Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks
Piens, Nicola; Van Hecke, Kristof; Vogt, Dieter; D'hooghe, Matthias; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00832E

data_7155654
_publ_section_title
;
 Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to
 versatile \b-lactam building blocks
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00832E
_journal_year                    2017
_chemical_formula_moiety         'C21 H25 N O4'
_chemical_formula_sum            'C21 H25 N O4'
_chemical_formula_weight         355.42
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-01-27 deposited with the CCDC.
2017-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.473(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6008(4)
_cell_length_b                   8.3244(3)
_cell_length_c                   15.3345(5)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.1510
_cell_measurement_theta_min      3.0540
_cell_volume                     1838.38(10)
_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 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega -108.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  147.0000  -73.0000 95

  2 omega -114.00  -59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798 -147.0000 -123.0000 55

  3 omega  -95.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  124.0000  121.0000 94

  4 omega   35.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798 -147.0000 -123.0000 77

  5 omega   95.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  124.0000  121.0000 83

  6 omega   36.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -147.0000 -123.0000 97

  7 omega   36.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -124.0000   42.0000 85

  8 omega   81.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  147.0000  -73.0000 93

  9 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798   38.0000   60.0000 83

 10 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798   38.0000  -60.0000 83

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

 12 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000  -60.0000 97

 13 omega   36.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000   60.0000 62

 14 omega   33.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000 -120.0000 58

 15 omega   36.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000 -180.0000 62

 16 omega -115.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -57.0000   30.0000 101

 17 omega -115.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -57.0000  150.0000 101

 18 omega -118.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -77.0000  -60.0000 109

 19 omega    9.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798   77.0000 -120.0000 109

 20 omega   83.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000 -150.0000 93
;
_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      0.1055495000
_diffrn_orient_matrix_UB_12      -0.0273568000
_diffrn_orient_matrix_UB_13      0.0232928000
_diffrn_orient_matrix_UB_21      -0.0150275000
_diffrn_orient_matrix_UB_22      -0.1824209000
_diffrn_orient_matrix_UB_23      -0.0114386000
_diffrn_orient_matrix_UB_31      0.0084255000
_diffrn_orient_matrix_UB_32      0.0152558000
_diffrn_orient_matrix_UB_33      -0.0985133000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17634
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.298
_diffrn_reflns_theta_min         3.069
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.980
_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    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1647
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0570P)^2^+0.5395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3279
_reflns_number_total             3696
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00832e2.cif
_cod_data_source_block           mdh013
_cod_database_code               7155654
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C21 H25 N O4'
_reflns_odcompleteness_completeness 99.91
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C10(H10), C20(H20), C12(H12), C19(H19), C21(H21), C18(H18),
 C17(H17)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C14(H14A,H14B,H14C), C6(H6A,H6B,H6C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              49937
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'