Deacetyl tenuazonic acid p-toluene­sulfonyl­hydrazone

Siegel, D.; Blaske, F.; Koch, M.; Emmerling, F.; Nehls, I.

doi:10.1107/S1600536809048958

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3136

doi:10.1107/S1600536809048958

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Deacetyl tenuazonic acid p-toluenesulfonylhydrazone

David Siegel,^a ^* Franziska Blaske,^a Matthias Koch,^a Franziska Emmerling ^a and Irene Nehls ^a

^aBAM Federal Institute for Materials Research and Testing, Abteilung Analytische Chemie; Referenzmaterialien, Richard-Willstätter-Strasse 11, D-12489 Berlin-Adlershof, Germany
^*Correspondence e-mail: david.siegel@bam.de

(Received 6 November 2009; accepted 17 November 2009; online 21 November 2009)

The title compound {systematic name: 4-methyl-N′-[(3E)-2-(1-methylpropyl)-5-oxopyrrolidin-3-ylidene]benzenesulfonohydrazide}, C₁₅H₂₁N₃O₃S, is the condensation product of deacetyl tenuazonic acid (DTA) and p-toluenesulfonohydrazide. The crystal structure consists of chains along [100] linked by N—H⋯O hydrogen bonds.

Related literature

For the occurrence of tenuazonic acid (TA) in various food matrices, see: Weidenbörner (2001 ). For potential uses of the title compound in food analysis, see: Siegel, Rasenko et al. (2009 ). For the crystal structure of DTA, see: Siegel, Koch et al. (2009 ) and for its synthesis, see: Lebrun et al. (1988 ); Stickings (1959 ). For the structure of p-toluenesulfonylhydrazine, see: Roy & Nangia (2007 ). For the structures of other p-toluenesulfonyhydrazones, see, for example: Glidewell et al. (2004 ); Ng (1997 ); Yan et al. (2008 ).

Experimental

Crystal data

C₁₅H₂₁N₃O₃S
M_r = 323.41
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.1286 (16) Å
b = 8.285 (3) Å
c = 38.430 (12) Å
V = 1633.0 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 294 K
0.14 × 0.12 × 0.02 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: ψ scan (SHELXTL; Bruker, 2001 ) T_min = 0.970, T_max = 0.995
13112 measured reflections
4755 independent reflections
2233 reflections with I > 2σ(I)
R_int = 0.102

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.097
S = 0.77
4755 reflections
196 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1905 Friedel pairs
Flack parameter: −0.11 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.86	2.27	3.104 (3)	162
N1—H1⋯O3ⁱⁱ	1.03	2.10	3.063 (3)	156
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048958/sj2674sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048958/sj2674Isup2.hkl

checkCIF report

Comment top

Deacetyl tenuazonic acid (DTA) is formed upon boiling the Alternaria. mycotoxin tenuazonic acid (TA) in 0.1 M HCl (Stickings, 1959). As TA is frequently encountered in various food matrices (Weidenbörner, 2001), traces of DTA are expected to occur in these matrices as well. We have recently reported a derivatization procedure for TA quantification in food, which is based on hydrazone formation with 2,4-dinitrophenylhydrazine (Siegel, Rasenko et al., 2009) and are currently evaluating a similar procedure for DTA quantification using p-toluenesulfonyl hydrazide. The title compound is the product of the latter derivatization reaction. The stucture of the title compound, (I), is shown below. Each molecule (Fig.1) is connected to three adjacent molecules via N—H···O hydrogen bonds. As a result isolated ribbons are formed along the a axis, as depicted in Fig. 2.

Related literature top

For the occurrence of tenuazonic acid (TA) in various food matrices, see: Weidenbörner (2001). For potential uses of the title compound in food analysis, see: Siegel, Rasenko et al. (2009). For the crystal structure of DTA, see: Siegel, Koch et al. (2009) and for its synthesis, see: Lebrun et al. (1988); Stickings (1959). For the structure of p-toluenesulfonylhydrazine, see: Roy & Nangia (2007). For the structures of other p-toluenesulfonyhydrazones, see, for example: Glidewell et al. (2004); Ng (1997); Yan et al. (2008).

