2-Hydr­oxy-5-nitro­benzaldehyde 2,4-dinitro­phenyl­hydrazone

Tameem, A.A.; Saad, B.; Salhin, A.M.; Jebas, S.R.; Fun, H.-K.

doi:10.1107/S1600536808005825

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages o679-o680

doi:10.1107/S1600536808005825

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2-Hydroxy-5-nitrobenzaldehyde 2,4-dinitrophenylhydrazone

Abdassalam A. Tameem,^a Bahruddin Saad,^a Abdussalam M. Salhin,^a Samuel Robinson Jebas ^b ‡ and Hoong-Kun Fun ^b ^*

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 1 March 2008; accepted 1 March 2008; online 7 March 2008)

In the title compound, C₁₃H₉N₅O₇, one of the nitro groups is twisted away from the attached benzene ring by 16.21 (8)°. The dihedral angle between the two benzene rings is 4.63 (1)°. The molecular structure is stabilized by intramolecular N—H⋯O and O—H⋯N hydrogen bonds which generate an S(6) ring motif. The molecules pack as layers parallel to the ab plane; molecules of adjacent layers are linked into chains along the [101] direction through N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Cordis et al. (1998 ); Fun et al. (1996 ); Guillaumont & Nakamura (2000 ); Hanoune et al. (2006 ); Lamberton et al. (1974 ); Niknam et al. (2005 ); Raj & Kurup (2007 ); Salhin et al. (2007 ); Shan, Xu et al. (2003 ); Shan, Yu et al. (2003 ); Tameem et al. (2007 ); Uchiyama et al. (2003 ); Vogel et al. (2000 ); Zegota (1999 ); Zlotorzynska & Lai (1999 ). For ring motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₉N₅O₇
M_r = 347.25
Monoclinic, P 2₁ /n
a = 12.7543 (5) Å
b = 8.1898 (3) Å
c = 13.8618 (5) Å
β = 112.683 (2)°
V = 1335.94 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 100.0 (1) K
0.29 × 0.27 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.960, T_max = 0.985
24539 measured reflections
5195 independent reflections
3513 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.145
S = 1.09
5195 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O4ⁱ	0.89 (2)	2.54 (2)	3.0666 (15)	118 (2)
N1—H1N1⋯O1	0.89 (2)	2.07 (2)	2.6477 (15)	121 (2)
O5—H1O5⋯N2	0.92 (3)	1.82 (3)	2.6656 (14)	150 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005825/ci2567sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005825/ci2567Isup2.hkl

checkCIF report

Comment top

Phenylhydrazone derivatives have been synthesized in order to investigate their structures and analytical applications. 2,4-Dinitrophenylhydrazones play an important role as stabilizers for the detection, characterization and protection of the carbonyl group of compounds than phenylhydrazones (Niknam et al., 2005). 2,4-Dinitrophenylhydrazone derivatives are widely used in various forms of analytical chemistry (Lamberton et al., 1974; Zegota, 1999; Cordis et al., 1998; Zlotorzynska & Lai, 1999) and are also used as dyes (Guillaumont & Nakamura, 2000). They are also found to have versatile coordinating abilities towards different metal ions (Raj et al., 2006). In addition, they are used to determine airborne aldehydes and ketones (Vogel et al., 2000) and as detectors of formaldehyde (Hanoune et al., 2006). These compounds can exist as E and Z stereoisomers (Uchiyama et al., 2003). Their existence as a keto tautomer in the solid state with an E configuration across the C—N bond have been reported (Fun et al., 1996). The title compound, whose structure is reported here, is one of the series of phenylhydrazone derivatives that we have prepared; the crystal structures of some of these compounds have been studied previously (Tameem et al., 2007; Salhin et al., 2007).

The bond lengths and angles in the title compound (Fig.1) have normal values. The molecule is nealy planar, with a maximum deviation from the mean plane of 0.487 (1) Å for atom O1. The dihedral angle between the two benzene rings is 4.63 (1)°. The C—N bond lengths in the hydrazone moiety agree well with those reported earlier (Shan, Xu et al., 2003; Shan, Yu et al., 2003). The asymmetry of the exocyclic angles at C7 [C7—C8—C13 = 118.2 (2)° and C7—C8—C9 = 123.3 (2)°] is more pronounced than that at C6 [N1—C6—C1 = 122.7 (1)° and N1—C6—C5 = 120.5 (1)°]. One of the hydrazone N atoms is involved in an O—H···N intramolecular hydrogen bond with the hydroxy group, while the other is involved in an N—H···O intramolecular hydrogen bond with the nitro group. Each of these hydrogen bonds generate an S(6) ring motif (Bernstein et al.,1995).

