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The title compound, C22H18Cl2N4, consists of four planar fragments. π–π interactions occur between the di­chloro­phenyl and tolyl groups. In the crystal structure, the mol­ecules are organized into layers by a network of N—H...N hydrogen-bond interactions. The compound shows considerable peroxy­nitrite scavenging activity, although weaker than the standards used, and antimicrobial activity against Gram-positive bacteria such as Staphyl­ococcus aureus ATCC 25923 and Bacillus subtilis ATCC 663.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006452/na6306sup1.cif
Contains datablocks 4, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006452/na63064sup2.hkl
Contains datablock 4

CCDC reference: 231737

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.052
  • wR factor = 0.094
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 33 Perc.
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.137 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14 PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl2 - C8 .. 5.84 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-(2,6-dichlorobenzylamino)-3-phenyl-5-p-tolyl-4H-1,2,4-triazole top
Crystal data top
C22H18Cl2N4F(000) = 1696
Mr = 409.30Dx = 1.368 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8102 reflections
a = 12.0008 (11) Åθ = 1.5–24.1°
b = 27.4501 (16) ŵ = 0.34 mm1
c = 12.068 (3) ÅT = 293 K
V = 3975.4 (10) Å3Plate, colourless
Z = 80.50 × 0.35 × 0.04 mm
Data collection top
Stoe IPDS 2
diffractometer
3901 independent reflections
Radiation source: sealed X-ray tube1304 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.137
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.5°
ω scansh = 1414
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 3033
Tmin = 0.866, Tmax = 0.986l = 1414
26654 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0112P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3901 reflectionsΔρmax = 0.34 e Å3
248 parametersΔρmin = 0.42 e Å3
74 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00079 (10)
Special details top

