Mutual Interference between Intramolecular Proton Transfer Sites through the Adjoining π-Conjugated System in Schiff Bases of Double-Headed, Fused Salicylaldehydes
Hirohiko Houjou; Hajime Shingai; Keisuke Yagi; Isao Yoshikawa; Koji Araki; Journal of Organic Chemistry 78 (2013) 9021–9031; doi:10.1021/jo401108z

data_4028588
_publ_section_title
;
 Mutual Interference between Intramolecular Proton Transfer Sites through
 the Adjoining \p-Conjugated System in Schiff Bases of Double-Headed,
 Fused Salicylaldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9021
_journal_page_last               9031
_journal_paper_doi               10.1021/jo401108z
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C26 H22 N2 O2'
_chemical_formula_sum            'C26 H22 N2 O2'
_chemical_formula_weight         394.46
_chemical_name_common
1,5-bis(benzyliminomethyl)-2,6-dihydroxynaphthalene
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                65.579(2)
_cell_angle_beta                 70.746(2)
_cell_angle_gamma                70.183(2)
_cell_formula_units_Z            2
_cell_length_a                   9.168(1)
_cell_length_b                   10.975(1)
_cell_length_c                   11.722(1)
_cell_measurement_reflns_used    8762
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      73.27
_cell_measurement_theta_min      4.25
_cell_volume                     985.28(16)
_computing_cell_refinement       Scalepack
_computing_data_collection       'MacScience Xpress'
_computing_data_reduction        'Denzo and Scalepack'
_computing_molecular_graphics    maXus
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'MacScience DIPLabo'
_diffrn_measurement_method       IP
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8762
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         73.27
_diffrn_reflns_theta_min         4.25
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.8861
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'abscor (MacScience Co. Ltd., 2000)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.826
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.826
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0880
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3532
_refine_ls_wR_factor_ref         0.3657
_reflns_number_gt                3474
_reflns_number_total             3695
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401108z_si_004.cif
_cod_data_source_block           15bnz
_cod_database_code               4028588