A convenient approach to β-heteroarylated (C-N bond) ketones from Cs(2)CO(3) promoted reaction between propargyl alcohols and nitrogen-heterocycles.
Bhanuchandra, M.; Kuram, Malleswara Rao; Sahoo, Akhila K.; Organic & biomolecular chemistry 10 (2012) 3538–3555; doi:10.1039/c2ob25165e

data_7152323
_publ_section_title
;
 A convenient approach to \b-heteroarylated (C-N bond) ketones from
 Cs(2)CO(3) promoted reaction between propargyl alcohols and
 nitrogen-heterocycles.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3538
_journal_page_last               3555
_journal_paper_doi               10.1039/c2ob25165e
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C22 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.7487(16)
_cell_length_b                   9.7599(8)
_cell_length_c                   18.4670(12)
_cell_measurement_temperature    298(2)
_cell_volume                     3559.4(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.868
_diffrn_measured_fraction_theta_max 0.868
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10966
_diffrn_reflns_theta_full        29.15
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9821
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.097
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(17)
_refine_ls_extinction_coef       0.0018(3)
_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   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         6639
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0343P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                3376
_reflns_number_total             6639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25165e.txt
_cod_data_source_block           aks29
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               7152323