#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/56/2015656.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_2015656
loop_
_publ_author_name
'Dinçer, Muharrem'
'Özdemir, Namık'
'Çetin, Ahmet'
'Keser, Tekin'
'Büyükgüngör, Orhan'
_publ_section_title
;N-Cyclohexyl-2-[5-(4-pyridyl)-4-(p-tolyl)-4H-1,2,4-triazol-3-ylsulfanyl]acetamide
 dihydrate
;
_journal_coeditor_code           SF3017
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o639
_journal_page_last               o642
_journal_paper_doi               10.1107/S0108270106037930
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C22 H25 N5 O S , 2H2 O'
_chemical_formula_moiety         'C22 H25 N5 O S , 2(H2 O)'
_chemical_formula_sum            'C22 H29 N5 O3 S'
_chemical_formula_weight         443.56
_chemical_name_systematic
;
N-Cyclohexyl-2-[5-(4-pyridyl)-4-(p-tolyl)-4H-1,2,4-triazol-3-
ylsulfanyl]acetamide dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.306(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3634(10)
_cell_length_b                   6.8031(4)
_cell_length_c                   28.077(2)
_cell_measurement_reflns_used    26172
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      1.45
_cell_volume                     2361.5(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            26676
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.45
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.9211
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.174
_refine_ls_extinction_coef       0.0066(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4135
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0382
_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)+(0.0634P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2947
_reflns_number_total             4135
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3017.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015656
_cod_database_fobs_code          2015656
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S S3 0.23210(5) 0.54135(9) 0.550646(18) 0.0722(2) Uani d . 1
O O1W 0.3081(2) -0.0792(3) 0.64499(8) 0.0966(6) Uani d D 1
H H11W 0.343(3) -0.064(5) 0.6184(12) 0.119(11) Uiso d . 1
H H12W 0.260(3) -0.165(6) 0.6411(17) 0.20(2) Uiso d D 1
O O2W 0.56974(18) 0.0079(3) 0.43530(7) 0.1030(7) Uani d . 1
H H21W 0.533(3) 0.095(6) 0.4479(12) 0.143(13) Uiso d . 1
H H22W 0.571(2) -0.095(5) 0.4527(10) 0.106(9) Uiso d . 1
O O3 0.16757(14) 0.5786(2) 0.64496(5) 0.0826(5) Uani d . 1
N N1 0.43480(13) 0.3257(2) 0.45999(5) 0.0593(4) Uani d . 1
N N2 0.38925(13) 0.3274(2) 0.50506(5) 0.0598(4) Uani d . 1
N N3 0.21820(13) 0.2839(2) 0.67360(5) 0.0598(4) Uani d . 1
H H3 0.2510 0.1756 0.6672 0.072 Uiso calc R 1
N N4 0.31391(11) 0.5604(2) 0.46182(5) 0.0503(4) Uani d . 1
N N5 0.48340(16) 0.5811(3) 0.29153(7) 0.0850(6) Uani d . 1
C C3 0.31735(15) 0.4685(3) 0.50519(6) 0.0536(4) Uani d . 1
C C5 0.38915(14) 0.4644(3) 0.43469(6) 0.0500(4) Uani d . 1
C C31 0.27660(16) 0.3733(3) 0.59562(6) 0.0622(5) Uani d . 1
H H31A 0.2619 0.2391 0.5858 0.075 Uiso calc R 1
