2,4-Dinitro-1-naphthyl 4-toluene­sulfonate

Ramachandran, G.; Kanakam, C.C.; Manivannan, V.

doi:10.1107/S1600536808010052

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o873

doi:10.1107/S1600536808010052

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2,4-Dinitro-1-naphthyl 4-toluenesulfonate

G. Ramachandran,^a Charles Christopher Kanakam ^a and V. Manivannan ^b ^*

^aDepartment of Chemistry, Valliammai Engineering College, Chennai, India, and ^bDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 8 April 2008; accepted 12 April 2008; online 18 April 2008)

In the title compound, C₁₇H₁₂N₂O₇S, the dihedral angle between the benzene ring and the naphthyl plane is 26.34 (6)°. The nitro groups make dihedral angles of 40.09 (4) and 37.05 (3)° with the naphthyl plane. In the crystal structure, weak intra- and intermolecular C—H⋯O interactions are observed.

Related literature

For biological activity, see: Yachi et al. (1989 ). For the structure of closely related compounds, see: Manivannan et al. (2005a ,b ).

Experimental

Crystal data

C₁₇H₁₂N₂O₇S
M_r = 388.35
Monoclinic, P 2₁ /c
a = 13.071 (2) Å
b = 7.8660 (13) Å
c = 16.595 (3) Å
β = 90.757 (3)°
V = 1706.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 295 (2) K
0.36 × 0.25 × 0.13 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.920, T_max = 0.970
12222 measured reflections
3116 independent reflections
2291 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.104
S = 1.02
3116 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5	0.93	2.55	3.194 (3)	127
C14—H14⋯O7	0.93	2.33	2.895 (3)	119
C17—H17⋯O3	0.93	2.48	2.798 (3)	100
C10—H10⋯O1ⁱ	0.93	2.45	3.327 (3)	157
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); 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/S1600536808010052/is2287sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010052/is2287Isup2.hkl

checkCIF report

Comment top

Aromatic sulfonates are used in monitoring the merging of lipids (Yachi et al., 1989). The geometric parameters in the title compound agree with the reported values of similar structures (Manivannan et al., 2005a,b). The dihedral angle between the mean planes of phenyl and naphthyl rings is 26.34 (6)°. The planes N1/O5/O4 and N2/O6/O7 make the dihedral angles of 40.09 (4) and 37.05 (3)°, respectively, with the naphthyl ring. The torsion angles [O1—S1—C1—C6 = -17.0 (2)° and O2—S1—C1—C2 = 27.9 (2)°] indicate a syn conformation of the sulfonyl moiety.

In addition to this, because of the presence of highly electron attracting nitro groups, there are strong dipole-dipole attractions between different molecules in the lattice arrangement. The nitro group substituted naphthylring, which is electron deficient is found to be lying over the electron rich tolyl benzene ring of another molecule in the lattice. This leads to a sort of charge transfer complex.

The enhanced stability of this compound and larger stability of the lattice when compared to other sulfonates reported already, is supported by thermoanalytic studies. This compound is having higher density, melting point and higher lattice energy when compared to others. Another interesting property of this compound is that it possesses antibacterial activity almost equivalent to those of antibiotics. This is attributed to the elongation of the S—O (S1—O3) bond in –S—O–naphthyl ring such that the dissociation to naphthoxy moiety is facilitated. The facile formation of the naphthoxy radical is further supported by the high intensity peak for this specy in the Mass spectra. Kinetic studies also indicate that the rate of hydrolysis (rate of cleavage of the –S—O– bond) is very high when compared to other toluene sulfonates reported already.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing of (I) (Fig. 2) is stabilized by weak intermolecular C—H···O interactions.

Related literature top

For biological activity, see: Yachi et al. (1989). For the structure of a closely related compound, see: Manivannan et al. (2005a,b)

Experimental top

Calculated quantity of (10 mmol) of alpha naphthol was dissolved in hot con. sulfuric acid (10 ml) and heated for 10 minutes over a water bath to get disulfonic acid. To this was added (10 ml) of fuming nitric acid in small quantity at a time with stirring. After the addition was over the reaction mixture was kept aside for an hour. It was poured into crushed ice with stirring. The precipitate was filtered, washed with cold water, dried and recrystallized from rectified spirit.

