rac-3,4-trans-Dichloro-1,2,3,4-tetra-hydro-2-naphthyl acetate.

The title compound, C(12)H(12)Cl(2)O(2), has a bicyclic skeleton containing cyclo-hexene and benzene fragments. The cyclo-hexene ring adopts a half-chair conformation with displacements of two atoms out of the least-squares plane of 0.311 (2) and -0.336 (2) Å. The Cl atoms are trans-positioned.

Related literature

For related literature, see: Frimer (1985a ▶,b ▶); March & Smith (2001 ▶); McBride et al. (1999 ▶); Metha & Ramesh (2003 ▶, 2005 ▶); Metha et al. (2003 ▶); Patai (1983 ▶); Ros et al. (2006 ▶); Wasserman & Murray (1979 ▶). For related structures, see: Kishali et al. (2006a ▶,b ▶).

Experimental

Crystal data

C12H12Cl2O2

M = 259.12

Monoclinic,

a = 12.931 (5) Å

b = 12.478 (5) Å

c = 7.441 (4) Å

β = 101.040 (5)°

V = 1178.4 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 293 (2) K

0.2 × 0.2 × 0.2 mm

Data collection

Rigaku R-AXIS conversion diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.897, T max = 0.898

34473 measured reflections

3627 independent reflections

2486 reflections with I > 2σ(I)

R int = 0.083

25 standard reflections every 200 reflections intensity decay: 3%

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.154

S = 1.09

3627 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035563/kp2181sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035563/kp2181Isup2.hkl

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

C12H12Cl2O2	F(000) = 536
Mr = 259.12	Dx = 1.461 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6382 reflections
a = 12.931 (5) Å	θ = 2.3–30.6°
b = 12.478 (5) Å	µ = 0.53 mm−1
c = 7.441 (4) Å	T = 293 K
β = 101.040 (5)°	Needle, pale white
V = 1178.4 (9) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Rigaku R-AXIS conversion diffractometer	Rint = 0.083
dtprofit.ref scans	θmax = 30.7°, θmin = 2.3°
Absorption correction: multi-scan (Blessing, 1995)	h = −18→18
Tmin = 0.897, Tmax = 0.898	k = −17→17
34473 measured reflections	l = −10→10
3627 independent reflections	25 standard reflections every 200 reflections
2486 reflections with I > 2σ(I)	intensity decay: 3%

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.063	w = 1/[σ2(Fo2) + (0.0549P)2 + 0.2956P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.154	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.21 e Å−3
3627 reflections	Δρmin = −0.34 e Å−3
146 parameters

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.

	x	y	z	Uiso*/Ueq
Cl1	0.22319 (6)	0.59964 (5)	0.18471 (9)	0.0666 (2)
Cl2	0.12465 (5)	0.59224 (5)	0.70388 (10)	0.0667 (2)
O1	0.13535 (12)	0.35895 (13)	0.5577 (2)	0.0535 (4)
O2	0.23303 (14)	0.22818 (15)	0.4683 (3)	0.0722 (5)
C1	0.34102 (17)	0.62147 (18)	0.5296 (3)	0.0486 (5)
C2	0.40917 (19)	0.7052 (2)	0.5078 (3)	0.0580 (6)
H2	0.3843	0.7623	0.4315	0.07*
C3	0.5123 (2)	0.7044 (2)	0.5973 (4)	0.0646 (7)
H3	0.5573	0.7601	0.5804	0.078*
C4	0.5489 (2)	0.6200 (2)	0.7129 (4)	0.0636 (7)
H4	0.6184	0.6197	0.7756	0.076*
C5	0.48316 (19)	0.5365 (2)	0.7357 (3)	0.0577 (6)
H5	0.5089	0.4802	0.8135	0.069*
C6	0.37804 (17)	0.53492 (18)	0.6436 (3)	0.0478 (5)
C7	0.30921 (18)	0.44074 (19)	0.6704 (3)	0.0533 (5)
H7A	0.3489	0.3748	0.6696	0.064*
H7B	0.2883	0.4467	0.7884	0.064*
C8	0.21251 (17)	0.43671 (18)	0.5214 (3)	0.0483 (5)
H8	0.2343	0.4166	0.4069	0.058*
C9	0.15676 (17)	0.54420 (18)	0.4929 (3)	0.0496 (5)
H9	0.0921	0.5369	0.4005	0.06*
C10	0.22906 (18)	0.62559 (18)	0.4281 (3)	0.0512 (5)
H10	0.2012	0.6975	0.4416	0.061*
C11	0.15545 (19)	0.25602 (19)	0.5198 (3)	0.0546 (6)
C12	0.0677 (2)	0.1837 (2)	0.5466 (4)	0.0707 (7)
H12A	0.0407	0.2066	0.6519	0.106*
H12B	0.0934	0.1116	0.5648	0.106*
H12C	0.0124	0.1865	0.4402	0.106*

