1-[2-(3,4-Dichloro-phen-yl)-5-(3,4,5-trimethoxy-phen-yl)-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone.

The title compound, C(19)H(18)Cl(2)N(2)O(5), was synthesized by the reaction of N'-(3,4-dichloro-benzyl-idene)-3,4,5-trimethoxy-benzo-hydrazide and acetic anhydride. The oxadiazole ring makes dihedral angles of 82.82 (7) and 9.92 (7)° with the 3,4-dichloro-benzene and the 3,4,5-trimethoxy-benzene ring planes, respectively. The crystal structure is stabilized by inter-molecular C-H⋯ O and C-H⋯ N hydrogen bonds. Intra-molecular C-H⋯O and C-H⋯N hydrogen bonds are also present.

Related literature

For related literature, see: Abdel et al. (2003 ▶); Abdel-Rahman & Farghaly (2004 ▶); Chai et al. (2002 ▶); Jin et al. (2006 ▶); Mohd et al. (2004 ▶).

Experimental

Crystal data

C19H18Cl2N2O5

M = 425.25

Monoclinic,

a = 7.6743 (4) Å

b = 15.9516 (8) Å

c = 15.7483 (8) Å

β = 90.8940 (10)°

V = 1927.63 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 173 (2) K

0.47 × 0.39 × 0.32 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.845, T max = 0.890

10032 measured reflections

4159 independent reflections

3238 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.125

S = 1.04

4159 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020771/wn2269sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020771/wn2269Isup2.hkl

