#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/70/2217042.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_2217042
loop_
_publ_author_name
'Perašínová, Lucia,'
'Martin Štefko'
'Végh, Daniel'
'Kožíšek, Jozef'
_publ_section_title
;
 2-(9H-Fluoren-9-ylidenemethyl)thiophene
;
_journal_coeditor_code           FJ2086
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o274
_journal_page_last               o274
_journal_paper_doi               10.1107/S1600536807065099
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H12 S'
_chemical_formula_moiety         'C18 H12 S'
_chemical_formula_sum            'C18 H12 S'
_chemical_formula_weight         260.34
_chemical_name_systematic
;
2-(9H-Fluoren-9-ylidenemethyl)thiophene
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            16
_cell_length_a                   20.757(4)
_cell_length_b                   44.434(9)
_cell_length_c                   5.6260(11)
_cell_measurement_reflns_used    4617
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      3.67
_cell_volume                     5189.0(18)
_computing_cell_refinement       'CrysAlis CCD  (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R CCD'
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ scans
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       58
_diffrn_reflns_limit_k_min       -59
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11725
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.05
_diffrn_reflns_theta_min         3.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9376
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(Clark & Reid, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.573
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.173
_refine_ls_abs_structure_details 'Flack (1983), 1110 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.07(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0485P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                1903
_reflns_number_total             3018
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            fj2086.cif
_cod_data_source_block           I
_cod_database_code               2217042
_cod_database_fobs_code          2217042
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.35040(9) 0.03543(4) -0.1480(3) 0.0504(5) Uani d . 1 . .
C C2 0.40287(10) 0.01668(4) -0.1107(4) 0.0605(6) Uani d . 1 . .
H H2A 0.4298 0.0194 0.0241 0.073 Uiso calc R 1 . .
C C3 0.41552(10) -0.00616(5) -0.2727(4) 0.0656(6) Uani d . 1 . .
H H3A 0.4516 -0.0189 -0.2475 0.079 Uiso calc R 1 . .
C C4 0.37726(11) -0.01069(5) -0.4680(4) 0.0640(6) Uani d . 1 . .
H H4A 0.3876 -0.0262 -0.5781 0.077 Uiso calc R 1 . .
C C5 0.32362(10) 0.00724(4) -0.5052(4) 0.0594(5) Uani d . 1 . .
H H5A 0.2965 0.0040 -0.6387 0.071 Uiso calc R 1 . .
C C6 0.31044(9) 0.02985(4) -0.3442(3) 0.0490(5) Uani d . 1 . .
C C7 0.25624(9) 0.05093(4) -0.3394(3) 0.0493(5) Uani d . 1 . .
C C8 0.20399(10) 0.05396(5) -0.4884(4) 0.0607(5) Uani d . 1 . .
H H8A 0.1994 0.0413 -0.6237 0.073 Uiso calc R 1 . .
C C9 0.15827(11) 0.07574(5) -0.4373(4) 0.0670(6) Uani d . 1 . .
H H9A 0.1219 0.0780 -0.5380 0.080 Uiso calc R 1 . .
C C10 0.16522(10) 0.09415(5) -0.2405(4) 0.0658(6) Uani d . 1 . .
H H10A 0.1334 0.1090 -0.2079 0.079 Uiso calc R 1 . .
C C11 0.21746(10) 0.09134(5) -0.0913(4) 0.0608(5) Uani d . 1 . .
H H11A 0.2221 0.1043 0.0419 0.073 Uiso calc R 1 . .
C C12 0.26339(9) 0.06932(4) -0.1380(3) 0.0490(5) Uani d . 1 . .
C C13 0.32372(9) 0.06148(4) -0.0145(3) 0.0490(5) Uani d . 1 B .
C C14 0.34399(9) 0.07789(4) 0.1761(3) 0.0518(5) Uani d . 1 . .
