#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006571.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_2006571
loop_
_publ_author_name
'Malhotra, S.'
'Parmar, V. S.'
'Errington, W.'
_publ_section_title
;
 3-Cyano-6-(2-methoxyphenyl)-4-methylthio-2<i>H</i>-pyran-2-one
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1442
_journal_page_last               1444
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C14 H11 N O3 S'
_chemical_formula_weight         273.30
_chemical_name_systematic
;
 3-cyano-6-(2'-methoxyphenyl)-4-methylthio-2-pyranone
;
_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                90.00
_cell_angle_beta                 99.608(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1163(9)
_cell_length_b                   16.050(2)
_cell_length_c                   8.7050(8)
_cell_measurement_reflns_used    3385
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      23.38
_cell_measurement_theta_min      2.27
_cell_volume                     1255.8(2)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994b)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996b)'
_computing_structure_solution    'SHELXTL/PC (Siemens, 1994a)'
_diffrn_ambient_temperature      230(2)
_diffrn_measurement_device       'Siemens SMART diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5252
_diffrn_reflns_theta_max         23.38
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996a)'
_exptl_crystal_colour            'intense orange'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.992
_refine_ls_goodness_of_fit_obs   1.049
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_restrained_S_obs      1.049
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_obs          0.0438
_refine_ls_shift/esd_max         0.006
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0808P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1232
_refine_ls_wR_factor_obs         0.1124
_reflns_number_observed          1373
_reflns_number_total             1789
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    cf1174.cif
_[local]_cod_data_source_block   sml2
_[local]_cod_cif_authors_sg_H-M  'P 21 /c'
_cod_original_cell_volume        1255.84(17)
_cod_database_code               2006571
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
S1 0.0422(5) 0.0294(5) 0.0432(5) -0.0005(3) -0.0104(3) -0.0023(3)
O1 0.0396(10) 0.0212(10) 0.0383(11) -0.0008(7) -0.0035(8) -0.0005(8)
O2 0.0496(11) 0.0184(10) 0.0505(12) -0.0012(8) -0.0017(9) -0.0002(8)
O3 0.0501(11) 0.0231(10) 0.0466(12) -0.0018(8) -0.0114(9) 0.0054(8)
N1 0.0562(16) 0.0406(15) 0.0549(17) 0.0113(12) -0.0087(14) 0.0061(12)
C1 0.0361(15) 0.0266(16) 0.0348(16) 0.0025(11) 0.0033(12) 0.0046(11)
C2 0.0346(14) 0.0240(14) 0.0333(15) 0.0023(11) 0.0021(12) -0.0002(11)
C3 0.0332(14) 0.0248(14) 0.0320(15) 0.0008(10) 0.0021(11) -0.0014(11)
C4 0.0383(15) 0.0210(13) 0.0352(15) -0.0018(11) 0.0004(12) -0.0002(11)
C5 0.0369(15) 0.0203(13) 0.0331(15) -0.0005(11) 0.0060(12) 0.0015(11)
C6 0.0412(16) 0.0245(14) 0.0396(17) 0.0016(12) 0.0031(14) -0.0027(12)
C7 0.0511(17) 0.0305(16) 0.0495(18) -0.0045(12) -0.0097(13) -0.0035(13)
C8 0.0321(13) 0.0291(15) 0.0325(14) -0.0001(11) 0.0002(11) 0.0002(11)
C9 0.0390(16) 0.0305(15) 0.0411(17) -0.0041(12) -0.0012(13) -0.0001(12)
C10 0.0369(16) 0.0457(18) 0.0465(18) -0.0090(13) -0.0110(13) -0.0013(14)
C11 0.0381(16) 0.052(2) 0.0469(18) 0.0030(14) -0.0110(14) 0.0073(15)
C12 0.0407(16) 0.0349(16) 0.0453(17) 0.0038(12) -0.0043(13) 0.0063(13)
C13 0.0353(14) 0.0269(15) 0.0358(15) 0.0002(11) 0.0020(12) -0.0006(11)
C14 0.0580(18) 0.0239(15) 0.0570(19) -0.0005(12) 0.0021(15) 0.0016(13)
