#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/00/2210095.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_2210095
loop_
_publ_author_name
'Choi, Hong Dae'
'Woo, Hyun Mi'
'Seo,  Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-Methyl-1-(methylsulfinyl)naphtho[2,1-b]furan
;
_journal_coeditor_code           BI2050
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3881
_journal_page_last               o3882
_journal_paper_doi               10.1107/S1600536806032144
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H12 O2 S'
_chemical_formula_moiety         'C14 H12 O2 S'
_chemical_formula_sum            'C14 H12 O2 S'
_chemical_formula_weight         244.30
_chemical_name_systematic
;
2-Methyl-1-(methylsulfinyl)naphtho[2,1-b]furan
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.3890(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3158(7)
_cell_length_b                   13.7980(10)
_cell_length_c                   10.3969(8)
_cell_measurement_reflns_used    3886
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.52
_cell_volume                     1144.48(15)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0946
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9694
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0655
_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)+(0.052P)²+1.6525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1513
_reflns_number_gt                2067
_reflns_number_total             2495
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2050.cif
_cod_data_source_block           I
_cod_original_cell_volume        1144.50(15)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210095
_cod_database_fobs_code          2210095
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
S S 0.09193(9) 0.74556(5) 0.06136(7) 0.0214(2) Uani d . 1
O O1 0.1832(3) 1.00803(15) 0.2044(2) 0.0254(5) Uani d . 1
O O2 -0.0091(3) 0.72686(15) -0.0806(2) 0.0273(5) Uani d . 1
C C1 0.1424(3) 0.86940(19) 0.0850(3) 0.0185(5) Uani d . 1
C C2 0.2098(3) 0.94113(19) 0.0115(3) 0.0185(6) Uani d . 1
C C3 0.2536(3) 0.9443(2) -0.1126(3) 0.0195(6) Uani d . 1
C C4 0.2295(4) 0.8662(2) -0.2047(3) 0.0212(6) Uani d . 1
H H4 0.1786 0.8094 -0.1879 0.025 Uiso calc R 1
C C5 0.2811(4) 0.8743(2) -0.3188(3) 0.0274(7) Uani d . 1
H H5 0.2662 0.8223 -0.3780 0.033 Uiso calc R 1
C C6 0.3560(4) 0.9600(2) -0.3473(3) 0.0305(7) Uani d . 1
H H6 0.3918 0.9640 -0.4242 0.037 Uiso calc R 1
C C7 0.3762(4) 1.0372(2) -0.2621(3) 0.0280(7) Uani d . 1
H H7 0.4238 1.0941 -0.2826 0.034 Uiso calc R 1
C C8 0.3255(3) 1.0321(2) -0.1428(3) 0.0229(6) Uani d . 1
C C9 0.3460(4) 1.1135(2) -0.0547(3) 0.0276(7) Uani d . 1
H H9 0.3933 1.1700 -0.0768 0.033 Uiso calc R 1
C C10 0.2985(4) 1.1113(2) 0.0604(3) 0.0270(7) Uani d . 1
H H10 0.3095 1.1650 0.1162 0.032 Uiso calc R 1
