(E)-1-(2,4-Dinitro­phen­yl)-2-[1-(2-nitro­phen­yl)ethyl­idene]hydrazine

Nilwanna, B.; Chantrapromma, S.; Jansrisewangwong, P.; Fun, H.-K.

doi:10.1107/S1600536811042620

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o3084-o3085

doi:10.1107/S1600536811042620

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(E)-1-(2,4-Dinitrophenyl)-2-[1-(2-nitrophenyl)ethylidene]hydrazine

Boonlerd Nilwanna,^a Suchada Chantrapromma,^a ^*‡ Patcharaporn Jansrisewangwong ^a and Hoong-Kun Fun ^b §

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 19 September 2011; accepted 14 October 2011; online 29 October 2011)

The title compound, C₁₄H₁₁N₅O₆, was obtained from the condensation reaction of 2,4-dinitrophenylhydrazine and 2-nitroacetophenone. The molecule displays an E conformation about the C=N double bond and an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. The dihedral angle between the benzene rings is 7.84 (6)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and π–π stacking interactions [centroid–centroid distance = 3.6447 (8) Å] into a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Fun et al. (2011 ); Shan et al. (2003 ). For background to and the physiological and biological activity of hydrozones, see: Bendre et al. (1998 ); Nakamura & Goto (1996 ); Rollas & Küçükgüzel (2007 ); Singh et al. (2005 ); Yacorb (1999 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₄H₁₁N₅O₆
M_r = 345.28
Monoclinic, P 2₁ /c
a = 11.9313 (9) Å
b = 8.6700 (7) Å
c = 15.2363 (9) Å
β = 112.455 (5)°
V = 1456.61 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 100 K
0.40 × 0.16 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.951, T_max = 0.984
16360 measured reflections
4244 independent reflections
3361 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.110
S = 1.04
4244 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.88	1.94	2.6026 (13)	131
C10—H10A⋯O4ⁱ	0.93	2.42	3.2313 (16)	146
C12—H12A⋯O4ⁱⁱ	0.93	2.55	3.4353 (18)	159
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y+1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811042620/rz2643sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042620/rz2643Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042620/rz2643Isup3.cml

checkCIF report

Comment top

Hydrazones exhibit physiological and biological activities in the treatment of several diseases with anticonvulsant, antidepressant, analgesic, antiinflammatory, antiplatelet, antimalarial, antimicrobial, antimycobacterial, antitumor, vasodilator, antiviral, antischistosomiasis (Singh et al., 2005; Rollas & Küçükgüzel, 2007) and tyrosinase inhibitory properties (Bendre et al., 1998). Furthermore, they were used in engineering and analytical studies for aldehydes and ketones sampling (Yacorb, 1999) and analysis of protein carbonyls (Nakamura & Goto, 1996). These interesting activities have led us to synthesize the title hydrazone derivative (I). It was screened for antioxidant and antibacterial activities. Our results found that (I) is inactive for these tests. Herein we report the synthesis and crystal structure of (I).

The whole molecule of (I) (Fig. 1), C₁₄H₁₁N₅O₆, is not planar and exists in an E configuration with respect to the ethylidene C═N double bond [1.2905 (15) Å] with the torsion angle N1–N2–C7–C8 = 177.22 (10)°. The dihedral angle between the two benzene rings is 7.84 (6)°. The middle ethylidenehydrazine fragment (C7/C14/N1/N2) is planar with the r.m.s deviation of 0.0047 (1) Å. This middle C/C/N/N plane makes the dihedral angles of 11.28 (8) and 9.78 (8)° with the C1–C6 and C8–C13 benzene rings, respectively. The two nitro groups of 2,4-dinitrophenyl are co-planar with the bound benzene ring with the r.m.s. deviation of 0.0369 (1) Å for the twelve non H-atoms. However the nitro group of the 2-nitrophenyl tilts away from its bound benzene ring with the dihedral angle of 81.19 (7)° between the C9/N5/O5/O6 plane and C8–C13 benzene ring. This orientation is caused by the steric interaction between the hydrazine and nitro group. An intramolecular N1—H1···O2 hydrogen bond between the hydrazone-NH and the ortho nitro group (Fig. 1 and Table 1) generates an S(6) ring motif (Bernstein et al., 1995). The bond distances are within the expected range (Allen et al., 1987) and are comparable with those of related structures (Fun et al., 2011; Shan et al., 2003).

