1-Naphthyl 9H-carbazole-4-sulfonate

Arulmozhi, R.; Vennila, J.P.; Babu, S.M.; Kavitha, H.P.; Manivannan, V.

doi:10.1107/S1600536808016334

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1208

doi:10.1107/S1600536808016334

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1-Naphthyl 9H-carbazole-4-sulfonate

R. Arulmozhi,^a Jasmine P. Vennila,^b Sunil Manohar Babu,^c Helen P. Kavitha ^d and V. Manivannan ^e ^*

^aDepartment of Chemistry, SRM University, Kattankulathur 603 203, Kanchipuram, India, ^bDepartment of Physics, Panimalar Institute of Technology, Chennai 600 095, India, ^cNicholas Piramal Research Centre, Nicholas Piramal India Limited, Mumbai 400 063, India, ^dDepartment of Chemistry, SRM University, Ramapuram, Chennai 600 089, India, and ^eDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 23 May 2008; accepted 29 May 2008; online 7 June 2008)

In the title compound, C₂₂H₁₅NO₃S, the plane of the carbazole ring system forms a dihedral angle of 65.06 (4)° with the naphthalene ring system. In the crystal structure, a weak intramolecular C—H⋯O interaction is observed between the naphthalene ring system and the sulfonate group. Two weak intermolecular C—H⋯O interactions are also observed.

Related literature

For biological activity, see: Itoigawa et al. (2000 ); Tachibana et al. (2001 ). For the structure of closely related compounds, see: Manivannan et al. (2005 ); Hosomi et al. (2000 ).

Experimental

Crystal data

C₂₂H₁₅NO₃S
M_r = 373.41
Orthorhombic, P b c a
a = 14.2365 (5) Å
b = 9.2098 (4) Å
c = 26.3865 (10) Å
V = 3459.7 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 (2) K
0.20 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.959, T_max = 0.971
22287 measured reflections
4600 independent reflections
2928 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.144
S = 1.05
4600 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.33 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⋯O2	0.93	2.42	2.835 (3)	107
C8—H8⋯O3ⁱ	0.93	2.50	3.403 (3)	164
C17—H17⋯O3ⁱⁱ	0.93	2.54	3.364 (3)	147
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2; cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016334/is2296sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016334/is2296Isup2.hkl

checkCIF report

Comment top

Carbazole derivatives possess various biological activities, such as antitumor (Itoigawa et al., 2000), antioxidative (Tachibana et al., 2001). We report the crystal structure of the title compound, (I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported structures (Manivannan et al., 2005; Hosomi et al., 2000).

The plane of the carbazole ring forms a dihedral angle of 65.06 (4)° with the naphthalene ring. The torsion angles C2—C1—S1—O2 and C10—C1—S1—O3 [4.21 (19) ° and 46.22 (18)°, respectively] indicate a syn conformation of sulfonyl moiety. The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing is stabilized by weak intermolecular C—H···O interactions.

Related literature top

For biological activity, see: Itoigawa et al. (2000); Tachibana et al. (2001). For the structure of closely related compounds, see: Manivannan et al. (2005); Hosomi et al. (2000).

Experimental top

1-Naphthalene sulfonyl chloride (1.19 g, 5.2 mmol) dissolved in methelene dichloride was slowly added to 9H carbazol-4-ol (0.9 g, 4.8 mmol), followed by the addition of triethylamine (0.72 g, 7 mmol) at 20 °C. The reaction mixture was warmed at 40 °C and maintained at that temperature for 4 h. The reaction mixture was cooled to 15 °C. and mixed with 10 ml of methelene dichloride and 10 ml of water. The methelene dichloride layer was separated, washed to neutral pH with 5% aqueous sodium dicarbonate solution, dried over anhydrous sodium sulfate and concentrated. The crude compound was recrystallized from toluene.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

1-Naphthyl 9H-carbazole-4-sulfonate top

Crystal data top

C₂₂H₁₅NO₃S	F(000) = 1552
M_r = 373.41	D_x = 1.434 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4996 reflections
a = 14.2365 (5) Å	θ = 2.6–25.7°
b = 9.2098 (4) Å	µ = 0.21 mm⁻¹
c = 26.3865 (10) Å	T = 295 K
V = 3459.7 (2) Å³	Block, colourless
Z = 8	0.20 × 0.16 × 0.14 mm

