#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:35:21 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178572 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/82/4068227.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_4068227
loop_
_publ_author_name
'Solovyev, Andrey'
'Geib, Steven J.'
'Lacôte, Emmanuel'
'Curran, Dennis P.'
_publ_section_title
;
 Reactions of Boron-Substituted N-Heterocyclic Carbene Boranes with
 Triflic Acid. Isolation of a New Dihydroxyborenium Cation
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              54
_journal_paper_doi               10.1021/om201260b
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C28 H37 B Cl F3 N2 O3 S'
_chemical_formula_weight         584.92
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.230(2)
_cell_length_b                   18.200(2)
_cell_length_c                   9.9966(13)
_cell_measurement_reflns_used    2956
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      19.17
_cell_measurement_theta_min      2.24
_cell_volume                     3134.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       '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  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23607
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.962
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0901
_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)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2474
_refine_ls_wR_factor_ref         0.2600
_reflns_number_gt                1899
_reflns_number_total             2854
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om201260b_si_001.cif
_cod_data_source_block           as82_14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3134.8(7)
_cod_database_code               4068227
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
Cl Cl 0.05148(11) 0.2500 0.68057(16) 0.1298(9) Uani 1 2 d S
S S -0.12748(11) 0.2500 0.4579(3) 0.1537(12) Uani 1 2 d S
B B 0.0209(4) 0.2500 0.5069(8) 0.103(3) Uani 1 2 d S
N1 N 0.13638(16) 0.30873(14) 0.3693(3) 0.0596(8) Uani 1 1 d .
C1 C 0.0952(3) 0.2500 0.4102(4) 0.0567(12) Uani 1 2 d S
O1 O -0.0440(3) 0.2883(2) 0.4714(5) 0.0700(13) Uani 0.50 1 d P
F1 F -0.1427(3) 0.3065(2) 0.6888(5) 0.1817(18) Uani 1 1 d .
C2 C 0.2025(2) 0.2859(2) 0.3047(4) 0.0716(11) Uani 1 1 d .
H2 H 0.2350(19) 0.3175(15) 0.273(3) 0.057(9) Uiso 1 1 d .
F2 F -0.2407(3) 0.2500 0.6142(8) 0.204(3) Uani 1 2 d S
O2 O -0.1527(3) 0.3135(3) 0.3990(5) 0.194(2) Uani 1 1 d .
C3 C 0.1116(2) 0.38525(19) 0.3729(4) 0.0638(9) Uani 1 1 d .
C4 C 0.1405(2) 0.4307(2) 0.4727(4) 0.0727(11) Uani 1 1 d .
C5 C 0.1156(3) 0.5040(2) 0.4679(5) 0.0930(14) Uani 1 1 d .
H5A H 0.1327 0.5366 0.5332 0.112 Uiso 1 1 calc R
C6 C 0.0668(3) 0.5290(2) 0.3696(6) 0.1030(16) Uani 1 1 d .
H6A H 0.0506 0.5777 0.3696 0.124 Uiso 1 1 calc R
C7 C 0.0422(3) 0.4830(3) 0.2730(5) 0.0952(13) Uani 1 1 d .
H7A H 0.0101 0.5012 0.2058 0.114 Uiso 1 1 calc R
C8 C 0.0629(2) 0.4097(2) 0.2703(4) 0.0773(11) Uani 1 1 d .
C9 C 0.1958(2) 0.4053(2) 0.5791(4) 0.0873(12) Uani 1 1 d .
H9A H 0.1973 0.3515 0.5759 0.105 Uiso 1 1 calc R
C10 C 0.2783(3) 0.4336(4) 0.5492(7) 0.158(3) Uani 1 1 d .
H10A H 0.2937 0.4181 0.4613 0.238 Uiso 1 1 calc R
H10B H 0.3139 0.4140 0.6140 0.238 Uiso 1 1 calc R
H10C H 0.2788 0.4863 0.5537 0.238 Uiso 1 1 calc R
C11 C 0.1711(4) 0.4275(3) 0.7191(5) 0.142(2) Uani 1 1 d .
H11A H 0.1211 0.4067 0.7386 0.214 Uiso 1 1 calc R
H11B H 0.1681 0.4801 0.7246 0.214 Uiso 1 1 calc R
H11C H 0.2084 0.4097 0.7827 0.214 Uiso 1 1 calc R
C12 C 0.0374(3) 0.3602(2) 0.1573(4) 0.0985(15) Uani 1 1 d .
H12A H 0.0421 0.3092 0.1882 0.118 Uiso 1 1 calc R
C13 C 0.0918(4) 0.3697(4) 0.0361(5) 0.147(2) Uani 1 1 d .
