#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:57:26 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178413 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/34/4023462.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_4023462
loop_
_publ_author_name
'Matthew J. O'Connor'
'Robert B. Yelle'
'Lev N. Zakharov'
'Michael M. Haley'
_publ_section_title
;
 Structure-Property Investigations of Conjugated Thiophenes
 Fused onto a Dehydro[14]annulene Scaffold
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4424
_journal_page_last               4432
_journal_paper_doi               10.1021/jo800225u
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C20 H6 S3'
_chemical_formula_weight         342.43
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 113.957(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.698(2)
_cell_length_b                   10.0144(13)
_cell_length_c                   19.344(3)
_cell_measurement_reflns_used    1383
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      2.30
_cell_volume                     3133.2(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1088
_diffrn_reflns_av_sigmaI/netI    0.0871
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29359
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.32
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5495
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0439P)²+0.0326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                3464
_reflns_number_total             5495
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800225u-File003.cif
_cod_data_source_block           mha14
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023462
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.28206(7) 1.26960(12) 0.11453(7) 0.0540(4) Uani 1 1 d . . .
S2 S 1.09403(7) 0.46647(10) 0.21418(7) 0.0425(3) Uani 1 1 d . . .
C1 C 1.2219(3) 1.4047(4) 0.0751(2) 0.0472(12) Uani 1 1 d . . .
H1A H 1.2431 1.4865 0.0656 0.057 Uiso 1 1 calc R . .
C2 C 1.1411(3) 1.3847(4) 0.0586(2) 0.0417(11) Uani 1 1 d . . .
H2A H 1.0994 1.4502 0.0361 0.050 Uiso 1 1 calc R . .
C3 C 1.1251(3) 1.2525(4) 0.0788(2) 0.0358(10) Uani 1 1 d . . .
C4 C 1.1973(2) 1.1796(4) 0.1101(2) 0.0346(10) Uani 1 1 d . . .
C5 C 0.9936(2) 0.4274(4) 0.1946(2) 0.0410(11) Uani 1 1 d . . .
H5A H 0.9767 0.3432 0.2060 0.049 Uiso 1 1 calc R . .
C6 C 0.9398(3) 0.5292(4) 0.1607(2) 0.0372(10) Uani 1 1 d . . .
H6A H 0.8817 0.5244 0.1460 0.045 Uiso 1 1 calc R . .
C7 C 0.9822(2) 0.6437(4) 0.1504(2) 0.0321(10) Uani 1 1 d . . .
C8 C 1.0665(2) 0.6238(4) 0.1757(2) 0.0327(10) Uani 1 1 d . . .
C9 C 0.9024(3) 1.1174(4) 0.0561(2) 0.0332(11) Uani 0.704(6) 1 d PD A 1
C10 C 0.8713(2) 0.9966(4) 0.0677(2) 0.0316(10) Uani 0.704(6) 1 d PD A 1
C11 C 0.7834(8) 1.0040(19) 0.0486(11) 0.060(8) Uani 0.704(6) 1 d PD A 1
H11A H 0.7518 0.9302 0.0529 0.072 Uiso 0.704(6) 1 calc PR A 1
C12 C 0.7500(7) 1.1268(10) 0.0238(7) 0.037(3) Uani 0.704(6) 1 d PD A 1
H12A H 0.6932 1.1487 0.0080 0.044 Uiso 0.704(6) 1 calc PR A 1
S3 S 0.82625(17) 1.2375(3) 0.02525(19) 0.0384(8) Uani 0.704(6) 1 d PD A 1
C9A C 0.9024(3) 1.1174(4) 0.0561(2) 0.0332(11) Uani 0.296(6) 1 d PD A 2
C10A C 0.8713(2) 0.9966(4) 0.0677(2) 0.0316(10) Uani 0.296(6) 1 d PD A 2
C11A C 0.8410(14) 1.216(3) 0.0287(17) 0.12(2) Uani 0.296(6) 1 d PD A 2
H11B H 0.8490 1.3029 0.0133 0.146 Uiso 0.296(6) 1 calc PR A 2
C12A C 0.7686(14) 1.1691(18) 0.0273(17) 0.024(6) Uani 0.296(6) 1 d PD A 2
H12B H 0.7208 1.2231 0.0154 0.029 Uiso 0.296(6) 1 calc PR A 2
S3A S 0.7715(6) 1.0033(13) 0.0490(6) 0.040(3) Uani 0.296(6) 1 d PD A 2
C13 C 1.1228(2) 0.7186(4) 0.1718(2) 0.0366(10) Uani 1 1 d . . .
