N-[2-(2-Hy-droxy-eth-oxy)pheneth-yl]phthalimide.

The title compound, C(18)H(17)NO(4), was obtained accidentally through acid-catalysed aromatization of a phthalimide-substituted 2-(1-hy-droxy-eth-yl)cyclo-hex-2-enone. It exhibits an intra-molecular O-H⋯O(c) (c = carbonyl) hydrogen bond and forms a three-dimensional network structure via π-π stacking inter-actions between adjacent benzene rings (phthalimide-to-phenyl-ene and phthalimide-to-phthalimide), with centroid-centroid distances of 3.8262 (6) and 3.6245 (5) Å.

Related literature

For background to the titanium(IV) chloride-promoted Baylis–Hillman reaction, see: Basavaiah et al. (2010 ▶); Park et al. (2004 ▶); Qi et al. (2011 ▶); Reggelin et al. (2006 ▶); Veale et al. (2008 ▶). For protection of ketones as 1,3-dioxolanes, see: Chen et al. (2011 ▶); Shih & Swenton (1982 ▶). For background and a possible mechanism of the aromatization reaction, see: Patra et al. (2002 ▶); Lewin et al. (2008 ▶).

Experimental

Crystal data

C18H17NO4

M = 311.33

Monoclinic,

a = 8.4799 (19) Å

b = 22.954 (5) Å

c = 8.5089 (19) Å

β = 110.077 (2)°

V = 1555.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.32 × 0.29 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.970, T max = 0.980

10978 measured reflections

2891 independent reflections

1867 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.146

S = 1.04

2891 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.25 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018429/zl2473sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018429/zl2473Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018429/zl2473Isup3.cml

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

C18H17NO4	F(000) = 656
Mr = 311.33	Dx = 1.329 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.4799 (19) Å	Cell parameters from 3059 reflections
b = 22.954 (5) Å	θ = 2.6–27.7°
c = 8.5089 (19) Å	µ = 0.09 mm−1
β = 110.077 (2)°	T = 296 K
V = 1555.6 (6) Å3	Block, colourless
Z = 4	0.32 × 0.29 × 0.21 mm

Bruker APEXII CCD diffractometer	2891 independent reflections
Radiation source: fine-focus sealed tube	1867 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
Tmin = 0.970, Tmax = 0.980	k = −27→26
10978 measured reflections	l = −9→10

