#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/87/2208788.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_2208788
loop_
_publ_author_name
'Xiao-Hua Zeng'
'Hong-Mei Wang'
'Ming-Wu Ding'
'Hong-Wu He'
_publ_section_title
3-Benzyl-6-isopropyl-5-methoxy-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one
_journal_coeditor_code           BH2011
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1888
_journal_page_last               o1890
_journal_paper_doi               10.1107/S160053680601292X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H17 N5 O2'
_chemical_formula_moiety         'C15 H17 N5 O2'
_chemical_formula_sum            'C15 H17 N5 O2'
_chemical_formula_weight         299.34
_chemical_melting_point          395
_chemical_name_systematic
;
3-Benzyl-6-isopropyl-5-methoxy-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                102.369(2)
_cell_angle_beta                 103.511(2)
_cell_angle_gamma                92.883(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0800(8)
_cell_length_b                   8.7574(10)
_cell_length_c                   13.0492(15)
_cell_measurement_reflns_used    2691
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      24.93
_cell_measurement_theta_min      3.02
_cell_volume                     764.13(15)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8856
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.297
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0559
_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)+(0.086P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1452
_reflns_number_gt                2475
_reflns_number_total             3454
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2011.cif
_cod_data_source_block           I
_cod_database_code               2208788
_cod_database_fobs_code          2208788
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C C1 0.2782(2) 0.61421(19) 0.67208(13) 0.0556(4) Uani d . 1
H H1 0.3389 0.5764 0.7316 0.067 Uiso calc R 1
C C2 0.3776(3) 0.6322(2) 0.59563(15) 0.0669(5) Uani d . 1
H H2 0.5049 0.6058 0.6037 0.080 Uiso calc R 1
C C3 0.2912(3) 0.6883(2) 0.50816(15) 0.0717(5) Uani d . 1
H H3 0.3598 0.7010 0.4573 0.086 Uiso calc R 1
C C4 0.1022(3) 0.7260(2) 0.49561(15) 0.0708(5) Uani d . 1
H H4 0.0419 0.7629 0.4356 0.085 Uiso calc R 1
C C5 0.0026(3) 0.70911(19) 0.57174(13) 0.0575(4) Uani d . 1
H H5 -0.1244 0.7364 0.5634 0.069 Uiso calc R 1
C C6 0.0882(2) 0.65220(17) 0.66051(11) 0.0460(4) Uani d . 1
C C7 -0.0293(2) 0.6317(2) 0.74010(12) 0.0562(4) Uani d . 1
H H7A -0.0754 0.7317 0.7662 0.067 Uiso calc R 1
H H7B -0.1432 0.5574 0.7022 0.067 Uiso calc R 1
C C8 0.1750(2) 0.66179(16) 0.93074(11) 0.0386(3) Uani d . 1
C C9 0.2366(2) 0.55336(15) 0.98909(11) 0.0403(3) Uani d . 1
C C10 0.3343(2) 0.60378(16) 1.10089(12) 0.0416(3) Uani d . 1
C C11 0.2999(2) 0.86568(15) 1.06526(11) 0.0392(3) Uani d . 1
C C12 0.2904(2) 1.12757(17) 1.04446(14) 0.0528(4) Uani d . 1
H H12A 0.3388 1.1017 0.9807 0.079 Uiso calc R 1
H H12B 0.3434 1.2321 1.0846 0.079 Uiso calc R 1
H H12C 0.1504 1.1221 1.0238 0.079 Uiso calc R 1
C C13 0.4546(3) 0.83833(19) 1.25289(13) 0.0628(5) Uani d . 1
H H13 0.4702 0.7483 1.2865 0.075 Uiso calc R 1
C C14 0.6594(3) 0.9168(2) 1.27075(17) 0.0852(7) Uani d . 1
H H14A 0.7331 0.8462 1.2329 0.128 Uiso calc R 1
H H14B 0.7223 0.9432 1.3468 0.128 Uiso calc R 1
H H14C 0.6524 1.0108 1.2439 0.128 Uiso calc R 1
C C15 0.3221(3) 0.9396(2) 1.30892(15) 0.0830(6) Uani d . 1
H H15A 0.3245 1.0403 1.2910 0.125 Uiso calc R 1
H H15B 0.3676 0.9535 1.3860 0.125 Uiso calc R 1
H H15C 0.1910 0.8887 1.2851 0.125 Uiso calc R 1
N N1 0.07521(18) 0.57722(14) 0.83268(10) 0.0476(3) Uani d . 1
N N2 0.0768(2) 0.42053(15) 0.83065(11) 0.0551(4) Uani d . 1
N N3 0.1742(2) 0.40548(14) 0.92482(11) 0.0512(3) Uani d . 1
N N4 0.20552(17) 0.82079(13) 0.96405(10) 0.0415(3) Uani d . 1
N N5 0.36121(18) 0.77107(13) 1.13574(9) 0.0429(3) Uani d . 1
O O1 0.38855(17) 0.52165(12) 1.16447(9) 0.0563(3) Uani d . 1
O O2 0.34870(16) 1.01695(11) 1.11139(9) 0.0518(3) Uani d . 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
_geom_angle_publ_flag
C2 C1 C6 120.13(16) ?
C2 C1 H1 119.9 ?
C6 C1 H1 119.9 ?
C3 C2 C1 120.75(18) ?
C3 C2 H2 119.6 ?
C1 C2 H2 119.6 ?
C2 C3 C4 119.64(18) ?
C2 C3 H3 120.2 ?
C4 C3 H3 120.2 ?
C5 C4 C3 119.91(17) ?
C5 C4 H4 120.0 ?
C3 C4 H4 120.0 ?
C4 C5 C6 121.01(17) ?
C4 C5 H5 119.5 ?
