#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2007428.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_2007428
loop_
_publ_author_name
'George, M.'
'Das, S.'
'Ashokan, C. V.'
'Rath, N. P.'
'George, M. V.'
_publ_section_title
;
 2-Phenyl-3-(5,6,7,7a-tetrahydro-1<i>H</i>,3<i>H</i>-pyrrolo[1,2-<i>c</i>]oxazol-3-ylidene)-1-propene-1,1-dicarbonitrile
 and 4-(4-Methoxyphenyl)-2,6-bis(methylthio)pyridine-3-carbonitrile
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1033
_journal_page_last               1036
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          'C17 H15 N3 O, 0.5C6 H6'
_chemical_formula_sum            'C20 H18 N3 O'
_chemical_formula_weight         316.37
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.87690(10)
_cell_length_b                   9.87690(10)
_cell_length_c                   35.3642(2)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     3449.89(5)
_computing_cell_refinement       'SAINT (Siemens, 1996a)'
_computing_data_collection       'SMART (Siemens, 1996b)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  SHELXTL-Plus
_computing_structure_solution    SHELXTL-Plus
_diffrn_ambient_temperature      223(2)
_diffrn_measurement_device       'Siemens CCD'
_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  0.10
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            73530
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 'area detector, see expt'
_diffrn_standards_number         'see expt'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.127
_refine_ls_abs_structure_details 'Flack (1983) parameter = -0.4(20)'
_refine_ls_extinction_coef       0.0036(6)
_refine_ls_extinction_method     SHELXTL-Plus_(Shedrick,_1995)
_refine_ls_goodness_of_fit_all   1.043
_refine_ls_goodness_of_fit_obs   1.110
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_restrained_S_obs      1.110
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_obs          0.0504
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.4285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1175
_refine_ls_wR_factor_obs         0.1030
_reflns_number_observed          2701
_reflns_number_total             3773
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fr1077.cif
_[local]_cod_data_source_block   3a
_cod_database_code               2007428
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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
O2' 0.0601(10) 0.0522(9) 0.0439(8) 0.0070(7) -0.0010(6) -0.0069(6)
N1 0.0712(14) 0.090(2) 0.0489(12) 0.0132(12) 0.0031(10) -0.0092(11)
N2 0.0717(14) 0.0535(13) 0.097(2) 0.0119(11) 0.0022(12) -0.0117(12)
N3'A 0.0490(10) 0.0440(9) 0.0544(10) 0.0039(8) 0.0032(8) -0.0050(8)
C1' 0.0654(14) 0.0659(14) 0.0488(12) 0.0067(12) -0.0014(10) -0.0201(11)
C1 0.0424(10) 0.0487(12) 0.0456(11) 0.0035(10) -0.0001(9) -0.0065(9)
C2 0.0326(10) 0.0463(11) 0.0435(10) -0.0021(8) 0.0030(8) -0.0030(9)
C3' 0.0411(11) 0.0482(12) 0.0425(11) -0.0013(9) 0.0010(8) -0.0010(9)
C3 0.0448(11) 0.0472(12) 0.0402(10) 0.0018(8) 0.0013(9) -0.0032(9)
C4' 0.0623(13) 0.0584(14) 0.0623(14) 0.0117(11) 0.0006(11) 0.0105(11)
