#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/91/1569196.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_1569196
loop_
_publ_author_name
'Odedokun, Omobola A.'
'Ikotun, Adebomi A.'
'Ajaelu, Chijioke J.'
'Bhuvanesh, Nattamai'
_publ_section_title
;
 1-Benzyl-3-[(4-methoxyphenyl)imino]indolin-2-one
;
_journal_coeditor_code           BH4074
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x230418
_journal_paper_doi               10.1107/S2414314623004182
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          'C22 H18 N2 O2'
_chemical_formula_moiety         'C22 H18 N2 O2'
_chemical_formula_sum            'C22 H18 N2 O2'
_chemical_formula_weight         342.38
_chemical_name_systematic
;
1-Benzyl-3-[(4-methoxyphenyl)imino]indolin-2-one
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                94.374(6)
_cell_angle_beta                 110.139(6)
_cell_angle_gamma                93.747(6)
_cell_formula_units_Z            2
_cell_length_a                   8.8872(19)
_cell_length_b                   8.8922(19)
_cell_length_c                   11.772(3)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    300
_cell_measurement_theta_max      27.500
_cell_measurement_theta_min      2.453
_cell_volume                     866.7(3)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX2 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT  (Bruker, 2018)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
and PLATON (Spek, 2020).
;
_computing_structure_refinement
;
SHELXL  (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT  (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII DUO (PHOTON 100)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24116
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_min         1.853
_diffrn_source_current           40.0
_diffrn_source_power             1.6
_diffrn_source_voltage           40.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.3576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.547
_exptl_crystal_size_mid          0.529
_exptl_crystal_size_min          0.443
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.181
_refine_ls_extinction_coef       0.184(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0571
_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)+(0.0428P)²+0.2626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                3219
_reflns_number_total             4003
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bh4074.cif
_cod_data_source_block           I
_cod_database_code               1569196
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.963
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O O1 0.32465(13) 0.09548(11) 0.17890(9) 0.0467(3) Uani d 1 . .
O O2 0.15900(14) 0.09727(14) 0.84290(10) 0.0546(3) Uani d 1 . .
N N1 0.33951(14) 0.35590(13) 0.20515(10) 0.0367(3) Uani d 1 . .
N N2 0.28029(13) 0.11348(12) 0.40997(10) 0.0340(3) Uani d 1 . .
C C1 0.32025(15) 0.21291(15) 0.23706(12) 0.0336(3) Uani d 1 . .
C C2 0.28984(14) 0.23196(14) 0.35726(11) 0.0290(3) Uani d 1 . .
C C3 0.29136(14) 0.39654(14) 0.38541(11) 0.0295(3) Uani d 1 . .
C C4 0.32480(15) 0.46621(15) 0.29236(12) 0.0324(3) Uani d 1 . .
C C5 0.34166(17) 0.62236(16) 0.29431(14) 0.0429(3) Uani d 1 . .
H H5 0.363199 0.667768 0.232234 0.051 Uiso calc 1 . .
C C6 0.32539(17) 0.70910(16) 0.39198(15) 0.0455(4) Uani d 1 . .
H H6 0.335311 0.814188 0.394595 0.055 Uiso calc 1 . .
C C7 0.29483(17) 0.64298(16) 0.48527(14) 0.0429(3) Uani d 1 . .
H H7 0.286015 0.703664 0.550177 0.051 Uiso calc 1 . .
C C8 0.27719(16) 0.48616(15) 0.48251(12) 0.0355(3) Uani d 1 . .
H H8 0.256098 0.441593 0.545095 0.043 Uiso calc 1 . .
C C9 0.37347(17) 0.38347(18) 0.09473(13) 0.0426(3) Uani d 1 . .
H H9A 0.352646 0.486352 0.076706 0.051 Uiso calc 1 . .
H H9B 0.300810 0.315234 0.027033 0.051 Uiso calc 1 . .
C C10 0.54526(17) 0.36126(16) 0.10615(12) 0.0364(3) Uani d 1 . .
C C11 0.5760(2) 0.24368(17) 0.03577(14) 0.0458(4) Uani d 1 . .
H H11 0.490557 0.178863 -0.017936 0.055 Uiso calc 1 . .
C C12 0.7322(2) 0.2210(2) 0.04411(17) 0.0576(4) Uani d 1 . .
H H12 0.751328 0.142265 -0.004234 0.069 Uiso calc 1 . .
C C13 0.8587(2) 0.3160(2) 0.12445(18) 0.0634(5) Uani d 1 . .
H H13 0.963785 0.301025 0.130876 0.076 Uiso calc 1 . .
C C14 0.8301(2) 0.4332(2) 0.19530(17) 0.0612(5) Uani d 1 . .
H H14 0.916046 0.496349 0.250138 0.073 Uiso calc 1 . .
C C15 0.67396(19) 0.45734(19) 0.18531(14) 0.0484(4) Uani d 1 . .
H H15 0.655276 0.538342 0.231865 0.058 Uiso calc 1 . .
C C16 0.24553(15) 0.11827(14) 0.51921(11) 0.0311(3) Uani d 1 . .
