Phase-transfer-catalyzed asymmetric conjugate cyanation of alkylidenemalonates with KCN in the presence of a Brønsted acid additive.
Liu, Yan; Shirakawa, Seiji; Maruoka, Keiji; Organic letters 15 (2013) 1230–1233; doi:10.1021/ol400143m

data_1556145
_publ_section_title
;
 Phase-transfer-catalyzed asymmetric conjugate cyanation of
 alkylidenemalonates with KCN in the presence of a Br\/onsted acid
 additive.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1230
_journal_page_last               1233
_journal_paper_doi               10.1021/ol400143m
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C50.50 H43 Cl I N O2'
_chemical_formula_sum            'C50.5 H43 Cl I N O2'
_chemical_formula_weight         858.26
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   12.6747(5)
_cell_length_b                   15.3867(6)
_cell_length_c                   23.8253(10)
_cell_measurement_reflns_used    23768
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.42
_cell_volume                     4646.5(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2011)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            49653
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         3.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.222
_exptl_absorpt_correction_T_max  0.537
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1756.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.77
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3750 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.015(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     500
_refine_ls_number_reflns         8480
_refine_ls_number_restraints     265
_refine_ls_R_factor_gt           0.1041
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1642P)^2^+2.9439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3708
_reflns_number_gt                2868
_reflns_number_total             8480
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol400143m_si_002.cif
_cod_data_source_block           2731
_cod_original_cell_volume        4646.4(3)
_cod_original_formula_sum        'C50.50 H43 Cl I N O2'
_cod_database_code               1556145