##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, 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.                                       #
#                                                                            #
# 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 journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2014-07-09
_journal_date_accepted     2014-07-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      9
_journal_page_first     o928
_journal_page_last     o929
_journal_paper_category     HO
_journal_paper_doi     10.1107/S1600536814016511
_journal_coeditor_code     IS5369
_publ_contact_author_name     'Sridhar, M. A.'
_publ_contact_author_address
;
Department of Studies in Physics Manasagangotri
University of Mysore, Mysore 570 006
India
;
_publ_contact_author_email     'mas@physics.uni-mysore.ac.in'
_publ_contact_author_fax     '+918212419363'
_publ_contact_author_phone     '+918212419333'
_publ_section_title
;\
Crystal structure of
(E)-N-phenyl-N'-[1-(thiophen-2-yl)ethylidene]\
formohydrazide
;
loop_
    _publ_author_name
    _publ_author_address
    'Dileep, C. S.'
;
Department of Studies in Physics
Manasagangotri
University of Mysore
Mysore 570 006
India
;
    'Raghavendra, K. R.'
;
Department of Chemistry
SBRR Mahajana College
Mysore 570 006
India
;
    'Lokanath, N. K.'
;
Department of Studies in Physics
Manasagangotri
University of Mysore
Mysore 570 006
India
;
    'Ajay Kumar, K.'
;
Post Graduate Department of Chemistry
Yuvaraja College
University of Mysore
Mysore 570 005
India
;
    'Sridhar, M. A.'
;
Department of Studies in Physics
Manasagangotri
University of Mysore
Mysore 570 006
India
;
data_I
_database_code_depnum_ccdc_archive     'CCDC 1014287'
_chemical_name_systematic
;\
(E)-N-Phenyl-N'-[1-(thiophen-2-\
yl)ethylidene]formohydrazide.
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H12 N2 O S'
_chemical_formula_sum     'C13 H12 N2 O S'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C13 H12 N2 O S'
_chemical_formula_weight     244.32
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,-y,1/2+z
    3 1/2+x,1/2-y,-z
    4 -x,1/2+y,1/2-z
_cell_length_a     5.4960(7)
_cell_length_b     11.0177(13)
_cell_length_c     20.249(2)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1226.1(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6298
_cell_measurement_theta_min     4.37
_cell_measurement_theta_max     64.63
_cell_measurement_temperature     296
_cell_special_details
;
;
_exptl_crystal_description     'block'
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.250
_exptl_crystal_size_mid     0.220
_exptl_crystal_size_min     0.200
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.324
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     2.217
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2013)'
_exptl_absorpt_correction_T_min     0.604
_exptl_absorpt_correction_T_max     0.662
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     'CuK\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'Bruker MicroStar microfocus rotating anode'
_diffrn_radiation_monochromator     'Helios multilayer optics'
_diffrn_measurement_device_type     'Bruker X8 Proteum'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     10.7
_diffrn_reflns_number     6298
_diffrn_reflns_av_R_equivalents     0.0423
_diffrn_reflns_av_sigmaI/netI     0.0480
_diffrn_reflns_theta_min     4.37
_diffrn_reflns_theta_max     64.63
_diffrn_reflns_theta_full     64.63
_diffrn_measured_fraction_theta_max     0.973
_diffrn_measured_fraction_theta_full     0.973
_diffrn_reflns_limit_h_min     -2
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     22
_diffrn_reflns_reduction_process
;
;
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs 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     2010
_reflns_number_gt     1904
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0406
_refine_ls_R_factor_gt     0.0384
_refine_ls_wR_factor_gt     0.0993
_refine_ls_wR_factor_ref     0.1016
_refine_ls_goodness_of_fit_ref     1.103
_refine_ls_restrained_S_all     1.103
_refine_ls_number_reflns     2010
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0605P)²+0.0861P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.213
_refine_diff_density_min     -0.203
_refine_ls_extinction_method     'shelxl'
_refine_ls_extinction_coef     0.0158(16)
_refine_ls_extinction_expression
                                  'FC^*^=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 805 Friedel pairs'
_refine_ls_abs_structure_Flack     0.02(2)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0181 0.0091 ' 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 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0492 0.0322 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.3331 0.5567 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2013)'
_computing_cell_refinement     'SAINT (Bruker, 2013)'
_computing_data_reduction     'SAINT (Bruker, 2013)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Mercury (Macrae et al., 2006)'
_computing_publication_material     '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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.05502(12) 0.12455(6) 0.72104(3) 0.0539(2) Uani d . 1.000 . .
