#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:18:43 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268907 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158152.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_7158152
loop_
_publ_author_name
'Nobuhara, Keita'
'Inagaki, Yusuke'
'Setaka, Wataru'
_publ_section_title
;
 Steric effects on the intramolecular charge transfer fluorescence of
 benzo[b]thiophene-1,1-dioxide bridged macrocages.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6328
_journal_page_last               6333
_journal_paper_doi               10.1039/d1ob01050f
_journal_volume                  19
_journal_year                    2021
_chemical_compound_source        no
_chemical_formula_moiety         'C14 H22 O2 S Si2'
_chemical_formula_sum            'C14 H22 O2 S Si2'
_chemical_formula_weight         310.55
_chemical_melting_point          353.5(5)
_chemical_name_common            TMSBTO2
_chemical_name_systematic
'2,5-is(trimethylsilyl)benzo[b]thiophene dioxide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2819rd
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-29 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.711(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.436(15)
_cell_length_b                   6.470(4)
_cell_length_c                   23.601(15)
_cell_measurement_reflns_used    4480
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     3386(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'WinGX 2020'
_computing_publication_material  'WinGX 2020'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR2019, IUCr'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16276
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.280
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear; Rigaku'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1328
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0511P)²+6.8952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3482
_reflns_number_total             3888
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01050f2.cif
_cod_data_source_block           TMSBTO2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '353-354 K' was changed to
'353.5(5)' -- the average value was taken and precision was
estimated.

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158152.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7158152
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.896
_shelx_estimated_absorpt_t_max   0.937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.35572(2) 0.34578(9) 0.46934(2) 0.02109(15) Uani 1 1 d . . . . .
Si2 Si 0.65164(3) 0.30826(9) 0.29465(2) 0.02235(15) Uani 1 1 d . . . . .
S1 S 0.42486(2) 0.66524(7) 0.39977(2) 0.02260(14) Uani 1 1 d . . . . .
O1 O 0.37243(7) 0.6898(3) 0.35677(7) 0.0338(4) Uani 1 1 d . . . . .
O2 O 0.43866(8) 0.8305(2) 0.44056(7) 0.0339(4) Uani 1 1 d . . . . .
C1 C 0.42308(9) 0.4243(3) 0.43533(8) 0.0217(4) Uani 1 1 d . . . . .
C2 C 0.47109(9) 0.3123(3) 0.42562(9) 0.0228(4) Uani 1 1 d . . . . .
H2 H 0.479631 0.180034 0.442405 0.027 Uiso 1 1 calc R U . . .
C3 C 0.50977(9) 0.4075(3) 0.38722(8) 0.0209(4) Uani 1 1 d . . . . .
C4 C 0.55964(9) 0.3227(3) 0.36719(9) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.574173 0.190541 0.380325 0.026 Uiso 1 1 calc R U . . .
C5 C 0.58865(9) 0.4317(3) 0.32754(8) 0.0213(4) Uani 1 1 d . . . . .
C6 C 0.56676(9) 0.6290(3) 0.31010(8) 0.0239(4) Uani 1 1 d . . . . .
H6 H 0.586416 0.704796 0.283817 0.029 Uiso 1 1 calc R U . . .
C7 C 0.51688(9) 0.7175(3) 0.33023(9) 0.0245(4) Uani 1 1 d . . . . .
H7 H 0.502578 0.850985 0.318150 0.029 Uiso 1 1 calc R U . . .
C8 C 0.48944(9) 0.6029(3) 0.36827(8) 0.0208(4) Uani 1 1 d . . . . .
C9 C 0.30385(10) 0.2079(4) 0.41222(10) 0.0299(5) Uani 1 1 d . . . . .
H9A H 0.291121 0.302648 0.380283 0.045 Uiso 1 1 calc R U . . .
H9B H 0.324879 0.089523 0.398487 0.045 Uiso 1 1 calc R U . . .
H9C H 0.268362 0.159190 0.427937 0.045 Uiso 1 1 calc R U . . .
C10 C 0.31971(10) 0.5853(4) 0.49255(10) 0.0314(5) Uani 1 1 d . . . . .
H10A H 0.307000 0.673534 0.459146 0.047 Uiso 1 1 calc R U . . .
H10B H 0.284478 0.547900 0.510344 0.047 Uiso 1 1 calc R U . . .
H10C H 0.348759 0.660261 0.520339 0.047 Uiso 1 1 calc R U . . .
C11 C 0.38095(10) 0.1711(3) 0.53079(9) 0.0275(4) Uani 1 1 d . . . . .
H11A H 0.399560 0.047470 0.517076 0.041 Uiso 1 1 calc R U . . .
H11B H 0.410435 0.243099 0.558858 0.041 Uiso 1 1 calc R U . . .
H11C H 0.346154 0.130738 0.548863 0.041 Uiso 1 1 calc R U . . .
C12 C 0.61519(12) 0.1612(4) 0.23056(10) 0.0341(5) Uani 1 1 d . . . . .
H12A H 0.588646 0.054875 0.242610 0.051 Uiso 1 1 calc R U . . .
H12B H 0.591471 0.256118 0.203682 0.051 Uiso 1 1 calc R U . . .
H12C H 0.646342 0.095481 0.211743 0.051 Uiso 1 1 calc R U . . .
C13 C 0.70264(10) 0.5125(4) 0.27357(10) 0.0346(5) Uani 1 1 d . . . . .
H13A H 0.679705 0.605018 0.245424 0.052 Uiso 1 1 calc R U . . .
