Cyclocondensation of α-Aminonitriles and Enones: A Short Access to 3,4-Dihydro-2H-pyrrole 2-carbonitriles and 2,3,5-Trisubstituted Pyrroles
Ines Bergner; Christine Wiebe; Nino Meyer; Till Opatz; Journal of Organic Chemistry 74 (2009) 8243–8253; doi:10.1021/jo901759u

data_4024965
_publ_section_title
;
Cyclocondensation of \a-Aminonitriles and Enones: A Short Access to
3,4-Dihydro-2H-pyrrole 2-carbonitriles and 2,3,5-Trisubstituted Pyrroles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8243
_journal_page_last               8253
_journal_paper_doi               10.1021/jo901759u
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C21 H15 Br N2'
_chemical_formula_weight         375.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.5643(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.4226(4)
_cell_length_b                   8.2183(3)
_cell_length_c                   33.1768(11)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2.4
_cell_volume                     3383.7(2)
_computing_cell_refinement       'APEX2 V2.0 (Bruker, 2006)'
_computing_data_collection       'APEX2 V2.0 (Bruker, 2006)'
_computing_data_reduction        'APEX2 V2.0 (Bruker, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SMART CCD'
_diffrn_measurement_method       'CCD scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            38676
_diffrn_reflns_theta_full        27.75
_diffrn_reflns_theta_max         27.75
_diffrn_reflns_theta_min         1.23
_diffrn_source                   'sealed Tube'
_exptl_absorpt_coefficient_mu    2.433
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.554
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Corinc (Dr\"ager, 1971)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.358
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0404P)^2^+3.4911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0947
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                5822
_reflns_number_total             7885
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901759u_si_003.cif
_cod_data_source_block           cw20
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024965