Enantioselective Syntheses of 4H-3,1-Benzoxazines via Catalytic Asymmetric Chlorocyclization of o-Vinylanilides.
Xie, Qinxia; Long, Hai-Jiao; Zhang, Qiong-Yin; Tang, Pei; Deng, Jun; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02395

data_4037806
_publ_section_title
;
 Enantioselective Syntheses of 4H-3,1-Benzoxazines via Catalytic
 Asymmetric Chlorocyclization of o-Vinylanilides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02395
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H16 Cl N O'
_chemical_formula_sum            'C21 H16 Cl N O'
_chemical_formula_weight         333.80
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6432(5)
_cell_length_b                   12.4568(6)
_cell_length_c                   14.2518(7)
_cell_measurement_reflns_used    2301
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.1990
_cell_measurement_theta_min      3.8860
_cell_volume                     1711.97(15)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7397
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.077
_diffrn_reflns_theta_min         3.555
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1008 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.1083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.815
_reflns_number_gt                3045
_reflns_number_total             3919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02395_si_002.cif
_cod_data_source_block           20190311-dengjun-aa
_cod_database_code               4037806
_shelx_shelxl_version_number     2014/7
_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:
 C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C16(H16), C9(H9), C1(H1), C20(H20), C12(H12), C4(H4), C11(H11),
 C19(H19), C10(H10), C18(H18), C3(H3), C2(H2), C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'