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The title compound, C22H18Cl2N4, displays the characteristic features of 1,2,4-triazole derivatives. There is an N—H...N intermolecular hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009080/bt6445sup1.cif
Contains datablocks hande3, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009080/bt6445Isup2.hkl
Contains datablock I

CCDC reference: 239269

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.074
  • wR factor = 0.133
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.149 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15 PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.60 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C8 .. 5.12 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C13 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C2 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 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 4 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; 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: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997).

4-(2,4-Dichlorobenzylamino)-3-phenyl-5-p-tolyl-4H- 1,2,4-triazole top
Crystal data top
C22H18Cl2N4Z = 2
Mr = 409.30F(000) = 424
Triclinic, P1Dx = 1.349 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2604 (12) ÅCell parameters from 4695 reflections
b = 11.952 (3) Åθ = 1.9–26.7°
c = 14.775 (3) ŵ = 0.34 mm1
α = 113.152 (16)°T = 293 K
β = 91.984 (15)°Plate, colourless
γ = 95.864 (17)°0.18 × 0.14 × 0.07 mm
V = 1007.8 (4) Å3
Data collection top
Stoe IPDS-II
diffractometer
3654 independent reflections
Radiation source: fine-focus sealed tube1272 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.149
w scansθmax = 25.3°, θmin = 2.8°
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
h = 77
Tmin = 0.924, Tmax = 0.969k = 1414
13341 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0303P)2]
where P = (Fo2 + 2Fc2)/3
3654 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.15 e Å3
Special details top

