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_7157516
_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         'C25 H20 Br N O3'
_chemical_formula_sum            'C25 H20 Br N O3'
_chemical_formula_weight         462.33
_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             2020-04-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-05-14 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                103.149(4)
_cell_angle_beta                 104.108(4)
_cell_angle_gamma                94.618(4)
_cell_formula_units_Z            2
_cell_length_a                   9.6348(5)
_cell_length_b                   10.2842(5)
_cell_length_c                   11.5040(5)
_cell_measurement_reflns_used    3810
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9270
_cell_measurement_theta_min      4.4540
_cell_volume                     1065.31(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     -2.00  73.00   1.00    1.00    --   54.00 -57.00 150.00   75
  2  \w     28.00 107.00   1.00    1.00    --   54.00-125.00 150.00   79
  3  \w     80.00 106.00   1.00    1.00    --  108.00-111.00  30.00   26
  4  \w     57.00 113.00   1.00    1.00    --  108.00-111.00 -90.00   56
  5  \w    107.00 138.00   1.00    1.00    --  108.00 -25.00-120.00   31
  6  \w    142.00 178.00   1.00    1.00    --  108.00  25.00-150.00   36
  7  \w    145.00 176.00   1.00    1.00    --  108.00  50.00 -90.00   31
  8  \w    114.00 161.00   1.00    1.00    --  108.00  63.00  60.00   47
  9  \w    126.00 171.00   1.00    1.00    --  108.00  25.00 150.00   45
 10  \w     72.00 121.00   1.00    1.00    --   54.00  57.00  30.00   49
 11  \w     74.00 107.00   1.00    1.00    --  108.00  25.00 150.00   33
 12  \w     54.00 138.00   1.00    1.00    --  108.00 -25.00  90.00   84
 13  \w     89.00 121.00   1.00    1.00    --  108.00  50.00 -90.00   32
 14  \w     38.00 125.00   1.00    1.00    --  108.00 -50.00 -60.00   87
 15  \w     33.00 121.00   1.00    1.00    --   54.00  57.00 120.00   88
 16  \w     43.00  68.00   1.00    1.00    --    0.00  57.00 120.00   25
 17  \w    -11.00  18.00   1.00    1.00    --    0.00 -57.00 -30.00   29
 18  \w    -12.00  69.00   1.00    1.00    --   54.00 -57.00 -30.00   81
 19  \w     38.00 109.00   1.00    1.00    --  108.00 -77.00 -90.00   71
 20  \w     35.00  78.00   1.00    1.00    --  108.00 -25.00-120.00   43
 21  \w    -14.00  68.00   1.00    1.00    --   54.00 -57.00-120.00   82
 22  \w     13.00  38.00   1.00    1.00    --    0.00  57.00-150.00   25
 23  \w     40.00 130.00   1.00    1.00    --  108.00 -63.00 120.00   90
 24  \w     38.00 116.00   1.00    1.00    --  108.00-111.00 150.00   78
 25  \w    -21.00  23.00   1.00    1.00    --    0.00  57.00 120.00   44
 26  \w    -57.00 -32.00   1.00    1.00    --    0.00 -57.00 -30.00   25
 27  \w     59.00 144.00   1.00    1.00    --  108.00 178.00-180.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1024457000
_diffrn_orient_matrix_UB_12      0.1056507000
_diffrn_orient_matrix_UB_13      -0.0265487000
_diffrn_orient_matrix_UB_21      -0.1297400000
_diffrn_orient_matrix_UB_22      0.0374803000
_diffrn_orient_matrix_UB_23      -0.0879539000
_diffrn_orient_matrix_UB_31      -0.0207256000
_diffrn_orient_matrix_UB_32      0.1076963000
_diffrn_orient_matrix_UB_33      0.1093550000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6650
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.584
_diffrn_reflns_theta_max         66.584
_diffrn_reflns_theta_min         4.099
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.441
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0079(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0418P)^2^+0.6776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3459
_reflns_number_total             3769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00826e2.cif
_cod_data_source_block           lsq_p192_3
_cod_depositor_comments
'Adding full bibliography for 7157515--7157516.cif.'
_cod_original_cell_volume        1065.30(9)
_cod_database_code               7157516
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.692
_shelx_estimated_absorpt_t_min   0.561
_reflns_odcompleteness_completeness 100.00
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              58105
_olex2_date_sample_data_collection 2020-04-07
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.705