##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     ?
_journal_date_recd_electronic     2017-03-21
_journal_date_accepted     2017-04-11
_journal_name_full     'IUCrData'
_journal_year     2017
_journal_volume     2
_journal_issue      4
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314617005491
_journal_coeditor_code     HB4134
_publ_contact_author
;
Dr. Ezzat Khan
Department of Chemistry
University of Malakand
Chakdara, Dir (lower), Khyber Pakhtunkhwa
Pakistan
;
_publ_contact_author_email     'ekhan@uom.edu.pk'
_publ_contact_author_fax     '0092 945 76 34 91'
_publ_contact_author_phone     '0092 945 76 23 55'
_publ_section_title
;
(2E)-3-Phenylprop-2-en-1-yl thiocyanate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'Khan, Ezzat'
;
Department of Chemistry
University of Malakand
Pakistan
;
    'Shahzad, Adnan'
;
Institute of Chemical Sciences
University of Swat, Khyber Pakhtunkhwa
Pakistan
;
    'Tahir, M. Nawaz'
;
Department of Physics
University of Sargodha
Sargodha
Pakistan
;
    'Ateeq, Muhammad'
;
HEJ Research Institute, University of Karachi, Karachi, Pakistan
;
_publ_section_synopsis
;
The C---S---C bond angle in the title compound is 99.41(9)°. In the crystal,
inversion dimers linked by pairs of extremely weak C---H...N interactions
occur, as does a short S...N contact.
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(2E)-3-Phenylprop-2-en-1-yl thiocyanate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H9 N S'
_chemical_formula_sum     'C10 H9 N S'
_chemical_formula_iupac     'C10 H9 N S'
_chemical_formula_weight     175.24
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_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     6.0108(5)
_cell_length_b     7.9243(6)
_cell_length_c     19.8388(16)
_cell_angle_alpha     90
_cell_angle_beta     94.271(4)
_cell_angle_gamma     90
_cell_volume     942.33(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1697
_cell_measurement_theta_min     2.769
_cell_measurement_theta_max     28.354
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.235
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     368
_exptl_absorpt_coefficient_mu     0.285
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2005)
;
_exptl_absorpt_correction_T_min     0.902
_exptl_absorpt_correction_T_max     0.932
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     7.50
_diffrn_reflns_number     8591
_diffrn_reflns_av_R_equivalents     0.0223
_diffrn_reflns_theta_min     2.769
_diffrn_reflns_theta_max     28.354
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2319
_reflns_number_gt     1697
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0630
_refine_ls_R_factor_gt     0.0426
_refine_ls_wR_factor_gt     0.1007
_refine_ls_wR_factor_ref     0.1120
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     2319
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0412P)²+0.2661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.391
_refine_diff_density_min     -0.392
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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.66511(8) 0.22408(8) 0.47818(3) 0.0691(2) Uani d 1 . .
    N N1 1.1334(3) 0.2485(3) 0.48932(12) 0.0962(7) Uani d 1 . .
    C C1 0.9445(3) 0.2408(3) 0.48395(10) 0.0633(5) Uani d 1 . .
    C C2 0.5958(3) 0.3977(3) 0.41956(10) 0.0676(5) Uani d 1 . .
    H H2A 0.4348 0.4037 0.4114 0.081 Uiso calc 1 . .
    H H2B 0.6457 0.5027 0.4408 0.081 Uiso calc 1 . .
    C C3 0.6953(3) 0.3822(2) 0.35388(9) 0.0564(4) Uani d 1 . .
    H H3 0.6398 0.3001 0.3236 0.068 Uiso calc 1 . .
    C C4 0.8586(3) 0.4791(2) 0.33626(9) 0.0522(4) Uani d 1 . .
    H H4 0.9140 0.5571 0.3683 0.063 Uiso calc 1 . .
    C C5 0.9632(3) 0.47826(19) 0.27201(8) 0.0465(4) Uani d 1 . .
    C C6 0.8665(3) 0.3994(2) 0.21446(9) 0.0534(4) Uani d 1 . .
    H H6 0.7302 0.3447 0.2162 0.064 Uiso calc 1 . .
    C C7 0.9699(3) 0.4015(2) 0.15505(9) 0.0623(5) Uani d 1 . .
    H H7 0.9031 0.3484 0.1169 0.075 Uiso calc 1 . .
    C C8 1.1715(3) 0.4817(2) 0.15159(10) 0.0660(5) Uani d 1 . .
    H H8 1.2413 0.4825 0.1113 0.079 Uiso calc 1 . .
    C C9 1.2691(3) 0.5602(2) 0.20754(11) 0.0650(5) Uani d 1 . .
    H H9 1.4057 0.6143 0.2053 0.078 Uiso calc 1 . .
