#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/34/2013413.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_2013413
loop_
_publ_author_name
'Avasthi, Kamlakar'
'Farooq, Sheikh M.'
'Rawat, Diwan S.'
'Sharon, Ashoke'
'Maulik, Prakas R.'
_publ_section_title
;
 A stacked pyrazolo[3,4-d]pyrimidine-based flexible molecule:
 the effect on stacking of a bulky isopropyl group in comparison with a
 methyl/ethyl group
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o523
_journal_page_last               o524
_journal_paper_doi               10.1107/S0108270103016676
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C25 H36 N8 S4'
_chemical_formula_moiety         'C25 H36 N8 S4'
_chemical_formula_sum            'C25 H36 N8 S4'
_chemical_formula_weight         576.90
_chemical_melting_point          358
_chemical_name_common            pyrazolo[3,4-d]pyrimidine
_chemical_name_systematic
;
1,3-bis(4,6-diisopropylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propane
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 118.070(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.044(2)
_cell_length_b                   8.8140(10)
_cell_length_c                   18.953(2)
_cell_measurement_reflns_used    44
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.504
_cell_measurement_theta_min      3.878
_cell_volume                     3101.9(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4 diffractometer'
_diffrn_measurement_method       θ-2θ
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3403
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.206
_refine_ls_extinction_coef       0.0045(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0402P)²+1.8299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0936
_reflns_number_gt                2352
_reflns_number_total             2738
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1217.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2013413
_cod_database_fobs_code          2013413
loop_
_symmetry_equiv_pos_as_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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.72652(3) 0.09840(6) 0.38944(3) 0.06254(18) Uani d . 1 . . S
S2 0.49839(3) 0.06907(5) 0.10838(3) 0.05883(17) Uani d . 1 . . S
N1 0.58349(8) 0.55675(16) 0.26696(8) 0.0488(4) Uani d . 1 . . N
N2 0.63817(8) 0.59195(18) 0.34150(9) 0.0598(4) Uani d . 1 . . N
C3 0.67177(10) 0.4644(2) 0.37210(11) 0.0581(5) Uani d . 1 . . C
H3 0.7115 0.4557 0.4225 0.070 Uiso calc R 1 . . H
C3' 0.64020(9) 0.34162(19) 0.31913(10) 0.0455(4) Uani d . 1 . . C
C4 0.65180(9) 0.18612(19) 0.31228(10) 0.0463(4) Uani d . 1 . . C
N5 0.60762(8) 0.11002(16) 0.24719(8) 0.0492(3) Uani d . 1 . . N
C6 0.55244(9) 0.18830(19) 0.18806(10) 0.0455(4) Uani d . 1 . . C
N7 0.53710(7) 0.33438(15) 0.18501(8) 0.0451(3) Uani d . 1 . . N
C7' 0.58319(9) 0.40652(18) 0.25234(10) 0.0428(4) Uani d . 1 . . C
C8 0.53726(10) 0.67407(19) 0.21351(10) 0.0515(4) Uani d . 1 . . C
H8A 0.5012 0.6269 0.1649 0.062 Uiso calc R 1 . . H
H8B 0.5660 0.7408 0.1991 0.062 Uiso calc R 1 . . H
C9 0.5000 0.7674(3) 0.2500 0.0518(6) Uani d S 1 . . C
H9A 0.4647 0.8323 0.2090 0.062 Uiso calc PR 0.50 . . H
H9B 0.5353 0.8323 0.2910 0.062 Uiso calc PR 0.50 . . H
C10 0.73466(11) -0.0806(2) 0.34705(13) 0.0635(5) Uani d . 1 . . C
H10 0.6883 -0.1336 0.3245 0.076 Uiso calc R 1 . . H
C11 0.75587(17) -0.0575(4) 0.28210(18) 0.1069(10) Uani d . 1 . . C
H11A 0.8025 -0.0108 0.3044 0.160 Uiso calc R 1 . . H
H11B 0.7212 0.0068 0.2413 0.160 Uiso calc R 1 . . H
H11C 0.7574 -0.1538 0.2593 0.160 Uiso calc R 1 . . H
C12 0.79013(14) -0.1723(3) 0.41677(17) 0.0990(9) Uani d . 1 . . C
H12A 0.7956 -0.2702 0.3981 0.149 Uiso calc R 1 . . H
H12B 0.7743 -0.1847 0.4564 0.149 Uiso calc R 1 . . H
H12C 0.8355 -0.1200 0.4399 0.149 Uiso calc R 1 . . H
C13 0.43175(10) 0.1936(2) 0.03455(11) 0.0566(5) Uani d . 1 . . C
