3-Halo-5,6-dihydro-4<i>H</i>-1,2-oxazine <i>N</i>-oxides as synthetic equivalents of unsaturated nitrile oxides in the [3 + 2]-cycloaddition with arynes: synthesis of substituted 3-vinyl-1,2-benzisoxazoles.
Lukoyanov, Alexander A.; Aksenova, Svetlana A.; Tabolin, Andrey A.; Sukhorukov, Alexey Yu; Organic & biomolecular chemistry 22 (2024) 3615–3621; doi:10.1039/d4ob00391h

data_7159889
_publ_section_title
;
 3-Halo-5,6-dihydro-4<i>H</i>-1,2-oxazine <i>N</i>-oxides as synthetic
 equivalents of unsaturated nitrile oxides in the [3 + 2]-cycloaddition
 with arynes: synthesis of substituted 3-vinyl-1,2-benzisoxazoles.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3615
_journal_page_last               3621
_journal_paper_doi               10.1039/d4ob00391h
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C19 H18 Br N O3'
_chemical_formula_sum            'C19 H18 Br N O3'
_chemical_formula_weight         388.25
_chemical_melting_point          395.0(10)
_chemical_properties_physical    Heat-sensitive
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-04-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-04-08 deposited with the CCDC.	2024-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.3390(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.15719(7)
_cell_length_b                   16.71710(15)
_cell_length_c                   12.13404(8)
_cell_measurement_reflns_used    15936
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.8150
_cell_measurement_theta_min      4.4770
_cell_volume                     1653.27(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.117a 64-bit (release 26-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -48.00 -23.00   0.50    0.20    --  -93.75  45.00-150.00   50
  2  \w    -26.00  31.00   0.50    0.05    --  -44.88  19.00 -30.00  114
  3  \w    -72.00  29.00   0.50    0.05    --  -44.88  80.00  -9.00  202
  4  \w   -121.00 -20.00   0.50    0.20    --  -93.75  80.00  -9.00  202
  5  \w    -40.00  29.00   0.50    0.05    --  -44.88  38.00  90.00  138
  6  \w     60.00  89.00   0.50    0.05    --   44.88-125.00  60.00   58
  7  \w     51.00  92.00   0.50    0.20    --  115.25 -95.00   0.00   82
  8  \w     47.00  73.00   0.50    0.20    --  115.25-125.00   0.00   52
  9  \w     53.00 109.00   0.50    0.20    --  115.25-125.00 -60.00  112
 10  \w     46.00 105.00   0.50    0.20    --  115.25-125.00-150.00  118
 11  \w     50.00  76.00   0.50    0.20    --  115.25 -87.00 -45.65   52
 12  \w     65.00  91.00   0.50    0.20    --  115.25 -95.00 -60.00   52
 13  \w     73.00  99.00   0.50    0.20    --  115.25 -95.00 -30.00   52
 14  \w     87.00 113.00   0.50    0.20    --  115.25 -87.00 -45.65   52
 15  \w     65.00 102.00   0.50    0.20    --  115.25 -95.00  90.00   74
 16  \w     86.00 115.00   0.50    0.20    --  115.25 -85.00  81.16   58
 17  \w    -21.00  72.00   0.50    0.05    --   44.88 -80.00-132.00  186
 18  \w     43.00 138.00   0.50    0.20    --  115.25 -80.00-132.00  190
 19  \w    113.00 139.00   0.50    0.20    --  115.25 -80.00-132.00   52
 20  \w     44.00  71.00   0.50    0.20    --  115.25 -61.00-180.00   54
 21  \w     43.00  68.00   0.50    0.20    --  115.25 -61.00 -90.00   50
 22  \w     46.00  71.00   0.50    0.20    --  115.25 -61.00   0.00   50
 23  \w     46.00  72.00   0.50    0.20    --  115.25 -77.00  60.00   52
 24  \w     49.00 104.00   0.50    0.20    --  115.25 -77.00  90.00  110
 25  \w     48.00 104.00   0.50    0.20    --  115.25 -77.00 150.00  112
 26  \w     43.00  68.00   0.50    0.20    --  115.25 -61.00  60.00   50
 27  \w    -24.00   2.00   0.50    0.05    --   44.88 -19.00-180.00   52
 28  \w     90.00 139.00   0.50    0.20    --  115.25  15.00-120.00   98
 29  \w    146.00 172.00   0.50    0.20    --  115.25  77.00 -60.00   52
 30  \w    101.00 129.00   0.50    0.20    --  115.25  80.00  -9.00   56
 31  \w     98.00 124.00   0.50    0.20    --  115.25  61.00 -60.00   52
 32  \w     97.00 123.00   0.50    0.20    --  115.25  77.00 -60.00   52
 33  \w    102.00 127.00   0.50    0.20    --  115.25  61.00-120.00   50
 34  \w    146.00 177.00   0.50    0.20    --  115.25  61.00-120.00   62
 35  \w    133.00 169.00   0.50    0.20    --  115.25  30.00-180.00   72
 36  \w     98.00 171.00   0.50    0.20    --  115.25  45.00 -60.00  146
 37  \w    101.00 157.00   0.50    0.20    --  115.25  30.00 -60.00  112
 38  \w    107.00 156.00   0.50    0.20    --  115.25  45.00 -30.00   98
 39  \w     93.00 150.00   0.50    0.20    --  115.25  15.00  90.00  114
 40  \w    101.00 176.00   0.50    0.20    --  115.25  61.00 120.00  150
 41  \w    140.00 173.00   0.50    0.20    --  115.25 125.00  60.00   66
 42  \w     96.00 123.00   0.50    0.20    --  115.25 125.00 -60.00   54
 43  \w    144.00 170.00   0.50    0.20    --  115.25 125.00 -60.00   52
 44  \w   -167.00 -79.00   0.50    0.20    --  -93.75 -80.00-132.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1448128000
_diffrn_orient_matrix_UB_12      -0.0261042000
_diffrn_orient_matrix_UB_13      -0.0771731000
_diffrn_orient_matrix_UB_21      -0.0971855000
_diffrn_orient_matrix_UB_22      0.0745630000
_diffrn_orient_matrix_UB_23      0.0336128000
_diffrn_orient_matrix_UB_31      0.0729415000
_diffrn_orient_matrix_UB_32      0.0474351000
_diffrn_orient_matrix_UB_33      -0.0951766000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19247
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.103
_diffrn_reflns_theta_min         4.505
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.534
_exptl_absorpt_correction_T_max  0.664
_exptl_absorpt_correction_T_min  0.351
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.117a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane, Ethyl Acetate'
_exptl_crystal_size_max          0.537
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.205
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.0061(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+1.3750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3575
_reflns_number_total             3602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00391h2.cif
_cod_data_source_block           AL538
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '394-396' was changed to
'395.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159888--7159889.cif.
;
_cod_database_code               7159889
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H18BrNO3
_chemical_oxdiff_usercomment     AL538
_shelx_estimated_absorpt_t_max   0.531
_shelx_estimated_absorpt_t_min   0.253
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              29593
_shelx_hkl_checksum              20441
_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 2.069
_oxdiff_exptl_absorpt_empirical_full_min 0.465