H H31B 0.3538 0.3871 0.6010 0.075 Uiso calc R 1
C C32 0.21543(15) 0.4212(3) 0.64068(7) 0.0578(5) Uani d . 1
C C33 0.16869(16) 0.3053(3) 0.72039(6) 0.0582(5) Uani d . 1
H H33 0.0953 0.3567 0.7158 0.070 Uiso calc R 1
C C34 0.1600(2) 0.1054(4) 0.74345(8) 0.0859(7) Uani d . 1
H H34A 0.2315 0.0485 0.7468 0.103 Uiso calc R 1
H H34B 0.1172 0.0192 0.7233 0.103 Uiso calc R 1
C C35 0.1071(3) 0.1219(4) 0.79251(9) 0.1012(9) Uani d . 1
H H35A 0.0332 0.1677 0.7889 0.121 Uiso calc R 1
H H35B 0.1053 -0.0065 0.8075 0.121 Uiso calc R 1
C C36 0.1691(2) 0.2624(5) 0.82340(9) 0.1010(9) Uani d . 1
H H36A 0.2413 0.2112 0.8290 0.121 Uiso calc R 1
H H36B 0.1335 0.2741 0.8540 0.121 Uiso calc R 1
C C37 0.1770(3) 0.4637(5) 0.80047(9) 0.0998(9) Uani d . 1
H H37A 0.2196 0.5502 0.8206 0.120 Uiso calc R 1
H H37B 0.1052 0.5198 0.7971 0.120 Uiso calc R 1
C C38 0.2299(2) 0.4475(4) 0.75134(8) 0.0863(7) Uani d . 1
H H38A 0.2309 0.5757 0.7363 0.104 Uiso calc R 1
H H38B 0.3040 0.4032 0.7550 0.104 Uiso calc R 1
C C41 0.23171(14) 0.7009(3) 0.44848(6) 0.0488(4) Uani d . 1
C C42 0.23571(17) 0.8886(3) 0.46582(8) 0.0664(5) Uani d . 1
H H42 0.2946 0.9311 0.4838 0.080 Uiso calc R 1
C C43 0.1500(2) 1.0144(3) 0.45603(9) 0.0781(6) Uani d . 1
H H43 0.1521 1.1421 0.4678 0.094 Uiso calc R 1
C C44 0.06237(17) 0.9557(4) 0.42949(8) 0.0755(7) Uani d . 1
C C45 0.06281(18) 0.7683(4) 0.41153(9) 0.0842(7) Uani d . 1
H H45 0.0056 0.7274 0.3923 0.101 Uiso calc R 1
C C46 0.14583(17) 0.6392(3) 0.42120(8) 0.0692(5) Uani d . 1
H H46 0.1437 0.5116 0.4094 0.083 Uiso calc R 1
C C47 -0.0318(2) 1.0943(5) 0.42092(12) 0.1224(12) Uani d . 1
H H47A -0.0267 1.2036 0.4425 0.184 Uiso calc R 1
H H47B -0.0985 1.0257 0.4262 0.184 Uiso calc R 1
H H47C -0.0298 1.1413 0.3887 0.184 Uiso calc R 1
C C51 0.41822(14) 0.5090(3) 0.38515(6) 0.0523(4) Uani d . 1
C C52 0.41153(17) 0.6946(3) 0.36565(8) 0.0697(6) Uani d . 1
H H52 0.3849 0.7992 0.3834 0.084 Uiso calc R 1
C C53 0.4450(2) 0.7223(4) 0.31934(9) 0.0837(7) Uani d . 1
H H53 0.4404 0.8485 0.3068 0.100 Uiso calc R 1
C C54 0.49046(18) 0.4045(4) 0.31104(8) 0.0777(6) Uani d . 1
H H54 0.5182 0.3030 0.2926 0.093 Uiso calc R 1
C C55 0.45952(16) 0.3614(3) 0.35676(7) 0.0638(5) Uani d . 1
H H55 0.4663 0.2341 0.3685 0.077 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'
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
C3 S3 C31 98.69(8) yes
H11W O1W H12W 109(4) ?
H21W O2W H22W 111(3) ?
C5 N1 N2 108.27(13) yes
C3 N2 N1 106.72(14) yes
C32 N3 C33 123.56(16) yes
C32 N3 H3 118.2 ?
C33 N3 H3 118.2 ?
C3 N4 C5 104.98(14) yes
C3 N4 C41 123.50(14) ?
C5 N4 C41 130.55(14) ?
C54 N5 C53 115.89(19) ?
N2 C3 N4 110.52(15) yes
N2 C3 S3 128.92(14) yes
N4 C3 S3 120.55(12) yes
N1 C5 N4 109.51(15) yes
N1 C5 C51 123.79(15) ?
N4 C5 C51 126.68(15) ?
C32 C31 S3 107.43(13) yes
C32 C31 H31A 110.2 ?
S3 C31 H31A 110.2 ?
C32 C31 H31B 110.2 ?
S3 C31 H31B 110.2 ?
H31A C31 H31B 108.5 ?
O3 C32 N3 124.11(17) yes
O3 C32 C31 120.80(17) yes
N3 C32 C31 115.09(16) yes
N3 C33 C38 111.88(16) ?
N3 C33 C34 109.10(16) ?
C38 C33 C34 111.63(19) ?
N3 C33 H33 108.0 ?
C38 C33 H33 108.0 ?