The molecules are linked into a chain along the [1 0 1] direction through N—H—O hydrogen bonds. The molecules pack as layers parallel to the ab plane. Within the layer, weak π-π interactions are observed between the C1—C6 and C8—C13 benzene rings, with a centroid-centroid distance of 3.7457 (8) Å.

Related literature top

For related literature, see: Cordis et al. (1998); Fun et al. (1996); Guillaumont & Nakamura (2000); Hanoune et al. (2006); Lamberton et al. (1974); Niknam et al. (2005); Raj & Kurup (2007); Salhin et al. (2007); Shan, Xu et al. (2003); Shan, Yu et al. (2003); Tameem et al. (2007); Uchiyama et al. (2003); Vogel et al. (2000); Zegota (1999); Zlotorzynska & Lai (1999). For ring motifs, see: Bernstein et al. (1995).

Experimental top

2,4-Dinitrophenylhydrazine (400 mg, 2 mmol) in concentrated sulfuric acid (5 ml) was slowly added to a solution of 2-hydroxy-5-nitrobenzaldehyde (337 mg, 2 mmol) in ethanol (95%, 20 ml). The mixture was stirred for 15 min, and was left to stand at room temperature for 30 min. The resulting product was filtered and washed with 95% ethanol (20 ml) and the orange powder product was collected. Crystals suitable for X-ray diffraction analysis were grown by slow evaporation of a saturated solution of the resulted compound in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

2-Hydroxy-5-nitrobenzaldehyde 2,4-dinitrophenylhydrazone top

Crystal data top

C₁₃H₉N₅O₇	F(000) = 712
M_r = 347.25	D_x = 1.726 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3255 reflections
a = 12.7543 (5) Å	θ = 2.8–33.1°
b = 8.1898 (3) Å	µ = 0.14 mm⁻¹
c = 13.8618 (5) Å	T = 100 K
β = 112.683 (2)°	Block, orange
V = 1335.94 (9) Å³	0.29 × 0.27 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3513 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	R_int = 0.056
ω scans	θ_max = 33.4°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→19
T_min = 0.960, T_max = 0.985	k = −10→12
24539 measured reflections	l = −21→20
5195 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.050	w = 1/[σ²(F_o²) + (0.0708P)² + 0.0132P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.145	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 0.47 e Å⁻³
5195 reflections	Δρ_min = −0.33 e Å⁻³
234 parameters

Crystal data top

C₁₃H₉N₅O₇	V = 1335.94 (9) Å³
M_r = 347.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.7543 (5) Å	µ = 0.14 mm⁻¹
b = 8.1898 (3) Å	T = 100 K
c = 13.8618 (5) Å	0.29 × 0.27 × 0.11 mm
β = 112.683 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5195 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3513 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.985	R_int = 0.056
24539 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.47 e Å⁻³
5195 reflections	Δρ_min = −0.33 e Å⁻³
234 parameters

Special details top

Geometry. Experimental. The low-temperature data was collected with the Oxford Crysosystem Cobra low-temperature attachement.

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.

