Reagent-Controlled Divergent Synthesis of 2-Amino-1,3-Benzoxazines and 2-Amino-1,3-Benzothiazines.
Putta, Venkata Pattabhi Rama Kishore; Vodnala, Nagaraju; Gujjarappa, Raghuram; Tyagi, Ujjawal; Garg, Aakriti; Gupta, Sreya; Pujar, Prasad P.; Malakar, Chandi Charan; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02384

data_4037751
_publ_section_title
;
 Reagent-Controlled Divergent Synthesis of 2-Amino-1,3-Benzoxazines and
 2-Amino-1,3-Benzothiazines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02384
_journal_year                    2019
_chemical_formula_moiety         'C15 H10 F N2 O2'
_chemical_formula_sum            'C15 H10 F N2 O2'
_chemical_formula_weight         269.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-06-21
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.527(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2439(6)
_cell_length_b                   8.4591(3)
_cell_length_c                   13.4174(6)
_cell_measurement_reflns_used    1807
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.7350
_cell_measurement_theta_min      6.3010
_cell_volume                     1274.15(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w      6.00  64.00   1.00    1.00    --   25.69 -57.00 -30.00   58
  2  \w     56.00  96.00   1.00    1.00    --   25.69  57.00 -90.00   40
  3  \w    116.00 142.00   1.00    5.00    --   66.85 111.00-120.00   26
  4  \w    111.00 149.00   1.00    5.00    --   66.85 111.00 -30.00   38
  5  \w    117.00 178.00   1.00   10.00    --  108.00 104.00 -30.00   61
  6  \w    106.00 147.00   1.00   10.00    --  108.00  77.00  90.00   41
  7  \w     91.00 174.00   1.00   10.00    --  108.00  54.00 150.00   83
  8  \w     70.00 177.00   1.00   10.00    --  108.00  77.00  60.00  107
  9  \w    101.00 142.00   1.00    5.00    --   66.85 178.00 -90.00   41
 10  \w     61.00  99.00   1.00    5.00    --   66.85 178.00  60.00   38
 11  \w     65.00 103.00   1.00   10.00    --  108.00  77.00  90.00   38
 12  \w     24.00 148.00   1.00    5.00    --   66.85  77.00  60.00  124
 13  \w     35.00 133.00   1.00    5.00    --   66.85  63.00-180.00   98
 14  \w     73.00 175.00   1.00   10.00    --  108.00  65.00-180.00  102
 15  \w    117.00 143.00   1.00   10.00    --  108.00 -89.00  30.00   26
 16  \w     48.00 108.00   1.00   10.00    --  108.00 -89.00  30.00   60
 17  \w     23.00 109.00   1.00   10.00    --  108.00-104.00 150.00   86
 18  \w    -13.00  42.00   1.00    1.00    --   25.69  57.00 -90.00   55
 19  \w    -45.00   1.00   1.00    1.00    --   25.69 -57.00 -30.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1103386000
_diffrn_orient_matrix_UB_12      -0.1016549000
_diffrn_orient_matrix_UB_13      0.0638625000
_diffrn_orient_matrix_UB_21      0.0598647000
_diffrn_orient_matrix_UB_22      0.1436451000
_diffrn_orient_matrix_UB_23      0.0715621000
_diffrn_orient_matrix_UB_31      -0.0554901000
_diffrn_orient_matrix_UB_32      -0.0470087000
_diffrn_orient_matrix_UB_33      0.0804830000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3959
_diffrn_reflns_theta_full        66.84
_diffrn_reflns_theta_max         66.84
_diffrn_reflns_theta_min         4.14
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0572
_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^)+(0.1050P)^2^+0.1819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1804
_refine_ls_wR_factor_ref         0.1900
_reflns_number_gt                1788
_reflns_number_total             2208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02384_si_002.cif
_cod_data_source_block           sps_05_f2_rt_cu
_cod_original_cell_volume        1274.15(9)
_cod_database_code               4037751
_chemical_oxdiff_formula         'C60 H40 F4 N8 O8'
_reflns_odcompleteness_completeness 96.93
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C5(H5), C13(H13), C2(H2), C12(H12), C3(H3), C4(H4)
;
_olex2_date_sample_data_collection 2019-06-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.594