1,7,8,9,10,10-Hexachloro-4-(2-phenyl­eth­yl)-4-aza­tricyclo­[5.2.1.02,6]dec-8-ene-3,5-dione

Manohar, R.; Harikrishna, M.; Ramanathan, C.R.; SureshKumar, M.; Gunasekaran, K.

doi:10.1107/S1600536811022495

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1708

doi:10.1107/S1600536811022495

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1,7,8,9,10,10-Hexachloro-4-(2-phenylethyl)-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

R. Manohar,^a M. Harikrishna,^b C. R. Ramanathan,^b M. SureshKumar ^c and K. Gunasekaran ^a ^*

^aCAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^bDepartment of Chemistry, Pondicherry University, Pondicherry 605 014, India, and ^cCentre for Bioinformatics, Pondicherry University, Pondicherry 605 014, India
^*Correspondence e-mail: gunaunom@gmail.com

(Received 8 May 2011; accepted 10 June 2011; online 18 June 2011)

In the title compound, C₁₇H₁₁Cl₆NO₂, the six-membered ring of the norbornene moiety adopts a boat conformation whereas the two five-membered rings adopt envelope conformations. The phenyl ring and the ring of the succinimide moiety are almost coplanar [dihedral angle = 7.44 (14)°]. The crystal packing is stabilized by a weak intermolecular C—H⋯O hydrogen bond.

Related literature

The interest in cyclic imides is due to their biological activity and wide application in the pharmaceutical industry, see: Duarte et al. (2006 ); Nakamura et al. (2006 ); Stefańska et al. (2010 ).

Experimental

Crystal data

C₁₇H₁₁Cl₆NO₂
M_r = 473.97
Monoclinic, P 2₁ /c
a = 13.3009 (5) Å
b = 13.6141 (5) Å
c = 11.4912 (4) Å
β = 111.276 (4)°
V = 1939.00 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.978, T_max = 0.984
9237 measured reflections
4457 independent reflections
2814 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.121
S = 0.72
4457 reflections
244 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H1⋯O2ⁱ	0.91 (3)	2.50 (3)	3.235 (3)	138 (2)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022495/bt5543sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022495/bt5543Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811022495/bt5543Isup3.cml

checkCIF report

Comment top

The ORTEP diagram for the molecule of the title compound is given in Fig. 1. In the crystal structure, the phenyl and the azatricyclo substitutions are in anti conformation about the C11—C12 bond which is confirmed by the torsion angle N4—C11—C12—C13 [169.3 (3)°]. In the crystal, molecules are linked by weak intermolecular C—H···O hydrogen bonds.

Related literature top

The interest in cyclic imides is due to their biological activity and wide application in the pharmaceutical industry (Duarte et al., 2006; Nakamura et al., 2006; Stefańska et al., 2010).

Experimental top

Phenethylamine (1 equiv) and 1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic anhydride (1 equiv) were stirred at room temperature in dry ethyl acetate for 30 min. Ethyl acetate was removed under reduced pressure; the resulting residue was dissolved in toluene. To this reaction mixture was added acetyl chloride (5 equiv) and refluxed for 1 h. The reaction mixture was brought to room temperature and washed with aqueous Na2CO3 and dried over anhydrous Na₂SO₄. Filtered and concentrated under reduced pressure followed by silica gel column purification afforded the imide,1,7,8,9,10,10-Hexachloro-4-(2-phenylethyl)-4-azatricyclo [5.2.1.02,6]dec-8-ene-3,5-dione,in 55% yield as colourless solid (m.p.: 161–163°C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Figures top

	Fig. 1. The ORTEP diagram of the compound with 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram.

1,7,8,9,10,10-Hexachloro-4-(2-phenylethyl)-4-azatricyclo[5.2.1.0^2,6]dec- 8-ene-3,5-dione top

Crystal data top

C₁₇H₁₁Cl₆NO₂	Z = 4
M_r = 473.97	F(000) = 952
Monoclinic, P2₁/c	D_x = 1.624 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.3009 (5) Å	θ = 3.0–29.3°
b = 13.6141 (5) Å	µ = 0.90 mm⁻¹
c = 11.4912 (4) Å	T = 293 K
β = 111.276 (4)°	Monoclinic, colourless
V = 1939.00 (12) Å³	0.20 × 0.20 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	4457 independent reflections
Radiation source: fine-focus sealed tube	2814 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 15.9821 pixels mm^-1	θ_max = 29.3°, θ_min = 3.0°
ω scans	h = −17→17
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −17→14
T_min = 0.978, T_max = 0.984	l = −15→8
9237 measured reflections

