2-[N-(4-{4-[(2-Hy-droxy-5-meth-oxy-benzyl-idene)amino]-benz-yl}phen-yl)carboximido-yl]-4-meth-oxy-phenol.

In the title Schiff base, C(29)H(26)N(2)O(4), the complete molecule is generated by a crystallographic twofold axis and is V-shaped. The planes of the benzene rings of the central diphenyl-methane unit make a dihedral angle of 78.11 (4)° while adjacent benzene and 5-meth-oxy-salicyl-idene rings are twisted with respect to each other by a dihedral angle of 11.84 (8)°. The Schiff base is in the enol-imino form and an intra-molecular O-H⋯N hydrogen bond is observed.

Related literature

For related bis-bidentate Schiff base ligand structures, see: Birkedal & Pattison (2006 ▶); Shahverdizadeh & Tiekink (2011 ▶). For Schiff base ligands, see: Chu & Huang (2007 ▶); Yoshida & Ichikawa, (1997 ▶); Kruger et al. (2001 ▶); Moutet & Ourari (1997 ▶). For applications of bis-bidentate Schiff base ligands, see: Lin et al. (2008 ▶); Sadeghi et al. (2003 ▶).

Experimental

Crystal data

C29H26N2O4

M = 466.52

Monoclinic,

a = 41.307 (4) Å

b = 4.5993 (3) Å

c = 12.2229 (13) Å

β = 93.653 (12)°

V = 2317.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.69 × 0.38 × 0.06 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: gaussian (ABSGAUSS in PLATON; Spek, 2009 ▶) T min = 0.953, T max = 0.993

10694 measured reflections

2244 independent reflections

1662 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.06

2244 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: EXPOSE (Stoe & Cie, 1995 ▶); cell refinement: X-RED (Stoe & Cie, 1995 ▶); data reduction: X-RED; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010550/qk2024sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010550/qk2024Isup2.hkl

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

C29H26N2O4	F(000) = 984
Mr = 466.52	Dx = 1.337 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8000 reflections
a = 41.307 (4) Å	θ = 2.0–25.9°
b = 4.5993 (3) Å	µ = 0.09 mm−1
c = 12.2229 (13) Å	T = 293 K
β = 93.653 (12)°	Plate, yellow
V = 2317.4 (4) Å3	0.69 × 0.38 × 0.06 mm
Z = 4

Stoe IPDS diffractometer	2244 independent reflections
Radiation source: normal-focus sealed tube	1662 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 6.66 pixels mm-1	θmax = 25.8°, θmin = 2.0°
0.6° φ scans	h = −50→50
Absorption correction: gaussian (PLATON-ABSGAUSS; Spek, 2009)	k = −5→5
Tmin = 0.953, Tmax = 0.993	l = −14→15
10694 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.072P)2 + 0.1658P] where P = (Fo2 + 2Fc2)/3
2244 reflections	(Δ/σ)max = 0.001
160 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.15 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
O1	0.37635 (3)	0.9988 (3)	0.40329 (8)	0.0634 (3)
H1	0.3881	0.8694	0.4423	0.076*
O2	0.28937 (3)	1.4522 (3)	0.68223 (9)	0.0651 (4)
N1	0.40032 (2)	0.7019 (2)	0.57231 (8)	0.0404 (3)
C1	0.35488 (3)	1.1095 (3)	0.47152 (10)	0.0435 (3)
C2	0.33158 (3)	1.3024 (4)	0.43070 (11)	0.0521 (4)
H2	0.3309	1.3538	0.3570	0.063*
C3	0.30928 (3)	1.4206 (3)	0.49763 (12)	0.0502 (4)
H3	0.2936	1.5494	0.4687	0.060*
C4	0.31021 (3)	1.3469 (3)	0.60828 (11)	0.0451 (3)
C5	0.33363 (3)	1.1561 (3)	0.64977 (11)	0.0438 (3)
H5	0.3345	1.1092	0.7239	0.053*
C6	0.35595 (3)	1.0324 (3)	0.58312 (10)	0.0377 (3)
C7	0.26320 (4)	1.6273 (4)	0.64047 (16)	0.0725 (5)
H7A	0.2715	1.8012	0.6091	0.109*
H7B	0.2498	1.6779	0.6989	0.109*
H7C	0.2506	1.5214	0.5851	0.109*
C8	0.37983 (3)	0.8291 (3)	0.63036 (10)	0.0405 (3)
H8	0.3803	0.7902	0.7051	0.049*
C9	0.42351 (3)	0.5050 (3)	0.62024 (10)	0.0381 (3)
C10	0.42235 (3)	0.3824 (3)	0.72409 (11)	0.0460 (3)
H10	0.4053	0.4280	0.7673	0.055*
C11	0.44638 (3)	0.1933 (3)	0.76319 (11)	0.0463 (3)
H11	0.4450	0.1111	0.8323	0.056*
C12	0.47241 (3)	0.1226 (3)	0.70280 (11)	0.0411 (3)
C13	0.47310 (3)	0.2425 (3)	0.59852 (12)	0.0489 (4)
H13	0.4902	0.1979	0.5556	0.059*
C14	0.44889 (3)	0.4265 (3)	0.55754 (11)	0.0467 (4)
H14	0.4496	0.4989	0.4867	0.056*
C15	0.5000	−0.0659 (4)	0.7500	0.0474 (5)
H15A	0.4922	−0.1658	0.8076	0.057*

