1-Alkynyl- and 1-Alkenyl-3-arylimidazo[1,5-a]pyridines: Synthesis, Photophysical Properties, and Observation of a Linear Correlation between the Fluorescent Wavelength and Hammett Substituent Constants
Eiji Yamaguchi; Fumitoshi Shibahara; Toshiaki Murai; Journal of Organic Chemistry 76 (2011) 6146–6158; doi:10.1021/jo200864x

data_4026488
_publ_section_title
;
 1-Alkynyl- and 1-Alkenyl-3-arylimidazo[1,5-a]pyridines: Synthesis,
 Photophysical Properties, and Observation of a Linear Correlation between
 the Fluorescent Wavelength and Hammett Substituent Constants
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6146
_journal_page_last               6158
_journal_paper_doi               10.1021/jo200864x
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C19 H12 N2 S'
_chemical_formula_sum            'C19 H12 N2 S'
_chemical_formula_weight         300.37
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.828(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.809(15)
_cell_length_b                   10.437(7)
_cell_length_c                   15.931(12)
_cell_measurement_reflns_used    5104
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      30.9
_cell_measurement_theta_min      2.1
_cell_volume                     2965(4)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 2.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_sigmaI/netI    0.1940
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11715
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.959
_refine_diff_density_rms         0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0817
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1533P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1994
_refine_ls_wR_factor_ref         0.3098
_reflns_number_gt                1284
_reflns_number_total             3404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200864x_si_004.cif
_cod_data_source_block           thio
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_database_code               4026488