##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/3'
_chemical_name_systematic
;
Ethyl
2-[4-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]acetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H12 N4 O2 S'
_chemical_formula_sum     'C10 H12 N4 O2 S'
_chemical_formula_iupac     'C10 H12 N4 O2 S'
_chemical_formula_weight     252.30
_chemical_melting_point     ?
_chemical_absolute_configuration     ad
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P n a 21'
_space_group_name_Hall     'P 2c -2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     15.207(2)
_cell_length_b     7.9249(11)
_cell_length_c     19.540(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2354.9(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9868
_cell_measurement_theta_min     2.7736
_cell_measurement_theta_max     29.1585
_cell_measurement_temperature     150.(2)
_exptl_crystal_description     column
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.396
_exptl_crystal_size_mid     0.170
_exptl_crystal_size_min     0.165
_exptl_crystal_density_diffrn     1.423
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1056
_exptl_absorpt_coefficient_mu     0.271
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_absorpt_correction_T_min     0.86
_exptl_absorpt_correction_T_max     0.96
_exptl_special_details
;
The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, collected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 20 sec/frame.
;
_diffrn_ambient_temperature     150(2)
_diffrn_source     'fine-focus sealed tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Smart APEX CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     43340
_diffrn_reflns_av_R_equivalents     0.0341
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_theta_min     2.085
_diffrn_reflns_theta_max     29.231
_diffrn_reflns_theta_full     29.200
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon
were placed in calculated positions (C---H = 0.95 - 0.99 Å). All were
included as riding contributions with isotropic displacement parameters
1.2 - 1.5 times those of the attached atoms. Although intensity statistics
indicated a centric space group, solution in the centric space group by
direct and Patterson methods indicated serious disorder while use of
dual space methods (SHELXT, Sheldrick, 2015a) gave an
ordered solution in the non-centric space group as the only option.
Inspection of the resulting two independent molecules indicated slight
differences in the rotational orientations of the methyl groups.
;
_reflns_number_total     6339
_reflns_number_gt     5436
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0492
_refine_ls_R_factor_gt     0.0426
_refine_ls_wR_factor_gt     0.1189
_refine_ls_wR_factor_ref     0.1224
_refine_ls_goodness_of_fit_ref     1.091
_refine_ls_restrained_S_all     1.091
_refine_ls_number_reflns     6339
_refine_ls_number_parameters     311
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0807P)²+0.1629P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.572
_refine_diff_density_min     -0.474
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 2355 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack     0.08(4)
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'
    'O' 'O' 0.0106 0.0060
                         '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'
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/1 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.74531(5) 1.26019(8) 0.57534(6) 0.0250(2) Uani d 1 . .
    O O1 0.59288(18) 0.5947(3) 0.71430(14) 0.0419(6) Uani d 1 . .
    O O2 0.54002(17) 0.3444(3) 0.67778(13) 0.0348(5) Uani d 1 . .
    N N1 0.81795(14) 0.9505(3) 0.57177(13) 0.0203(4) Uani d 1 . .
    N N2 0.73831(15) 0.6863(3) 0.57468(14) 0.0204(5) Uani d 1 . .
    N N3 0.58118(17) 0.7265(3) 0.58391(18) 0.0197(6) Uani d 1 . .
    N N4 0.52384(15) 0.8591(3) 0.58972(14) 0.0231(5) Uani d 1 . .
    C C1 0.66249(16) 0.9581(3) 0.57980(16) 0.0184(5) Uani d 1 . .
    C C2 0.74420(16) 1.0407(3) 0.57571(17) 0.0188(5) Uani d 1 . .
    C C3 0.8103(2) 0.7801(4) 0.5709(2) 0.0212(6) Uani d 1 . .
    H H3 0.863935 0.719525 0.567069 0.025 Uiso calc 1 . .
    C C4 0.66523(19) 0.7812(4) 0.57899(19) 0.0180(5) Uani d 1 . .
    C C5 0.57179(18) 0.9976(4) 0.58628(16) 0.0216(6) Uani d 1 . .
    H H5 0.548698 1.108876 0.587910 0.026 Uiso calc 1 . .
    C C6 0.86041(19) 1.3043(5) 0.5889(2) 0.0373(8) Uani d 1 . .
    H H6A 0.895983 1.226210 0.561563 0.056 Uiso calc 1 . .
    H H6B 0.874605 1.290078 0.637458 0.056 Uiso calc 1 . .
    H H6C 0.873159 1.420555 0.574958 0.056 Uiso calc 1 . .