Experimental. Melting points were determined on a Büchi oil heated melting point apparatus and are uncorrected. 1H NMR and 13C NMR spectra (s, p.p.m.) were recorded on a Varian 200 A s pectrometer using tetramethylsilane as the internal reference. IR spectra (ν, cm-1) were run on a Perkin-Elmer 1600 FTIR spectrophotometer in KBr pellets. The UV absorption measurements were carried out in 1.10-4-1.10-6 M ethanolic solutions and the spectra were measured between 200 and 400 nm with a Shimadzu 1201 spectrophotometer using 10 mm quartz cells. Combustion analyses were performed on a Carlo Erba 1106 elemental analyzer. The necessary chemicals were obtained from Merck and Fluka.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.23394 (7)0.35384 (4)0.06790 (9)0.0994 (4)
Cl20.63722 (8)0.43631 (4)0.00082 (9)0.0974 (4)
N10.6103 (2)0.33255 (15)0.2429 (3)0.0844 (11)
N20.6284 (3)0.37772 (16)0.2878 (3)0.0878 (11)
N30.4664 (2)0.37917 (13)0.2064 (2)0.0598 (8)
N40.3703 (2)0.39825 (11)0.1578 (2)0.0729 (9)
H40.30550.39550.18760.087*
C10.5415 (3)0.40637 (19)0.2666 (3)0.0700 (11)
C20.5127 (3)0.33453 (17)0.1929 (3)0.0633 (10)
C30.4389 (3)0.39158 (14)0.0361 (3)0.0572 (10)
C40.3760 (3)0.35828 (16)0.0943 (3)0.0697 (11)
C50.4227 (4)0.32729 (17)0.1730 (3)0.0922 (14)
H50.37870.30450.20970.111*
C60.5321 (5)0.33078 (19)0.1953 (4)0.1038 (16)
H60.56370.30990.24730.125*
C70.5968 (4)0.36369 (18)0.1443 (3)0.0893 (14)
H70.67210.36610.16180.107*
C80.5503 (3)0.39404 (14)0.0652 (3)0.0673 (10)
C90.3884 (3)0.42273 (13)0.0545 (3)0.0655 (10)
H9A0.31760.43530.02830.079*
H9B0.43700.45040.06740.079*
C100.4643 (3)0.29276 (15)0.1348 (3)0.0612 (10)
C110.5343 (3)0.26407 (17)0.0713 (3)0.0757 (12)
H110.60980.27150.06790.091*
C120.4947 (3)0.22527 (17)0.0139 (3)0.0811 (12)
H120.54330.20690.02930.097*
C130.3832 (4)0.21254 (17)0.0184 (3)0.0951 (10)
C140.3137 (3)0.24096 (16)0.0831 (3)0.0740 (11)
H140.23870.23280.08790.089*
C150.3520 (3)0.28078 (15)0.1405 (3)0.0626 (10)
H150.30330.29950.18270.075*
C160.3434 (3)0.16967 (15)0.0428 (3)0.0951 (10)
H16A0.40450.15510.08190.143*
H16B0.31270.14650.00840.143*
H16C0.28700.17940.09460.143*
C170.5287 (4)0.45646 (19)0.2986 (3)0.0763 (12)
C180.4300 (4)0.47469 (19)0.3396 (3)0.0936 (14)
H180.36860.45430.34580.112*
C190.4208 (5)0.5234 (2)0.3720 (4)0.1231 (19)
H190.35280.53500.39790.148*
C200.5107 (5)0.5547 (2)0.3663 (4)0.133 (2)
H200.50570.58680.39070.160*
C210.6071 (5)0.5365 (2)0.3232 (4)0.123 (2)
H210.66760.55730.31430.147*
C220.6190 (4)0.4875 (2)0.2917 (3)0.1025 (15)
H220.68730.47610.26640.123*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0761 (7)0.1224 (11)0.0997 (8)0.0150 (7)0.0312 (6)0.0128 (8)
Cl20.0762 (6)0.1030 (9)0.1129 (8)0.0226 (7)0.0132 (7)0.0128 (8)
N10.0480 (19)0.127 (3)0.078 (2)0.014 (2)0.0145 (16)0.002 (2)
N20.054 (2)0.129 (3)0.081 (2)0.003 (2)0.0165 (19)0.008 (2)
