2-Amino-3-[(E)-(2-hy-droxy-3-methyl-benzyl-idene)amino]-but-2-ene-dinitrile.

The title compound, C(12)H(10)N(4)O, is a Schiff base obtained from the condensation of diamino-maleonitrile and 2-hy-droxy-3-methyl-benzaldehyde. The mol-ecule is roughly planar, with an r.m.s. deviation of 0.0354 Å, and adopts the phenol-imine tautomeric form. An intra-molecular O-H⋯N hydrogen bond involving the O-H group and the azomethine N atom generates an S(6) ring. In the crystal, there are two N-H⋯N hydrogen bonds.

Related literature

For the biological properties of Schiff bases see: Da Silva et al. (2011 ▶) and for their use in coordination chemistry, see: Aazam et al. (2011 ▶); Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For graph-set notation, see: Bernstein et al., (1995 ▶). For related structures, see: Aazam & Büyükgüngör (2010 ▶); Hökelek et al. (2000 ▶); Odabaşoğlu et al. (2005 ▶); Rivera et al. (2006 ▶).

Experimental

Crystal data

C12H10N4O

M = 226.24

Monoclinic,

a = 6.9041 (6) Å

b = 11.8791 (7) Å

c = 14.0282 (11) Å

β = 101.600 (7)°

V = 1127.02 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.76 × 0.48 × 0.03 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.949, T max = 0.996

16504 measured reflections

2336 independent reflections

1700 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.132

S = 1.14

2336 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2001 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015243/go2051sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015243/go2051Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015243/go2051Isup3.cml

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

C12H10N4O	F(000) = 472
Mr = 226.24	Dx = 1.333 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16504 reflections
a = 6.9041 (6) Å	θ = 2.3–28.0°
b = 11.8791 (7) Å	µ = 0.09 mm−1
c = 14.0282 (11) Å	T = 296 K
β = 101.600 (7)°	Plate, brown
V = 1127.02 (15) Å3	0.76 × 0.48 × 0.03 mm
Z = 4

Stoe IPDS 2 diffractometer	2336 independent reflections
Radiation source: fine-focus sealed tube	1700 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
rotation method scans	θmax = 26.5°, θmin = 2.3°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −8→8
Tmin = 0.949, Tmax = 0.996	k = −14→14
16504 measured reflections	l = −17→17

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)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.0085P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
2336 reflections	Δρmax = 0.15 e Å−3
168 parameters	Δρmin = −0.16 e Å−3
0 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: 0.008 (2)

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
C1	0.2927 (3)	0.39788 (16)	0.57527 (14)	0.0412 (5)
C2	0.2741 (3)	0.30861 (18)	0.50843 (15)	0.0451 (5)
C3	0.2980 (3)	0.19643 (18)	0.53978 (17)	0.0507 (5)
C4	0.3421 (3)	0.1774 (2)	0.63866 (19)	0.0579 (6)
H4	0.3581	0.1036	0.6609	0.069*
C5	0.3637 (3)	0.2639 (2)	0.70634 (17)	0.0597 (6)
H5	0.3951	0.2480	0.7726	0.072*
C6	0.3382 (3)	0.3731 (2)	0.67447 (16)	0.0518 (5)
H6	0.3514	0.4313	0.7196	0.062*
C7	0.2734 (4)	0.1024 (2)	0.4671 (2)	0.0730 (7)
H7A	0.3735	0.1081	0.4287	0.088*
H7B	0.1452	0.1073	0.4254	0.088*
H7C	0.2860	0.0315	0.5006	0.088*
C8	0.2653 (3)	0.51404 (16)	0.54458 (14)	0.0426 (5)
H8	0.2785	0.5698	0.5920	0.051*
C9	0.2013 (3)	0.65633 (15)	0.42752 (14)	0.0393 (5)
C10	0.1644 (3)	0.68409 (16)	0.33180 (14)	0.0405 (5)
C11	0.2178 (3)	0.74210 (17)	0.50067 (15)	0.0461 (5)
C12	0.1464 (3)	0.80158 (18)	0.30383 (15)	0.0482 (5)
N1	0.2236 (2)	0.54359 (13)	0.45456 (11)	0.0405 (4)
N2	0.1385 (3)	0.61018 (17)	0.25795 (15)	0.0563 (5)
H2A	0.112 (4)	0.538 (3)	0.2695 (19)	0.077 (8)*
H2B	0.130 (4)	0.637 (2)	0.199 (2)	0.076 (8)*
N3	0.2305 (3)	0.80465 (17)	0.56309 (15)	0.0664 (6)
N4	0.1280 (3)	0.89245 (17)	0.27921 (17)	0.0709 (6)
O1	0.2304 (3)	0.32719 (15)	0.41171 (12)	0.0668 (5)
H1	0.217 (4)	0.400 (3)	0.405 (2)	0.081 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0386 (10)	0.0447 (11)	0.0419 (11)	0.0035 (8)	0.0116 (8)	0.0071 (9)
C2	0.0471 (11)	0.0469 (12)	0.0413 (12)	0.0045 (9)	0.0090 (9)	0.0061 (9)
C3	0.0485 (12)	0.0429 (12)	0.0594 (14)	0.0028 (9)	0.0076 (10)	0.0095 (10)
C4	0.0520 (13)	0.0504 (13)	0.0705 (17)	0.0023 (10)	0.0108 (11)	0.0236 (12)
C5	0.0649 (14)	0.0679 (16)	0.0466 (13)	0.0040 (11)	0.0120 (11)	0.0215 (12)
C6	0.0563 (13)	0.0597 (14)	0.0417 (12)	0.0015 (10)	0.0149 (10)	0.0064 (10)
C7	0.0825 (17)	0.0444 (13)	0.0863 (19)	0.0090 (12)	0.0027 (14)	−0.0023 (13)
C8	0.0473 (11)	0.0408 (11)	0.0415 (12)	0.0017 (8)	0.0135 (8)	0.0006 (9)
C9	0.0416 (10)	0.0355 (10)	0.0421 (11)	−0.0004 (8)	0.0113 (8)	0.0004 (8)
C10	0.0430 (10)	0.0345 (10)	0.0436 (12)	−0.0030 (8)	0.0077 (8)	0.0026 (8)
C11	0.0566 (13)	0.0382 (11)	0.0446 (12)	0.0035 (9)	0.0127 (10)	0.0029 (10)
C12	0.0548 (12)	0.0404 (12)	0.0482 (12)	−0.0029 (9)	0.0072 (9)	0.0055 (10)
N1	0.0450 (9)	0.0367 (8)	0.0411 (10)	0.0015 (7)	0.0114 (7)	0.0039 (7)
N2	0.0836 (14)	0.0420 (11)	0.0416 (11)	−0.0110 (10)	0.0084 (9)	0.0022 (9)
N3	0.0917 (15)	0.0538 (12)	0.0540 (12)	0.0047 (10)	0.0151 (11)	−0.0096 (10)
N4	0.0901 (15)	0.0433 (11)	0.0779 (15)	0.0048 (10)	0.0134 (12)	0.0155 (10)
O1	0.1120 (14)	0.0444 (9)	0.0415 (10)	0.0164 (9)	0.0098 (9)	0.0023 (7)

