#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:55:58 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178730 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/41/4084185.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_4084185
loop_
_publ_author_name
'Seidel, Günter'
'Fürstner, Alois'
_publ_section_title
;
 A Novel Boron Heterocycle Comprised of an Inner Boronium/Borate Adduct
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              4336
_journal_paper_doi               10.1021/om500619x
_journal_volume                  33
_journal_year                    2014
_chemical_compound_source        toluene
_chemical_formula_moiety         'C20 H38 B2 S2'
_chemical_formula_sum            'C20 H38 B2 S2'
_chemical_formula_weight         364.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.500(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4997(2)
_cell_length_b                   12.9246(4)
_cell_length_c                   12.0586(4)
_cell_measurement_reflns_used    53289
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.14
_cell_measurement_theta_min      2.91
_cell_volume                     976.15(5)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD ω-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30859
_diffrn_reflns_theta_full        27.75
_diffrn_reflns_theta_max         33.16
_diffrn_reflns_theta_min         3.25
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack, Otwinowski (1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.805
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         3841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.805
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0361
_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)+(0.0734P)²+0.8244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                3486
_reflns_number_total             3841
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om500619x_si_001.cif
_cod_data_source_block           5504
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (16
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (21
time).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (27
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (53
times).

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4084185--4084191.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P21/m
_cod_database_code               4084185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.27495(3) 0.124835(16) 0.250020(17) 0.01221(7) Uani 1 1 d .
B1 B 0.2886(2) 0.2500 0.34251(11) 0.0115(2) Uani 1 2 d S
B2 B 0.0826(2) 0.2500 0.03432(12) 0.0116(2) Uani 1 2 d S
C1 C 0.52435(15) 0.10925(8) 0.21337(8) 0.01721(17) Uani 1 1 d .
H1A H 0.5239 0.0432 0.1734 0.026 Uiso 1 1 calc R
H1B H 0.6423 0.1100 0.2838 0.026 Uiso 1 1 calc R
H1C H 0.5425 0.1661 0.1630 0.026 Uiso 1 1 calc R
C2 C 0.07646(14) 0.14640(7) 0.11370(7) 0.01334(15) Uani 1 1 d .
H2A H 0.0809 0.0854 0.0647 0.016 Uiso 1 1 calc R
H2B H -0.0649 0.1456 0.1300 0.016 Uiso 1 1 calc R
C11 C 0.08282(19) 0.2500 0.39502(11) 0.0136(2) Uani 1 2 d S
H11 H -0.0499 0.2500 0.3298 0.016 Uiso 1 2 calc SR
C12 C 0.08640(15) 0.15027(8) 0.46697(8) 0.01735(17) Uani 1 1 d .
H12A H -0.0304 0.1544 0.5053 0.021 Uiso 1 1 calc R
H12B H 0.0565 0.0904 0.4139 0.021 Uiso 1 1 calc R
C13 C 0.29770(16) 0.13006(8) 0.55946(9) 0.01968(18) Uani 1 1 d .
H13A H 0.3019 0.1747 0.6268 0.024 Uiso 1 1 calc R
H13B H 0.2989 0.0573 0.5851 0.024 Uiso 1 1 calc R
C14 C 0.50119(15) 0.14986(8) 0.52005(8) 0.01763(17) Uani 1 1 d .
H14A H 0.5236 0.0902 0.4731 0.021 Uiso 1 1 calc R
H14B H 0.6246 0.1528 0.5890 0.021 Uiso 1 1 calc R
C15 C 0.49902(19) 0.2500 0.44926(11) 0.0137(2) Uani 1 2 d S
H15 H 0.6275 0.2500 0.4185 0.016 Uiso 1 2 calc SR
C21 C 0.26749(18) 0.2500 -0.03590(10) 0.0126(2) Uani 1 2 d S
H21 H 0.4100 0.2500 0.0220 0.015 Uiso 1 2 calc SR
C22 C 0.25104(14) 0.15056(7) -0.10882(8) 0.01573(16) Uani 1 1 d .
H22A H 0.3581 0.1545 -0.1536 0.019 Uiso 1 1 calc R
H22B H 0.2892 0.0908 -0.0560 0.019 Uiso 1 1 calc R
C23 C 0.03051(15) 0.12974(8) -0.19287(8) 0.01746(17) Uani 1 1 d .
H23A H 0.0155 0.1734 -0.2620 0.021 Uiso 1 1 calc R
H23B H 0.0248 0.0566 -0.2178 0.021 Uiso 1 1 calc R
C24 C -0.16061(14) 0.15086(8) -0.14296(8) 0.01683(17) Uani 1 1 d .
H24A H -0.1778 0.0910 -0.0950 0.020 Uiso 1 1 calc R
H24B H -0.2916 0.1557 -0.2075 0.020 Uiso 1 1 calc R
C25 C -0.14202(19) 0.2500 -0.06949(10) 0.0137(2) Uani 1 2 d S
H25 H -0.2629 0.2500 -0.0327 0.016 Uiso 1 2 calc SR
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C2 105.23(4) . . y
C1 S1 B1 109.02(5) . . y
C2 S1 B1 107.58(5) . . y
C15 B1 C11 107.48(10) . . y
C15 B1 S1 110.87(5) . 4_565 ?
C11 B1 S1 107.80(5) . 4_565 ?
