5-Meth-oxy-2-{[4-(morpholin-4-yl)phen-yl]imino-meth-yl}phenol.

In the title compound, C(18)H(20)N(2)O(3), the dihedral angle between the two aromatic rings is 33.66 (6)°. The morpholine ring adopts a chair conformation. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond. In the crystal, mol-ecules are linked via weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For the biological activity of morpholine derivatives, see: Lan et al. (2010 ▶); Raparti et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For a related structure, see: Yang et al. (2011 ▶). For the definition of puckering parameters, see: Cremer & Pople (1975 ▶). For graph-set notation, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C18H20N2O3

M = 312.36

Monoclinic,

a = 10.623 (6) Å

b = 9.106 (5) Å

c = 16.640 (5) Å

β = 97.446 (6)°

V = 1596.2 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.982

21296 measured reflections

4941 independent reflections

2761 reflections with I > 2σ(I)

R int = 0.031

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.204

S = 1.05

4941 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034659/bt5628sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034659/bt5628Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034659/bt5628Isup3.cml

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

C18H20N2O3	F(000) = 664
Mr = 312.36	Dx = 1.300 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4380 reflections
a = 10.623 (6) Å	θ = 2.5–30.6°
b = 9.106 (5) Å	µ = 0.09 mm−1
c = 16.640 (5) Å	T = 295 K
β = 97.446 (6)°	Block, colourless
V = 1596.2 (13) Å3	0.28 × 0.24 × 0.20 mm
Z = 4

Bruker Kappa APEXII diffractometer	4941 independent reflections
Radiation source: fine-focus sealed tube	2761 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω and φ scans	θmax = 30.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→15
Tmin = 0.975, Tmax = 0.982	k = −12→12
21296 measured reflections	l = −23→23

