#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220708.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_2220708
loop_
_publ_author_name
'Xiao, Shan-Mei'
_publ_section_title
1-(4-Bromophenyl)-2-{5-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-phenyl-4H-1,2,4-triazol-3-ylsulfanyl}ethanone
_journal_coeditor_code           BQ2115
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o273
_journal_paper_doi               10.1107/S1600536809000403
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H20 Br N5 O S'
_chemical_formula_moiety         'C22 H20 Br N5 O S'
_chemical_formula_sum            'C22 H20 Br N5 O S'
_chemical_formula_weight         482.40
_chemical_name_systematic
;1-(4-Bromophenyl)-2-{5-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-phenyl-
4H-1,2,4-triazol-3-ylsulfanyl}ethanone
;
_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           SHELXL-97
_cell_angle_alpha                94.561(4)
_cell_angle_beta                 97.659(4)
_cell_angle_gamma                103.086(4)
_cell_formula_units_Z            2
_cell_length_a                   8.705(2)
_cell_length_b                   9.173(2)
_cell_length_c                   14.564(4)
_cell_measurement_reflns_used    1669
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.98
_cell_measurement_theta_min      2.56
_cell_volume                     1115.4(5)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5704
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    1.960
_exptl_absorpt_correction_T_max  0.6744
_exptl_absorpt_correction_T_min  0.5916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.371
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0409
_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)+(0.0351P)²+0.4689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                2419
_reflns_number_total             3914
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2115.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_cell_volume        1115.3(5)
_cod_database_code               2220708
_cod_database_fobs_code          2220708
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.29289(6) 0.67651(6) -0.50744(3) 0.0905(2) Uani d . 1 . .
S S1 0.55698(11) 0.71293(10) 0.09603(6) 0.0490(3) Uani d . 1 . .
O O1 0.6651(3) 0.6235(2) -0.07550(16) 0.0513(6) Uani d . 1 . .
N N1 1.0999(3) 1.1534(3) 0.3101(2) 0.0510(7) Uani d . 1 . .
N N2 1.1688(3) 1.0707(3) 0.25343(19) 0.0454(7) Uani d . 1 . .
N N3 0.8643(4) 1.0825(3) 0.07347(19) 0.0501(7) Uani d . 1 . .
N N4 0.7096(3) 0.9911(3) 0.05655(19) 0.0499(7) Uani d . 1 . .
N N5 0.8674(3) 0.8715(3) 0.13335(16) 0.0364(6) Uani d . 1 . .
C C1 1.1192(6) 1.2185(5) 0.4789(3) 0.0941(15) Uani d . 1 . .
H H1A 1.0703 1.2973 0.4597 0.141 Uiso calc R 1 . .
H H1B 1.2134 1.2611 0.5236 0.141 Uiso calc R 1 . .
H H1C 1.0455 1.1474 0.5066 0.141 Uiso calc R 1 . .
C C2 1.1639(5) 1.1397(4) 0.3953(3) 0.0590(10) Uani d . 1 . .
C C3 1.2727(5) 1.0505(4) 0.3942(3) 0.0640(11) Uani d . 1 . .
H H3 1.3327 1.0254 0.4456 0.077 Uiso calc R 1 . .
C C4 1.2744(4) 1.0070(4) 0.3029(3) 0.0548(10) Uani d . 1 . .
C C5 1.3679(5) 0.9113(5) 0.2587(3) 0.0835(14) Uani d . 1 . .
H H5A 1.2977 0.8172 0.2309 0.125 Uiso calc R 1 . .
H H5B 1.4481 0.8926 0.3052 0.125 Uiso calc R 1 . .
H H5C 1.4182 0.9623 0.2115 0.125 Uiso calc R 1 . .
C C6 1.1288(4) 1.0667(4) 0.1533(2) 0.0507(9) Uani d . 1 . .
H H6A 1.1863 1.0030 0.1228 0.061 Uiso calc R 1 . .
