(E)-1-(2,4-Dinitro­phen­yl)-2-(2-fluoro­benzyl­idene)hydrazine

Jasinski, J.P.; Braley, A.N.; Chidan Kumar, C.S.; Yathirajan, H.S.; Mayekar, A.N.

doi:10.1107/S1600536811014383

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1200-o1201

doi:10.1107/S1600536811014383

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(E)-1-(2,4-Dinitrophenyl)-2-(2-fluorobenzylidene)hydrazine

Jerry P. Jasinski,^a ^* Adam N. Braley,^a C. S. Chidan Kumar,^b H. S. Yathirajan ^b and A. N. Mayekar ^c

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cSeQuent Scientific Ltd, Baikampady, New Mangalore 575 011, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 13 April 2011; accepted 16 April 2011; online 22 April 2011)

In the title compound, C₁₃H₉FN₄O₄, the dihedral angle between the mean planes of the two benzene rings of the nearly planar molecule is 6.6 (9)°. The dihedral angles between the mean planes of the benzene ring and its two attached nitro groups are 6.7 (7) and 7.2 (9)°. Crystal packing is stabilized by N—H⋯O hydrogen bonds, weak C—H⋯O and C—H⋯F intermolecular interactions and centroid–centroid π-ring stacking interactions.

Related literature

For Schiff base propeties, see: Liang (2007 ). For nonlinear optical and crystalline properties, see: Baughman et al. (2004 ). For DNA-damaging and mutagenic agents, see: Okabe et al. (1993 ). For related structures, see: Bolte & Dill (1998 ); Shan et al. (2002 ); Fan et al. (2004 ); Motherwell & Ramsay, (2007 ); Shi et al. (2008 ); Ji et al. (2010 ); Kia et al. (2009 ); Jasinski et al. (2010 ).

Experimental

Crystal data

C₁₃H₉FN₄O₄
M_r = 304.24
Triclinic, $[P \overline 1]$
a = 7.0961 (8) Å
b = 8.2714 (9) Å
c = 11.7230 (8) Å
α = 88.614 (7)°
β = 80.544 (8)°
γ = 71.368 (10)°
V = 642.86 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 173 K
0.20 × 0.18 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.967, T_max = 1.000
6346 measured reflections
3466 independent reflections
2802 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.143
S = 1.09
3466 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.31 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
N2—H2A⋯O1	0.88	2.02	2.6317 (15)	126
N2—H2A⋯O1ⁱ	0.88	2.51	3.3424 (15)	158
C2—H2B⋯F1ⁱⁱ	0.95	2.45	3.3386 (17)	156
C3—H3A⋯O4ⁱⁱⁱ	0.95	2.48	3.3177 (19)	148
C5—H5A⋯O3^iv	0.95	2.43	3.2694 (17)	148
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+3, -y, -z+1; (iii) x+2, y-1, z; (iv) -x+1, -y, -z.

Table 2
Cg⋯Cg π-ring stacking interactions

Cg1 and Cg2 are the centroids of rings C1–C6 and C8–C13, respectively.

CgI⋯CgJ	Cg⋯Cg (Å)	Cg I_Perp (Å)	CgJ_Perp (Å)
Cg1⋯Cg2ⁱ	3.6916 (10)	−3.4632 (6)	3.3267 (5)
Cg2⋯Cg1ⁱⁱ	3.6916 (10)	3.3267 (5)	−3.4632 (6)
Symmetry codes: (i) 1 + x, y, z; (ii) −1 + x, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014383/ng5151sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014383/ng5151Isup2.hkl