    C C7 0.55178(19) 0.5563(4) 0.59599(17) 0.0232(6) Uani d 1 . .
    H H7A 0.584817 0.478246 0.565940 0.028 Uiso calc 1 . .
    H H7B 0.488659 0.547292 0.584154 0.028 Uiso calc 1 . .
    C C8 0.56492(19) 0.5045(4) 0.67034(17) 0.0257(6) Uani d 1 . .
    C C9 0.5480(4) 0.2701(5) 0.7460(3) 0.0477(12) Uani d 1 . .
    H H9A 0.542499 0.359900 0.780977 0.057 Uiso calc 1 . .
    H H9B 0.499792 0.188164 0.753279 0.057 Uiso calc 1 . .
    C C10 0.6321(4) 0.1852(10) 0.7541(3) 0.090(2) Uani d 1 . .
    H H10A 0.631397 0.078866 0.728508 0.135 Uiso calc 1 . .
    H H10B 0.642387 0.161832 0.802687 0.135 Uiso calc 1 . .
    H H10C 0.679172 0.257702 0.736533 0.135 Uiso calc 1 . .
    S S2 0.50616(5) 1.26544(10) 0.41974(6) 0.0261(3) Uani d 1 . .
    O O3 0.64984(17) 0.5962(3) 0.28477(13) 0.0395(6) Uani d 1 . .
    O O4 0.71465(15) 0.3538(3) 0.31719(13) 0.0300(5) Uani d 1 . .
    N N5 0.43223(15) 0.9564(3) 0.42506(13) 0.0213(5) Uani d 1 . .
    N N6 0.51119(14) 0.6911(3) 0.42374(14) 0.0201(5) Uani d 1 . .
    N N7 0.66818(17) 0.7297(3) 0.4129(2) 0.0209(6) Uani d 1 . .
    N N8 0.72609(15) 0.8609(3) 0.40662(15) 0.0232(5) Uani d 1 . .
    C C11 0.58765(16) 0.9615(3) 0.41661(15) 0.0184(5) Uani d 1 . .
    C C12 0.50642(16) 1.0450(3) 0.42037(17) 0.0200(5) Uani d 1 . .
    C C13 0.4397(2) 0.7853(4) 0.4266(2) 0.0213(6) Uani d 1 . .
    H H13 0.385810 0.725187 0.430208 0.026 Uiso calc 1 . .
    C C14 0.58423(18) 0.7855(4) 0.41793(19) 0.0174(5) Uani d 1 . .
    C C15 0.67840(18) 1.0008(4) 0.40924(17) 0.0220(6) Uani d 1 . .
    H H15 0.701635 1.111868 0.406561 0.026 Uiso calc 1 . .
    C C16 0.3923(2) 1.3134(4) 0.4044(2) 0.0348(8) Uani d 1 . .
    H H16A 0.384436 1.436092 0.402463 0.052 Uiso calc 1 . .
    H H16B 0.356391 1.267027 0.441574 0.052 Uiso calc 1 . .
    H H16C 0.373922 1.263363 0.360831 0.052 Uiso calc 1 . .
    C C17 0.69686(19) 0.5584(4) 0.40147(17) 0.0207(6) Uani d 1 . .
    H H17A 0.663159 0.481025 0.431350 0.025 Uiso calc 1 . .
    H H17B 0.759899 0.548007 0.413395 0.025 Uiso calc 1 . .
    C C18 0.68337(19) 0.5091(4) 0.32713(16) 0.0248(6) Uani d 1 . .
    C C19 0.7050(3) 0.2858(6) 0.2481(2) 0.0409(9) Uani d 1 . .
    H H19A 0.756035 0.213066 0.237211 0.049 Uiso calc 1 . .
    H H19B 0.703735 0.379662 0.214671 0.049 Uiso calc 1 . .
    C C20 0.6230(3) 0.1864(8) 0.2426(2) 0.0609(13) Uani d 1 . .
    H H20A 0.572189 0.262094 0.246137 0.091 Uiso calc 1 . .
    H H20B 0.620777 0.103087 0.279587 0.091 Uiso calc 1 . .
    H H20C 0.621549 0.128263 0.198327 0.091 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 . 1.740(3) ?
    S1 C6 . 1.804(3) ?
    O1 C8 . 1.196(4) ?
    O2 C8 . 1.332(4) ?
    O2 C9 . 1.463(5) ?
    N1 C2 . 1.332(3) ?
    N1 C3 . 1.356(4) ?
    N2 C3 . 1.325(4) ?
    N2 C4 . 1.344(4) ?
    N3 C4 . 1.353(4) ?
    N3 N4 . 1.370(3) ?
    N3 C7 . 1.440(4) ?
    N4 C5 . 1.319(4) ?
    C1 C4 . 1.403(4) ?
    C1 C2 . 1.406(3) ?
    C1 C5 . 1.420(4) ?
    C3 H3 . 0.9500 ?
    C5 H5 . 0.9500 ?
    C6 H6A . 0.9800 ?
    C6 H6B . 0.9800 ?
    C6 H6C . 0.9800 ?
    C7 C8 . 1.523(4) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C9 C10 . 1.453(6) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    S2 C12 . 1.747(3) ?
    S2 C16 . 1.798(3) ?
    O3 C18 . 1.192(4) ?
    O4 C18 . 1.334(3) ?
    O4 C19 . 1.461(5) ?
    N5 C12 . 1.332(3) ?
    N5 C13 . 1.361(4) ?
    N6 C13 . 1.320(4) ?
    N6 C14 . 1.344(4) ?
    N7 C14 . 1.355(4) ?
    N7 N8 . 1.368(3) ?
    N7 C17 . 1.443(4) ?
    N8 C15 . 1.326(4) ?
    C11 C14 . 1.396(4) ?
    C11 C12 . 1.403(3) ?
    C11 C15 . 1.422(4) ?
    C13 H13 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 C18 . 1.518(4) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C19 C20 . 1.480(6) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
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
    C2 S1 C6 . . 101.68(14) ?
    C8 O2 C9 . . 117.3(3) ?
    C2 N1 C3 . . 117.5(2) ?
    C3 N2 C4 . . 111.9(3) ?
    C4 N3 N4 . . 111.2(2) ?
    C4 N3 C7 . . 127.2(3) ?
    N4 N3 C7 . . 120.5(2) ?
    C5 N4 N3 . . 106.4(2) ?
    C4 C1 C2 . . 116.0(2) ?
    C4 C1 C5 . . 104.5(2) ?
    C2 C1 C5 . . 139.6(2) ?
    N1 C2 C1 . . 119.9(2) ?
    N1 C2 S1 . . 121.86(19) ?
    C1 C2 S1 . . 118.28(19) ?
    N2 C3 N1 . . 129.0(3) ?
    N2 C3 H3 . . 115.5 ?
    N1 C3 H3 . . 115.5 ?
    N2 C4 N3 . . 127.3(3) ?
    N2 C4 C1 . . 125.7(3) ?
    N3 C4 C1 . . 106.9(2) ?
    N4 C5 C1 . . 111.0(2) ?
    N4 C5 H5 . . 124.5 ?
    C1 C5 H5 . . 124.5 ?
    S1 C6 H6A . . 109.5 ?
    S1 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    S1 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    N3 C7 C8 . . 111.6(3) ?
    N3 C7 H7A . . 109.3 ?
    C8 C7 H7A . . 109.3 ?
    N3 C7 H7B . . 109.3 ?
    C8 C7 H7B . . 109.3 ?
    H7A C7 H7B . . 108.0 ?
    O1 C8 O2 . . 126.3(3) ?
    O1 C8 C7 . . 124.8(3) ?
    O2 C8 C7 . . 108.9(3) ?
    C10 C9 O2 . . 111.0(4) ?
    C10 C9 H9A . . 109.4 ?
    O2 C9 H9A . . 109.4 ?
    C10 C9 H9B . . 109.4 ?
    O2 C9 H9B . . 109.4 ?
    H9A C9 H9B . . 108.0 ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C12 S2 C16 . . 102.41(14) ?
    C18 O4 C19 . . 116.0(3) ?
    C12 N5 C13 . . 117.1(2) ?
    C13 N6 C14 . . 111.7(3) ?
    C14 N7 N8 . . 111.4(2) ?
    C14 N7 C17 . . 127.1(3) ?
    N8 N7 C17 . . 120.4(2) ?
    C15 N8 N7 . . 106.3(2) ?
    C14 C11 C12 . . 115.9(2) ?
    C14 C11 C15 . . 104.9(2) ?
    C12 C11 C15 . . 139.2(2) ?
    N5 C12 C11 . . 120.1(2) ?
    N5 C12 S2 . . 121.70(19) ?
    C11 C12 S2 . . 118.22(19) ?
    N6 C13 N5 . . 129.1(3) ?
    N6 C13 H13 . . 115.5 ?
    N5 C13 H13 . . 115.5 ?
