Organocatalytic Asymmetric Cascade Reaction of 2-Hydroxyphenyl-Substituted Enones and Isocyanates To Construct 1,3-Benzoxazin-2-ones.
Guo, Songsong; Liu, Xiaohua; Shen, Bin; Lin, Lili; Feng, Xiaoming; Organic letters 18 (2016) 5070–5073; doi:10.1021/acs.orglett.6b02522

data_1555808
_publ_section_title
;
 Organocatalytic Asymmetric Cascade Reaction of
 2-Hydroxyphenyl-Substituted Enones and Isocyanates To Construct
 1,3-Benzoxazin-2-ones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5070
_journal_page_last               5073
_journal_paper_doi               10.1021/acs.orglett.6b02522
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H16 F N O3, C2 H3 N'
_chemical_formula_sum            'C24 H19 F N2 O3'
_chemical_formula_weight         402.41
_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
_audit_creation_date             2016-02-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_a                   5.86821(12)
_cell_length_b                   16.6995(3)
_cell_length_c                   20.8172(5)
_cell_measurement_reflns_used    4566
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.6740
_cell_measurement_theta_min      4.9930
_cell_volume                     2040.01(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8740  -99.0000    0.0000 74

  2 omega   19.00  103.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8740   57.0000  -90.0000 84

  3 omega  -32.00   63.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8740  -77.0000 -150.0000 95

  4 omega    1.00   75.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8740  -99.0000  -60.0000 74

  5 omega    1.00   29.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8740   91.0000 -147.5966 28

  6 omega    9.00  103.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8740   77.0000  -60.0000 94

  7 omega   37.00  146.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   90.0000 109

  8 omega   40.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

  9 omega   40.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 10 omega   38.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 11 omega   38.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 12 omega   39.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 13 omega   38.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 14 omega   39.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 15 omega   40.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 16 omega    1.00   75.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8740  -99.0000  120.0000 74

 17 omega   17.00   85.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8740   38.0000 -150.0000 68

 18 omega    9.00  103.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8740   77.0000   90.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0919661000
_diffrn_orient_matrix_UB_12      -0.0863473000
_diffrn_orient_matrix_UB_13      0.0009546000
_diffrn_orient_matrix_UB_21      -0.0179601000
_diffrn_orient_matrix_UB_22      -0.0010772000
_diffrn_orient_matrix_UB_23      0.0738286000
_diffrn_orient_matrix_UB_31      -0.2453712000
_diffrn_orient_matrix_UB_32      -0.0323140000
_diffrn_orient_matrix_UB_33      -0.0050676000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11324
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.194
_diffrn_reflns_theta_min         5.007
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0929P)^2^+0.1079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                3596
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02522_si_001.cif
_cod_data_source_block           fxm-cc-1
_cod_original_cell_volume        2040.01(8)
_cod_database_code               1555808
_reflns_odcompleteness_completeness 99.81
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S),
 C00T(H00T)
2.d Idealised Me refined as rotating group:
 C00U(H00C,H00D,H00G)
;
_shelx_res_checksum              96137
_shelx_hkl_checksum              64242
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-23
_olex2_submission_special_instructions 'No special instructions were received'