rac-Methyl 4-azido-3-hydr­oxy-3-(2-nitro­phen­yl)butanoate

Vallat, O.; Buciumas, A.-M.; Neier, R.; Stoeckli-Evans, H.

doi:10.1107/S1600536808043857

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages o396-o397

doi:10.1107/S1600536808043857

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rac-Methyl 4-azido-3-hydroxy-3-(2-nitrophenyl)butanoate

Olivier Vallat,^a Ana-Maria Buciumas,^a Reinhard Neier ^a ^* and Helen Stoeckli-Evans ^b

^aInstitute of Chemistry, University of Neuchâtel, Rue Emile-Argand 11, CH-2009 Neuchâtel, Switzerland, and ^bInstitute of Physics, University of Neuchâtel, Rue Emile-Argand 11, CH-2009 Neuchâtel, Switzerland
^*Correspondence e-mail: reinhard.neier@unine.ch

(Received 18 December 2008; accepted 24 December 2008; online 28 January 2009)

In the title compound, C₁₁H₁₂N₄O₅, the mean plane through the nitro substituent on the benzene ring is inclined to the benzene mean plane by 85.8 (2)°, which avoids steric interactions with the ortho substituents. The hydroxy group is involved in bifurcated hydrogen bonds. The first is an intramolecular O—H⋯O hydrogen bond, involving the ester carbonyl O atom, which gives rise to the formation of a boat-like hydrogen-bonded chelate ring. The second is an intermolecular O—H⋯N hydrogen bond involving the first N atom of the azide group of a symmetry-related molecule. In the crystal structure this leads to the formation of a polmer chain extending in the c-axis direction.

Related literature

For literature related to the antitumor properties of rhazinilam, see: Bonneau et al. (2007 ). For literature related to the synthesis and structure–activity relationships of rhazinilam analogues, see: Decor et al. (2006 ); Baudoin et al. (2002 ); Ghosez et al. (2001 ); Rubio & Bornmann (2001 ); Dupont et al. (2000 , 1999 ); Alazard et al. (1996 ). For details of the Mukaiyama reaction, see: Mukaiyama et al. (1974 ). For literature related to the synthesis of pyrrolinone precursors, see: Vallat (2004 ); Vallat et al. (2009 ).

Experimental

Crystal data

C₁₁H₁₂N₄O₅
M_r = 280.25
Monoclinic, P 2₁ /n
a = 9.4772 (11) Å
b = 14.0710 (12) Å
c = 10.1861 (12) Å
β = 110.496 (13)°
V = 1272.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 153 (2) K
0.40 × 0.30 × 0.30 mm

Data collection

Stoe IPDS diffractometer
Absorption correction: none
8743 measured reflections
2451 independent reflections
1587 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.088
S = 0.87
2451 reflections
230 parameters
All H-atom parameters refined
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4	0.825 (19)	2.30 (2)	2.9439 (16)	135.5 (18)
O3—H3O⋯N2ⁱ	0.825 (19)	2.27 (2)	2.9193 (18)	135.6 (18)
C10—H10B⋯O4ⁱⁱ	0.95 (2)	2.557 (19)	3.350 (2)	141.0 (15)
C11—H11B⋯O1ⁱⁱⁱ	0.95 (3)	2.57 (2)	3.268 (3)	130.9 (16)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}]$ , $[z+{\script{1\over 2}}]$ .

Data collection: EXPOSE in IPDS Software (Stoe & Cie, 2000 ); cell refinement: CELL in IPDS Software; data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043857/lh2749sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043857/lh2749Isup2.hkl

checkCIF report

Comment top

Rhazinilam, a natural product, has been shown to possess antitumoral properties. It induces in vitro spiralization of microtubules [vinblastin effect] and inhibits the disassembly of these microtubules [paclitaxel effect](Bonneau et al., 2007). It has shown significant in vitro cytotoxicity towards various cancer cells, but it is not active in vivo. Several groups have been interested in synthesizing and studying the structure-activity relationship of rhazinilam analogues (Decor et al., 2006; Baudoin et al., 2002; Ghosez et al., 2001; Rubia & Bornmann, 2001; Dupont et al., 2000; Dupont et al., 1999; Alazard et al., 1996).

