Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines.
Samanta, Sadhanendu; Jana, Sourav; Mondal, Susmita; Monir, Kamarul; Chandra, Swapan K.; Hajra, Alakananda; Organic & biomolecular chemistry 14 (2016) 5073–5078; doi:10.1039/c6ob00656f

data_7155107
_publ_section_title
;
 Switching the regioselectivity in the copper-catalyzed synthesis of
 iodoimidazo[1,2-a]pyridines.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5073
_journal_page_last               5078
_journal_paper_doi               10.1039/c6ob00656f
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C14 H11 I N2'
_chemical_formula_weight         334.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-05-01 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.2657(4)
_cell_length_b                   14.1996(6)
_cell_length_c                   21.2896(9)
_cell_measurement_reflns_used    7256
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.24
_cell_volume                     2498.75(19)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            83026
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.786
_diffrn_reflns_theta_min         1.724
_exptl_absorpt_coefficient_mu    2.541
_exptl_absorpt_correction_T_max  0.7517
_exptl_absorpt_correction_T_min  0.5488
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.733
_refine_diff_density_min         -2.843
_refine_diff_density_rms         0.356
_refine_ls_abs_structure_details
;
 Flack x determined using 2559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0395
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1313
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                6047
_reflns_number_total             6479
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00656f2.cif
_cod_data_source_block           vbchem146_0m_a
_cod_depositor_comments
'Adding full bibliography for 7155106--7155108.cif.'
_cod_database_code               7155107
_shelxl_version_number           2014/6
_shelx_res_checksum              67917