(E)-2-{[(Furan-2-ylmeth-yl)imino]-meth-yl}-4-nitro-phenol.

In the title compound, C12H10N2O4, the furan-2-ylmethyl group is disordered over two sets of sites, with refined occupancies of 0.858 (3) and 0.143 (3). In the major component of disorder, the dihedral angle between the furan and benzene rings is 63.1 (2)° and for the minor component this value is 67.9 (6)°. The planes of the nitro group and the attached benzene ring form a dihedral angle of 4.34 (17)°. In the crystal, inversion-related mol-ecules are linked by two pairs of weak C-H⋯O inter-actions, one involving the nitro group and the other involving the O-H group as an acceptor. As a result of these associations, ribbons are formed along [120]. A strong intra-molecular O-H⋯N hydrogen bond is observed.

Related literature

For the use of salicyl­idene compounds as anion sensors, see: Hijji et al. (2009 ▶) and for the use of related compounds as anion sensors, see: Hijji et al. (2004 ▶). For the bioactivity of metal complexes of structurally related salicyl­idene derivatives, see: Mandal et al. (2009a ▶,b ▶). For related structures, see: Song et al. (2008 ▶); Khalaji et al. (2011a ▶,b ▶).

Experimental

Crystal data

C12H10N2O4

M = 246.22

Triclinic,

a = 5.4427 (7) Å

b = 8.2488 (10) Å

c = 12.4701 (14) Å

α = 98.901 (9)°

β = 92.04 (1)°

γ = 91.69 (1)°

V = 552.41 (12) Å3

Z = 2

Cu Kα radiation

μ = 0.96 mm−1

T = 123 K

0.34 × 0.26 × 0.17 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.912, T max = 1.000

3400 measured reflections

2210 independent reflections

2047 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.122

S = 1.06

2210 reflections

186 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO (Agilent, 2012 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814005583/lh5694sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005583/lh5694Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005583/lh5694Isup3.cml

CCDC reference: 991243

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H10N2O4	Z = 2
Mr = 246.22	F(000) = 256
Triclinic, P1	Dx = 1.480 Mg m−3
a = 5.4427 (7) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.2488 (10) Å	Cell parameters from 2639 reflections
c = 12.4701 (14) Å	θ = 3.6–75.5°
α = 98.901 (9)°	µ = 0.96 mm−1
β = 92.04 (1)°	T = 123 K
γ = 91.69 (1)°	Prism, pale yellow
V = 552.41 (12) Å3	0.34 × 0.26 × 0.17 mm

Agilent Xcalibur (Ruby, Gemini) diffractometer	2047 reflections with I > 2σ(I)
Detector resolution: 10.5081 pixels mm-1	Rint = 0.019
ω scans	θmax = 75.6°, θmin = 3.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −6→6
Tmin = 0.912, Tmax = 1.000	k = −10→10
3400 measured reflections	l = −11→15
2210 independent reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0764P)2 + 0.0922P] where P = (Fo2 + 2Fc2)/3
2210 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.32 e Å−3
13 restraints	Δρmin = −0.27 e Å−3

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.1H-NMR (400 MHz): d ppm (CDCl3): 14.41(br. s 1H), 8.39 (t, J = 1.25 Hz, 1H) 8.255 (d, J = 2.85 Hz, 1H), 8.205 (dd, J = 8.25, 2.85 Hz, 1H), 7.44 ( dd, J = 1.75, 0.75 Hz, 1H), 7.01 ( d, J = 7.30 Hz, 1H), 6.395 (dd, J = 3.45, 1.85 Hz, 1H), 6.35 dt, J = 3.45, 0.75 Hz, 1 H), 4.84 (s, 2 H). 13C-NMR (100 MHz) d ppm (CDCl3): 167.64, 164.96, 149.57, 143.12, 139.45, 128.23, 128.08, 118.46, 117.44, 110.05, 108.99, 54.01. Mass spec: M+ = 246.

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.24922 (16)	0.42490 (11)	0.60178 (7)	0.0282 (2)
H1O	0.352 (5)	0.424 (3)	0.665 (2)	0.082 (8)*
O2	0.51829 (18)	0.00193 (12)	0.16611 (7)	0.0345 (2)
O3	0.83082 (19)	−0.04412 (13)	0.26772 (8)	0.0406 (3)
N1	0.6361 (2)	0.02267 (13)	0.25331 (9)	0.0281 (2)
N2	0.6077 (2)	0.34958 (13)	0.72346 (8)	0.0281 (2)
C1	0.3478 (2)	0.33032 (14)	0.51862 (9)	0.0226 (2)
C2	0.2310 (2)	0.31430 (15)	0.41515 (10)	0.0244 (2)
H2A	0.0863	0.3727	0.4049	0.029*
C3	0.3249 (2)	0.21438 (14)	0.32834 (9)	0.0242 (2)
H3A	0.2450	0.2024	0.2585	0.029*
C4	0.5397 (2)	0.13099 (14)	0.34469 (9)	0.0233 (2)
C5	0.6607 (2)	0.14649 (14)	0.44537 (10)	0.0240 (2)
H5A	0.8072	0.0893	0.4542	0.029*
C6	0.5667 (2)	0.24627 (14)	0.53369 (9)	0.0222 (2)
C7	0.6911 (2)	0.26050 (14)	0.64088 (10)	0.0256 (3)
H7A	0.8368	0.2022	0.6491	0.031*
O4	0.6949 (2)	0.62761 (19)	0.92624 (12)	0.0322 (3)	0.858 (3)
C8	0.7459 (4)	0.3535 (3)	0.8281 (2)	0.0320 (5)	0.858 (3)
H8A	0.8813	0.2757	0.8180	0.038*	0.858 (3)
H8B	0.6350	0.3170	0.8816	0.038*	0.858 (3)
C9	0.8503 (5)	0.5208 (3)	0.8716 (3)	0.0253 (3)	0.858 (3)
C10	1.0759 (3)	0.5895 (2)	0.87026 (14)	0.0297 (4)	0.858 (3)
H10A	1.2147	0.5405	0.8362	0.036*	0.858 (3)
C11	1.0658 (4)	0.7526 (2)	0.93068 (14)	0.0318 (4)	0.858 (3)
H11A	1.1970	0.8325	0.9449	0.038*	0.858 (3)
C12	0.8342 (4)	0.76926 (19)	0.96289 (13)	0.0328 (4)	0.858 (3)
H12A	0.7744	0.8649	1.0049	0.039*	0.858 (3)
O4A	0.7528 (18)	0.6486 (14)	0.9445 (9)	0.0322 (3)	0.142 (3)
C8A	0.694 (3)	0.3590 (19)	0.8374 (16)	0.0320 (5)	0.142 (3)
H8A1	0.8057	0.2681	0.8444	0.038*	0.142 (3)
H8A2	0.5526	0.3481	0.8836	0.038*	0.142 (3)
C9A	0.827 (3)	0.519 (2)	0.8736 (17)	0.0253 (3)	0.142 (3)
C10A	1.0441 (18)	0.5434 (14)	0.8316 (9)	0.0297 (4)	0.142 (3)
H10B	1.1253	0.4736	0.7772	0.036*	0.142 (3)
C11A	1.1230 (19)	0.6970 (14)	0.8873 (9)	0.0318 (4)	0.142 (3)
H11B	1.2789	0.7477	0.8793	0.038*	0.142 (3)
C12A	0.950 (3)	0.7651 (13)	0.9539 (9)	0.0328 (4)	0.142 (3)
H12B	0.9601	0.8700	0.9981	0.039*	0.142 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0281 (4)	0.0311 (4)	0.0245 (4)	0.0086 (3)	0.0018 (3)	0.0001 (3)
O2	0.0409 (5)	0.0361 (5)	0.0247 (4)	0.0025 (4)	0.0013 (4)	−0.0014 (4)
O3	0.0365 (5)	0.0429 (6)	0.0409 (5)	0.0172 (4)	0.0048 (4)	−0.0024 (4)
N1	0.0291 (5)	0.0253 (5)	0.0298 (5)	0.0021 (4)	0.0052 (4)	0.0034 (4)
N2	0.0347 (5)	0.0247 (5)	0.0245 (5)	0.0003 (4)	−0.0056 (4)	0.0040 (4)
C1	0.0220 (5)	0.0210 (5)	0.0252 (5)	0.0008 (4)	0.0021 (4)	0.0048 (4)
C2	0.0205 (5)	0.0249 (5)	0.0283 (6)	0.0036 (4)	−0.0002 (4)	0.0059 (4)
C3	0.0243 (5)	0.0261 (5)	0.0229 (5)	−0.0002 (4)	−0.0010 (4)	0.0063 (4)
C4	0.0246 (5)	0.0203 (5)	0.0249 (6)	0.0009 (4)	0.0038 (4)	0.0027 (4)
C5	0.0212 (5)	0.0209 (5)	0.0308 (6)	0.0030 (4)	0.0016 (4)	0.0067 (4)
C6	0.0225 (5)	0.0202 (5)	0.0244 (5)	0.0003 (4)	−0.0007 (4)	0.0054 (4)
C7	0.0263 (5)	0.0211 (5)	0.0299 (6)	0.0011 (4)	−0.0047 (4)	0.0064 (4)
O4	0.0284 (7)	0.0340 (6)	0.0326 (7)	0.0038 (5)	0.0018 (5)	−0.0002 (5)
C8	0.0410 (13)	0.0279 (6)	0.0266 (8)	0.0046 (8)	−0.0087 (8)	0.0042 (5)
C9	0.0277 (8)	0.0287 (6)	0.0195 (5)	0.0067 (5)	−0.0021 (5)	0.0030 (4)
C10	0.0246 (7)	0.0411 (10)	0.0230 (8)	0.0050 (6)	0.0016 (6)	0.0032 (7)
C11	0.0386 (9)	0.0338 (9)	0.0222 (8)	−0.0078 (7)	−0.0049 (7)	0.0047 (6)
C12	0.0441 (10)	0.0261 (7)	0.0268 (7)	0.0069 (7)	−0.0003 (7)	−0.0011 (5)
O4A	0.0284 (7)	0.0340 (6)	0.0326 (7)	0.0038 (5)	0.0018 (5)	−0.0002 (5)
C8A	0.0410 (13)	0.0279 (6)	0.0266 (8)	0.0046 (8)	−0.0087 (8)	0.0042 (5)
C9A	0.0277 (8)	0.0287 (6)	0.0195 (5)	0.0067 (5)	−0.0021 (5)	0.0030 (4)
C10A	0.0246 (7)	0.0411 (10)	0.0230 (8)	0.0050 (6)	0.0016 (6)	0.0032 (7)
C11A	0.0386 (9)	0.0338 (9)	0.0222 (8)	−0.0078 (7)	−0.0049 (7)	0.0047 (6)
C12A	0.0441 (10)	0.0261 (7)	0.0268 (7)	0.0069 (7)	−0.0003 (7)	−0.0011 (5)

O1—C1	1.3363 (14)	C8—C9	1.491 (3)
O1—H1O	0.95 (3)	C8—H8A	0.9900
O2—N1	1.2286 (15)	C8—H8B	0.9900
O3—N1	1.2289 (15)	C9—C10	1.339 (3)
N1—C4	1.4586 (15)	C10—C11	1.440 (3)
N2—C7	1.2747 (17)	C10—H10A	0.9500
N2—C8A	1.47 (2)	C11—C12	1.341 (3)
N2—C8	1.479 (3)	C11—H11A	0.9500
C1—C2	1.4036 (16)	C12—H12A	0.9500
C1—C6	1.4172 (16)	O4A—C9A	1.359 (14)
C2—C3	1.3788 (17)	O4A—C12A	1.410 (14)
C2—H2A	0.9500	C8A—C9A	1.483 (14)
C3—C4	1.3982 (17)	C8A—H8A1	0.9900
C3—H3A	0.9500	C8A—H8A2	0.9900
C4—C5	1.3830 (17)	C9A—C10A	1.333 (14)
C5—C6	1.3917 (17)	C10A—C11A	1.395 (12)
C5—H5A	0.9500	C10A—H10B	0.9500
C6—C7	1.4633 (16)	C11A—C12A	1.354 (13)
C7—H7A	0.9500	C11A—H11B	0.9500
O4—C9	1.362 (3)	C12A—H12B	0.9500
O4—C12	1.381 (2)
C1—O1—H1O	108.3 (17)	H8A—C8—H8B	107.9
O2—N1—O3	123.29 (11)	C10—C9—O4	111.09 (19)
O2—N1—C4	118.49 (10)	C10—C9—C8	132.3 (2)
O3—N1—C4	118.22 (11)	O4—C9—C8	116.55 (19)
C7—N2—C8A	127.0 (7)	C9—C10—C11	106.24 (16)
C7—N2—C8	116.83 (12)	C9—C10—H10A	126.9
O1—C1—C2	119.08 (10)	C11—C10—H10A	126.9
O1—C1—C6	120.99 (10)	C12—C11—C10	106.29 (14)
C2—C1—C6	119.92 (11)	C12—C11—H11A	126.9
C3—C2—C1	120.40 (11)	C10—C11—H11A	126.9
C3—C2—H2A	119.8	C11—C12—O4	110.34 (14)
C1—C2—H2A	119.8	C11—C12—H12A	124.8
C2—C3—C4	119.02 (11)	O4—C12—H12A	124.8
C2—C3—H3A	120.5	C9A—O4A—C12A	104.9 (10)
C4—C3—H3A	120.5	N2—C8A—C9A	109.4 (15)
C5—C4—C3	121.81 (11)	N2—C8A—H8A1	109.8
C5—C4—N1	119.21 (10)	C9A—C8A—H8A1	109.8
C3—C4—N1	118.97 (11)	N2—C8A—H8A2	109.8
C4—C5—C6	119.65 (11)	C9A—C8A—H8A2	109.8
C4—C5—H5A	120.2	H8A1—C8A—H8A2	108.2
C6—C5—H5A	120.2	C10A—C9A—O4A	114.2 (11)
C5—C6—C1	119.19 (11)	C10A—C9A—C8A	117.8 (13)
C5—C6—C7	119.90 (10)	O4A—C9A—C8A	128.0 (13)
C1—C6—C7	120.90 (11)	C9A—C10A—C11A	102.9 (10)
N2—C7—C6	121.28 (11)	C9A—C10A—H10B	128.6
N2—C7—H7A	119.4	C11A—C10A—H10B	128.6
C6—C7—H7A	119.4	C12A—C11A—C10A	111.8 (9)
C9—O4—C12	106.02 (16)	C12A—C11A—H11B	124.1
N2—C8—C9	112.0 (2)	C10A—C11A—H11B	124.1
N2—C8—H8A	109.2	C11A—C12A—O4A	106.0 (9)
C9—C8—H8A	109.2	C11A—C12A—H12B	127.0
N2—C8—H8B	109.2	O4A—C12A—H12B	127.0
C9—C8—H8B	109.2
O1—C1—C2—C3	−178.40 (10)	C8A—N2—C8—C9	−94 (3)
C6—C1—C2—C3	1.40 (18)	C12—O4—C9—C10	−1.4 (3)
C1—C2—C3—C4	−0.77 (18)	C12—O4—C9—C8	177.1 (3)
C2—C3—C4—C5	−0.24 (18)	N2—C8—C9—C10	−100.0 (4)
C2—C3—C4—N1	178.74 (10)	N2—C8—C9—O4	81.9 (3)
O2—N1—C4—C5	175.41 (10)	O4—C9—C10—C11	1.2 (3)
O3—N1—C4—C5	−4.15 (17)	C8—C9—C10—C11	−177.0 (4)
O2—N1—C4—C3	−3.60 (17)	C9—C10—C11—C12	−0.4 (2)
O3—N1—C4—C3	176.84 (11)	C10—C11—C12—O4	−0.44 (18)
C3—C4—C5—C6	0.62 (18)	C9—O4—C12—C11	1.1 (2)
N1—C4—C5—C6	−178.37 (10)	C7—N2—C8A—C9A	108.4 (12)
C4—C5—C6—C1	0.02 (17)	C8—N2—C8A—C9A	74 (3)
C4—C5—C6—C7	178.74 (10)	C12A—O4A—C9A—C10A	−4 (2)
O1—C1—C6—C5	178.78 (10)	C12A—O4A—C9A—C8A	177 (2)
C2—C1—C6—C5	−1.01 (17)	N2—C8A—C9A—C10A	−70 (2)
O1—C1—C6—C7	0.07 (17)	N2—C8A—C9A—O4A	109 (2)
C2—C1—C6—C7	−179.72 (10)	O4A—C9A—C10A—C11A	5 (2)
C8A—N2—C7—C6	171.7 (8)	C8A—C9A—C10A—C11A	−176.2 (18)
C8—N2—C7—C6	179.22 (13)	C9A—C10A—C11A—C12A	−4.2 (16)
C5—C6—C7—N2	−179.25 (11)	C10A—C11A—C12A—O4A	2.1 (13)
C1—C6—C7—N2	−0.55 (18)	C9A—O4A—C12A—C11A	0.9 (16)
C7—N2—C8—C9	116.69 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.95 (3)	1.72 (3)	2.5784 (14)	148 (2)
C2—H2A···O1i	0.95	2.52	3.4548 (16)	169
C7—H7A···O3ii	0.95	2.54	3.4567 (16)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2	0.95 (3)	1.72 (3)	2.5784 (14)	148 (2)
C2—H2A⋯O1i	0.95	2.52	3.4548 (16)	169
C7—H7A⋯O3ii	0.95	2.54	3.4567 (16)	161

Symmetry codes: (i) ; (ii) .