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_7058163
_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_absolute_configuration unk
_chemical_formula_moiety         'C21 H18 F N3 O'
_chemical_formula_sum            'C21 H18 F N3 O'
_chemical_formula_weight         347.38
_chemical_name_systematic        1
_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     dual
_audit_creation_date             2018-11-28
_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                 91.446(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1744(2)
_cell_length_b                   23.9422(5)
_cell_length_c                   16.3375(4)
_cell_measurement_reflns_used    10391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3140
_cell_measurement_theta_min      3.2750
_cell_volume                     3587.48(14)
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.960
_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    -29.00   3.00   0.50    0.28    --  -43.80  82.00  43.00   64
  2  \w    -72.00 -35.00   0.50    0.28    --  -43.80  82.00  43.00   74
  3  \w    -93.00 -68.00   0.50    1.14    --  -90.25  82.00  43.00   50
  4  \w   -117.00 -13.00   0.50    0.28    --  -43.80 -82.00 -77.00  208
  5  \w     41.00  66.00   0.50    0.28    --   43.80  82.00  43.00   50
  6  \w     82.00 177.00   0.50    1.14    --  111.75  82.00  43.00  190
  7  \w    120.00 174.00   0.50    1.14    --  111.75  77.00   0.00  108
  8  \w    130.00 174.00   0.50    1.14    --  111.75 125.00 -90.00   88
  9  \w    100.00 126.00   0.50    1.14    --  111.75 125.00 -90.00   52
 10  \w     77.00 122.00   0.50    0.28    --   43.80 178.00 -30.00   90
 11  \w     38.00 134.00   0.50    1.14    --  111.75 -61.00 -30.00  192
 12  \w    108.00 136.00   0.50    1.14    --  111.75 -82.00 -77.00   56
 13  \w     69.00 121.00   0.50    1.14    --  111.75-125.00-180.00  104
 14  \w     54.00  94.00   0.50    1.14    --  111.75 -82.00 -77.00   80
 15  \w     52.00 107.00   0.50    1.14    --  111.75 -94.00-120.00  110
 16  \w     38.00  64.00   0.50    1.14    --  111.75-125.00-180.00   52
 17  \w      0.00  78.00   0.50    0.28    --   43.80 -99.00  90.00  156
 18  \w     38.00  78.00   0.50    1.14    --  111.75 -94.00 120.00   80
 19  \w    -86.00 -61.00   0.50    1.14    --  -90.25 -82.00 -77.00   50
 20  \w   -164.00 -86.00   0.50    1.14    --  -90.25 -94.00   0.00  156
 21  \w   -160.00 -62.00   0.50    1.14    --  -90.25 -77.00 -30.00  196
;
_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      -0.0898603000
_diffrn_orient_matrix_UB_12      -0.0540324000
_diffrn_orient_matrix_UB_13      0.0076384000
_diffrn_orient_matrix_UB_21      -0.0388731000
_diffrn_orient_matrix_UB_22      0.0164008000
_diffrn_orient_matrix_UB_23      0.0880173000
_diffrn_orient_matrix_UB_31      -0.1365347000
_diffrn_orient_matrix_UB_32      0.0308373000
_diffrn_orient_matrix_UB_33      -0.0330127000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23757
_diffrn_reflns_point_group_measured_fraction_full 0.734
_diffrn_reflns_point_group_measured_fraction_max 0.694
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.886
_diffrn_reflns_theta_min         2.705
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58545
_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    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 2078 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     929
_refine_ls_number_reflns         10531
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.533
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.1235
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.2295
_reflns_Friedel_coverage         0.412
_reflns_Friedel_fraction_full    0.457
_reflns_Friedel_fraction_max     0.416
_reflns_number_gt                8470
_reflns_number_total             10531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj00030e2.cif
_cod_data_source_block           fengchuanqi-cy-36-2
_cod_depositor_comments
'Adding full bibliography for 7058163--7058164.cif.'
_cod_database_code               7058163
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C O N H'
_reflns_odcompleteness_completeness 99.70
_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
 F53, C31
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O89, N88
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C57, C58, C59
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C84, C85
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F79, C58
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F105, C85
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C80, C85
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C80, C81
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
F53 \\sim C31: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
O89 \\sim N88: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
C57 \\sim C58 \\sim C59: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004
C84 \\sim C85: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
F79 \\sim C58: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
F105 \\sim C85: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
C80 \\sim C85: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
C80 \\sim C81: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(F79) = Uanis(C58)
Uanis(F105) = Uanis(C85)
4.a Ternary CH refined with riding coordinates:
 C34(H34), C61(H61), C87(H87), C7(H7)
4.b Aromatic/amide H refined with riding coordinates:
 C32(H32), C13(H13), C82(H82), C73(H73), C9(H9), C55(H55), C70(H70), C92(H92),
 C28(H28), C59(H59), C16(H16), C66(H66), C74(H74), C12(H12), C11(H11), C20(H20),
  C18(H18), C49(H49), C56(H56), C76(H76), C80(H80), C77(H77), C2(H2), C46(H46),
 C68(H68), C45(H45), C50(H50), C43(H43), C84(H84), C96(H96), C83(H83), C6(H6),
 C95(H95), C4(H4), C48(H48), C69(H69), C99(H99), C93(H93), C30(H30), C19(H19),
 C39(H39), C29(H29), C17(H17), C94(H94), C3(H3), C100(H100), C41(H41), C42(H42),
  C67(H67), C75(H75), C103(H103), C57(H57), C5(H5), C40(H40), C101(H101),
 C102(H102)
4.c Idealised Me refined as rotating group:
 C78(H78A,H78B,H78C), C104(H10A,H10B,H10C), C52(H52A,H52B,H52C), C21(H21A,H21B,
 H21C)
;
_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 1.895
_oxdiff_exptl_absorpt_empirical_full_min 0.395