2-Benzyl-oxybenzaldehyde azine.

The complete mol-ecule of the title compound, C(28)H(24)N(2)O(2), is generated by a centre of inversion (at the mid-point of the N-N bond). The substituents at the ends of the C=N bonds adopt an E,E configuration. The central -CH=N-N=CH- fragment is planar, but as a whole the mol-ecule is not: the benz-yloxy group is rotated about the O-C bond by 69.3 (2)° with respect to the plane of the benzyl-idene hydrazine unit.

Related literature

For general background to the coordination capability and biological activity of Schiff bases, see: Amadei et al. (1998 ▶); Xu et al. (2007 ▶). For related structures, see: Glidewell et al. (2006 ▶); Chattopadhyay et al. (2008 ▶). For the synthesis, see: Fu (2007 ▶).

Experimental

Crystal data

C28H24N2O2

M = 420.49

Monoclinic,

a = 11.222 (2) Å

b = 8.1157 (15) Å

c = 12.799 (2) Å

β = 102.297 (3)°

V = 1138.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 294 K

0.30 × 0.22 × 0.06 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

8428 measured reflections

2125 independent reflections

1143 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.119

S = 1.02

2125 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046728/rn2064sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046728/rn2064Isup2.hkl

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

C28H24N2O2	F(000) = 444
Mr = 420.49	Dx = 1.226 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.222 (2) Å	Cell parameters from 930 reflections
b = 8.1157 (15) Å	θ = 2.7–20.6°
c = 12.799 (2) Å	µ = 0.08 mm−1
β = 102.297 (3)°	T = 294 K
V = 1138.9 (4) Å3	BLOCK, yellow
Z = 2	0.30 × 0.22 × 0.06 mm

Bruker SMART APEX CCD area-detector diffractometer	1143 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
graphite	θmax = 25.5°, θmin = 2.7°
φ and ω scans	h = −13→13
8428 measured reflections	k = −9→9
2125 independent reflections	l = −15→15

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.043P)2 + 0.1257P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2125 reflections	Δρmax = 0.12 e Å−3
146 parameters	Δρmin = −0.12 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: 0.015 (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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.76645 (18)	0.1813 (2)	−0.07028 (15)	0.0456 (5)
C2	0.7692 (2)	0.2275 (3)	−0.17414 (17)	0.0558 (6)
H2	0.8364	0.1990	−0.2022	0.067*
C3	0.6754 (2)	0.3140 (3)	−0.23634 (18)	0.0665 (7)
H3	0.6790	0.3436	−0.3058	0.080*
C4	0.5764 (2)	0.3566 (3)	−0.1955 (2)	0.0692 (7)
H4	0.5130	0.4163	−0.2374	0.083*
C5	0.5694 (2)	0.3123 (3)	−0.09323 (19)	0.0651 (7)
H5	0.5013	0.3405	−0.0665	0.078*
C6	0.66432 (19)	0.2253 (3)	−0.03029 (17)	0.0529 (6)
C7	0.86788 (18)	0.0949 (2)	−0.00285 (16)	0.0475 (5)
H7	0.8684	0.0807	0.0693	0.057*
C8	0.5779 (2)	0.2404 (4)	0.1251 (2)	0.0907 (9)
H8A	0.4976	0.1985	0.0925	0.109*
H8B	0.5762	0.3596	0.1194	0.109*
C9	0.6111 (2)	0.1903 (3)	0.2398 (2)	0.0626 (7)
C10	0.7017 (2)	0.2695 (3)	0.3102 (3)	0.0799 (8)
H10	0.7445	0.3551	0.2866	0.096*
C11	0.7299 (3)	0.2228 (5)	0.4164 (3)	0.0935 (9)
H11	0.7907	0.2782	0.4643	0.112*
C12	0.6691 (4)	0.0959 (5)	0.4514 (2)	0.0952 (10)
H12	0.6888	0.0640	0.5228	0.114*
C13	0.5805 (3)	0.0169 (4)	0.3821 (3)	0.0938 (9)
H13	0.5391	−0.0699	0.4059	0.113*
C14	0.5506 (2)	0.0633 (3)	0.2766 (2)	0.0742 (8)
H14	0.4888	0.0081	0.2297	0.089*
N1	0.95554 (14)	0.0385 (2)	−0.04001 (12)	0.0503 (5)
O1	0.66609 (13)	0.17497 (19)	0.07219 (12)	0.0690 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0451 (12)	0.0464 (13)	0.0445 (12)	0.0027 (10)	0.0074 (10)	0.0012 (10)
C2	0.0595 (14)	0.0573 (14)	0.0508 (14)	0.0035 (12)	0.0126 (12)	0.0019 (11)
C3	0.0826 (18)	0.0636 (16)	0.0512 (14)	0.0121 (14)	0.0092 (14)	0.0112 (12)
C4	0.0698 (17)	0.0688 (17)	0.0615 (16)	0.0169 (13)	−0.0027 (14)	0.0088 (13)
C5	0.0565 (15)	0.0718 (17)	0.0654 (16)	0.0181 (13)	0.0095 (13)	0.0077 (13)
C6	0.0550 (14)	0.0542 (14)	0.0496 (13)	0.0073 (11)	0.0113 (11)	0.0055 (11)
C7	0.0486 (12)	0.0534 (13)	0.0411 (12)	0.0016 (10)	0.0104 (10)	−0.0024 (10)
C8	0.0831 (18)	0.124 (2)	0.0752 (19)	0.0530 (17)	0.0391 (16)	0.0188 (17)
C9	0.0586 (15)	0.0706 (17)	0.0656 (17)	0.0217 (13)	0.0291 (13)	0.0060 (14)
C10	0.0663 (18)	0.080 (2)	0.100 (2)	0.0011 (15)	0.0325 (17)	0.0067 (17)
C11	0.0693 (19)	0.113 (3)	0.092 (2)	0.0163 (18)	0.0034 (18)	−0.022 (2)
C12	0.115 (3)	0.107 (3)	0.069 (2)	0.046 (2)	0.030 (2)	0.0131 (19)
C13	0.123 (3)	0.076 (2)	0.096 (2)	0.0074 (19)	0.053 (2)	0.0160 (18)
C14	0.0758 (18)	0.0684 (18)	0.083 (2)	0.0021 (14)	0.0279 (16)	−0.0083 (15)
N1	0.0446 (10)	0.0636 (12)	0.0415 (10)	0.0078 (9)	0.0067 (8)	−0.0011 (8)
O1	0.0666 (10)	0.0865 (12)	0.0603 (10)	0.0333 (9)	0.0278 (8)	0.0168 (9)