C14 C 1.1585(2) 0.8148(4) 0.1628(2) 0.0360(10) Uani 1 1 d . . .
C15 C 1.1867(2) 0.9361(4) 0.1489(2) 0.0370(11) Uani 1 1 d . . .
C16 C 1.2006(2) 1.0460(4) 0.1337(2) 0.0379(11) Uani 1 1 d . . .
C17 C 1.0466(3) 1.2009(4) 0.0693(2) 0.0366(10) Uani 1 1 d . A .
C18 C 0.9823(3) 1.1544(4) 0.0643(2) 0.0336(10) Uani 1 1 d . . .
C19 C 0.9139(2) 0.8754(4) 0.0946(2) 0.0328(10) Uani 1 1 d . . .
C20 C 0.9441(2) 0.7682(4) 0.1197(2) 0.0353(10) Uani 1 1 d . A .
S1' S 0.81176(6) 0.24879(10) 0.21488(6) 0.0363(3) Uani 1 1 d . . .
S2' S 0.51884(7) 0.86985(11) -0.14675(6) 0.0456(3) Uani 1 1 d . . .
C1' C 0.7930(2) 0.2163(4) 0.2932(2) 0.0375(11) Uani 1 1 d . . .
H1'A H 0.8276 0.1614 0.3338 0.045 Uiso 1 1 calc R . .
C2' C 0.7242(2) 0.2765(4) 0.2917(2) 0.0332(10) Uani 1 1 d . . .
H2'A H 0.7050 0.2677 0.3307 0.040 Uiso 1 1 calc R . .
C3' C 0.6834(2) 0.3550(4) 0.2250(2) 0.0299(9) Uani 1 1 d . . .
C4' C 0.7259(2) 0.3504(3) 0.1780(2) 0.0273(9) Uani 1 1 d . . .
C5' C 0.4384(2) 0.9602(4) -0.1461(2) 0.0425(11) Uani 1 1 d . . .
H5'A H 0.4105 1.0266 -0.1827 0.051 Uiso 1 1 calc R . .
C6' C 0.4178(2) 0.9282(4) -0.0880(2) 0.0393(11) Uani 1 1 d . . .
H6'A H 0.3740 0.9695 -0.0795 0.047 Uiso 1 1 calc R . .
C7' C 0.4688(2) 0.8262(4) -0.0410(2) 0.0328(10) Uani 1 1 d . . .
C8' C 0.5273(2) 0.7831(4) -0.0668(2) 0.0337(10) Uani 1 1 d . . .
