#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/89/7108946.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_7108946
loop_
_publ_author_name
'Erich F. Altenhofer'
'Michael Harmata'
_publ_section_title
;
 Generation and alkylation of 2-boryl allylic sulfone anions
;
_journal_name_full               Chem.Commun.
_journal_page_first              2365
_journal_paper_doi               10.1039/c3cc00030c
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C15 H21 B O4 S'
_chemical_formula_weight         308.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 110.706(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5821(19)
_cell_length_b                   14.345(3)
_cell_length_c                   12.465(3)
_cell_measurement_reflns_used    9577
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     1602.7(6)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18510
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.25
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Data were corrected for decay and absorption using the program SADABS
(Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
Göttingen, Germany).
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.6038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                3355
_reflns_number_total             3682
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc00030c.txt
_cod_data_source_block           EA1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7108946
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 0.96239(3) 0.12467(2) 0.37268(3) 0.02554(10) Uani 1 1 d .
O1 O 1.09099(10) 0.11415(7) 0.33933(10) 0.0377(2) Uani 1 1 d .
O2 O 0.98340(11) 0.11793(7) 0.49278(8) 0.0355(2) Uani 1 1 d .
O3 O 0.56814(9) 0.14343(6) 0.12107(7) 0.02682(19) Uani 1 1 d .
O4 O 0.40798(10) 0.10322(7) 0.21239(8) 0.0303(2) Uani 1 1 d .
C1 C 0.82895(13) 0.03916(8) 0.29574(11) 0.0274(3) Uani 1 1 d .
H1A H 0.8154 0.0434 0.2134 0.033 Uiso 1 1 calc R
H1B H 0.8692 -0.0235 0.3230 0.033 Uiso 1 1 calc R
C2 C 0.67877(13) 0.04913(8) 0.30820(10) 0.0255(2) Uani 1 1 d .
C3 C 0.42048(13) 0.17417(8) 0.04412(10) 0.0234(2) Uani 1 1 d .
C4 C 0.32340(13) 0.16828(9) 0.12237(10) 0.0253(2) Uani 1 1 d .
C5 C 0.65563(15) 0.01419(10) 0.39951(12) 0.0343(3) Uani 1 1 d .
H5A H 0.7340 -0.0172 0.4572 0.041 Uiso 1 1 calc R
H5B H 0.5608 0.0207 0.4069 0.041 Uiso 1 1 calc R
C6 C 0.43714(16) 0.27158(9) 0.00215(12) 0.0325(3) Uani 1 1 d .
H6A H 0.4690 0.3146 0.0674 0.049 Uiso 1 1 calc R
H6B H 0.3412 0.2922 -0.0532 0.049 Uiso 1 1 calc R
H6C H 0.5120 0.2707 -0.0348 0.049 Uiso 1 1 calc R
C7 C 0.37157(16) 0.10568(9) -0.05550(11) 0.0317(3) Uani 1 1 d .
H7A H 0.3612 0.0434 -0.0269 0.048 Uiso 1 1 calc R
H7B H 0.4465 0.1040 -0.0924 0.048 Uiso 1 1 calc R
H7C H 0.2755 0.1255 -0.1114 0.048 Uiso 1 1 calc R
C8 C 0.31455(17) 0.25944(10) 0.18159(12) 0.0372(3) Uani 1 1 d .
H8A H 0.4151 0.2850 0.2181 0.056 Uiso 1 1 calc R
H8B H 0.2699 0.2482 0.2400 0.056 Uiso 1 1 calc R
H8C H 0.2529 0.3039 0.1249 0.056 Uiso 1 1 calc R
C9 C 0.16779(15) 0.12832(10) 0.06500(13) 0.0360(3) Uani 1 1 d .
H9A H 0.1742 0.0694 0.0273 0.054 Uiso 1 1 calc R
H9B H 0.1066 0.1726 0.0078 0.054 Uiso 1 1 calc R
H9C H 0.1222 0.1172 0.1229 0.054 Uiso 1 1 calc R
C10 C 0.88030(12) 0.23410(8) 0.32380(10) 0.0239(2) Uani 1 1 d .
C11 C 0.79877(14) 0.27817(9) 0.38171(12) 0.0303(3) Uani 1 1 d .
H11 H 0.7825 0.2486 0.4445 0.036 Uiso 1 1 calc R
C12 C 0.74161(16) 0.36645(10) 0.34575(14) 0.0385(3) Uani 1 1 d .
H12 H 0.6860 0.3978 0.3846 0.046 Uiso 1 1 calc R
C13 C 0.76481(16) 0.40919(10) 0.25418(14) 0.0398(3) Uani 1 1 d .
H13 H 0.7260 0.4698 0.2309 0.048 Uiso 1 1 calc R
C14 C 0.84438(16) 0.36403(10) 0.19625(13) 0.0369(3) Uani 1 1 d .
H14 H 0.8589 0.3933 0.1326 0.044 Uiso 1 1 calc R
C15 C 0.90306(14) 0.27602(9) 0.23093(11) 0.0301(3) Uani 1 1 d .
H15 H 0.9582 0.2448 0.1916 0.036 Uiso 1 1 calc R
B1 B 0.54980(15) 0.10012(9) 0.21231(12) 0.0242(3) Uani 1 1 d .
