N-(2-Acetyl­phen­yl)acetamide

The title compound, C₁₀H₁₁NO₂, was synthesized from 2′-amino­acetophenone in acetic anhydride. In the mol­ecular structure, an intra­molecular N—H...O hydrogen bond [H...O = 1.893 (18) Å] appears to affect the overall planar conformation of the mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.118
• Data-to-parameter ratio = 13.2

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:      0.809     0.975
            Tmin(prime) and Tmax expected:      0.962     0.976
            RR(prime) =      0.842
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.84

   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

   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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

N-(2-acetylphenyl)acetamide

Crystal data

C10H11NO2	F(000) = 376
Mr = 177.20	Dx = 1.265 Mg m^−3
Monoclinic, P21/c	Melting point: 349 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.765 (7) Å	Cell parameters from 5840 reflections
b = 8.699 (7) Å	θ = 3.8–32.9°
c = 15.805 (13) Å	µ = 0.09 mm^−1
β = 119.35 (7)°	T = 298 K
V = 930.6 (14) Å^3	Needle, orange
Z = 4	0.43 × 0.31 × 0.27 mm

Data collection

Oxford Diffraction Sapphire3 diffractometer	1639 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1019 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 16.1790 pixels mm^-1	θmax = 25.0°, θmin = 3.8°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)'	k = −10→10
Tmin = 0.809, Tmax = 0.975	l = −18→18
19878 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0807P)^2] where P = (Fo^2 + 2Fc^2)/3
1639 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. Spectroscopic analysis: R_f = 0.46 (Al₂O₃, 80% hexanes/20% ethyl acetate); m.p. 349 K; IR (nujol, ν, cm^-1): 3222, 3065, 1687, 1652, 1584, 1529, 1454, 1251, 765, 723; ¹H NMR (400 MHz, CDCl₃, δ, p.p.m.): 11.706 (s, 1H), 8.735 (dd, 1H, J = 8.3 and 0.9 Hz), 7.888 (dd, 1H, J = 7.8 and 1.4 Hz), 7.546 (dt, 1H, J = 8.3 and 1.4 Hz), 7.104 (dt, 1H, J = 7.8 and 0.9 Hz), 2.661 (s, 3H), 2.222 (s, 3H); ¹³C NMR (400 MHz, CDCl₃, δ, p.p.m.): 202.94, 169.96, 141.09, 135.26, 131.67, 122.39, 121.78, 120.83, 28.72, 25.69; UV–Vis (CH₂Cl₂; λ_max, logε): 326 nm, 3.72; EI–MS calculated for C₁₀H₁₁NO₂: M⁺ 177; found: 177.

During model refinement, H atoms bonded to C atoms were placed in calculated postions with C—H = 0.93 or C—H = 0.96 Å (for methyl groups) and included in the refinement in a riding-model approximation with U_iso(H) = either 1.2U_eq(C) or 1.5U_eq(C) for methyl H atoms. The H atom bonded to N was refined independently with an isotropic displacement parameter.

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
O1	0.44758 (18)	0.62062 (15)	1.16119 (8)	0.0760 (4)
C2	0.3075 (2)	0.69817 (19)	1.10181 (12)	0.0564 (5)
C1	0.2635 (3)	0.8482 (2)	1.13399 (15)	0.0837 (6)
H1A	0.3648	0.8701	1.1992	0.126*
H1B	0.1380	0.8418	1.1318	0.126*
H1C	0.2596	0.9288	1.0916	0.126*
C3	0.1809 (2)	0.64701 (18)	0.99938 (10)	0.0491 (4)
C4	0.0316 (2)	0.7457 (2)	0.93336 (11)	0.0636 (5)
H4	0.0113	0.8391	0.9557	0.076*
C5	−0.0850 (2)	0.7088 (2)	0.83715 (13)	0.0733 (6)
H5	−0.1831	0.7759	0.7953	0.088*
C6	−0.0546 (3)	0.5712 (3)	0.80362 (12)	0.0744 (6)
H6	−0.1309	0.5468	0.7382	0.089*
C7	0.0878 (2)	0.4684 (2)	0.86553 (11)	0.0629 (5)
H7	0.1050	0.3755	0.8415	0.075*
C8	0.2056 (2)	0.50359 (18)	0.96393 (10)	0.0488 (4)
N1	0.35145 (18)	0.40136 (16)	1.02846 (10)	0.0521 (4)
C9	0.3767 (2)	0.2500 (2)	1.01831 (12)	0.0581 (4)
O2	0.2685 (2)	0.17495 (16)	0.94641 (10)	0.1004 (5)
C10	0.5472 (3)	0.1773 (2)	1.10576 (12)	0.0672 (5)
H10A	0.5074	0.1528	1.1529	0.101*
H10B	0.6562	0.2478	1.1336	0.101*
H10C	0.5866	0.0850	1.0865	0.101*
H1	0.423 (2)	0.443 (2)	1.0867 (12)	0.064 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0757 (8)	0.0732 (9)	0.0541 (7)	0.0048 (6)	0.0124 (6)	−0.0073 (6)
C2	0.0643 (11)	0.0505 (10)	0.0561 (10)	−0.0087 (8)	0.0308 (9)	−0.0010 (8)
C1	0.1073 (16)	0.0580 (12)	0.0802 (13)	−0.0036 (11)	0.0415 (12)	−0.0104 (10)
C3	0.0458 (9)	0.0539 (10)	0.0489 (9)	−0.0031 (7)	0.0241 (7)	0.0052 (7)
C4	0.0600 (10)	0.0667 (12)	0.0662 (11)	0.0067 (9)	0.0326 (9)	0.0126 (9)
C5	0.0542 (11)	0.0897 (15)	0.0648 (12)	0.0091 (10)	0.0203 (9)	0.0228 (11)
C6	0.0625 (12)	0.0962 (16)	0.0466 (9)	−0.0153 (11)	0.0129 (9)	0.0056 (10)
C7	0.0659 (11)	0.0677 (12)	0.0480 (9)	−0.0113 (9)	0.0224 (8)	−0.0037 (8)
C8	0.0441 (8)	0.0555 (10)	0.0472 (8)	−0.0071 (7)	0.0226 (7)	0.0034 (7)
N1	0.0562 (8)	0.0490 (9)	0.0459 (8)	−0.0035 (6)	0.0210 (7)	−0.0009 (6)
C9	0.0623 (10)	0.0544 (11)	0.0608 (10)	−0.0014 (8)	0.0328 (9)	−0.0051 (9)
O2	0.1082 (11)	0.0686 (9)	0.0853 (10)	0.0103 (8)	0.0171 (8)	−0.0232 (8)
C10	0.0752 (12)	0.0581 (11)	0.0718 (11)	0.0057 (9)	0.0387 (10)	0.0094 (9)

