#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/05/2010558.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_2010558
loop_
_publ_author_name
'Kansikas, Jarno'
'Sipilä, Kaija'
_publ_section_title
;
 Two 9-alkylthiophenanthrenes at 193K (alkyl = dodecyl and tetradecyl)
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              69
_journal_page_last               71
_journal_paper_doi               10.1107/S0108270199012871
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C26 H34 S'
_chemical_formula_weight         378.59
_chemical_melting_point          353
_chemical_name_systematic
;
 9-(Dodecylthio)phenanthrene
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 99.28(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.105(2)
_cell_length_b                   35.679(7)
_cell_length_c                   6.7840(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      10
_cell_measurement_theta_min      4
_cell_volume                     2175.0(8)
_computing_cell_refinement       'CAD4 Express'
_computing_data_collection       'CAD4 Express (Enraf-Nonius, 1994)'
_computing_data_reduction        'WINGX (Farrugia, 1998)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  .0170
_diffrn_reflns_av_sigmaI/netI    .0172
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3928
_diffrn_reflns_theta_max         64.95
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        .8
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.348
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          .31
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .10
_refine_diff_density_max         .390
_refine_diff_density_min         -.353
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.102
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.301
_refine_ls_restrained_S_obs      1.136
_refine_ls_R_factor_all          .0655
_refine_ls_R_factor_gt           .0493
_refine_ls_shift/esd_mean        .000
_refine_ls_shift/su_max          -.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
  calc w = 1/[\s^2^(Fo^2^)+(0.0466P)^2^+1.4963P]
  where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_wR_factor_all         .1444
_refine_ls_wR_factor_ref         .1183
_reflns_number_gt                3198
_reflns_number_total             3688
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            os1072.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (12 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (12
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (14
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (10 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2010558
_cod_database_fobs_code          2010558
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
S .78808(6) .13583(2) .33972(8) .0380(2) Uani d . 1 . S
C1 1.3331(2) .18312(6) .3556(3) .0347(5) Uani d . 1 . C
H1A 1.3585 .17032 .4792 .042 Uiso calc R 1 . H
C2 1.4417(2) .20153(6) .2758(3) .0365(5) Uani d . 1 . C
H2A 1.5420 .20093 .3418 .044 Uiso calc R 1 . H
C3 1.4040(2) .22116(6) .0967(3) .0358(5) Uani d . 1 . C
H3A 1.4786 .23451 .0427 .043 Uiso calc R 1 . H
C4b .9935(2) .20064(5) -.0272(3) .0288(4) Uani d . 1 . C
C4a 1.1466(2) .20193(5) .0741(3) .0278(4) Uani d . 1 . C
C4 1.2611(2) .22132(6) -.0012(3) .0331(5) Uani d . 1 . C
