##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.0.1.  #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_(I)
_audit_creation_method     SHELXL
_chemical_name_systematic
;
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C13 H12 N2 O S'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     244.31
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
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'
_cell_length_a     6.4590(13)
_cell_length_b     15.662(3)
_cell_length_c     12.276(3)
_cell_angle_alpha     90.00
_cell_angle_beta     95.51(3)
_cell_angle_gamma     90.00
_cell_volume     1236.1(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     24
_cell_measurement_theta_min     11
_cell_measurement_theta_max     12
_cell_measurement_temperature     295(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max      .45
_exptl_crystal_size_mid      .30
_exptl_crystal_size_min      .25
_exptl_crystal_density_diffrn     1.313
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu      .246
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     θ/2θ
_diffrn_reflns_number     2922
_diffrn_reflns_av_R_equivalents      .112
_diffrn_reflns_av_sigmaI/netI      .0866
_diffrn_reflns_theta_min     2.11
_diffrn_reflns_theta_max     26.96
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     5
_reflns_number_total     2688
_reflns_number_gt     1283
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .167
_refine_ls_R_factor_gt      .076
_refine_ls_wR_factor_all      .306
_refine_ls_wR_factor_ref      .201
_refine_ls_goodness_of_fit_all     1.098
_refine_ls_goodness_of_fit_ref     1.334
_refine_ls_restrained_S_all     1.372
_refine_ls_restrained_S_obs     1.334
_refine_ls_number_reflns     2655
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme
             'calc w = 1/[\s^2^(Fo^2^)+(0.1213P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/esd_mean      .000
_refine_diff_density_max      .32
_refine_diff_density_min      -.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S'  .1246  .1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'SHELXTL-Plus (Sheldrick, 1994)'
_computing_structure_solution     'SHELXTL-Plus'
_computing_structure_refinement     'SHELXTL-Plus'
_computing_molecular_graphics     'SHELXTL-Plus'
_computing_publication_material     'SHELXTL-Plus'
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_disorder_group
    _atom_site_type_symbol
    S1  .1221(2)  .74352(7)  .15076(11)  .0685(5) Uani d . 1 . S
    O1 1.3971(5)  .5001(2)  -.2771(3)  .0676(9) Uani d . 1 . O
    N1  .6636(7)  .9262(3)  -.0180(4)  .0787(13) Uani d . 1 . N
    N2  .2078(6)  .9008(2)  .1019(3)  .0578(10) Uani d . 1 . N
    H1N  .279(7)    .943(3)    .069(4)    .080(16) Uiso d . 1 . H
    H2N  .099(7)    .913(3)    .130(4)    .062(14) Uiso d . 1 . H
    C1  .8939(6)  .5876(3)  -.1211(3)  .0482(10) Uani d . 1 . C
    C2  .9184(6)  .4997(3)  -.1393(4)  .0560(11) Uani d . 1 . C
    H2A  .8214(6)  .4617(3)  -.1158(4)  .067 Uiso calc R 1 . H
    C3 1.0828(7)  .4683(3)  -.1915(4)  .0563(11) Uani d . 1 . C
    H3A 1.0948(7)  .4099(3)  -.2031(4)  .068 Uiso calc R 1 . H
    C4 1.2280(6)  .5231(3)  -.2259(3)  .0506(10) Uani d . 1 . C
    C5 1.2062(7)  .6111(3)  -.2093(4)  .0580(11) Uani d . 1 . C
    H5A 1.3030(7)  .6487(3)  -.2336(4)  .070 Uiso calc R 1 . H
    C6 1.0431(6)  .6419(3)  -.1573(3)  .0557(11) Uani d . 1 . C