Data collection top

Bruker Kappa APEXII diffractometer	4600 independent reflections
Radiation source: fine-focus sealed tube	2928 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scans	θ_max = 29.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
T_min = 0.959, T_max = 0.971	k = −12→5
22287 measured reflections	l = −36→36

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0727P)² + 0.3846P] where P = (F_o² + 2F_c²)/3
4600 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₂H₁₅NO₃S	V = 3459.7 (2) Å³
M_r = 373.41	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.2365 (5) Å	µ = 0.21 mm⁻¹
b = 9.2098 (4) Å	T = 295 K
c = 26.3865 (10) Å	0.20 × 0.16 × 0.14 mm

Data collection top

Bruker Kappa APEXII diffractometer	4600 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2928 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.971	R_int = 0.034
22287 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
4600 reflections	Δρ_min = −0.31 e Å⁻³
244 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.97004 (12)	0.1799 (2)	0.69244 (7)	0.0401 (4)
C2	1.04048 (14)	0.2223 (2)	0.72412 (9)	0.0533 (5)
H2	1.0934	0.2681	0.7111	0.064*
C3	1.03320 (16)	0.1971 (3)	0.77633 (9)	0.0604 (6)
H3	1.0817	0.2255	0.7978	0.072*
C4	0.95682 (15)	0.1322 (2)	0.79553 (8)	0.0534 (5)
H4	0.9527	0.1177	0.8303	0.064*
C5	0.88229 (13)	0.0854 (2)	0.76414 (7)	0.0422 (4)
C6	0.80228 (14)	0.0161 (2)	0.78423 (8)	0.0515 (5)
H6	0.7964	0.0055	0.8191	0.062*
C7	0.73420 (15)	−0.0349 (3)	0.75369 (8)	0.0593 (6)
H7	0.6819	−0.0804	0.7676	0.071*
C8	0.74173 (14)	−0.0200 (3)	0.70142 (9)	0.0559 (5)
H8	0.6950	−0.0579	0.6807	0.067*
C9	0.81644 (13)	0.0493 (2)	0.68008 (7)	0.0463 (5)
H9	0.8197	0.0595	0.6451	0.056*
C10	0.88882 (11)	0.1055 (2)	0.71077 (6)	0.0380 (4)
C11	1.06625 (13)	0.0248 (2)	0.58490 (7)	0.0427 (4)
C12	1.10910 (12)	0.0642 (2)	0.53991 (7)	0.0399 (4)
C13	1.08949 (12)	0.1663 (2)	0.49984 (6)	0.0410 (4)
C14	1.01942 (14)	0.2671 (2)	0.49088 (7)	0.0484 (5)
H14	0.9690	0.2756	0.5131	0.058*
C15	1.02502 (17)	0.3552 (3)	0.44849 (8)	0.0625 (6)
H15	0.9786	0.4240	0.4423	0.075*
C16	1.0999 (2)	0.3407 (3)	0.41514 (8)	0.0716 (7)
H16	1.1027	0.4011	0.3869	0.086*
C17	1.16910 (19)	0.2414 (3)	0.42234 (8)	0.0677 (7)
H17	1.2180	0.2317	0.3992	0.081*
C18	1.16462 (14)	0.1546 (3)	0.46542 (7)	0.0520 (5)
C19	1.19433 (14)	−0.0056 (3)	0.52798 (8)	0.0541 (5)
C20	1.23384 (18)	−0.1090 (3)	0.55964 (10)	0.0730 (8)
H20	1.2903	−0.1537	0.5513	0.088*
C21	1.1879 (2)	−0.1435 (3)	0.60317 (11)	0.0749 (8)
