#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/35/2203549.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_2203549
loop_
_publ_author_name
'Petek, Hande '
'Şenel, İsmet'
'Bekircan, Olcay'
'Aǧar, Erbil'
'Şaşmaz, Selami'
_publ_section_title
4-(2,4-Dichlorobenzylamino)-3-phenyl-5-p-tolyl-4H-1,2,4-triazole
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o831
_journal_page_last               o832
_journal_paper_doi               10.1107/S1600536804009080
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C22 H18 Cl2 N4'
_chemical_formula_moiety         'C22 H18 Cl2 N4'
_chemical_formula_sum            'C22 H18 Cl2 N4'
_chemical_formula_weight         409.30
_chemical_name_systematic
;
4-(2,4-Dichlorobenzylamino)-3-phenyl-5-p-tolyl-4H-
1,2,4-triazole
;
_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
_cell_angle_alpha                113.152(16)
_cell_angle_beta                 91.984(15)
_cell_angle_gamma                95.864(17)
_cell_formula_units_Z            2
_cell_length_a                   6.2604(12)
_cell_length_b                   11.952(3)
_cell_length_c                   14.775(3)
_cell_measurement_reflns_used    4695
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      1.88
_cell_volume                     1007.8(4)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'WinGX (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       w
_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  0.1494
_diffrn_reflns_av_sigmaI/netI    0.1668
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13341
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_correction_T_min  0.9243
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.2289
_refine_ls_R_factor_gt           0.0741
_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)+(0.0303P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1330
_reflns_number_gt                1272
_reflns_number_total             3654
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6445.cif
_cod_data_source_block           I
_cod_database_code               2203549
_cod_database_fobs_code          2203549
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_type_symbol
Cl1 0.0895(3) 0.80955(16) 0.26166(12) 0.0877(6) Uani d . 1 Cl
Cl2 0.3895(3) 1.21594(18) 0.57630(12) 0.1069(7) Uani d . 1 Cl
N3 -0.0715(7) 0.9924(5) 0.1264(3) 0.0557(13) Uani d . 1 N
N1 0.1851(7) 0.8939(5) 0.0446(4) 0.0677(15) Uani d . 1 N
C8 -0.0217(9) 0.8853(7) 0.0591(4) 0.0562(16) Uani d . 1 C
N2 0.2725(7) 1.0134(5) 0.1069(4) 0.0716(16) Uani d . 1 N
N4 -0.2646(6) 1.0130(4) 0.1741(3) 0.0621(14) Uani d . 1 N
H4 -0.3550 1.0579 0.1650 0.075 Uiso calc R 1 H
C18 0.0516(9) 0.9574(5) 0.3420(4) 0.0587(16) Uani d . 1 C
C16 -0.2936(8) 0.9500(5) 0.2403(4) 0.0658(17) Uani d . 1 C
H16A -0.2755 0.8642 0.2057 0.079 Uiso calc R 1 H
H16B -0.4379 0.9545 0.2622 0.079 Uiso calc R 1 H
C19 0.2096(9) 1.0186(7) 0.4171(4) 0.0678(17) Uani d . 1 C
H19 0.3290 0.9812 0.4235 0.081 Uiso calc R 1 H
C22 -0.1456(10) 1.1249(7) 0.3970(5) 0.0754(19) Uani d . 1 C
H22 -0.2675 1.1609 0.3913 0.090 Uiso calc R 1 H
C10 0.1437(9) 1.1996(7) 0.2276(4) 0.0686(18) Uani d . 1 C
