#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/35/2223542.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_2223542
loop_
_publ_author_name
'Zeng, Xiao-Hua'
'Liu, Xiao-Ling'
'Deng, Shou-Heng'
'Chen, Ping'
'Wang, Hong-Mei'
_publ_section_title
5-(4-Chlorophenoxy)-6-isopropyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one
_journal_coeditor_code           RZ2362
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2583
_journal_page_last               o2584
_journal_paper_doi               10.1107/S160053680903788X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H16 Cl N5 O2'
_chemical_formula_moiety         'C19 H16 Cl N5 O2'
_chemical_formula_sum            'C19 H16 Cl N5 O2'
_chemical_formula_weight         381.82
_chemical_name_systematic
;
5-(4-Chlorophenoxy)-6-isopropyl-3-phenyl-3H-1,2,3-
triazolo[4,5-d]pyrimidin-7(6H)-one
;
_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                 91.737(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.8429(3)
_cell_length_b                   11.7890(2)
_cell_length_c                   18.8309(3)
_cell_measurement_reflns_used    2541
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.58
_cell_measurement_theta_min      2.35
_cell_volume                     3737.36(11)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10890
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0820
_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)+(0.064P)²+5.7684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.1882
_reflns_number_gt                2697
_reflns_number_total             3290
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2362.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223542
_cod_database_fobs_code          2223542
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_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 -0.09358(19) 0.1023(3) 0.18512(17) 0.0439(8) Uani d . 1 . .
C C2 -0.1566(2) 0.0468(3) 0.2139(2) 0.0642(11) Uani d . 1 . .
H H2 -0.1984 0.0882 0.2319 0.077 Uiso calc R 1 . .
C C3 -0.1583(3) -0.0702(3) 0.2161(2) 0.0737(12) Uani d . 1 . .
H H3 -0.2009 -0.1075 0.2360 0.088 Uiso calc R 1 . .
C C4 -0.0973(3) -0.1310(3) 0.1891(2) 0.0689(12) Uani d . 1 . .
H H4 -0.0982 -0.2099 0.1903 0.083 Uiso calc R 1 . .
C C5 -0.0348(3) -0.0757(3) 0.1601(2) 0.0673(11) Uani d . 1 . .
H H5 0.0067 -0.1175 0.1417 0.081 Uiso calc R 1 . .
C C6 -0.0322(2) 0.0415(3) 0.1578(2) 0.0560(10) Uani d . 1 . .
H H6 0.0105 0.0785 0.1379 0.067 Uiso calc R 1 . .
C C7 -0.06815(19) 0.4035(3) 0.17494(18) 0.0453(8) Uani d . 1 . .
C C8 -0.03822(18) 0.2986(3) 0.16141(16) 0.0397(7) Uani d . 1 . .
C C9 0.0704(2) 0.3664(3) 0.11400(18) 0.0462(8) Uani d . 1 . .
C C10 -0.0258(2) 0.5037(3) 0.15489(19) 0.0510(9) Uani d . 1 . .
C C11 0.16545(19) 0.2430(3) 0.06917(19) 0.0476(8) Uani d . 1 . .
C C12 0.2136(2) 0.1916(3) 0.1182(2) 0.0666(11) Uani d . 1 . .
H H12 0.2299 0.2299 0.1592 0.080 Uiso calc R 1 . .
C C13 0.2380(3) 0.0818(4) 0.1064(2) 0.0727(12) Uani d . 1 . .
H H13 0.2708 0.0449 0.1396 0.087 Uiso calc R 1 . .
C C14 0.2136(2) 0.0283(3) 0.0458(2) 0.0618(11) Uani d . 1 . .
C C15 0.1683(3) 0.0821(4) -0.0042(2) 0.0762(13) Uani d . 1 . .
H H15 0.1541 0.0454 -0.0465 0.091 Uiso calc R 1 . .
C C16 0.1431(2) 0.1920(4) 0.0077(2) 0.0687(11) Uani d . 1 . .
H H16 0.1114 0.2299 -0.0260 0.082 Uiso calc R 1 . .
C C17 0.1015(2) 0.5730(3) 0.1032(2) 0.0568(10) Uani d . 1 . .
H H17 0.1501 0.5378 0.0864 0.068 Uiso calc R 1 . .
C C18 0.1260(3) 0.6448(4) 0.1659(3) 0.0860(14) Uani d . 1 . .
H H18A 0.0816 0.6893 0.1804 0.129 Uiso calc R 1 . .
H H18B 0.1685 0.6943 0.1530 0.129 Uiso calc R 1 . .
H H18C 0.1436 0.5968 0.2044 0.129 Uiso calc R 1 . .
