Enantioselective isothiourea-catalysed reversible Michael addition of aryl esters to 2-benzylidene malononitriles.
Nimmo, Alastair J.; Bitai, Jacqueline; Young, Claire M.; McLaughlin, Calum; Slawin, Alexandra M. Z.; Cordes, David B.; Smith, Andrew D.; Chemical science 14 (2023) 7537–7544; doi:10.1039/d3sc02101g

data_1569765
_publ_section_title
;
 Enantioselective isothiourea-catalysed reversible Michael addition of
 aryl esters to 2-benzylidene malononitriles.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              7537
_journal_page_last               7544
_journal_paper_doi               10.1039/d3sc02101g
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H19 N3 O4'
_chemical_formula_sum            'C25 H19 N3 O4'
_chemical_formula_weight         425.44
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-03-05
_audit_creation_method           'by CrystalStructure 4.3'
_audit_update_record
;
2023-04-04 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.65320(10)
_cell_length_b                   13.39570(11)
_cell_length_c                   14.02840(12)
_cell_measurement_reflns_used    19791
_cell_measurement_temperature    125
_cell_measurement_theta_max      75.24
_cell_measurement_theta_min      3.13
_cell_volume                     2189.87(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      125
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0087
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24536
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.417
_diffrn_reflns_theta_min         4.564
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             888.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform/hexane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_details
;
 Flack x determined using 1869 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.0109(8)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.3304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                4432
_reflns_number_total             4447
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d3sc02101g2.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1569765
_shelx_res_checksum              35060
_shelx_hkl_checksum              5030