Synthesis and Characterization of Thieno[3,4-b]pyrazine-Based Terthienyls: Tunable Precursors for Low Band Gap Conjugated Materials
Ryan L. Schwiderski; Seth C. Rasmussen; Journal of Organic Chemistry 78 (2013) 5453–5462; doi:10.1021/jo400577q

data_4028295
_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
;
 Synthesis and Characterization of Thieno[3,4-b]pyrazine-Based
 Terthienyls: Tunable Precursors for Low Band Gap Conjugated Materials
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5453
_journal_page_last               5462
_journal_paper_doi               10.1021/jo400577q
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C26 H32 N2 O2 S3'
_chemical_formula_sum            'C26 H32 N2 O2 S3'
_chemical_formula_weight         500.72
_chemical_melting_point          386
_chemical_name_systematic
;
 2,3-Dihexyloxy-5,7-bis(2-thienyl)thieno[3,4-b]pyrazine
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_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                 94.945(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7138(4)
_cell_length_b                   5.5493(2)
_cell_length_c                   33.3099(10)
_cell_measurement_reflns_used    6010
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.42
_cell_measurement_theta_min      2.66
_cell_volume                     2525.51(14)
_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 0.972
_diffrn_measured_fraction_theta_max 0.972
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            16117
_diffrn_reflns_theta_full        66.61
_diffrn_reflns_theta_max         66.61
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    2.886
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Acta Cryst (1995). A51, 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0507P)^2^+0.9279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                3724
_reflns_number_total             4348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400577q_si_002_1.cif
_cod_data_source_block           cu_rxs8_0m
_cod_database_code               4028295