H13A H 0.1448 0.3654 0.0648 0.221 Uiso 1 1 calc R
H13B H 0.0838 0.4172 -0.0030 0.221 Uiso 1 1 calc R
H13C H 0.0808 0.3324 -0.0291 0.221 Uiso 1 1 calc R
C14 C -0.0463(4) 0.3723(4) 0.1148(6) 0.148(2) Uani 1 1 d .
H14A H -0.0799 0.3660 0.1906 0.222 Uiso 1 1 calc R
H14B H -0.0599 0.3373 0.0469 0.222 Uiso 1 1 calc R
H14C H -0.0521 0.4211 0.0800 0.222 Uiso 1 1 calc R
C15 C -0.1636(5) 0.2500 0.6225(11) 0.133(3) Uani 1 2 d S
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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
O2 S O2 115.3(4) 7_565 .
O2 S O1 133.5(3) 7_565 .
O2 S O1 87.4(3) . .
O2 S O1 87.4(3) 7_565 7_565
O2 S O1 133.5(3) . 7_565
O1 S O1 51.5(3) . 7_565
O2 S C15 106.9(3) 7_565 .
O2 S C15 106.9(3) . .
O1 S C15 103.8(4) . .
O1 S C15 103.8(4) 7_565 .
O1 B O1 61.4(5) 7_565 .
O1 B C1 119.8(5) 7_565 .
O1 B C1 119.8(5) . .
O1 B Cl 119.1(4) 7_565 .
O1 B Cl 119.1(4) . .
C1 B Cl 110.2(5) . .
C1 N1 C2 109.9(3) . .
C1 N1 C3 126.6(3) . .
C2 N1 C3 123.0(3) . .
N1 C1 N1 105.0(4) 7_565 .
N1 C1 B 127.15(19) 7_565 .
N1 C1 B 127.15(19) . .
B O1 O1 59.3(3) . 7_565
B O1 S 122.3(4) . .
O1 O1 S 64.26(16) 7_565 .
C2 C2 N1 107.6(2) 7_565 .
C2 C2 H2 132(2) 7_565 .
N1 C2 H2 120(2) . .
C4 C3 C8 123.6(3) . .
C4 C3 N1 118.9(3) . .
C8 C3 N1 117.5(3) . .
C3 C4 C5 115.7(4) . .
C3 C4 C9 123.5(3) . .
C5 C4 C9 120.8(4) . .
C6 C5 C4 121.8(4) . .
C6 C5 H5A 119.1 . .
C4 C5 H5A 119.1 . .
C7 C6 C5 120.1(4) . .
C7 C6 H6A 119.9 . .
C5 C6 H6A 119.9 . .
C6 C7 C8 122.1(5) . .
C6 C7 H7A 118.9 . .
C8 C7 H7A 118.9 . .
C7 C8 C3 116.7(4) . .
C7 C8 C12 121.0(4) . .
C3 C8 C12 122.3(3) . .
C4 C9 C11 113.1(4) . .
C4 C9 C10 110.2(4) . .
C11 C9 C10 110.4(5) . .
C4 C9 H9A 107.6 . .
C11 C9 H9A 107.6 . .
C10 C9 H9A 107.6 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C8 C12 C14 113.5(4) . .
C8 C12 C13 110.1(4) . .
C14 C12 C13 109.9(4) . .
C8 C12 H12A 107.7 . .
C14 C12 H12A 107.7 . .
C13 C12 H12A 107.7 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C12 C14 H14A 109.5 . .
C12 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C12 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
F1 C15 F1 107.5(10) . 7_565
F1 C15 F2 108.3(5) . .
F1 C15 F2 108.3(5) 7_565 .
F1 C15 S 112.7(4) . .
F1 C15 S 112.7(4) 7_565 .
F2 C15 S 107.1(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl B 1.814(8) .
S O2 1.368(5) 7_565
S O2 1.368(5) .
S O1 1.604(5) .
S O1 1.604(5) 7_565
S C15 1.759(10) .
B O1 1.364(8) 7_565
B O1 1.364(8) .
B C1 1.603(8) .
N1 C1 1.347(4) .
N1 C2 1.375(4) .
N1 C3 1.457(4) .
C1 N1 1.347(4) 7_565
O1 O1 1.394(9) 7_565
F1 C15 1.276(7) .
C2 C2 1.305(8) 7_565
C2 H2 0.86(3) .
F2 C15 1.331(10) .
C3 C4 1.389(5) .
C3 C8 1.397(5) .
C4 C5 1.402(6) .
C4 C9 1.501(6) .
C5 C6 1.372(7) .
C5 H5A 0.9300 .
C6 C7 1.346(7) .
C6 H6A 0.9300 .
C7 C8 1.382(5) .
C7 H7A 0.9300 .
C8 C12 1.511(6) .
C9 C11 1.518(6) .
C9 C10 1.542(6) .
C9 H9A 0.9800 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C14 1.521(7) .
C12 C13 1.541(7) .
C12 H12A 0.9800 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 F1 1.276(7) 7_565
