Palladium-catalyzed regioselective [3 + 2] annulation of internal alkynes and iodo-pyranoquinolines with concomitant ring opening.
Aggarwal, Trapti; Jha, Rajeev R.; Tiwari, Rakesh K.; Kumar, Sonu; Kotla, Siva K Reddy; Kumar, Sushil; Verma, Akhilesh K.; Organic letters 14 (2012) 5184–5187; doi:10.1021/ol3022935

data_1508670
_publ_section_title
;
 Palladium-catalyzed regioselective [3 + 2] annulation of internal alkynes
 and iodo-pyranoquinolines with concomitant ring opening.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5184
_journal_page_last               5187
_journal_paper_doi               10.1021/ol3022935
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C30 H25 N O2'
_chemical_formula_sum            'C30 H25 N O2'
_chemical_formula_weight         431.51
_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                 101.406(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.248(3)
_cell_length_b                   9.8892(14)
_cell_length_c                   18.728(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.10
_cell_volume                     2223.6(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\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  0.0914
_diffrn_reflns_av_sigmaI/netI    0.1249
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14793
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0049(10)
_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   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1526
_refine_ls_R_factor_gt           0.0905
_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^)+(0.0589P)^2^+0.1178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.1790
_reflns_number_gt                2418
_reflns_number_total             3918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3022935_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        2223.7(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1508670