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_7160974
_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         'C44 H33 Cl2 N3 O5 S2, C4 H10 O'
_chemical_formula_sum            'C48 H43 Cl2 N3 O6 S2'
_chemical_formula_weight         892.87
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-11-29
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2681(6)
_cell_length_b                   15.8022(6)
_cell_length_c                   34.5237(12)
_cell_measurement_reflns_used    8888
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.03
_cell_measurement_theta_min      3.16
_cell_volume                     8875.1(6)
_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      173.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            115884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.101
_diffrn_reflns_theta_max         53.101
_diffrn_reflns_theta_min         3.248
_exptl_absorpt_coefficient_mu    1.708
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1418 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.8159.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             3728
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     576
_refine_ls_number_reflns         7864
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0670P)^2^+7.1654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6036
_reflns_number_total             7864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01832c2.cif
_cod_data_source_block           ga_241128a_a
_cod_database_code               7160974
_shelx_estimated_absorpt_t_max   0.848
_shelx_estimated_absorpt_t_min   0.726
_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. Restrained distances
 C47'-O6
 1.42 with sigma of 0.01
 C47-C48 = C47'-C48'
 1.52 with sigma of 0.01
 C46-C47 = C46-C47'
 2.4 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C47 \\sim C47': within 2A with sigma of 0.02 and sigma for terminal atoms of
0.05
Uanis(C47) \\sim Ueq, Uanis(C47') \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C48')
\\sim Ueq: with sigma of 0.006 and sigma for terminal atoms of 0.012
4. Others
 Sof(C48')=Sof(H48D)=Sof(H48E)=Sof(H48F)=Sof(C47')=Sof(H47C)=Sof(H47D)=1-FVAR(1)
 Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C47(H47A,H47B), C47'(H47C,H47D)
5.b Me refined with riding coordinates:
 C36(H36A,H36B,H36C)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C10(H10), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C21(H21), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33),
  C34(H34), C38(H38), C39(H39), C41(H41), C42(H42)
5.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,
 H45C), C48(H48A,H48B,H48C), C48'(H48D,H48E,H48F)
;
_shelx_res_checksum              63593
_shelx_shelxl_version_number     2019/2
_olex2_submission_special_instructions 'No special instructions were received'