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.089P)2 + 0.3452P] where P = (Fo2 + 2Fc2)/3
4941 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.4258 (2)	0.3507 (4)	0.86902 (17)	0.0858 (8)
H1A	0.3592	0.4221	0.8539	0.103*
H1B	0.3974	0.2575	0.8448	0.103*
C2	0.5421 (2)	0.3978 (3)	0.83441 (17)	0.0756 (7)
H2A	0.5265	0.3921	0.7758	0.091*
H2B	0.5609	0.4993	0.8491	0.091*
C3	0.6624 (2)	0.2790 (4)	0.94823 (13)	0.0993 (11)
H3A	0.6977	0.3649	0.9774	0.119*
H3B	0.7214	0.1985	0.9605	0.119*
C4	0.5395 (2)	0.2410 (4)	0.97652 (15)	0.1022 (11)
H4A	0.5149	0.1435	0.9570	0.123*
H4B	0.5519	0.2374	1.0353	0.123*
C5	0.75890 (16)	0.31894 (19)	0.82520 (9)	0.0409 (4)
C6	0.76084 (19)	0.3993 (2)	0.75393 (12)	0.0559 (5)
H6	0.6885	0.4501	0.7320	0.067*
C7	0.86803 (19)	0.4047 (2)	0.71547 (11)	0.0549 (5)
H7	0.8667	0.4599	0.6683	0.066*
C8	0.97710 (16)	0.33047 (18)	0.74518 (9)	0.0396 (4)
C9	0.97771 (17)	0.2539 (2)	0.81688 (10)	0.0472 (4)
H9	1.0510	0.2051	0.8390	0.057*
C10	0.87091 (18)	0.2490 (2)	0.85609 (10)	0.0482 (4)
H10	0.8741	0.1974	0.9045	0.058*
C11	1.16925 (16)	0.24530 (19)	0.70644 (10)	0.0421 (4)
H11	1.1595	0.1603	0.7360	0.051*
C12	1.28060 (16)	0.26119 (18)	0.66578 (9)	0.0393 (4)
C13	1.30539 (17)	0.39126 (18)	0.62486 (10)	0.0402 (4)
C14	1.41223 (17)	0.40335 (19)	0.58674 (10)	0.0450 (4)
H14	1.4284	0.4902	0.5605	0.054*
C15	1.49540 (17)	0.2874 (2)	0.58729 (10)	0.0461 (4)
C16	1.47404 (19)	0.1582 (2)	0.62718 (13)	0.0559 (5)
H16	1.5307	0.0802	0.6280	0.067*
C17	1.36751 (19)	0.1477 (2)	0.66548 (12)	0.0532 (5)
H17	1.3530	0.0609	0.6923	0.064*
C18	1.6838 (2)	0.1948 (3)	0.54114 (18)	0.0868 (8)
H18A	1.7226	0.1680	0.5944	0.130*
H18B	1.7482	0.2261	0.5094	0.130*
H18C	1.6397	0.1117	0.5157	0.130*
N1	0.64900 (14)	0.30818 (19)	0.86311 (8)	0.0491 (4)
N2	1.08397 (14)	0.34434 (16)	0.70305 (8)	0.0420 (3)
O1	0.44192 (16)	0.3353 (2)	0.95242 (11)	0.0846 (6)
O2	1.22521 (14)	0.50605 (14)	0.62211 (9)	0.0607 (4)
H2	1.1635	0.4839	0.6445	0.091*
O3	1.59655 (14)	0.31149 (17)	0.54691 (9)	0.0650 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0467 (13)	0.118 (2)	0.0978 (19)	0.0095 (14)	0.0282 (13)	0.0384 (16)
C2	0.0460 (12)	0.0875 (17)	0.0984 (18)	0.0089 (12)	0.0296 (12)	0.0292 (14)
C3	0.0464 (13)	0.211 (4)	0.0423 (11)	−0.0168 (18)	0.0123 (9)	0.0158 (15)
C4	0.0513 (14)	0.204 (4)	0.0542 (13)	0.0027 (19)	0.0187 (11)	0.0345 (17)
C5	0.0358 (9)	0.0504 (10)	0.0378 (8)	−0.0008 (7)	0.0096 (7)	0.0001 (7)
C6	0.0391 (10)	0.0789 (14)	0.0515 (10)	0.0145 (9)	0.0124 (8)	0.0206 (9)
C7	0.0457 (11)	0.0742 (13)	0.0474 (9)	0.0086 (9)	0.0165 (8)	0.0204 (9)
C8	0.0379 (9)	0.0430 (9)	0.0400 (8)	−0.0018 (7)	0.0131 (7)	−0.0021 (6)
C9	0.0398 (9)	0.0576 (11)	0.0457 (9)	0.0105 (8)	0.0118 (7)	0.0082 (8)
C10	0.0458 (10)	0.0589 (11)	0.0422 (8)	0.0064 (9)	0.0142 (8)	0.0119 (8)
C11	0.0431 (10)	0.0409 (9)	0.0443 (8)	−0.0020 (8)	0.0131 (7)	0.0012 (7)
C12	0.0381 (9)	0.0408 (9)	0.0407 (8)	0.0013 (7)	0.0119 (7)	0.0012 (6)
C13	0.0420 (10)	0.0385 (8)	0.0415 (8)	0.0030 (7)	0.0112 (7)	−0.0010 (6)
C14	0.0479 (11)	0.0416 (9)	0.0483 (9)	−0.0017 (8)	0.0169 (8)	0.0034 (7)
C15	0.0383 (9)	0.0576 (11)	0.0454 (9)	0.0020 (8)	0.0161 (7)	0.0031 (8)
C16	0.0473 (11)	0.0549 (11)	0.0693 (12)	0.0179 (9)	0.0218 (9)	0.0137 (9)
C17	0.0519 (11)	0.0478 (10)	0.0640 (11)	0.0099 (9)	0.0228 (9)	0.0160 (8)
C18	0.0587 (15)	0.106 (2)	0.105 (2)	0.0246 (14)	0.0441 (14)	0.0078 (16)
N1	0.0366 (8)	0.0714 (11)	0.0413 (7)	0.0044 (7)	0.0120 (6)	0.0086 (7)
N2	0.0387 (8)	0.0472 (8)	0.0425 (7)	0.0013 (6)	0.0141 (6)	−0.0004 (6)
O1	0.0549 (10)	0.1205 (15)	0.0859 (12)	−0.0139 (10)	0.0373 (9)	−0.0139 (10)
O2	0.0624 (9)	0.0448 (7)	0.0820 (10)	0.0152 (7)	0.0362 (8)	0.0122 (6)
O3	0.0515 (8)	0.0765 (10)	0.0743 (9)	0.0092 (7)	0.0351 (7)	0.0138 (7)

