Diclomezine: 6-(3,5-dichloro-4-methyl-phen-yl)pyridazin-3(2H)-one.

In the title compound, C(11)H(8)Cl(2)N(2)O, the benzene and pyridazine rings are tilted by 8.6 (1)° relative to each other. In the crystal, pairs of inter-molecular N-H⋯O hydrogen bonds form centrosymmetric dimers. π-π contacts with centroid-centroid distances of 3.698 (2) and 3.751 (1) Å and halogen-halogen inter-actions [3.379 (1) Å] also stabilize the structure.

Related literature

For information on the toxicity and fungicidal properties of the title compound, see: Sankyo (1998 ▶). For a related structure, see: Prout et al. (1994 ▶).

Experimental

Crystal data

C11H8Cl2N2O

M = 255.09

Monoclinic,

a = 9.745 (4) Å

b = 13.850 (5) Å

c = 8.481 (3) Å

β = 111.557 (6)°

V = 1064.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.59 mm−1

T = 173 K

0.19 × 0.09 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.897, T max = 0.955

10410 measured reflections

2657 independent reflections

2038 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.07

2657 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and DIAMOND (Brandenburg, 1998 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047409/sj5054sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047409/sj5054Isup2.hkl

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

C11H8Cl2N2O	F(000) = 520
Mr = 255.09	Dx = 1.591 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3791 reflections
a = 9.745 (4) Å	θ = 2.9–28.2°
b = 13.850 (5) Å	µ = 0.59 mm−1
c = 8.481 (3) Å	T = 173 K
β = 111.557 (6)°	Block, colourless
V = 1064.7 (7) Å3	0.19 × 0.09 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	2657 independent reflections
Radiation source: fine-focus sealed tube	2038 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.897, Tmax = 0.955	k = −18→17
10410 measured reflections	l = −11→11

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0323P)2 + 0.5573P] where P = (Fo2 + 2Fc2)/3
2657 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.11909 (5)	0.35378 (4)	0.82090 (6)	0.03367 (14)
Cl2	0.15267 (6)	0.72198 (3)	0.62638 (7)	0.03884 (15)
O1	0.52503 (15)	0.37232 (9)	0.02888 (17)	0.0290 (3)
N1	0.42007 (16)	0.47759 (11)	0.15589 (18)	0.0240 (3)
H1	0.4313	0.5229	0.0888	0.029*
N2	0.35554 (16)	0.50487 (11)	0.26436 (18)	0.0239 (3)
C1	0.47026 (19)	0.38769 (13)	0.1379 (2)	0.0234 (4)
C2	0.45389 (19)	0.31751 (13)	0.2541 (2)	0.0258 (4)
H2	0.4893	0.2536	0.2543	0.031*
C3	0.38829 (19)	0.34224 (13)	0.3631 (2)	0.0246 (4)
H3	0.3760	0.2954	0.4387	0.029*
C4	0.33735 (18)	0.43848 (12)	0.3652 (2)	0.0214 (3)
C5	0.26737 (18)	0.47099 (12)	0.4848 (2)	0.0218 (3)
C6	0.22820 (18)	0.40586 (13)	0.5865 (2)	0.0239 (4)
H6	0.2436	0.3386	0.5781	0.029*
C7	0.16682 (18)	0.43931 (13)	0.6996 (2)	0.0243 (4)
C8	0.13991 (18)	0.53629 (13)	0.7192 (2)	0.0241 (4)
C9	0.17893 (19)	0.59892 (13)	0.6130 (2)	0.0254 (4)
C10	0.23982 (18)	0.56857 (13)	0.4983 (2)	0.0238 (4)
H10	0.2630	0.6143	0.4284	0.029*
C11	0.0760 (2)	0.57125 (15)	0.8451 (2)	0.0332 (4)
H11C	0.1557	0.5816	0.9551	0.050*
H11A	0.0072	0.5229	0.8573	0.050*
H11B	0.0235	0.6321	0.8053	0.050*

	U11	U22	U33	U12	U13	U23
Cl1	0.0373 (3)	0.0338 (3)	0.0379 (3)	−0.00164 (19)	0.0233 (2)	0.0084 (2)
Cl2	0.0529 (3)	0.0248 (2)	0.0479 (3)	0.0092 (2)	0.0292 (3)	0.0019 (2)
O1	0.0396 (7)	0.0248 (7)	0.0304 (7)	0.0001 (5)	0.0220 (6)	−0.0012 (5)
N1	0.0319 (8)	0.0224 (7)	0.0227 (8)	0.0001 (6)	0.0157 (6)	0.0023 (6)
N2	0.0283 (7)	0.0235 (7)	0.0240 (8)	0.0003 (6)	0.0147 (6)	0.0006 (6)
C1	0.0247 (8)	0.0223 (8)	0.0242 (9)	−0.0025 (6)	0.0101 (7)	−0.0022 (7)
C2	0.0304 (9)	0.0192 (8)	0.0292 (10)	−0.0006 (7)	0.0127 (8)	0.0000 (7)
C3	0.0286 (9)	0.0219 (9)	0.0250 (9)	−0.0022 (7)	0.0120 (7)	0.0017 (7)
C4	0.0222 (8)	0.0216 (8)	0.0210 (8)	−0.0020 (6)	0.0087 (7)	−0.0003 (7)
C5	0.0202 (8)	0.0243 (9)	0.0203 (8)	−0.0014 (6)	0.0068 (6)	0.0003 (7)
C6	0.0239 (8)	0.0230 (9)	0.0265 (9)	−0.0003 (7)	0.0112 (7)	0.0009 (7)
C7	0.0226 (8)	0.0285 (9)	0.0231 (9)	−0.0019 (7)	0.0099 (7)	0.0037 (7)
C8	0.0197 (8)	0.0303 (9)	0.0220 (9)	0.0008 (7)	0.0072 (7)	−0.0012 (7)
C9	0.0261 (9)	0.0233 (9)	0.0266 (9)	0.0038 (7)	0.0096 (7)	0.0002 (7)
C10	0.0241 (8)	0.0244 (9)	0.0246 (9)	0.0010 (7)	0.0109 (7)	0.0037 (7)
C11	0.0374 (10)	0.0373 (11)	0.0296 (10)	0.0043 (8)	0.0178 (8)	−0.0001 (9)