    O O1 0.0434(4) -0.24121(15) 0.55887(8) 0.0526(6) Uani d . 1.000 . .
    N N1 0.0078(3) 0.00557(16) 0.59394(8) 0.0348(5) Uani d . 1.000 . .
    N N2 0.0086(3) -0.04249(15) 0.52882(8) 0.0344(5) Uani d . 1.000 . .
    C C1 -0.0682(6) 0.1399(3) 0.79702(12) 0.0623(10) Uani d . 1.000 . .
    C C2 -0.2635(6) 0.0712(3) 0.80591(13) 0.0648(10) Uani d . 1.000 . .
    C C3 -0.3227(5) 0.0016(2) 0.74907(11) 0.0513(8) Uani d . 1.000 . .
    C C4 -0.1639(4) 0.02325(18) 0.69777(10) 0.0358(6) Uani d . 1.000 . .
    C C5 -0.1724(4) -0.02503(18) 0.63061(10) 0.0331(6) Uani d . 1.000 . .
    C C6 -0.3905(4) -0.0972(2) 0.61062(13) 0.0509(8) Uani d . 1.000 . .
    C C7 0.0373(4) -0.16179(19) 0.51733(10) 0.0410(7) Uani d . 1.000 . .
    C C8 0.0373(4) 0.04484(17) 0.47710(9) 0.0325(6) Uani d . 1.000 . .
    C C9 0.2273(4) 0.0366(2) 0.43330(11) 0.0397(6) Uani d . 1.000 . .
    C C10 0.2429(4) 0.1192(2) 0.38203(12) 0.0479(7) Uani d . 1.000 . .
    C C11 0.0710(5) 0.2091(2) 0.37516(11) 0.0469(7) Uani d . 1.000 . .
    C C12 -0.1151(5) 0.2185(2) 0.41975(12) 0.0463(8) Uani d . 1.000 . .
    C C13 -0.1322(4) 0.1365(2) 0.47156(11) 0.0413(6) Uani d . 1.000 . .
    H H1 -0.00560 0.19130 0.82930 0.0750 Uiso c R 1.000 . .
    H H2 -0.35200 0.06880 0.84500 0.0780 Uiso c R 1.000 . .
    H H3 -0.45300 -0.05220 0.74680 0.0620 Uiso c R 1.000 . .
    H H6A -0.39060 -0.10770 0.56360 0.0760 Uiso c R 1.000 . .
    H H6B -0.53550 -0.05510 0.62380 0.0760 Uiso c R 1.000 . .
    H H6C -0.38540 -0.17530 0.63170 0.0760 Uiso c R 1.000 . .
    H H7 0.05420 -0.18570 0.47350 0.0490 Uiso c R 1.000 . .
    H H9 0.34410 -0.02390 0.43800 0.0480 Uiso c R 1.000 . .
    H H10 0.37060 0.11400 0.35200 0.0570 Uiso c R 1.000 . .
    H H11 0.08130 0.26340 0.34010 0.0560 Uiso c R 1.000 . .
    H H12 -0.23010 0.27990 0.41530 0.0560 Uiso c R 1.000 . .
    H H13 -0.25720 0.14340 0.50230 0.0500 Uiso c R 1.000 . .