	U11	U22	U33	U12	U13	U23
Cl1	0.0761 (5)	0.0694 (4)	0.0518 (4)	−0.0055 (3)	0.0059 (3)	0.0081 (3)
Cl2	0.0632 (4)	0.0683 (4)	0.0735 (5)	0.0053 (3)	0.0256 (3)	−0.0070 (3)
O1	0.0468 (9)	0.0490 (9)	0.0664 (10)	−0.0052 (7)	0.0152 (8)	0.0032 (7)
O2	0.0656 (11)	0.0582 (11)	0.0966 (15)	−0.0020 (9)	0.0247 (10)	−0.0128 (10)
C1	0.0485 (12)	0.0474 (11)	0.0511 (12)	−0.0018 (9)	0.0125 (10)	−0.0053 (9)
C2	0.0639 (15)	0.0509 (13)	0.0615 (14)	−0.0085 (11)	0.0179 (12)	−0.0030 (11)
C3	0.0614 (15)	0.0659 (16)	0.0701 (16)	−0.0204 (12)	0.0216 (13)	−0.0162 (13)
C4	0.0460 (13)	0.0794 (18)	0.0653 (16)	−0.0074 (12)	0.0108 (12)	−0.0163 (13)
C5	0.0487 (13)	0.0634 (15)	0.0601 (14)	0.0002 (11)	0.0082 (11)	−0.0047 (11)
C6	0.0444 (11)	0.0518 (12)	0.0482 (12)	−0.0019 (9)	0.0114 (9)	−0.0028 (9)
C7	0.0474 (12)	0.0509 (12)	0.0605 (14)	0.0011 (10)	0.0076 (11)	0.0062 (11)
C8	0.0430 (11)	0.0455 (11)	0.0579 (13)	−0.0031 (9)	0.0131 (10)	0.0016 (10)
C9	0.0438 (11)	0.0513 (12)	0.0532 (12)	0.0022 (9)	0.0083 (10)	−0.0018 (10)
C10	0.0533 (13)	0.0455 (11)	0.0544 (13)	0.0019 (9)	0.0094 (10)	0.0015 (10)
C11	0.0545 (13)	0.0508 (13)	0.0566 (14)	−0.0052 (10)	0.0055 (11)	0.0025 (10)
C12	0.0676 (16)	0.0600 (16)	0.0823 (19)	−0.0171 (13)	0.0092 (14)	0.0069 (14)

