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_7157975
_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 H15 I N2 O3'
_chemical_formula_sum            'C19 H15 I N2 O3'
_chemical_formula_weight         446.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-03
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0555(10)
_cell_length_b                   7.4291(5)
_cell_length_c                   23.0509(12)
_cell_measurement_reflns_used    4260
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.8250
_cell_measurement_theta_min      2.9270
_cell_volume                     3434.5(3)
_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    'ShelXT (Sheldrick, 2015)'
_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 0.999
_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    -18.00  16.00   1.00    5.00    --   11.74 -99.00-150.00   34
  2  \w    -12.00  24.00   1.00    5.00    --   11.74  37.00-180.00   36
  3  \w    -53.00  14.00   1.00    5.00    --   11.74 -77.00   0.00   67
;
_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      -0.0083538000
_diffrn_orient_matrix_UB_12      0.0551143000
_diffrn_orient_matrix_UB_13      0.0240319000
_diffrn_orient_matrix_UB_21      0.0304437000
_diffrn_orient_matrix_UB_22      -0.0238719000
_diffrn_orient_matrix_UB_23      0.0136585000
_diffrn_orient_matrix_UB_31      0.0159865000
_diffrn_orient_matrix_UB_32      0.0742167000
_diffrn_orient_matrix_UB_33      -0.0134507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9747
_diffrn_reflns_point_group_measured_fraction_full 0.848
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.215
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61121
_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    1.726
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 1561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         5136
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0241P)^2^+2.1151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0678
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.688
_reflns_Friedel_fraction_max     0.688
_reflns_number_gt                4555
_reflns_number_total             5136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00421b2.cif
_cod_data_source_block           yst-i
_cod_depositor_comments
'Adding full bibliography for 7157974--7157975.cif.'
_cod_database_code               7157975
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.849
_shelx_estimated_absorpt_t_min   0.805
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C18B) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C14B) \\sim Ueq, Uanis(C17B) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
3.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C9B(H9B), C11B(H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C18(H18), C16B(H16B), C3(H3), C15(H15), C17B(H17B),
 C6B(H6B), C18B(H18B), C19B(H19B), C15B(H15B), C6(H6), C5B(H5B), C2B(H2B),
 C19(H19), C4(H4), C3B(H3B), C2(H2), C5(H5), C4B(H4B)
3.c Idealised Me refined as rotating group:
 C13(H13D,H13E,H13F), C13B(H13A,H13B,H13C)
;
_olex2_date_sample_data_collection 2019-05-03
_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 1.632
_oxdiff_exptl_absorpt_empirical_full_min 0.650