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_7155367
_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_absolute_configuration ad
_chemical_formula_moiety         'C14 H17 N O3'
_chemical_formula_sum            'C14 H17 N O3'
_chemical_formula_weight         247.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-11
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.3439(5)
_cell_length_b                   5.9484(2)
_cell_length_c                   12.9762(5)
_cell_measurement_reflns_used    2647
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.8230
_cell_measurement_theta_min      5.3910
_cell_volume                     1261.55(8)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega -114.00  -66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798 -136.0000   39.0000 48

  2 omega -116.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -73.0000  -82.0000 106

  3 omega   83.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   47.0000 -124.0000 95

  4 omega   35.00  141.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -73.0000  -82.0000 106

  5 omega   37.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -133.0000 -141.0000 88

  6 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798   38.0000  120.0000 83

  7 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798 -125.0000  -60.0000 75

  8 omega   33.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -30.0000 58

  9 omega   33.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000   90.0000 58

 10 omega   33.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -60.0000 58

 11 omega   36.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000   30.0000 62

 12 omega -116.00  -91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -38.0000  150.0000 25

 13 omega -118.00   -9.00   1.0000    1.0000
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      0.0291014000
_diffrn_orient_matrix_UB_12      -0.2011252000
_diffrn_orient_matrix_UB_13      0.0652808000
_diffrn_orient_matrix_UB_21      0.0896971000
_diffrn_orient_matrix_UB_22      0.0638878000
_diffrn_orient_matrix_UB_23      -0.0220540000
_diffrn_orient_matrix_UB_31      0.0007469000
_diffrn_orient_matrix_UB_32      0.1499133000
_diffrn_orient_matrix_UB_33      0.0966847000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6703
_diffrn_reflns_point_group_measured_fraction_full 0.828
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.410
_diffrn_reflns_theta_min         5.413
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.983
_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    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.1551
_exptl_crystal_size_mid          0.1455
_exptl_crystal_size_min          0.1014
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 636 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.49(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2069
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0396P)^2^+0.0995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.549
_reflns_Friedel_fraction_full    0.638
_reflns_Friedel_fraction_max     0.587
_reflns_number_gt                1907
_reflns_number_total             2069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02221a2.cif
_cod_data_source_block           mdh015
_cod_depositor_comments
'Adding full bibliography for 7155367--7155368.cif.'
_cod_database_code               7155367
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C14 H17 N O3'
_reflns_odcompleteness_completeness 99.93
_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.a Ternary CH refined with riding coordinates:
 C4(H4), C2(H2), C5(H5), C3(H3A), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C9(H9), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              41269
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'