#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006404.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_2006404
loop_
_publ_author_name
'Kansikas, J.'
'Sipil\"a, K.'
_publ_section_title
;
 Four 9-Alkylthiophenanthrenes at 193K (Alkyl = Methyl, Ethyl, Propyl
 and Butyl)
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1127
_journal_page_last               1131
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C16 H14 S'
_chemical_formula_weight         238.35
_chemical_melting_point          353
_chemical_name_systematic
;
 9-Ethylthiophenanthrene
;
_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                 98.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.054(4)
_cell_length_b                   20.644(9)
_cell_length_c                   6.659(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      10
_cell_measurement_theta_min      5
_cell_volume                     1232.2(9)
_computing_cell_refinement       'AFC7S Software'
_computing_data_collection
'AFC7S Software (Molecular Structure Corporation, 1992)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1993)'
_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       'Rigaku AFC7S'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0825
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1897
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.343
_refine_ls_extinction_coef       0.0032(19)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.030
_refine_ls_goodness_of_fit_obs   1.103
_refine_ls_hydrogen_treatment    'H atoms: riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_restrained_S_obs      1.103
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_obs          0.0679
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0485P)^2^+1.4260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1553
_refine_ls_wR_factor_obs         0.1378
_reflns_number_observed          1389
_reflns_number_total             1851
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ka1230.cif
_[local]_cod_data_source_block   2
_[local]_cod_cif_authors_sg_H-M  P2~1~/c
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1232.2(10)
_cod_database_code               2006404
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S 0.0382(6) 0.0378(6) 0.0377(6) 0.0034(6) 0.0074(5) -0.0095(6)
C1 0.036(3) 0.032(2) 0.035(3) -0.002(2) 0.001(2) -0.003(2)
C2 0.034(3) 0.031(2) 0.040(3) 0.000(2) -0.002(2) 0.004(2)
C3 0.033(3) 0.032(2) 0.044(3) 0.004(2) 0.008(2) 0.000(2)
C4 0.040(3) 0.026(2) 0.033(2) -0.001(2) 0.006(2) -0.004(2)
C4a 0.035(2) 0.023(2) 0.027(2) -0.001(2) 0.007(2) 0.001(2)
C4b 0.033(2) 0.024(2) 0.030(2) -0.003(2) 0.003(2) 0.003(2)
C5 0.041(3) 0.034(3) 0.035(3) 0.002(2) 0.000(2) -0.004(2)
C6 0.045(3) 0.039(3) 0.032(3) -0.006(2) 0.003(2) -0.005(2)
C7 0.034(3) 0.037(3) 0.040(3) 0.003(2) -0.006(2) 0.005(2)
C8 0.039(3) 0.033(2) 0.029(2) -0.004(2) 0.005(2) 0.000(2)
C8a 0.034(2) 0.022(2) 0.030(2) -0.003(2) 0.006(2) 0.004(2)
C9 0.036(3) 0.022(2) 0.031(2) 0.000(2) 0.006(2) 0.001(2)
C10 0.042(3) 0.027(2) 0.028(2) -0.005(2) 0.005(2) -0.006(2)
