2,2,7-Trichloro-3,4-dihydro-naphthalen-1(2H)-one.

The title compound, C(10)H(7)Cl(3)O, obtained as a major byproduct from a classical Schmidt reaction. The cyclohexyl ring is distorted from a classical chair conformation, as observed for monocyclic analogues, presumably due to conjugation of the planar annulated benzo ring and the ketone group (r.m.s. deviation 0.024 Å). There are no significant intermolecular interactions.

Related literature

For the Schmidt reaction, see: Schmidt (1923 ▶). Lactams and their derived amidines are common structural moieties in a variety of phamaceutical agents (Fylaktakidou et al., 2008 ▶), and are common in anti­psychotics (Capuano et al., 2002 ▶, 2008 ▶). For the conformation of the cyclo­hexyl ring in monocyclic analogues, see: Lectard et al. (1973 ▶); Lichanot et al. (1974 ▶).

Experimental

Crystal data

C10H7Cl3O

M = 249.51

Monoclinic,

a = 8.5233 (1) Å

b = 8.0182 (2) Å

c = 14.8698 (3) Å

β = 102.561 (1)°

V = 991.90 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.88 mm−1

T = 123 K

0.28 × 0.10 × 0.10 mm

Data collection

Nonius Kappa CCD diffractometer

Absorption correction: none

9399 measured reflections

2275 independent reflections

1859 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.06

2275 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.34 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: CIFTAB (Sheldrick, 1997 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032772/hg2549sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032772/hg2549Isup2.hkl

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

C10H7Cl3O	F(000) = 504
Mr = 249.51	Dx = 1.671 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9399 reflections
a = 8.5233 (1) Å	θ = 2.8–27.5°
b = 8.0182 (2) Å	µ = 0.88 mm−1
c = 14.8698 (3) Å	T = 123 K
β = 102.561 (1)°	Prism, colourless
V = 991.90 (3) Å3	0.28 × 0.10 × 0.10 mm
Z = 4

Nonius Kappa CCD diffractometer	1859 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
graphite	θmax = 27.5°, θmin = 2.8°
φ and ω scans	h = −11→11
9399 measured reflections	k = −10→10
2275 independent reflections	l = −19→19

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) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.6127P] where P = (Fo2 + 2Fc2)/3
2275 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	−0.11870 (6)	0.58915 (7)	0.26554 (4)	0.02493 (16)
Cl2	0.48515 (6)	1.11552 (6)	0.63056 (4)	0.02410 (15)
Cl3	0.25735 (6)	0.91201 (7)	0.70159 (4)	0.02542 (16)
O1	0.20373 (18)	1.05238 (18)	0.48477 (11)	0.0256 (4)
C1	0.2039 (2)	0.7561 (2)	0.48441 (13)	0.0167 (4)
C2	0.2751 (2)	0.6089 (2)	0.52503 (14)	0.0165 (4)
C3	0.2196 (2)	0.4562 (3)	0.48443 (14)	0.0199 (4)
H3	0.2659	0.3555	0.5116	0.024*
C4	0.0986 (2)	0.4492 (3)	0.40537 (14)	0.0200 (4)
H4	0.0616	0.3449	0.3786	0.024*
C5	0.0320 (2)	0.5981 (3)	0.36575 (14)	0.0187 (4)
C6	0.0818 (2)	0.7514 (2)	0.40393 (13)	0.0180 (4)
H6	0.0346	0.8514	0.3763	0.022*
C7	0.2542 (2)	0.9236 (2)	0.52247 (14)	0.0182 (4)
C8	0.3773 (2)	0.9241 (2)	0.61578 (14)	0.0173 (4)
C9	0.4939 (2)	0.7787 (3)	0.62603 (14)	0.0200 (4)
H9A	0.5645	0.7810	0.6884	0.024*
H9B	0.5627	0.7904	0.5806	0.024*
C10	0.4060 (2)	0.6127 (2)	0.61131 (14)	0.0198 (4)
H10A	0.4845	0.5231	0.6079	0.024*
H10B	0.3583	0.5894	0.6650	0.024*

