2-[((E)-2-{2-[(E)-2-Hy-droxy-benzyl-idene]hydrazinecarbon-yl}hydrazinyl-idene)meth-yl]phenol.

The mol-ecule of the title compound, C(15)H(14)N(4)O(3), is completed by the application of crystallographic twofold symmetry, with the carbonyl group lying on the rotation axis. The mol-ecule is close to planar: the greatest deviation of a torsion angle from 0° is 7.3 (2)° about the bond linking the phenol ring to the rest of the mol-ecule. An intra-molecular O-H⋯N(imine) hydrogen bond is formed in each half of the mol-ecule. The carbonyl O atom is anti with respect to the amine H atoms and this allows for the formation of N-H⋯O(hydrox-yl) hydrogen bonds in the crystal, which results in supra-molecular layers lying parallel to (100).

Related literature

For the structures of related carbohydrazides, see: Bikas et al. (2010a ▶,b ▶).

Experimental

Crystal data

C15H14N4O3

M = 298.30

Orthorhombic,

a = 14.3101 (4) Å

b = 9.3620 (2) Å

c = 10.2697 (2) Å

V = 1375.84 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.86 mm−1

T = 100 K

0.25 × 0.25 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.342, T max = 1.000

2323 measured reflections

757 independent reflections

750 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.075

S = 1.10

757 reflections

110 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053268/hb6561sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053268/hb6561Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053268/hb6561Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14N4O3	F(000) = 624
Mr = 298.30	Dx = 1.440 Mg m−3
Orthorhombic, Aba2	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: A 2 -2ac	Cell parameters from 1858 reflections
a = 14.3101 (4) Å	θ = 3.1–76.5°
b = 9.3620 (2) Å	µ = 0.86 mm−1
c = 10.2697 (2) Å	T = 100 K
V = 1375.84 (6) Å3	Prism, colourless
Z = 4	0.25 × 0.25 × 0.10 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	757 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	750 reflections with I > 2σ(I)
Mirror	Rint = 0.014
Detector resolution: 10.4041 pixels mm-1	θmax = 76.7°, θmin = 6.2°
ω scan	h = −17→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→10
Tmin = 0.342, Tmax = 1.000	l = −10→12
2323 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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.2173P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
757 reflections	Δρmax = 0.16 e Å−3
110 parameters	Δρmin = −0.21 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (7)

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	0.5000	0.5000	0.50067 (16)	0.0218 (4)
O2	0.59665 (8)	0.87891 (12)	0.43307 (12)	0.0197 (3)
N1	0.52439 (9)	0.61383 (13)	0.69670 (15)	0.0186 (3)
N2	0.55917 (9)	0.73346 (13)	0.63891 (13)	0.0170 (3)
C1	0.5000	0.5000	0.6191 (2)	0.0174 (4)
C2	0.57681 (11)	0.84255 (16)	0.71089 (15)	0.0172 (3)
H2A	0.5646	0.8395	0.8018	0.021*
C3	0.61574 (10)	0.97076 (15)	0.65176 (15)	0.0159 (4)
C4	0.64432 (11)	1.08454 (17)	0.73122 (16)	0.0191 (4)
H4	0.6380	1.0769	0.8230	0.023*
C5	0.68171 (11)	1.20828 (18)	0.67764 (18)	0.0211 (4)
H5	0.7009	1.2847	0.7324	0.025*
C6	0.69086 (11)	1.21928 (18)	0.54321 (19)	0.0219 (4)
H6	0.7165	1.3036	0.5062	0.026*
C7	0.66290 (11)	1.10842 (16)	0.46270 (15)	0.0195 (4)
H7	0.6698	1.1169	0.3710	0.023*
C8	0.62482 (9)	0.98474 (16)	0.51579 (14)	0.0159 (4)
H1	0.5006 (17)	0.614 (2)	0.777 (3)	0.023 (5)*
H2	0.579 (2)	0.809 (3)	0.481 (3)	0.051 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0307 (8)	0.0208 (7)	0.0138 (8)	−0.0031 (6)	0.000	0.000
O2	0.0260 (6)	0.0186 (5)	0.0146 (5)	−0.0020 (4)	−0.0006 (5)	−0.0009 (4)
N1	0.0253 (7)	0.0169 (7)	0.0136 (6)	−0.0027 (5)	0.0024 (5)	0.0014 (5)
N2	0.0183 (6)	0.0166 (7)	0.0160 (7)	0.0001 (5)	−0.0004 (5)	0.0014 (5)
C1	0.0181 (10)	0.0175 (10)	0.0167 (10)	0.0017 (7)	0.000	0.000
C2	0.0176 (6)	0.0190 (7)	0.0149 (7)	0.0010 (5)	−0.0001 (5)	0.0002 (6)
C3	0.0147 (7)	0.0180 (7)	0.0150 (7)	0.0022 (6)	−0.0004 (6)	0.0005 (6)
C4	0.0181 (7)	0.0219 (8)	0.0174 (8)	0.0007 (6)	−0.0004 (6)	−0.0010 (7)
C5	0.0195 (7)	0.0197 (8)	0.0241 (8)	−0.0025 (5)	0.0002 (6)	−0.0040 (6)
C6	0.0186 (8)	0.0209 (8)	0.0261 (9)	−0.0031 (5)	0.0009 (7)	0.0035 (7)
C7	0.0190 (7)	0.0230 (7)	0.0166 (8)	−0.0003 (6)	0.0009 (6)	0.0027 (6)
C8	0.0136 (7)	0.0181 (7)	0.0161 (9)	0.0016 (5)	−0.0009 (6)	−0.0003 (6)

