#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/30/2233066.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_2233066
loop_
_publ_author_name
'Qasem Ali, Amna'
'Eltayeb, Naser Eltaher'
'Teoh, Siang Guan'
'Salhin, Abdussalam'
'Fun, Hoong-Kun'
_publ_section_title
;
 (Z)-2-(5-Methyl-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide
;
_journal_coeditor_code           ZS2160
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3476
_journal_page_last               o3477
_journal_paper_doi               10.1107/S1600536811049154
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H14 N4 O S'
_chemical_formula_moiety         'C16 H14 N4 O S'
_chemical_formula_sum            'C16 H14 N4 O S'
_chemical_formula_weight         310.37
_chemical_melting_point_gt       511.8
_chemical_melting_point_lt       512.3
_chemical_name_systematic
;
(Z)-2-(5-Methyl-2-oxoindolin-3-ylidene)-N-
phenylhydrazinecarbothioamide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.105(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6875(3)
_cell_length_b                   17.9405(8)
_cell_length_c                   14.5658(6)
_cell_measurement_reflns_used    4470
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      30.22
_cell_measurement_theta_min      3.02
_cell_volume                     1485.97(12)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25266
_diffrn_reflns_theta_full        30.86
_diffrn_reflns_theta_max         30.86
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.9206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.303
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.9076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                3565
_reflns_number_total             4645
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2160.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233066
_cod_database_fobs_code          2233066
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
_atom_site_symmetry_multiplicity
S S1 0.07706(8) 0.29276(3) 0.01263(3) 0.02056(12) Uani d . 1 1
O O1 0.7096(2) 0.44974(7) 0.01110(8) 0.0187(3) Uani d . 1 1
N N1 0.9164(3) 0.52631(8) 0.11276(10) 0.0179(3) Uani d . 1 1
N N2 0.3961(2) 0.43175(8) 0.17539(10) 0.0150(3) Uani d . 1 1
N N3 0.3233(2) 0.39394(8) 0.09997(10) 0.0162(3) Uani d . 1 1
N N4 0.0280(2) 0.34699(8) 0.18614(10) 0.0159(3) Uani d . 1 1
C C1 0.6987(3) 0.51350(9) 0.24304(12) 0.0165(3) Uani d . 1 1
C C2 0.6453(3) 0.52430(10) 0.33500(12) 0.0184(3) Uani d . 1 1
H H2A 0.5077 0.5027 0.3598 0.022 Uiso calc R 1 1
C C3 0.7961(3) 0.56718(10) 0.39045(12) 0.0193(3) Uani d . 1 1
C C4 0.9965(3) 0.59863(10) 0.35161(13) 0.0206(4) Uani d . 1 1
H H4A 1.0989 0.6276 0.3895 0.025 Uiso calc R 1 1
C C5 1.0518(3) 0.58900(10) 0.25912(13) 0.0208(4) Uani d . 1 1
H H5A 1.1879 0.6110 0.2338 0.025 Uiso calc R 1 1
C C6 0.8998(3) 0.54610(10) 0.20639(12) 0.0169(3) Uani d . 1 1
C C7 0.7392(3) 0.47997(9) 0.08672(12) 0.0161(3) Uani d . 1 1
C C8 0.5860(3) 0.47119(9) 0.16929(11) 0.0155(3) Uani d . 1 1
C C9 0.1363(3) 0.34475(9) 0.10484(11) 0.0149(3) Uani d . 1 1
C C10 -0.1620(3) 0.30520(9) 0.22098(11) 0.0153(3) Uani d . 1 1
C C11 -0.3260(3) 0.26716(9) 0.16670(12) 0.0173(3) Uani d . 1 1
H H11A -0.3118 0.2663 0.1018 0.021 Uiso calc R 1 1
C C12 -0.5113(3) 0.23029(10) 0.20818(13) 0.0200(3) Uani d . 1 1
H H12A -0.6224 0.2039 0.1711 0.024 Uiso calc R 1 1
C C13 -0.5366(3) 0.23132(10) 0.30262(13) 0.0230(4) Uani d . 1 1
H H13A -0.6641 0.2060 0.3301 0.028 Uiso calc R 1 1
C C14 -0.3733(3) 0.26977(12) 0.35662(13) 0.0250(4) Uani d . 1 1
H H14A -0.3896 0.2711 0.4214 0.030 Uiso calc R 1 1
C C15 -0.1861(3) 0.30627(11) 0.31617(12) 0.0218(4) Uani d . 1 1
H H15A -0.0740 0.3321 0.3535 0.026 Uiso calc R 1 1
