An epoxide-opening cyclization/double Smiles rearrangement cascade approach to <i>N</i>-aryl-1,4-benzoxazines and <i>N</i>-arylindolines.
Das, Jonali; Gogoi, Abhijit; Borah, Biraj Jyoti; Das, Sajal Kumar; Organic & biomolecular chemistry 21 (2023) 4755–4759; doi:10.1039/d3ob00440f

data_7159363
_publ_section_title
;
 An epoxide-opening cyclization/double Smiles rearrangement cascade
 approach to <i>N</i>-aryl-1,4-benzoxazines and <i>N</i>-arylindolines.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4755
_journal_page_last               4759
_journal_paper_doi               10.1039/d3ob00440f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C21 H18 N2 O4'
_chemical_formula_weight         362.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2022-02-01 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.735(2)
_cell_angle_gamma                90
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_cell_length_c                   23.5961(16)
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_cell_measurement_temperature    273(2)
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_computing_cell_refinement       'Bruker SAINT'
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_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
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_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_number            70401
_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
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_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
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_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.307
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_refine_ls_extinction_coef       0.0135(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0370P)^2^+0.8431P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3439
_reflns_number_total             3948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00440f2.cif
_cod_data_source_block           JD_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159363.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159363
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              27311
_shelx_hkl_checksum              44096