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
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 C1 . . 1.690(3) n
    S1 C4 . . 1.707(2) n
    O1 C7 . . 1.214(3) n
    N1 N2 . . 1.421(2) n
    N1 C5 . . 1.283(3) n
    N2 C7 . . 1.344(3) n
    N2 C8 . . 1.431(2) n
    C1 C2 . . 1.326(5) no
    C2 C3 . . 1.421(4) no
    C3 C4 . . 1.378(3) no
    C4 C5 . . 1.461(3) no
    C5 C6 . . 1.494(3) no
    C8 C9 . . 1.373(3) no
    C8 C13 . . 1.379(3) no
    C9 C10 . . 1.383(3) no
    C10 C11 . . 1.376(3) no
    C11 C12 . . 1.368(4) no
    C12 C13 . . 1.388(3) no
    C1 H1 . . 0.9300 no
    C2 H2 . . 0.9300 no
    C3 H3 . . 0.9300 no
    C6 H6A . . 0.9600 no
    C6 H6B . . 0.9600 no
    C6 H6C . . 0.9600 no
    C7 H7 . . 0.9300 no
    C9 H9 . . 0.9300 no
    C10 H10 . . 0.9300 no
    C11 H11 . . 0.9300 no
    C12 H12 . . 0.9300 no
    C13 H13 . . 0.9300 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
    C1 S1 C4 . . . 91.96(13) n
    N2 N1 C5 . . . 116.20(17) n
    N1 N2 C7 . . . 121.70(16) n
    N1 N2 C8 . . . 115.40(15) n
    C7 N2 C8 . . . 121.19(16) n
    S1 C1 C2 . . . 113.0(2) n
    C1 C2 C3 . . . 112.6(2) no
    C2 C3 C4 . . . 111.9(2) no
    S1 C4 C3 . . . 110.58(16) n
    S1 C4 C5 . . . 121.16(16) n
    C3 C4 C5 . . . 128.2(2) no
    N1 C5 C4 . . . 114.73(19) n
    N1 C5 C6 . . . 127.04(19) n
    C4 C5 C6 . . . 118.13(19) no
    O1 C7 N2 . . . 126.02(19) n
    N2 C8 C9 . . . 120.81(18) n
    N2 C8 C13 . . . 118.53(18) n
    C9 C8 C13 . . . 120.65(19) no
    C8 C9 C10 . . . 119.2(2) no
    C9 C10 C11 . . . 120.5(2) no
    C10 C11 C12 . . . 120.1(2) no
    C11 C12 C13 . . . 120.0(2) no
    C8 C13 C12 . . . 119.5(2) no
    S1 C1 H1 . . . 124.00 no
    C2 C1 H1 . . . 123.00 no
    C1 C2 H2 . . . 124.00 no
    C3 C2 H2 . . . 124.00 no
    C2 C3 H3 . . . 124.00 no
    C4 C3 H3 . . . 124.00 no
    C5 C6 H6A . . . 109.00 no
    C5 C6 H6B . . . 109.00 no
    C5 C6 H6C . . . 109.00 no
    H6A C6 H6B . . . 109.00 no
    H6A C6 H6C . . . 109.00 no
    H6B C6 H6C . . . 109.00 no
    O1 C7 H7 . . . 117.00 no
    N2 C7 H7 . . . 117.00 no
    C8 C9 H9 . . . 120.00 no
    C10 C9 H9 . . . 120.00 no
    C9 C10 H10 . . . 120.00 no
    C11 C10 H10 . . . 120.00 no
    C10 C11 H11 . . . 120.00 no
    C12 C11 H11 . . . 120.00 no
    C11 C12 H12 . . . 120.00 no
    C13 C12 H12 . . . 120.00 no
    C8 C13 H13 . . . 120.00 no
    C12 C13 H13 . . . 120.00 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
    C4 S1 C1 C2 . . . . 0.9(3) no
    C1 S1 C4 C3 . . . . -1.3(2) no
    C1 S1 C4 C5 . . . . 176.4(2) no
    C5 N1 N2 C7 . . . . -67.0(2) no
    C5 N1 N2 C8 . . . . 127.7(2) no
    N2 N1 C5 C4 . . . . 178.38(16) no
    N2 N1 C5 C6 . . . . -5.3(3) no
    C7 N2 C8 C13 . . . . 135.3(2) no
    N1 N2 C7 O1 . . . . 6.9(3) no
    C8 N2 C7 O1 . . . . 171.3(2) no
    N1 N2 C8 C9 . . . . 121.6(2) no
    C7 N2 C8 C9 . . . . -43.7(3) no
    N1 N2 C8 C13 . . . . -59.4(2) no
    S1 C1 C2 C3 . . . . -0.3(4) no
    C1 C2 C3 C4 . . . . -0.7(4) no
    C2 C3 C4 C5 . . . . -176.1(2) no
    C2 C3 C4 S1 . . . . 1.4(3) no
    S1 C4 C5 N1 . . . . 6.3(3) no
    C3 C4 C5 N1 . . . . -176.4(2) no
    C3 C4 C5 C6 . . . . 7.0(3) no
    S1 C4 C5 C6 . . . . -170.31(16) no
    N2 C8 C9 C10 . . . . 176.94(19) no
    C13 C8 C9 C10 . . . . -2.1(3) no
    N2 C8 C13 C12 . . . . -176.7(2) no
    C9 C8 C13 C12 . . . . 2.3(3) no
    C8 C9 C10 C11 . . . . 0.4(3) no
    C9 C10 C11 C12 . . . . 1.0(4) no
    C10 C11 C12 C13 . . . . -0.7(4) no
    C11 C12 C13 C8 . . . . -0.9(3) no
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
    _geom_hbond_publ_flag
    C1 H1 O1 4_556 0.93 2.39 3.202(3) 145 yes