    C C10 1.1658(3) 0.5595(2) 0.26705(10) 0.0571(4) Uani d 1 . .
    H H10 1.2329 0.6145 0.3047 0.068 Uiso calc 1 . .
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 0.0554(3) 0.0917(4) 0.0609(3) -0.0079(2) 0.0080(2) 0.0169(3)
    N1 0.0577(11) 0.1294(19) 0.1012(16) 0.0042(11) 0.0046(10) 0.0073(13)
    C1 0.0601(11) 0.0766(13) 0.0537(10) 0.0024(9) 0.0081(8) -0.0006(9)
    C2 0.0608(11) 0.0811(14) 0.0625(11) 0.0112(10) 0.0148(8) 0.0083(10)
    C3 0.0561(10) 0.0601(11) 0.0533(10) 0.0004(8) 0.0049(7) 0.0036(8)
    C4 0.0591(10) 0.0442(9) 0.0529(10) 0.0018(7) 0.0015(7) -0.0023(7)
    C5 0.0516(9) 0.0361(8) 0.0516(9) 0.0024(6) 0.0022(7) 0.0037(7)
    C6 0.0542(9) 0.0490(10) 0.0567(10) -0.0080(7) 0.0026(7) 0.0016(8)
    C7 0.0783(12) 0.0558(11) 0.0529(10) -0.0051(9) 0.0046(9) -0.0020(8)
    C8 0.0779(12) 0.0569(12) 0.0658(12) 0.0006(9) 0.0235(10) 0.0063(9)
    C9 0.0574(10) 0.0531(11) 0.0863(14) -0.0071(8) 0.0177(9) 0.0056(10)
    C10 0.0573(10) 0.0462(10) 0.0668(11) -0.0056(8) -0.0012(8) -0.0031(8)
_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_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C1 . 1.680(2) ?
    S1 C2 . 1.829(2) ?
    N1 C1 . 1.134(2) ?
    C2 C3 . 1.479(2) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.313(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.463(2) ?
    C4 H4 . 0.9300 ?
    C5 C10 . 1.388(2) ?
    C5 C6 . 1.390(2) ?
    C6 C7 . 1.373(2) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.374(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.366(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.374(3) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
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_3
    _geom_angle
    _geom_angle_publ_flag
    C1 S1 C2 . . 99.41(9) ?
    N1 C1 S1 . . 178.0(2) ?
    C3 C2 S1 . . 114.20(14) ?
    C3 C2 H2A . . 108.7 ?
    S1 C2 H2A . . 108.7 ?
    C3 C2 H2B . . 108.7 ?
    S1 C2 H2B . . 108.7 ?
    H2A C2 H2B . . 107.6 ?
    C4 C3 C2 . . 123.06(18) ?
    C4 C3 H3 . . 118.5 ?
    C2 C3 H3 . . 118.5 ?
    C3 C4 C5 . . 127.41(16) ?
    C3 C4 H4 . . 116.3 ?
    C5 C4 H4 . . 116.3 ?
    C10 C5 C6 . . 117.75(16) ?
    C10 C5 C4 . . 119.76(15) ?
    C6 C5 C4 . . 122.49(15) ?
    C7 C6 C5 . . 120.76(16) ?
    C7 C6 H6 . . 119.6 ?
    C5 C6 H6 . . 119.6 ?
    C6 C7 C8 . . 120.36(18) ?
    C6 C7 H7 . . 119.8 ?
    C8 C7 H7 . . 119.8 ?
    C9 C8 C7 . . 119.79(18) ?
    C9 C8 H8 . . 120.1 ?
    C7 C8 H8 . . 120.1 ?
    C8 C9 C10 . . 120.13(17) ?
    C8 C9 H9 . . 119.9 ?
    C10 C9 H9 . . 119.9 ?
    C9 C10 C5 . . 121.19(17) ?
    C9 C10 H10 . . 119.4 ?
    C5 C10 H10 . . 119.4 ?
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 S1 C2 C3 . . . . 58.62(17) ?
    S1 C2 C3 C4 . . . . -108.73(19) ?
    C2 C3 C4 C5 . . . . -177.71(16) ?
    C3 C4 C5 C10 . . . . -164.85(18) ?
    C3 C4 C5 C6 . . . . 15.7(3) ?
    C10 C5 C6 C7 . . . . 0.5(2) ?
    C4 C5 C6 C7 . . . . 179.97(16) ?
    C5 C6 C7 C8 . . . . 0.1(3) ?
    C6 C7 C8 C9 . . . . -0.2(3) ?
    C7 C8 C9 C10 . . . . -0.2(3) ?
    C8 C9 C10 C5 . . . . 0.7(3) ?
    C6 C5 C10 C9 . . . . -0.9(3) ?
