1-(2,5-Dichloro­phen­yl)-2-(1H-1,2,4-triazol-1-yl)ethanone oxime

Mol­ecules of the title compound, C₁₀H₈Cl₂N₄O, are linked into infinite chains along the c axis via O—H...N inter­molecular hydrogen bonds. The packing is further stabilized by π–π inter­actions involving the triazole rings.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.120
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-(2,5-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone oxime

Crystal data

C10H8Cl2N4O	F(000) = 552
Mr = 271.10	Dx = 1.519 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 1832 reflections
a = 15.106 (3) Å	θ = 2.8–24.0°
b = 9.1538 (16) Å	µ = 0.54 mm^−1
c = 8.7550 (16) Å	T = 293 K
β = 101.673 (3)°	Block, colourless
V = 1185.5 (4) Å^3	0.35 × 0.29 × 0.20 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2330 independent reflections
Radiation source: fine-focus sealed tube	1810 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.6°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→9
Tmin = 0.835, Tmax = 0.901	l = −8→10
6420 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.7342P] where P = (Fo^2 + 2Fc^2)/3
2330 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.59097 (6)	0.59725 (9)	0.10660 (11)	0.0859 (3)
Cl2	0.69603 (7)	1.25266 (9)	0.12027 (13)	0.0935 (3)
O1	0.89083 (11)	1.0387 (2)	−0.16775 (18)	0.0588 (5)
H0A	0.8892	1.0278	−0.2612	0.088*
N1	0.89130 (13)	1.0040 (2)	0.28292 (19)	0.0436 (5)
C7	0.80796 (15)	1.0105 (3)	0.0113 (2)	0.0418 (5)
N4	0.80851 (13)	0.9947 (2)	−0.1330 (2)	0.0493 (5)
C6	0.72360 (15)	0.9670 (3)	0.0627 (2)	0.0422 (5)
N2	0.91632 (16)	0.8652 (3)	0.3165 (3)	0.0636 (6)
C5	0.69811 (16)	0.8216 (3)	0.0603 (3)	0.0484 (6)
H5A	0.7328	0.7513	0.0230	0.058*
C1	0.66943 (19)	1.0677 (3)	0.1185 (3)	0.0577 (7)
C4	0.62166 (18)	0.7800 (3)	0.1126 (3)	0.0548 (7)
N3	0.88149 (16)	0.9735 (3)	0.5234 (2)	0.0655 (7)
C9	0.87106 (19)	1.0654 (3)	0.4071 (3)	0.0593 (7)
H9A	0.8519	1.1616	0.4116	0.071*
C3	0.56953 (19)	0.8807 (4)	0.1702 (4)	0.0710 (8)
H3B	0.5187	0.8515	0.2069	0.085*
C10	0.90900 (19)	0.8514 (3)	0.4642 (3)	0.0606 (7)
H10A	0.9218	0.7653	0.5208	0.073*
C8	0.88837 (17)	1.0651 (3)	0.1288 (2)	0.0535 (7)
H8A	0.9434	1.0393	0.0943	0.064*
H8B	0.8856	1.1708	0.1346	0.064*
C2	0.5939 (2)	1.0251 (4)	0.1727 (4)	0.0779 (9)
H2B	0.5592	1.0947	0.2111	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0806 (6)	0.0665 (5)	0.1171 (7)	−0.0274 (4)	0.0355 (5)	−0.0097 (5)
Cl2	0.1012 (7)	0.0475 (5)	0.1427 (9)	0.0037 (4)	0.0505 (6)	−0.0084 (5)
O1	0.0589 (11)	0.0885 (14)	0.0327 (8)	−0.0062 (10)	0.0184 (8)	−0.0001 (9)
N1	0.0498 (11)	0.0538 (12)	0.0290 (9)	−0.0069 (10)	0.0117 (8)	−0.0019 (9)
C7	0.0456 (12)	0.0478 (14)	0.0330 (11)	−0.0013 (11)	0.0103 (9)	0.0006 (10)
N4	0.0521 (12)	0.0606 (14)	0.0370 (10)	−0.0002 (10)	0.0136 (9)	0.0009 (9)
C6	0.0426 (12)	0.0499 (14)	0.0345 (11)	0.0000 (10)	0.0089 (9)	−0.0010 (10)
N2	0.0767 (16)	0.0614 (15)	0.0518 (13)	−0.0031 (13)	0.0110 (11)	−0.0048 (11)
C5	0.0451 (13)	0.0522 (15)	0.0497 (14)	0.0005 (11)	0.0135 (11)	−0.0086 (11)
C1	0.0594 (16)	0.0507 (16)	0.0661 (17)	0.0027 (13)	0.0202 (13)	−0.0058 (13)
C4	0.0513 (14)	0.0574 (16)	0.0568 (15)	−0.0106 (12)	0.0131 (12)	−0.0040 (12)
N3	0.0694 (15)	0.099 (2)	0.0313 (11)	−0.0100 (14)	0.0174 (10)	−0.0002 (12)
C9	0.0750 (18)	0.0670 (18)	0.0359 (13)	0.0023 (15)	0.0111 (12)	−0.0095 (12)
C3	0.0529 (16)	0.080 (2)	0.089 (2)	−0.0092 (15)	0.0344 (15)	−0.0092 (17)
C10	0.0670 (17)	0.0630 (18)	0.0487 (15)	−0.0141 (15)	0.0046 (13)	0.0116 (14)
C8	0.0565 (15)	0.0741 (18)	0.0311 (12)	−0.0148 (13)	0.0112 (11)	0.0058 (11)
C2	0.0657 (19)	0.074 (2)	0.106 (3)	0.0061 (16)	0.0475 (18)	−0.0161 (19)

