15) 0.1665(13) 0.1583(15) 0.027 Uiso 1 1 d .
F1 F 0.49406(7) 0.36634(6) -0.03596(7) 0.02623(17) Uani 1 1 d .
F2 F 0.28714(7) 0.35556(6) 0.03994(8) 0.02736(17) Uani 1 1 d .
F3 F 0.26971(7) 0.16722(6) 0.18748(8) 0.02616(16) Uani 1 1 d .
F4 F 0.46259(7) -0.01487(6) 0.25726(7) 0.02244(15) Uani 1 1 d .
F5 F 0.66900(7) -0.00728(6) 0.18128(8) 0.02494(16) Uani 1 1 d .
N1 N 0.93285(10) 0.34925(8) 0.20826(10) 0.01746(19) Uani 1 1 d .
C1 C 0.59066(12) 0.18050(10) 0.07003(11) 0.0189(2) Uani 1 1 d .
C2 C 0.48972(12) 0.27049(10) 0.03612(11) 0.0199(2) Uani 1 1 d .
C3 C 0.38264(11) 0.26680(10) 0.07493(12) 0.0203(2) Uani 1 1 d .
C4 C 0.37384(11) 0.17084(10) 0.15014(12) 0.0194(2) Uani 1 1 d .
C5 C 0.47145(11) 0.07911(10) 0.18550(11) 0.0183(2) Uani 1 1 d .
C6 C 0.57754(11) 0.08470(10) 0.14552(11) 0.0185(2) Uani 1 1 d .
C7 C 1.06531(12) 0.35643(11) 0.33836(13) 0.0274(3) Uani 1 1 d .
H7A H 1.0941 0.4406 0.3587 0.041 Uiso 1 1 calc R
H7B H 1.1398 0.3110 0.3295 0.041 Uiso 1 1 calc R
H7C H 1.0491 0.3224 0.4124 0.041 Uiso 1 1 calc R
C8 C 0.95902(14) 0.40526(11) 0.09850(13) 0.0256(3) Uani 1 1 d .
H8A H 0.8734 0.4000 0.0117 0.038 Uiso 1 1 calc R
H8B H 1.0360 0.3628 0.0908 0.038 Uiso 1 1 calc R
H8C H 0.9849 0.4898 0.1208 0.038 Uiso 1 1 calc R
C9 C 0.82118(12) 0.41874(10) 0.22348(13) 0.0233(2) Uani 1 1 d .
H9A H 0.8547 0.5007 0.2532 0.035 Uiso 1 1 calc R
H9B H 0.7989 0.3798 0.2915 0.035 Uiso 1 1 calc R
H9C H 0.7364 0.4216 0.1358 0.035 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 B1 103.54(6)
N1 B1 S1 112.45(8)
N1 B1 H1A 106.4(8)
S1 B1 H1A 110.8(8)
N1 B1 H1B 106.7(8)
S1 B1 H1B 104.8(8)
H1A B1 H1B 115.9(11)
C9 N1 C8 108.72(9)
C9 N1 C7 108.73(9)
C8 N1 C7 108.34(9)
C9 N1 B1 112.15(8)
C8 N1 B1 111.54(9)
C7 N1 B1 107.24(9)
C2 C1 C6 116.06(10)
C2 C1 S1 121.86(9)
C6 C1 S1 122.01(9)
F1 C2 C3 117.16(10)
F1 C2 C1 120.31(10)
C3 C2 C1 122.53(10)
F2 C3 C4 119.74(10)
F2 C3 C2 120.65(10)
C4 C3 C2 119.60(10)
F3 C4 C3 119.55(10)
F3 C4 C5 120.62(10)
C3 C4 C5 119.83(10)
F4 C5 C4 120.10(10)
F4 C5 C6 120.34(10)
C4 C5 C6 119.55(10)
F5 C6 C5 117.28(10)
F5 C6 C1 120.30(10)
C5 C6 C1 122.42(10)
N1 C7 H7A 109.5
N1 C7 H7B 109.5
H7A C7 H7B 109.5
N1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
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
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7667(11)
S1 B1 1.9155(14)
B1 N1 1.6178(15)
B1 H1A 1.096(15)
B1 H1B 1.111(15)
F1 C2 1.3417(13)
F2 C3 1.3425(13)
F3 C4 1.3412(13)
F4 C5 1.3382(12)
F5 C6 1.3429(13)
N1 C9 1.4866(14)
N1 C8 1.4898(14)
N1 C7 1.4903(15)
C1 C2 1.3901(16)
C1 C6 1.3956(15)
C2 C3 1.3822(16)
C3 C4 1.3789(16)
C4 C5 1.3807(16)
C5 C6 1.3817(16)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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
C1 S1 B1 N1 -92.33(9)
S1 B1 N1 C9 60.16(11)
S1 B1 N1 C8 -62.07(11)
S1 B1 N1 C7 179.47(8)
B1 S1 C1 C2 112.28(10)
B1 S1 C1 C6 -70.84(10)
C6 C1 C2 F1 179.79(9)
S1 C1 C2 F1 -3.15(15)
C6 C1 C2 C3 0.39(16)
S1 C1 C2 C3 177.45(9)
F1 C2 C3 F2 0.63(16)
C1 C2 C3 F2 -179.94(10)
F1 C2 C3 C4 -179.47(10)
C1 C2 C3 C4 -0.04(17)
F2 C3 C4 F3 0.05(16)
C2 C3 C4 F3 -179.85(10)
F2 C3 C4 C5 179.60(10)
C2 C3 C4 C5 -0.30(17)
F3 C4 C5 F4 0.25(16)
C3 C4 C5 F4 -179.30(10)
F3 C4 C5 C6 179.82(10)
C3 C4 C5 C6 0.27(16)
F4 C5 C6 F5 0.22(15)
C4 C5 C6 F5 -179.36(10)
F4 C5 C6 C1 179.67(10)
C4 C5 C6 C1 0.09(17)
C2 C1 C6 F5 179.02(9)
S1 C1 C6 F5 1.97(15)
C2 C1 C6 C5 -0.41(16)
S1 C1 C6 C5 -177.47(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139137567