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

	x	y	z	U_iso*/U_eq
O1	0.71240 (8)	0.91583 (13)	0.22343 (8)	0.0228 (2)
O2	0.61439 (9)	1.12841 (14)	0.22968 (8)	0.0282 (2)
O3	0.39947 (10)	1.41385 (15)	−0.08171 (9)	0.0340 (3)
O4	0.45224 (10)	1.41148 (14)	−0.21219 (8)	0.0307 (3)
O5	0.94762 (8)	0.81549 (12)	−0.11896 (7)	0.0189 (2)
O6	1.34597 (9)	0.33913 (14)	0.11735 (8)	0.0300 (3)
O7	1.29887 (9)	0.41281 (13)	0.24496 (8)	0.0259 (2)
N1	0.80661 (9)	0.91651 (14)	0.08340 (9)	0.0164 (2)
N2	0.87737 (9)	0.86266 (13)	0.03680 (8)	0.0157 (2)
N3	0.66026 (9)	1.04241 (14)	0.18460 (8)	0.0187 (2)
N4	0.46053 (10)	1.36459 (15)	−0.12555 (9)	0.0208 (2)
N5	1.28791 (9)	0.41996 (14)	0.15301 (9)	0.0184 (2)
C1	0.64902 (11)	1.08800 (16)	0.07968 (9)	0.0160 (2)
C2	0.56488 (11)	1.20121 (16)	0.02874 (10)	0.0179 (2)
H2A	0.5209	1.2465	0.062	0.021*
C3	0.54779 (10)	1.24505 (16)	−0.07199 (10)	0.0172 (2)
C4	0.61284 (11)	1.17695 (16)	−0.12363 (10)	0.0171 (2)
H4A	0.5993	1.2067	−0.1921	0.02*
C5	0.69644 (11)	1.06624 (16)	−0.07233 (10)	0.0165 (2)
H5A	0.7392	1.0211	−0.1069	0.02*
C6	0.71925 (10)	1.01896 (15)	0.03210 (9)	0.0150 (2)
C7	0.96469 (10)	0.78013 (15)	0.09632 (9)	0.0151 (2)
H7A	0.9782	0.7678	0.1668	0.018*
C8	1.04195 (10)	0.70636 (15)	0.05474 (9)	0.0142 (2)
C9	1.03109 (10)	0.72528 (15)	−0.05001 (9)	0.0151 (2)
C10	1.10725 (11)	0.64726 (16)	−0.08556 (10)	0.0168 (2)
H10A	1.1009	0.6634	−0.154	0.02*
C11	1.19152 (10)	0.54678 (16)	−0.02006 (10)	0.0169 (2)
H11A	1.2412	0.4933	−0.044	0.02*
C12	1.20051 (10)	0.52732 (15)	0.08265 (10)	0.0159 (2)
C13	1.12875 (10)	0.60635 (15)	0.12052 (10)	0.0153 (2)
H13A	1.1382	0.593	0.19	0.018*
H1N1	0.8262 (16)	0.891 (2)	0.1508 (16)	0.038 (5)*
H1O5	0.905 (2)	0.854 (3)	−0.082 (2)	0.067 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0238 (5)	0.0253 (5)	0.0220 (5)	0.0056 (4)	0.0118 (4)	0.0049 (4)
O2	0.0377 (6)	0.0307 (6)	0.0253 (5)	0.0079 (5)	0.0222 (5)	−0.0004 (4)
O3	0.0317 (6)	0.0461 (7)	0.0298 (6)	0.0207 (5)	0.0181 (5)	0.0077 (5)
O4	0.0379 (6)	0.0342 (6)	0.0228 (5)	0.0153 (5)	0.0150 (5)	0.0087 (4)
O5	0.0201 (4)	0.0210 (5)	0.0162 (4)	0.0047 (4)	0.0076 (3)	0.0023 (3)
O6	0.0284 (5)	0.0335 (6)	0.0285 (5)	0.0145 (5)	0.0114 (4)	0.0014 (4)
O7	0.0269 (5)	0.0307 (6)	0.0197 (5)	0.0070 (4)	0.0086 (4)	0.0059 (4)
N1	0.0163 (5)	0.0196 (5)	0.0155 (5)	0.0030 (4)	0.0085 (4)	0.0005 (4)
N2	0.0158 (5)	0.0157 (5)	0.0177 (5)	0.0000 (4)	0.0089 (4)	−0.0017 (4)
N3	0.0193 (5)	0.0220 (6)	0.0183 (5)	−0.0015 (4)	0.0112 (4)	−0.0006 (4)
N4	0.0209 (5)	0.0224 (6)	0.0204 (5)	0.0049 (4)	0.0097 (4)	0.0004 (4)
N5	0.0170 (5)	0.0177 (5)	0.0203 (5)	0.0010 (4)	0.0070 (4)	0.0005 (4)
C1	0.0177 (5)	0.0183 (6)	0.0144 (5)	−0.0009 (4)	0.0088 (4)	−0.0011 (4)
C2	0.0176 (5)	0.0191 (6)	0.0195 (6)	0.0006 (5)	0.0099 (5)	−0.0033 (5)
C3	0.0161 (5)	0.0174 (6)	0.0194 (6)	0.0029 (5)	0.0081 (5)	0.0005 (4)
C4	0.0194 (6)	0.0174 (6)	0.0158 (5)	−0.0005 (5)	0.0085 (4)	−0.0005 (4)
C5	0.0169 (5)	0.0185 (6)	0.0160 (5)	0.0001 (5)	0.0085 (4)	−0.0023 (4)
C6	0.0147 (5)	0.0150 (6)	0.0163 (5)	−0.0019 (4)	0.0070 (4)	−0.0017 (4)
C7	0.0161 (5)	0.0151 (6)	0.0158 (5)	−0.0009 (4)	0.0081 (4)	−0.0004 (4)
C8	0.0151 (5)	0.0143 (5)	0.0142 (5)	−0.0009 (4)	0.0068 (4)	−0.0013 (4)
C9	0.0156 (5)	0.0142 (6)	0.0156 (5)	−0.0007 (4)	0.0062 (4)	−0.0002 (4)
C10	0.0190 (6)	0.0181 (6)	0.0156 (5)	−0.0011 (5)	0.0093 (4)	−0.0010 (4)
C11	0.0159 (5)	0.0174 (6)	0.0200 (6)	−0.0012 (4)	0.0096 (5)	−0.0024 (4)
C12	0.0134 (5)	0.0140 (6)	0.0190 (6)	0.0010 (4)	0.0048 (4)	0.0005 (4)
C13	0.0160 (5)	0.0147 (6)	0.0161 (5)	−0.0009 (4)	0.0072 (4)	0.0000 (4)

