2-Acetyl-3′-chloro­acetanilide

In the title compound [alternatively called N-(3-chloro­phenyl)-3-oxobutanamide], C₁₀H₁₀ClNO₂, the C=O bond lengths are 1.2108 (19) and 1.179 (2) Å, which implies that the molecule is in the keto form. The crystal structure is stabilized by an N—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.075
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293

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

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-(3-chlorophenyl)-3-oxobutanamide

Crystal data

C10H10ClNO2	F(000) = 880
Mr = 211.64	Dx = 1.381 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 702 reflections
a = 9.5485 (16) Å	θ = 2.6–18.3°
b = 8.2197 (13) Å	µ = 0.35 mm^−1
c = 25.940 (4) Å	T = 293 K
V = 2035.9 (6) Å^3	Plate, colourless
Z = 8	0.32 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1988 independent reflections
Radiation source: sealed tube	1285 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.90, Tmax = 0.92	k = −7→10
10164 measured reflections	l = −29→31

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.03P)^2] where P = (Fo^2 + 2Fc^2)/3
1988 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

Experimental. All commercially available reagents were used as supplied. Carbon, hydrogen and nitrogen were determined using a Elementar Vario EL elemental analyzer. Infrared spectra were recorded with KBr optics on a Nicolet AVATAR 360 spectrophotometer. Mass spectrum (FAB) was measured using a MASPEC II system analyzer.

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	0.58989 (7)	0.23432 (7)	0.52633 (2)	0.0703 (2)
N1	0.42667 (13)	0.25024 (16)	0.71108 (5)	0.0385 (3)
H1	0.5134	0.2364	0.7189	0.046*
O1	0.20787 (11)	0.24572 (17)	0.74412 (5)	0.0572 (4)
O2	0.36625 (18)	0.42013 (18)	0.83242 (6)	0.0734 (5)
C1	0.39771 (17)	0.29927 (19)	0.66060 (7)	0.0339 (4)
C2	0.49338 (19)	0.2525 (2)	0.62307 (7)	0.0410 (4)
H2	0.5719	0.1920	0.6320	0.049*
C3	0.4714 (2)	0.2960 (2)	0.57296 (7)	0.0445 (5)
C4	0.3579 (2)	0.3849 (2)	0.55802 (8)	0.0552 (5)
H4	0.3438	0.4135	0.5237	0.066*
C5	0.2656 (2)	0.4300 (3)	0.59573 (9)	0.0561 (6)
H5	0.1875	0.4912	0.5866	0.067*
C6	0.28399 (19)	0.3882 (2)	0.64642 (7)	0.0481 (5)
H6	0.2189	0.4206	0.6710	0.058*
C7	0.33240 (17)	0.2223 (2)	0.74891 (7)	0.0361 (4)
C8	0.39229 (17)	0.1587 (2)	0.79803 (7)	0.0387 (4)
H8A	0.4885	0.1256	0.7921	0.046*
H8B	0.3399	0.0632	0.8085	0.046*
C9	0.38898 (19)	0.2817 (3)	0.84083 (8)	0.0499 (5)
C10	0.4198 (3)	0.2174 (3)	0.89323 (9)	0.0753 (7)
H10A	0.4216	0.3057	0.9175	0.113*
H10B	0.5092	0.1640	0.8930	0.113*
H10C	0.3485	0.1411	0.9030	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0908 (4)	0.0710 (4)	0.0491 (3)	0.0327 (3)	0.0127 (3)	0.0063 (3)
N1	0.0163 (6)	0.0550 (9)	0.0442 (8)	−0.0007 (7)	0.0000 (6)	0.0040 (7)
O1	0.0204 (7)	0.0863 (12)	0.0650 (9)	0.0015 (7)	0.0033 (6)	0.0052 (8)
O2	0.0871 (12)	0.0517 (9)	0.0814 (10)	0.0124 (8)	−0.0154 (10)	−0.0107 (8)
C1	0.0261 (8)	0.0312 (9)	0.0444 (10)	−0.0028 (7)	−0.0063 (8)	−0.0013 (7)
C2	0.0264 (9)	0.0473 (11)	0.0492 (10)	−0.0041 (8)	0.0019 (7)	0.0014 (9)
C3	0.0429 (11)	0.0485 (10)	0.0420 (12)	−0.0009 (9)	0.0006 (8)	−0.0003 (9)
C4	0.0573 (13)	0.0587 (13)	0.0497 (12)	−0.0054 (11)	−0.0189 (11)	0.0073 (10)
C5	0.0462 (12)	0.0575 (14)	0.0645 (14)	0.0161 (9)	−0.0183 (11)	0.0032 (10)
C6	0.0367 (11)	0.0554 (12)	0.0523 (12)	0.0097 (9)	−0.0101 (9)	−0.0048 (10)
C7	0.0267 (9)	0.0366 (9)	0.0450 (10)	0.0019 (7)	0.0022 (7)	−0.0050 (8)
C8	0.0266 (8)	0.0406 (10)	0.0489 (11)	0.0005 (7)	0.0033 (8)	0.0102 (7)
C9	0.0366 (10)	0.0527 (13)	0.0605 (12)	0.0069 (10)	−0.0064 (9)	0.0054 (9)
C10	0.0644 (15)	0.1007 (19)	0.0609 (15)	0.0202 (15)	−0.0061 (12)	0.0081 (13)

