1-(4-Nitro­phenoxy­meth­yl)-1H-1,2,4-triazole

Li, J.

doi:10.1107/S1600536807060758

organic compounds

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Volume 64| Part 1| January 2008| Page o17

https://doi.org/10.1107/S1600536807060758

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1-(4-Nitrophenoxymethyl)-1H-1,2,4-triazole

Jian Li ^a ^*

^aDepartment of Mathematics and Physics, Huangshi Institute of Technology, Huangshi 435000, People's Republic of China
^*Correspondence e-mail: hslijian2006@yahoo.com

(Received 16 November 2007; accepted 19 November 2007; online 6 December 2007)

The asymmetric unit of the title compound, C₉H₈N₄O₃, contains two independent molecules. The dihedral angles formed by the triazole and benzene rings in the two independent molecules are 83.3 (3) and 86.9 (4)°. The molecular packing involves weak C—H⋯N and C—H⋯O interactions, and π–π stacking interactions [centroid-to-centroid distance 3.745 (1) Å] between the aromatic rings of pairs of molecules.

Related literature

For the synthesis of related energetic polynitro and heterocyclic compounds, see: Jin et al. (2005 , 2006 ); Wang et al. (2007 ).

Experimental

Crystal data

C₉H₈N₄O₃
M_r = 220.19
Monoclinic, P 2₁ /n
a = 11.2344 (4) Å
b = 7.7197 (3) Å
c = 22.789 (1) Å
β = 94.730 (1)°
V = 1969.65 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.977, T_max = 0.989
18061 measured reflections
3863 independent reflections
2540 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.134
S = 1.07
3863 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.59	3.367 (3)	141
C14—H14⋯O3ⁱ	0.93	2.41	3.249 (3)	150
C17—H17⋯N4ⁱⁱ	0.93	2.56	3.351 (3)	144
Symmetry codes: (i) x, y-1, z; (ii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807060758/ln2005sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807060758/ln2005Isup2.hkl

checkCIF report

Comment top

The derivatives of 1,2,4-triazole are of great significance as pharmaceuticals, pesticides and high energetic materials. In recent years, the synthesis of energetic, polynitro and heterocyclic compounds have attracted considerable interest (Wang et al., 2007; Jin et al., 2005, 2006). This paper reports the crystal structure of the title 1,3,4-triazole derivative, (I).

The asymmetric unit of the title compound contains two independent molecules (Fig. 1). The dihedral angles formed by the triazole and benzene rings in the two independent molecules are 83.3 (3)° and 86.9 (4)°, respectively. The molecular packing involves weak C—H···N and C—H···O interactions (Table 1), and π···π stacking interactions of aromatic rings with the centroid to centroid distance being 3.745 (1) Å for adjacent benzene rings in pairs of molecules.

Related literature top

For the synthesis of energetic, polynitro and heterocyclic compounds, see: Jin et al. (2005, 2006); Wang et al. (2007).

Experimental top

Anhydrous K₂CO₃(420 mg, 3.0 mmol) was added to a solution of p-nitrophenol (139 mg, 1.0 mmol) in anhydrous acetonitrile (30 ml). After stirring for 30 min at 333 K, 1-chloromethyl-1H-1, 2, 4-triazole (117 mg, 1.0 mmol) was added. The mixture was refluxed for 12 h. After cooling, a small amount of precipitate was removed by filtration. The residue was purified by column chromatography to obtain a white solid (yield 86.2%, m.p. 465 K decomp.). Suitable crystals were obtained by evaporation of an ethyl acetate solution of the product.

Structure description top

For the synthesis of energetic, polynitro and heterocyclic compounds, see: Jin et al. (2005, 2006); Wang et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

Fig. 1. A view of the asymmetric unit of title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are omitted for clarity.

1-(4-Nitrophenoxymethyl)-1H-1,2,4-triazole top

Crystal data top

C₉H₈N₄O₃	F(000) = 912
M_r = 220.19	D_x = 1.485 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2528 reflections
a = 11.2344 (4) Å	θ = 3.1–21.4°
b = 7.7197 (3) Å	µ = 0.12 mm⁻¹
c = 22.789 (1) Å	T = 296 K
β = 94.730 (1)°	Block, colorless
V = 1969.65 (14) Å³	0.20 × 0.10 × 0.10 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3863 independent reflections
Radiation source: fine-focus sealed tube	2540 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
phi and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.977, T_max = 0.989	k = −9→9
18061 measured reflections	l = −28→26

