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_4022266
_publ_contact_author_address
;
Department of Chemistry
North Dakota State University
Fargo, North Dakota 58105
;
_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
;
 Thieno[3,4-b]pyrazines: Synthesis, Structure, and Reactivity
;
_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            'C4 Br2 N2 O4 S'
_chemical_formula_weight         331.94
_chemical_melting_point          408.15
_chemical_name_common            2,5-dibromo-3,4-ditnitrothiophene
_chemical_name_systematic        2,5-dibromo-3,4-ditnitrothiophene
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 128.837(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5483(19)
_cell_length_b                   7.3661(10)
_cell_length_c                   10.7779(14)
_cell_measurement_temperature    296(2)
_cell_volume                     899.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_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  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2658
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    9.224
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51(1995) pp. 33-38'
_exptl_crystal_colour            yellow-ora
_exptl_crystal_density_diffrn    2.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'broken ang'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.006
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.183
_refine_ls_extinction_coef       0.0163(14)
_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   0.799
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         1036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.799
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0749P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                668
_reflns_number_total             1036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0262255-3_s2_1.cif
_cod_data_source_block           d
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_chemical_melting_point' value '135 C' was changed to '408.15' - 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 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022266