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#$Date: 2018-01-06 03:57:52 +0200 (Sat, 06 Jan 2018) $
#$Revision: 204802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/32/4033231.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_4033231
loop_
_publ_author_name
'Messersmith, Reid E.'
'Yadav, Sangeeta'
'Siegler, Maxime A.'
'Ottosson, Henrik'
'Tovar, John D.'
_publ_section_title
;
 Benzo[b]thiophene Fusion Enhances Local Borepin Aromaticity in Polycyclic
 Heteroaromatic Compounds.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13440
_journal_page_last               13448
_journal_paper_doi               10.1021/acs.joc.7b02512
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C27 H21 B S2'
_chemical_formula_sum            'C27 H21 B S2'
_chemical_formula_weight         420.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           54
_space_group_name_Hall           '-P 2a 2ac'
_space_group_name_H-M_alt        'P c c a'
_symmetry_space_group_name_Hall  '-P 2a 2ac'
_symmetry_space_group_name_H-M   'P c c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8938(4)
_cell_length_b                   15.0422(4)
_cell_length_c                   8.53393(18)
_cell_measurement_reflns_used    3739
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      71.85
_cell_measurement_theta_min      3.82
_cell_volume                     2297.01(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7243
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.891
_diffrn_reflns_theta_min         2.938
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2267
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0337
_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)+(0.0483P)²+0.7259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1975
_reflns_number_total             2267
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02512_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4033231--4033232.cif.'
_cod_database_code               4033231
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.55713(8) 0.12173(10) 0.14183(16) 0.0242(3) Uani 1 1 d . . .
C2 C 0.60974(8) 0.16656(11) 0.03513(16) 0.0266(3) Uani 1 1 d . . .
C3 C 0.61629(9) 0.25680(12) -0.00764(19) 0.0328(4) Uani 1 1 d . . .
H3 H 0.5848 0.2998 0.0401 0.039 Uiso 1 1 calc R U .
C4 C 0.66833(9) 0.28329(13) -0.1188(2) 0.0388(4) Uani 1 1 d . . .
H4 H 0.6717 0.3443 -0.1465 0.047 Uiso 1 1 calc R U .
C5 C 0.71598(9) 0.22182(13) -0.19110(19) 0.0371(4) Uani 1 1 d . . .
H5 H 0.7509 0.2413 -0.2676 0.044 Uiso 1 1 calc R U .
C6 C 0.71224(8) 0.13368(12) -0.15152(17) 0.0329(4) Uani 1 1 d . . .
H6 H 0.7446 0.0915 -0.1991 0.040 Uiso 1 1 calc R U .
C7 C 0.65969(8) 0.10708(11) -0.03941(17) 0.0282(3) Uani 1 1 d . . .
C8 C 0.56950(8) 0.03012(10) 0.13687(16) 0.0257(3) Uani 1 1 d . . .
C9 C 0.53069(8) -0.04344(10) 0.20344(17) 0.0279(3) Uani 1 1 d . . .
H9 H 0.5506 -0.1004 0.1792 0.033 Uiso 1 1 calc R U .
C10 C 0.5000 0.27474(14) 0.2500 0.0250(4) Uani 1 2 d S T P
C11 C 0.45184(8) 0.32264(10) 0.15056(17) 0.0274(3) Uani 1 1 d . . .
C12 C 0.45226(10) 0.41513(11) 0.15232(17) 0.0339(4) Uani 1 1 d . . .
H12 H 0.4192 0.4466 0.0852 0.041 Uiso 1 1 calc R U .
C13 C 0.5000 0.46268(16) 0.2500 0.0364(5) Uani 1 2 d S T P
C14 C 0.40186(9) 0.27355(12) 0.03643(19) 0.0335(4) Uani 1 1 d . . .
H14A H 0.3607 0.3125 0.0041 0.050 Uiso 1 1 calc R U .
H14B H 0.3815 0.2204 0.0872 0.050 Uiso 1 1 calc R U .
H14C H 0.4310 0.2561 -0.0558 0.050 Uiso 1 1 calc R U .
C15 C 0.5000 0.56309(18) 0.2500 0.0536(8) Uani 1 2 d S T P
H15A H 0.4854 0.5848 0.1461 0.080 Uiso 0.5 1 calc R U P
H15B H 0.5502 0.5848 0.2755 0.080 Uiso 0.5 1 calc R U P
H15C H 0.4644 0.5848 0.3284 0.080 Uiso 0.5 1 calc R U P
B1 B 0.5000 0.16962(17) 0.2500 0.0243(5) Uani 1 2 d S T P
S1 S 0.64415(2) -0.00125(3) 0.01827(4) 0.02940(13) 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 0.0181 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'
S S 0.3331 0.5567 '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
C8 C1 C2 109.37(13) . .
C8 C1 B1 125.43(15) . .
C2 C1 B1 125.11(15) . .
C3 C2 C7 116.07(14) . .
C3 C2 C1 130.81(14) . .
