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_4024247
_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         'C10 H6 Br N O2'
_chemical_formula_sum            'C10 H6 Br N O2'
_chemical_formula_weight         252.07
_chemical_name_systematic
; 
cif-1-Bromo-4-4(4-nitrophenyl)but-1-en-3-yne
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 and encifer'
_cell_angle_alpha                82.759(10)
_cell_angle_beta                 73.703(10)
_cell_angle_gamma                89.824(12)
_cell_formula_units_Z            2
_cell_length_a                   7.2030(10)
_cell_length_b                   7.4440(14)
_cell_length_c                   9.2950(10)
_cell_measurement_reflns_used    16617
_cell_measurement_temperature    122(5)
_cell_measurement_theta_max      37
_cell_measurement_theta_min      2.3
_cell_volume                     474.28(12)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18866
_diffrn_reflns_theta_full        37.00
_diffrn_reflns_theta_max         37.00
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    4.303
_exptl_absorpt_correction_T_max  0.69344
_exptl_absorpt_correction_T_min  0.15876
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         4712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                4152
_reflns_number_total             4712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802190q_si_003.cif
_cod_data_source_block           kcd337
_cod_database_code               4024247