2-{(1E)-1-[(3-{(E)-[1-(2-Hy­droxy-4-meth­oxy­phen­yl)ethyl­idene]amino}-2,2-di­methyl­prop­yl)imino]­eth­yl}-5-meth­oxy­phenol

Ghaemi, A.; Rayati, S.; Elahi, E.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811038815

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2760

https://doi.org/10.1107/S1600536811038815

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2-{(1E)-1-[(3-{(E)-[1-(2-Hydroxy-4-methoxyphenyl)ethylidene]amino}-2,2-dimethylpropyl)imino]ethyl}-5-methoxyphenol

Akbar Ghaemi,^a ‡ Saeed Rayati,^b Ehsan Elahi,^a Seik Weng Ng ^c,^d and Edward R. T. Tiekink ^c ^*

^aDepartment of Chemistry, Saveh Branch, Islamic Azad University, Saveh, Iran, ^bDepartment of Chemistry, K. N. Toosi University of Technology, PO Box, 16315-1618, Tehran, Iran, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 19 September 2011; accepted 21 September 2011; online 30 September 2011)

Molecules of the title compound, C₂₃H₃₀N₂O₄, are located on a crystallographic mirror plane. The molecule has a curved shape with the dihedral angle formed between the two benzene rings being 55.26 (5)°. Intramolecular O—H⋯N hydrogen bonds are noted. In the crystal, supramolecular layers are formed in the ac plane owing to the presence of C—H⋯π interactions.

Related literature

For our previous work on Schiff base complexes, see: Rayati et al. (2007 , 2010 ).

Experimental

Crystal data

C₂₃H₃₀N₂O₄
M_r = 398.49
Orthorhombic, P n m a
a = 10.0764 (7) Å
b = 36.069 (2) Å
c = 5.8322 (4) Å
V = 2119.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.793, T_max = 1.000
6816 measured reflections
2419 independent reflections
1952 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.155
S = 1.08
2419 reflections
141 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.86 (1)	1.70 (2)	2.507 (2)	157 (4)
C7—H7c⋯Cg1ⁱ	0.96	2.75	3.547 (2)	141
C9—H9b⋯Cg1ⁱⁱ	0.96	2.66	3.456 (2)	140
Symmetry codes: (i) $[x-{\script{3\over 2}}, y, -z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811038815/bt5648sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038815/bt5648Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038815/bt5648Isup3.cml

checkCIF report

Comment top

The crystallographic investigation of the title compound, (I), was motivated by recent research in Schiff base complexes (Rayati et al., 2007; Rayati et al., 2010). The molecule of (I), Fig. 1, has crystallographically imposed mirror symmetry. The dihedral angle formed between the two benzene rings is 55.26 (5) ° indicating that, overall, the molecule has a curved shape. The presence of an intramolecular O—H···N hydrogen bond is noted, Table 1. The methoxy group is co-planar with the benzene ring to which it is attached as seen in the value of the C7—O2—C4—C3 torsion angle of -3.4 (3) °.

Molecules are assembled into layers in the ac plane through the agency of C—H···π interactions, Table 1 and Fig. 2, formed by methyl-H and the (C1—C6) benzene ring, indicating that the latter is bridging. Layers stack along the b axis, Fig. 3.

Related literature top

For our previous work on Schiff base complexes, see: Rayati et al. (2007, 2010).

Experimental top

To a stirred ethanolic solution (30 ml) of 2,2-dimethylpropylenediamine (0.102 g, 1 mmol), 2-hydroxy-4-methoxyacetophenone (0.332 g, 2 mmol) was added. The bright-yellow solution was stirred and heated under reflux for 1 h. Crystals were obtained by evaporation of an ethanol solution of the product at room temperature. Yield: 85%; M.pt. 423 K. Selected FT—IR data (cm^-1): 3427 ν(O—H), 2929–2965 ν(C—H), 1607 ν(C═N), 1446 ν(C═C), 1022 ν(C—O). ¹H NMR (δ): 1.23 (s, 6H, C(CH₃)₂), 2.31 (s, 6H, OCH₃C═ N), 3.47 (s, 4H, NCH₂), 3.80 (s, 6H, OCH₃), 6.24–7.37 (m, 6H, ArH), 12.35 (s, 2H, OH) p.p.m..