C9' C 0.4781(2) 0.5686(4) 0.1889(2) 0.0271(9) Uani 0.505(6) 1 d PD B 1
C10' C 0.4375(2) 0.6682(4) 0.1379(2) 0.0269(9) Uani 0.505(6) 1 d PD B 1
C11' C 0.3695(13) 0.709(3) 0.1551(15) 0.035(7) Uani 0.505(6) 1 d PD B 1
H11C H 0.3330 0.7770 0.1264 0.042 Uiso 0.505(6) 1 calc PR B 1
C12' C 0.3575(15) 0.649(2) 0.2120(13) 0.036(5) Uani 0.505(6) 1 d PD B 1
H12C H 0.3147 0.6677 0.2282 0.043 Uiso 0.505(6) 1 calc PR B 1
S3' S 0.4336(4) 0.5331(6) 0.2496(3) 0.0303(11) Uani 0.505(6) 1 d PD B 1
C9B C 0.4781(2) 0.5686(4) 0.1889(2) 0.0271(9) Uani 0.495(6) 1 d PD B 2
C10B C 0.4375(2) 0.6682(4) 0.1379(2) 0.0269(9) Uani 0.495(6) 1 d PD B 2
C11B C 0.4391(15) 0.547(2) 0.2400(13) 0.069(12) Uani 0.495(6) 1 d PD B 2
H11D H 0.4574 0.4849 0.2805 0.083 Uiso 0.495(6) 1 calc PR B 2
C12B C 0.3731(15) 0.628(2) 0.2230(12) 0.042(6) Uani 0.495(6) 1 d PD B 2
H12D H 0.3401 0.6273 0.2513 0.050 Uiso 0.495(6) 1 calc PR B 2
S3'B S 0.3530(5) 0.7290(8) 0.1478(4) 0.0326(13) Uani 0.495(6) 1 d PD B 2
C13' C 0.5846(2) 0.6814(4) -0.0321(2) 0.0345(10) Uani 1 1 d . . .
C14' C 0.6274(3) 0.5934(4) 0.0061(2) 0.0360(10) Uani 1 1 d . . .
C15' C 0.6710(2) 0.4979(4) 0.0578(2) 0.0356(10) Uani 1 1 d . . .
C16' C 0.7023(2) 0.4230(4) 0.1101(2) 0.0327(10) Uani 1 1 d . . .
C17' C 0.6100(2) 0.4302(4) 0.2083(2) 0.0308(10) Uani 1 1 d . B .
C18' C 0.5495(2) 0.4957(4) 0.1962(2) 0.0291(9) Uani 1 1 d . . .
C19' C 0.4555(2) 0.7201(4) 0.0782(2) 0.0315(10) Uani 1 1 d . . .
C20' C 0.4618(2) 0.7697(4) 0.0240(2) 0.0327(10) Uani 1 1 d . B .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 91.1(2) . . ?
C5 S2 C8 91.6(2) . . ?
C2 C1 S1 113.5(3) . . ?
C1 C2 C3 112.3(4) . . ?
C4 C3 C17 123.1(4) . . ?
C4 C3 C2 110.9(4) . . ?
C17 C3 C2 126.0(4) . . ?
C3 C4 C16 123.6(4) . . ?
C3 C4 S1 112.2(3) . . ?
C16 C4 S1 124.2(3) . . ?
C6 C5 S2 113.4(3) . . ?
C5 C6 C7 111.2(4) . . ?
C8 C7 C20 122.2(4) . . ?
C8 C7 C6 112.8(4) . . ?
C20 C7 C6 125.0(4) . . ?
C7 C8 C13 124.9(4) . . ?
C7 C8 S2 111.0(3) . . ?
C13 C8 S2 124.1(3) . . ?
C10 C9 C18 131.2(4) . . ?
C10 C9 S3 111.1(3) . . ?
C18 C9 S3 117.7(3) . . ?
C9 C10 C19 128.6(4) . . ?
C9 C10 C11 111.7(8) . . ?
C19 C10 C11 119.7(8) . . ?
C12 C11 C10 113.7(14) . . ?
C11 C12 S3 110.3(11) . . ?
C9 S3 C12 93.1(5) . . ?
C11A C12A S3A 113(2) . . ?
C14 C13 C8 168.0(4) . . ?
C13 C14 C15 170.2(4) . . ?
C16 C15 C14 171.4(4) . . ?
C15 C16 C4 166.9(4) . . ?
C18 C17 C3 177.1(5) . . ?
C17 C18 C9 172.2(4) . . ?
C20 C19 C10 173.6(4) . . ?
C19 C20 C7 178.2(4) . . ?
C1' S1' C4' 91.36(19) . . ?
C5' S2' C8' 91.7(2) . . ?
C2' C1' S1' 113.2(3) . . ?
C1' C2' C3' 112.7(3) . . ?
