Ethyl 2-[N-(2-formyl­phen­yl)benzene­sulfonamido]acetate

Ranjith, S.; Sugumar, P.; Sureshbabu, R.; Mohanakrishnan, A.K.; Ponnuswamy, M.N.

doi:10.1107/S160053680900292X

organic compounds

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Volume 65| Part 3| March 2009| Page o483

doi:10.1107/S160053680900292X

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Ethyl 2-[N-(2-formylphenyl)benzenesulfonamido]acetate

S. Ranjith,^a P. Sugumar,^a R. Sureshbabu,^b A. K. Mohanakrishnan ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 1 December 2008; accepted 23 January 2009; online 6 February 2009)

In the molecule of the title compound, C₁₇H₁₇NO₅S, the two aromatic rings are oriented at an angle of 30.13 (10)°. The ethyl acetate group assumes an extended conformation. Molecules are linked into C(7) chains running along the a axis by intermolecular C—H⋯O hydrogen bonds, and the chains are crosslinked via C—H⋯π interactions, with the sulfonyl-bound phenyl ring acting as an acceptor.

Related literature

For the activities of sulfonamides, see: Krishnaiah et al. (1995 ); Dupont et al. (1978 ); Sethu Sankar et al. (2002 ). For related literature, see: Bassindale (1984 ).

Experimental

Crystal data

C₁₇H₁₇NO₅S
M_r = 347.38
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.3512 (6) Å
b = 11.7820 (6) Å
c = 12.8045 (6) Å
V = 1712.47 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 (2) K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.948, T_max = 0.960
13978 measured reflections
5831 independent reflections
3738 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.109
S = 1.02
5831 reflections
218 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), with 2533 Friedel pairs
Flack parameter: 0.04 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4ⁱ	0.93	2.57	3.220 (2)	127
C16—H16B⋯Cg1ⁱⁱ	0.97	2.75	3.615 (2)	150
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900292X/ci2739sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900292X/ci2739Isup2.hkl

checkCIF report

Comment top

The title compound is a potential intermediate for the synthesis of 2-alkylbenzoic acid and exhibits insecticidal, germicidal and antimicrobial activities (Krishnaiah et al., 1995; Dupont et al., 1978). The sulfonamides inhibit the growth of bacterial organism and are also useful for treating urinary and gastrointestinal infections (Sethu Sankar et al., 2002).

Atom S1 has a distorted tetrahedral configuration. The widening of angle O2—S1—O3 [120.46 (10)°] and narrowing of angle C8—S1—N1 [105.97 (8)°] from the ideal tetrahedral value are attributed to the Thorpe-Ingold effect (Bassindale, 1984). The two phenyl rings are oriented at an angle of 30.13 (10)°. The ethylacetate moiety assumes an extended conformation as can be seen from torsion angles C14—C15—O5—C16 of 178.12 (15)° and C15—O5—C16—C17 of 173.12 (19)°.

The molecules are linked into C(7) chains running along the a axis by C—H···O hydrogen bonding (Table 1). In addition C—H···π interactions (Table 1) with C8–C13 ring (centroid Cg1) as an acceptor is observed.

Related literature top

For the activities of sulfonamides, see: Krishnaiah et al. (1995); Dupont et al. (1978); Sethu Sankar et al. (2002). For related literature, see: Bassindale (1984).

Experimental top

2-(Benzenesulfonylamino)benzaldehyde (2 mmol) was added with ethyl bromoacetate (2.2 mmol) in the presence of potassium carbonate (4.7 mmol) and dimethyl acetamide (15 ml). The mixture was stirred at room temperature for 6 h. The reaction mass was poured into crushed ice (50 g) containing 4 to 5 drops of concentrated HCl and extracted with ethyl acetate. The product was obtained by column chromatography (hexane-ethyl acetate 9:1). The removal of the solvent followed by column chromatography of the residue (ethyl acetate) afforded white crystalline solid (yield 25%, m.p. 381-383 K). Single crystals suitable for the X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution of the title compound at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004; 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, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Molecular packing in the title compound, viewed down the b axis. Dashed lines represent hydrogen bonds.

