1-[5-(3,6-Dichloro­pyridin-2-yl)-2,2-dimethyl-1,3,4-oxadiazol-3-yl]ethanone

The title compound, C₁₁H₁₁Cl₂N₃O₂, shows an approximately planar oxadiazo­line ring and a small twist between its two ring systems. In the crystal structure, molecules are linked into chains via C—H...O interactions and centrosymmetrically related chains are connected into double chains via weaker C—H...N interactions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.135
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.668     1.000
            Tmin(prime) and Tmax expected:      0.755     0.985
            RR(prime) =      0.872
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B    ..  CL1     ..       2.89 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Rigaku Americas Corporation, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

1-[5-(3,6-Dichloropyridin-2-yl)-2,2-dimethyl-1,3,4-oxadiazol-3-yl]ethanone

Crystal data

C11H11Cl2N3O2	F(000) = 592
Mr = 288.13	Dx = 1.491 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5183 reflections
a = 11.1149 (19) Å	θ = 2.9–30.6°
b = 8.1943 (13) Å	µ = 0.50 mm^−1
c = 14.122 (2) Å	T = 173 K
β = 93.554 (3)°	Plate, colourless
V = 1283.8 (4) Å^3	0.55 × 0.35 × 0.03 mm
Z = 4

Data collection

Rigaku AFC12κ/SATURN724 CCD diffractometer	2924 independent reflections
Radiation source: fine-focus sealed tube	2887 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.668, Tmax = 1.000	k = −10→9
32711 measured reflections	l = −18→18

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0762P)^2 + 0.4744P] where P = (Fo^2 + 2Fc^2)/3
2924 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.35 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	0.93462 (4)	0.87254 (8)	−0.10314 (4)	0.0523 (2)
Cl2	0.77170 (4)	0.48665 (7)	0.24046 (3)	0.04466 (18)
O1	0.54047 (10)	0.80222 (15)	0.04455 (9)	0.0317 (3)
O2	0.22748 (11)	0.57282 (17)	0.13400 (10)	0.0380 (3)
N1	0.54303 (12)	0.56763 (18)	0.12651 (10)	0.0278 (3)
N2	0.42304 (12)	0.61429 (17)	0.10955 (10)	0.0275 (3)
N3	0.77364 (13)	0.76615 (18)	0.00831 (11)	0.0298 (3)
C1	0.60406 (14)	0.67882 (19)	0.08809 (11)	0.0258 (3)
C2	0.41458 (14)	0.7796 (2)	0.06637 (11)	0.0264 (3)
C3	0.33179 (15)	0.5243 (2)	0.14320 (12)	0.0280 (3)
C4	0.36809 (16)	0.3651 (2)	0.18937 (12)	0.0319 (4)
H4A	0.2958	0.3045	0.2046	0.048*
H4B	0.4179	0.3863	0.2477	0.048*
H4C	0.4142	0.3005	0.1458	0.048*
C5	0.38273 (19)	0.9073 (2)	0.13736 (14)	0.0388 (4)
H5A	0.2985	0.8935	0.1526	0.058*
H5B	0.3936	1.0161	0.1104	0.058*
H5C	0.4353	0.8954	0.1953	0.058*
C6	0.33842 (15)	0.7869 (2)	−0.02577 (12)	0.0331 (4)
H6A	0.2534	0.7722	−0.0131	0.050*
H6B	0.3633	0.7001	−0.0681	0.050*
H6C	0.3491	0.8932	−0.0560	0.050*
C7	0.73568 (14)	0.6799 (2)	0.08202 (11)	0.0261 (3)
C8	0.88991 (15)	0.7670 (2)	−0.00442 (13)	0.0332 (4)
C9	0.97700 (16)	0.6893 (3)	0.05348 (14)	0.0380 (4)
H9	1.0600	0.6955	0.0412	0.046*
C10	0.93898 (16)	0.6032 (2)	0.12927 (14)	0.0368 (4)
H10	0.9957	0.5488	0.1713	0.044*
C11	0.81627 (15)	0.5962 (2)	0.14419 (12)	0.0300 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0358 (3)	0.0712 (4)	0.0506 (3)	−0.0075 (2)	0.0071 (2)	0.0240 (3)
Cl2	0.0358 (3)	0.0605 (4)	0.0368 (3)	−0.0013 (2)	−0.00417 (19)	0.0194 (2)
O1	0.0215 (5)	0.0303 (6)	0.0433 (7)	0.0020 (4)	0.0022 (5)	0.0093 (5)
O2	0.0234 (6)	0.0408 (7)	0.0503 (8)	0.0004 (5)	0.0054 (5)	0.0048 (6)
N1	0.0217 (6)	0.0295 (7)	0.0322 (7)	0.0025 (5)	0.0009 (5)	0.0027 (5)
N2	0.0205 (6)	0.0271 (7)	0.0348 (7)	0.0027 (5)	0.0014 (5)	0.0050 (5)
N3	0.0245 (6)	0.0318 (7)	0.0329 (7)	−0.0001 (5)	0.0002 (5)	0.0034 (6)
C1	0.0250 (7)	0.0250 (8)	0.0269 (7)	0.0009 (6)	−0.0012 (6)	−0.0008 (6)
C2	0.0217 (7)	0.0257 (8)	0.0319 (8)	0.0013 (6)	0.0026 (6)	0.0019 (6)
C3	0.0251 (7)	0.0297 (8)	0.0293 (7)	−0.0010 (6)	0.0036 (6)	−0.0022 (6)
C4	0.0336 (8)	0.0289 (8)	0.0338 (8)	−0.0026 (6)	0.0064 (6)	0.0016 (6)
C5	0.0452 (11)	0.0329 (9)	0.0389 (9)	0.0037 (8)	0.0067 (8)	−0.0045 (7)
C6	0.0296 (8)	0.0356 (9)	0.0336 (8)	0.0011 (7)	−0.0020 (7)	0.0031 (7)
C7	0.0243 (7)	0.0269 (8)	0.0270 (7)	−0.0005 (6)	−0.0004 (6)	−0.0001 (6)
C8	0.0265 (8)	0.0381 (9)	0.0350 (8)	−0.0028 (7)	0.0017 (6)	0.0054 (7)
C9	0.0222 (7)	0.0447 (10)	0.0469 (10)	0.0002 (7)	0.0009 (7)	0.0051 (8)
C10	0.0259 (8)	0.0416 (10)	0.0417 (9)	0.0031 (7)	−0.0066 (7)	0.0066 (8)
C11	0.0276 (8)	0.0328 (9)	0.0293 (7)	−0.0012 (6)	−0.0022 (6)	0.0020 (6)