H H6B 1.1632 1.1676 0.1360 0.061 Uiso calc R 1 . .
C C7 0.9553(4) 1.0093(3) 0.1199(2) 0.0405(8) Uani d . 1 . .
C C8 0.7156(4) 0.8664(3) 0.0931(2) 0.0398(8) Uani d . 1 . .
C C9 0.9262(4) 0.7495(3) 0.1701(2) 0.0363(7) Uani d . 1 . .
C C10 0.9932(4) 0.6635(4) 0.1140(3) 0.0571(10) Uani d . 1 . .
H H10 1.0027 0.6845 0.0533 0.069 Uiso calc R 1 . .
C C11 1.0469(5) 0.5443(4) 0.1486(3) 0.0730(12) Uani d . 1 . .
H H11 1.0928 0.4846 0.1112 0.088 Uiso calc R 1 . .
C C12 1.0322(5) 0.5149(4) 0.2383(3) 0.0658(11) Uani d . 1 . .
H H12 1.0665 0.4340 0.2613 0.079 Uiso calc R 1 . .
C C13 0.9675(5) 0.6034(4) 0.2940(3) 0.0635(11) Uani d . 1 . .
H H13 0.9603 0.5840 0.3552 0.076 Uiso calc R 1 . .
C C14 0.9126(4) 0.7216(4) 0.2602(2) 0.0514(9) Uani d . 1 . .
H H14 0.8671 0.7813 0.2978 0.062 Uiso calc R 1 . .
C C15 0.4513(4) 0.7061(4) -0.0201(2) 0.0461(9) Uani d . 1 . .
H H15A 0.3481 0.6353 -0.0262 0.055 Uiso calc R 1 . .
H H15B 0.4326 0.8047 -0.0291 0.055 Uiso calc R 1 . .
C C16 0.5408(4) 0.6597(3) -0.0953(2) 0.0395(8) Uani d . 1 . .
C C17 0.4720(4) 0.6607(3) -0.1940(2) 0.0420(8) Uani d . 1 . .
C C18 0.3491(4) 0.7294(4) -0.2204(2) 0.0509(9) Uani d . 1 . .
H H18 0.3023 0.7726 -0.1749 0.061 Uiso calc R 1 . .
C C19 0.2954(4) 0.7345(4) -0.3134(3) 0.0587(10) Uani d . 1 . .
H H19 0.2140 0.7820 -0.3308 0.070 Uiso calc R 1 . .
C C20 0.3635(5) 0.6689(4) -0.3794(2) 0.0557(10) Uani d . 1 . .
C C21 0.4837(5) 0.5963(4) -0.3557(3) 0.0638(11) Uani d . 1 . .
H H21 0.5276 0.5505 -0.4015 0.077 Uiso calc R 1 . .
C C22 0.5363(4) 0.5937(4) -0.2631(3) 0.0547(10) Uani d . 1 . .
H H22 0.6173 0.5457 -0.2463 0.066 Uiso calc R 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C8 S1 C15 . . 98.77(15) ?
C2 N1 N2 . . 104.6(3) ?
C4 N2 N1 . . 111.8(3) ?
C4 N2 C6 . . 129.2(3) ?
N1 N2 C6 . . 118.9(3) ?
C7 N3 N4 . . 107.4(3) ?
C8 N4 N3 . . 106.9(3) ?
C8 N5 C7 . . 105.1(2) ?
C8 N5 C9 . . 127.1(3) ?
C7 N5 C9 . . 127.3(3) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 C3 . . 111.3(3) ?
N1 C2 C1 . . 120.7(4) ?
C3 C2 C1 . . 127.9(4) ?
C4 C3 C2 . . 106.4(3) ?
C4 C3 H3 . . 126.8 ?
C2 C3 H3 . . 126.8 ?
N2 C4 C3 . . 105.9(3) ?
