#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/99/2239910.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_2239910
loop_
_publ_author_name
'El Fal, Mohammed'
'Ramli, Youssef'
'Essassi, El Mokhtar'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 Crystal structure of
 1-ethylpyrazolo[3,4-d]pyrimidine-4(5H)-thione
;
_journal_coeditor_code           HB7262
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1005
_journal_page_last               o1006
_journal_paper_doi               10.1107/S160053681401825X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C7 H8 N4 S'
_chemical_formula_moiety         'C7 H8 N4 S'
_chemical_formula_sum            'C7 H8 N4 S'
_chemical_formula_weight         180.23
_chemical_name_systematic
;
1-Ethylpyrazolo[3,4-d]pyrimidine-4(5H)-thione
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.71(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.472(4)
_cell_length_b                   5.353(4)
_cell_length_c                   17.573(12)
_cell_measurement_reflns_used    1704
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.49
_cell_volume                     419.8(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8 APEX CCD'
_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  0.0587
_diffrn_reflns_av_sigmaI/netI    0.1334
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4028
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.360
_refine_ls_abs_structure_details
'Flack & Bernardinelli (2000), 652 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.11(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1704
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0531
_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)+(0.0000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1387
_reflns_number_gt                1242
_reflns_number_total             1704
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7262sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        419.8(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2239910
_cod_database_fobs_code          2239910
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
C C1 0.2656(8) 0.2169(7) 0.6200(2) 0.0340(9) Uani d . 1 1
C C2 0.3666(8) 0.2465(8) 0.6972(2) 0.0349(9) Uani d . 1 1
C C3 0.5729(9) 0.1222(9) 0.7490(2) 0.0421(10) Uani d . 1 1
H H3 0.6856 -0.0166 0.7370 0.050 Uiso calc R 1 1
C C4 0.2506(9) 0.4396(7) 0.7391(2) 0.0386(10) Uani d . 1 1
C C5 -0.0448(9) 0.5752(8) 0.6444(2) 0.0438(11) Uani d . 1 1
H H5 -0.1874 0.6853 0.6230 0.053 Uiso calc R 1 1
C C6 0.3360(13) 0.5872(10) 0.8749(3) 0.0669(16) Uani d . 1 1
H H6A 0.1925 0.7165 0.8595 0.080 Uiso calc R 1 1
H H6B 0.5229 0.6675 0.8919 0.080 Uiso calc R 1 1
C C7 0.2207(15) 0.4383(15) 0.9390(3) 0.091(3) Uani d . 1 1
H H7A 0.1876 0.5471 0.9810 0.137 Uiso calc R 1 1
H H7B 0.3652 0.3131 0.9550 0.137 Uiso calc R 1 1
H H7C 0.0355 0.3592 0.9221 0.137 Uiso calc R 1 1
N N1 0.0543(7) 0.3928(6) 0.59849(19) 0.0407(9) Uani d . 1 1
H H1 -0.0256 0.4046 0.5509 0.049 Uiso d R 1 1
N N2 0.0419(8) 0.6091(7) 0.71546(19) 0.0435(9) Uani d . 1 1
N N3 0.3849(9) 0.4260(7) 0.80986(17) 0.0482(10) Uani d . 1 1
N N4 0.5830(8) 0.2300(8) 0.81616(19) 0.0513(10) Uani d . 1 1
S S1 0.3799(2) 0.0022(2) 0.55937(5) 0.0413(3) Uani d . 1 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
N1 C1 C2 111.1(3)
N1 C1 S1 122.1(3)
C2 C1 S1 126.8(3)
C4 C2 C1 119.1(4)
C4 C2 C3 104.9(3)
C1 C2 C3 136.0(4)
N4 C3 C2 110.8(4)
N4 C3 H3 124.6
C2 C3 H3 124.6
N3 C4 N2 125.4(4)
N3 C4 C2 106.9(4)
N2 C4 C2 127.7(3)
N2 C5 N1 125.7(4)
N2 C5 H5 117.1
N1 C5 H5 117.1
N3 C6 C7 110.5(5)
N3 C6 H6A 109.5
C7 C6 H6A 109.5
N3 C6 H6B 109.5
C7 C6 H6B 109.5
H6A C6 H6B 108.1
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C5 N1 C1 125.2(3)
C5 N1 H1 112.4
C1 N1 H1 122.4
C5 N2 C4 111.2(3)
C4 N3 N4 111.2(3)
C4 N3 C6 127.6(4)
N4 N3 C6 121.2(4)
C3 N4 N3 106.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.370(5)
C1 C2 1.410(5)
C1 S1 1.669(4)
C2 C4 1.390(5)
C2 C3 1.419(6)
C3 N4 1.312(5)
C3 H3 0.9300
C4 N3 1.347(5)
C4 N2 1.348(5)
C5 N2 1.296(5)
C5 N1 1.359(5)
C5 H5 0.9300
C6 N3 1.459(5)
C6 C7 1.499(7)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
N1 H1 0.8900
N3 N4 1.373(5)
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
N1 H1 S1 2_556 0.89 2.48 3.333(4) 161
C5 H5 S1 1_465 0.93 2.75 3.685(5) 179
C3 H3 N2 1_645 0.93 2.60 3.528(6) 174
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086892
