Organocatalytic Asymmetric Synthesis of Dihydrobenzoxazinones Bearing Trifluoromethylated Quaternary Stereocenters.
Lou, Hengqiao; Wang, Yongtao; Jin, Enze; Lin, Xufeng; The Journal of organic chemistry 81 (2016) 2019–2026; doi:10.1021/acs.joc.5b02848

data_4036586
_publ_section_title
;
 Organocatalytic Asymmetric Synthesis of Dihydrobenzoxazinones Bearing
 Trifluoromethylated Quaternary Stereocenters.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2019
_journal_page_last               2026
_journal_paper_doi               10.1021/acs.joc.5b02848
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H9 F3 N2 O2'
_chemical_formula_sum            'C13 H9 F3 N2 O2'
_chemical_formula_weight         282.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.958(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6828(5)
_cell_length_b                   6.4475(3)
_cell_length_c                   11.5604(7)
_cell_measurement_reflns_used    2435
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.0473
_cell_measurement_theta_min      3.8489
_cell_volume                     642.41(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1297462000
_diffrn_orient_matrix_UB_12      -0.0305609000
_diffrn_orient_matrix_UB_13      -0.0783934000
_diffrn_orient_matrix_UB_21      -0.1183079000
_diffrn_orient_matrix_UB_22      0.0338599000
_diffrn_orient_matrix_UB_23      -0.1088452000
_diffrn_orient_matrix_UB_31      0.0338492000
_diffrn_orient_matrix_UB_32      0.2344264000
_diffrn_orient_matrix_UB_33      0.0053932000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5391
_diffrn_reflns_theta_full        67.16
_diffrn_reflns_theta_max         67.16
_diffrn_reflns_theta_min         3.85
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack (1983), 973 Friedel pairs'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2231
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                1968
_reflns_number_total             2231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02848_si_002.cif
_cod_data_source_block           141222_lhq1222_cu
_cod_database_code               4036586
_chemical_oxdiff_formula         'c10 h10 n2 o8 f3'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12)
;