(1S,3R,8R)-9-(1-Amino­ethyl­idene)-2,2-dichloro-3,7,7-trimethyl­tricyclo­[6.4.0.01,3]undecan-10-one

Benharref, A.; Lassaba, E.; Avignant, D.; Oudahmane, A.; Berraho, M.

doi:10.1107/S1600536811005307

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o645-o646

doi:10.1107/S1600536811005307

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(1S,3R,8R)-9-(1-Aminoethylidene)-2,2-dichloro-3,7,7-trimethyltricyclo[6.4.0.0^1,3]undecan-10-one

Ahmed Benharref,^a Essêdiya Lassaba,^a ^* Daniel Avignant,^b Abdelghani Oudahmane ^b and Moha Berraho ^a

^aLaboratoire de Chimie Biomoléculaires, Substances Naturelles et Réactivité, URAC16, Faculté des Sciences, Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and ^bUniversité Blaise Pascal, Laboratoire des Matériaux Inorganiques, UMR CNRS 6002, 24 Avenue des Landais, 63177 Aubière, France
^*Correspondence e-mail: elassaba@gmail.com

(Received 9 February 2011; accepted 12 February 2011; online 16 February 2011)

The title compound, C₁₆H₂₃Cl₂NO, was synthesised from β-himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The molecule contains a seven membered ring, which is fused to a five- and a three-membered ring. The five-membered ring has a twisted conformation, whereas the seven-membered ring displays a chair conformation. The dihedral angle between the five- and seven-membered rings is 45.26 (9)°. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, molecules are linked into chains propagating along the b axis by intermolecular N—H⋯O hydrogen bonds; an intramolecular N—H⋯O link also occurs.

Related literature

For the isolation of β-himachalene, see: Joseph & Dev (1968 ); Plattier & Teisseire (1974 ). For the reactivity of β-himachalene, see: Lassaba et al. (1998 ); Chekroun et al. (2000 ); El Jamili et al. (2002 ); Dakir et al. (2004 ). For the biological activity of β-himachalene, see: Daoubi et al. (2004 ). For conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₂₃Cl₂NO
M_r = 316.25
Monoclinic, P 2₁
a = 7.7570 (7) Å
b = 9.7041 (9) Å
c = 10.6901 (10) Å
β = 93.432 (3)°
V = 803.25 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 298 K
0.41 × 0.33 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer
4954 measured reflections
2355 independent reflections
2297 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.080
S = 1.08
2355 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack & Bernardinelli (2000 ), 614 Friedel pairs
Flack parameter: −0.02 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2⋯O1ⁱ	0.85 (3)	2.03 (3)	2.865 (3)	170 (2)
N1—H1⋯O1	0.83 (4)	1.98 (4)	2.672 (3)	140 (3)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005307/fj2396sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005307/fj2396Isup2.hkl

checkCIF report

Comment top

The essential oil of the Alas cedar (Cedrus atlantica) consist mainly (50%) of a bicyclic hydrocarbon called β-himachalene (Joseph & Dev (1968); Plattier & Teisseire(1974)). The reactivity of this sesquiterpene and its derivatives has been studied extensively by our team in order to prepare new products having biological proprieties (Lassaba et al., 1998; Chekroun et al., 2000; El Jamili et al., 2002; Dakir et al., 2004). Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against phytopathogen Botrytis cinerea (Daoubi et al., 2004). Thus the action of one equivalent of dichlorocarbene, generated in situ from chloroform in the presence of sodium hydroxide as base and n-benzyltriethylammonium chloride as catalyst, on β-himachalene produces only (1S,3R,8R)-2,2-dichloro-3,7,7,10- tetramethyltricyclo[6.4.0.0^1,3] dodec-9-ene (El Jamili et al., 2002). Treatment of the latter by two equivalents of N-bromosccinimide (NBS) give (1S, 3R, 8R, 11R)-2,2-dichloro-3,7,7,10-tetralethyltricyclo[6.4.0.0^1,3] dodec-9-en-11-one(Dakir et al., 2004). This enone was treated with the sodium azide in trifluoroacetic acide medium, give with a yield (60%) (1S, 3R, 8R) -9-(1-aminoethylidene)-2,2-dichloro-3,7,7- trimethyltricyclo[6.3.0.0^1,3]undecan -10-one. The structure of this new product was determined by NMR spectral analysis of 1H, 13 C and mass spectroscopy and confirmed by its single-crystal X-ray structure. The molecule is built up from two fused five-membered and seven-membered rings (Fig. 1). The five-membered ring adopts a twisted conformation,as indicated by Cremer & Pople (1975) puckering parameters Q = 0.2822 (2) Å and ϕ = 199.2 (4)°. The seven-membered ring displays a chair conformation with QT = 0.7470 (2) Å, θ2 = 27.72 (2)°, ϕ2 = -51.85 (14)° and ϕ3 =-78.15 (2)°. In the crystal structure, molecules are linked into chains (Fig. 2) running along the b axis by intermolecular N—H···O hydrogen bonds (Table 1) involving the O1 and N atoms. Owing to the presence of Cl atoms, the absolute configuration could be fully confirmed, by refining the Flack parameter (Flack & Bernardinelli (2000)) as C1(S), C3(R)and C8(R).

