#------------------------------------------------------------------------------
#$Date: 2015-10-06 16:02:45 +0200 (mar 06 de oct de 2015) $
#$Revision: 160564 $
#$URL: svn://www.crystallography.net/cod/cif/1/53/24/1532461.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_1532461
loop_
_publ_author_name
'Mitsudo, Koichi'
'Sato, Hidehiko'
'Yamasaki, Arata'
'Kamimoto, Natsuyo'
'Goto, Jun'
'Mandai, Hiroki'
'Suga, Seiji'
_publ_section_title
;
 Synthesis and Properties of Ethene-Bridged Terthiophenes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4858
_journal_page_last               4861
_journal_paper_doi               10.1021/acs.orglett.5b02417
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C16 H8 S3'
_chemical_formula_sum            'C16 H8 S3'
_chemical_formula_weight         296.40
_chemical_name_common            EBTT
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 103.214(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.033(7)
_cell_length_b                   3.916(2)
_cell_length_c                   24.464(13)
_cell_measurement_reflns_used    3220
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1215.5(11)
_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 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.981
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_laue_measured_fraction_full 0.991
_diffrn_reflns_laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16125
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         3.211
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0347
_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)+(0.0303P)²+1.2957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2401
_reflns_number_total             2726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b02417_si_006.cif
_cod_data_source_block           1e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1532457--1532461.cif.
;
_cod_database_code               1532461
_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   0.892
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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 0.64453(4) 0.14485(12) 0.28293(2) 0.01452(12) Uani 1 1 d . .
C1 C 0.75579(15) -0.0075(5) 0.33087(8) 0.0151(4) Uani 1 1 d . .
C2 C 0.77458(15) -0.0027(5) 0.38962(8) 0.0146(4) Uani 1 1 d . .
S2 S 0.69563(4) 0.15919(13) 0.43162(2) 0.01608(12) Uani 1 1 d . .
C3 C 0.78756(16) 0.0415(5) 0.49188(8) 0.0188(4) Uani 1 1 d . .
H3 H 0.7786 0.0821 0.5288 0.023 Uiso 1 1 calc R U
C4 C 0.87292(16) -0.1133(5) 0.48089(8) 0.0181(4) Uani 1 1 d . .
H4 H 0.9299 -0.1959 0.5093 0.022 Uiso 1 1 calc R U
C5 C 0.86897(15) -0.1409(5) 0.42192(8) 0.0164(4) Uani 1 1 d . .
C6 C 0.94467(15) -0.2777(5) 0.39506(8) 0.0179(4) Uani 1 1 d . .
H6 H 1.0088 -0.3675 0.4169 0.022 Uiso 1 1 calc R U
C7 C 0.92600(15) -0.2816(5) 0.33743(8) 0.0173(4) Uani 1 1 d . .
H7 H 0.9773 -0.3742 0.3196 0.021 Uiso 1 1 calc R U
C8 C 0.83098(15) -0.1486(5) 0.30468(8) 0.0146(4) Uani 1 1 d . .
C9 C 0.79717(15) -0.1341(5) 0.24394(8) 0.0144(4) Uani 1 1 d . .
C10 C 0.85007(16) -0.2532(5) 0.20337(8) 0.0171(4) Uani 1 1 d . .
H10 H 0.9173 -0.3575 0.2151 0.021 Uiso 1 1 calc R U
C11 C 0.80490(16) -0.2195(5) 0.14696(8) 0.0177(4) Uani 1 1 d . .
H11 H 0.8413 -0.2987 0.1199 0.021 Uiso 1 1 calc R U
C12 C 0.70477(16) -0.0676(5) 0.12935(8) 0.0164(4) Uani 1 1 d . .
C13 C 0.64260(16) -0.0094(5) 0.07336(8) 0.0180(4) Uani 1 1 d . .
H13 H 0.6646 -0.0743 0.0404 0.022 Uiso 1 1 calc R U
C14 C 0.54996(16) 0.1469(5) 0.07261(8) 0.0188(4) Uani 1 1 d . .
H14 H 0.5004 0.2052 0.0390 0.023 Uiso 1 1 calc R U
S3 S 0.53052(4) 0.23016(13) 0.13899(2) 0.01633(12) Uani 1 1 d . .
C15 C 0.65138(15) 0.0533(5) 0.16967(8) 0.0148(4) Uani 1 1 d . .
