Enantioselective cyclopropanation of (Z)-3-substituted-2-(4-pyridyl)-acrylonitriles catalyzed by Cinchona ammonium salts.
Del Fiandra, Claudia; Moccia, Maria; Adamo, Mauro F. A.; Organic & biomolecular chemistry 14 (2016) 3105–3111; doi:10.1039/c6ob00154h

data_7154977
_publ_section_title
;
 Enantioselective cyclopropanation of
 (Z)-3-substituted-2-(4-pyridyl)-acrylonitriles catalyzed by Cinchona
 ammonium salts.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3105
_journal_page_last               3111
_journal_paper_doi               10.1039/c6ob00154h
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C19 H16 N2 O4'
_chemical_formula_sum            'C19 H16 N2 O4'
_chemical_formula_weight         336.34
_chemical_melting_point          103.5(15)
_chemical_name_systematic
'(2R,3R)-dimethyl 2-cyano-3-phenyl-2-(pyridin-4-yl)cyclopropane-1,1-dicarboxylate '
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-01-18 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.4013(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5857(4)
_cell_length_b                   10.4800(5)
_cell_length_c                   16.9107(8)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.45
_cell_volume                     1670.90(13)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker-AXS, 2008-2014)'
_computing_publication_material  'SHELXTL (Bruker-AXS, 2008-2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_detector_area_resol_mean 8.258
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0182
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32841
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.160
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0552P)^2^+0.5066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3459
_reflns_number_total             3841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00154h2.cif
_cod_data_source_block           tcd239
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '102-105' was changed to '103.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154977.cif.
;
_cod_database_code               7154977
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              81555