    H6A 1.0321(6)  .7004(3)  -.1461(3)  .067 Uiso calc R 1 . H
    C7  .7203(6)  .6166(3)  -.0663(3)  .0528(11) Uani d . 1 . C
    H7A  .6301(6)  .5749(3)  -.0449(3)  .063 Uiso calc R 1 . H
    C8  .6748(6)  .6979(3)  -.0428(3)  .0529(10) Uani d . 1 . C
    H8A  .7622(6)  .7411(3)  -.0632(3)  .063 Uiso calc R 1 . H
    C9  .4982(7)  .7207(3)  .0120(3)  .0508(10) Uani d . 1 . C
    H9A  .4129(7)  .6763(3)  .0310(3)  .061 Uiso calc R 1 . H
    C10  .4428(6)  .8005(2)  .0390(3)  .0489(10) Uani d . 1 . C
    C11  .2559(6)  .8197(2)  .0960(3)  .0496(10) Uani d . 1 . C
    C12  .5662(7)  .8700(3)  .0074(4)  .0588(11) Uani d . 1 . C
    C13 1.4261(8)  .4114(3)  -.2968(5)  .0757(14) Uani d . 1 . C
    H13A 1.5499(8)  .4035(3)  -.3331(5)  .114 Uiso calc R 1 . H
    H13B 1.3084(8)  .3897(3)  -.3422(5)  .114 Uiso calc R 1 . H
    H13C 1.4396(8)  .3812(3)  -.2284(5)  .114 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  .0753(8)  .0490(7)  .0867(9)  -.0128(6)  .0372(7)  -.0034(6)
    O1  .066(2)  .060(2)  .081(2)  .007(2)  .031(2)  .004(2)
    N1  .079(3)  .057(2)  .107(3)  -.003(2)  .041(2)  .013(2)
    N2  .065(2)  .043(2)  .071(3)  -.002(2)  .034(2)  .004(2)
    C1  .048(2)  .049(2)  .047(2)  -.003(2)  .004(2)  -.004(2)
    C2  .063(2)  .044(2)  .063(3)  -.006(2)  .018(2)  .006(2)
    C3  .070(3)  .043(2)  .057(3)  .005(2)  .010(2)  .000(2)
    C4  .052(2)  .054(2)  .046(2)  .000(2)  .008(2)  .006(2)
    C5  .057(2)  .044(2)  .075(3)  -.007(2)  .013(2)  .002(2)
    C6  .060(2)  .043(2)  .065(3)  -.001(2)  .011(2)  -.003(2)
    C7  .058(2)  .047(2)  .054(3)  -.006(2)  .009(2)  .004(2)
    C8  .058(2)  .050(2)  .051(2)  .001(2)  .010(2)  .002(2)
    C9  .055(2)  .048(2)  .050(2)  -.005(2)  .008(2)  .000(2)
    C10  .055(2)  .040(2)  .053(2)  -.007(2)  .009(2)  .001(2)
    C11  .059(2)  .039(2)  .052(2)  -.005(2)  .009(2)  -.001(2)
    C12  .062(3)  .051(3)  .067(3)  .002(2)  .022(2)  .003(2)
    C13  .080(3)  .067(3)  .085(4)  .007(3)  .033(3)  -.006(3)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix. The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry. An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C11 . . 1.653(4) yes
    O1 C4 . . 1.361(5) yes
    O1 C13 . . 1.425(6) yes
    N1 C12 . . 1.143(6) yes
    N2 C11 . . 1.312(5) yes
    N2 H1N . .  .92(5) yes
    N2 H2N . .  .83(5) yes
    C1 C6 . . 1.390(6) no
    C1 C2 . . 1.407(6) no
    C1 C7 . . 1.435(6) yes
    C2 C3 . . 1.382(6) no
    C2 H2A . .  .93 no
    C3 C4 . . 1.368(6) no
    C3 H3A . .  .93 no
    C4 C5 . . 1.401(6) no
    C5 C6 . . 1.370(6) no
    C5 H5A . .  .93 no
    C6 H6A . .  .93 no
    C7 C8 . . 1.344(6) yes
    C7 H7A . .  .93 no
    C8 C9 . . 1.424(6) yes
    C8 H8A . .  .93 no
    C9 C10 . . 1.351(6) yes
    C9 H9A . .  .93 no
    C10 C12 . . 1.425(6) yes
    C10 C11 . . 1.483(6) yes
    C13 H13A . .  .96 no
    C13 H13B . .  .96 no
    C13 H13C . .  .96 no
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_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C4 O1 C13 . . . 117.5(4) yes
    C11 N2 H1N . . . 123(3) yes
    C11 N2 H2N . . . 117(3) yes
    H1N N2 H2N . . . 120(4) yes
    C6 C1 C2 . . . 117.1(4) yes
    C6 C1 C7 . . . 123.6(4) yes
    C2 C1 C7 . . . 119.3(4) yes
    C3 C2 C1 . . . 121.7(4) no
    C3 C2 H2A . . . 119.1(2) no
    C1 C2 H2A . . . 119.1(2) no
    C4 C3 C2 . . . 120.0(4) no
    C4 C3 H3A . . . 120.0(3) no