	U11	U22	U33	U12	U13	U23
Cl1	0.0203 (3)	0.0295 (3)	0.0223 (3)	−0.0046 (2)	−0.0012 (2)	−0.0031 (2)
Cl2	0.0264 (3)	0.0186 (3)	0.0248 (3)	−0.0065 (2)	0.0002 (2)	−0.0013 (2)
Cl3	0.0253 (3)	0.0289 (3)	0.0240 (3)	0.0017 (2)	0.0097 (2)	0.0008 (2)
O1	0.0284 (8)	0.0142 (7)	0.0295 (8)	0.0003 (6)	−0.0037 (7)	0.0008 (6)
C1	0.0165 (9)	0.0157 (10)	0.0181 (9)	−0.0002 (7)	0.0043 (8)	0.0014 (8)
C2	0.0156 (9)	0.0158 (10)	0.0188 (9)	0.0010 (7)	0.0054 (7)	0.0017 (8)
C3	0.0206 (10)	0.0152 (10)	0.0250 (10)	0.0018 (8)	0.0070 (8)	0.0012 (8)
C4	0.0207 (10)	0.0168 (9)	0.0240 (10)	−0.0026 (8)	0.0083 (8)	−0.0040 (8)
C5	0.0157 (9)	0.0225 (11)	0.0178 (9)	−0.0038 (8)	0.0035 (8)	−0.0020 (8)
C6	0.0176 (9)	0.0176 (10)	0.0190 (10)	0.0012 (8)	0.0043 (8)	0.0017 (8)
C7	0.0173 (9)	0.0169 (10)	0.0198 (10)	0.0005 (8)	0.0029 (8)	0.0006 (8)
C8	0.0190 (9)	0.0148 (9)	0.0186 (9)	−0.0027 (8)	0.0050 (8)	0.0006 (8)
C9	0.0174 (9)	0.0214 (10)	0.0203 (10)	−0.0007 (8)	0.0021 (8)	0.0012 (8)
C10	0.0208 (10)	0.0157 (10)	0.0215 (10)	0.0012 (8)	0.0018 (8)	0.0027 (8)

Cl1—C5	1.744 (2)	C4—C5	1.396 (3)
Cl2—C8	1.778 (2)	C4—H4	0.9500
Cl3—C8	1.803 (2)	C5—C6	1.382 (3)
O1—C7	1.208 (2)	C6—H6	0.9500
C1—C2	1.402 (3)	C7—C8	1.547 (3)
C1—C6	1.405 (3)	C8—C9	1.518 (3)
C1—C7	1.484 (3)	C9—C10	1.520 (3)
C2—C3	1.401 (3)	C9—H9A	0.9900
C2—C10	1.506 (3)	C9—H9B	0.9900
C3—C4	1.386 (3)	C10—H10A	0.9900
C3—H3	0.9500	C10—H10B	0.9900
C2—C1—C6	120.99 (18)	C1—C7—C8	115.33 (16)
C2—C1—C7	122.35 (17)	C9—C8—C7	112.93 (16)
C6—C1—C7	116.65 (17)	C9—C8—Cl2	109.90 (14)
C3—C2—C1	118.42 (18)	C7—C8—Cl2	110.16 (13)
C3—C2—C10	120.16 (17)	C9—C8—Cl3	110.33 (14)
C1—C2—C10	121.41 (17)	C7—C8—Cl3	104.88 (13)
C4—C3—C2	121.35 (19)	Cl2—C8—Cl3	108.46 (11)
C4—C3—H3	119.3	C8—C9—C10	111.50 (16)
C2—C3—H3	119.3	C8—C9—H9A	109.3
C3—C4—C5	118.84 (19)	C10—C9—H9A	109.3
C3—C4—H4	120.6	C8—C9—H9B	109.3
C5—C4—H4	120.6	C10—C9—H9B	109.3
C6—C5—C4	121.79 (19)	H9A—C9—H9B	108.0
C6—C5—Cl1	119.40 (16)	C2—C10—C9	112.99 (16)
C4—C5—Cl1	118.80 (15)	C2—C10—H10A	109.0
C5—C6—C1	118.60 (18)	C9—C10—H10A	109.0
C5—C6—H6	120.7	C2—C10—H10B	109.0
C1—C6—H6	120.7	C9—C10—H10B	109.0
O1—C7—C1	123.49 (19)	H10A—C10—H10B	107.8
O1—C7—C8	121.17 (18)