C34 C33 H33 108.0 ?
C33 C34 C35 110.6(2) ?
C33 C34 H34A 109.5 ?
C35 C34 H34A 109.5 ?
C33 C34 H34B 109.5 ?
C35 C34 H34B 109.5 ?
H34A C34 H34B 108.1 ?
C36 C35 C34 110.3(2) ?
C36 C35 H35A 109.6 ?
C34 C35 H35A 109.6 ?
C36 C35 H35B 109.6 ?
C34 C35 H35B 109.6 ?
H35A C35 H35B 108.1 ?
C35 C36 C37 111.3(2) ?
C35 C36 H36A 109.4 ?
C37 C36 H36A 109.4 ?
C35 C36 H36B 109.4 ?
C37 C36 H36B 109.4 ?
H36A C36 H36B 108.0 ?
C36 C37 C38 110.2(2) ?
C36 C37 H37A 109.6 ?
C38 C37 H37A 109.6 ?
C36 C37 H37B 109.6 ?
C38 C37 H37B 109.6 ?
H37A C37 H37B 108.1 ?
C33 C38 C37 110.54(19) ?
C33 C38 H38A 109.5 ?
C37 C38 H38A 109.5 ?
C33 C38 H38B 109.5 ?
C37 C38 H38B 109.5 ?
H38A C38 H38B 108.1 ?
C42 C41 C46 120.73(17) ?
C42 C41 N4 120.11(16) ?
C46 C41 N4 118.98(16) ?
C41 C42 C43 118.6(2) ?
C41 C42 H42 120.7 ?
C43 C42 H42 120.7 ?
C44 C43 C42 121.9(2) ?
C44 C43 H43 119.1 ?
C42 C43 H43 119.1 ?
C43 C44 C45 117.78(19) ?
C43 C44 C47 120.6(3) ?
C45 C44 C47 121.6(3) ?
C44 C45 C46 121.7(2) ?
C44 C45 H45 119.2 ?
C46 C45 H45 119.2 ?
C41 C46 C45 119.3(2) ?
C41 C46 H46 120.4 ?
C45 C46 H46 120.4 ?
C44 C47 H47A 109.5 ?
C44 C47 H47B 109.5 ?
H47A C47 H47B 109.5 ?
C44 C47 H47C 109.5 ?
H47A C47 H47C 109.5 ?
H47B C47 H47C 109.5 ?
C52 C51 C55 117.27(18) ?
C52 C51 C5 123.40(17) ?
C55 C51 C5 119.26(17) ?
C51 C52 C53 118.8(2) ?
C51 C52 H52 120.6 ?
C53 C52 H52 120.6 ?
N5 C53 C52 124.4(2) ?
N5 C53 H53 117.8 ?
C52 C53 H53 117.8 ?
N5 C54 C55 124.3(2) ?
N5 C54 H54 117.9 ?
C55 C54 H54 117.9 ?
C54 C55 C51 119.3(2) ?
C54 C55 H55 120.3 ?
C51 C55 H55 120.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S3 C3 1.7319(18) ?
S3 C31 1.7880(19) ?
O1W H11W 0.87(3) ?
O1W H12W 0.84(2) ?
O2W H21W 0.83(4) ?
O2W H22W 0.86(3) ?
O3 C32 1.230(2) yes
N1 C5 1.308(2) yes
N1 N2 1.388(2) ?
N2 C3 1.308(2) yes
N3 C32 1.314(2) ?
N3 C33 1.460(2) ?
N3 H3 0.8600 ?
N4 C3 1.369(2) yes
N4 C5 1.371(2) yes
N4 C41 1.443(2) yes
N5 C54 1.323(3) ?
N5 C53 1.328(3) ?
C5 C51 1.470(2) yes
C31 C32 1.513(2) yes
C31 H31A 0.9700 ?
C31 H31B 0.9700 ?
C33 C38 1.502(3) ?
C33 C34 1.510(3) ?
C33 H33 0.9800 ?
C34 C35 1.532(3) ?
C34 H34A 0.9700 ?
C34 H34B 0.9700 ?
C35 C36 1.499(4) ?
C35 H35A 0.9700 ?
C35 H35B 0.9700 ?
C36 C37 1.517(4) ?
C36 H36A 0.9700 ?
C36 H36B 0.9700 ?
C37 C38 1.534(3) ?
C37 H37A 0.9700 ?
C37 H37B 0.9700 ?
