Formation of 2-Imino Benzo[<i>e</i>]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies.
Leas, Derek A.; Wu, Jianbo; Ezell, Edward L.; Garrison, Jered C.; Vennerstrom, Jonathan L.; Dong, Yuxiang; ACS omega 3 (2018) 781–787; doi:10.1021/acsomega.7b01824

data_4515909
_publ_section_title
;
 Formation of 2-Imino Benzo[<i>e</i>]-1,3-oxazin-4-ones from Reactions of
 Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic
 Studies.
;
_journal_issue                   1
_journal_name_full               'ACS omega'
_journal_page_first              781
_journal_page_last               787
_journal_paper_doi               10.1021/acsomega.7b01824
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C21 H15 Br N2 O2'
_chemical_formula_sum            'C21 H15 Br N2 O2'
_chemical_formula_weight         407.26
_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   geom
_audit_creation_date             2017-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.0814(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.92936(8)
_cell_length_b                   12.80330(9)
_cell_length_c                   13.37608(11)
_cell_measurement_reflns_used    37494
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.9770
_cell_measurement_theta_min      3.5440
_cell_volume                     1734.45(3)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2603
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_diffrn_measurement_details
;
  1 omega -116.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9628  -77.0000    0.0000 102

  2 omega -113.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9628  -57.0000  -90.0000 93

  3 omega -116.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9628  -77.0000 -120.0000 102

  4 omega -130.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9628  178.0000 -150.0000 96

  5 omega -116.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9628  -77.0000   90.0000 102

  6 omega -116.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9628  -77.0000 -180.0000 102

  7 omega  -25.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628  -57.0000    0.0000 93

  8 omega  -25.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628  -57.0000 -180.0000 93

  9 omega   35.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628  178.0000 -120.0000 97

 10 omega   21.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628   38.0000   90.0000 94

 11 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000   90.0000 99

 12 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000  120.0000 94

 13 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000   60.0000 94

 14 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000  -30.0000 99

 15 omega   37.00  121.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000 -125.0000   90.0000 84

 16 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000 -120.0000 94

 17 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000  150.0000 99

 18 omega   28.00  109.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -95.0000  -60.0000 81

 19 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000    0.0000 99

 20 omega   37.00  139.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -77.0000    0.0000 102

 21 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000  -60.0000 94

 22 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000  120.0000 99

 23 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000   30.0000 99

 24 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000 -150.0000 94

 25 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000 -150.0000 99

 26 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000 -120.0000 99

 27 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000 -180.0000 94

 28 omega   37.00  121.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000 -125.0000  -90.0000 84

 29 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000  -90.0000 94

 30 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000  -30.0000 94

 31 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000  -90.0000 99

 32 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000    0.0000 94

 33 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000   60.0000 99

 34 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000  -60.0000 99

 35 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000   30.0000 94

 36 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000   90.0000 94

 37 omega   79.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   77.0000 -180.0000 99

 38 omega   84.00  178.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000   61.0000  150.0000 94

 39 omega   37.00  139.00   1.0000    1.4850
omega____ theta____ kappa____ phi______ frames
    -      109.0000  -77.0000  120.0000 102

 40 omega -115.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9628  -38.0000   60.0000 94

 41 omega -113.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9628  -57.0000   30.0000 93

 42 omega  -30.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628    0.0000 -150.0000 148

 43 omega  -30.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628    0.0000 -180.0000 148

 44 omega  -30.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628    0.0000  -90.0000 148

 45 omega  -30.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628    0.0000 -120.0000 148

 46 omega   16.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628   19.0000  -60.0000 104

 47 omega  -30.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628    0.0000  -60.0000 148

 48 omega  -30.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628    0.0000  -30.0000 148

 49 omega  -30.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628    0.0000    0.0000 148

 50 omega   14.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9628   77.0000    0.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_13      -0.0615634000
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_diffrn_orient_matrix_UB_23      0.0755553000
_diffrn_orient_matrix_UB_31      0.0501503000
_diffrn_orient_matrix_UB_32      -0.0595477000
_diffrn_orient_matrix_UB_33      -0.0771577000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            59123
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.165
_diffrn_reflns_theta_min         4.366
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40804
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0462P)^2^+1.2975P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3418
_reflns_number_total             3619
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b01824_si_002.cif
_cod_data_source_block           vennerstrom-4f
_cod_original_cell_volume        1734.45(2)
_cod_database_code               4515909
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H17N2O2Br1
_reflns_odcompleteness_completeness 99.97
_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
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C1(H1), C17(H17), C10(H10), C11(H11), C13(H13), C2(H2),
 C4(H4), C20(H20), C21(H21), C3(H3), C14(H14)
;
_shelx_res_checksum              57709
_shelx_hkl_checksum              77354
_olex2_date_sample_data_collection 2017-10-10
_olex2_exptl_crystal_mounting_method 'mounted on a Kyroloop using paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'