C C17 0.10870(16) 0.17623(15) 0.52979(12) 0.0360(3) Uani d 1 . .
H H17 0.039392 0.220029 0.465081 0.043 Uiso calc 1 . .
C C18 0.07458(16) 0.16936(16) 0.63595(13) 0.0372(3) Uani d 1 . .
H H18 -0.017670 0.207542 0.641944 0.045 Uiso calc 1 . .
C C19 0.17839(17) 0.10545(15) 0.73296(12) 0.0370(3) Uani d 1 . .
C C20 0.31359(17) 0.04389(16) 0.72204(13) 0.0403(3) Uani d 1 . .
H H20 0.382694 -0.000043 0.786762 0.048 Uiso calc 1 . .
C C21 0.34513(16) 0.04796(15) 0.61558(12) 0.0360(3) Uani d 1 . .
H H21 0.433457 0.003537 0.607830 0.043 Uiso calc 1 . .
C C22 0.0133(2) 0.1394(2) 0.85474(16) 0.0595(5) Uani d 1 . .
H H22A -0.076403 0.080458 0.793597 0.089 Uiso calc 1 . .
H H22B 0.005243 0.245081 0.844710 0.089 Uiso calc 1 . .
H H22C 0.012674 0.121264 0.933923 0.089 Uiso calc 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'
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
C19 O2 C22 . . 118.34(12) ?
C1 N1 C4 . . 110.94(10) ?
C1 N1 C9 . . 122.28(12) ?
C4 N1 C9 . . 126.77(12) ?
C2 N2 C16 . . 122.11(11) ?
O1 C1 N1 . . 125.81(12) ?
O1 C1 C2 . . 127.73(12) ?
N1 C1 C2 . . 106.44(11) ?
N2 C2 C1 . . 117.81(11) ?
N2 C2 C3 . . 136.54(12) ?
C3 C2 C1 . . 105.47(10) ?
C4 C3 C2 . . 106.74(11) ?
C8 C3 C2 . . 133.75(12) ?
C8 C3 C4 . . 119.38(12) ?
C3 C4 N1 . . 110.38(11) ?
C5 C4 N1 . . 128.15(12) ?
C5 C4 C3 . . 121.46(12) ?
C4 C5 H5 . . 121.1 ?
C4 C5 C6 . . 117.89(13) ?
C6 C5 H5 . . 121.1 ?
C5 C6 H6 . . 119.2 ?
C7 C6 C5 . . 121.59(13) ?
C7 C6 H6 . . 119.2 ?
C6 C7 H7 . . 119.9 ?
C6 C7 C8 . . 120.26(13) ?
C8 C7 H7 . . 119.9 ?
C3 C8 C7 . . 119.41(13) ?
C3 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
N1 C9 H9A . . 109.0 ?
N1 C9 H9B . . 109.0 ?
N1 C9 C10 . . 112.92(11) ?
H9A C9 H9B . . 107.8 ?
C10 C9 H9A . . 109.0 ?
C10 C9 H9B . . 109.0 ?
C11 C10 C9 . . 119.80(13) ?
C11 C10 C15 . . 118.76(14) ?
C15 C10 C9 . . 121.44(13) ?
C10 C11 H11 . . 119.5 ?
C10 C11 C12 . . 121.00(15) ?
C12 C11 H11 . . 119.5 ?
C11 C12 H12 . . 120.2 ?
C13 C12 C11 . . 119.51(16) ?
C13 C12 H12 . . 120.2 ?
C12 C13 H13 . . 119.9 ?
C14 C13 C12 . . 120.16(16) ?
C14 C13 H13 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C13 C14 C15 . . 120.28(16) ?
C15 C14 H14 . . 119.9 ?
C10 C15 H15 . . 119.9 ?
C14 C15 C10 . . 120.27(15) ?
C14 C15 H15 . . 119.9 ?
C17 C16 N2 . . 122.85(12) ?
C17 C16 C21 . . 118.87(12) ?
C21 C16 N2 . . 117.96(11) ?
C16 C17 H17 . . 119.7 ?
C18 C17 C16 . . 120.69(12) ?
C18 C17 H17 . . 119.7 ?
C17 C18 H18 . . 120.1 ?
C19 C18 C17 . . 119.80(12) ?
C19 C18 H18 . . 120.1 ?
O2 C19 C18 . . 124.58(12) ?
O2 C19 C20 . . 115.57(12) ?
C18 C19 C20 . . 119.85(12) ?
C19 C20 H20 . . 119.9 ?
C21 C20 C19 . . 120.15(13) ?
C21 C20 H20 . . 119.9 ?
C16 C21 H21 . . 119.7 ?
C20 C21 C16 . . 120.53(12) ?
C20 C21 H21 . . 119.7 ?
O2 C22 H22A . . 109.5 ?
O2 C22 H22B . . 109.5 ?
O2 C22 H22C . . 109.5 ?
H22A C22 H22B . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
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
O1 C1 . 1.2147(16) ?
O2 C19 . 1.3697(16) ?
O2 C22 . 1.4197(19) ?
N1 C1 . 1.3695(17) ?
N1 C4 . 1.4102(17) ?
N1 C9 . 1.4663(17) ?
N2 C2 . 1.2753(16) ?
N2 C16 . 1.4205(16) ?
C1 C2 . 1.5286(17) ?
C2 C3 . 1.4739(17) ?
C3 C4 . 1.4056(18) ?
C3 C8 . 1.3895(18) ?
C4 C5 . 1.3843(19) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.390(2) ?
C6 H6 . 0.9300 ?
C6 C7 . 1.381(2) ?
C7 H7 . 0.9300 ?
C7 C8 . 1.3897(19) ?
C8 H8 . 0.9300 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C9 C10 . 1.513(2) ?
C10 C11 . 1.384(2) ?
C10 C15 . 1.387(2) ?
C11 H11 . 0.9300 ?
C11 C12 . 1.387(2) ?
C12 H12 . 0.9300 ?
C12 C13 . 1.376(3) ?
C13 H13 . 0.9300 ?
C13 C14 . 1.376(3) ?
C14 H14 . 0.9300 ?
C14 C15 . 1.384(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.3915(18) ?
C16 C21 . 1.3966(19) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.3884(19) ?
C18 H18 . 0.9300 ?
C18 C19 . 1.386(2) ?
C19 C20 . 1.3934(19) ?
C20 H20 . 0.9300 ?
C20 C21 . 1.3776(19) ?
C21 H21 . 0.9300 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
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
O1 C1 C2 N2 . . . . 6.2(2) ?
O1 C1 C2 C3 . . . . -177.95(13) ?
O2 C19 C20 C21 . . . . -179.24(13) ?
N1 C1 C2 N2 . . . . -174.78(11) ?
N1 C1 C2 C3 . . . . 1.07(13) ?
N1 C4 C5 C6 . . . . -178.48(13) ?
N1 C9 C10 C11 . . . . 113.49(15) ?
N1 C9 C10 C15 . . . . -67.07(18) ?
N2 C2 C3 C4 . . . . 172.91(14) ?
N2 C2 C3 C8 . . . . -2.5(2) ?
N2 C16 C17 C18 . . . . 175.73(12) ?
N2 C16 C21 C20 . . . . -177.48(12) ?
C1 N1 C4 C3 . . . . -1.19(15) ?
C1 N1 C4 C5 . . . . 177.75(13) ?
C1 N1 C9 C10 . . . . -74.72(17) ?
C1 C2 C3 C4 . . . . -1.74(13) ?
C1 C2 C3 C8 . . . . -177.20(13) ?
C2 N2 C16 C17 . . . . 56.00(18) ?
C2 N2 C16 C21 . . . . -130.53(13) ?
C2 C3 C4 N1 . . . . 1.84(14) ?
C2 C3 C4 C5 . . . . -177.19(12) ?
C2 C3 C8 C7 . . . . 175.61(13) ?
C3 C4 C5 C6 . . . . 0.4(2) ?
C4 N1 C1 O1 . . . . 179.06(13) ?
C4 N1 C1 C2 . . . . 0.02(14) ?
C4 N1 C9 C10 . . . . 104.17(15) ?
C4 C3 C8 C7 . . . . 0.60(19) ?
C4 C5 C6 C7 . . . . 0.6(2) ?
C5 C6 C7 C8 . . . . -0.9(2) ?
C6 C7 C8 C3 . . . . 0.3(2) ?
C8 C3 C4 N1 . . . . 178.07(11) ?
C8 C3 C4 C5 . . . . -0.95(19) ?
C9 N1 C1 O1 . . . . -1.9(2) ?
C9 N1 C1 C2 . . . . 179.07(11) ?
C9 N1 C4 C3 . . . . 179.82(12) ?
C9 N1 C4 C5 . . . . -1.2(2) ?
C9 C10 C11 C12 . . . . 179.78(14) ?
C9 C10 C15 C14 . . . . 179.05(14) ?
C10 C11 C12 C13 . . . . 0.6(3) ?
C11 C10 C15 C14 . . . . -1.5(2) ?
C11 C12 C13 C14 . . . . -0.4(3) ?
C12 C13 C14 C15 . . . . -0.7(3) ?
C13 C14 C15 C10 . . . . 1.7(3) ?
C15 C10 C11 C12 . . . . 0.3(2) ?
C16 N2 C2 C1 . . . . -177.27(11) ?
C16 N2 C2 C3 . . . . 8.6(2) ?
C16 C17 C18 C19 . . . . 0.6(2) ?
C17 C16 C21 C20 . . . . -3.7(2) ?
C17 C18 C19 O2 . . . . 177.83(13) ?
C17 C18 C19 C20 . . . . -2.1(2) ?
C18 C19 C20 C21 . . . . 0.7(2) ?
C19 C20 C21 C16 . . . . 2.3(2) ?
C21 C16 C17 C18 . . . . 2.3(2) ?
C22 O2 C19 C18 . . . . 8.2(2) ?
C22 O2 C19 C20 . . . . -171.81(14) ?