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.063P)² + 0.0478P] where P = (F_o² + 2F_c²)/3
3863 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₉H₈N₄O₃	V = 1969.65 (14) Å³
M_r = 220.19	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.2344 (4) Å	µ = 0.12 mm⁻¹
b = 7.7197 (3) Å	T = 296 K
c = 22.789 (1) Å	0.20 × 0.10 × 0.10 mm
β = 94.730 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3863 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2540 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.989	R_int = 0.056
18061 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.07	Δρ_max = 0.19 e Å⁻³
3863 reflections	Δρ_min = −0.17 e Å⁻³
290 parameters

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	0.81377 (17)	0.3196 (3)	1.03182 (8)	0.0408 (5)
C2	0.93247 (17)	0.3426 (3)	1.04813 (8)	0.0458 (5)
H2	0.9670	0.4517	1.0461	0.055*
C3	1.00048 (18)	0.2022 (3)	1.06769 (9)	0.0462 (5)
H3	1.0817	0.2155	1.0783	0.055*
C4	0.94708 (17)	0.0410 (3)	1.07144 (8)	0.0413 (5)
C5	0.82669 (17)	0.0197 (3)	1.05410 (9)	0.0465 (5)
H5	0.7916	−0.0890	1.0559	0.056*
C6	0.75967 (18)	0.1595 (3)	1.03423 (9)	0.0452 (5)
H6	0.6789	0.1466	1.0225	0.054*
C7	1.12463 (17)	−0.0840 (3)	1.11700 (10)	0.0521 (6)
H7A	1.1301	0.0134	1.1440	0.063*
H7B	1.1768	−0.0623	1.0860	0.063*
C8	1.15858 (19)	−0.2774 (3)	1.20432 (10)	0.0543 (6)
H8	1.1336	−0.2011	1.2324	0.065*
C9	1.22169 (18)	−0.4899 (3)	1.16231 (11)	0.0572 (6)
H9	1.2515	−0.6003	1.1563	0.069*
C10	0.1692 (2)	0.7068 (3)	0.80842 (8)	0.0473 (5)
C11	0.2882 (2)	0.7309 (3)	0.82472 (9)	0.0533 (6)
H11	0.3213	0.8413	0.8243	0.064*
C12	0.35811 (18)	0.5906 (3)	0.84169 (9)	0.0494 (6)
H12	0.4390	0.6050	0.8529	0.059*
C13	0.30677 (17)	0.4276 (3)	0.84194 (9)	0.0440 (5)
C14	0.18569 (18)	0.4057 (3)	0.82638 (10)	0.0529 (6)
H14	0.1515	0.2962	0.8278	0.064*
C15	0.11677 (19)	0.5457 (3)	0.80901 (10)	0.0536 (6)
H15	0.0358	0.5323	0.7978	0.064*
C16	0.49184 (17)	0.2917 (3)	0.87293 (10)	0.0522 (6)
H16A	0.5060	0.3587	0.9088	0.063*
H16B	0.5322	0.3479	0.8421	0.063*
C17	0.58384 (17)	0.0123 (3)	0.84480 (10)	0.0543 (6)
H17	0.5990	0.0408	0.8065	0.065*
C18	0.5699 (2)	−0.1152 (3)	0.92397 (12)	0.0624 (6)
H18	0.5755	−0.2018	0.9524	0.075*
N1	0.74171 (17)	0.4702 (2)	1.01202 (8)	0.0516 (5)
N2	1.15923 (14)	−0.2405 (2)	1.14761 (7)	0.0444 (4)
N3	1.20085 (17)	−0.3790 (3)	1.11895 (8)	0.0605 (5)
N4	1.19720 (17)	−0.4338 (3)	1.21593 (9)	0.0617 (5)
N5	0.0937 (2)	0.8560 (3)	0.79082 (8)	0.0630 (6)
N6	0.53437 (14)	0.1182 (2)	0.88181 (7)	0.0460 (4)
N7	0.52429 (16)	0.0362 (3)	0.93374 (8)	0.0588 (5)
N8	0.60847 (16)	−0.1386 (3)	0.86990 (9)	0.0631 (6)
O1	0.79196 (15)	0.6084 (2)	1.00659 (8)	0.0747 (5)
O2	0.63420 (14)	0.4506 (2)	1.00168 (8)	0.0744 (5)
