#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/62/2226281.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_2226281
loop_
_publ_author_name
'Pervez, Humayun'
'Iqbal, Mohammad S.'
'Saira, Naveeda'
'Yaqub, Muhammad'
'Tahir, M. Nawaz'
_publ_section_title
;
 4-(3-Methoxyphenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide
;
_journal_coeditor_code           SI2262
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1404
_journal_paper_doi               10.1107/S1600536810018052
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H14 N4 O2 S'
_chemical_formula_moiety         'C16 H14 N4 O2 S'
_chemical_formula_sum            'C16 H14 N4 O2 S'
_chemical_formula_weight         326.37
_chemical_name_systematic
;
4-(3-Methoxyphenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 111.179(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1793(5)
_cell_length_b                   7.2473(2)
_cell_length_c                   15.4764(5)
_cell_measurement_reflns_used    2898
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      3.24
_cell_volume                     1587.55(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13861
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         3.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.353
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0539P)²+0.6227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1248
_reflns_number_gt                2898
_reflns_number_total             3925
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2262.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226281
_cod_database_fobs_code          2226281
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'
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_disorder_assembly
_atom_site_disorder_group
C C1 0.19826(11) 0.3610(2) 0.45348(11) 0.0329(3) Uani d . 1 . .
C C2 0.26044(11) 0.3126(2) 0.54720(11) 0.0345(3) Uani d . 1 . .
C C3 0.35347(12) 0.2547(3) 0.58412(12) 0.0434(4) Uani d . 1 . .
H H3 0.3882 0.2332 0.5464 0.052 Uiso calc R 1 . .
C C4 0.39313(14) 0.2298(3) 0.67919(13) 0.0515(5) Uani d . 1 . .
H H4 0.4555 0.1908 0.7057 0.062 Uiso calc R 1 . .
C C5 0.34181(15) 0.2617(3) 0.73516(13) 0.0529(5) Uani d . 1 . .
H H5 0.3705 0.2446 0.7988 0.063 Uiso calc R 1 . .
C C6 0.24859(14) 0.3187(3) 0.69884(12) 0.0491(5) Uani d . 1 . .
H H6 0.2140 0.3403 0.7367 0.059 Uiso calc R 1 . .
C C7 0.20928(11) 0.3419(2) 0.60448(11) 0.0382(4) Uani d . 1 . .
C C8 0.10524(11) 0.4125(2) 0.46058(11) 0.0359(4) Uani d . 1 . .
C C9 0.17432(11) 0.4498(2) 0.22293(11) 0.0360(4) Uani d . 1 . .
C C10 0.30202(12) 0.3962(2) 0.16100(12) 0.0388(4) Uani d . 1 . .
C C11 0.24941(12) 0.3445(2) 0.07119(12) 0.0407(4) Uani d . 1 . .
H H11 0.1865 0.3103 0.0552 0.049 Uiso calc R 1 . .
C C12 0.29128(13) 0.3440(3) 0.00497(13) 0.0446(4) Uani d . 1 . .
C C13 0.38568(14) 0.3931(3) 0.02993(15) 0.0539(5) Uani d . 1 . .
H H13 0.4139 0.3948 -0.0143 0.065 Uiso calc R 1 . .
C C14 0.43705(14) 0.4392(3) 0.11998(16) 0.0554(5) Uani d . 1 . .
H H14 0.5006 0.4689 0.1366 0.066 Uiso calc R 1 . .
C C15 0.39605(13) 0.4423(3) 0.18678(14) 0.0477(4) Uani d . 1 . .
H H15 0.4313 0.4748 0.2476 0.057 Uiso calc R 1 . .
C C16 0.14733(15) 0.2526(3) -0.11290(15) 0.0613(6) Uani d . 1 . .
H H16A 0.1142 0.3578 -0.1023 0.092 Uiso calc R 1 . .
H H16B 0.1387 0.1496 -0.0777 0.092 Uiso calc R 1 . .
H H16C 0.1230 0.2222 -0.1776 0.092 Uiso calc R 1 . .
