Cobalt-catalyzed tandem one-pot synthesis of polysubstituted imidazo[1,5-<i>a</i>]pyridines and imidazo[1,5-<i>a</i>]isoquinolines.
Meena, Neha; Dhiman, Shiv; Rangan, Krishnan; Kumar, Anil; Organic & biomolecular chemistry 20 (2022) 4215–4223; doi:10.1039/d2ob00526c

data_7158666
_publ_section_title
;
 Cobalt-catalyzed tandem one-pot synthesis of polysubstituted
 imidazo[1,5-<i>a</i>]pyridines and imidazo[1,5-<i>a</i>]isoquinolines.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4215
_journal_page_last               4223
_journal_paper_doi               10.1039/d2ob00526c
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C19 H14 N2 O S'
_chemical_formula_sum            'C19 H14 N2 O S'
_chemical_formula_weight         318.38
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-08-04
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-03-17 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.026(2)
_cell_angle_beta                 97.054(2)
_cell_angle_gamma                114.557(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6918(2)
_cell_length_b                   7.7847(2)
_cell_length_c                   13.7184(3)
_cell_measurement_reflns_used    5498
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.6750
_cell_measurement_theta_min      6.2490
_cell_volume                     740.27(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.957
_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    -22.00  32.00   0.50    1.34    --    0.00  19.00   0.00  108
  2  \w    -36.00  14.00   0.50    1.34    --    0.00 -37.00   0.00  100
  3  \w     29.00  86.00   0.50    1.34    --    0.00  77.00 120.00  114
  4  \w     55.00  89.00   0.50    1.34    --    0.00  19.00   0.00   68
  5  \w    -28.00  10.00   0.50    1.34    --    0.00  77.00 120.00   76
  6  \w    -82.00 -56.00   0.50    1.34    --    0.00 -37.00   0.00   52
  7  \w     95.00 126.00   0.50    5.40    --  107.20 -45.00  90.00   62
  8  \w     89.00 126.00   0.50    5.40    --  107.20  30.00 -90.00   74
  9  \w    154.00 197.00   0.50    5.40    --  107.20  15.00-150.00   86
 10  \w     35.00 138.00   0.50    5.40    --  107.20 -82.00   0.00  206
 11  \w    147.00 173.00   0.50    5.40    --  107.20  30.00 -60.00   52
 12  \w    130.00 158.00   0.50    5.40    --  107.20  30.00 -90.00   56
 13  \w    163.00 195.00   0.50    5.40    --  107.20  30.00 -90.00   64
 14  \w     19.00 139.00   0.50    5.40    --  107.20 -82.00-150.00  240
 15  \w     86.00 127.00   0.50    5.40    --  107.20 -82.00 120.00   82
 16  \w     80.00 194.00   0.50    5.40    --  107.20  15.00   0.00  228
 17  \w     75.00 110.00   0.50    5.40    --  107.20 -61.00 -30.00   70
 18  \w     39.00  65.00   0.50    5.40    --  107.20 -61.00 -30.00   52
 19  \w     18.00  86.00   0.50    5.40    --  107.20 -30.00   0.00  136
 20  \w     65.00 129.00   0.50    5.40    --  107.20 -82.00 -90.00  128
 21  \w     18.00 128.00   0.50    5.40    --  107.20 -61.00  90.00  220
 22  \w     99.00 126.00   0.50    5.40    --  107.20  30.00 -60.00   54
 23  \w     85.00 130.00   0.50    5.40    --  107.20  15.00-150.00   90
 24  \w     93.00 118.00   0.50    5.40    --  107.20 -82.00  60.00   50
 25  \w     63.00 106.00   0.50    5.40    --  107.20 -82.00  90.00   86
 26  \w     23.00  95.00   0.50    5.40    --  107.20 -45.00-120.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0301338000
_diffrn_orient_matrix_UB_12      0.0638969000
_diffrn_orient_matrix_UB_13      0.1094440000
_diffrn_orient_matrix_UB_21      0.0822800000
_diffrn_orient_matrix_UB_22      -0.1459526000
_diffrn_orient_matrix_UB_23      0.0275096000
_diffrn_orient_matrix_UB_31      0.2042439000
_diffrn_orient_matrix_UB_32      0.1486892000
_diffrn_orient_matrix_UB_33      -0.0105507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7457
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.208
_diffrn_reflns_theta_min         6.261
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.982
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0891P)^2^+0.2026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2876
_reflns_number_total             3095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00526c2.cif
_cod_data_source_block           exp_665_ak_nm-288
_cod_depositor_comments          'Adding full bibliography for 7158666.cif.'
_cod_database_code               7158666
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H13 N2 O S'
_shelx_estimated_absorpt_t_max   0.907
_shelx_estimated_absorpt_t_min   0.826
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17A-C16
 1.4 with sigma of 0.02
 C18-C17A
 1.49 with sigma of 0.02
3. Others
 Fixed Sof: S1A(0.7) C17A(0.7) H17A(0.7) H19(0.7) H19A(0.3) H18(0.7) H18A(0.3)
 S1B(0.3) C17B(0.3) H17B(0.3)
4.a Aromatic/amide H refined with riding coordinates:
 C17A(H17A), C11(H11), C12(H12), C3(H3), C13(H13), C7(H7), C14(H14), C4(H4),
 C15(H15), C19(H19), C19(H19A), C18(H18), C18(H18A), C17B(H17B)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              59119
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.172
_oxdiff_exptl_absorpt_empirical_full_min 0.617