In the synthesis of Rhazinilam analogues developed in our group the Mukaiyama reaction, a versatile synthetic tool in organic chemistry, is a key step reaction (Mukaiyama et al., 1974). In one of our retrosynthetic approaches (1-methoxyvinyloxy)trimethysilane was used as a nucleophile, 2-azido-1-(2-nitrophenyl)ethanone as an electrophile and TiCl₄ as a Lewis acid, to synthesize the title hydroxyester, in high yield. This hydroxyester is a suitable precursor for the formation of the pyrrolinone required for the next step in the synthesis of Rhazinilam analogues (Vallat, 2004; Vallat et al., 2009).

The molecular structure of the title compound is illustrated in Fig. 1. The bond distances and angles are normal. The mean plane through the nitro group is inclined to the benzene mean plane by 85.8 (2)°, so avoiding steric interactions with the ortho substituents. The hydroxyl group (O3) is involved in bifurcated hydrogen bonds (Table 1). The first is an intramolecular O—H···O hydrogen bond, involving the ester carbonyl O-atom (O4), and gives rise to the formation of a boat-like hydrogen bonded chelate ring. The second is an intermolecular O—H···N hydrogen bond involving the first N-atom (N2) of the azide group (Table 1). This leads to the formation of a polymer chain extending in the c direction. (Fig. 2). There are also two weak intermolecular C—H···O interactions involving atoms O1 and O4 and the hydrogen atoms of the butanoate moiety (Table 1).

Related literature top

For literature related to the antitumoral properties of rhazinilam, see: Bonneau et al. (2007). For literature related to the synthesis and structure–activity relationships of rhazinilam analogues, see: Decor et al. (2006); Baudoin et al. (2002); Ghosez et al. (2001); Rubia or??? Rubio & Bornmann (2001); Dupont et al. (2000, 1999); Alazard et al. (1996). For details of the Mukaiyama reaction, see: Mukaiyama et al. (1974). For literature related to the synthesis of pyrrolinone precursors, see: Vallat (2004); Vallat et al. (2009).

Experimental top

Under an atmosphere of Ar, (1-methoxyvinyloxy)trimethylsilane (1.06 g, 7.3 mmol) was dissolved in dry CH₂Cl₂ (15 ml) and the temperature lowered to 243K. 2-Azido-1- (2-nitrophenyl)ethanone (0.5 g, 2.4 mmol) dissolved in dry CH₂Cl₂ (6 ml) was added to the reaction mixture dropwise. A solution of TiCl₄ (0.13 ml, 1.2 mmol), freshly distilled over polyvinylpyridine, in dry CH₂Cl₂ (4 ml), was added slowly. The solution became immediately red and then dark red. The reaction mixture was stirred at 243K for 15 min and then at 258K for 30 min. The cold mixture was then poured into an aqueous solution of 2 N NaOH (2.4 ml) and extracted with chloroform. The combined organic layers were washed with brine, dried over MgSO₄ and concentrated under vacuum. Purification of the residue by flash chromatography (silica gel, CH₂Cl₂) followed by crystallization (ether/hexane) gave a white solid (Yield 76%). Colourless plate-like crystals, suitable for X-ray analysis, were obtained by slow evaporation of a solution in ether/hexane (v:v = 1:1)

Computing details top

Data collection: EXPOSE in IPDS Software (Stoe & Cie, 2000); cell refinement: CELL in IPDS Software (Stoe & Cie, 2000); data reduction: INTEGRATE in IPDS Software (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and the displacement ellipsoids drawn at the 50% probability level. The intramolecular O—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. A view along the a axis of the crystal packing of the title compound, showing the intra and intermolecular hydrogen bonds as dashed lines (see Table 1 for details).

rac-Methyl 4-azido-3-hydroxy-3-(2-nitrophenyl)butanoate top

Crystal data top

C₁₁H₁₂N₄O₅	F(000) = 584
M_r = 280.25	D_x = 1.463 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5300 reflections
a = 9.4772 (11) Å	θ = 2.6–25.8°
b = 14.0710 (12) Å	µ = 0.12 mm⁻¹
c = 10.1861 (12) Å	T = 153 K
β = 110.496 (13)°	Plate, colourless
V = 1272.4 (2) Å³	0.40 × 0.30 × 0.30 mm
Z = 4

Data collection top

Stoe IPDS diffractometer	1587 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.074
Graphite monochromator	θ_max = 25.9°, θ_min = 2.5°
ϕ oscillation scans	h = −11→11
8743 measured reflections	k = −17→17
2451 independent reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	All H-atom parameters refined
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0487P)²] where P = (F_o² + 2F_c²)/3
S = 0.87	(Δ/σ)_max < 0.001
2451 reflections	Δρ_max = 0.23 e Å⁻³
230 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0087 (18)