Geometric parameters (Å, º)

Cl1—C8	1.7392 (18)	C4—H4A	0.980
Cl2—C11	1.7270 (18)	C4—H4B	0.980
O1—C1	1.3587 (19)	C4—H4C	0.980
O1—C2	1.4630 (18)	C5—H5A	0.980
O2—C3	1.225 (2)	C5—H5B	0.980
N1—C1	1.277 (2)	C5—H5C	0.980
N1—N2	1.3938 (18)	C6—H6A	0.980
N2—C2	1.486 (2)	C6—H6B	0.980
N2—C3	1.363 (2)	C6—H6C	0.980
N3—C7	1.347 (2)	C7—C11	1.395 (2)
N3—C8	1.316 (2)	C8—C9	1.383 (3)
C1—C7	1.471 (2)	C9—C10	1.370 (3)
C2—C5	1.506 (2)	C9—H9	0.950
C2—C6	1.509 (2)	C10—C11	1.394 (2)
C3—C4	1.503 (2)	C10—H10	0.950
C1—O1—C2	106.74 (12)	H5A—C5—H5B	109.5
N2—N1—C1	105.01 (13)	C2—C5—H5C	109.5
N1—N2—C2	110.86 (12)	H5A—C5—H5C	109.5
N1—N2—C3	121.08 (14)	H5B—C5—H5C	109.5
C2—N2—C3	127.35 (13)	C2—C6—H6A	109.5
C8—N3—C7	117.74 (15)	C2—C6—H6B	109.5
N1—C1—O1	116.63 (14)	H6A—C6—H6B	109.5
N1—C1—C7	125.84 (15)	C2—C6—H6C	109.5
O1—C1—C7	117.42 (14)	H6A—C6—H6C	109.5
O1—C2—N2	99.48 (11)	H6B—C6—H6C	109.5
O1—C2—C5	108.65 (14)	N3—C7—C11	121.64 (15)
N2—C2—C5	111.81 (14)	N3—C7—C1	114.10 (14)
O1—C2—C6	107.83 (13)	C11—C7—C1	124.23 (15)
N2—C2—C6	114.05 (14)	N3—C8—C9	125.05 (17)
C5—C2—C6	113.84 (14)	N3—C8—Cl1	116.35 (13)
O2—C3—N2	120.47 (16)	C9—C8—Cl1	118.59 (14)
O2—C3—C4	123.71 (16)	C8—C9—C10	117.40 (16)
N2—C3—C4	115.82 (14)	C8—C9—H9	121.3
C3—C4—H4A	109.5	C10—C9—H9	121.3
C3—C4—H4B	109.5	C11—C10—C9	119.43 (16)
H4A—C4—H4B	109.5	C11—C10—H10	120.3
C3—C4—H4C	109.5	C9—C10—H10	120.3
H4A—C4—H4C	109.5	C7—C11—C10	118.71 (16)
H4B—C4—H4C	109.5	C7—C11—Cl2	123.14 (13)
C2—C5—H5A	109.5	C10—C11—Cl2	118.14 (13)
C2—C5—H5B	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2^i	0.95	2.43	3.092 (2)	127
C6—H6B···N1^ii	0.98	2.59	3.526 (2)	161
C4—H4B···Cl1^iii	0.98	2.89	3.672 (2)	138

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) x−1/2, −y+3/2, z+1/2.