Molecular Clips with Extended Aromatic Sidewalls as Receptors for Electron-Acceptor Molecules. Synthesis and NMR, Photophysical, and Electrochemical Properties
Barbara Branchi; Vincenzo Balzani; Paola Ceroni; Mireia Campañá Kuchenbrandt; Frank-Gerrit Klärner; Dieter Bläser; Roland Boese; Journal of Organic Chemistry 73 (2008) 5839–5851; doi:10.1021/jo8007513

data_4023582
_publ_contact_author
;
         Prof. Dr. Boese, Roland
         Fachbereich Chemie der
         Universit\"at Duisburg-Essen
         Campus Essen Universit\"atsstr. 3-5
         D-45117 Essen, Germany
;
_publ_contact_author_email       roland.boese@.uni-essen.de
_publ_contact_author_fax         '++49 (0)201 183 2535'
_publ_contact_author_phone       '++49 (0)201 183 2416'
_publ_section_title
;
 Molecular Clips with Extended Aromatic Sidewalls as Receptors
 for Electron-Acceptor Molecules. Synthesis and NMR,
 Photophysical, and Electrochemical Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5839
_journal_page_last               5851
_journal_paper_doi               10.1021/jo8007513
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C54 H34 O2 * 0.5 C10 H2 N4 * 2 C H Cl3 '
_chemical_formula_sum            'C61 H37 Cl6 N2 O2'
_chemical_formula_weight         1042.63
_chemical_name_systematic
; 
 8,19-Dimethoxy-(7a,9a,18a,20a)-7,9,18,20-tetrahydro-
 7,20:9,18-dimethanononaphthacene tetracyanobenzene 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 117.776(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   34.167(3)
_cell_length_b                   14.8708(15)
_cell_length_c                   22.173(2)
_cell_measurement_reflns_used    7950
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      1.66
_cell_volume                     9967.8(17)
_computing_cell_refinement       'BRUKER AXS SMART APEX 2 Vers. 1.0-27'
_computing_data_collection       'BRUKER AXS SMART APEX 2 Vers. 1.0-27'
_computing_data_reduction        'BRUKER AXS SMART APEX 2 Vers. 1.0-27'
_computing_molecular_graphics    'BRUKER AXS SHELXTL (c) 2001 / Vers.6.12'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2001 / Vers.6.12'
_computing_structure_refinement  'BRUKER AXS SHELXTL (c) 2001 / Vers.6.12'
_computing_structure_solution    'BRUKER AXS SHELXTL (c) 2001 / Vers.6.12'
_diffrn_ambient_temperature      203(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
; 
 Siemens SMART three axis goniometer with APEX II area detector system
;
_diffrn_measurement_method
;
 Data collection strategy APEX 2 / COSMO
;
_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  0.1309
_diffrn_reflns_av_sigmaI/netI    0.1122
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            64258
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 BRUKER AXS SMART APEX 2 Vers. 1.0-27
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4280
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.00043(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment
;
 Riding model on idealized geometrics 
 with the 1.2 fold (1.5 fold for methyl 
 groups) isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         12403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.2173
_refine_ls_R_factor_gt           0.0865
_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^)+(0.1043P)^2^+38.1829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2122
_refine_ls_wR_factor_ref         0.2868
_reflns_number_gt                4948
_reflns_number_total             12403
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8007513-File002.cif
_cod_data_source_block           tcyknmm
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C54 H34 O2, 0.5(C10 H2 N4), 2(C H Cl3)'
_cod_database_code               4023582