Structural Effects on the Electronic Properties of Extended Fused-Ring Thieno[3,4-b]pyrazine Analogues
Jon P. Nietfeld; Ryan L. Schwiderski; Thomas P. Gonnella; Seth C. Rasmussen; Journal of Organic Chemistry 76 (2011) 6383–6388; doi:10.1021/jo200850w

data_4026484
_publ_contact_author_address
;
Department of Chemistry and Biochemistry
North Dakota State University
NDSU Dept. 2735, P.O. Box 6050
Fargo, ND 58108-6050
;
_publ_contact_author_email       seth.rasmussen@ndsu.edu
_publ_contact_author_fax         '701 231-8831'
_publ_contact_author_name        'Seth C. Rasmussen'
_publ_contact_author_phone       '701 231-8747'
_publ_section_title
;
 Structural Effects on the Electronic Properties of Extended Fused-Ring
 Thieno[3,4-b]pyrazine Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6383
_journal_page_last               6388
_journal_paper_doi               10.1021/jo200850w
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C16 H8 N2 S'
_chemical_formula_sum            'C16 H8 N2 S'
_chemical_formula_weight         260.31
_chemical_melting_point          150
_chemical_name_common            Acenaphtho[1,2-b]thieno[3,4-e]pyrazine
_chemical_name_systematic
;
Acenaphtho[1,2-b]thieno[3,4-e]pyrazine
;
_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                 92.939(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8298(2)
_cell_length_b                   12.6432(7)
_cell_length_c                   23.0950(14)
_cell_measurement_reflns_used    6810
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.99
_cell_measurement_theta_min      3.83
_cell_volume                     1116.81(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8480
_diffrn_reflns_theta_full        67.29
_diffrn_reflns_theta_max         67.29
_diffrn_reflns_theta_min         3.83
_exptl_absorpt_coefficient_mu    2.421
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Acta Cryst (1995). A51, 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+0.5416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                1879
_reflns_number_total             1937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200850w_si_002.cif
_cod_data_source_block           cu_rxs1_0m
_cod_database_code               4026484