Formal [3+2] cycloaddition of 1-cyanocyclopropane 1-ester with pyridine, quinoline or isoquinoline: a general and efficient strategy for construction of cyanoindolizine skeletons
Juanjuan Liu; Lanxiang Zhou; Weijian Ye; Cunde Wang; Chem.Commun. 50 (2014) 9068–; doi:10.1039/C4cc03267E

data_7115440
_publ_section_title
;
 Formal [3+2] cycloaddition of 1-cyanocyclopropane 1-ester with pyridine,
 quinoline or isoquinoline: a general and efficient strategy for
 construction of cyanoindolizine skeletons
;
_journal_name_full               Chem.Commun.
_journal_page_first              9068
_journal_paper_doi               10.1039/C4cc03267E
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C22 H12 Br Cl N2 O'
_chemical_formula_sum            'C22 H12 Br Cl N2 O'
_chemical_formula_weight         435.69
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.526(6)
_cell_angle_beta                 80.859(6)
_cell_angle_gamma                70.826(6)
_cell_formula_units_Z            2
_cell_length_a                   7.7273(16)
_cell_length_b                   8.9408(18)
_cell_length_c                   14.824(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.46
_cell_volume                     936.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8463
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    2.350
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0618
_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^)+(0.0636P)^2^+1.6047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                2134
_reflns_number_total             3220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03267e2.cif
_cod_data_source_block           0509
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7115440