#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:28:28 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298027 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/42/7134228.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_7134228
loop_
_publ_author_name
'Tyagi, Kartikay'
'Dixit, Tejal'
'Venkatesh, V.'
_publ_section_title
;
 Visible light-induced photoisomerization of indole-oxindole constructs:
 molecular disassembly and ROS-mediated apoptosis.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3892
_journal_page_last               3895
_journal_paper_doi               10.1039/d4cc06624c
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '0.5(C19 H14 N2 O)'
_chemical_formula_sum            'C9.5 H7 N O0.5'
_chemical_formula_weight         143.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-10-01 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.737(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.576(4)
_cell_length_b                   4.7113(16)
_cell_length_c                   14.303(5)
_cell_measurement_reflns_used    822
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      19.456
_cell_measurement_theta_min      2.181
_cell_volume                     695.1(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL n/a (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1125
_diffrn_reflns_av_unetI/netI     0.1515
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7573
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        24.544
_diffrn_reflns_theta_max         24.544
_diffrn_reflns_theta_min         1.974
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.5348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0862 after correction.
The Ratio of minimum to maximum transmission is 0.7178.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.019
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 393 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0792
_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)+(0.0648P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1728
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                1381
_reflns_number_total             2326
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc06624c2.cif
_cod_data_source_block           vv_kt_784_1026_0m
_cod_depositor_comments
'Adding full bibliography for 7134227--7134231.cif.'
_cod_original_formula_sum        'C9.50 H7 N O0.50'
_cod_database_code               7134228
_shelx_shelxl_version_number     2019/1
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C17(H17), C6(H6), C11(H11), C18(H18), C5(H5), C16(H16), C14(H14),
 C15(H15), C7(H7), C8(H8), C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.4728(5) 0.5086(10) 0.8932(4) 0.0405(16) Uani 1 1 d . . . . .
N2 N 0.4692(6) -0.0558(12) 0.6695(5) 0.0326(17) Uani 1 1 d . . . . .
N1 N 0.3461(6) 0.8498(12) 0.9419(4) 0.0344(18) Uani 1 1 d . . . . .
H1 H 0.398991 0.891382 0.996758 0.041 Uiso 1 1 calc R U . . .
C13 C 0.2723(7) 0.1141(14) 0.5949(5) 0.0261(19) Uani 1 1 d . . . . .
C3 C 0.1678(7) 0.8590(14) 0.8182(5) 0.028(2) Uani 1 1 d . . . . .
C2 C 0.2590(7) 0.6454(14) 0.7972(5) 0.0256(19) Uani 1 1 d . . . . .
C4 C 0.2244(8) 0.9771(15) 0.9067(6) 0.032(2) Uani 1 1 d . . . . .
C12 C 0.3720(7) -0.0871(15) 0.5885(5) 0.029(2) Uani 1 1 d . . . . .
C1 C 0.3696(8) 0.6511(16) 0.8776(6) 0.036(2) Uani 1 1 d . . . . .
C17 C 0.3621(8) -0.2649(15) 0.5104(6) 0.035(2) Uani 1 1 d . . . . .
H17 H 0.428863 -0.396546 0.506779 0.043 Uiso 1 1 calc R U . . .
C6 C 0.0416(8) 1.2728(15) 0.9010(6) 0.036(2) Uani 1 1 d . . . . .
H6 H -0.003741 1.412356 0.928621 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3146(7) 0.2627(15) 0.6838(6) 0.030(2) Uani 1 1 d . . . . .
C11 C 0.4339(8) 0.1563(15) 0.7267(6) 0.034(2) Uani 1 1 d . . . . .
H11 H 0.484906 0.217787 0.786525 0.040 Uiso 1 1 calc R U . . .
C18 C 0.5835(8) -0.2174(15) 0.6903(7) 0.038(2) Uani 1 1 d . . . . .
H18 H 0.595744 -0.351461 0.643515 0.045 Uiso 1 1 calc R U . . .
C5 C 0.1628(8) 1.1867(15) 0.9503(6) 0.036(2) Uani 1 1 d . . . . .
H5 H 0.202453 1.265553 1.010807 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2530(8) -0.2453(15) 0.4384(6) 0.039(2) Uani 1 1 d . . . . .
H16 H 0.244955 -0.364555 0.383788 0.047 Uiso 1 1 calc R U . . .
