#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/11/2201113.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_2201113
loop_
_publ_author_name
'Jarno Kansikas'
'Kaija Sipilä'
_publ_section_title
;
 2-(Phenanthren-9-ylthiomethylthio)tetrahydropyran at 193K
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o600
_journal_page_last               o602
_journal_paper_doi               10.1107/S1600536802006542
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C20 H20 O S2'
_chemical_formula_moiety         'C20 H20 O S2'
_chemical_formula_sum            'C20 H20 O S2'
_chemical_formula_weight         340.48
_chemical_name_systematic
;
2-(phenanthren-9-ylthiomethylthio)tetrahydropyran
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.42(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.793(3)
_cell_length_b                   14.890(3)
_cell_length_c                   8.9570(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      4
_cell_volume                     1683.2(6)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'WINGX (Farrugia, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5817
_diffrn_reflns_theta_full        67.84
_diffrn_reflns_theta_max         67.84
_diffrn_reflns_theta_min         3.50
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.865
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0353
_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)+(0.0394P)²+0.5652P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                2427
_reflns_number_total             2995
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6107.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2201113
_cod_database_fobs_code          2201113
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O 0.86501(11) 0.81451(9) 0.45082(15) 0.0448(3) Uani d . 1 . . O
S1 0.72832(4) 1.04354(4) 0.31959(6) 0.04932(16) Uani d . 1 . . S
C1 0.34993(18) 0.92378(15) 0.1111(2) 0.0481(5) Uani d . 1 . . C
H1A 0.3825 0.8819 0.0533 0.058 Uiso calc R 1 . . H
S2 0.89634(4) 0.93130(4) 0.22843(6) 0.04928(17) Uani d . 1 . . S
C2 0.24204(19) 0.92351(16) 0.1017(3) 0.0539(6) Uani d . 1 . . C
H2A 0.2001 0.8818 0.0376 0.065 Uiso calc R 1 . . H
C3 0.19404(18) 0.98479(16) 0.1867(3) 0.0533(6) Uani d . 1 . . C
H3A 0.1191 0.9852 0.1792 0.064 Uiso calc R 1 . . H
C4 0.25368(17) 1.04420(15) 0.2804(2) 0.0464(5) Uani d . 1 . . C
H4A 0.2194 1.0845 0.3389 0.056 Uiso calc R 1 . . H
C5 0.38945(19) 1.17406(14) 0.4789(2) 0.0487(5) Uani d . 1 . . C
H5A 0.3148 1.1786 0.4728 0.058 Uiso calc R 1 . . H
C6 0.4540(2) 1.23054(15) 0.5733(3) 0.0587(6) Uani d . 1 . . C
H6A 0.4235 1.2738 0.6312 0.070 Uiso calc R 1 . . H
C7 0.5632(2) 1.22525(15) 0.5852(2) 0.0556(6) Uani d . 1 . . C
H7A 0.6073 1.2639 0.6526 0.067 Uiso calc R 1 . . H
C8 0.60745(19) 1.16391(14) 0.4993(2) 0.0470(5) Uani d . 1 . . C
H8A 0.6823 1.1609 0.5071 0.056 Uiso calc R 1 . . H
