#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/15/2241516.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_2241516
loop_
_publ_author_name
'Thomann, Andreas'
'Huch, Volker'
'Hartmann, Rolf W.'
_publ_section_title
;
 Crystal structure of
 4-methylsulfanyl-2-(2H-tetrazol-2-yl)pyrimidine
;
_journal_coeditor_code           SU5253
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1051
_journal_page_last               o1052
_journal_paper_doi               10.1107/S2056989015023634
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C6 H6 N6 S'
_chemical_formula_moiety         'C6 H6 N6 S'
_chemical_formula_sum            'C6 H6 N6 S'
_chemical_formula_weight         194.23
_chemical_name_systematic
;
4-Methylsulfanyl-2-(2H-tetrazol-2-yl)pyrimidine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                91.407(7)
_cell_angle_beta                 95.864(7)
_cell_angle_gamma                102.695(8)
_cell_formula_units_Z            4
_cell_length_a                   6.3001(17)
_cell_length_b                   7.393(2)
_cell_length_c                   18.159(5)
_cell_measurement_reflns_used    728
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      3.64
_cell_volume                     819.8(4)
_computing_cell_refinement
;
SAINT (Bruker, 2010)
;
_computing_data_collection
;
APEX2 (Bruker, 2010)
;
_computing_data_reduction
;
SAINT (Bruker, 2010)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick 2008)
;
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15501
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.582
_diffrn_reflns_theta_min         2.257
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.302
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0376P)²+0.2718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                3596
_reflns_number_total             4581
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5253sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        819.9(4)
_cod_database_code               2241516
_cod_database_fobs_code          2241516
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.995
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_occupancy
S S1 0.84117(6) 0.83334(5) 0.58281(2) 0.01975(9) Uani d 1
N N1 1.04303(18) 0.69484(15) 0.84617(6) 0.0152(2) Uani d 1
N N2 1.00906(19) 0.60999(17) 0.90974(6) 0.0208(3) Uani d 1
N N3 1.24517(19) 0.79683(17) 0.84553(7) 0.0209(3) Uani d 1
N N4 1.3498(2) 0.77865(18) 0.91059(7) 0.0233(3) Uani d 1
N N5 0.93885(18) 0.76012(15) 0.72442(6) 0.0159(2) Uani d 1
N N6 0.56784(19) 0.65519(16) 0.66803(7) 0.0200(3) Uani d 1
C C1 0.8749(2) 0.67900(17) 0.78527(7) 0.0148(3) Uani d 1
C C2 0.6647(2) 0.58341(19) 0.79335(8) 0.0184(3) Uani d 1
C C3 0.5146(2) 0.5770(2) 0.73096(8) 0.0203(3) Uani d 1
C C4 0.7801(2) 0.74205(18) 0.66783(8) 0.0162(3) Uani d 1
C C5 1.2034(2) 0.6651(2) 0.94818(8) 0.0209(3) Uani d 1
C C6 1.1309(2) 0.9298(2) 0.60068(9) 0.0230(3) Uani d 1
H H1 0.629(3) 0.532(2) 0.8352(10) 0.028(5) Uiso d 1
H H2 0.366(3) 0.512(2) 0.7313(9) 0.023(4) Uiso d 1
H H3 1.235(3) 0.634(2) 0.9944(11) 0.030(5) Uiso d 1
H H4 1.204(3) 0.833(2) 0.6178(10) 0.032(5) Uiso d 1
H H5 1.160(3) 1.037(2) 0.6366(10) 0.030(5) Uiso d 1
H H6 1.172(3) 0.969(3) 0.5531(11) 0.040(5) Uiso d 1
