4-Amino-5-(2-hydroxy-benzyl-idene-amino)benzene-1,2-dicarbonitrile.

A new tetra-dentate unsymmetrical Schiff base, C(15)H(10)N(4)O, has been synthesized from 4,5-dicyano-o-phenyl-enediamine and o-vanillin in refluxing ethanol. The dihedral angle between the two benzene rings is 39.0 (1)°. There are intra-molecular O-H⋯N and weak inter-molecular N-H⋯O and N-H⋯N inter-actions.

Related literature

For the biological activity of Schiff bases, see: Boskovic et al. (2003 ▶); Koizumi et al. (2005 ▶); Oshiob et al. (2005 ▶). For related structures, see: Kannappan et al. (2005 ▶); Zhang et al. (2003 ▶).

Experimental

Crystal data

C15H10N4O

M = 262.27

Monoclinic,

a = 14.0158 (15) Å

b = 12.3650 (13) Å

c = 7.3557 (8) Å

β = 99.904 (2)°

V = 1255.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.989, T max = 0.993

7234 measured reflections

2838 independent reflections

1770 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.170

S = 1.00

2838 reflections

187 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901157X/fl2237sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901157X/fl2237Isup2.hkl

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

C15H10N4O	F(000) = 544
Mr = 262.27	Dx = 1.387 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1728 reflections
a = 14.0158 (15) Å	θ = 2.2–26.3°
b = 12.3650 (13) Å	µ = 0.09 mm−1
c = 7.3557 (8) Å	T = 273 K
β = 99.904 (2)°	Block, yellow
V = 1255.8 (2) Å3	0.12 × 0.10 × 0.08 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2838 independent reflections
Radiation source: fine-focus sealed tube	1770 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→15
Tmin = 0.989, Tmax = 0.993	k = −16→11
7234 measured reflections	l = −9→9

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.105P)2] where P = (Fo2 + 2Fc2)/3
2838 reflections	(Δ/σ)max = 0.001
187 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.16 e Å−3

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	0.91817 (12)	0.53191 (15)	0.1796 (2)	0.0451 (5)
H1	0.9143	0.4649	0.1213	0.054*
C2	0.75504 (12)	0.55664 (15)	0.0486 (2)	0.0447 (5)
C3	0.72462 (12)	0.45035 (16)	0.0422 (3)	0.0467 (5)
H3	0.7640	0.3982	0.1084	0.056*
C4	1.01931 (14)	0.66149 (16)	0.3888 (3)	0.0495 (5)
C5	0.60770 (13)	0.60523 (16)	−0.1573 (3)	0.0513 (5)
H5	0.5687	0.6568	−0.2258	0.062*
C6	0.48595 (14)	0.46643 (17)	−0.2707 (3)	0.0517 (5)
C7	1.00930 (12)	0.56357 (15)	0.2900 (2)	0.0433 (5)
C8	0.57855 (12)	0.49920 (16)	−0.1632 (3)	0.0478 (5)
C9	0.63646 (13)	0.41989 (15)	−0.0612 (3)	0.0487 (5)
C10	0.69528 (13)	0.63652 (15)	−0.0496 (3)	0.0491 (5)
C11	0.60376 (14)	0.30994 (18)	−0.0585 (3)	0.0585 (6)
C12	1.09021 (14)	0.49709 (18)	0.2966 (3)	0.0551 (5)
H12	1.0840	0.4315	0.2338	0.066*
C13	1.10904 (16)	0.69001 (19)	0.4891 (3)	0.0629 (6)
H13	1.1160	0.7542	0.5559	0.075*
C14	1.18721 (16)	0.6233 (2)	0.4895 (3)	0.0685 (7)
H14	1.2472	0.6437	0.5554	0.082*
C15	1.17898 (14)	0.5268 (2)	0.3944 (3)	0.0671 (7)
H15	1.2327	0.4824	0.3962	0.080*
N1	0.57748 (15)	0.22349 (18)	−0.0536 (3)	0.0888 (7)
N2	0.41430 (13)	0.43718 (16)	−0.3475 (3)	0.0680 (6)
N3	0.72491 (14)	0.74135 (15)	−0.0435 (3)	0.0700 (6)
N4	0.84233 (10)	0.59191 (12)	0.1583 (2)	0.0462 (4)
O1	0.94357 (11)	0.72904 (11)	0.3901 (2)	0.0692 (5)
H1A	0.8950	0.7034	0.3268	0.104*
H1B	0.6802 (13)	0.7949 (13)	−0.087 (3)	0.080*
H1C	0.7813 (10)	0.7570 (18)	0.039 (3)	0.080*

