Directed regioselective arylation of imidazo[1,2-<i>a</i>]pyridine-3-carboxamides using Rh(III) catalysis.
Jahan, Kousar; Sood, Mehak; Jain, Osheen; Sahoo, Subash C.; Bharatam, Prasad V.; Organic & biomolecular chemistry 22 (2024) 7121–7127; doi:10.1039/d4ob01166j

data_7160095
_publ_section_title
;
 Directed regioselective arylation of
 imidazo[1,2-<i>a</i>]pyridine-3-carboxamides using Rh(III) catalysis.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7121
_journal_page_last               7127
_journal_paper_doi               10.1039/d4ob01166j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H19 N3 O3'
_chemical_formula_sum            'C18 H19 N3 O3'
_chemical_formula_weight         325.36
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-07-29
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-29 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4420(2)
_cell_length_b                   14.9737(5)
_cell_length_c                   17.2226(7)
_cell_measurement_reflns_used    6590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3340
_cell_measurement_theta_min      3.4340
_cell_volume                     1661.30(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -63.00 -38.00   0.50   10.00    --   -9.79 149.00 -89.00   50
  2  \w    -54.00 -29.00   0.50   10.00    --   -9.79 124.00 106.00   50
  3  \w      6.00  31.00   0.50   10.00    --   10.07-124.00  26.00   50
  4  \w     20.00  45.00   0.50   10.00    --   10.07-149.00-136.00   50
  5  \w    -23.00  54.00   0.50   10.00    --   -9.79  38.00 150.00  154
  6  \w    -62.00   8.00   0.50   10.00    --   -9.79 -57.00 -60.00  140
  7  \w    -22.00  54.00   0.50   10.00    --   -9.79  38.00-120.00  152
  8  \w      1.00  29.00   0.50   10.00    --   10.07  77.00  60.00   56
  9  \w     35.00  73.00   0.50   10.00    --   10.07  38.00 -90.00   76
 10  \w     34.00  60.00   0.50   10.00    --   10.07  77.00  60.00   52
 11  \w    -14.00  72.00   0.50   10.00    --   10.07  77.00  30.00  172
 12  \w     23.00  58.00   0.50   10.00    --   10.07-125.00 -30.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16477
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'microfocused selaed tube'
_diffrn_source_type              supernova
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
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    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 722 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0603P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2304
_reflns_number_total             3362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01166j2.cif
_cod_data_source_block           scs-ksl-niper
_cod_depositor_comments          'Adding full bibliography for 7160095.cif.'
_cod_original_cell_volume        1661.31(11)
_cod_database_code               7160095
_shelx_shelxl_version_number     2017/1
_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:
 N3(H3), C12(H12), C11(H11), C3(H3A), C4(H4), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C13(H13A,H13B,H13C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              6213
_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
;