#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/14/7151421.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151421
loop_
_publ_author_name
'Ito, Shunji'
'Kubo, Takahiro'
'Kondo, Mao'
'Kabuto, Chizuko'
'Morita, Noboru'
'Asao, Toyonobu'
'Fujimori, Kunihide'
'Watanabe, Masataka'
'Harada, Nobuyuki'
'Yasunami, Masafumi'
_publ_section_title
;
 Synthesis, stability and bonding situation of tris-, bis- and
 mono[9-(azuleno[1,2-b]thienyl)]methyl cationsElectronic supplementary
 information (ESI) available: CV waves of compounds 7a, 8a and 9a,
 redox details of compounds 7a,b, 8a,b, and 9a,b along with those of
 4a, 5a and 6a, ORTEP drawings and details of the X-ray analyses of
 compounds 2b and 9b and NMR details of the compounds reported. See
 http://www.rsc.org/suppdata/ob/b3/b302688d/
;
_journal_issue                   14
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              2572
_journal_paper_doi               10.1039/b302688d
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C15 H14 S '
_chemical_formula_sum            'C15 H14 S'
_chemical_formula_weight         226.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90
_cell_angle_beta                 106.348(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.228(4)
_cell_length_b                   6.064(2)
_cell_length_c                   22.113(9)
_cell_measurement_reflns_used    4319
_cell_measurement_temperature    173.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1187.4(8)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10892
_diffrn_reflns_theta_full        26.00
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0356
_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)+(0.0434P)²+0.2406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0928
_cod_data_source_file            b302688d.txt
_cod_data_source_block           morita-konndo0203
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C15 H14 S '
_cod_database_code               7151421
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.97792(5) -0.08033(7) 0.408636(18) 0.03675(16) Uani 1 1 d . . .
C1 C 0.90318(16) 0.0503(2) 0.33726(7) 0.0263(3) Uani 1 1 d . . .
C2 C 0.78739(15) 0.0123(2) 0.28078(6) 0.0242(3) Uani 1 1 d . . .
C3 C 0.69098(16) -0.1642(2) 0.26602(7) 0.0265(3) Uani 1 1 d . . .
C4 C 0.57507(16) -0.2080(2) 0.21044(7) 0.0279(3) Uani 1 1 d . . .
C5 C 0.52754(16) -0.0885(2) 0.15521(7) 0.0281(3) Uani 1 1 d . . .
C6 C 0.58692(18) 0.1166(3) 0.14230(7) 0.0307(3) Uani 1 1 d . . .
C7 C 0.70092(17) 0.2452(2) 0.17918(7) 0.0297(3) Uani 1 1 d . . .
C8 C 0.79308(16) 0.2103(2) 0.24076(7) 0.0260(3) Uani 1 1 d . . .
C9 C 0.90611(17) 0.3493(2) 0.27426(7) 0.0294(3) Uani 1 1 d . . .
C10 C 0.97495(16) 0.2518(2) 0.33415(7) 0.0284(3) Uani 1 1 d . . .
C11 C 1.09219(18) 0.2973(3) 0.39057(8) 0.0366(4) Uani 1 1 d . . .
C12 C 1.10508(19) 0.1357(3) 0.43354(8) 0.0411(4) Uani 1 1 d . . .
C13 C 0.40344(18) -0.1938(3) 0.10224(7) 0.0344(4) Uani 1 1 d . . .
C14 C 0.4704(2) -0.2866(4) 0.05181(9) 0.0474(5) Uani 1 1 d . . .
C15 C 0.2721(2) -0.0416(4) 0.07335(10) 0.0489(5) Uani 1 1 d . . .
H1 H 0.7040(18) -0.276(3) 0.2990(8) 0.033(4) Uiso 1 1 d . . .
H2 H 0.5200(18) -0.341(3) 0.2114(7) 0.029(4) Uiso 1 1 d . . .
H3 H 0.5436(19) 0.169(3) 0.1018(8) 0.036(4) Uiso 1 1 d . . .
H4 H 0.7243(18) 0.385(3) 0.1612(8) 0.030(4) Uiso 1 1 d . . .
H5 H 0.9280(19) 0.484(3) 0.2606(8) 0.038(5) Uiso 1 1 d . . .
H6 H 1.158(2) 0.430(3) 0.3968(9) 0.051(5) Uiso 1 1 d . . .
H7 H 1.170(2) 0.128(3) 0.4756(10) 0.054(6) Uiso 1 1 d . . .
H8 H 0.553(3) -0.397(4) 0.0696(10) 0.062(6) Uiso 1 1 d . . .
H9 H 0.393(2) -0.364(4) 0.0195(10) 0.057(6) Uiso 1 1 d . . .
