Synthesis of 4-amino-7-oxyindoles <i>via</i> dearomatization of 4-alkyl-2-alkynylanilines and dual fragment incorporation with <i>O</i>-benzoylhydroxylamines.
Wu, Zhengping; Fan, Renhua; He, Qiuqin; Organic & biomolecular chemistry 24 (2026) 989–994; doi:10.1039/d5ob01832c

data_7160973
_publ_section_title
;
 Synthesis of 4-amino-7-oxyindoles <i>via</i> dearomatization of
 4-alkyl-2-alkynylanilines and dual fragment incorporation with
 <i>O</i>-benzoylhydroxylamines.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              989
_journal_page_last               994
_journal_paper_doi               10.1039/d5ob01832c
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C29 H22 Br N3 O6 S'
_chemical_formula_sum            'C29 H22 Br N3 O6 S'
_chemical_formula_weight         620.46
_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   mixed
_audit_creation_date             2024-09-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2025-11-05 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                81.247(4)
_cell_angle_beta                 67.573(3)
_cell_angle_gamma                79.206(4)
_cell_formula_units_Z            2
_cell_length_a                   10.8071(12)
_cell_length_b                   11.4940(12)
_cell_length_c                   11.7684(12)
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.49
_cell_volume                     1322.1(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11487
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.145
_diffrn_reflns_theta_min         2.492
_exptl_absorpt_coefficient_mu    1.684
_exptl_absorpt_correction_T_max  0.8014
_exptl_absorpt_correction_T_min  0.7036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1162 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.8780.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5820
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.5515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0854
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5008
_reflns_number_total             5820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01832c2.cif
_cod_data_source_block           mo_240907b_a
_cod_database_code               7160973
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.751
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2A = N2-H2B
 0.95 with sigma of 0.05
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C18(H18),
 C20(H20), C21(H21), C25(H25), C26(H26), C28(H28), C29(H29)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              60827
_shelx_shelxl_version_number     2019/2
_olex2_submission_special_instructions 'No special instructions were received'