H21	1.2137	−0.2129	0.6247	0.090*
C22	1.10310 (17)	−0.0774 (2)	0.61653 (8)	0.0588 (6)
H22	1.0724	−0.1026	0.6464	0.071*
N1	1.22599 (12)	0.0506 (2)	0.48255 (7)	0.0658 (6)
H1	1.2766	0.0244	0.4673	0.079*
O1	0.97919 (8)	0.08998 (15)	0.59681 (5)	0.0457 (3)
O2	1.06505 (11)	0.30915 (17)	0.62191 (5)	0.0598 (4)
O3	0.89333 (11)	0.30371 (18)	0.61460 (6)	0.0626 (4)
S1	0.97877 (3)	0.23577 (6)	0.628849 (18)	0.04546 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0447 (9)	0.0339 (10)	0.0415 (9)	−0.0010 (8)	0.0063 (7)	−0.0057 (7)
C2	0.0490 (11)	0.0476 (13)	0.0633 (12)	−0.0106 (9)	0.0029 (9)	−0.0084 (10)
C3	0.0636 (13)	0.0608 (16)	0.0568 (12)	−0.0069 (11)	−0.0150 (10)	−0.0117 (11)
C4	0.0691 (13)	0.0501 (13)	0.0410 (10)	0.0017 (11)	−0.0053 (9)	−0.0041 (9)
C5	0.0507 (10)	0.0343 (11)	0.0415 (9)	0.0051 (8)	0.0033 (8)	0.0004 (7)
C6	0.0607 (12)	0.0488 (13)	0.0452 (10)	0.0043 (10)	0.0121 (9)	0.0085 (9)
C7	0.0482 (12)	0.0624 (16)	0.0674 (14)	−0.0075 (10)	0.0138 (10)	0.0132 (11)
C8	0.0442 (11)	0.0612 (15)	0.0624 (12)	−0.0120 (10)	−0.0029 (9)	0.0051 (10)
C9	0.0447 (10)	0.0512 (13)	0.0432 (10)	−0.0032 (9)	0.0001 (8)	0.0022 (8)
C10	0.0389 (9)	0.0338 (10)	0.0414 (9)	0.0029 (8)	0.0046 (7)	−0.0014 (7)
C11	0.0463 (10)	0.0393 (11)	0.0426 (9)	−0.0011 (8)	−0.0025 (8)	−0.0088 (8)
C12	0.0386 (9)	0.0385 (11)	0.0425 (9)	−0.0004 (8)	−0.0005 (7)	−0.0118 (8)
C13	0.0425 (9)	0.0443 (12)	0.0362 (8)	−0.0069 (8)	0.0027 (7)	−0.0110 (8)
C14	0.0557 (11)	0.0483 (13)	0.0411 (10)	−0.0015 (10)	0.0005 (8)	−0.0048 (8)
C15	0.0870 (17)	0.0538 (15)	0.0466 (11)	−0.0035 (12)	−0.0115 (11)	−0.0014 (10)
C16	0.106 (2)	0.0670 (18)	0.0423 (11)	−0.0281 (16)	0.0004 (12)	−0.0027 (11)
C17	0.0813 (16)	0.0796 (19)	0.0423 (11)	−0.0303 (15)	0.0199 (11)	−0.0164 (11)
C18	0.0510 (11)	0.0589 (14)	0.0462 (10)	−0.0113 (10)	0.0086 (8)	−0.0190 (9)
C19	0.0454 (11)	0.0576 (14)	0.0594 (12)	0.0075 (10)	−0.0022 (9)	−0.0221 (10)
C20	0.0644 (15)	0.0709 (18)	0.0836 (17)	0.0301 (13)	−0.0190 (13)	−0.0302 (14)
C21	0.0970 (19)	0.0535 (16)	0.0741 (16)	0.0224 (14)	−0.0333 (15)	−0.0095 (12)
C22	0.0841 (16)	0.0438 (13)	0.0485 (11)	0.0015 (11)	−0.0115 (10)	−0.0025 (9)
N1	0.0471 (10)	0.0849 (16)	0.0656 (11)	0.0042 (10)	0.0176 (8)	−0.0262 (10)
O1	0.0445 (7)	0.0488 (9)	0.0439 (7)	−0.0075 (6)	0.0085 (5)	−0.0082 (6)
O2	0.0657 (10)	0.0492 (10)	0.0646 (9)	−0.0207 (8)	0.0269 (7)	−0.0099 (7)
O3	0.0674 (10)	0.0622 (11)	0.0582 (9)	0.0180 (8)	0.0182 (7)	0.0154 (7)
S1	0.0501 (3)	0.0403 (3)	0.0459 (3)	−0.0033 (2)	0.0158 (2)	−0.0008 (2)