C16 C 0.69791(15) 0.0180(5) 0.22684(7) 0.0140(4) 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 0.0033 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'
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
C16 S1 C1 90.67(10)
C8 C1 C2 119.84(17)
C8 C1 S1 112.79(14)
C2 C1 S1 127.37(15)
C1 C2 C5 119.69(17)
C1 C2 S2 128.67(15)
C5 C2 S2 111.64(14)
C2 S2 C3 91.05(10)
C4 C3 S2 113.03(15)
C4 C3 H3 123.5
S2 C3 H3 123.5
C3 C4 C5 113.13(17)
C3 C4 H4 123.4
C5 C4 H4 123.4
C2 C5 C6 119.91(17)
C2 C5 C4 111.14(17)
C6 C5 C4 128.94(18)
C7 C6 C5 120.22(18)
C7 C6 H6 119.9
C5 C6 H6 119.9
C6 C7 C8 120.29(18)
C6 C7 H7 119.9
C8 C7 H7 119.9
C1 C8 C7 120.03(17)
C1 C8 C9 111.87(17)
C7 C8 C9 128.10(17)
C16 C9 C10 119.85(17)
C16 C9 C8 111.50(16)
C10 C9 C8 128.64(18)
C11 C10 C9 120.49(18)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 120.05(18)
C10 C11 H11 120.0
C12 C11 H11 120.0
C11 C12 C15 119.84(17)
C11 C12 C13 129.61(18)
C15 C12 C13 110.55(18)
C14 C13 C12 113.05(17)
C14 C13 H13 123.5
C12 C13 H13 123.5
C13 C14 S3 113.26(15)
C13 C14 H14 123.4
S3 C14 H14 123.4
C15 S3 C14 91.01(10)
C16 C15 C12 119.68(18)
C16 C15 S3 128.19(15)
C12 C15 S3 112.13(14)
C15 C16 C9 120.09(17)
C15 C16 S1 126.74(15)
C9 C16 S1 113.17(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C16 1.7466(19)
S1 C1 1.748(2)
C1 C8 1.401(3)
C1 C2 1.402(3)
C2 C5 1.409(3)
C2 S2 1.732(2)
S2 C3 1.736(2)
C3 C4 1.347(3)
C3 H3 0.9500
C4 C5 1.436(3)
C4 H4 0.9500
C5 C6 1.410(3)
C6 C7 1.375(3)
C6 H6 0.9500
C7 C8 1.412(3)
C7 H7 0.9500
C8 C9 1.451(3)
C9 C16 1.399(3)
C9 C10 1.411(3)
C10 C11 1.377(3)
C10 H10 0.9500
C11 C12 1.409(3)
C11 H11 0.9500
C12 C15 1.413(3)
C12 C13 1.441(3)
C13 C14 1.350(3)
C13 H13 0.9500
C14 S3 1.731(2)
C14 H14 0.9500
S3 C15 1.727(2)
C15 C16 1.398(3)
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
C16 S1 C1 C8 0.26(15)
C16 S1 C1 C2 -179.29(19)
C8 C1 C2 C5 -0.2(3)
S1 C1 C2 C5 179.37(15)
C8 C1 C2 S2 179.27(15)
S1 C1 C2 S2 -1.2(3)
C1 C2 S2 C3 -179.76(19)
C5 C2 S2 C3 -0.29(15)
C2 S2 C3 C4 -0.34(17)
S2 C3 C4 C5 0.9(2)
C1 C2 C5 C6 1.1(3)
S2 C2 C5 C6 -178.46(15)
C1 C2 C5 C4 -179.67(17)
S2 C2 C5 C4 0.8(2)
C3 C4 C5 C2 -1.1(2)
C3 C4 C5 C6 178.1(2)
C2 C5 C6 C7 -1.0(3)
C4 C5 C6 C7 179.87(19)
C5 C6 C7 C8 0.0(3)
C2 C1 C8 C7 -0.8(3)
S1 C1 C8 C7 179.60(15)
C2 C1 C8 C9 179.33(17)
S1 C1 C8 C9 -0.3(2)
C6 C7 C8 C1 0.9(3)
C6 C7 C8 C9 -179.29(19)
C1 C8 C9 C16 0.1(2)
C7 C8 C9 C16 -179.74(19)
C1 C8 C9 C10 -179.09(19)
C7 C8 C9 C10 1.1(3)
C16 C9 C10 C11 0.3(3)
C8 C9 C10 C11 179.45(19)
C9 C10 C11 C12 -0.5(3)
C10 C11 C12 C15 0.7(3)
C10 C11 C12 C13 -179.32(19)
C11 C12 C13 C14 -179.5(2)
C15 C12 C13 C14 0.5(2)
C12 C13 C14 S3 -0.7(2)
C13 C14 S3 C15 0.52(17)
C11 C12 C15 C16 -0.7(3)
C13 C12 C15 C16 179.34(17)
C11 C12 C15 S3 179.86(15)
C13 C12 C15 S3 -0.1(2)
C14 S3 C15 C16 -179.61(19)
C14 S3 C15 C12 -0.21(15)
C12 C15 C16 C9 0.5(3)
S3 C15 C16 C9 179.84(15)
C12 C15 C16 S1 -179.14(14)
S3 C15 C16 S1 0.2(3)
C10 C9 C16 C15 -0.3(3)
C8 C9 C16 C15 -179.57(17)
C10 C9 C16 S1 179.37(14)
C8 C9 C16 S1 0.1(2)
C1 S1 C16 C15 179.43(18)
C1 S1 C16 C9 -0.20(15)
