Access to 2-pyridinylamide and imidazopyridine from 2-fluoropyridine and amidine hydrochloride
Li, Yibiao; Huang, Shuo; Li, Jiaming; Li, Jian; Ji, Xiaoliang; Liu, Jiasheng; Chen, Lu; Peng, Shiyong; Zhang, Kun; Organic & Biomolecular Chemistry 18 (2020) 9292–9299; doi:10.1039/D0OB01904F

data_7157746
_publ_section_title
;
 Access to 2-pyridinylamide and imidazopyridine from 2-fluoropyridine and
 amidine hydrochloride
;
_journal_issue                   45
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              9292
_journal_page_last               9299
_journal_paper_doi               10.1039/D0OB01904F
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C7 H7 Br N2 O'
_chemical_formula_sum            'C7 H7 Br N2 O'
_chemical_formula_weight         215.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-15 deposited with the CCDC.	2020-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                81.742(8)
_cell_angle_beta                 88.786(9)
_cell_angle_gamma                85.859(10)
_cell_formula_units_Z            4
_cell_length_a                   3.8839(6)
_cell_length_b                   8.7474(9)
_cell_length_c                   22.6670(14)
_cell_measurement_reflns_used    2534
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3760
_cell_measurement_theta_min      5.1030
_cell_volume                     760.07(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -65.00  27.00   1.00    1.00    --  -40.73  38.00  90.00   92
  2  \w    -47.00  -2.00   1.00    1.00    --  -40.73 125.00 150.00   45
  3  \w   -112.00 -16.00   1.00    1.00    --  -40.73 -38.00 -90.00   96
  4  \w      1.00  33.00   1.00    1.00    --   40.73 -99.00 150.00   32
  5  \w     30.00 102.00   1.00    1.00    --  106.95 -95.00  30.00   72
  6  \w     74.00 106.00   1.00    1.00    --  106.95-111.00 -30.00   32
  7  \w     82.00 109.00   1.00    1.00    --  106.95-111.00-150.00   27
  8  \w     49.00  96.00   1.00    1.00    --   40.73-125.00 -60.00   47
  9  \w     34.00  75.00   1.00    1.00    --  106.95-111.00-150.00   41
 10  \w     36.00 136.00   1.00    1.00    --  106.95 -61.00-150.00  100
 11  \w     63.00 177.00   1.00    1.00    --  106.95  15.00   0.00  114
 12  \w    123.00 150.00   1.00    1.00    --  106.95 107.00 125.00   27
 13  \w    105.00 141.00   1.00    1.00    --  106.95 111.00   0.00   36
 14  \w    113.00 151.00   1.00    1.00    --  106.95 178.00 -60.00   38
 15  \w     84.00 111.00   1.00    1.00    --  106.95 178.00 -60.00   27
 16  \w     85.00 171.00   1.00    1.00    --  106.95  45.00  60.00   86
 17  \w     37.00 122.00   1.00    1.00    --  106.95 -45.00  30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1142516000
_diffrn_orient_matrix_UB_12      0.1609892000
_diffrn_orient_matrix_UB_13      0.0164762000
_diffrn_orient_matrix_UB_21      0.1308188000
_diffrn_orient_matrix_UB_22      -0.0520381000
_diffrn_orient_matrix_UB_23      0.0639263000
_diffrn_orient_matrix_UB_31      0.3577890000
_diffrn_orient_matrix_UB_32      0.0565732000
_diffrn_orient_matrix_UB_33      -0.0189492000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4416
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.119
_diffrn_reflns_theta_min         1.970
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.546
_refine_diff_density_min         -1.059
_refine_diff_density_rms         0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0997P)^2^+8.9635P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.1915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2649
_reflns_number_total             2924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01904f2.cif
_cod_data_source_block           hs-201-1
_cod_database_code               7157746
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N006(H006), C4(H4), C1(H1A), C2(H2), C00J(H00J), C00L(H00L), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C00G(H00A,H00B,H00C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.348
_oxdiff_exptl_absorpt_empirical_full_min 0.601