Diastereoselective synthesis of α-dicarbonyl cyclopropanes via a lanthanide amide-catalysed reaction.
Sun, Wenxi; Peng, Cheng; Yao, Zhigang; Xu, Fan; Organic & biomolecular chemistry 17 (2019) 6620–6628; doi:10.1039/c9ob00732f

data_7156918
_publ_section_title
;
 Diastereoselective synthesis of \a-dicarbonyl cyclopropanes via a
 lanthanide amide-catalysed reaction.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6620
_journal_page_last               6628
_journal_paper_doi               10.1039/c9ob00732f
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C26 H24 O4'
_chemical_formula_sum            'C26 H24 O4'
_chemical_formula_weight         400.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
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  Olex2 1.2-ac2
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2018-09-11 deposited with the CCDC.    2019-06-17 downloaded from the CCDC.
;
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_cell_formula_units_Z            8
_cell_length_a                   11.9937(5)
_cell_length_b                   11.8843(4)
_cell_length_c                   30.2028(11)
_cell_measurement_reflns_used    2260
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      72.7670
_cell_measurement_theta_min      3.9830
_cell_volume                     4305.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_measurement_details
;
  1 omega  -41.00    2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000 -180.0000 43

  2 omega  -45.00   15.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000   90.0000 60

  3 omega  -21.00   29.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000  -60.0000 50

  4 omega   41.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000  -30.0000 57

  5 omega   38.00   68.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000 -150.0000 30

  6 omega   29.00   85.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000  -90.0000 56

  7 omega   50.00   97.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000   60.0000 47

  8 omega   29.00   77.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000   30.0000 48

  9 omega   34.00   66.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000 -120.0000 32

 10 omega   49.00   75.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000    0.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1224334000
_diffrn_orient_matrix_UB_12      -0.0061062000
_diffrn_orient_matrix_UB_13      0.0152001000
_diffrn_orient_matrix_UB_21      -0.0282362000
_diffrn_orient_matrix_UB_22      0.1021604000
_diffrn_orient_matrix_UB_23      -0.0293126000
_diffrn_orient_matrix_UB_31      -0.0266842000
_diffrn_orient_matrix_UB_32      -0.0795869000
_diffrn_orient_matrix_UB_33      -0.0388685000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10729
_diffrn_reflns_theta_full        73.69
_diffrn_reflns_theta_max         73.69
_diffrn_reflns_theta_min         4.71
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4248
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1990
_reflns_number_gt                2708
_reflns_number_total             4248
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00732f2.cif
_cod_data_source_block           g160314a
_cod_depositor_comments
'Adding full bibliography for 7156917--7156919.cif.'
_cod_database_code               7156918
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_submission_special_instructions 'No special instructions were received'