##############################################################################
#                                                                            #
# 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     2014-07-27
_journal_date_accepted     2014-08-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      9
_journal_page_first     o1038
_journal_page_last     o1038
_journal_paper_category     HO
_journal_paper_doi     10.1107/S1600536814018042
_journal_coeditor_code     IS5372
_publ_contact_author_name     'Mohammed El Fal'
_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     'elfal_mohammed@yahoo.fr'
_publ_contact_author_fax     '212 537 77 54 40'
_publ_contact_author_phone     '212 537 77 54 40'
_publ_section_title
;
Crystal structure of 4-allylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine
;
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-Agdal, Rabat, Morocco
;
    'Ramli, Youssef'
;\
Laboratoire National de Contrôle des Médicaments, D M P, Ministère \
de la Santé, Madinat Al Irnane, BP 6206, 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-Agdal, Rabat, Morocco
;
    'Saadi, Mohamed'
;
Laboratoire de Chimie du Solide Appliquée,
Faculté des Sciences, Université Mohammed V-Agdal
Avenue Ibn Battouta, BP 1014, Rabat, Morocco
;
    'El Ammari, Lahcen'
;
Laboratoire de Chimie du Solide Appliquée,
Faculté des Sciences, Université Mohammed V-Agdal
Avenue Ibn Battouta, BP 1014, Rabat, Morocco
;
_database_code_depnum_ccdc_archive     'CCDC 1018090'
_chemical_name_systematic
;
4-Allylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H8 N4 S'
_chemical_formula_sum     'C8 H8 N4 S'
_chemical_formula_iupac     'C8 H8 N4 S'
_chemical_formula_weight     192.24
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c n'
_symmetry_space_group_name_Hall     '-p 2n 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    '-x, y, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    'x, -y, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     18.537(6)
_cell_length_b     5.1997(17)
_cell_length_c     19.059(7)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1837.0(11)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2189
_cell_measurement_theta_min     2.40
_cell_measurement_theta_max     27.87
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.39
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.29
_exptl_crystal_density_diffrn     1.390
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     800
_exptl_absorpt_coefficient_mu     0.308
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.6414
_exptl_absorpt_correction_T_max     0.7464
_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     20928
_diffrn_reflns_av_R_equivalents     0.0675
_diffrn_reflns_av_sigmaI/netI     0.0406
_diffrn_reflns_theta_min     2.40
_diffrn_reflns_theta_max     27.87
_diffrn_reflns_theta_full     27.87
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_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     2189
_reflns_number_gt     1093
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1212
_refine_ls_R_factor_gt     0.0560
_refine_ls_wR_factor_gt     0.1458
_refine_ls_wR_factor_ref     0.1805
_refine_ls_goodness_of_fit_ref     1.019
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     2189
_refine_ls_number_parameters     128
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0784P)²+0.5307P] 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     0.278
_refine_diff_density_min     -0.314
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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
    S S1 0.66313(5) 0.15662(17) 0.85306(5) 0.0890(4) Uani d D 1 1 . .
    N N1 0.53488(15) 0.3882(5) 0.85359(15) 0.0819(8) Uani d . 1 1 . .
    N N2 0.49883(12) 0.7352(5) 0.92947(15) 0.0759(8) Uani d . 1 1 . .
    N N3 0.58954(12) 0.8446(5) 1.01342(15) 0.0760(8) Uani d . 1 1 . .
    H H3N 0.5667 0.9680 1.0337 0.091 Uiso calc R 1 1 A .
    N N4 0.65714(13) 0.7630(6) 1.03189(17) 0.0867(9) Uani d . 1 1 A .
    C C1 0.48931(17) 0.5665(7) 0.8781(2) 0.0887(10) Uani d . 1 1 A .
    H H1 0.4446 0.5730 0.8561 0.106 Uiso calc R 1 1 . .
    C C2 0.56370(15) 0.7078(5) 0.96002(17) 0.0639(8) Uani d . 1 1 A .
    C C3 0.67252(15) 0.5738(7) 0.98923(19) 0.0787(9) Uani d . 1 1 . .
    H H3 0.7154 0.4812 0.9902 0.094 Uiso calc R 1 1 A .
    C C4 0.61592(14) 0.5282(5) 0.94180(17) 0.0654(8) Uani d . 1 1 A .
    C C5 0.59890(15) 0.3712(5) 0.88464(18) 0.0710(9) Uani d . 1 1 A .
