1-(4-Chloro­phenyl)­propane-1,2-dione 2-oxime

In the title mol­ecule, C₉H₈NO₂Cl, the dihedral angle between the aromatic ring and propan-2-one oxime moiety is 54.05 (4)°. In the crystal structure, the mol­ecules exist as O—H...N hydrogen-bonded dimers around the inversion centres.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.125
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  Cl1      =       3.41 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: PLATON.

1-(4-chlorophenyl)propane-1,2-dione 2-oxime

Crystal data

C9H8ClNO2	F(000) = 408
Mr = 197.61	Dx = 1.456 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7478 reflections
a = 11.066 (2) Å	θ = 1.9–28.0°
b = 5.9348 (13) Å	µ = 0.39 mm^−1
c = 14.075 (3) Å	T = 293 K
β = 102.809 (4)°	Plate, colorless
V = 901.4 (3) Å^3	0.3 × 0.2 × 0.1 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2116 independent reflections
Radiation source: fine-focus sealed tube	1827 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 0.3 pixels mm^-1	θmax = 28.0°, θmin = 1.9°
φ and ω scans	h = −14→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→7
Tmin = 0.930, Tmax = 0.964	l = −18→18
7478 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0784P)^2 + 0.2853P] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.001
2116 reflections	Δρmax = 0.21 e Å^−3
140 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (5)

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	0.05231 (5)	0.20157 (11)	0.58546 (4)	0.0719 (2)
O1	0.28572 (13)	0.7137 (2)	1.00137 (10)	0.0594 (4)
O2	0.50727 (12)	0.0870 (2)	1.10942 (8)	0.0489 (3)
N2	0.43038 (12)	0.2005 (2)	1.03279 (9)	0.0396 (3)
C1	0.30377 (14)	0.5182 (2)	0.98319 (11)	0.0409 (3)
C2	0.38269 (13)	0.3775 (2)	1.06140 (10)	0.0393 (3)
C3	0.40766 (17)	0.4612 (3)	1.16376 (12)	0.0533 (4)
H3A	0.3959	0.3408	1.2063	0.080*
H3B	0.3517	0.5822	1.1686	0.080*
H3C	0.4915	0.5147	1.1823	0.080*
C4	0.12963 (14)	0.2871 (3)	0.70064 (12)	0.0451 (4)
C5	0.13464 (14)	0.1433 (3)	0.77855 (13)	0.0448 (4)
C6	0.19671 (14)	0.2102 (2)	0.87075 (12)	0.0414 (3)
C7	0.24950 (13)	0.4241 (2)	0.88476 (11)	0.0383 (3)
C8	0.24267 (15)	0.5652 (3)	0.80475 (12)	0.0458 (4)
C9	0.18444 (16)	0.4970 (3)	0.71215 (12)	0.0504 (4)
H2	0.535 (2)	−0.009 (4)	1.0783 (16)	0.069 (7)*
H5	0.0959 (18)	0.009 (4)	0.7711 (14)	0.053 (5)*
H6	0.2013 (18)	0.116 (3)	0.9252 (15)	0.052 (5)*
H8	0.2786 (19)	0.713 (4)	0.8168 (15)	0.055 (5)*
H9	0.187 (2)	0.593 (4)	0.6565 (18)	0.084 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0710 (4)	0.0893 (4)	0.0486 (3)	−0.0117 (3)	−0.0016 (2)	−0.0149 (2)
O1	0.0765 (9)	0.0363 (6)	0.0614 (8)	0.0058 (5)	0.0069 (7)	−0.0092 (5)
O2	0.0620 (7)	0.0442 (6)	0.0351 (6)	0.0078 (5)	−0.0011 (5)	−0.0014 (5)
N2	0.0469 (7)	0.0348 (6)	0.0344 (6)	−0.0007 (5)	0.0032 (5)	−0.0001 (5)
C1	0.0437 (7)	0.0337 (7)	0.0456 (8)	−0.0023 (6)	0.0107 (6)	−0.0028 (6)
C2	0.0424 (7)	0.0374 (7)	0.0383 (7)	−0.0056 (6)	0.0093 (6)	−0.0048 (6)
C3	0.0591 (10)	0.0594 (10)	0.0403 (8)	0.0021 (8)	0.0090 (7)	−0.0134 (7)
C4	0.0369 (7)	0.0521 (9)	0.0442 (8)	0.0016 (6)	0.0043 (6)	−0.0067 (6)
C5	0.0411 (8)	0.0374 (7)	0.0552 (9)	−0.0048 (6)	0.0094 (7)	−0.0070 (6)
C6	0.0439 (8)	0.0345 (7)	0.0460 (8)	−0.0028 (6)	0.0101 (6)	0.0005 (6)
C7	0.0375 (7)	0.0337 (7)	0.0427 (7)	0.0015 (5)	0.0067 (6)	−0.0010 (5)
C8	0.0494 (8)	0.0352 (7)	0.0504 (9)	−0.0035 (6)	0.0058 (7)	0.0034 (6)
C9	0.0531 (9)	0.0499 (9)	0.0457 (8)	−0.0017 (7)	0.0055 (7)	0.0072 (7)

