#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/79/2227973.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227973
loop_
_publ_author_name
'Wang, Hong-Mei'
'Deng, Shou-Heng'
'Zeng, Xiao-Hua'
'Chen, Ping'
'Chen, Li-Li'
_publ_section_title
;
 6-Butyl-5-(4-methylphenoxy)-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one
;
_journal_coeditor_code           RZ2502
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2990
_journal_page_last               o2991
_journal_paper_doi               10.1107/S160053681004300X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H21 N5 O2'
_chemical_formula_moiety         'C21 H21 N5 O2'
_chemical_formula_sum            'C21 H21 N5 O2'
_chemical_formula_weight         375.43
_chemical_name_systematic
;6-Butyl-5-(4-methylphenoxy)-3-phenyl-3H-1,2,3-
triazolo[4,5-d]pyrimidin-7(6H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.6430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0954(10)
_cell_length_b                   16.4478(15)
_cell_length_c                   11.3484(11)
_cell_measurement_reflns_used    6350
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.80
_cell_measurement_theta_min      2.25
_cell_volume                     1973.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20458
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3876
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0541
_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)+(0.1122P)²+0.0419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.1822
_reflns_number_gt                2663
_reflns_number_total             3876
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2502.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227973
_cod_database_fobs_code          2227973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
C C1 0.42419(17) 0.24051(13) 0.45138(17) 0.0654(5) Uani d . 1 . .
C C2 0.5223(2) 0.26001(14) 0.5541(2) 0.0797(6) Uani d . 1 . .
H H2 0.5810 0.2208 0.5936 0.096 Uiso calc R 1 . .
C C3 0.5326(2) 0.33854(15) 0.5978(2) 0.0904(7) Uani d . 1 . .
H H3 0.5980 0.3523 0.6682 0.108 Uiso calc R 1 . .
C C4 0.4468(3) 0.39682(15) 0.5381(3) 0.0909(7) Uani d . 1 . .
H H4 0.4543 0.4499 0.5677 0.109 Uiso calc R 1 . .
C C5 0.3502(2) 0.37608(16) 0.4348(3) 0.0923(7) Uani d . 1 . .
H H5 0.2922 0.4154 0.3942 0.111 Uiso calc R 1 . .
C C6 0.3380(2) 0.29824(14) 0.3907(2) 0.0764(6) Uani d . 1 . .
H H6 0.2723 0.2845 0.3205 0.092 Uiso calc R 1 . .
C C7 0.49373(17) 0.10245(12) 0.39629(16) 0.0616(5) Uani d . 1 A .
C C8 0.42311(18) 0.03487(12) 0.34748(17) 0.0659(5) Uani d . 1 . .
C C9 0.4821(2) -0.03604(13) 0.31905(17) 0.0681(5) Uani d . 1 A .
C C10 0.67331(18) 0.04538(13) 0.39924(17) 0.0670(5) Uani d . 1 A .
C C11 0.6857(6) -0.0970(5) 0.3246(5) 0.0795(18) Uani d PD 0.77 A 1
H H11A 0.6320 -0.1448 0.3109 0.095 Uiso calc PR 0.77 A 1
H H11B 0.7589 -0.1073 0.3956 0.095 Uiso calc PR 0.77 A 1
C C12 0.7294(5) -0.0808(4) 0.2082(5) 0.138(2) Uani d PD 0.77 A 1
H H12A 0.7829 -0.0328 0.2238 0.166 Uiso calc PR 0.77 A 1
H H12B 0.7810 -0.1263 0.1980 0.166 Uiso calc PR 0.77 A 1
C C13 0.6379(6) -0.0699(3) 0.1027(5) 0.149(2) Uani d PD 0.77 A 1
H H13A 0.6006 -0.0168 0.1050 0.179 Uiso calc PR 0.77 A 1
H H13B 0.5726 -0.1101 0.0979 0.179 Uiso calc PR 0.77 A 1
C C14 0.6776(10) -0.0757(5) -0.0175(6) 0.142(4) Uani d PD 0.77 A 1
H H14A 0.7472 -0.0395 -0.0114 0.213 Uiso calc PR 0.77 A 1
H H14B 0.6074 -0.0606 -0.0874 0.213 Uiso calc PR 0.77 A 1
H H14C 0.7026 -0.1304 -0.0279 0.213 Uiso calc PR 0.77 A 1
C C11' 0.704(2) -0.0825(18) 0.3141(15) 0.104(10) Uani d PD 0.23 A 2
H H11C 0.7847 -0.0555 0.3291 0.125 Uiso calc PR 0.23 A 2
H H11D 0.7168 -0.1296 0.3679 0.125 Uiso calc PR 0.23 A 2
C C12' 0.6617(12) -0.1107(8) 0.1849(10) 0.081(3) Uani d PD 0.23 A 2
H H12C 0.6172 -0.1610 0.1880 0.097 Uiso calc PR 0.23 A 2
H H12D 0.5967 -0.0720 0.1431 0.097 Uiso calc PR 0.23 A 2
C C13' 0.7276(11) -0.1267(7) 0.0973(8) 0.104(4) Uani d PD 0.23 A 2
H H13C 0.8104 -0.1024 0.1329 0.125 Uiso calc PR 0.23 A 2
H H13D 0.7414 -0.1850 0.1015 0.125 Uiso calc PR 0.23 A 2
C C14' 0.695(2) -0.1081(15) -0.0281(18) 0.101(6) Uani d PD 0.23 A 2
H H14D 0.6086 -0.1234 -0.0676 0.152 Uiso calc PR 0.23 A 2
H H14E 0.7492 -0.1374 -0.0650 0.152 Uiso calc PR 0.23 A 2
H H14F 0.7046 -0.0508 -0.0381 0.152 Uiso calc PR 0.23 A 2
C C15 0.87510(18) 0.10857(13) 0.4721(2) 0.0717(6) Uani d . 1 A .
