A new synthetic approach to the 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indole system from ethyl 1H-indole-2-carboxylates and activated glycerol carbonate
Zagorskytė, Inesa; Arbačiauskienė, Eglė; Račkauskienė, Greta; Belyakov, Sergey; Bieliauskas, Aurimas; Rollin, Patrick; Šačkus, Algirdas; RSC Advances 15 (2025) 18947–18970; doi:10.1039/D5RA02996A

data_7250515
_publ_section_title
;
 A new synthetic approach to the 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indole
 system from ethyl 1H-indole-2-carboxylates and activated glycerol
 carbonate
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              18947
_journal_page_last               18970
_journal_paper_doi               10.1039/D5RA02996A
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C19 H14 N2 O4 S2'
_chemical_formula_sum            'C19 H14 N2 O4 S2'
_chemical_formula_weight         398.466
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2025-02-23
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2025-03-01 deposited with the CCDC.	2025-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                93.795(3)
_cell_angle_beta                 92.677(2)
_cell_angle_gamma                105.124(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8591(1)
_cell_length_b                   11.0368(4)
_cell_length_c                   11.7919(4)
_cell_measurement_reflns_used    2569
_cell_measurement_temperature    160.0(3)
_cell_measurement_theta_max      75.0
_cell_measurement_theta_min      0.9
_cell_volume                     857.97(5)
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-ac4 (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2014  (Burla et al.,  2007)'
_diffrn_ambient_temperature      160.0(3)
_diffrn_measured_fraction_theta_full 0.9958
_diffrn_measured_fraction_theta_max 0.9736
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.9958
_diffrn_reflns_Laue_measured_fraction_max 0.9736
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12166
_diffrn_reflns_point_group_measured_fraction_full 0.9958
_diffrn_reflns_point_group_measured_fraction_max 0.9736
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         80.15
_diffrn_reflns_theta_min         3.77
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       'Needle '
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.8992
_refine_diff_density_min         -0.5394
_refine_diff_density_rms         0.1359
_refine_ls_d_res_high            0.7825
_refine_ls_d_res_low             11.7401
_refine_ls_goodness_of_fit_ref   1.0381
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0381
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.0073
_refine_ls_shift/su_mean         0.0008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0615P)^2^+4.8040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1924
_refine_ls_wR_factor_ref         0.1933
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3385
_reflns_number_total             3655
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ra02996a2.cif
_cod_data_source_block           IZ341
_cod_database_code               7250515
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C12(H12a,H12b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C19(H19), C20(H20), C21(H21),
 C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'