O1—C1	1.217 (3)	C3—C4	1.403 (2)
O2—C8	1.3660 (19)	C3—C8	1.408 (2)
O2—H2	0.86 (3)	C4—C5	1.390 (2)
N1—N2	1.3617 (16)	C4—H4	0.9500
N1—C1	1.3754 (19)	C5—C6	1.391 (3)
N1—H1	0.89 (3)	C5—H5	0.9500
N2—C2	1.2857 (19)	C6—C7	1.386 (2)
C1—N1i	1.3754 (19)	C6—H6	0.9500
C2—C3	1.456 (2)	C7—C8	1.391 (2)
C2—H2A	0.9500	C7—H7	0.9500
C8—O2—H2	106 (2)	C5—C4—H4	119.5
N2—N1—C1	118.53 (14)	C3—C4—H4	119.5
N2—N1—H1	122.6 (13)	C4—C5—C6	119.41 (17)
C1—N1—H1	116.2 (14)	C4—C5—H5	120.3
C2—N2—N1	118.33 (13)	C6—C5—H5	120.3
O1—C1—N1	125.38 (10)	C7—C6—C5	120.64 (16)
O1—C1—N1i	125.38 (10)	C7—C6—H6	119.7
N1—C1—N1i	109.2 (2)	C5—C6—H6	119.7
N2—C2—C3	119.35 (14)	C6—C7—C8	120.17 (15)
N2—C2—H2A	120.3	C6—C7—H7	119.9
C3—C2—H2A	120.3	C8—C7—H7	119.9
C4—C3—C8	118.64 (14)	O2—C8—C7	118.40 (14)
C4—C3—C2	119.67 (14)	O2—C8—C3	121.46 (14)
C8—C3—C2	121.69 (14)	C7—C8—C3	120.14 (14)
C5—C4—C3	120.99 (16)
C1—N1—N2—C2	176.05 (12)	C4—C5—C6—C7	0.1 (2)
N2—N1—C1—O1	−5.97 (14)	C5—C6—C7—C8	0.3 (2)
N2—N1—C1—N1i	174.03 (14)	C6—C7—C8—O2	178.90 (13)
N1—N2—C2—C3	178.82 (12)	C6—C7—C8—C3	−0.9 (2)
N2—C2—C3—C4	−173.31 (13)	C4—C3—C8—O2	−178.76 (13)
N2—C2—C3—C8	7.3 (2)	C2—C3—C8—O2	0.6 (2)
C8—C3—C4—C5	−0.6 (2)	C4—C3—C8—C7	1.1 (2)
C2—C3—C4—C5	−179.99 (13)	C2—C3—C8—C7	−179.58 (13)
C3—C4—C5—C6	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.86 (3)	1.79 (4)	2.5710 (17)	150 (3)
N1—H1···O2ii	0.89 (3)	2.12 (3)	2.983 (2)	161 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.86 (3)	1.79 (4)	2.5710 (17)	150 (3)
N1—H1⋯O2i	0.89 (3)	2.12 (3)	2.983 (2)	161 (2)

Symmetry code: (i) .