Palladium(II)-catalysed regioselective synthesis of 3,4-disubstituted quinolines and 2,3,5-trisubstituted pyrroles from alkenes via anti-Markovnikov selectivity
Gopal Chandru Senadi; Wan-Ping Hu; Amol Milind Garkhedkar; Siva Senthil Kumar Boominathan; Jeh-Jeng Wang; Chem.Commun. 51 (2015) 13795–; doi:10.1039/C5cc05196G

data_7117699
_publ_section_title
;
 Palladium(II)-catalysed regioselective synthesis of 3,4-disubstituted
 quinolines and 2,3,5-trisubstituted pyrroles from alkenes via
 anti-Markovnikov selectivity
;
_journal_name_full               Chem.Commun.
_journal_page_first              13795
_journal_paper_doi               10.1039/C5cc05196G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C22 H14 N2'
_chemical_formula_sum            'C22 H14 N2'
_chemical_formula_weight         306.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_update_record
;
2015-05-07 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                83.981(8)
_cell_angle_beta                 81.526(8)
_cell_angle_gamma                76.578(8)
_cell_formula_units_Z            2
_cell_length_a                   5.8666(5)
_cell_length_b                   11.4535(10)
_cell_length_c                   12.2113(12)
_cell_measurement_reflns_used    1393
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.7440
_cell_measurement_theta_min      3.5870
_cell_volume                     787.26(13)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6123
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0485P)^2^+0.1069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                2541
_reflns_number_total             3630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05196g2.cif
_cod_data_source_block           sgcnitrile
_cod_original_cell_volume        787.26(12)
_cod_database_code               7117699