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In the title compound, C12H11Cl2N5O2, the triazole and benzene rings make a dihedral angle of 89.79 (2)°. Inter­molecular N—H...N and C—H...O hydrogen bonds link the mol­ecules into zigzag chains running in the [101] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033880/sg2181sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033880/sg2181Isup2.hkl
Contains datablock I

CCDC reference: 657777

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.111
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

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Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The derivatives of 1H-1,2,4-triazoles have been reported to possess various biological activities (Xu et al., 2002). In a search for new triazole compounds with better biological activity, the title compound, (I), was synthesized. We report here the crystal structure of (I).

Bond lengths and angles of the triazole rings are in agreement with those in previous reports (Çoruh et al., 2003; Li et al., 2005). The N=C bond length [N4=C7 = 1.285 (4) Å] are close to the value reported in the literature (Puviarasan et al., 1999). Atoms Cl1/Cl2/O1/N4/C7/C8/C11 lies in the benzene ring (C1/C2/C3/C4/C5/C6) plane, and the deviations from the least-squares plane through the ring atoms are all smaller than 0.046 (2) Å. The dihedral angle between the plane of benzene and triazole (N1/N2/N3/C9/C10) ring is 89.79 (2)°. Intermolecular hydrogen bonds N—H···N and C—H···O link the molecules into zigzag chains running in the [101] direction. The crystal packing (Fig. 2) is further stabilized by van der Waals forces.

Related literature top

For the crystal structures of related compounds, see: Çoruh et al. (2003); Li et al. (2005); Puviarasan et al. (1999). For details of the biological activities of triazole compounds, see: Xu et al. (2002).

Experimental top

1-(3,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanoxime (0.01 mol) was treated with triethylamine (0.0105 mol) and 40 ml trichloromethane, then the mixture was refluxed for 20 h. The resulting product was filtered off and dried in vacuo. The residue was purified by silica gel flash chromatography using a gradient from a 3:1 mixture of petroleum ether:ethyl acetate as eluent. (72% yield). mp 421–423 K. 1H NMR (CDCl3, 600 MHz) δ: 8.35 (s, 1H), 7.95 (s, 1H), 7.93–7.54 (m, 3H), 6.28 (s, 1H), 5.52 (s, 2H). IR (KBr) cm-1: 3337, 3098, 2945, 2852, 1743, 1508. Anal. Calc. for C12H11Cl2N5O2 (Mr=328.1): C 43.92, H 3.38, N 21.34; Found C 44.25, H 3.19, N 21.78.

Refinement top

All H atoms were placed in calculated positions, with N—H = 0.86 and C—H = 0.93–0.97 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2(1.5 for methyl groups) times Ueq(C,N).

Structure description top

The derivatives of 1H-1,2,4-triazoles have been reported to possess various biological activities (Xu et al., 2002). In a search for new triazole compounds with better biological activity, the title compound, (I), was synthesized. We report here the crystal structure of (I).

Bond lengths and angles of the triazole rings are in agreement with those in previous reports (Çoruh et al., 2003; Li et al., 2005). The N=C bond length [N4=C7 = 1.285 (4) Å] are close to the value reported in the literature (Puviarasan et al., 1999). Atoms Cl1/Cl2/O1/N4/C7/C8/C11 lies in the benzene ring (C1/C2/C3/C4/C5/C6) plane, and the deviations from the least-squares plane through the ring atoms are all smaller than 0.046 (2) Å. The dihedral angle between the plane of benzene and triazole (N1/N2/N3/C9/C10) ring is 89.79 (2)°. Intermolecular hydrogen bonds N—H···N and C—H···O link the molecules into zigzag chains running in the [101] direction. The crystal packing (Fig. 2) is further stabilized by van der Waals forces.