Geometric parameters (Å, º) top

C1—C2	1.363 (3)	C12—C13	1.442 (3)
C1—C10	1.429 (2)	C13—C14	1.383 (3)
C1—S1	1.7594 (19)	C13—C18	1.407 (2)
C2—C3	1.401 (3)	C14—C15	1.384 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.340 (3)	C15—C16	1.388 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.413 (3)	C16—C17	1.358 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.409 (3)	C17—C18	1.391 (3)
C5—C10	1.424 (2)	C17—H17	0.9300
C6—C7	1.345 (3)	C18—N1	1.373 (3)
C6—H6	0.9300	C19—N1	1.381 (3)
C7—C8	1.390 (3)	C19—C20	1.386 (3)
C7—H7	0.9300	C20—C21	1.359 (4)
C8—C9	1.362 (3)	C20—H20	0.9300
C8—H8	0.9300	C21—C22	1.398 (3)
C9—C10	1.409 (2)	C21—H21	0.9300
C9—H9	0.9300	C22—H22	0.9300
C11—C22	1.363 (3)	N1—H1	0.8600
C11—C12	1.383 (3)	O1—S1	1.5867 (14)
C11—O1	1.413 (2)	O2—S1	1.4139 (15)
C12—C19	1.409 (3)	O3—S1	1.4186 (15)

C2—C1—C10	121.70 (18)	C18—C13—C12	106.01 (17)
C2—C1—S1	116.71 (15)	C13—C14—C15	119.3 (2)
C10—C1—S1	121.35 (13)	C13—C14—H14	120.3
C1—C2—C3	120.09 (19)	C15—C14—H14	120.3
C1—C2—H2	120.0	C14—C15—C16	120.0 (2)
C3—C2—H2	120.0	C14—C15—H15	120.0
C4—C3—C2	120.4 (2)	C16—C15—H15	120.0
C4—C3—H3	119.8	C17—C16—C15	122.2 (2)
C2—C3—H3	119.8	C17—C16—H16	118.9
C3—C4—C5	121.59 (19)	C15—C16—H16	118.9
C3—C4—H4	119.2	C16—C17—C18	117.9 (2)
C5—C4—H4	119.2	C16—C17—H17	121.0
C6—C5—C4	121.64 (18)	C18—C17—H17	121.0
C6—C5—C10	118.94 (17)	N1—C18—C17	129.9 (2)
C4—C5—C10	119.40 (17)	N1—C18—C13	108.96 (18)
C7—C6—C5	121.01 (19)	C17—C18—C13	121.2 (2)
C7—C6—H6	119.5	N1—C19—C20	130.4 (2)
C5—C6—H6	119.5	N1—C19—C12	107.7 (2)
C6—C7—C8	120.28 (19)	C20—C19—C12	121.9 (2)
C6—C7—H7	119.9	C21—C20—C19	118.3 (2)
C8—C7—H7	119.9	C21—C20—H20	120.8
C9—C8—C7	121.1 (2)	C19—C20—H20	120.8
C9—C8—H8	119.4	C20—C21—C22	121.8 (2)
C7—C8—H8	119.4	C20—C21—H21	119.1
C8—C9—C10	120.37 (18)	C22—C21—H21	119.1
C8—C9—H9	119.8	C11—C22—C21	118.6 (2)
C10—C9—H9	119.8	C11—C22—H22	120.7
C9—C10—C5	118.22 (16)	C21—C22—H22	120.7
C9—C10—C1	125.02 (16)	C18—N1—C19	109.83 (16)
C5—C10—C1	116.75 (16)	C18—N1—H1	125.1
C22—C11—C12	122.49 (19)	C19—N1—H1	125.1
C22—C11—O1	119.68 (18)	C11—O1—S1	118.79 (11)
C12—C11—O1	117.78 (17)	O2—S1—O3	119.98 (11)
C11—C12—C19	116.86 (19)	O2—S1—O1	109.40 (8)
C11—C12—C13	135.65 (17)	O3—S1—O1	103.61 (9)
C19—C12—C13	107.48 (17)	O2—S1—C1	108.93 (9)
C14—C13—C18	119.31 (19)	O3—S1—C1	108.73 (9)
C14—C13—C12	134.63 (16)	O1—S1—C1	105.14 (8)

