#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/17/1511797.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_1511797
loop_
_publ_author_name
'Zhou, Weidong'
'Hernández-Burgos, Kenneth'
'Burkhardt, Stephen E.'
'Qian, Hualei'
'Abru Héctor D.'
_publ_section_title
;
 Synthesis and Electrochemical and Computational Analysis of Two New
 Families of Thiophene-Carbonyl Molecules
;
_journal_issue                   12
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              6022
_journal_paper_doi               10.1021/jp310555b
_journal_volume                  117
_journal_year                    2013
_chemical_formula_moiety         'C16 H8 O4 S3'
_chemical_formula_sum            'C16 H8 O4 S3'
_chemical_formula_weight         360.40
_chemical_name_systematic        ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.185(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.4433(8)
_cell_length_b                   7.3062(3)
_cell_length_c                   11.3446(5)
_cell_measurement_reflns_used    3858
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.62
_cell_measurement_theta_min      3.32
_cell_volume                     1444.75(11)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11811
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.8159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0661P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                2828
_reflns_number_total             3568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp310555b_si_003.cif
_cod_data_source_block           wz4
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1511797
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.18269(2) 0.28335(6) 0.12363(4) 0.02017(13) Uani 1 1 d . . .
O1 O 0.04562(7) 0.29435(19) 0.00609(11) 0.0290(3) Uani 1 1 d . . .
O2 O 0.00555(7) 0.00928(18) 0.23836(11) 0.0262(3) Uani 1 1 d . . .
O3 O 0.33633(8) 0.4433(2) 0.10963(12) 0.0336(3) Uani 1 1 d . . .
O4 O 0.37610(8) 0.3736(2) 0.40063(12) 0.0360(4) Uani 1 1 d . A .
S1 S -0.14137(3) 0.07347(7) 0.13043(4) 0.02613(14) Uani 1 1 d . . .
C1 C -0.21630(11) 0.1342(3) 0.03791(18) 0.0292(4) Uani 1 1 d . . .
H1 H -0.2775(11) 0.078(3) 0.0514(17) 0.026(5) Uiso 1 1 d . . .
C2 C -0.19398(11) 0.2380(3) -0.05409(18) 0.0272(4) Uani 1 1 d . . .
H2 H -0.2243(13) 0.283(3) -0.1135(19) 0.037(6) Uiso 1 1 d . . .
C3 C -0.11451(10) 0.2712(2) -0.05104(16) 0.0204(4) Uani 1 1 d . . .
H3 H -0.0935(11) 0.331(3) -0.0961(18) 0.022(5) Uiso 1 1 d . . .
C4 C -0.07731(9) 0.1891(2) 0.04615(15) 0.0190(3) Uani 1 1 d . . .
C5 C 0.00501(10) 0.2084(2) 0.07089(15) 0.0194(4) Uani 1 1 d . . .
C6 C 0.04268(9) 0.1138(2) 0.17944(15) 0.0187(3) Uani 1 1 d . . .
C7 C 0.12442(9) 0.1518(2) 0.20818(14) 0.0185(3) Uani 1 1 d . . .
C8 C 0.16229(10) 0.0926(2) 0.31045(15) 0.0208(4) Uani 1 1 d . . .
H8 H 0.1398(10) 0.029(2) 0.3684(15) 0.015(5) Uiso 1 1 d . . .
C9 C 0.23785(10) 0.1565(3) 0.32160(15) 0.0224(4) Uani 1 1 d . . .
H9 H 0.2701(12) 0.137(3) 0.3852(18) 0.031(6) Uiso 1 1 d . . .
C10 C 0.25724(9) 0.2623(2) 0.22618(15) 0.0204(4) Uani 1 1 d . . .
C11 C 0.32861(10) 0.3587(3) 0.20113(16) 0.0230(4) Uani 1 1 d . A .
C12 C 0.39330(10) 0.3636(3) 0.29700(16) 0.0246(4) Uani 1 1 d D . .
