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_7156917
_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         'C25 H22 O3'
_chemical_formula_sum            'C25 H22 O3'
_chemical_formula_weight         370.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-11 deposited with the CCDC.    2019-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.83(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.207(11)
_cell_length_b                   7.147(5)
_cell_length_c                   18.155(12)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.30
_cell_volume                     1978(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1238
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            38641
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.39
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1743 before and 0.1181 after correction.
The Ratio of minimum to maximum transmission is 0.4199.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0787P)^2^+0.5610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1760
_reflns_number_gt                3542
_reflns_number_total             4538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00732f2.cif
_cod_data_source_block           mo_b180412a_0m_a_a
_cod_depositor_comments
'Adding full bibliography for 7156917--7156919.cif.'
_cod_database_code               7156917
_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:
 C6(H6), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'