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
Cl10.0895 (3)0.80955 (16)0.26166 (12)0.0877 (6)
Cl20.3895 (3)1.21594 (18)0.57630 (12)0.1069 (7)
N30.0715 (7)0.9924 (5)0.1264 (3)0.0557 (13)
N10.1851 (7)0.8939 (5)0.0446 (4)0.0677 (15)
C80.0217 (9)0.8853 (7)0.0591 (4)0.0562 (16)
N20.2725 (7)1.0134 (5)0.1069 (4)0.0716 (16)
N40.2646 (6)1.0130 (4)0.1741 (3)0.0621 (14)
H40.35501.05790.16500.075*
C180.0516 (9)0.9574 (5)0.3420 (4)0.0587 (16)
C160.2936 (8)0.9500 (5)0.2403 (4)0.0658 (17)
H16A0.27550.86420.20570.079*
H16B0.43790.95450.26220.079*
C190.2096 (9)1.0186 (7)0.4171 (4)0.0678 (17)
H190.32900.98120.42350.081*
C220.1456 (10)1.1249 (7)0.3970 (5)0.0754 (19)
H220.26751.16090.39130.090*
C100.1437 (9)1.1996 (7)0.2276 (4)0.0686 (18)
C200.1903 (10)1.1356 (7)0.4829 (4)0.0726 (19)
C50.1631 (9)0.7704 (6)0.0066 (4)0.0566 (17)
C90.1167 (8)1.0736 (7)0.1565 (5)0.0591 (18)
C210.0086 (11)1.1909 (6)0.4742 (4)0.0795 (19)
H210.00801.26950.51880.095*
C70.4997 (9)0.6520 (7)0.0806 (4)0.0663 (18)
H70.64270.65050.10090.080*
C150.0157 (9)1.2761 (8)0.2390 (5)0.082 (2)
H150.14831.24640.20240.099*
C170.1287 (8)1.0097 (6)0.3287 (4)0.0577 (16)
C60.3802 (8)0.7627 (6)0.0262 (4)0.0649 (17)
H60.44370.83430.01070.078*
C40.0824 (10)0.6592 (7)0.0183 (5)0.077 (2)
H4A0.05920.66010.00350.093*
C20.4147 (11)0.5427 (7)0.1062 (4)0.0738 (18)
C110.3382 (9)1.2476 (8)0.2842 (5)0.085 (2)
H110.44661.19800.27780.102*
C30.1997 (12)0.5486 (8)0.0729 (5)0.089 (2)
H30.13680.47690.08820.107*
C130.2174 (14)1.4519 (9)0.3659 (6)0.127 (3)
H130.24081.53330.41090.153*
C140.0267 (14)1.3974 (8)0.3061 (6)0.111 (3)
H140.08181.44680.31170.133*
C10.5446 (12)0.4255 (7)0.1643 (5)0.118 (3)
H1A0.69080.43900.17370.177*
H1B0.54060.37210.13000.177*
H1C0.48780.38850.22730.177*
C120.3713 (13)1.3684 (9)0.3498 (6)0.114 (3)
H120.50421.39730.38620.137*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0873 (12)0.1008 (15)0.0744 (12)0.0316 (11)0.0025 (9)0.0301 (11)
Cl20.0869 (13)0.1475 (19)0.0696 (12)0.0040 (12)0.0113 (10)0.0314 (12)
N30.037 (3)0.091 (4)0.055 (3)0.020 (3)0.008 (2)0.042 (3)
N10.030 (3)0.116 (5)0.079 (4)0.029 (3)0.018 (2)0.057 (3)
C80.040 (4)0.088 (5)0.057 (4)0.009 (4)0.001 (3)0.046 (4)
N20.038 (3)0.114 (5)0.078 (4)0.011 (3)0.007 (3)0.055 (4)
N40.032 (2)0.110 (4)0.068 (3)0.031 (3)0.020 (2)0.054 (3)
C180.052 (4)0.081 (5)0.051 (4)0.016 (3)0.010 (3)0.033 (3)
C160.043 (3)0.114 (5)0.063 (4)0.016 (3)0.018 (3)0.057 (4)
C190.050 (4)0.111 (6)0.056 (4)0.016 (4)0.009 (3)0.046 (4)
C220.076 (5)0.100 (6)0.058 (4)0.029 (4)0.024 (4)0.034 (4)
C100.056 (4)0.107 (6)0.051 (4)0.005 (4)0.009 (3)0.041 (4)
C200.069 (4)0.108 (6)0.049 (4)0.013 (4)0.006 (3)0.040 (4)
C50.050 (4)0.089 (5)0.060 (4)0.041 (4)0.026 (3)0.051 (4)
C90.018 (3)0.116 (6)0.069 (4)0.007 (4)0.001 (3)0.066 (4)
C210.096 (5)0.085 (5)0.057 (4)0.025 (4)0.014 (4)0.024 (4)
C70.045 (4)0.092 (6)0.061 (4)0.015 (4)0.009 (3)0.028 (4)
C150.052 (4)0.120 (7)0.099 (6)0.016 (5)0.000 (4)0.069 (5)
C170.044 (3)0.097 (5)0.045 (4)0.009 (3)0.011 (3)0.041 (4)
C60.045 (4)0.101 (6)0.069 (4)0.020 (4)0.013 (3)0.051 (4)
C40.061 (4)0.109 (6)0.076 (5)0.024 (5)0.014 (4)0.048 (5)
C20.084 (5)0.077 (6)0.060 (4)0.004 (5)0.009 (4)0.027 (4)
C110.044 (4)0.133 (7)0.084 (5)0.002 (4)0.010 (4)0.056 (5)
C30.091 (6)0.110 (7)0.084 (5)0.052 (5)0.027 (4)0.047 (5)
C130.078 (6)0.191 (10)0.135 (8)0.024 (7)0.001 (6)0.086 (7)
C140.121 (8)0.103 (7)0.121 (7)0.043 (6)0.038 (6)0.049 (6)
C10.129 (7)0.117 (7)0.085 (5)0.007 (6)0.007 (5)0.020 (5)
C120.080 (6)0.131 (8)0.107 (7)0.030 (6)0.019 (5)0.036 (6)
Geometric parameters (Å, º) top
Cl1—C181.745 (6)C5—C41.386 (7)
Cl2—C201.725 (6)C5—C61.409 (7)
N3—C81.352 (6)C21—H210.9300
N3—C91.385 (6)C7—C61.370 (7)
N3—N41.415 (5)C7—C21.379 (7)
N1—C81.320 (6)C7—H70.9300
N1—N21.399 (6)C15—C141.389 (9)
C8—C51.461 (7)C15—H150.9300
N2—C91.336 (6)C6—H60.9300
N4—C161.456 (6)C4—C31.364 (7)
N4—H40.8600C4—H4A0.9300
C18—C191.373 (7)C2—C31.402 (8)
C18—C171.389 (7)C2—C11.460 (8)
C16—C171.519 (7)C11—C121.375 (9)
C16—H16A0.9700C11—H110.9300
C16—H16B0.9700C3—H30.9300
C19—C201.373 (8)C13—C141.395 (9)
C19—H190.9300C13—C121.417 (10)
C22—C171.367 (7)C13—H130.9300
C22—C211.384 (7)C14—H140.9300
C22—H220.9300C1—H1A0.9600
C10—C111.386 (7)C1—H1B0.9600
C10—C151.391 (8)C1—H1C0.9600
C10—C91.447 (7)C12—H120.9300
C20—C211.400 (7)
C8—N3—C9107.2 (5)C20—C21—H21121.1
C8—N3—N4127.2 (5)C6—C7—C2122.0 (5)
C9—N3—N4124.3 (5)C6—C7—H7119.0
C8—N1—N2106.0 (5)C2—C7—H7119.0
N1—C8—N3110.7 (6)C14—C15—C10118.8 (6)
N1—C8—C5120.8 (6)C14—C15—H15120.6
N3—C8—C5128.6 (5)C10—C15—H15120.6
C9—N2—N1109.2 (5)C22—C17—C18116.4 (5)
N3—N4—C16112.7 (4)C22—C17—C16119.8 (5)
N3—N4—H4123.7C18—C17—C16123.6 (6)
C16—N4—H4123.7C7—C6—C5121.4 (6)
C19—C18—C17122.4 (6)C7—C6—H6119.3
C19—C18—Cl1116.6 (5)C5—C6—H6119.3
C17—C18—Cl1121.0 (5)C3—C4—C5123.5 (6)
N4—C16—C17109.3 (5)C3—C4—H4A118.3
N4—C16—H16A109.8C5—C4—H4A118.3
C17—C16—H16A109.8C7—C2—C3117.3 (6)
N4—C16—H16B109.8C7—C2—C1121.3 (6)
C17—C16—H16B109.8C3—C2—C1121.5 (7)
H16A—C16—H16B108.3C12—C11—C10120.2 (7)
C18—C19—C20119.6 (5)C12—C11—H11119.9
C18—C19—H19120.2C10—C11—H11119.9
C20—C19—H19120.2C4—C3—C2120.3 (6)
C17—C22—C21123.6 (6)C4—C3—H3119.9
C17—C22—H22118.2C2—C3—H3119.9
C21—C22—H22118.2C14—C13—C12111.8 (9)
C11—C10—C15118.6 (7)C14—C13—H13124.1
C11—C10—C9118.9 (6)C12—C13—H13124.1
C15—C10—C9122.5 (6)C15—C14—C13125.9 (8)
C19—C20—C21120.1 (6)C15—C14—H14117.0
C19—C20—Cl2120.6 (5)C13—C14—H14117.0
C21—C20—Cl2119.4 (6)C2—C1—H1A109.5
C4—C5—C6115.5 (6)C2—C1—H1B109.5
C4—C5—C8119.9 (5)H1A—C1—H1B109.5
C6—C5—C8124.5 (5)C2—C1—H1C109.5
N2—C9—N3106.8 (6)H1A—C1—H1C109.5
N2—C9—C10125.7 (6)H1B—C1—H1C109.5
N3—C9—C10127.5 (5)C11—C12—C13124.7 (8)
C22—C21—C20117.8 (6)C11—C12—H12117.7
C22—C21—H21121.1C13—C12—H12117.7
N2—N1—C8—N30.5 (6)C19—C20—C21—C221.1 (9)
N2—N1—C8—C5178.8 (4)Cl2—C20—C21—C22178.5 (5)
C9—N3—C8—N10.4 (6)C11—C10—C15—C140.4 (10)
N4—N3—C8—N1167.8 (4)C9—C10—C15—C14177.3 (6)
C9—N3—C8—C5178.8 (5)C21—C22—C17—C182.3 (9)
N4—N3—C8—C511.3 (8)C21—C22—C17—C16173.3 (5)
C8—N1—N2—C90.4 (6)C19—C18—C17—C222.3 (8)
C8—N3—N4—C1666.5 (6)Cl1—C18—C17—C22178.6 (4)
C9—N3—N4—C1699.0 (6)C19—C18—C17—C16173.2 (5)
N3—N4—C16—C1769.5 (6)Cl1—C18—C17—C166.0 (8)
C17—C18—C19—C200.6 (9)N4—C16—C17—C2269.8 (6)
Cl1—C18—C19—C20179.8 (5)N4—C16—C17—C18105.5 (6)
C18—C19—C20—C211.1 (9)C2—C7—C6—C50.1 (9)
C18—C19—C20—Cl2178.5 (4)C4—C5—C6—C71.1 (8)
N1—C8—C5—C432.0 (7)C8—C5—C6—C7175.7 (5)
N3—C8—C5—C4147.1 (5)C6—C5—C4—C31.6 (8)
N1—C8—C5—C6144.8 (5)C8—C5—C4—C3175.4 (6)
N3—C8—C5—C636.1 (8)C6—C7—C2—C30.9 (9)
N1—N2—C9—N30.2 (6)C6—C7—C2—C1179.9 (6)
N1—N2—C9—C10179.6 (5)C15—C10—C11—C120.2 (10)
C8—N3—C9—N20.1 (5)C9—C10—C11—C12177.6 (7)
N4—N3—C9—N2168.0 (4)C5—C4—C3—C20.9 (10)
C8—N3—C9—C10179.9 (5)C7—C2—C3—C40.5 (9)
N4—N3—C9—C1012.2 (8)C1—C2—C3—C4179.6 (6)
C11—C10—C9—N231.7 (8)C10—C15—C14—C130.8 (12)
C15—C10—C9—N2146.0 (6)C12—C13—C14—C150.9 (12)
C11—C10—C9—N3148.5 (5)C10—C11—C12—C130.3 (13)
C15—C10—C9—N333.7 (9)C14—C13—C12—C110.6 (13)
C17—C22—C21—C200.7 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···N2i0.862.393.031 (6)132
Symmetry code: (i) x1, y, z.
 

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