##############################################################################
#                                                                            #
# 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-97
_journal_date_recd_electronic     2014-12-24
_journal_date_accepted     2014-12-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      2
_journal_page_first     o95
_journal_page_last     o96
_journal_paper_category     HO
_journal_paper_doi     10.1107/S205698901402828X
_journal_coeditor_code     TK5354
_publ_contact_author_name     'El Mokhtar Essassi'
_publ_contact_author_address
;
Laboratoire de Chimie Organique Hétérocyclique URAC 21,
Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014,
Faculté des Sciences, Université Mohammed V-Agdal, Rabat, Morocco
;
_publ_contact_author_email     'em_essassi@yahoo.fr'
_publ_contact_author_fax     '212 537 77 54 40'
_publ_contact_author_phone     '212 537 77 54 40'
_publ_section_title
;
The crystal structure of
1,5-dibenzyl-1H-pyrazolo[3,4-d]pyrimidine-4(5H)-thione
;
loop_
    _publ_author_name
    _publ_author_address
    'El Fal, Mohammed'
;
Laboratoire de Chimie Organique Hétérocyclique URAC 21,
Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014,
Faculté des Sciences, Université Mohammed V, Rabat, Morocco
;
    'Ramli, Youssef'
;\
Medicinal Chemistry Laboratory, Faculty of Medicine and Pharmacy,
Mohammed V University, Rabat, Morocco
;
    'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique Hétérocyclique URAC 21,
Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014,
Faculté des Sciences, Université Mohammed V, Rabat, Morocco
;
    'Saadi, Mohamed'
;
Laboratoire de Chimie du Solide Appliquée,
Faculté des Sciences, Université Mohammed V
Avenue Ibn Battouta, BP 1014, Rabat, Morocco
;
    'El Ammari, Lahcen'
;
Laboratoire de Chimie du Solide Appliquée,
Faculté des Sciences, Université Mohammed V
Avenue Ibn Battouta, BP 1014, Rabat, Morocco
;
_database_code_depnum_ccdc_archive     'CCDC 1041681'
_chemical_name_systematic
;
1,5-Dibenzyl-1H-pyrazolo[3,4-d]pyrimidine-4(5H)-thione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H16 N4 S'
_chemical_formula_sum     'C19 H16 N4 S'
_chemical_formula_iupac     'C19 H16 N4 S'
_chemical_formula_weight     332.42
_chemical_melting_point     563
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     4.4953(12)
_cell_length_b     29.140(8)
_cell_length_c     6.3889(16)
_cell_angle_alpha     90.00
_cell_angle_beta     97.860(9)
_cell_angle_gamma     90.00
_cell_volume     829.0(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3582
_cell_measurement_theta_min     2.80
_cell_measurement_theta_max     27.09
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.29
_exptl_crystal_density_diffrn     1.332
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     348
_exptl_absorpt_coefficient_mu     0.202
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_absorpt_correction_T_min     0.5888
_exptl_absorpt_correction_T_max     0.7455
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker X8 APEX'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     9214
_diffrn_reflns_av_R_equivalents     0.0403
_diffrn_reflns_av_sigmaI/netI     0.0609
_diffrn_reflns_theta_min     2.80
_diffrn_reflns_theta_max     27.09
_diffrn_reflns_theta_full     27.09
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -37
_diffrn_reflns_limit_k_max     37
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_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 >
σ(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.
;
_reflns_number_total     3582
_reflns_number_gt     2406
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0745
_refine_ls_R_factor_gt     0.0407
_refine_ls_wR_factor_gt     0.0742
_refine_ls_wR_factor_ref     0.0840
_refine_ls_goodness_of_fit_ref     0.974
_refine_ls_restrained_S_all     0.974
_refine_ls_number_reflns     3582
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0318P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.136
_refine_diff_density_min     -0.119
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
;
Flack & Bernardinelli (2000), 1730 Friedel pairs
;
_refine_ls_abs_structure_Flack     -0.11(7)
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'
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2009)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009) and 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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.5941(5) 0.48633(8) 0.9980(3) 0.0412(6) Uani d . 1 1 . .
    C C2 0.4720(5) 0.44502(8) 1.0570(3) 0.0411(6) Uani d . 1 1 . .
    C C3 0.5145(7) 0.41623(9) 1.2377(4) 0.0586(7) Uani d . 1 1 . .
    H H3 0.6506 0.4222 1.3578 0.070 Uiso calc R 1 1 . .
