Double Protonation of 1,5-Bis(triarylaminoethynyl)anthraquinone To Form a Paramagnetic Pentacyclic Dipyrylium Salt
Koya Prabhakara Rao; Tetsuro Kusamoto; Fumiyuki Toshimitsu; Kiyotaka Inayoshi; Shoko Kume; Ryota Sakamoto; Hiroshi Nishihara; Journal of the American Chemical Society 132 (2010) 12472–12479; doi:10.1021/ja105250f

data_4103016
_publ_contact_author_address
;
Department of Chemistry
University of Tokyo
7-3-1 Hongo, Bunkyo-ku,
Tokyo  Japan
;
_publ_contact_author_email       nisihara@chem.s.u-tokyo.ac.jp
_publ_contact_author_fax         '+81 3 5841 4346'
_publ_contact_author_name        'Hiroshi Nishihara'
_publ_contact_author_phone       '+81 3 5841 8063'
_publ_section_title
;
 Double Protonation of 1,5-Bis(triarylaminoethynyl)anthraquinone To Form a
 Paramagnetic Pentacyclic Dipyrylium Salt
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12472
_journal_page_last               12479
_journal_paper_doi               10.1021/ja105250f
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C59 H46 Cl2 N2 O6'
_chemical_formula_sum            'C59 H46 Cl2 N2 O6'
_chemical_formula_weight         949.88
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 111.302(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.183(4)
_cell_length_b                   12.104(2)
_cell_length_c                   21.435(4)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    113.1500
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.0598
_cell_volume                     4637.0(15)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  wingx
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113.115
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       dtcell.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35773
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8397
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.797
_refine_diff_density_min         -1.281
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         10600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0912
_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^)+(0.1552P)^2^+3.6528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2544
_refine_ls_wR_factor_ref         0.2767
_reflns_number_gt                8027
_reflns_number_total             10600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja105250f_si_004.cif
_cod_data_source_block           1,5-Am2pyl2
_cod_original_cell_volume        4637.1(15)
_cod_database_code               4103016