C20 0.1903(10) 1.1356(7) 0.4829(4) 0.0726(19) Uani d . 1 C
C5 -0.1631(9) 0.7704(6) 0.0066(4) 0.0566(17) Uani d . 1 C
C9 0.1167(8) 1.0736(7) 0.1565(5) 0.0591(18) Uani d . 1 C
C21 0.0086(11) 1.1909(6) 0.4742(4) 0.0795(19) Uani d . 1 C
H21 -0.0080 1.2695 0.5188 0.095 Uiso calc R 1 H
C7 -0.4997(9) 0.6520(7) -0.0806(4) 0.0663(18) Uani d . 1 C
H7 -0.6427 0.6505 -0.1009 0.080 Uiso calc R 1 H
C15 -0.0157(9) 1.2761(8) 0.2390(5) 0.082(2) Uani d . 1 C
H15 -0.1483 1.2464 0.2024 0.099 Uiso calc R 1 H
C17 -0.1287(8) 1.0097(6) 0.3287(4) 0.0577(16) Uani d . 1 C
C6 -0.3802(8) 0.7627(6) -0.0262(4) 0.0649(17) Uani d . 1 C
H6 -0.4437 0.8343 -0.0107 0.078 Uiso calc R 1 H
C4 -0.0824(10) 0.6592(7) -0.0183(5) 0.077(2) Uani d . 1 C
H4A 0.0592 0.6601 0.0035 0.093 Uiso calc R 1 H
C2 -0.4147(11) 0.5427(7) -0.1062(4) 0.0738(18) Uani d . 1 C
C11 0.3382(9) 1.2476(8) 0.2842(5) 0.085(2) Uani d . 1 C
H11 0.4466 1.1980 0.2778 0.102 Uiso calc R 1 H
C3 -0.1997(12) 0.5486(8) -0.0729(5) 0.089(2) Uani d . 1 C
H3 -0.1368 0.4769 -0.0882 0.107 Uiso calc R 1 H
C13 0.2174(14) 1.4519(9) 0.3659(6) 0.127(3) Uani d . 1 C
H13 0.2408 1.5333 0.4109 0.153 Uiso calc R 1 H
C14 0.0267(14) 1.3974(8) 0.3061(6) 0.111(3) Uani d . 1 C
H14 -0.0818 1.4468 0.3117 0.133 Uiso calc R 1 H
C1 -0.5446(12) 0.4255(7) -0.1643(5) 0.118(3) Uani d . 1 C
H1A -0.6908 0.4390 -0.1737 0.177 Uiso calc R 1 H
H1B -0.5406 0.3721 -0.1300 0.177 Uiso calc R 1 H
H1C -0.4878 0.3885 -0.2273 0.177 Uiso calc R 1 H
C12 0.3713(13) 1.3684(9) 0.3498(6) 0.114(3) Uani d . 1 C
H12 0.5042 1.3973 0.3862 0.137 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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'
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
C8 N3 C9 107.2(5) ?
C8 N3 N4 127.2(5) ?
C9 N3 N4 124.3(5) ?
C8 N1 N2 106.0(5) ?
N1 C8 N3 110.7(6) ?
N1 C8 C5 120.8(6) ?
N3 C8 C5 128.6(5) ?
C9 N2 N1 109.2(5) ?
N3 N4 C16 112.7(4) yes
N3 N4 H4 123.7 ?
C16 N4 H4 123.7 ?
C19 C18 C17 122.4(6) ?
C19 C18 Cl1 116.6(5) ?
C17 C18 Cl1 121.0(5) ?
N4 C16 C17 109.3(5) ?
N4 C16 H16A 109.8 ?
C17 C16 H16A 109.8 ?
N4 C16 H16B 109.8 ?
C17 C16 H16B 109.8 ?
H16A C16 H16B 108.3 ?
C18 C19 C20 119.6(5) ?
C18 C19 H19 120.2 ?
C20 C19 H19 120.2 ?
C17 C22 C21 123.6(6) ?
C17 C22 H22 118.2 ?
C21 C22 H22 118.2 ?
C11 C10 C15 118.6(7) ?
C11 C10 C9 118.9(6) ?
C15 C10 C9 122.5(6) ?
C19 C20 C21 120.1(6) ?
C19 C20 Cl2 120.6(5) ?
C21 C20 Cl2 119.4(6) ?
C4 C5 C6 115.5(6) ?
C4 C5 C8 119.9(5) ?
C6 C5 C8 124.5(5) ?
N2 C9 N3 106.8(6) ?
N2 C9 C10 125.7(6) ?
N3 C9 C10 127.5(5) ?
C22 C21 C20 117.8(6) ?
C22 C21 H21 121.1 ?
C20 C21 H21 121.1 ?
C6 C7 C2 122.0(5) ?
C6 C7 H7 119.0 ?
C2 C7 H7 119.0 ?
C14 C15 C10 118.8(6) ?
C14 C15 H15 120.6 ?
C10 C15 H15 120.6 ?
C22 C17 C18 116.4(5) ?
C22 C17 C16 119.8(5) ?
C18 C17 C16 123.6(6) ?
C7 C6 C5 121.4(6) ?
C7 C6 H6 119.3 ?
C5 C6 H6 119.3 ?
C3 C4 C5 123.5(6) ?
C3 C4 H4A 118.3 ?
C5 C4 H4A 118.3 ?
C7 C2 C3 117.3(6) ?
C7 C2 C1 121.3(6) ?
C3 C2 C1 121.5(7) ?
C12 C11 C10 120.2(7) ?
C12 C11 H11 119.9 ?
C10 C11 H11 119.9 ?
C4 C3 C2 120.3(6) ?
C4 C3 H3 119.9 ?
C2 C3 H3 119.9 ?
C14 C13 C12 111.8(9) ?
C14 C13 H13 124.1 ?
C12 C13 H13 124.1 ?