Crystal data top

C₁₁H₁₂N₄O₅	V = 1272.4 (2) Å³
M_r = 280.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4772 (11) Å	µ = 0.12 mm⁻¹
b = 14.0710 (12) Å	T = 153 K
c = 10.1861 (12) Å	0.40 × 0.30 × 0.30 mm
β = 110.496 (13)°

Data collection top

Stoe IPDS diffractometer	1587 reflections with I > 2σ(I)
8743 measured reflections	R_int = 0.074
2451 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.088	All H-atom parameters refined
S = 0.87	Δρ_max = 0.23 e Å⁻³
2451 reflections	Δρ_min = −0.21 e Å⁻³
230 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
O1	0.32528 (17)	−0.00702 (10)	0.18798 (17)	0.0599 (6)
O2	0.39794 (16)	0.06178 (11)	0.39169 (15)	0.0653 (5)
O3	0.20867 (11)	0.19457 (8)	0.17217 (12)	0.0272 (4)
O4	0.13982 (13)	0.26155 (8)	0.41688 (11)	0.0370 (4)
O5	−0.07815 (12)	0.34053 (9)	0.35528 (11)	0.0372 (4)
N1	0.30233 (17)	0.02628 (11)	0.28967 (16)	0.0424 (5)
N2	−0.03288 (14)	0.22705 (10)	−0.10334 (13)	0.0321 (4)
N3	0.08103 (17)	0.25861 (10)	−0.12165 (13)	0.0340 (5)
N4	0.17267 (19)	0.29547 (14)	−0.15016 (17)	0.0535 (6)
C1	0.1474 (2)	0.01792 (12)	0.29231 (16)	0.0330 (5)
C2	0.1235 (3)	−0.06299 (14)	0.35997 (18)	0.0472 (7)
C3	−0.0179 (3)	−0.07913 (17)	0.3639 (2)	0.0574 (9)
C4	−0.1334 (3)	−0.01579 (16)	0.3016 (2)	0.0524 (8)
C5	−0.1057 (2)	0.06436 (14)	0.23568 (19)	0.0391 (6)
C6	0.03622 (18)	0.08457 (11)	0.22890 (15)	0.0277 (5)
C7	0.05471 (16)	0.17238 (11)	0.14778 (15)	0.0253 (5)
C8	−0.01067 (19)	0.14495 (13)	−0.00855 (16)	0.0293 (5)
C9	0.02297 (16)	0.28584 (12)	0.32851 (16)	0.0263 (5)
C10	−0.02665 (18)	0.25954 (13)	0.17665 (17)	0.0293 (5)
C11	−0.0434 (3)	0.36959 (19)	0.4988 (2)	0.0489 (8)
H2	0.210 (2)	−0.1090 (17)	0.404 (2)	0.062 (6)*
H3	−0.039 (3)	−0.1301 (18)	0.409 (2)	0.071 (7)*
H3O	0.242 (2)	0.2153 (14)	0.253 (2)	0.043 (6)*
H4	−0.235 (3)	−0.0267 (16)	0.307 (2)	0.064 (6)*
H5	−0.183 (2)	0.1080 (15)	0.186 (2)	0.053 (6)*
