Synthesis and Optical Properties of Excited-State Intramolecular Proton Transfer Active π-Conjugated Benzimidazole Compounds: Influence of Structural Rigidification by Ring Fusion.
Takagi, Koji; Ito, Kaede; Yamada, Yoshihiro; Nakashima, Takuya; Fukuda, Ryoichi; Ehara, Masahiro; Masu, Hyuma; The Journal of organic chemistry 82 (2017) 12173–12180; doi:10.1021/acs.joc.7b01967

data_4033123
_publ_section_title
;
 Synthesis and Optical Properties of Excited-State Intramolecular Proton
 Transfer Active \p-Conjugated Benzimidazole Compounds: Influence of
 Structural Rigidification by Ring Fusion.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12173
_journal_page_last               12180
_journal_paper_doi               10.1021/acs.joc.7b01967
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30
_chemical_name_common            K1250
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 111.4780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.83360(10)
_cell_length_b                   17.8733(2)
_cell_length_c                   9.14300(10)
_cell_measurement_reflns_used    6364
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.2685
_cell_measurement_theta_min      4.9488
_cell_volume                     1343.31(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9476
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.263
_diffrn_reflns_theta_min         4.949
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
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_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0547P)^2^+0.3118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                2281
_reflns_number_total             2440
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           u150703mas1
_cod_depositor_comments
'Adding full bibliography for 4033123--4033124.cif.'
_cod_database_code               4033123
_shelx_res_checksum              25064
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