C4' C3' C17' 123.6(4) . . ?
C4' C3' C2' 111.2(3) . . ?
C17' C3' C2' 125.2(3) . . ?
C3' C4' C16' 123.8(3) . . ?
C3' C4' S1' 111.5(3) . . ?
C16' C4' S1' 124.7(3) . . ?
C6' C5' S2' 113.0(3) . . ?
C5' C6' C7' 112.8(4) . . ?
C8' C7' C6' 111.4(3) . . ?
C8' C7' C20' 122.4(4) . . ?
C6' C7' C20' 126.1(4) . . ?
C7' C8' C13' 123.7(4) . . ?
C7' C8' S2' 111.1(3) . . ?
C13' C8' S2' 125.2(3) . . ?
C10' C9' C18' 128.8(4) . . ?
C10' C9' S3' 113.2(4) . . ?
C18' C9' S3' 118.0(4) . . ?
C9' C10' C19' 128.7(4) . . ?
C9' C10' C11' 106.2(11) . . ?
C19' C10' C11' 125.1(12) . . ?
C12' C11' C10' 119(2) . . ?
C11' C12' S3' 107(2) . . ?
C9' S3' C12' 94.0(10) . . ?
C11B C12B S3'B 115.4(18) . . ?
C14' C13' C8' 168.8(4) . . ?
C13' C14' C15' 170.9(4) . . ?
C16' C15' C14' 168.9(4) . . ?
C15' C16' C4' 166.1(4) . . ?
C18' C17' C3' 178.0(4) . . ?
C17' C18' C9' 174.3(4) . . ?
C20' C19' C10' 172.7(4) . . ?
C19' C20' C7' 179.0(4) . . ?
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 1.699(4) . ?
S1 C4 1.722(4) . ?
S2 C5 1.705(4) . ?
S2 C8 1.726(4) . ?
C1 C2 1.348(5) . ?
C2 C3 1.440(5) . ?
C3 C4 1.381(5) . ?
C3 C17 1.423(6) . ?
C4 C16 1.407(6) . ?
C5 C6 1.367(5) . ?
C6 C7 1.429(5) . ?
C7 C8 1.383(5) . ?
C7 C20 1.428(5) . ?
C8 C13 1.400(5) . ?
C9 C10 1.385(5) . ?
C9 C18 1.408(6) . ?
C9 S3 1.721(4) . ?
C10 C19 1.411(5) . ?
C10 C11 1.449(14) . ?
C11 C12 1.364(15) . ?
C12 S3 1.737(9) . ?
C11A C12A 1.355(19) . ?
C12A S3A 1.708(16) . ?
C13 C14 1.204(5) . ?
C14 C15 1.380(6) . ?
C15 C16 1.190(5) . ?
C17 C18 1.195(5) . ?
C19 C20 1.209(5) . ?
S1' C1' 1.709(4) . ?
S1' C4' 1.724(4) . ?
S2' C5' 1.692(4) . ?
S2' C8' 1.727(4) . ?
C1' C2' 1.348(5) . ?
C2' C3' 1.431(5) . ?
C3' C4' 1.396(5) . ?
C3' C17' 1.420(5) . ?
C4' C16' 1.408(5) . ?
C5' C6' 1.353(5) . ?
C6' C7' 1.420(5) . ?
C7' C8' 1.388(5) . ?
C7' C20' 1.428(5) . ?
C8' C13' 1.402(5) . ?
C9' C10' 1.382(5) . ?
C9' C18' 1.416(5) . ?
C9' S3' 1.696(6) . ?
C10' C19' 1.414(5) . ?
C10' C11' 1.432(16) . ?
C11' C12' 1.343(17) . ?
C12' S3' 1.700(16) . ?
C11B C12B 1.342(17) . ?
C12B S3'B 1.689(15) . ?
C13' C14' 1.200(5) . ?
C14' C15' 1.373(6) . ?
C15' C16' 1.199(5) . ?
C17' C18' 1.196(5) . ?
C19' C20' 1.206(5) . ?
