Synthesis and Characterization of New 2,3-Disubstituted Thieno[3,4-b]pyrazines: Tunable Building Blocks for Low Band Gap Conjugated Materials
Li Wen; Jon P. Nietfeld; Chad M. Amb; Seth C. Rasmussen; Journal of Organic Chemistry 73 (2008) 8529–8536; doi:10.1021/jo801632z

data_4023820
_publ_contact_author_address
;
Department of Chemistry and Molecular Biology
North Dakota State University
Fargo, ND 58105
;
_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 New 2,3-Disubstituted
 Thieno[3,4-b]pyrazines: Tunable Building Blocks for
 Low Band Gap Conjugated Materials
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8529
_journal_page_last               8536
_journal_paper_doi               10.1021/jo801632z
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C8 H6 Br2 N2 S'
_chemical_formula_sum            'C8 H6 Br2 N2 S'
_chemical_formula_weight         322.03
_chemical_melting_point          107.2
_chemical_name_common            2,3-bis(bromomethyl)thieno[3,4-b]pyrazine
_chemical_name_systematic
;
 2,3-bis(bromomethyl)thieno[3,4-b]pyrazine
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.577(9)
_cell_length_b                   12.475(10)
_cell_length_c                   7.715(6)
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      56
_cell_measurement_theta_min      2
_cell_volume                     1018.0(14)
_computing_cell_refinement       'SMART 5.63'
_computing_data_collection       'SMART 5.63'
_computing_data_reduction        'SHELXS 6.14'
_computing_molecular_graphics    XP
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL 6.14'
_computing_structure_solution    'SHELXS 6.14'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  '1K CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8403
_diffrn_reflns_theta_full        27.91
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    8.120
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.281291
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.101
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          .68
_exptl_crystal_size_mid          .56
_exptl_crystal_size_min          .28
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.087(16)
_refine_ls_extinction_coef       0.0153(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.2602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                2135
_reflns_number_total             2396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801632z_si_002.cif
_cod_data_source_block           (BrMe)2TP
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023820