Crystal structure of (Z)-3-benz­yloxy-6-[(2-hy­droxy-5-methyl­anilino)methyl­idene]cyclo­hexa-2,4-dien-1-one

Ghichi, N.; Benosmane, A.; Benboudiaf, A.; Merazig, H.

doi:10.1107/S1600536814016936

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o957-o958

doi:10.1107/S1600536814016936

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Crystal structure of (Z)-3-benzyloxy-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one

Nadir Ghichi,^a Ali Benosmane,^a ^* Ali Benboudiaf ^a and Hocine Merazig ^a

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université Constantine 1, Algeria
^*Correspondence e-mail: king.ali@hotmail.fr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 July 2014; accepted 22 July 2014; online 1 August 2014)

In the title Schiff base compound, C₂₁H₁₉NO₃, the conformation about the C=C bond is Z. The N—H group and carbonyl O atom form an intramolecular N—H⋯O hydrogen bond with an S(6) ring motif. The benzyloxy ring and the 2-hydroxy-5-methylphenyl ring are inclined to the central six-membered ring by 13.68 (9) and 9.13 (8)°, respectively, and to one another by 21.95 (9)°. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming helical chains along [010].

Keywords: crystal structure; Schiff base; azomethines.

CCDC reference: 1015522

1. Related literature

For some general background on Schiff bases and their various biological activities, see: Arora et al. (2002 ); El-Masry et al. (2000 ); Jarrahpour & Khalili (2006 ); More et al. (2001 ); Phatak et al. (2000 ). For related structures, see: Akkurt et al. (2005 , 2008 ). For pharmaceutical and industrial applications of azomethines, see: Prakash & Adhikari (2011 ). For the effect of hydrophilicity on drug properties, see: Lin & Lu (1997 ).

2. Experimental

2.1. Crystal data

C₂₁H₁₉NO₃
M_r = 333.37
Monoclinic, P 2₁ /c
a = 12.594 (5) Å
b = 9.303 (5) Å
c = 14.997 (5) Å
β = 96.402 (5)°
V = 1746.1 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.03 × 0.02 × 0.01 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
19603 measured reflections
5148 independent reflections
2672 reflections with I > 2σ(I)
R_int = 0.037

2.3. Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.158
S = 1.01
5148 reflections
238 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O2	0.94 (2)	1.83 (2)	2.609 (2)	138.7 (16)
O1—H1o⋯O2ⁱ	0.96 (2)	1.63 (2)	2.590 (2)	176.1 (17)
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; 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, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1015522

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814016936/su2761sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016936/su2761Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814016936/su2761Isup3.cml

checkCIF report

Related literature top

For some general background on Schiff bases and their various biological activities, see: Arora et al. (2002); El-Masry et al. (2000); Jarrahpour & Khalili (2006); More et al. (2001); Phatak et al. (2000). For related structures, see: Akkurt et al. (2005, 2008). For pharmaceutical and industrial applications of azomethines, see: Prakash & Adhikari (2011). For the effect of hydrophilicity on drug properties, see: Lin & Lu (1997).

Experimental top

A mixture of 2-amino-4-methylphenol (1 mmol) and 4-(benzyloxy)-2-hydroxybenzaldehyde (1 mmol) was heated to form a clear solution. To this a few drops of conc. HCL was added as a catalyst and the mixture was refluxed for 12 h. After cooling the solution to 80°C it was stirred for 45 min the a precipitate formed. It was filtered off and washed with ice cold ethyl acetate to give the pure title Schiff base compound as an orange solid (yield 35%). This crude product was dissolved in ethyl acetate and two spoons of activated charcoal were added. The mixture was filtered over celiteµ000174 and the product was crystallized from ethyl acetate. The compound was very difficult to crystalize and only after several attempts over a period of four months were crystals suitable for X-ray diffraction analysis finally obtained.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. View of the molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Partial view along the b axis of the crystal packing of the title compound, showing the hydrogen bonds as dashed lines (see Table 1 for details).