C6 C5 H5 119.5 ?
C5 C6 C1 118.56(15) ?
C5 C6 C7 118.90(14) ?
C1 C6 C7 122.54(14) ?
N1 C7 C6 114.88(13) ?
N1 C7 H7A 108.5 ?
C6 C7 H7A 108.5 ?
N1 C7 H7B 108.5 ?
C6 C7 H7B 108.5 ?
H7A C7 H7B 107.5 ?
N1 C8 N4 126.96(13) ?
N1 C8 C9 105.16(13) ?
N4 C8 C9 127.88(13) ?
C8 C9 N3 109.01(13) ?
C8 C9 C10 119.92(13) ?
N3 C9 C10 130.86(13) ?
O1 C10 C9 127.50(13) ?
O1 C10 N5 120.86(13) ?
C9 C10 N5 111.62(12) ?
N4 C11 O2 120.40(12) ?
N4 C11 N5 127.08(12) ?
O2 C11 N5 112.52(12) ?
O2 C12 H12A 109.5 ?
O2 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
O2 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
N5 C13 C14 111.94(15) ?
N5 C13 C15 112.16(15) ?
C14 C13 C15 114.52(16) ?
N5 C13 H13 105.8 ?
C14 C13 H13 105.8 ?
C15 C13 H13 105.8 ?
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 ?
C8 N1 N2 109.48(12) y
C8 N1 C7 128.93(13) ?
N2 N1 C7 121.55(13) ?
N3 N2 N1 108.57(12) ?
N2 N3 C9 107.77(12) ?
C11 N4 C8 111.65(12) ?
C11 N5 C10 121.68(12) y
C11 N5 C13 121.65(12) ?
C10 N5 C13 116.65(11) ?
C11 O2 C12 117.18(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.378(2) ?
C1 C6 1.383(2) ?
C1 H1 0.9300 ?
C2 C3 1.365(3) ?
C2 H2 0.9300 ?
C3 C4 1.375(3) ?
C3 H3 0.9300 ?
C4 C5 1.373(2) ?
C4 H4 0.9300 ?
C5 C6 1.381(2) ?
C5 H5 0.9300 ?
C6 C7 1.507(2) ?
C7 N1 1.4491(19) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 N1 1.3432(18) y
C8 N4 1.3568(17) y
C8 C9 1.367(2) y
C9 N3 1.3711(18) y
C9 C10 1.422(2) y
C10 O1 1.2198(16) ?
C10 N5 1.4267(17) y
C11 N4 1.2978(18) y
C11 O2 1.3235(16) ?
C11 N5 1.3772(17) y
C12 O2 1.4512(17) ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C13 N5 1.4912(19) ?
C13 C14 1.518(3) ?
C13 C15 1.525(3) ?
C13 H13 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 ?
N1 N2 1.3674(18) y
N2 N3 1.2982(18) y
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
C1 H1 N1 . 0.93 2.52 2.866(2) 102 no
C15 H15A O2 . 0.96 2.36 2.846(2) 111 y
C14 H14C O2 . 0.96 2.44 2.961(2) 114 y
C12 H12B O1 1_565 0.96 2.50 3.4322(19) 164 y
C1 H1 O1 2_667 0.93 2.40 3.2481(19) 152 y
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
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(3) ?
C1 C2 C3 C4 -0.6(3) ?
C2 C3 C4 C5 0.9(3) ?
C3 C4 C5 C6 -1.0(3) ?
C4 C5 C6 C1 0.8(2) ?
C4 C5 C6 C7 -178.34(16) ?
C2 C1 C6 C5 -0.5(2) ?
C2 C1 C6 C7 178.63(15) ?
C5 C6 C7 N1 -177.72(14) ?
C1 C6 C7 N1 3.2(2) ?
N1 C8 C9 N3 0.51(16) ?
N4 C8 C9 N3 179.92(13) y
N1 C8 C9 C10 -174.77(12) ?
N4 C8 C9 C10 4.6(2) ?
C8 C9 C10 O1 175.96(14) ?
N3 C9 C10 O1 1.9(3) ?
C8 C9 C10 N5 -2.47(19) ?
N3 C9 C10 N5 -176.57(13) ?
N4 C8 N1 N2 -179.89(13) ?
C9 C8 N1 N2 -0.47(15) ?
N4 C8 N1 C7 -2.3(2) ?
C9 C8 N1 C7 177.12(14) ?
C6 C7 N1 C8 92.87(18) ?
C6 C7 N1 N2 -89.79(17) ?
C8 N1 N2 N3 0.26(16) ?
C7 N1 N2 N3 -177.54(13) ?
N1 N2 N3 C9 0.07(16) ?
C8 C9 N3 N2 -0.37(16) ?
C10 C9 N3 N2 174.22(15) ?
O2 C11 N4 C8 177.85(12) ?
N5 C11 N4 C8 -1.8(2) ?
N1 C8 N4 C11 176.90(13) ?
C9 C8 N4 C11 -2.4(2) ?
N4 C11 N5 C10 3.5(2) ?
O2 C11 N5 C10 -176.11(11) ?
N4 C11 N5 C13 -174.93(14) ?
O2 C11 N5 C13 5.44(19) ?
O1 C10 N5 C11 -179.63(13) ?
C9 C10 N5 C11 -1.09(19) ?
O1 C10 N5 C13 -1.1(2) ?
C9 C10 N5 C13 177.44(13) ?
C14 C13 N5 C11 -71.65(19) ?
C15 C13 N5 C11 58.7(2) ?
C14 C13 N5 C10 109.83(16) ?
C15 C13 N5 C10 -119.85(15) ?
N4 C11 O2 C12 0.63(19) ?
N5 C11 O2 C12 -179.71(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128433