C9 0.58913(16) 1.04156(13) 0.3063(2) 0.0382(4) Uani d . 1 . . C
C10 0.52523(16) 0.98509(14) 0.2134(2) 0.0416(5) Uani d . 1 . . C
H10A 0.5563 0.9442 0.1519 0.050 Uiso calc R 1 . . H
C11 0.41325(16) 0.98521(13) 0.2053(2) 0.0385(4) Uani d . 1 . . C
C12 0.36497(16) 1.04736(13) 0.2927(2) 0.0368(4) Uani d . 1 . . C
C13 0.43170(16) 1.10909(13) 0.3902(2) 0.0379(4) Uani d . 1 . . C
C14 0.54329(16) 1.10551(13) 0.3998(2) 0.0375(4) Uani d . 1 . . C
C15 0.75555(17) 0.94369(15) 0.2172(2) 0.0466(5) Uani d . 1 . . C
H15A 0.7261 0.8903 0.2615 0.056 Uiso calc R 1 . . H
H15B 0.7216 0.9487 0.1100 0.056 Uiso calc R 1 . . H
C16 0.93230(16) 0.88494(14) 0.4210(2) 0.0435(5) Uani d . 1 . . C
H16A 0.9260 0.9344 0.4945 0.052 Uiso calc R 1 . . H
C17 0.87337(18) 0.73456(15) 0.3628(2) 0.0508(5) Uani d . 1 . . C
H17A 0.8497 0.7482 0.2544 0.061 Uiso calc R 1 . . H
H17B 0.8258 0.6878 0.3928 0.061 Uiso calc R 1 . . H
C18 0.98513(19) 0.69871(15) 0.3841(3) 0.0513(5) Uani d . 1 . . C
H18A 0.9887 0.6473 0.3150 0.062 Uiso calc R 1 . . H
H18B 1.0057 0.6770 0.4893 0.062 Uiso calc R 1 . . H
C19 1.06218(17) 0.77151(15) 0.3518(2) 0.0499(5) Uani d . 1 . . C
H19A 1.0495 0.7861 0.2424 0.060 Uiso calc R 1 . . H
H19B 1.1359 0.7495 0.3790 0.060 Uiso calc R 1 . . H
C20 1.04724(17) 0.85562(15) 0.4433(2) 0.0472(5) Uani d . 1 . . C
H20A 1.0720 0.8435 0.5520 0.057 Uiso calc R 1 . . H
H20B 1.0910 0.9049 0.4121 0.057 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C16 O C17 114.09(15) yes
C9 S1 C15 103.17(10) yes
C2 C1 C11 121.0(2) ?
C2 C1 H1A 119.5 ?
C11 C1 H1A 119.5 ?
C15 S2 C16 100.66(10) yes
C1 C2 C3 119.6(2) ?
C1 C2 H2A 120.2 ?
C3 C2 H2A 120.2 ?
C4 C3 C2 120.6(2) ?
C4 C3 H3A 119.7 ?
C2 C3 H3A 119.7 ?
C3 C4 C12 121.7(2) ?
C3 C4 H4A 119.1 ?
C12 C4 H4A 119.1 ?
C6 C5 C13 121.3(2) ?
C6 C5 H5A 119.3 ?
C13 C5 H5A 119.3 ?
C5 C6 C7 120.7(2) ?
C5 C6 H6A 119.6 ?
C7 C6 H6A 119.6 ?
C8 C7 C6 119.8(2) ?
C8 C7 H7A 120.1 ?
C6 C7 H7A 120.1 ?
C7 C8 C14 120.9(2) ?
C7 C8 H8A 119.6 ?
C14 C8 H8A 119.6 ?
C10 C9 C14 119.96(19) ?
C10 C9 S1 123.42(15) yes
C14 C9 S1 116.61(15) yes
C9 C10 C11 122.04(18) ?
C9 C10 H10A 119.0 ?
C11 C10 H10A 119.0 ?
C1 C11 C12 119.68(19) ?
C1 C11 C10 120.39(19) ?
C12 C11 C10 119.93(18) ?
C4 C12 C11 117.40(19) ?
C4 C12 C13 123.86(19) ?
C11 C12 C13 118.73(18) ?
C5 C13 C14 117.75(19) ?
C5 C13 C12 122.11(19) ?
C14 C13 C12 120.14(17) ?
C8 C14 C13 119.49(19) ?
C8 C14 C9 121.36(19) ?
C13 C14 C9 119.15(18) ?
S2 C15 S1 109.29(12) yes
S2 C15 H15A 109.8 ?
S1 C15 H15A 109.8 ?
S2 C15 H15B 109.8 ?
S1 C15 H15B 109.8 ?
H15A C15 H15B 108.3 ?
O C16 C20 111.72(17) yes
O C16 S2 112.90(14) yes
C20 C16 S2 108.63(14) ?
O C16 H16A 107.8 ?
C20 C16 H16A 107.8 ?
S2 C16 H16A 107.8 ?
O C17 C18 112.13(17) ?
O C17 H17A 109.2 ?
C18 C17 H17A 109.2 ?
O C17 H17B 109.2 ?
C18 C17 H17B 109.2 ?
H17A C17 H17B 107.9 ?
C17 C18 C19 110.68(18) ?
C17 C18 H18A 109.5 ?
C19 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
C19 C18 H18B 109.5 ?