Geometric parameters (Å, º) top

O1—N3	1.2372 (15)	C2—H2A	0.93
O2—N3	1.2291 (15)	C3—C4	1.4035 (18)
O3—N4	1.2262 (15)	C4—C5	1.3711 (18)
O4—N4	1.2259 (15)	C4—H4A	0.93
O5—C9	1.3446 (15)	C5—C6	1.4159 (17)
O5—H1O5	0.92 (3)	C5—H5A	0.93
O6—N5	1.2302 (15)	C7—C8	1.4514 (17)
O7—N5	1.2288 (14)	C7—H7A	0.93
N1—C6	1.3565 (16)	C8—C13	1.3962 (17)
N1—N2	1.3697 (15)	C8—C9	1.4128 (16)
N1—H1N1	0.89 (2)	C9—C10	1.4014 (18)
N2—C7	1.2920 (16)	C10—C11	1.3799 (18)
N3—C1	1.4541 (16)	C10—H10A	0.93
N4—C3	1.4530 (17)	C11—C12	1.3927 (17)
N5—C12	1.4589 (16)	C11—H11A	0.93
C1—C2	1.3876 (18)	C12—C13	1.3795 (17)
C1—C6	1.4187 (17)	C13—H13A	0.93
C2—C3	1.3753 (17)

C9—O5—H1O5	105.4 (15)	C4—C5—H5A	119.2
C6—N1—N2	120.62 (11)	C6—C5—H5A	119.2
C6—N1—H1N1	122.4 (13)	N1—C6—C5	120.57 (11)
N2—N1—H1N1	116.6 (13)	N1—C6—C1	122.75 (11)
C7—N2—N1	115.45 (10)	C5—C6—C1	116.66 (11)
O2—N3—O1	122.71 (11)	N2—C7—C8	120.94 (11)
O2—N3—C1	118.60 (11)	N2—C7—H7A	119.5
O1—N3—C1	118.64 (11)	C8—C7—H7A	119.5
O4—N4—O3	123.45 (12)	C13—C8—C9	118.32 (11)
O4—N4—C3	118.12 (11)	C13—C8—C7	118.27 (11)
O3—N4—C3	118.43 (11)	C9—C8—C7	123.37 (11)
O7—N5—O6	123.08 (11)	O5—C9—C10	117.82 (11)
O7—N5—C12	118.31 (11)	O5—C9—C8	121.85 (11)
O6—N5—C12	118.60 (11)	C10—C9—C8	120.32 (11)
C2—C1—C6	122.19 (11)	C11—C10—C9	120.67 (11)
C2—C1—N3	116.05 (11)	C11—C10—H10A	119.7
C6—C1—N3	121.76 (11)	C9—C10—H10A	119.7
C3—C2—C1	118.67 (12)	C10—C11—C12	118.49 (12)
C3—C2—H2A	120.7	C10—C11—H11A	120.8
C1—C2—H2A	120.7	C12—C11—H11A	120.8
C2—C3—C4	121.38 (12)	C13—C12—C11	122.02 (11)
C2—C3—N4	119.01 (11)	C13—C12—N5	118.45 (11)
C4—C3—N4	119.61 (11)	C11—C12—N5	119.53 (11)
C5—C4—C3	119.51 (12)	C12—C13—C8	120.14 (11)
C5—C4—H4A	120.2	C12—C13—H13A	119.9
C3—C4—H4A	120.2	C8—C13—H13A	119.9
C4—C5—C6	121.55 (12)