C C19 0.0657(3) 0.6376(4) 0.0409(3) 0.0867(14) Uani d . 1 . .
H H19A 0.0589 0.5875 0.0010 0.130 Uiso calc R 1 . .
H H19B 0.1005 0.6987 0.0287 0.130 Uiso calc R 1 . .
H H19C 0.0151 0.6678 0.0534 0.130 Uiso calc R 1 . .
Cl Cl1 0.24101(10) -0.11289(10) 0.03223(8) 0.1080(6) Uani d . 1 . .
N N1 -0.09221(15) 0.2236(2) 0.18491(14) 0.0435(7) Uani d . 1 . .
N N2 -0.15423(17) 0.2844(3) 0.21305(17) 0.0555(8) Uani d . 1 . .
N N3 -0.13910(18) 0.3917(3) 0.20656(17) 0.0562(8) Uani d . 1 . .
N N4 0.03181(15) 0.2756(2) 0.13053(15) 0.0451(7) Uani d . 1 . .
N N5 0.04809(16) 0.4770(2) 0.12434(15) 0.0470(7) Uani d . 1 . .
O O1 -0.04809(17) 0.6008(2) 0.16009(17) 0.0747(9) Uani d . 1 . .
O O2 0.14044(14) 0.35551(19) 0.08206(14) 0.0595(7) 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 . . 120.0(3) ?
C6 C1 N1 . . 120.6(3) ?
C2 C1 N1 . . 119.4(3) ?
C1 C2 C3 . . 120.4(4) ?
C1 C2 H2 . . 119.8 ?
C3 C2 H2 . . 119.8 ?
C4 C3 C2 . . 119.8(4) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 119.8(4) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.9(4) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C1 C6 C5 . . 119.1(4) ?
C1 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
N3 C7 C8 . . 109.0(3) ?
N3 C7 C10 . . 130.5(3) ?
C8 C7 C10 . . 120.5(3) ?
N1 C8 N4 . . 127.7(3) ?
N1 C8 C7 . . 106.0(3) ?
N4 C8 C7 . . 126.3(3) ?
N4 C9 O2 . . 118.8(3) ?
N4 C9 N5 . . 127.5(3) ?
O2 C9 N5 . . 113.7(3) ?
O1 C10 N5 . . 121.3(3) ?
O1 C10 C7 . . 126.9(3) ?
N5 C10 C7 . . 111.8(3) ?
C16 C11 C12 . . 122.1(4) ?
C16 C11 O2 . . 119.3(3) ?
C12 C11 O2 . . 118.6(3) ?
C11 C12 C13 . . 119.1(4) ?
C11 C12 H12 . . 120.4 ?
C13 C12 H12 . . 120.4 ?
C14 C13 C12 . . 119.2(4) ?
C14 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
C15 C14 C13 . . 121.2(4) ?
C15 C14 Cl1 . . 119.4(3) ?
C13 C14 Cl1 . . 119.4(3) ?
C14 C15 C16 . . 119.7(4) ?
C14 C15 H15 . . 120.2 ?
C16 C15 H15 . . 120.2 ?
C11 C16 C15 . . 118.6(4) ?
C11 C16 H16 . . 120.7 ?
C15 C16 H16 . . 120.7 ?
C18 C17 N5 . . 111.7(3) ?
C18 C17 C19 . . 114.9(4) ?
N5 C17 C19 . . 111.0(3) ?
C18 C17 H17 . . 106.2 ?
N5 C17 H17 . . 106.2 ?
C19 C17 H17 . . 106.2 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C8 N1 N2 . . 108.0(3) ?
C8 N1 C1 . . 131.7(3) ?
N2 N1 C1 . . 120.2(3) ?
N3 N2 N1 . . 108.4(3) ?
N2 N3 C7 . . 108.6(3) ?
C9 N4 C8 . . 112.7(3) ?
C9 N5 C10 . . 121.0(3) ?
C9 N5 C17 . . 120.5(3) ?
C10 N5 C17 . . 118.5(3) ?
C9 O2 C11 . . 115.8(3) ?
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 C6 . 1.371(5) ?
C1 C2 . 1.372(5) ?
C1 N1 . 1.431(4) ?
C2 C3 . 1.380(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.365(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.366(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.383(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N3 . 1.358(4) ?
C7 C8 . 1.362(4) ?
C7 C10 . 1.436(5) ?
C8 N1 . 1.352(4) ?
C8 N4 . 1.358(4) ?
C9 N4 . 1.296(4) ?
C9 O2 . 1.346(4) ?
C9 N5 . 1.372(4) ?
C10 O1 . 1.210(4) ?