Structure description top

For our previous work on Schiff base complexes, see: Rayati et al. (2007, 2010).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. The molecule has mirror symmetry and the unlabelled atoms are related by the symmetry operation x, 3/2 - y, z.
	Fig. 2. Supramolecular layer in the ac plane in (I) sustained by C—H···π interactions shown as purple dashed lines.
	Fig. 3. A view in projection down the c axis of the unit-cell contents of (I), highlighting the stacking of layers along the b axis. The C—H···π interactions are shown as purple dashed lines.

2-{(1E)-1-[(3-{(E)-[1-(2-Hydroxy-4- methoxyphenyl)ethylidene]amino}-2,2-dimethylpropyl)imino]ethyl}-5-methoxyphenol top

Crystal data top

C₂₃H₃₀N₂O₄	F(000) = 856
M_r = 398.49	D_x = 1.249 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2488 reflections
a = 10.0764 (7) Å	θ = 2.3–27.5°
b = 36.069 (2) Å	µ = 0.09 mm⁻¹
c = 5.8322 (4) Å	T = 294 K
V = 2119.7 (2) Å³	Prism, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	2419 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1952 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.039
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.4°
ω scan	h = −9→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −33→46
T_min = 0.793, T_max = 1.000	l = −5→7
6816 measured reflections

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0642P)² + 0.9075P] where P = (F_o² + 2F_c²)/3
2419 reflections	(Δ/σ)_max = 0.001
141 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₃H₃₀N₂O₄	V = 2119.7 (2) Å³
M_r = 398.49	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 10.0764 (7) Å	µ = 0.09 mm⁻¹
b = 36.069 (2) Å	T = 294 K
c = 5.8322 (4) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	2419 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1952 reflections with I > 2σ(I)
T_min = 0.793, T_max = 1.000	R_int = 0.039
6816 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.23 e Å⁻³
2419 reflections	Δρ_min = −0.18 e Å⁻³
141 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.30246 (15)	0.64954 (4)	0.1933 (2)	0.0531 (4)
H1	0.354 (3)	0.6654 (8)	0.256 (6)	0.122 (13)*
O2	0.13785 (15)	0.53184 (4)	0.4322 (3)	0.0574 (4)
N1	0.46777 (15)	0.68176 (4)	0.4452 (3)	0.0419 (4)
C1	0.39243 (16)	0.62163 (5)	0.5332 (3)	0.0352 (4)