(Z)-3-Benzyloxy-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one top

Crystal data top

C₂₁H₁₉NO₃	Z = 4
M_r = 333.37	F(000) = 704
Monoclinic, P2₁/c	D_x = 1.268 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.594 (5) Å	µ = 0.09 mm⁻¹
b = 9.303 (5) Å	T = 293 K
c = 14.997 (5) Å	Block, orange
β = 96.402 (5)°	0.03 × 0.02 × 0.01 mm
V = 1746.1 (13) Å³

Data collection top

Bruker APEXII CCD diffractometer	2672 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 30.2°, θ_min = 2.6°
phi and ω scans	h = −17→17
19603 measured reflections	k = −13→13
5148 independent reflections	l = −21→20

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0718P)² + 0.1066P] where P = (F_o² + 2F_c²)/3
5148 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₁H₁₉NO₃	V = 1746.1 (13) Å³
M_r = 333.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.594 (5) Å	µ = 0.09 mm⁻¹
b = 9.303 (5) Å	T = 293 K
c = 14.997 (5) Å	0.03 × 0.02 × 0.01 mm
β = 96.402 (5)°

Data collection top

Bruker APEXII CCD diffractometer	2672 reflections with I > 2σ(I)
19603 measured reflections	R_int = 0.037
5148 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.22 e Å⁻³
5148 reflections	Δρ_min = −0.16 e Å⁻³
238 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.00597 (9)	0.00730 (11)	0.29239 (8)	0.0607 (4)
O2	0.11904 (9)	0.35839 (11)	0.32139 (8)	0.0632 (4)
O3	0.35952 (9)	0.74624 (12)	0.39999 (9)	0.0686 (4)
N1	0.14153 (10)	0.12579 (13)	0.41887 (9)	0.0466 (4)
C1	0.10315 (13)	−0.23275 (17)	0.52145 (11)	0.0543 (5)
C2	0.03317 (14)	−0.29008 (17)	0.45329 (12)	0.0599 (6)
C3	−0.00117 (13)	−0.21414 (16)	0.37654 (11)	0.0557 (5)
C4	0.03510 (12)	−0.07513 (15)	0.36568 (10)	0.0464 (5)
C5	0.10653 (11)	−0.01575 (15)	0.43336 (10)	0.0435 (4)
C6	0.13925 (12)	−0.09409 (16)	0.51009 (10)	0.0502 (5)
C7	0.21681 (12)	0.19787 (17)	0.46691 (11)	0.0500 (5)
C8	0.24727 (11)	0.33802 (16)	0.44826 (10)	0.0488 (5)
C9	0.19690 (11)	0.41507 (16)	0.37232 (11)	0.0488 (5)
C10	0.23632 (12)	0.55360 (16)	0.35497 (11)	0.0535 (5)
C11	0.31795 (12)	0.61279 (17)	0.41101 (11)	0.0549 (6)
C12	0.36589 (14)	0.53810 (18)	0.48665 (13)	0.0654 (6)
C13	0.33182 (13)	0.40505 (18)	0.50384 (12)	0.0626 (6)
C14	0.31877 (13)	0.82640 (18)	0.32322 (12)	0.0600 (6)
C15	0.37303 (14)	0.96959 (18)	0.32326 (12)	0.0597 (6)
C16	0.32694 (18)	1.0777 (2)	0.26853 (13)	0.0769 (8)
C17	0.3757 (2)	1.2105 (2)	0.26580 (14)	0.0893 (9)
C18	0.4695 (2)	1.2378 (2)	0.31800 (16)	0.0918 (10)
C19	0.51594 (18)	1.1327 (2)	0.37257 (18)	0.0933 (9)
C20	0.46785 (16)	0.9979 (2)	0.37561 (16)	0.0781 (8)
C21	0.13941 (16)	−0.3163 (2)	0.60556 (13)	0.0792 (8)
H1o	−0.0411 (17)	−0.044 (2)	0.2490 (16)	0.101 (7)*