Experimental top

DTA was supplied by the workgroup of Professor R. Faust (University of Kassel, Germany) by synthesis according to a literature procedure (Lebrun et al., 1988). Its identity was confirmed by x-ray crystallography (Siegel, Koch et al., 2009). The title compound was synthesized by dissolving 20 mg (1 eq., 0.13 mmol) of DTA and a five fold molar excess of p-toluenesulfonyl hydrazide (5 eq., 0.65 mmol, 121 mg) in 50 ml 2 M HCl. After 30 minutes of shaking the precipitate was collected, washed with water, dissolved in ethyl acetate and dried with sodium sulfate. After evaporation of the solvent, a yellow powder was obtained, which was recrystallized from ethanol twice. For single-crystal x-ray crystallography, orange crystals of the title compound were grown by solvent evaporation (methanol:water 50:50 v:v) at ambient temperature over a period of three weeks.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. View of the unit cell of the title compound along [100] (upper picture) and [010] (lower picture) showing the hydrogen bond system drawn as dashed lines.

4-methyl-N'-[(3E)-2-(1-methylpropyl)-5-oxopyrrolidin-3- ylidene]benzenesulfonohydrazide top

Crystal data top

C₁₅H₂₁N₃O₃S	F(000) = 688
M_r = 323.41	D_x = 1.315 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 122 reflections
a = 5.1286 (16) Å	θ = 4–23°
b = 8.285 (3) Å	µ = 0.21 mm⁻¹
c = 38.430 (12) Å	T = 294 K
V = 1633.0 (9) Å³	Needle, colourless
Z = 4	0.14 × 0.12 × 0.02 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	4755 independent reflections
Radiation source: fine-focus sealed tube	2233 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.102
ω/2θ scans	θ_max = 31.1°, θ_min = 2.1°
Absorption correction: ψ scan (SHELXTL; Bruker, 2001)	h = −7→7
T_min = 0.970, T_max = 0.995	k = −12→12
13112 measured reflections	l = −55→55

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0333P)²] where P = (F_o² + 2F_c²)/3
S = 0.77	(Δ/σ)_max = 0.008
4755 reflections	Δρ_max = 0.21 e Å⁻³
196 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1905 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.11 (10)