C7 C2 C1 113.07(14) . .
C4 C3 C2 120.59(16) . .
C4 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
C3 C4 C5 121.32(17) . .
C3 C4 H4 119.3 . .
C5 C4 H4 119.3 . .
C6 C5 C4 120.04(15) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
C5 C6 C7 118.55(15) . .
C5 C6 H6 120.7 . .
C7 C6 H6 120.7 . .
C6 C7 C2 123.41(16) . .
C6 C7 S1 124.98(13) . .
C2 C7 S1 111.54(12) . .
C1 C8 C9 132.62(14) . .
C1 C8 S1 114.00(11) . .
C9 C8 S1 113.29(11) . .
C9 C9 C8 128.96(9) 3_655 .
C9 C9 H9 115.5 3_655 .
C8 C9 H9 115.5 . .
C11 C10 C11 118.4(2) . 3_655
C11 C10 B1 120.79(10) . .
C11 C10 B1 120.79(10) 3_655 .
C12 C11 C10 120.13(15) . .
C12 C11 C14 119.85(14) . .
C10 C11 C14 119.97(15) . .
C11 C12 C13 121.58(16) . .
C11 C12 H12 119.2 . .
C13 C12 H12 119.2 . .
C12 C13 C12 118.1(2) . 3_655
C12 C13 C15 120.93(11) . .
C12 C13 C15 120.93(11) 3_655 .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C1 B1 C1 124.8(2) 3_655 .
C1 B1 C10 117.61(10) 3_655 .
C1 B1 C10 117.61(10) . .
C7 S1 C8 91.92(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C8 1.396(2) .
C1 C2 1.473(2) .
C1 B1 1.5544(18) .
C2 C3 1.410(2) .
C2 C7 1.416(2) .
C3 C4 1.388(2) .
C3 H3 0.9500 .
C4 C5 1.401(2) .
C4 H4 0.9500 .
C5 C6 1.370(3) .
C5 H5 0.9500 .
C6 C7 1.400(2) .
C6 H6 0.9500 .
C7 S1 1.7249(17) .
C8 C9 1.425(2) .
C8 S1 1.7411(15) .
C9 C9 1.356(3) 3_655
C9 H9 0.9500 .
C10 C11 1.4078(18) .
C10 C11 1.4078(18) 3_655
C10 B1 1.581(3) .
C11 C12 1.391(2) .
C11 C14 1.515(2) .
C12 C13 1.391(2) .
C12 H12 0.9500 .
C13 C12 1.392(2) 3_655
C13 C15 1.510(3) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
B1 C1 1.5544(18) 3_655
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
_geom_torsion_site_symmetry_4
C8 C1 C2 C3 175.62(15) . .
B1 C1 C2 C3 -7.6(2) . .
C8 C1 C2 C7 -1.86(17) . .
B1 C1 C2 C7 174.89(11) . .
C7 C2 C3 C4 1.1(2) . .
C1 C2 C3 C4 -176.29(15) . .
C2 C3 C4 C5 -0.3(3) . .
C3 C4 C5 C6 -0.6(3) . .
C4 C5 C6 C7 0.6(2) . .
C5 C6 C7 C2 0.3(2) . .
C5 C6 C7 S1 176.92(12) . .
C3 C2 C7 C6 -1.1(2) . .
C1 C2 C7 C6 176.75(13) . .
C3 C2 C7 S1 -178.16(11) . .
C1 C2 C7 S1 -0.29(15) . .
C2 C1 C8 C9 -172.99(14) . .
B1 C1 C8 C9 10.3(2) . .
C2 C1 C8 S1 3.22(15) . .
B1 C1 C8 S1 -173.51(8) . .
C1 C8 C9 C9 -1.6(3) . 3_655
S1 C8 C9 C9 -177.86(18) . 3_655
C11 C10 C11 C12 -0.26(10) 3_655 .
B1 C10 C11 C12 179.74(10) . .
C11 C10 C11 C14 177.10(15) 3_655 .
B1 C10 C11 C14 -2.90(15) . .
C10 C11 C12 C13 0.5(2) . .
C14 C11 C12 C13 -176.83(12) . .
C11 C12 C13 C12 -0.27(11) . 3_655
C11 C12 C13 C15 179.73(11) . .
C8 C1 B1 C1 -5.90(11) . 3_655
C2 C1 B1 C1 177.87(14) . 3_655
C8 C1 B1 C10 174.10(11) . .
C2 C1 B1 C10 -2.13(14) . .
C11 C10 B1 C1 -86.65(9) . 3_655
C11 C10 B1 C1 93.36(9) 3_655 3_655
C11 C10 B1 C1 93.35(9) . .
C11 C10 B1 C1 -86.64(9) 3_655 .
C6 C7 S1 C8 -175.19(13) . .
C2 C7 S1 C8 1.78(11) . .
C1 C8 S1 C7 -2.98(12) . .
C9 C8 S1 C7 173.98(11) . .