H2	0.00830	−0.38330	0.45937	0.0719*
H1n	0.1091 (14)	0.1794 (19)	0.3701 (13)	0.075 (6)*
H3	−0.04862	−0.25606	0.33208	0.0668*
H6	0.18647	−0.05266	0.55491	0.0603*
H7	0.2525 (13)	0.1493 (17)	0.5192 (12)	0.065 (5)*
H10	0.20650	0.60482	0.30510	0.0642*
H12	0.42068	0.58043	0.52442	0.0785*
H13	0.36443	0.35558	0.55341	0.0750*
H14A	0.24242	0.84004	0.32335	0.0720*
H14B	0.33057	0.77387	0.26933	0.0720*
H16	0.26261	1.06082	0.23328	0.0922*
H17	0.34437	1.28183	0.22815	0.1070*
H18	0.50154	1.32764	0.31634	0.1101*
H19	0.57997	1.15094	0.40792	0.1119*
H20	0.49987	0.92686	0.41309	0.0937*
H21A	0.10696	−0.40980	0.60202	0.1186*
H21B	0.11862	−0.26601	0.65674	0.1186*
H21C	0.21574	−0.32628	0.61143	0.1186*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0764 (8)	0.0485 (6)	0.0514 (7)	−0.0042 (5)	−0.0186 (6)	0.0026 (5)
O2	0.0626 (7)	0.0505 (6)	0.0687 (8)	−0.0121 (5)	−0.0277 (6)	0.0067 (5)
O3	0.0682 (7)	0.0572 (7)	0.0771 (9)	−0.0194 (6)	−0.0061 (6)	−0.0054 (6)
N1	0.0481 (7)	0.0460 (7)	0.0435 (7)	0.0016 (5)	−0.0050 (6)	−0.0001 (6)
C1	0.0591 (10)	0.0511 (9)	0.0523 (9)	0.0110 (7)	0.0047 (8)	0.0065 (7)
C2	0.0691 (10)	0.0415 (8)	0.0684 (11)	0.0006 (7)	0.0041 (9)	0.0038 (8)
C3	0.0612 (10)	0.0449 (8)	0.0580 (10)	−0.0016 (7)	−0.0066 (8)	−0.0057 (7)
C4	0.0490 (8)	0.0436 (8)	0.0448 (8)	0.0055 (6)	−0.0029 (7)	−0.0017 (6)
C5	0.0430 (7)	0.0412 (7)	0.0456 (8)	0.0057 (6)	0.0019 (6)	−0.0023 (6)
C6	0.0502 (9)	0.0533 (9)	0.0457 (9)	0.0052 (7)	−0.0014 (7)	0.0000 (7)
C7	0.0501 (9)	0.0538 (9)	0.0436 (9)	0.0020 (7)	−0.0060 (7)	−0.0022 (7)
C8	0.0449 (8)	0.0508 (8)	0.0487 (9)	−0.0029 (7)	−0.0041 (7)	−0.0059 (7)
C9	0.0426 (8)	0.0482 (8)	0.0529 (9)	−0.0017 (6)	−0.0063 (7)	−0.0075 (7)
C10	0.0517 (9)	0.0491 (8)	0.0569 (10)	−0.0032 (7)	−0.0069 (7)	−0.0011 (7)
C11	0.0484 (9)	0.0501 (9)	0.0650 (11)	−0.0082 (7)	0.0013 (8)	−0.0106 (8)
C12	0.0581 (10)	0.0642 (11)	0.0682 (11)	−0.0130 (8)	−0.0182 (9)	−0.0096 (9)
C13	0.0612 (10)	0.0634 (10)	0.0576 (10)	−0.0062 (8)	−0.0178 (8)	−0.0039 (8)
C14	0.0588 (10)	0.0554 (9)	0.0659 (11)	−0.0070 (8)	0.0075 (9)	−0.0090 (8)
C15	0.0650 (11)	0.0543 (9)	0.0630 (11)	−0.0093 (8)	0.0210 (9)	−0.0150 (8)
C16	0.1016 (15)	0.0646 (12)	0.0650 (12)	−0.0107 (11)	0.0122 (11)	−0.0092 (10)
C17	0.140 (2)	0.0627 (12)	0.0685 (14)	−0.0114 (13)	0.0257 (14)	−0.0049 (10)
C18	0.127 (2)	0.0675 (13)	0.0879 (17)	−0.0338 (13)	0.0433 (15)	−0.0139 (12)
C19	0.0841 (15)	0.0798 (15)	0.1170 (19)	−0.0316 (12)	0.0161 (14)	−0.0185 (14)
C20	0.0707 (12)	0.0616 (11)	0.1026 (16)	−0.0153 (9)	0.0123 (11)	−0.0092 (10)
C21	0.0904 (14)	0.0737 (12)	0.0710 (13)	0.0068 (10)	−0.0014 (11)	0.0239 (10)

