#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/53/2215304.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_2215304
loop_
_publ_author_name
'Wu, Guang-Hui'
'Wu, Xin-Min'
'Zhang, Jing-Ping'
'Liu, Tian-Bao'
_publ_section_title
;
 4,4',6,6'-Tetramethyl-2,2'-(ethylenedithio)dipyrimidine
;
_journal_coeditor_code           XU2299
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3776
_journal_page_last               o3776
_journal_paper_doi               10.1107/S1600536807038858
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H18 N4 S2'
_chemical_formula_moiety         'C14 H18 N4 S2'
_chemical_formula_sum            'C14 H18 N4 S2'
_chemical_formula_weight         306.44
_chemical_name_systematic
;
4,4',6,6'-Tetramethyl-2,2'-(ethylenedithio)dipyrimidine
;
_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           SHELXL97
_cell_angle_alpha                85.282(5)
_cell_angle_beta                 83.264(5)
_cell_angle_gamma                89.711(5)
_cell_formula_units_Z            2
_cell_length_a                   8.487(5)
_cell_length_b                   9.167(5)
_cell_length_c                   10.557(5)
_cell_measurement_reflns_used    5112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.9
_cell_volume                     812.9(8)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altamore et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11764
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.9
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange-yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.375
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.375
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0741P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.136
_refine_ls_wR_factor_ref         0.144
_reflns_number_gt                3008
_reflns_number_total             3721
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2299.cif
_cod_data_source_block           I
_cod_database_code               2215304
_cod_database_fobs_code          2215304
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
C C1 -0.1753(2) 0.1379(2) 0.4757(2) 0.0806(6) Uani d . 1 . .
H H1A -0.1925 0.1757 0.3909 0.121 Uiso calc R 1 . .
H H1B -0.2735 0.1379 0.5309 0.121 Uiso calc R 1 . .
H H1C -0.1358 0.0397 0.4734 0.121 Uiso calc R 1 . .
C C2 -0.05600(17) 0.23267(15) 0.52551(16) 0.0548(4) Uani d . 1 . .
C C3 -0.08802(18) 0.29944(17) 0.63776(15) 0.0570(4) Uani d . 1 . .
H H3 -0.1856 0.2861 0.6875 0.068 Uiso calc R 1 . .
C C4 0.02799(18) 0.38698(17) 0.67507(15) 0.0548(4) Uani d . 1 . .
C C5 0.0014(2) 0.4651(2) 0.79489(18) 0.0830(6) Uani d . 1 . .
H H5A 0.0663 0.4221 0.8564 0.125 Uiso calc R 1 . .
H H5B -0.1083 0.4567 0.8295 0.125 Uiso calc R 1 . .
H H5C 0.0290 0.5666 0.7755 0.125 Uiso calc R 1 . .
C C6 0.18869(18) 0.33423(17) 0.49854(14) 0.0544(4) Uani d . 1 . .
C C7 0.5087(5) 0.4183(5) 0.5078(5) 0.0581(14) Uani d P 0.498(10) . 2
H H7A 0.4760 0.3784 0.5948 0.070 Uiso calc PR 0.498(10) . 2
H H7B 0.6158 0.3871 0.4804 0.070 Uiso calc PR 0.498(10) . 2
C C8 0.3687(3) 0.0925(2) 0.7483(2) 0.0881(6) Uani d . 1 . .
H H8A 0.3110 0.0028 0.7725 0.132 Uiso calc R 1 . .
H H8B 0.4025 0.0993 0.6580 0.132 Uiso calc R 1 . .
H H8C 0.3014 0.1739 0.7686 0.132 Uiso calc R 1 . .
C C9 0.5109(2) 0.09497(17) 0.81995(15) 0.0595(4) Uani d . 1 . .
C C10 0.6268(2) -0.00835(17) 0.80949(16) 0.0642(4) Uani d . 1 . .
H H10 0.6211 -0.0824 0.7550 0.077 Uiso calc R 1 . .
C C11 0.7522(2) -0.00184(18) 0.88059(16) 0.0630(4) Uani d . 1 . .
