Ipso- or Cine-Substitutions of 6-Haloimidazo[1,2-a]pyridine Derivatives with Different Azoles Depending on the Reaction Conditions
Cécile Enguehard; Hassan Allouchi; Alain Gueiffier; Stephen L. Buchwald; Journal of Organic Chemistry 68 (2003) 5614–5617; doi:10.1021/jo034439w

data_4022463
_publ_section_title
;
 Ipso- or Cine-Substitutions of 6-Haloimidazo[1,2-a]pyridine Derivatives
 with Different Azoles Depending on the Reaction Conditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5614
_journal_page_last               5617
_journal_paper_doi               10.1021/jo034439w
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C16 H13 F N4 O'
_chemical_formula_weight         296.30
_chemical_name_systematic        compound-7
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.59(3)
_cell_angle_beta                 90.06(8)
_cell_angle_gamma                93.60(7)
_cell_formula_units_Z            4
_cell_length_a                   7.247(8)
_cell_length_b                   14.078(6)
_cell_length_c                   14.564(7)
_cell_measurement_temperature    296(2)
_cell_volume                     1387.8(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5269
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9555
_exptl_absorpt_correction_type   scalepack
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         4852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.1972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                2868
_reflns_number_total             4852
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034439wsi20030408_124707.cif
_cod_data_source_block
N-[2-(4-fluorophenyl)imidazo[1,2-a]pyridin-6-yl]imidazole
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022463