Synthesis of 1-Substituted Benzo[c]isoxazol-3(1H)-imines via Tandem Nitroso-Ene/Intramolecular Cyclizations of 2-Nitrosobenzonitrile
Jenna L. Jeffrey; Sean P. McClintock; Michael M. Haley; Journal of Organic Chemistry 73 (2008) 3288–3291; doi:10.1021/jo800055e

data_4023368
_publ_section_title
;
 Synthesis of 1-Substituted Benzo[c]isoxazol-3(1H)-imines
 via Tandem Nitroso-Ene/Intramolecular Cyclizations of
 2-Nitrosobenzonitrile
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3288
_journal_page_last               3291
_journal_paper_doi               10.1021/jo800055e
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C26 H30 B F4 N3 O2'
_chemical_formula_weight         503.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.700(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.710(2)
_cell_length_b                   10.795(2)
_cell_length_c                   21.519(5)
_cell_measurement_reflns_used    789
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.20
_cell_measurement_theta_min      2.18
_cell_volume                     2482.9(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21628
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.18
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_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.459
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         4357
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_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1478
_refine_ls_R_factor_gt           0.0662
_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^)+(0.0548P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1608
_reflns_number_gt                2187
_reflns_number_total             4357
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800055e-File004.cif
_cod_data_source_block           mh24
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

2020-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         251.67
_cod_original_formula_units_Z            8
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C13 H15 B0.50 F2 N1.50 O'
_cod_database_code               4023368