Donor-Substituted Octacyano[4]dendralenes: Investigation of π-Electron Delocalization in Their Radical Ions
Benjamin Breiten; Markus Jordan; Daisuke Taura; Michal Zalibera; Markus Griesser; Daria Confortin; Corinne Boudon; Jean-Paul Gisselbrecht; W. Bernd Schweizer; Georg Gescheidt; François Diederich; Journal of Organic Chemistry 78 (2013) 1760–1767; doi:10.1021/jo301194y

data_4027977
_publ_contact_author_email       schweizer@org.chem.ethz.ch
_publ_contact_author_name        'B. Schweizer'
_publ_section_title
;
 Donor-Substituted Octacyano[4]dendralenes: Investigation of \p-Electron
 Delocalization in Their Radical Ions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1760
_journal_page_last               1767
_journal_paper_doi               10.1021/jo301194y
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C52 H28 N10 , 2 ( C H2 Cl2) '
_chemical_formula_sum            'C54 H32 Cl4 N10'
_chemical_formula_weight         962.70
_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                91.016(7)
_cell_angle_beta                 94.203(8)
_cell_angle_gamma                93.318(8)
_cell_formula_units_Z            2
_cell_length_a                   8.480(3)
_cell_length_b                   15.471(4)
_cell_length_c                   18.112(5)
_cell_measurement_reflns_used    2052
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.19
_cell_measurement_theta_min      2.59
_cell_volume                     2365.2(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Platon, Ortep'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement
'OLEX2 (Dolomanov, 2009), SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0882
_diffrn_reflns_av_sigmaI/netI    0.1820
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18025
_diffrn_reflns_theta_full        25.77
_diffrn_reflns_theta_max         25.77
_diffrn_reflns_theta_min         1.13
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_type   mulit-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      0
_exptl_crystal_description       plate
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.015
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         8382
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.2141
_refine_ls_R_factor_gt           0.0956
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2149
_refine_ls_wR_factor_ref         0.2696
_reflns_number_gt                3665
_reflns_number_total             8382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301194y_si_002.cif
_cod_data_source_block           3
_cod_database_code               4027977