O3	0.13855 (18)	0.9998 (2)	0.79477 (7)	0.0843 (6)
O4	−0.01089 (19)	0.8306 (3)	0.77307 (8)	0.0874 (6)
O5	0.36738 (12)	0.27844 (18)	0.85648 (7)	0.0563 (4)
O6	1.00523 (12)	−0.10510 (18)	1.09272 (6)	0.0532 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0475 (11)	0.0415 (12)	0.0333 (11)	0.0041 (10)	0.0032 (9)	−0.0001 (9)
C2	0.0503 (12)	0.0425 (12)	0.0443 (12)	−0.0069 (10)	0.0025 (10)	0.0053 (10)
C3	0.0406 (11)	0.0508 (14)	0.0474 (13)	−0.0034 (10)	0.0042 (9)	0.0055 (10)
C4	0.0445 (11)	0.0418 (12)	0.0377 (11)	0.0039 (10)	0.0043 (9)	−0.0005 (10)
C5	0.0494 (12)	0.0384 (12)	0.0511 (13)	−0.0060 (10)	0.0008 (10)	−0.0018 (10)
C6	0.0419 (11)	0.0501 (14)	0.0434 (12)	−0.0017 (10)	0.0018 (9)	−0.0028 (10)
C7	0.0435 (12)	0.0524 (14)	0.0602 (14)	0.0039 (10)	0.0030 (10)	0.0046 (11)
C8	0.0630 (14)	0.0564 (16)	0.0435 (14)	−0.0004 (12)	0.0039 (11)	−0.0047 (11)
C9	0.0490 (13)	0.0460 (14)	0.0765 (17)	0.0087 (11)	0.0041 (12)	0.0014 (14)
C10	0.0656 (14)	0.0413 (13)	0.0356 (12)	0.0079 (11)	0.0083 (10)	−0.0034 (10)
C11	0.0730 (16)	0.0407 (13)	0.0469 (13)	−0.0105 (11)	0.0085 (11)	−0.0050 (10)
C12	0.0474 (12)	0.0472 (14)	0.0532 (13)	−0.0077 (10)	0.0022 (10)	−0.0052 (11)
C13	0.0452 (11)	0.0410 (13)	0.0462 (12)	0.0001 (10)	0.0065 (9)	−0.0038 (10)
C14	0.0477 (12)	0.0400 (13)	0.0710 (16)	−0.0056 (10)	0.0047 (11)	−0.0036 (11)
C15	0.0484 (12)	0.0510 (14)	0.0608 (15)	0.0015 (11)	0.0008 (11)	−0.0052 (11)
C16	0.0452 (12)	0.0528 (14)	0.0575 (14)	−0.0006 (10)	−0.0027 (10)	0.0005 (11)
C17	0.0420 (12)	0.0655 (16)	0.0559 (14)	0.0025 (11)	0.0069 (10)	−0.0078 (13)
C18	0.0598 (14)	0.0543 (16)	0.0716 (18)	0.0023 (12)	−0.0028 (13)	0.0067 (14)
N1	0.0583 (12)	0.0486 (12)	0.0478 (11)	0.0069 (10)	0.0038 (9)	−0.0010 (9)
N2	0.0447 (9)	0.0428 (11)	0.0460 (11)	0.0058 (8)	0.0052 (8)	0.0018 (9)
N3	0.0677 (12)	0.0589 (13)	0.0562 (12)	0.0249 (10)	0.0133 (10)	−0.0016 (10)
N4	0.0680 (13)	0.0552 (13)	0.0609 (13)	0.0003 (10)	−0.0007 (10)	0.0084 (11)
N5	0.0972 (17)	0.0528 (14)	0.0397 (11)	0.0174 (13)	0.0100 (11)	0.0012 (10)
N6	0.0450 (10)	0.0490 (11)	0.0433 (10)	0.0028 (8)	0.0000 (8)	0.0018 (9)
N7	0.0703 (12)	0.0585 (13)	0.0475 (12)	0.0035 (10)	0.0040 (9)	0.0055 (10)
N8	0.0540 (12)	0.0585 (14)	0.0766 (15)	0.0068 (10)	0.0034 (10)	−0.0082 (12)
O1	0.0813 (12)	0.0423 (10)	0.0994 (14)	0.0034 (9)	0.0008 (10)	0.0088 (9)
O2	0.0509 (10)	0.0748 (12)	0.0957 (13)	0.0124 (8)	−0.0050 (9)	0.0076 (10)
O3	0.1379 (17)	0.0431 (11)	0.0728 (13)	0.0136 (11)	0.0146 (11)	0.0049 (9)
O4	0.0864 (13)	0.0898 (15)	0.0835 (13)	0.0339 (11)	−0.0075 (11)	0.0022 (11)
O5	0.0418 (8)	0.0452 (9)	0.0807 (11)	−0.0004 (7)	−0.0024 (7)	0.0013 (8)
O6	0.0479 (8)	0.0434 (9)	0.0667 (10)	0.0016 (7)	−0.0057 (7)	0.0056 (8)