    C C6A 0.6154(5) -0.011(2) 0.7877(4) 0.1188(19) Uani d PD 0.512(6) 1 A 1
    H H6A1 0.6140 -0.1915 0.7999 0.143 Uiso calc PR 0.512(6) 1 A 1
    H H6A2 0.5660 0.0515 0.7869 0.143 Uiso calc PR 0.512(6) 1 A 1
    C C7A 0.6458(4) 0.0154(16) 0.7178(5) 0.0919(15) Uani d PD 0.512(6) 1 A 1
    H H7A 0.6385 0.1722 0.6954 0.110 Uiso calc PR 0.512(6) 1 A 1
    C C8A 0.682(3) -0.155(6) 0.6835(9) 0.121(3) Uani d PD 0.512(6) 1 A 1
    H H8A1 0.6906 -0.3151 0.7035 0.145 Uiso calc PR 0.512(6) 1 A 1
    H H8A2 0.6989 -0.1179 0.6388 0.145 Uiso calc PR 0.512(6) 1 A 1
    C C6B 0.6188(5) 0.019(2) 0.7806(4) 0.1188(19) Uani d PD 0.488(6) 1 A 2
    H H6B1 0.5749 -0.0628 0.7973 0.143 Uiso calc PR 0.488(6) 1 A 2
    H H6B2 0.6046 0.1563 0.7491 0.143 Uiso calc PR 0.488(6) 1 A 2
    C C7B 0.6598(4) -0.1692(16) 0.7409(5) 0.0919(15) Uani d PD 0.488(6) 1 A 2
    H H7B 0.6757 -0.3111 0.7663 0.110 Uiso calc PR 0.488(6) 1 A 2
    C C8B 0.677(3) -0.168(7) 0.6756(10) 0.121(3) Uani d PD 0.488(6) 1 A 2
    H H8B1 0.6634 -0.0313 0.6470 0.145 Uiso calc PR 0.488(6) 1 A 2
    H H8B2 0.7042 -0.3024 0.6569 0.145 Uiso calc PR 0.488(6) 1 A 2
_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
    S1 C5 . 1.739(3) ?
    S1 C6A . 1.759(2) ?
    S1 C6B . 1.759(2) ?
    N1 C5 . 1.329(4) ?
    N1 C1 . 1.339(4) ?
    N2 C1 . 1.326(4) ?
    N2 C2 . 1.344(4) ?
    N3 C2 . 1.331(4) ?
    N3 N4 . 1.369(3) ?
    N3 H3N . 0.8600 ?
    N4 C3 . 1.308(4) ?
    C1 H1 . 0.9300 ?
    C2 C4 . 1.389(4) ?
    C3 C4 . 1.405(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.397(4) ?
    C6A C7A . 1.452(2) ?
    C6A H6A1 . 0.9700 ?
    C6A H6A2 . 0.9700 ?
    C7A C8A . 1.287(2) ?
    C7A H7A . 0.9300 ?
    C8A H8A1 . 0.9300 ?
    C8A H8A2 . 0.9300 ?
    C6B C7B . 1.453(2) ?
    C6B H6B1 . 0.9700 ?
    C6B H6B2 . 0.9700 ?
    C7B C8B . 1.287(2) ?
    C7B H7B . 0.9300 ?
    C8B H8B1 . 0.9300 ?
    C8B H8B2 . 0.9300 ?
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
    C5 S1 C6A . . 102.6(4) ?
    C5 S1 C6B . . 102.3(4) ?
    C5 N1 C1 . . 117.0(3) ?
    C1 N2 C2 . . 111.6(3) ?
    C2 N3 N4 . . 111.1(3) ?
    C2 N3 H3N . . 124.4 ?
    N4 N3 H3N . . 124.4 ?
    C3 N4 N3 . . 105.8(3) ?
    N2 C1 N1 . . 129.2(3) ?
    N2 C1 H1 . . 115.4 ?
    N1 C1 H1 . . 115.4 ?
    N3 C2 N2 . . 126.7(3) ?
    N3 C2 C4 . . 107.4(3) ?
    N2 C2 C4 . . 125.9(3) ?
    N4 C3 C4 . . 111.4(3) ?
    N4 C3 H3 . . 124.3 ?
    C4 C3 H3 . . 124.3 ?
    C2 C4 C5 . . 115.5(3) ?
    C2 C4 C3 . . 104.2(3) ?
    C5 C4 C3 . . 140.2(3) ?
    N1 C5 C4 . . 120.7(3) ?
    N1 C5 S1 . . 120.0(3) ?
    C4 C5 S1 . . 119.3(2) ?
    C7A C6A S1 . . 114.1(6) ?
    C7A C6A H6A1 . . 108.7 ?
    S1 C6A H6A1 . . 108.7 ?
    C7A C6A H6A2 . . 108.7 ?
    S1 C6A H6A2 . . 108.7 ?
    H6A1 C6A H6A2 . . 107.6 ?
    C8A C7A C6A . . 127.1(11) ?
    C8A C7A H7A . . 116.5 ?
    C6A C7A H7A . . 116.5 ?
    C7A C8A H8A1 . . 120.0 ?
    C7A C8A H8A2 . . 120.0 ?
    H8A1 C8A H8A2 . . 120.0 ?
    C7B C6B S1 . . 116.0(7) ?
    C7B C6B H6B1 . . 108.3 ?
    S1 C6B H6B1 . . 108.3 ?
    C7B C6B H6B2 . . 108.3 ?
    S1 C6B H6B2 . . 108.3 ?
    H6B1 C6B H6B2 . . 107.4 ?
    C8B C7B C6B . . 129.2(10) ?
    C8B C7B H7B . . 115.4 ?
    C6B C7B H7B . . 115.4 ?
    C7B C8B H8B1 . . 120.0 ?
    C7B C8B H8B2 . . 120.0 ?
    H8B1 C8B H8B2 . . 120.0 ?
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
    N3 H3N N2 5_677 0.86 2.09 2.940(4) 172
