#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/46/2014673.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_2014673
loop_
_publ_author_name
'Yilmaz, Veysel T.'
'Kazak, Canan'
'Ağar, Erbil'
'Kahveci, Bahittin'
'Guven, Kutalmis'
_publ_section_title
;
 Three 1,2,4-triazole derivatives containing subtituted benzyl and
 benzylamino groups
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o101
_journal_page_last               o104
_journal_paper_doi               10.1107/S0108270104033931
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H18 N4 O'
_chemical_formula_moiety         'C17 H18 N4 O'
_chemical_formula_sum            'C17 H18 N4 O'
_chemical_formula_weight         294.35
_chemical_name_systematic
;
4-Benzylamino-3-(4-methylbenzyl)-4,5-dihydro-1H-1,2,4-triazol-5-one
;
_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                 108.496(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.0906(13)
_cell_length_b                   5.9866(3)
_cell_length_c                   15.6784(15)
_cell_measurement_reflns_used    12405
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      1.26
_cell_volume                     1521.3(2)
_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 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       rotation
_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  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20832
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         1.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.199
_refine_ls_extinction_coef       0.020(2)
_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   0.929
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0697P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2054
_reflns_number_total             3008
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1519.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014673
_cod_database_fobs_code          2014673
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_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
_atom_site_type_symbol
C1 0.57217(11) 0.6733(4) 0.93832(13) 0.0849(6) Uani d . 1 . . C
H1A 0.5642 0.6610 0.9961 0.102 Uiso calc R 1 . . H
H1B 0.6155 0.7785 0.9419 0.102 Uiso calc R 1 . . H
H1C 0.5870 0.5300 0.9206 0.102 Uiso calc R 1 . . H
C2 0.49347(9) 0.7526(3) 0.86998(11) 0.0585(4) Uani d . 1 . . C
C3 0.46243(10) 0.9645(3) 0.87452(11) 0.0619(4) Uani d . 1 . . C
H3 0.4905 1.0601 0.9209 0.074 Uiso calc R 1 . . H
C4 0.39017(9) 1.0364(3) 0.81101(11) 0.0558(4) Uani d . 1 . . C
H4 0.3700 1.1784 0.8161 0.067 Uiso calc R 1 . . H
C5 0.34760(8) 0.9009(2) 0.74039(10) 0.0463(3) Uani d . 1 . . C
C6 0.37900(9) 0.6908(3) 0.73539(11) 0.0564(4) Uani d . 1 . . C
H6 0.3514 0.5963 0.6884 0.068 Uiso calc R 1 . . H
C7 0.45080(10) 0.6179(3) 0.79909(12) 0.0610(4) Uani d . 1 . . C
H7 0.4706 0.4755 0.7940 0.073 Uiso calc R 1 . . H
C8 0.27072(8) 0.9855(2) 0.66970(10) 0.0480(3) Uani d . 1 . . C
H8A 0.2759 1.1456 0.6637 0.058 Uiso calc R 1 . . H
H8B 0.2677 0.9181 0.6125 0.058 Uiso calc R 1 . . H
C9 0.19207(8) 0.9396(2) 0.68817(9) 0.0424(3) Uani d . 1 . . C
C10 0.07857(8) 0.7662(2) 0.69513(9) 0.0467(3) Uani d . 1 . . C
C11 0.12621(10) 0.5108(3) 0.54312(11) 0.0611(4) Uani d . 1 . . C
H11A 0.0682 0.5376 0.5342 0.073 Uiso calc R 1 . . H
H11B 0.1323 0.3573 0.5265 0.073 Uiso calc R 1 . . H
C12 0.15530(9) 0.6651(3) 0.48429(10) 0.0533(4) Uani d . 1 . . C
C13 0.22901(10) 0.6247(3) 0.46771(11) 0.0626(4) Uani d . 1 . . C
H13 0.2582 0.4943 0.4892 0.075 Uiso calc R 1 . . H
C14 0.25978(12) 0.7760(4) 0.41962(12) 0.0761(5) Uani d . 1 . . C
H14 0.3095 0.7472 0.4093 0.091 Uiso calc R 1 . . H
C15 0.21718(14) 0.9675(4) 0.38727(12) 0.0803(6) Uani d . 1 . . C
H15 0.2382 1.0705 0.3558 0.096 Uiso calc R 1 . . H
C16 0.14365(14) 1.0070(3) 0.40136(13) 0.0794(6) Uani d . 1 . . C
H16 0.1141 1.1359 0.3784 0.095 Uiso calc R 1 . . H
C17 0.11291(11) 0.8574(3) 0.44934(11) 0.0672(5) Uani d . 1 . . C
H17 0.0627 0.8867 0.4583 0.081 Uiso calc R 1 . . H
N1 0.08248(7) 0.9776(2) 0.72416(9) 0.0530(3) Uani d . 1 . . N
N2 0.15298(7) 1.08727(19) 0.72013(9) 0.0508(3) Uani d . 1 . . N
N3 0.14967(6) 0.74315(18) 0.67181(7) 0.0424(3) Uani d . 1 . . N
N4 0.17394(7) 0.5454(2) 0.63873(9) 0.0485(3) Uani d . 1 . . N
O1 0.02578(6) 0.62074(18) 0.68820(8) 0.0600(3) Uani d . 1 . . O
H1 0.0438(12) 1.044(3) 0.7510(13) 0.088(6) Uiso d . 1 . . H
H4A 0.1644(10) 0.432(3) 0.6707(11) 0.061(5) Uiso d . 1 . . H
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 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 ?
C7 C2 C3 117.61(15) ?
C7 C2 C1 120.92(16) ?
C3 C2 C1 121.46(17) ?
C2 C3 C4 121.04(16) ?
C2 C3 H3 119.5 ?