H4A 1.2378 .23480 -.1230 .040 Uiso calc R 1 . H
C5 .9467(2) .21934(6) -.2092(3) .0345(5) Uani d . 1 . C
H5A 1.0177 .23298 -.2688 .041 Uiso calc R 1 . H
C6 .8024(3) .21844(6) -.3023(3) .0398(5) Uani d . 1 . C
H6A .7742 .23135 -.4250 .048 Uiso calc R 1 . H
C7 .6961(3) .19855(7) -.2175(3) .0390(5) Uani d . 1 . C
H7A .5954 .19803 -.2819 .047 Uiso calc R 1 . H
C8a .8853(2) .18045(6) .0590(3) .0285(4) Uani d . 1 . C
C8 .7376(2) .17981(6) -.0412(3) .0350(5) Uani d . 1 . C
H8A .6650 .16606 .0147 .042 Uiso calc R 1 . H
C9 .9297(2) .16113(6) .2480(3) .0313(5) Uani d . 1 . C
C10a 1.1852(2) .18284(6) .2584(3) .0312(5) Uani d . 1 . C
C10 1.0721(2) .16298(6) .3418(3) .0328(5) Uani d . 1 . C
H10A 1.0984 .15076 .4670 .039 Uiso calc R 1 . H
C12 .8815(2) .11545(6) .5705(3) .0362(5) Uani d . 1 . C
H12A .9660 .09979 .5444 .043 Uiso calc R 1 . H
H12B .9206 .13550 .6655 .043 Uiso calc R 1 . H
C13 .7692(3) .09148(6) .6587(3) .0380(5) Uani d . 1 . C
H13A .6866 .10753 .6878 .046 Uiso calc R 1 . H
H13B .7269 .07236 .5598 .046 Uiso calc R 1 . H
C14 .8417(3) .07208(6) .8499(3) .0387(5) Uani d . 1 . C
H14A .8858 .09136 .9467 .046 Uiso calc R 1 . H
H14B .9237 .05599 .8193 .046 Uiso calc R 1 . H
C15 .7343(3) .04812(7) .9468(4) .0411(5) Uani d . 1 . C
H15A .6539 .06427 .9818 .049 Uiso calc R 1 . H
H15B .6881 .02920 .8493 .049 Uiso calc R 1 . H
C16 .8106(3) .02825(7) 1.1337(3) .0401(5) Uani d . 1 . C
H16A .8904 .01204 1.0974 .048 Uiso calc R 1 . H
H16B .8582 .04728 1.2294 .048 Uiso calc R 1 . H
C17 .7073(3) .00437(7) 1.2368(4) .0417(5) Uani d . 1 . C
H17A .6274 .02050 1.2732 .050 Uiso calc R 1 . H
H17B .6600 -.01479 1.1416 .050 Uiso calc R 1 . H
C18 .7858(3) -.01514(7) 1.4235(4) .0411(5) Uani d . 1 . C
H18A .8659 -.03113 1.3866 .049 Uiso calc R 1 . H
H18B .8331 .00411 1.5181 .049 Uiso calc R 1 . H
C19 .6850(3) -.03922(7) 1.5292(4) .0438(6) Uani d . 1 . C
H19A .6043 -.02334 1.5653 .053 Uiso calc R 1 . H
H19B .6385 -.05870 1.4354 .053 Uiso calc R 1 . H
C20 .7645(3) -.05813(7) 1.7158(4) .0426(6) Uani d . 1 . C
H20A .8127 -.03864 1.8082 .051 Uiso calc R 1 . H
H20B .8441 -.07434 1.6789 .051 Uiso calc R 1 . H
C21 .6642(3) -.08182(7) 1.8254(4) .0418(5) Uani d . 1 . C
H21A .5817 -.06601 1.8568 .050 Uiso calc R 1 . H
H21B .6202 -.10224 1.7361 .050 Uiso calc R 1 . H
C22 .7453(3) -.09881(7) 2.0174(3) .0415(5) Uani d . 1 . C
H22A .7884 -.07842 2.1075 .050 Uiso calc R 1 . H
H22B .8285 -.11447 1.9864 .050 Uiso calc R 1 . H
C23 .6446(3) -.12269(8) 2.1243(4) .0532(7) Uani d . 1 . C
H23A .7021 -.13294 2.2470 .080 Uiso calc R 1 . H
H23B .6034 -.14329 2.0370 .080 Uiso calc R 1 . H
H23C .5632 -.10722 2.1579 .080 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 .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .3331 .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
C9 S C12 104.01(10) y
C2 C1 C10a 121.2(2) ?
C1 C2 C3 119.5(2) ?
C4 C3 C2 120.5(2) ?
C4 C4a C4b 123.5(2) y
C4b C4a C10a 119.0(2) y
C4a C4b C5 122.1(2) y
C4a C4b C8a 119.9(2) y
C5 C4b C8a 118.0(2) ?
C4 C4a C10a 117.5(2) ?
C3 C4 C4a 121.6(2) ?
C6 C5 C4b 121.9(2) ?
C5 C6 C7 120.1(2) ?
C8 C7 C6 119.7(2) ?
C8 C8a C4b 118.8(2) ?
C8 C8a C9 121.8(2) ?
C4b C8a C9 119.4(2) y
C7 C8 C8a 121.5(2) ?
C8a C9 C10 120.1(2) y
C8a C9 S 116.0(2) y
C10 C9 S 123.9(2) y
C1 C10a C4a 119.6(2) ?
C1 C10a C10 120.9(2) ?