C14 C 0.1625(7) 0.1260(16) 0.5208(6) 0.033(2) Uani 1 1 d . . . . .
H14 H 0.094800 0.256265 0.523366 0.040 Uiso 1 1 calc R U . . .
C15 C 0.1532(7) -0.0549(16) 0.4429(6) 0.034(2) Uani 1 1 d . . . . .
H15 H 0.078162 -0.049249 0.392201 0.041 Uiso 1 1 calc R U . . .
C7 C -0.0156(8) 1.1604(16) 0.8120(6) 0.034(2) Uani 1 1 d . . . . .
H7 H -0.098656 1.225858 0.779446 0.041 Uiso 1 1 calc R U . . .
C8 C 0.0473(8) 0.9529(16) 0.7699(6) 0.036(2) Uani 1 1 d . . . . .
H8 H 0.007914 0.876890 0.708927 0.044 Uiso 1 1 calc R U . . .
C9 C 0.2408(7) 0.4849(16) 0.7162(6) 0.033(2) Uani 1 1 d . . . . .
H9 H 0.162585 0.528469 0.671453 0.040 Uiso 1 1 calc R U . . .
C19 C 0.6757(11) -0.200(2) 0.7693(8) 0.044(3) Uani 1 1 d . . . . .
H19A H 0.660(8) -0.10(2) 0.829(6) 0.07(3) Uiso 1 1 d . . . . .
H19B H 0.736(8) -0.32(2) 0.768(6) 0.06(4) Uiso 1 1 d . . . . .
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
C12 N2 C11 108.9(6) . . ?
C12 N2 C18 124.7(7) . . ?
C11 N2 C18 126.4(7) . . ?
C4 N1 H1 125.1 . . ?
C1 N1 H1 125.1 . . ?
C1 N1 C4 109.7(6) . . ?
C10 C13 C12 106.8(6) . . ?
C14 C13 C12 118.7(7) . . ?
C14 C13 C10 134.6(7) . . ?
C4 C3 C2 106.8(6) . . ?
C8 C3 C2 133.7(7) . . ?
C8 C3 C4 119.5(7) . . ?
C1 C2 C3 106.0(7) . . ?
C9 C2 C3 125.3(6) . . ?
C9 C2 C1 128.6(7) . . ?
C3 C4 N1 109.4(7) . . ?
C3 C4 C5 122.4(7) . . ?
C5 C4 N1 128.2(7) . . ?
N2 C12 C13 107.3(6) . . ?
N2 C12 C17 130.9(7) . . ?
C17 C12 C13 121.8(7) . . ?
O1 C1 N1 121.5(7) . . ?
O1 C1 C2 130.4(8) . . ?
N1 C1 C2 108.1(7) . . ?
C12 C17 H17 121.0 . . ?
C16 C17 C12 117.9(7) . . ?
C16 C17 H17 121.0 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.7(7) . . ?
C7 C6 H6 119.2 . . ?
C13 C10 C9 123.6(7) . . ?
C11 C10 C13 107.2(7) . . ?
C11 C10 C9 129.2(7) . . ?
N2 C11 H11 125.1 . . ?
C10 C11 N2 109.7(7) . . ?
C10 C11 H11 125.1 . . ?
N2 C18 H18 117.1 . . ?
C19 C18 N2 125.9(9) . . ?
C19 C18 H18 117.1 . . ?
C4 C5 H5 121.7 . . ?
C6 C5 C4 116.7(7) . . ?
C6 C5 H5 121.7 . . ?
C17 C16 H16 119.1 . . ?
C17 C16 C15 121.8(8) . . ?
C15 C16 H16 119.1 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.1(7) . . ?
C15 C14 H14 120.4 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.7(7) . . ?
C14 C15 H15 119.7 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.7(7) . . ?
C8 C7 H7 119.6 . . ?
C3 C8 C7 119.0(7) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C2 C9 C10 133.8(7) . . ?
C2 C9 H9 113.1 . . ?
C10 C9 H9 113.1 . . ?
C18 C19 H19A 121(5) . . ?
C18 C19 H19B 111(6) . . ?
H19A C19 H19B 126(8) . . ?
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 C1 1.258(9) . ?
N2 C12 1.377(9) . ?
N2 C11 1.394(9) . ?
N2 C18 1.404(9) . ?
N1 H1 0.8800 . ?
