Isonitrile alkylations: a rapid route to imidazo[1,5-a]pyridines.
Li, Yajun; Chao, Allen; Fleming, Fraser F.; Chemical communications (Cambridge, England) 52 (2016) 2111–2113; doi:10.1039/c5cc08724d

data_7118625
_publ_section_title
;
 Isonitrile alkylations: a rapid route to imidazo[1,5-a]pyridines.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2111
_journal_page_last               2113
_journal_paper_doi               10.1039/c5cc08724d
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C13 H10 N2'
_chemical_formula_weight         194.23
_chemical_name_systematic        1-phenylimidazo[1,5-a]pyridine
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-10-12 deposited with the CCDC.
2015-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2543(11)
_cell_length_b                   10.8861(17)
_cell_length_c                   12.636(2)
_cell_measurement_temperature    296(2)
_cell_volume                     997.9(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13412
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.290
_diffrn_reflns_theta_min         2.469
_exptl_absorpt_coefficient_mu    0.078
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       Platy
_exptl_crystal_F_000             408
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          1.254
_exptl_crystal_size_mid          1.079
_exptl_crystal_size_min          0.993
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.198
_refine_ls_abs_structure_details
;
 Flack x determined using 1234 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0577
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                3154
_reflns_number_total             3620
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc08724d2.cif
_cod_data_source_block           AC_YJ_040215_0m
_cod_database_code               7118625
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.926
_shelxl_version_number           2013-2
_shelx_res_checksum              93789
_shelx_hkl_checksum              2714