Synthesis of Ring-Fused Pyridinium Salts by Intramolecular Nucleophilic Aromatic Substitution Reaction and Their Optoelectronic Properties.
Asanuma, Yuki; Eguchi, Hiroshi; Nishiyama, Hiroki; Tomita, Ikuyoshi; Inagi, Shinsuke; Organic letters  (2017) –; doi:10.1021/acs.orglett.7b00590

data_1546605
_publ_section_title
;
 Synthesis of Ring-Fused Pyridinium Salts by Intramolecular Nucleophilic
 Aromatic Substitution Reaction and Their Optoelectronic Properties.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.7b00590
_journal_year                    2017
_chemical_formula_sum            'C18 H8 F7 N O3 S'
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
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_cell_formula_units_Z            2
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_cell_length_c                   10.8500(6)
_cell_measurement_reflns_used    6936
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.06
_cell_volume                     833.32(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'rigaku raxis rapid'
_diffrn_measurement_method       'oscillation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
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_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_max       12
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_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.060
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_description       needle
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.570
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_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0500P)^2^+0.3841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0979
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_reflns_number_gt                3158
_reflns_number_total             3784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00590_si_002.cif
_cod_data_source_block           2a
_cod_database_code               1546605
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.851
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              27774
_shelx_hkl_checksum              30881