Iodine mediated oxidative cross coupling of 2-aminopyridine and aromatic terminal alkyne: a practical route to imidazo[1,2-a]pyridine derivatives.
Samanta, Surya Kanta; Bera, Mrinal K.; Organic & biomolecular chemistry 17 (2019) 6441–6449; doi:10.1039/c9ob00812h

data_7156889
_publ_section_title
;
 Iodine mediated oxidative cross coupling of 2-aminopyridine and aromatic
 terminal alkyne: a practical route to imidazo[1,2-a]pyridine derivatives.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6441
_journal_page_last               6449
_journal_paper_doi               10.1039/c9ob00812h
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C13 H9 F N2'
_chemical_formula_sum            'C13 H9 F N2'
_chemical_formula_weight         212.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-31 deposited with the CCDC.    2019-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.299(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6177(10)
_cell_length_b                   14.1889(12)
_cell_length_c                   6.2178(5)
_cell_measurement_reflns_used    4583
_cell_measurement_temperature    293.0(2)
_cell_measurement_theta_max      23.84
_cell_measurement_theta_min      2.27
_cell_volume                     1024.69(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.0(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16438
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.124
_diffrn_reflns_theta_max         25.124
_diffrn_reflns_theta_min         2.266
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1639 before and 0.0908 after correction. The Ratio of minimum to maximum transmission is 0.6373. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0502P)^2^+0.2538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1245
_reflns_number_total             1824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00812h2.cif
_cod_data_source_block           xrout
_cod_depositor_comments          'Adding full bibliography for 7156889.cif.'
_cod_database_code               7156889
_shelx_shelxl_version_number     2018/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C9(H9), C1(H1), C10(H10), C12(H12), C4(H4), C3(H3), C2(H2)
;
_shelx_res_checksum              60964
_olex2_submission_special_instructions 'No special instructions were received'