C C12 0.8825(3) -0.1125(3) 0.8756(3) 0.0996(7) Uani d . 1 . .
H H12A 0.9827 -0.0639 0.8738 0.149 Uiso calc R 1 . .
H H12B 0.8822 -0.1638 0.7999 0.149 Uiso calc R 1 . .
H H12C 0.8661 -0.1810 0.9498 0.149 Uiso calc R 1 . .
C C13 0.64045(18) 0.19983(16) 0.96409(14) 0.0519(3) Uani d . 1 . .
C C14 0.4877(2) 0.44566(18) 1.05891(16) 0.0666(4) Uani d . 1 . .
H H14A 0.3960 0.3848 1.0533 0.080 Uiso calc R 1 A 1
H H14B 0.4659 0.4989 1.1347 0.080 Uiso calc R 1 A 1
C C7' 0.4535(4) 0.5207(6) 0.4450(4) 0.0563(14) Uani d P 0.502(10) . 1
H H7C 0.5195 0.5677 0.3719 0.068 Uiso calc PR 0.502(10) . 1
H H7D 0.3642 0.5830 0.4692 0.068 Uiso calc PR 0.502(10) . 1
N N1 0.08528(15) 0.24921(13) 0.45450(12) 0.0554(3) Uani d . 1 . .
N N2 0.16878(15) 0.40563(15) 0.60426(12) 0.0580(3) Uani d . 1 . .
N N3 0.51650(15) 0.20336(14) 0.89806(12) 0.0573(3) Uani d . 1 B .
N N4 0.75976(15) 0.10482(15) 0.95989(13) 0.0609(4) Uani d . 1 B .
S S1 0.3561(4) 0.3698(6) 0.3876(3) 0.0653(6) Uani d P 0.498(10) . 2
S S2 0.65828(6) 0.33032(5) 1.07490(4) 0.06776(18) Uani d . 1 B 1
S S1' 0.3855(4) 0.3241(4) 0.4131(4) 0.0627(6) Uani d P 0.502(10) . 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
C2 C1 H1A . 109.5
C2 C1 H1B . 109.5
H1A C1 H1B . 109.5
C2 C1 H1C . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
N1 C2 C3 . 121.02(13)
N1 C2 C1 . 116.35(15)
C3 C2 C1 . 122.63(16)
C2 C3 C4 . 118.66(15)
C2 C3 H3 . 120.7
C4 C3 H3 . 120.7
N2 C4 C3 . 120.86(15)
N2 C4 C5 . 117.29(14)
C3 C4 C5 . 121.85(15)
C4 C5 H5A . 109.5
C4 C5 H5B . 109.5
H5A C5 H5B . 109.5
C4 C5 H5C . 109.5
H5A C5 H5C . 109.5
H5B C5 H5C . 109.5
N1 C6 N2 . 127.90(14)
N1 C6 S1 . 111.75(14)
N2 C6 S1 . 119.71(14)
N1 C6 S1' . 112.50(14)
N2 C6 S1' . 118.89(14)
C7 C7 S1 2_666 97.3(4)
C7 C7 H7A 2_666 112.3
S1 C7 H7A . 112.3
C7 C7 H7B 2_666 112.3
S1 C7 H7B . 112.3
H7A C7 H7B . 109.9
C9 C8 H8A . 109.5
C9 C8 H8B . 109.5
H8A C8 H8B . 109.5
C9 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
N3 C9 C10 . 121.50(14)
N3 C9 C8 . 116.28(16)
C10 C9 C8 . 122.20(16)
C9 C10 C11 . 119.23(15)
C9 C10 H10 . 120.4
C11 C10 H10 . 120.4
N4 C11 C10 . 120.31(15)
N4 C11 C12 . 117.42(16)
C10 C11 C12 . 122.26(16)
C11 C12 H12A . 109.5
C11 C12 H12B . 109.5
H12A C12 H12B . 109.5
C11 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
N3 C13 N4 . 127.89(14)
N3 C13 S2 . 119.91(12)
N4 C13 S2 . 112.20(11)
