Electrochemical oxidative cascade cyclization of olefinic amides and alcohols leading to the synthesis of alkoxylated 4H-3,1-benzoxazines and indolines
Wei, Wan-Jie; Zhan, Lei; Jiang, Cai-Na; Tang, Hai-Tao; Pan, Ying-Ming; Ma, Xian-Li; Mo, Zu-Yu; Green Chemistry 25 (2023) 928–933; doi:10.1039/D2GC04645H

data_7246166
_publ_section_title
;
 Electrochemical oxidative cascade cyclization of olefinic amides and
 alcohols leading to the synthesis of alkoxylated 4H-3,1-benzoxazines and
 indolines
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              928
_journal_page_last               933
_journal_paper_doi               10.1039/D2GC04645H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C19 H19 N O3'
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.35
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2d7qds
_audit_creation_date             2022-09-24
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-10-10 deposited with the CCDC.	2023-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0732(3)
_cell_length_b                   8.28431(18)
_cell_length_c                   20.8875(4)
_cell_measurement_reflns_used    8042
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.5740
_cell_measurement_theta_min      2.4390
_cell_volume                     3127.36(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.973
_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   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00   0.00   99
  2  \w    -35.00  73.00   1.00    1.00    --   40.73 -77.00-180.00  108
  3  \w    -34.00  65.00   1.00    1.00    --   40.73 -38.00-180.00   99
  4  \w     78.00 178.00   1.00    2.42    --  107.58  61.00-180.00  100
  5  \w     31.00 136.00   1.00    2.42    --  107.58 -30.00 150.00  105
  6  \w     94.00 178.00   1.00    2.42    --  107.58 125.00 120.00   84
  7  \w     82.00 178.00   1.00    2.42    --  107.58  45.00  90.00   96
  8  \w     94.00 178.00   1.00    2.42    --  107.58 125.00-120.00   84
  9  \w     34.00  50.00   1.00    2.42    --  107.58-125.00 120.00   16
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0281072000
_diffrn_orient_matrix_UB_12      -0.0705147000
_diffrn_orient_matrix_UB_13      -0.0637393000
_diffrn_orient_matrix_UB_21      -0.0803655000
_diffrn_orient_matrix_UB_22      0.0160205000
_diffrn_orient_matrix_UB_23      0.0237110000
_diffrn_orient_matrix_UB_31      -0.0039844000
_diffrn_orient_matrix_UB_32      0.1713943000
_diffrn_orient_matrix_UB_33      -0.0285009000
_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  0.0297
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13555
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.749
_diffrn_reflns_theta_min         4.233
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0510P)^2^+1.0792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2850
_reflns_number_total             3076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04645h2.cif
_cod_data_source_block           1788
_cod_depositor_comments          'Adding full bibliography for 7246166.cif.'
_cod_original_cell_volume        3127.35(10)
_cod_database_code               7246166
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.894
_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.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              25600
_olex2_date_sample_data_collection 2022-09-23
_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 1.822
_oxdiff_exptl_absorpt_empirical_full_min 0.444