Geometric parameters (Å, º) top

C1—C2	1.366 (3)	C11—C12	1.375 (3)
C1—C6	1.381 (3)	C11—H11	0.9300
C1—N1	1.466 (3)	C12—C13	1.384 (3)
C2—C3	1.379 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—O5	1.365 (2)
C3—C4	1.387 (3)	C13—C14	1.387 (3)
C3—H3	0.9300	C14—C15	1.369 (3)
C4—O6	1.372 (2)	C14—H14	0.9300
C4—C5	1.387 (3)	C15—H15	0.9300
C5—C6	1.371 (3)	C16—O5	1.421 (2)
C5—H5	0.9300	C16—N6	1.431 (3)
C6—H6	0.9300	C16—H16A	0.9700
C7—O6	1.418 (2)	C16—H16B	0.9700
C7—N2	1.433 (3)	C17—N8	1.317 (3)
C7—H7A	0.9700	C17—N6	1.329 (3)
C7—H7B	0.9700	C17—H17	0.9300
C8—N4	1.303 (3)	C18—N7	1.302 (3)
C8—N2	1.324 (2)	C18—N8	1.352 (3)
C8—H8	0.9300	C18—H18	0.9300
C9—N3	1.314 (3)	N1—O1	1.218 (2)
C9—N4	1.346 (3)	N1—O2	1.221 (2)
C9—H9	0.9300	N2—N3	1.356 (2)
C10—C11	1.370 (3)	N5—O3	1.219 (3)
C10—C15	1.376 (3)	N5—O4	1.226 (3)
C10—N5	1.467 (3)	N6—N7	1.355 (2)

C2—C1—C6	121.91 (19)	O5—C13—C14	114.73 (18)
C2—C1—N1	118.85 (19)	C12—C13—C14	120.7 (2)
C6—C1—N1	119.23 (18)	C15—C14—C13	119.8 (2)
C1—C2—C3	119.2 (2)	C15—C14—H14	120.1
C1—C2—H2	120.4	C13—C14—H14	120.1
C3—C2—H2	120.4	C14—C15—C10	118.9 (2)
C2—C3—C4	119.62 (19)	C14—C15—H15	120.5
C2—C3—H3	120.2	C10—C15—H15	120.5
C4—C3—H3	120.2	O5—C16—N6	106.23 (16)
O6—C4—C3	124.31 (17)	O5—C16—H16A	110.5
O6—C4—C5	115.34 (18)	N6—C16—H16A	110.5
C3—C4—C5	120.34 (19)	O5—C16—H16B	110.5
C6—C5—C4	119.80 (19)	N6—C16—H16B	110.5
C6—C5—H5	120.1	H16A—C16—H16B	108.7
C4—C5—H5	120.1	N8—C17—N6	110.6 (2)
C5—C6—C1	119.09 (19)	N8—C17—H17	124.7
C5—C6—H6	120.5	N6—C17—H17	124.7
C1—C6—H6	120.5	N7—C18—N8	115.9 (2)
O6—C7—N2	107.66 (16)	N7—C18—H18	122.1
O6—C7—H7A	110.2	N8—C18—H18	122.1
N2—C7—H7A	110.2	O1—N1—O2	123.24 (19)
O6—C7—H7B	110.2	O1—N1—C1	118.48 (18)
N2—C7—H7B	110.2	O2—N1—C1	118.28 (19)
H7A—C7—H7B	108.5	C8—N2—N3	109.30 (18)
N4—C8—N2	111.6 (2)	C8—N2—C7	129.31 (19)
N4—C8—H8	124.2	N3—N2—C7	121.39 (17)
N2—C8—H8	124.2	C9—N3—N2	101.46 (18)
N3—C9—N4	115.9 (2)	C8—N4—C9	101.73 (19)
N3—C9—H9	122.1	O3—N5—O4	123.3 (2)
N4—C9—H9	122.1	O3—N5—C10	117.9 (2)
C11—C10—C15	121.9 (2)	O4—N5—C10	118.8 (2)
C11—C10—N5	119.8 (2)	C17—N6—N7	109.65 (18)
C15—C10—N5	118.3 (2)	C17—N6—C16	129.68 (19)
C10—C11—C12	119.4 (2)	N7—N6—C16	120.66 (18)
C10—C11—H11	120.3	C18—N7—N6	101.97 (19)
C12—C11—H11	120.3	C17—N8—C18	101.9 (2)
C11—C12—C13	119.25 (19)	N1—O2—H16A	132.4
C11—C12—H12	120.4	C13—O5—C16	117.61 (16)
C13—C12—H12	120.4	C4—O6—C7	116.82 (16)
O5—C13—C12	124.62 (18)