H18A C18 H18B 108.1 ?
C18 C19 C20 109.86(17) ?
C18 C19 H19A 109.7 ?
C20 C19 H19A 109.7 ?
C18 C19 H19B 109.7 ?
C20 C19 H19B 109.7 ?
H19A C19 H19B 108.2 ?
C16 C20 C19 111.70(17) ?
C16 C20 H20A 109.3 ?
C19 C20 H20A 109.3 ?
C16 C20 H20B 109.3 ?
C19 C20 H20B 109.3 ?
H20A C20 H20B 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O C16 . 1.410(2) yes
O C17 . 1.441(3) yes
S1 C9 . 1.765(2) yes
S1 C15 . 1.810(2) yes
C1 C2 . 1.369(3) ?
C1 C11 . 1.407(3) ?
C1 H1A . 0.9500 ?
S2 C15 . 1.797(2) yes
S2 C16 . 1.845(2) yes
C2 C3 . 1.394(3) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.364(3) ?
C3 H3A . 0.9500 ?
C4 C12 . 1.411(3) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.369(3) ?
C5 C13 . 1.414(3) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.386(4) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.375(3) ?
C7 H7A . 0.9500 ?
C8 C14 . 1.409(3) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.358(3) ?
C9 C14 . 1.453(3) ?
C10 C11 . 1.423(3) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.418(3) ?
C12 C13 . 1.446(3) ?
C13 C14 . 1.417(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C20 . 1.515(3) ?
C16 H16A . 1.0000 ?
C17 C18 . 1.509(3) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 C19 . 1.525(3) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C19 C20 . 1.526(3) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
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
_geom_torsion_publ_flag
C11 C1 C2 C3 -0.1(3) ?
C1 C2 C3 C4 -0.8(3) ?
C2 C3 C4 C12 1.3(3) ?
C13 C5 C6 C7 -0.4(3) ?
C5 C6 C7 C8 1.3(3) ?
C6 C7 C8 C14 -0.6(3) ?
C15 S1 C9 C10 -11.0(2) yes
C15 S1 C9 C14 169.89(14) yes
C14 C9 C10 C11 -0.9(3) ?
S1 C9 C10 C11 -179.97(15) ?
C2 C1 C11 C12 0.5(3) ?
C2 C1 C11 C10 -179.7(2) ?
C9 C10 C11 C1 -178.01(18) ?
C9 C10 C11 C12 1.8(3) ?
C3 C4 C12 C11 -0.9(3) ?
C3 C4 C12 C13 179.92(18) ?
C1 C11 C12 C4 0.0(3) ?
C10 C11 C12 C4 -179.85(17) ?
C1 C11 C12 C13 179.21(17) ?
C10 C11 C12 C13 -0.6(3) ?
C6 C5 C13 C14 -1.3(3) ?
C6 C5 C13 C12 178.41(19) ?
C4 C12 C13 C5 -1.9(3) ?
C11 C12 C13 C5 178.89(17) ?
C4 C12 C13 C14 177.71(17) ?
C11 C12 C13 C14 -1.5(3) ?
C7 C8 C14 C13 -1.1(3) ?
C7 C8 C14 C9 178.82(18) ?
C5 C13 C14 C8 1.9(3) ?
C12 C13 C14 C8 -177.74(17) ?
C5 C13 C14 C9 -177.95(17) ?
C12 C13 C14 C9 2.4(3) ?
C10 C9 C14 C8 178.89(18) ?
S1 C9 C14 C8 -2.0(2) ?
C10 C9 C14 C13 -1.2(3) ?
S1 C9 C14 C13 177.92(14) ?
C16 S2 C15 S1 78.31(12) yes
C9 S1 C15 S2 -176.73(10) yes
C17 O C16 C20 -56.0(2) ?
C17 O C16 S2 66.77(19) yes
C15 S2 C16 O 46.56(16) yes
C15 S2 C16 C20 171.05(14) ?
C16 O C17 C18 56.9(2) ?
O C17 C18 C19 -54.1(2) ?
C17 C18 C19 C20 52.0(2) ?
O C16 C20 C19 53.7(2) ?
S2 C16 C20 C19 -71.50(19) ?
C18 C19 C20 C16 -51.9(2) ?