Cl1—C10	1.827 (3)	C7—H7A	0.97
Cl2—C9	1.802 (3)	C7—H7B	0.97
O1—C11	1.351 (3)	C8—H8	0.98
O1—C8	1.454 (3)	C10—H10	0.98
C9—C8	1.518 (3)	C4—C5	1.376 (4)
C9—C10	1.520 (3)	C4—C3	1.385 (4)
C9—H9	0.98	C4—H4	0.93
C6—C1	1.400 (3)	C5—H5	0.93
C6—C5	1.401 (3)	C2—C3	1.372 (4)
C6—C7	1.510 (3)	C2—H2	0.93
C1—C2	1.396 (3)	C3—H3	0.93
C1—C10	1.500 (3)	C12—H12A	0.96
O2—C11	1.192 (3)	C12—H12B	0.96
C11—C12	1.493 (3)	C12—H12C	0.96
C7—C8	1.504 (3)
C11—O1—C8	115.45 (18)	C7—C8—H8	108.2
C8—C9—C10	109.28 (18)	C9—C8—H8	108.2
C8—C9—Cl2	110.77 (17)	C1—C10—C9	114.21 (19)
C10—C9—Cl2	108.22 (16)	C1—C10—Cl1	110.26 (16)
C8—C9—H9	109.5	C9—C10—Cl1	106.55 (16)
C10—C9—H9	109.5	C1—C10—H10	108.6
Cl2—C9—H9	109.5	C9—C10—H10	108.6
C1—C6—C5	118.2 (2)	Cl1—C10—H10	108.6
C1—C6—C7	122.58 (19)	C5—C4—C3	120.4 (2)
C5—C6—C7	119.2 (2)	C5—C4—H4	119.8
C2—C1—C6	119.8 (2)	C3—C4—H4	119.8
C2—C1—C10	119.1 (2)	C4—C5—C6	121.0 (2)
C6—C1—C10	121.1 (2)	C4—C5—H5	119.5
O2—C11—O1	123.5 (2)	C6—C5—H5	119.5
O2—C11—C12	125.1 (2)	C3—C2—C1	121.0 (2)
O1—C11—C12	111.4 (2)	C3—C2—H2	119.5
C8—C7—C6	110.88 (19)	C1—C2—H2	119.5
C8—C7—H7A	109.5	C2—C3—C4	119.5 (2)
C6—C7—H7A	109.5	C2—C3—H3	120.3
C8—C7—H7B	109.5	C4—C3—H3	120.3
C6—C7—H7B	109.5	C11—C12—H12A	109.5
H7A—C7—H7B	108.1	C11—C12—H12B	109.5
O1—C8—C7	112.88 (18)	H12A—C12—H12B	109.5
O1—C8—C9	106.93 (17)	C11—C12—H12C	109.5
C7—C8—C9	112.26 (19)	H12A—C12—H12C	109.5
O1—C8—H8	108.2	H12B—C12—H12C	109.5
C5—C6—C1—C2	1.2 (3)	C2—C1—C10—C9	−167.4 (2)
C7—C6—C1—C2	−178.7 (2)	C6—C1—C10—C9	13.3 (3)
C5—C6—C1—C10	−179.4 (2)	C2—C1—C10—Cl1	72.7 (2)
C7—C6—C1—C10	0.6 (3)	C6—C1—C10—Cl1	−106.6 (2)
C8—O1—C11—O2	3.4 (3)	C8—C9—C10—C1	−43.7 (3)
C8—O1—C11—C12	−175.2 (2)	Cl2—C9—C10—C1	77.0 (2)
C1—C6—C7—C8	17.2 (3)	C8—C9—C10—Cl1	78.3 (2)
C5—C6—C7—C8	−162.8 (2)	Cl2—C9—C10—Cl1	−161.00 (12)
C11—O1—C8—C7	−79.8 (2)	C3—C4—C5—C6	−0.2 (4)
C11—O1—C8—C9	156.3 (2)	C1—C6—C5—C4	−1.0 (3)
C6—C7—C8—O1	−170.16 (18)	C7—C6—C5—C4	179.0 (2)
C6—C7—C8—C9	−49.2 (3)	C6—C1—C2—C3	−0.3 (4)
C10—C9—C8—O1	−172.10 (18)	C10—C1—C2—C3	−179.6 (2)
Cl2—C9—C8—O1	68.8 (2)	C1—C2—C3—C4	−0.9 (4)
C10—C9—C8—C7	63.6 (2)	C5—C4—C3—C2	1.2 (4)
Cl2—C9—C8—C7	−55.5 (2)