3,5-Dimeth-oxy-2-[(4-propyl-phen-yl)imino-meth-yl]phenol.

The title compound, C(18)H(21)NO(3), crystallizes in the phenol-imine tautomeric form, with the H atom attached to oxygen rather than on nitro-gen. This H atom is involved in a strong intra-molecular O-H⋯N hydrogen bond. A C-H⋯π inter-action is also present. The dihedral angle between the aromatic rings is 12.23 (7)°.

Related literature

Schiff base compounds can be classified by their photochromic and thermochromic characteristics, see: Cohen et al. (1964 ▶); Hadjoudis et al. (1987 ▶); Calligaris et al. (1972 ▶); Hökelek et al. (2000 ▶); Dey et al. (2001 ▶); Ünver et al. (2002 ▶); Karadayı et al. (2003 ▶). Bernstein et al. (1995 ▶) describe the use of graph-set models for the description of hydrogen bonds.

Experimental

Crystal data

C18H21NO3

M = 299.36

Monoclinic,

a = 15.1143 (15) Å

b = 7.2587 (5) Å

c = 17.737 (2) Å

β = 123.669 (7)°

V = 1619.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.48 × 0.26 × 0.12 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: none

18964 measured reflections

3353 independent reflections

1337 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 0.86

3353 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007958/zl2174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007958/zl2174Isup2.hkl

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

C18H21NO3	F(000) = 640
Mr = 299.36	Dx = 1.228 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10898 reflections
a = 15.1143 (15) Å	θ = 1.4–28.0°
b = 7.2587 (5) Å	µ = 0.08 mm−1
c = 17.737 (2) Å	T = 296 K
β = 123.669 (7)°	Prism, yellow
V = 1619.5 (3) Å3	0.48 × 0.26 × 0.12 mm
Z = 4

Stoe IPDS-II diffractometer	1337 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.075
graphite	θmax = 26.5°, θmin = 1.6°
Detector resolution: 6.67 pixels mm-1	h = −18→18
ω scans	k = −8→9
18964 measured reflections	l = −22→22
3353 independent 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 0.86	w = 1/[σ2(Fo2) + (0.0666P)2] where P = (Fo2 + 2Fc2)/3
3353 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.21 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	0.53442 (17)	0.1004 (3)	0.80353 (15)	0.0667 (6)
C2	0.57933 (17)	0.1123 (3)	0.75252 (15)	0.0672 (6)
C3	0.68738 (17)	0.1079 (3)	0.79200 (16)	0.0722 (7)
H3	0.7155	0.1170	0.7569	0.087*
C4	0.75352 (18)	0.0896 (3)	0.88549 (17)	0.0730 (7)
C5	0.71280 (19)	0.0762 (4)	0.93799 (17)	0.0825 (8)
H5	0.7584	0.0629	1.0004	0.099*
C6	0.60502 (18)	0.0825 (3)	0.89829 (16)	0.0732 (7)
C7	0.26549 (18)	0.0884 (3)	0.76044 (16)	0.0678 (6)
C8	0.1924 (2)	0.1356 (4)	0.67118 (18)	0.0873 (8)
H8	0.2159	0.1722	0.6348	0.105*
C9	0.0850 (2)	0.1289 (4)	0.63550 (19)	0.0919 (8)
H9	0.0375	0.1597	0.5749	0.110*
C10	0.0452 (2)	0.0787 (4)	0.6858 (2)	0.0817 (7)
C11	0.1189 (2)	0.0343 (4)	0.7747 (2)	0.0931 (9)
H11	0.0953	0.0002	0.8112	0.112*
C12	0.2272 (2)	0.0384 (4)	0.81199 (18)	0.0870 (8)
H12	0.2745	0.0069	0.8725	0.104*
C16	0.42105 (17)	0.1008 (3)	0.76044 (16)	0.0719 (7)
H16	0.3775	0.1081	0.6976	0.086*
C18	0.90908 (19)	0.1115 (4)	0.8815 (2)	0.1004 (9)
H18A	0.9850	0.1025	0.9219	0.151*
H18B	0.8904	0.2318	0.8546	0.151*
H18C	0.8840	0.0200	0.8349	0.151*
C17	0.5443 (2)	0.1229 (5)	0.60388 (16)	0.0988 (9)
H17A	0.4853	0.1357	0.5421	0.148*
H17B	0.5792	0.0074	0.6113	0.148*
H17C	0.5936	0.2219	0.6191	0.148*
C13	−0.0731 (2)	0.0740 (5)	0.6453 (2)	0.1140 (11)
H13A	−0.0832	0.0528	0.6941	0.137*
H13B	−0.1018	0.1950	0.6205	0.137*
C14	−0.1353 (2)	−0.0597 (5)	0.5758 (2)	0.1255 (12)
H14A	−0.1062	−0.1811	0.5996	0.151*
H14B	−0.1278	−0.0367	0.5257	0.151*
C15	−0.2534 (2)	−0.0615 (5)	0.5394 (2)	0.1338 (14)
H15A	−0.2886	−0.1549	0.4937	0.201*
H15B	−0.2838	0.0566	0.5136	0.201*
H15C	−0.2621	−0.0872	0.5880	0.201*
N1	0.37759 (14)	0.0914 (3)	0.80506 (13)	0.0738 (6)
O1	0.86157 (12)	0.0821 (3)	0.93083 (11)	0.0921 (6)
O2	0.56789 (13)	0.0725 (3)	0.95188 (11)	0.0995 (7)
H2	0.5027	0.0758	0.9205	0.149*
O3	0.50721 (11)	0.1284 (3)	0.66174 (10)	0.0869 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0666 (14)	0.0706 (17)	0.0586 (14)	−0.0048 (12)	0.0320 (13)	−0.0038 (13)
C2	0.0695 (15)	0.0707 (17)	0.0538 (14)	−0.0022 (12)	0.0293 (13)	−0.0031 (13)
C3	0.0699 (15)	0.0791 (18)	0.0677 (16)	−0.0023 (13)	0.0382 (13)	−0.0020 (15)
C4	0.0604 (14)	0.0728 (18)	0.0689 (16)	−0.0079 (12)	0.0254 (13)	−0.0030 (14)
C5	0.0741 (16)	0.106 (2)	0.0550 (14)	−0.0098 (15)	0.0280 (13)	−0.0006 (15)
C6	0.0744 (16)	0.0859 (19)	0.0553 (15)	−0.0108 (13)	0.0334 (14)	−0.0040 (14)
C7	0.0701 (15)	0.0712 (17)	0.0626 (15)	0.0008 (13)	0.0370 (14)	0.0005 (13)
C8	0.0779 (17)	0.100 (2)	0.0752 (18)	−0.0001 (15)	0.0368 (15)	0.0181 (16)
C9	0.0726 (17)	0.103 (2)	0.0811 (19)	0.0046 (15)	0.0309 (15)	0.0133 (17)
C10	0.0770 (16)	0.0770 (19)	0.094 (2)	0.0042 (14)	0.0491 (17)	−0.0086 (16)
C11	0.092 (2)	0.112 (2)	0.094 (2)	0.0066 (17)	0.0632 (19)	−0.0021 (19)
C12	0.0814 (18)	0.111 (2)	0.0739 (17)	0.0118 (15)	0.0463 (16)	0.0044 (15)
C16	0.0728 (15)	0.0767 (18)	0.0590 (14)	0.0011 (13)	0.0322 (13)	−0.0028 (14)
C18	0.0740 (16)	0.115 (2)	0.109 (2)	−0.0058 (16)	0.0486 (17)	0.0204 (19)
C17	0.0904 (17)	0.151 (3)	0.0602 (16)	0.0001 (18)	0.0451 (15)	−0.0106 (18)
C13	0.0812 (18)	0.124 (3)	0.131 (3)	0.0047 (18)	0.0549 (19)	−0.025 (2)
C14	0.0813 (19)	0.153 (3)	0.137 (3)	−0.007 (2)	0.057 (2)	−0.023 (3)
C15	0.0733 (19)	0.149 (3)	0.162 (3)	−0.0030 (19)	0.054 (2)	0.006 (3)
N1	0.0709 (12)	0.0871 (16)	0.0628 (12)	−0.0019 (11)	0.0367 (11)	−0.0005 (11)
O1	0.0646 (10)	0.1177 (16)	0.0783 (12)	−0.0085 (10)	0.0298 (10)	0.0050 (11)
O2	0.0793 (11)	0.156 (2)	0.0590 (10)	−0.0110 (13)	0.0359 (9)	0.0003 (12)
O3	0.0715 (10)	0.1344 (16)	0.0519 (10)	0.0047 (10)	0.0324 (9)	0.0013 (11)

C1—C2	1.403 (3)	C11—H11	0.9300
C1—C6	1.411 (3)	C12—H12	0.9300
C1—C16	1.438 (3)	C16—N1	1.280 (3)
C2—O3	1.360 (2)	C16—H16	0.9300
C2—C3	1.375 (3)	C18—O1	1.422 (3)
C3—C4	1.389 (3)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—O1	1.364 (3)	C18—H18C	0.9600
C4—C5	1.375 (3)	C17—O3	1.417 (2)
C5—C6	1.371 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—O2	1.347 (3)	C17—H17C	0.9600
C7—C12	1.374 (3)	C13—C14	1.435 (4)
C7—C8	1.380 (3)	C13—H13A	0.9700
C7—N1	1.418 (3)	C13—H13B	0.9700
C8—C9	1.379 (3)	C14—C15	1.525 (3)
C8—H8	0.9300	C14—H14A	0.9700
C9—C10	1.373 (3)	C14—H14B	0.9700
C9—H9	0.9300	C15—H15A	0.9600
C10—C11	1.373 (4)	C15—H15B	0.9600
C10—C13	1.514 (3)	C15—H15C	0.9600
C11—C12	1.385 (3)	O2—H2	0.8200
C2—C1—C6	117.2 (2)	N1—C16—H16	118.7
C2—C1—C16	121.1 (2)	C1—C16—H16	118.7
C6—C1—C16	121.6 (2)	O1—C18—H18A	109.5
O3—C2—C3	123.5 (2)	O1—C18—H18B	109.5
O3—C2—C1	114.34 (19)	H18A—C18—H18B	109.5
C3—C2—C1	122.2 (2)	O1—C18—H18C	109.5
C2—C3—C4	118.4 (2)	H18A—C18—H18C	109.5
C2—C3—H3	120.8	H18B—C18—H18C	109.5
C4—C3—H3	120.8	O3—C17—H17A	109.5
O1—C4—C5	115.9 (2)	O3—C17—H17B	109.5
O1—C4—C3	122.8 (2)	H17A—C17—H17B	109.5
C5—C4—C3	121.3 (2)	O3—C17—H17C	109.5
C6—C5—C4	120.0 (2)	H17A—C17—H17C	109.5
C6—C5—H5	120.0	H17B—C17—H17C	109.5
C4—C5—H5	120.0	C14—C13—C10	117.5 (3)
O2—C6—C5	118.5 (2)	C14—C13—H13A	107.9
O2—C6—C1	120.6 (2)	C10—C13—H13A	107.9
C5—C6—C1	120.9 (2)	C14—C13—H13B	107.9
C12—C7—C8	117.7 (2)	C10—C13—H13B	107.9
C12—C7—N1	116.5 (2)	H13A—C13—H13B	107.2
C8—C7—N1	125.8 (2)	C13—C14—C15	115.1 (3)
C9—C8—C7	120.5 (2)	C13—C14—H14A	108.5
C9—C8—H8	119.8	C15—C14—H14A	108.5
C7—C8—H8	119.8	C13—C14—H14B	108.5
C10—C9—C8	122.7 (3)	C15—C14—H14B	108.5
C10—C9—H9	118.7	H14A—C14—H14B	107.5
C8—C9—H9	118.7	C14—C15—H15A	109.5
C9—C10—C11	116.1 (2)	C14—C15—H15B	109.5
C9—C10—C13	121.7 (3)	H15A—C15—H15B	109.5
C11—C10—C13	122.2 (3)	C14—C15—H15C	109.5
C10—C11—C12	122.3 (3)	H15A—C15—H15C	109.5
C10—C11—H11	118.8	H15B—C15—H15C	109.5
C12—C11—H11	118.8	C16—N1—C7	121.3 (2)
C7—C12—C11	120.7 (3)	C4—O1—C18	118.6 (2)
C7—C12—H12	119.7	C6—O2—H2	109.5
C11—C12—H12	119.7	C2—O3—C17	118.41 (18)
N1—C16—C1	122.7 (2)
C6—C1—C2—O3	179.7 (2)	C8—C9—C10—C11	−0.2 (4)
C16—C1—C2—O3	1.6 (3)	C8—C9—C10—C13	179.5 (3)
C6—C1—C2—C3	−0.3 (4)	C9—C10—C11—C12	−0.4 (4)
C16—C1—C2—C3	−178.5 (2)	C13—C10—C11—C12	180.0 (3)
O3—C2—C3—C4	−179.5 (2)	C8—C7—C12—C11	0.6 (4)
C1—C2—C3—C4	0.5 (4)	N1—C7—C12—C11	179.0 (2)
C2—C3—C4—O1	179.3 (2)	C10—C11—C12—C7	0.2 (4)
C2—C3—C4—C5	−0.1 (4)	C2—C1—C16—N1	−179.5 (2)
O1—C4—C5—C6	180.0 (2)	C6—C1—C16—N1	2.5 (4)
C3—C4—C5—C6	−0.6 (4)	C9—C10—C13—C14	66.0 (4)
C4—C5—C6—O2	−178.8 (2)	C11—C10—C13—C14	−114.4 (4)
C4—C5—C6—C1	0.8 (4)	C10—C13—C14—C15	178.4 (3)
C2—C1—C6—O2	179.2 (2)	C1—C16—N1—C7	−178.7 (2)
C16—C1—C6—O2	−2.7 (4)	C12—C7—N1—C16	166.3 (2)
C2—C1—C6—C5	−0.3 (4)	C8—C7—N1—C16	−15.5 (4)
C16—C1—C6—C5	177.8 (2)	C5—C4—O1—C18	−174.5 (2)
C12—C7—C8—C9	−1.1 (4)	C3—C4—O1—C18	6.1 (4)
N1—C7—C8—C9	−179.3 (2)	C3—C2—O3—C17	6.2 (4)
C7—C8—C9—C10	0.9 (4)	C1—C2—O3—C17	−173.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.87	2.602 (2)	148
C18—H18B···Cg2i	0.96	2.80	3.764 (3)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.87	2.602 (2)	148
C18—H18B⋯Cg2i	0.96	2.80	3.764 (3)	178

Symmetry code: (i) . Cg2 is the centroid of the C7–C12 ring.