#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/03/2240378.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_2240378
loop_
_publ_author_name
'El Fal, Mohammed'
'Ramli, Youssef'
'Essassi, El Mokhtar'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 The crystal structure of
 1,5-dibenzyl-1H-pyrazolo[3,4-d]pyrimidine-4(5H)-thione
;
_journal_coeditor_code           TK5354
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o95
_journal_page_last               o96
_journal_paper_doi               10.1107/S205698901402828X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C19 H16 N4 S'
_chemical_formula_moiety         'C19 H16 N4 S'
_chemical_formula_sum            'C19 H16 N4 S'
_chemical_formula_weight         332.42
_chemical_melting_point          563
_chemical_name_systematic
;
1,5-Dibenzyl-1H-pyrazolo[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                 97.860(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.4953(12)
_cell_length_b                   29.140(8)
_cell_length_c                   6.3889(16)
_cell_measurement_reflns_used    3582
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.80
_cell_volume                     829.0(4)
_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'
_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  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9214
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.119
_refine_ls_abs_structure_details
;
Flack & Bernardinelli (2000), 1730 Friedel pairs
;
_refine_ls_abs_structure_Flack   -0.11(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0407
_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)+(0.0318P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                2406
_reflns_number_total             3582
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            tk5354sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2240378
_cod_database_fobs_code          2240378
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 0.5941(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
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