A solution of the above 2,4-dinitronaphthol and triethylamine in acetone was treated with sulfonyl chloride in acetone. This was left as such overnight. The solvent was evaporated and the residue was washed with triethylamine solution. The crude product was recrystallized from ethanol to get diffraction quality crystal of 2,4-dintro-1-naphthyl-4-toluene sulfonate.

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.

2,4-Dinitro-1-naphthyl 4-toluenesulfonate top

Crystal data top

C₁₇H₁₂N₂O₇S	F(000) = 800
M_r = 388.35	D_x = 1.512 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4023 reflections
a = 13.071 (2) Å	θ = 1.8–25.2°
b = 7.8660 (13) Å	µ = 0.24 mm⁻¹
c = 16.595 (3) Å	T = 295 K
β = 90.757 (3)°	Block, colourless
V = 1706.0 (5) Å³	0.36 × 0.25 × 0.13 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	3116 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 25.4°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.920, T_max = 0.970	k = −9→9
12222 measured reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0486P)² + 0.4765P] where P = (F_o² + 2F_c²)/3
3116 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₇H₁₂N₂O₇S	V = 1706.0 (5) Å³
M_r = 388.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.071 (2) Å	µ = 0.24 mm⁻¹
b = 7.8660 (13) Å	T = 295 K
c = 16.595 (3) Å	0.36 × 0.25 × 0.13 mm
β = 90.757 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	3116 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2291 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.970	R_int = 0.031
12222 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
3116 reflections	Δρ_min = −0.23 e Å⁻³
245 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.75961 (5)	0.14928 (8)	0.91732 (3)	0.04636 (19)
N2	0.47400 (18)	0.4441 (3)	1.21402 (12)	0.0509 (5)
N1	0.77051 (15)	0.1383 (3)	1.12836 (11)	0.0511 (5)
C8	0.62399 (17)	0.1694 (3)	1.03092 (12)	0.0379 (5)
C9	0.66905 (17)	0.2018 (3)	1.10432 (13)	0.0396 (5)
C10	0.61838 (18)	0.2985 (3)	1.16206 (13)	0.0418 (5)
H10	0.6505	0.3244	1.2109	0.050*
C11	0.52268 (18)	0.3540 (3)	1.14659 (12)	0.0394 (5)
C12	0.47017 (17)	0.3258 (3)	1.07210 (12)	0.0383 (5)
C13	0.52516 (16)	0.2336 (3)	1.01249 (12)	0.0366 (5)
C14	0.37180 (18)	0.3875 (3)	1.05167 (14)	0.0462 (6)
H14	0.3347	0.4476	1.0897	0.055*
C15	0.33082 (18)	0.3603 (3)	0.97732 (15)	0.0502 (6)
H15	0.2658	0.4016	0.9651	0.060*
C16	0.38494 (19)	0.2709 (3)	0.91879 (15)	0.0494 (6)
H16	0.3558	0.2542	0.8680	0.059*
C17	0.47966 (18)	0.2082 (3)	0.93546 (13)	0.0421 (5)
H17	0.5148	0.1484	0.8962	0.051*
C1	0.82025 (17)	−0.0380 (3)	0.88993 (14)	0.0467 (6)
C4	0.9179 (2)	−0.3362 (4)	0.84598 (18)	0.0639 (7)
C2	0.8941 (2)	−0.1075 (4)	0.94025 (17)	0.0660 (8)
H2	0.9113	−0.0548	0.9888	0.079*
C3	0.9421 (2)	−0.2557 (4)	0.91778 (19)	0.0744 (9)