Geometric parameters (Å, º)

Cl1—C4	1.7330 (16)	C4—C9	1.379 (2)
O1—C1	1.2138 (19)	C4—C5	1.381 (2)
O2—N2	1.3906 (16)	C5—C6	1.385 (2)
O2—H2	0.82 (2)	C5—H5	0.90 (2)
N2—C2	1.2801 (19)	C6—C7	1.393 (2)
C1—C7	1.491 (2)	C6—H6	0.94 (2)
C1—C2	1.499 (2)	C7—C8	1.392 (2)
C2—C3	1.491 (2)	C8—C9	1.381 (2)
C3—H3A	0.96	C8—H8	0.96 (2)
C3—H3B	0.96	C9—H9	0.97 (3)
C3—H3C	0.96
N2—O2—H2	99.2 (16)	C5—C4—Cl1	119.11 (13)
C2—N2—O2	112.17 (12)	C4—C5—C6	119.43 (15)
O1—C1—C7	120.18 (15)	C4—C5—H5	121.4 (13)
O1—C1—C2	118.30 (14)	C6—C5—H5	119.2 (13)
C7—C1—C2	121.52 (12)	C5—C6—C7	119.94 (15)
N2—C2—C3	125.21 (14)	C5—C6—H6	121.2 (12)
N2—C2—C1	116.11 (13)	C7—C6—H6	118.8 (12)
C3—C2—C1	118.49 (14)	C8—C7—C6	119.21 (14)
C2—C3—H3A	109.5	C8—C7—C1	117.69 (13)
C2—C3—H3B	109.5	C6—C7—C1	122.88 (13)
H3A—C3—H3B	109.5	C9—C8—C7	121.16 (15)
C2—C3—H3C	109.5	C9—C8—H8	121.5 (13)
H3A—C3—H3C	109.5	C7—C8—H8	117.3 (13)
H3B—C3—H3C	109.5	C4—C9—C8	118.49 (16)
C9—C4—C5	121.71 (15)	C4—C9—H9	121.7 (15)
C9—C4—Cl1	119.18 (14)	C8—C9—H9	119.7 (15)
O2—N2—C2—C3	1.8 (2)	C5—C6—C7—C1	172.17 (14)
O2—N2—C2—C1	176.77 (12)	O1—C1—C7—C8	35.9 (2)
O1—C1—C2—N2	−159.49 (15)	C2—C1—C7—C8	−143.27 (15)
C7—C1—C2—N2	19.7 (2)	O1—C1—C7—C6	−138.57 (17)
O1—C1—C2—C3	15.8 (2)	C2—C1—C7—C6	42.3 (2)
C7—C1—C2—C3	−164.99 (14)	C6—C7—C8—C9	0.1 (2)
C9—C4—C5—C6	−0.3 (2)	C1—C7—C8—C9	−174.57 (15)
Cl1—C4—C5—C6	179.73 (12)	C5—C4—C9—C8	−1.8 (3)
C4—C5—C6—C7	2.3 (2)	Cl1—C4—C9—C8	178.20 (13)
C5—C6—C7—C8	−2.2 (2)	C7—C8—C9—C4	1.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2^i	0.82 (2)	2.04 (2)	2.830 (2)	163 (2)
O2—H2···O2^i	0.82 (2)	2.62 (2)	3.219 (2)	131 (2)
C3—H3B···O1	0.96	2.43	2.815 (2)	103

Symmetry code: (i) −x+1, −y, −z+2.