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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S1 0.00397(7) 0.66902(4) 0.18346(8) 0.0403(3) Uani d . 1 S
O1 0.34425(17) 0.80508(10) 0.52624(19) 0.0342(5) Uani d . 1 O
O2 0.24850(19) 0.92701(10) 0.4436(2) 0.0407(5) Uani d . 1 O
O3 0.36997(19) 0.54791(10) 0.6083(2) 0.0422(5) Uani d . 1 O
N1 -0.0476(3) 0.88445(15) 0.1090(3) 0.0526(7) Uani d . 1 N
C1 0.2427(3) 0.85229(15) 0.4255(3) 0.0328(6) Uani d . 1 C
C2 0.1399(3) 0.80589(15) 0.3129(3) 0.0310(6) Uani d . 1 C
C3 0.1391(3) 0.72022(15) 0.3133(3) 0.0304(6) Uani d . 1 C
C4 0.2474(3) 0.67689(15) 0.4210(3) 0.0321(6) Uani d . 1 C
H4 0.2497 0.6183 0.4203 0.039 Uiso calc R 1 H
C5 0.3464(3) 0.71947(14) 0.5239(3) 0.0301(6) Uani d . 1 C
C6 0.0367(3) 0.85184(16) 0.2028(3) 0.0355(7) Uani d . 1 C
C7 0.0362(3) 0.56066(16) 0.2284(3) 0.0458(7) Uani d . 1 C
H7A 0.1333 0.5448 0.2065 0.069 Uiso calc R 1 H
H7B -0.0399 0.5274 0.1652 0.069 Uiso calc R 1 H
H7C 0.0327 0.5513 0.3378 0.069 Uiso calc R 1 H
C8 0.4632(3) 0.68557(15) 0.6453(3) 0.0318(6) Uani d . 1 C
C9 0.5694(3) 0.74053(16) 0.7268(3) 0.0378(7) Uani d . 1 C
H9 0.5657 0.7973 0.6998 0.045 Uiso calc R 1 H
C10 0.6781(3) 0.71325(17) 0.8446(3) 0.0451(7) Uani d . 1 C
H10 0.7479 0.7509 0.8974 0.054 Uiso calc R 1 H
C11 0.6835(3) 0.63002(18) 0.8847(3) 0.0478(8) Uani d . 1 C
H11 0.7574 0.6112 0.9657 0.057 Uiso calc R 1 H
C12 0.5824(3) 0.57383(17) 0.8079(3) 0.0416(7) Uani d . 1 C
H12 0.5875 0.5173 0.8366 0.050 Uiso calc R 1 H
C13 0.4731(3) 0.60119(15) 0.6882(3) 0.0331(6) Uani d . 1 C
C14 0.3694(3) 0.46250(16) 0.6567(3) 0.0471(7) Uani d . 1 C
H14A 0.4614 0.4360 0.6411 0.071 Uiso calc R 1 H
H14B 0.2858 0.4338 0.5955 0.071 Uiso calc R 1 H
H14C 0.3606 0.4600 0.7661 0.071 Uiso calc R 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'
N N 0.0061 0.0033 '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
C3 S1 C7 104.14(12) y
C5 O1 C1 123.07(18) y
C13 O3 C14 118.9(2) y
O2 C1 O1 116.7(2) ?
O2 C1 C2 127.5(2) y
O1 C1 C2 115.8(2) ?
C3 C2 C6 120.9(2) ?
C3 C2 C1 121.1(2) ?
C6 C2 C1 117.9(2) ?
C2 C3 C4 119.1(2) ?
C2 C3 S1 118.40(17) ?
C4 C3 S1 122.47(18) ?
C5 C4 C3 120.3(2) ?
C4 C5 O1 120.5(2) ?
C4 C5 C8 127.9(2) y
O1 C5 C8 111.64(19) y
N1 C6 C2 175.8(3) y
C13 C8 C9 117.5(2) ?
C13 C8 C5 123.6(2) y
C9 C8 C5 118.9(2) y
C10 C9 C8 121.7(2) ?
C9 C10 C11 119.3(2) ?
C12 C11 C10 121.2(3) ?
C11 C12 C13 119.7(3) ?
O3 C13 C12 121.9(2) ?
O3 C13 C8 117.3(2) ?
C12 C13 C8 120.8(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C3 1.734(3) y
S1 C7 1.796(3) y
O1 C5 1.374(3) y
O1 C1 1.389(3) y
O2 C1 1.210(3) y
O3 C13 1.372(3) y
O3 C14 1.434(3) y
N1 C6 1.150(3) y
C1 C2 1.445(4) ?
C2 C3 1.375(3) ?
C2 C6 1.431(4) y
C3 C4 1.424(3) ?
C4 C5 1.347(3) ?
C5 C8 1.474(3) y
C8 C13 1.404(4) ?
C8 C9 1.411(4) ?
C9 C10 1.373(4) ?
C10 C11 1.379(4) ?
C11 C12 1.380(4) ?
C12 C13 1.387(4) ?
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
_geom_torsion_publ_flag
C5 O1 C1 O2 177.1(2) ?
C5 O1 C1 C2 -1.6(3) ?
O2 C1 C2 C3 -175.0(2) ?
O1 C1 C2 C3 3.5(3) ?
O2 C1 C2 C6 3.7(4) ?
O1 C1 C2 C6 -177.8(2) ?
C6 C2 C3 C4 177.7(2) ?
C1 C2 C3 C4 -3.7(3) ?
C6 C2 C3 S1 -3.1(3) ?
C1 C2 C3 S1 175.55(18) ?
C7 S1 C3 C2 -177.22(19) y
C7 S1 C3 C4 2.0(2) ?
C2 C3 C4 C5 1.9(4) ?
S1 C3 C4 C5 -177.32(18) y
C3 C4 C5 O1 0.0(4) ?
C3 C4 C5 C8 178.5(2) ?
C1 O1 C5 C4 0.0(3) ?
C1 O1 C5 C8 -178.74(19) ?
C3 C2 C6 N1 -19.(4) ?
C1 C2 C6 N1 163.(4) ?
C4 C5 C8 C13 -10.7(4) y
O1 C5 C8 C13 167.9(2) ?
C4 C5 C8 C9 171.1(2) ?
O1 C5 C8 C9 -10.4(3) ?
C13 C8 C9 C10 -0.5(4) ?
C5 C8 C9 C10 177.9(2) ?
C8 C9 C10 C11 -0.1(4) ?
C9 C10 C11 C12 0.4(4) ?
C10 C11 C12 C13 0.1(4) ?
C14 O3 C13 C12 4.0(4) y
C14 O3 C13 C8 -175.3(2) ?
C11 C12 C13 O3 -179.9(2) ?
C11 C12 C13 C8 -0.7(4) ?
C9 C8 C13 O3 -179.8(2) ?
C5 C8 C13 O3 1.9(3) ?
C9 C8 C13 C12 0.9(4) ?
C5 C8 C13 C12 -177.4(2) ?