H3	0.9918	−0.3026	0.9516	0.089*
C6	0.7943 (2)	−0.1167 (4)	0.81845 (15)	0.0583 (7)
H6	0.7439	−0.0708	0.7848	0.070*
C5	0.8437 (2)	−0.2639 (4)	0.79741 (18)	0.0671 (8)
H5	0.8264	−0.3163	0.7489	0.081*
C7	0.9719 (2)	−0.4974 (4)	0.8216 (2)	0.0947 (11)
H7A	1.0222	−0.4715	0.7818	0.142*
H7B	0.9230	−0.5762	0.7995	0.142*
H7C	1.0049	−0.5470	0.8680	0.142*
O1	0.70983 (14)	0.2246 (2)	0.84979 (9)	0.0613 (5)
O2	0.82266 (13)	0.2523 (2)	0.96766 (10)	0.0584 (5)
O3	0.67103 (11)	0.06829 (18)	0.97377 (8)	0.0431 (4)
O4	0.82359 (15)	0.2326 (3)	1.16921 (12)	0.0810 (6)
O5	0.79512 (14)	−0.0046 (3)	1.10830 (11)	0.0644 (5)
O6	0.53013 (16)	0.5300 (3)	1.25734 (11)	0.0738 (6)
O7	0.38300 (16)	0.4246 (3)	1.22514 (11)	0.0713 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0527 (4)	0.0503 (4)	0.0362 (3)	−0.0065 (3)	0.0072 (3)	−0.0017 (3)
N2	0.0698 (15)	0.0451 (12)	0.0382 (11)	0.0054 (11)	0.0093 (11)	0.0005 (9)
N1	0.0516 (13)	0.0644 (15)	0.0372 (11)	−0.0010 (12)	−0.0001 (9)	0.0005 (11)
C8	0.0473 (13)	0.0341 (12)	0.0324 (11)	−0.0068 (10)	0.0055 (10)	0.0000 (9)
C9	0.0447 (13)	0.0384 (12)	0.0358 (12)	−0.0044 (10)	0.0001 (10)	0.0041 (10)
C10	0.0582 (15)	0.0389 (12)	0.0285 (11)	−0.0081 (11)	0.0000 (10)	0.0002 (10)
C11	0.0532 (14)	0.0313 (11)	0.0338 (11)	−0.0022 (10)	0.0087 (10)	0.0017 (9)
C12	0.0485 (13)	0.0300 (11)	0.0364 (12)	−0.0069 (10)	0.0043 (10)	0.0048 (9)
C13	0.0446 (13)	0.0309 (11)	0.0344 (11)	−0.0090 (10)	0.0013 (10)	0.0028 (9)
C14	0.0521 (14)	0.0383 (13)	0.0485 (14)	−0.0017 (11)	0.0078 (11)	0.0060 (11)
C15	0.0448 (14)	0.0490 (14)	0.0566 (15)	−0.0038 (11)	−0.0045 (12)	0.0106 (13)
C16	0.0564 (15)	0.0488 (14)	0.0427 (13)	−0.0126 (12)	−0.0088 (12)	0.0061 (11)
C17	0.0517 (14)	0.0394 (12)	0.0352 (12)	−0.0088 (11)	0.0001 (10)	0.0011 (10)
C1	0.0405 (13)	0.0579 (15)	0.0420 (13)	−0.0071 (11)	0.0076 (11)	−0.0057 (11)
C4	0.0484 (15)	0.0653 (18)	0.078 (2)	−0.0063 (14)	0.0158 (14)	−0.0175 (16)
C2	0.0531 (16)	0.087 (2)	0.0578 (16)	0.0052 (15)	−0.0036 (13)	−0.0213 (15)
C3	0.0555 (17)	0.089 (2)	0.079 (2)	0.0164 (16)	−0.0041 (15)	−0.0103 (18)
C6	0.0564 (16)	0.0690 (18)	0.0496 (15)	0.0026 (14)	0.0009 (12)	−0.0111 (13)
C5	0.0612 (17)	0.076 (2)	0.0641 (18)	−0.0081 (15)	0.0040 (14)	−0.0264 (16)
C7	0.075 (2)	0.077 (2)	0.133 (3)	0.0067 (18)	0.022 (2)	−0.028 (2)
O1	0.0794 (12)	0.0660 (12)	0.0387 (9)	0.0039 (9)	0.0059 (9)	0.0086 (8)
O2	0.0630 (11)	0.0584 (11)	0.0539 (10)	−0.0189 (9)	0.0080 (8)	−0.0100 (9)
O3	0.0514 (9)	0.0404 (9)	0.0377 (8)	−0.0031 (7)	0.0076 (7)	−0.0054 (7)
O4	0.0617 (12)	0.1075 (17)	0.0734 (13)	−0.0049 (11)	−0.0180 (11)	−0.0267 (12)
O5	0.0660 (12)	0.0632 (12)	0.0640 (12)	0.0149 (10)	−0.0005 (9)	0.0042 (10)
O6	0.0898 (15)	0.0723 (13)	0.0593 (12)	0.0021 (11)	0.0009 (11)	−0.0308 (10)
O7	0.0664 (13)	0.0885 (15)	0.0596 (12)	0.0031 (11)	0.0229 (10)	−0.0065 (10)

