Highly enantioselective conjugate addition of malononitrile to 2-enoylpyridines with bifunctional organocatalyst.
Molleti, Nagaraju; Rana, Nirmal K.; Singh, Vinod K.; Organic letters 14 (2012) 4322–4325; doi:10.1021/ol3015607

data_1508584
_publ_section_title
;
 Highly enantioselective conjugate addition of malononitrile to
 2-enoylpyridines with bifunctional organocatalyst.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4322
_journal_page_last               4325
_journal_paper_doi               10.1021/ol3015607
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C17 H13 N3 O,O2'
_chemical_formula_sum            'C17 H13 N3 O3'
_chemical_formula_weight         307.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 103.121(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   11.859(5)
_cell_length_b                   5.765(5)
_cell_length_c                   12.062(5)
_cell_measurement_reflns_used    966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.17
_cell_measurement_theta_min      2.74
_cell_volume                     803.1(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3699
_diffrn_reflns_theta_full        23.52
_diffrn_reflns_theta_max         23.52
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2211
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1547P)^2^+0.5485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.2043
_reflns_number_gt                1865
_reflns_number_total             2211
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3015607_si_002.cif
_cod_data_source_block           Chiral
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1508584