A mechanistic study of the Lewis acid–Brønsted base–Brønsted acid catalysed asymmetric Michael addition of diethyl malonate to cyclohexenone
Samoilichenko, Yuri; Kondratenko, Veronica; Ezernitskaya, Mariam; Lyssenko, Konstantin; Peregudov, Alexander; Khrustalev, Victor; Maleev, Victor; Moskalenko, Margarita; North, Michael; Tsaloev, Alan; Gugkaeva, Zalina T.; Belokon, Yuri; Catal. Sci. Technol. 7 (2017) 90–; doi:10.1039/C6CY01697A

data_1544553
_publ_section_title
;
 A mechanistic study of the Lewis acid--Br\/onsted base--Br\/onsted acid
 catalysed asymmetric Michael addition of diethyl malonate to
 cyclohexenone
;
_journal_issue                   1
_journal_name_full               'Catal. Sci. Technol.'
_journal_page_first              90
_journal_paper_doi               10.1039/C6CY01697A
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C46 H30 O4, H2 O'
_chemical_formula_sum            'C46 H32 O5'
_chemical_formula_weight         664.71
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-06-29 deposited with the CCDC.
2016-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6965(4)
_cell_length_b                   17.3653(7)
_cell_length_c                   19.2464(8)
_cell_measurement_reflns_used    8084
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.35
_cell_volume                     3240.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            44815
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_min         2.116
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       prism
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 2621 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         9922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0846P)^2^+0.0074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1457
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7141
_reflns_number_total             9922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cy01697a2.cif
_cod_data_source_block           Sam2
_cod_depositor_comments          'Adding full bibliography for 1544553.cif.'
_cod_database_code               1544553
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2014/6
_shelx_res_checksum              34169