2-(2,4-Dichloro-phen-oxy)-1-(1H-pyrazol-1-yl)ethanone.

In the title compound, C(11)H(8)Cl(2)N(2)O(2), the 2,4-dichloro-phen-oxy and 1H-pyrazole groups are almost planar [r.m.s. deviations of 0.0157 and 0.0008 Å, respectively] and are oriented at a dihedral angle of 64.17 (5)° with respect to one another. In the crystal, the mol-ecules are stabilized in the form of dimers due to inversion-related C-H⋯O hydrogen bonds, with R(2) (2)(10) ring motifs.

Related literature

Aryl­oxyacetic acid and its various derivatives are used as herbicides and pesticides, see: Crafts (1957 ▶). For our work on the synthesis of heterocyclic compounds, see: Khan et al. (2009 ▶). For a related structure, see: Wang et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H8Cl2N2O2

M = 271.09

Triclinic,

a = 4.2030 (1) Å

b = 10.3074 (3) Å

c = 13.4966 (4) Å

α = 87.510 (2)°

β = 83.774 (1)°

γ = 88.335 (1)°

V = 580.53 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.55 mm−1

T = 296 K

0.30 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.982, T max = 0.988

10353 measured reflections

2861 independent reflections

2232 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.04

2861 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035087/si2292sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035087/si2292Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H8Cl2N2O2	Z = 2
Mr = 271.09	F(000) = 276
Triclinic, P1	Dx = 1.551 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.2030 (1) Å	Cell parameters from 2920 reflections
b = 10.3074 (3) Å	θ = 2.6–27.9°
c = 13.4966 (4) Å	µ = 0.55 mm−1
α = 87.510 (2)°	T = 296 K
β = 83.774 (1)°	Prismatic, pale brown
γ = 88.335 (1)°	0.30 × 0.22 × 0.18 mm
V = 580.53 (3) Å3

Bruker Kappa APEXII CCD diffractometer	2861 independent reflections
Radiation source: fine-focus sealed tube	2232 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 7.50 pixels mm-1	θmax = 28.4°, θmin = 2.0°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.982, Tmax = 0.988	l = −17→17
10353 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0378P)2 + 0.1536P] where P = (Fo2 + 2Fc2)/3
2861 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
Cl1	0.18429 (10)	1.01977 (4)	0.34325 (3)	0.0568 (2)
Cl2	0.65932 (16)	0.65004 (6)	0.58253 (4)	0.0775 (2)
O1	0.5309 (3)	0.88439 (11)	0.18509 (8)	0.0484 (4)
O2	0.4918 (3)	0.66285 (12)	0.08285 (9)	0.0547 (4)
N1	0.8767 (3)	0.72296 (12)	−0.03954 (9)	0.0409 (4)
N2	1.0808 (3)	0.81744 (14)	−0.07931 (11)	0.0508 (5)
C1	0.5754 (3)	0.82450 (15)	0.27460 (11)	0.0409 (5)
C2	0.4121 (3)	0.87940 (15)	0.35859 (12)	0.0414 (5)
C3	0.4354 (4)	0.82649 (16)	0.45278 (12)	0.0484 (5)
C4	0.6248 (4)	0.71690 (17)	0.46376 (13)	0.0499 (5)
C5	0.7924 (4)	0.66131 (17)	0.38241 (13)	0.0534 (6)
C6	0.7676 (4)	0.71501 (17)	0.28800 (13)	0.0498 (5)
C7	0.7588 (4)	0.86184 (16)	0.10197 (12)	0.0456 (5)
C8	0.6884 (4)	0.74046 (15)	0.05091 (11)	0.0404 (5)
C9	1.2064 (5)	0.77078 (19)	−0.16381 (13)	0.0589 (6)
C10	1.0901 (5)	0.6484 (2)	−0.17990 (13)	0.0609 (7)
C11	0.8813 (4)	0.62017 (17)	−0.09989 (13)	0.0523 (6)
H3	0.32501	0.86416	0.50819	0.0580*
H5	0.92191	0.58786	0.39101	0.0641*
H6	0.88072	0.67744	0.23299	0.0597*
H7A	0.97086	0.85358	0.12400	0.0547*
H7B	0.75702	0.93557	0.05484	0.0547*
H9	1.35614	0.81406	−0.20817	0.0706*
H10	1.14575	0.59735	−0.23456	0.0731*
H11	0.76304	0.54516	−0.08799	0.0627*

