(S)-4-(2-Chloro-propan-2-yl)-1-(2,2,2-trichloro-eth-yl)cyclo-hexene.

The title compound, C(11)H(16)Cl(4), was synthesized by the reaction of (1S)-β-pinene with triethyl-amine in the presence of ZnCl(2). The cyclo-hexene ring assumes a half-boat conformation. The crystal packing is governed only by van der Waals inter-actions. The structure, which has been refined in P2(1), presents a striking P2(1)/m pseudosymmetry.

Related literature

For background to the synthesis of polyhalogenated compounds, see: Delaude et al. (2004 ▶); Borguet et al. (2007 ▶). For the synthesis and structure of natural chlorinated compounds reported by our group, see: Ziyat et al. (2002 ▶, 2004 ▶); Boualy et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C11H16Cl4

M = 290.04

Monoclinic,

a = 10.6558 (7) Å

b = 10.3017 (6) Å

c = 6.3119 (3) Å

β = 91.251 (5)°

V = 692.71 (7) Å3

Z = 2

Cu Kα radiation

μ = 7.50 mm−1

T = 294 K

0.21 × 0.09 × 0.07 mm

Data collection

Siemens AED diffractometer

Absorption correction: refined from ΔF (DIFABS; Walker & Stuart, 1983 ▶) T min = 0.456, T max = 0.601

2764 measured reflections

2528 independent reflections

2206 reflections with I > 2σ(I)

R int = 0.038

3 standard reflections every 100 reflections intensity decay: 0.02%

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.129

S = 1.16

2528 reflections

136 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶); 1188 Friedel pairs

Flack parameter: −0.04 (3)

Data collection: AED (Belletti et al., 1993 ▶); cell refinement: AED; data reduction: AED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and SCHAKAL97 (Keller, 1997 ▶); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010257/bg2395sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010257/bg2395Isup2.hkl

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

C11H16Cl4	F(000) = 300
Mr = 290.04	Dx = 1.391 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 48 reflections
a = 10.6558 (7) Å	θ = 19.3–31.4°
b = 10.3017 (6) Å	µ = 7.50 mm−1
c = 6.3119 (3) Å	T = 294 K
β = 91.251 (5)°	Irregular block, colourless
V = 692.71 (7) Å3	0.21 × 0.09 × 0.07 mm
Z = 2

Siemens AED diffractometer	2206 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
graphite	θmax = 68.0°, θmin = 4.2°
θ/2θ scans	h = −12→12
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983)	k = −12→12
Tmin = 0.456, Tmax = 0.601	l = −1→7
2764 measured reflections	3 standard reflections every 100 reflections
2528 independent reflections	intensity decay: 0.02%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0811P)2] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max < 0.001
2528 reflections	Δρmax = 0.27 e Å−3
136 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983); 1188 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (3)

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	0.92140 (14)	0.06856 (10)	−0.3180 (2)	0.0976 (4)
Cl2	1.15231 (7)	0.20291 (18)	−0.23878 (15)	0.0990 (3)
Cl3	0.92735 (12)	0.34740 (9)	−0.3247 (2)	0.0954 (4)
Cl4	0.46844 (7)	0.21653 (15)	0.60646 (11)	0.0855 (3)
C1	0.8287 (2)	0.2091 (4)	0.1030 (4)	0.0667 (6)
C2	0.7742 (4)	0.1006 (3)	0.1658 (7)	0.0733 (9)
H2	0.8213	0.0247	0.1630	0.088*
C3	0.6416 (4)	0.0915 (3)	0.2416 (7)	0.0762 (11)
H3A	0.6436	0.0713	0.3917	0.091*
H3B	0.5996	0.0205	0.1683	0.091*
C4	0.5658 (2)	0.2149 (4)	0.2064 (4)	0.0630 (5)
H4	0.5460	0.2189	0.0542	0.076*
C5	0.6483 (4)	0.3326 (4)	0.2565 (7)	0.0766 (11)
H5A	0.5994	0.4114	0.2382	0.092*
H5B	0.6776	0.3285	0.4029	0.092*
C6	0.7592 (5)	0.3362 (4)	0.1129 (8)	0.0912 (13)
H6A	0.8167	0.4032	0.1621	0.109*
H6B	0.7302	0.3596	−0.0288	0.109*
C7	0.9642 (2)	0.2108 (5)	0.0397 (4)	0.0721 (6)
H7A	1.0063	0.1370	0.1052	0.086*
H7B	1.0031	0.2887	0.0971	0.086*
C8	0.9870 (2)	0.2066 (5)	−0.1959 (4)	0.0696 (6)
C9	0.4387 (2)	0.2159 (4)	0.3195 (4)	0.0657 (6)
C10	0.3606 (4)	0.3349 (4)	0.2697 (7)	0.0826 (11)
H10A	0.4088	0.4115	0.3014	0.124*
H10B	0.2866	0.3341	0.3539	0.124*
H10C	0.3367	0.3347	0.1222	0.124*
C11	0.3614 (5)	0.0931 (4)	0.2681 (8)	0.0870 (13)
H11A	0.4109	0.0175	0.3001	0.131*
H11B	0.3379	0.0929	0.1204	0.131*
H11C	0.2872	0.0924	0.3518	0.131*

