Iodine-promoted amide formation via oxidative cleavage of indoles: novel quinazoline-4(3H)-one and tryptanthrin syntheses
Le, Phong Q.; Dinh, Van M.; Nguyen, Huong D. T.; Ha, Hiep Q.; Truong, Thanh V.; RSC Advances 14 (2024) 15597–15603; doi:10.1039/D4RA01807A

data_7248605
_publ_section_title
;
 Iodine-promoted amide formation via oxidative cleavage of indoles: novel
 quinazoline-4(3H)-one and tryptanthrin syntheses
;
_journal_issue                   22
_journal_name_full               'RSC Advances'
_journal_page_first              15597
_journal_page_last               15603
_journal_paper_doi               10.1039/D4RA01807A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C15 H6 Cl2 N2 O2'
_chemical_formula_sum            'C15 H6 Cl2 N2 O2'
_chemical_formula_weight         317.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-01-19 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.556(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6414(2)
_cell_length_b                   32.4145(13)
_cell_length_c                   6.7458(3)
_cell_measurement_temperature    0(2)
_cell_volume                     1222.85(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      0.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9836
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.257
_diffrn_reflns_theta_min         3.110
_exptl_absorpt_coefficient_mu    0.567
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.8478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2278
_reflns_number_total             3004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra01807a2.cif
_cod_data_source_block           nhhcm_t5cl_0m
_cod_depositor_comments
;

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H2 Cl N4 O3'
_cod_original_formula_weight         153.52
_cod_original_formula_moiety         '0.5(C15 H6 Cl2 N2 O2)'
_cod_original_formula_units_Z            8
_cod_database_code               7248605
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.826
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00F(H00F), C00H(H00H), C00K(H00K), C00L(H00L)
;
_shelx_res_checksum              33466
_shelx_hkl_checksum              48991
_olex2_submission_special_instructions 'No special instructions were received'