H13B H 0.719677 0.592105 0.307522 0.052 Uiso 1 1 calc R U . . .
H13C H 0.735329 0.447897 0.256684 0.052 Uiso 1 1 calc R U . . .
C14 C 0.69403(11) 0.1293(4) 0.34832(10) 0.0370(6) Uani 1 1 d . . . . .
H14A H 0.666607 0.023075 0.358922 0.056 Uiso 1 1 calc R U . . .
H14B H 0.726693 0.063384 0.331684 0.056 Uiso 1 1 calc R U . . .
H14C H 0.711040 0.207592 0.382522 0.056 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
C11 Si1 C10 111.71(11) . . ?
C11 Si1 C9 110.83(11) . . ?
C10 Si1 C9 110.97(11) . . ?
C11 Si1 C1 109.10(10) . . ?
C10 Si1 C1 108.14(10) . . ?
C9 Si1 C1 105.86(10) . . ?
C13 Si2 C14 110.52(12) . . ?
C13 Si2 C12 110.86(12) . . ?
C14 Si2 C12 110.44(13) . . ?
C13 Si2 C5 109.71(11) . . ?
C14 Si2 C5 108.63(10) . . ?
C12 Si2 C5 106.57(11) . . ?
O2 S1 O1 117.29(11) . . ?
O2 S1 C8 110.03(10) . . ?
O1 S1 C8 111.21(11) . . ?
O2 S1 C1 110.73(11) . . ?
O1 S1 C1 110.83(10) . . ?
C8 S1 C1 94.42(9) . . ?
C2 C1 S1 108.47(15) . . ?
C2 C1 Si1 129.85(16) . . ?
S1 C1 Si1 121.02(11) . . ?
C1 C2 C3 115.99(19) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 H2 122.0 . . ?
C4 C3 C8 119.29(18) . . ?
C4 C3 C2 128.30(19) . . ?
C8 C3 C2 112.33(18) . . ?
C3 C4 C5 120.30(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.25(18) . . ?
C6 C5 Si2 120.88(15) . . ?
C4 C5 Si2 120.73(15) . . ?
C7 C6 C5 122.17(18) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C8 C7 C6 117.32(19) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C7 C8 C3 122.65(19) . . ?
C7 C8 S1 128.67(16) . . ?
C3 C8 S1 108.67(14) . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si2 C12 H12A 109.5 . . ?
Si2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si2 C13 H13A 109.5 . . ?
Si2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si2 C14 H14A 109.5 . . ?
Si2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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
Si1 C11 1.858(2) . ?
Si1 C10 1.868(2) . ?
Si1 C9 1.869(2) . ?
Si1 C1 1.885(2) . ?
Si2 C13 1.864(2) . ?
Si2 C14 1.867(2) . ?
Si2 C12 1.867(2) . ?
Si2 C5 1.889(2) . ?
S1 O2 1.4406(18) . ?
S1 O1 1.4414(18) . ?
S1 C8 1.772(2) . ?
S1 C1 1.774(2) . ?
C1 C2 1.347(3) . ?
C2 C3 1.481(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 C8 1.395(3) . ?
C4 C5 1.408(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(3) . ?
C6 C7 1.403(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 C2 -110.09(16) . . . . ?
O1 S1 C1 C2 117.95(16) . . . . ?
C8 S1 C1 C2 3.27(16) . . . . ?
O2 S1 C1 Si1 78.35(14) . . . . ?
O1 S1 C1 Si1 -53.60(15) . . . . ?
C8 S1 C1 Si1 -168.28(12) . . . . ?
C11 Si1 C1 C2 39.3(2) . . . . ?
C10 Si1 C1 C2 161.0(2) . . . . ?
C9 Si1 C1 C2 -80.0(2) . . . . ?
C11 Si1 C1 S1 -151.14(12) . . . . ?
C10 Si1 C1 S1 -29.44(15) . . . . ?
C9 Si1 C1 S1 89.55(14) . . . . ?
S1 C1 C2 C3 -3.0(2) . . . . ?
Si1 C1 C2 C3 167.59(15) . . . . ?
C1 C2 C3 C4 -175.8(2) . . . . ?
C1 C2 C3 C8 1.0(3) . . . . ?
C8 C3 C4 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 175.63(19) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C3 C4 C5 Si2 -174.16(15) . . . . ?
C13 Si2 C5 C6 30.89(19) . . . . ?
C14 Si2 C5 C6 151.81(17) . . . . ?
C12 Si2 C5 C6 -89.19(18) . . . . ?
C13 Si2 C5 C4 -153.57(17) . . . . ?
C14 Si2 C5 C4 -32.6(2) . . . . ?
C12 Si2 C5 C4 86.35(18) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
Si2 C5 C6 C7 174.67(16) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C3 0.7(3) . . . . ?
C6 C7 C8 S1 -177.88(16) . . . . ?
C4 C3 C8 C7 -0.1(3) . . . . ?
C2 C3 C8 C7 -177.26(19) . . . . ?
C4 C3 C8 S1 178.65(15) . . . . ?
C2 C3 C8 S1 1.5(2) . . . . ?
O2 S1 C8 C7 -70.1(2) . . . . ?
O1 S1 C8 C7 61.6(2) . . . . ?
C1 S1 C8 C7 176.0(2) . . . . ?
O2 S1 C8 C3 111.22(16) . . . . ?
O1 S1 C8 C3 -117.10(15) . . . . ?
C1 S1 C8 C3 -2.74(15) . . . . ?
