2-{Hy-droxy[1-(4-meth-oxy-phen-yl)-4-oxo-3-phenyl-azetidin-2-yl]meth-yl}acrylonitrile.

In the title compound, C(20)H(18)N(2)O(3), the β-lactam ring is essentially planar, having a maximum deviation of 0.0291 (15) Å for the N atom, and perpendicular to the phenyl ring [dihedral angle = 85.55 (11)°]. The carbonitrile side chain is almost linear, the C-C-N angle being 176.8 (2)°. The crystal packing is stabilized by inter-molecular O-H⋯O and C-H⋯O inter-actions.

Related literature

For uses of acrylonitrile derivatives, see: Ambrosi et al. (1994 ▶). For the pharmacological properties of β-lactam derivatives, see: Brakhage (1998 ▶). For related structures, see: Sundaresan et al. (2008 ▶); Kamala et al. (2008 ▶). For related geometrical parameters, see: Nizam Mohideen et al. (2007 ▶).

Experimental

Crystal data

C20H18N2O3

M = 334.36

Monoclinic,

a = 9.9694 (3) Å

b = 19.8196 (6) Å

c = 9.6013 (3) Å

β = 112.718 (1)°

V = 1749.93 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

10596 measured reflections

4368 independent reflections

3621 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.100

S = 1.01

4368 reflections

228 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032247/rk2289sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032247/rk2289Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032247/rk2289Isup3.cml

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

C20H18N2O3	F(000) = 704
Mr = 334.36	Dx = 1.269 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4368 reflections
a = 9.9694 (3) Å	θ = 2.4–29.7°
b = 19.8196 (6) Å	µ = 0.09 mm−1
c = 9.6013 (3) Å	T = 295 K
β = 112.718 (1)°	Block, colourless
V = 1749.93 (9) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3621 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 29.7°, θmin = 2.4°
ω and φ scans	h = −13→13
10596 measured reflections	k = −25→27
4368 independent reflections	l = −11→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.1723P] where P = (Fo2 + 2Fc2)/3
4368 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.16 e Å−3
2 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.6009 (3)	0.19499 (12)	0.1527 (3)	0.0809 (7)
H1	0.6877	0.2116	0.1515	0.097*
C2	0.6025 (2)	0.15799 (11)	0.2755 (3)	0.0630 (5)
H2	0.6902	0.1499	0.3558	0.076*
C3	0.47523 (17)	0.13317 (8)	0.27943 (17)	0.0401 (3)
C4	0.3470 (2)	0.14539 (10)	0.1573 (2)	0.0579 (5)
H4	0.2599	0.1284	0.1570	0.069*
C5	0.3470 (3)	0.18264 (12)	0.0352 (2)	0.0779 (7)
H5	0.2600	0.1908	−0.0461	0.093*
C6	0.4739 (3)	0.20732 (11)	0.0336 (3)	0.0746 (7)
H6	0.4737	0.2324	−0.0482	0.089*
C7	0.38921 (15)	0.13134 (7)	0.50213 (17)	0.0340 (3)
H7	0.3452	0.1742	0.4561	0.041*
C8	0.36425 (16)	0.03948 (7)	0.39009 (16)	0.0379 (3)
C9	0.47470 (16)	0.09626 (7)	0.41628 (17)	0.0362 (3)
H9	0.5727	0.0827	0.4844	0.043*
C10	0.16463 (15)	0.06120 (7)	0.49049 (16)	0.0359 (3)
C11	0.10281 (17)	0.11362 (8)	0.5408 (2)	0.0443 (4)
H11	0.1396	0.1571	0.5466	0.053*
C12	−0.01237 (18)	0.10169 (8)	0.5822 (2)	0.0471 (4)
H12	−0.0528	0.1371	0.6165	0.057*
C13	−0.06861 (16)	0.03725 (8)	0.57319 (18)	0.0414 (3)
C14	−0.00915 (17)	−0.01503 (8)	0.51980 (19)	0.0425 (4)
H14	−0.0471	−0.0584	0.5123	0.051*
C15	0.10649 (17)	−0.00288 (8)	0.47766 (18)	0.0410 (3)
H15	0.1452	−0.0379	0.4406	0.049*
C16	−0.2330 (2)	−0.03522 (11)	0.6291 (3)	0.0599 (5)
H16A	−0.2710	−0.0556	0.5308	0.090*
H16B	−0.3083	−0.0327	0.6680	0.090*
H16C	−0.1540	−0.0620	0.6957	0.090*
C17	0.47215 (16)	0.13644 (8)	0.67345 (17)	0.0391 (3)
H17	0.4046	0.1492	0.7208	0.047*
C18	0.58853 (18)	0.19031 (8)	0.70558 (18)	0.0433 (4)
C19	0.7295 (2)	0.17793 (11)	0.7631 (2)	0.0607 (5)
H19A	0.7953	0.2131	0.7778	0.073*
H19B	0.7629	0.1341	0.7890	0.073*
C20	0.5348 (2)	0.25736 (10)	0.6650 (3)	0.0602 (5)
N1	0.28665 (13)	0.07467 (6)	0.45591 (15)	0.0381 (3)
N2	0.4860 (3)	0.30955 (10)	0.6326 (4)	0.1008 (8)
O1	0.34670 (14)	−0.01631 (6)	0.33461 (15)	0.0505 (3)
O2	−0.18217 (13)	0.03094 (6)	0.61854 (16)	0.0557 (3)
O3	0.53772 (13)	0.07510 (6)	0.73290 (14)	0.0525 (3)
H3	0.4856	0.0542	0.7661	0.079*

