#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006405.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_2006405
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            'C17 H16 S'
_chemical_formula_weight         252.37
_chemical_melting_point          374
_chemical_name_systematic
;
 9-Propylthiophenanthrene
;
_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                90.0
_cell_angle_beta                 99.12(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   9.067(3)
_cell_length_b                   21.123(7)
_cell_length_c                   7.007(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      10
_cell_measurement_theta_min      4
_cell_volume                     1325.0(8)
_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  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2654
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.040
_refine_ls_goodness_of_fit_obs   1.041
_refine_ls_hydrogen_treatment
'H atoms: refined coordinates and isotropic U'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.312
_refine_ls_restrained_S_obs      1.041
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_obs          0.0504
_refine_ls_shift/esd_max         0.004
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.1420P)^2^+0.1790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1856
_refine_ls_wR_factor_obs         0.1419
_reflns_number_observed          2419
_reflns_number_total             2599
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ka1230.cif
_[local]_cod_data_source_block   3
_[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        1325.05(.9)
_cod_database_code               2006405
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 0.0361(3) 0.0568(4) 0.0424(3) -0.0078(2) 0.0036(2) 0.0099(2)
C1 0.0354(9) 0.0432(10) 0.0468(10) 0.0039(7) 0.0015(7) 0.0048(7)
C2 0.0304(8) 0.0459(10) 0.0553(11) 0.0026(7) 0.0026(7) -0.0034(8)
C3 0.0344(9) 0.0421(9) 0.0533(11) -0.0029(7) 0.0097(7) -0.0008(7)
C4 0.0372(9) 0.0387(9) 0.0441(10) -0.0022(7) 0.0078(7) 0.0026(7)
C4a 0.0334(8) 0.0307(8) 0.0404(9) 0.0013(6) 0.0057(6) -0.0014(6)
C4b 0.0348(8) 0.0300(8) 0.0380(8) 0.0000(6) 0.0050(6) -0.0015(6)
C5 0.0400(9) 0.0400(9) 0.0443(10) -0.0035(7) 0.0028(7) 0.0052(7)
C6 0.0449(10) 0.0447(10) 0.0419(10) -0.0031(7) -0.0024(8) 0.0081(7)
C7 0.0372(9) 0.0481(10) 0.0461(10) -0.0013(7) -0.0029(7) 0.0006(8)
C8 0.0338(9) 0.0419(9) 0.0422(9) -0.0025(7) 0.0044(7) -0.0007(7)
C8a 0.0333(8) 0.0326(8) 0.0367(8) 0.0005(6) 0.0043(6) -0.0028(6)
C9 0.0346(8) 0.0358(8) 0.0392(9) -0.0011(6) 0.0073(6) -0.0002(6)
C10 0.0364(8) 0.0417(9) 0.0403(9) 0.0008(7) 0.0042(7) 0.0050(7)
C10a 0.0328(8) 0.0347(8) 0.0414(9) 0.0020(6) 0.0051(6) -0.0004(6)
C12 0.0419(9) 0.0391(9) 0.0382(9) -0.0001(7) 0.0063(7) 0.0029(7)
C13 0.0523(11) 0.0448(10) 0.0462(10) -0.0083(8) 0.0126(8) 0.0005(8)
C14 0.0773(15) 0.0496(12) 0.0478(12) -0.0010(11) 0.0145(10) 0.0078(9)
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_occupancy
_atom_site_type_symbol
S 0.21051(5) 0.05987(2) 0.99819(7) 0.0454(2) Uani d 1 S
C1 0.7608(2) 0.13722(9) 1.0140(3) 0.0423(4) Uani d 1 C
C2 0.8698(2) 0.16899(9) 0.9396(3) 0.0443(4) Uani d 1 C
C3 0.8334(2) 0.20272(9) 0.7683(3) 0.0430(4) Uani d 1 C
C4 0.6887(2) 0.20321(8) 0.6707(3) 0.0398(4) Uani d 1 C
C4a 0.5741(2) 0.17015(7) 0.7429(2) 0.0349(4) Uani d 1 C
C4b 0.4196(2) 0.16854(7) 0.6439(2) 0.0344(4) Uani d 1 C
C5 0.3746(2) 0.20038(9) 0.4678(3) 0.0418(4) Uani d 1 C
C6 0.2285(2) 0.19888(9) 0.3755(3) 0.0449(4) Uani d 1 C
C7 0.1213(2) 0.16554(9) 0.4576(3) 0.0448(4) Uani d 1 C
C8 0.1616(2) 0.13400(9) 0.6284(3) 0.0395(4) Uani d 1 C
C8a 0.3104(2) 0.13451(8) 0.7261(2) 0.0343(4) Uani d 1 C
C9 0.3536(2) 0.10147(8) 0.9081(2) 0.0363(4) Uani d 1 C
C10 0.4981(2) 0.10327(8) 0.9986(3) 0.0397(4) Uani d 1 C
C10a 0.6109(2) 0.13699(8) 0.9188(2) 0.0363(4) Uani d 1 C
C12 0.3004(2) 0.02962(9) 1.2286(3) 0.0397(4) Uani d 1 C
C13 0.1830(2) -0.00642(10) 1.3184(3) 0.0473(5) Uani d 1 C
C14 0.2496(3) -0.03598(11) 1.5090(3) 0.0577(5) Uani d 1 C
H1 0.780(3) 0.1141(12) 1.124(4) 0.054(6) Uiso d 1 H
H2 0.968(3) 0.1669(12) 1.006(3) 0.058(6) Uiso d 1 H
H3 0.912(3) 0.2265(12) 0.714(3) 0.058(6) Uiso d 1 H
H4 0.669(2) 0.2244(10) 0.556(3) 0.044(5) Uiso d 1 H
H5 0.445(3) 0.2245(11) 0.406(3) 0.055(6) Uiso d 1 H
H6 0.201(3) 0.2176(12) 0.259(3) 0.054(6) Uiso d 1 H
H7 0.018(3) 0.1658(13) 0.395(4) 0.068(7) Uiso d 1 H
H8 0.090(3) 0.1140(11) 0.687(3) 0.048(6) Uiso d 1 H
H10 0.527(3) 0.0801(11) 1.134(3) 0.049(6) Uiso d 1 H
H12A 0.379(3) 0.0019(12) 1.209(3) 0.055(6) Uiso d 1 H
H12B 0.337(2) 0.0655(10) 1.314(3) 0.041(5) Uiso d 1 H
H13A 0.138(3) -0.0404(12) 1.228(3) 0.053(6) Uiso d 1 H
H13B 0.100(3) 0.0234(13) 1.341(4) 0.069(7) Uiso d 1 H
H14A 0.173(4) -0.0588(14) 1.565(5) 0.081(9) Uiso d 1 H
H14B 0.293(3) -0.0053(13) 1.608(4) 0.070(7) Uiso d 1 H
H14C 0.332(4) -0.0646(13) 1.492(4) 0.070(8) Uiso d 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 104.06(9) yes
C2 C1 C10a 121.4(2) ?
C2 C1 H1 122.3(15) ?
C10a C1 H1 116.2(15) ?
C1 C2 C3 119.6(2) ?
C1 C2 H2 118.4(15) ?
C3 C2 H2 122.0(15) ?
C4 C3 C2 120.6(2) ?
C4 C3 H3 119.2(14) ?
C2 C3 H3 120.2(14) ?
C3 C4 C4a 121.0(2) ?
C3 C4 H4 118.9(14) ?
C4a C4 H4 120.1(14) ?
C4 C4a C10a 118.3(2) ?
C4 C4a C4b 123.1(2) yes
C4b C4a C10a 118.6(2) yes
C4a C4b C5 121.9(2) yes
C4a C4b C8a 119.8(2) yes
C5 C4b C8a 118.3(2) ?
C6 C5 C4b 121.6(2) ?
C6 C5 H5 116.9(14) ?
C4b C5 H5 121.6(14) ?
C5 C6 C7 119.8(2) ?
C5 C6 H6 121.5(15) ?
C7 C6 H6 118.6(15) ?
C8 C7 C6 120.0(2) ?
C8 C7 H7 120.2(15) ?
C6 C7 H7 119.7(15) ?
C7 C8 C8a 121.5(2) ?
C7 C8 H8 120.3(14) ?
C8a C8 H8 118.2(14) ?
C8 C8a C4b 118.8(2) ?
C8 C8a C9 121.7(2) ?
C4b C8a C9 119.47(15) yes
C10 C9 C8a 120.1(2) yes
C10 C9 S 123.68(14) yes
C8a C9 S 116.26(12) yes
C9 C10 C10a 121.7(2) yes
C9 C10 H10 118.8(12) ?
C10a C10 H10 119.4(12) ?
C4a C10a C1 119.1(2) ?
C4a C10a C10 120.3(2) yes
C1 C10a C10 120.7(2) ?
C13 C12 S 107.45(13) yes
C13 C12 H12A 109.9(15) ?
S C12 H12A 109.3(14) ?
C13 C12 H12B 108.8(12) ?
S C12 H12B 109.2(12) ?
H12A C12 H12B 112.1(19) ?
C14 C13 C12 111.3(2) yes
C14 C13 H13A 109.3(13) ?
C12 C13 H13A 109.5(14) ?
C14 C13 H13B 108.9(15) ?
C12 C13 H13B 109.7(15) ?
H13A C13 H13B 108.(2) ?
C13 C14 H14A 110.5(19) ?
C13 C14 H14B 114.1(16) ?
H14A C14 H14B 106.(2) ?
C13 C14 H14C 110.6(16) ?
H14A C14 H14C 110.(2) ?
H14B C14 H14C 105.(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C9 1.764(2) yes
S C12 1.806(2) yes
C1 C2 1.365(3) ?
C1 C10a 1.417(2) ?
C1 H1 0.90(3) ?
C2 C3 1.390(3) ?
C2 H2 0.94(2) ?
C3 C4 1.380(3) ?
C3 H3 0.99(2) ?
C4 C4a 1.411(2) yes
C4 H4 0.91(2) ?
C4a C4b 1.462(2) yes
C4a C10a 1.411(3) yes
C4b C5 1.407(3) yes
C4b C8a 1.418(2) yes
C5 C6 1.380(3) ?
C5 H5 0.97(2) ?
C6 C7 1.396(3) ?
C6 H6 0.91(2) ?
C7 C8 1.368(3) ?
C7 H7 0.97(3) ?
C8 H8 0.92(2) ?
C8a C8 1.413(2) ?
C8a C9 1.452(3) yes
C9 C10 1.363(3) yes
C10 H10 1.06(2) ?
C10 C10a 1.430(2) yes
C12 C13 1.524(3) yes
C12 H12A 0.95(2) ?
C12 H12B 0.99(2) ?
C13 C14 1.511(3) yes
C13 H13A 1.00(2) ?
C13 H13B 1.01(3) ?
C14 H14A 0.98(3) ?
C14 H14B 0.98(3) ?
C14 H14C 0.98(3) ?