In the crystal structure, the molecules are linked by weak C—H···O hydrogen bonds (Table 1) into a three-dimensional network (Fig. 2) enforced by π···π stacking interactions (Cg₁···Cg₂ ⁱ = 3.6447 (8) Å; Cg₁ and Cg₂ are the centroids of C1–C6 and C8–C13 benzenre rings, respectively; symmetry code: (i) 2 - x, 2 - y, 1 - z). Short C···O (2.9999 (15) Å] contacts are also observed.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Fun et al. (2011); Shan et al. (2003). For background to and the physiological and biological activity of hydrozones, see: Bendre et al. (1998); Nakamura & Goto (1996); Rollas & Küçükgüzel (2007); Singh et al. (2005); Yacorb (1999). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).

Experimental top

The title compound was synthesized by dissolving 2,4-dinitrophenylhydrazine (0.40 g, 2 mmol) in ethanol (10.00 ml), and H₂SO₄ (98%, 0.50 ml) was slowly added with stirring. 2-Nitroacetophenone (0.27 ml, 2 mmol) was then added to the solution with continuous stirring. The solution was refluxed for 1 h yielding a yellow solid, which was filtered off and washed with methanol. Yellow block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from ethanol by slow evaporation of the solvent at room temperature over several days. M.p. 443–444 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (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, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. Hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound viewed along the c axis, showing molecular stacking along the b axis. Hydrogen bonds are shown as dashed lines.

(E)-1-(2,4-Dinitrophenyl)-2-[1-(2-nitrophenyl)ethylidene]hydrazine top

Crystal data top

C₁₄H₁₁N₅O₆	F(000) = 712
M_r = 345.28	D_x = 1.574 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 443–444 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.9313 (9) Å	Cell parameters from 4244 reflections
b = 8.6700 (7) Å	θ = 1.9–30.0°
c = 15.2363 (9) Å	µ = 0.13 mm⁻¹
β = 112.455 (5)°	T = 100 K
V = 1456.61 (19) Å³	Block, yellow
Z = 4	0.40 × 0.16 × 0.13 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4244 independent reflections
Radiation source: sealed tube	3361 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
T_min = 0.951, T_max = 0.984	k = −9→12
16360 measured reflections	l = −21→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0493P)² + 0.498P] where P = (F_o² + 2F_c²)/3
4244 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₄H₁₁N₅O₆	V = 1456.61 (19) Å³
M_r = 345.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9313 (9) Å	µ = 0.13 mm⁻¹
b = 8.6700 (7) Å	T = 100 K
c = 15.2363 (9) Å	0.40 × 0.16 × 0.13 mm
β = 112.455 (5)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4244 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3361 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.984	R_int = 0.033
16360 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
4244 reflections	Δρ_min = −0.28 e Å⁻³
227 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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
O1	1.32132 (8)	0.59779 (12)	0.77977 (6)	0.0221 (2)
O2	1.14527 (9)	0.70362 (12)	0.74461 (6)	0.0233 (2)
O3	1.44309 (8)	0.36901 (13)	0.55130 (7)	0.0265 (2)
O4	1.33701 (8)	0.39821 (12)	0.40099 (6)	0.0229 (2)
O5	0.76820 (8)	0.73691 (11)	0.30121 (6)	0.0191 (2)
O6	0.87386 (8)	0.93847 (12)	0.29701 (6)	0.0200 (2)
N1	1.01173 (9)	0.76742 (13)	0.56858 (7)	0.0166 (2)
H1	1.0252	0.7860	0.6283	0.020*
N2	0.91649 (9)	0.83451 (13)	0.49714 (7)	0.0160 (2)
N3	1.22384 (9)	0.64213 (13)	0.72129 (7)	0.0168 (2)
N4	1.35479 (9)	0.42076 (13)	0.48519 (7)	0.0168 (2)
N5	0.79296 (9)	0.87393 (13)	0.31434 (7)	0.0147 (2)
C1	1.09536 (10)	0.68522 (15)	0.54842 (8)	0.0145 (2)
C2	1.19951 (11)	0.62140 (14)	0.62097 (8)	0.0143 (2)
C3	1.28425 (10)	0.53651 (14)	0.59994 (8)	0.0151 (2)
H3A	1.3523	0.4966	0.6483	0.018*
C4	1.26628 (10)	0.51219 (15)	0.50638 (8)	0.0151 (2)
C5	1.16558 (11)	0.57308 (15)	0.43212 (8)	0.0170 (2)
H5A	1.1555	0.5560	0.3693	0.020*
C6	1.08201 (11)	0.65806 (16)	0.45296 (8)	0.0171 (2)
H6A	1.0153	0.6987	0.4037	0.021*
C7	0.83449 (11)	0.89627 (15)	0.52181 (8)	0.0152 (2)
C8	0.73396 (10)	0.97562 (15)	0.44578 (8)	0.0156 (2)
C9	0.71612 (10)	0.97024 (14)	0.34927 (8)	0.0143 (2)
C10	0.62471 (11)	1.04965 (15)	0.27935 (9)	0.0182 (3)
H10A	0.6165	1.0430	0.2163	0.022*
C11	0.54516 (11)	1.13956 (16)	0.30456 (10)	0.0207 (3)
H11A	0.4835	1.1942	0.2585	0.025*
C12	0.55861 (11)	1.14699 (17)	0.39886 (10)	0.0214 (3)
H12A	0.5048	1.2056	0.4159	0.026*
C13	0.65176 (11)	1.06765 (16)	0.46806 (9)	0.0192 (3)
H13A	0.6600	1.0757	0.5311	0.023*
C14	0.83892 (12)	0.89321 (17)	0.62186 (9)	0.0212 (3)
H14A	0.8708	0.7959	0.6507	0.032*
H14B	0.7586	0.9067	0.6209	0.032*
H14C	0.8902	0.9750	0.6578	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0217 (4)	0.0283 (6)	0.0134 (4)	0.0021 (4)	0.0035 (3)	0.0030 (4)
O2	0.0306 (5)	0.0261 (6)	0.0165 (4)	0.0090 (4)	0.0126 (4)	0.0021 (4)
O3	0.0211 (4)	0.0347 (6)	0.0202 (5)	0.0117 (4)	0.0041 (4)	0.0004 (4)
O4	0.0234 (4)	0.0294 (6)	0.0170 (4)	0.0045 (4)	0.0091 (4)	−0.0032 (4)
O5	0.0240 (4)	0.0140 (5)	0.0189 (4)	−0.0013 (4)	0.0079 (4)	−0.0031 (3)
O6	0.0177 (4)	0.0241 (5)	0.0204 (4)	−0.0010 (4)	0.0098 (3)	0.0028 (4)
N1	0.0187 (5)	0.0190 (6)	0.0121 (4)	0.0042 (4)	0.0059 (4)	0.0001 (4)
N2	0.0165 (4)	0.0168 (6)	0.0141 (4)	0.0026 (4)	0.0053 (4)	0.0002 (4)
N3	0.0218 (5)	0.0157 (6)	0.0134 (4)	0.0002 (4)	0.0074 (4)	0.0019 (4)
N4	0.0160 (4)	0.0171 (6)	0.0177 (5)	0.0008 (4)	0.0070 (4)	−0.0014 (4)
N5	0.0150 (4)	0.0171 (6)	0.0113 (4)	0.0008 (4)	0.0042 (4)	0.0006 (4)
C1	0.0166 (5)	0.0130 (6)	0.0147 (5)	−0.0006 (4)	0.0067 (4)	−0.0006 (4)
C2	0.0178 (5)	0.0138 (6)	0.0116 (5)	−0.0004 (4)	0.0060 (4)	0.0009 (4)
C3	0.0156 (5)	0.0140 (6)	0.0151 (5)	−0.0008 (4)	0.0053 (4)	0.0013 (4)
C4	0.0159 (5)	0.0146 (6)	0.0160 (5)	0.0006 (4)	0.0073 (4)	−0.0005 (4)
C5	0.0193 (5)	0.0185 (7)	0.0133 (5)	0.0008 (5)	0.0065 (4)	−0.0008 (5)
C6	0.0183 (5)	0.0192 (7)	0.0128 (5)	0.0024 (5)	0.0047 (4)	−0.0003 (5)
C7	0.0186 (5)	0.0128 (6)	0.0164 (5)	−0.0011 (4)	0.0091 (4)	−0.0011 (4)
C8	0.0155 (5)	0.0143 (6)	0.0182 (5)	−0.0016 (4)	0.0078 (4)	−0.0018 (4)
C9	0.0135 (5)	0.0119 (6)	0.0183 (5)	−0.0013 (4)	0.0070 (4)	−0.0026 (4)
C10	0.0166 (5)	0.0175 (7)	0.0182 (5)	−0.0004 (5)	0.0040 (4)	−0.0016 (5)
C11	0.0149 (5)	0.0167 (7)	0.0263 (6)	0.0011 (5)	0.0030 (5)	−0.0016 (5)
C12	0.0159 (5)	0.0193 (7)	0.0303 (7)	0.0011 (5)	0.0102 (5)	−0.0051 (5)
C13	0.0190 (5)	0.0180 (7)	0.0237 (6)	−0.0003 (5)	0.0118 (5)	−0.0035 (5)
C14	0.0239 (6)	0.0262 (8)	0.0172 (6)	0.0030 (5)	0.0121 (5)	0.0011 (5)

Geometric parameters (Å, º) top

O1—N3	1.2259 (13)	C5—C6	1.3710 (17)
O2—N3	1.2424 (14)	C5—H5A	0.9300
O3—N4	1.2309 (14)	C6—H6A	0.9300
O4—N4	1.2332 (13)	C7—C8	1.4807 (17)
O5—N5	1.2220 (14)	C7—C14	1.5051 (16)
O6—N5	1.2284 (13)	C8—C13	1.4029 (16)
N1—C1	1.3535 (15)	C8—C9	1.4037 (16)
N1—N2	1.3672 (14)	C9—C10	1.3824 (17)
N1—H1	0.8766	C10—C11	1.3909 (18)
N2—C7	1.2909 (15)	C10—H10A	0.9300
N3—C2	1.4539 (14)	C11—C12	1.3849 (19)
N4—C4	1.4521 (15)	C11—H11A	0.9300
N5—C9	1.4812 (15)	C12—C13	1.3874 (18)
C1—C6	1.4210 (16)	C12—H12A	0.9300
C1—C2	1.4224 (16)	C13—H13A	0.9300
C2—C3	1.3835 (16)	C14—H14A	0.9600
C3—C4	1.3744 (16)	C14—H14B	0.9600
C3—H3A	0.9300	C14—H14C	0.9600
C4—C5	1.4014 (16)

C1—N1—N2	120.26 (10)	C5—C6—H6A	119.4
C1—N1—H1	118.2	C1—C6—H6A	119.4
N2—N1—H1	121.0	N2—C7—C8	116.26 (10)
C7—N2—N1	115.88 (10)	N2—C7—C14	123.38 (11)
O1—N3—O2	122.46 (10)	C8—C7—C14	120.34 (10)
O1—N3—C2	118.58 (10)	C13—C8—C9	115.60 (11)
O2—N3—C2	118.96 (10)	C13—C8—C7	120.47 (11)
O3—N4—O4	123.16 (10)	C9—C8—C7	123.89 (11)
O3—N4—C4	119.00 (10)	C10—C9—C8	123.37 (11)
O4—N4—C4	117.84 (10)	C10—C9—N5	114.72 (10)
O5—N5—O6	124.63 (10)	C8—C9—N5	121.88 (10)
O5—N5—C9	117.57 (10)	C9—C10—C11	119.14 (12)
O6—N5—C9	117.73 (10)	C9—C10—H10A	120.4
N1—C1—C6	121.03 (11)	C11—C10—H10A	120.4
N1—C1—C2	121.97 (10)	C12—C11—C10	119.46 (12)
C6—C1—C2	117.01 (11)	C12—C11—H11A	120.3
C3—C2—C1	121.72 (10)	C10—C11—H11A	120.3
C3—C2—N3	116.05 (10)	C11—C12—C13	120.47 (12)
C1—C2—N3	122.23 (10)	C11—C12—H12A	119.8
C4—C3—C2	118.92 (11)	C13—C12—H12A	119.8
C4—C3—H3A	120.5	C12—C13—C8	121.95 (12)
C2—C3—H3A	120.5	C12—C13—H13A	119.0
C3—C4—C5	121.71 (11)	C8—C13—H13A	119.0
C3—C4—N4	118.41 (10)	C7—C14—H14A	109.5
C5—C4—N4	119.88 (10)	C7—C14—H14B	109.5
C6—C5—C4	119.37 (11)	H14A—C14—H14B	109.5
C6—C5—H5A	120.3	C7—C14—H14C	109.5
C4—C5—H5A	120.3	H14A—C14—H14C	109.5
C5—C6—C1	121.27 (11)	H14B—C14—H14C	109.5

C1—N1—N2—C7	172.81 (11)	C2—C1—C6—C5	0.48 (19)
N2—N1—C1—C6	−4.25 (18)	N1—N2—C7—C8	177.22 (10)
N2—N1—C1—C2	176.20 (11)	N1—N2—C7—C14	−1.52 (18)
N1—C1—C2—C3	179.52 (11)	N2—C7—C8—C13	−169.40 (12)
C6—C1—C2—C3	−0.04 (18)	C14—C7—C8—C13	9.39 (18)
N1—C1—C2—N3	−0.93 (19)	N2—C7—C8—C9	8.14 (18)
C6—C1—C2—N3	179.51 (11)	C14—C7—C8—C9	−173.07 (12)
O1—N3—C2—C3	7.08 (17)	C13—C8—C9—C10	0.25 (18)
O2—N3—C2—C3	−172.76 (11)	C7—C8—C9—C10	−177.40 (12)
O1—N3—C2—C1	−172.51 (12)	C13—C8—C9—N5	−177.90 (11)
O2—N3—C2—C1	7.65 (18)	C7—C8—C9—N5	4.45 (18)
C1—C2—C3—C4	−0.68 (19)	O5—N5—C9—C10	−96.72 (13)
N3—C2—C3—C4	179.74 (11)	O6—N5—C9—C10	80.43 (13)
C2—C3—C4—C5	1.00 (19)	O5—N5—C9—C8	81.58 (14)
C2—C3—C4—N4	−178.99 (11)	O6—N5—C9—C8	−101.27 (13)
O3—N4—C4—C3	−0.47 (18)	C8—C9—C10—C11	−0.28 (19)
O4—N4—C4—C3	179.19 (11)	N5—C9—C10—C11	177.99 (11)
O3—N4—C4—C5	179.54 (12)	C9—C10—C11—C12	−0.39 (19)
O4—N4—C4—C5	−0.81 (17)	C10—C11—C12—C13	1.1 (2)
C3—C4—C5—C6	−0.6 (2)	C11—C12—C13—C8	−1.1 (2)
N4—C4—C5—C6	179.41 (12)	C9—C8—C13—C12	0.45 (18)
C4—C5—C6—C1	−0.2 (2)	C7—C8—C13—C12	178.18 (12)
N1—C1—C6—C5	−179.09 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.88	1.94	2.6026 (13)	131
C10—H10A···O4ⁱ	0.93	2.42	3.2313 (16)	146
C12—H12A···O4ⁱⁱ	0.93	2.55	3.4353 (18)	159

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₅O₆
M_r	345.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.9313 (9), 8.6700 (7), 15.2363 (9)
β (°)	112.455 (5)
V (Å³)	1456.61 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.40 × 0.16 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.951, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	16360, 4244, 3361
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.110, 1.04
No. of reflections	4244
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.88	1.94	2.6026 (13)	131
C10—H10A···O4ⁱ	0.93	2.42	3.2313 (16)	146
C12—H12A···O4ⁱⁱ	0.93	2.55	3.4353 (18)	159

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

BN and PJ thank the Crystal Materials Research Unit, Prince of Songkla University, for financial support. The authors thank the Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. Mr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, is acknowledged for the bacterial assay.

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