Synthesis of five-membered cyclic nitrones based on the Lewis acid-catalysed [3+2]-annulation reaction of donor-acceptor cyclopropanes with 1,4,2-dioxazoles.
Wang, Zhe-Hao; Zhang, Huan-Huan; Xu, Peng-Fei; Luo, Yong-Chun; Chemical communications (Cambridge, England) 54 (2018) 10128–10131; doi:10.1039/c8cc04656e

data_7122210
_publ_section_title
;
 Synthesis of five-membered cyclic nitrones based on the Lewis
 acid-catalysed [3+2]-annulation reaction of donor-acceptor cyclopropanes
 with 1,4,2-dioxazoles.
;
_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10128
_journal_page_last               10131
_journal_paper_doi               10.1039/c8cc04656e
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-07-23 deposited with the CCDC.
2018-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.079(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2648(2)
_cell_length_b                   10.1169(2)
_cell_length_c                   10.9096(3)
_cell_measurement_reflns_used    2809
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      69.7450
_cell_measurement_theta_min      4.3640
_cell_volume                     876.51(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega  -85.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   30.0000 43

  2 omega  -26.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -150.0000 27

  3 omega  -74.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -90.0000 27

  4 omega  -86.00  -43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  150.0000 43

  5 omega   32.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 86

  6 omega   48.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 26

  7 omega   79.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 42

  8 omega   42.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 54

  9 omega   38.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 44

 10 omega   55.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 47

 11 omega   37.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  150.0000 52

 12 omega  100.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 75

 13 omega   65.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 26

 14 omega   40.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 44

 15 omega   49.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 42

 16 omega   61.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000  -60.0000 95

 17 omega  121.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 41

 18 omega  -79.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000   30.0000 94

 19 omega  -81.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -38.0000  -90.0000 100

 20 omega  -79.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000 -171.0000 94

 21 omega   23.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -30.0000 89

 22 omega  -20.00    5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000   60.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0417994000
_diffrn_orient_matrix_UB_12      0.0138205000
_diffrn_orient_matrix_UB_13      -0.1460823000
_diffrn_orient_matrix_UB_21      -0.1473548000
_diffrn_orient_matrix_UB_22      0.0927412000
_diffrn_orient_matrix_UB_23      0.0008219000
_diffrn_orient_matrix_UB_31      0.1191062000
_diffrn_orient_matrix_UB_32      0.1199508000
_diffrn_orient_matrix_UB_33      0.0162781000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3576
_diffrn_reflns_theta_full        66.54
_diffrn_reflns_theta_max         66.54
_diffrn_reflns_theta_min         5.57
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.0687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0747
_reflns_number_gt                2242
_reflns_number_total             2269
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc04656e3.cif
_cod_data_source_block           luoych_0720
_cod_depositor_comments
'Adding full bibliography for 7122210--7122211.cif.'
_cod_database_code               7122210
_reflns_odcompleteness_completeness 97.48
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_olex2_date_sample_data_collection 2018-07-23
_olex2_submission_special_instructions 'No special instructions were received'