    N6 C14 N7 . . 127.1(3) ?
    N6 C14 C11 . . 126.0(3) ?
    N7 C14 C11 . . 106.8(2) ?
    N8 C15 C11 . . 110.6(2) ?
    N8 C15 H15 . . 124.7 ?
    C11 C15 H15 . . 124.7 ?
    S2 C16 H16A . . 109.5 ?
    S2 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    S2 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    N7 C17 C18 . . 110.5(3) ?
    N7 C17 H17A . . 109.6 ?
    C18 C17 H17A . . 109.6 ?
    N7 C17 H17B . . 109.6 ?
    C18 C17 H17B . . 109.6 ?
    H17A C17 H17B . . 108.1 ?
    O3 C18 O4 . . 125.8(3) ?
    O3 C18 C17 . . 125.0(3) ?
    O4 C18 C17 . . 109.2(3) ?
    O4 C19 C20 . . 110.4(3) ?
    O4 C19 H19A . . 109.6 ?
    C20 C19 H19A . . 109.6 ?
    O4 C19 H19B . . 109.6 ?
    C20 C19 H19B . . 109.6 ?
    H19A C19 H19B . . 108.1 ?
    C19 C20 H20A . . 109.5 ?
    C19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
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
    C4 N3 N4 C5 . . . . 1.9(4) ?
    C7 N3 N4 C5 . . . . 170.6(3) ?
    C3 N1 C2 C1 . . . . 0.9(5) ?
    C3 N1 C2 S1 . . . . -178.6(3) ?
    C4 C1 C2 N1 . . . . -0.4(4) ?
    C5 C1 C2 N1 . . . . 177.9(3) ?
    C4 C1 C2 S1 . . . . 179.2(3) ?
    C5 C1 C2 S1 . . . . -2.6(6) ?
    C6 S1 C2 N1 . . . . -12.7(3) ?
    C6 S1 C2 C1 . . . . 167.8(3) ?
    C4 N2 C3 N1 . . . . 0.9(6) ?
    C2 N1 C3 N2 . . . . -1.3(6) ?
    C3 N2 C4 N3 . . . . -179.6(4) ?
    C3 N2 C4 C1 . . . . -0.2(5) ?
    N4 N3 C4 N2 . . . . 177.9(3) ?
    C7 N3 C4 N2 . . . . 10.2(7) ?
    N4 N3 C4 C1 . . . . -1.6(5) ?
    C7 N3 C4 C1 . . . . -169.3(3) ?
    C2 C1 C4 N2 . . . . 0.0(5) ?
    C5 C1 C4 N2 . . . . -178.8(3) ?
    C2 C1 C4 N3 . . . . 179.5(3) ?
    C5 C1 C4 N3 . . . . 0.7(4) ?
    N3 N4 C5 C1 . . . . -1.5(4) ?
    C4 C1 C5 N4 . . . . 0.5(4) ?
    C2 C1 C5 N4 . . . . -177.9(4) ?
    C4 N3 C7 C8 . . . . 74.9(5) ?
    N4 N3 C7 C8 . . . . -91.8(4) ?
    C9 O2 C8 O1 . . . . -0.5(5) ?
    C9 O2 C8 C7 . . . . 179.7(3) ?
    N3 C7 C8 O1 . . . . 2.7(4) ?
    N3 C7 C8 O2 . . . . -177.5(2) ?
    C8 O2 C9 C10 . . . . -92.6(5) ?
    C14 N7 N8 C15 . . . . 1.4(5) ?
    C17 N7 N8 C15 . . . . 170.3(3) ?
    C13 N5 C12 C11 . . . . 0.6(5) ?
    C13 N5 C12 S2 . . . . -178.6(3) ?
    C14 C11 C12 N5 . . . . 0.2(5) ?
    C15 C11 C12 N5 . . . . 177.4(3) ?
    C14 C11 C12 S2 . . . . 179.4(3) ?
    C15 C11 C12 S2 . . . . -3.4(6) ?
    C16 S2 C12 N5 . . . . -14.1(3) ?
    C16 S2 C12 C11 . . . . 166.6(3) ?
    C14 N6 C13 N5 . . . . -0.7(6) ?
    C12 N5 C13 N6 . . . . -0.3(5) ?
    C13 N6 C14 N7 . . . . -179.2(4) ?
    C13 N6 C14 C11 . . . . 1.6(5) ?
    N8 N7 C14 N6 . . . . 179.0(3) ?
    C17 N7 C14 N6 . . . . 11.1(7) ?