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

C19H18Cl2N2O5	F000 = 880
Mr = 425.25	Dx = 1.465 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5138 reflections
a = 7.6743 (4) Å	θ = 2.6–27.1º
b = 15.9516 (8) Å	µ = 0.37 mm−1
c = 15.7483 (8) Å	T = 173 (2) K
β = 90.8940 (10)º	Block, colorless
V = 1927.63 (17) Å3	0.47 × 0.39 × 0.32 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	4159 independent reflections
Radiation source: fine-focus sealed tube	3238 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 173(2) K	θmax = 27.2º
ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −8→9
Tmin = 0.845, Tmax = 0.891	k = −20→18
10032 measured reflections	l = −13→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0625P)2 + 1.3473P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4159 reflections	Δρmax = 0.34 e Å−3
257 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.29475 (7)	0.36125 (4)	0.89108 (4)	0.04132 (18)
Cl2	0.44596 (8)	0.54237 (4)	0.85758 (4)	0.03835 (17)
C1	0.7817 (3)	0.05267 (12)	0.99579 (13)	0.0233 (4)
C2	0.7051 (3)	−0.00409 (13)	1.05104 (13)	0.0243 (4)
H2	0.6667	0.0136	1.1053	0.029*
C3	0.6857 (3)	−0.08687 (12)	1.02552 (13)	0.0254 (4)
C4	0.7416 (3)	−0.11303 (12)	0.94532 (13)	0.0250 (4)
C5	0.8160 (3)	−0.05492 (13)	0.89080 (12)	0.0239 (4)
C6	0.8351 (3)	0.02847 (12)	0.91572 (13)	0.0245 (4)
H6	0.8842	0.0683	0.8782	0.029*
C7	0.8153 (3)	0.13859 (12)	1.02448 (13)	0.0229 (4)
C8	0.9032 (3)	0.27301 (12)	1.00923 (13)	0.0240 (4)
H8	1.0284	0.2903	1.0080	0.029*
C9	0.7883 (3)	0.33955 (12)	0.97007 (12)	0.0231 (4)
C10	0.6145 (3)	0.32243 (12)	0.95089 (13)	0.0248 (4)
H10	0.5676	0.2685	0.9619	0.030*
C11	0.5100 (3)	0.38450 (13)	0.91558 (13)	0.0262 (4)
C12	0.5775 (3)	0.46408 (12)	0.90009 (13)	0.0263 (4)
C13	0.7498 (3)	0.48130 (13)	0.91895 (14)	0.0297 (5)
H13	0.7963	0.5354	0.9081	0.036*
C14	0.8548 (3)	0.41901 (13)	0.95392 (13)	0.0268 (4)
H14	0.9735	0.4308	0.9670	0.032*
C15	0.9181 (3)	0.29242 (13)	1.16484 (14)	0.0297 (5)
C16	0.8863 (4)	0.25497 (16)	1.25067 (15)	0.0428 (6)
H16A	0.9930	0.2277	1.2717	0.064*
H16B	0.7925	0.2134	1.2461	0.064*
H16C	0.8525	0.2993	1.2902	0.064*
C17	0.5778 (3)	−0.12792 (16)	1.16051 (15)	0.0383 (6)
H17A	0.6858	−0.1100	1.1892	0.058*
H17B	0.5312	−0.1774	1.1893	0.058*
H17C	0.4923	−0.0824	1.1623	0.058*
C18	0.6289 (3)	−0.22110 (15)	0.85465 (16)	0.0368 (5)
H18A	0.5145	−0.1941	0.8580	0.055*
H18B	0.6143	−0.2821	0.8544	0.055*
H18C	0.6861	−0.2036	0.8024	0.055*
C19	0.9654 (3)	−0.03053 (15)	0.76156 (14)	0.0351 (5)
H19A	0.8912	0.0169	0.7450	0.053*
H19B	1.0019	−0.0607	0.7106	0.053*
H19C	1.0685	−0.0098	0.7925	0.053*
N1	0.7969 (2)	0.16636 (10)	1.09988 (11)	0.0248 (4)
N2	0.8524 (2)	0.25043 (10)	1.09633 (10)	0.0251 (4)
O1	0.6131 (2)	−0.14829 (9)	1.07411 (10)	0.0345 (4)
O2	0.7344 (2)	−0.19688 (9)	0.92680 (10)	0.0354 (4)
O3	0.8701 (2)	−0.08591 (9)	0.81492 (9)	0.0304 (3)
O4	0.87792 (19)	0.19385 (8)	0.96599 (9)	0.0265 (3)
O5	0.9955 (2)	0.35859 (10)	1.15404 (11)	0.0401 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0272 (3)	0.0402 (3)	0.0563 (4)	−0.0036 (2)	−0.0087 (2)	0.0089 (3)
Cl2	0.0433 (3)	0.0298 (3)	0.0419 (3)	0.0081 (2)	−0.0035 (2)	0.0093 (2)
C1	0.0220 (9)	0.0187 (9)	0.0290 (10)	0.0012 (8)	−0.0052 (8)	0.0011 (8)
C2	0.0229 (10)	0.0251 (10)	0.0249 (10)	0.0007 (8)	−0.0009 (8)	−0.0016 (8)
C3	0.0252 (10)	0.0206 (10)	0.0303 (11)	−0.0032 (8)	−0.0026 (8)	0.0056 (8)
C4	0.0283 (10)	0.0160 (9)	0.0307 (11)	0.0004 (8)	−0.0043 (8)	0.0000 (8)
C5	0.0243 (10)	0.0225 (10)	0.0247 (10)	0.0030 (8)	−0.0026 (8)	−0.0024 (7)
C6	0.0255 (10)	0.0217 (10)	0.0261 (10)	0.0000 (8)	−0.0034 (8)	0.0027 (8)
C7	0.0217 (9)	0.0210 (10)	0.0260 (10)	0.0009 (8)	−0.0011 (7)	0.0024 (7)
C8	0.0276 (10)	0.0172 (9)	0.0273 (10)	−0.0030 (8)	0.0015 (8)	−0.0023 (7)
C9	0.0280 (10)	0.0194 (9)	0.0219 (9)	0.0003 (8)	0.0017 (8)	−0.0018 (7)
C10	0.0277 (10)	0.0201 (10)	0.0266 (10)	−0.0032 (8)	0.0012 (8)	0.0004 (8)
C11	0.0243 (10)	0.0283 (11)	0.0261 (10)	−0.0029 (8)	0.0004 (8)	0.0007 (8)
C12	0.0328 (11)	0.0211 (10)	0.0250 (10)	0.0042 (8)	0.0020 (8)	0.0035 (8)
C13	0.0363 (12)	0.0201 (10)	0.0328 (11)	−0.0040 (9)	0.0030 (9)	0.0025 (8)
C14	0.0257 (10)	0.0216 (10)	0.0332 (11)	−0.0039 (8)	0.0016 (8)	−0.0016 (8)
C15	0.0363 (12)	0.0215 (10)	0.0312 (11)	0.0032 (9)	−0.0006 (9)	−0.0070 (8)
C16	0.0668 (17)	0.0339 (13)	0.0277 (12)	−0.0001 (12)	−0.0001 (11)	−0.0065 (10)
C17	0.0478 (14)	0.0373 (13)	0.0300 (12)	−0.0120 (11)	0.0034 (10)	0.0064 (10)
C18	0.0350 (12)	0.0305 (12)	0.0448 (13)	−0.0101 (10)	−0.0005 (10)	−0.0107 (10)
C19	0.0431 (13)	0.0345 (12)	0.0279 (11)	−0.0098 (10)	0.0052 (9)	−0.0017 (9)
N1	0.0291 (9)	0.0177 (8)	0.0277 (9)	−0.0016 (7)	−0.0018 (7)	−0.0001 (7)
N2	0.0309 (9)	0.0199 (8)	0.0245 (9)	−0.0015 (7)	0.0001 (7)	−0.0013 (7)
O1	0.0480 (10)	0.0232 (8)	0.0325 (8)	−0.0107 (7)	0.0041 (7)	0.0023 (6)
O2	0.0520 (10)	0.0185 (7)	0.0355 (9)	−0.0018 (7)	−0.0072 (7)	−0.0029 (6)
O3	0.0388 (9)	0.0246 (8)	0.0278 (8)	−0.0043 (6)	0.0048 (6)	−0.0035 (6)
O4	0.0367 (8)	0.0168 (7)	0.0262 (7)	−0.0013 (6)	0.0029 (6)	−0.0010 (5)
O5	0.0531 (10)	0.0255 (8)	0.0416 (10)	−0.0062 (7)	−0.0027 (8)	−0.0096 (7)