Geometric parameters (Å, º) top

S1—O1	1.4179 (17)	C14—H14	0.9300
S1—O2	1.4196 (16)	C15—C16	1.399 (3)
S1—O3	1.6287 (16)	C15—H15	0.9300
S1—C1	1.736 (3)	C16—C17	1.358 (3)
N2—O7	1.216 (3)	C16—H16	0.9300
N2—O6	1.224 (3)	C17—H17	0.9300
N2—C11	1.476 (3)	C1—C6	1.377 (3)
N1—O4	1.216 (3)	C1—C2	1.381 (3)
N1—O5	1.216 (3)	C4—C5	1.376 (4)
N1—C9	1.467 (3)	C4—C3	1.382 (4)
C8—C9	1.370 (3)	C4—C7	1.509 (4)
C8—O3	1.388 (2)	C2—C3	1.378 (4)
C8—C13	1.416 (3)	C2—H2	0.9300
C9—C10	1.397 (3)	C3—H3	0.9300
C10—C11	1.346 (3)	C6—C5	1.373 (4)
C10—H10	0.9300	C6—H6	0.9300
C11—C12	1.423 (3)	C5—H5	0.9300
C12—C14	1.411 (3)	C7—H7A	0.9600
C12—C13	1.429 (3)	C7—H7B	0.9600
C13—C17	1.417 (3)	C7—H7C	0.9600
C14—C15	1.356 (3)

O1—S1—O2	118.91 (11)	C14—C15—H15	119.5
O1—S1—O3	107.20 (10)	C16—C15—H15	119.5
O2—S1—O3	107.24 (9)	C17—C16—C15	120.6 (2)
O1—S1—C1	110.71 (11)	C17—C16—H16	119.7
O2—S1—C1	112.01 (11)	C15—C16—H16	119.7
O3—S1—C1	98.58 (10)	C16—C17—C13	120.2 (2)
O7—N2—O6	124.1 (2)	C16—C17—H17	119.9
O7—N2—C11	119.1 (2)	C13—C17—H17	119.9
O6—N2—C11	116.7 (2)	C6—C1—C2	120.4 (2)
O4—N1—O5	124.4 (2)	C6—C1—S1	119.9 (2)
O4—N1—C9	116.8 (2)	C2—C1—S1	119.70 (19)
O5—N1—C9	118.8 (2)	C5—C4—C3	117.8 (3)
C9—C8—O3	121.7 (2)	C5—C4—C7	121.3 (3)
C9—C8—C13	120.4 (2)	C3—C4—C7	120.9 (3)
O3—C8—C13	117.89 (18)	C3—C2—C1	119.2 (3)
C8—C9—C10	120.6 (2)	C3—C2—H2	120.4
C8—C9—N1	123.7 (2)	C1—C2—H2	120.4
C10—C9—N1	115.71 (19)	C2—C3—C4	121.4 (3)
C11—C10—C9	119.6 (2)	C2—C3—H3	119.3
C11—C10—H10	120.2	C4—C3—H3	119.3
C9—C10—H10	120.2	C5—C6—C1	119.2 (3)
C10—C11—C12	123.4 (2)	C5—C6—H6	120.4
C10—C11—N2	114.8 (2)	C1—C6—H6	120.4
C12—C11—N2	121.7 (2)	C6—C5—C4	122.0 (3)
C14—C12—C11	125.6 (2)	C6—C5—H5	119.0
C14—C12—C13	118.3 (2)	C4—C5—H5	119.0
C11—C12—C13	116.1 (2)	C4—C7—H7A	109.5
C8—C13—C17	121.0 (2)	C4—C7—H7B	109.5
C8—C13—C12	119.83 (19)	H7A—C7—H7B	109.5
C17—C13—C12	119.1 (2)	C4—C7—H7C	109.5
C15—C14—C12	120.8 (2)	H7A—C7—H7C	109.5
C15—C14—H14	119.6	H7B—C7—H7C	109.5
C12—C14—H14	119.6	C8—O3—S1	119.58 (13)
C14—C15—C16	120.9 (2)