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0784P)² + 2.150P] where P = (F_o² + 2F_c²)/3
S = 0.72	(Δ/σ)_max < 0.001
4457 reflections	Δρ_max = 0.49 e Å⁻³
244 parameters	Δρ_min = −0.54 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0027 (7)

Crystal data top

C₁₇H₁₁Cl₆NO₂	V = 1939.00 (12) Å³
M_r = 473.97	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3009 (5) Å	µ = 0.90 mm⁻¹
b = 13.6141 (5) Å	T = 293 K
c = 11.4912 (4) Å	0.20 × 0.20 × 0.20 mm
β = 111.276 (4)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	4457 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2814 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.984	R_int = 0.021
9237 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 0.72	Δρ_max = 0.49 e Å⁻³
4457 reflections	Δρ_min = −0.54 e Å⁻³
244 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.2561 (2)	0.08000 (19)	0.4510 (2)	0.0363 (5)
C2	0.31543 (19)	0.02382 (19)	0.3771 (2)	0.0333 (5)
C3	0.36261 (19)	−0.0735 (2)	0.4348 (2)	0.0379 (6)
C5	0.2247 (2)	−0.1141 (2)	0.2485 (2)	0.0415 (6)
C6	0.22344 (19)	−0.0031 (2)	0.2548 (2)	0.0359 (6)
C7	0.1224 (2)	0.0410 (2)	0.2729 (2)	0.0418 (6)
C8	0.1055 (2)	−0.0167 (2)	0.3772 (3)	0.0460 (7)
C9	0.1842 (2)	0.0067 (2)	0.4824 (2)	0.0428 (6)
C10	0.1697 (2)	0.1367 (2)	0.3446 (2)	0.0399 (6)
C11	0.3368 (3)	−0.2506 (2)	0.3813 (3)	0.0522 (7)
H11A	0.4144	−0.2567	0.4224	0.063*
H11B	0.3154	−0.2875	0.3039	0.063*
C12	0.2821 (3)	−0.2937 (2)	0.4645 (4)	0.0644 (9)
H12A	0.2923	−0.2501	0.5346	0.077*
H12B	0.2052	−0.2993	0.4178	0.077*
C13	0.3272 (2)	−0.3936 (2)	0.5125 (3)	0.0426 (6)
C14	0.4205 (3)	−0.4027 (2)	0.6155 (3)	0.0570 (8)
H14	0.4556	−0.3463	0.6557	0.068*
C15	0.4629 (3)	−0.4925 (3)	0.6604 (3)	0.0676 (9)
H15	0.5260	−0.4965	0.7305	0.081*
C16	0.4133 (3)	−0.5759 (3)	0.6031 (3)	0.0661 (9)
H16	0.4424	−0.6369	0.6338	0.079*
C17	0.3213 (3)	−0.5699 (2)	0.5008 (3)	0.0634 (9)
H17	0.2874	−0.6270	0.4613	0.076*
C18	0.2779 (2)	−0.4794 (2)	0.4550 (3)	0.0526 (7)
H18	0.2149	−0.4760	0.3848	0.063*
N4	0.30886 (18)	−0.14704 (16)	0.3532 (2)	0.0403 (5)
O1	0.16542 (18)	−0.16633 (17)	0.16898 (19)	0.0610 (6)
O2	0.43337 (15)	−0.08669 (16)	0.53428 (18)	0.0539 (5)
Cl1	0.22370 (7)	0.21660 (6)	0.26068 (7)	0.0601 (2)
Cl2	0.07822 (7)	0.20423 (6)	0.39214 (7)	0.0620 (2)
Cl3	0.33930 (7)	0.15230 (6)	0.57446 (7)	0.0663 (3)
Cl4	0.21264 (9)	−0.04238 (8)	0.62570 (8)	0.0806 (3)
Cl5	0.01097 (7)	0.05813 (9)	0.13594 (8)	0.0834 (3)
Cl6	0.00951 (8)	−0.10391 (8)	0.35359 (11)	0.0894 (4)
H1	0.368 (2)	0.062 (2)	0.366 (2)	0.043 (7)*
H2	0.232 (2)	0.0211 (19)	0.183 (2)	0.039 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0423 (13)	0.0338 (14)	0.0295 (11)	0.0036 (11)	0.0092 (10)	−0.0045 (10)
C2	0.0310 (12)	0.0318 (14)	0.0393 (13)	−0.0037 (11)	0.0152 (10)	−0.0033 (10)
C3	0.0329 (12)	0.0386 (15)	0.0460 (14)	0.0032 (11)	0.0188 (11)	0.0005 (12)
C5	0.0459 (14)	0.0467 (16)	0.0421 (14)	−0.0073 (13)	0.0280 (12)	−0.0097 (12)
C6	0.0377 (13)	0.0444 (15)	0.0294 (12)	−0.0014 (12)	0.0166 (10)	−0.0042 (11)
C7	0.0340 (12)	0.0560 (18)	0.0323 (12)	0.0029 (12)	0.0084 (10)	−0.0037 (12)
C8	0.0456 (15)	0.0471 (17)	0.0577 (17)	−0.0020 (13)	0.0336 (14)	−0.0047 (13)
C9	0.0601 (16)	0.0410 (15)	0.0392 (14)	0.0146 (13)	0.0323 (13)	0.0061 (12)
C10	0.0452 (14)	0.0411 (15)	0.0350 (13)	0.0101 (12)	0.0166 (11)	0.0044 (11)
C11	0.070 (2)	0.0319 (15)	0.0702 (19)	0.0018 (14)	0.0446 (17)	−0.0006 (14)
C12	0.072 (2)	0.051 (2)	0.091 (2)	0.0183 (17)	0.055 (2)	0.0242 (17)
C13	0.0465 (15)	0.0388 (15)	0.0510 (15)	0.0044 (13)	0.0279 (13)	0.0049 (12)
C14	0.0562 (18)	0.0514 (19)	0.0609 (19)	−0.0132 (16)	0.0182 (15)	−0.0101 (15)
C15	0.0499 (18)	0.081 (3)	0.063 (2)	0.0035 (19)	0.0097 (15)	0.0122 (19)
C16	0.075 (2)	0.051 (2)	0.083 (2)	0.0209 (19)	0.041 (2)	0.0135 (18)
C17	0.087 (2)	0.0437 (19)	0.071 (2)	−0.0118 (18)	0.043 (2)	−0.0190 (16)
C18	0.0504 (16)	0.066 (2)	0.0403 (14)	−0.0050 (15)	0.0150 (12)	−0.0024 (14)
N4	0.0498 (12)	0.0322 (12)	0.0466 (12)	−0.0012 (10)	0.0266 (10)	−0.0038 (10)
O1	0.0680 (13)	0.0623 (15)	0.0557 (12)	−0.0209 (12)	0.0260 (10)	−0.0277 (11)
O2	0.0415 (10)	0.0529 (13)	0.0573 (12)	0.0088 (10)	0.0061 (9)	0.0043 (10)
Cl1	0.0820 (6)	0.0462 (4)	0.0617 (5)	0.0098 (4)	0.0376 (4)	0.0159 (3)
Cl2	0.0724 (5)	0.0608 (5)	0.0613 (5)	0.0312 (4)	0.0343 (4)	0.0060 (4)
Cl3	0.0743 (5)	0.0543 (5)	0.0504 (4)	0.0050 (4)	−0.0010 (4)	−0.0221 (4)
Cl4	0.1149 (8)	0.0892 (7)	0.0602 (5)	0.0396 (6)	0.0587 (5)	0.0350 (5)
Cl5	0.0491 (4)	0.1271 (9)	0.0517 (5)	0.0178 (5)	−0.0085 (4)	−0.0190 (5)
Cl6	0.0718 (6)	0.0813 (7)	0.1426 (9)	−0.0319 (5)	0.0716 (6)	−0.0264 (6)

