Iron-catalyzed 1,3-dipolar cycloaddition of alkynes and aryl nitrones for the synthesis of chiral Δ<sup>4</sup>-isoxazolines.
Zhao, Zhen-Ni; Li, Shuo; Zhu, Shi-Xuan; Liu, Guo-Hua; Li, Sheng-Yu; Li, Yi-Chao; Wang, Yi-Long; Huang, Yi-Yong; Organic & biomolecular chemistry 23 (2025) 3372–3379; doi:10.1039/d5ob00143a

data_7160399
_publ_section_title
;
 Iron-catalyzed 1,3-dipolar cycloaddition of alkynes and aryl nitrones for
 the synthesis of chiral &#x394;<sup>4</sup>-isoxazolines.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3372
_journal_page_last               3379
_journal_paper_doi               10.1039/d5ob00143a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_sum            'C32 H26 N2 O4'
_chemical_formula_weight         502.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-09-20 deposited with the CCDC.	2025-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.245(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6168(6)
_cell_length_b                   15.7680(12)
_cell_length_c                   9.6852(7)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.26
_cell_measurement_theta_min      4.88
_cell_volume                     1280.92(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker PHOTON III'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29868
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.345
_diffrn_reflns_theta_min         4.080
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 2735 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         7579
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0556P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                6544
_reflns_number_total             7579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00143a2.cif
_cod_data_source_block           230914f_0m
_cod_depositor_comments          'Adding full bibliography for 7160399.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7160399
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.957
_shelx_res_checksum              90895