A metal-free hydrogenation of 3-substituted 2H-1,4-benzoxazines.
Wei, Simin; Feng, Xiangqing; Du, Haifeng; Organic & biomolecular chemistry 14 (2016) 8026–8029; doi:10.1039/c6ob01556e

data_7155224
_publ_section_title
;
 A metal-free hydrogenation of 3-substituted 2H-1,4-benzoxazines.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8026
_journal_page_last               8029
_journal_paper_doi               10.1039/c6ob01556e
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C20 H17 N O'
_chemical_formula_sum            'C20 H17 N O'
_chemical_formula_weight         287.35
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2yn'
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_symmetry_space_group_name_Hall  '-P 2yn'
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_atom_sites_solution_hydrogens   mixed
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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;
2016-07-19 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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'SHELXT (Sheldrick, 2014)'
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_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 45.0484
              2theta: -20.0255
scan:
    Number of images: 358
               Slice: -110.0000 - 69.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.0484
              2theta: -20.0255
;
_diffrn_measurement_device
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Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
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_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0744
_diffrn_orient_matrix_UB_12      -0.0220
_diffrn_orient_matrix_UB_13      0.0222
_diffrn_orient_matrix_UB_21      -0.0101
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_diffrn_orient_matrix_UB_32      -0.0371
_diffrn_orient_matrix_UB_33      0.0278
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11253
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
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_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         1.752
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.080
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_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
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_exptl_crystal_description       plate
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_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.05
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_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0423P)^2^+0.5778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                3106
_reflns_number_total             3338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01556e2.cif
_cod_data_source_block           mx4584
_cod_depositor_comments          'Adding full bibliography for 7155224.cif.'
_cod_database_code               7155224
_diffrn_number_total             3692
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              44556
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'