7,8,9,10-Tetra­hydro­cyclo­hepta­[b]indol-6(5H)-one

Sridharan, M.; Prasad, K.J.R.; Gunaseelan, A.T.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S160053680802463X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1697

doi:10.1107/S160053680802463X

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7,8,9,10-Tetrahydrocyclohepta[b]indol-6(5H)-one

M. Sridharan,^a K. J. Rajendra Prasad,^a A. Thomas Gunaseelan,^b A. Thiruvalluvar ^b ^* and R. J. Butcher ^c

^aDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, ^bPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: athiru@vsnl.net

(Received 30 July 2008; accepted 31 July 2008; online 6 August 2008)

In the title molecule, C₁₃H₁₃NO, the dihedral angle between the benzene and pyrrole rings is 1.05 (5)°. The cycloheptene ring adopts a slightly distorted boat conformation. In the crystal structure, intermolecular N—H⋯O hydrogen bonds form centrosymmetric dimers. A C—H⋯π interaction, involving the benzene ring, is also found in the structure.

Related literature

For a related structure, see: Sridharan et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₃NO
M_r = 199.24
Monoclinic, P 2₁ /c
a = 14.0914 (4) Å
b = 8.0883 (2) Å
c = 9.2503 (3) Å
β = 108.937 (3)°
V = 997.24 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 200 (2) K
0.56 × 0.38 × 0.31 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.985, T_max = 1.000 (expected range = 0.960–0.974)
15925 measured reflections
4127 independent reflections
3036 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.145
S = 1.01
4127 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O6ⁱ	0.891 (16)	1.976 (16)	2.8188 (11)	157.3 (13)
C10—H10A⋯Cgⁱⁱ	0.99	2.90	3.7087 (10)	139
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg is the centroid of the benzene ring.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; 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: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802463X/wn2274sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802463X/wn2274Isup2.hkl

checkCIF report

Comment top

Sridharan et al. (2008) have reported the crystal structure of 7,8,9,10-tetrahydro-2-methylcyclohepta[b]indol-6(5H)-one, in which the cycloheptene ring adopts a slightly distorted envelope conformation. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The dihedral angle between the benzene ring and the pyrrole ring is 1.05 (5)°. The cycloheptene ring adopts a slightly distorted boat conformation. Intermolecular N5—H5···O6 (-x, -y, 1 - z) hydrogen bonds form centrosymmetric dimers in the crystal structure (Fig. 2). A C—H···π interaction, involving the benzene ring, is also found in the structure.

Related literature top

For a related structure, see: Sridharan et al. (2008).

Experimental top

A solution of 2-(2-(4-phenyl)hydrazono)cycloheptanone (0.216 g, 0.001 mol) in a mixture of acetic acid (20 ml) and concentrated hydrochloric acid (5 ml) was refluxed on an oil bath pre-heated to 398–403 K for 2 h. The reaction was monitored by TLC. After the completion of reaction the contents were cooled and poured into ice water with stirring. The separated brown solid was filtered and purified by passing through a column of silica gel and eluting with petroleum ether-ethyl acetate (95:5 v/v) mixture to yield the title compound (0.129 g, 61%). The product thus obtained was recrystallized using ethanol.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); 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: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are represented by spheres of arbitrary radius.
	Fig. 2. The molecular packing of the title compound, viewed down the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

7,8,9,10-Tetrahydrocyclohepta[b]indol-6(5H)-one top

Crystal data top

C₁₃H₁₃NO	F(000) = 424
M_r = 199.24	D_x = 1.327 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 425(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.0914 (4) Å	Cell parameters from 7034 reflections
b = 8.0883 (2) Å	θ = 5.0–34.8°
c = 9.2503 (3) Å	µ = 0.08 mm⁻¹
β = 108.937 (3)°	T = 200 K
V = 997.24 (5) Å³	Chunk, pale-yellow
Z = 4	0.56 × 0.38 × 0.31 mm

Data collection top

Oxford Diffraction R Gemini diffractometer	4127 independent reflections
Radiation source: fine-focus sealed tube	3036 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.5081 pixels mm^-1	θ_max = 34.9°, θ_min = 5.0°
ϕ and ω scans	h = −22→22
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −12→12
T_min = 0.985, T_max = 1.000	l = −11→14
15925 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.097P)²] where P = (F_o² + 2F_c²)/3
4127 reflections	(Δ/σ)_max = 0.001
140 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₃H₁₃NO	V = 997.24 (5) Å³
M_r = 199.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.0914 (4) Å	µ = 0.08 mm⁻¹
b = 8.0883 (2) Å	T = 200 K
c = 9.2503 (3) Å	0.56 × 0.38 × 0.31 mm
β = 108.937 (3)°

