Regioselective Preferential Nucleophilic Addition of N-Heterocycles onto Haloarylalkynes over N-Arylation of Aryl Halides.
Joshi, Megha; Tiwari, Rakesh; Verma, Akhilesh Kumar; Organic letters 14 (2012) 1106–1109; doi:10.1021/ol203491p

data_1503621
_publ_section_title
;
 Regioselective Preferential Nucleophilic Addition of N-Heterocycles onto
 Haloarylalkynes over N-Arylation of Aryl Halides.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1106
_journal_page_last               1109
_journal_paper_doi               10.1021/ol203491p
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C17 H14 Br N O'
_chemical_formula_sum            'C17 H14 Br N O'
_chemical_formula_weight         328.20
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.49(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.568(7)
_cell_length_b                   6.3111(16)
_cell_length_c                   7.901(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.50
_cell_volume                     1415.4(7)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.898
_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  0.0880
_diffrn_reflns_av_sigmaI/netI    0.0783
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6253
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    2.899
_exptl_absorpt_correction_T_max  0.6385
_exptl_absorpt_correction_T_min  0.5310
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.047
_refine_diff_density_min         -1.650
_refine_diff_density_rms         0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.280
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.280
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.1248
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3341
_refine_ls_wR_factor_ref         0.3858
_reflns_number_gt                1296
_reflns_number_total             2238
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203491p_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1415.3(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503621