#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/60/2016090.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2016090
loop_
_publ_author_name
'Mague, Joel T.'
'Balakrishna, Maravanji S.'
'Punji, Banudhar'
'Suresh, Devarajan'
_publ_section_title
;
 Two crystalline modifications of 1,1'-thiobis(2-naphthol)
;
_journal_coeditor_code           FA3098
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o487
_journal_page_last               o488
_journal_paper_doi               10.1107/S0108270107032738
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H14 O2 S'
_chemical_formula_moiety         'C20 H14 O2 S'
_chemical_formula_sum            'C20 H14 O2 S'
_chemical_formula_weight         318.37
_chemical_name_systematic
;
1,1'-thiobis(2-naphthol)
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.181(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8053(6)
_cell_length_b                   11.4200(10)
_cell_length_c                   26.732(3)
_cell_measurement_reflns_used    4149
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.35
_cell_volume                     1464.7(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12389
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            'Light brown'
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0503P)²+0.3449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2472
_reflns_number_total             3339
_reflns_threshold_expression     'I >2σ(I)'
_cod_data_source_file            fa3098.cif
_cod_data_source_block           Ia
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2016090
_cod_database_fobs_code          2016090
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.63179(10) 0.06039(4) 0.091079(18) 0.01418(14) Uani d . 1
O O1 0.1705(3) 0.10880(12) 0.01702(6) 0.0190(3) Uani d . 1
H H1 0.022(7) 0.123(2) 0.0006(11) 0.050(9) Uiso d . 1
O O2 0.3124(3) -0.14148(13) 0.04670(5) 0.0176(3) Uani d . 1
H H2 0.442(6) -0.095(2) 0.0387(10) 0.041(8) Uiso d . 1
C C1 0.4929(4) 0.20012(16) 0.07384(7) 0.0137(4) Uani d . 1
C C2 0.2772(4) 0.20957(17) 0.03784(7) 0.0149(4) Uani d . 1
C C3 0.1780(4) 0.32021(18) 0.02190(7) 0.0164(4) Uani d . 1
H H3 0.0262 0.3254 -0.0023 0.020 Uiso calc R 1
C C4 0.2980(4) 0.41948(18) 0.04092(7) 0.0182(4) Uani d . 1
H H4 0.2305 0.4935 0.0294 0.022 Uiso calc R 1
C C5 0.5229(4) 0.41472(17) 0.07776(7) 0.0148(4) Uani d . 1
C C6 0.6486(4) 0.51749(18) 0.09808(8) 0.0197(5) Uani d . 1
H H6 0.5828 0.5919 0.0868 0.024 Uiso calc R 1
C C7 0.8636(4) 0.51122(18) 0.13375(7) 0.0192(5) Uani d . 1
H H7 0.9463 0.5809 0.1471 0.023 Uiso calc R 1
C C8 0.9620(4) 0.40112(18) 0.15064(8) 0.0190(4) Uani d . 1
H H8 1.1109 0.3970 0.1755 0.023 Uiso calc R 1
C C9 0.8459(4) 0.30034(17) 0.13173(7) 0.0161(4) Uani d . 1
H H9 0.9165 0.2269 0.1434 0.019 Uiso calc R 1
C C10 0.6204(4) 0.30343(17) 0.09482(7) 0.0140(4) Uani d . 1
C C11 0.3527(4) -0.01347(17) 0.11877(7) 0.0146(4) Uani d . 1
C C12 0.2380(4) -0.10835(17) 0.09357(7) 0.0146(4) Uani d . 1
C C13 0.0309(4) -0.17787(17) 0.11432(8) 0.0175(4) Uani d . 1
H H13 -0.0463 -0.2428 0.0962 0.021 Uiso calc R 1
C C14 -0.0580(4) -0.15143(18) 0.16057(8) 0.0189(5) Uani d . 1
H H14 -0.1974 -0.1986 0.1744 0.023 Uiso calc R 1
C C15 0.0531(4) -0.05489(18) 0.18849(8) 0.0175(4) Uani d . 1
C C16 -0.0407(4) -0.02594(19) 0.23601(8) 0.0213(5) Uani d . 1
H H16 -0.1784 -0.0731 0.2503 0.026 Uiso calc R 1
C C17 0.0642(4) 0.0693(2) 0.26174(8) 0.0230(5) Uani d . 1
H H17 -0.0010 0.0881 0.2937 0.028 Uiso calc R 1
C C18 0.2681(4) 0.13923(19) 0.24090(8) 0.0215(5) Uani d . 1
H H18 0.3391 0.2056 0.2588 0.026 Uiso calc R 1
C C19 0.3661(4) 0.11332(18) 0.19518(8) 0.0181(4) Uani d . 1
H H19 0.5059 0.1612 0.1819 0.022 Uiso calc R 1
C C20 0.2612(4) 0.01570(17) 0.16735(7) 0.0149(4) Uani d . 1
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
_geom_angle_publ_flag
C11 S1 C1 104.60(9) y
C2 O1 H1 109.7(19) ?
