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_7115438
_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_sum            'C27 H17 Cl N2 O'
_chemical_formula_weight         420.88
_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                71.680(5)
_cell_angle_beta                 73.572(4)
_cell_angle_gamma                67.431(5)
_cell_formula_units_Z            2
_cell_length_a                   10.4826(16)
_cell_length_b                   10.6458(17)
_cell_length_c                   10.9600(15)
_cell_measurement_reflns_used    4444
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.56
_cell_volume                     1053.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0746
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16987
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0088(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0493P)^2^+0.2216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                2714
_reflns_number_total             4861
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03267e2.cif
_cod_data_source_block           001
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7115438