C15 B1 S1 110.87(5) . . y
C11 B1 S1 107.80(5) . . y
S1 B1 S1 111.82(6) 4_565 . y
C25 B2 C21 103.27(9) . . y
C25 B2 C2 106.62(6) . . y
C21 B2 C2 115.61(6) . . y
C25 B2 C2 106.62(6) . 4_565 ?
C21 B2 C2 115.61(6) . 4_565 ?
C2 B2 C2 108.24(10) . 4_565 ?
S1 C1 H1A 109.5 . . n
S1 C1 H1B 109.5 . . n
H1A C1 H1B 109.5 . . n
S1 C1 H1C 109.5 . . n
H1A C1 H1C 109.5 . . n
H1B C1 H1C 109.5 . . n
B2 C2 S1 121.76(7) . . y
B2 C2 H2A 106.9 . . n
S1 C2 H2A 106.9 . . n
B2 C2 H2B 106.9 . . n
S1 C2 H2B 106.9 . . n
H2A C2 H2B 106.7 . . n
C12 C11 C12 112.47(11) . 4_565 ?
C12 C11 B1 109.09(6) . . y
C12 C11 B1 109.09(7) 4_565 . y
C12 C11 H11 108.7 . . n
C12 C11 H11 108.7 4_565 . n
B1 C11 H11 108.7 . . n
C13 C12 C11 115.00(8) . . y
C13 C12 H12A 108.5 . . n
C11 C12 H12A 108.5 . . n
C13 C12 H12B 108.5 . . n
C11 C12 H12B 108.5 . . n
H12A C12 H12B 107.5 . . n
C14 C13 C12 114.86(8) . . y
C14 C13 H13A 108.6 . . n
C12 C13 H13A 108.6 . . n
C14 C13 H13B 108.6 . . n
C12 C13 H13B 108.6 . . n
H13A C13 H13B 107.5 . . n
C13 C14 C15 115.25(8) . . y
C13 C14 H14A 108.5 . . n
C15 C14 H14A 108.5 . . n
C13 C14 H14B 108.5 . . n
C15 C14 H14B 108.5 . . n
H14A C14 H14B 107.5 . . n
C14 C15 C14 113.41(11) . 4_565 ?
C14 C15 B1 108.77(7) . . y
C14 C15 B1 108.77(7) 4_565 . y
C14 C15 H15 108.6 . . n
C14 C15 H15 108.6 4_565 . n
B1 C15 H15 108.6 . . n
C22 C21 C22 112.61(10) 4_565 . y
C22 C21 B2 110.13(6) 4_565 . y
C22 C21 B2 110.13(6) . . y
C22 C21 H21 107.9 4_565 . n
C22 C21 H21 107.9 . . n
B2 C21 H21 107.9 . . n
C23 C22 C21 115.48(8) . . y
C23 C22 H22A 108.4 . . n
C21 C22 H22A 108.4 . . n
C23 C22 H22B 108.4 . . n
C21 C22 H22B 108.4 . . n
H22A C22 H22B 107.5 . . n
C24 C23 C22 114.63(7) . . y
C24 C23 H23A 108.6 . . n
C22 C23 H23A 108.6 . . n
C24 C23 H23B 108.6 . . n
C22 C23 H23B 108.6 . . n
H23A C23 H23B 107.6 . . n
C23 C24 C25 115.03(8) . . y
C23 C24 H24A 108.5 . . n
C25 C24 H24A 108.5 . . n
C23 C24 H24B 108.5 . . n
C25 C24 H24B 108.5 . . n
H24A C24 H24B 107.5 . . n
C24 C25 C24 112.17(11) 4_565 . y
C24 C25 B2 110.67(6) 4_565 . y
C24 C25 B2 110.67(6) . . y
C24 C25 H25 107.7 4_565 . n
C24 C25 H25 107.7 . . n
B2 C25 H25 107.7 . . n
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
S1 C1 1.8018(9) . y
S1 C2 1.8196(9) . y
S1 B1 1.9534(8) . y
B1 C15 1.6081(18) . y
B1 C11 1.6258(18) . y
B1 S1 1.9534(8) 4_565 ?
B2 C25 1.6498(18) . y
B2 C21 1.6447(18) . y
B2 C2 1.6526(12) . y
B2 C2 1.6526(12) 4_565 ?
C1 H1A 0.9800 . n
C1 H1B 0.9800 . n
C1 H1C 0.9800 . n
C2 H2A 0.9900 . n
C2 H2B 0.9900 . n
C11 C12 1.5504(12) . y
C11 C12 1.5505(12) 4_565 ?
C11 H11 1.0000 . n
C12 C13 1.5427(14) . y
C12 H12A 0.9900 . n
C12 H12B 0.9900 . n
C13 C14 1.5416(14) . y
C13 H13A 0.9900 . n
C13 H13B 0.9900 . n
C14 C15 1.5484(12) . y
C14 H14A 0.9900 . n
C14 H14B 0.9900 . n
C15 C14 1.5484(12) 4_565 ?
C15 H15 1.0000 . n
C21 C22 1.5447(11) 4_565 ?
C21 C22 1.5447(11) . y
C21 H21 1.0000 . n
C22 C23 1.5420(13) . y
C22 H22A 0.9900 . n
C22 H22B 0.9900 . n
C23 C24 1.5426(13) . y
C23 H23A 0.9900 . n
C23 H23B 0.9900 . n
C24 C25 1.5440(12) . y
C24 H24A 0.9900 . n
C24 H24B 0.9900 . n
C25 C24 1.5440(12) 4_565 ?
C25 H25 1.0000 . n