    C C4 0.2489(6) 0.42310(9) 0.9208(4) 0.0457(6) Uani d . 1 1 . .
    C C5 0.2551(6) 0.47501(9) 0.6716(4) 0.0488(6) Uani d . 1 1 . .
    H H5 0.1885 0.4864 0.5375 0.059 Uiso calc R 1 1 . .
    C C6 0.5892(5) 0.54088(9) 0.6906(4) 0.0477(6) Uani d . 1 1 . .
    H H6A 0.6197 0.5330 0.5476 0.057 Uiso calc R 1 1 . .
    H H6B 0.7826 0.5495 0.7672 0.057 Uiso calc R 1 1 . .
    C C7 0.3812(5) 0.58142(8) 0.6832(4) 0.0425(6) Uani d . 1 1 . .
    C C8 0.3274(6) 0.60388(9) 0.8650(4) 0.0545(7) Uani d . 1 1 . .
    H H8 0.4188 0.5935 0.9959 0.065 Uiso calc R 1 1 . .
    C C9 0.1404(7) 0.64137(10) 0.8546(5) 0.0651(8) Uani d . 1 1 . .
    H H9 0.1070 0.6563 0.9780 0.078 Uiso calc R 1 1 . .
    C C10 0.0034(7) 0.65686(11) 0.6635(5) 0.0700(8) Uani d . 1 1 . .
    H H10 -0.1242 0.6821 0.6569 0.084 Uiso calc R 1 1 . .
    C C11 0.0546(7) 0.63514(11) 0.4817(5) 0.0701(9) Uani d . 1 1 . .
    H H11 -0.0375 0.6458 0.3515 0.084 Uiso calc R 1 1 . .
    C C12 0.2421(6) 0.59761(9) 0.4912(4) 0.0551(7) Uani d . 1 1 . .
    H H12 0.2754 0.5830 0.3671 0.066 Uiso calc R 1 1 . .
    C C13 -0.0331(7) 0.34855(9) 0.9311(5) 0.0701(9) Uani d . 1 1 . .
    H H13A -0.1746 0.3609 0.8167 0.084 Uiso calc R 1 1 . .
    H H13B -0.1461 0.3374 1.0396 0.084 Uiso calc R 1 1 . .
    C C14 0.1353(6) 0.30957(9) 0.8500(5) 0.0538(7) Uani d . 1 1 . .
    C C15 0.1948(7) 0.27009(11) 0.9677(5) 0.0701(8) Uani d . 1 1 . .
    H H15 0.1235 0.2673 1.0970 0.084 Uiso calc R 1 1 . .
    C C16 0.3567(8) 0.23521(11) 0.8969(8) 0.0926(12) Uani d . 1 1 . .
    H H16 0.3946 0.2088 0.9778 0.111 Uiso calc R 1 1 . .
    C C17 0.4635(8) 0.23889(15) 0.7078(9) 0.0961(13) Uani d . 1 1 . .
    H H17 0.5758 0.2152 0.6605 0.115 Uiso calc R 1 1 . .
    C C18 0.4049(8) 0.27764(16) 0.5874(6) 0.0898(11) Uani d . 1 1 . .
    H H18 0.4766 0.2801 0.4581 0.108 Uiso calc R 1 1 . .
    C C19 0.2406(7) 0.31279(11) 0.6575(5) 0.0705(8) Uani d . 1 1 . .
    H H19 0.2000 0.3389 0.5748 0.085 Uiso calc R 1 1 . .
    N N1 0.3381(6) 0.38019(8) 1.2147(4) 0.0633(6) Uani d . 1 1 . .
    N N2 0.1709(5) 0.38498(7) 1.0188(4) 0.0575(6) Uani d . 1 1 . .
    N N3 0.1303(5) 0.43742(7) 0.7249(3) 0.0529(5) Uani d . 1 1 . .
    N N4 0.4758(4) 0.49978(6) 0.7928(3) 0.0422(5) Uani d . 1 1 . .
    S S1 0.85051(15) 0.51743(3) 1.14918(10) 0.0571(2) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    C1 C2 . 1.396(3) ?
    C1 N4 . 1.402(3) ?
    C1 S1 . 1.667(2) ?
    C2 C4 . 1.390(3) ?
    C2 C3 . 1.419(3) ?
    C3 N1 . 1.312(3) ?
    C3 H3 . 0.9300 ?
    C4 N2 . 1.345(3) ?
    C4 N3 . 1.357(3) ?
    C5 N3 . 1.297(3) ?
    C5 N4 . 1.376(3) ?