C38 H38A 0.9700 ?
C38 H38B 0.9700 ?
C41 C42 1.368(3) ?
C41 C46 1.372(3) ?
C42 C43 1.389(3) ?
C42 H42 0.9300 ?
C43 C44 1.371(4) ?
C43 H43 0.9300 ?
C44 C45 1.371(4) ?
C44 C47 1.516(3) ?
C45 C46 1.377(3) ?
C45 H45 0.9300 ?
C46 H46 0.9300 ?
C47 H47A 0.9600 ?
C47 H47B 0.9600 ?
C47 H47C 0.9600 ?
C51 C52 1.378(3) ?
C51 C55 1.382(3) ?
C52 C53 1.380(3) ?
C52 H52 0.9300 ?
C53 H53 0.9300 ?
C54 C55 1.373(3) ?
C54 H54 0.9300 ?
C55 H55 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
O1W H11W O2W 3_656 0.87(3) 1.90(3) 2.763(3) 172(3)
N3 H3 O1W . 0.86 1.97 2.827(2) 170.9
O2W H22W N2 3_656 0.86(3) 2.03(3) 2.873(2) 167(3)
O2W H21W N1 . 0.83(4) 2.01(4) 2.819(2) 165(3)
O1W H12W O3 1_545 0.84(2) 2.09(2) 2.905(3) 164(5)
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
C5 N1 N2 C3 -0.1(2) ?
N1 N2 C3 N4 -0.1(2) ?
N1 N2 C3 S3 178.86(15) ?
C5 N4 C3 N2 0.3(2) ?
C41 N4 C3 N2 170.03(16) ?
C5 N4 C3 S3 -178.82(14) ?
C41 N4 C3 S3 -9.0(3) ?
C31 S3 C3 N2 1.9(2) ?
C31 S3 C3 N4 -179.24(16) ?
N2 N1 C5 N4 0.2(2) ?
N2 N1 C5 C51 178.91(17) ?
C3 N4 C5 N1 -0.3(2) ?
C41 N4 C5 N1 -169.07(17) ?
C3 N4 C5 C51 -178.93(17) ?
C41 N4 C5 C51 12.3(3) ?
C3 S3 C31 C32 176.56(15) yes
C33 N3 C32 O3 -2.9(3) yes
C33 N3 C32 C31 177.03(17) yes
S3 C31 C32 O3 -16.0(3) yes
S3 C31 C32 N3 164.05(15) ?
C32 N3 C33 C38 -71.5(3) ?
C32 N3 C33 C34 164.5(2) ?
N3 C33 C34 C35 -179.4(2) ?
C38 C33 C34 C35 56.5(3) ?
C33 C34 C35 C36 -56.4(3) ?
C34 C35 C36 C37 57.4(3) ?
C35 C36 C37 C38 -57.3(3) ?
N3 C33 C38 C37 -179.0(2) ?
C34 C33 C38 C37 -56.4(3) ?
C36 C37 C38 C33 56.1(3) ?
C3 N4 C41 C42 76.5(2) ?
C5 N4 C41 C42 -116.5(2) ?
C3 N4 C41 C46 -98.6(2) ?
C5 N4 C41 C46 68.3(3) ?
C46 C41 C42 C43 1.2(3) ?
N4 C41 C42 C43 -173.85(18) ?
C41 C42 C43 C44 -0.2(3) ?
C42 C43 C44 C45 -1.7(3) ?
C42 C43 C44 C47 177.8(2) ?
C43 C44 C45 C46 2.7(4) ?
C47 C44 C45 C46 -176.8(2) ?
C42 C41 C46 C45 -0.3(3) ?
N4 C41 C46 C45 174.84(19) ?
C44 C45 C46 C41 -1.7(4) ?
N1 C5 C51 C52 -149.1(2) ?
N4 C5 C51 C52 29.3(3) ?
N1 C5 C51 C55 27.6(3) ?
N4 C5 C51 C55 -153.98(19) ?
C55 C51 C52 C53 0.6(3) ?
C5 C51 C52 C53 177.4(2) ?
C54 N5 C53 C52 -1.2(4) ?
C51 C52 C53 N5 0.4(4) ?
C53 N5 C54 C55 1.0(4) ?
N5 C54 C55 C51 -0.1(4) ?
C52 C51 C55 C54 -0.7(3) ?
C5 C51 C55 C54 -177.60(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133368
