Synthesis of imidazo[1,5-a]pyridines via I<sub>2</sub>-mediated sp<sup>3</sup> C-H amination.
Hu, Zhiyuan; Hou, Jiao; Liu, Jie; Yu, Wenquan; Chang, Junbiao; Organic & biomolecular chemistry 16 (2018) 5653–5660; doi:10.1039/c8ob01501e

data_7156321
_publ_section_title
;
 Synthesis of imidazo[1,5-a]pyridines via I<sub>2</sub>-mediated
 sp<sup>3</sup> C-H amination.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5653
_journal_page_last               5660
_journal_paper_doi               10.1039/c8ob01501e
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C19 H14 N2'
_chemical_formula_sum            'C19 H14 N2'
_chemical_formula_weight         270.32
_chemical_melting_point          383.5(5)
_chemical_name_systematic        1,3-diphenylimidazo[1,5-a]pyridine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-04-23 deposited with the CCDC.
2018-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.8510(10)
_cell_length_b                   7.4217(4)
_cell_length_c                   7.8859(4)
_cell_measurement_reflns_used    1174
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5100
_cell_measurement_theta_min      5.6510
_cell_volume                     1395.92(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -103.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000    0.0000 98

  2 omega  -33.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 98

  3 omega   57.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 53

  4 omega  -34.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -120.0000 93

  5 omega   57.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 53

  6 omega   57.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 53

  7 omega   37.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 54

  8 omega   38.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 71

  9 omega   82.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 96

 10 omega   91.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

 11 omega   39.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 26

 12 omega  106.00  169.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 63

 13 omega   59.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 29

 14 omega  112.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0571581000
_diffrn_orient_matrix_UB_12      0.0864225000
_diffrn_orient_matrix_UB_13      0.0408322000
_diffrn_orient_matrix_UB_21      -0.0194733000
_diffrn_orient_matrix_UB_22      -0.1771708000
_diffrn_orient_matrix_UB_23      0.0832066000
_diffrn_orient_matrix_UB_31      0.0230489500
_diffrn_orient_matrix_UB_32      0.0652386500
_diffrn_orient_matrix_UB_33      0.1717654000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2575
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.024
_diffrn_reflns_theta_max         67.024
_diffrn_reflns_theta_min         3.706
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1.6(13)
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1020
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0485P)^2^+0.1257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
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_reflns_Friedel_coverage         0.844
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_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                965
_reflns_number_total             1020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01501e2.cif
_cod_data_source_block           20170457
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '383-384' was changed to '383.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156321.cif.
;
_cod_database_code               7156321
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H70N2O2
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 2.6(13)
 -1.6(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Shared sites
{N2, C10}
4. Uiso/Uaniso restraints and constraints
Uiso(N2) = Uiso(C10)
5. Others
 Fixed Sof: C10(0.5) N2(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'