	U11	U22	U33	U12	U13	U23
Cl1	0.1090 (9)	0.0869 (6)	0.0972 (9)	−0.0153 (6)	0.0089 (8)	−0.0282 (6)
Cl2	0.0705 (4)	0.1114 (7)	0.1159 (6)	0.0073 (6)	0.0184 (4)	0.0098 (8)
Cl3	0.0994 (8)	0.0875 (7)	0.0998 (8)	0.0092 (6)	0.0124 (7)	0.0294 (6)
Cl4	0.0896 (5)	0.1015 (6)	0.0658 (4)	−0.0017 (7)	0.0100 (3)	−0.0054 (6)
C1	0.0785 (14)	0.0560 (12)	0.0656 (13)	0.011 (2)	0.0025 (11)	−0.002 (2)
C2	0.084 (2)	0.0530 (17)	0.083 (2)	0.0111 (15)	0.0145 (18)	0.0110 (15)
C3	0.090 (3)	0.0472 (18)	0.092 (3)	0.0030 (16)	0.020 (2)	0.0037 (17)
C4	0.0766 (14)	0.0513 (12)	0.0611 (12)	0.0043 (18)	0.0036 (10)	0.0010 (18)
C5	0.079 (2)	0.0523 (17)	0.099 (3)	−0.0007 (16)	0.013 (2)	−0.009 (2)
C6	0.091 (2)	0.0473 (15)	0.136 (4)	0.0015 (16)	0.028 (3)	0.008 (2)
C7	0.0728 (14)	0.0695 (14)	0.0736 (14)	0.000 (2)	−0.0061 (11)	0.007 (2)
C8	0.0673 (13)	0.0629 (13)	0.0787 (15)	0.0014 (19)	0.0050 (11)	0.005 (2)
C9	0.0712 (14)	0.0567 (13)	0.0691 (13)	−0.0005 (18)	−0.0036 (10)	−0.0042 (19)
C10	0.078 (3)	0.071 (2)	0.099 (3)	0.0121 (19)	0.002 (2)	0.001 (2)
C11	0.089 (3)	0.071 (3)	0.100 (4)	−0.007 (2)	−0.001 (3)	−0.008 (2)

Cl1—C8	1.755 (4)	C5—H5A	0.9700
Cl2—C8	1.789 (3)	C5—H5B	0.9700
Cl3—C8	1.774 (4)	C6—H6A	0.9700
Cl4—C9	1.832 (3)	C6—H6B	0.9700
C1—C2	1.324 (5)	C7—C8	1.512 (4)
C1—C6	1.506 (5)	C7—H7A	0.9700
C1—C7	1.507 (4)	C7—H7B	0.9700
C2—C3	1.504 (6)	C9—C10	1.511 (5)
C2—H2	0.9300	C9—C11	1.541 (6)
C3—C4	1.520 (5)	C10—H10A	0.9600
C3—H3A	0.9700	C10—H10B	0.9600
C3—H3B	0.9700	C10—H10C	0.9600
C4—C5	1.526 (5)	C11—H11A	0.9600
C4—C9	1.545 (4)	C11—H11B	0.9600
C4—H4	0.9800	C11—H11C	0.9600
C5—C6	1.505 (6)
C2—C1—C6	120.1 (3)	C1—C7—C8	115.8 (2)
C2—C1—C7	121.2 (4)	C1—C7—H7A	108.3
C6—C1—C7	118.5 (4)	C8—C7—H7A	108.3
C1—C2—C3	124.7 (3)	C1—C7—H7B	108.3
C1—C2—H2	117.7	C8—C7—H7B	108.3
C3—C2—H2	117.7	H7A—C7—H7B	107.4
C2—C3—C4	113.6 (3)	C7—C8—Cl1	112.6 (3)
C2—C3—H3A	108.8	C7—C8—Cl3	111.3 (3)
C4—C3—H3A	108.8	Cl1—C8—Cl3	109.02 (15)
C2—C3—H3B	108.8	C7—C8—Cl2	109.21 (18)
C4—C3—H3B	108.8	Cl1—C8—Cl2	107.5 (2)
H3A—C3—H3B	107.7	Cl3—C8—Cl2	107.0 (2)
C3—C4—C5	109.4 (2)	C10—C9—C11	109.4 (2)
C3—C4—C9	114.0 (3)	C10—C9—C4	113.2 (3)
C5—C4—C9	113.9 (3)	C11—C9—C4	111.5 (3)
C3—C4—H4	106.3	C10—C9—Cl4	106.6 (2)
C5—C4—H4	106.3	C11—C9—Cl4	106.9 (3)
C9—C4—H4	106.3	C4—C9—Cl4	108.81 (17)
C6—C5—C4	110.5 (3)	C9—C10—H10A	109.5
C6—C5—H5A	109.5	C9—C10—H10B	109.5
C4—C5—H5A	109.5	H10A—C10—H10B	109.5
C6—C5—H5B	109.5	C9—C10—H10C	109.5
C4—C5—H5B	109.5	H10A—C10—H10C	109.5
H5A—C5—H5B	108.1	H10B—C10—H10C	109.5
C5—C6—C1	113.4 (3)	C9—C11—H11A	109.5
C5—C6—H6A	108.9	C9—C11—H11B	109.5
C1—C6—H6A	108.9	H11A—C11—H11B	109.5
C5—C6—H6B	108.9	C9—C11—H11C	109.5
C1—C6—H6B	108.9	H11A—C11—H11C	109.5
H6A—C6—H6B	107.7	H11B—C11—H11C	109.5