Geometric parameters (Å, º) top

O1—C4	1.357 (2)	C15—C20	1.379 (3)
O2—C9	1.287 (2)	C15—C16	1.384 (3)
O3—C11	1.365 (2)	C16—C17	1.382 (3)
O3—C14	1.419 (2)	C17—C18	1.366 (4)
O1—H1o	0.96 (2)	C18—C19	1.364 (3)
N1—C5	1.413 (2)	C19—C20	1.396 (3)
N1—C7	1.310 (2)	C2—H2	0.9300
N1—H1n	0.940 (19)	C3—H3	0.9300
C1—C6	1.385 (2)	C6—H6	0.9300
C1—C21	1.508 (3)	C7—H7	0.971 (17)
C1—C2	1.380 (3)	C10—H10	0.9300
C2—C3	1.378 (2)	C12—H12	0.9300
C3—C4	1.387 (2)	C13—H13	0.9300
C4—C5	1.393 (2)	C14—H14A	0.9700
C5—C6	1.385 (2)	C14—H14B	0.9700
C7—C8	1.396 (2)	C16—H16	0.9300
C8—C13	1.421 (2)	C17—H17	0.9300
C8—C9	1.433 (2)	C18—H18	0.9300
C9—C10	1.416 (2)	C19—H19	0.9300
C10—C11	1.369 (2)	C20—H20	0.9300
C11—C12	1.408 (3)	C21—H21A	0.9600
C12—C13	1.344 (2)	C21—H21B	0.9600
C14—C15	1.497 (3)	C21—H21C	0.9600

C11—O3—C14	117.87 (13)	C18—C19—C20	120.3 (2)
C4—O1—H1o	111.1 (13)	C15—C20—C19	120.28 (19)
C5—N1—C7	127.71 (13)	C1—C2—H2	119.00
C5—N1—H1n	119.9 (11)	C3—C2—H2	119.00
C7—N1—H1n	112.4 (11)	C2—C3—H3	120.00
C2—C1—C6	117.40 (15)	C4—C3—H3	120.00
C2—C1—C21	121.94 (15)	C1—C6—H6	119.00
C6—C1—C21	120.67 (15)	C5—C6—H6	119.00
C1—C2—C3	122.37 (15)	N1—C7—H7	116.6 (10)
C2—C3—C4	119.94 (15)	C8—C7—H7	118.9 (10)
C3—C4—C5	118.58 (14)	C9—C10—H10	120.00
O1—C4—C3	124.00 (14)	C11—C10—H10	120.00
O1—C4—C5	117.41 (13)	C11—C12—H12	120.00
N1—C5—C4	116.40 (13)	C13—C12—H12	120.00
N1—C5—C6	123.29 (13)	C8—C13—H13	119.00
C4—C5—C6	120.31 (13)	C12—C13—H13	119.00
C1—C6—C5	121.40 (14)	O3—C14—H14A	110.00
N1—C7—C8	124.48 (15)	O3—C14—H14B	110.00
C9—C8—C13	118.89 (14)	C15—C14—H14A	110.00
C7—C8—C9	121.29 (14)	C15—C14—H14B	110.00
C7—C8—C13	119.80 (14)	H14A—C14—H14B	108.00
O2—C9—C8	120.49 (13)	C15—C16—H16	120.00
O2—C9—C10	121.57 (14)	C17—C16—H16	120.00
C8—C9—C10	117.93 (14)	C16—C17—H17	120.00
C9—C10—C11	120.54 (15)	C18—C17—H17	120.00
C10—C11—C12	121.43 (15)	C17—C18—H18	120.00
O3—C11—C12	114.26 (14)	C19—C18—H18	120.00
O3—C11—C10	124.31 (15)	C18—C19—H19	120.00
C11—C12—C13	119.45 (16)	C20—C19—H19	120.00
C8—C13—C12	121.72 (16)	C15—C20—H20	120.00
O3—C14—C15	110.09 (14)	C19—C20—H20	120.00
C14—C15—C16	119.02 (16)	C1—C21—H21A	109.00
C14—C15—C20	122.43 (16)	C1—C21—H21B	109.00
C16—C15—C20	118.55 (17)	C1—C21—H21C	109.00
C15—C16—C17	120.6 (2)	H21A—C21—H21B	109.00
C16—C17—C18	120.52 (19)	H21A—C21—H21C	109.00
C17—C18—C19	119.73 (19)	H21B—C21—H21C	109.00