Ethyl 2-[N-(2-formylphenyl)benzenesulfonamido]acetate top

Crystal data top

C₁₇H₁₇NO₅S	F(000) = 728
M_r = 347.38	D_x = 1.347 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5831 reflections
a = 11.3512 (6) Å	θ = 2.4–31.9°
b = 11.7820 (6) Å	µ = 0.22 mm⁻¹
c = 12.8045 (6) Å	T = 293 K
V = 1712.47 (15) Å³	Block, white
Z = 4	0.25 × 0.22 × 0.19 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5831 independent reflections
Radiation source: fine-focus sealed tube	3738 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scans	θ_max = 31.9°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.948, T_max = 0.960	k = −17→14
13978 measured reflections	l = −19→17

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-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0543P)² + 0.0353P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5831 reflections	Δρ_max = 0.29 e Å⁻³
218 parameters	Δρ_min = −0.25 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2533 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (6)

Crystal data top

C₁₇H₁₇NO₅S	V = 1712.47 (15) Å³
M_r = 347.38	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.3512 (6) Å	µ = 0.22 mm⁻¹
b = 11.7820 (6) Å	T = 293 K
c = 12.8045 (6) Å	0.25 × 0.22 × 0.19 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5831 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3738 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.960	R_int = 0.024
13978 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.109	Δρ_max = 0.29 e Å⁻³
S = 1.02	Δρ_min = −0.25 e Å⁻³
5831 reflections	Absolute structure: Flack (1983), 2533 Friedel pairs
218 parameters	Absolute structure parameter: 0.04 (6)
2 restraints

