Regiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a]pyridines by Suzuki-Miyaura and Sonogashira cross-coupling reactions
Delaye, Pierre-Olivier; Pénichon, Mélanie; Allouchi, Hassan; Enguehard-Gueiffier, Cecile; Gueiffier, Alain; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00624A

data_7155573
_publ_section_title
;
 Regiocontrolled functionalization of
 2,3-dihalogenoimidazo[1,2-a]pyridines by Suzuki-Miyaura and Sonogashira
 cross-coupling reactions
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00624A
_journal_year                    2017
_chemical_formula_moiety         'C20 H16 N2'
_chemical_formula_sum            'C20 H16 N2'
_chemical_formula_weight         284.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-13 deposited with the CCDC.
2017-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.532(13)
_cell_angle_beta                 92.165(15)
_cell_angle_gamma                100.461(14)
_cell_formula_units_Z            2
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_cell_length_b                   9.0008(13)
_cell_length_c                   12.130(2)
_cell_measurement_reflns_used    1625
_cell_measurement_temperature    297(2)
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_cell_volume                     756.9(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
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_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -12.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6530   77.0000  -60.0000 113

  2 omega  -13.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6530   77.0000 -180.0000 114

  3 omega  -13.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6530   77.0000   60.0000 114

;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0325935000
_diffrn_orient_matrix_UB_12      0.0792046000
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_diffrn_orient_matrix_UB_21      -0.0102528000
_diffrn_orient_matrix_UB_22      0.0060695000
_diffrn_orient_matrix_UB_23      -0.0580962000
_diffrn_orient_matrix_UB_31      -0.0964289000
_diffrn_orient_matrix_UB_32      0.0106464000
_diffrn_orient_matrix_UB_33      0.0052790000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_unetI/netI     0.1095
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.746
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       'fragment of plate'
_exptl_crystal_F_000             300
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0709
_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^)+(0.0777P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.2152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1651
_reflns_number_total             3069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00624a2.cif
_cod_data_source_block           pod236-a_296k_2e
_cod_database_code               7155573
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              98194