C1—C2	1.388 (3)	C8—C9	1.492 (3)
C1—C6	1.398 (3)	C8—H8A	0.9700
C1—C7	1.454 (3)	C8—H8B	0.9700
C2—C3	1.370 (3)	C9—C10	1.368 (3)
C2—H2	0.9300	C9—C14	1.372 (3)
C3—C4	1.370 (3)	C10—C11	1.382 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.376 (3)	C11—C12	1.362 (4)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.384 (3)	C12—C13	1.346 (4)
C5—H5	0.9300	C12—H12	0.9300
C6—O1	1.370 (2)	C13—C14	1.373 (4)
C7—N1	1.266 (2)	C13—H13	0.9300
C7—H7	0.9300	C14—H14	0.9300
C8—O1	1.417 (2)	N1—N1i	1.414 (3)
C2—C1—C6	117.99 (19)	O1—C8—H8B	110.0
C2—C1—C7	121.61 (19)	C9—C8—H8B	110.0
C6—C1—C7	120.36 (18)	H8A—C8—H8B	108.4
C3—C2—C1	121.6 (2)	C10—C9—C14	118.7 (2)
C3—C2—H2	119.2	C10—C9—C8	121.0 (3)
C1—C2—H2	119.2	C14—C9—C8	120.3 (3)
C4—C3—C2	119.5 (2)	C9—C10—C11	120.1 (3)
C4—C3—H3	120.2	C9—C10—H10	119.9
C2—C3—H3	120.2	C11—C10—H10	119.9
C3—C4—C5	120.8 (2)	C12—C11—C10	120.3 (3)
C3—C4—H4	119.6	C12—C11—H11	119.8
C5—C4—H4	119.6	C10—C11—H11	119.8
C4—C5—C6	119.7 (2)	C13—C12—C11	119.7 (3)
C4—C5—H5	120.2	C13—C12—H12	120.1
C6—C5—H5	120.2	C11—C12—H12	120.1
O1—C6—C5	124.2 (2)	C12—C13—C14	120.6 (3)
O1—C6—C1	115.37 (18)	C12—C13—H13	119.7
C5—C6—C1	120.4 (2)	C14—C13—H13	119.7
N1—C7—C1	121.61 (18)	C9—C14—C13	120.6 (3)
N1—C7—H7	119.2	C9—C14—H14	119.7
C1—C7—H7	119.2	C13—C14—H14	119.7
O1—C8—C9	108.35 (19)	C7—N1—N1i	111.88 (19)
O1—C8—H8A	110.0	C6—O1—C8	118.49 (17)
C9—C8—H8A	110.0
C6—C1—C2—C3	0.2 (3)	O1—C8—C9—C14	−102.1 (3)
C7—C1—C2—C3	−177.7 (2)	C14—C9—C10—C11	−0.8 (4)
C1—C2—C3—C4	0.1 (3)	C8—C9—C10—C11	179.1 (2)
C2—C3—C4—C5	−0.6 (4)	C9—C10—C11—C12	1.1 (4)
C3—C4—C5—C6	0.8 (4)	C10—C11—C12—C13	−0.6 (4)
C4—C5—C6—O1	−179.8 (2)	C11—C12—C13—C14	−0.1 (4)
C4—C5—C6—C1	−0.5 (3)	C10—C9—C14—C13	0.1 (3)
C2—C1—C6—O1	179.35 (18)	C8—C9—C14—C13	−179.8 (2)
C7—C1—C6—O1	−2.8 (3)	C12—C13—C14—C9	0.4 (4)
C2—C1—C6—C5	0.0 (3)	C1—C7—N1—N1i	179.20 (19)
C7—C1—C6—C5	177.9 (2)	C5—C6—O1—C8	−12.4 (3)
C2—C1—C7—N1	−9.7 (3)	C1—C6—O1—C8	168.4 (2)
C6—C1—C7—N1	172.5 (2)	C9—C8—O1—C6	−170.5 (2)
O1—C8—C9—C10	78.1 (3)