#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/22/2222285.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222285
loop_
_publ_author_name
'Zhu, Hai-Bin'
'Wang, Hai'
'Li, Lei'
_publ_section_title
;
 4,4'-Di-4-pyridyl-2,2'-dithiodipyrimidine
;
_journal_coeditor_code           CV2571
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1588
_journal_paper_doi               10.1107/S1600536809022004
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H12 N6 S2'
_chemical_formula_moiety         'C18 H12 N6 S2'
_chemical_formula_sum            'C18 H12 N6 S2'
_chemical_formula_weight         376.48
_chemical_name_systematic
;
4,4'-Di-4-pyridyl-2,2'-dithiodipyrimidine
;
_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                84.2280(10)
_cell_angle_beta                 74.9260(10)
_cell_angle_gamma                72.9830(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1060(8)
_cell_length_b                   9.3861(9)
_cell_length_c                   10.9176(10)
_cell_measurement_reflns_used    3982
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.26
_cell_volume                     861.27(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0927
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5665
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  0.9201
_exptl_absorpt_correction_T_min  0.8835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.498
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.092P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1577
_reflns_number_gt                3283
_reflns_number_total             3982
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2571.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2222285
_cod_database_fobs_code          2222285
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 0.17317(7) 0.15307(5) 0.45673(4) 0.04865(18) Uani d . 1 . .
S S2 0.04746(6) 0.10746(6) 0.34511(5) 0.05008(19) Uani d . 1 . .
N N5 0.33888(18) -0.04716(16) 0.21420(13) 0.0350(3) Uani d . 1 . .
N N3 0.23093(18) 0.39811(16) 0.49060(14) 0.0390(3) Uani d . 1 . .
C C13 0.4305(2) -0.12822(18) 0.11230(16) 0.0350(4) Uani d . 1 . .
C C10 0.1865(2) 0.00258(19) 0.21737(17) 0.0372(4) Uani d . 1 . .
C C14 0.6028(2) -0.18393(19) 0.10565(16) 0.0359(4) Uani d . 1 . .
N N4 0.1100(2) -0.01902(19) 0.13474(17) 0.0465(4) Uani d . 1 . .
N N2 0.1638(2) 0.39133(19) 0.29373(16) 0.0488(4) Uani d . 1 . .
C C18 0.7094(2) -0.2658(2) 0.00391(19) 0.0450(4) Uani d . 1 . .
H H18A 0.6733 -0.2889 -0.0618 0.054 Uiso calc R 1 . .
C C9 0.1901(2) 0.3355(2) 0.40474(17) 0.0391(4) Uani d . 1 . .
C C15 0.6663(2) -0.1528(2) 0.19982(18) 0.0445(4) Uani d . 1 . .
H H15A 0.6009 -0.0976 0.2695 0.053 Uiso calc R 1 . .
C C6 0.2505(2) 0.53454(19) 0.45950(17) 0.0382(4) Uani d . 1 . .
C C5 0.2986(2) 0.6052(2) 0.55342(17) 0.0398(4) Uani d . 1 . .
N N6 0.9295(2) -0.2845(2) 0.09198(18) 0.0547(5) Uani d . 1 . .
C C1 0.3575(2) 0.7282(2) 0.5210(2) 0.0477(5) Uani d . 1 . .
H H1A 0.3689 0.7692 0.4391 0.057 Uiso calc R 1 . .
C C17 0.8683(3) -0.3123(3) 0.0009(2) 0.0537(5) Uani d . 1 . .
H H17A 0.9372 -0.3662 -0.0684 0.064 Uiso calc R 1 . .
C C11 0.2021(2) -0.0998(2) 0.03537(19) 0.0481(5) Uani d . 1 . .
H H11A 0.1556 -0.1189 -0.0254 0.058 Uiso calc R 1 . .
C C7 0.2231(3) 0.6050(2) 0.3465(2) 0.0510(5) Uani d . 1 . .
H H7A 0.2337 0.7005 0.3253 0.061 Uiso calc R 1 . .
C C12 0.3641(2) -0.1563(2) 0.01909(19) 0.0445(4) Uani d . 1 . .
H H12A 0.4265 -0.2112 -0.0517 0.053 Uiso calc R 1 . .
C C16 0.8274(3) -0.2050(3) 0.1883(2) 0.0525(5) Uani d . 1 . .
H H16A 0.8673 -0.1831 0.2522 0.063 Uiso calc R 1 . .
C C4 0.2837(3) 0.5510(3) 0.6763(2) 0.0586(6) Uani d . 1 . .
H H4B 0.2450 0.4686 0.7018 0.070 Uiso calc R 1 . .
N N1 0.3860(3) 0.7375(2) 0.7322(2) 0.0695(6) Uani d . 1 . .
C C8 0.1796(3) 0.5286(2) 0.2664(2) 0.0546(5) Uani d . 1 . .
H H8A 0.1605 0.5747 0.1904 0.066 Uiso calc R 1 . .
C C2 0.3989(3) 0.7884(3) 0.6135(2) 0.0584(6) Uani d . 1 . .
H H2B 0.4387 0.8704 0.5905 0.070 Uiso calc R 1 . .