C1—O1	1.383 (3)	C9—C10	1.381 (2)
C1—C2	1.492 (3)	C9—H9	0.9300
C1—H1A	0.9700	C10—H10	0.9300
C1—H1B	0.9700	C11—N2	1.274 (2)
C2—N1	1.430 (3)	C11—C12	1.444 (2)
C2—H2A	0.9700	C11—H11	0.9300
C2—H2B	0.9700	C12—C17	1.386 (2)
C3—N1	1.430 (3)	C12—C13	1.408 (2)
C3—C4	1.485 (3)	C13—O2	1.345 (2)
C3—H3A	0.9700	C13—C14	1.374 (2)
C3—H3B	0.9700	C14—C15	1.376 (3)
C4—O1	1.365 (3)	C14—H14	0.9300
C4—H4A	0.9700	C15—O3	1.357 (2)
C4—H4B	0.9700	C15—C16	1.384 (3)
C5—C10	1.388 (2)	C16—C17	1.372 (3)
C5—C6	1.396 (2)	C16—H16	0.9300
C5—N1	1.400 (2)	C17—H17	0.9300
C6—C7	1.378 (3)	C18—O3	1.421 (3)
C6—H6	0.9300	C18—H18A	0.9600
C7—C8	1.377 (3)	C18—H18B	0.9600
C7—H7	0.9300	C18—H18C	0.9600
C8—C9	1.381 (2)	O2—H2	0.8200
C8—N2	1.415 (2)
O1—C1—C2	114.5 (2)	C8—C9—H9	119.6
O1—C1—H1A	108.6	C9—C10—C5	121.83 (16)
C2—C1—H1A	108.6	C9—C10—H10	119.1
O1—C1—H1B	108.6	C5—C10—H10	119.1
C2—C1—H1B	108.6	N2—C11—C12	121.94 (16)
H1A—C1—H1B	107.6	N2—C11—H11	119.0
N1—C2—C1	111.6 (2)	C12—C11—H11	119.0
N1—C2—H2A	109.3	C17—C12—C13	117.33 (16)
C1—C2—H2A	109.3	C17—C12—C11	120.88 (16)
N1—C2—H2B	109.3	C13—C12—C11	121.79 (15)
C1—C2—H2B	109.3	O2—C13—C14	118.62 (15)
H2A—C2—H2B	108.0	O2—C13—C12	120.85 (16)
N1—C3—C4	112.25 (18)	C14—C13—C12	120.53 (15)
N1—C3—H3A	109.2	C13—C14—C15	120.22 (16)
C4—C3—H3A	109.2	C13—C14—H14	119.9
N1—C3—H3B	109.2	C15—C14—H14	119.9
C4—C3—H3B	109.2	O3—C15—C14	114.92 (16)
H3A—C3—H3B	107.9	O3—C15—C16	124.38 (17)
O1—C4—C3	115.2 (3)	C14—C15—C16	120.70 (17)
O1—C4—H4A	108.5	C17—C16—C15	118.59 (17)
C3—C4—H4A	108.5	C17—C16—H16	120.7
O1—C4—H4B	108.5	C15—C16—H16	120.7
C3—C4—H4B	108.5	C16—C17—C12	122.63 (17)
H4A—C4—H4B	107.5	C16—C17—H17	118.7
C10—C5—C6	116.66 (16)	C12—C17—H17	118.7
C10—C5—N1	121.72 (15)	O3—C18—H18A	109.5
C6—C5—N1	121.62 (16)	O3—C18—H18B	109.5
C7—C6—C5	121.18 (17)	H18A—C18—H18B	109.5
C7—C6—H6	119.4	O3—C18—H18C	109.5
C5—C6—H6	119.4	H18A—C18—H18C	109.5
C8—C7—C6	121.55 (17)	H18B—C18—H18C	109.5