Data collection top

Oxford Diffraction R Gemini diffractometer	4127 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	3036 reflections with I > 2σ(I)
T_min = 0.985, T_max = 1.000	R_int = 0.023
15925 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.31 e Å⁻³
4127 reflections	Δρ_min = −0.35 e Å⁻³
140 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O6	−0.00855 (5)	0.08244 (11)	0.30591 (9)	0.0440 (2)
N5	0.15340 (5)	−0.04196 (9)	0.54651 (8)	0.0256 (2)
C1	0.42047 (7)	−0.01523 (11)	0.66953 (11)	0.0298 (2)
C2	0.44834 (7)	−0.08626 (12)	0.81195 (11)	0.0343 (3)
C3	0.37614 (7)	−0.14708 (12)	0.87403 (11)	0.0332 (3)
C4	0.27498 (7)	−0.13868 (10)	0.79473 (10)	0.0284 (2)
C4A	0.24673 (6)	−0.06767 (10)	0.64909 (9)	0.0232 (2)
C5A	0.16322 (6)	0.03677 (10)	0.41960 (10)	0.0242 (2)
C6	0.07608 (6)	0.08971 (11)	0.29509 (10)	0.0280 (2)
C7	0.09234 (7)	0.15126 (12)	0.15191 (11)	0.0321 (3)
C8	0.16098 (8)	0.03791 (13)	0.09678 (11)	0.0349 (3)
C9	0.27357 (7)	0.06922 (12)	0.16778 (11)	0.0312 (2)
C10	0.30600 (6)	0.14407 (11)	0.32855 (10)	0.0293 (2)
C10A	0.26382 (6)	0.05963 (10)	0.43769 (10)	0.0235 (2)
C10B	0.31807 (6)	−0.00584 (10)	0.58454 (10)	0.0235 (2)
H1	0.46963	0.02683	0.62920	0.0357*
H2	0.51753	−0.09456	0.86970	0.0412*
H3	0.39782	−0.19511	0.97311	0.0398*
H4	0.22650	−0.17934	0.83711	0.0340*
H5	0.0970 (11)	−0.0616 (16)	0.5673 (16)	0.049 (4)*
H7A	0.02662	0.16053	0.07022	0.0385*
H7B	0.12233	0.26314	0.17084	0.0385*
H8A	0.14277	0.04968	−0.01546	0.0419*
H8B	0.14723	−0.07800	0.11811	0.0419*
H9A	0.30934	−0.03693	0.17193	0.0375*
H9B	0.29503	0.14442	0.09981	0.0375*
H10A	0.28542	0.26165	0.32052	0.0351*
H10B	0.38014	0.14072	0.37110	0.0351*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O6	0.0248 (3)	0.0711 (5)	0.0371 (4)	0.0026 (3)	0.0116 (3)	0.0130 (4)
N5	0.0247 (3)	0.0298 (3)	0.0240 (3)	−0.0015 (3)	0.0102 (3)	0.0031 (3)
C1	0.0252 (4)	0.0355 (4)	0.0284 (4)	−0.0014 (3)	0.0084 (3)	−0.0035 (3)
C2	0.0296 (4)	0.0410 (5)	0.0283 (4)	0.0012 (4)	0.0038 (3)	−0.0013 (4)
C3	0.0391 (5)	0.0331 (4)	0.0239 (4)	0.0006 (3)	0.0055 (3)	0.0021 (3)
C4	0.0358 (4)	0.0266 (4)	0.0231 (4)	−0.0022 (3)	0.0101 (3)	0.0008 (3)
C4A	0.0262 (3)	0.0217 (3)	0.0224 (4)	−0.0004 (3)	0.0088 (3)	−0.0016 (3)
C5A	0.0252 (4)	0.0256 (3)	0.0229 (4)	−0.0003 (3)	0.0094 (3)	0.0017 (3)
C6	0.0262 (4)	0.0316 (4)	0.0268 (4)	0.0006 (3)	0.0096 (3)	0.0035 (3)
C7	0.0308 (4)	0.0386 (5)	0.0270 (4)	0.0031 (3)	0.0097 (3)	0.0091 (3)
C8	0.0370 (5)	0.0436 (5)	0.0250 (4)	−0.0005 (4)	0.0113 (4)	−0.0009 (4)
C9	0.0358 (4)	0.0367 (4)	0.0261 (4)	0.0016 (3)	0.0168 (3)	0.0049 (3)
C10	0.0295 (4)	0.0326 (4)	0.0289 (4)	−0.0038 (3)	0.0139 (3)	0.0023 (3)
C10A	0.0257 (4)	0.0240 (3)	0.0230 (4)	−0.0010 (3)	0.0109 (3)	−0.0006 (3)
C10B	0.0247 (3)	0.0238 (3)	0.0226 (4)	−0.0007 (3)	0.0087 (3)	−0.0024 (3)