Crystal data top

C₁₅H₂₁N₃O₃S	V = 1633.0 (9) Å³
M_r = 323.41	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.1286 (16) Å	µ = 0.21 mm⁻¹
b = 8.285 (3) Å	T = 294 K
c = 38.430 (12) Å	0.14 × 0.12 × 0.02 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	4755 independent reflections
Absorption correction: ψ scan (SHELXTL; Bruker, 2001)	2233 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.995	R_int = 0.102
13112 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.097	Δρ_max = 0.21 e Å⁻³
S = 0.77	Δρ_min = −0.29 e Å⁻³
4755 reflections	Absolute structure: Flack (1983), 1905 Friedel pairs
196 parameters	Absolute structure parameter: −0.11 (10)
0 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
S1	0.74721 (13)	0.49291 (7)	0.097917 (14)	0.04011 (15)
O1	−0.0629 (4)	0.3828 (2)	0.23977 (4)	0.0606 (5)
O2	0.6752 (4)	0.63657 (18)	0.08020 (4)	0.0527 (5)
O3	1.0099 (3)	0.4666 (2)	0.10814 (4)	0.0519 (5)
N1	0.5727 (4)	0.4954 (2)	0.13411 (4)	0.0390 (4)
H1	0.3769	0.5132	0.1302	0.047*
N2	0.6024 (4)	0.3487 (2)	0.15275 (5)	0.0383 (5)
N3	0.2395 (4)	0.1958 (2)	0.22262 (5)	0.0448 (5)
H3	0.1936	0.1221	0.2371	0.054*
C1	0.4445 (5)	0.3286 (3)	0.17784 (6)	0.0347 (5)
C2	0.2331 (6)	0.4344 (3)	0.19185 (6)	0.0462 (6)
H2A	0.3038	0.5354	0.2005	0.055*
H2B	0.1039	0.4574	0.1741	0.055*
C3	0.1172 (5)	0.3376 (3)	0.22082 (6)	0.0445 (6)
C4	0.4556 (5)	0.1730 (3)	0.19850 (6)	0.0364 (6)
H4	0.6190	0.1700	0.2117	0.044*
C5	0.4380 (4)	0.0220 (3)	0.17583 (5)	0.0366 (5)
H5	0.5686	0.0339	0.1574	0.044*
C6	0.1756 (4)	0.0098 (3)	0.15812 (6)	0.0542 (7)
H6A	0.1396	0.1114	0.1465	0.065*
H6B	0.0428	−0.0054	0.1758	0.065*
C7	0.1531 (6)	−0.1253 (4)	0.13175 (7)	0.0741 (10)
H7A	0.2885	−0.1145	0.1147	0.111*
H7B	−0.0139	−0.1197	0.1205	0.111*
H7C	0.1703	−0.2274	0.1433	0.111*
C8	0.5103 (4)	−0.1307 (2)	0.19639 (5)	0.0529 (8)
H8A	0.6778	−0.1162	0.2071	0.079*
H8B	0.5166	−0.2214	0.1809	0.079*
H8C	0.3816	−0.1498	0.2141	0.079*
C9	0.6413 (3)	0.32472 (18)	0.07366 (4)	0.0374 (6)
C10	0.7575 (3)	0.17800 (18)	0.07827 (4)	0.0494 (6)
H10	0.8985	0.1674	0.0933	0.059*
C11	0.6641 (6)	0.0458 (3)	0.06047 (7)	0.0565 (8)
H11	0.7440	−0.0539	0.0637	0.068*
C12	0.4556 (6)	0.0576 (3)	0.03813 (7)	0.0529 (7)
C13	0.3442 (6)	0.2071 (4)	0.03385 (7)	0.0593 (8)
H13	0.2038	0.2183	0.0187	0.071*
C14	0.4359 (5)	0.3420 (3)	0.05156 (6)	0.0488 (7)
H14	0.3583	0.4424	0.0483	0.059*
C15	0.3523 (7)	−0.0880 (4)	0.01904 (8)	0.0868 (11)
H15A	0.4174	−0.0880	−0.0044	0.130*
H15B	0.1652	−0.0843	0.0186	0.130*
H15C	0.4083	−0.1844	0.0307	0.130*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0445 (3)	0.0340 (3)	0.0418 (3)	−0.0070 (4)	0.0058 (3)	0.0019 (3)
O1	0.0621 (12)	0.0658 (13)	0.0540 (11)	−0.0020 (10)	0.0229 (11)	−0.0140 (9)
O2	0.0702 (14)	0.0343 (10)	0.0538 (10)	−0.0042 (9)	0.0046 (10)	0.0118 (8)
O3	0.0363 (9)	0.0603 (12)	0.0590 (10)	−0.0088 (9)	0.0040 (8)	−0.0056 (9)
N1	0.0412 (10)	0.0320 (10)	0.0438 (10)	−0.0030 (11)	0.0070 (9)	0.0008 (10)
N2	0.0399 (11)	0.0344 (11)	0.0405 (11)	−0.0056 (9)	0.0043 (11)	0.0034 (9)
N3	0.0547 (13)	0.0410 (12)	0.0387 (11)	−0.0104 (13)	0.0126 (12)	0.0005 (9)
C1	0.0347 (13)	0.0331 (13)	0.0364 (13)	−0.0067 (11)	−0.0005 (12)	−0.0063 (11)
C2	0.0526 (16)	0.0364 (13)	0.0497 (14)	−0.0069 (14)	0.0110 (14)	−0.0034 (10)
C3	0.0502 (16)	0.0458 (17)	0.0375 (14)	−0.0101 (14)	0.0051 (13)	−0.0131 (12)
C4	0.0351 (14)	0.0401 (14)	0.0339 (13)	−0.0102 (12)	0.0025 (11)	0.0021 (11)
C5	0.0367 (13)	0.0353 (14)	0.0378 (12)	0.0002 (12)	0.0025 (10)	0.0004 (11)
C6	0.0496 (16)	0.0443 (15)	0.0685 (17)	0.0041 (14)	−0.0143 (13)	−0.0161 (15)
C7	0.088 (3)	0.0531 (19)	0.082 (2)	0.0056 (17)	−0.0259 (19)	−0.0128 (16)
C8	0.061 (2)	0.0438 (17)	0.0543 (17)	−0.0015 (14)	0.0013 (14)	0.0120 (13)
C9	0.0390 (15)	0.0374 (14)	0.0357 (14)	−0.0051 (12)	0.0044 (12)	0.0051 (11)
C10	0.0548 (16)	0.0423 (14)	0.0511 (15)	0.0011 (17)	−0.0117 (15)	0.0008 (12)
C11	0.071 (2)	0.0400 (17)	0.0582 (17)	0.0025 (13)	−0.0077 (15)	0.0011 (12)
C12	0.0618 (19)	0.0510 (18)	0.0460 (16)	−0.0095 (15)	−0.0003 (15)	−0.0076 (13)
C13	0.0557 (19)	0.071 (2)	0.0515 (17)	0.0002 (16)	−0.0091 (15)	−0.0086 (15)
C14	0.0549 (17)	0.0453 (16)	0.0462 (15)	0.0059 (14)	−0.0019 (14)	−0.0006 (12)
C15	0.104 (3)	0.068 (2)	0.089 (2)	−0.014 (2)	−0.015 (2)	−0.0270 (18)