checkCIF report

Comment top

Schiff bases and their complexes are widely used in the fields of biology, catalysis etc. (Liang, 2007). Especially, the dinitrophenyl hydrazones exhibit good nonlinear optical (NLO) and crystalline properties (Baughman et al., 2004) and are found to have versatile coordinating abilities towards different metal ions. In addition, some 2,4-dinitrophenyl hydrazone derivatives have been shown to be potentially DNA-damaging and mutagenic agents (Okabe et al., 1993). As a result of their significant molecular nonlinearities many x-ray structural studies of 2,4-dinitrophenylhydrazones have been reported. Among them, the most closely related structures are (E)-p-methoxy-acetophenone 2,4-dinitrophenylhydrazone (Bolte & Dill, 1998), acetophenone (2,4-dinitrophenyl)hydrazone (Shan et al., 2002), 3-chloroacetophenone 2,4-dintrophenyl- hydrazone (Fan et al., 2004), 2,4-dihydroxyacetophenone 2,4-dinitrophenylhydrazone (Baughman et al., 2004), syn-acetophenone (2,4-dinitrophenyl) hydrazone (Motherwell & Ramsay, 2007), 1-(2-chlorobenzylidene)-2-(2,4-dinitrophenyl)hydrazine (Shi et al., 2008), N-(2,4-dinitrophenyl)-N'-(1-p-tolylethylidene) hydrazine (Kia et al., 2009), N-(2,4-dinitrophenyl)-N'-(1-phenylethylidene)hydrazine (Ji et al., 2010) and (1E)-1-(3-bromophenyl)ethanone 2,4-dinitrophenylhydrazone (Jasinski et al., 2010). In view of the importance of 2,4-dinitrophenylhydrazones, this paper reports the crystal structure of the title compound, C₁₃H₉FN₄O₄, (I).

In the title compound the dihedral angle between the mean planes of the two benzene rings of a nearly planar molecule is 6.69°, (Fig. 2). The dihedral angle between the mean planes of the benzene ring and its two bonded nitro groups are 6.7 (7)° and 7.2 (9)°, respectively. Crystal packing is stabilized by N—H···O hydrogen bonds (Fig. 3), weak C—H···O intermolecular interactions and Cg—Cg π-ring stacking interactions (Table 2).

Related literature top

For Schiff base propeties, see: Liang et al. (2007). For nonlinear optical and crystalline properties, see: Baughman et al. (2004). For DNA-damaging and mutagenic agents, see: Okabe et al. (1993). For related structures, see: Bolte & Dill (1998); Shan et al. (2002); Fan et al. (2004); Motherwell & Ramsay, (2007); Shi et al. (2008); Ji et al. (2010); Kia et al. (2009); Jasinski et al. (2010).

Experimental top

A mixture of 2,4-dinitrophenylhydrazine (1.98 g) and 2-fluorobenzaldehyde (1.24 g) was dissolved in methanol and refluxed for about 6h. The precipitate formed was filtered, dried and recrystallized in ethlyacetate. X-ray quality crystals of the title compound (I), were obtained after three days by the slow evaporation of a 1:1 mixture of dimethylformamide and pyridine at room temperature. (mp: 502 - 505 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed down the b axis. Dashed lines indicate N—H···O hydrogen bonds and weak N—H···O intermolecular interactions.

(E)-1-(2,4-Dinitrophenyl)-2-(2-fluorobenzylidene)hydrazine top

Crystal data top

C₁₃H₉FN₄O₄	Z = 2
M_r = 304.24	F(000) = 312
Triclinic, P1	D_x = 1.572 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0961 (8) Å	Cell parameters from 3528 reflections
b = 8.2714 (9) Å	θ = 3.1–32.2°
c = 11.7230 (8) Å	µ = 0.13 mm⁻¹
α = 88.614 (7)°	T = 173 K
β = 80.544 (8)°	Block, orange-red
γ = 71.368 (10)°	0.20 × 0.18 × 0.15 mm
V = 642.86 (11) Å³