H H14A 0.3125 0.0921 0.2256 0.062 Uiso calc R 1 A 1
C C15A 0.40114(9) 0.07913(4) 0.3214(3) 0.0513(5) Uani d P 0.900(3) B 1
C C18A 0.50774(12) 0.07874(5) 0.5125(5) 0.0731(7) Uani d P 0.900(3) B 1
H H18A 0.5513 0.0759 0.5592 0.088 Uiso calc PR 0.900(3) B 1
C C17A 0.46607(12) 0.09565(5) 0.6332(4) 0.0670(6) Uani d PD 0.900(3) B 1
H H17A 0.4767 0.1058 0.7767 0.080 Uiso calc PR 0.900(3) B 1
C C16A 0.4056(4) 0.0970(4) 0.529(3) 0.0747(14) Uani d PD 0.900(3) B 1
H H16A 0.3710 0.1087 0.5900 0.090 Uiso calc PR 0.900(3) B 1
S S1A 0.47511(8) 0.06280(3) 0.26734(16) 0.0755(3) Uani d P 0.900(3) B 1
C C15B 0.40114(9) 0.07913(4) 0.3214(3) 0.0513(5) Uani d P 0.100(3) B 2
C C17B 0.46607(12) 0.09565(5) 0.6332(4) 0.0670(6) Uani d PD 0.100(3) B 2
H H17B 0.4781 0.1058 0.7750 0.080 Uiso calc PR 0.100(3) B 2
C C18B 0.50774(12) 0.07874(5) 0.5125(5) 0.0731(7) Uani d PD 0.100(3) B 2
H H18B 0.5512 0.0758 0.5602 0.088 Uiso calc PR 0.100(3) B 2
C C16B 0.481(3) 0.0659(10) 0.311(4) 0.0755(3) Uani d PD 0.100(3) B 2
H H16B 0.5013 0.0532 0.1960 0.091 Uiso calc PR 0.100(3) B 2
S S1B 0.3980(11) 0.0978(10) 0.532(7) 0.0747(14) Uani d PD 0.100(3) B 2
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
C2 C1 C6 118.53(18)
C2 C1 C13 133.10(18)
C6 C1 C13 108.35(17)
C1 C2 C3 119.2(2)
C1 C2 H2A 120.4
C3 C2 H2A 120.4
C4 C3 C2 121.6(2)
C4 C3 H3A 119.2
C2 C3 H3A 119.2
C3 C4 C5 120.2(2)
C3 C4 H4A 119.9
C5 C4 H4A 119.9
C6 C5 C4 118.6(2)
C6 C5 H5A 120.7
C4 C5 H5A 120.7
C5 C6 C1 121.84(18)
C5 C6 C7 129.06(17)
C1 C6 C7 109.09(16)
C8 C7 C12 121.16(18)
C8 C7 C6 131.03(19)
C12 C7 C6 107.78(17)
C7 C8 C9 118.8(2)
C7 C8 H8A 120.6
C9 C8 H8A 120.6
C10 C9 C8 120.5(2)
C10 C9 H9A 119.8
C8 C9 H9A 119.8
C11 C10 C9 121.1(2)
C11 C10 H10A 119.5
C9 C10 H10A 119.5
C10 C11 C12 119.2(2)
C10 C11 H11A 120.4
C12 C11 H11A 120.4
C11 C12 C7 119.26(19)
C11 C12 C13 131.25(18)
C7 C12 C13 109.45(17)
C14 C13 C12 120.45(17)
C14 C13 C1 134.33(19)
C12 C13 C1 105.19(16)
C13 C14 C15A 136.09(18)
C13 C14 H14A 112.0
C15A C14 H14A 112.0
C16A C15A C14 122.8(4)
C16A C15A S1A 108.9(4)
C14 C15A S1A 128.03(14)
C17A C18A S1A 113.1(2)
C17A C18A H18A 123.5
S1A C18A H18A 123.5
C18A C17A C16A 113.4(9)
C18A C17A H17A 123.3
C16A C17A H17A 123.3
C17A C16A C15A 112.5(12)
C17A C16A H16A 123.8
C15A C16A H16A 123.8
C18A S1A C15A 92.08(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.387(3)
C1 C6 1.403(3)
C1 C13 1.487(3)
C2 C3 1.389(3)
C2 H2A 0.9500
C3 C4 1.371(3)
C3 H3A 0.9500
C4 C5 1.385(3)
C4 H4A 0.9500
C5 C6 1.380(3)
C5 H5A 0.9500
C6 C7 1.464(3)
C7 C8 1.377(3)
C7 C12 1.405(3)
C8 C9 1.386(3)
C8 H8A 0.9500
C9 C10 1.384(3)
C9 H9A 0.9500
C10 C11 1.377(3)
C10 H10A 0.9500
C11 C12 1.391(3)
C11 H11A 0.9500
C12 C13 1.474(3)
C13 C14 1.363(3)
C14 C15A 1.442(3)
C14 H14A 0.9500
C15A C16A 1.416(19)
C15A S1A 1.725(3)
C18A C17A 1.332(3)
C18A S1A 1.692(3)
C18A H18A 0.9500
C17A C16A 1.388(3)
C17A H17A 0.9500
C16A H16A 0.9500
C16B H16B 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2A S1A 1_555 0.95 2.55 3.311(4) 138.51
