Organocatalytic Stereoselective Epoxidation of Trisubstituted Acrylonitriles
Claudia De Fusco; Consiglia Tedesco; Alessandra Lattanzi; Journal of Organic Chemistry 76 (2011) 676–679; doi:10.1021/jo102020a

data_4025988
_publ_section_title
;
 Organocatalytic Stereoselective Epoxidation of Trisubstituted
 Acrylonitriles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              676
_journal_page_last               679
_journal_paper_doi               10.1021/jo102020a
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H10 Br N O2'
_chemical_formula_sum            'C16 H10 Br N O2'
_chemical_formula_weight         328.16
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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                90.00
_cell_angle_beta                 91.449(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.132(4)
_cell_length_b                   8.188(4)
_cell_length_c                   10.529(5)
_cell_measurement_reflns_used    901
_cell_measurement_temperature    292(1)
_cell_measurement_theta_max      62.3158
_cell_measurement_theta_min      17.6053
_cell_volume                     700.8(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Il Milione (Burla et al., 2007)'
_diffrn_ambient_temperature      292(1)
_diffrn_measured_fraction_theta_full 0.886
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_device
;
Saturn944 (2x2 bin mode)
;
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.541870
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.1395
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3597
_diffrn_reflns_theta_full        62.31
_diffrn_reflns_theta_max         62.31
_diffrn_reflns_theta_min         8.42
_exptl_absorpt_coefficient_mu    4.003
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1771
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1168P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.2247
_reflns_number_gt                1211
_reflns_number_total             1771
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102020a_si_001.cif
_cod_data_source_block           ale16
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025988