H8A	0.0553 (19)	0.0951 (13)	−0.0298 (16)	0.032 (4)*
H8B	−0.113 (2)	0.1209 (12)	−0.0262 (17)	0.035 (4)*
H10A	−0.0016 (19)	0.3118 (13)	0.1284 (17)	0.037 (5)*
H10B	−0.133 (2)	0.2515 (14)	0.1442 (19)	0.047 (5)*
H11A	−0.035 (3)	0.315 (2)	0.560 (3)	0.084 (8)*
H11B	−0.128 (3)	0.4060 (17)	0.497 (2)	0.067 (7)*
H11C	0.044 (3)	0.4065 (17)	0.525 (2)	0.062 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0611 (9)	0.0464 (10)	0.0834 (11)	0.0058 (7)	0.0395 (8)	−0.0098 (8)
O2	0.0494 (8)	0.0595 (10)	0.0596 (9)	0.0016 (7)	−0.0151 (7)	0.0141 (8)
O3	0.0215 (6)	0.0308 (7)	0.0259 (6)	−0.0016 (5)	0.0039 (4)	−0.0006 (5)
O4	0.0298 (6)	0.0426 (8)	0.0307 (6)	0.0080 (5)	0.0006 (5)	−0.0054 (5)
O5	0.0262 (6)	0.0445 (8)	0.0401 (7)	0.0067 (5)	0.0108 (5)	−0.0081 (5)
N1	0.0440 (9)	0.0276 (9)	0.0482 (10)	0.0104 (7)	0.0069 (8)	0.0091 (7)
N2	0.0236 (7)	0.0413 (9)	0.0279 (7)	−0.0005 (6)	0.0048 (5)	0.0044 (6)
N3	0.0352 (8)	0.0377 (9)	0.0257 (7)	0.0053 (7)	0.0063 (6)	0.0049 (6)
N4	0.0431 (10)	0.0645 (12)	0.0571 (10)	−0.0023 (9)	0.0228 (8)	0.0169 (9)
C1	0.0452 (10)	0.0269 (10)	0.0264 (8)	−0.0012 (8)	0.0118 (7)	−0.0025 (7)
C2	0.0829 (15)	0.0269 (11)	0.0336 (10)	−0.0010 (11)	0.0226 (10)	0.0010 (8)
C3	0.109 (2)	0.0334 (13)	0.0435 (12)	−0.0247 (13)	0.0437 (13)	−0.0082 (9)
C4	0.0721 (15)	0.0475 (14)	0.0494 (12)	−0.0280 (12)	0.0360 (11)	−0.0173 (10)
C5	0.0432 (10)	0.0397 (11)	0.0370 (9)	−0.0133 (9)	0.0174 (8)	−0.0097 (9)
C6	0.0341 (9)	0.0255 (9)	0.0229 (7)	−0.0046 (7)	0.0091 (7)	−0.0049 (6)
C7	0.0201 (7)	0.0260 (9)	0.0269 (8)	−0.0015 (6)	0.0045 (6)	0.0003 (6)
C8	0.0272 (9)	0.0297 (10)	0.0272 (8)	−0.0021 (7)	0.0047 (7)	−0.0003 (7)
C9	0.0230 (8)	0.0223 (9)	0.0322 (8)	−0.0018 (7)	0.0080 (7)	0.0002 (7)
C10	0.0226 (8)	0.0299 (10)	0.0304 (9)	0.0017 (7)	0.0032 (7)	0.0012 (7)
C11	0.0456 (12)	0.0569 (15)	0.0476 (12)	0.0028 (11)	0.0207 (10)	−0.0157 (11)

