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_4024964
_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            'C19 H14 N2 O'
_chemical_formula_weight         286.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.68(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.205(15)
_cell_length_b                   5.6691(7)
_cell_length_c                   14.706(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      21
_cell_volume                     1507.6(15)
_computing_cell_refinement       'Enraf Nonius Software V5'
_computing_data_collection       'Enraf Nonius Software V5'
_computing_data_reduction        'Corinc (Dr\"ager, 1971)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'CAD4 Enraf Nonius'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2981
_diffrn_reflns_theta_full        70.33
_diffrn_reflns_theta_max         70.33
_diffrn_reflns_theta_min         2.44
_diffrn_source                   'rotating anode'
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  0.8847
_exptl_absorpt_correction_T_min  0.8101
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'Corinc (Dr\"ager, 1971)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0960P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1714
_refine_ls_wR_factor_ref         0.2071
_reflns_number_gt                1632
_reflns_number_total             2856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901759u_si_002.cif
_cod_data_source_block           cw14
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024964