Geometric parameters (Å, º)

Cl1—C3	1.7322 (19)	C4—H4	0.9300
N1—C7	1.351 (2)	C5—C6	1.370 (3)
N1—C1	1.398 (2)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
O1—C7	1.2108 (19)	C7—C8	1.491 (2)
O2—C9	1.179 (2)	C8—C9	1.502 (3)
C1—C6	1.360 (2)	C8—H8A	0.9700
C1—C2	1.389 (2)	C8—H8B	0.9700
C2—C3	1.364 (3)	C9—C10	1.488 (3)
C2—H2	0.9300	C10—H10A	0.9600
C3—C4	1.363 (3)	C10—H10B	0.9600
C4—C5	1.368 (3)	C10—H10C	0.9600
C7—N1—C1	126.69 (14)	C5—C6—H6	120.1
C7—N1—H1	116.7	O1—C7—N1	123.56 (17)
C1—N1—H1	116.7	O1—C7—C8	121.33 (17)
C6—C1—C2	118.95 (17)	N1—C7—C8	115.11 (14)
C6—C1—N1	124.51 (16)	C7—C8—C9	112.82 (15)
C2—C1—N1	116.54 (15)	C7—C8—H8A	109.0
C3—C2—C1	119.61 (17)	C9—C8—H8A	109.0
C3—C2—H2	120.2	C7—C8—H8B	109.0
C1—C2—H2	120.2	C9—C8—H8B	109.0
C4—C3—C2	122.25 (18)	H8A—C8—H8B	107.8
C4—C3—Cl1	118.53 (15)	O2—C9—C10	123.3 (2)
C2—C3—Cl1	119.22 (14)	O2—C9—C8	121.10 (18)
C3—C4—C5	117.01 (19)	C10—C9—C8	115.62 (19)
C3—C4—H4	121.5	C9—C10—H10A	109.5
C5—C4—H4	121.5	C9—C10—H10B	109.5
C4—C5—C6	122.40 (18)	H10A—C10—H10B	109.5
C4—C5—H5	118.8	C9—C10—H10C	109.5
C6—C5—H5	118.8	H10A—C10—H10C	109.5
C1—C6—C5	119.78 (18)	H10B—C10—H10C	109.5
C1—C6—H6	120.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	2.09	2.9259 (18)	163

Symmetry code: (i) x+1/2, y, −z+3/2.