Geometric parameters (Å, º) top

S1—O3	1.4200 (17)	C6—H6A	0.9700
S1—O2	1.4201 (16)	C6—H6B	0.9700
S1—N1	1.6542 (18)	C7—H7A	0.9600
S1—C9	1.7624 (18)	C7—H7B	0.9600
O1—C3	1.235 (3)	C7—H7C	0.9600
N1—N2	1.419 (2)	C8—H8A	0.9600
N1—H1	1.0263	C8—H8B	0.9600
N2—C1	1.270 (3)	C8—H8C	0.9600
N3—C3	1.333 (3)	C9—C10	1.3653
N3—C4	1.457 (3)	C9—C14	1.361 (3)
N3—H3	0.8600	C10—C11	1.377 (3)
C1—C2	1.494 (3)	C10—H10	0.9300
C1—C4	1.515 (3)	C11—C12	1.375 (4)
C2—C3	1.495 (3)	C11—H11	0.9300
C2—H2A	0.9700	C12—C13	1.374 (4)
C2—H2B	0.9700	C12—C15	1.508 (4)
C4—C5	1.527 (3)	C13—C14	1.391 (3)
C4—H4	0.9800	C13—H13	0.9300
C5—C6	1.511 (3)	C14—H14	0.9300
C5—C8	1.537 (3)	C15—H15A	0.9600
C5—H5	0.9800	C15—H15B	0.9600
C6—C7	1.515 (3)	C15—H15C	0.9600

O3—S1—O2	120.52 (11)	C5—C6—H6B	108.6
O3—S1—N1	106.41 (10)	C7—C6—H6B	108.6
O2—S1—N1	104.60 (10)	H6A—C6—H6B	107.6
O3—S1—C9	108.51 (10)	C6—C7—H7A	109.5
O2—S1—C9	109.21 (9)	C6—C7—H7B	109.5
N1—S1—C9	106.72 (9)	H7A—C7—H7B	109.5
N2—N1—S1	110.85 (14)	C6—C7—H7C	109.5
N2—N1—H1	107.6	H7A—C7—H7C	109.5
S1—N1—H1	114.1	H7B—C7—H7C	109.5
C1—N2—N1	115.28 (18)	C5—C8—H8A	109.5
C3—N3—C4	116.02 (19)	C5—C8—H8B	109.5
C3—N3—H3	122.0	H8A—C8—H8B	109.5
C4—N3—H3	122.0	C5—C8—H8C	109.5
N2—C1—C2	131.2 (2)	H8A—C8—H8C	109.5
N2—C1—C4	119.1 (2)	H8B—C8—H8C	109.5
C2—C1—C4	109.71 (19)	C10—C9—C14	120.84 (13)
C3—C2—C1	104.0 (2)	C10—C9—S1	120.06 (6)
C3—C2—H2A	111.0	C14—C9—S1	119.04 (15)
C1—C2—H2A	111.0	C9—C10—C11	119.48 (14)
C3—C2—H2B	111.0	C9—C10—H10	120.3
C1—C2—H2B	111.0	C11—C10—H10	120.3
H2A—C2—H2B	109.0	C12—C11—C10	121.6 (2)
O1—C3—N3	126.1 (2)	C12—C11—H11	119.2
O1—C3—C2	125.0 (2)	C10—C11—H11	119.2
N3—C3—C2	108.9 (2)	C11—C12—C13	117.5 (2)
N3—C4—C1	101.24 (19)	C11—C12—C15	121.4 (3)
N3—C4—C5	115.09 (18)	C13—C12—C15	121.1 (3)
C1—C4—C5	113.32 (18)	C12—C13—C14	121.7 (3)
N3—C4—H4	109.0	C12—C13—H13	119.2
C1—C4—H4	109.0	C14—C13—H13	119.2
C5—C4—H4	109.0	C9—C14—C13	118.8 (2)
C6—C5—C4	111.3 (2)	C9—C14—H14	120.6
C6—C5—C8	113.0 (2)	C13—C14—H14	120.6
C4—C5—C8	111.52 (17)	C12—C15—H15A	109.5
C6—C5—H5	106.8	C12—C15—H15B	109.5
C4—C5—H5	106.8	H15A—C15—H15B	109.5
C8—C5—H5	106.8	C12—C15—H15C	109.5
C5—C6—C7	114.8 (2)	H15A—C15—H15C	109.5
C5—C6—H6A	108.6	H15B—C15—H15C	109.5
C7—C6—H6A	108.6

