2-Chloro-1,2-diphenyl-ethanone (desyl chloride).

The title compound, C(14)H(11)ClO, is a racemic derivative of benzoin. Its carbonyl group adopts a nearly eclipsed conformation with the Cl substituent characterized by a dihedral angle of 17.5 (2)°. The closest intermolecular π-π contact is 4.258 (1) Å.

Related literature

For the crystal structure of benzoin, see: Haisa et al. (1980 ▶); Sole et al. (1998 ▶). For the crystal structure of 2-phenyl­acetophenone, see: Rieker et al. (1993 ▶). For the crystal structure of 2-chloro­acetophenone, see: Grossert et al. (1984 ▶). Structures containing similar angles were retrieved from the Cambridge Structural Database (Allen, 2002 ▶).

Experimental

Crystal data

C14H11ClO

M = 230.68

Monoclinic,

a = 12.6233 (11) Å

b = 5.8227 (5) Å

c = 15.6745 (14) Å

β = 97.317 (3)°

V = 1142.72 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 200 K

0.53 × 0.29 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

9777 measured reflections

2816 independent reflections

2366 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.07

2816 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014541/ld2009sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811014541/ld2009Isup2.cdx

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014541/ld2009Isup3.hkl

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

C14H11ClO	F(000) = 480
Mr = 230.68	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5815 reflections
a = 12.6233 (11) Å	θ = 2.6–28.3°
b = 5.8227 (5) Å	µ = 0.31 mm−1
c = 15.6745 (14) Å	T = 200 K
β = 97.317 (3)°	Rod, colourless
V = 1142.72 (17) Å3	0.53 × 0.29 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	2366 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 28.3°, θmin = 2.6°
φ and ω scans	h = −16→16
9777 measured reflections	k = −7→6
2816 independent reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0471P)2 + 0.3595P] where P = (Fo2 + 2Fc2)/3
2816 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.36760 (3)	0.54577 (9)	0.02422 (2)	0.05873 (16)
O1	0.19610 (9)	0.8528 (2)	0.05035 (8)	0.0585 (3)
C1	0.17721 (11)	0.6644 (2)	0.07711 (8)	0.0369 (3)
C2	0.26188 (10)	0.4753 (2)	0.08663 (8)	0.0361 (3)
H2	0.2277	0.3291	0.0637	0.043*
C11	0.07080 (10)	0.6085 (2)	0.10402 (7)	0.0318 (3)
C12	0.04806 (11)	0.4010 (2)	0.14191 (9)	0.0369 (3)
H12	0.1014	0.2853	0.1511	0.044*
C13	−0.05239 (11)	0.3628 (3)	0.16633 (10)	0.0436 (3)
H13	−0.0673	0.2221	0.1931	0.052*
C14	−0.13073 (11)	0.5290 (3)	0.15188 (10)	0.0454 (3)
H14	−0.1996	0.5017	0.1682	0.054*
C15	−0.10909 (12)	0.7350 (3)	0.11366 (10)	0.0456 (3)
H15	−0.1632	0.8486	0.1032	0.055*
C16	−0.00869 (11)	0.7752 (2)	0.09067 (8)	0.0395 (3)
H16	0.0063	0.9181	0.0655	0.047*
C21	0.30932 (9)	0.4355 (2)	0.17883 (8)	0.0313 (3)
C22	0.36130 (11)	0.2294 (2)	0.20111 (10)	0.0411 (3)
H22	0.3639	0.1128	0.1590	0.049*
C23	0.40932 (12)	0.1938 (3)	0.28445 (11)	0.0485 (4)
H23	0.4461	0.0542	0.2991	0.058*
C24	0.40391 (12)	0.3604 (3)	0.34634 (10)	0.0483 (4)
H24	0.4364	0.3348	0.4036	0.058*
C25	0.35139 (12)	0.5639 (3)	0.32497 (9)	0.0451 (3)
H25	0.3470	0.6780	0.3677	0.054*
C26	0.30485 (11)	0.6021 (2)	0.24116 (8)	0.0372 (3)
H26	0.2697	0.7436	0.2265	0.045*

	U11	U22	U33	U12	U13	U23
Cl1	0.0447 (2)	0.0974 (4)	0.0365 (2)	−0.0071 (2)	0.01475 (15)	−0.00083 (19)
O1	0.0538 (6)	0.0513 (7)	0.0703 (8)	−0.0085 (5)	0.0077 (6)	0.0241 (6)
C1	0.0385 (6)	0.0400 (7)	0.0312 (6)	−0.0051 (5)	0.0003 (5)	0.0047 (5)
C2	0.0319 (6)	0.0449 (7)	0.0321 (6)	−0.0058 (5)	0.0068 (5)	−0.0049 (5)
C11	0.0332 (6)	0.0338 (6)	0.0271 (5)	−0.0019 (5)	−0.0011 (4)	0.0001 (5)
C12	0.0344 (6)	0.0325 (6)	0.0429 (7)	−0.0001 (5)	0.0020 (5)	0.0033 (5)
C13	0.0412 (7)	0.0392 (7)	0.0508 (8)	−0.0069 (6)	0.0075 (6)	0.0037 (6)
C14	0.0335 (7)	0.0558 (9)	0.0472 (8)	−0.0025 (6)	0.0066 (6)	−0.0046 (7)
C15	0.0403 (7)	0.0479 (8)	0.0474 (8)	0.0116 (6)	0.0010 (6)	−0.0026 (6)
C16	0.0459 (7)	0.0355 (7)	0.0358 (7)	0.0032 (6)	0.0003 (5)	0.0031 (5)
C21	0.0268 (5)	0.0337 (6)	0.0339 (6)	−0.0021 (5)	0.0063 (4)	−0.0003 (5)
C22	0.0364 (7)	0.0336 (7)	0.0539 (8)	0.0008 (5)	0.0081 (6)	−0.0030 (6)
C23	0.0386 (7)	0.0413 (8)	0.0646 (10)	0.0038 (6)	0.0026 (6)	0.0153 (7)
C24	0.0422 (7)	0.0584 (9)	0.0423 (7)	−0.0050 (7)	−0.0018 (6)	0.0155 (7)
C25	0.0503 (8)	0.0510 (9)	0.0335 (7)	−0.0008 (7)	0.0029 (6)	−0.0026 (6)
C26	0.0413 (7)	0.0348 (7)	0.0351 (6)	0.0041 (5)	0.0031 (5)	−0.0002 (5)

