1,7,8,9,10,10-Hexachloro-4-(thio­phen-2-ylmeth­yl)-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/S1600536811032788

organic compounds

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Volume 67| Part 9| September 2011| Page o2391

doi:10.1107/S1600536811032788

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1,7,8,9,10,10-Hexachloro-4-(thiophen-2-ylmethyl)-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 600025, India, ^bDepartment of Chemistry, Pondicherry University, Pondicherry 605014, India, and ^cCentre for Bioinformatics, Pondicherry University, Pondicherry 605014, India
^*Correspondence e-mail: gunaunom@gmail.com

(Received 21 July 2011; accepted 12 August 2011; online 27 August 2011)

In the title compound, C₁₄H₇Cl₆NO₂S, the six-membered ring of the azatricyclo system has a boat conformation whereas the five-membered rings have an envelope conformation. The thiophene ring and the ring of the succinimide moiety enclose a dihedral angle of 67.2 (1)°. The crystal packing is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of cyclic imides, see: Duarte et al. (2006 ); Nakamura et al. (2006 ); Stefańska et al. (2010 ).

Experimental

Crystal data

C₁₄H₇Cl₆NO₂S
M_r = 465.97
Tetragonal, I 4₁ /a
a = 23.8136 (10) Å
c = 12.6240 (9) Å
V = 7158.9 (7) Å³
Z = 16
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm Is this OK?

Data collection

Xcalibur, Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.978, T_max = 0.984
8488 measured reflections
4156 independent reflections
2283 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.075
S = 0.82
4156 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.98	2.54	3.064 (3)	113
C6—H6⋯O2ⁱ	0.98	2.51	3.042 (3)	114
Symmetry code: (i) $[y-{\script{1\over 4}}, -x+{\script{7\over 4}}, z-{\script{1\over 4}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 I, global. DOI: 10.1107/S1600536811032788/bt5586sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032788/bt5586Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032788/bt5586Isup3.cml

checkCIF report

Comment top

Azatricyclo dec-8-ene 3,5 dione derivatives have anti bacterial and anti fungal activities with other important biological activities (Stefańska et al., 2010).

In these structure, the six-membered ring of the norbornene moiety adopts a boat conformation whereas the two five-membered rings adopt envelope conformation.The fusion at atoms C6 and C2 is in cis conformation. The planarity around N4 and C3—N4 [1.38 (4) Å] and N4—C5 [1.38 (4) Å] reveals the partial double bond charater to facilitate the electron delocalization from one keto oxygen to other through N4. The crystal structure is stabilized by weak inter-molecular C-H···O interactions.

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

1-(thiophen-2-yl)methanamine (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-(thiophen-2-yl-methyl)-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione, in 92% yield as colorless solid.

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 (Sheldrick, 2008) 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-(thiophen-2-ylmethyl)-4- azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione top

Crystal data top

C₁₄H₇Cl₆NO₂S	F(000) = 3712
M_r = 465.97	D_x = 1.729 Mg m⁻³
Tetragonal, I4₁/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 4ad	µ = 1.08 mm⁻¹
a = 23.8136 (10) Å	T = 293 K
c = 12.6240 (9) Å	Tetragonal, colourless
V = 7158.9 (7) Å³	0.20 × 0.20 × 0.20 mm
Z = 16

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	4156 independent reflections
Radiation source: fine-focus sealed tube	2283 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 15.9821 pixels mm^-1	θ_max = 29.2°, θ_min = 3.0°
ω scans	h = −29→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −28→32
T_min = 0.978, T_max = 0.984	l = −15→17
8488 measured reflections

Refinement top

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) = 0.075	H-atom parameters constrained
S = 0.82	w = 1/[σ²(F_o²) + (0.0329P)²] where P = (F_o² + 2F_c²)/3
4156 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₄H₇Cl₆NO₂S	Z = 16
M_r = 465.97	Mo Kα radiation
Tetragonal, I4₁/a	µ = 1.08 mm⁻¹
a = 23.8136 (10) Å	T = 293 K
c = 12.6240 (9) Å	0.20 × 0.20 × 0.20 mm
V = 7158.9 (7) Å³