O3—C8—C9—C10	−177.46 (19)	C11—C12—C14—C15	176.7 (2)
C13—C8—C9—C10	0.0 (3)	C13—C12—C14—C15	−0.2 (3)
O3—C8—C9—N1	1.8 (3)	C12—C14—C15—C16	−0.2 (3)
C13—C8—C9—N1	179.21 (19)	C14—C15—C16—C17	0.5 (3)
O4—N1—C9—C8	143.2 (2)	C15—C16—C17—C13	−0.3 (3)
O5—N1—C9—C8	−38.6 (3)	C8—C13—C17—C16	−179.9 (2)
O4—N1—C9—C10	−37.5 (3)	C12—C13—C17—C16	−0.1 (3)
O5—N1—C9—C10	140.7 (2)	O1—S1—C1—C6	−17.0 (2)
C8—C9—C10—C11	2.9 (3)	O2—S1—C1—C6	−152.30 (19)
N1—C9—C10—C11	−176.4 (2)	O3—S1—C1—C6	95.1 (2)
C9—C10—C11—C12	−2.8 (3)	O1—S1—C1—C2	163.2 (2)
C9—C10—C11—N2	175.77 (19)	O2—S1—C1—C2	27.9 (2)
O7—N2—C11—C10	−143.1 (2)	O3—S1—C1—C2	−84.7 (2)
O6—N2—C11—C10	34.3 (3)	C6—C1—C2—C3	0.5 (4)
O7—N2—C11—C12	35.5 (3)	S1—C1—C2—C3	−179.7 (2)
O6—N2—C11—C12	−147.1 (2)	C1—C2—C3—C4	0.0 (5)
C10—C11—C12—C14	−177.1 (2)	C5—C4—C3—C2	−0.3 (4)
N2—C11—C12—C14	4.5 (3)	C7—C4—C3—C2	179.2 (3)
C10—C11—C12—C13	−0.1 (3)	C2—C1—C6—C5	−0.8 (4)
N2—C11—C12—C13	−178.59 (19)	S1—C1—C6—C5	179.4 (2)
C9—C8—C13—C17	176.87 (19)	C1—C6—C5—C4	0.6 (4)
O3—C8—C13—C17	−5.6 (3)	C3—C4—C5—C6	0.0 (4)
C9—C8—C13—C12	−2.9 (3)	C7—C4—C5—C6	−179.5 (3)
O3—C8—C13—C12	174.60 (17)	C9—C8—O3—S1	−80.6 (2)
C14—C12—C13—C8	−179.86 (19)	C13—C8—O3—S1	101.93 (19)
C11—C12—C13—C8	3.0 (3)	O1—S1—O3—C8	−86.68 (17)
C14—C12—C13—C17	0.3 (3)	O2—S1—O3—C8	42.07 (17)
C11—C12—C13—C17	−176.83 (19)	C1—S1—O3—C8	158.41 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5	0.93	2.55	3.194 (3)	127
C14—H14···O7	0.93	2.33	2.895 (3)	119
C17—H17···O3	0.93	2.48	2.798 (3)	100
C10—H10···O1ⁱ	0.93	2.45	3.327 (3)	157

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂N₂O₇S
M_r	388.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	13.071 (2), 7.8660 (13), 16.595 (3)
β (°)	90.757 (3)
V (Å³)	1706.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.36 × 0.25 × 0.13

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.920, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	12222, 3116, 2291
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.104, 1.02
No. of reflections	3116
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.23

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···O5	0.93	2.55	3.194 (3)	127
C14—H14···O7	0.93	2.33	2.895 (3)	119
C17—H17···O3	0.93	2.48	2.798 (3)	100
C10—H10···O1ⁱ	0.93	2.45	3.327 (3)	157

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The authors acknowledge Professor T. N. Guru Row and Dr Vijay Thiruvenkatam, Indian Institute of Science, Bangalore, India, for the data collection.

References

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Manivannan, V., Vembu, N., Nallu, M., Sivakumar, K. & Fronczek, F. R. (2005a). Acta Cryst. E61, o239–o241. Web of Science CSD CrossRef IUCr Journals Google Scholar
Manivannan, V., Vembu, N., Nallu, M., Sivakumar, K. & Fronczek, F. R. (2005b). Acta Cryst. E61, o242–o244. 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
Yachi, K., Sugiyama, Y., Sawada, Y., Iga, T., Ikeda, Y., Toda, G. & Hananon, M. (1989). Biochim. Biophys. Acta, 978, 1–7. CrossRef CAS PubMed Web of Science Google Scholar