#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/10/2231082.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_2231082
loop_
_publ_author_name
'Alsubari, Abdulsalam'
'Ramli, Youssef'
'Essassi, El Mokhtar'
'Zouihri, Hafid'
_publ_section_title
;
 5-(Pyridin-4-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
;
_journal_coeditor_code           FJ2436
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1926
_journal_paper_doi               10.1107/S1600536811025025
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H9 N5 O'
_chemical_formula_moiety         'C11 H9 N5 O'
_chemical_formula_sum            'C11 H9 N5 O'
_chemical_formula_weight         227.23
_chemical_name_systematic
;5-(Pyridin-4-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-
4(5H)-one
;
_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                 102.498(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.6371(3)
_cell_length_b                   19.2731(10)
_cell_length_c                   5.8593(3)
_cell_measurement_pressure       101
_cell_measurement_reflns_used    342
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      2.4
_cell_volume                     511.24(5)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  '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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6285
_diffrn_reflns_theta_full        28.88
_diffrn_reflns_theta_max         28.88
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0355
_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)+(0.0427P)²+0.0014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0845
_reflns_number_gt                2201
_reflns_number_total             2603
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2436.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2231082
_cod_database_fobs_code          2231082
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
N N2 0.7680(3) 1.03978(7) 0.5859(2) 0.0280(3) Uani d . 1 1
N N1 0.3899(3) 0.95388(6) 0.5329(2) 0.0242(3) Uani d . 1 1
N N3 0.7129(3) 1.11511(7) 0.2529(2) 0.0275(3) Uani d D 1 1
N N5 0.8324(3) 0.71619(7) 0.6387(3) 0.0326(3) Uani d . 1 1
N N4 0.5292(3) 1.12382(7) 0.0394(2) 0.0312(3) Uani d . 1 1
O O1 0.0403(3) 0.93783(6) 0.1944(2) 0.0343(3) Uani d . 1 1
C C8 0.3807(3) 1.03227(8) 0.2246(3) 0.0233(3) Uani d . 1 1
C C11 0.6365(3) 0.98760(8) 0.6577(3) 0.0257(3) Uani d . 1 1
H H11 0.7155 0.9713 0.8075 0.031 Uiso calc R 1 1
C C10 0.6293(3) 1.06125(8) 0.3675(3) 0.0235(3) Uani d . 1 1
C C7 0.2488(4) 0.97246(8) 0.3022(3) 0.0242(3) Uani d . 1 1
C C1 0.4678(3) 0.83113(8) 0.6455(3) 0.0250(3) Uani d . 1 1
C C6 0.2764(4) 0.89454(8) 0.6453(3) 0.0289(4) Uani d . 1 1
H H6A 0.0764 0.8842 0.5626 0.035 Uiso calc R 1 1
H H6B 0.2708 0.9066 0.8050 0.035 Uiso calc R 1 1
C C2 0.6726(4) 0.81124(9) 0.8437(3) 0.0298(4) Uani d . 1 1
H H2 0.6926 0.8360 0.9825 0.036 Uiso calc R 1 1
C C5 0.4487(4) 0.79196(8) 0.4448(3) 0.0322(4) Uani d . 1 1
H H5 0.3130 0.8036 0.3087 0.039 Uiso calc R 1 1
C C4 0.6333(4) 0.73540(8) 0.4486(3) 0.0351(4) Uani d . 1 1
H H4 0.6181 0.7095 0.3125 0.042 Uiso calc R 1 1
C C9 0.3281(4) 1.07419(8) 0.0210(3) 0.0286(3) Uani d . 1 1
H H9 0.1735 1.0677 -0.1078 0.034 Uiso calc R 1 1
C C3 0.8469(4) 0.75365(9) 0.8304(3) 0.0332(4) Uani d . 1 1
H H3 0.9827 0.7404 0.9646 0.040 Uiso calc R 1 1
H H3N 0.869(4) 1.1429(12) 0.304(4) 0.060(7) Uiso d 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'
O O 0.0106 0.0060 '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
C11 N2 C10 112.37(14)
C11 N1 C7 123.10(13)
C11 N1 C6 117.67(14)
C7 N1 C6 119.20(13)
C10 N3 N4 111.39(14)
C10 N3 H3N 126.6(15)
N4 N3 H3N 122.0(15)
C3 N5 C4 117.08(15)
C9 N4 N3 105.96(13)
C10 C8 C9 104.34(14)
C10 C8 C7 119.42(14)
C9 C8 C7 136.22(15)
N2 C11 N1 126.12(15)
N2 C11 H11 116.9
N1 C11 H11 116.9
N3 C10 N2 125.17(14)
N3 C10 C8 107.61(13)
N2 C10 C8 127.23(14)
O1 C7 N1 120.18(14)
O1 C7 C8 128.22(16)
N1 C7 C8 111.59(14)
C5 C1 C2 117.87(15)
C5 C1 C6 120.77(15)
C2 C1 C6 121.35(15)
N1 C6 C1 111.23(11)
N1 C6 H6A 109.4
C1 C6 H6A 109.4
N1 C6 H6B 109.4
C1 C6 H6B 109.4
H6A C6 H6B 108.0
C3 C2 C1 118.49(16)
C3 C2 H2 120.8
C1 C2 H2 120.8
C4 C5 C1 119.39(16)
C4 C5 H5 120.3
C1 C5 H5 120.3
N5 C4 C5 123.05(16)
N5 C4 H4 118.5
C5 C4 H4 118.5
N4 C9 C8 110.70(15)
N4 C9 H9 124.7
C8 C9 H9 124.7
N5 C3 C2 124.12(17)
N5 C3 H3 117.9
C2 C3 H3 117.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C11 1.293(2)
N2 C10 1.366(2)
N1 C11 1.379(2)
N1 C7 1.415(2)
N1 C6 1.4725(19)
N3 C10 1.339(2)
N3 N4 1.363(2)
N3 H3N 0.897(16)
N5 C3 1.325(2)
N5 C4 1.336(2)
N4 C9 1.324(2)
O1 C7 1.231(2)
C8 C10 1.387(2)
C8 C9 1.418(2)
C8 C7 1.425(2)
C11 H11 0.9300
C1 C5 1.384(2)
C1 C2 1.386(2)
C1 C6 1.510(2)
C6 H6A 0.9700
C6 H6B 0.9700
C2 C3 1.385(3)
C2 H2 0.9300
C5 C4 1.383(2)
C5 H5 0.9300
C4 H4 0.9300
C9 H9 0.9300
C3 H3 0.9300
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
N3 H3N N5 2_756 0.90(2) 1.96(2) 2.840(2) 168(2) yes
C4 H4 N4 2_645 0.93 2.61 3.526(2) 167 yes
C9 H9 N2 1_454 0.93 2.36 3.289(2) 174 yes
C11 H11 O1 1_656 0.93 2.52 3.430(2) 167 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7989078
