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_7155653
_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         'C14 H17 N O2'
_chemical_formula_sum            'C14 H17 N O2'
_chemical_formula_weight         231.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-09
_audit_creation_method
;
Olex2 1.2
(compiled Dec 12 2016 15:38:10 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-01-27 deposited with the CCDC.
2017-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                78.616(6)
_cell_angle_beta                 88.105(7)
_cell_angle_gamma                69.424(9)
_cell_formula_units_Z            4
_cell_length_a                   8.9339(9)
_cell_length_b                   11.2293(11)
_cell_length_c                   13.7571(8)
_cell_measurement_reflns_used    4753
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.8900
_cell_measurement_theta_min      3.3030
_cell_volume                     1265.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    '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 0.985
_diffrn_measured_fraction_theta_max 0.914
_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   -117.00 -17.00   1.00    6.00    --  -41.68 -34.00-164.00  100
  2  \w    -66.00  33.00   1.00    6.00    --  -41.68  34.00  -7.00   99
  3  \w     17.00 117.00   1.00    6.00    --   41.68  34.00  -7.00  100
  4  \w     84.00 178.00   1.00   30.00    --  109.13  34.00  -7.00   94
  5  \w     34.00 134.00   1.00   30.00    --  109.13 -34.00-164.00  100
  6  \w    -66.00  33.00   1.00    6.00    --  -41.68  38.00 150.00   99
  7  \w     23.00  98.00   1.00    6.00    --   41.68-125.00  60.00   75
  8  \w    -33.00  66.00   1.00    6.00    --   41.68 -34.00-164.00   99
  9  \w     36.00 111.00   1.00   30.00    --  109.13-125.00  90.00   75
 10  \w     83.00 178.00   1.00   30.00    --  109.13  45.00-120.00   95
 11  \w     94.00 178.00   1.00   30.00    --  109.13 125.00 -90.00   84
 12  \w     37.00 138.00   1.00   30.00    --  109.13 -61.00 -60.00  101
 13  \w     26.00  96.00   1.00   30.00    --  109.13 -94.00 -60.00   70
 14  \w     26.00 106.00   1.00   30.00    --  109.13 -94.00 120.00   80
 15  \w     26.00  91.00   1.00   30.00    --  109.13 -94.00-150.00   65
 16  \w      9.00 118.00   1.00    6.00    --   41.68  77.00  90.00  109
 17  \w      1.00  83.00   1.00    6.00    --   41.68 -99.00-180.00   82
 18  \w     14.00 115.00   1.00    6.00    --   41.68  57.00  90.00  101
 19  \w      9.00 118.00   1.00    6.00    --   41.68  77.00 -30.00  109
 20  \w      9.00 118.00   1.00    6.00    --   41.68  77.00-180.00  109
 21  \w     81.00 178.00   1.00   30.00    --  109.13  30.00  60.00   97
 22  \w     83.00 178.00   1.00   30.00    --  109.13  45.00 -90.00   95
 23  \w     81.00 178.00   1.00   30.00    --  109.13  30.00 150.00   97
 24  \w     80.00 178.00   1.00   30.00    --  109.13  61.00   0.00   98
 25  \w     83.00 178.00   1.00   30.00    --  109.13  45.00  90.00   95
 26  \w     80.00 178.00   1.00   30.00    --  109.13  61.00-180.00   98
 27  \w     80.00 178.00   1.00   30.00    --  109.13  61.00 150.00   98
 28  \w     80.00 178.00   1.00   30.00    --  109.13  61.00-150.00   98
 29  \w     80.00 178.00   1.00   30.00    --  109.13  61.00 -60.00   98
 30  \w     83.00 178.00   1.00   30.00    --  109.13  45.00 -60.00   95
 31  \w   -116.00 -17.00   1.00    6.00    --  -41.68 -38.00 -30.00   99
 32  \w   -115.00 -14.00   1.00    6.00    --  -41.68 -57.00  90.00  101
 33  \w   -115.00 -14.00   1.00    6.00    --  -41.68 -57.00 -60.00  101
 34  \w     23.00  98.00   1.00    6.00    --   41.68-125.00  30.00   75
 35  \w      9.00 118.00   1.00    6.00    --   41.68  77.00 -90.00  109
 36  \w     80.00 178.00   1.00   30.00    --  109.13  61.00  90.00   98
 37  \w     80.00 178.00   1.00   30.00    --  109.13  61.00 -90.00   98
 38  \w     77.00 178.00   1.00   30.00    --  109.13  77.00  30.00  101
 39  \w     80.00 178.00   1.00   30.00    --  109.13  61.00  30.00   98
 40  \w     80.00 178.00   1.00   30.00    --  109.13  61.00-120.00   98
 41  \w     80.00 178.00   1.00   30.00    --  109.13  61.00 120.00   98
 42  \w     80.00 178.00   1.00   30.00    --  109.13  61.00  60.00   98
 43  \w     77.00 178.00   1.00   30.00    --  109.13  77.00 -30.00  101
 44  \w     77.00 178.00   1.00   30.00    --  109.13  77.00-180.00  101
 45  \w     80.00 178.00   1.00   30.00    --  109.13  61.00 -30.00   98
 46  \w   -116.00 -17.00   1.00    6.00    --  -41.68 -38.00  90.00   99
 47  \w   -115.00 -14.00   1.00    6.00    --  -41.68 -57.00-180.00  101
 48  \w   -116.00 -17.00   1.00    6.00    --  -41.68 -38.00 150.00   99
 49  \w      9.00 118.00   1.00    6.00    --   41.68  77.00  30.00  109
 50  \w      1.00  72.00   1.00    6.00    --   41.68  19.00-180.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1786659000
_diffrn_orient_matrix_UB_12      0.0170078000
_diffrn_orient_matrix_UB_13      -0.0032359000
_diffrn_orient_matrix_UB_21      0.0417686000
_diffrn_orient_matrix_UB_22      -0.1438541000
_diffrn_orient_matrix_UB_23      0.0497006000
_diffrn_orient_matrix_UB_31      -0.0176923000
_diffrn_orient_matrix_UB_32      0.0370380000
_diffrn_orient_matrix_UB_33      0.1029000000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1469
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35490
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         80.015
_diffrn_reflns_theta_min         3.280
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.214
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0831
_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^)+3.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.1880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3219
_reflns_number_total             5062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00832e2.cif
_cod_data_source_block           mdh036b
_cod_database_code               7155653
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C14 H17 N O2'
_cell_oxdiff_angle_alpha         78.616(6)
_cell_oxdiff_angle_beta          88.105(7)
_cell_oxdiff_angle_gamma         69.424(9)
_cell_oxdiff_length_a            8.9339(9)
_cell_oxdiff_length_b            11.2293(11)
_cell_oxdiff_length_c            13.7571(8)
_cell_oxdiff_measurement_reflns_used 4753
_cell_oxdiff_volume              1265.68(19)
_reflns_odcompleteness_completeness 99.09
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              14123
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.844
_oxdiff_exptl_absorpt_empirical_full_min 0.591