Geometric parameters (Å, º) top

C1—C9	1.514 (4)	C10—Cl2	1.762 (3)
C1—C10	1.547 (3)	C10—Cl1	1.769 (3)
C1—C2	1.554 (3)	C11—N4	1.464 (3)
C1—Cl3	1.751 (2)	C11—C12	1.515 (4)
C2—C3	1.512 (4)	C11—H11A	0.9700
C2—C6	1.535 (3)	C11—H11B	0.9700
C2—H1	0.91 (3)	C12—C13	1.507 (4)
C3—O2	1.202 (3)	C12—H12A	0.9700
C3—N4	1.381 (3)	C12—H12B	0.9700
C5—O1	1.200 (3)	C13—C14	1.375 (4)
C5—N4	1.387 (3)	C13—C18	1.384 (4)
C5—C6	1.514 (4)	C14—C15	1.366 (5)
C6—C7	1.552 (3)	C14—H14	0.9300
C6—H2	0.93 (3)	C15—C16	1.357 (5)
C7—C8	1.517 (4)	C15—H15	0.9300
C7—C10	1.548 (4)	C16—C17	1.357 (5)
C7—Cl5	1.742 (3)	C16—H16	0.9300
C8—C9	1.319 (4)	C17—C18	1.382 (5)
C8—Cl6	1.692 (3)	C17—H17	0.9300
C9—Cl4	1.688 (3)	C18—H18	0.9300