N2 C4 C5 . . 123.3(4) ?
C3 C4 C5 . . 130.9(4) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N2 C6 C7 . . 112.5(3) ?
N2 C6 H6A . . 109.1 ?
C7 C6 H6A . . 109.1 ?
N2 C6 H6B . . 109.1 ?
C7 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.8 ?
N3 C7 N5 . . 110.1(3) ?
N3 C7 C6 . . 125.2(3) ?
N5 C7 C6 . . 124.7(3) ?
N4 C8 N5 . . 110.5(3) ?
N4 C8 S1 . . 127.3(3) ?
N5 C8 S1 . . 122.2(2) ?
C10 C9 C14 . . 121.4(3) ?
C10 C9 N5 . . 119.1(3) ?
C14 C9 N5 . . 119.5(3) ?
C9 C10 C11 . . 119.2(3) ?
C9 C10 H10 . . 120.4 ?
C11 C10 H10 . . 120.4 ?
C12 C11 C10 . . 119.7(4) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C13 C12 C11 . . 120.4(3) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 120.4(4) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C9 C14 C13 . . 118.9(3) ?
C9 C14 H14 . . 120.6 ?
C13 C14 H14 . . 120.6 ?
C16 C15 S1 . . 112.9(2) ?
C16 C15 H15A . . 109.0 ?
S1 C15 H15A . . 109.0 ?
C16 C15 H15B . . 109.0 ?
S1 C15 H15B . . 109.0 ?
H15A C15 H15B . . 107.8 ?
O1 C16 C17 . . 120.9(3) ?
O1 C16 C15 . . 121.0(3) ?
C17 C16 C15 . . 118.1(3) ?
C22 C17 C18 . . 118.4(3) ?
C22 C17 C16 . . 118.5(3) ?
C18 C17 C16 . . 123.1(3) ?
C19 C18 C17 . . 120.7(3) ?
C19 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C20 C19 C18 . . 119.0(3) ?
C20 C19 H19 . . 120.5 ?
C18 C19 H19 . . 120.5 ?
C19 C20 C21 . . 121.8(3) ?
C19 C20 Br1 . . 119.6(3) ?
C21 C20 Br1 . . 118.6(3) ?
C22 C21 C20 . . 118.3(3) ?
C22 C21 H21 . . 120.9 ?
C20 C21 H21 . . 120.9 ?
C21 C22 C17 . . 121.7(3) ?
C21 C22 H22 . . 119.1 ?
C17 C22 H22 . . 119.1 ?
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
Br1 C20 . 1.896(3) ?
S1 C8 . 1.742(3) ?
S1 C15 . 1.803(3) ?
O1 C16 . 1.208(3) ?
N1 C2 . 1.319(4) ?
N1 N2 . 1.362(4) ?
N2 C4 . 1.356(4) ?
N2 C6 . 1.449(4) ?
N3 C7 . 1.306(4) ?
N3 N4 . 1.395(4) ?
N4 C8 . 1.308(4) ?
N5 C8 . 1.361(4) ?
N5 C7 . 1.365(4) ?
N5 C9 . 1.443(4) ?
C1 C2 . 1.506(5) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.385(5) ?
C3 C4 . 1.360(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.491(5) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 C7 . 1.483(5) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C9 C10 . 1.365(4) ?
C9 C14 . 1.372(4) ?
C10 C11 . 1.387(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.371(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.363(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.380(5) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.514(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.484(4) ?
C17 C22 . 1.382(4) ?
C17 C18 . 1.387(4) ?
C18 C19 . 1.381(5) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.363(5) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.382(5) ?
C21 C22 . 1.369(5) ?
C21 H21 . 0.9300 ?
C22 H22 . 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
C6 H6B O1 2_775 0.97 2.45 3.365(3) 157
C15 H15B N4 2_675 0.97 2.50 3.429(3) 161
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
C2 N1 N2 C4 . . . . -0.2(4) ?