Geometric parameters (Å, º) top

O6—C6	1.2301 (12)	C9—C10	1.5316 (13)
N5—C4A	1.3650 (11)	C10—C10A	1.4928 (12)
N5—C5A	1.3814 (11)	C10A—C10B	1.4269 (12)
N5—H5	0.891 (16)	C1—H1	0.9500
C1—C10B	1.4035 (14)	C2—H2	0.9500
C1—C2	1.3726 (14)	C3—H3	0.9500
C2—C3	1.4093 (14)	C4—H4	0.9500
C3—C4	1.3770 (14)	C7—H7A	0.9900
C4—C4A	1.3983 (12)	C7—H7B	0.9900
C4A—C10B	1.4166 (12)	C8—H8A	0.9900
C5A—C6	1.4491 (12)	C8—H8B	0.9900
C5A—C10A	1.3849 (13)	C9—H9A	0.9900
C6—C7	1.5005 (13)	C9—H9B	0.9900
C7—C8	1.5350 (15)	C10—H10A	0.9900
C8—C9	1.5285 (15)	C10—H10B	0.9900

O6···N5	2.8066 (11)	H2···H9B^vii	2.6000
O6···N5ⁱ	2.8188 (11)	H3···C1^v	2.9200
O6···H5	2.661 (14)	H3···C10B^v	2.9900
O6···H5ⁱ	1.976 (16)	H5···O6	2.661 (14)
N5···O6	2.8066 (11)	H5···O6ⁱ	1.976 (16)
N5···O6ⁱ	2.8188 (11)	H5···H7Bⁱⁱ	2.5800
N5···H7Bⁱⁱ	2.6300	H7A···C8^vi	3.0500
C2···C2ⁱⁱⁱ	3.5893 (14)	H7A···H8B^vi	2.5900
C1···H10B	2.9200	H7B···C10	2.7000
C1···H3^iv	2.9200	H7B···C10A	3.1000
C3···H2ⁱⁱⁱ	3.0600	H7B···H10A	2.2700
C4···H8B^v	3.0400	H7B···N5^viii	2.6300
C4···H9A^v	2.9600	H7B···C4A^viii	3.0700
C4···H10Aⁱⁱ	3.0600	H7B···C5A^viii	3.0400
C4A···H7Bⁱⁱ	3.0700	H7B···H5^viii	2.5800
C4A···H10Aⁱⁱ	2.8900	H8B···C5A	2.8800
C5A···H8B	2.8800	H8B···C10A	3.0900
C5A···H7Bⁱⁱ	3.0400	H8B···H7A^vi	2.5900
C7···H10A	2.8100	H8B···C4^iv	3.0400
C8···H7A^vi	3.0500	H9A···C4^iv	2.9600
C9···H2^vii	3.0800	H9B···H2^vii	2.6000
C10···H7B	2.7000	H9B···C10^viii	3.0800
C10···H9Bⁱⁱ	3.0800	H9B···C10A^viii	2.7800
C10A···H7B	3.1000	H9B···C10B^viii	2.9500
C10A···H8B	3.0900	H10A···C7	2.8100
C10A···H9Bⁱⁱ	2.7800	H10A···H7B	2.2700
C10B···H3^iv	2.9900	H10A···C4^viii	3.0600
C10B···H9Bⁱⁱ	2.9500	H10A···C4A^viii	2.8900
C10B···H10Aⁱⁱ	3.0900	H10A···C10B^viii	3.0900
H1···H10B	2.4900	H10B···C1	2.9200
H1···H10B^vii	2.5100	H10B···H1	2.4900
H2···C3ⁱⁱⁱ	3.0600	H10B···H1^vii	2.5100
H2···C9^vii	3.0800