C C16 0.9372(2) 0.14531(16) 0.4005(2) 0.0856(7) Uani d . 1 . .
H H16 0.9238 0.1289 0.3191 0.103 Uiso calc R 1 . .
C C17 1.0212(2) 0.20782(16) 0.4509(2) 0.0895(7) Uani d . 1 . .
H H17 1.0632 0.2338 0.4020 0.107 Uiso calc R 1 . .
C C18 1.04316(19) 0.23192(14) 0.5710(2) 0.0809(6) Uani d . 1 . .
C C19 0.9782(2) 0.19289(17) 0.6399(2) 0.0904(7) Uani d . 1 . .
H H19 0.9913 0.2088 0.7215 0.108 Uiso calc R 1 . .
C C20 0.8938(2) 0.13042(16) 0.5914(2) 0.0865(7) Uani d . 1 . .
H H20 0.8511 0.1042 0.6396 0.104 Uiso calc R 1 . .
C C21 1.1367(3) 0.29832(18) 0.6258(3) 0.1124(9) Uani d . 1 . .
H H21A 1.2173 0.2847 0.6163 0.169 Uiso calc R 1 . .
H H21B 1.1449 0.3040 0.7121 0.169 Uiso calc R 1 . .
H H21C 1.1074 0.3486 0.5840 0.169 Uiso calc R 1 . .
N N1 0.40888(13) 0.15838(10) 0.40749(14) 0.0651(4) Uani d . 1 . .
N N2 0.28911(15) 0.12506(12) 0.36653(17) 0.0760(5) Uani d . 1 . .
N N3 0.29856(15) 0.05057(12) 0.33090(16) 0.0763(5) Uani d . 1 . .
N N4 0.61476(15) -0.02544(10) 0.34970(14) 0.0686(5) Uani d D 1 . .
N N5 0.62063(14) 0.11114(10) 0.42446(15) 0.0660(4) Uani d . 1 . .
O O1 0.43198(15) -0.09929(10) 0.27448(15) 0.0877(5) Uani d . 1 . .
O O2 0.79833(13) 0.04150(9) 0.41997(15) 0.0840(5) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.1(2) ?
C2 C1 N1 . . 119.77(18) ?
C6 C1 N1 . . 119.07(18) ?
C1 C2 C3 . . 118.9(2) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 120.5(2) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C5 C4 C3 . . 119.5(2) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C6 C5 C4 . . 120.8(2) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C1 . . 119.1(2) ?
C5 C6 H6 . . 120.4 ?
C1 C6 H6 . . 120.4 ?
N1 C7 N5 . . 127.68(18) ?
N1 C7 C8 . . 105.08(17) ?
N5 C7 C8 . . 127.23(19) ?
N3 C8 C7 . . 109.43(18) ?
N3 C8 C9 . . 129.96(19) ?
C7 C8 C9 . . 120.58(19) ?
O1 C9 N4 . . 121.2(2) ?
O1 C9 C8 . . 127.7(2) ?
N4 C9 C8 . . 111.04(18) ?
N5 C10 O2 . . 120.81(18) ?
N5 C10 N4 . . 127.48(18) ?
O2 C10 N4 . . 111.70(18) ?
N4 C11 C12 . . 110.1(5) ?
N4 C11 H11A . . 109.6 ?
C12 C11 H11A . . 109.6 ?
N4 C11 H11B . . 109.6 ?
C12 C11 H11B . . 109.6 ?
H11A C11 H11B . . 108.2 ?
C13 C12 C11 . . 115.9(5) ?
C13 C12 H12A . . 108.3 ?
C11 C12 H12A . . 108.3 ?
C13 C12 H12B . . 108.3 ?
C11 C12 H12B . . 108.3 ?
H12A C12 H12B . . 107.4 ?
C12 C13 C14 . . 116.1(6) ?