C4 0.0459(11) 0.0623(14) 0.0491(13) 0.0078(10) 0.0017(10) -0.0138(11)
C5' 0.0523(13) 0.0554(14) 0.092(2) 0.0102(11) 0.0114(13) 0.0071(13)
C5 0.0462(12) 0.0547(15) 0.0592(13) 0.0024(10) 0.0026(10) -0.0128(11)
C6'A 0.0464(11) 0.0515(12) 0.0648(14) -0.0030(10) 0.0000(10) -0.0161(11)
C6' 0.0499(13) 0.0488(13) 0.087(2) 0.0029(10) 0.0099(12) -0.0111(12)
C6 0.0400(10) 0.0423(11) 0.0444(10) 0.0033(9) 0.0017(8) -0.0044(9)
C7 0.0401(12) 0.100(2) 0.0622(14) -0.0018(12) -0.0003(10) 0.0190(14)
C8 0.0511(14) 0.144(3) 0.0638(15) 0.013(2) -0.0045(12) 0.030(2)
C9 0.073(2) 0.087(2) 0.0567(14) 0.0124(14) 0.0035(13) 0.0223(13)
C10 0.0639(15) 0.0712(15) 0.0526(13) -0.0124(13) 0.0092(11) 0.0038(11)
C11 0.0425(12) 0.0690(14) 0.0505(12) -0.0084(10) 0.0003(10) -0.0005(10)
C1S 0.101(2) 0.101(2) 0.100(3) -0.015(3) 0.009(2) -0.009(2)
C2S 0.139(3) 0.074(2) 0.084(2) 0.023(2) 0.026(2) 0.004(2)
C3S 0.082(2) 0.134(3) 0.063(2) 0.031(2) 0.0117(15) 0.019(2)
C4S 0.097(2) 0.097(2) 0.064(2) -0.012(3) -0.008(2) 0.008(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O2' 0.70980(15) 0.47391(14) 0.07500(4) 0.0521(4) Uani d . 1 O
N1 0.6390(2) 0.6815(2) 0.23384(6) 0.0701(6) Uani d . 1 N
N2 0.5432(2) 1.0106(2) 0.15521(7) 0.0739(6) Uani d . 1 N
N3'A 0.7479(2) 0.3203(2) 0.11890(5) 0.0491(4) Uani d . 1 N
C1' 0.7676(2) 0.3567(2) 0.05503(6) 0.0601(6) Uani d . 1 C
H1'A 0.8595(2) 0.3768(2) 0.04617(6) 0.072 Uiso calc R 1 H
H1'B 0.7115(2) 0.3320(2) 0.03324(6) 0.072 Uiso calc R 1 H
C1 0.6237(2) 0.7653(2) 0.16503(5) 0.0456(5) Uani d . 1 C
C2 0.6550(2) 0.6798(2) 0.13463(5) 0.0408(4) Uani d . 1 C
C3' 0.7193(2) 0.4497(2) 0.11213(5) 0.0439(5) Uani d . 1 C
C3 0.6940(2) 0.5457(2) 0.14001(5) 0.0441(5) Uani d . 1 C
H3A 0.7044(2) 0.5170(2) 0.16518(5) 0.053 Uiso calc R 1 H
C4' 0.8160(2) 0.2602(2) 0.15152(6) 0.0610(6) Uani d . 1 C
H4'A 0.7513(2) 0.2378(2) 0.17158(6) 0.073 Uiso calc R 1 H
H4'B 0.8854(2) 0.3210(2) 0.16171(6) 0.073 Uiso calc R 1 H
C4 0.6317(2) 0.7197(2) 0.20332(6) 0.0525(5) Uani d . 1 C
C5' 0.8793(2) 0.1326(2) 0.13461(7) 0.0667(6) Uani d . 1 C
H5'A 0.9665(2) 0.1126(2) 0.14663(7) 0.080 Uiso calc R 1 H
H5'B 0.8192(2) 0.0545(2) 0.13781(7) 0.080 Uiso calc R 1 H
C5 0.5796(2) 0.9009(2) 0.15940(6) 0.0533(6) Uani d . 1 C
C6'A 0.7696(2) 0.2438(2) 0.08382(6) 0.0542(5) Uani d . 1 C
H6'A 0.6935(2) 0.1805(2) 0.07935(6) 0.065 Uiso calc R 1 H
C6' 0.8983(2) 0.1658(2) 0.09276(7) 0.0617(6) Uani d . 1 C
H6'B 0.9790(2) 0.2217(2) 0.08866(7) 0.074 Uiso calc R 1 H
H6'C 0.9053(2) 0.0834(2) 0.07748(7) 0.074 Uiso calc R 1 H
C6 0.6419(2) 0.7416(2) 0.09625(5) 0.0422(4) Uani d . 1 C
C7 0.5179(2) 0.7467(3) 0.07829(6) 0.0673(7) Uani d . 1 C
H7A 0.4418(2) 0.7076(3) 0.08993(6) 0.081 Uiso calc R 1 H
C8 0.5041(3) 0.8085(3) 0.04344(7) 0.0863(10) Uani d . 1 C
H8A 0.4194(3) 0.8103(3) 0.03132(7) 0.104 Uiso calc R 1 H
C9 0.6146(3) 0.8673(3) 0.02660(7) 0.0723(7) Uani d . 1 C
H9A 0.6052(3) 0.9104(3) 0.00304(7) 0.087 Uiso calc R 1 H
C10 0.7379(2) 0.8635(2) 0.04387(6) 0.0626(6) Uani d . 1 C
H10A 0.8135(2) 0.9034(2) 0.03219(6) 0.075 Uiso calc R 1 H
C11 0.7516(2) 0.8007(2) 0.07856(6) 0.0540(5) Uani d . 1 C
H11A 0.8369(2) 0.7982(2) 0.09031(6) 0.065 Uiso calc R 1 H
C1S 0.3822(4) 0.3822(4) 0.0000 0.1008(14) Uani d S 1 C