Related literature top

For the isolation of β-himachalene, see: Joseph & Dev (1968); Plattier & Teisseire (1974). For the reactivity of β-himachalene, see: Lassaba et al. (1998); Chekroun et al. (2000); El Jamili et al. (2002); Dakir et al. (2004). For the biological activity of β-himachalene, see: Daoubi et al. (2004). For conformational analysis, see: Cremer & Pople (1975).

Experimental top

To a solution of enone 1 g (3.32 mmol) in 20 ml of trifluoroacetic acid at 10 °C was added with stirring 1 g (15.38 mmol) of NaN3. After being stirred at room temperature for 24 h, the reaction mixture was neutralized with a solution of Na2CO3 (10%) and extracted three time with diethylether (3x20ml). The combined organic phases were dried on Na2SO4, filtred and concentrated at reduced pressure to give the crude product which was chromatographed on a silica gel column with hexane- ether as eluent (20/80) to give 630 mg(1.99 mmol) of (1S, 3R, 8R)-9-(1-aminoethylidene)-2,2-dichloro-3,7,7-trimethyltricyclo [6.3.0.0^1,3]undecan -10-one.The title compound was recrystallized in diethylether.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); 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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. : Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability. level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. : Partial packing view showing the C—H···O interactions (dashed lines) and the formation of a chain parallel to the c axis. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code:(i) 2 - y, x-y, z - 1/3]

(1S,3R,8R)-9-(1-Aminoethylidene)-2,2-dichloro-3,7,7- trimethyltricyclo[6.4.0.0^1,3]undecan-10-one top

Crystal data top

C₁₆H₂₃Cl₂NO	F(000) = 336
M_r = 316.25	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4954 reflections
a = 7.7570 (7) Å	θ = 3.4–26.4°
b = 9.7041 (9) Å	µ = 0.40 mm⁻¹
c = 10.6901 (10) Å	T = 298 K
β = 93.432 (3)°	Prism, colourless
V = 803.25 (13) Å³	0.41 × 0.33 × 0.26 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	2297 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.015
Graphite monochromator	θ_max = 26.4°, θ_min = 3.4°
ω and ϕ scans	h = −9→9
4954 measured reflections	k = −12→6
2355 independent reflections	l = −12→13

Refinement top

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0528P)² + 0.0821P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2355 reflections	Δρ_max = 0.24 e Å⁻³
193 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack & Bernardinelli (2000), 614 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (5)

Crystal data top

C₁₆H₂₃Cl₂NO	V = 803.25 (13) Å³
M_r = 316.25	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.7570 (7) Å	µ = 0.40 mm⁻¹
b = 9.7041 (9) Å	T = 298 K
c = 10.6901 (10) Å	0.41 × 0.33 × 0.26 mm
β = 93.432 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2297 reflections with I > 2σ(I)
4954 measured reflections	R_int = 0.015
2355 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.080	Δρ_max = 0.24 e Å⁻³
S = 1.08	Δρ_min = −0.22 e Å⁻³
2355 reflections	Absolute structure: Flack & Bernardinelli (2000), 614 Friedel pairs
193 parameters	Absolute structure parameter: −0.02 (5)
1 restraint

