1,2-Bis(2-hy-droxy-5-methyl-benzyl-idene)hydrazine.

The mol-ecular structure of the title compound, C16H16N2O2, is stabilized by intra-molecular O-H⋯N hydrogen bonds with S(6) graph-set motifs, so that the mol-ecule is almost planar, with a C=N-N=C torsion angle of -179.7 (2)° and a dihedral angle of 1.82 (12)° between the aromatic rings. In the crystal, weak C-H⋯π inter-actions lead to the formation of a three-dimensional network.

Related literature

For the biological activity of Schiff base ligands, see: Kelley et al. (1995 ▶); Pandeya et al. (1999 ▶); Singh & Dash (1988 ▶); Tarafder et al. (2002 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For related strucutures, see: Chantrapromma et al. (2010 ▶); Fun et al. (2010 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H16N2O2

M = 268.31

Orthorhombic,

a = 6.0108 (5) Å

b = 7.3394 (5) Å

c = 31.674 (2) Å

V = 1397.32 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.22 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.982, T max = 0.987

5699 measured reflections

2952 independent reflections

1780 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.154

S = 1.02

2952 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681302148X/is5296sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302148X/is5296Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302148X/is5296Isup3.cml

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

C16H16N2O2	F(000) = 568
Mr = 268.31	Dx = 1.275 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2658 reflections
a = 6.0108 (5) Å	θ = 2.4–27.2°
b = 7.3394 (5) Å	µ = 0.09 mm−1
c = 31.674 (2) Å	T = 295 K
V = 1397.32 (17) Å3	Block, yellow
Z = 4	0.22 × 0.18 × 0.16 mm

Bruker Kappa APEXII diffractometer	2952 independent reflections
Radiation source: fine-focus sealed tube	1780 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω and φ scans	θmax = 27.2°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
Tmin = 0.982, Tmax = 0.987	k = −9→9
5699 measured reflections	l = −40→39

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0788P)2] where P = (Fo2 + 2Fc2)/3
2952 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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 > 2sigma(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
C1	−0.1393 (4)	0.8872 (3)	0.28106 (7)	0.0424 (6)
C2	−0.0535 (4)	0.9211 (3)	0.24097 (7)	0.0467 (6)
H2	0.0874	0.9726	0.2387	0.056*
C3	−0.1689 (5)	0.8812 (4)	0.20427 (8)	0.0528 (7)
C4	−0.3790 (5)	0.8051 (4)	0.20879 (8)	0.0558 (7)
H4	−0.4604	0.7765	0.1847	0.067*
C5	−0.4700 (5)	0.7708 (3)	0.24753 (9)	0.0540 (7)
H5	−0.6106	0.7185	0.2493	0.065*
C6	−0.3559 (4)	0.8129 (4)	0.28389 (8)	0.0474 (7)
C7	−0.0682 (6)	0.9219 (4)	0.16150 (7)	0.0766 (10)
H7A	−0.0947	0.8212	0.1428	0.115*
H7B	0.0891	0.9405	0.1645	0.115*
H7C	−0.1352	1.0299	0.1500	0.115*
C8	−0.0071 (4)	0.9275 (3)	0.31799 (7)	0.0454 (6)
H8	0.1363	0.9726	0.3145	0.055*
C9	−0.0019 (4)	0.9213 (3)	0.42464 (7)	0.0451 (6)
H9	−0.1451	0.8758	0.4282	0.054*
C10	0.1302 (5)	0.9612 (3)	0.46142 (7)	0.0429 (6)
C11	0.0395 (5)	0.9322 (3)	0.50158 (7)	0.0478 (7)
H11	−0.1016	0.8810	0.5035	0.057*
C12	0.1501 (5)	0.9762 (3)	0.53841 (8)	0.0527 (7)
C13	0.3625 (6)	1.0501 (4)	0.53396 (8)	0.0578 (8)
H13	0.4417	1.0814	0.5581	0.069*
C14	0.4593 (5)	1.0786 (4)	0.49519 (8)	0.0556 (7)
H14	0.6019	1.1271	0.4935	0.067*
C15	0.3451 (5)	1.0352 (3)	0.45871 (8)	0.0460 (6)
C16	0.0438 (6)	0.9530 (4)	0.58087 (8)	0.0718 (9)
H16A	−0.0435	1.0588	0.5874	0.108*
H16B	0.1573	0.9378	0.6019	0.108*
H16C	−0.0504	0.8474	0.5805	0.108*
N1	−0.0818 (3)	0.9027 (3)	0.35543 (6)	0.0498 (6)
N2	0.0716 (4)	0.9465 (3)	0.38727 (6)	0.0498 (6)
O1	−0.4551 (3)	0.7801 (3)	0.32150 (5)	0.0680 (6)
H1	−0.3751	0.8171	0.3406	0.102*
O2	0.4451 (3)	1.0657 (3)	0.42094 (6)	0.0650 (6)
H2A	0.3623	1.0328	0.4018	0.098*

	U11	U22	U33	U12	U13	U23
C1	0.0381 (15)	0.0357 (12)	0.0534 (14)	0.0023 (12)	−0.0003 (12)	0.0034 (10)
C2	0.0442 (15)	0.0392 (13)	0.0565 (16)	0.0000 (13)	−0.0007 (12)	0.0069 (11)
C3	0.0594 (19)	0.0491 (15)	0.0499 (15)	0.0053 (16)	−0.0034 (13)	0.0016 (12)
C4	0.0553 (19)	0.0488 (15)	0.0633 (17)	0.0011 (16)	−0.0152 (15)	−0.0051 (13)
C5	0.0412 (15)	0.0494 (14)	0.0715 (17)	−0.0039 (14)	−0.0070 (15)	−0.0016 (14)
C6	0.0417 (16)	0.0458 (14)	0.0548 (15)	0.0020 (14)	0.0002 (13)	0.0028 (11)
C7	0.102 (3)	0.076 (2)	0.0512 (16)	−0.006 (2)	−0.0028 (17)	0.0065 (14)
C8	0.0386 (16)	0.0415 (13)	0.0562 (15)	−0.0024 (13)	−0.0057 (12)	0.0003 (12)
C9	0.0395 (15)	0.0413 (13)	0.0546 (14)	−0.0010 (13)	0.0000 (12)	0.0035 (11)
C10	0.0412 (17)	0.0358 (12)	0.0518 (14)	0.0041 (12)	−0.0031 (12)	0.0002 (10)
C11	0.0465 (17)	0.0399 (13)	0.0570 (15)	0.0003 (13)	−0.0003 (13)	0.0042 (12)
C12	0.058 (2)	0.0425 (14)	0.0572 (16)	0.0059 (15)	−0.0035 (14)	0.0008 (12)
C13	0.061 (2)	0.0471 (15)	0.0656 (18)	0.0036 (16)	−0.0186 (15)	−0.0005 (13)
C14	0.0401 (17)	0.0508 (15)	0.0759 (19)	−0.0037 (15)	−0.0086 (14)	0.0047 (14)
C15	0.0379 (16)	0.0436 (14)	0.0564 (15)	−0.0008 (13)	−0.0007 (13)	0.0036 (12)
C16	0.091 (3)	0.0697 (18)	0.0550 (16)	0.005 (2)	0.0022 (17)	0.0006 (14)
N1	0.0458 (13)	0.0551 (13)	0.0485 (11)	−0.0018 (12)	−0.0044 (10)	0.0023 (10)
N2	0.0476 (13)	0.0490 (12)	0.0527 (11)	−0.0004 (11)	−0.0053 (11)	0.0021 (9)
O1	0.0460 (12)	0.0922 (16)	0.0658 (12)	−0.0134 (12)	0.0067 (10)	0.0055 (12)
O2	0.0490 (12)	0.0778 (14)	0.0683 (11)	−0.0112 (12)	0.0037 (10)	0.0053 (11)