C C16 0.7427(4) 0.58122(12) 0.48997(13) 0.0275(4) Uani d . 1 1
H H16A 0.5743 0.5738 0.4998 0.041 Uiso calc R 1 1
H H16B 0.7858 0.6325 0.5061 0.041 Uiso calc R 1 1
H H16C 0.8332 0.5465 0.5287 0.041 Uiso calc R 1 1
H H1N4 0.095(4) 0.3741(12) 0.2252(15) 0.021(5) Uiso d . 1 1
H H1N1 1.034(4) 0.5376(13) 0.0759(16) 0.033(6) Uiso d . 1 1
H H1N3 0.410(4) 0.3965(12) 0.0486(15) 0.026(6) Uiso d . 1 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 0.0000 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'
S S 0.1246 0.1234 '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
C7 N1 C6 111.17(14)
C7 N1 H1N1 122.3(15)
C6 N1 H1N1 126.2(15)
C8 N2 N3 117.49(14)
N2 N3 C9 120.16(14)
N2 N3 H1N3 119.0(14)
C9 N3 H1N3 120.3(14)
C9 N4 C10 131.63(15)
C9 N4 H1N4 113.8(15)
C10 N4 H1N4 114.0(15)
C2 C1 C6 120.24(16)
C2 C1 C8 133.01(15)
C6 C1 C8 106.74(15)
C1 C2 C3 119.32(16)
C1 C2 H2A 120.3
C3 C2 H2A 120.3
C2 C3 C4 118.91(17)
C2 C3 C16 120.98(16)
C4 C3 C16 120.09(16)
C5 C4 C3 122.58(17)
C5 C4 H4A 118.7
C3 C4 H4A 118.7
C6 C5 C4 117.04(16)
C6 C5 H5A 121.5
C4 C5 H5A 121.5
C5 C6 C1 121.91(16)
C5 C6 N1 128.63(15)
C1 C6 N1 109.45(15)
O1 C7 N1 127.33(15)
O1 C7 C8 126.46(15)
N1 C7 C8 106.20(15)
N2 C8 C1 126.19(15)
N2 C8 C7 127.40(16)
C1 C8 C7 106.37(13)
N4 C9 N3 113.02(15)
N4 C9 S1 129.63(13)
N3 C9 S1 117.35(12)
C11 C10 C15 119.59(15)
C11 C10 N4 124.33(15)
C15 C10 N4 116.02(15)
C10 C11 C12 119.45(16)
C10 C11 H11A 120.3
C12 C11 H11A 120.3
C13 C12 C11 121.24(17)
C13 C12 H12A 119.4
C11 C12 H12A 119.4
C12 C13 C14 119.17(17)
C12 C13 H13A 120.4
C14 C13 H13A 120.4
C13 C14 C15 120.20(17)
C13 C14 H14A 119.9
C15 C14 H14A 119.9
C14 C15 C10 120.33(17)
C14 C15 H15A 119.8
C10 C15 H15A 119.8
C3 C16 H16A 109.5
C3 C16 H16B 109.5
H16A C16 H16B 109.5
C3 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.6643(17)
O1 C7 1.236(2)
N1 C7 1.355(2)
N1 C6 1.414(2)
N1 H1N1 0.89(3)
N2 C8 1.296(2)
N2 N3 1.349(2)
N3 C9 1.385(2)
N3 H1N3 0.91(2)
N4 C9 1.346(2)
N4 C10 1.417(2)
N4 H1N4 0.84(2)
C1 C2 1.393(2)
C1 C6 1.400(2)
C1 C8 1.454(2)
C2 C3 1.397(2)
C2 H2A 0.9500
C3 C4 1.401(2)
C3 C16 1.508(3)
C4 C5 1.400(3)
C4 H4A 0.9500
C5 C6 1.380(2)
C5 H5A 0.9500
C7 C8 1.507(2)
C10 C11 1.390(2)
C10 C15 1.396(2)
C11 C12 1.392(2)
C11 H11A 0.9500
C12 C13 1.386(3)
C12 H12A 0.9500
C13 C14 1.389(3)
C13 H13A 0.9500
C14 C15 1.391(2)
C14 H14A 0.9500
C15 H15A 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
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
N4 H1N4 N2 . 0.84(2) 2.14(2) 2.5947(18) 114.1(18) no
N1 H1N1 O1 3_765 0.89(2) 1.96(2) 2.848(2) 173(2) yes
N3 H1N3 O1 . 0.91(2) 2.04(2) 2.7595(17) 135.8(19) yes
C11 H11A S1 . 0.95 2.63 3.2712(18) 125 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
C8 N2 N3 C9 173.20(15)
C6 C1 C2 C3 -0.8(3)
C8 C1 C2 C3 177.80(17)
C1 C2 C3 C4 0.5(3)
C1 C2 C3 C16 179.03(17)
C2 C3 C4 C5 0.2(3)
C16 C3 C4 C5 -178.40(18)
C3 C4 C5 C6 -0.5(3)
C4 C5 C6 C1 0.1(3)
C4 C5 C6 N1 -178.48(17)
C2 C1 C6 C5 0.5(3)
C8 C1 C6 C5 -178.41(16)
C2 C1 C6 N1 179.35(15)
C8 C1 C6 N1 0.42(19)
C7 N1 C6 C5 176.62(17)
C7 N1 C6 C1 -2.1(2)
C6 N1 C7 O1 -176.20(16)
C6 N1 C7 C8 2.77(18)
N3 N2 C8 C1 -177.47(15)
N3 N2 C8 C7 -0.2(2)
C2 C1 C8 N2 0.2(3)
C6 C1 C8 N2 178.90(16)
C2 C1 C8 C7 -177.55(18)
C6 C1 C8 C7 1.20(18)
O1 C7 C8 N2 -1.1(3)
N1 C7 C8 N2 179.90(16)
O1 C7 C8 C1 176.55(16)
N1 C7 C8 C1 -2.43(18)
C10 N4 C9 N3 -177.56(16)
C10 N4 C9 S1 2.6(3)
N2 N3 C9 N4 7.3(2)
N2 N3 C9 S1 -172.89(12)
C9 N4 C10 C11 -21.0(3)
C9 N4 C10 C15 161.84(18)
C15 C10 C11 C12 -0.4(3)
N4 C10 C11 C12 -177.43(16)
C10 C11 C12 C13 0.6(3)
C11 C12 C13 C14 -0.2(3)
C12 C13 C14 C15 -0.4(3)
C13 C14 C15 C10 0.6(3)
C11 C10 C15 C14 -0.2(3)
N4 C10 C15 C14 177.06(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4698553