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	4156 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2283 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.984	R_int = 0.032
8488 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 0.82	Δρ_max = 0.31 e Å⁻³
4156 reflections	Δρ_min = −0.31 e Å⁻³
217 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	0.60327 (10)	1.16190 (10)	0.08398 (18)	0.0301 (6)
C2	0.66296 (9)	1.13668 (9)	0.09872 (19)	0.0295 (6)
H2	0.6864	1.1422	0.0358	0.035*
C3	0.69158 (10)	1.15740 (10)	0.1978 (2)	0.0326 (6)
C5	0.67499 (10)	1.06286 (10)	0.2282 (2)	0.0344 (6)
C6	0.65133 (9)	1.07395 (9)	0.11968 (18)	0.0288 (6)
H6	0.6690	1.0500	0.0660	0.035*
C7	0.58607 (9)	1.07054 (9)	0.11446 (18)	0.0276 (5)
C8	0.56310 (9)	1.10361 (10)	0.20743 (17)	0.0291 (6)
C9	0.57323 (9)	1.15729 (10)	0.18980 (18)	0.0285 (6)
C10	0.57402 (9)	1.11314 (11)	0.02405 (18)	0.0342 (6)
C11	0.72133 (10)	1.11804 (11)	0.3724 (2)	0.0432 (7)
H11A	0.7054	1.0897	0.4187	0.052*
H11B	0.7116	1.1546	0.4009	0.052*
C12	0.78385 (11)	1.11200 (10)	0.37121 (19)	0.0391 (7)
C13	0.82275 (11)	1.15206 (11)	0.3454 (2)	0.0485 (8)
H13	0.8140	1.1888	0.3269	0.058*
C14	0.87777 (12)	1.13051 (13)	0.3504 (2)	0.0617 (9)
H14	0.9094	1.1520	0.3355	0.074*
C15	0.88049 (12)	1.07617 (13)	0.3788 (2)	0.0573 (8)
H15	0.9137	1.0559	0.3857	0.069*
N4	0.69675 (8)	1.11223 (8)	0.26664 (16)	0.0321 (5)
O1	0.70632 (7)	1.20435 (7)	0.21805 (15)	0.0486 (5)
O2	0.67518 (8)	1.01900 (7)	0.27599 (16)	0.0550 (5)
S	0.81534 (3)	1.04915 (3)	0.40044 (6)	0.0562 (2)
Cl1	0.60119 (3)	1.22738 (3)	0.02283 (6)	0.0557 (2)
Cl2	0.55865 (3)	1.00296 (3)	0.09833 (6)	0.0508 (2)
Cl3	0.53529 (3)	1.07338 (3)	0.31710 (6)	0.0528 (2)
Cl4	0.56334 (3)	1.21203 (3)	0.27281 (6)	0.0553 (2)
Cl5	0.50195 (3)	1.12482 (3)	0.00103 (6)	0.0524 (2)
