Organocatalytic Conjugate Addition of Malononitrile to Conformationally Restricted Dienones
Zhi-Peng Hu; Chun-Liang Lou; Jin-Jia Wang; Chun-Xia Chen; Ming Yan; Journal of Organic Chemistry 76 (2011) 3797–3804; doi:10.1021/jo200112r

data_4026285
_publ_section_title
;
 Organocatalytic Conjugate Addition of Malononitrile to Conformationally
 Restricted Dienones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3797
_journal_page_last               3804
_journal_paper_doi               10.1021/jo200112r
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H19 Br2 N3 O'
_chemical_formula_weight         513.23
_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
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_cell_angle_beta                 90.9830(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.02500(10)
_cell_length_b                   6.61660(10)
_cell_length_c                   15.4445(2)
_cell_measurement_reflns_used    8004
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.1202
_cell_measurement_theta_min      2.8592
_cell_volume                     1024.30(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.2417
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8343
_diffrn_reflns_theta_full        71.22
_diffrn_reflns_theta_max         71.22
_diffrn_reflns_theta_min         2.86
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    5.175
_exptl_absorpt_correction_T_max  0.6257
_exptl_absorpt_correction_T_min  0.3059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.032(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    geom
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3718
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0203
_refine_ls_R_factor_gt           0.0197
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.2544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0541
_reflns_number_gt                3666
_reflns_number_total             3718
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200112r_si_002.cif
_cod_data_source_block           2
_cod_database_code               4026285