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	0.6483 (2)	0.49883 (17)	0.57621 (17)	0.0725 (5)
H1	0.6643	0.5535	0.6266	0.087*
C2	0.7343 (2)	0.46784 (15)	0.50573 (16)	0.0599 (4)
H2	0.8076	0.5030	0.5079	0.072*
C3	0.71222 (15)	0.38413 (13)	0.43117 (13)	0.0455 (4)
C4	0.60095 (14)	0.33360 (13)	0.42953 (13)	0.0439 (4)
C5	0.51443 (18)	0.36705 (17)	0.49915 (16)	0.0601 (5)
H5	0.4401	0.3341	0.4965	0.072*
C6	0.5388 (2)	0.44896 (19)	0.57199 (17)	0.0749 (5)
H6	0.4807	0.4711	0.6190	0.090*
C7	0.80521 (16)	0.35124 (16)	0.35744 (16)	0.0541 (4)
H7	0.7922	0.2885	0.3149	0.065*
C8	0.38129 (14)	0.27847 (14)	0.23805 (13)	0.0441 (3)
C9	0.31891 (18)	0.18498 (16)	0.20531 (16)	0.0567 (5)
H9	0.3582	0.1211	0.1807	0.068*
C10	0.1974 (2)	0.18686 (19)	0.20932 (19)	0.0706 (6)
H10	0.1544	0.1243	0.1867	0.085*
C11	0.14047 (18)	0.2805 (2)	0.24649 (18)	0.0712 (6)
H11	0.0586	0.2811	0.2499	0.085*
C12	0.20264 (19)	0.37386 (19)	0.27891 (17)	0.0684 (6)
H12	0.1627	0.4371	0.3041	0.082*
C13	0.32368 (18)	0.37453 (15)	0.27450 (15)	0.0554 (4)
H13	0.3661	0.4381	0.2955	0.066*
C14	0.54399 (17)	0.13373 (14)	0.39808 (16)	0.0540 (4)
H14A	0.5015	0.0911	0.3453	0.065*
H14B	0.4919	0.1444	0.4573	0.065*
C15	0.65056 (17)	0.06720 (14)	0.43210 (14)	0.0493 (4)
C16	0.7056 (2)	−0.10263 (15)	0.51699 (17)	0.0665 (6)
H16A	0.7630	−0.0624	0.5592	0.080*
H16B	0.7459	−0.1367	0.4580	0.080*
C17	0.6456 (3)	−0.1912 (2)	0.5801 (3)	0.1116 (11)
H17A	0.6075	−0.1565	0.6389	0.167*
H17B	0.7026	−0.2453	0.6044	0.167*
H17C	0.5879	−0.2292	0.5378	0.167*
N1	0.57707 (12)	0.24388 (11)	0.35598 (11)	0.0472 (3)
O1	0.89698 (13)	0.40067 (14)	0.34903 (16)	0.0853 (5)
O2	0.58147 (12)	0.38549 (11)	0.21580 (11)	0.0643 (4)
O3	0.57026 (13)	0.18131 (14)	0.17302 (12)	0.0758 (4)
O4	0.75012 (13)	0.09354 (12)	0.41701 (15)	0.0768 (5)
O5	0.61509 (11)	−0.02585 (10)	0.48124 (11)	0.0592 (3)
S1	0.53632 (4)	0.27483 (4)	0.23629 (3)	0.04953 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.1104 (14)	0.0522 (10)	0.0549 (11)	0.0040 (10)	−0.0043 (10)	−0.0089 (9)
C2	0.0728 (13)	0.0477 (9)	0.0593 (10)	−0.0020 (9)	−0.0145 (8)	0.0032 (8)
C3	0.0469 (9)	0.0410 (8)	0.0484 (8)	0.0041 (7)	−0.0058 (7)	0.0073 (7)
C4	0.0445 (9)	0.0421 (8)	0.0451 (8)	0.0043 (7)	−0.0039 (7)	0.0069 (7)
C5	0.0544 (11)	0.0629 (11)	0.0629 (11)	0.0072 (9)	0.0080 (9)	0.0063 (9)
C6	0.0906 (13)	0.0731 (12)	0.0611 (11)	0.0163 (12)	0.0180 (13)	−0.0021 (10)
C7	0.0456 (10)	0.0544 (10)	0.0624 (11)	0.0023 (9)	−0.0015 (8)	0.0070 (8)
C8	0.0436 (8)	0.0493 (8)	0.0395 (7)	0.0012 (7)	−0.0038 (6)	−0.0011 (8)
C9	0.0585 (12)	0.0463 (9)	0.0653 (12)	0.0026 (9)	−0.0056 (9)	−0.0044 (8)
C10	0.0562 (12)	0.0676 (12)	0.0879 (15)	−0.0114 (11)	−0.0087 (11)	0.0002 (11)
C11	0.0472 (10)	0.0903 (16)	0.0763 (14)	0.0025 (11)	0.0026 (10)	−0.0014 (13)
C12	0.0615 (12)	0.0784 (14)	0.0653 (12)	0.0238 (11)	−0.0038 (10)	−0.0146 (11)
C13	0.0579 (11)	0.0552 (10)	0.0532 (9)	0.0078 (8)	−0.0074 (8)	−0.0093 (8)
C14	0.0459 (10)	0.0443 (8)	0.0719 (10)	−0.0015 (8)	−0.0038 (9)	0.0079 (8)
C15	0.0518 (10)	0.0414 (8)	0.0546 (9)	−0.0014 (8)	−0.0071 (8)	−0.0024 (8)
C16	0.0828 (15)	0.0493 (9)	0.0674 (12)	0.0114 (10)	−0.0237 (11)	0.0029 (9)
C17	0.133 (3)	0.0727 (16)	0.129 (3)	−0.0176 (16)	−0.048 (2)	0.0442 (17)
N1	0.0434 (7)	0.0416 (7)	0.0567 (8)	−0.0004 (6)	−0.0075 (6)	0.0048 (6)
O1	0.0493 (8)	0.0925 (11)	0.1142 (13)	−0.0147 (8)	0.0139 (8)	−0.0077 (10)
O2	0.0613 (8)	0.0729 (9)	0.0587 (7)	−0.0149 (7)	−0.0028 (6)	0.0174 (7)
O3	0.0589 (9)	0.0942 (11)	0.0743 (9)	0.0085 (8)	0.0091 (7)	−0.0305 (8)
O4	0.0472 (8)	0.0625 (8)	0.1207 (13)	0.0017 (7)	−0.0119 (8)	0.0208 (9)
O5	0.0664 (8)	0.0460 (6)	0.0652 (8)	0.0016 (6)	−0.0078 (6)	0.0095 (6)
S1	0.0434 (2)	0.0569 (2)	0.0483 (2)	0.0004 (2)	0.00160 (19)	−0.00257 (19)