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.9244P] where P = (Fo2 + 2Fc2)/3
2891 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.25 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	0.3135 (3)	0.43925 (12)	0.1572 (4)	0.0526 (7)
C2	0.4828 (3)	0.45631 (11)	0.2714 (4)	0.0510 (7)
C3	0.5941 (4)	0.49717 (13)	0.2529 (4)	0.0678 (9)
H3	0.5698	0.5191	0.1556	0.081*
C4	0.7434 (4)	0.50426 (16)	0.3846 (6)	0.0807 (11)
H4	0.8209	0.5315	0.3757	0.097*
C5	0.7792 (4)	0.47205 (16)	0.5276 (5)	0.0784 (11)
H5	0.8809	0.4778	0.6139	0.094*
C6	0.6675 (4)	0.43115 (14)	0.5464 (4)	0.0656 (8)
H6	0.6920	0.4091	0.6436	0.079*
C7	0.5189 (3)	0.42441 (11)	0.4159 (4)	0.0502 (7)
C8	0.3739 (3)	0.38582 (11)	0.3991 (4)	0.0500 (7)
C9	0.0948 (3)	0.36841 (11)	0.1771 (3)	0.0502 (7)
H9A	0.1011	0.3308	0.2308	0.060*
H9B	0.0678	0.3617	0.0581	0.060*
C10	−0.0443 (3)	0.40388 (10)	0.2042 (3)	0.0435 (6)
H10A	−0.0109	0.4153	0.3209	0.052*
H10B	−0.0623	0.4391	0.1373	0.052*
C11	−0.2049 (3)	0.36999 (10)	0.1575 (3)	0.0404 (6)
C12	−0.3276 (3)	0.37546 (13)	0.0032 (3)	0.0581 (7)
H12	−0.3116	0.4017	−0.0731	0.070*
C13	−0.4738 (4)	0.34333 (15)	−0.0424 (4)	0.0710 (9)
H13	−0.5541	0.3475	−0.1484	0.085*
C14	−0.4990 (4)	0.30551 (14)	0.0690 (4)	0.0681 (9)
H14	−0.5974	0.2837	0.0389	0.082*
C15	−0.3807 (3)	0.29891 (12)	0.2265 (4)	0.0575 (7)
H15	−0.3995	0.2733	0.3029	0.069*
C16	−0.2334 (3)	0.33096 (10)	0.2697 (3)	0.0425 (6)
C17	−0.1242 (4)	0.29088 (13)	0.5486 (4)	0.0621 (8)
H17A	−0.1393	0.2507	0.5108	0.075*
H17B	−0.2202	0.3025	0.5783	0.075*
C18	0.0337 (5)	0.29740 (15)	0.6943 (4)	0.0761 (10)
H18A	0.0512	0.3383	0.7242	0.091*
H18B	0.0229	0.2766	0.7892	0.091*
N1	0.2576 (2)	0.39694 (9)	0.2431 (3)	0.0467 (5)
O1	0.2337 (3)	0.45710 (10)	0.0197 (3)	0.0780 (7)
O2	0.3549 (3)	0.35172 (9)	0.4993 (3)	0.0696 (6)
O3	−0.1065 (2)	0.32785 (8)	0.4213 (2)	0.0543 (5)