C9—C1—C10	99.5 (2)	C7—C10—Cl2	114.29 (18)
C9—C1—C2	107.2 (2)	C1—C10—Cl1	113.92 (18)
C10—C1—C2	101.12 (18)	C7—C10—Cl1	113.21 (17)
C9—C1—Cl3	116.46 (17)	Cl2—C10—Cl1	108.11 (15)
C10—C1—Cl3	115.44 (18)	N4—C11—C12	111.8 (2)
C2—C1—Cl3	115.00 (18)	N4—C11—H11A	109.3
C3—C2—C6	105.0 (2)	C12—C11—H11A	109.3
C3—C2—C1	113.8 (2)	N4—C11—H11B	109.3
C6—C2—C1	102.91 (19)	C12—C11—H11B	109.3
C3—C2—H1	110.1 (17)	H11A—C11—H11B	107.9
C6—C2—H1	113.8 (17)	C13—C12—C11	111.3 (2)
C1—C2—H1	111.1 (17)	C13—C12—H12A	109.4
O2—C3—N4	124.8 (3)	C11—C12—H12A	109.4
O2—C3—C2	127.3 (3)	C13—C12—H12B	109.4
N4—C3—C2	107.9 (2)	C11—C12—H12B	109.4
O1—C5—N4	124.7 (3)	H12A—C12—H12B	108.0
O1—C5—C6	127.8 (3)	C14—C13—C18	117.3 (3)
N4—C5—C6	107.5 (2)	C14—C13—C12	120.8 (3)
C5—C6—C2	105.2 (2)	C18—C13—C12	122.0 (3)
C5—C6—C7	114.7 (2)	C15—C14—C13	121.7 (3)
C2—C6—C7	103.08 (18)	C15—C14—H14	119.1
C5—C6—H2	107.6 (16)	C13—C14—H14	119.1
C2—C6—H2	114.6 (16)	C16—C15—C14	120.2 (3)
C7—C6—H2	111.6 (16)	C16—C15—H15	119.9
C8—C7—C6	106.8 (2)	C14—C15—H15	119.9
C8—C7—C10	99.4 (2)	C15—C16—C17	119.8 (3)
C6—C7—C10	101.1 (2)	C15—C16—H16	120.1
C8—C7—Cl5	117.48 (19)	C17—C16—H16	120.1
C6—C7—Cl5	115.15 (17)	C16—C17—C18	120.3 (3)
C10—C7—Cl5	114.6 (2)	C16—C17—H17	119.9
C9—C8—C7	107.7 (2)	C18—C17—H17	119.9
C9—C8—Cl6	128.2 (2)	C13—C18—C17	120.7 (3)
C7—C8—Cl6	123.8 (2)	C13—C18—H18	119.6
C8—C9—C1	107.5 (2)	C17—C18—H18	119.6
C8—C9—Cl4	128.4 (2)	C3—N4—C5	114.2 (2)
C1—C9—Cl4	123.8 (2)	C3—N4—C11	121.4 (2)
C1—C10—C7	92.4 (2)	C5—N4—C11	124.3 (2)
C1—C10—Cl2	114.45 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H1···O2ⁱ	0.91 (3)	2.50 (3)	3.235 (3)	138 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁Cl₆NO₂
M_r	473.97
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.3009 (5), 13.6141 (5), 11.4912 (4)
β (°)	111.276 (4)
V (Å³)	1939.00 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.978, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9237, 4457, 2814
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.121, 0.72
No. of reflections	4457
No. of parameters	244
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.54

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H1···O2ⁱ	0.91 (3)	2.50 (3)	3.235 (3)	138 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

CRR thanks DST-FIST for the single-crystal X-ray facility at the Department of Chemistry, Pondicherry University, Pondicherry.

References

Duarte, F. S., Andrade, E. S., Vieira, R. A., Uieara, M., Nunes, R. J. & de Lima, T. C. M. (2006). Bioorg. Med. Chem. 14, 5397–5401. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Nakamura, T., Noguchi, T., Kobayashi, H., Miyachi, H. & Hashimoto, Y. (2006). Chem. Pharm. Bull. 54, 1709–1714. Web of Science CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stefańska, J., Bielenica, A., Struga, M., Tyski, S., Kossakowski, J., Colla, P. L., Tamburini, E. & Loddo, R. (2010). Ann. Microbiol. 60, 151–155. Google Scholar

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Volume 67| Part 7| July 2011| Page o1708

doi:10.1107/S1600536811022495

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

1,7,8,9,10,10-Hexa­chloro-4-(2-phenyl­eth­yl)-4-aza­tri­cyclo­[5.2.1.02,6]dec-8-ene-3,5-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,7,8,9,10,10-Hexachloro-4-(2-phenylethyl)-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione