#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/01/2240102.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_2240102
loop_
_publ_author_name
'Halasangi, Bhimashankar M.'
'Badami, Prema S.'
'Patil, Sangamesh A.'
'Anil Kumar, G. N.'
_publ_section_title
;
 Crystal structure of
 3-[(E)-2-(4-phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]indolin-2-one
;
_journal_coeditor_code           LH5732
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1177
_journal_page_last               o1178
_journal_paper_doi               10.1107/S1600536814022715
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C17 H12 N4 O S'
_chemical_formula_moiety         'C17 H12 N4 O S'
_chemical_formula_sum            'C17 H12 N4 O S'
_chemical_formula_weight         320.37
_chemical_name_systematic
;
3-[(E)-2-(4-Phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]indolin-2-one
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.706(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7108(8)
_cell_length_b                   5.1411(2)
_cell_length_c                   15.9065(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1443.45(10)
_computing_cell_refinement
;
SAINT (Bruker, 1998)
;
_computing_data_collection
;
SMART (Bruker, 1998)
;
_computing_data_reduction
;
SAINT (Bruker, 1998)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and CAMERON (Watkin et al.,
1993)
;
_computing_publication_material
;
PARST (Nardelli, 1995) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  1994)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11530
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         2.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0451P)²+0.0098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                2124
_reflns_number_total             3142
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5732sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2240102
_cod_database_fobs_code          2240102
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_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_refinement_flags
_atom_site_occupancy
S S1 0.33816(3) 0.66660(12) 0.39879(3) 0.04097(19) Uani d . 1
O O1 0.08908(8) 0.2212(3) 0.51706(8) 0.0481(4) Uani d . 1
N N1 0.28727(8) 0.7985(3) 0.54037(9) 0.0325(4) Uani d . 1
N N2 0.21944(9) 0.4599(3) 0.46996(9) 0.0369(4) Uani d . 1
H H2 0.1873 0.4489 0.5075 0.044 Uiso calc R 1
N N3 0.21516(9) 0.3013(3) 0.40283(9) 0.0341(4) Uani d . 1
N N4 0.05982(9) -0.1170(3) 0.42364(9) 0.0387(5) Uani d . 1
H H4 0.0225 -0.1842 0.4474 0.046 Uiso calc R 1
C C1 0.43038(11) 1.3281(4) 0.58140(12) 0.0359(5) Uani d . 1
H H1 0.4504 1.335 0.5292 0.043 Uiso calc R 1
C C2 0.45583(11) 1.5006(4) 0.64372(12) 0.0419(5) Uani d . 1
H H2A 0.4931 1.6214 0.6335 0.05 Uiso calc R 1
C C3 0.42631(12) 1.4945(4) 0.72089(12) 0.0410(5) Uani d . 1
H H3 0.4433 1.6113 0.7629 0.049 Uiso calc R 1
C C4 0.37150(12) 1.3150(4) 0.73568(12) 0.0415(5) Uani d . 1
H H4A 0.3512 1.3113 0.7877 0.05 Uiso calc R 1
C C5 0.34649(11) 1.1406(4) 0.67384(12) 0.0376(5) Uani d . 1
H H5 0.3098 1.0188 0.6849 0.045 Uiso calc R 1
C C6 0.37525(10) 1.1438(4) 0.59528(11) 0.0304(5) Uani d . 1
C C7 0.34960(10) 0.9552(4) 0.52935(11) 0.0309(5) Uani d . 1
C C8 0.38282(11) 0.9102(4) 0.45680(11) 0.0367(5) Uani d . 1
H H8 0.4247 1.0007 0.4406 0.044 Uiso calc R 1
C C9 0.27677(11) 0.6406(4) 0.47676(11) 0.0314(5) Uani d . 1
C C10 0.16106(11) 0.1315(4) 0.39588(11) 0.0319(5) Uani d . 1
C C11 0.14763(10) -0.0560(4) 0.32827(11) 0.0317(5) Uani d . 1
C C12 0.18154(11) -0.1039(4) 0.25430(12) 0.0409(5) Uani d . 1
H H12 0.222 -0.003 0.2397 0.049 Uiso calc R 1
C C13 0.15406(12) -0.3045(4) 0.20274(12) 0.0451(6) Uani d . 1