Cl1—C11	1.730 (2)	C11—C12	1.394 (3)
Cl2—C12	1.734 (2)	C12—C13	1.378 (3)
C1—C6	1.387 (3)	C13—C14	1.388 (3)
C1—C2	1.392 (3)	C13—H13	0.9500
C1—C7	1.465 (3)	C14—H14	0.9500
C2—C3	1.388 (3)	C15—O5	1.224 (3)
C2—H2	0.9500	C15—N2	1.360 (3)
C3—O1	1.367 (2)	C15—C16	1.501 (3)
C3—C4	1.404 (3)	C16—H16A	0.9800
C4—O2	1.370 (2)	C16—H16B	0.9800
C4—C5	1.392 (3)	C16—H16C	0.9800
C5—O3	1.364 (2)	C17—O1	1.429 (3)
C5—C6	1.394 (3)	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C7—N1	1.277 (3)	C17—H17C	0.9800
C7—O4	1.368 (2)	C18—O2	1.438 (3)
C8—O4	1.446 (2)	C18—H18A	0.9800
C8—N2	1.476 (3)	C18—H18B	0.9800
C8—C9	1.506 (3)	C18—H18C	0.9800
C8—H8	1.0000	C19—O3	1.429 (3)
C9—C10	1.390 (3)	C19—H19A	0.9800
C9—C14	1.391 (3)	C19—H19B	0.9800
C10—C11	1.385 (3)	C19—H19C	0.9800
C10—H10	0.9500	N1—N2	1.409 (2)
C6—C1—C2	121.40 (18)	C12—C13—H13	120.3
C6—C1—C7	119.20 (18)	C14—C13—H13	120.3
C2—C1—C7	119.32 (18)	C13—C14—C9	120.8 (2)
C3—C2—C1	118.83 (19)	C13—C14—H14	119.6
C3—C2—H2	120.6	C9—C14—H14	119.6
C1—C2—H2	120.6	O5—C15—N2	119.3 (2)
O1—C3—C2	124.24 (19)	O5—C15—C16	123.7 (2)
O1—C3—C4	115.06 (18)	N2—C15—C16	117.0 (2)
C2—C3—C4	120.70 (18)	C15—C16—H16A	109.5
O2—C4—C5	122.30 (19)	C15—C16—H16B	109.5
O2—C4—C3	118.03 (18)	H16A—C16—H16B	109.5
C5—C4—C3	119.42 (18)	C15—C16—H16C	109.5
O3—C5—C4	115.61 (18)	H16A—C16—H16C	109.5
O3—C5—C6	124.10 (19)	H16B—C16—H16C	109.5
C4—C5—C6	120.27 (19)	O1—C17—H17A	109.5
C1—C6—C5	119.37 (19)	O1—C17—H17B	109.5
C1—C6—H6	120.3	H17A—C17—H17B	109.5
C5—C6—H6	120.3	O1—C17—H17C	109.5
N1—C7—O4	116.60 (17)	H17A—C17—H17C	109.5
N1—C7—C1	126.14 (18)	H17B—C17—H17C	109.5
O4—C7—C1	117.22 (17)	O2—C18—H18A	109.5
O4—C8—N2	100.90 (14)	O2—C18—H18B	109.5
O4—C8—C9	110.42 (16)	H18A—C18—H18B	109.5
N2—C8—C9	113.01 (16)	O2—C18—H18C	109.5
O4—C8—H8	110.7	H18A—C18—H18C	109.5
N2—C8—H8	110.7	H18B—C18—H18C	109.5
C9—C8—H8	110.7	O3—C19—H19A	109.5
C10—C9—C14	119.51 (18)	O3—C19—H19B	109.5
C10—C9—C8	120.30 (18)	H19A—C19—H19B	109.5
C14—C9—C8	120.18 (18)	O3—C19—H19C	109.5
C11—C10—C9	119.63 (19)	H19A—C19—H19C	109.5
C11—C10—H10	120.2	H19B—C19—H19C	109.5
C9—C10—H10	120.2	C7—N1—N2	104.79 (16)
C10—C11—C12	120.43 (19)	C15—N2—N1	123.09 (17)
C10—C11—Cl1	118.75 (16)	C15—N2—C8	121.12 (17)
C12—C11—Cl1	120.82 (16)	N1—N2—C8	110.70 (15)
C13—C12—C11	120.13 (19)	C3—O1—C17	117.06 (17)