For the crystal structures of related compounds, see: Çoruh et al. (2003); Li et al. (2005); Puviarasan et al. (1999). For details of the biological activities of triazole compounds, see: Xu et al. (2002).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the title compound (I), with displacement ellipsoids drawn at the 40% probability level.
[Figure 2] Fig. 2. A packing diagram of the molecule of the title compound. Hydrogen bonds are shown as dashed lines.
1-(3,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethyleneamino N-methylcarbamate top
Crystal data top
C12H11Cl2N5O2Z = 2
Mr = 328.16F(000) = 336
Triclinic, P1Dx = 1.522 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.016 (2) ÅCell parameters from 1527 reflections
b = 8.430 (2) Åθ = 2.9–26.3°
c = 14.721 (4) ŵ = 0.47 mm1
α = 101.501 (4)°T = 294 K
β = 100.057 (4)°Block, white
γ = 93.977 (4)°0.30 × 0.20 × 0.18 mm
V = 716.1 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2497 independent reflections
Radiation source: fine-focus sealed tube1863 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 76
Tmin = 0.873, Tmax = 0.921k = 105
3665 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1094P]
where P = (Fo2 + 2Fc2)/3
2497 reflections(Δ/σ)max = 0.004
191 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C12H11Cl2N5O2γ = 93.977 (4)°
Mr = 328.16V = 716.1 (3) Å3
Triclinic, P1Z = 2
a = 6.016 (2) ÅMo Kα radiation
b = 8.430 (2) ŵ = 0.47 mm1
c = 14.721 (4) ÅT = 294 K
α = 101.501 (4)°0.30 × 0.20 × 0.18 mm
β = 100.057 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2497 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1863 reflections with I > 2σ(I)
Tmin = 0.873, Tmax = 0.921Rint = 0.019
3665 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.04Δρmax = 0.23 e Å3
2497 reflectionsΔρmin = 0.23 e Å3
191 parameters
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
Cl11.29314 (11)0.19171 (9)0.01383 (5)0.0566 (2)
Cl20.87282 (14)0.36122 (8)0.07119 (6)0.0773 (3)
O10.5256 (3)0.19831 (19)0.37808 (11)0.0459 (4)
O20.2410 (3)0.2024 (2)0.45331 (12)0.0561 (5)
N10.6867 (3)0.4563 (2)0.29428 (14)0.0410 (5)
N20.5955 (4)0.4215 (2)0.20095 (15)0.0516 (6)
N30.4610 (5)0.6417 (3)0.27541 (19)0.0683 (7)
N40.6348 (3)0.0963 (2)0.31413 (13)0.0396 (5)
N50.3195 (3)0.0440 (2)0.37867 (14)0.0458 (5)
H50.40900.09340.34570.055*
C11.1004 (4)0.1653 (3)0.19469 (17)0.0454 (6)
H11.14680.27540.21950.054*
C21.2155 (4)0.0786 (3)0.13105 (17)0.0467 (6)
H21.33870.13040.11410.056*
C31.1487 (4)0.0836 (3)0.09290 (16)0.0404 (6)
C40.9628 (4)0.1587 (3)0.11822 (17)0.0427 (6)