	U11	U22	U33	U12	U13	U23
Cl1	0.0547 (3)	0.0481 (2)	0.0649 (3)	0.0094 (2)	0.0060 (2)	−0.0084 (2)
Cl2	0.1045 (4)	0.0712 (3)	0.0552 (3)	0.0028 (3)	−0.0074 (3)	0.0102 (2)
O1	0.0497 (6)	0.0498 (7)	0.0447 (6)	0.0070 (5)	−0.0004 (5)	−0.0064 (5)
O2	0.0566 (7)	0.0542 (7)	0.0528 (7)	−0.0212 (6)	0.0022 (5)	−0.0033 (5)
N1	0.0431 (7)	0.0386 (7)	0.0406 (7)	−0.0048 (5)	−0.0022 (5)	−0.0017 (5)
N2	0.0541 (8)	0.0445 (8)	0.0516 (8)	−0.0087 (6)	0.0033 (6)	0.0038 (6)
C1	0.0385 (8)	0.0399 (8)	0.0448 (8)	−0.0053 (6)	−0.0030 (6)	−0.0079 (6)
C2	0.0361 (8)	0.0366 (8)	0.0511 (9)	−0.0043 (6)	0.0006 (6)	−0.0085 (6)
C3	0.0473 (9)	0.0488 (9)	0.0476 (9)	−0.0087 (7)	0.0058 (7)	−0.0087 (7)
C4	0.0561 (10)	0.0465 (9)	0.0476 (9)	−0.0078 (8)	−0.0065 (7)	−0.0006 (7)
C5	0.0583 (10)	0.0432 (9)	0.0600 (11)	0.0039 (8)	−0.0119 (8)	−0.0065 (8)
C6	0.0516 (9)	0.0471 (9)	0.0509 (9)	0.0043 (7)	−0.0042 (7)	−0.0130 (7)
C7	0.0496 (9)	0.0410 (8)	0.0451 (8)	−0.0060 (7)	0.0028 (7)	−0.0059 (7)
C8	0.0407 (8)	0.0400 (8)	0.0408 (8)	−0.0041 (6)	−0.0049 (6)	−0.0005 (6)
C9	0.0600 (11)	0.0630 (12)	0.0498 (10)	0.0000 (9)	0.0086 (8)	0.0045 (8)
C10	0.0696 (12)	0.0647 (12)	0.0471 (10)	0.0031 (10)	0.0024 (8)	−0.0134 (9)
C11	0.0586 (10)	0.0470 (9)	0.0524 (10)	−0.0032 (8)	−0.0067 (8)	−0.0114 (8)