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
H2	1.000 (3)	−0.257 (3)	0.553 (2)	0.042 (6)*
H1	0.933 (3)	−0.125 (4)	0.502 (3)	0.050 (7)*
Cl1	0.88492 (8)	0.36063 (7)	0.85606 (7)	0.06081 (18)
Cl2	0.79425 (7)	0.12962 (6)	1.00496 (4)	0.05055 (16)
C9	0.7491 (2)	−0.0408 (2)	0.66044 (16)	0.0293 (4)
O1	0.8629 (2)	0.07077 (17)	0.48287 (13)	0.0448 (4)
C8	0.6205 (2)	0.0004 (2)	0.75543 (15)	0.0274 (4)
H8	0.6565	−0.0383	0.8375	0.033*
C1	0.6443 (2)	0.15793 (19)	0.75843 (15)	0.0297 (4)
C12	0.8402 (2)	−0.16350 (19)	0.65295 (17)	0.0321 (4)
C10	0.7797 (2)	0.0713 (2)	0.57971 (17)	0.0333 (4)
N1	0.9341 (3)	−0.1878 (2)	0.5548 (2)	0.0444 (4)
C7	0.4310 (2)	−0.0475 (2)	0.71640 (17)	0.0357 (4)
C3	0.5434 (3)	0.2575 (2)	0.83808 (17)	0.0362 (4)
C2	0.7312 (2)	0.2285 (2)	0.87178 (18)	0.0363 (4)
C4	0.4090 (3)	0.2029 (3)	0.9238 (2)	0.0462 (5)
H4A	0.4656	0.1417	0.9852	0.055*
H4B	0.3620	0.2797	0.9688	0.055*
C16	0.4318 (3)	−0.2036 (3)	0.6976 (2)	0.0451 (5)
H16A	0.5082	−0.2267	0.6333	0.068*
H16B	0.3171	−0.2344	0.6731	0.068*
H16C	0.4707	−0.2478	0.7745	0.068*
C11	0.7012 (3)	0.2010 (2)	0.62976 (17)	0.0386 (5)
H11A	0.6033	0.2311	0.5759	0.046*
H11B	0.7855	0.2747	0.6371	0.046*
C14	0.4943 (4)	0.3966 (3)	0.7812 (2)	0.0543 (6)
H14A	0.5823	0.4261	0.7276	0.082*
H14B	0.4834	0.4629	0.8469	0.082*
H14C	0.3863	0.3887	0.7330	0.082*
C5	0.2612 (3)	0.1259 (3)	0.8557 (2)	0.0551 (6)
H5A	0.2260	0.1757	0.7798	0.066*
H5B	0.1637	0.1242	0.9084	0.066*
C6	0.3060 (3)	−0.0212 (3)	0.8212 (2)	0.0491 (5)
H6A	0.1986	−0.0681	0.7975	0.059*
H6B	0.3545	−0.0657	0.8966	0.059*
C15	0.3604 (3)	0.0199 (3)	0.5944 (2)	0.0512 (6)
H15A	0.3540	0.1178	0.6058	0.077*
H15B	0.2472	−0.0157	0.5721	0.077*
H15C	0.4358	−0.0003	0.5287	0.077*
C13	0.8492 (3)	−0.2716 (3)	0.7522 (2)	0.0488 (5)
H13A	0.9673	−0.2981	0.7700	0.073*
H13B	0.7832	−0.3504	0.7236	0.073*
H13C	0.8028	−0.2358	0.8268	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0562 (3)	0.0361 (3)	0.0907 (4)	−0.0136 (3)	0.0093 (3)	−0.0118 (3)
Cl2	0.0568 (3)	0.0510 (3)	0.0424 (2)	0.0037 (3)	−0.0094 (2)	−0.0038 (2)
C9	0.0310 (8)	0.0247 (9)	0.0331 (8)	−0.0017 (7)	0.0087 (6)	−0.0004 (7)
O1	0.0579 (9)	0.0357 (8)	0.0439 (7)	−0.0015 (7)	0.0276 (6)	0.0035 (6)
C8	0.0315 (8)	0.0246 (9)	0.0266 (7)	−0.0005 (7)	0.0060 (6)	0.0011 (6)
C1	0.0335 (8)	0.0239 (10)	0.0326 (8)	0.0028 (7)	0.0085 (6)	0.0003 (7)
C12	0.0317 (8)	0.0242 (11)	0.0406 (9)	−0.0021 (7)	0.0043 (7)	−0.0033 (7)
C10	0.0380 (9)	0.0274 (10)	0.0354 (8)	−0.0023 (8)	0.0103 (7)	0.0017 (7)
N1	0.0467 (10)	0.0312 (10)	0.0571 (11)	0.0074 (9)	0.0187 (8)	−0.0038 (10)
C7	0.0328 (9)	0.0380 (11)	0.0365 (9)	−0.0049 (8)	0.0048 (7)	−0.0009 (8)
C3	0.0429 (10)	0.0292 (10)	0.0372 (9)	0.0069 (8)	0.0097 (7)	−0.0042 (8)
C2	0.0410 (10)	0.0262 (10)	0.0419 (9)	−0.0012 (8)	0.0055 (8)	−0.0051 (8)
C4	0.0469 (11)	0.0492 (14)	0.0444 (10)	0.0094 (10)	0.0175 (8)	−0.0066 (10)
C16	0.0449 (11)	0.0412 (13)	0.0493 (11)	−0.0131 (10)	0.0039 (9)	−0.0024 (10)
C11	0.0546 (12)	0.0245 (10)	0.0382 (9)	0.0020 (8)	0.0159 (8)	0.0049 (8)
C14	0.0698 (15)	0.0353 (13)	0.0589 (13)	0.0194 (11)	0.0119 (11)	−0.0001 (11)
C5	0.0365 (10)	0.0652 (17)	0.0656 (12)	0.0064 (12)	0.0196 (9)	−0.0057 (14)
C6	0.0361 (10)	0.0549 (15)	0.0579 (12)	−0.0084 (10)	0.0156 (9)	−0.0035 (11)
C15	0.0459 (12)	0.0577 (16)	0.0484 (11)	0.0006 (11)	−0.0093 (9)	0.0019 (11)
C13	0.0531 (12)	0.0324 (12)	0.0613 (12)	0.0075 (10)	0.0052 (10)	0.0115 (10)

