#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006406.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_2006406
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            'C18 H18 S'
_chemical_formula_weight         266.38
_chemical_melting_point          350
_chemical_name_systematic
;
9-Butylthiophenantrene
;
_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                 97.81(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   9.010(4)
_cell_length_b                   23.124(8)
_cell_length_c                   6.888(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      8
_cell_measurement_theta_min      4
_cell_volume                     1421.8(10)
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2851
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_min         2.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         20
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.631
_refine_ls_extinction_coef       0.0016(14)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.964
_refine_ls_goodness_of_fit_obs   2.169
_refine_ls_hydrogen_treatment    'H atoms: riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.469
_refine_ls_restrained_S_obs      2.169
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_obs          0.0596
_refine_ls_shift/esd_max         -0.077
_refine_ls_shift/esd_mean        0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0016P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1664
_refine_ls_wR_factor_obs         0.1303
_reflns_number_observed          2273
_reflns_number_total             2851
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ka1230.cif
_[local]_cod_data_source_block   4
_[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_database_code               2006406
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 0.0372(4) 0.0459(4) 0.0392(4) 0.0071(3) 0.0093(3) -0.0108(3)
C1 0.0347(14) 0.0344(15) 0.0394(15) -0.0028(12) 0.0062(12) -0.0035(12)
C2 0.0343(15) 0.036(2) 0.044(2) -0.0031(12) 0.0052(13) 0.0005(12)
C3 0.0339(15) 0.0323(15) 0.049(2) 0.0018(12) 0.0153(13) -0.0016(13)
C4 0.039(2) 0.0293(14) 0.039(2) -0.0005(12) 0.0110(13) -0.0038(12)
C4a 0.0334(13) 0.0216(12) 0.0346(14) -0.0014(10) 0.0096(11) 0.0003(10)
C4b 0.0343(14) 0.0224(13) 0.0321(13) -0.0026(10) 0.0084(11) -0.0006(10)
C5 0.043(2) 0.0293(14) 0.039(2) 0.0015(12) 0.0096(13) -0.0062(12)
C6 0.048(2) 0.036(2) 0.039(2) -0.0012(13) 0.0051(14) -0.0090(13)
C7 0.0368(15) 0.039(2) 0.0377(15) -0.0018(13) 0.0003(12) -0.0019(12)
C8 0.0344(14) 0.0331(14) 0.0374(14) 0.0025(12) 0.0090(12) -0.0013(12)
C8a 0.0330(13) 0.0250(13) 0.0323(13) -0.0025(10) 0.0090(11) 0.0014(10)
C9 0.0367(14) 0.0276(13) 0.0323(13) -0.0002(11) 0.0130(12) -0.0026(11)
C10 0.040(2) 0.0311(14) 0.0341(14) 0.0002(12) 0.0100(12) -0.0045(11)
C10a 0.0345(14) 0.0266(13) 0.0337(14) -0.0032(11) 0.0087(11) -0.0006(11)
C12 0.0338(14) 0.0320(15) 0.0375(15) 0.0003(12) 0.0115(12) -0.0032(12)
C13 0.0380(15) 0.0338(15) 0.0387(15) 0.0011(12) 0.0111(12) -0.0057(12)
C14 0.045(2) 0.036(2) 0.038(2) 0.0040(13) 0.0126(13) -0.0046(13)
C15 0.055(2) 0.050(2) 0.052(2) 0.006(2) 0.017(2) -0.017(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_occupancy