Cl6	0.60575 (3)	1.09588 (3)	−0.09771 (5)	0.0593 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0295 (13)	0.0306 (13)	0.0303 (14)	0.0027 (11)	0.0006 (11)	0.0069 (11)
C2	0.0227 (12)	0.0304 (13)	0.0353 (14)	−0.0024 (11)	0.0064 (11)	0.0025 (11)
C3	0.0210 (12)	0.0312 (14)	0.0456 (17)	−0.0027 (12)	0.0021 (12)	−0.0004 (13)
C5	0.0246 (13)	0.0282 (14)	0.0502 (17)	0.0013 (11)	−0.0019 (12)	0.0016 (13)
C6	0.0233 (12)	0.0267 (12)	0.0363 (15)	0.0006 (11)	0.0046 (11)	−0.0074 (11)
C7	0.0259 (12)	0.0271 (13)	0.0300 (14)	−0.0056 (11)	−0.0008 (11)	−0.0045 (11)
C8	0.0221 (12)	0.0384 (14)	0.0269 (14)	−0.0004 (12)	0.0030 (10)	0.0015 (12)
C9	0.0239 (12)	0.0318 (14)	0.0298 (14)	0.0080 (12)	0.0016 (11)	−0.0028 (11)
C10	0.0250 (13)	0.0519 (16)	0.0258 (13)	0.0007 (13)	−0.0012 (11)	−0.0058 (12)
C11	0.0458 (16)	0.0434 (16)	0.0404 (17)	0.0009 (14)	−0.0096 (14)	−0.0005 (13)
C12	0.0431 (16)	0.0383 (15)	0.0358 (16)	0.0025 (14)	−0.0143 (13)	0.0004 (13)
C13	0.0452 (17)	0.0378 (16)	0.062 (2)	−0.0073 (15)	−0.0266 (15)	0.0034 (14)
C14	0.0424 (18)	0.065 (2)	0.078 (2)	−0.0156 (18)	−0.0232 (16)	0.0116 (19)
C15	0.0419 (17)	0.067 (2)	0.064 (2)	0.0061 (17)	−0.0172 (15)	0.0063 (17)
N4	0.0287 (11)	0.0289 (11)	0.0388 (13)	−0.0024 (10)	−0.0077 (10)	0.0019 (10)
O1	0.0490 (11)	0.0291 (10)	0.0678 (14)	−0.0106 (9)	−0.0153 (10)	−0.0003 (9)
O2	0.0545 (12)	0.0307 (10)	0.0798 (16)	−0.0019 (10)	−0.0175 (11)	0.0179 (10)
S	0.0603 (5)	0.0458 (4)	0.0625 (5)	0.0053 (4)	−0.0086 (4)	0.0148 (4)
Cl1	0.0628 (5)	0.0437 (4)	0.0607 (5)	0.0027 (4)	−0.0044 (4)	0.0242 (4)
Cl2	0.0489 (4)	0.0382 (4)	0.0653 (5)	−0.0164 (3)	−0.0050 (4)	−0.0117 (3)
Cl3	0.0537 (4)	0.0620 (5)	0.0427 (4)	−0.0081 (4)	0.0166 (4)	0.0107 (4)
Cl4	0.0606 (5)	0.0437 (4)	0.0617 (5)	0.0095 (4)	0.0148 (4)	−0.0194 (4)
Cl5	0.0325 (3)	0.0753 (5)	0.0494 (4)	−0.0002 (4)	−0.0142 (3)	0.0020 (4)
Cl6	0.0611 (5)	0.0861 (6)	0.0308 (4)	−0.0023 (5)	0.0084 (4)	−0.0126 (4)