Geometric parameters (Å, º)

Cl1—C4	1.734 (3)	C5—C4	1.380 (3)
Cl2—C1	1.740 (3)	C5—H5A	0.9300
O1—N4	1.398 (2)	C1—C2	1.378 (4)
O1—H0A	0.8200	C4—C3	1.373 (4)
N1—C9	1.314 (3)	N3—C9	1.305 (3)
N1—N2	1.342 (3)	N3—C10	1.333 (4)
N1—C8	1.453 (3)	C9—H9A	0.9300
C7—N4	1.274 (3)	C3—C2	1.371 (4)
C7—C6	1.489 (3)	C3—H3B	0.9300
C7—C8	1.510 (3)	C10—H10A	0.9300
C6—C5	1.385 (3)	C8—H8A	0.9700
C6—C1	1.385 (3)	C8—H8B	0.9700
N2—C10	1.326 (3)	C2—H2B	0.9300
N4—O1—H0A	109.5	C5—C4—Cl1	119.5 (2)
C9—N1—N2	109.0 (2)	C9—N3—C10	103.6 (2)
C9—N1—C8	129.4 (2)	N3—C9—N1	111.0 (3)
N2—N1—C8	121.5 (2)	N3—C9—H9A	124.5
N4—C7—C6	116.6 (2)	N1—C9—H9A	124.5
N4—C7—C8	123.2 (2)	C2—C3—C4	118.8 (3)
C6—C7—C8	120.15 (18)	C2—C3—H3B	120.6
C7—N4—O1	111.56 (19)	C4—C3—H3B	120.6
C5—C6—C1	117.6 (2)	N2—C10—N3	113.2 (3)
C5—C6—C7	120.3 (2)	N2—C10—H10A	123.4
C1—C6—C7	122.1 (2)	N3—C10—H10A	123.4
C10—N2—N1	103.2 (2)	N1—C8—C7	112.01 (19)
C4—C5—C6	120.6 (2)	N1—C8—H8A	109.2
C4—C5—H5A	119.7	C7—C8—H8A	109.2
C6—C5—H5A	119.7	N1—C8—H8B	109.2
C2—C1—C6	121.5 (3)	C7—C8—H8B	109.2
C2—C1—Cl2	118.6 (2)	H8A—C8—H8B	107.9
C6—C1—Cl2	119.9 (2)	C3—C2—C1	120.4 (3)
C3—C4—C5	121.2 (3)	C3—C2—H2B	119.8
C3—C4—Cl1	119.3 (2)	C1—C2—H2B	119.8
C6—C7—N4—O1	−179.9 (2)	C6—C5—C4—Cl1	179.46 (19)
C8—C7—N4—O1	−2.1 (3)	C10—N3—C9—N1	−0.2 (3)
N4—C7—C6—C5	67.7 (3)	N2—N1—C9—N3	0.0 (3)
C8—C7—C6—C5	−110.2 (3)	C8—N1—C9—N3	179.3 (2)
N4—C7—C6—C1	−114.2 (3)	C5—C4—C3—C2	1.1 (5)
C8—C7—C6—C1	67.8 (3)	Cl1—C4—C3—C2	−179.2 (3)
C9—N1—N2—C10	0.2 (3)	N1—N2—C10—N3	−0.3 (3)
C8—N1—N2—C10	−179.1 (2)	C9—N3—C10—N2	0.4 (3)
C1—C6—C5—C4	−0.3 (4)	C9—N1—C8—C7	−104.4 (3)
C7—C6—C5—C4	177.8 (2)	N2—N1—C8—C7	74.7 (3)
C5—C6—C1—C2	1.3 (4)	N4—C7—C8—N1	−149.3 (2)
C7—C6—C1—C2	−176.8 (3)	C6—C7—C8—N1	28.5 (3)
C5—C6—C1—Cl2	−178.43 (19)	C4—C3—C2—C1	−0.1 (5)
C7—C6—C1—Cl2	3.5 (3)	C6—C1—C2—C3	−1.0 (5)
C6—C5—C4—C3	−0.8 (4)	Cl2—C1—C2—C3	178.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H0A···N3^i	0.82	1.93	2.745 (2)	172

Symmetry code: (i) x, y, z−1.