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_4028881
_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_compound_source        Synthesis
_chemical_formula_moiety         'C20 H16 N2'
_chemical_formula_sum            'C20 H16 N2'
_chemical_formula_weight         284.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 117.66(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.244(9)
_cell_length_b                   8.151(3)
_cell_length_c                   10.261(10)
_cell_measurement_temperature    293(2)
_cell_volume                     758.9(11)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.661
_diffrn_measured_fraction_theta_max 0.834
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.02837
_diffrn_orient_matrix_UB_12      -0.09738
_diffrn_orient_matrix_UB_13      0.04310
_diffrn_orient_matrix_UB_21      -0.10247
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      0.06746
_diffrn_orient_matrix_UB_31      -0.03421
_diffrn_orient_matrix_UB_32      -0.09076
_diffrn_orient_matrix_UB_33      -0.05196
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4295
_diffrn_reflns_point_group_measured_fraction_max 0.451
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         23.154
_diffrn_reflns_theta_min         3.840
_exptl_absorpt_coefficient_mu    0.074
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       Block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0(8)
_refine_ls_extinction_coef       0.094(16)
_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   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         977
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0631P)^2^+0.3196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                861
_reflns_number_total             977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo402304s_si_002_1.cif
_cod_data_source_block           9a
_cod_database_code               4028881
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups, All N(H) groups
2. Restrained distances
 N18-H18A
 0.96 with sigma of 0.02
 N18-H18B
 0.96 with sigma of 0.02
3.a Riding coordinates:
 N1(H1), C19(H19), C16(H16), C17(H17), C5(H5), C20(H20), C2(H2), C10(H10),
 C14(H14), C12(H12), C13(H13), C11(H11), C4(H4), C3(H3)
;
_shelx_res_checksum              10450
_shelxl_version_number           2013-4