[4 + 3] Annulation of diazoenals and 3-substituted 2-oxindoles: rapid access to indolo-oxazepines and a 5-HT<sub>4</sub> receptor antagonist core.
Lad, Bapurao Sudam; Kundu, Chayan Kumar; Tripathi, Sanchita; Katukojvala, Sreenivas; Organic & biomolecular chemistry 24 (2026) 1447–1451; doi:10.1039/d5ob01964h

data_7160994
_publ_section_title
;
 [4 + 3] Annulation of diazoenals and 3-substituted 2-oxindoles: rapid
 access to indolo-oxazepines and a 5-HT<sub>4</sub> receptor antagonist
 core.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1447
_journal_page_last               1451
_journal_paper_doi               10.1039/d5ob01964h
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         274.342
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2ptg66
_audit_creation_date             2025-10-22
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-10-22 deposited with the CCDC.	2026-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.2002(4)
_cell_length_b                   8.2262(3)
_cell_length_c                   37.1993(15)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      4.31
_cell_volume                     2815.3(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.9771
_diffrn_measured_fraction_theta_max 0.9820
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.9771
_diffrn_reflns_Laue_measured_fraction_max 0.9820
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            64808
_diffrn_reflns_point_group_measured_fraction_full 0.9771
_diffrn_reflns_point_group_measured_fraction_max 0.9820
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         3.71
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7138
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.9573.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       needle
_exptl_crystal_F_000             1176.770
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.3223
_refine_diff_density_min         -0.2770
_refine_diff_density_rms         0.0402
_refine_ls_d_res_high            0.7582
_refine_ls_d_res_low             5.4969
_refine_ls_goodness_of_fit_ref   0.9387
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9387
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+1.3620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              48
_reflns_limit_l_min              0
_reflns_number_gt                3059
_reflns_number_total             3325
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01964h2.cif
_cod_data_source_block           F1_a
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7160994
_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:
 C00G(H00k)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00a,H00b), C00D(H00f,H00g), C00F(H00i,H00j), C00J(H00o,H00p)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00c), C00B(H00d), C00C(H00e), C00E(H00h)
2.d Idealised Me refined as rotating group:
 C00I(H00l,H00m,H00n), C00K(H00q,H00r,H00s)
;
_olex2_exptl_crystal_mounting_method Lalit
_olex2_submission_special_instructions 'No special instructions were received'