#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:08:28 +0200 (vie 13 de oct de 2017) $
#$Revision: 201955 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/91/2009199.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_2009199
loop_
_publ_author_name
'Jayanta Kumar Ray'
'Dipanjan Pan'
'S. Shanmuga Sundara Raj'
'Hoong-Kun Fun'
_publ_section_title
;
 7-Methoxy-2-methylnaphtho[1,2-b]thiophene
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1849
_journal_page_last               1850
_journal_paper_doi               10.1107/S0108270199009543
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C14 H12 O S'
_chemical_formula_weight         228.30
_chemical_name_systematic
;
7-Methoxy-2-methylnaphtho[1,2-b]thiophene
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.7980(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5611(2)
_cell_length_b                   8.13930(10)
_cell_length_c                   18.9671(4)
_cell_measurement_reflns_used    4959
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.16
_cell_volume                     1163.18(4)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL  and PLATON (Spek, 1990)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Siemens SMART CCD area detector'
_diffrn_measurement_method       'ω 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  0.034
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7772
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.041
_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)+(0.0597P)²+0.1025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.121
_reflns_number_gt                2157
_reflns_number_total             2845
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk1318.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2009199
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_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
_atom_site_type_symbol
S1 .48062(6) .90574(5) .12587(2) .06203(17) Uani d . 1 . . S
O1 1.23560(17) .78197(15) .33888(6) .0712(3) Uani d . 1 . . O
C1 .4054(2) .8284(2) .04326(9) .0625(4) Uani d . 1 . . C
C2 .5225(2) .7224(2) .01894(9) .0639(4) Uani d . 1 . . C
H2A .5034 .6692 -.0244 .077 Uiso calc R 1 . . H
C3 .6789(2) .69880(17) .06566(8) .0528(3) Uani d . 1 . . C
C4 .8298(2) .59966(19) .05755(8) .0600(4) Uani d . 1 . . C
H4A .8346 .5359 .0171 .072 Uiso calc R 1 . . H
C5 .9676(2) .59682(18) .10843(8) .0567(4) Uani d . 1 . . C
H5A 1.0654 .5308 .1020 .068 Uiso calc R 1 . . H
C6 .96606(19) .69251(16) .17126(7) .0456(3) Uani d . 1 . . C
C7 1.1095(2) .68781(17) .22392(8) .0512(3) Uani d . 1 . . C
H7A 1.2080 .6229 .2173 .061 Uiso calc R 1 . . H
C8 1.1046(2) .77824(18) .28471(8) .0545(4) Uani d . 1 . . C
C9 .9566(2) .8778(2) .29487(8) .0609(4) Uani d . 1 . . C
H9A .9543 .9394 .3361 .073 Uiso calc R 1 . . H
C10 .8161(2) .88483(18) .24465(8) .0557(4) Uani d . 1 . . C
H10A .7193 .9512 .2521 .067 Uiso calc R 1 . . H
C11 .81630(19) .79228(15) .18143(7) .0453(3) Uani d . 1 . . C
C12 .67533(19) .79287(16) .12733(7) .0474(3) Uani d . 1 . . C
C13 .2293(3) .8867(3) .00833(11) .0817(6) Uani d . 1 . . C
H13A .2098 .8384 -.0378 .123 Uiso calc R 1 . . H
H13B .2308 1.0042 .0041 .123 Uiso calc R 1 . . H
H13C .1356 .8545 .0366 .123 Uiso calc R 1 . . H
C14 1.3925(3) .6884(3) .32979(11) .0845(6) Uani d . 1 . . C
H14A 1.4774 .7059 .3696 .127 Uiso calc R 1 . . H
H14B 1.4423 .7228 .2873 .127 Uiso calc R 1 . . H
H14C 1.3628 .5738 .3264 .127 Uiso calc R 1 . . H
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
S1 .0546(3) .0633(3) .0682(3) .00889(18) .00551(18) .00240(18)
O1 .0676(8) .0720(8) .0711(7) -.0020(6) -.0112(6) -.0075(6)
C1 .0597(10) .0599(9) .0665(10) -.0103(7) -.0034(8) .0148(8)
C2 .0734(11) .0600(9) .0569(9) -.0127(8) -.0027(8) .0035(7)
C3 .0644(9) .0448(7) .0496(7) -.0062(6) .0080(7) .0024(6)
C4 .0745(11) .0563(9) .0502(8) .0027(7) .0122(7) -.0099(6)
C5 .0655(10) .0507(8) .0559(8) .0079(7) .0179(7) -.0039(6)
C6 .0529(8) .0383(6) .0471(7) -.0009(5) .0140(6) .0039(5)
C7 .0511(8) .0450(7) .0589(8) .0029(6) .0116(6) .0029(6)
C8 .0582(9) .0503(8) .0546(8) -.0055(6) .0027(7) .0031(6)
C9 .0721(11) .0585(9) .0530(8) .0016(7) .0094(7) -.0110(7)
C10 .0598(9) .0527(8) .0556(8) .0078(7) .0115(7) -.0074(6)
C11 .0520(8) .0384(6) .0470(7) -.0004(5) .0125(6) .0029(5)
C12 .0534(8) .0401(7) .0497(7) -.0012(6) .0100(6) .0039(5)
C13 .0630(11) .0865(13) .0923(14) -.0107(9) -.0124(10) .0241(11)
C14 .0648(12) .0854(13) .0988(15) .0029(10) -.0186(10) -.0013(11)
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'
O O 0.0106 0.0060 '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
C12 S1 C1 92.10(10) y
C8 O1 C14 117.00(10) y
C2 C1 C13 129.15(17) ?
C2 C1 S1 111.50(10) y
C13 C1 S1 119.37(15) ?
C1 C2 C3 114.1(2) y
C12 C3 C4 118.32(14) ?
C12 C3 C2 111.80(10) y
C4 C3 C2 129.88(14) ?
C5 C4 C3 120.61(14) ?
C4 C5 C6 121.65(14) ?
C7 C6 C11 119.57(12) ?
C7 C6 C5 121.15(13) ?
C11 C6 C5 119.28(14) ?
C8 C7 C6 120.49(14) ?
O1 C8 C7 125.15(15) ?
O1 C8 C9 114.76(14) ?
C7 C8 C9 120.10(14) ?
C10 C9 C8 120.59(14) ?
C9 C10 C11 120.79(14) ?
C10 C11 C12 123.89(13) ?
C10 C11 C6 118.47(13) ?
C12 C11 C6 117.64(12) ?
C3 C12 C11 122.50(13) ?
C3 C12 S1 110.62(11) ?
C11 C12 S1 126.87(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C12 . 1.734(2) y
S1 C1 . 1.740(2) y
O1 C8 . 1.366(2) y
O1 C14 . 1.432(2) y
C1 C2 . 1.345(3) ?
C1 C13 . 1.513(2) y
C2 C3 . 1.431(2) ?
C3 C12 . 1.400(2) ?
C3 C4 . 1.416(2) ?
C4 C5 . 1.360(2) ?
C5 C6 . 1.424(2) ?
C6 C7 . 1.412(2) ?
C6 C11 . 1.420(2) ?
C7 C8 . 1.371(2) ?
C8 C9 . 1.408(2) ?
C9 C10 . 1.367(2) ?
C10 C11 . 1.416(2) ?
C11 C12 . 1.416(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4425278
