#------------------------------------------------------------------------------
#$Date: 2019-11-24 20:39:41 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239367 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/60/1556046.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_1556046
loop_
_publ_author_name
'Mitsudo, Koichi'
'Kurimoto, Yuji'
'Mandai, Hiroki'
'Suga, Seiji'
_publ_section_title
;
 Synthesis of 3-Benzo[b]thienyl 3-Thienyl Ether via an
 Addition-Elimination Reaction and Its Transformation to an Oxygen-Fused
 Dithiophene Skeleton: Synthesis and Properties of Benzodithienofuran and
 Its π-Extended Derivatives.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2821
_journal_page_last               2824
_journal_paper_doi               10.1021/acs.orglett.7b00969
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C12 H6 O S2'
_chemical_formula_sum            'C12 H6 O S2'
_chemical_formula_weight         230.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.541(4)
_cell_length_b                   15.387(12)
_cell_length_c                   22.574(18)
_cell_measurement_reflns_used    5867
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.2
_cell_measurement_theta_min      2.6
_cell_volume                     1925(3)
_computing_cell_refinement
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1446
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21198
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.205
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.581
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     147
_refine_ls_restrained_S_all      1.530
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.1377
_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)+13.7498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2094
_refine_ls_wR_factor_ref         0.2114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2139
_reflns_number_total             2210
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b00969_si_002.cif
_cod_data_source_block           ydkr
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1556046
_shelx_shelxl_version_number     2016/6
_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   0.918
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 1.0204(3) 0.57443(11) 0.57456(8) 0.0167(4) Uani 1 1 d . .
O1 O 0.5833(8) 0.4835(3) 0.69009(19) 0.0144(10) Uani 1 1 d . .
S2 S 0.4662(3) 0.39823(11) 0.53234(7) 0.0142(4) Uani 1 1 d . .
C1 C 1.0910(13) 0.6172(4) 0.6445(3) 0.0183(15) Uani 1 1 d . U
H1 H 1.220354 0.656509 0.651223 0.022 Uiso 1 1 calc R U
C2 C 0.9399(13) 0.5881(4) 0.6884(3) 0.0184(15) Uani 1 1 d . U
H2 H 0.949944 0.604136 0.728925 0.022 Uiso 1 1 calc R U
C3 C 0.7673(13) 0.5306(4) 0.6642(3) 0.0150(14) Uani 1 1 d . U
C4 C 0.7842(12) 0.5156(4) 0.6043(3) 0.0124(13) Uani 1 1 d . U