H1SA 0.4495(4) 0.4495(4) 0.0000 0.121 Uiso calc SR 1 H
C2S 0.2486(4) 0.4173(3) 0.00247(9) 0.0991(10) Uani d . 1 C
H2SA 0.2235(4) 0.5089(3) 0.00435(9) 0.119 Uiso calc R 1 H
C3S 0.1516(3) 0.3180(4) 0.00219(8) 0.0930(10) Uani d . 1 C
H3SA 0.0598(3) 0.3424(4) 0.00355(8) 0.112 Uiso calc R 1 H
C4S 0.1859(3) 0.1859(3) 0.0000 0.0860(12) Uani d S 1 C
H4SA 0.1186(3) 0.1186(3) 0.0000 0.103 Uiso calc SR 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
C3' O2' C1' . 107.6(2)
C3' N3'A C4' . 129.1(2)
C3' N3'A C6'A . 111.9(2)
C4' N3'A C6'A . 113.0(2)
O2' C1' C6'A . 105.2(2)
C2 C1 C5 . 121.8(2)
C2 C1 C4 . 121.6(2)
C5 C1 C4 . 116.5(2)
C3 C2 C1 . 122.0(2)
C3 C2 C6 . 122.5(2)
C1 C2 C6 . 115.6(2)
N3'A C3' O2' . 111.3(2)
N3'A C3' C3 . 124.4(2)
O2' C3' C3 . 124.1(2)
C3' C3 C2 . 127.0(2)
N3'A C4' C5' . 102.4(2)
N1 C4 C1 . 179.0(2)
C6' C5' C4' . 104.6(2)
N2 C5 C1 . 179.3(2)
N3'A C6'A C1' . 100.8(2)
N3'A C6'A C6' . 101.9(2)
C1' C6'A C6' . 121.6(2)
C6'A C6' C5' . 102.0(2)
C7 C6 C11 . 118.2(2)
C7 C6 C2 . 120.6(2)
C11 C6 C2 . 121.1(2)
C6 C7 C8 . 120.9(2)
C9 C8 C7 . 119.7(2)
C10 C9 C8 . 120.3(2)
C9 C10 C11 . 119.9(2)
C6 C11 C10 . 121.0(2)
C2S C1S C2S 7 119.6(5)
C1S C2S C3S . 119.5(3)
C4S C3S C2S . 121.1(3)
C3S C4S C3S 7 119.2(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O2' C3' . 1.338(2)
O2' C1' . 1.471(2)
N1 C4 . 1.146(3)
N2 C5 . 1.151(3)
N3'A C3' . 1.330(2)
N3'A C4' . 1.462(3)
N3'A C6'A . 1.469(2)
C1' C6'A . 1.510(3)
C1 C2 . 1.401(3)
C1 C5 . 1.422(3)
C1 C4 . 1.429(3)
C2 C3 . 1.393(3)
C2 C6 . 1.494(3)
C3' C3 . 1.390(3)
C4' C5' . 1.529(3)
C5' C6' . 1.527(3)
C6'A C6' . 1.520(3)
C6 C7 . 1.380(3)
C6 C11 . 1.381(3)
C7 C8 . 1.382(3)
C8 C9 . 1.372(4)
C9 C10 . 1.363(3)
C10 C11 . 1.381(3)
C1S C2S 7 1.367(4)
C1S C2S . 1.367(4)
C2S C3S . 1.371(5)
C3S C4S . 1.351(4)
C4S C3S 7 1.351(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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C3' O2' C1' C6'A . . 18.1(2)
C5 C1 C2 C3 . . -177.9(2)
C4 C1 C2 C3 . . 0.7(3)
C5 C1 C2 C6 . . 1.3(3)
C4 C1 C2 C6 . . 180.0(2)
C4' N3'A C3' O2' . . 154.1(2)
C6'A N3'A C3' O2' . . 3.8(2)
C4' N3'A C3' C3 . . -29.7(3)
C6'A N3'A C3' C3 . . 180.0(2)
C1' O2' C3' N3'A . . -13.9(2)
C1' O2' C3' C3 . . 169.8(2)
N3'A C3' C3 C2 . . -175.4(2)
O2' C3' C3 C2 . . 0.3(3)
C1 C2 C3 C3' . . 175.8(2)
C6 C2 C3 C3' . . -3.4(3)
C3' N3'A C4' C5' . . -152.6(2)
C6'A N3'A C4' C5' . . -2.5(2)
C2 C1 C4 N1 . . 10.(14)
C5 C1 C4 N1 . . -17.E1(10)
N3'A C4' C5' C6' . . 26.0(2)
C2 C1 C5 N2 . . 15.E1(3)
C4 C1 C5 N2 . . -2.E1(3)
C3' N3'A C6'A C1' . . 7.6(2)
C4' N3'A C6'A C1' . . -147.7(2)
C3' N3'A C6'A C6' . . 133.5(2)
C4' N3'A C6'A C6' . . -21.8(2)
O2' C1' C6'A N3'A . . -14.8(2)
O2' C1' C6'A C6' . . -126.2(2)
N3'A C6'A C6' C5' . . 36.6(2)
C1' C6'A C6' C5' . . 147.4(2)
C4' C5' C6' C6'A . . -39.5(2)
C3 C2 C6 C7 . . 95.5(2)
C1 C2 C6 C7 . . -83.7(2)
C3 C2 C6 C11 . . -87.6(2)
C1 C2 C6 C11 . . 93.2(2)
C11 C6 C7 C8 . . 0.4(4)
C2 C6 C7 C8 . . 177.4(2)
C6 C7 C8 C9 . . -0.9(5)
C7 C8 C9 C10 . . 0.8(5)
C8 C9 C10 C11 . . -0.3(4)
C7 C6 C11 C10 . . 0.1(3)
C2 C6 C11 C10 . . -176.9(2)
C9 C10 C11 C6 . . -0.1(4)
C2S C1S C2S C3S 7 . -0.4(2)
C1S C2S C3S C4S . . 0.8(4)
C2S C3S C4S C3S . 7 -0.4(2)