N30.0382 (16)0.089 (3)0.0523 (18)0.0039 (18)0.0002 (15)0.0019 (18)
N40.0379 (16)0.124 (3)0.0568 (18)0.0181 (19)0.0036 (15)0.0171 (19)
C10.043 (2)0.112 (4)0.055 (2)0.005 (3)0.006 (2)0.005 (3)
C20.039 (2)0.097 (3)0.054 (2)0.007 (2)0.0036 (18)0.006 (2)
C30.063 (2)0.058 (3)0.051 (2)0.000 (2)0.0045 (17)0.0051 (19)
C40.074 (2)0.076 (3)0.060 (3)0.007 (2)0.016 (2)0.016 (2)
C50.133 (4)0.091 (4)0.053 (3)0.020 (3)0.016 (3)0.003 (2)
C60.133 (4)0.107 (4)0.072 (3)0.004 (4)0.015 (3)0.016 (3)
C70.101 (3)0.100 (4)0.067 (3)0.003 (3)0.025 (2)0.004 (3)
C80.069 (2)0.075 (3)0.058 (2)0.010 (2)0.002 (2)0.003 (2)
C90.057 (2)0.073 (3)0.066 (2)0.004 (2)0.0099 (19)0.006 (2)
C100.047 (2)0.084 (3)0.052 (2)0.014 (2)0.0011 (18)0.007 (2)
C110.059 (2)0.098 (4)0.070 (3)0.010 (2)0.010 (2)0.007 (2)
C120.083 (3)0.096 (4)0.064 (3)0.025 (3)0.015 (2)0.004 (2)
C130.110 (2)0.092 (3)0.083 (2)0.003 (2)0.003 (2)0.0063 (18)
C140.061 (2)0.094 (4)0.066 (3)0.003 (2)0.005 (2)0.008 (2)
C150.048 (2)0.090 (3)0.050 (2)0.008 (2)0.0009 (19)0.002 (2)
C160.110 (2)0.092 (3)0.083 (2)0.003 (2)0.003 (2)0.0063 (18)
C170.061 (3)0.106 (4)0.062 (3)0.009 (3)0.011 (2)0.006 (3)
C180.078 (3)0.114 (4)0.089 (3)0.006 (3)0.003 (3)0.011 (3)
C190.130 (4)0.130 (5)0.109 (4)0.021 (4)0.013 (4)0.037 (4)
C200.133 (5)0.146 (6)0.120 (4)0.015 (4)0.024 (4)0.005 (4)
C210.130 (5)0.128 (5)0.110 (4)0.052 (4)0.028 (3)0.009 (4)
C220.074 (3)0.143 (4)0.091 (3)0.031 (3)0.012 (3)0.010 (3)
Geometric parameters (Å, º) top
Cl1—C41.739 (4)C10—C151.389 (4)
Cl2—C81.743 (4)C11—C121.357 (5)
N1—C21.319 (4)C11—H110.9300
N1—N21.370 (4)C12—C131.384 (5)
N2—C11.330 (4)C12—H120.9300
N3—C21.355 (4)C13—C141.383 (5)
N3—C11.378 (4)C13—C161.469 (5)
N3—N41.395 (3)C14—C151.373 (4)
N4—C91.434 (4)C14—H140.9300
N4—H40.8600C15—H150.9300
C1—C171.436 (5)C16—H16A0.9600
C2—C101.464 (5)C16—H16B0.9600
C3—C41.378 (4)C16—H16C0.9600
C3—C81.384 (4)C17—C181.377 (5)
C3—C91.514 (4)C17—C221.381 (5)
C4—C51.392 (5)C18—C191.398 (6)
C5—C61.344 (5)C18—H180.9300
C5—H50.9300C19—C201.381 (6)
C6—C71.341 (5)C19—H190.9300
C6—H60.9300C20—C211.365 (6)
C7—C81.385 (5)C20—H200.9300
C7—H70.9300C21—C221.403 (6)
C9—H9A0.9700C21—H210.9300
C9—H9B0.9700C22—H220.9300
C10—C111.383 (4)
C2—N1—N2106.5 (4)C15—C10—C2123.1 (3)
C1—N2—N1109.6 (3)C12—C11—C10121.2 (4)
C2—N3—C1106.6 (3)C12—C11—H11119.4
C2—N3—N4128.9 (3)C10—C11—H11119.4
C1—N3—N4124.0 (4)C11—C12—C13121.1 (4)
N3—N4—C9114.6 (2)C11—C12—H12119.4
N3—N4—H4122.7C13—C12—H12119.4
C9—N4—H4122.7C14—C13—C12117.5 (4)
N2—C1—N3107.1 (4)C14—C13—C16122.7 (4)
N2—C1—C17126.7 (4)C12—C13—C16119.8 (5)