C14—O3—C11—C10	−3.0 (2)	C7—C8—C9—C10	−176.46 (14)
C14—O3—C11—C12	177.39 (14)	C13—C8—C9—O2	−178.95 (14)
C11—O3—C14—C15	179.43 (14)	C13—C8—C9—C10	1.8 (2)
C7—N1—C5—C4	−171.50 (15)	C7—C8—C13—C12	177.89 (16)
C7—N1—C5—C6	8.9 (2)	C9—C8—C13—C12	−0.4 (2)
C5—N1—C7—C8	179.88 (14)	O2—C9—C10—C11	178.81 (15)
C6—C1—C2—C3	−0.4 (3)	C8—C9—C10—C11	−1.9 (2)
C21—C1—C2—C3	179.41 (16)	C9—C10—C11—O3	−178.96 (14)
C2—C1—C6—C5	0.0 (2)	C9—C10—C11—C12	0.7 (2)
C21—C1—C6—C5	−179.84 (15)	O3—C11—C12—C13	−179.54 (15)
C1—C2—C3—C4	0.3 (3)	C10—C11—C12—C13	0.8 (3)
C2—C3—C4—O1	179.74 (15)	C11—C12—C13—C8	−0.9 (3)
C2—C3—C4—C5	0.3 (2)	O3—C14—C15—C16	−163.21 (16)
O1—C4—C5—N1	0.2 (2)	O3—C14—C15—C20	17.1 (2)
O1—C4—C5—C6	179.81 (14)	C14—C15—C16—C17	−178.97 (18)
C3—C4—C5—N1	179.66 (14)	C20—C15—C16—C17	0.7 (3)
C3—C4—C5—C6	−0.7 (2)	C14—C15—C20—C19	179.30 (19)
N1—C5—C6—C1	−179.83 (14)	C16—C15—C20—C19	−0.4 (3)
C4—C5—C6—C1	0.6 (2)	C15—C16—C17—C18	−0.9 (3)
N1—C7—C8—C9	−0.4 (2)	C16—C17—C18—C19	0.7 (4)
N1—C7—C8—C13	−178.58 (15)	C17—C18—C19—C20	−0.3 (4)
C7—C8—C9—O2	2.8 (2)	C18—C19—C20—C15	0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2	0.94 (2)	1.83 (2)	2.609 (2)	138.7 (16)
O1—H1o···O2ⁱ	0.96 (2)	1.63 (2)	2.590 (2)	176.1 (17)

Symmetry code: (i) −x, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2	0.94 (2)	1.83 (2)	2.609 (2)	138.7 (16)
O1—H1o···O2ⁱ	0.96 (2)	1.63 (2)	2.590 (2)	176.1 (17)

Symmetry code: (i) −x, y−1/2, −z+1/2.

Acknowledgements

The authors thank the MESRS (Algeria) for financial support. We also thank all researchers of the CHEMS Research Unit, University of Constantine 1, Algeria, for their valuable assistance.

References

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Volume 70| Part 9| September 2014| Pages o957-o958

doi:10.1107/S1600536814016936

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

Crystal structure of (Z)-3-benz­yl­oxy-6-[(2-hy­dr­oxy-5-methyl­anilino)methyl­­idene]cyclo­hexa-2,4-dien-1-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (Z)-3-benzyloxy-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one