C13—C12—Cl2	119.37 (16)	C4—O2—C18	116.81 (17)
C11—C12—Cl2	120.49 (17)	C5—O3—C19	117.18 (16)
C12—C13—C14	119.45 (19)	C7—O4—C8	106.95 (15)
C6—C1—C2—C3	1.4 (3)	C10—C11—C12—Cl2	−178.89 (16)
C7—C1—C2—C3	−175.26 (18)	Cl1—C11—C12—Cl2	1.2 (3)
C1—C2—C3—O1	179.76 (19)	C11—C12—C13—C14	−0.4 (3)
C1—C2—C3—C4	−0.2 (3)	Cl2—C12—C13—C14	179.24 (16)
O1—C3—C4—O2	−6.1 (3)	C12—C13—C14—C9	0.0 (3)
C2—C3—C4—O2	173.88 (18)	C10—C9—C14—C13	0.0 (3)
O1—C3—C4—C5	179.51 (18)	C8—C9—C14—C13	−179.09 (19)
C2—C3—C4—C5	−0.5 (3)	O4—C7—N1—N2	−0.3 (2)
O2—C4—C5—O3	4.6 (3)	C1—C7—N1—N2	177.36 (18)
C3—C4—C5—O3	178.68 (18)	O5—C15—N2—N1	165.36 (19)
O2—C4—C5—C6	−174.01 (18)	C16—C15—N2—N1	−16.2 (3)
C3—C4—C5—C6	0.1 (3)	O5—C15—N2—C8	12.9 (3)
C2—C1—C6—C5	−1.8 (3)	C16—C15—N2—C8	−168.66 (19)
C7—C1—C6—C5	174.89 (18)	C7—N1—N2—C15	−153.3 (2)
O3—C5—C6—C1	−177.46 (18)	C7—N1—N2—C8	1.6 (2)
C4—C5—C6—C1	1.0 (3)	O4—C8—N2—C15	153.32 (18)
C6—C1—C7—N1	−169.31 (19)	C9—C8—N2—C15	−88.8 (2)
C2—C1—C7—N1	7.4 (3)	O4—C8—N2—N1	−2.2 (2)
C6—C1—C7—O4	8.3 (3)	C9—C8—N2—N1	115.70 (18)
C2—C1—C7—O4	−174.95 (17)	C2—C3—O1—C17	−9.0 (3)
O4—C8—C9—C10	45.1 (2)	C4—C3—O1—C17	171.03 (19)
N2—C8—C9—C10	−67.1 (2)	C5—C4—O2—C18	−65.1 (3)
O4—C8—C9—C14	−135.80 (19)	C3—C4—O2—C18	120.8 (2)
N2—C8—C9—C14	112.0 (2)	C4—C5—O3—C19	−172.83 (18)
C14—C9—C10—C11	0.3 (3)	C6—C5—O3—C19	5.7 (3)
C8—C9—C10—C11	179.43 (18)	N1—C7—O4—C8	−1.2 (2)
C9—C10—C11—C12	−0.7 (3)	C1—C7—O4—C8	−179.02 (17)
C9—C10—C11—Cl1	179.22 (15)	N2—C8—O4—C7	1.92 (19)
C10—C11—C12—C13	0.7 (3)	C9—C8—O4—C7	−117.85 (17)
Cl1—C11—C12—C13	−179.17 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4	0.95	2.43	2.772 (2)	101
C8—H8···O2i	1.00	2.56	3.184 (3)	121
C10—H10···O1ii	0.95	2.43	3.302 (3)	153
C13—H13···O5iii	0.95	2.53	3.426 (3)	156
C16—H16B···N1	0.98	2.42	2.839 (3)	105
C18—H18A···N1ii	0.98	2.53	3.468 (3)	160
C18—H18C···O3	0.98	2.36	2.916 (3)	116
C19—H19A···O5iv	0.98	2.58	3.233 (3)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O4	0.95	2.43	2.772 (2)	101
C8—H8⋯O2i	1.00	2.56	3.184 (3)	121
C10—H10⋯O1ii	0.95	2.43	3.302 (3)	153
C13—H13⋯O5iii	0.95	2.53	3.426 (3)	156
C16—H16B⋯N1	0.98	2.42	2.839 (3)	105
C18—H18A⋯N1ii	0.98	2.53	3.468 (3)	160
C18—H18C⋯O3	0.98	2.36	2.916 (3)	116
C19—H19A⋯O5iv	0.98	2.58	3.233 (3)	124

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .