Synthesis and Characterization of Tetrathiafulvalene-Substituted Di- and Tetraethynylethenes with p-Nitrophenyl Acceptors
Asbjørn S. Andersson; Lasse Kerndrup; Anders Ø. Madsen; Kristine Kilså; Mogens Brøndsted Nielsen; Philip R. La Porta; Ivan Biaggio; Journal of Organic Chemistry 74 (2009) 375–382; doi:10.1021/jo802190q

data_4024246
_publ_contact_author_address
;
Department of Chemistry, University of Copenhagen, 
Universitetsparken 5, DK-2100 Copenhagen \/O, Denmark.
;
_publ_contact_author_email       mbn@kiku.dk
_publ_contact_author_fax         '+45 35320212'
_publ_contact_author_name        'Nielsen, Mogens Br\/ondsted'
_publ_contact_author_phone       '+45 35320210'
_publ_section_title
;
Synthesis and Characterization of Tetrathiafulvalene-Substituted Di- and
Tetraethynylethenes with p-Nitrophenyl Acceptors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              375
_journal_page_last               382
_journal_paper_doi               10.1021/jo802190q
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C18 H9 N O2 S4'
_chemical_formula_sum            'C18 H9 N O2 S4'
_chemical_formula_weight         399.50
_chemical_name_systematic
; 
trans-4-[6-(4-Nitrophenyl)hex-3-ene-1,5-diynyl]tetrathiafulvalene
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      43
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 and encifer'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   25.862(1)
_cell_length_b                   12.875(1)
_cell_length_c                   20.539(1)
_cell_measurement_reflns_used    284
_cell_measurement_temperature    122.4(5)
_cell_measurement_theta_max      24
_cell_measurement_theta_min      5
_cell_volume                     6838.9(7)
_computing_cell_refinement       'Nonius Collect postrefinement'
_computing_data_collection       'Nonius Collect suite'
_computing_data_reduction        'Nonius Collect suite'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122.4(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       \w
_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  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            60444
_diffrn_reflns_theta_full        37.02
_diffrn_reflns_theta_max         37.02
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             3264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         8617
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+6.1097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                7926
_reflns_number_total             8617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802190q_si_002.cif
_cod_data_source_block           kcd330
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               4024246