Cl1—C7	1.7404 (18)	C5—C10	1.391 (3)
Cl2—C9	1.733 (2)	C5—C6	1.395 (2)
O1—C1	1.244 (2)	C6—C7	1.384 (2)
N1—N2	1.345 (2)	C6—H6	0.9500
N1—C1	1.367 (2)	C7—C8	1.390 (3)
N1—H1	0.8800	C8—C9	1.400 (3)
N2—C4	1.311 (2)	C8—C11	1.500 (2)
C1—C2	1.435 (3)	C9—C10	1.378 (2)
C2—C3	1.347 (3)	C10—H10	0.9500
C2—H2	0.9500	C11—H11C	0.9800
C3—C4	1.425 (2)	C11—H11A	0.9800
C3—H3	0.9500	C11—H11B	0.9800
C4—C5	1.485 (2)
N2—N1—C1	127.50 (15)	C7—C6—H6	120.1
N2—N1—H1	116.2	C5—C6—H6	120.1
C1—N1—H1	116.2	C6—C7—C8	123.71 (16)
C4—N2—N1	117.27 (15)	C6—C7—Cl1	117.35 (14)
O1—C1—N1	120.54 (16)	C8—C7—Cl1	118.93 (14)
O1—C1—C2	125.54 (17)	C7—C8—C9	114.45 (16)
N1—C1—C2	113.92 (16)	C7—C8—C11	122.88 (17)
C3—C2—C1	120.00 (17)	C9—C8—C11	122.67 (17)
C3—C2—H2	120.0	C10—C9—C8	123.67 (17)
C1—C2—H2	120.0	C10—C9—Cl2	117.27 (14)
C2—C3—C4	120.11 (16)	C8—C9—Cl2	119.06 (14)
C2—C3—H3	119.9	C9—C10—C5	120.05 (16)
C4—C3—H3	119.9	C9—C10—H10	120.0
N2—C4—C3	121.12 (16)	C5—C10—H10	120.0
N2—C4—C5	116.03 (15)	C8—C11—H11C	109.5
C3—C4—C5	122.79 (15)	C8—C11—H11A	109.5
C10—C5—C6	118.21 (16)	H11C—C11—H11A	109.5
C10—C5—C4	120.12 (15)	C8—C11—H11B	109.5
C6—C5—C4	121.67 (16)	H11C—C11—H11B	109.5
C7—C6—C5	119.90 (17)	H11A—C11—H11B	109.5
C1—N1—N2—C4	−0.2 (3)	C4—C5—C6—C7	178.27 (15)
N2—N1—C1—O1	178.37 (16)	C5—C6—C7—C8	0.3 (3)
N2—N1—C1—C2	−2.0 (3)	C5—C6—C7—Cl1	179.41 (13)
O1—C1—C2—C3	−177.86 (17)	C6—C7—C8—C9	0.6 (3)
N1—C1—C2—C3	2.6 (2)	Cl1—C7—C8—C9	−178.51 (13)
C1—C2—C3—C4	−1.1 (3)	C6—C7—C8—C11	−178.75 (17)
N1—N2—C4—C3	1.9 (2)	Cl1—C7—C8—C11	2.2 (2)
N1—N2—C4—C5	179.33 (14)	C7—C8—C9—C10	−0.3 (3)
C2—C3—C4—N2	−1.3 (3)	C11—C8—C9—C10	178.98 (17)
C2—C3—C4—C5	−178.51 (16)	C7—C8—C9—Cl2	−179.37 (13)
N2—C4—C5—C10	−6.9 (2)	C11—C8—C9—Cl2	−0.1 (2)
C3—C4—C5—C10	170.44 (16)	C8—C9—C10—C5	−0.8 (3)
N2—C4—C5—C6	173.38 (16)	Cl2—C9—C10—C5	178.26 (13)
C3—C4—C5—C6	−9.3 (3)	C6—C5—C10—C9	1.7 (3)
C10—C5—C6—C7	−1.5 (3)	C4—C5—C10—C9	−178.06 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	1.90	2.771 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	1.90	2.771 (2)	172

Symmetry code: (i) .