C10a 0.035(2) 0.027(2) 0.028(2) 0.000(2) 0.008(2) 0.002(2)
C12 0.044(3) 0.033(2) 0.034(2) -0.001(2) 0.010(2) -0.005(2)
C13 0.071(4) 0.040(3) 0.045(3) 0.008(3) 0.021(3) -0.005(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_type_symbol
S 0.26226(13) 0.04865(6) 0.4474(2) 0.0377(4) Uani d . 1 S
C1 -0.2849(5) 0.1309(2) 0.4344(6) 0.0349(11) Uani d . 1 C
H1 -0.3090(5) 0.1085(2) 0.3131(6) 0.042 Uiso calc R 1 H
C2 -0.3942(5) 0.1637(2) 0.5154(7) 0.0359(11) Uani d . 1 C
H2 -0.4921(5) 0.1626(2) 0.4504(7) 0.043 Uiso calc R 1 H
C3 -0.3594(5) 0.1986(2) 0.6941(7) 0.0363(11) Uani d . 1 C
H3 -0.4335(5) 0.2216(2) 0.7468(7) 0.044 Uiso calc R 1 H
C4 -0.2157(5) 0.1992(2) 0.7931(6) 0.0330(10) Uani d . 1 C
H4 -0.1935(5) 0.2227(2) 0.9127(6) 0.040 Uiso calc R 1 H
C4a -0.1011(5) 0.1647(2) 0.7162(6) 0.0280(9) Uani d . 1 C
C4b 0.0531(4) 0.1632(2) 0.8173(6) 0.0290(10) Uani d . 1 C
C5 0.0969(5) 0.1963(2) 1.0006(6) 0.0372(11) Uani d . 1 C
H5 0.0255(5) 0.2188(2) 1.0605(6) 0.045 Uiso calc R 1 H
C6 0.2419(5) 0.1962(2) 1.0934(7) 0.0387(11) Uani d . 1 C
H6 0.2688(5) 0.2187(2) 1.2141(7) 0.046 Uiso calc R 1 H
C7 0.3491(5) 0.1618(2) 1.0043(7) 0.0380(11) Uani d . 1 C
H7 0.4478(5) 0.1616(2) 1.0662(7) 0.046 Uiso calc R 1 H
C8 0.3102(5) 0.1285(2) 0.8272(6) 0.0336(10) Uani d . 1 C
H8 0.3830(5) 0.1059(2) 0.7706(6) 0.040 Uiso calc R 1 H
C8a 0.1627(5) 0.1279(2) 0.7294(6) 0.0284(9) Uani d . 1 C
C9 0.1197(5) 0.0933(2) 0.5410(6) 0.0296(10) Uani d . 1 C
C10 -0.0239(5) 0.0957(2) 0.4482(6) 0.0322(10) Uani d . 1 C
H10 -0.0498(5) 0.0738(2) 0.3262(6) 0.039 Uiso calc R 1 H
C10a -0.1360(5) 0.1308(2) 0.5328(6) 0.0299(10) Uani d . 1 C
C12 0.1753(5) 0.0189(2) 0.2062(6) 0.0364(11) Uani d . 1 C
H12A 0.0926(5) -0.0093(2) 0.2244(6) 0.044 Uiso calc R 1 H
H12B 0.1371(5) 0.0548(2) 0.1201(6) 0.044 Uiso calc R 1 H
C13 0.2919(6) -0.0184(2) 0.1082(7) 0.0508(13) Uani d . 1 C
H13A 0.2473(6) -0.0347(2) -0.0213(7) 0.076 Uiso calc R 1 H
H13B 0.3286(6) -0.0539(2) 0.1940(7) 0.076 Uiso calc R 1 H
H13C 0.3730(6) 0.0100(2) 0.0901(7) 0.076 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 0.0033 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_publ_flag
C9 S C12 104.1(2) yes
C2 C1 C10a 120.8(4) ?
C1 C2 C3 120.3(4) ?
C4 C3 C2 120.1(4) ?
C3 C4 C4a 121.1(4) ?
C4 C4a C4b 123.1(4) yes
C4 C4a C10a 118.6(4) ?
C4b C4a C10a 118.2(4) yes
C4a C4b C5 121.6(4) yes
C4a C4b C8a 119.9(4) yes
C5 C4b C8a 118.6(4) ?
C4b C5 C6 121.7(4) ?
C5 C6 C7 119.1(4) ?
C8 C7 C6 120.7(4) ?
C7 C8 C8a 121.2(4) ?
C4b C8a C8 118.6(4) ?
C4b C8a C9 119.4(4) yes
C8 C8a C9 121.9(4) ?
C10 C9 C8a 119.9(4) yes
C10 C9 S 123.9(3) yes
C8a C9 S 116.2(3) yes
C9 C10 C10a 121.8(4) yes
C4a C10a C1 119.1(4) ?
C4a C10a C10 120.7(4) yes
C1 C10a C10 120.2(4) ?
C13 C12 S 108.2(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C9 1.769(4) yes
S C12 1.794(4) yes
C1 C2 1.371(6) ?
C1 C10a 1.413(6) ?
C2 C3 1.389(6) ?
C3 C4 1.373(6) ?
C4 C4a 1.412(6) yes
C4a C4b 1.462(5) yes
C4a C10a 1.405(6) yes
C4b C5 1.406(6) yes
C4b C8a 1.422(6) yes
C5 C6 1.371(6) ?
C6 C7 1.400(6) ?
C7 C8 1.367(6) ?
C8 C8a 1.401(6) ?
C8a C9 1.449(5) yes
C9 C10 1.360(6) yes
C10 C10a 1.426(6) yes
C12 C13 1.526(6) yes