H10 H 0.516(3) -0.157(4) 0.0303(10) 0.065(6) Uiso 1 1 d . . .
H11 H 0.302(2) 0.083(3) 0.0535(9) 0.039(5) Uiso 1 1 d . . .
H12 H 0.230(3) 0.017(4) 0.1055(12) 0.079(7) Uiso 1 1 d . . .
H13 H 0.196(3) -0.120(4) 0.0427(10) 0.059(6) Uiso 1 1 d . . .
H14 H 0.3628(19) -0.318(3) 0.1209(8) 0.039(5) Uiso 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C12 90.25(8) . . ?
C10 C1 C2 110.38(13) . . ?
C10 C1 S1 111.86(11) . . ?
C2 C1 S1 137.75(11) . . ?
C3 C2 C1 127.94(13) . . ?
C3 C2 C8 127.74(13) . . ?
C1 C2 C8 104.32(12) . . ?
C2 C3 C4 129.55(14) . . ?
C2 C3 H1 115.4(10) . . ?
C4 C3 H1 115.1(10) . . ?
C5 C4 C3 130.32(14) . . ?
C5 C4 H2 115.1(10) . . ?
C3 C4 H2 114.6(10) . . ?
C4 C5 C6 126.35(14) . . ?
C4 C5 C13 116.20(14) . . ?
C6 C5 C13 117.40(14) . . ?
C7 C6 C5 130.57(14) . . ?
C7 C6 H3 115.2(11) . . ?
C5 C6 H3 114.2(11) . . ?
C6 C7 C8 129.98(14) . . ?
C6 C7 H4 117.7(10) . . ?
C8 C7 H4 112.3(10) . . ?
C9 C8 C7 125.99(14) . . ?
C9 C8 C2 108.53(13) . . ?
C7 C8 C2 125.47(13) . . ?
C8 C9 C10 108.44(13) . . ?
C8 C9 H5 124.8(11) . . ?
C10 C9 H5 126.6(11) . . ?
C1 C10 C9 108.32(13) . . ?
C1 C10 C11 112.19(14) . . ?
C9 C10 C11 139.48(14) . . ?
C12 C11 C10 111.71(15) . . ?
C12 C11 H6 124.1(11) . . ?
C10 C11 H6 124.1(11) . . ?
C11 C12 S1 113.98(13) . . ?
C11 C12 H7 128.7(13) . . ?
S1 C12 H7 117.2(13) . . ?
C15 C13 C14 110.91(16) . . ?
C15 C13 C5 114.00(15) . . ?
C14 C13 C5 110.12(14) . . ?
C15 C13 H14 106.8(10) . . ?
C14 C13 H14 107.8(10) . . ?
C5 C13 H14 106.9(10) . . ?
C13 C14 H8 112.1(13) . . ?
C13 C14 H9 110.4(12) . . ?
H8 C14 H9 106.5(17) . . ?
C13 C14 H10 110.3(12) . . ?
H8 C14 H10 108.4(17) . . ?
H9 C14 H10 108.9(17) . . ?
C13 C15 H11 112.0(11) . . ?
C13 C15 H12 110.6(15) . . ?
H11 C15 H12 106.0(19) . . ?
C13 C15 H13 109.7(13) . . ?
H11 C15 H13 108.7(17) . . ?
H12 C15 H13 110(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7266(15) . ?
S1 C12 1.7412(18) . ?
C1 C10 1.401(2) . ?
C1 C2 1.4153(19) . ?
C2 C3 1.372(2) . ?
C2 C8 1.5013(19) . ?
C3 C4 1.409(2) . ?
C3 H1 0.978(17) . ?
C4 C5 1.381(2) . ?
C4 H2 0.956(17) . ?
C5 C6 1.420(2) . ?
C5 C13 1.528(2) . ?
C6 C7 1.377(2) . ?
C6 H3 0.929(18) . ?
C7 C8 1.404(2) . ?
C7 H4 0.983(17) . ?
C8 C9 1.383(2) . ?
C9 C10 1.426(2) . ?
C9 H5 0.913(19) . ?
C10 C11 1.430(2) . ?
C11 C12 1.347(3) . ?
C11 H6 1.00(2) . ?
C12 H7 0.96(2) . ?
C13 C15 1.515(2) . ?
C13 C14 1.526(2) . ?
C13 H14 0.981(19) . ?
C14 H8 1.01(2) . ?
C14 H9 0.97(2) . ?
C14 H10 1.06(2) . ?
C15 H11 0.955(19) . ?
C15 H12 0.97(3) . ?
C15 H13 0.96(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9086524