N N1 0.11680(10) 0.3984(2) 0.55058(10) 0.0429(4) Uani d . 1 . .
H H1 0.0733 0.4210 0.5725 0.051 Uiso calc R 1 . .
N N2 0.22156(9) 0.36975(19) 0.38155(9) 0.0351(3) Uani d . 1 . .
N N3 0.15482(9) 0.4293(2) 0.30214(9) 0.0374(3) Uani d . 1 . .
H H3A 0.0992 0.4548 0.3013 0.045 Uiso calc R 1 . .
N N4 0.26118(10) 0.3955(2) 0.23067(10) 0.0416(4) Uani d . 1 . .
H H4A 0.2966 0.3552 0.2842 0.050 Uiso calc R 1 . .
O O1 0.03312(8) 0.45962(19) 0.39631(8) 0.0452(3) Uani d . 1 . .
O O2 0.24526(10) 0.2944(2) -0.08484(9) 0.0610(4) Uani d . 1 . .
S S1 0.09025(3) 0.53985(8) 0.13109(3) 0.04856(16) 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C2 . . 126.25(14) ?
N2 C1 C8 . . 127.64(14) ?
C2 C1 C8 . . 105.94(13) ?
C3 C2 C7 . . 120.33(15) ?
C3 C2 C1 . . 132.91(15) ?
C7 C2 C1 . . 106.72(13) ?
C2 C3 C4 . . 117.73(17) ?
C2 C3 H3 . . 121.1 ?
C4 C3 H3 . . 121.1 ?
C5 C4 C3 . . 121.22(17) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C4 C5 C6 . . 121.48(17) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C7 C6 C5 . . 117.13(17) ?
C7 C6 H6 . . 121.4 ?
C5 C6 H6 . . 121.4 ?
C6 C7 C2 . . 122.09(16) ?
C6 C7 N1 . . 128.44(16) ?
C2 C7 N1 . . 109.47(14) ?
O1 C8 N1 . . 127.11(15) ?
O1 C8 C1 . . 126.47(15) ?
N1 C8 C1 . . 106.42(13) ?
N4 C9 N3 . . 114.35(14) ?
N4 C9 S1 . . 128.21(13) ?
N3 C9 S1 . . 117.43(12) ?
C15 C10 C11 . . 121.28(16) ?
C15 C10 N4 . . 118.06(16) ?
C11 C10 N4 . . 120.61(15) ?
C10 C11 C12 . . 119.44(16) ?
C10 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
O2 C12 C11 . . 123.55(17) ?
O2 C12 C13 . . 116.72(17) ?
C11 C12 C13 . . 119.72(18) ?
C14 C13 C12 . . 119.75(18) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C13 C14 C15 . . 121.26(18) ?
C13 C14 H14 . . 119.4 ?
C15 C14 H14 . . 119.4 ?
C10 C15 C14 . . 118.52(18) ?
C10 C15 H15 . . 120.7 ?
C14 C15 H15 . . 120.7 ?
O2 C16 H16A . . 109.5 ?
O2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O2 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C8 N1 C7 . . 111.39(14) ?
C8 N1 H1 . . 124.3 ?
C7 N1 H1 . . 124.3 ?
C1 N2 N3 . . 116.95(13) ?
N2 N3 C9 . . 121.05(13) ?
N2 N3 H3A . . 119.5 ?
C9 N3 H3A . . 119.5 ?
C9 N4 C10 . . 127.93(14) ?
C9 N4 H4A . . 116.0 ?
C10 N4 H4A . . 116.0 ?
C12 O2 C16 . . 117.57(15) ?
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
C1 N2 . 1.286(2) ?
C1 C2 . 1.459(2) ?
C1 C8 . 1.503(2) ?
C2 C3 . 1.383(2) ?
C2 C7 . 1.390(2) ?
C3 C4 . 1.386(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.374(2) ?
C6 H6 . 0.9300 ?
C7 N1 . 1.410(2) ?
C8 O1 . 1.2319(19) ?
C8 N1 . 1.343(2) ?
