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_7250516
_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_absolute_configuration unk
_chemical_formula_moiety         'C12 H11 N O3'
_chemical_formula_sum            'C12 H11 N O3'
_chemical_formula_weight         217.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_Int_Tables_number      33
_audit_creation_date             2025-02-18
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_audit_update_record
;
2025-03-01 deposited with the CCDC.	2025-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.9767(6)
_cell_length_b                   6.3602(2)
_cell_length_c                   4.9575(1)
_cell_measurement_reflns_used    5660
_cell_measurement_temperature    160.0(1)
_cell_measurement_theta_max      78.1530
_cell_measurement_theta_min      2.8320
_cell_volume                     976.72(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.9381
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     45.00  94.00   0.50    0.75    --  113.25-125.00-180.00   98
  2  \w     78.00 126.00   0.50    0.75    --  113.25-146.00-117.00   96
  3  \w     51.00  98.00   0.50    0.75    --  113.25-125.00 -60.00   94
  4  \w     56.00  82.00   0.50    0.75    --  113.25-125.00-150.00   52
  5  \w     52.00  77.00   0.50    0.75    --  113.25-112.00 -49.00   50
  6  \w     57.00 106.00   0.50    0.75    --  113.25 -94.00 -30.00   98
  7  \w     95.00 132.00   0.50    0.75    --  113.25-153.00  87.46   74
  8  \w     82.00 109.00   0.50    0.75    --  113.25-125.00 120.00   54
  9  \w     50.00  75.00   0.50    0.75    --  113.25-125.00 150.00   50
 10  \w     79.00 105.00   0.50    0.75    --  113.25 -94.00 120.00   52
 11  \w     78.00 103.00   0.50    0.75    --  113.25 -94.00  30.00   50
 12  \w     43.00  68.00   0.50    0.75    --  113.25 -61.00  90.00   50
 13  \w     61.00  87.00   0.50    0.75    --  113.25 -77.00  30.00   52
 14  \w     42.00  67.00   0.50    0.75    --  113.25 -61.00 -60.00   50
 15  \w     42.00  67.00   0.50    0.75    --  113.25 -77.00-120.00   50
 16  \w     55.00  80.00   0.50    0.75    --  113.25 -77.00-180.00   50
 17  \w    116.00 168.00   0.50    0.75    --  113.25  15.00-150.00  104
 18  \w    121.00 146.00   0.50    0.75    --  113.25  45.00-180.00   50
 19  \w    112.00 137.00   0.50    0.75    --  113.25  30.00-150.00   50
 20  \w    111.00 136.00   0.50    0.75    --  113.25  15.00  90.00   50
 21  \w    109.00 134.00   0.50    0.75    --  113.25  15.00 150.00   50
 22  \w     92.00 178.00   0.50    0.75    --  113.25  77.00 120.00  172
 23  \w     96.00 122.00   0.50    0.75    --  113.25  77.00  60.00   52
 24  \w    118.00 144.00   0.50    0.75    --  113.25 112.00  43.00   52
 25  \w    118.00 164.00   0.50    0.75    --  113.25 125.00 150.00   92
 26  \w    142.00 178.00   0.50    0.75    --  113.25 125.00-150.00   72
 27  \w     96.00 132.00   0.50    0.75    --  113.25 125.00-150.00   72
 28  \w     88.00 117.00   0.50    0.20    --   47.39  77.00-120.00   58
 29  \w     89.00 115.00   0.50    0.20    --   47.39  77.00 -60.00   52
 30  \w     89.00 117.00   0.50    0.20    --   47.39  77.00  90.00   56
 31  \w    -43.00 -17.00   0.50    0.75    --  -91.75  30.00-150.00   52
 32  \w    -44.00 -18.00   0.50    0.75    --  -91.75  15.00 -75.00   52
 33  \w    -76.00  -7.00   0.50    0.20    --  -47.39 112.00  43.00  138
 34  \w    -85.00 -39.00   0.50    0.20    --  -47.39 -15.00 114.00   92
 35  \w   -165.00-139.00   0.50    0.75    --  -91.75 -15.00 114.00   52
 36  \w   -114.00 -88.00   0.50    0.20    --  -47.39 -77.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0095721000
_diffrn_orient_matrix_UB_12      -0.2373472000
_diffrn_orient_matrix_UB_13      0.0132885000
_diffrn_orient_matrix_UB_21      -0.0032936000
_diffrn_orient_matrix_UB_22      0.0137017000
_diffrn_orient_matrix_UB_23      0.3096448000
_diffrn_orient_matrix_UB_31      -0.0487015000
_diffrn_orient_matrix_UB_32      0.0457815000
_diffrn_orient_matrix_UB_33      -0.0236869000
_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  0.0401
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7627
_diffrn_reflns_theta_full        75.0
_diffrn_reflns_theta_max         80.03
_diffrn_reflns_theta_min         2.85
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.4771
_exptl_crystal_description       Block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.3596
_refine_diff_density_min         -0.1934
_refine_diff_density_rms         0.0446
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_d_res_high            0.7827
_refine_ls_d_res_low             15.4883
_refine_ls_goodness_of_fit_ref   1.0612
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2001
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0612
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.0027
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.3022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.862
_reflns_limit_h_max              39
_reflns_limit_h_min              -38
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              6
_reflns_limit_l_min              -6
_reflns_number_gt                1935
_reflns_number_total             2001
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ra02996a2.cif
_cod_data_source_block           IZ214
_cod_original_sg_symbol_Hall     ' P 2c -2n'
_cod_database_code               7250516
_chemical_oxdiff_formula         'C48 H48 Cl4 N4 O12 '
_chemical_oxdiff_usercomment     Lithuania
_diffrn_oxdiff_digest_frames
;
01f7381580371c75ae22482ad11b32795a00030df10
;
_diffrn_oxdiff_digest_hkl
;
01c577034d32e2b552565c9642ba34bf3ef0e7
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C12(H12a,H12b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.654
_oxdiff_exptl_absorpt_empirical_full_min 0.650