Cl1—C2	1.7997 (13)	C15—C16	1.381 (2)
O1—C1	1.2092 (18)	C15—H15	0.9500
C1—C11	1.4941 (18)	C16—H16	0.9500
C1—C2	1.529 (2)	C21—C26	1.3829 (18)
C2—C21	1.5100 (18)	C21—C22	1.3910 (18)
C2—H2	1.0000	C22—C23	1.384 (2)
C11—C12	1.3921 (18)	C22—H22	0.9500
C11—C16	1.3929 (18)	C23—C24	1.379 (2)
C12—C13	1.3883 (19)	C23—H23	0.9500
C12—H12	0.9500	C24—C25	1.378 (2)
C13—C14	1.381 (2)	C24—H24	0.9500
C13—H13	0.9500	C25—C26	1.3871 (19)
C14—C15	1.384 (2)	C25—H25	0.9500
C14—H14	0.9500	C26—H26	0.9500
O1—C1—C11	121.31 (13)	C14—C15—H15	120.1
O1—C1—C2	121.41 (13)	C15—C16—C11	120.67 (13)
C11—C1—C2	117.27 (11)	C15—C16—H16	119.7
C21—C2—C1	113.02 (10)	C11—C16—H16	119.7
C21—C2—Cl1	108.91 (9)	C26—C21—C22	119.22 (12)
C1—C2—Cl1	109.90 (10)	C26—C21—C2	121.45 (12)
C21—C2—H2	108.3	C22—C21—C2	119.30 (12)
C1—C2—H2	108.3	C23—C22—C21	120.13 (13)
Cl1—C2—H2	108.3	C23—C22—H22	119.9
C12—C11—C16	119.03 (12)	C21—C22—H22	119.9
C12—C11—C1	123.44 (12)	C24—C23—C22	120.25 (14)
C16—C11—C1	117.52 (12)	C24—C23—H23	119.9
C13—C12—C11	120.11 (13)	C22—C23—H23	119.9
C13—C12—H12	119.9	C25—C24—C23	119.92 (14)
C11—C12—H12	119.9	C25—C24—H24	120.0
C14—C13—C12	120.18 (14)	C23—C24—H24	120.0
C14—C13—H13	119.9	C24—C25—C26	120.06 (14)
C12—C13—H13	119.9	C24—C25—H25	120.0
C13—C14—C15	120.10 (13)	C26—C25—H25	120.0
C13—C14—H14	120.0	C21—C26—C25	120.40 (13)
C15—C14—H14	120.0	C21—C26—H26	119.8
C16—C15—C14	119.89 (13)	C25—C26—H26	119.8
C16—C15—H15	120.1
O1—C1—C2—C21	104.41 (15)	C12—C11—C16—C15	−0.8 (2)
C11—C1—C2—C21	−74.29 (14)	C1—C11—C16—C15	179.73 (12)
O1—C1—C2—Cl1	−17.47 (17)	C1—C2—C21—C26	−21.38 (17)
C11—C1—C2—Cl1	163.83 (9)	Cl1—C2—C21—C26	101.06 (13)
O1—C1—C11—C12	−174.40 (14)	C1—C2—C21—C22	160.45 (11)
C2—C1—C11—C12	4.30 (18)	Cl1—C2—C21—C22	−77.11 (13)
O1—C1—C11—C16	5.09 (19)	C26—C21—C22—C23	−1.02 (19)
C2—C1—C11—C16	−176.21 (11)	C2—C21—C22—C23	177.18 (12)
C16—C11—C12—C13	−0.4 (2)	C21—C22—C23—C24	1.4 (2)
C1—C11—C12—C13	179.07 (12)	C22—C23—C24—C25	−0.6 (2)
C11—C12—C13—C14	1.1 (2)	C23—C24—C25—C26	−0.6 (2)
C12—C13—C14—C15	−0.6 (2)	C22—C21—C26—C25	−0.2 (2)
C13—C14—C15—C16	−0.6 (2)	C2—C21—C26—C25	−178.35 (13)
C14—C15—C16—C11	1.3 (2)	C24—C25—C26—C21	1.0 (2)