Cl1—C2	1.7290 (15)	C4—C5	1.376 (2)
Cl2—C4	1.7362 (18)	C5—C6	1.380 (2)
O1—C1	1.3613 (18)	C7—C8	1.506 (2)
O1—C7	1.417 (2)	C9—C10	1.400 (3)
O2—C8	1.200 (2)	C10—C11	1.343 (3)
N1—N2	1.3695 (19)	C3—H3	0.9300
N1—C8	1.397 (2)	C5—H5	0.9300
N1—C11	1.363 (2)	C6—H6	0.9300
N2—C9	1.309 (2)	C7—H7A	0.9700
C1—C2	1.393 (2)	C7—H7B	0.9700
C1—C6	1.386 (2)	C9—H9	0.9300
C2—C3	1.374 (2)	C10—H10	0.9300
C3—C4	1.375 (2)	C11—H11	0.9300
Cl1···O1	2.8447 (12)	C2···C6i	3.476 (2)
Cl1···C1i	3.5263 (15)	C3···C5i	3.474 (2)
Cl1···C2i	3.5736 (14)	C5···C2viii	3.469 (2)
Cl1···Cl2ii	3.6862 (7)	C5···C3viii	3.474 (2)
Cl2···Cl1ii	3.6862 (7)	C6···O2	3.188 (2)
Cl1···H9iii	3.0200	C6···C1viii	3.592 (2)
Cl1···H3iv	3.0300	C6···C2viii	3.476 (2)
Cl2···H10v	3.1400	C6···C8	3.252 (2)
Cl2···H5vi	3.0100	C7···N2iii	3.387 (2)
O1···Cl1	2.8447 (12)	C8···N2i	3.313 (2)
O1···O2	2.7368 (17)	C8···C6	3.252 (2)
O2···N2i	3.2665 (19)	C9···C11viii	3.370 (3)
O2···O1	2.7368 (17)	C9···N1viii	3.445 (2)
O2···N1i	3.2466 (18)	C11···C9i	3.370 (3)
O2···C1	3.1942 (19)	C11···O2vii	3.339 (2)
O2···C6	3.188 (2)	C6···H7A	2.6600
O2···C11vii	3.339 (2)	C7···H6	2.6200
O1···H7Ai	2.6100	C8···H6	2.7200
O2···H6	2.7500	H3···Cl1iv	3.0300
O2···H11	2.7700	H5···Cl2vi	3.0100
O2···H11vii	2.4200	H6···O2	2.7500
N1···O2viii	3.2466 (18)	H6···C7	2.6200
N1···C9i	3.445 (2)	H6···C8	2.7200
N2···O2viii	3.2665 (19)	H6···H7A	2.3000
N2···C8viii	3.313 (2)	H7A···O1viii	2.6100
N2···C7iii	3.387 (2)	H7A···N2	2.7700
N2···H7A	2.7700	H7A···C6	2.6600
N2···H7B	2.4800	H7A···H6	2.3000
N2···H7Biii	2.7000	H7B···N2	2.4800
C1···Cl1viii	3.5263 (14)	H7B···N2iii	2.7000
C1···O2	3.1942 (19)	H9···Cl1iii	3.0200
C1···C6i	3.592 (2)	H10···Cl2ix	3.1400
C2···Cl1viii	3.5736 (14)	H11···O2	2.7700
C2···C5i	3.469 (2)	H11···O2vii	2.4200
C1—O1—C7	118.85 (12)	N2—C9—C10	112.42 (17)
N2—N1—C8	120.45 (13)	C9—C10—C11	105.58 (16)
N2—N1—C11	111.72 (13)	N1—C11—C10	106.55 (16)
C8—N1—C11	127.80 (13)	C2—C3—H3	121.00
N1—N2—C9	103.74 (14)	C4—C3—H3	121.00
O1—C1—C2	116.28 (13)	C4—C5—H5	120.00
O1—C1—C6	125.34 (14)	C6—C5—H5	120.00
C2—C1—C6	118.38 (14)	C1—C6—H6	120.00
Cl1—C2—C1	118.80 (12)	C5—C6—H6	120.00
Cl1—C2—C3	119.68 (12)	O1—C7—H7A	109.00
C1—C2—C3	121.49 (14)	O1—C7—H7B	109.00
C2—C3—C4	118.88 (15)	C8—C7—H7A	109.00
Cl2—C4—C3	119.31 (13)	C8—C7—H7B	109.00
Cl2—C4—C5	119.64 (14)	H7A—C7—H7B	108.00
C3—C4—C5	121.04 (16)	N2—C9—H9	124.00
C4—C5—C6	119.73 (16)	C10—C9—H9	124.00
C1—C6—C5	120.47 (16)	C9—C10—H10	127.00
O1—C7—C8	111.44 (13)	C11—C10—H10	127.00
O2—C8—N1	121.06 (14)	N1—C11—H11	127.00
O2—C8—C7	124.89 (14)	C10—C11—H11	127.00
N1—C8—C7	114.05 (13)
C7—O1—C1—C2	160.01 (13)	C6—C1—C2—C3	−0.8 (2)
C7—O1—C1—C6	−20.0 (2)	O1—C1—C6—C5	−179.24 (15)
C1—O1—C7—C8	85.03 (17)	C2—C1—C6—C5	0.8 (2)
C8—N1—N2—C9	−177.90 (15)	Cl1—C2—C3—C4	−178.20 (13)
C11—N1—N2—C9	0.21 (18)	C1—C2—C3—C4	0.0 (2)
N2—N1—C8—O2	174.44 (14)	C2—C3—C4—Cl2	179.37 (12)
N2—N1—C8—C7	−6.0 (2)	C2—C3—C4—C5	0.8 (3)
C11—N1—C8—O2	−3.3 (3)	Cl2—C4—C5—C6	−179.41 (14)
C11—N1—C8—C7	176.21 (15)	C3—C4—C5—C6	−0.9 (3)
N2—N1—C11—C10	−0.18 (19)	C4—C5—C6—C1	0.0 (3)
C8—N1—C11—C10	177.76 (16)	O1—C7—C8—O2	−9.1 (2)
N1—N2—C9—C10	−0.2 (2)	O1—C7—C8—N1	171.34 (13)
O1—C1—C2—Cl1	−2.56 (18)	N2—C9—C10—C11	0.1 (2)
O1—C1—C2—C3	179.19 (14)	C9—C10—C11—N1	0.1 (2)
C6—C1—C2—Cl1	177.44 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2vii	0.93	2.42	3.339 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2i	0.93	2.42	3.339 (2)	170

Symmetry code: (i) .