S3 S 0.54432(9) 0.3767(3) 0.36650(17) 0.0298(4) Uani 0.750(3) 1 d PD A 1
C13 C 0.4722(3) 0.3641(15) 0.2561(15) 0.020(2) Uani 0.750(3) 1 d PD A 1
C14 C 0.5018(7) 0.3581(16) 0.1463(12) 0.047(4) Uani 0.750(3) 1 d PD A 1
H14A H 0.4706 0.3489 0.0760 0.056 Uiso 0.750(3) 1 calc PR A 1
C15 C 0.5818(6) 0.3668(19) 0.1463(8) 0.0334(17) Uani 0.750(3) 1 d PD A 1
H15A H 0.6114 0.3676 0.0777 0.040 Uiso 0.750(3) 1 calc PR A 1
C16 C 0.6113(6) 0.374(2) 0.2600(13) 0.037(3) Uani 0.750(3) 1 d PD A 1
H16A H 0.6648 0.3769 0.2783 0.045 Uiso 0.750(3) 1 calc PR A 1
S3' S 0.4986(4) 0.3654(12) 0.1252(11) 0.0334(12) Uani 0.250(3) 1 d PD A 2
C13' C 0.4737(11) 0.369(5) 0.273(5) 0.024(5) Uani 0.250(3) 1 d PDU A 2
C14' C 0.5411(14) 0.374(4) 0.3361(17) 0.038(6) Uani 0.250(3) 1 d PDU A 2
H14B H 0.5412 0.3747 0.4199 0.046 Uiso 0.250(3) 1 calc PR A 2
C15' C 0.6076(18) 0.378(7) 0.281(4) 0.036(5) Uani 0.250(3) 1 d PDU A 2
H15B H 0.6574 0.3893 0.3178 0.043 Uiso 0.250(3) 1 calc PR A 2
C16' C 0.5917(16) 0.364(6) 0.172(2) 0.031(5) Uani 0.250(3) 1 d PDU A 2
H16B H 0.6313 0.3539 0.1171 0.037 Uiso 0.250(3) 1 calc PR A 2
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
C10 S2 C7 91.18(8)
C1 S1 C4 91.67(9)
C2 C1 S1 112.52(15)
C1 C2 C3 112.86(17)
C4 C3 C2 111.95(17)
C3 C4 C5 122.38(16)
C3 C4 S1 111.01(13)
C5 C4 S1 126.58(13)
O1 C5 C4 121.71(16)
O1 C5 C6 118.41(15)
C4 C5 C6 119.86(15)
O2 C6 C7 121.75(15)
O2 C6 C5 120.10(15)
C7 C6 C5 118.15(15)
C8 C7 C6 123.56(16)
C8 C7 S2 111.70(13)
C6 C7 S2 124.67(12)
C7 C8 C9 112.93(16)
C10 C9 C8 111.93(15)
C9 C10 C11 130.89(16)
C9 C10 S2 112.25(13)
C11 C10 S2 116.85(13)
O3 C11 C10 122.00(16)
O3 C11 C12 119.22(16)
C10 C11 C12 118.65(15)
O4 C12 C13 124.7(7)
O4 C12 C13' 117(2)
C13 C12 C13' 8(3)
O4 C12 C11 118.66(16)
C13 C12 C11 116.6(7)
C13' C12 C11 124(2)
C16 S3 C13 89.1(6)
C14 C13 C12 132.8(11)
C14 C13 S3 111.7(6)
C12 C13 S3 115.6(10)
C15 C14 C13 114.2(11)
C16 C15 C14 109.9(10)
C15 C16 S3 115.0(8)
C16' S3' C13' 88.2(14)
C14' C13' C12 138(4)
C14' C13' S3' 105.3(16)
C12 C13' S3' 117(3)
C15' C14' C13' 121(3)
C14' C15' C16' 107(3)
C15' C16' S3' 119(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 C10 1.7184(17)
S2 C7 1.7180(17)
O1 C5 1.215(2)
O2 C6 1.217(2)
O3 C11 1.220(2)
O4 C12 1.227(2)
S1 C1 1.703(2)
S1 C4 1.7198(17)
C1 C2 1.359(3)
C2 C3 1.406(2)
C3 C4 1.394(2)
C4 C5 1.460(2)
C5 C6 1.538(2)
C6 C7 1.477(2)
C7 C8 1.383(2)
C8 C9 1.399(2)
C9 C10 1.383(2)
C10 C11 1.467(2)
C11 C12 1.537(2)
C12 C13 1.469(5)
C12 C13' 1.439(15)
S3 C16 1.712(12)
S3 C13 1.744(15)
C13 C14 1.367(19)
C14 C15 1.397(16)
C15 C16 1.371(13)
S3' C16' 1.69(3)
S3' C13' 1.75(5)
C13' C14' 1.35(5)
C14' C15' 1.34(4)
C15' C16' 1.27(4)
