Regioselectivity of Larock Heteroannulation: A Contribution from Electronic Properties of Diarylacetylenes
Nared Phetrak; Thanya Rukkijakan; Jakkapan Sirijaraensre; Samran Prabpai; Palangpon Kongsaeree; Chayada Klinchan; Pitak Chuawong; Journal of Organic Chemistry 78 (2013) 12703–12709; doi:10.1021/jo402304s

data_4028882
_publ_contact_author_address
;Department of Chemistry, Faculty of Science
Mahidol University
Bangkok 10400, Thailand    
;
_publ_contact_author_email       palangpon.kon@mahidol.ac.th
_publ_contact_author_fax         +662-354-7151
_publ_contact_author_name        'Palangpon Kongsaeree'
_publ_contact_author_phone       +662-201-5190
_publ_section_title
;
 Regioselectivity of Larock Heteroannulation: A Contribution from
 Electronic Properties of Diarylacetylenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12703
_journal_page_last               12709
_journal_paper_doi               10.1021/jo402304s
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C22 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 102.5120(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7580(3)
_cell_length_b                   19.8830(6)
_cell_length_c                   9.7210(3)
_cell_measurement_reflns_used    2173
_cell_measurement_temperature    298(2)
_cell_volume                     1652.57(9)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.861
_diffrn_measured_fraction_theta_max 0.976
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.01482
_diffrn_orient_matrix_UB_12      0.09629
_diffrn_orient_matrix_UB_13      0.06472
_diffrn_orient_matrix_UB_21      0.04903
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      -0.01122
_diffrn_orient_matrix_UB_31      -0.01600
_diffrn_orient_matrix_UB_32      0.07719
_diffrn_orient_matrix_UB_33      -0.06992
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6611
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.178
_diffrn_reflns_theta_min         4.088
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       Prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.023(5)
_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   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0897P)^2^+0.0868P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1797
_reflns_number_total             2584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo402304s_si_002_2.cif
_cod_data_source_block           9c
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028882
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C16(H16), C19(H19), C20(H20), C4(H4), C17(H17), C13(H13),
 C11(H11), C5(H5), C3(H3), C14(H14), C10(H10), C12(H12)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              60190
_shelxl_version_number           2013-4