_atom_site_type_symbol
S 0.23298(8) 0.07309(3) 0.06408(10) 0.0404(2) Uani d 1 S
C1 -0.3174(3) 0.14610(12) 0.0482(4) 0.0360(6) Uani d 1 C
H1 -0.338(3) 0.1238(13) -0.069(5) 0.050 Uiso d 1 H
C2 -0.4278(3) 0.17553(12) 0.1249(4) 0.0383(7) Uani d 1 C
H2 -0.527(3) 0.1736(12) 0.061(4) 0.050 Uiso d 1 H
C3 -0.3919(3) 0.20668(12) 0.2991(4) 0.0375(7) Uani d 1 C
H3 -0.469(3) 0.2285(12) 0.348(4) 0.050 Uiso d 1 H
C4 -0.2491(3) 0.20671(11) 0.3956(4) 0.0352(6) Uani d 1 C
H4 -0.237(3) 0.2283(13) 0.511(4) 0.050 Uiso d 1 H
C4a -0.1333(3) 0.17597(10) 0.3227(4) 0.0294(6) Uani d 1 C
C4b 0.0190(3) 0.17408(10) 0.4222(4) 0.0293(6) Uani d 1 C
C5 0.0635(3) 0.20312(12) 0.6019(4) 0.0368(6) Uani d 1 C
H5 -0.006(3) 0.2254(12) 0.660(4) 0.050 Uiso d 1 H
C6 0.2069(3) 0.20120(12) 0.6935(4) 0.0410(7) Uani d 1 C
H6 0.224(3) 0.2219(12) 0.809(4) 0.050 Uiso d 1 H
C7 0.3166(3) 0.17048(12) 0.6116(4) 0.0383(6) Uani d 1 C
H7 0.421(3) 0.1695(13) 0.676(4) 0.050 Uiso d 1 H
C8 0.2765(3) 0.14137(11) 0.4374(4) 0.0346(6) Uani d 1 C
H8 0.349(3) 0.1213(13) 0.388(4) 0.050 Uiso d 1 H
C8a 0.1314(3) 0.14244(10) 0.3393(4) 0.0297(6) Uani d 1 C
C9 0.0886(3) 0.11222(11) 0.1543(4) 0.0314(6) Uani d 1 C
C10 -0.0544(3) 0.11449(11) 0.0622(4) 0.0346(6) Uani d 1 C
H10 -0.083(3) 0.0929(12) -0.072(4) 0.050 Uiso d 1 H
C10a -0.1682(3) 0.14572(11) 0.1436(4) 0.0312(6) Uani d 1 C
C12 0.1466(3) 0.04416(12) -0.1671(4) 0.0339(6) Uani d 1 C
H12A 0.074(3) 0.0189(13) -0.140(4) 0.050 Uiso d 1 H
H12B 0.117(3) 0.0757(13) -0.253(4) 0.050 Uiso d 1 H
C13 0.2659(3) 0.00971(12) -0.2549(4) 0.0363(6) Uani d 1 C
H13B 0.355(3) 0.0364(13) -0.271(4) 0.050 Uiso d 1 H
H13A 0.316(3) -0.0209(13) -0.156(4) 0.050 Uiso d 1 H
C14 0.2016(3) -0.01953(13) -0.4465(4) 0.0389(7) Uani d 1 C
H14A 0.124(3) -0.0477(13) -0.419(4) 0.050 Uiso d 1 H
H14B 0.161(3) 0.0087(13) -0.544(4) 0.050 Uiso d 1 H
C15 0.3197(4) -0.0538(2) -0.5354(5) 0.0513(8) Uani d 1 C
H15C 0.372(3) -0.0797(13) -0.439(5) 0.050 Uiso d 1 H
H15B 0.386(3) -0.0293(13) -0.582(4) 0.050 Uiso d 1 H
H15A 0.281(3) -0.0772(13) -0.631(5) 0.050 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 104.51(13) yes
C2 C1 C10a 121.2(3) ?
C1 C2 C3 119.5(3) ?
C4 C3 C2 120.7(3) ?
C3 C4 C4a 121.3(3) ?
C4 C4a C4b 123.1(2) yes
C4 C4a C10a 118.1(2) ?
C4b C4a C10a 118.8(2) yes
C4a C4b C5 122.5(2) yes
C4a C4b C8a 120.2(2) yes
C5 C4b C8a 117.3(2) ?
C6 C5 C4b 121.9(3) ?
C5 C6 C7 120.6(3) ?
C8 C7 C6 118.9(3) ?
C7 C8 C8a 122.2(3) ?
C8 C8a C4b 119.1(2) ?
C8 C8a C9 122.5(2) ?
C4b C8a C9 118.4(2) yes
C10 C9 C8a 120.7(2) yes
C10 C9 S 123.6(2) yes
C8a C9 S 115.7(2) yes
C9 C10 C10a 121.5(2) yes
C1 C10a C4a 119.1(2) ?
C1 C10a C10 120.6(2) ?
C4a C10a C10 120.3(2) yes
C13 C12 S 107.5(2) yes
C14 C13 C12 111.7(2) yes
C15 C14 C13 112.1(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C9 1.766(3) yes
S C12 1.803(3) yes
C1 C2 1.369(4) ?
C1 C10a 1.413(4) ?
C2 C3 1.399(4) ?
C3 C4 1.365(4) ?
C4 C4a 1.410(3) yes
C4a C4b 1.449(4) yes
C4a C10a 1.416(4) yes
C4b C5 1.418(4) yes
C4b C8a 1.430(3) yes
C5 C6 1.359(4) ?
C6 C7 1.397(4) ?
C7 C8 1.380(4) ?
C8 C8a 1.388(4) ?
C8a C9 1.459(4) yes
C9 C10 1.357(4) yes
C10 C10a 1.430(4) yes
C12 C13 1.527(4) yes
C13 C14 1.525(4) yes
C14 C15 1.521(4) yes