A base-catalyzed cycloisomerization of 5-cyano-pentyne derivatives: an efficient synthesis of 3-cyano-4,5-dihydro-1H-pyrroles
Jia Meng; Yi-Jin Li; Yu-Long Zhao; Xiu-Bin Bu; Qun Liu; Chem.Commun. 50 (2014) 12490–; doi:10.1039/C4cc04409F

data_7115760
_publ_section_title
;
 A base-catalyzed cycloisomerization of 5-cyano-pentyne derivatives: an
 efficient synthesis of 3-cyano-4,5-dihydro-1H-pyrroles
;
_journal_name_full               Chem.Commun.
_journal_page_first              12490
_journal_paper_doi               10.1039/C4cc04409F
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C12 H12 N2'
_chemical_formula_weight         184.24
_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                 93.859(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7787(10)
_cell_length_b                   8.3955(11)
_cell_length_c                   15.691(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1022.4(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5534
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.072
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1485
_reflns_number_gt                1225
_reflns_number_total             2015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc04409f2.cif
_cod_data_source_block           sa115m
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7115760