C14 C14 S2 2_667 112.22(17)
C14 C14 H14A 2_667 109.2
S2 C14 H14A . 109.2
C14 C14 H14B 2_667 109.2
S2 C14 H14B . 109.2
H14A C14 H14B . 107.9
C7' C7' S1' 2_666 98.6(4)
C7' C7' H7C 2_666 112.1
S1' C7' H7C . 112.1
C7' C7' H7D 2_666 112.1
S1' C7' H7D . 112.1
H7C C7' H7D . 109.7
C6 N1 C2 . 115.82(14)
C6 N2 C4 . 115.73(13)
C13 N3 C9 . 115.11(13)
C13 N4 C11 . 115.95(13)
C6 S1 C7 . 98.73(17)
C13 S2 C14 . 103.18(8)
C6 S1' C7' . 96.10(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.505(2)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
C2 N1 . 1.340(2)
C2 C3 . 1.377(2)
C3 C4 . 1.385(2)
C3 H3 . 0.9300
C4 N2 . 1.337(2)
C4 C5 . 1.498(2)
C5 H5A . 0.9600
C5 H5B . 0.9600
C5 H5C . 0.9600
C6 N1 . 1.3253(19)
C6 N2 . 1.3331(19)
C6 S1 . 1.746(3)
C6 S1' . 1.808(3)
C7 C7 2_666 1.501(9)
C7 S1 . 1.993(6)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 C9 . 1.499(2)
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C9 N3 . 1.347(2)
C9 C10 . 1.363(2)
C10 C11 . 1.377(2)
C10 H10 . 0.9300
C11 N4 . 1.3450(19)
C11 C12 . 1.496(3)
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C13 N3 . 1.3272(18)
C13 N4 . 1.331(2)
C13 S2 . 1.7595(16)
C14 C14 2_667 1.523(3)
C14 S2 . 1.804(2)
C14 H14A . 0.9700
C14 H14B . 0.9700
C7' C7' 2_666 1.503(9)
C7' S1' . 1.962(6)
C7' H7C . 0.9700
C7' H7D . 0.9700
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
N1 C2 C3 C4 . 1.3(2)
C1 C2 C3 C4 . -178.81(16)
C2 C3 C4 N2 . -0.5(2)
C2 C3 C4 C5 . 179.09(15)
N3 C9 C10 C11 . 0.1(3)
C8 C9 C10 C11 . -178.30(17)
C9 C10 C11 N4 . 0.3(3)
C9 C10 C11 C12 . 179.08(19)
N2 C6 N1 C2 . -0.4(2)
S1 C6 N1 C2 . -171.1(2)
S1' C6 N1 C2 . 169.7(2)
C3 C2 N1 C6 . -0.8(2)
C1 C2 N1 C6 . 179.23(13)
N1 C6 N2 C4 . 1.1(2)
S1 C6 N2 C4 . 171.2(2)
S1' C6 N2 C4 . -168.4(2)
C3 C4 N2 C6 . -0.6(2)
C5 C4 N2 C6 . 179.79(15)
N4 C13 N3 C9 . 1.6(2)
S2 C13 N3 C9 . -177.29(10)
C10 C9 N3 C13 . -1.0(2)
C8 C9 N3 C13 . 177.51(14)
N3 C13 N4 C11 . -1.2(2)
S2 C13 N4 C11 . 177.79(11)
C10 C11 N4 C13 . 0.1(2)
C12 C11 N4 C13 . -178.68(18)
N1 C6 S1 C7 . -157.0(2)
N2 C6 S1 C7 . 31.4(4)
S1' C6 S1 C7 . -61.0(5)
C7 C7 S1 C6 2_666 -96.1(3)
N3 C13 S2 C14 . -2.25(14)
N4 C13 S2 C14 . 178.69(12)
C14 C14 S2 C13 2_667 -78.53(18)
N1 C6 S1' C7' . 153.0(2)
N2 C6 S1' C7' . -35.9(4)
S1 C6 S1' C7' . 61.7(5)
C7' C7' S1' C6 2_666 99.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139073024