C5 C 0.5964(12) 0.4558(4) 0.5905(3) 0.0104(13) Uani 1 1 d . U
C6 C 0.4830(12) 0.4378(4) 0.6428(3) 0.0146(13) Uani 1 1 d . U
C7 C 0.2835(12) 0.3783(4) 0.6413(3) 0.0116(13) Uani 1 1 d . U
C8 C 0.2578(13) 0.3512(4) 0.5816(3) 0.0138(13) Uani 1 1 d . U
C9 C 0.0758(13) 0.2919(4) 0.5658(3) 0.0175(14) Uani 1 1 d . U
H9 H 0.059709 0.272748 0.525951 0.021 Uiso 1 1 calc R U
C10 C -0.0801(13) 0.2620(4) 0.6094(3) 0.0172(15) Uani 1 1 d . U
H10 H -0.204461 0.222168 0.599262 0.021 Uiso 1 1 calc R U
C11 C -0.0561(13) 0.2898(4) 0.6682(3) 0.0166(14) Uani 1 1 d . U
H11 H -0.164236 0.268430 0.697428 0.020 Uiso 1 1 calc R U
C12 C 0.1235(12) 0.3483(4) 0.6845(3) 0.0156(14) Uani 1 1 d . U
H12 H 0.137129 0.367441 0.724345 0.019 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'
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
C4 S1 C1 90.9(3)
C3 O1 C6 103.6(5)
C5 S2 C8 90.3(3)
C2 C1 S1 113.0(5)
C2 C1 H1 123.5
S1 C1 H1 123.5
C1 C2 C3 109.8(6)
C1 C2 H2 125.1
C3 C2 H2 125.1
C4 C3 O1 112.2(6)
C4 C3 C2 116.0(6)
O1 C3 C2 131.7(6)
C3 C4 C5 105.9(6)
C3 C4 S1 110.2(5)
C5 C4 S1 143.8(5)
C6 C5 C4 106.1(6)
C6 C5 S2 111.0(5)
C4 C5 S2 142.9(5)
C5 C6 O1 112.1(6)
C5 C6 C7 117.6(6)
O1 C6 C7 130.3(6)
C12 C7 C8 120.2(6)
C12 C7 C6 133.1(6)
C8 C7 C6 106.7(6)
C9 C8 C7 120.3(6)
C9 C8 S2 125.3(5)
C7 C8 S2 114.4(5)
C10 C9 C8 118.8(6)
C10 C9 H9 120.6
C8 C9 H9 120.6
C9 C10 C11 120.8(6)
C9 C10 H10 119.6
C11 C10 H10 119.6
C12 C11 C10 121.1(6)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C7 118.9(6)
C11 C12 H12 120.5
C7 C12 H12 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.728(7)
S1 C1 1.754(7)
O1 C3 1.380(8)
O1 C6 1.395(8)
S2 C5 1.739(7)
S2 C8 1.759(7)
C1 C2 1.373(10)
C1 H1 0.9500
C2 C3 1.412(10)
C2 H2 0.9500
C3 C4 1.376(9)
C4 C5 1.423(9)
C5 C6 1.365(9)
C6 C7 1.436(10)
C7 C12 1.397(9)
C7 C8 1.418(9)
C8 C9 1.405(9)
C9 C10 1.389(10)
C9 H9 0.9500
C10 C11 1.401(9)
C10 H10 0.9500
C11 C12 1.390(10)
C11 H11 0.9500
C12 H12 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
C4 S1 C1 C2 -0.3(6)
S1 C1 C2 C3 0.1(8)
C6 O1 C3 C4 -0.3(7)
C6 O1 C3 C2 -178.5(7)
C1 C2 C3 C4 0.2(9)
C1 C2 C3 O1 178.3(7)
O1 C3 C4 C5 0.9(8)
C2 C3 C4 C5 179.3(6)
O1 C3 C4 S1 -178.9(4)
C2 C3 C4 S1 -0.4(8)
C1 S1 C4 C3 0.4(5)
C1 S1 C4 C5 -179.2(9)
C3 C4 C5 C6 -1.1(7)
S1 C4 C5 C6 178.5(7)
C3 C4 C5 S2 180.0(7)
S1 C4 C5 S2 -0.4(15)
C8 S2 C5 C6 0.2(5)
C8 S2 C5 C4 179.2(8)
C4 C5 C6 O1 0.9(7)
S2 C5 C6 O1 -179.7(4)
C4 C5 C6 C7 -180.0(6)
S2 C5 C6 C7 -0.7(8)
C3 O1 C6 C5 -0.4(7)
C3 O1 C6 C7 -179.4(7)
C5 C6 C7 C12 -177.0(7)
O1 C6 C7 C12 1.8(13)
C5 C6 C7 C8 0.8(8)
O1 C6 C7 C8 179.7(6)
C12 C7 C8 C9 -1.9(10)
C6 C7 C8 C9 179.9(6)
C12 C7 C8 S2 177.6(5)
C6 C7 C8 S2 -0.6(7)
C5 S2 C8 C9 179.7(6)
C5 S2 C8 C7 0.2(6)
C7 C8 C9 C10 1.2(10)
S2 C8 C9 C10 -178.3(5)
C8 C9 C10 C11 -0.3(10)
C9 C10 C11 C12 0.2(11)
C10 C11 C12 C7 -0.9(10)
C8 C7 C12 C11 1.7(10)
C6 C7 C12 C11 179.3(7)
