Diastereoselective synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and their transformation into 3,4-oxolane-fused bicyclic β-lactams.
Piens, Nicola; De Craene, Sven; Franceus, Jorick; Mollet, Karen; Van Hecke, Kristof; Desmet, Tom; D'hooghe, Matthias; Organic & biomolecular chemistry 14 (2016) 11279–11288; doi:10.1039/c6ob02221a

data_7155368
_publ_section_title
;
 Diastereoselective synthesis of
 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and their transformation
 into 3,4-oxolane-fused bicyclic \b-lactams.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11279
_journal_page_last               11288
_journal_paper_doi               10.1039/c6ob02221a
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C18 H17 N O4'
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-05-14 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                94.767(3)
_cell_angle_beta                 94.714(4)
_cell_angle_gamma                99.371(4)
_cell_formula_units_Z            8
_cell_length_a                   6.7690(4)
_cell_length_b                   17.4058(7)
_cell_length_c                   26.8238(9)
_cell_measurement_reflns_used    6191
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.5990
_cell_measurement_theta_min      3.1810
_cell_volume                     3092.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
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_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
  1 omega  -50.00   32.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798   39.0000   16.0000 82

  2 omega -116.00  -17.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -39.0000 -137.0000 99

  3 omega  -32.00   66.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798  -39.0000 -137.0000 98

  4 omega   17.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798   39.0000   16.0000 99

  5 omega   84.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   39.0000   16.0000 94

  6 omega   35.00   93.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -39.0000 -137.0000 58

  7 omega  -96.00   -2.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  125.0000   90.0000 94

  8 omega   33.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000   90.0000 58

  9 omega   33.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -30.0000 58

 10 omega   56.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   15.0000  150.0000 122

 11 omega   36.00  106.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -125.0000 -120.0000 70

 12 omega   94.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  125.0000 -150.0000 84

 13 omega   33.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000 -180.0000 58

 14 omega   36.00  102.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -125.0000 -180.0000 66

 15 omega   26.00  109.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000    0.0000 83

 16 omega   26.00  109.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -120.0000 83

 17 omega    9.00  118.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798   77.0000 -150.0000 109

 18 omega    9.00   62.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798   77.0000    0.0000 53

 19 omega    9.00  118.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798   77.0000   90.0000 109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1932247000
_diffrn_orient_matrix_UB_12      -0.0496337000
_diffrn_orient_matrix_UB_13      0.0142858000
_diffrn_orient_matrix_UB_21      -0.1267610000
_diffrn_orient_matrix_UB_22      0.0547179000
_diffrn_orient_matrix_UB_23      -0.0250717000
_diffrn_orient_matrix_UB_31      -0.0177009000
_diffrn_orient_matrix_UB_32      -0.0516501000
_diffrn_orient_matrix_UB_33      -0.0502050000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            28410
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.342
_diffrn_reflns_theta_min         2.933
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.337
_exptl_crystal_description       rod
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2574
_exptl_crystal_size_mid          0.0804
_exptl_crystal_size_min          0.0436
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     837
_refine_ls_number_reflns         12222
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0617
_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^)+(0.0460P)^2^+1.7130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7953
_reflns_number_total             12222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02221a2.cif
_cod_data_source_block           mdh016b
_cod_depositor_comments
'Adding full bibliography for 7155367--7155368.cif.'
_cod_database_code               7155368
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C18 H17 N O4'
_reflns_odcompleteness_completeness 99.31
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C67 \\sim C68 \\sim C69 \\sim C70 \\sim C71 \\sim C72: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C11(H11), C12(H12), C19(H19), C20(H20), C29(H29), C30(H30),
 C37(H37), C38(H38), C47(H47), C48(H48), C55(H55), C56(H56), C65(H65), C66(H66)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C23(H23), C24(H24), C26(H26), C27(H27), C32(H32), C33(H33), C34(H34),
  C35(H35), C36(H36), C41(H41), C42(H42), C44(H44), C45(H45), C50(H50),
 C51(H51), C52(H52), C53(H53), C54(H54), C59(H59), C60(H60), C62(H62), C63(H63),
  C68(H68), C69(H69), C70(H70), C71(H71), C72(H72)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C28(H28A,H28B,H28C), C46(H46A,H46B,H46C), C64(H64A,H64B,
 H64C)
3.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8A), O12(H12A), O16(H16A)
;
_shelx_res_checksum              78615
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'