H13 0.4108 0.2573 0.0607 0.068 Uiso calc R 1 . . H
C14 0.37376(12) 0.0888(3) -0.02454(14) 0.0809(7) Uani d . 1 . . C
H14A 0.3358 0.1483 -0.0648 0.121 Uiso calc R 1 . . H
H14B 0.3547 0.0280 0.0032 0.121 Uiso calc R 1 . . H
H14C 0.3942 0.0240 -0.0493 0.121 Uiso calc R 1 . . H
C15 0.46332(14) 0.2940(3) -0.00501(12) 0.0800(7) Uani d . 1 . . C
H15A 0.4835 0.2324 -0.0313 0.120 Uiso calc R 1 . . H
H15B 0.5004 0.3562 0.0346 0.120 Uiso calc R 1 . . H
H15C 0.4263 0.3576 -0.0437 0.120 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
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'
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
C6 S1 C13 . 104.79(9)
C4 S2 C10 . 104.48(9)
C4 N5 C6 . 117.56(15)
C6 N7 C7' . 111.54(14)
N7 C6 N5 . 128.69(16)
N7 C6 S1 . 120.07(13)
N5 C6 S1 . 111.24(12)
N7 C7' N1 . 126.11(15)
N7 C7' C3' . 126.58(15)
N1 C7' C3' . 107.29(15)
C7' N1 N2 . 110.66(14)
C7' N1 C8 . 128.07(15)
N2 N1 C8 . 121.20(14)
C3 N2 N1 . 106.16(14)
N5 C4 C3' . 120.14(16)
N5 C4 S2 . 121.10(13)
C3' C4 S2 . 118.73(13)
C7' C3' C4 . 115.37(15)
C7' C3' C3 . 104.30(15)
C4 C3' C3 . 140.13(17)
N1 C8 C9 . 112.99(13)
N1 C8 H8A . 109.0
C9 C8 H8A . 109.0
N1 C8 H8B . 109.0
C9 C8 H8B . 109.0
H8A C8 H8B . 107.8
N2 C3 C3' . 111.58(16)
N2 C3 H3 . 124.2
C3' C3 H3 . 124.2
C15 C13 C14 . 112.36(18)
C15 C13 S1 . 112.32(15)
C14 C13 S1 . 105.22(15)
C15 C13 H13 . 108.9
C14 C13 H13 . 108.9
S1 C13 H13 . 108.9
C8 C9 C8 2_655 113.9(2)
C8 C9 H9A 2_655 108.8
C8 C9 H9A . 108.8
C8 C9 H9B 2_655 108.8
C8 C9 H9B . 108.8
H9A C9 H9B . 107.7
C11 C10 C12 . 112.3(2)
C11 C10 S2 . 111.65(16)
C12 C10 S2 . 105.75(16)
C11 C10 H10 . 109.0
C12 C10 H10 . 109.0
S2 C10 H10 . 109.0
C13 C14 H14A . 109.5
C13 C14 H14B . 109.5
H14A C14 H14B . 109.5
C13 C14 H14C . 109.5
H14A C14 H14C . 109.5
H14B C14 H14C . 109.5
C13 C15 H15A . 109.5
C13 C15 H15B . 109.5
H15A C15 H15B . 109.5
C13 C15 H15C . 109.5
H15A C15 H15C . 109.5
H15B C15 H15C . 109.5
C10 C12 H12A . 109.5
C10 C12 H12B . 109.5
H12A C12 H12B . 109.5
C10 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
C10 C11 H11A . 109.5
C10 C11 H11B . 109.5
H11A C11 H11B . 109.5
C10 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 109.5
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 C6 . 1.7497(17) ?
S1 C13 . 1.8117(19) ?
S2 C4 . 1.7452(17) ?
S2 C10 . 1.815(2) ?
N5 C4 . 1.325(2) ?
N5 C6 . 1.362(2) ?
N7 C6 . 1.322(2) ?
N7 C7' . 1.345(2) ?
C7' N1 . 1.352(2) ?
C7' C3' . 1.393(2) ?
N1 N2 . 1.373(2) ?
N1 C8 . 1.454(2) ?
N2 C3 . 1.309(2) ?
C4 C3' . 1.409(2) ?
C3' C3 . 1.412(2) ?
C8 C9 . 1.509(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C3 H3 . 0.9300 ?
C13 C15 . 1.501(3) ?
C13 C14 . 1.520(3) ?
C13 H13 . 0.9800 ?
C9 C8 2_655 1.509(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.508(3) ?
C10 C12 . 1.520(3) ?
C10 H10 . 0.9800 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
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_4
_geom_torsion
C7' N1 N2 C3 . 0.7(2)
C8 N1 N2 C3 . -176.34(16)
N1 N2 C3 C3' . -0.3(2)
N2 C3 C3' C7' . -0.2(2)
N2 C3 C3' C4 . 174.1(2)
C7' C3' C4 N5 . -3.4(2)
C3 C3' C4 N5 . -177.3(2)
C7' C3' C4 S1 . 174.67(12)
C3 C3' C4 S1 . 0.8(3)
C10 S1 C4 N5 . 12.30(16)
C10 S1 C4 C3' . -165.77(14)
C3' C4 N5 C6 . 1.0(2)
S1 C4 N5 C6 . -177.00(12)
C4 N5 C6 N7 . 2.1(3)
C4 N5 C6 S2 . -178.28(12)
C13 S2 C6 N7 . 2.52(16)
C13 S2 C6 N5 . -177.16(12)
N5 C6 N7 C7' . -2.2(2)
S2 C6 N7 C7' . 178.21(11)
C6 N7 C7' N1 . 177.79(16)
C6 N7 C7' C3' . -0.8(2)
N2 N1 C7' N7 . -179.63(15)
C8 N1 C7' N7 . -2.8(3)
N2 N1 C7' C3' . -0.82(19)
C8 N1 C7' C3' . 175.97(15)
C4 C3' C7' N7 . 3.4(2)
C3 C3' C7' N7 . 179.39(16)
C4 C3' C7' N1 . -175.37(15)
C3 C3' C7' N1 . 0.59(18)
C7' N1 C8 C9 . 126.74(18)
N2 N1 C8 C9 . -56.8(2)
N1 C8 C9 C8 2_655 -49.76(11)
C4 S1 C10 C11 . 67.79(19)
C4 S1 C10 C12 . -169.71(15)
C6 S2 C13 C15 . 71.75(15)
C6 S2 C13 C14 . -165.75(14)