C4 C3 H3 119.5 ?
C5 C4 C3 121.13(15) ?
C5 C4 H4 119.4 ?
C3 C4 H4 119.4 ?
C4 C5 C6 117.80(14) ?
C4 C5 C8 120.39(13) ?
C6 C5 C8 121.78(13) ?
C5 C6 C7 121.21(15) ?
C5 C6 H6 119.4 ?
C7 C6 H6 119.4 ?
C2 C7 C6 121.21(15) ?
C2 C7 H7 119.4 ?
C6 C7 H7 119.4 ?
C9 C8 C5 115.10(11) ?
C9 C8 H8A 108.5 ?
C5 C8 H8A 108.5 ?
C9 C8 H8B 108.5 ?
C5 C8 H8B 108.5 ?
H8A C8 H8B 107.5 ?
N2 C9 N3 110.59(11) yes
N2 C9 C8 123.78(12) ?
N3 C9 C8 125.59(12) ?
O1 C10 N1 130.79(13) ?
O1 C10 N3 125.85(13) ?
N1 C10 N3 103.36(11) yes
N4 C11 C12 110.77(12) yes
N4 C11 H11A 109.5 ?
C12 C11 H11A 109.5 ?
N4 C11 H11B 109.5 ?
C12 C11 H11B 109.5 ?
H11A C11 H11B 108.1 ?
C17 C12 C13 117.76(16) ?
C17 C12 C11 121.66(15) ?
C13 C12 C11 120.47(15) ?
C14 C13 C12 120.86(17) ?
C14 C13 H13 119.6 ?
C12 C13 H13 119.6 ?
C15 C14 C13 120.09(18) ?
C15 C14 H14 120.0 ?
C13 C14 H14 120.0 ?
C16 C15 C14 119.66(19) ?
C16 C15 H15 120.2 ?
C14 C15 H15 120.2 ?
C15 C16 C17 120.46(19) ?
C15 C16 H16 119.8 ?
C17 C16 H16 119.8 ?
C16 C17 C12 121.15(17) ?
C16 C17 H17 119.4 ?
C12 C17 H17 119.4 ?
C10 N1 N2 112.41(11) yes
C10 N1 H1 124.3(12) ?
N2 N1 H1 123.0(12) ?
C9 N2 N1 104.76(11) ?
C9 N3 C10 108.87(11) yes
C9 N3 N4 126.48(10) ?
C10 N3 N4 124.63(11) ?
N3 N4 C11 111.08(12) yes
N3 N4 H4A 107.8(11) ?
C11 N4 H4A 108.9(11) ?
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 . 1.506(2) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C7 . 1.379(2) ?
C2 C3 . 1.386(2) ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(2) ?
C5 C8 . 1.512(2) ?
C6 C7 . 1.384(2) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.4875(18) yes
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N2 . 1.3004(17) yes
C9 N3 . 1.3625(17) yes
C10 O1 . 1.2338(17) ?
C10 N1 . 1.3390(19) yes
C10 N3 . 1.3825(16) yes
C11 N4 . 1.476(2) yes
C11 C12 . 1.497(2) yes
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C17 . 1.378(2) ?
C12 C13 . 1.386(2) ?
C13 C14 . 1.384(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.367(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.364(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.376(3) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
N1 N2 . 1.3911(17) yes
N1 H1 . 0.97(2) ?
N3 N4 . 1.4069(16) yes
N4 H4A . 0.888(18) ?
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
N1 H1 O1 2_556 0.97(2) 1.81(2) 2.7676(15) 169.9(18)
N4 H4A N2 1_545 0.888(18) 2.236(19) 3.0933(18) 162.2(15)
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
C7 C2 C3 C4 1.3(2) ?
C1 C2 C3 C4 179.65(16) ?
C2 C3 C4 C5 -1.2(2) ?
C3 C4 C5 C6 0.5(2) ?
C3 C4 C5 C8 -177.57(13) ?
C4 C5 C6 C7 0.1(2) ?
C8 C5 C6 C7 178.04(13) ?
C3 C2 C7 C6 -0.8(2) ?
C1 C2 C7 C6 -179.15(16) ?
C5 C6 C7 C2 0.1(2) ?
C4 C5 C8 C9 -91.23(16) ?
C6 C5 C8 C9 90.83(16) ?
C5 C8 C9 N2 100.90(16) ?
C5 C8 C9 N3 -81.30(17) ?
N4 C11 C12 C17 -101.01(17) ?
N4 C11 C12 C13 75.09(18) ?
C17 C12 C13 C14 1.7(2) ?
C11 C12 C13 C14 -174.60(15) ?
C12 C13 C14 C15 -0.4(3) ?
C13 C14 C15 C16 -1.1(3) ?
C14 C15 C16 C17 1.2(3) ?
C15 C16 C17 C12 0.1(3) ?
C13 C12 C17 C16 -1.5(2) ?
C11 C12 C17 C16 174.72(15) ?
O1 C10 N1 N2 -179.27(15) ?
N3 C10 N1 N2 -0.11(16) ?
N3 C9 N2 N1 0.10(15) ?
C8 C9 N2 N1 178.19(12) ?
C10 N1 N2 C9 0.01(16) ?
N2 C9 N3 C10 -0.17(16) ?
C8 C9 N3 C10 -178.22(13) ?
N2 C9 N3 N4 -178.74(12) ?
C8 C9 N3 N4 3.2(2) ?
O1 C10 N3 C9 179.38(14) ?
N1 C10 N3 C9 0.17(15) ?
O1 C10 N3 N4 -2.0(2) ?
N1 C10 N3 N4 178.76(12) ?
C9 N3 N4 C11 -104.49(15) ?
C10 N3 N4 C11 77.16(16) ?
C12 C11 N4 N3 75.04(15) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133959
