#------------------------------------------------------------------------------
#$Date: 2017-10-13 13:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201982 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/22/4022267.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4022267
loop_
_publ_author_name
'Don D. Kenning'
'Kari A. Mitchell'
'Tessa R. Calhoun'
'Melanie R. Funfar'
'Daniel J. Sattler'
'Seth C. Rasmussen'
_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            '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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0461P)²+0.0633P] where P=(Fo²+2Fc²)/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
;
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 
;
_cod_database_code               4022267
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.03621(9) 0.75397(8) 0.96664(8) 0.0618(2) Uani 1 1 d .
C1 C 0.0481(3) 0.8479(3) 0.7468(3) 0.0545(5) Uani 1 1 d .
H1 H -0.0498 0.9186 0.6934 0.078(7) Uiso 1 1 calc R
C2 C 0.2223(3) 0.8053(2) 0.6584(2) 0.0424(4) Uani 1 1 d .
N1 N 0.2811(2) 0.8588(2) 0.4786(2) 0.0450(4) Uani 1 1 d .
C3 C 0.4550(3) 0.8049(2) 0.4223(2) 0.0424(4) Uani 1 1 d .
C4 C 0.5812(3) 0.6949(2) 0.5414(3) 0.0419(4) Uani 1 1 d .
N2 N 0.5270(2) 0.6397(2) 0.7122(2) 0.0442(4) Uani 1 1 d .
C5 C 0.3442(3) 0.6947(2) 0.7745(2) 0.0407(4) Uani 1 1 d .
C6 C 0.2589(3) 0.6548(3) 0.9488(3) 0.0520(5) Uani 1 1 d .
H6 H 0.3156 0.5836 1.0432 0.073(7) Uiso 1 1 calc R
C7 C 0.5223(4) 0.8571(3) 0.2275(3) 0.0592(6) Uani 1 1 d .
H7A H 0.4253 0.9327 0.1686 0.073(7) Uiso 1 1 calc R
H7B H 0.5395 0.7502 0.1903 0.092(9) Uiso 1 1 calc R
H7C H 0.6451 0.9219 0.1988 0.097(9) Uiso 1 1 calc R
C8 C 0.7815(3) 0.6418(3) 0.4701(3) 0.0587(6) Uani 1 1 d .
H8A H 0.8403 0.5629 0.5647 0.094(9) Uiso 1 1 calc R
H8B H 0.8623 0.7481 0.4149 0.089(9) Uiso 1 1 calc R
H8C H 0.7704 0.5803 0.3850 0.078(8) Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0580(4) 0.0669(4) 0.0551(4) -0.0169(3) 0.0022(3) 0.0083(3)
C1 0.0471(11) 0.0582(12) 0.0576(13) -0.0151(10) -0.0141(10) 0.0146(10)
C2 0.0420(10) 0.0414(10) 0.0454(11) -0.0119(8) -0.0154(8) 0.0091(8)
N1 0.0470(9) 0.0477(9) 0.0405(9) -0.0092(7) -0.0169(8) 0.0100(7)
C3 0.0483(11) 0.0399(10) 0.0401(10) -0.0108(8) -0.0129(9) 0.0013(8)
C4 0.0404(10) 0.0399(10) 0.0479(11) -0.0144(9) -0.0123(9) 0.0055(8)
N2 0.0428(9) 0.0439(9) 0.0455(10) -0.0097(7) -0.0155(8) 0.0102(7)
C5 0.0439(10) 0.0378(9) 0.0407(10) -0.0092(8) -0.0139(8) 0.0064(8)
C6 0.0584(13) 0.0498(11) 0.0442(11) -0.0077(9) -0.0119(10) 0.0083(10)
C7 0.0685(15) 0.0644(14) 0.0428(12) -0.0118(10) -0.0127(11) 0.0035(12)
C8 0.0473(12) 0.0630(14) 0.0648(14) -0.0194(12) -0.0081(11) 0.0108(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C6 94.27(10)
C2 C1 S1 110.52(16)
C1 C2 N1 126.21(18)
C1 C2 C5 112.44(18)
N1 C2 C5 121.35(16)
C3 N1 C2 116.05(16)
N1 C3 C4 122.51(17)
N1 C3 C7 117.60(18)
C4 C3 C7 119.88(18)
N2 C4 C3 122.50(17)
N2 C4 C8 117.22(18)
C3 C4 C8 120.28(18)
C4 N2 C5 115.99(16)
N2 C5 C6 125.86(17)
N2 C5 C2 121.58(16)
C6 C5 C2 112.56(17)
C5 C6 S1 110.21(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.691(2)
S1 C6 1.691(2)
C1 C2 1.372(3)
C2 N1 1.377(2)
C2 C5 1.427(2)
N1 C3 1.308(2)
C3 C4 1.460(3)
C3 C7 1.495(3)
C4 N2 1.306(2)
C4 C8 1.495(3)
N2 C5 1.376(2)
C5 C6 1.377(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21155561