C4A—N5—C5A	108.75 (7)	C10B—C1—H1	121.00
C4A—N5—H5	123.3 (9)	C1—C2—H2	119.00
C5A—N5—H5	127.5 (9)	C3—C2—H2	119.00
C2—C1—C10B	118.83 (9)	C2—C3—H3	119.00
C1—C2—C3	121.18 (9)	C4—C3—H3	119.00
C2—C3—C4	121.68 (9)	C3—C4—H4	121.00
C3—C4—C4A	117.09 (9)	C4A—C4—H4	121.00
N5—C4A—C4	129.88 (8)	C6—C7—H7A	109.00
N5—C4A—C10B	107.98 (7)	C6—C7—H7B	109.00
C4—C4A—C10B	122.14 (8)	C8—C7—H7A	109.00
N5—C5A—C6	121.26 (8)	C8—C7—H7B	109.00
C6—C5A—C10A	128.81 (8)	H7A—C7—H7B	108.00
N5—C5A—C10A	109.86 (8)	C7—C8—H8A	108.00
O6—C6—C7	121.16 (8)	C7—C8—H8B	108.00
C5A—C6—C7	117.83 (8)	C9—C8—H8A	108.00
O6—C6—C5A	121.00 (8)	C9—C8—H8B	108.00
C6—C7—C8	112.85 (8)	H8A—C8—H8B	107.00
C7—C8—C9	115.87 (8)	C8—C9—H9A	109.00
C8—C9—C10	115.07 (8)	C8—C9—H9B	108.00
C9—C10—C10A	114.65 (8)	C10—C9—H9A	109.00
C5A—C10A—C10B	106.06 (8)	C10—C9—H9B	109.00
C10—C10A—C10B	127.28 (8)	H9A—C9—H9B	108.00
C5A—C10A—C10	126.58 (8)	C9—C10—H10A	109.00
C4A—C10B—C10A	107.34 (8)	C9—C10—H10B	109.00
C1—C10B—C4A	119.08 (8)	C10A—C10—H10A	109.00
C1—C10B—C10A	133.56 (8)	C10A—C10—H10B	109.00
C2—C1—H1	121.00	H10A—C10—H10B	108.00

C5A—N5—C4A—C4	178.26 (8)	C10A—C5A—C6—O6	−168.79 (9)
C5A—N5—C4A—C10B	−0.94 (9)	C10A—C5A—C6—C7	12.09 (14)
C4A—N5—C5A—C6	−176.03 (8)	N5—C5A—C10A—C10	−178.13 (8)
C4A—N5—C5A—C10A	1.30 (10)	N5—C5A—C10A—C10B	−1.11 (9)
C2—C1—C10B—C10A	179.18 (9)	C6—C5A—C10A—C10	−1.05 (15)
C2—C1—C10B—C4A	0.89 (13)	C6—C5A—C10A—C10B	175.96 (8)
C10B—C1—C2—C3	−0.89 (14)	O6—C6—C7—C8	−132.19 (10)
C1—C2—C3—C4	0.30 (15)	C5A—C6—C7—C8	46.93 (11)
C2—C3—C4—C4A	0.29 (13)	C6—C7—C8—C9	−85.91 (11)
C3—C4—C4A—C10B	−0.27 (12)	C7—C8—C9—C10	27.65 (12)
C3—C4—C4A—N5	−179.36 (9)	C8—C9—C10—C10A	48.32 (11)
N5—C4A—C10B—C1	178.95 (8)	C9—C10—C10A—C5A	−57.72 (12)
C4—C4A—C10B—C10A	−179.02 (8)	C9—C10—C10A—C10B	125.89 (9)
N5—C4A—C10B—C10A	0.25 (9)	C5A—C10A—C10B—C1	−177.91 (9)
C4—C4A—C10B—C1	−0.32 (12)	C5A—C10A—C10B—C4A	0.53 (9)
N5—C5A—C6—O6	7.99 (13)	C10—C10A—C10B—C1	−0.92 (16)
N5—C5A—C6—C7	−171.13 (8)	C10—C10A—C10B—C4A	177.51 (8)

Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+2; (iv) x, −y−1/2, z−1/2; (v) x, −y−1/2, z+1/2; (vi) −x, −y, −z; (vii) −x+1, −y, −z+1; (viii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O6ⁱ	0.891 (16)	1.976 (16)	2.8188 (11)	157.3 (13)
C10—H10A···Cg^viii	0.99	2.90	3.7087 (10)	139

Symmetry codes: (i) −x, −y, −z+1; (viii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO
M_r	199.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	14.0914 (4), 8.0883 (2), 9.2503 (3)
β (°)	108.937 (3)
V (Å³)	997.24 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.56 × 0.38 × 0.31

Data collection
Diffractometer	Oxford Diffraction R Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.985, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15925, 4127, 3036
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.806

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.145, 1.01
No. of reflections	4127
No. of parameters	140
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.35

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O6ⁱ	0.891 (16)	1.976 (16)	2.8188 (11)	157.3 (13)
C10—H10A···Cgⁱⁱ	0.99	2.90	3.7087 (10)	139

Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y+1/2, z−1/2.

Acknowledgements

MS thanks the UGC, New Delhi, India, for the award of a research fellowship. KJR acknowledges the UGC, New Delhi, India, for the award of Major Research Project Grant No. F.No.31–122/2005. AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007]. RJB acknowledges the NSF-MRI program for funding to purchase the X-ray CCD diffractometer.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, 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. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008). Acta Cryst. E64, o1207. Web of Science CSD CrossRef IUCr Journals Google Scholar