	U11	U22	U33	U12	U13	U23
O1	0.0703 (7)	0.0835 (8)	0.0375 (5)	0.0297 (6)	0.0109 (5)	0.0061 (5)
O2	0.0592 (6)	0.0793 (8)	0.0583 (6)	0.0268 (6)	0.0149 (5)	0.0052 (6)
N1	0.0401 (5)	0.0405 (6)	0.0402 (6)	0.0025 (5)	−0.0008 (4)	−0.0006 (5)
C1	0.0460 (7)	0.0490 (8)	0.0353 (6)	0.0034 (6)	0.0015 (5)	−0.0016 (6)
C2	0.0586 (8)	0.0599 (10)	0.0372 (7)	0.0101 (7)	−0.0021 (6)	0.0062 (6)
C3	0.0472 (7)	0.0528 (9)	0.0496 (8)	0.0094 (6)	−0.0055 (6)	0.0050 (6)
C4	0.0417 (6)	0.0468 (8)	0.0471 (7)	0.0038 (6)	0.0050 (6)	−0.0013 (6)
C5	0.0463 (7)	0.0481 (8)	0.0370 (6)	0.0028 (6)	0.0029 (5)	0.0038 (6)
C6	0.0387 (6)	0.0378 (7)	0.0363 (6)	−0.0012 (5)	−0.0011 (5)	−0.0008 (5)
C7	0.0619 (10)	0.0752 (12)	0.0819 (12)	0.0267 (9)	0.0173 (9)	0.0054 (10)
C8	0.0444 (7)	0.0419 (8)	0.0348 (6)	0.0008 (6)	−0.0003 (5)	0.0013 (5)
C9	0.0380 (6)	0.0358 (7)	0.0399 (6)	−0.0009 (5)	−0.0026 (5)	−0.0017 (5)
C10	0.0411 (7)	0.0519 (9)	0.0451 (7)	0.0042 (6)	0.0050 (5)	0.0047 (6)
C11	0.0462 (7)	0.0477 (8)	0.0444 (7)	−0.0017 (6)	−0.0020 (6)	0.0080 (6)
C12	0.0393 (7)	0.0312 (7)	0.0516 (7)	−0.0039 (5)	−0.0059 (5)	−0.0040 (6)
C13	0.0471 (7)	0.0487 (9)	0.0515 (8)	0.0076 (6)	0.0075 (6)	−0.0037 (6)
C14	0.0518 (7)	0.0485 (9)	0.0401 (7)	0.0070 (6)	0.0055 (6)	0.0015 (6)
C15	0.0445 (10)	0.0342 (11)	0.0626 (12)	0.000	−0.0055 (9)	0.000

O1—C1	1.3548 (15)	C7—H7B	0.9600
O1—H1	0.8879	C7—H7C	0.9600
O2—C4	1.3754 (16)	C8—H8	0.9300
O2—C7	1.4168 (19)	C9—C14	1.3852 (17)
N1—C8	1.2802 (16)	C9—C10	1.3926 (18)
N1—C9	1.4176 (16)	C10—C11	1.3822 (19)
C1—C2	1.379 (2)	C10—H10	0.9300
C1—C6	1.4074 (18)	C11—C12	1.3814 (18)
C2—C3	1.3819 (19)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.3908 (19)
C3—C4	1.392 (2)	C12—C15	1.5161 (17)
C3—H3	0.9300	C13—C14	1.3795 (19)
C4—C5	1.3787 (19)	C13—H13	0.9300
C5—C6	1.3901 (18)	C14—H14	0.9300
C5—H5	0.9300	C15—C12i	1.5161 (17)
C6—C8	1.4520 (18)	C15—H15A	0.9160
C7—H7A	0.9600
C1—O1—H1	106.2	H7B—C7—H7C	109.5
C4—O2—C7	117.30 (12)	N1—C8—C6	122.03 (12)
C8—N1—C9	121.08 (11)	N1—C8—H8	119.0
O1—C1—C2	119.22 (12)	C6—C8—H8	119.0
O1—C1—C6	121.38 (12)	C14—C9—C10	118.04 (12)
C2—C1—C6	119.40 (12)	C14—C9—N1	116.95 (11)
C1—C2—C3	121.01 (13)	C10—C9—N1	125.00 (11)
C1—C2—H2	119.5	C11—C10—C9	120.28 (12)
C3—C2—H2	119.5	C11—C10—H10	119.9
C2—C3—C4	120.06 (13)	C9—C10—H10	119.9
C2—C3—H3	120.0	C12—C11—C10	122.00 (13)
C4—C3—H3	120.0	C12—C11—H11	119.0
O2—C4—C5	115.87 (12)	C10—C11—H11	119.0
O2—C4—C3	124.94 (13)	C11—C12—C13	117.28 (12)
C5—C4—C3	119.19 (12)	C11—C12—C15	121.54 (11)
C4—C5—C6	121.39 (12)	C13—C12—C15	121.11 (11)
C4—C5—H5	119.3	C14—C13—C12	121.29 (12)
C6—C5—H5	119.3	C14—C13—H13	119.4
C5—C6—C1	118.95 (12)	C12—C13—H13	119.4
C5—C6—C8	119.31 (11)	C13—C14—C9	121.04 (13)
C1—C6—C8	121.75 (11)	C13—C14—H14	119.5
O2—C7—H7A	109.5	C9—C14—H14	119.5
O2—C7—H7B	109.5	C12i—C15—C12	110.27 (15)
H7A—C7—H7B	109.5	C12i—C15—H15A	106.7
O2—C7—H7C	109.5	C12—C15—H15A	106.6
H7A—C7—H7C	109.5
C6—C8—N1—C9	179.75 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.89	1.81	2.6177 (15)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.89	1.81	2.6177 (15)	151