    C5 H5 . 0.9300 ?
    C6 N4 . 1.487(3) ?
    C6 C7 . 1.503(3) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C12 . 1.381(3) ?
    C7 C8 . 1.383(3) ?
    C8 C9 . 1.374(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.367(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.370(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.377(4) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
    C13 N2 . 1.463(3) ?
    C13 C14 . 1.496(4) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 C19 . 1.380(4) ?
    C14 C15 . 1.380(4) ?
    C15 C16 . 1.363(5) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.364(5) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.371(5) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.373(5) ?
    C18 H18 . 0.9300 ?
    C19 H19 . 0.9300 ?
    N1 N2 . 1.376(3) ?
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 C1 N4 . . 112.4(2) ?
    C2 C1 S1 . . 125.35(18) ?
    N4 C1 S1 . . 122.28(18) ?
    C4 C2 C1 . . 120.3(2) ?
    C4 C2 C3 . . 104.1(2) ?
    C1 C2 C3 . . 135.7(2) ?
    N1 C3 C2 . . 111.7(3) ?
    N1 C3 H3 . . 124.1 ?
    C2 C3 H3 . . 124.1 ?
    N2 C4 N3 . . 126.1(2) ?
    N2 C4 C2 . . 107.4(2) ?
    N3 C4 C2 . . 126.5(2) ?
    N3 C5 N4 . . 126.9(2) ?
    N3 C5 H5 . . 116.6 ?
    N4 C5 H5 . . 116.6 ?
    N4 C6 C7 . . 113.42(17) ?
    N4 C6 H6A . . 108.9 ?
    C7 C6 H6A . . 108.9 ?
    N4 C6 H6B . . 108.9 ?
    C7 C6 H6B . . 108.9 ?
    H6A C6 H6B . . 107.7 ?
    C12 C7 C8 . . 118.3(2) ?
    C12 C7 C6 . . 120.0(2) ?
    C8 C7 C6 . . 121.7(2) ?
    C9 C8 C7 . . 120.7(3) ?
    C9 C8 H8 . . 119.6 ?
    C7 C8 H8 . . 119.6 ?
    C10 C9 C8 . . 120.3(3) ?
    C10 C9 H9 . . 119.9 ?
    C8 C9 H9 . . 119.9 ?
    C9 C10 C11 . . 119.8(3) ?
    C9 C10 H10 . . 120.1 ?
    C11 C10 H10 . . 120.1 ?
    C10 C11 C12 . . 120.1(3) ?
    C10 C11 H11 . . 119.9 ?
    C12 C11 H11 . . 119.9 ?
    C11 C12 C7 . . 120.7(3) ?
    C11 C12 H12 . . 119.6 ?
    C7 C12 H12 . . 119.6 ?
    N2 C13 C14 . . 111.3(2) ?
    N2 C13 H13A . . 109.4 ?
    C14 C13 H13A . . 109.4 ?
    N2 C13 H13B . . 109.4 ?
    C14 C13 H13B . . 109.4 ?
    H13A C13 H13B . . 108.0 ?
    C19 C14 C15 . . 118.5(3) ?
    C19 C14 C13 . . 120.5(3) ?
    C15 C14 C13 . . 120.9(3) ?
    C16 C15 C14 . . 120.9(3) ?
    C16 C15 H15 . . 119.6 ?
    C14 C15 H15 . . 119.6 ?
    C15 C16 C17 . . 120.3(4) ?
    C15 C16 H16 . . 119.9 ?
    C17 C16 H16 . . 119.9 ?
    C16 C17 C18 . . 119.8(4) ?
    C16 C17 H17 . . 120.1 ?
    C18 C17 H17 . . 120.1 ?
    C17 C18 C19 . . 120.1(4) ?
    C17 C18 H18 . . 119.9 ?
    C19 C18 H18 . . 119.9 ?
    C18 C19 C14 . . 120.3(3) ?
    C18 C19 H19 . . 119.8 ?
    C14 C19 H19 . . 119.8 ?
    C3 N1 N2 . . 105.5(2) ?
    C4 N2 N1 . . 111.2(2) ?
    C4 N2 C13 . . 127.6(2) ?
    N1 N2 C13 . . 120.7(2) ?
    C5 N3 C4 . . 111.8(2) ?
    C5 N4 C1 . . 122.1(2) ?
    C5 N4 C6 . . 116.1(2) ?
    C1 N4 C6 . . 121.78(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
    C5 H5 S1 1_454 0.93 2.87 3.784(3) 167