    C4 C5 C10 C9 . . . . 179.60(16) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C2 H2B N1 3_766 0.97 2.70 3.652(2) 167
_shelx_res_file
;
TITL T19UOM_0m in P2(1)/n WHITE PRISM
CELL 0.71073 6.0108 7.9243 19.8388 90.000 94.271 90.000
ZERR 4.00 0.0005 0.0006 0.0016 0.000 0.004 0.000
LATT 1
SYMM -x+1/2, y+1/2, -z+1/2
SFAC C  H  N    S
UNIT 40 36  4  4
L.S. 40
ACTA
BOND $H
HTAB
CONF
LIST 4
FMAP 2
PLAN 8
SIZE 0.37 0.27 0.25
omit 0   0   2
TEMP 23.000
WGHT    0.041200    0.266100
FVAR       0.25488
S1    4    0.665113    0.224081    0.478182    11.00000    0.05536    0.09171 =
         0.06089    0.01685    0.00800   -0.00789
N1    3    1.133385    0.248493    0.489325    11.00000    0.05767    0.12944 =
         0.10123    0.00731    0.00460    0.00418
C1    1    0.944503    0.240761    0.483947    11.00000    0.06012    0.07663 =
         0.05371   -0.00064    0.00814    0.00242
C2    1    0.595759    0.397666    0.419564    11.00000    0.06080    0.08114 =
         0.06250    0.00832    0.01483    0.01122
AFIX  23
H2A   2    0.434833    0.403719    0.411387    11.00000   -1.20000
H2B   2    0.645713    0.502674    0.440779    11.00000   -1.20000
AFIX   0
C3    1    0.695339    0.382237    0.353878    11.00000    0.05606    0.06011 =
         0.05328    0.00364    0.00490    0.00042
AFIX  43
H3    2    0.639767    0.300134    0.323639    11.00000   -1.20000
AFIX   0
C4    1    0.858578    0.479074    0.336262    11.00000    0.05914    0.04424 =
         0.05292   -0.00233    0.00151    0.00176
AFIX  43
H4    2    0.913970    0.557055    0.368289    11.00000   -1.20000
AFIX   0
C5    1    0.963195    0.478262    0.272015    11.00000    0.05162    0.03614 =
         0.05159    0.00366    0.00225    0.00236
C6    1    0.866507    0.399448    0.214463    11.00000    0.05418    0.04896 =
         0.05669    0.00158    0.00259   -0.00798
AFIX  43
H6    2    0.730217    0.344689    0.216230    11.00000   -1.20000
AFIX   0
C7    1    0.969889    0.401513    0.155048    11.00000    0.07833    0.05578 =
         0.05289   -0.00195    0.00464   -0.00508
AFIX  43
H7    2    0.903142    0.348377    0.116931    11.00000   -1.20000
AFIX   0
C8    1    1.171497    0.481685    0.151592    11.00000    0.07790    0.05692 =
         0.06582    0.00625    0.02346    0.00064
AFIX  43
H8    2    1.241261    0.482451    0.111295    11.00000   -1.20000
AFIX   0
C9    1    1.269086    0.560242    0.207536    11.00000    0.05740    0.05305 =
         0.08628    0.00558    0.01774   -0.00713
AFIX  43
H9    2    1.405688    0.614299    0.205341    11.00000   -1.20000
AFIX   0
C10   1    1.165799    0.559546    0.267050    11.00000    0.05734    0.04625 =
         0.06676   -0.00308   -0.00124   -0.00564
AFIX  43
H10   2    1.232899    0.614543    0.304674    11.00000   -1.20000
AFIX   0
HKLF 4 1 1 0 0 0 1 0 0 0 1
REM  T19UOM_0m in P2(1)/n WHITE PRISM
REM R1 =  0.0426 for    1697 Fo > 4sig(Fo)  and  0.0630 for all    2319 data
REM    109 parameters refined using      0 restraints
END
WGHT      0.0413      0.2662
REM No hydrogen bonds found for HTAB generation
REM Highest difference peak  0.391,  deepest hole -0.392,  1-sigma level  0.035
Q1    1   0.7335  0.1578  0.4562  11.00000  0.05    0.39
Q2    1   1.0151  0.5521  0.2636  11.00000  0.05    0.14
Q3    1   0.8793  0.4726  0.2403  11.00000  0.05    0.14
Q4    1   0.7307  0.4601  0.3305  11.00000  0.05    0.13
Q5    1   1.0824  0.4753  0.2734  11.00000  0.05    0.13
Q6    1   0.7414  0.3045  0.5022  11.00000  0.05    0.13
Q7    1   1.1745  0.6066  0.2311  11.00000  0.05    0.12
Q8    1   0.8191  0.2256  0.4976  11.00000  0.05    0.12
;
_shelxl_version_number        2.013