C6—C1—C2—C3	−0.1 (3)	O6—C7—N2—C8	−96.5 (2)
N1—C1—C2—C3	178.99 (17)	O6—C7—N2—N3	84.1 (2)
C1—C2—C3—C4	−1.1 (3)	N4—C9—N3—N2	−0.1 (2)
C2—C3—C4—O6	−176.99 (18)	C8—N2—N3—C9	0.2 (2)
C2—C3—C4—C5	1.8 (3)	C7—N2—N3—C9	179.73 (17)
O6—C4—C5—C6	177.62 (18)	N2—C8—N4—C9	0.1 (2)
C3—C4—C5—C6	−1.3 (3)	N3—C9—N4—C8	0.0 (3)
C4—C5—C6—C1	0.1 (3)	C11—C10—N5—O3	−4.4 (3)
C2—C1—C6—C5	0.6 (3)	C15—C10—N5—O3	174.4 (2)
N1—C1—C6—C5	−178.46 (17)	C11—C10—N5—O4	175.75 (19)
C15—C10—C11—C12	0.6 (3)	C15—C10—N5—O4	−5.5 (3)
N5—C10—C11—C12	179.39 (18)	N8—C17—N6—N7	−0.4 (2)
C10—C11—C12—C13	0.0 (3)	N8—C17—N6—C16	−178.74 (19)
C11—C12—C13—O5	178.33 (19)	O5—C16—N6—C17	94.9 (2)
C11—C12—C13—C14	−1.2 (3)	O5—C16—N6—N7	−83.2 (2)
O5—C13—C14—C15	−177.77 (19)	N8—C18—N7—N6	−0.2 (2)
C12—C13—C14—C15	1.8 (3)	C17—N6—N7—C18	0.3 (2)
C13—C14—C15—C10	−1.2 (3)	C16—N6—N7—C18	178.84 (18)
C11—C10—C15—C14	0.0 (3)	N6—C17—N8—C18	0.3 (2)
N5—C10—C15—C14	−178.81 (19)	N7—C18—N8—C17	−0.1 (3)
C2—C1—N1—O1	5.4 (3)	C12—C13—O5—C16	0.5 (3)
C6—C1—N1—O1	−175.47 (19)	C14—C13—O5—C16	−179.93 (18)
C2—C1—N1—O2	−174.71 (18)	N6—C16—O5—C13	−176.10 (17)
C6—C1—N1—O2	4.4 (3)	C3—C4—O6—C7	5.8 (3)
N4—C8—N2—N3	−0.2 (2)	C5—C4—O6—C7	−173.07 (17)
N4—C8—N2—C7	−179.68 (19)	N2—C7—O6—C4	167.68 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.59	3.367 (3)	141
C14—H14···O3ⁱ	0.93	2.41	3.249 (3)	150
C17—H17···N4ⁱⁱ	0.93	2.56	3.351 (3)	144

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

Experimental details

Crystal data
Chemical formula	C₉H₈N₄O₃
M_r	220.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.2344 (4), 7.7197 (3), 22.789 (1)
β (°)	94.730 (1)
V (Å³)	1969.65 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.977, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	18061, 3863, 2540
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.134, 1.07
No. of reflections	3863
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.59	3.367 (3)	141
C14—H14···O3ⁱ	0.93	2.41	3.249 (3)	150
C17—H17···N4ⁱⁱ	0.93	2.56	3.351 (3)	144

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

Acknowledgements

The author gratefully acknowledges the financial support of the National Science Funds for Distinguished Young Scholars Program and Hubei Provincial Department of Education, People's Republic of China.

References

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