	U11	U22	U33	U12	U13	U23
C1	0.0428 (10)	0.0454 (10)	0.0451 (10)	−0.0030 (8)	0.0018 (8)	0.0023 (8)
C2	0.0359 (9)	0.0493 (11)	0.0464 (10)	−0.0008 (8)	0.0002 (8)	−0.0008 (8)
C3	0.0373 (10)	0.0505 (11)	0.0491 (11)	0.0030 (8)	−0.0015 (8)	0.0021 (8)
C4	0.0475 (11)	0.0520 (11)	0.0461 (11)	−0.0053 (9)	0.0000 (8)	0.0062 (9)
C5	0.0389 (10)	0.0566 (12)	0.0540 (12)	0.0045 (9)	−0.0047 (8)	0.0050 (9)
C6	0.0411 (11)	0.0574 (12)	0.0544 (12)	0.0012 (9)	0.0019 (9)	−0.0047 (9)
C7	0.0367 (10)	0.0496 (11)	0.0412 (10)	−0.0016 (8)	−0.0003 (7)	0.0078 (8)
C8	0.0355 (10)	0.0589 (12)	0.0464 (11)	0.0001 (8)	−0.0006 (8)	−0.0024 (8)
C9	0.0391 (10)	0.0527 (12)	0.0522 (11)	−0.0018 (8)	0.0019 (8)	−0.0026 (8)
C10	0.0408 (10)	0.0495 (11)	0.0539 (11)	0.0007 (8)	−0.0004 (8)	0.0031 (9)
C11	0.0426 (11)	0.0556 (13)	0.0708 (15)	−0.0043 (10)	−0.0088 (10)	−0.0018 (10)
C12	0.0479 (11)	0.0643 (13)	0.0514 (12)	0.0038 (9)	0.0036 (9)	0.0068 (9)
C13	0.0586 (13)	0.0691 (14)	0.0556 (13)	−0.0205 (11)	−0.0052 (10)	0.0022 (10)
C14	0.0441 (12)	0.0998 (19)	0.0557 (13)	−0.0192 (12)	−0.0083 (10)	0.0163 (13)
C15	0.0405 (11)	0.0969 (19)	0.0615 (14)	0.0076 (11)	0.0022 (10)	0.0150 (12)
N1	0.0665 (13)	0.0643 (14)	0.124 (2)	−0.0132 (11)	−0.0155 (12)	0.0018 (12)
N2	0.0467 (10)	0.0788 (14)	0.0724 (13)	−0.0042 (9)	−0.0071 (9)	−0.0107 (10)
N3	0.0556 (11)	0.0517 (11)	0.0917 (15)	−0.0012 (9)	−0.0185 (10)	0.0126 (10)
N4	0.0375 (8)	0.0481 (9)	0.0490 (9)	0.0002 (7)	−0.0036 (7)	0.0033 (7)
O1	0.0627 (10)	0.0562 (9)	0.0816 (11)	0.0064 (7)	−0.0076 (8)	−0.0126 (8)

C1—N4	1.283 (2)	C7—C12	1.395 (3)
C1—C7	1.445 (2)	C8—C9	1.405 (3)
C1—H1	0.9300	C9—C11	1.436 (3)
C2—C3	1.380 (3)	C10—N3	1.360 (3)
C2—C10	1.411 (3)	C11—N1	1.133 (3)
C2—N4	1.414 (2)	C12—C15	1.376 (3)
C3—C9	1.387 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.371 (3)
C4—O1	1.352 (2)	C13—H13	0.9300
C4—C13	1.390 (3)	C14—C15	1.378 (3)
C4—C7	1.407 (3)	C14—H14	0.9300
C5—C8	1.372 (3)	C15—H15	0.9300
C5—C10	1.396 (3)	N3—H1B	0.930 (18)
C5—H5	0.9300	N3—H1C	0.930 (19)
C6—N2	1.124 (2)	O1—H1A	0.8200
C6—C8	1.456 (2)
N4—C1—C7	123.06 (17)	C3—C9—C11	120.39 (17)
N4—C1—H1	118.5	C8—C9—C11	120.79 (16)
C7—C1—H1	118.5	N3—C10—C5	121.11 (18)
C3—C2—C10	119.77 (16)	N3—C10—C2	119.97 (17)
C3—C2—N4	123.04 (16)	C5—C10—C2	118.88 (17)
C10—C2—N4	117.10 (16)	N1—C11—C9	178.9 (3)
C2—C3—C9	121.21 (17)	C15—C12—C7	121.2 (2)
C2—C3—H3	119.4	C15—C12—H12	119.4
C9—C3—H3	119.4	C7—C12—H12	119.4
O1—C4—C13	118.65 (19)	C14—C13—C4	119.9 (2)
O1—C4—C7	121.79 (16)	C14—C13—H13	120.1
C13—C4—C7	119.57 (19)	C4—C13—H13	120.1
C8—C5—C10	120.72 (18)	C13—C14—C15	121.5 (2)
C8—C5—H5	119.6	C13—C14—H14	119.2
C10—C5—H5	119.6	C15—C14—H14	119.2
N2—C6—C8	176.6 (2)	C12—C15—C14	119.1 (2)
C12—C7—C4	118.76 (17)	C12—C15—H15	120.5
C12—C7—C1	119.65 (18)	C14—C15—H15	120.5
C4—C7—C1	121.57 (17)	C10—N3—H1B	118.9 (14)
C5—C8—C9	120.58 (16)	C10—N3—H1C	116.1 (14)
C5—C8—C6	121.05 (17)	H1B—N3—H1C	122 (2)
C9—C8—C6	118.34 (17)	C1—N4—C2	120.57 (16)
C3—C9—C8	118.78 (17)	C4—O1—H1A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1B···N2i	0.93 (2)	2.21 (2)	3.126 (3)	171 (2)
N3—H1C···O1ii	0.93 (2)	2.69 (2)	3.206 (3)	116 (2)
O1—H1A···N4	0.82	1.91	2.639 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1B⋯N2i	0.930 (18)	2.205 (17)	3.126 (3)	171 (2)
N3—H1C⋯O1ii	0.930 (19)	2.69 (2)	3.206 (3)	115.5 (17)
O1—H1A⋯N4	0.82	1.91	2.639 (2)	147

Symmetry codes: (i) ; (ii) .