C6—N1—N2—C7	172.84 (11)	C2—C1—C6—C5	−2.48 (18)
O2—N3—C1—C2	−15.33 (17)	N3—C1—C6—C5	176.74 (11)
O1—N3—C1—C2	162.33 (11)	N1—N2—C7—C8	175.64 (11)
O2—N3—C1—C6	165.40 (12)	N2—C7—C8—C13	−174.24 (11)
O1—N3—C1—C6	−16.94 (18)	N2—C7—C8—C9	3.12 (19)
C6—C1—C2—C3	1.35 (19)	C13—C8—C9—O5	177.95 (11)
N3—C1—C2—C3	−177.92 (11)	C7—C8—C9—O5	0.58 (19)
C1—C2—C3—C4	0.5 (2)	C13—C8—C9—C10	−1.09 (18)
C1—C2—C3—N4	−179.46 (11)	C7—C8—C9—C10	−178.46 (11)
O4—N4—C3—C2	174.55 (13)	O5—C9—C10—C11	−176.95 (11)
O3—N4—C3—C2	−5.12 (19)	C8—C9—C10—C11	2.12 (19)
O4—N4—C3—C4	−5.37 (19)	C9—C10—C11—C12	−1.25 (19)
O3—N4—C3—C4	174.96 (13)	C10—C11—C12—C13	−0.63 (19)
C2—C3—C4—C5	−1.0 (2)	C10—C11—C12—N5	179.16 (11)
N4—C3—C4—C5	178.90 (11)	O7—N5—C12—C13	−4.77 (17)
C3—C4—C5—C6	−0.22 (19)	O6—N5—C12—C13	174.17 (12)
N2—N1—C6—C5	2.89 (18)	O7—N5—C12—C11	175.44 (12)
N2—N1—C6—C1	−175.04 (11)	O6—N5—C12—C11	−5.62 (18)
C4—C5—C6—N1	−176.16 (12)	C11—C12—C13—C8	1.65 (19)
C4—C5—C6—C1	1.89 (18)	N5—C12—C13—C8	−178.14 (11)
C2—C1—C6—N1	175.52 (12)	C9—C8—C13—C12	−0.75 (18)
N3—C1—C6—N1	−5.25 (19)	C7—C8—C13—C12	176.75 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O4ⁱ	0.89 (2)	2.54 (2)	3.0666 (15)	118 (2)
N1—H1N1···O1	0.89 (2)	2.07 (2)	2.6477 (15)	121 (2)
O5—H1O5···N2	0.92 (3)	1.82 (3)	2.6656 (14)	150 (2)

Symmetry code: (i) x+1/2, −y+5/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉N₅O₇
M_r	347.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	12.7543 (5), 8.1898 (3), 13.8618 (5)
β (°)	112.683 (2)
V (Å³)	1335.94 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.29 × 0.27 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.960, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	24539, 5195, 3513
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.775

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.145, 1.09
No. of reflections	5195
No. of parameters	234
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.33

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O4ⁱ	0.89 (2)	2.54 (2)	3.0666 (15)	118 (2)
N1—H1N1···O1	0.89 (2)	2.07 (2)	2.6477 (15)	121 (2)
O5—H1O5···N2	0.92 (3)	1.82 (3)	2.6656 (14)	150 (2)

Symmetry code: (i) x+1/2, −y+5/2, z+1/2.

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for the award of a post-doctoral research fellowship.

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