S S2 0.91337(6) 0.35407(5) 0.59998(2) 0.02003(10) Uani d 1
N N7 1.07557(18) 0.19569(15) 0.85809(6) 0.0156(2) Uani d 1
N N8 1.0376(2) 0.11547(17) 0.92240(7) 0.0219(3) Uani d 1
N N9 1.28032(19) 0.29223(17) 0.85739(7) 0.0218(3) Uani d 1
N N10 1.3817(2) 0.27602(18) 0.92304(7) 0.0241(3) Uani d 1
N N11 0.97742(18) 0.26119(15) 0.73636(6) 0.0159(2) Uani d 1
N N12 0.60819(19) 0.16413(16) 0.67866(7) 0.0192(2) Uani d 1
C C7 0.9101(2) 0.18161(17) 0.79690(7) 0.0146(3) Uani d 1
C C8 0.6975(2) 0.08981(19) 0.80433(8) 0.0181(3) Uani d 1
C C9 0.5511(2) 0.0862(2) 0.74162(8) 0.0204(3) Uani d 1
C C10 0.8194(2) 0.24779(18) 0.67912(8) 0.0162(3) Uani d 1
C C11 1.2311(2) 0.1686(2) 0.96118(8) 0.0218(3) Uani d 1
C C12 0.6629(3) 0.3216(2) 0.53901(9) 0.0256(3) Uani d 1
H H7 0.658(3) 0.041(2) 0.8462(10) 0.028(5) Uiso d 1
H H8 0.400(3) 0.022(2) 0.7410(10) 0.027(4) Uiso d 1
H H9 1.264(3) 0.138(3) 1.0104(11) 0.035(5) Uiso d 1
H H10 0.564(3) 0.385(2) 0.5600(10) 0.035(5) Uiso d 1
H H11 0.702(3) 0.373(3) 0.4949(11) 0.037(5) Uiso d 1
H H12 0.600(3) 0.192(3) 0.5294(10) 0.038(5) Uiso d 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
C4 S1 C6 101.92(7)
N3 N1 N2 113.78(11)
N3 N1 C1 123.45(11)
N2 N1 C1 122.75(11)
C5 N2 N1 101.28(11)
N4 N3 N1 105.82(12)
N3 N4 C5 106.17(12)
C1 N5 C4 114.47(12)
C3 N6 C4 115.71(12)
N5 C1 C2 125.31(12)
N5 C1 N1 115.33(12)
C2 C1 N1 119.36(12)
C1 C2 C3 114.59(13)
C1 C2 H1 122.4(11)
C3 C2 H1 123.0(12)
N6 C3 C2 123.19(13)
N6 C3 H2 116.5(10)
C2 C3 H2 120.3(10)
N5 C4 N6 126.72(13)
N5 C4 S1 119.87(10)
N6 C4 S1 113.41(10)
N2 C5 N4 112.96(13)
N2 C5 H3 124.0(12)
N4 C5 H3 123.0(12)
S1 C6 H4 108.9(11)
S1 C6 H5 110.3(10)
H4 C6 H5 112.5(14)
S1 C6 H6 103.5(11)
H4 C6 H6 110.8(15)
H5 C6 H6 110.4(15)
C10 S2 C12 101.37(8)
N9 N7 N8 113.63(11)
N9 N7 C7 123.40(11)
N8 N7 C7 122.96(11)
C11 N8 N7 101.34(12)
N10 N9 N7 105.89(12)
N9 N10 C11 106.19(12)
C7 N11 C10 114.67(12)
C10 N12 C9 115.82(12)
N11 C7 C8 125.20(12)
N11 C7 N7 115.25(12)
C8 C7 N7 119.55(12)
C7 C8 C9 114.40(13)
C7 C8 H7 122.5(11)
C9 C8 H7 123.1(12)
N12 C9 C8 123.46(14)
N12 C9 H8 116.1(11)
C8 C9 H8 120.5(11)
N12 C10 N11 126.44(13)
N12 C10 S2 119.96(10)
N11 C10 S2 113.60(10)
N8 C11 N10 112.94(13)
N8 C11 H9 124.6(12)
N10 C11 H9 122.5(12)
S2 C12 H10 109.7(11)
S2 C12 H11 105.7(12)
H10 C12 H11 110.6(16)
S2 C12 H12 110.3(11)
H10 C12 H12 111.9(16)
H11 C12 H12 108.4(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.7453(15)
S1 C6 1.8004(16)
N1 N3 1.3311(16)
N1 N2 1.3412(16)
N1 C1 1.4347(17)
N2 C5 1.3207(19)
N3 N4 1.3176(17)
N4 C5 1.356(2)
N5 C1 1.3267(17)
N5 C4 1.3412(17)
N6 C3 1.3336(19)
N6 C4 1.3506(18)
C1 C2 1.3815(19)
C2 C3 1.393(2)
C2 H1 0.885(19)
C3 H2 0.951(17)
C5 H3 0.891(19)
C6 H4 0.974(17)
C6 H5 0.988(17)
C6 H6 0.96(2)
S2 C10 1.7487(15)
S2 C12 1.7992(16)
N7 N9 1.3314(16)
N7 N8 1.3421(16)
N7 C7 1.4291(17)
N8 C11 1.3182(19)
N9 N10 1.3148(17)
N10 C11 1.3566(19)
N11 C7 1.3237(17)
N11 C10 1.3496(17)
N12 C10 1.3377(18)
N12 C9 1.3393(19)
C7 C8 1.3837(19)
C8 C9 1.386(2)
C8 H7 0.886(19)
C9 H8 0.965(18)
C11 H9 0.940(19)
C12 H10 0.955(19)
C12 H11 0.93(2)
C12 H12 0.957(19)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H1 N9 1_455 0.89(2) 2.58(2) 3.203(2) 129(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139087938
