#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/78/2227899.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_2227899
loop_
_publ_author_name
'Akbar, Muhammad'
'Quereshi, Fahim Ashraf'
'Nasir, Waqar'
'Adnan, Ahmad'
'Ng, Seik Weng'
_publ_section_title
;
 1,4-Bis(pyrimidin-2-ylsulfanyl)butane
;
_journal_coeditor_code           PK2276
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2849
_journal_paper_doi               10.1107/S1600536810041103
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H14 N4 S2'
_chemical_formula_moiety         'C12 H14 N4 S2'
_chemical_formula_sum            'C12 H14 N4 S2'
_chemical_formula_weight         278.39
_chemical_name_systematic
;
1,4-Bis(pyrimidin-2-ylsulfanyl)butane
;
_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                86.9150(10)
_cell_angle_beta                 87.2530(10)
_cell_angle_gamma                75.8530(10)
_cell_formula_units_Z            1
_cell_length_a                   5.50250(10)
_cell_length_b                   7.66170(10)
_cell_length_c                   8.3598(2)
_cell_measurement_reflns_used    3569
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.4
_cell_volume                     341.033(11)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker Kappa APEXII diffractometer'
_diffrn_measurement_method       'φ and ω 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5571
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             146
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0684P)²+0.0791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                1384
_reflns_number_total             1524
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2276.cif
_cod_data_source_block           I
_cod_original_cell_volume        341.030(10)
_cod_database_code               2227899
_cod_database_fobs_code          2227899
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.00757(8) 0.83807(5) 0.36197(5) 0.0497(2) Uani d . 1 . .
N N1 0.2131(3) 0.68013(19) 0.09155(18) 0.0464(3) Uani d . 1 . .
N N2 -0.2078(3) 0.8589(2) 0.09199(19) 0.0505(4) Uani d . 1 . .
C C1 0.3698(3) 0.5370(2) 0.46719(19) 0.0437(4) Uani d . 1 . .
H H1A 0.3522 0.4713 0.3742 0.052 Uiso calc R 1 . .
H H1B 0.2444 0.5191 0.5479 0.052 Uiso calc R 1 . .
C C2 0.3247(3) 0.7362(2) 0.4204(2) 0.0469(4) Uani d . 1 . .
H H2A 0.4395 0.7516 0.3321 0.056 Uiso calc R 1 . .
H H2B 0.3622 0.7989 0.5103 0.056 Uiso calc R 1 . .
C C3 0.0099(3) 0.78350(19) 0.16033(19) 0.0396(3) Uani d . 1 . .
C C4 0.1936(3) 0.6518(3) -0.0632(2) 0.0533(4) Uani d . 1 . .
H H4 0.3305 0.5800 -0.1171 0.064 Uiso calc R 1 . .
C C5 -0.0195(4) 0.7241(3) -0.1458(2) 0.0541(4) Uani d . 1 . .
H H5 -0.0289 0.7042 -0.2539 0.065 Uiso calc R 1 . .
C C6 -0.2187(3) 0.8274(3) -0.0615(2) 0.0539(4) Uani d . 1 . .
H H6 -0.3667 0.8770 -0.1140 0.065 Uiso calc R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0475(3) 0.0499(3) 0.0434(3) 0.00536(19) -0.00486(18) -0.00421(18)
N1 0.0412(7) 0.0462(7) 0.0472(8) -0.0017(6) -0.0016(6) -0.0023(6)
N2 0.0391(7) 0.0549(8) 0.0517(9) 0.0004(6) -0.0063(6) -0.0012(6)
C1 0.0419(8) 0.0443(8) 0.0420(8) -0.0037(6) -0.0078(7) -0.0004(6)
C2 0.0467(8) 0.0440(8) 0.0470(9) -0.0035(7) -0.0116(7) -0.0020(7)
C3 0.0384(7) 0.0352(7) 0.0428(8) -0.0048(6) -0.0032(6) 0.0013(6)
C4 0.0500(10) 0.0566(10) 0.0485(10) -0.0038(8) 0.0045(7) -0.0067(8)
C5 0.0603(11) 0.0596(10) 0.0419(9) -0.0130(8) -0.0047(8) -0.0021(7)
C6 0.0474(9) 0.0605(10) 0.0514(10) -0.0075(8) -0.0134(8) 0.0033(8)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 S1 C2 . . 103.41(8) ?
C3 N1 C4 . . 115.09(14) ?
C6 N2 C3 . . 115.78(15) ?
C2 C1 C1 . 2_666 111.38(17) ?
C2 C1 H1A . . 109.4 ?
C1 C1 H1A 2_666 . 109.4 ?
C2 C1 H1B . . 109.4 ?
C1 C1 H1B 2_666 . 109.4 ?
H1A C1 H1B . . 108.0 ?
C1 C2 S1 . . 113.63(12) ?
C1 C2 H2A . . 108.8 ?
S1 C2 H2A . . 108.8 ?
C1 C2 H2B . . 108.8 ?
S1 C2 H2B . . 108.8 ?
H2A C2 H2B . . 107.7 ?
N1 C3 N2 . . 127.07(15) ?
N1 C3 S1 . . 120.73(12) ?
N2 C3 S1 . . 112.20(12) ?
N1 C4 C5 . . 122.81(16) ?
N1 C4 H4 . . 118.6 ?
C5 C4 H4 . . 118.6 ?
C4 C5 C6 . . 116.83(17) ?
C4 C5 H5 . . 121.6 ?
C6 C5 H5 . . 121.6 ?
N2 C6 C5 . . 122.41(16) ?
N2 C6 H6 . . 118.8 ?
C5 C6 H6 . . 118.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C3 . 1.7571(17) ?
S1 C2 . 1.8076(16) ?
N1 C3 . 1.328(2) ?
N1 C4 . 1.337(2) ?
N2 C6 . 1.325(2) ?
N2 C3 . 1.337(2) ?
C1 C2 . 1.517(2) ?
C1 C1 2_666 1.524(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C4 C5 . 1.370(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C1 C2 S1 2_666 . . . -173.69(15) ?
C3 S1 C2 C1 . . . . -82.52(14) ?
C4 N1 C3 N2 . . . . 0.6(3) ?
C4 N1 C3 S1 . . . . -178.46(12) ?
C6 N2 C3 N1 . . . . -0.7(3) ?
C6 N2 C3 S1 . . . . 178.47(13) ?
C2 S1 C3 N1 . . . . 3.47(15) ?
C2 S1 C3 N2 . . . . -175.76(12) ?
C3 N1 C4 C5 . . . . 0.2(3) ?
N1 C4 C5 C6 . . . . -0.8(3) ?
C3 N2 C6 C5 . . . . -0.1(3) ?
C4 C5 C6 N2 . . . . 0.8(3) ?