Geometric parameters (Å, º) top

Cl1—C2	1.766 (2)	C4—C5	1.517 (4)
Cl2—C2	1.762 (2)	C4—H4A	0.9700
C9—C12	1.389 (3)	C4—H4B	0.9700
C9—C10	1.418 (3)	C16—H16A	0.9600
C9—C8	1.519 (2)	C16—H16B	0.9600
O1—C10	1.253 (2)	C16—H16C	0.9600
C8—C1	1.539 (3)	C11—H11A	0.9700
C8—C7	1.574 (2)	C11—H11B	0.9700
C8—H8	0.9800	C14—H14A	0.9600
C1—C2	1.515 (3)	C14—H14B	0.9600
C1—C11	1.528 (2)	C14—H14C	0.9600
C1—C3	1.533 (2)	C5—C6	1.519 (4)
C12—N1	1.334 (3)	C5—H5A	0.9700
C12—C13	1.490 (3)	C5—H5B	0.9700
C10—C11	1.509 (3)	C6—H6A	0.9700
N1—H2	0.84 (3)	C6—H6B	0.9700
N1—H1	0.83 (3)	C15—H15A	0.9600
C7—C16	1.528 (3)	C15—H15B	0.9600
C7—C15	1.531 (3)	C15—H15C	0.9600
C7—C6	1.546 (3)	C13—H13A	0.9600
C3—C2	1.506 (3)	C13—H13B	0.9600
C3—C14	1.520 (3)	C13—H13C	0.9600
C3—C4	1.524 (3)