Geometric parameters (Å, º)

O1—C2	1.232 (2)	C6—C7	1.385 (3)
C2—C3	1.492 (3)	C6—H6	0.9300
C2—C1	1.500 (3)	C7—C8	1.398 (3)
C1—H1A	0.9600	C7—H7	0.9300
C1—H1B	0.9600	C8—N1	1.408 (2)
C1—H1C	0.9600	N1—C9	1.352 (2)
C3—C4	1.409 (2)	N1—H1	0.888 (17)
C3—C8	1.419 (2)	C9—O2	1.220 (2)
C4—C5	1.373 (3)	C9—C10	1.506 (3)
C4—H4	0.9300	C10—H10A	0.9600
C5—C6	1.375 (3)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
O1—C2—C3	121.95 (17)	C7—C6—H6	119.4
O1—C2—C1	118.75 (17)	C6—C7—C8	120.34 (19)
C3—C2—C1	119.29 (16)	C6—C7—H7	119.8
C2—C1—H1A	109.5	C8—C7—H7	119.8
C2—C1—H1B	109.5	C7—C8—N1	121.55 (17)
H1A—C1—H1B	109.5	C7—C8—C3	119.36 (14)
C2—C1—H1C	109.5	N1—C8—C3	119.08 (14)
H1A—C1—H1C	109.5	C9—N1—C8	129.88 (15)
H1B—C1—H1C	109.5	C9—N1—H1	118.0 (11)
C4—C3—C8	117.71 (15)	C8—N1—H1	111.4 (11)
C4—C3—C2	119.17 (17)	O2—C9—N1	123.91 (17)
C8—C3—C2	123.11 (14)	O2—C9—C10	121.64 (18)
C5—C4—C3	122.30 (19)	N1—C9—C10	114.40 (15)
C5—C4—H4	118.8	C9—C10—H10A	109.5
C3—C4—H4	118.8	C9—C10—H10B	109.5
C4—C5—C6	119.05 (17)	H10A—C10—H10B	109.5
C4—C5—H5	120.5	C9—C10—H10C	109.5
C6—C5—H5	120.5	H10A—C10—H10C	109.5
C5—C6—C7	121.19 (17)	H10B—C10—H10C	109.5
C5—C6—H6	119.4
O1—C2—C3—C4	−175.63 (15)	C6—C7—C8—C3	−1.3 (2)
C1—C2—C3—C4	4.4 (2)	C4—C3—C8—C7	2.4 (2)
O1—C2—C3—C8	3.1 (2)	C2—C3—C8—C7	−176.39 (14)
C1—C2—C3—C8	−176.83 (14)	C4—C3—C8—N1	−179.00 (13)
C8—C3—C4—C5	−1.5 (2)	C2—C3—C8—N1	2.3 (2)
C2—C3—C4—C5	177.30 (14)	C7—C8—N1—C9	−16.6 (2)
C3—C4—C5—C6	−0.5 (3)	C3—C8—N1—C9	164.75 (14)
C4—C5—C6—C7	1.6 (3)	C8—N1—C9—O2	0.0 (3)
C5—C6—C7—C8	−0.7 (3)	C8—N1—C9—C10	−177.64 (14)
C6—C7—C8—N1	−179.94 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.888 (17)	1.893 (18)	2.657 (2)	143.1 (15)