C50.8491 (4)0.0720 (3)0.18221 (17)0.0417 (6)
H5A0.72530.12380.19880.050*
C60.9175 (4)0.0918 (3)0.22214 (15)0.0354 (5)
C70.7949 (4)0.1808 (3)0.29180 (15)0.0369 (5)
C80.8565 (4)0.3608 (3)0.33421 (19)0.0482 (6)
H8A0.86730.38000.40210.058*
H8B1.00370.39520.32200.058*
C90.6048 (5)0.5866 (3)0.3364 (2)0.0624 (8)
H90.64380.63300.40060.075*
C100.4608 (5)0.5358 (3)0.1939 (2)0.0580 (7)
H100.37180.54330.13680.070*
C110.3497 (4)0.1160 (3)0.40575 (16)0.0417 (6)
C120.1374 (5)0.1376 (3)0.4038 (2)0.0616 (8)
H12A0.16420.12710.47100.092*
H12B0.13160.25010.37340.092*
H12C0.00440.09750.38350.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0555 (4)0.0657 (5)0.0554 (4)0.0165 (3)0.0292 (3)0.0097 (3)
Cl20.0810 (6)0.0403 (4)0.1080 (7)0.0039 (3)0.0551 (5)0.0184 (4)
O10.0534 (10)0.0356 (9)0.0479 (10)0.0124 (7)0.0190 (8)0.0032 (7)
O20.0617 (11)0.0552 (11)0.0528 (10)0.0217 (9)0.0260 (9)0.0035 (8)
N10.0464 (12)0.0286 (10)0.0475 (12)0.0063 (8)0.0165 (9)0.0001 (8)
N20.0702 (15)0.0400 (12)0.0470 (13)0.0127 (11)0.0180 (11)0.0063 (10)
N30.0821 (18)0.0472 (14)0.0761 (17)0.0288 (13)0.0179 (14)0.0045 (13)
N40.0458 (12)0.0331 (11)0.0412 (11)0.0143 (9)0.0155 (9)0.0012 (8)
N50.0538 (13)0.0392 (12)0.0514 (12)0.0166 (9)0.0264 (10)0.0080 (9)
C10.0487 (15)0.0377 (13)0.0485 (14)0.0001 (11)0.0099 (12)0.0075 (11)
C20.0441 (14)0.0474 (15)0.0504 (15)0.0014 (11)0.0162 (12)0.0106 (12)
C30.0394 (13)0.0477 (15)0.0368 (12)0.0117 (11)0.0118 (10)0.0094 (11)
C40.0449 (14)0.0342 (13)0.0490 (14)0.0074 (10)0.0149 (11)0.0029 (11)
C50.0392 (13)0.0343 (13)0.0520 (14)0.0039 (10)0.0182 (11)0.0022 (11)
C60.0353 (13)0.0332 (12)0.0373 (12)0.0083 (10)0.0048 (10)0.0070 (10)
C70.0361 (13)0.0312 (12)0.0401 (13)0.0080 (10)0.0031 (10)0.0023 (10)
C80.0440 (15)0.0357 (14)0.0576 (16)0.0055 (11)0.0076 (12)0.0054 (11)
C90.077 (2)0.0445 (16)0.0593 (17)0.0199 (14)0.0163 (15)0.0105 (13)
C100.0747 (19)0.0424 (16)0.0625 (18)0.0124 (14)0.0167 (15)0.0188 (13)
C110.0429 (14)0.0489 (15)0.0342 (12)0.0145 (11)0.0086 (11)0.0065 (11)
C120.0643 (18)0.0607 (18)0.0730 (19)0.0128 (14)0.0342 (15)0.0255 (15)
Geometric parameters (Å, º) top
Cl1—C31.727 (2)C1—H10.9300
Cl2—C41.719 (2)C2—C31.373 (3)
O1—C111.388 (3)C2—H20.9300
O1—N41.424 (2)C3—C41.390 (3)
O2—C111.213 (3)C4—C51.382 (3)
N1—C91.320 (3)C5—C61.391 (3)
N1—N21.352 (3)C5—H5A0.9300
N1—C81.460 (3)C6—C71.481 (3)
N2—C101.309 (3)C7—C81.514 (3)
N3—C91.312 (4)C8—H8A0.9700
N3—C101.345 (4)C8—H8B0.9700
N4—C71.285 (3)C9—H90.9300
N5—C111.318 (3)C10—H100.9300
N5—C121.448 (3)C12—H12A0.9600
N5—H50.8600C12—H12B0.9600
C1—C21.384 (3)C12—H12C0.9600
C1—C61.385 (3)