C2	0.30646 (17)	0.62129 (5)	0.3409 (3)	0.0372 (4)
C3	0.22205 (18)	0.59119 (5)	0.3013 (3)	0.0409 (4)
H3	0.1682	0.5908	0.1719	0.049*
C4	0.21869 (18)	0.56202 (5)	0.4543 (3)	0.0422 (4)
C5	0.3005 (2)	0.56209 (5)	0.6471 (3)	0.0477 (5)
H5	0.2975	0.5425	0.7506	0.057*
C6	0.38514 (19)	0.59118 (5)	0.6829 (3)	0.0436 (4)
H6	0.4399	0.5908	0.8112	0.052*
C7	0.0463 (2)	0.53147 (6)	0.2451 (5)	0.0660 (6)
H7A	−0.0043	0.5089	0.2490	0.099*
H7B	0.0942	0.5329	0.1031	0.099*
H7C	−0.0125	0.5523	0.2576	0.099*
C8	0.47861 (17)	0.65354 (5)	0.5787 (3)	0.0360 (4)
C9	0.5749 (2)	0.65215 (6)	0.7746 (4)	0.0538 (5)
H9A	0.6438	0.6701	0.7504	0.081*
H9B	0.6134	0.6278	0.7836	0.081*
H9C	0.5293	0.6576	0.9151	0.081*
C10	0.54167 (19)	0.71600 (5)	0.4786 (4)	0.0460 (5)
H10A	0.6219	0.7153	0.3869	0.055*
H10B	0.5674	0.7181	0.6384	0.055*
C11	0.4589 (2)	0.7500	0.4108 (4)	0.0342 (5)
C12	0.4327 (3)	0.7500	0.1527 (4)	0.0441 (6)
H12A	0.5157	0.7500	0.0719	0.066*
H12B	0.3830	0.7717	0.1121	0.066*	0.50
H12C	0.3830	0.7283	0.1121	0.066*	0.50
C13	0.3269 (3)	0.7500	0.5407 (5)	0.0493 (7)
H13A	0.3437	0.7500	0.7027	0.074*
H13B	0.2770	0.7283	0.5005	0.074*	0.50
H13C	0.2770	0.7717	0.5005	0.074*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0641 (9)	0.0448 (7)	0.0504 (8)	−0.0113 (7)	−0.0195 (7)	0.0126 (6)
O2	0.0598 (9)	0.0403 (7)	0.0721 (10)	−0.0103 (7)	−0.0096 (8)	0.0061 (7)
N1	0.0415 (8)	0.0358 (7)	0.0482 (8)	−0.0012 (6)	−0.0100 (7)	0.0021 (6)
C1	0.0334 (8)	0.0348 (8)	0.0375 (8)	0.0061 (7)	0.0004 (7)	−0.0005 (7)
C2	0.0387 (9)	0.0364 (8)	0.0365 (8)	0.0052 (7)	−0.0004 (7)	0.0000 (7)
C3	0.0405 (9)	0.0397 (9)	0.0425 (9)	0.0020 (8)	−0.0043 (8)	−0.0016 (7)
C4	0.0394 (9)	0.0352 (9)	0.0518 (10)	0.0020 (8)	0.0028 (8)	−0.0021 (8)
C5	0.0526 (11)	0.0398 (9)	0.0507 (10)	0.0033 (9)	−0.0001 (9)	0.0104 (8)
C6	0.0434 (10)	0.0439 (9)	0.0435 (9)	0.0057 (8)	−0.0071 (8)	0.0054 (8)
C7	0.0645 (14)	0.0506 (11)	0.0829 (16)	−0.0150 (11)	−0.0162 (13)	−0.0018 (12)
C8	0.0310 (8)	0.0375 (8)	0.0396 (8)	0.0071 (7)	−0.0012 (7)	−0.0025 (7)
C9	0.0536 (12)	0.0484 (10)	0.0594 (12)	0.0001 (9)	−0.0215 (10)	0.0064 (9)
C10	0.0389 (10)	0.0398 (9)	0.0594 (11)	−0.0008 (8)	−0.0164 (9)	0.0033 (8)
C11	0.0301 (11)	0.0377 (12)	0.0348 (11)	0.000	−0.0039 (9)	0.000
C12	0.0476 (14)	0.0482 (14)	0.0366 (12)	0.000	−0.0019 (11)	0.000
C13	0.0399 (14)	0.0658 (18)	0.0422 (14)	0.000	0.0010 (11)	0.000

Geometric parameters (Å, º) top

O1—C2	1.334 (2)	C7—H7C	0.9600
O1—H1	0.857 (10)	C8—C9	1.500 (2)
O2—C4	1.366 (2)	C9—H9A	0.9600
O2—C7	1.429 (3)	C9—H9B	0.9600
N1—C8	1.286 (2)	C9—H9C	0.9600
N1—C10	1.455 (2)	C10—C11	1.535 (2)
C1—C6	1.405 (2)	C10—H10A	0.9700
C1—C2	1.417 (2)	C10—H10B	0.9700
C1—C8	1.466 (2)	C11—C12	1.528 (3)
C2—C3	1.399 (2)	C11—C13	1.531 (3)
C3—C4	1.380 (3)	C11—C10ⁱ	1.535 (2)
C3—H3	0.9300	C12—H12A	0.9600
C4—C5	1.394 (3)	C12—H12B	0.9600
C5—C6	1.369 (3)	C12—H12C	0.9600
C5—H5	0.9300	C13—H13A	0.9600
C6—H6	0.9300	C13—H13B	0.9600
C7—H7A	0.9600	C13—H13C	0.9600
C7—H7B	0.9600

C2—O1—H1	103 (3)	C8—C9—H9A	109.5
C4—O2—C7	117.70 (16)	C8—C9—H9B	109.5
C8—N1—C10	123.15 (15)	H9A—C9—H9B	109.5
C6—C1—C2	116.94 (16)	C8—C9—H9C	109.5
C6—C1—C8	122.15 (16)	H9A—C9—H9C	109.5
C2—C1—C8	120.81 (15)	H9B—C9—H9C	109.5
O1—C2—C3	117.90 (15)	N1—C10—C11	111.42 (14)
O1—C2—C1	121.50 (16)	N1—C10—H10A	109.3
C3—C2—C1	120.60 (16)	C11—C10—H10A	109.3
C4—C3—C2	120.01 (17)	N1—C10—H10B	109.3
C4—C3—H3	120.0	C11—C10—H10B	109.3
C2—C3—H3	120.0	H10A—C10—H10B	108.0
O2—C4—C3	124.15 (17)	C12—C11—C13	109.7 (2)
O2—C4—C5	115.47 (16)	C12—C11—C10	110.34 (14)
C3—C4—C5	120.38 (17)	C13—C11—C10	110.17 (14)
C6—C5—C4	119.53 (17)	C12—C11—C10ⁱ	110.34 (14)
C6—C5—H5	120.2	C13—C11—C10ⁱ	110.17 (14)
C4—C5—H5	120.2	C10—C11—C10ⁱ	106.04 (19)
C5—C6—C1	122.50 (17)	C11—C12—H12A	109.5
C5—C6—H6	118.8	C11—C12—H12B	109.5
C1—C6—H6	118.8	H12A—C12—H12B	109.5
O2—C7—H7A	109.5	C11—C12—H12C	109.5
O2—C7—H7B	109.5	H12A—C12—H12C	109.5
H7A—C7—H7B	109.5	H12B—C12—H12C	109.5
O2—C7—H7C	109.5	C11—C13—H13A	109.5
H7A—C7—H7C	109.5	C11—C13—H13B	109.5
H7B—C7—H7C	109.5	H13A—C13—H13B	109.5
N1—C8—C1	117.46 (15)	C11—C13—H13C	109.5
N1—C8—C9	122.87 (16)	H13A—C13—H13C	109.5
C1—C8—C9	119.67 (15)	H13B—C13—H13C	109.5

C6—C1—C2—O1	177.56 (17)	C2—C1—C6—C5	0.5 (3)
C8—C1—C2—O1	1.1 (3)	C8—C1—C6—C5	176.91 (17)
C6—C1—C2—C3	−2.0 (2)	C10—N1—C8—C1	176.40 (16)
C8—C1—C2—C3	−178.41 (16)	C10—N1—C8—C9	−3.9 (3)
O1—C2—C3—C4	−177.35 (17)	C6—C1—C8—N1	−172.62 (17)
C1—C2—C3—C4	2.2 (3)	C2—C1—C8—N1	3.6 (2)
C7—O2—C4—C3	−3.4 (3)	C6—C1—C8—C9	7.7 (3)
C7—O2—C4—C5	176.26 (19)	C2—C1—C8—C9	−176.04 (16)
C2—C3—C4—O2	178.73 (17)	C8—N1—C10—C11	−144.49 (18)
C2—C3—C4—C5	−0.9 (3)	N1—C10—C11—C12	−66.5 (2)
O2—C4—C5—C6	179.79 (17)	N1—C10—C11—C13	54.8 (2)
C3—C4—C5—C6	−0.5 (3)	N1—C10—C11—C10ⁱ	173.97 (11)
C4—C5—C6—C1	0.7 (3)

Symmetry code: (i) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.86 (1)	1.70 (2)	2.507 (2)	157 (4)
C7—H7c···Cg1ⁱⁱ	0.96	2.75	3.547 (2)	141
C9—H9b···Cg1ⁱⁱⁱ	0.96	2.66	3.456 (2)	140

Symmetry codes: (ii) x−3/2, y, −z−1/2; (iii) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₃₀N₂O₄
M_r	398.49
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	294
a, b, c (Å)	10.0764 (7), 36.069 (2), 5.8322 (4)
V (Å³)	2119.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.793, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6816, 2419, 1952
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.155, 1.08
No. of reflections	2419
No. of parameters	141
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.857 (10)	1.695 (17)	2.507 (2)	157 (4)
C7—H7c···Cg1ⁱ	0.96	2.75	3.547 (2)	141
C9—H9b···Cg1ⁱⁱ	0.96	2.66	3.456 (2)	140

Symmetry codes: (i) x−3/2, y, −z−1/2; (ii) x−1/2, y, −z+1/2.

Footnotes

‡Additional correspondence author, e-mail: akbarghaemi@yahoo.com.

Acknowledgements

We gratefully acknowledge practical support of this study by K. N. Toosi University of Technology, Islamic Azad University (Saveh Branch), and thank the University of Malaya for support of the crystallographic facility.

References

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Volume 67| Part 10| October 2011| Page o2760

https://doi.org/10.1107/S1600536811038815

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-{(1E)-1-[(3-{(E)-[1-(2-Hy­dr­oxy-4-meth­­oxy­phen­yl)ethyl­­idene]amino}-2,2-di­methyl­prop­yl)imino]­eth­yl}-5-meth­­oxy­phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2-{(1E)-1-[(3-{(E)-[1-(2-Hydroxy-4-methoxyphenyl)ethylidene]amino}-2,2-dimethylpropyl)imino]ethyl}-5-methoxyphenol