P(NMe<sub>2</sub>)<sub>3</sub> mediated cyclopropanation of α-methylene-β-lactams for rapid syntheses of spirocyclopropyl β-lactams.
Luo, Si-Qin; Liu, Wei; Ruan, Ban-Feng; Fan, Shi-Lu; Zhu, Hui-Xia; Tao, Wei; Xiao, Hua; Organic & biomolecular chemistry 18 (2020) 4599–4603; doi:10.1039/d0ob00826e

data_7157515
_publ_section_title
;
 P(NMe<sub>2</sub>)<sub>3</sub> mediated cyclopropanation of
 \a-methylene-\b-lactams for rapid syntheses of spirocyclopropyl
 \b-lactams.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4599
_journal_page_last               4603
_journal_paper_doi               10.1039/d0ob00826e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C28 H25 N O6'
_chemical_formula_sum            'C28 H25 N O6'
_chemical_formula_weight         471.49
_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             2019-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-20 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                103.598(4)
_cell_angle_beta                 99.511(4)
_cell_angle_gamma                95.686(4)
_cell_formula_units_Z            4
_cell_length_a                   10.6091(5)
_cell_length_b                   11.9396(5)
_cell_length_c                   20.1405(8)
_cell_measurement_reflns_used    5846
_cell_measurement_temperature    292.01(10)
_cell_measurement_theta_max      69.7230
_cell_measurement_theta_min      6.1370
_cell_volume                     2420.12(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      292.01(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -63.00  -23.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000   60.0000 40

  2 omega  -84.00  -38.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  120.0000 46

  3 omega   29.00   60.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000   30.0000 31

  4 omega  -15.00   11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000   60.0000 26

  5 omega  -27.00    4.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000   30.0000 31

  6 omega  -85.00  -34.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -150.0000 51

  7 omega   41.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 69

  8 omega   -9.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -30.0000 33

  9 omega   32.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 91

 10 omega   29.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -30.0000 47

 11 omega   32.00  111.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 79

 12 omega   20.00   45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  -60.9645 25

 13 omega   74.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 36

 14 omega   82.00  162.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 80

 15 omega   50.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 38

 16 omega   89.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 26

 17 omega  146.00  173.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 27

 18 omega   35.00   87.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 52

 19 omega   97.00  172.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -90.0000 75

 20 omega   35.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -90.0000 44

 21 omega   66.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 25

 22 omega   82.00  135.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 53

 23 omega   38.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 69

 24 omega   40.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 54

 25 omega   54.00   80.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 26

 26 omega   57.00  137.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 80

 27 omega   88.00  113.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -30.0000 25

 28 omega   77.00  132.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -90.0000 55

 29 omega   35.00  147.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -60.0000 112

 30 omega   46.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 46

 31 omega   45.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 26

 32 omega  120.00  146.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 26

 33 omega   41.00  131.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  150.0000 90

 34 omega  -79.00   23.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -30.0000 102

 35 omega  -30.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000   90.0000 91

 36 omega   27.00  127.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -150.0000 100

 37 omega   32.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 91

 38 omega   20.00   46.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  -99.4191 26

 39 omega   22.00   49.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   80.8289 27

 40 omega  -15.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   30.0000 91

 41 omega   32.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 91

 42 omega  -15.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 91

 43 omega   76.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 102

 44 omega   76.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 102

 45 omega   81.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -150.0000 97

 46 omega   68.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  120.0000 110
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0488413000
_diffrn_orient_matrix_UB_12      0.1076485000
_diffrn_orient_matrix_UB_13      0.0618287000
_diffrn_orient_matrix_UB_21      0.1391527000
_diffrn_orient_matrix_UB_22      -0.0058499000
_diffrn_orient_matrix_UB_23      -0.0120126000
_diffrn_orient_matrix_UB_31      -0.0196906000
_diffrn_orient_matrix_UB_32      0.0798305000
_diffrn_orient_matrix_UB_33      -0.0497056000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26969
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         3.849
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.043
_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     635
_refine_ls_number_reflns         8518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0630P)^2^+0.4582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6086
_reflns_number_total             8518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00826e2.cif
_cod_data_source_block           xc-1
_cod_depositor_comments
'Adding full bibliography for 7157515--7157516.cif.'
_cod_original_cell_volume        2420.12(18)
_cod_database_code               7157515
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.63
_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:
 C9(H9A,H9B), C10(H10A,H10B), C37(H37A,H37B), C38(H38A,H38B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33), C42(H42), C43(H43), C44(H44),
 C45(H45), C46(H46), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C28(H28A,H28B,H28C), C48(H48A,H48B,H48C), C50(H50A,H50B,
 H50C)
;
_shelx_res_checksum              42117
_olex2_submission_special_instructions 'No special instructions were received'