C12 C13 H13A . . 108.3 ?
C14 C13 H13A . . 108.3 ?
C12 C13 H13B . . 108.3 ?
C14 C13 H13B . . 108.3 ?
H13A C13 H13B . . 107.4 ?
C12' C11' N4 . . 115.4(11) ?
C12' C11' H11C . . 108.4 ?
N4 C11' H11C . . 108.4 ?
C12' C11' H11D . . 108.4 ?
N4 C11' H11D . . 108.4 ?
H11C C11' H11D . . 107.5 ?
C13' C12' C11' . . 132.7(14) ?
C13' C12' H12C . . 104.1 ?
C11' C12' H12C . . 104.1 ?
C13' C12' H12D . . 104.1 ?
C11' C12' H12D . . 104.1 ?
H12C C12' H12D . . 105.5 ?
C14' C13' C12' . . 130.0(14) ?
C14' C13' H13C . . 104.8 ?
C12' C13' H13C . . 104.8 ?
C14' C13' H13D . . 104.8 ?
C12' C13' H13D . . 104.8 ?
H13C C13' H13D . . 105.8 ?
C13' C14' H14D . . 109.5 ?
C13' C14' H14E . . 109.5 ?
H14D C14' H14E . . 109.5 ?
C13' C14' H14F . . 109.5 ?
H14D C14' H14F . . 109.5 ?
H14E C14' H14F . . 109.5 ?
C20 C15 C16 . . 121.9(2) ?
C20 C15 O2 . . 121.1(2) ?
C16 C15 O2 . . 116.70(19) ?
C15 C16 C17 . . 118.9(2) ?
C15 C16 H16 . . 120.6 ?
C17 C16 H16 . . 120.6 ?
C18 C17 C16 . . 121.3(2) ?
C18 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
C17 C18 C19 . . 117.8(2) ?
C17 C18 C21 . . 120.9(2) ?
C19 C18 C21 . . 121.3(2) ?
C18 C19 C20 . . 121.9(2) ?
C18 C19 H19 . . 119.0 ?
C20 C19 H19 . . 119.0 ?
C15 C20 C19 . . 118.2(2) ?
C15 C20 H20 . . 120.9 ?
C19 C20 H20 . . 120.9 ?
C18 C21 H21A . . 109.5 ?
C18 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C18 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C7 N1 N2 . . 108.99(17) ?
C7 N1 C1 . . 131.55(16) ?
N2 N1 C1 . . 119.47(15) ?
N3 N2 N1 . . 108.51(16) ?
N2 N3 C8 . . 107.99(16) ?
C10 N4 C9 . . 122.28(17) ?
C10 N4 C11 . . 122.6(4) ?
C9 N4 C11 . . 115.2(4) ?
C10 N4 C11' . . 111.9(13) ?
C9 N4 C11' . . 125.1(12) ?
C11 N4 C11' . . 13.6(18) ?
C10 N5 C7 . . 111.38(17) ?
C10 O2 C15 . . 119.97(16) ?
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
C1 C2 . 1.370(3) ?
C1 C6 . 1.375(3) ?
C1 N1 . 1.432(3) ?
C2 C3 . 1.376(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.376(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.371(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.366(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.349(2) ?
C7 N5 . 1.354(2) ?
C7 C8 . 1.376(3) ?
C8 N3 . 1.362(3) ?
C8 C9 . 1.422(3) ?
C9 O1 . 1.215(2) ?
C9 N4 . 1.416(3) ?
C10 N5 . 1.302(3) ?
C10 O2 . 1.336(2) ?
C10 N4 . 1.369(3) ?
C11 N4 . 1.491(4) ?
C11 C12 . 1.562(8) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.326(6) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.559(7) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C11' C12' . 1.473(10) ?
C11' N4 . 1.502(10) ?
C11' H11C . 0.9700 ?
C11' H11D . 0.9700 ?
C12' C13' . 1.426(9) ?
C12' H12C . 0.9700 ?
C12' H12D . 0.9700 ?
C13' C14' . 1.39(2) ?
C13' H13C . 0.9700 ?
C13' H13D . 0.9700 ?
C14' H14D . 0.9600 ?
C14' H14E . 0.9600 ?
C14' H14F . 0.9600 ?
C15 C20 . 1.355(3) ?
C15 C16 . 1.356(3) ?
C15 O2 . 1.410(3) ?
C16 C17 . 1.389(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.369(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.373(3) ?
C18 C21 . 1.505(3) ?
C19 C20 . 1.387(3) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
N1 N2 . 1.381(2) ?
N2 N3 . 1.304(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
_geom_hbond_publ_flag
C12 H12A O2 . 0.97 2.50 3.048(5) 115.7 y
C2 H2 O1 3_656 0.93 2.53 3.230(3) 132.6 y
C3 H3 N2 4_666 0.93 2.61 3.535(2) 174 y
