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_4028297
_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         'C16 H10 Br2 N2 S3'
_chemical_formula_sum            'C16 H10 Br2 N2 S3'
_chemical_formula_weight         486.26
_chemical_melting_point          433
_chemical_name_systematic
;
 2,3-Bis(bromomethyl)-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                 95.5760(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1751(4)
_cell_length_b                   13.4330(3)
_cell_length_c                   7.5616(2)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.42
_cell_measurement_theta_min      2.74
_cell_volume                     1635.21(7)
_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 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13535
_diffrn_reflns_theta_full        67.52
_diffrn_reflns_theta_max         67.52
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    9.858
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Acta Cryst (1995). A51, 33-38'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     261
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0191
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+1.0796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                2785
_reflns_number_total             2841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400577q_si_002_3.cif
_cod_data_source_block           cu_rxs2_0ma
_cod_database_code               4028297