Catalyst-free synthesis of isoxazolidine from nitrosoarene and haloalkyne via a 1,2-halo-migration/[3 + 2] cycloaddition cascade.
Qiu, Shaotong; Cao, Tongxiang; Zhu, Shifa; Organic & biomolecular chemistry 19 (2021) 3139–3143; doi:10.1039/d1ob00421b

data_7157974
_publ_section_title
;
 Catalyst-free synthesis of isoxazolidine from nitrosoarene and haloalkyne
 via a 1,2-halo-migration/[3 + 2] cycloaddition cascade.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3139
_journal_page_last               3143
_journal_paper_doi               10.1039/d1ob00421b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H17 Br N2 O3'
_chemical_formula_sum            'C19 H17 Br N2 O3'
_chemical_formula_weight         401.25
_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
_audit_creation_date             2019-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-15 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.834(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4819(3)
_cell_length_b                   5.4926(2)
_cell_length_c                   25.2518(7)
_cell_measurement_reflns_used    3261
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3840
_cell_measurement_theta_min      3.5600
_cell_volume                     1694.42(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_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     70.00 119.00   1.00    1.00    --   40.98  19.00 120.00   49
  2  \w    124.00 164.00   1.00    1.00    --  106.95 125.00   0.00   40
  3  \w    105.00 168.00   1.00    1.00    --  106.95 125.00 120.00   63
  4  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 -90.00   97
  5  \w    138.00 165.00   1.00    1.00    --  106.95 125.00-120.00   27
  6  \w     36.00 130.00   1.00    1.00    --  106.95 -61.00 120.00   94
  7  \w     25.00  96.00   1.00    1.00    --   40.98-125.00 150.00   71
  8  \w     28.00 104.00   1.00    1.00    --  106.95 -94.00  60.00   76
  9  \w      6.00  35.00   1.00    1.00    --   40.98 -99.00-180.00   29
 10  \w    -24.00  65.00   1.00    1.00    --   40.98 -57.00-150.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1089999000
_diffrn_orient_matrix_UB_12      0.1398479000
_diffrn_orient_matrix_UB_13      0.0148480000
_diffrn_orient_matrix_UB_21      0.0163343000
_diffrn_orient_matrix_UB_22      -0.0282852000
_diffrn_orient_matrix_UB_23      -0.0585140000
_diffrn_orient_matrix_UB_31      -0.0612858000
_diffrn_orient_matrix_UB_32      0.2415083000
_diffrn_orient_matrix_UB_33      -0.0154983000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.578
_diffrn_reflns_theta_min         3.577
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.573
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0376P)^2^+0.2301P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2860
_reflns_number_total             3295
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00421b2.cif
_cod_data_source_block           9st229
_cod_depositor_comments
'Adding full bibliography for 7157974--7157975.cif.'
_cod_database_code               7157974
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.97
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C6(H6), C3(H3A), C14(H14), C10(H10), C13(H13),
 C12(H12), C11(H11)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 1.752
_oxdiff_exptl_absorpt_empirical_full_min 0.649