C1—C6	1.395 (3)	C7—H7C	0.9600
C1—C2	1.404 (3)	C8—N1	1.286 (2)
C1—C8	1.447 (3)	C8—H8	0.9300
C2—O1	1.348 (3)	C9—C10	1.356 (3)
C2—C3	1.403 (3)	C9—N1	1.392 (2)
C3—C4	1.378 (3)	C9—C11	1.434 (3)
C3—C7	1.499 (3)	C10—N2	1.342 (3)
C4—C5	1.386 (4)	C10—C12	1.448 (3)
C4—H4	0.9300	C11—N3	1.138 (3)
C5—C6	1.372 (3)	C12—N4	1.133 (3)
C5—H5	0.9300	N2—H2A	0.89 (3)
C6—H6	0.9300	N2—H2B	0.88 (3)
C7—H7A	0.9600	O1—H1	0.88 (3)
C7—H7B	0.9600
C6—C1—C2	118.59 (18)	H7A—C7—H7B	109.5
C6—C1—C8	119.22 (19)	C3—C7—H7C	109.5
C2—C1—C8	122.19 (18)	H7A—C7—H7C	109.5
O1—C2—C3	117.37 (19)	H7B—C7—H7C	109.5
O1—C2—C1	121.37 (18)	N1—C8—C1	122.86 (18)
C3—C2—C1	121.26 (19)	N1—C8—H8	118.6
C4—C3—C2	117.4 (2)	C1—C8—H8	118.6
C4—C3—C7	122.3 (2)	C10—C9—N1	119.49 (17)
C2—C3—C7	120.3 (2)	C10—C9—C11	120.52 (17)
C3—C4—C5	122.7 (2)	N1—C9—C11	119.99 (17)
C3—C4—H4	118.7	N2—C10—C9	125.07 (19)
C5—C4—H4	118.7	N2—C10—C12	115.50 (19)
C6—C5—C4	119.2 (2)	C9—C10—C12	119.43 (18)
C6—C5—H5	120.4	N3—C11—C9	175.5 (2)
C4—C5—H5	120.4	N4—C12—C10	177.7 (2)
C5—C6—C1	120.9 (2)	C8—N1—C9	121.38 (16)
C5—C6—H6	119.6	C10—N2—H2A	118.9 (17)
C1—C6—H6	119.6	C10—N2—H2B	117.7 (18)
C3—C7—H7A	109.5	H2A—N2—H2B	123 (2)
C3—C7—H7B	109.5	C2—O1—H1	105.2 (19)
C6—C1—C2—O1	179.99 (18)	C2—C1—C6—C5	−0.2 (3)
C8—C1—C2—O1	0.3 (3)	C8—C1—C6—C5	179.5 (2)
C6—C1—C2—C3	0.8 (3)	C6—C1—C8—N1	179.86 (18)
C8—C1—C2—C3	−178.93 (19)	C2—C1—C8—N1	−0.4 (3)
O1—C2—C3—C4	−179.80 (19)	N1—C9—C10—N2	2.9 (3)
C1—C2—C3—C4	−0.6 (3)	C11—C9—C10—N2	−177.18 (19)
O1—C2—C3—C7	−0.5 (3)	N1—C9—C10—C12	−178.38 (17)
C1—C2—C3—C7	178.8 (2)	C11—C9—C10—C12	1.5 (3)
C2—C3—C4—C5	−0.2 (3)	C1—C8—N1—C9	−178.97 (18)
C7—C3—C4—C5	−179.5 (2)	C10—C9—N1—C8	177.62 (18)
C3—C4—C5—C6	0.8 (3)	C11—C9—N1—C8	−2.3 (3)
C4—C5—C6—C1	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.88 (3)	1.83 (3)	2.643 (2)	153 (3)
N2—H2A···N4i	0.89 (3)	2.40 (3)	3.156 (3)	142 (2)
N2—H2B···N3ii	0.88 (3)	2.26 (3)	3.098 (3)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.88 (3)	1.83 (3)	2.643 (2)	153 (3)
N2—H2A⋯N4i	0.89 (3)	2.40 (3)	3.156 (3)	142 (2)
N2—H2B⋯N3ii	0.88 (3)	2.26 (3)	3.098 (3)	159 (2)

Symmetry codes: (i) ; (ii) .