Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines
Tong, Mengchao; Zhang, Yong; Qin, Cong; Fu, Yiwei; Liu, Yonghai; Li, Hao; Wang, Wei; Organic Chemistry Frontiers 5 (2018) 2945–; doi:10.1039/C8QO00826D

data_1554422
_publ_section_title
;
 Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of
 nitrones: regioselectivity-switchable and highly diastereoselective
 synthesis of multisubstituted isoxazolidines
;
_journal_issue                   20
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2945
_journal_paper_doi               10.1039/C8QO00826D
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C24 H19 Cl N2 O'
_chemical_formula_sum            'C24 H19 Cl N2 O'
_chemical_formula_weight         386.86
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2018-08-01 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                87.715(3)
_cell_angle_beta                 87.737(3)
_cell_angle_gamma                86.465(3)
_cell_formula_units_Z            2
_cell_length_a                   5.7976(9)
_cell_length_b                   9.4263(14)
_cell_length_c                   17.097(3)
_cell_measurement_reflns_used    1384
_cell_measurement_temperature    130
_cell_measurement_theta_max      26.363
_cell_measurement_theta_min      2.17
_cell_volume                     931.2(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9492
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_min         1.193
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0478 before and 0.0375 after correction.
The Ratio of minimum to maximum transmission is 0.8953.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0475P)^2^+0.0969P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3455
_reflns_number_total             5658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00826d2.cif
_cod_data_source_block           mo_dm14659_0m
_cod_original_cell_volume        931.2(2)
_cod_database_code               1554422
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.842
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_shelx_res_checksum              49405
_shelx_hkl_checksum              27496
_olex2_submission_special_instructions 'No special instructions were received'