C C11 0.2322(4) 1.0236(2) 0.0899(3) 0.0222(6) Uani d . 1
C C12 0.1292(4) 0.9143(2) 0.1981(3) 0.0232(6) Uani d . 1
C C13 0.0742(4) 0.8803(2) 0.3151(3) 0.0305(7) Uani d . 1
H H13A -0.0160 0.9203 0.3248 0.037 Uiso calc R 1
H H13B 0.1665 0.8844 0.3950 0.037 Uiso calc R 1
H H13C 0.0369 0.8143 0.3009 0.037 Uiso calc R 1
C C14 0.2984(4) 0.6988(2) 0.0786(3) 0.0279(7) Uani d . 1
H H14A 0.2929 0.6297 0.0674 0.042 Uiso calc R 1
H H14B 0.3699 0.7144 0.1661 0.042 Uiso calc R 1
H H14C 0.3429 0.7273 0.0116 0.042 Uiso calc R 1
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S C1 110.45(12)
O2 S C14 106.89(13)
C1 S C14 98.70(14)
C12 O1 C11 106.2(2)
C12 C1 C2 106.3(2)
C12 C1 S 119.2(2)
C2 C1 S 134.3(2)
C11 C2 C3 118.6(3)
C11 C2 C1 105.0(2)
C3 C2 C1 136.4(2)
C4 C3 C8 119.1(2)
C4 C3 C2 124.1(2)
C8 C3 C2 116.9(2)
C5 C4 C3 120.1(3)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 121.0(3)
C4 C5 H5 119.5
C6 C5 H5 119.5
C7 C6 C5 120.0(3)
C7 C6 H6 120.0
C5 C6 H6 120.0
C6 C7 C8 121.0(3)
C6 C7 H7 119.5
C8 C7 H7 119.5
C7 C8 C3 118.8(3)
C7 C8 C9 120.6(3)
C3 C8 C9 120.6(3)
C10 C9 C8 122.2(3)
C10 C9 H9 118.9
C8 C9 H9 118.9
C9 C10 C11 116.2(3)
C9 C10 H10 121.9
C11 C10 H10 121.9
O1 C11 C2 110.9(2)
O1 C11 C10 123.7(3)
C2 C11 C10 125.4(3)
C1 C12 O1 111.6(2)
C1 C12 C13 132.9(3)
O1 C12 C13 115.5(2)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
S C14 H14A 109.5
S C14 H14B 109.5
H14A C14 H14B 109.5
S C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S O2 1.501(2)
S C1 1.760(3)
S C14 1.796(3)
O1 C12 1.365(4)
O1 C11 1.380(3)
C1 C12 1.361(4)
C1 C2 1.456(4)
C2 C11 1.382(4)
C2 C3 1.436(4)
C3 C4 1.418(4)
C3 C8 1.425(4)
C4 C5 1.375(4)
C4 H4 0.930
C5 C6 1.407(4)
C5 H5 0.930
C6 C7 1.365(5)
C6 H6 0.930
C7 C8 1.420(4)
C7 H7 0.930
C8 C9 1.429(4)
C9 C10 1.362(4)
C9 H9 0.930
C10 C11 1.399(4)
C10 H10 0.930
C12 C13 1.491(4)
C13 H13A 0.960
C13 H13B 0.960
C13 H13C 0.960
C14 H14A 0.960
C14 H14B 0.960
C14 H14C 0.960
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 S C1 C12 137.1(2)
C14 S C1 C12 -111.2(3)
O2 S C1 C2 -47.6(3)
C14 S C1 C2 64.2(3)
C12 C1 C2 C11 0.5(3)
S C1 C2 C11 -175.3(2)
C12 C1 C2 C3 -179.5(3)
S C1 C2 C3 4.7(5)
C11 C2 C3 C4 -177.0(3)
C1 C2 C3 C4 3.0(5)
C11 C2 C3 C8 3.0(4)
C1 C2 C3 C8 -177.0(3)
C8 C3 C4 C5 2.5(4)
C2 C3 C4 C5 -177.5(3)
C3 C4 C5 C6 -1.0(4)
C4 C5 C6 C7 -1.0(5)
C5 C6 C7 C8 1.3(5)
C6 C7 C8 C3 0.3(4)
C6 C7 C8 C9 -179.5(3)
C4 C3 C8 C7 -2.2(4)
C2 C3 C8 C7 177.8(3)
C4 C3 C8 C9 177.6(3)
C2 C3 C8 C9 -2.3(4)
C7 C8 C9 C10 179.8(3)
C3 C8 C9 C10 0.0(4)
C8 C9 C10 C11 1.6(4)
C12 O1 C11 C2 0.1(3)
C12 O1 C11 C10 -178.8(3)
C3 C2 C11 O1 179.7(2)
C1 C2 C11 O1 -0.3(3)
C3 C2 C11 C10 -1.5(4)
C1 C2 C11 C10 178.5(3)
C9 C10 C11 O1 177.8(3)
C9 C10 C11 C2 -0.9(4)
C2 C1 C12 O1 -0.5(3)
S C1 C12 O1 176.08(19)
C2 C1 C12 C13 -178.0(3)
S C1 C12 C13 -1.4(5)
C11 O1 C12 C1 0.3(3)
C11 O1 C12 C13 178.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127606