O4	0.1750 (3)	0.27578 (10)	0.6595 (3)	0.0903 (8)
H4A	0.2069	0.3003	0.6069	0.136*

	U11	U22	U33	U12	U13	U23
C1	0.0511 (16)	0.0515 (17)	0.072 (2)	0.0004 (13)	0.0424 (15)	0.0039 (15)
C2	0.0478 (15)	0.0466 (15)	0.0762 (19)	−0.0039 (12)	0.0438 (14)	−0.0084 (14)
C3	0.063 (2)	0.0561 (18)	0.109 (3)	−0.0071 (15)	0.061 (2)	−0.0051 (18)
C4	0.059 (2)	0.071 (2)	0.138 (3)	−0.0224 (17)	0.067 (2)	−0.040 (2)
C5	0.0486 (19)	0.085 (3)	0.113 (3)	−0.0090 (17)	0.041 (2)	−0.044 (2)
C6	0.0549 (18)	0.070 (2)	0.079 (2)	0.0012 (16)	0.0325 (17)	−0.0209 (17)
C7	0.0442 (15)	0.0469 (15)	0.0706 (19)	−0.0007 (12)	0.0342 (14)	−0.0151 (14)
C8	0.0539 (16)	0.0433 (15)	0.0646 (18)	0.0013 (12)	0.0353 (15)	−0.0044 (14)
C9	0.0506 (16)	0.0481 (16)	0.0617 (17)	−0.0097 (12)	0.0319 (14)	−0.0089 (13)
C10	0.0452 (14)	0.0389 (14)	0.0516 (16)	−0.0021 (11)	0.0234 (12)	0.0027 (12)
C11	0.0405 (13)	0.0377 (14)	0.0455 (15)	0.0026 (10)	0.0177 (12)	−0.0018 (11)
C12	0.0565 (18)	0.0641 (19)	0.0531 (18)	0.0021 (14)	0.0179 (15)	0.0012 (14)
C13	0.0510 (18)	0.083 (2)	0.068 (2)	−0.0031 (16)	0.0060 (15)	−0.0138 (18)
C14	0.0438 (17)	0.067 (2)	0.091 (3)	−0.0118 (15)	0.0202 (18)	−0.0215 (19)
C15	0.0546 (17)	0.0498 (16)	0.080 (2)	−0.0072 (13)	0.0389 (17)	−0.0042 (15)
C16	0.0407 (14)	0.0403 (14)	0.0508 (15)	0.0024 (11)	0.0213 (12)	−0.0012 (12)
C17	0.078 (2)	0.0573 (18)	0.0635 (19)	0.0014 (15)	0.0398 (17)	0.0141 (15)
C18	0.108 (3)	0.069 (2)	0.0548 (19)	−0.005 (2)	0.0320 (19)	0.0149 (16)
N1	0.0442 (12)	0.0442 (13)	0.0620 (14)	−0.0060 (10)	0.0312 (11)	−0.0030 (11)
O1	0.0679 (14)	0.0947 (17)	0.0812 (16)	−0.0007 (12)	0.0382 (13)	0.0271 (14)
O2	0.0753 (14)	0.0670 (13)	0.0737 (14)	−0.0095 (11)	0.0348 (12)	0.0137 (11)
O3	0.0542 (11)	0.0581 (12)	0.0530 (11)	−0.0049 (9)	0.0213 (9)	0.0157 (9)
O4	0.0798 (17)	0.0854 (17)	0.0969 (19)	−0.0082 (13)	0.0190 (14)	0.0303 (14)