C9 N4 . 1.339(2) ?
C9 N3 . 1.369(2) ?
C9 S1 . 1.6624(17) ?
C10 C15 . 1.377(2) ?
C10 C11 . 1.381(2) ?
C10 N4 . 1.425(2) ?
C11 C12 . 1.387(2) ?
C11 H11 . 0.9300 ?
C12 O2 . 1.359(2) ?
C12 C13 . 1.389(3) ?
C13 C14 . 1.370(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.386(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 O2 . 1.422(3) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
N1 H1 . 0.8600 ?
N2 N3 . 1.3504(18) ?
N3 H3A . 0.8600 ?
N4 H4A . 0.8600 ?
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
N1 H1 O1 3_566 0.8600 2.0400 2.875(2) 164.00 yes
N3 H3A O1 . 0.8600 2.0600 2.7441(19) 136.00 yes
N4 H4A N2 . 0.8600 2.1900 2.620(2) 110.00 yes
N4 H4A S1 2_545 0.8600 2.8700 3.5806(16) 141.00 yes
C11 H11 S1 . 0.9300 2.7400 3.212(2) 112.00 yes
C8 O1 Cg3 2_555 1.2319(19) 3.63660(10) 3.7399(17) 85.16(10) 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
N2 C1 C2 C3 . . . . -4.6(3) ?
C8 C1 C2 C3 . . . . 179.95(19) ?
N2 C1 C2 C7 . . . . 172.98(16) ?
C8 C1 C2 C7 . . . . -2.51(18) ?
C7 C2 C3 C4 . . . . -0.8(3) ?
C1 C2 C3 C4 . . . . 176.49(19) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 0.4(3) ?
C4 C5 C6 C7 . . . . 0.1(3) ?
C5 C6 C7 C2 . . . . -0.9(3) ?
C5 C6 C7 N1 . . . . -179.92(19) ?
C3 C2 C7 C6 . . . . 1.3(3) ?
C1 C2 C7 C6 . . . . -176.60(17) ?
C3 C2 C7 N1 . . . . -179.52(16) ?
C1 C2 C7 N1 . . . . 2.6(2) ?
N2 C1 C8 O1 . . . . 5.7(3) ?
C2 C1 C8 O1 . . . . -178.91(17) ?
N2 C1 C8 N1 . . . . -173.84(17) ?
C2 C1 C8 N1 . . . . 1.57(19) ?
C15 C10 C11 C12 . . . . -1.8(3) ?
N4 C10 C11 C12 . . . . -179.12(16) ?
C10 C11 C12 O2 . . . . 179.65(17) ?
C10 C11 C12 C13 . . . . 0.8(3) ?
O2 C12 C13 C14 . . . . -178.02(19) ?
C11 C12 C13 C14 . . . . 0.9(3) ?
C12 C13 C14 C15 . . . . -1.6(3) ?
C11 C10 C15 C14 . . . . 1.2(3) ?
N4 C10 C15 C14 . . . . 178.50(17) ?
C13 C14 C15 C10 . . . . 0.6(3) ?
O1 C8 N1 C7 . . . . -179.55(17) ?
C1 C8 N1 C7 . . . . 0.0(2) ?
C6 C7 N1 C8 . . . . 177.47(19) ?
C2 C7 N1 C8 . . . . -1.6(2) ?
C2 C1 N2 N3 . . . . -175.68(15) ?
C8 C1 N2 N3 . . . . -1.2(2) ?
C1 N2 N3 C9 . . . . 177.49(15) ?
N4 C9 N3 N2 . . . . 3.9(2) ?
S1 C9 N3 N2 . . . . -175.20(12) ?
N3 C9 N4 C10 . . . . 178.85(16) ?
S1 C9 N4 C10 . . . . -2.1(3) ?
C15 C10 N4 C9 . . . . 142.08(19) ?
C11 C10 N4 C9 . . . . -40.6(3) ?
C11 C12 O2 C16 . . . . 4.2(3) ?
C13 C12 O2 C16 . . . . -176.89(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6272023
2 PubChem 135763556
