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#$Date: 2025-08-22 11:56:18 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301860 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/60/7126089.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7126089
loop_
_publ_author_name
'Zhang, Cong-Hai'
'Huang, Rong'
'Qing, Xia'
'Lin, Jun'
'Yan, Sheng-Jiao'
_publ_section_title
;
 Cascade reaction of isatins with nitro-substituted enamines: highly
 selective synthesis of functionalized
 (Z)-3-(1-(arylamino)-2-oxoarylidene)indolin-2-ones.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3488
_journal_page_last               3491
_journal_paper_doi               10.1039/d0cc00923g
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-12-09 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.529(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3098(15)
_cell_length_b                   10.3197(17)
_cell_length_c                   18.503(3)
_cell_measurement_reflns_used    3482
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.993
_cell_measurement_theta_min      0.233
_cell_volume                     1777.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10634
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.188
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'LIGHT YELLOW'
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.864
_refine_ls_R_factor_all          0.1567
_refine_ls_R_factor_gt           0.0494
_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)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1464
_reflns_number_total             3482
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc00923g3.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7126089.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7126089
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5971(2) 0.46609(17) 0.08960(8) 0.0558(5) Uani 1 1 d . . . . .
O2 O 0.3999(2) 0.19281(19) 0.29475(9) 0.0736(6) Uani 1 1 d . . . . .
N1 N 0.3605(2) 0.43633(19) 0.05025(10) 0.0523(6) Uani 1 1 d . . . . .
H1 H 0.3694 0.4608 0.0062 0.063 Uiso 1 1 calc R U . . .
N2 N 0.6322(2) 0.4004(2) 0.23318(10) 0.0551(6) Uani 1 1 d . . . . .
H2 H 0.6642 0.4414 0.1965 0.066 Uiso 1 1 calc R U . . .
C1 C 0.2324(3) 0.3937(2) 0.07954(13) 0.0484(7) Uani 1 1 d . . . . .
C2 C 0.2571(3) 0.3641(2) 0.15287(13) 0.0472(7) Uani 1 1 d . . . . .
C3 C 0.1408(3) 0.3242(3) 0.19282(15) 0.0616(8) Uani 1 1 d . . . . .
H3 H 0.1524 0.3057 0.2418 0.074 Uiso 1 1 calc R U . . .
C4 C 0.0072(3) 0.3124(3) 0.15856(16) 0.0710(9) Uani 1 1 d . . . . .
H4 H -0.0706 0.2852 0.1852 0.085 Uiso 1 1 calc R U . . .
C5 C -0.0137(3) 0.3398(3) 0.08600(17) 0.0701(9) Uani 1 1 d . . . . .
H5 H -0.1045 0.3300 0.0645 0.084 Uiso 1 1 calc R U . . .
C6 C 0.0994(3) 0.3815(3) 0.04525(14) 0.0589(8) Uani 1 1 d . . . . .
H6 H 0.0866 0.4007 -0.0036 0.071 Uiso 1 1 calc R U . . .
C7 C 0.4099(3) 0.3874(2) 0.16802(12) 0.0459(7) Uani 1 1 d . . . . .
C8 C 0.4701(3) 0.4341(2) 0.10079(13) 0.0473(7) Uani 1 1 d . . . . .
C9 C 0.4927(3) 0.3676(2) 0.22922(12) 0.0461(7) Uani 1 1 d . . . . .
C10 C 0.4276(3) 0.3078(3) 0.29562(13) 0.0499(7) Uani 1 1 d . . . . .
C11 C 0.3940(3) 0.3935(2) 0.35682(12) 0.0466(7) Uani 1 1 d . . . . .
C12 C 0.4066(3) 0.5266(3) 0.35155(13) 0.0578(8) Uani 1 1 d . . . . .
H12 H 0.4412 0.5638 0.3097 0.069 Uiso 1 1 calc R U . . .
C13 C 0.3676(3) 0.6043(3) 0.40855(16) 0.0731(9) Uani 1 1 d . . . . .
H13 H 0.3735 0.6939 0.4046 0.088 Uiso 1 1 calc R U . . .
C14 C 0.3201(3) 0.5492(3) 0.47112(16) 0.0774(10) Uani 1 1 d . . . . .
H14 H 0.2954 0.6016 0.5097 0.093 Uiso 1 1 calc R U . . .
C15 C 0.3090(3) 0.4167(4) 0.47680(14) 0.0730(9) Uani 1 1 d . . . . .
H15 H 0.2768 0.3799 0.5193 0.088 Uiso 1 1 calc R U . . .
C16 C 0.3451(3) 0.3385(3) 0.42017(13) 0.0596(8) Uani 1 1 d . . . . .
H16 H 0.3369 0.2490 0.4241 0.072 Uiso 1 1 calc R U . . .
C17 C 0.7342(3) 0.3758(3) 0.29060(12) 0.0502(7) Uani 1 1 d . . . . .
C18 C 0.8239(3) 0.4740(3) 0.31188(14) 0.0646(8) Uani 1 1 d . . . . .
H18 H 0.8141 0.5557 0.2911 0.078 Uiso 1 1 calc R U . . .
C19 C 0.9291(3) 0.4518(3) 0.36428(16) 0.0779(10) Uani 1 1 d . . . . .
H19 H 0.9903 0.5187 0.3788 0.093 Uiso 1 1 calc R U . . .
C20 C 0.9437(3) 0.3326(3) 0.39476(16) 0.0808(10) Uani 1 1 d . . . . .
H20 H 1.0149 0.3180 0.4300 0.097 Uiso 1 1 calc R U . . .
C21 C 0.8546(4) 0.2348(3) 0.37375(17) 0.0849(11) Uani 1 1 d . . . . .
H21 H 0.8641 0.1536 0.3952 0.102 Uiso 1 1 calc R U . . .
C22 C 0.7496(3) 0.2551(3) 0.32067(15) 0.0696(9) Uani 1 1 d . . . . .
H22 H 0.6901 0.1875 0.3055 0.084 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 111.1(2) . . ?
C9 N2 C17 128.2(2) . . ?
C6 C1 N1 128.0(2) . . ?
C6 C1 C2 123.1(3) . . ?
N1 C1 C2 108.9(2) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 C7 135.6(2) . . ?
C1 C2 C7 106.4(2) . . ?
C4 C3 C2 119.0(3) . . ?
C5 C4 C3 121.9(3) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C1 117.7(3) . . ?
C9 C7 C8 122.3(2) . . ?
C9 C7 C2 131.1(2) . . ?
C8 C7 C2 106.5(2) . . ?
O1 C8 N1 125.1(2) . . ?
O1 C8 C7 127.9(2) . . ?
N1 C8 C7 107.0(2) . . ?
N2 C9 C7 122.0(2) . . ?
N2 C9 C10 117.7(2) . . ?
C7 C9 C10 120.2(2) . . ?
O2 C10 C11 123.1(2) . . ?
O2 C10 C9 118.4(2) . . ?
C11 C10 C9 118.4(2) . . ?
C12 C11 C16 119.7(2) . . ?
C12 C11 C10 121.4(2) . . ?
C16 C11 C10 118.9(2) . . ?
C13 C12 C11 119.9(3) . . ?
C14 C13 C12 120.0(3) . . ?
C13 C14 C15 120.2(3) . . ?
C16 C15 C14 120.4(3) . . ?
C15 C16 C11 119.8(3) . . ?
C18 C17 C22 120.1(3) . . ?
C18 C17 N2 118.2(2) . . ?
C22 C17 N2 121.6(2) . . ?
C17 C18 C19 119.8(3) . . ?
C20 C19 C18 120.3(3) . . ?
C21 C20 C19 120.0(3) . . ?
C20 C21 C22 120.4(3) . . ?
C17 C22 C21 119.4(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.250(3) . ?
O2 C10 1.215(3) . ?
N1 C8 1.365(3) . ?
N1 C1 1.394(3) . ?
N2 C9 1.342(3) . ?
N2 C17 1.429(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.404(3) . ?
C2 C3 1.390(4) . ?
C2 C7 1.462(3) . ?
C3 C4 1.386(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.380(4) . ?
C7 C9 1.368(3) . ?
C7 C8 1.460(3) . ?
C9 C10 1.515(3) . ?
C10 C11 1.477(3) . ?
C11 C12 1.382(3) . ?
C11 C16 1.390(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.373(4) . ?
C14 C15 1.375(4) . ?
C15 C16 1.371(4) . ?
C17 C18 1.365(3) . ?
C17 C22 1.370(3) . ?
C18 C19 1.379(3) . ?
C19 C20 1.358(4) . ?
C20 C21 1.357(4) . ?
C21 C22 1.383(4) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C6 -179.5(2) . . . . ?
C8 N1 C1 C2 1.1(3) . . . . ?
C6 C1 C2 C3 -1.9(4) . . . . ?
N1 C1 C2 C3 177.7(2) . . . . ?
C6 C1 C2 C7 179.1(2) . . . . ?
N1 C1 C2 C7 -1.4(3) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C7 C2 C3 C4 -179.7(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
N1 C1 C6 C5 -178.5(2) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C3 C2 C7 C9 5.3(5) . . . . ?
C1 C2 C7 C9 -175.9(3) . . . . ?
C3 C2 C7 C8 -177.6(3) . . . . ?
C1 C2 C7 C8 1.2(3) . . . . ?
C1 N1 C8 O1 179.4(2) . . . . ?
C1 N1 C8 C7 -0.2(3) . . . . ?
C9 C7 C8 O1 -2.7(4) . . . . ?
C2 C7 C8 O1 179.8(2) . . . . ?
C9 C7 C8 N1 176.8(2) . . . . ?
C2 C7 C8 N1 -0.6(3) . . . . ?
C17 N2 C9 C7 -174.2(2) . . . . ?
C17 N2 C9 C10 6.3(4) . . . . ?
C8 C7 C9 N2 5.9(4) . . . . ?
C2 C7 C9 N2 -177.4(2) . . . . ?
C8 C7 C9 C10 -174.6(2) . . . . ?
C2 C7 C9 C10 2.2(4) . . . . ?
N2 C9 C10 O2 -107.2(3) . . . . ?
C7 C9 C10 O2 73.2(3) . . . . ?
N2 C9 C10 C11 75.9(3) . . . . ?
C7 C9 C10 C11 -103.7(3) . . . . ?
O2 C10 C11 C12 -169.9(3) . . . . ?
C9 C10 C11 C12 6.8(4) . . . . ?
O2 C10 C11 C16 8.3(4) . . . . ?
C9 C10 C11 C16 -174.9(2) . . . . ?
C16 C11 C12 C13 -1.4(4) . . . . ?
C10 C11 C12 C13 176.8(2) . . . . ?
C11 C12 C13 C14 1.8(4) . . . . ?
C12 C13 C14 C15 -1.1(5) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C15 C16 C11 0.4(4) . . . . ?
C12 C11 C16 C15 0.3(4) . . . . ?
C10 C11 C16 C15 -177.9(3) . . . . ?
C9 N2 C17 C18 -135.6(3) . . . . ?
C9 N2 C17 C22 48.8(4) . . . . ?
C22 C17 C18 C19 -0.7(4) . . . . ?
N2 C17 C18 C19 -176.3(2) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C19 C20 C21 -0.1(5) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C18 C17 C22 C21 1.4(4) . . . . ?
N2 C17 C22 C21 176.9(3) . . . . ?
C20 C21 C22 C17 -1.5(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168351768