C C3 0.3270(4) 0.6206(3) 0.7623(2) 0.0737(8) Uani d . 1 . .
H H3B 0.3142 0.5837 0.8455 0.088 Uiso calc R 1 . .
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
C9 S1 S2 . . 104.02(6) ?
C10 S2 S1 . . 106.81(6) ?
C10 N5 C13 . . 115.68(14) ?
C9 N3 C6 . . 115.86(16) ?
N5 C13 C12 . . 120.70(17) ?
N5 C13 C14 . . 116.75(15) ?
C12 C13 C14 . . 122.55(16) ?
N5 C10 N4 . . 128.71(17) ?
N5 C10 S2 . . 122.14(13) ?
N4 C10 S2 . . 109.10(13) ?
C18 C14 C15 . . 116.68(17) ?
C18 C14 C13 . . 121.97(16) ?
C15 C14 C13 . . 121.33(16) ?
C10 N4 C11 . . 114.73(16) ?
C8 N2 C9 . . 114.58(16) ?
C17 C18 C14 . . 119.77(18) ?
C17 C18 H18A . . 120.1 ?
C14 C18 H18A . . 120.1 ?
N3 C9 N2 . . 128.50(18) ?
N3 C9 S1 . . 111.00(14) ?
N2 C9 S1 . . 120.50(14) ?
C16 C15 C14 . . 119.14(18) ?
C16 C15 H15A . . 120.4 ?
C14 C15 H15A . . 120.4 ?
N3 C6 C7 . . 120.54(17) ?
N3 C6 C5 . . 116.60(16) ?
C7 C6 C5 . . 122.84(17) ?
C4 C5 C1 . . 117.73(18) ?
C4 C5 C6 . . 120.55(18) ?
C1 C5 C6 . . 121.71(18) ?
C17 N6 C16 . . 116.21(18) ?
C2 C1 C5 . . 118.5(2) ?
C2 C1 H1A . . 120.8 ?
C5 C1 H1A . . 120.8 ?
N6 C17 C18 . . 123.76(19) ?
N6 C17 H17A . . 118.1 ?
C18 C17 H17A . . 118.1 ?
N4 C11 C12 . . 122.50(16) ?
N4 C11 H11A . . 118.8 ?
C12 C11 H11A . . 118.7 ?
C8 C7 C6 . . 117.84(19) ?
C8 C7 H7A . . 121.1 ?
C6 C7 H7A . . 121.1 ?
C11 C12 C13 . . 117.66(17) ?
C11 C12 H12A . . 121.2 ?
C13 C12 H12A . . 121.2 ?
N6 C16 C15 . . 124.43(18) ?
N6 C16 H16A . . 117.8 ?
C15 C16 H16A . . 117.8 ?
C5 C4 C3 . . 119.3(2) ?
C5 C4 H4B . . 120.4 ?
C3 C4 H4B . . 120.4 ?
C2 N1 C3 . . 116.0(2) ?
N2 C8 C7 . . 122.63(19) ?
N2 C8 H8A . . 118.7 ?
C7 C8 H8A . . 118.7 ?
N1 C2 C1 . . 124.7(2) ?
N1 C2 H2B . . 117.6 ?
C1 C2 H2B . . 117.6 ?
N1 C3 C4 . . 123.8(2) ?
N1 C3 H3B . . 118.1 ?
C4 C3 H3B . . 118.1 ?
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 C9 . 1.7867(19) ?
S1 S2 . 2.0238(7) ?
S2 C10 . 1.7734(19) ?
N5 C10 . 1.321(2) ?
N5 C13 . 1.352(2) ?
N3 C9 . 1.335(2) ?
N3 C6 . 1.342(2) ?
C13 C12 . 1.392(2) ?
C13 C14 . 1.486(3) ?
C10 N4 . 1.336(2) ?
C14 C18 . 1.393(3) ?
C14 C15 . 1.395(3) ?
N4 C11 . 1.332(3) ?
N2 C8 . 1.333(3) ?
N2 C9 . 1.323(2) ?
C18 C17 . 1.377(3) ?
C18 H18A . 0.9300 ?
C15 C16 . 1.380(3) ?
C15 H15A . 0.9300 ?
C6 C7 . 1.386(3) ?
C6 C5 . 1.491(2) ?
C5 C4 . 1.374(3) ?
C5 C1 . 1.388(3) ?
N6 C17 . 1.339(3) ?
N6 C16 . 1.331(3) ?
C1 C2 . 1.385(3) ?
C1 H1A . 0.9300 ?
C17 H17A . 0.9300 ?
C11 C12 . 1.384(3) ?
C11 H11A . 0.9300 ?
C7 C8 . 1.382(3) ?
C7 H7A . 0.9300 ?
C12 H12A . 0.9300 ?
C16 H16A . 0.9300 ?
C4 C3 . 1.389(3) ?
C4 H4B . 0.9300 ?
N1 C2 . 1.323(3) ?
N1 C3 . 1.335(3) ?
C8 H8A . 0.9300 ?
C2 H2B . 0.9300 ?
C3 H3B . 0.9300 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cg1 Cg2 3.888(2) . 2_666 n
Cg3 Cg4 3.5720(10) . 2_655 n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742589