Geometric parameters (Å, º) top

C1—C9	1.519 (3)	C8—C9	1.320 (3)
C1—C10	1.551 (3)	C8—Cl3	1.695 (2)
C1—C2	1.554 (3)	C9—Cl4	1.689 (2)
C1—Cl1	1.741 (2)	C10—Cl6	1.761 (2)
C2—C3	1.508 (3)	C10—Cl5	1.763 (2)
C2—C6	1.542 (3)	C11—N4	1.464 (3)
C2—H2	0.9800	C11—C12	1.496 (3)
C3—O1	1.199 (3)	C11—H11A	0.9700
C3—N4	1.388 (3)	C11—H11B	0.9700
C5—O2	1.206 (3)	C12—C13	1.369 (3)
C5—N4	1.374 (3)	C12—S	1.714 (3)
C5—C6	1.504 (3)	C13—C14	1.409 (4)
C6—C7	1.558 (3)	C13—H13	0.9300
C6—H6	0.9800	C14—C15	1.344 (4)
C7—C8	1.516 (3)	C14—H14	0.9300
C7—C10	1.554 (3)	C15—S	1.701 (3)
C7—Cl2	1.749 (2)	C15—H15	0.9300

C9—C1—C10	99.40 (18)	C7—C8—Cl3	123.56 (17)
C9—C1—C2	107.31 (18)	C8—C9—C1	107.72 (19)
C10—C1—C2	100.37 (18)	C8—C9—Cl4	128.13 (19)
C9—C1—Cl1	116.18 (16)	C1—C9—Cl4	123.74 (18)
C10—C1—Cl1	116.20 (16)	C1—C10—C7	92.72 (17)
C2—C1—Cl1	115.16 (16)	C1—C10—Cl6	114.06 (17)
C3—C2—C6	104.81 (19)	C7—C10—Cl6	114.17 (17)
C3—C2—C1	112.73 (19)	C1—C10—Cl5	113.56 (17)
C6—C2—C1	103.33 (17)	C7—C10—Cl5	113.82 (16)
C3—C2—H2	111.8	Cl6—C10—Cl5	108.10 (12)
C6—C2—H2	111.8	N4—C11—C12	112.3 (2)
C1—C2—H2	111.8	N4—C11—H11A	109.1
O1—C3—N4	124.3 (2)	C12—C11—H11A	109.1
O1—C3—C2	127.9 (2)	N4—C11—H11B	109.1
N4—C3—C2	107.8 (2)	C12—C11—H11B	109.1
O2—C5—N4	124.2 (2)	H11A—C11—H11B	107.9
O2—C5—C6	127.5 (2)	C13—C12—C11	127.5 (2)
N4—C5—C6	108.2 (2)	C13—C12—S	111.32 (19)
C5—C6—C2	105.01 (19)	C11—C12—S	121.1 (2)
C5—C6—C7	113.76 (19)	C12—C13—C14	111.4 (2)
C2—C6—C7	102.84 (18)	C12—C13—H13	124.3
C5—C6—H6	111.6	C14—C13—H13	124.3
C2—C6—H6	111.6	C15—C14—C13	114.0 (3)
C7—C6—H6	111.6	C15—C14—H14	123.0
C8—C7—C10	99.38 (18)	C13—C14—H14	123.0
C8—C7—C6	107.48 (18)	C14—C15—S	111.3 (2)
C10—C7—C6	100.44 (17)	C14—C15—H15	124.4
C8—C7—Cl2	115.70 (16)	S—C15—H15	124.4
C10—C7—Cl2	116.52 (16)	C5—N4—C3	114.1 (2)
C6—C7—Cl2	115.18 (16)	C5—N4—C11	123.7 (2)
C9—C8—C7	107.86 (19)	C3—N4—C11	122.2 (2)
C9—C8—Cl3	128.35 (19)	C15—S—C12	91.96 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.98	2.54	3.064 (3)	113
C6—H6···O2ⁱ	0.98	2.51	3.042 (3)	114

Symmetry code: (i) y−1/4, −x+7/4, z−1/4.

Experimental details

Crystal data
Chemical formula	C₁₄H₇Cl₆NO₂S
M_r	465.97
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	293
a, c (Å)	23.8136 (10), 12.6240 (9)
V (Å³)	7158.9 (7)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
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	8488, 4156, 2283
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.075, 0.82
No. of reflections	4156
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.31

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.98	2.54	3.064 (3)	113.3
C6—H6···O2ⁱ	0.98	2.51	3.042 (3)	114.2

Symmetry code: (i) y−1/4, −x+7/4, z−1/4.

Acknowledgements

CRR is grateful to the DST–FIST single-crystal X-ray facility of the Department of Chemistry, Pondicherry University, Pondicherry.

References

Duarte, F. S., Andrade, E. S., Vieira, R. A., Uieara, M., de Nunes, R. J. & Lima, T. C. M. (2006). Bioorg. Med. Chem. 14, 5397–5401. CrossRef 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, 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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1,7,8,9,10,10-Hexa­chloro-4-(thio­phen-2-ylmeth­yl)-4-aza­tri­cyclo­[5.2.1.02,6]dec-8-ene-3,5-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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