N1 C4 1.408(10) . ?
N1 C1 1.373(9) . ?
C13 C12 1.436(10) . ?
C13 C10 1.434(9) . ?
C13 C14 1.390(9) . ?
C3 C2 1.471(10) . ?
C3 C4 1.391(10) . ?
C3 C8 1.382(10) . ?
C2 C1 1.449(9) . ?
C2 C9 1.361(9) . ?
C4 C5 1.404(10) . ?
C12 C17 1.381(10) . ?
C17 H17 0.9500 . ?
C17 C16 1.370(10) . ?
C6 H6 0.9500 . ?
C6 C5 1.380(10) . ?
C6 C7 1.388(10) . ?
C10 C11 1.371(10) . ?
C10 C9 1.443(10) . ?
C11 H11 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.322(12) . ?
C5 H5 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.398(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(10) . ?
C15 H15 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.392(10) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C19 H19A 1.02(9) . ?
C19 H19B 0.85(9) . ?
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
N2 C12 C17 C16 -178.8(7) . . . . ?
N1 C4 C5 C6 -178.9(7) . . . . ?
C13 C12 C17 C16 -0.3(11) . . . . ?
C13 C10 C11 N2 -0.5(9) . . . . ?
C13 C10 C9 C2 177.6(8) . . . . ?
C13 C14 C15 C16 -0.5(11) . . . . ?
C3 C2 C1 O1 -179.9(8) . . . . ?
C3 C2 C1 N1 0.5(8) . . . . ?
C3 C2 C9 C10 -177.7(8) . . . . ?
C3 C4 C5 C6 -0.1(10) . . . . ?
C2 C3 C4 N1 0.2(8) . . . . ?
C2 C3 C4 C5 -178.8(6) . . . . ?
C2 C3 C8 C7 178.8(7) . . . . ?
C4 N1 C1 O1 180.0(7) . . . . ?
C4 N1 C1 C2 -0.4(8) . . . . ?
C4 C3 C2 C1 -0.4(8) . . . . ?
C4 C3 C2 C9 -178.8(7) . . . . ?
C4 C3 C8 C7 -1.2(10) . . . . ?
C12 N2 C11 C10 0.1(8) . . . . ?
C12 N2 C18 C19 -177.0(8) . . . . ?
C12 C13 C10 C11 0.7(8) . . . . ?
C12 C13 C10 C9 179.6(7) . . . . ?
C12 C13 C14 C15 -0.4(11) . . . . ?
C12 C17 C16 C15 -0.7(11) . . . . ?
C1 N1 C4 C3 0.1(8) . . . . ?
C1 N1 C4 C5 179.1(7) . . . . ?
C1 C2 C9 C10 4.2(13) . . . . ?
C17 C16 C15 C14 1.1(12) . . . . ?
C6 C7 C8 C3 0.2(11) . . . . ?
C10 C13 C12 N2 -0.6(8) . . . . ?
C10 C13 C12 C17 -179.4(7) . . . . ?
C10 C13 C14 C15 180.0(8) . . . . ?
C11 N2 C12 C13 0.3(8) . . . . ?
C11 N2 C12 C17 179.0(8) . . . . ?
C11 N2 C18 C19 1.8(12) . . . . ?
C11 C10 C9 C2 -3.7(14) . . . . ?
C18 N2 C12 C13 179.3(7) . . . . ?
C18 N2 C12 C17 -2.0(12) . . . . ?
C18 N2 C11 C10 -178.9(7) . . . . ?
C5 C6 C7 C8 0.9(11) . . . . ?
C14 C13 C12 N2 179.7(7) . . . . ?
C14 C13 C12 C17 0.8(11) . . . . ?
C14 C13 C10 C11 -179.7(8) . . . . ?
C14 C13 C10 C9 -0.7(13) . . . . ?
C7 C6 C5 C4 -0.9(11) . . . . ?
C8 C3 C2 C1 179.6(8) . . . . ?
C8 C3 C2 C9 1.2(13) . . . . ?
C8 C3 C4 N1 -179.9(6) . . . . ?
C8 C3 C4 C5 1.1(11) . . . . ?
C9 C2 C1 O1 -1.6(13) . . . . ?
C9 C2 C1 N1 178.8(7) . . . . ?
C9 C10 C11 N2 -179.4(7) . . . . ?
