Unprecedented regiochemical control in the formation of aryl[1,2-a]imidazopyridines from alkynyliodonium salts: mechanistic insights.
Dixon, Luke I.; Carroll, Michael A.; Gregson, Thomas J.; Ellames, George J.; Harrington, Ross W.; Clegg, William; Organic & biomolecular chemistry 11 (2013) 5877–5884; doi:10.1039/c3ob41112e

data_7153051
_publ_section_title
;
 Unprecedented regiochemical control in the formation of
 aryl[1,2-a]imidazopyridines from alkynyliodonium salts: mechanistic
 insights.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5877
_journal_page_last               5884
_journal_paper_doi               10.1039/c3ob41112e
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C13 H11 N2 +,Cl -,H2 O'
_chemical_formula_sum            'C13 H13 Cl N2 O'
_chemical_formula_weight         248.70
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.573(5)
_cell_angle_beta                 74.634(5)
_cell_angle_gamma                71.501(5)
_cell_formula_units_Z            2
_cell_length_a                   6.8922(4)
_cell_length_b                   9.1653(6)
_cell_length_c                   10.6422(6)
_cell_measurement_reflns_used    6311
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      3.17
_cell_volume                     602.44(7)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type
'Oxford Diffraction Gemini A Ultra diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9325
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0462P)^2^+0.2544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                2116
_reflns_number_total             2571
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c3ob41112e.txt
_cod_data_source_block           mac68_3a.HCl.H2O
_cod_original_cell_volume        602.44(6)
_cod_database_code               7153051