N3—C1—C17126.2 (4)C15—C14—C13122.2 (4)
N1—C2—N3110.2 (4)C15—C14—H14118.9
N1—C2—C10122.6 (4)C13—C14—H14118.9
N3—C2—C10127.1 (3)C14—C15—C10119.2 (3)
C4—C3—C8115.6 (3)C14—C15—H15120.4
C4—C3—C9121.6 (3)C10—C15—H15120.4
C8—C3—C9122.8 (3)C13—C16—H16A109.5
C3—C4—C5122.2 (4)C13—C16—H16B109.5
C3—C4—Cl1119.3 (3)H16A—C16—H16B109.5
C5—C4—Cl1118.5 (4)C13—C16—H16C109.5
C6—C5—C4119.1 (4)H16A—C16—H16C109.5
C6—C5—H5120.5H16B—C16—H16C109.5
C4—C5—H5120.5C18—C17—C22118.1 (5)
C7—C6—C5121.5 (5)C18—C17—C1122.4 (4)
C7—C6—H6119.3C22—C17—C1119.4 (5)
C5—C6—H6119.3C17—C18—C19121.1 (5)
C6—C7—C8119.2 (4)C17—C18—H18119.5
C6—C7—H7120.4C19—C18—H18119.5
C8—C7—H7120.4C20—C19—C18121.3 (6)
C3—C8—C7122.4 (4)C20—C19—H19119.3
C3—C8—Cl2119.8 (3)C18—C19—H19119.3
C7—C8—Cl2117.8 (3)C21—C20—C19116.9 (7)
N4—C9—C3115.1 (3)C21—C20—H20121.5
N4—C9—H9A108.5C19—C20—H20121.5
C3—C9—H9A108.5C20—C21—C22122.7 (6)
N4—C9—H9B108.5C20—C21—H21118.6
C3—C9—H9B108.5C22—C21—H21118.6
H9A—C9—H9B107.5C17—C22—C21119.7 (5)
C11—C10—C15118.8 (4)C17—C22—H22120.1
C11—C10—C2118.1 (4)C21—C22—H22120.1
C2—N1—N2—C11.1 (4)N3—N4—C9—C359.6 (4)
C2—N3—N4—C989.7 (4)C4—C3—C9—N477.1 (4)
C1—N3—N4—C980.4 (4)C8—C3—C9—N4102.1 (4)
N1—N2—C1—N30.4 (4)N1—C2—C10—C1140.8 (5)
N1—N2—C1—C17179.4 (4)N3—C2—C10—C11141.0 (4)
C2—N3—C1—N20.5 (4)N1—C2—C10—C15139.3 (3)
N4—N3—C1—N2172.4 (3)N3—C2—C10—C1539.0 (5)
C2—N3—C1—C17178.5 (4)C15—C10—C11—C121.0 (6)
N4—N3—C1—C176.6 (5)C2—C10—C11—C12178.9 (4)
N2—N1—C2—N31.4 (4)C10—C11—C12—C131.2 (6)
N2—N1—C2—C10179.9 (3)C11—C12—C13—C140.3 (6)
C1—N3—C2—N11.2 (4)C11—C12—C13—C16178.6 (4)
N4—N3—C2—N1172.6 (3)C12—C13—C14—C150.7 (6)
C1—N3—C2—C10179.6 (3)C16—C13—C14—C15179.5 (3)
N4—N3—C2—C108.9 (6)C13—C14—C15—C100.8 (5)
C8—C3—C4—C53.4 (5)C11—C10—C15—C140.1 (5)
C9—C3—C4—C5176.0 (3)C2—C10—C15—C14179.9 (3)
C8—C3—C4—Cl1177.6 (3)N2—C1—C17—C18137.4 (4)
C9—C3—C4—Cl13.1 (5)N3—C1—C17—C1843.7 (6)
C3—C4—C5—C61.8 (6)N2—C1—C17—C2240.4 (6)
Cl1—C4—C5—C6179.1 (3)N3—C1—C17—C22138.5 (4)
C4—C5—C6—C70.7 (7)C22—C17—C18—C190.9 (6)
C5—C6—C7—C81.4 (7)C1—C17—C18—C19178.7 (4)
C4—C3—C8—C72.6 (5)C17—C18—C19—C201.4 (7)
C9—C3—C8—C7176.7 (3)C18—C19—C20—C212.7 (8)
C4—C3—C8—Cl2177.7 (3)C19—C20—C21—C223.8 (9)
C9—C3—C8—Cl23.0 (5)C18—C17—C22—C211.9 (6)
C6—C7—C8—C30.3 (6)C1—C17—C22—C21179.8 (4)
C6—C7—C8—Cl2180.0 (3)C20—C21—C22—C173.5 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···N2i0.862.203.030 (4)162
C9—H9B···Cl20.972.573.082 (3)113
Symmetry code: (i) x1/2, y, z1/2.
 

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