O3—S1—N1—N2	−58.11 (17)	N3—C4—C5—C8	−76.8 (2)
O2—S1—N1—N2	173.28 (14)	C1—C4—C5—C8	167.36 (18)
C9—S1—N1—N2	57.61 (15)	C4—C5—C6—C7	172.9 (2)
S1—N1—N2—C1	−169.08 (16)	C8—C5—C6—C7	−60.6 (3)
N1—N2—C1—C2	−1.3 (4)	O3—S1—C9—C10	24.73 (9)
N1—N2—C1—C4	177.98 (18)	O2—S1—C9—C10	157.88 (8)
N2—C1—C2—C3	178.5 (2)	N1—S1—C9—C10	−89.58 (8)
C4—C1—C2—C3	−0.8 (2)	O3—S1—C9—C14	−158.08 (16)
C4—N3—C3—O1	−177.0 (2)	O2—S1—C9—C14	−24.93 (18)
C4—N3—C3—C2	3.1 (3)	N1—S1—C9—C14	87.61 (17)
C1—C2—C3—O1	178.9 (2)	C14—C9—C10—C11	−0.46 (17)
C1—C2—C3—N3	−1.3 (3)	S1—C9—C10—C11	176.68 (18)
C3—N3—C4—C1	−3.4 (2)	C9—C10—C11—C12	−0.1 (3)
C3—N3—C4—C5	−126.0 (2)	C10—C11—C12—C13	0.6 (4)
N2—C1—C4—N3	−177.1 (2)	C10—C11—C12—C15	−179.3 (2)
C2—C1—C4—N3	2.3 (2)	C11—C12—C13—C14	−0.5 (4)
N2—C1—C4—C5	−53.3 (3)	C15—C12—C13—C14	179.4 (3)
C2—C1—C4—C5	126.1 (2)	C10—C9—C14—C13	0.5 (3)
N3—C4—C5—C6	50.5 (3)	S1—C9—C14—C13	−176.63 (18)
C1—C4—C5—C6	−65.4 (3)	C12—C13—C14—C9	0.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.86	2.27	3.104 (3)	162
N1—H1···O3ⁱⁱ	1.03	2.10	3.063 (3)	156

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

Experimental details

Crystal data
Chemical formula	C₁₅H₂₁N₃O₃S
M_r	323.41
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	5.1286 (16), 8.285 (3), 38.430 (12)
V (Å³)	1633.0 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.14 × 0.12 × 0.02

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	ψ scan (SHELXTL; Bruker, 2001)
T_min, T_max	0.970, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	13112, 4755, 2233
R_int	0.102
(sin θ/λ)_max (Å⁻¹)	0.727

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.097, 0.77
No. of reflections	4755
No. of parameters	196
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.29
Absolute structure	Flack (1983), 1905 Friedel pairs
Absolute structure parameter	−0.11 (10)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.86	2.27	3.104 (3)	162.4
N1—H1···O3ⁱⁱ	1.03	2.10	3.063 (3)	155.5

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

References

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Volume 65| Part 12| December 2009| Page o3136

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