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3466 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2802 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 16.1500 pixels mm^-1	θ_max = 29.1°, θ_min = 3.1°
ϕ and ω scans	h = −9→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −11→11
T_min = 0.967, T_max = 1.000	l = −16→15
6346 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0733P)² + 0.0845P] where P = (F_o² + 2F_c²)/3
3466 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₃H₉FN₄O₄	γ = 71.368 (10)°
M_r = 304.24	V = 642.86 (11) Å³
Triclinic, P1	Z = 2
a = 7.0961 (8) Å	Mo Kα radiation
b = 8.2714 (9) Å	µ = 0.13 mm⁻¹
c = 11.7230 (8) Å	T = 173 K
α = 88.614 (7)°	0.20 × 0.18 × 0.15 mm
β = 80.544 (8)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3466 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2802 reflections with I > 2σ(I)
T_min = 0.967, T_max = 1.000	R_int = 0.016
6346 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.09	Δρ_max = 0.31 e Å⁻³
3466 reflections	Δρ_min = −0.17 e Å⁻³
199 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
F1	1.25967 (13)	0.08268 (12)	0.46347 (7)	0.0542 (3)
O1	0.33061 (16)	0.49706 (16)	0.46244 (9)	0.0576 (3)
O2	0.04251 (15)	0.62057 (14)	0.41195 (9)	0.0539 (3)
O3	0.0526 (2)	0.21724 (19)	−0.01824 (12)	0.0791 (4)
O4	−0.15820 (15)	0.42413 (15)	0.08977 (10)	0.0561 (3)
N1	0.79790 (15)	0.14775 (14)	0.28682 (9)	0.0377 (2)
N2	0.61603 (16)	0.26801 (15)	0.32453 (9)	0.0391 (3)
H2A	0.5959	0.3291	0.3884	0.047*
N3	0.00969 (19)	0.32023 (16)	0.06233 (11)	0.0443 (3)
N4	0.20937 (16)	0.51447 (14)	0.39505 (10)	0.0393 (3)
C1	1.2885 (2)	−0.02327 (17)	0.37123 (11)	0.0381 (3)
C2	1.4763 (2)	−0.1424 (2)	0.33969 (14)	0.0499 (3)
H2B	1.5823	−0.1511	0.3819	0.060*
C3	1.5057 (2)	−0.2487 (2)	0.24485 (15)	0.0534 (4)
H3A	1.6336	−0.3321	0.2214	0.064*
C4	1.3510 (2)	−0.23481 (18)	0.18385 (13)	0.0482 (3)
H4A	1.3727	−0.3086	0.1187	0.058*
C5	1.1651 (2)	−0.11396 (17)	0.21735 (11)	0.0404 (3)
H5A	1.0595	−0.1052	0.1747	0.049*
C6	1.12930 (18)	−0.00419 (15)	0.31287 (10)	0.0332 (3)
C7	0.93392 (18)	0.12582 (16)	0.34949 (11)	0.0358 (3)
H7A	0.9091	0.1924	0.4185	0.043*
C8	0.46749 (17)	0.29040 (15)	0.26058 (10)	0.0329 (3)
C9	0.26980 (18)	0.40469 (15)	0.29198 (10)	0.0324 (3)
C10	0.12047 (18)	0.41764 (14)	0.22616 (10)	0.0336 (3)
H10A	−0.0115	0.4954	0.2487	0.040*
C11	0.16630 (19)	0.31661 (15)	0.12820 (11)	0.0345 (3)
C12	0.3609 (2)	0.20726 (17)	0.09136 (11)	0.0396 (3)
H12A	0.3909	0.1412	0.0216	0.048*
C13	0.50799 (19)	0.19515 (17)	0.15534 (11)	0.0390 (3)
H13A	0.6408	0.1213	0.1290	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0485 (5)	0.0679 (6)	0.0446 (5)	−0.0099 (4)	−0.0184 (4)	−0.0156 (4)
O1	0.0428 (6)	0.0767 (7)	0.0512 (6)	−0.0123 (5)	−0.0111 (5)	−0.0292 (5)
O2	0.0424 (6)	0.0553 (6)	0.0517 (6)	0.0007 (5)	−0.0030 (4)	−0.0189 (5)
O3	0.0686 (8)	0.0871 (9)	0.0790 (9)	−0.0060 (7)	−0.0370 (7)	−0.0388 (7)
O4	0.0380 (5)	0.0613 (7)	0.0664 (7)	−0.0057 (5)	−0.0209 (5)	−0.0032 (5)
N1	0.0290 (5)	0.0430 (6)	0.0384 (6)	−0.0080 (4)	−0.0046 (4)	−0.0036 (4)
N2	0.0292 (5)	0.0480 (6)	0.0373 (5)	−0.0077 (4)	−0.0053 (4)	−0.0108 (4)
N3	0.0440 (6)	0.0463 (6)	0.0455 (6)	−0.0131 (5)	−0.0174 (5)	−0.0022 (5)
N4	0.0348 (5)	0.0427 (6)	0.0392 (6)	−0.0121 (4)	−0.0013 (4)	−0.0110 (4)
C1	0.0385 (6)	0.0426 (6)	0.0338 (6)	−0.0116 (5)	−0.0102 (5)	−0.0005 (5)
C2	0.0391 (7)	0.0540 (8)	0.0529 (8)	−0.0048 (6)	−0.0174 (6)	0.0011 (6)
C3	0.0407 (7)	0.0461 (7)	0.0613 (9)	0.0020 (6)	−0.0060 (6)	−0.0041 (7)
C4	0.0529 (8)	0.0415 (7)	0.0455 (8)	−0.0103 (6)	−0.0031 (6)	−0.0091 (6)
C5	0.0408 (7)	0.0430 (7)	0.0393 (7)	−0.0136 (5)	−0.0107 (5)	−0.0040 (5)
C6	0.0317 (6)	0.0357 (6)	0.0329 (6)	−0.0113 (5)	−0.0061 (4)	0.0007 (4)
C7	0.0333 (6)	0.0418 (6)	0.0331 (6)	−0.0129 (5)	−0.0054 (5)	−0.0042 (5)
C8	0.0286 (5)	0.0363 (6)	0.0339 (6)	−0.0108 (5)	−0.0044 (4)	−0.0034 (4)
C9	0.0313 (6)	0.0335 (5)	0.0318 (6)	−0.0103 (4)	−0.0027 (4)	−0.0058 (4)
C10	0.0298 (6)	0.0313 (5)	0.0382 (6)	−0.0076 (4)	−0.0056 (4)	−0.0021 (4)
C11	0.0354 (6)	0.0335 (6)	0.0363 (6)	−0.0104 (5)	−0.0115 (5)	−0.0006 (5)
C12	0.0394 (7)	0.0403 (6)	0.0361 (6)	−0.0071 (5)	−0.0077 (5)	−0.0092 (5)
C13	0.0316 (6)	0.0416 (6)	0.0385 (6)	−0.0044 (5)	−0.0045 (5)	−0.0090 (5)

Geometric parameters (Å, º) top

F1—C1	1.3555 (15)	C3—H3A	0.9500
O1—N4	1.2343 (15)	C4—C5	1.3785 (19)
O2—N4	1.2161 (15)	C4—H4A	0.9500
O3—N3	1.2204 (16)	C5—C6	1.3967 (17)
O4—N3	1.2225 (15)	C5—H5A	0.9500
N1—C7	1.2724 (16)	C6—C7	1.4618 (17)
N1—N2	1.3653 (15)	C7—H7A	0.9500
N2—C8	1.3548 (16)	C8—C9	1.4131 (17)
N2—H2A	0.8800	C8—C13	1.4181 (16)
N3—C11	1.4463 (16)	C9—C10	1.3863 (16)
N4—C9	1.4500 (15)	C10—C11	1.3685 (17)
C1—C2	1.3783 (19)	C10—H10A	0.9500
C1—C6	1.3800 (17)	C11—C12	1.3916 (18)
C2—C3	1.381 (2)	C12—C13	1.3597 (18)
C2—H2B	0.9500	C12—H12A	0.9500
C3—C4	1.379 (2)	C13—H13A	0.9500

C7—N1—N2	117.04 (11)	C1—C6—C5	116.70 (11)
C8—N2—N1	117.99 (10)	C1—C6—C7	121.17 (11)
C8—N2—H2A	121.0	C5—C6—C7	122.12 (11)
N1—N2—H2A	121.0	N1—C7—C6	118.51 (11)
O3—N3—O4	123.15 (12)	N1—C7—H7A	120.7
O3—N3—C11	117.69 (12)	C6—C7—H7A	120.7
O4—N3—C11	119.16 (11)	N2—C8—C9	123.98 (11)
O2—N4—O1	122.32 (11)	N2—C8—C13	119.48 (11)
O2—N4—C9	119.24 (11)	C9—C8—C13	116.55 (11)
O1—N4—C9	118.44 (11)	C10—C9—C8	121.82 (10)
F1—C1—C2	118.20 (12)	C10—C9—N4	115.72 (11)
F1—C1—C6	118.24 (11)	C8—C9—N4	122.45 (11)
C2—C1—C6	123.55 (12)	C11—C10—C9	118.91 (11)
C1—C2—C3	118.00 (13)	C11—C10—H10A	120.5
C1—C2—H2B	121.0	C9—C10—H10A	120.5
C3—C2—H2B	121.0	C10—C11—C12	121.27 (11)
C4—C3—C2	120.60 (14)	C10—C11—N3	119.78 (11)
C4—C3—H3A	119.7	C12—C11—N3	118.93 (11)
C2—C3—H3A	119.7	C13—C12—C11	119.89 (11)
C5—C4—C3	120.00 (13)	C13—C12—H12A	120.1
C5—C4—H4A	120.0	C11—C12—H12A	120.1
C3—C4—H4A	120.0	C12—C13—C8	121.44 (11)
C4—C5—C6	121.14 (12)	C12—C13—H13A	119.3
C4—C5—H5A	119.4	C8—C13—H13A	119.3
C6—C5—H5A	119.4

C7—N1—N2—C8	−178.38 (11)	N2—C8—C9—N4	2.32 (19)
F1—C1—C2—C3	−179.24 (13)	C13—C8—C9—N4	−177.74 (11)
C6—C1—C2—C3	−0.3 (2)	O2—N4—C9—C10	−6.98 (17)
C1—C2—C3—C4	0.2 (2)	O1—N4—C9—C10	173.40 (12)
C2—C3—C4—C5	0.0 (2)	O2—N4—C9—C8	173.56 (12)
C3—C4—C5—C6	−0.1 (2)	O1—N4—C9—C8	−6.07 (19)
F1—C1—C6—C5	179.17 (11)	C8—C9—C10—C11	0.07 (18)
C2—C1—C6—C5	0.3 (2)	N4—C9—C10—C11	−179.40 (11)
F1—C1—C6—C7	−0.39 (18)	C9—C10—C11—C12	−2.71 (19)
C2—C1—C6—C7	−179.28 (13)	C9—C10—C11—N3	176.08 (11)
C4—C5—C6—C1	0.0 (2)	O3—N3—C11—C10	−173.46 (14)
C4—C5—C6—C7	179.51 (12)	O4—N3—C11—C10	6.06 (19)
N2—N1—C7—C6	178.86 (10)	O3—N3—C11—C12	5.4 (2)
C1—C6—C7—N1	173.99 (12)	O4—N3—C11—C12	−175.12 (12)
C5—C6—C7—N1	−5.54 (19)	C10—C11—C12—C13	2.3 (2)
N1—N2—C8—C9	177.09 (11)	N3—C11—C12—C13	−176.51 (12)
N1—N2—C8—C13	−2.85 (18)	C11—C12—C13—C8	0.8 (2)
N2—C8—C9—C10	−177.12 (11)	N2—C8—C13—C12	176.68 (12)
C13—C8—C9—C10	2.82 (18)	C9—C8—C13—C12	−3.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.88	2.02	2.6317 (15)	126
N2—H2A···O1ⁱ	0.88	2.51	3.3424 (15)	158
C2—H2B···F1ⁱⁱ	0.95	2.45	3.3386 (17)	156
C3—H3A···O4ⁱⁱⁱ	0.95	2.48	3.3177 (19)	148
C5—H5A···O3^iv	0.95	2.43	3.2694 (17)	148

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3, −y, −z+1; (iii) x+2, y−1, z; (iv) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₉FN₄O₄
M_r	304.24
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.0961 (8), 8.2714 (9), 11.7230 (8)
α, β, γ (°)	88.614 (7), 80.544 (8), 71.368 (10)
V (Å³)	642.86 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.967, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6346, 3466, 2802
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.143, 1.09
No. of reflections	3466
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.88	2.02	2.6317 (15)	125.7
N2—H2A···O1ⁱ	0.88	2.51	3.3424 (15)	158.3
C2—H2B···F1ⁱⁱ	0.95	2.45	3.3386 (17)	156.4
C3—H3A···O4ⁱⁱⁱ	0.95	2.48	3.3177 (19)	147.7
C5—H5A···O3^iv	0.95	2.43	3.2694 (17)	147.6

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3, −y, −z+1; (iii) x+2, y−1, z; (iv) −x+1, −y, −z.

Cg···Cg π-ring stacking interactions, Cg1 and Cg2 are the centroids of rings C1–C6 and C8–C13; [Symmetry codes: (i) 1+x,y,z; (ii) -1+x, y, z] top

CgI···CgJ	Cg···Cg (Å)	Cg I_Perp (Å)	CgJ_Perp (Å)
Cg1···Cg2ⁱ	3.6916 (10)	-3.4632 (6)	3.3267 (5)
Cg2···Cg1ⁱⁱ	3.6916 (10)	3.3267 (5)	-3.4632 (6)

Acknowledgements

CSCK and HSY thank the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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