C10—C1—C2—C3	−1.9 (3)	C15—C16—C17—C18	−1.5 (3)
S1—C1—C2—C3	172.46 (18)	C16—C17—C18—N1	−177.6 (2)
C1—C2—C3—C4	−0.5 (4)	C16—C17—C18—C13	1.6 (3)
C2—C3—C4—C5	1.0 (4)	C14—C13—C18—N1	178.73 (17)
C3—C4—C5—C6	179.5 (2)	C12—C13—C18—N1	0.9 (2)
C3—C4—C5—C10	0.9 (3)	C14—C13—C18—C17	−0.6 (3)
C4—C5—C6—C7	−176.4 (2)	C12—C13—C18—C17	−178.51 (18)
C10—C5—C6—C7	2.2 (3)	C11—C12—C19—N1	−178.93 (17)
C5—C6—C7—C8	0.0 (4)	C13—C12—C19—N1	−0.1 (2)
C6—C7—C8—C9	−1.6 (4)	C11—C12—C19—C20	0.0 (3)
C7—C8—C9—C10	1.0 (3)	C13—C12—C19—C20	178.8 (2)
C8—C9—C10—C5	1.2 (3)	N1—C19—C20—C21	179.0 (2)
C8—C9—C10—C1	−179.92 (19)	C12—C19—C20—C21	0.3 (4)
C6—C5—C10—C9	−2.7 (3)	C19—C20—C21—C22	−0.2 (4)
C4—C5—C10—C9	175.89 (18)	C12—C11—C22—C21	0.7 (3)
C6—C5—C10—C1	178.26 (17)	O1—C11—C22—C21	178.11 (18)
C4—C5—C10—C1	−3.1 (3)	C20—C21—C22—C11	−0.3 (4)
C2—C1—C10—C9	−175.26 (19)	C17—C18—N1—C19	178.3 (2)
S1—C1—C10—C9	10.6 (3)	C13—C18—N1—C19	−1.0 (2)
C2—C1—C10—C5	3.7 (3)	C20—C19—N1—C18	−178.2 (2)
S1—C1—C10—C5	−170.45 (14)	C12—C19—N1—C18	0.6 (2)
C22—C11—C12—C19	−0.6 (3)	C22—C11—O1—S1	91.6 (2)
O1—C11—C12—C19	−177.99 (16)	C12—C11—O1—S1	−90.91 (17)
C22—C11—C12—C13	−179.0 (2)	C11—O1—S1—O2	25.23 (16)
O1—C11—C12—C13	3.6 (3)	C11—O1—S1—O3	154.30 (13)
C11—C12—C13—C14	0.7 (4)	C11—O1—S1—C1	−91.63 (14)
C19—C12—C13—C14	−177.9 (2)	C2—C1—S1—O2	4.21 (19)
C11—C12—C13—C18	178.1 (2)	C10—C1—S1—O2	178.61 (15)
C19—C12—C13—C18	−0.5 (2)	C2—C1—S1—O3	−128.18 (17)
C18—C13—C14—C15	−0.6 (3)	C10—C1—S1—O3	46.22 (18)
C12—C13—C14—C15	176.6 (2)	C2—C1—S1—O1	121.38 (16)
C13—C14—C15—C16	0.8 (3)	C10—C1—S1—O1	−64.22 (16)
C14—C15—C16—C17	0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.42	2.835 (3)	107
C8—H8···O3ⁱ	0.93	2.50	3.403 (3)	164
C17—H17···O3ⁱⁱ	0.93	2.54	3.364 (3)	147

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₅NO₃S
M_r	373.41
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	14.2365 (5), 9.2098 (4), 26.3865 (10)
V (Å³)	3459.7 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.20 × 0.16 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.959, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	22287, 4600, 2928
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.683

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.144, 1.06
No. of reflections	4600
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.31

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.42	2.835 (3)	107
C8—H8···O3ⁱ	0.93	2.50	3.403 (3)	164
C17—H17···O3ⁱⁱ	0.93	2.54	3.364 (3)	147

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x+1/2, −y+1/2, −z+1.

Acknowledgements

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Chennai, for the data collection.

References

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hosomi, H., Ohba, S. & Ito, Y. (2000). Acta Cryst. C56, e144–e146. CSD CrossRef CAS IUCr Journals Google Scholar
Itoigawa, M., Kashiwada, Y., Ito, C., Furukawa, H., Tachibana, Y., Bastow, K. F. & Lee, K. H. (2000). J. Nat. Prod. 63, 893–897. Web of Science CrossRef PubMed CAS Google Scholar
Manivannan, V., Vembu, N., Nallu, M., Sivakumar, K. & Fronczek, F. R. (2005). Acta Cryst. E61, o528–o530. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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
Tachibana, Y., Kikuzaki, H., Lajis, N. H. & Nakatani, N. (2001). J. Agric. Food Chem. 49, 5589–5594. Web of Science CrossRef PubMed CAS Google Scholar