Geometric parameters (Å, º) top

C1—C6	1.376 (3)	C11—C12	1.371 (3)
C1—C2	1.378 (3)	C11—H11	0.93
C1—H1	0.93	C12—C13	1.375 (3)
C2—C3	1.395 (3)	C12—H12	0.93
C2—H2	0.93	C13—H13	0.93
C3—C4	1.396 (2)	C14—N1	1.455 (2)
C3—C7	1.468 (2)	C14—C15	1.506 (3)
C4—C5	1.384 (2)	C14—H14A	0.97
C4—N1	1.442 (2)	C14—H14B	0.97
C5—C6	1.370 (3)	C15—O4	1.188 (2)
C5—H5	0.93	C15—O5	1.327 (2)
C6—H6	0.93	C16—O5	1.443 (2)
C7—O1	1.198 (2)	C16—C17	1.486 (3)
C7—H7	0.93	C16—H16A	0.97
C8—C9	1.375 (2)	C16—H16B	0.97
C8—C13	1.388 (2)	C17—H17A	0.96
C8—S1	1.7605 (16)	C17—H17B	0.96
C9—C10	1.380 (3)	C17—H17C	0.96
C9—H9	0.93	N1—S1	1.6419 (14)
C10—C11	1.365 (3)	O2—S1	1.4253 (13)
C10—H10	0.93	O3—S1	1.4209 (15)

C6—C1—C2	120.05 (19)	C13—C12—H12	119.8
C6—C1—H1	120.0	C12—C13—C8	118.67 (18)
C2—C1—H1	120.0	C12—C13—H13	120.7
C1—C2—C3	120.5 (2)	C8—C13—H13	120.7
C1—C2—H2	119.7	N1—C14—C15	111.36 (15)
C3—C2—H2	119.7	N1—C14—H14A	109.4
C2—C3—C4	118.28 (17)	C15—C14—H14A	109.4
C2—C3—C7	119.84 (17)	N1—C14—H14B	109.4
C4—C3—C7	121.88 (16)	C15—C14—H14B	109.4
C5—C4—C3	120.73 (16)	H14A—C14—H14B	108.0
C5—C4—N1	119.76 (16)	O4—C15—O5	125.58 (17)
C3—C4—N1	119.50 (15)	O4—C15—C14	125.54 (16)
C6—C5—C4	119.74 (19)	O5—C15—C14	108.88 (15)
C6—C5—H5	120.1	O5—C16—C17	106.6 (2)
C4—C5—H5	120.1	O5—C16—H16A	110.4
C5—C6—C1	120.6 (2)	C17—C16—H16A	110.4
C5—C6—H6	119.7	O5—C16—H16B	110.4
C1—C6—H6	119.7	C17—C16—H16B	110.4
O1—C7—C3	123.7 (2)	H16A—C16—H16B	108.6
O1—C7—H7	118.2	C16—C17—H17A	109.5
C3—C7—H7	118.2	C16—C17—H17B	109.5
C9—C8—C13	120.88 (16)	H17A—C17—H17B	109.5
C9—C8—S1	119.43 (13)	C16—C17—H17C	109.5
C13—C8—S1	119.68 (14)	H17A—C17—H17C	109.5
C8—C9—C10	119.37 (18)	H17B—C17—H17C	109.5
C8—C9—H9	120.3	C4—N1—C14	117.44 (14)
C10—C9—H9	120.3	C4—N1—S1	119.99 (10)
C11—C10—C9	119.9 (2)	C14—N1—S1	118.12 (12)
C11—C10—H10	120.0	C15—O5—C16	116.89 (15)
C9—C10—H10	120.0	O3—S1—O2	120.46 (10)
C10—C11—C12	120.7 (2)	O3—S1—N1	106.47 (9)
C10—C11—H11	119.7	O2—S1—N1	105.88 (8)
C12—C11—H11	119.7	O3—S1—C8	107.29 (9)
C11—C12—C13	120.43 (19)	O2—S1—C8	109.85 (9)
C11—C12—H12	119.8	N1—S1—C8	105.97 (8)