C11—O1—N4113.69 (16)C1—C6—C7122.5 (2)
C9—N1—N2109.4 (2)C5—C6—C7119.6 (2)
C9—N1—C8129.2 (2)N4—C7—C6116.11 (19)
N2—N1—C8121.33 (18)N4—C7—C8122.3 (2)
C10—N2—N1102.3 (2)C6—C7—C8121.6 (2)
C9—N3—C10102.4 (2)N1—C8—C7110.93 (19)
C7—N4—O1110.06 (18)N1—C8—H8A109.5
C11—N5—C12120.7 (2)C7—C8—H8A109.5
C11—N5—H5119.6N1—C8—H8B109.5
C12—N5—H5119.6C7—C8—H8B109.5
C2—C1—C6121.4 (2)H8A—C8—H8B108.0
C2—C1—H1119.3N3—C9—N1110.9 (3)
C6—C1—H1119.3N3—C9—H9124.6
C3—C2—C1120.2 (2)N1—C9—H9124.6
C3—C2—H2119.9N2—C10—N3114.9 (3)
C1—C2—H2119.9N2—C10—H10122.5
C2—C3—C4119.2 (2)N3—C10—H10122.5
C2—C3—Cl1120.16 (19)O2—C11—N5127.4 (2)
C4—C3—Cl1120.65 (19)O2—C11—O1114.8 (2)
C5—C4—C3120.4 (2)N5—C11—O1117.73 (19)
C5—C4—Cl2119.09 (19)N5—C12—H12A109.5
C3—C4—Cl2120.48 (18)N5—C12—H12B109.5
C4—C5—C6120.8 (2)H12A—C12—H12B109.5
C4—C5—H5A119.6N5—C12—H12C109.5
C6—C5—H5A119.6H12A—C12—H12C109.5
C1—C6—C5117.9 (2)H12B—C12—H12C109.5
C9—N1—N2—C100.4 (3)C1—C6—C7—N4177.0 (2)
C8—N1—N2—C10177.9 (2)C5—C6—C7—N42.8 (3)
C11—O1—N4—C7179.96 (19)C1—C6—C7—C82.7 (3)
C6—C1—C2—C30.5 (4)C5—C6—C7—C8177.5 (2)
C1—C2—C3—C40.7 (4)C9—N1—C8—C7141.5 (3)
C1—C2—C3—Cl1179.79 (19)N2—N1—C8—C741.6 (3)
C2—C3—C4—C51.1 (4)N4—C7—C8—N174.3 (3)
Cl1—C3—C4—C5179.40 (18)C6—C7—C8—N1106.1 (2)
C2—C3—C4—Cl2179.50 (19)C10—N3—C9—N10.2 (3)
Cl1—C3—C4—Cl20.0 (3)N2—N1—C9—N30.1 (3)
C3—C4—C5—C60.3 (4)C8—N1—C9—N3177.3 (2)
Cl2—C4—C5—C6179.70 (19)N1—N2—C10—N30.6 (3)
C2—C1—C6—C51.3 (4)C9—N3—C10—N20.6 (4)
C2—C1—C6—C7178.5 (2)C12—N5—C11—O21.3 (4)
C4—C5—C6—C10.9 (3)C12—N5—C11—O1179.1 (2)
C4—C5—C6—C7178.9 (2)N4—O1—C11—O2173.63 (18)
O1—N4—C7—C6177.40 (17)N4—O1—C11—N56.7 (3)
O1—N4—C7—C82.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···N3i0.862.333.035 (3)139
C9—H9···O2ii0.932.283.191 (3)167
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC12H11Cl2N5O2
Mr328.16
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)6.016 (2), 8.430 (2), 14.721 (4)
α, β, γ (°)101.501 (4), 100.057 (4), 93.977 (4)
V3)716.1 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.47
Crystal size (mm)0.30 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.873, 0.921
No. of measured, independent and
observed [I > 2σ(I)] reflections
3665, 2497, 1863
Rint0.019
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.111, 1.04
No. of reflections2497
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.23

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···N3i0.862.333.035 (3)139.0
C9—H9···O2ii0.932.283.191 (3)167.3
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1.
 

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