C8—C7—H7	119.2	C5—N1—C2	118.82 (16)
C6—C7—H7	119.2	C5—N1—C3	118.53 (16)
C7—C8—C9	117.88 (16)	C2—N1—C3	114.18 (19)
C7—C8—N2	118.04 (15)	C11—N2—C8	121.75 (15)
C9—C8—N2	123.97 (16)	C4—O1—C1	110.42 (19)
C10—C9—C8	120.83 (16)	C13—O2—H2	109.5
C10—C9—H9	119.6	C15—O3—C18	118.55 (17)
O1—C1—C2—N1	50.7 (3)	C13—C14—C15—C16	−1.1 (3)
N1—C3—C4—O1	−49.6 (4)	O3—C15—C16—C17	−179.70 (19)
C10—C5—C6—C7	1.8 (3)	C14—C15—C16—C17	0.6 (3)
N1—C5—C6—C7	−177.56 (19)	C15—C16—C17—C12	0.0 (3)
C5—C6—C7—C8	0.5 (3)	C13—C12—C17—C16	−0.2 (3)
C6—C7—C8—C9	−2.3 (3)	C11—C12—C17—C16	179.64 (19)
C6—C7—C8—N2	−178.64 (18)	C10—C5—N1—C2	171.9 (2)
C7—C8—C9—C10	1.8 (3)	C6—C5—N1—C2	−8.8 (3)
N2—C8—C9—C10	177.85 (17)	C10—C5—N1—C3	25.7 (3)
C8—C9—C10—C5	0.6 (3)	C6—C5—N1—C3	−155.0 (2)
C6—C5—C10—C9	−2.3 (3)	C1—C2—N1—C5	167.9 (2)
N1—C5—C10—C9	177.01 (17)	C1—C2—N1—C3	−44.4 (3)
N2—C11—C12—C17	−175.33 (17)	C4—C3—N1—C5	−168.5 (3)
N2—C11—C12—C13	4.5 (3)	C4—C3—N1—C2	43.8 (4)
C17—C12—C13—O2	179.68 (17)	C12—C11—N2—C8	−177.88 (15)
C11—C12—C13—O2	−0.2 (3)	C7—C8—N2—C11	−154.33 (18)
C17—C12—C13—C14	−0.2 (3)	C9—C8—N2—C11	29.6 (3)
C11—C12—C13—C14	179.93 (16)	C3—C4—O1—C1	54.7 (4)
O2—C13—C14—C15	−179.05 (17)	C2—C1—O1—C4	−55.3 (3)
C12—C13—C14—C15	0.9 (3)	C14—C15—O3—C18	−177.0 (2)
C13—C14—C15—O3	179.24 (16)	C16—C15—O3—C18	3.3 (3)

Cg2 and Cg3 are the centroids of the C5–C10 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.87	2.600 (2)	148
C14—H14···O3i	0.93	2.53	3.412 (3)	158
C18—H18B···O1ii	0.96	2.44	3.289 (3)	148
C2—H2A···Cg3iii	0.97	2.92	3.799 (4)	152
C16—H16···Cg2iv	0.93	2.86	3.663 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C5–C10 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.87	2.600 (2)	148
C14—H14⋯O3i	0.93	2.53	3.412 (3)	158
C18—H18B⋯O1ii	0.96	2.44	3.289 (3)	148
C2—H2A⋯Cg3iii	0.97	2.92	3.799 (4)	152
C16—H16⋯Cg2iv	0.93	2.86	3.663 (3)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .