N'-[(E)-Furan-2-ylmethyl-idene]-4-hydroxy-benzohydrazide.

The title compound, C12H10N2O3, exists in the E conformation. The five-membered ring and the phenyl rings form dihedral angles of 36.73 (10) and 12.22 (10)°, respectively, with the central C(=O)N2C unit. The crystal packing is dominated by strong N-H⋯O and O-H⋯N hydrogen bonds. Together with weaker C-H⋯O inter-actions, these establish a three-dimensional supra-molecular network.

Related literature

For biological applications of benzohydrazones and derivatives, see: Sreeja et al. (2004 ▶); Rakha et al. (1996 ▶). For the synthesis of related compounds, see: Emmanuel et al. (2011 ▶). For a related structure, see: Datta et al. (2013 ▶).

Experimental

Crystal data

C12H10N2O3

M = 230.22

Orthorhombic,

a = 9.5934 (3) Å

b = 11.1939 (4) Å

c = 10.3332 (3) Å

V = 1109.66 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.25 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.975, T max = 0.984

3425 measured reflections

1014 independent reflections

992 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.064

S = 1.05

1014 reflections

163 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.10 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) Global, I. DOI: 10.1107/S1600536814001822/fj2657sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001822/fj2657Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001822/fj2657Isup3.cml

CCDC reference:

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

C12H10N2O3	F(000) = 480
Mr = 230.22	Dx = 1.378 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	θ = 2.7–28.4°
a = 9.5934 (3) Å	µ = 0.10 mm−1
b = 11.1939 (4) Å	T = 298 K
c = 10.3332 (3) Å	Block, light orange
V = 1109.66 (6) Å3	0.25 × 0.20 × 0.16 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	1014 independent reflections
Radiation source: fine-focus sealed tube	992 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.33 pixels mm-1	θmax = 25.0°, θmin = 2.7°
phi and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −13→9
Tmin = 0.975, Tmax = 0.984	l = −10→12
3425 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.0363P)2 + 0.1774P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1014 reflections	Δρmax = 0.13 e Å−3
163 parameters	Δρmin = −0.10 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.046 (5)

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.

	x	y	z	Uiso*/Ueq
O1	1.10537 (16)	0.44042 (12)	0.85962 (16)	0.0487 (4)
O2	1.15292 (13)	0.82491 (12)	0.64988 (16)	0.0454 (4)
O3	0.79142 (15)	1.25293 (13)	0.43449 (17)	0.0509 (4)
N1	1.00354 (16)	0.64857 (13)	0.74734 (17)	0.0346 (4)
N2	0.94150 (15)	0.74797 (14)	0.69195 (18)	0.0357 (4)
C1	1.1354 (3)	0.3230 (2)	0.8813 (3)	0.0609 (7)
H1	1.2119	0.2956	0.9279	0.073*
C2	1.0401 (3)	0.2529 (2)	0.8265 (3)	0.0655 (7)
H2	1.0390	0.1698	0.8271	0.079*
C3	0.9410 (3)	0.32850 (19)	0.7673 (3)	0.0528 (6)
H3	0.8614	0.3054	0.7224	0.063*
C4	0.9853 (2)	0.44092 (17)	0.7889 (2)	0.0394 (5)
C5	0.9330 (2)	0.55207 (17)	0.7401 (2)	0.0389 (5)
H5	0.8452	0.5539	0.7019	0.047*
C6	1.02519 (18)	0.83589 (16)	0.64733 (19)	0.0332 (4)
C7	0.95845 (19)	0.94475 (16)	0.5952 (2)	0.0327 (4)
C8	0.81588 (19)	0.96915 (18)	0.6015 (2)	0.0422 (5)
H8	0.7566	0.9156	0.6428	0.051*
C9	0.7622 (2)	1.07164 (18)	0.5474 (2)	0.0464 (5)
H9	0.6670	1.0866	0.5525	0.056*
C10	0.8484 (2)	1.15259 (16)	0.48562 (19)	0.0363 (5)
C11	0.9907 (2)	1.13042 (17)	0.4805 (2)	0.0400 (5)
H11	1.0502	1.1850	0.4410	0.048*
C12	1.04335 (19)	1.02759 (17)	0.5340 (2)	0.0383 (5)
H12	1.1387	1.0131	0.5291	0.046*
H2'	0.8518 (11)	0.7474 (18)	0.676 (2)	0.041 (6)*
H3'	0.853 (2)	1.288 (2)	0.389 (2)	0.062 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0473 (8)	0.0475 (9)	0.0515 (9)	0.0037 (7)	−0.0047 (7)	0.0042 (8)
O2	0.0233 (6)	0.0449 (8)	0.0679 (10)	0.0008 (5)	−0.0012 (7)	0.0128 (8)
O3	0.0378 (8)	0.0491 (9)	0.0657 (11)	0.0131 (7)	0.0115 (9)	0.0196 (8)
N1	0.0280 (7)	0.0328 (8)	0.0428 (9)	0.0011 (6)	0.0003 (7)	0.0026 (7)
N2	0.0235 (7)	0.0349 (8)	0.0488 (10)	0.0005 (6)	−0.0024 (8)	0.0037 (7)
C1	0.0719 (16)	0.0551 (15)	0.0556 (14)	0.0205 (13)	0.0011 (14)	0.0138 (12)
C2	0.098 (2)	0.0364 (12)	0.0621 (15)	0.0059 (13)	0.0102 (16)	0.0116 (12)
C3	0.0609 (14)	0.0396 (11)	0.0578 (14)	−0.0100 (10)	0.0026 (12)	0.0031 (11)
C4	0.0360 (9)	0.0397 (10)	0.0426 (11)	−0.0017 (8)	0.0032 (9)	0.0006 (9)
C5	0.0302 (9)	0.0388 (10)	0.0478 (12)	−0.0020 (7)	−0.0008 (10)	−0.0004 (9)
C6	0.0261 (8)	0.0356 (9)	0.0380 (10)	−0.0006 (7)	−0.0014 (8)	−0.0012 (8)
C7	0.0271 (9)	0.0337 (9)	0.0372 (10)	−0.0006 (7)	−0.0001 (9)	−0.0020 (8)
C8	0.0283 (9)	0.0430 (10)	0.0554 (12)	0.0004 (8)	0.0087 (10)	0.0099 (11)
C9	0.0260 (9)	0.0519 (12)	0.0614 (13)	0.0090 (8)	0.0089 (11)	0.0101 (12)
C10	0.0328 (10)	0.0362 (10)	0.0399 (12)	0.0054 (8)	0.0017 (9)	0.0015 (9)
C11	0.0295 (10)	0.0416 (10)	0.0488 (13)	−0.0036 (8)	0.0037 (9)	0.0084 (10)
C12	0.0227 (9)	0.0419 (10)	0.0504 (13)	0.0010 (7)	0.0001 (9)	0.0044 (9)

O1—C4	1.364 (3)	C3—H3	0.9300
O1—C1	1.364 (3)	C4—C5	1.433 (3)
O2—C6	1.232 (2)	C5—H5	0.9300
O3—C10	1.356 (2)	C6—C7	1.478 (2)
O3—H3'	0.847 (10)	C7—C12	1.387 (2)
N1—C5	1.277 (2)	C7—C8	1.396 (3)
N1—N2	1.386 (2)	C8—C9	1.376 (3)
N2—C6	1.351 (2)	C8—H8	0.9300
N2—H2'	0.876 (10)	C9—C10	1.383 (3)
C1—C2	1.331 (4)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.389 (3)
C2—C3	1.412 (4)	C11—C12	1.373 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.347 (3)	C12—H12	0.9300
C4—O1—C1	105.67 (19)	O2—C6—N2	120.73 (17)
C10—O3—H3'	108.7 (18)	O2—C6—C7	121.39 (16)
C5—N1—N2	115.31 (16)	N2—C6—C7	117.87 (15)
C6—N2—N1	118.08 (14)	C12—C7—C8	117.77 (17)
C6—N2—H2'	121.6 (14)	C12—C7—C6	117.59 (15)
N1—N2—H2'	119.6 (14)	C8—C7—C6	124.63 (17)
C2—C1—O1	110.7 (2)	C9—C8—C7	120.71 (19)
C2—C1—H1	124.7	C9—C8—H8	119.6
O1—C1—H1	124.7	C7—C8—H8	119.6
C1—C2—C3	107.1 (2)	C8—C9—C10	120.64 (17)
C1—C2—H2	126.5	C8—C9—H9	119.7
C3—C2—H2	126.5	C10—C9—H9	119.7
C4—C3—C2	106.0 (2)	O3—C10—C9	118.77 (17)
C4—C3—H3	127.0	O3—C10—C11	121.97 (18)
C2—C3—H3	127.0	C9—C10—C11	119.24 (18)
C3—C4—O1	110.59 (19)	C12—C11—C10	119.74 (18)
C3—C4—C5	129.9 (2)	C12—C11—H11	120.1
O1—C4—C5	119.19 (18)	C10—C11—H11	120.1
N1—C5—C4	121.89 (19)	C11—C12—C7	121.88 (16)
N1—C5—H5	119.1	C11—C12—H12	119.1
C4—C5—H5	119.1	C7—C12—H12	119.1
C5—N1—N2—C6	−152.8 (2)	N2—C6—C7—C12	−171.64 (19)
C4—O1—C1—C2	0.4 (3)	O2—C6—C7—C8	−172.9 (2)
O1—C1—C2—C3	−0.9 (3)	N2—C6—C7—C8	7.4 (3)
C1—C2—C3—C4	1.0 (3)	C12—C7—C8—C9	0.7 (3)
C2—C3—C4—O1	−0.8 (3)	C6—C7—C8—C9	−178.4 (2)
C2—C3—C4—C5	173.0 (2)	C7—C8—C9—C10	0.0 (4)
C1—O1—C4—C3	0.2 (3)	C8—C9—C10—O3	−179.5 (2)
C1—O1—C4—C5	−174.3 (2)	C8—C9—C10—C11	−1.1 (3)
N2—N1—C5—C4	177.85 (18)	O3—C10—C11—C12	179.84 (19)
C3—C4—C5—N1	−164.8 (3)	C9—C10—C11—C12	1.5 (3)
O1—C4—C5—N1	8.5 (3)	C10—C11—C12—C7	−0.8 (3)
N1—N2—C6—O2	3.7 (3)	C8—C7—C12—C11	−0.3 (3)
N1—N2—C6—C7	−176.57 (16)	C6—C7—C12—C11	178.9 (2)
O2—C6—C7—C12	8.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O2i	0.88 (1)	2.09 (1)	2.9187 (19)	157 (2)
O3—H3′···N1ii	0.85 (1)	2.13 (1)	2.971 (2)	169 (3)
C5—H5···O2i	0.93	2.35	3.160 (2)	145
C11—H11···O3iii	0.93	2.42	3.202 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O2i	0.88 (1)	2.09 (1)	2.9187 (19)	157 (2)
O3—H3′⋯N1ii	0.85 (1)	2.13 (1)	2.971 (2)	169 (3)
C5—H5⋯O2i	0.93	2.35	3.160 (2)	145
C11—H11⋯O3iii	0.93	2.42	3.202 (2)	142

Symmetry codes: (i) ; (ii) ; (iii) .