C1—O1	1.205 (3)	C10—H10A	0.9700
C1—N1	1.393 (3)	C10—H10B	0.9700
C1—C2	1.483 (4)	C11—C12	1.373 (3)
C2—C7	1.372 (4)	C11—C16	1.390 (3)
C2—C3	1.378 (4)	C12—C13	1.378 (4)
C3—C4	1.382 (5)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.356 (4)
C4—C5	1.366 (5)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.379 (4)
C5—C6	1.382 (4)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.386 (3)
C6—C7	1.373 (4)	C15—H15	0.9300
C6—H6	0.9300	C16—O3	1.369 (3)
C7—C8	1.482 (4)	C17—O3	1.424 (3)
C8—O2	1.208 (3)	C17—C18	1.488 (4)
C8—N1	1.379 (3)	C17—H17A	0.9700
C9—N1	1.455 (3)	C17—H17B	0.9700
C9—C10	1.515 (3)	C18—O4	1.419 (4)
C9—H9A	0.9700	C18—H18A	0.9700
C9—H9B	0.9700	C18—H18B	0.9700
C10—C11	1.498 (3)	O4—H4A	0.8200
O1—C1—N1	124.6 (3)	C12—C11—C16	117.5 (2)
O1—C1—C2	129.9 (3)	C12—C11—C10	121.9 (2)
N1—C1—C2	105.5 (2)	C16—C11—C10	120.6 (2)
C7—C2—C3	121.0 (3)	C11—C12—C13	122.3 (3)
C7—C2—C1	108.3 (2)	C11—C12—H12	118.9
C3—C2—C1	130.7 (3)	C13—C12—H12	118.9
C2—C3—C4	117.4 (3)	C14—C13—C12	119.2 (3)
C2—C3—H3	121.3	C14—C13—H13	120.4
C4—C3—H3	121.3	C12—C13—H13	120.4
C5—C4—C3	121.4 (3)	C13—C14—C15	120.9 (3)
C5—C4—H4	119.3	C13—C14—H14	119.6
C3—C4—H4	119.3	C15—C14—H14	119.6
C4—C5—C6	121.3 (3)	C14—C15—C16	119.2 (3)
C4—C5—H5	119.4	C14—C15—H15	120.4
C6—C5—H5	119.4	C16—C15—H15	120.4
C5—C6—C7	117.3 (3)	O3—C16—C15	124.6 (2)
C5—C6—H6	121.4	O3—C16—C11	114.5 (2)
C7—C6—H6	121.4	C15—C16—C11	120.9 (2)
C2—C7—C6	121.7 (3)	O3—C17—C18	105.9 (2)
C2—C7—C8	108.0 (2)	O3—C17—H17A	110.5
C6—C7—C8	130.3 (3)	C18—C17—H17A	110.5
O2—C8—N1	125.1 (2)	O3—C17—H17B	110.5
O2—C8—C7	128.8 (3)	C18—C17—H17B	110.5
N1—C8—C7	106.2 (2)	H17A—C17—H17B	108.7
N1—C9—C10	112.6 (2)	O4—C18—C17	112.0 (3)
N1—C9—H9A	109.1	O4—C18—H18A	109.2
C10—C9—H9A	109.1	C17—C18—H18A	109.2
N1—C9—H9B	109.1	O4—C18—H18B	109.2
C10—C9—H9B	109.1	C17—C18—H18B	109.2
H9A—C9—H9B	107.8	H18A—C18—H18B	107.9
C11—C10—C9	111.38 (19)	C8—N1—C1	112.0 (2)
C11—C10—H10A	109.4	C8—N1—C9	124.0 (2)
C9—C10—H10A	109.4	C1—N1—C9	124.1 (2)
C11—C10—H10B	109.4	C16—O3—C17	119.6 (2)
C9—C10—H10B	109.4	C18—O4—H4A	109.5
H10A—C10—H10B	108.0
O1—C1—C2—C7	178.8 (3)	C11—C12—C13—C14	0.9 (4)
N1—C1—C2—C7	0.0 (3)	C12—C13—C14—C15	0.0 (5)
O1—C1—C2—C3	0.5 (5)	C13—C14—C15—C16	−0.8 (4)
N1—C1—C2—C3	−178.3 (3)	C14—C15—C16—O3	−179.5 (2)
C7—C2—C3—C4	0.5 (4)	C14—C15—C16—C11	0.8 (4)
C1—C2—C3—C4	178.6 (3)	C12—C11—C16—O3	−179.7 (2)
C2—C3—C4—C5	0.0 (4)	C10—C11—C16—O3	1.1 (3)
C3—C4—C5—C6	−0.1 (5)	C12—C11—C16—C15	0.0 (4)
C4—C5—C6—C7	−0.3 (4)	C10—C11—C16—C15	−179.2 (2)
C3—C2—C7—C6	−1.0 (4)	O3—C17—C18—O4	−65.5 (3)
C1—C2—C7—C6	−179.4 (2)	O2—C8—N1—C1	178.8 (2)
C3—C2—C7—C8	178.5 (2)	C7—C8—N1—C1	−0.1 (3)
C1—C2—C7—C8	0.0 (3)	O2—C8—N1—C9	−0.5 (4)
C5—C6—C7—C2	0.8 (4)	C7—C8—N1—C9	−179.3 (2)
C5—C6—C7—C8	−178.5 (2)	O1—C1—N1—C8	−178.9 (3)
C2—C7—C8—O2	−178.8 (3)	C2—C1—N1—C8	0.1 (3)
C6—C7—C8—O2	0.6 (5)	O1—C1—N1—C9	0.4 (4)
C2—C7—C8—N1	0.1 (3)	C2—C1—N1—C9	179.3 (2)
C6—C7—C8—N1	179.4 (3)	C10—C9—N1—C8	95.6 (3)
N1—C9—C10—C11	−171.9 (2)	C10—C9—N1—C1	−83.5 (3)
C9—C10—C11—C12	−96.2 (3)	C15—C16—O3—C17	−1.9 (4)
C9—C10—C11—C16	82.9 (3)	C11—C16—O3—C17	177.8 (2)
C16—C11—C12—C13	−0.9 (4)	C18—C17—O3—C16	179.7 (2)
C10—C11—C12—C13	178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2	0.82	2.14	2.941 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O2	0.82	2.14	2.941 (3)	164