A TBADT-enabled photo-induced radical cyclization pathway: concise access to functionalized oxindoles
Gowda, Punith S.; Sharada, Duddu S.; Satyanarayana, Gedu; Chemical Communications 61 (2025) 8391–8394; doi:10.1039/D5CC01590A

data_7134500
_publ_section_title
;
 A TBADT-enabled photo-induced radical cyclization pathway: concise access
 to functionalized oxindoles
;
_journal_issue                   46
_journal_name_full               'Chemical Communications'
_journal_page_first              8391
_journal_page_last               8394
_journal_paper_doi               10.1039/D5CC01590A
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C13 H15 N O3'
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-12
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.11.02 svn.r19aeb66f for OlexSys, GUI svn.r7078)
;
_audit_update_record
;
2024-11-12 deposited with the CCDC.	2025-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.300(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1369(3)
_cell_length_b                   9.3444(5)
_cell_length_c                   25.1733(16)
_cell_measurement_reflns_used    3808
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.554
_cell_measurement_theta_min      2.716
_cell_volume                     1207.38(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-V Photon II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            16379
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.142
_diffrn_reflns_theta_min         2.325
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0890 before and 0.0661 after correction.
The Ratio of minimum to maximum transmission is 0.7096.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear brownish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0845
_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
'w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.4193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1835
_reflns_number_total             2675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01590a2.cif
_cod_data_source_block           mo_gs_ps_p4me_2
_cod_depositor_comments
'Adding full bibliography for 7134498--7134500.cif.'
_cod_database_code               7134500
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              27131
_shelx_hkl_checksum              72606
_olex2_exptl_crystal_mounting_method 'nylon loop used'
_olex2_submission_special_instructions 'No special instructions were received'