Enantioselective Michael Reaction of Cyclic β-Ketoesters with Morita-Baylis-Hillman Derivatives Using a Phase-Transfer Catalyst.
Takagi, Ryukichi; Fujii, Emi; Kondo, Hirotoshi; The Journal of organic chemistry 83 (2018) 11191–11203; doi:10.1021/acs.joc.8b01777

data_4035635
_publ_section_title
;
 Enantioselective Michael Reaction of Cyclic \b-Ketoesters with
 Morita-Baylis-Hillman Derivatives Using a Phase-Transfer Catalyst.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11191
_journal_page_last               11203
_journal_paper_doi               10.1021/acs.joc.8b01777
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H29 Br O6'
_chemical_formula_weight         445.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8906(6)
_cell_length_b                   13.1404(7)
_cell_length_c                   14.9044(8)
_cell_measurement_reflns_used    8471
_cell_measurement_temperature    123.(2)
_cell_measurement_theta_max      27.9203
_cell_measurement_theta_min      2.3161
_cell_volume                     2132.9(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX2(Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multilayered conforcal mirror'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12774
_diffrn_reflns_theta_full        27.95
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         2.07
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'
_exptl_absorpt_coefficient_mu    1.958
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.176
_refine_ls_abs_structure_details
;

Flack x determined using 1881 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0201
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0470
_refine_ls_wR_factor_ref         0.0474
_reflns_number_gt                4675
_reflns_number_total             4991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01777_si_003.cif
_cod_data_source_block           20171018tr14472_1107
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_database_code               4035635
_shelx_res_checksum              62697
_shelx_hkl_checksum              88751