    N8 N7 C14 C11 . . . . -1.6(5) ?
    C17 N7 C14 C11 . . . . -169.5(3) ?
    C12 C11 C14 N6 . . . . -1.4(5) ?
    C15 C11 C14 N6 . . . . -179.5(3) ?
    C12 C11 C14 N7 . . . . 179.2(3) ?
    C15 C11 C14 N7 . . . . 1.1(4) ?
    N7 N8 C15 C11 . . . . -0.7(4) ?
    C14 C11 C15 N8 . . . . -0.3(4) ?
    C12 C11 C15 N8 . . . . -177.7(4) ?
    C14 N7 C17 C18 . . . . 75.6(5) ?
    N8 N7 C17 C18 . . . . -91.4(4) ?
    C19 O4 C18 O3 . . . . -1.0(5) ?
    C19 O4 C18 C17 . . . . 178.8(3) ?
    N7 C17 C18 O3 . . . . -3.4(4) ?
    N7 C17 C18 O4 . . . . 176.7(2) ?
    C18 O4 C19 C20 . . . . -93.3(4) ?
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
    _geom_hbond_publ_flag
    C3 H3 N4 3_565 0.95 2.55 3.450(4) 158 yes
    C5 H5 O2 1_565 0.95 2.57 3.314(4) 136 yes
    C13 H13 N8 3_465 0.95 2.56 3.470(4) 159 yes
    C19 H19A O1 4_644 0.99 2.52 3.490(5) 166 yes
_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     0.900
_shelx_estimated_absorpt_T_max     0.957
data_global
_journal_date_recd_electronic     2022-10-10
_journal_date_accepted     2022-11-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2022
_journal_volume     78
_journal_issue     12
_journal_page_first     1265
_journal_page_last     1270
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989022011112
_journal_coeditor_code     WM5664
_publ_contact_author
;
'Sebbar, Nada Kheira'
Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team,
Faculty of Sciences,
Ibn Zohr University,
Agadir,
Morocco
Laboratory of Heterocyclic Organic Chemistry, Medicines Science Research Center
Pharmacochemistry Competence Center, Mohammed V University in Rabat,
Faculty of Sciences,
Morocco
;
_publ_contact_author_email     n.sebbar@uiz.ac.ma
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Crystal structure, Hirshfeld surface analysis and DFT calculations of ethyl
2-[4-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]acetate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Elmachkouri, Younesse Ait' .
;
Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team,
Faculty of Sciences,
Ibn Zohr University,
Agadir,
Morocco
;
    'Irrou, Ezaddine' .
;
Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team,
Faculty of Sciences, Ibn Zohr University, Agadir,
Morocco
;
    'Dalbouha, Samira' .
;
Laboratory of Organic Chemistry and Physical Chemistry, Research Team: Molecular
Modeling, Materials and Environment, Department of Chemistry, Faculty of
Sciences, University Ibn Zohr in Agadir, BP 8106 Agadir,
Morocco
Laboratory of Spectroscopy, Molecular Modeling, Materials, Nanomaterials, Water
and Environment, CERNE2D, Faculty of Sciences, Mohammed V University in Rabat,
Av. Ibn Battouta, BP 1014, Rabat,
Morocco
;
    'Ouachtak, Hassan' .
;
Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team,
Faculty of Sciences, Ibn Zohr University, Agadir,
Morocco
;
    'Mague, Joel T.' .
;
Department of Chemistry
Tulane University
New Orleans, LA 70118
USA
;
    'Hökelek, Tuncer' .
;
Department of Physics
Hacettepe University
06800 Beytepe
Ankara
Turkey
;
    'El Ghayati, Lhoussaine' .
;
Laboratory of Heterocyclic Organic Chemistry, Medicines Science Research Center
Pharmacochemistry Competence Center, Mohammed V University in Rabat,
Faculty of Sciences,
Morocco
;
    'Sebbar, Nada Kheira' .
;
Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team,
Faculty of Sciences,
Ibn Zohr University,
Agadir,
Morocco
Laboratory of Heterocyclic Organic Chemistry, Medicines Science Research Center
Pharmacochemistry Competence Center, Mohammed V University in Rabat,
Faculty of Sciences,
Morocco
;
    'Taha, Mohamed Labd' .
;
Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team,
Faculty of Sciences, Ibn Zohr University, Agadir,
Morocco
;
_publ_section_synopsis
;
The asymmetric unit of the title compound contains two molecules differing
slightly in the rotational orientations of the methyl groups.
;
