Thieno[3,4-b]pyrazines: Synthesis, Structure, and Reactivity
Don D. Kenning; Kari A. Mitchell; Tessa R. Calhoun; Melanie R. Funfar; Daniel J. Sattler; Seth C. Rasmussen; Journal of Organic Chemistry 67 (2002) 9073–9076; doi:10.1021/jo0262255

data_4022267
_publ_contact_author_address
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Department of Chemistry
North Dakota State University
Fargo, North Dakota 58105
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_publ_contact_author_email       seth.rasmussen@ndsu.nodak.edu
_publ_contact_author_fax         701-231-8831
_publ_contact_author_name        'Seth Rasmussen'
_publ_contact_author_phone       701-231-8747
_publ_section_title
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 Thieno[3,4-b]pyrazines: Synthesis, Structure, and Reactivity
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9073
_journal_page_last               9076
_journal_paper_doi               10.1021/jo0262255
_journal_volume                  67
_journal_year                    2002
_chemical_formula_sum            'C8 H8 N2 S'
_chemical_formula_weight         164.22
_chemical_melting_point          417.15
_chemical_name_common            2,3-dimethylthieno[3,4-b]pyrazine
_chemical_name_systematic        2,3-dimethylthieno[3,4-b]pyrazine
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.509(2)
_cell_angle_beta                 80.435(2)
_cell_angle_gamma                87.671(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8858(6)
_cell_length_b                   7.7556(8)
_cell_length_c                   8.0654(8)
_cell_measurement_temperature    298(2)
_cell_volume                     405.08(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'CCD Area Detector'
_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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2582
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51(1995) pp. 33-38'
_exptl_crystal_colour            'light tan'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.030(6)
_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   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0461P)^2^+0.0633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                1212
_reflns_number_total             1806
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0262255-3_s2_2.cif
_cod_data_source_block           don021s
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '144 C' was changed to '417.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
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_cod_database_code               4022267