H H13 0.1762 -0.3386 0.1528 0.054 Uiso calc R 1
C C14 0.09393(12) -0.4556(4) 0.22454(12) 0.0422(6) Uani d . 1
H H14 0.0768 -0.5912 0.1893 0.051 Uiso calc R 1
C C15 0.05887(11) -0.4091(4) 0.29754(12) 0.0392(5) Uani d . 1
H H15 0.0183 -0.51 0.312 0.047 Uiso calc R 1
C C16 0.08638(10) -0.2078(4) 0.34775(11) 0.0319(5) Uani d . 1
C C17 0.10069(11) 0.0896(4) 0.45404(12) 0.0362(5) Uani d . 1
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 0 '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 0.006 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 0 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 S1 C9 87.69(9)
C9 N1 C7 109.19(15)
N3 N2 C9 117.83(15)
N3 N2 H2 121.1
C9 N2 H2 121.1
C10 N3 N2 118.11(16)
C17 N4 C16 111.08(16)
C17 N4 H4 124.5
C16 N4 H4 124.5
C2 C1 C6 121.10(18)
C2 C1 H1 119.5
C6 C1 H1 119.5
C3 C2 C1 120.2(2)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
C2 C3 C4 119.63(19)
C2 C3 H3 120.2
C4 C3 H3 120.2
C3 C4 C5 120.37(19)
C3 C4 H4A 119.8
C5 C4 H4A 119.8
C4 C5 C6 121.01(19)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 C1 117.73(18)
C5 C6 C7 121.26(18)
C1 C6 C7 121.00(17)
C8 C7 N1 114.38(17)
C8 C7 C6 126.00(18)
N1 C7 C6 119.59(16)
C7 C8 S1 111.71(15)
C7 C8 H8 124.1
S1 C8 H8 124.1
N1 C9 N2 122.80(17)
N1 C9 S1 117.03(15)
N2 C9 S1 120.17(14)
N3 C10 C11 125.96(17)
N3 C10 C17 127.60(18)
C11 C10 C17 106.44(17)
C12 C11 C16 119.27(18)
C12 C11 C10 133.79(19)
C16 C11 C10 106.93(16)
C13 C12 C11 118.73(19)
C13 C12 H12 120.6
C11 C12 H12 120.6
C12 C13 C14 120.71(19)
C12 C13 H13 119.6
C14 C13 H13 119.6
C15 C14 C13 121.4(2)
C15 C14 H14 119.3
C13 C14 H14 119.3
C16 C15 C14 117.20(19)
C16 C15 H15 121.4
C14 C15 H15 121.4
C15 C16 C11 122.65(18)
C15 C16 N4 128.34(18)
C11 C16 N4 109.01(17)
O1 C17 N4 126.73(19)
O1 C17 C10 126.84(19)
N4 C17 C10 106.42(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.711(2)
S1 C9 1.7203(19)
O1 C17 1.240(2)
N1 C9 1.299(2)
N1 C7 1.389(2)
N2 N3 1.341(2)
N2 C9 1.374(2)
N2 H2 0.86
N3 C10 1.294(2)
N4 C17 1.352(2)
N4 C16 1.411(2)
N4 H4 0.86
C1 C2 1.378(3)
C1 C6 1.391(3)
C1 H1 0.93
C2 C3 1.373(3)
C2 H2A 0.93
C3 C4 1.373(3)
C3 H3 0.93
C4 C5 1.377(3)
C4 H4A 0.93
C5 C6 1.388(2)
C5 H5 0.93
C6 C7 1.472(3)
C7 C8 1.358(2)
C8 H8 0.93
C10 C11 1.449(3)
C10 C17 1.486(3)
C11 C12 1.386(2)
C11 C16 1.392(3)
C12 C13 1.381(3)
C12 H12 0.93
C13 C14 1.385(3)
C13 H13 0.93
C14 C15 1.382(3)
C14 H14 0.93
C15 C16 1.372(3)
C15 H15 0.93
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
N2 H2 O1 . 0.86 2.12 2.771(2) 133 yes
N4 H4 O1 3_556 0.86 2.11 2.922(2) 158 yes
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
C9 N2 N3 C10 -179.69(17)
C6 C1 C2 C3 -0.6(3)
C1 C2 C3 C4 0.2(3)
C2 C3 C4 C5 0.4(3)
C3 C4 C5 C6 -0.7(3)
C4 C5 C6 C1 0.3(3)
C4 C5 C6 C7 179.04(18)
C2 C1 C6 C5 0.3(3)
C2 C1 C6 C7 -178.37(17)
C9 N1 C7 C8 0.9(2)
C9 N1 C7 C6 -177.30(17)
C5 C6 C7 C8 -167.50(19)
C1 C6 C7 C8 11.2(3)
C5 C6 C7 N1 10.4(3)
C1 C6 C7 N1 -170.89(17)
N1 C7 C8 S1 -0.5(2)
C6 C7 C8 S1 177.49(15)
C9 S1 C8 C7 0.06(16)
C7 N1 C9 N2 179.57(17)
C7 N1 C9 S1 -0.8(2)
N3 N2 C9 N1 -178.05(17)
N3 N2 C9 S1 2.4(2)
C8 S1 C9 N1 0.48(16)
C8 S1 C9 N2 -179.92(16)
N2 N3 C10 C11 -179.72(16)
N2 N3 C10 C17 0.7(3)
N3 C10 C11 C12 -3.6(4)
C17 C10 C11 C12 176.1(2)
N3 C10 C11 C16 177.11(18)
C17 C10 C11 C16 -3.2(2)
C16 C11 C12 C13 -1.0(3)
C10 C11 C12 C13 179.7(2)
C11 C12 C13 C14 -0.2(3)
C12 C13 C14 C15 0.9(3)
C13 C14 C15 C16 -0.3(3)
C14 C15 C16 C11 -0.9(3)
C14 C15 C16 N4 178.32(18)
C12 C11 C16 C15 1.6(3)
C10 C11 C16 C15 -178.92(17)
C12 C11 C16 N4 -177.75(17)
C10 C11 C16 N4 1.7(2)
C17 N4 C16 C15 -178.68(18)
C17 N4 C16 C11 0.7(2)
C16 N4 C17 O1 176.05(19)
C16 N4 C17 C10 -2.7(2)
N3 C10 C17 O1 4.6(3)
C11 C10 C17 O1 -175.10(19)
N3 C10 C17 N4 -176.72(18)
C11 C10 C17 N4 3.6(2)