C15 C14 C13 125.9(8) ?
C15 C14 H14 117.0 ?
C13 C14 H14 117.0 ?
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 ?
C11 C12 C13 124.7(8) ?
C11 C12 H12 117.7 ?
C13 C12 H12 117.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C18 1.745(6) yes
Cl2 C20 1.725(6) yes
N3 C8 1.352(6) yes
N3 C9 1.385(6) yes
N3 N4 1.415(5) ?
N1 C8 1.320(6) yes
N1 N2 1.399(6) yes
C8 C5 1.461(7) ?
N2 C9 1.336(6) yes
N4 C16 1.456(6) ?
N4 H4 0.8600 ?
C18 C19 1.373(7) ?
C18 C17 1.389(7) ?
C16 C17 1.519(7) ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C19 C20 1.373(8) ?
C19 H19 0.9300 ?
C22 C17 1.367(7) ?
C22 C21 1.384(7) ?
C22 H22 0.9300 ?
C10 C11 1.386(7) ?
C10 C15 1.391(8) ?
C10 C9 1.447(7) ?
C20 C21 1.400(7) ?
C5 C4 1.386(7) ?
C5 C6 1.409(7) ?
C21 H21 0.9300 ?
C7 C6 1.370(7) ?
C7 C2 1.379(7) ?
C7 H7 0.9300 ?
C15 C14 1.389(9) ?
C15 H15 0.9300 ?
C6 H6 0.9300 ?
C4 C3 1.364(7) ?
C4 H4A 0.9300 ?
C2 C3 1.402(8) ?
C2 C1 1.460(8) ?
C11 C12 1.375(9) ?
C11 H11 0.9300 ?
C3 H3 0.9300 ?
C13 C14 1.395(9) ?
C13 C12 1.417(10) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C12 H12 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
N4 H4 N2 1_455 0.86 2.39 3.031(6) 132
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
N2 N1 C8 N3 0.5(6)
N2 N1 C8 C5 -178.8(4)
C9 N3 C8 N1 -0.4(6)
N4 N3 C8 N1 -167.8(4)
C9 N3 C8 C5 178.8(5)
N4 N3 C8 C5 11.3(8)
C8 N1 N2 C9 -0.4(6)
C8 N3 N4 C16 66.5(6)
C9 N3 N4 C16 -99.0(6)
N3 N4 C16 C17 69.5(6)
C17 C18 C19 C20 0.6(9)
Cl1 C18 C19 C20 179.8(5)
C18 C19 C20 C21 1.1(9)
C18 C19 C20 Cl2 -178.5(4)
N1 C8 C5 C4 32.0(7)
N3 C8 C5 C4 -147.1(5)
N1 C8 C5 C6 -144.8(5)
N3 C8 C5 C6 36.1(8)
N1 N2 C9 N3 0.2(6)
N1 N2 C9 C10 -179.6(5)
C8 N3 C9 N2 0.1(5)
N4 N3 C9 N2 168.0(4)
C8 N3 C9 C10 179.9(5)
N4 N3 C9 C10 -12.2(8)
C11 C10 C9 N2 -31.7(8)
C15 C10 C9 N2 146.0(6)
C11 C10 C9 N3 148.5(5)
C15 C10 C9 N3 -33.7(9)
C17 C22 C21 C20 -0.7(10)
C19 C20 C21 C22 -1.1(9)
Cl2 C20 C21 C22 178.5(5)
C11 C10 C15 C14 0.4(10)
C9 C10 C15 C14 -177.3(6)
C21 C22 C17 C18 2.3(9)
C21 C22 C17 C16 -173.3(5)
C19 C18 C17 C22 -2.3(8)
Cl1 C18 C17 C22 178.6(4)
C19 C18 C17 C16 173.2(5)
Cl1 C18 C17 C16 -6.0(8)
N4 C16 C17 C22 69.8(6)
N4 C16 C17 C18 -105.5(6)
C2 C7 C6 C5 -0.1(9)
C4 C5 C6 C7 -1.1(8)
C8 C5 C6 C7 175.7(5)
C6 C5 C4 C3 1.6(8)
C8 C5 C4 C3 -175.4(6)
C6 C7 C2 C3 0.9(9)
C6 C7 C2 C1 -179.9(6)
C15 C10 C11 C12 -0.2(10)
C9 C10 C11 C12 177.6(7)
C5 C4 C3 C2 -0.9(10)
C7 C2 C3 C4 -0.5(9)
C1 C2 C3 C4 -179.6(6)
C10 C15 C14 C13 -0.8(12)
C12 C13 C14 C15 0.9(12)
C10 C11 C12 C13 0.3(13)
C14 C13 C12 C11 -0.6(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130892