C1—C2	1.393 (3)	C9—H9	0.9300
C1—C6	1.415 (3)	C10—C11	1.400 (3)
C1—C8	1.445 (3)	C10—C15	1.404 (3)
C2—C3	1.385 (3)	C11—C12	1.381 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.388 (4)	C12—C13	1.395 (4)
C3—C7	1.514 (3)	C12—C16	1.499 (3)
C4—C5	1.367 (4)	C13—C14	1.375 (4)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.376 (3)	C14—C15	1.381 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—O1	1.354 (3)	C15—O2	1.357 (3)
C7—H7A	0.9600	C16—H16A	0.9600
C7—H7B	0.9600	C16—H16B	0.9600
C7—H7C	0.9600	C16—H16C	0.9600
C8—N1	1.281 (3)	N1—N2	1.404 (3)
C8—H8	0.9300	O1—H1	0.8200
C9—N2	1.277 (3)	O2—H2A	0.8200
C9—C10	1.440 (3)
C2—C1—C6	117.9 (2)	C10—C9—H9	119.0
C2—C1—C8	119.9 (2)	C11—C10—C15	118.2 (2)
C6—C1—C8	122.3 (2)	C11—C10—C9	119.3 (3)
C3—C2—C1	122.8 (2)	C15—C10—C9	122.5 (2)
C3—C2—H2	118.6	C12—C11—C10	123.0 (3)
C1—C2—H2	118.6	C12—C11—H11	118.5
C2—C3—C4	117.0 (2)	C10—C11—H11	118.5
C2—C3—C7	120.6 (3)	C11—C12—C13	116.5 (3)
C4—C3—C7	122.4 (3)	C11—C12—C16	121.8 (3)
C5—C4—C3	122.0 (3)	C13—C12—C16	121.7 (3)
C5—C4—H4	119.0	C14—C13—C12	122.5 (3)
C3—C4—H4	119.0	C14—C13—H13	118.8
C4—C5—C6	120.7 (3)	C12—C13—H13	118.8
C4—C5—H5	119.6	C13—C14—C15	120.1 (3)
C6—C5—H5	119.6	C13—C14—H14	119.9
O1—C6—C5	118.5 (2)	C15—C14—H14	119.9
O1—C6—C1	122.0 (2)	O2—C15—C14	118.6 (3)
C5—C6—C1	119.5 (2)	O2—C15—C10	121.7 (2)
C3—C7—H7A	109.5	C14—C15—C10	119.7 (2)
C3—C7—H7B	109.5	C12—C16—H16A	109.5
H7A—C7—H7B	109.5	C12—C16—H16B	109.5
C3—C7—H7C	109.5	H16A—C16—H16B	109.5
H7A—C7—H7C	109.5	C12—C16—H16C	109.5
H7B—C7—H7C	109.5	H16A—C16—H16C	109.5
N1—C8—C1	121.8 (2)	H16B—C16—H16C	109.5
N1—C8—H8	119.1	C8—N1—N2	113.7 (2)
C1—C8—H8	119.1	C9—N2—N1	113.9 (2)
N2—C9—C10	122.0 (2)	C6—O1—H1	109.5
N2—C9—H9	119.0	C15—O2—H2A	109.5
C6—C1—C2—C3	−1.5 (4)	C15—C10—C11—C12	1.3 (4)
C8—C1—C2—C3	178.2 (2)	C9—C10—C11—C12	−176.3 (2)
C1—C2—C3—C4	0.3 (4)	C10—C11—C12—C13	−0.9 (4)
C1—C2—C3—C7	179.6 (2)	C10—C11—C12—C16	176.6 (2)
C2—C3—C4—C5	0.2 (4)	C11—C12—C13—C14	0.0 (4)
C7—C3—C4—C5	−179.1 (3)	C16—C12—C13—C14	−177.6 (2)
C3—C4—C5—C6	0.7 (4)	C12—C13—C14—C15	0.6 (4)
C4—C5—C6—O1	178.5 (2)	C13—C14—C15—O2	179.7 (2)
C4—C5—C6—C1	−1.9 (4)	C13—C14—C15—C10	−0.3 (4)
C2—C1—C6—O1	−178.2 (2)	C11—C10—C15—O2	179.4 (2)
C8—C1—C6—O1	2.1 (4)	C9—C10—C15—O2	−3.1 (4)
C2—C1—C6—C5	2.3 (4)	C11—C10—C15—C14	−0.6 (3)
C8—C1—C6—C5	−177.4 (2)	C9—C10—C15—C14	176.9 (2)
C2—C1—C8—N1	178.2 (2)	C1—C8—N1—N2	179.0 (2)
C6—C1—C8—N1	−2.0 (4)	C10—C9—N2—N1	−179.07 (19)
N2—C9—C10—C11	179.4 (2)	C8—N1—N2—C9	−179.7 (2)
N2—C9—C10—C15	2.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82	1.91	2.635 (3)	146
O1—H1···N1	0.82	1.93	2.646 (3)	145
C5—H5···Cg1i	0.93	2.84	3.519 (3)	130
C14—H14···Cg2ii	0.93	2.85	3.519 (3)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N2	0.82	1.91	2.635 (3)	146
O1—H1⋯N1	0.82	1.93	2.646 (3)	145
C5—H5⋯Cg1i	0.93	2.84	3.519 (3)	130
C14—H14⋯Cg2ii	0.93	2.85	3.519 (3)	130

Symmetry codes: (i) ; (ii) .