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_7155655
_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         'C19 H19 N O4'
_chemical_formula_sum            'C19 H19 N O4'
_chemical_formula_weight         325.35
_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     iterative
_audit_creation_date             2015-03-13
_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                96.857(3)
_cell_angle_beta                 98.399(3)
_cell_angle_gamma                100.637(3)
_cell_formula_units_Z            6
_cell_length_a                   7.6298(2)
_cell_length_b                   18.0069(7)
_cell_length_c                   18.6575(6)
_cell_measurement_reflns_used    9543
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.9540
_cell_measurement_theta_min      3.2070
_cell_volume                     2463.87(15)
_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    'olex2.solve (Bourhis et al., 2015)'
_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  -97.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  127.0000  100.0000 94

  2 omega -114.00  -62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798 -143.0000 -144.0000 52

  3 omega   25.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798 -127.0000   25.0000 74

  4 omega   33.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798 -143.0000 -144.0000 76

  5 omega   84.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  143.0000  -89.0000 92

  6 omega   93.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  127.0000  100.0000 85

  7 omega   37.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -143.0000 -144.0000 93

  8 omega   36.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -127.0000   25.0000 86

  9 omega -105.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  143.0000  -89.0000 93

 10 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798   38.0000 -150.0000 83

 11 omega -116.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -38.0000   30.0000 99

 12 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798   38.0000  -30.0000 83

 13 omega   33.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -77.0000  -90.0000 109

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

 15 omega   26.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000   30.0000 83

 16 omega   26.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -150.0000 83

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

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

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

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

 21 omega -118.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -77.0000   30.0000 109

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

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

 24 omega  -33.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798  -38.0000    0.0000 99

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

 26 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000 -150.0000 97

 27 omega   83.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000    0.0000 46

 28 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000  -90.0000 97

 29 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000  120.0000 97
;
_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      0.0355767000
_diffrn_orient_matrix_UB_12      -0.0678958000
_diffrn_orient_matrix_UB_13      0.0389429000
_diffrn_orient_matrix_UB_21      0.0075432000
_diffrn_orient_matrix_UB_22      0.0483546000
_diffrn_orient_matrix_UB_23      0.0747239000
_diffrn_orient_matrix_UB_31      -0.2053663000
_diffrn_orient_matrix_UB_32      -0.0283785000
_diffrn_orient_matrix_UB_33      -0.0052806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36965
_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         75.302
_diffrn_reflns_theta_min         3.226
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.978
_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    1.316
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.509
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.1346
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         9909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0789P)^2^+0.0838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6755
_reflns_number_total             9909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00832e2.cif
_cod_data_source_block           mdh012
_cod_database_code               7155655
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C19 H19 N O4'
_chemical_oxdiff_usercomment     NP265
_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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C32(H32A,H32B), C41(H41A,H41B), C3(H3A,H3B), C22(H22A,H22B),
 C51(H51A,H51B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C7(H7), C25(H25), C44(H44), C47(H47), C28(H28), C48(H48),
 C6(H6), C45(H45), C18(H18), C53(H53), C54(H54), C26(H26), C36(H36), C57(H57),
 C56(H56), C37(H37), C19(H19), C34(H34), C29(H29), C16(H16), C15(H15), C38(H38),
  C55(H55), C35(H35), C17(H17)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C49(H49A,H49B,H49C), C30(H30A,H30B,H30C), C12(H12A,H12B,
 H12C), C50(H50A,H50B,H50C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              72464
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'