C6—C1—C2—C3	−1.4 (3)	N1—C14—C15—O5	172.45 (14)
C1—C2—C3—C4	0.5 (3)	C5—C4—N1—C14	−59.0 (2)
C1—C2—C3—C7	−179.31 (18)	C3—C4—N1—C14	119.59 (16)
C2—C3—C4—C5	0.9 (2)	C5—C4—N1—S1	96.88 (17)
C7—C3—C4—C5	−179.28 (16)	C3—C4—N1—S1	−84.51 (17)
C2—C3—C4—N1	−177.66 (14)	C15—C14—N1—C4	−81.22 (19)
C7—C3—C4—N1	2.1 (2)	C15—C14—N1—S1	122.42 (14)
C3—C4—C5—C6	−1.4 (3)	O4—C15—O5—C16	−1.6 (3)
N1—C4—C5—C6	177.22 (17)	C14—C15—O5—C16	178.12 (15)
C4—C5—C6—C1	0.4 (3)	C17—C16—O5—C15	173.12 (19)
C2—C1—C6—C5	1.0 (3)	C4—N1—S1—O3	154.32 (14)
C2—C3—C7—O1	−8.5 (3)	C14—N1—S1—O3	−49.95 (15)
C4—C3—C7—O1	171.70 (19)	C4—N1—S1—O2	24.99 (16)
C13—C8—C9—C10	−0.3 (3)	C14—N1—S1—O2	−179.28 (13)
S1—C8—C9—C10	178.31 (17)	C4—N1—S1—C8	−91.66 (14)
C8—C9—C10—C11	−0.6 (3)	C14—N1—S1—C8	64.07 (15)
C9—C10—C11—C12	0.8 (3)	C9—C8—S1—O3	15.45 (17)
C10—C11—C12—C13	0.0 (3)	C13—C8—S1—O3	−165.94 (15)
C11—C12—C13—C8	−0.9 (3)	C9—C8—S1—O2	148.05 (15)
C9—C8—C13—C12	1.0 (3)	C13—C8—S1—O2	−33.34 (17)
S1—C8—C13—C12	−177.55 (16)	C9—C8—S1—N1	−98.00 (15)
N1—C14—C15—O4	−7.8 (3)	C13—C8—S1—N1	80.61 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.93	2.57	3.220 (2)	127
C16—H16B···Cg1ⁱⁱ	0.97	2.75	3.615 (2)	150

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₅S
M_r	347.38
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	11.3512 (6), 11.7820 (6), 12.8045 (6)
V (Å³)	1712.47 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.948, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	13978, 5831, 3738
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.744

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.109, 1.02
No. of reflections	5831
No. of parameters	218
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.25
Absolute structure	Flack (1983), 2533 Friedel pairs
Absolute structure parameter	0.04 (6)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT (Bruker, 2004, SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.93	2.57	3.220 (2)	127
C16—H16B···Cg1ⁱⁱ	0.97	2.75	3.615 (2)	150

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

Acknowledgements

SR and MNP thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

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