    C2 C3 H3A . . . 120.0(2) no
    O1 C4 C3 . . . 125.5(4) yes
    O1 C4 C5 . . . 115.2(4) yes
    C3 C4 C5 . . . 119.4(4) no
    C6 C5 C4 . . . 120.5(4) no
    C6 C5 H5A . . . 119.8(3) no
    C4 C5 H5A . . . 119.8(3) no
    C5 C6 C1 . . . 121.4(4) no
    C5 C6 H6A . . . 119.3(3) no
    C1 C6 H6A . . . 119.3(2) no
    C8 C7 C1 . . . 126.6(4) yes
    C8 C7 H7A . . . 116.7(3) no
    C1 C7 H7A . . . 116.7(2) no
    C7 C8 C9 . . . 122.7(4) yes
    C7 C8 H8A . . . 118.7(3) no
    C9 C8 H8A . . . 118.7(3) no
    C10 C9 C8 . . . 126.2(4) yes
    C10 C9 H9A . . . 116.9(2) no
    C8 C9 H9A . . . 116.9(2) no
    C9 C10 C12 . . . 118.2(4) yes
    C9 C10 C11 . . . 123.4(4) yes
    C12 C10 C11 . . . 118.4(4) yes
    N2 C11 C10 . . . 115.5(4) yes
    N2 C11 S1 . . . 122.7(3) yes
    C10 C11 S1 . . . 121.8(3) yes
    N1 C12 C10 . . . 179.3(5) yes
    O1 C13 H13A . . . 109.5(2) no
    O1 C13 H13B . . . 109.5(3) no
    H13A C13 H13B . . . 109.5 no
    O1 C13 H13C . . . 109.5(3) no
    H13A C13 H13C . . . 109.5 no
    H13B C13 H13C . . . 109.5 no
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . .  -.3(6) no
    C7 C1 C2 C3 . . . . -179.9(4) no
    C1 C2 C3 C4 . . . .  .5(7) no
    C13 O1 C4 C3 . . . .  .1(6) yes
    C13 O1 C4 C5 . . . . -179.6(4) yes
    C2 C3 C4 O1 . . . . 179.4(4) no
    C2 C3 C4 C5 . . . .  -.9(6) no
    O1 C4 C5 C6 . . . . -179.2(4) no
    C3 C4 C5 C6 . . . . 1.1(6) no
    C4 C5 C6 C1 . . . .  -.9(7) no
    C2 C1 C6 C5 . . . .  .4(6) no
    C7 C1 C6 C5 . . . . -180.0(4) no
    C6 C1 C7 C8 . . . .  .5(7) no
    C2 C1 C7 C8 . . . . -179.9(4) yes
    C1 C7 C8 C9 . . . . 180.0(4) yes
    C7 C8 C9 C10 . . . . 179.6(4) yes
    C8 C9 C10 C12 . . . . 2.2(6) yes
    C8 C9 C10 C11 . . . . 179.9(4) yes
    C9 C10 C11 N2 . . . . -170.5(4) yes
    C12 C10 C11 N2 . . . . 7.1(6) yes
    C9 C10 C11 S1 . . . . 11.0(6) yes
    C12 C10 C11 S1 . . . . -171.4(3) yes
    C9 C10 C12 N1 . . . .  15E1(5)   no
    C11 C10 C12 N1 . . . .  -3E1(5)   no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N2 H1N N1 . . 3_675  .92(5) 2.18(5) 3.042(5) 155(4) yes
    N2 H2N O1 . . 4_476  .83(5) 2.27(5) 3.035(5) 153(4) yes
data_global
_journal_date_recd_electronic     1999-09-01
_journal_date_accepted     1999-10-12
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2000
_journal_volume     56
_journal_issue      1
_journal_page_first     88
_journal_page_last     89
_journal_paper_category     FO
_publ_contact_author_name     'Vladimir N. Nesterov'
_publ_contact_author_address
;
Institute of Organoelement Compounds
Russian Academy of Sciences
28 Vavilov St.
B-334, Moscow
Russian Federation
;
_publ_contact_author_email     vlad@kremlin.nmhu.edu
_publ_contact_author_fax     '(505)454-31-03'
_publ_contact_author_phone     '(505)454-32-08'
_publ_section_title
;
trans,trans-2-Cyano-5-(4-methoxyphenyl)penta-2,4-dienethioamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Nesterov, Vladimir N.'
;
Institute of Organoelement Compounds
Russian Academy of Sciences
28 Vavilov St.
Moscow
Russian Federation
;
    'Antipin, Mikhail Yu.'
;
Institute of Organoelement Compounds
Russian Academy of Sciences
28 Vavilov St.
Moscow
Russian Federation
;
    'Timofeeva, Tatiana V.'
;
Department of Physical Sciences
New Mexico Highlands University
Las Vegas
NM 87701
USA
;
    'Clark, Ronald D.'
;
Department of Physical Sciences
New Mexico Highlands University
Las Vegas
NM 87701
USA
;
