Expanding the Chemical Structure Space of Opto-Electronic Molecular Materials: Unprecedented Push-Pull Chromophores by Reaction of a Donor-Substituted Tetracyanofulvene with Electron-Rich Alkynes
Govindasamy Jayamurugan; Oliver Dumele; Jean-Paul Gisselbrecht; Corinne Boudon; W. Bernd Schweizer; Bruno Bernet; François Diederich; Journal of the American Chemical Society 135 (2013) 3599–3606; doi:10.1021/ja312084s

data_4119415
_publ_contact_author_email       schweizer@org.chem.ethz.ch
_publ_contact_author_name        'B. Schweizer'
_publ_section_title
;
 Expanding the Chemical Structure Space of Opto-Electronic Molecular
 Materials: Unprecedented Push-Pull Chromophores by Reaction of a
 Donor-Substituted Tetracyanofulvene with Electron-Rich Alkynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3599
_journal_page_last               3606
_journal_paper_doi               10.1021/ja312084s
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C44 H40 N8, 4(C7 H8)'
_chemical_formula_sum            'C72 H72 N8'
_chemical_formula_weight         1049.38
_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                 93.109(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2956(9)
_cell_length_b                   19.8622(10)
_cell_length_c                   19.6049(9)
_cell_measurement_reflns_used    4437
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.31
_cell_measurement_theta_min      2.32
_cell_volume                     5947.3(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0813
_diffrn_reflns_av_sigmaI/netI    0.1057
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            52950
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9986
_exptl_absorpt_correction_T_min  0.9863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       plate
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.010
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         13655
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.1604
_refine_ls_R_factor_gt           0.0776
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.2165
_reflns_number_gt                7206
_reflns_number_total             13655
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja312084s_si_005.cif
_cod_data_source_block           9
_cod_database_code               4119415