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_4119412
_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         '3(C36 H31 N7, C H Cl3'
_chemical_formula_sum            'C36.33333 H31.33333 Cl N7'
_chemical_formula_weight         601.37
_chemical_name_systematic
; 
 ? 
;
_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                80.594(2)
_cell_angle_beta                 81.100(3)
_cell_angle_gamma                80.250(2)
_cell_formula_units_Z            6
_cell_length_a                   16.0228(11)
_cell_length_b                   16.8314(11)
_cell_length_c                   17.8423(11)
_cell_measurement_reflns_used    8837
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.48
_cell_measurement_theta_min      2.22
_cell_volume                     4638.5(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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0867
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            64273
_diffrn_reflns_theta_full        27.63
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       prism
_exptl_crystal_F_000             1892
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1559
_refine_ls_number_reflns         21360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.1828
_reflns_number_gt                12681
_reflns_number_total             21360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja312084s_si_002.cif
_cod_data_source_block           5
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