Enantioselective Conjugate Hydrocyanation of α,β-Unsaturated N-Acylpyrroles Catalyzed by Chiral Lithium(I) Phosphoryl Phenoxide
Hatano, Manabu; Yamakawa, Katsuya; Ishihara, Kazuaki; ACS Catalysis 7 (2017) 6686–; doi:10.1021/acscatal.7b02551

data_4514286
_publ_section_title
;
 Enantioselective Conjugate Hydrocyanation of \a,\b-Unsaturated
 N-Acylpyrroles Catalyzed by Chiral Lithium(I) Phosphoryl Phenoxide
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              6686
_journal_paper_doi               10.1021/acscatal.7b02551
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration S
_chemical_formula_sum            'C14 H11 Br N2 O'
_chemical_formula_weight         303.16
_chemical_name_common
;
(S)-2-(4-Bromophenyl)-4-oxo-4-(1H-pyrrol-1-yl)butanenitrile
;
_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
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1494(9)
_cell_length_b                   10.5103(18)
_cell_length_c                   23.635(4)
_cell_measurement_reflns_used    4710
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.486
_cell_measurement_theta_min      3.232
_cell_volume                     1279.2(4)
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_collection       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Rigaku CrystalStructure'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10436
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         3.232
_exptl_absorpt_coefficient_mu    3.202
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.854
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1052 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0188
_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^)+(0.0050P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0391
_refine_ls_wR_factor_ref         0.0393
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2692
_reflns_number_total             2875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b02551_si_002.cif
_cod_data_source_block           CrystalClear
_cod_database_code               4514286
_shelx_estimated_absorpt_t_min   0.400
_shelx_estimated_absorpt_t_max   0.645
_shelxl_version_number           2014/6
_shelx_res_checksum              6495
_shelx_hkl_checksum              71255