The development of aryl-substituted 2-phenylimidazo[1,2-a]pyridines (PIP) with various colors of excited-state intramolecular proton transfer (ESIPT) luminescence in the solid state
Toshiki Mutai; Tatsuya Ohkawa; Hideaki Shono; Koji Araki; Journal of Materials Chemistry C 4 (2016) 3599–3606; doi:10.1039/C6TC00376A

data_7234684
_publ_section_title
;
 The development of aryl-substituted 2-phenylimidazo[1,2-a]pyridines (PIP)
 with various colors of excited-state intramolecular proton transfer
 (ESIPT) luminescence in the solid state
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3599
_journal_page_last               3606
_journal_paper_doi               10.1039/C6TC00376A
_journal_volume                  4
_journal_year                    2016
_chemical_absolute_configuration .
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35
_chemical_name_common            '6-p-Methoxyphenyl HPIP'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 102.177(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.686(3)
_cell_length_b                   10.175(3)
_cell_length_c                   16.709(6)
_cell_measurement_reflns_used    3874
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.20
_cell_volume                     1609.7(9)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16626
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         2.151
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1294 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.7(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         5856
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0402P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0862
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                4114
_reflns_number_total             5856
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-3599.cif
_cod_data_source_block           6MeOPh
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7234684
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2013-4
_shelx_res_checksum              71292
_shelx_hkl_checksum              89886