C10 N5 . 1.422(4) ?
C11 C16 . 1.348(5) ?
C11 C12 . 1.353(5) ?
C11 O2 . 1.414(4) ?
C12 C13 . 1.378(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.357(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.352(6) ?
C14 Cl1 . 1.749(4) ?
C15 C16 . 1.384(6) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 C18 . 1.500(6) ?
C17 N5 . 1.506(4) ?
C17 C19 . 1.509(6) ?
C17 H17 . 0.9800 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
N1 N2 . 1.385(4) ?
N2 N3 . 1.297(4) ?
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
C17 H17 O2 . 0.98 2.16 2.679(4) 111.7 y
C6 H6 N4 . 0.93 2.36 3.013(4) 127.4 y
C4 H4 O1 1_545 0.93 2.46 3.317(5) 153.5 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.7(6) ?
N1 C1 C2 C3 . . . . -178.5(4) ?
C1 C2 C3 C4 . . . . -0.6(7) ?
C2 C3 C4 C5 . . . . 0.2(7) ?
C3 C4 C5 C6 . . . . 0.1(7) ?
C2 C1 C6 C5 . . . . -0.4(5) ?
N1 C1 C6 C5 . . . . 178.7(3) ?
C4 C5 C6 C1 . . . . 0.0(6) ?
N3 C7 C8 N1 . . . . 0.3(4) ?
C10 C7 C8 N1 . . . . -178.6(3) ?
N3 C7 C8 N4 . . . . -179.7(3) ?
C10 C7 C8 N4 . . . . 1.4(5) ?
N3 C7 C10 O1 . . . . -3.4(6) ?
C8 C7 C10 O1 . . . . 175.3(4) ?
N3 C7 C10 N5 . . . . 178.6(3) ?
C8 C7 C10 N5 . . . . -2.7(5) ?
C16 C11 C12 C13 . . . . -2.7(6) ?
O2 C11 C12 C13 . . . . 179.7(3) ?
C11 C12 C13 C14 . . . . 0.4(6) ?
C12 C13 C14 C15 . . . . 2.5(7) ?
C12 C13 C14 Cl1 . . . . -177.4(3) ?
C13 C14 C15 C16 . . . . -3.1(7) ?
Cl1 C14 C15 C16 . . . . 176.8(3) ?
C12 C11 C16 C15 . . . . 2.2(6) ?
O2 C11 C16 C15 . . . . 179.8(4) ?
C14 C15 C16 C11 . . . . 0.7(7) ?
N4 C8 N1 N2 . . . . 179.5(3) ?
C7 C8 N1 N2 . . . . -0.5(3) ?
N4 C8 N1 C1 . . . . 0.0(6) ?
C7 C8 N1 C1 . . . . -180.0(3) ?
C6 C1 N1 C8 . . . . -0.1(5) ?
C2 C1 N1 C8 . . . . 179.0(3) ?
C6 C1 N1 N2 . . . . -179.6(3) ?
C2 C1 N1 N2 . . . . -0.4(5) ?
C8 N1 N2 N3 . . . . 0.4(4) ?
C1 N1 N2 N3 . . . . -180.0(3) ?
N1 N2 N3 C7 . . . . -0.2(4) ?
C8 C7 N3 N2 . . . . -0.1(4) ?
C10 C7 N3 N2 . . . . 178.8(4) ?
O2 C9 N4 C8 . . . . -179.1(3) ?
N5 C9 N4 C8 . . . . 0.0(5) ?
N1 C8 N4 C9 . . . . -179.9(3) ?
C7 C8 N4 C9 . . . . 0.1(5) ?
N4 C9 N5 C10 . . . . -1.6(5) ?
O2 C9 N5 C10 . . . . 177.5(3) ?
N4 C9 N5 C17 . . . . 178.6(3) ?
O2 C9 N5 C17 . . . . -2.3(4) ?
O1 C10 N5 C9 . . . . -175.3(3) ?
C7 C10 N5 C9 . . . . 2.8(4) ?
O1 C10 N5 C17 . . . . 4.4(5) ?
C7 C10 N5 C17 . . . . -177.4(3) ?
C18 C17 N5 C9 . . . . -119.2(4) ?
C19 C17 N5 C9 . . . . 111.3(4) ?
C18 C17 N5 C10 . . . . 61.1(4) ?
C19 C17 N5 C10 . . . . -68.5(4) ?
N4 C9 O2 C11 . . . . 0.2(5) ?
N5 C9 O2 C11 . . . . -179.0(3) ?
C16 C11 O2 C9 . . . . 89.1(4) ?
C12 C11 O2 C9 . . . . -93.2(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743345