Geometric parameters (Å, º) top

O1—N1	1.224 (2)	C5—C6	1.400 (3)
O2—N1	1.221 (2)	C6—C7	1.530 (2)
O3—C7	1.426 (2)	C7—C10	1.531 (2)
O4—C9	1.206 (2)	C7—C8	1.542 (2)
O5—C9	1.330 (2)	C9—C10	1.497 (2)
O5—C11	1.441 (2)	C2—H2	1.02 (2)
O3—H3O	0.825 (19)	C3—H3	0.91 (2)
N1—C1	1.483 (3)	C4—H4	1.00 (3)
N2—C8	1.473 (2)	C5—H5	0.95 (2)
N2—N3	1.240 (2)	C8—H8A	1.012 (19)
N3—N4	1.133 (2)	C8—H8B	0.983 (19)
C1—C6	1.389 (2)	C10—H10A	0.959 (18)
C1—C2	1.390 (3)	C10—H10B	0.95 (2)
C2—C3	1.374 (4)	C11—H11A	0.98 (3)
C3—C4	1.382 (4)	C11—H11B	0.95 (3)
C4—C5	1.384 (3)	C11—H11C	0.93 (3)

C9—O5—C11	116.57 (15)	O4—C9—C10	125.11 (15)
C7—O3—H3O	105.2 (14)	C7—C10—C9	113.54 (14)
O1—N1—O2	125.32 (18)	C1—C2—H2	119.6 (12)
O2—N1—C1	117.49 (15)	C3—C2—H2	121.7 (12)
O1—N1—C1	117.11 (15)	C2—C3—H3	122.3 (18)
N3—N2—C8	116.57 (14)	C4—C3—H3	117.5 (18)
N2—N3—N4	171.07 (18)	C3—C4—H4	120.1 (13)
N1—C1—C6	122.19 (15)	C5—C4—H4	120.3 (13)
C2—C1—C6	123.7 (2)	C4—C5—H5	122.8 (13)
N1—C1—C2	114.10 (18)	C6—C5—H5	114.6 (12)
C1—C2—C3	118.7 (2)	N2—C8—H8A	111.1 (10)
C2—C3—C4	120.3 (2)	N2—C8—H8B	104.2 (10)
C3—C4—C5	119.6 (3)	C7—C8—H8A	109.8 (9)
C4—C5—C6	122.56 (19)	C7—C8—H8B	106.8 (10)
C1—C6—C7	125.77 (16)	H8A—C8—H8B	111.5 (15)
C5—C6—C7	118.97 (15)	C7—C10—H10A	106.5 (11)
C1—C6—C5	115.17 (16)	C7—C10—H10B	112.4 (12)
O3—C7—C6	112.72 (13)	C9—C10—H10A	107.2 (10)
O3—C7—C10	110.15 (13)	C9—C10—H10B	107.4 (11)
C6—C7—C8	105.96 (13)	H10A—C10—H10B	109.6 (16)
O3—C7—C8	104.56 (13)	O5—C11—H11A	111.3 (17)
C8—C7—C10	110.58 (13)	O5—C11—H11B	104.1 (12)
C6—C7—C10	112.49 (13)	O5—C11—H11C	108.2 (13)
N2—C8—C7	113.22 (14)	H11A—C11—H11B	109 (2)
O4—C9—O5	123.38 (14)	H11A—C11—H11C	113 (2)
O5—C9—C10	111.52 (14)	H11B—C11—H11C	111 (2)

C11—O5—C9—O4	−1.0 (3)	C4—C5—C6—C1	0.5 (3)
C11—O5—C9—C10	179.32 (17)	C4—C5—C6—C7	177.10 (16)
O1—N1—C1—C2	91.99 (19)	C1—C6—C7—O3	−15.3 (2)
O1—N1—C1—C6	−86.4 (2)	C1—C6—C7—C8	98.52 (18)
O2—N1—C1—C2	−84.7 (2)	C1—C6—C7—C10	−140.54 (16)
O2—N1—C1—C6	96.86 (19)	C5—C6—C7—O3	168.49 (14)
N3—N2—C8—C7	78.29 (18)	C5—C6—C7—C8	−77.74 (18)
N1—C1—C2—C3	−177.75 (16)	C5—C6—C7—C10	43.21 (19)
C6—C1—C2—C3	0.6 (3)	O3—C7—C8—N2	−73.41 (17)
N1—C1—C6—C5	177.43 (15)	C6—C7—C8—N2	167.29 (14)
N1—C1—C6—C7	1.1 (2)	C10—C7—C8—N2	45.12 (19)
C2—C1—C6—C5	−0.8 (2)	O3—C7—C10—C9	−69.34 (17)
C2—C1—C6—C7	−177.19 (15)	C6—C7—C10—C9	57.34 (19)
C1—C2—C3—C4	0.0 (3)	C8—C7—C10—C9	175.59 (14)
C2—C3—C4—C5	−0.3 (3)	O4—C9—C10—C7	19.8 (2)
C3—C4—C5—C6	0.1 (3)	O5—C9—C10—C7	−160.54 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.825 (19)	2.30 (2)	2.9439 (16)	135.5 (18)
O3—H3O···N2ⁱ	0.825 (19)	2.27 (2)	2.9193 (18)	135.6 (18)
C10—H10B···O4ⁱⁱ	0.95 (2)	2.557 (19)	3.350 (2)	141.0 (15)
C11—H11B···O1ⁱⁱⁱ	0.95 (3)	2.57 (2)	3.268 (3)	130.9 (16)

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₄O₅
M_r	280.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	153
a, b, c (Å)	9.4772 (11), 14.0710 (12), 10.1861 (12)
β (°)	110.496 (13)
V (Å³)	1272.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.30 × 0.30

Data collection
Diffractometer	Stoe IPDS diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8743, 2451, 1587
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.088, 0.87
No. of reflections	2451
No. of parameters	230
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: EXPOSE in IPDS Software (Stoe & Cie, 2000), CELL in IPDS Software (Stoe & Cie, 2000), INTEGRATE in IPDS Software (Stoe & Cie, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.825 (19)	2.30 (2)	2.9439 (16)	135.5 (18)
O3—H3O···N2ⁱ	0.825 (19)	2.27 (2)	2.9193 (18)	135.6 (18)
C10—H10B···O4ⁱⁱ	0.95 (2)	2.557 (19)	3.350 (2)	141.0 (15)
C11—H11B···O1ⁱⁱⁱ	0.95 (3)	2.57 (2)	3.268 (3)	130.9 (16)

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

Acknowledgements

This work was partially financed by the Swiss National Science Foundation.

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