C9 C10 C10a 122.1(2) y
C4a C10a C10 119.5(2) y
C13 C12 S 108.2(2) y
C12 C13 C14 111.2(2) y
C13 C14 C15 113.7(2) y
C16 C15 C14 112.5(2) ?
C15 C16 C17 114.3(2) ?
C16 C17 C18 113.5(2) ?
C19 C18 C17 114.5(2) ?
C20 C19 C18 113.8(2) ?
C19 C20 C21 114.4(2) ?
C22 C21 C20 113.2(2) ?
C21 C22 C23 112.7(2) ?
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
S C9 . 1.767(2) y
S C12 . 1.809(2) y
C1 C2 . 1.370(3) ?
C1 C10a . 1.401(3) ?
C2 C3 . 1.396(3) ?
C3 C4 . 1.362(3) ?
C4 C4a . 1.413(3) y
C4a C4b . 1.453(3) y
C4a C10a . 1.418(3) y
C4b C5 . 1.407(3) y
C4b C8a . 1.420(3) y
C5 C6 . 1.363(3) ?
C6 C7 . 1.397(3) ?
C7 C8 . 1.369(3) ?
C8 C8a . 1.406(3) ?
C8a C9 . 1.455(3) y
C9 C10 . 1.350(3) y
C10 C10a . 1.439(3) y
C12 C13 . 1.527(3) y
C13 C14 . 1.524(3) y
C14 C15 . 1.526(3) ?
C15 C16 . 1.520(3) ?
C16 C17 . 1.520(3) ?
C17 C18 . 1.519(3) ?
C18 C19 . 1.518(3) ?
C19 C20 . 1.512(4) ?
C20 C21 . 1.523(3) ?
C21 C22 . 1.516(3) ?
C22 C23 . 1.519(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
_geom_torsion_publ_flag
C10a C1 C2 C3 1.6(3) ?
C1 C2 C3 C4 -1.7(3) ?
C5 C4b C4a C4 -.9(3) ?
C8a C4b C4a C4 180.0(2) ?
C5 C4b C4a C10a 179.1(2) ?
C8a C4b C4a C10a .0(3) y
C2 C3 C4 C4a .2(3) ?
C10a C4a C4 C3 1.4(3) ?
C4b C4a C4 C3 -178.6(2) ?
C8a C4b C5 C6 .0(3) ?
C4a C4b C5 C6 -179.1(2) ?
C4b C5 C6 C7 .0(3) ?
C5 C6 C7 C8 -.4(3) ?
C5 C4b C8a C8 .4(3) ?
C4a C4b C8a C8 179.6(2) ?
C5 C4b C8a C9 -179.4(2) ?
C4a C4b C8a C9 -.2(3) y
C6 C7 C8 C8a .8(3) ?
C4b C8a C8 C7 -.9(3) ?
C9 C8a C8 C7 178.9(2) ?
C8 C8a C9 C10 -178.7(2) y
C4b C8a C9 C10 1.1(3) y
C8 C8a C9 S 1.8(3) y
C4b C8a C9 S -178.44(15) y
C12 S C9 C10 -.1(2) y
C12 S C9 C8a 179.4(2) y
C2 C1 C10a C4a .0(3) ?
C2 C1 C10a C10 179.1(2) ?
C4 C4a C10a C1 -1.4(3) ?
C4b C4a C10a C1 178.6(2) ?
C4 C4a C10a C10 179.5(2) ?
C4b C4a C10a C10 -.6(3) ?
C8a C9 C10 C10a -1.7(3) y
S C9 C10 C10a 177.8(2) y
C1 C10a C10 C9 -177.6(2) ?
C4a C10a C10 C9 1.5(3) ?
C9 S C12 C13 -177.79(15) ?
S C12 C13 C14 177.7(2) ?
C12 C13 C14 C15 179.2(2) ?
C13 C14 C15 C16 178.3(2) ?
C14 C15 C16 C17 179.3(2) ?
C15 C16 C17 C18 -179.8(2) ?
C16 C17 C18 C19 -179.9(2) ?
C17 C18 C19 C20 -179.4(2) ?
C18 C19 C20 C21 178.9(2) ?
C19 C20 C21 C22 -177.1(2) ?
C20 C21 C22 C23 -179.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135955
