Synthesis of 1,2,4-oxadiazolidines via [3+2] cycloaddition of nitrones with carbodiimides
Chen, Yuan; Fuyue, Liuting; Wang, Gangqiang; Wang, Hang; Lu, Chun; Guo, Haibing; St. Amant, Chiara; Sun, Shaofa; Xing, Yalan; New Journal of Chemistry 43 (2019) 4329–; doi:10.1039/C9NJ00030E

data_7058164
_publ_section_title
;
 Synthesis of 1,2,4-oxadiazolidines via [3+2] cycloaddition of nitrones
 with carbodiimides
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4329
_journal_paper_doi               10.1039/C9NJ00030E
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         '2(C22 H21 N3 O)'
_chemical_formula_sum            'C44 H42 N6 O2'
_chemical_formula_weight         686.83
_chemical_name_systematic        1
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-19 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.279(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.91010(10)
_cell_length_b                   25.8295(4)
_cell_length_c                   18.5500(3)
_cell_measurement_reflns_used    14756
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2100
_cell_measurement_theta_min      2.9150
_cell_volume                     3789.98(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     43.00  68.00   0.50    2.00    --   43.80  75.00 -37.00   50
  2  \w     85.00 164.00   0.50   10.00    --  111.75  75.00 -37.00  158
  3  \w    120.00 162.00   0.50   10.00    --  111.75  30.00 -90.00   84
  4  \w     94.00 127.00   0.50   10.00    --  111.75 -45.00  30.00   66
  5  \w     91.00 126.00   0.50   10.00    --  111.75  45.00  60.00   70
  6  \w     88.00 156.00   0.50   10.00    --  111.75  61.00  60.00  136
  7  \w    109.00 172.00   0.50   10.00    --  111.75  15.00 150.00  126
  8  \w     79.00 105.00   0.50   10.00    --  111.75  15.00 150.00   52
  9  \w     68.00 102.00   0.50   10.00    --  111.75 -30.00 150.00   68
 10  \w     65.00  97.00   0.50   10.00    --  111.75 -94.00 150.00   64
 11  \w     31.00 153.00   0.50   10.00    --  111.75 -15.00 150.00  244
 12  \w     85.00 175.00   0.50   10.00    --  111.75  77.00 -90.00  180
 13  \w     88.00 113.00   0.50   10.00    --  111.75 -30.00-120.00   50
 14  \w     43.00 139.00   0.50   10.00    --  111.75 -75.00-165.00  192
 15  \w     53.00 121.00   0.50   10.00    --  111.75-125.00-180.00  136
 16  \w     36.00  62.00   0.50   10.00    --  111.75 -30.00-120.00   52
 17  \w     -3.00  22.00   0.50    2.00    --   43.80 -75.00-165.00   50
 18  \w    -72.00  28.00   0.50    2.00    --  -43.80  75.00 -37.00  200
 19  \w    -48.00 -23.00   0.50   10.00    --  -90.25  75.00 -37.00   50
 20  \w    -92.00 -16.00   0.50   10.00    --  -90.25 125.00  60.00  152
 21  \w   -116.00 -21.00   0.50    2.00    --  -43.80 -57.00  60.00  190
 22  \w    -96.00 -71.00   0.50   10.00    --  -90.25 -45.00  60.00   50
 23  \w   -114.00 -81.00   0.50   10.00    --  -90.25 -94.00 -60.00   66
 24  \w   -101.00 -17.00   0.50    2.00    --  -43.80 -75.00-165.00  168
 25  \w     69.00 104.00   0.50    2.00    --   43.80 178.00-120.00   70
 26  \w     36.00  61.00   0.50   10.00    --  111.75 -30.00 150.00   50
 27  \w     43.00  79.00   0.50   10.00    --  111.75 -45.00  30.00   72
 28  \w   -105.00 -79.00   0.50   10.00    --  -90.25 -75.00-165.00   52
 29  \w   -163.00-137.00   0.50   10.00    --  -90.25 -94.00 -60.00   52
 30  \w   -163.00-124.00   0.50   10.00    --  -90.25 -45.00  60.00   78
 31  \w   -149.00 -67.00   0.50   10.00    --  -90.25 -30.00  90.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0677011000
_diffrn_orient_matrix_UB_12      0.0209512000
_diffrn_orient_matrix_UB_13      -0.0723318000
_diffrn_orient_matrix_UB_21      -0.1344791000
_diffrn_orient_matrix_UB_22      -0.0431444000
_diffrn_orient_matrix_UB_23      -0.0016733000
_diffrn_orient_matrix_UB_31      -0.1235821000
_diffrn_orient_matrix_UB_32      0.0354348000
_diffrn_orient_matrix_UB_33      0.0407952000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33415
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         2.933
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6763
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0738P)^2^+0.6493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5441
_reflns_number_total             6763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj00030e2.cif
_cod_data_source_block           fengchuanqi-cy-39
_cod_depositor_comments
'Adding full bibliography for 7058163--7058164.cif.'
_cod_database_code               7058164
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C O N H'
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Rigid bond restraints
 C32, C52
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Ternary CH refined with riding coordinates:
 C35(H35), C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 C50(H50), C46(H46), C24(H24), C20(H20), C18(H18), C49(H49), C14(H14),
 C40(H40), C44(H44), C6(H6), C48(H48), C17(H17), C47(H47), C23(H23), C15(H15),
 C3(H3), C4(H4), C16(H16), C5(H5), C21(H21), C42(H42), C43(H43), C22(H22),
 C41(H41), C28(H28), C30(H30), C31(H31), C29(H29)
3.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C51(H51A,H51B,H51C), C26(H26A,H26B,H26C), C52(H52A,H52B,
 H52C)
;
_shelx_res_checksum              41997
_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 3.578
_oxdiff_exptl_absorpt_empirical_full_min 0.303