C12—C9—C10	121.23 (16)	C5—C4—H4B	108.7
C12—C9—C8	128.39 (17)	C3—C4—H4B	108.7
C10—C9—C8	110.19 (16)	H4A—C4—H4B	107.6
C9—C8—C1	101.12 (14)	C7—C16—H16A	109.5
C9—C8—C7	112.64 (14)	C7—C16—H16B	109.5
C1—C8—C7	114.08 (16)	H16A—C16—H16B	109.5
C9—C8—H8	109.6	C7—C16—H16C	109.5
C1—C8—H8	109.6	H16A—C16—H16C	109.5
C7—C8—H8	109.6	H16B—C16—H16C	109.5
C2—C1—C11	117.28 (17)	C10—C11—C1	103.64 (15)
C2—C1—C3	59.21 (12)	C10—C11—H11A	111.0
C11—C1—C3	120.82 (16)	C1—C11—H11A	111.0
C2—C1—C8	120.85 (16)	C10—C11—H11B	111.0
C11—C1—C8	107.05 (14)	C1—C11—H11B	111.0
C3—C1—C8	124.93 (16)	H11A—C11—H11B	109.0
N1—C12—C9	120.03 (19)	C3—C14—H14A	109.5
N1—C12—C13	115.56 (19)	C3—C14—H14B	109.5
C9—C12—C13	124.34 (17)	H14A—C14—H14B	109.5
O1—C10—C9	127.82 (19)	C3—C14—H14C	109.5
O1—C10—C11	122.38 (17)	H14A—C14—H14C	109.5
C9—C10—C11	109.76 (15)	H14B—C14—H14C	109.5
C12—N1—H2	120.9 (16)	C4—C5—C6	113.71 (19)
C12—N1—H1	115.2 (19)	C4—C5—H5A	108.8
H2—N1—H1	123 (2)	C6—C5—H5A	108.8
C16—C7—C15	108.37 (18)	C4—C5—H5B	108.8
C16—C7—C6	105.49 (18)	C6—C5—H5B	108.8
C15—C7—C6	109.80 (18)	H5A—C5—H5B	107.7
C16—C7—C8	108.48 (17)	C5—C6—C7	119.6 (2)
C15—C7—C8	112.35 (17)	C5—C6—H6A	107.4
C6—C7—C8	112.04 (16)	C7—C6—H6A	107.4
C2—C3—C14	118.5 (2)	C5—C6—H6B	107.4
C2—C3—C4	118.56 (17)	C7—C6—H6B	107.4
C14—C3—C4	112.69 (18)	H6A—C6—H6B	107.0
C2—C3—C1	59.77 (12)	C7—C15—H15A	109.5
C14—C3—C1	117.47 (17)	C7—C15—H15B	109.5
C4—C3—C1	120.35 (18)	H15A—C15—H15B	109.5
C3—C2—C1	61.01 (12)	C7—C15—H15C	109.5
C3—C2—Cl2	120.86 (14)	H15A—C15—H15C	109.5
C1—C2—Cl2	119.26 (15)	H15B—C15—H15C	109.5
C3—C2—Cl1	119.40 (16)	C12—C13—H13A	109.5
C1—C2—Cl1	121.53 (14)	C12—C13—H13B	109.5
Cl2—C2—Cl1	108.41 (11)	H13A—C13—H13B	109.5
C5—C4—C3	114.04 (18)	C12—C13—H13C	109.5
C5—C4—H4A	108.7	H13A—C13—H13C	109.5
C3—C4—H4A	108.7	H13B—C13—H13C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O1ⁱ	0.85 (3)	2.03 (3)	2.865 (3)	170 (2)
N1—H1···O1	0.83 (4)	1.98 (4)	2.672 (3)	140 (3)

Symmetry code: (i) −x+2, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₃Cl₂NO
M_r	316.25
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	7.7570 (7), 9.7041 (9), 10.6901 (10)
β (°)	93.432 (3)
V (Å³)	803.25 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.41 × 0.33 × 0.26

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4954, 2355, 2297
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.080, 1.08
No. of reflections	2355
No. of parameters	193
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22
Absolute structure	Flack & Bernardinelli (2000), 614 Friedel pairs
Absolute structure parameter	−0.02 (5)

Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O1ⁱ	0.85 (3)	2.03 (3)	2.865 (3)	170 (2)
N1—H1···O1	0.83 (4)	1.98 (4)	2.672 (3)	140 (3)

Symmetry code: (i) −x+2, y−1/2, −z+1.

Acknowledgements

We thank the National Center of Scientific and Technological Research (CNRST) which supports our scientific research.

References

Bruker (2009). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 67| Part 3| March 2011| Pages o645-o646

doi:10.1107/S1600536811005307

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(1S,3R,8R)-9-(1-Amino­ethyl­­idene)-2,2-di­chloro-3,7,7-tri­methyl­tri­cyclo­[6.4.0.01,3]undecan-10-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1S,3R,8R)-9-(1-Aminoethylidene)-2,2-dichloro-3,7,7-trimethyltricyclo[6.4.0.0^1,3]undecan-10-one