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_7159888
_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         'C15 H10 Cl N O'
_chemical_formula_sum            'C15 H10 Cl N O'
_chemical_formula_weight         255.69
_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
_audit_creation_date             2024-03-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-04 deposited with the CCDC.	2024-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.37990(10)
_cell_length_b                   13.7636(3)
_cell_length_c                   11.7474(2)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.28
_cell_volume                     1192.74(4)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15544
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_min         2.280
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1034 before and 0.0384 after correction.
The Ratio of minimum to maximum transmission is 0.9129.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0390P)^2^+0.5323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2982
_reflns_number_total             3168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00391h2.cif
_cod_data_source_block           al332
_cod_depositor_comments
'Adding full bibliography for 7159888--7159889.cif.'
_cod_database_code               7159888
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.863
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C6(H6), C14(H14), C11(H11), C4(H4), C12(H12), C3(H3), C5(H5)
2.b X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
;
_shelx_res_checksum              98727
_shelx_hkl_checksum              41411
_olex2_submission_special_instructions 'No special instructions were received'