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'
O O 0.0106 0.0060 '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
O1 S1 O2 118.23(6)
O1 S1 C10 108.40(6)
O2 S1 C10 107.45(6)
O1 S1 C1 107.21(6)
O2 S1 C1 108.79(6)
C10 S1 C1 106.16(6)
B1 O3 C3 107.68(9)
B1 O4 C4 107.62(9)
C2 C1 S1 114.05(9)
C2 C1 H1A 108.7
S1 C1 H1A 108.7
C2 C1 H1B 108.7
S1 C1 H1B 108.7
H1A C1 H1B 107.6
C5 C2 C1 120.37(11)
C5 C2 B1 120.25(12)
C1 C2 B1 119.38(11)
O3 C3 C6 107.86(10)
O3 C3 C7 106.67(9)
C6 C3 C7 110.62(10)
O3 C3 C4 102.92(9)
C6 C3 C4 114.87(10)
C7 C3 C4 113.14(10)
O4 C4 C8 106.69(10)
O4 C4 C9 107.78(10)
C8 C4 C9 109.84(11)
O4 C4 C3 102.79(9)
C8 C4 C3 113.75(11)
C9 C4 C3 115.23(11)
C2 C5 H5A 120.0
C2 C5 H5B 120.0
H5A C5 H5B 120.0
C3 C6 H6A 109.5
C3 C6 H6B 109.5
H6A C6 H6B 109.5
C3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C3 C7 H7A 109.5
C3 C7 H7B 109.5
H7A C7 H7B 109.5
C3 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C4 C9 H9A 109.5
C4 C9 H9B 109.5
H9A C9 H9B 109.5
C4 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C15 C10 C11 121.27(12)
C15 C10 S1 119.40(9)
C11 C10 S1 119.29(10)
C10 C11 C12 118.49(13)
C10 C11 H11 120.8
C12 C11 H11 120.8
C13 C12 C11 120.72(13)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 120.22(13)
C12 C13 H13 119.9
C14 C13 H13 119.9
C13 C14 C15 120.08(14)
C13 C14 H14 120.0
C15 C14 H14 120.0
C14 C15 C10 119.21(12)
C14 C15 H15 120.4
C10 C15 H15 120.4
O4 B1 O3 114.21(10)
O4 B1 C2 122.30(11)
O3 B1 C2 123.48(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4410(11)
S1 O2 1.4415(11)
S1 C10 1.7650(12)
S1 C1 1.7867(12)
O3 B1 1.3608(16)
O3 C3 1.4685(13)
O4 B1 1.3600(16)
O4 C4 1.4642(14)
C1 C2 1.5078(17)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C5 1.3321(19)
C2 B1 1.5641(17)
C3 C6 1.5202(17)
C3 C7 1.5216(17)
C3 C4 1.5702(17)
C4 C8 1.5187(18)
C4 C9 1.5196(18)
C5 H5A 0.9500
C5 H5B 0.9500
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
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
C10 C15 1.3884(18)
C10 C11 1.3892(17)
C11 C12 1.390(2)
C11 H11 0.9500
C12 C13 1.381(2)
C12 H12 0.9500
C13 C14 1.383(2)
C13 H13 0.9500
C14 C15 1.3874(19)
C14 H14 0.9500
C15 H15 0.9500
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
O1 S1 C1 C2 -171.97(9)
O2 S1 C1 C2 59.11(10)
C10 S1 C1 C2 -56.25(10)
S1 C1 C2 C5 -82.51(14)
S1 C1 C2 B1 98.04(12)
B1 O3 C3 C6 138.05(11)
B1 O3 C3 C7 -103.08(11)
B1 O3 C3 C4 16.23(12)
B1 O4 C4 C8 -100.68(12)
B1 O4 C4 C9 141.41(11)
B1 O4 C4 C3 19.27(12)
O3 C3 C4 O4 -21.25(11)
C6 C3 C4 O4 -138.19(10)
C7 C3 C4 O4 93.47(11)
O3 C3 C4 C8 93.69(11)
C6 C3 C4 C8 -23.26(14)
C7 C3 C4 C8 -151.60(11)
O3 C3 C4 C9 -138.20(10)
C6 C3 C4 C9 104.86(13)
C7 C3 C4 C9 -23.48(14)
O1 S1 C10 C15 24.44(12)
O2 S1 C10 C15 153.28(10)
C1 S1 C10 C15 -90.46(11)
O1 S1 C10 C11 -153.18(10)
O2 S1 C10 C11 -24.35(11)
C1 S1 C10 C11 91.92(11)
C15 C10 C11 C12 -0.94(19)
S1 C10 C11 C12 176.64(10)
C10 C11 C12 C13 0.3(2)
C11 C12 C13 C14 0.6(2)
C12 C13 C14 C15 -0.9(2)
C13 C14 C15 C10 0.3(2)
C11 C10 C15 C14 0.67(19)
S1 C10 C15 C14 -176.91(10)
C4 O4 B1 O3 -10.16(14)
C4 O4 B1 C2 171.00(11)
C3 O3 B1 O4 -4.74(14)
C3 O3 B1 C2 174.08(11)
C5 C2 B1 O4 -6.29(19)
C1 C2 B1 O4 173.16(11)
C5 C2 B1 O3 174.98(12)
C1 C2 B1 O3 -5.56(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71524556