C12 O2 H2 106.4(18) ?
C2 C1 C10 119.89(17) ?
C2 C1 S1 120.49(15) ?
C10 C1 S1 119.46(14) ?
O1 C2 C1 117.98(17) ?
O1 C2 C3 121.30(17) ?
C1 C2 C3 120.68(18) ?
C4 C3 C2 120.41(18) ?
C4 C3 H3 119.8 ?
C2 C3 H3 119.8 ?
C3 C4 C5 121.19(18) ?
C3 C4 H4 119.4 ?
C5 C4 H4 119.4 ?
C6 C5 C10 119.51(18) ?
C6 C5 C4 121.74(18) ?
C10 C5 C4 118.74(18) ?
C7 C6 C5 120.94(19) ?
C7 C6 H6 119.5 ?
C5 C6 H6 119.5 ?
C6 C7 C8 119.79(19) ?
C6 C7 H7 120.1 ?
C8 C7 H7 120.1 ?
C9 C8 C7 120.76(19) ?
C9 C8 H8 119.6 ?
C7 C8 H8 119.6 ?
C8 C9 C10 121.02(18) ?
C8 C9 H9 119.5 ?
C10 C9 H9 119.5 ?
C5 C10 C9 117.97(17) ?
C5 C10 C1 119.06(18) ?
C9 C10 C1 122.96(17) ?
C12 C11 C20 119.49(18) ?
C12 C11 S1 117.42(15) ?
C20 C11 S1 122.87(15) ?
C11 C12 O2 123.10(18) ?
C11 C12 C13 121.56(18) ?
O2 C12 C13 115.34(18) ?
C14 C13 C12 119.68(19) ?
C14 C13 H13 120.2 ?
C12 C13 H13 120.2 ?
C13 C14 C15 121.39(19) ?
C13 C14 H14 119.3 ?
C15 C14 H14 119.3 ?
C16 C15 C14 121.73(19) ?
C16 C15 C20 119.40(19) ?
C14 C15 C20 118.86(18) ?
C17 C16 C15 120.8(2) ?
C17 C16 H16 119.6 ?
C15 C16 H16 119.6 ?
C16 C17 C18 119.9(2) ?
C16 C17 H17 120.0 ?
C18 C17 H17 120.0 ?
C19 C18 C17 121.0(2) ?
C19 C18 H18 119.5 ?
C17 C18 H18 119.5 ?
C18 C19 C20 120.6(2) ?
C18 C19 H19 119.7 ?
C20 C19 H19 119.7 ?
C19 C20 C15 118.27(18) ?
C19 C20 C11 122.71(18) ?
C15 C20 C11 119.02(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C11 1.780(2) y
S1 C1 1.780(2) y
O1 C2 1.366(2) ?
O1 H1 0.83(3) ?
O2 C12 1.375(2) ?
O2 H2 0.86(3) ?
C1 C2 1.379(3) ?
C1 C10 1.430(3) ?
C2 C3 1.408(3) ?
C3 C4 1.358(3) ?
C3 H3 0.9500 ?
C4 C5 1.422(3) ?
C4 H4 0.9500 ?
C5 C6 1.415(3) ?
C5 C10 1.421(3) ?
C6 C7 1.369(3) ?
C6 H6 0.9500 ?
C7 C8 1.409(3) ?
C7 H7 0.9500 ?
C8 C9 1.364(3) ?
C8 H8 0.9500 ?
C9 C10 1.425(3) ?
C9 H9 0.9500 ?
C11 C12 1.375(3) ?
C11 C20 1.433(3) ?
C12 C13 1.411(3) ?
C13 C14 1.364(3) ?
C13 H13 0.9500 ?
C14 C15 1.419(3) ?
C14 H14 0.9500 ?
C15 C16 1.411(3) ?
C15 C20 1.425(3) ?
C16 C17 1.368(3) ?
C16 H16 0.9500 ?
C17 C18 1.403(3) ?
C17 H17 0.9500 ?
C18 C19 1.366(3) ?
C18 H18 0.9500 ?
C19 C20 1.417(3) ?
C19 H19 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O2 3 0.83(3) 2.00(3) 2.826(2) 171(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 78439
