tert-Butyl nitrite triggered radical cascade reaction for synthesizing isoxazoles by a one-pot multicomponent strategy
Chen, Leijing; Wang, Zhen; Liu, Hui; Li, Xinyue; Wang, Bin; Chemical Communications  (2022) –; doi:10.1039/D2CC02823A

data_7130420
_publ_section_title
;
 &#x000D; tert-Butyl nitrite triggered radical cascade reaction for
 synthesizing isoxazoles by a one-pot multicomponent strategy
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02823A
_journal_year                    2022
_chemical_formula_moiety         'C16 H9 F3 N2 O3'
_chemical_formula_sum            'C16 H9 F3 N2 O3'
_chemical_formula_weight         334.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2021-11-23 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.722(2)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   21.1543(5)
_cell_length_b                   14.2842(3)
_cell_length_c                   30.5779(7)
_cell_measurement_reflns_used    9744
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7900
_cell_measurement_theta_min      3.7590
_cell_volume                     8894.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_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   -113.00 -17.00   1.00    4.00    --  -41.76 -38.00-120.00   96
  2  \w    -74.00  25.00   1.00    4.00    --  -41.76  77.00 150.00   99
  3  \w    -66.00  26.00   1.00    4.00    --  -41.76  38.00  60.00   92
  4  \w    106.00 170.00   1.00    7.50    --  106.05  77.00-180.00   64
  5  \w     53.00 112.00   1.00    7.50    --  106.05-125.00 -90.00   59
  6  \w     29.00 107.00   1.00    7.50    --  106.05 -94.00 -90.00   78
  7  \w     41.00 116.00   1.00    7.50    --  106.05 -45.00-120.00   75
  8  \w    103.00 173.00   1.00    7.50    --  106.05  77.00 -30.00   70
  9  \w     34.00 114.00   1.00    7.50    --  106.05 -45.00  30.00   80
 10  \w     33.00 112.00   1.00    7.50    --  106.05-125.00-150.00   79
 11  \w     27.00 107.00   1.00    7.50    --  106.05 -94.00  30.00   80
 12  \w     59.00 170.00   1.00    7.50    --  106.05  15.00 -60.00  111
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0165801000
_diffrn_orient_matrix_UB_12      0.0704055000
_diffrn_orient_matrix_UB_13      -0.0334302000
_diffrn_orient_matrix_UB_21      0.0181410000
_diffrn_orient_matrix_UB_22      -0.0815897000
_diffrn_orient_matrix_UB_23      -0.0272520000
_diffrn_orient_matrix_UB_31      -0.0715513000
_diffrn_orient_matrix_UB_32      -0.0043540000
_diffrn_orient_matrix_UB_33      -0.0296481000
_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  0.0216
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            26501
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.057
_diffrn_reflns_theta_min         3.780
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       block
_exptl_crystal_F_000             4080
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         8678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0703
_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^)+(0.0847P)^2^+6.7067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1927
_refine_ls_wR_factor_ref         0.2115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6235
_reflns_number_total             8678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02823a2.cif
_cod_data_source_block           wb20211018_autored
_cod_database_code               7130420
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         c20h20o2f3
_shelx_estimated_absorpt_t_max   0.797
_shelx_estimated_absorpt_t_min   0.773
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Sof: F2(0.5) F1(0.5) F3(0.5) F9'(0.5) F8'(0.5) F7'(0.5) F5(0.5) F6(0.5)
 F4(0.5) F6'(0.5) F5'(0.5) F4'(0.5) F7(0.5) F9(0.5) F8(0.5) F2'(0.5) F3'(0.5)
 F1'(0.5)
2.a Aromatic/amide H refined with riding coordinates:
 C25(H25), C42(H42), C9(H9), C4(H4), C28(H28), C32(H32), C48(H48), C3(H3),
 C20(H20), C6(H6), C7(H7), C31(H31), C12(H12), C47(H47), C29(H29), C16(H16),
 C44(H44), C22(H22), C23(H23), C19(H19), C39(H39), C13(H13), C38(H38), C45(H45),
  C15(H15), C36(H36), C35(H35)
;
_shelx_res_checksum              43629
_shelx_hkl_checksum              28654
_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 1.359
_oxdiff_exptl_absorpt_empirical_full_min 0.621