C2 N1 N2 C6 . . . . -177.5(3) ?
C7 N3 N4 C8 . . . . -0.5(3) ?
N2 N1 C2 C3 . . . . 0.3(4) ?
N2 N1 C2 C1 . . . . 179.0(3) ?
N1 C2 C3 C4 . . . . -0.2(5) ?
C1 C2 C3 C4 . . . . -178.9(4) ?
N1 N2 C4 C3 . . . . 0.0(4) ?
C6 N2 C4 C3 . . . . 177.0(3) ?
N1 N2 C4 C5 . . . . -179.6(3) ?
C6 N2 C4 C5 . . . . -2.6(5) ?
C2 C3 C4 N2 . . . . 0.1(4) ?
C2 C3 C4 C5 . . . . 179.7(4) ?
C4 N2 C6 C7 . . . . 124.9(4) ?
N1 N2 C6 C7 . . . . -58.3(4) ?
N4 N3 C7 N5 . . . . 0.9(3) ?
N4 N3 C7 C6 . . . . -179.1(3) ?
C8 N5 C7 N3 . . . . -0.9(3) ?
C9 N5 C7 N3 . . . . 171.0(3) ?
C8 N5 C7 C6 . . . . 179.0(3) ?
C9 N5 C7 C6 . . . . -9.0(5) ?
N2 C6 C7 N3 . . . . 122.0(3) ?
N2 C6 C7 N5 . . . . -58.0(4) ?
N3 N4 C8 N5 . . . . -0.1(3) ?
N3 N4 C8 S1 . . . . 178.2(2) ?
C7 N5 C8 N4 . . . . 0.6(3) ?
C9 N5 C8 N4 . . . . -171.4(3) ?
C7 N5 C8 S1 . . . . -177.8(2) ?
C9 N5 C8 S1 . . . . 10.3(4) ?
C15 S1 C8 N4 . . . . 40.6(3) ?
C15 S1 C8 N5 . . . . -141.3(3) ?
C8 N5 C9 C10 . . . . 93.5(4) ?
C7 N5 C9 C10 . . . . -76.7(4) ?
C8 N5 C9 C14 . . . . -86.0(4) ?
C7 N5 C9 C14 . . . . 103.8(4) ?
C14 C9 C10 C11 . . . . 0.7(5) ?
N5 C9 C10 C11 . . . . -178.7(3) ?
C9 C10 C11 C12 . . . . -0.1(6) ?
C10 C11 C12 C13 . . . . -1.1(6) ?
C11 C12 C13 C14 . . . . 1.5(6) ?
C10 C9 C14 C13 . . . . -0.3(5) ?
N5 C9 C14 C13 . . . . 179.2(3) ?
C12 C13 C14 C9 . . . . -0.9(6) ?
C8 S1 C15 C16 . . . . 68.2(2) ?
S1 C15 C16 O1 . . . . 4.1(4) ?
S1 C15 C16 C17 . . . . -175.6(2) ?
O1 C16 C17 C22 . . . . 11.7(5) ?
C15 C16 C17 C22 . . . . -168.6(3) ?
O1 C16 C17 C18 . . . . -166.4(3) ?
C15 C16 C17 C18 . . . . 13.2(4) ?
C22 C17 C18 C19 . . . . -1.8(5) ?
C16 C17 C18 C19 . . . . 176.3(3) ?
C17 C18 C19 C20 . . . . 0.9(5) ?
C18 C19 C20 C21 . . . . 0.6(6) ?
C18 C19 C20 Br1 . . . . -179.3(3) ?
C19 C20 C21 C22 . . . . -1.2(6) ?
Br1 C20 C21 C22 . . . . 178.8(3) ?
C20 C21 C22 C17 . . . . 0.3(6) ?
C18 C17 C22 C21 . . . . 1.2(5) ?
C16 C17 C22 C21 . . . . -177.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741531