	U11	U22	U33	U12	U13	U23
C1	0.0945 (18)	0.0779 (15)	0.098 (2)	−0.0164 (13)	0.0673 (17)	0.0082 (13)
C2	0.0580 (11)	0.0681 (11)	0.0739 (13)	−0.0036 (9)	0.0375 (10)	0.0104 (10)
C3	0.0488 (8)	0.0364 (7)	0.0431 (8)	0.0012 (6)	0.0268 (7)	−0.0027 (6)
C4	0.0618 (10)	0.0669 (11)	0.0434 (10)	−0.0110 (9)	0.0186 (8)	0.0037 (8)
C5	0.1023 (18)	0.0790 (15)	0.0425 (11)	−0.0110 (13)	0.0172 (11)	0.0081 (10)
C6	0.129 (2)	0.0563 (12)	0.0573 (12)	−0.0166 (12)	0.0570 (14)	−0.0006 (9)
C7	0.0361 (7)	0.0303 (6)	0.0398 (7)	−0.0006 (5)	0.0192 (6)	−0.0018 (5)
C8	0.0429 (8)	0.0365 (7)	0.0377 (8)	0.0052 (6)	0.0193 (7)	0.0000 (6)
C9	0.0379 (7)	0.0364 (7)	0.0381 (7)	0.0036 (5)	0.0186 (6)	−0.0004 (5)
C10	0.0334 (7)	0.0358 (7)	0.0390 (7)	0.0036 (6)	0.0146 (6)	−0.0007 (6)
C11	0.0438 (8)	0.0321 (7)	0.0628 (11)	0.0002 (6)	0.0271 (7)	−0.0025 (7)
C12	0.0438 (8)	0.0399 (8)	0.0655 (11)	0.0089 (7)	0.0298 (8)	0.0003 (7)
C13	0.0322 (7)	0.0448 (8)	0.0474 (9)	0.0027 (6)	0.0155 (6)	0.0056 (6)
C14	0.0415 (8)	0.0352 (8)	0.0521 (9)	−0.0046 (6)	0.0195 (7)	−0.0016 (6)
C15	0.0432 (8)	0.0359 (7)	0.0442 (8)	0.0009 (6)	0.0171 (7)	−0.0056 (6)
C16	0.0520 (10)	0.0602 (11)	0.0747 (14)	−0.0111 (8)	0.0324 (10)	0.0041 (9)
C17	0.0426 (8)	0.0425 (8)	0.0381 (8)	−0.0011 (6)	0.0221 (6)	−0.0006 (6)
C18	0.0497 (9)	0.0449 (9)	0.0386 (8)	−0.0053 (7)	0.0206 (7)	−0.0064 (6)
C19	0.0509 (10)	0.0615 (11)	0.0645 (12)	−0.0068 (9)	0.0166 (9)	−0.0034 (9)
C20	0.0520 (10)	0.0496 (11)	0.0780 (13)	−0.0107 (8)	0.0239 (9)	−0.0131 (9)
N1	0.0395 (6)	0.0323 (6)	0.0473 (7)	−0.0010 (5)	0.0221 (5)	−0.0062 (5)
N2	0.0825 (14)	0.0460 (11)	0.161 (3)	−0.0015 (9)	0.0328 (14)	−0.0037 (12)
O1	0.0618 (7)	0.0393 (6)	0.0584 (7)	−0.0014 (5)	0.0321 (6)	−0.0114 (5)
O2	0.0462 (7)	0.0517 (7)	0.0801 (9)	0.0010 (5)	0.0364 (6)	0.0068 (6)
O3	0.0558 (7)	0.0535 (7)	0.0536 (7)	0.0034 (5)	0.0271 (6)	0.0171 (5)

C1—C6	1.361 (4)	C11—C12	1.373 (2)
C1—C2	1.383 (3)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.384 (2)
C2—C3	1.375 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—O2	1.367 (2)
C3—C4	1.382 (2)	C13—C14	1.387 (2)
C3—C9	1.506 (2)	C14—C15	1.382 (2)
C4—C5	1.385 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.361 (4)	C16—O2	1.423 (2)
C5—H5	0.9300	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—N1	1.4675 (18)	C16—H16C	0.9600
C7—C17	1.533 (2)	C17—O3	1.3938 (19)
C7—C9	1.559 (2)	C17—C18	1.518 (2)
C7—H7	0.9800	C17—H17	0.9800
C8—O1	1.2105 (18)	C18—C19	1.319 (3)
C8—N1	1.3645 (19)	C18—C20	1.429 (3)
C8—C9	1.526 (2)	C19—H19A	0.9300
C9—H9	0.9800	C19—H19B	0.9300
C10—C15	1.382 (2)	C20—N2	1.134 (3)
C10—C11	1.387 (2)	O3—H3	0.8200
C10—N1	1.4047 (19)
C6—C1—C2	120.8 (2)	C10—C11—H11	119.8
C6—C1—H1	119.6	C11—C12—C13	120.30 (14)
C2—C1—H1	119.6	C11—C12—H12	119.8
C3—C2—C1	120.4 (2)	C13—C12—H12	119.8
C3—C2—H2	119.8	O2—C13—C12	115.46 (14)
C1—C2—H2	119.8	O2—C13—C14	125.06 (14)
C2—C3—C4	118.34 (16)	C12—C13—C14	119.48 (14)
C2—C3—C9	120.81 (15)	C15—C14—C13	120.13 (14)
C4—C3—C9	120.79 (14)	C15—C14—H14	119.9
C3—C4—C5	120.60 (19)	C13—C14—H14	119.9
C3—C4—H4	119.7	C10—C15—C14	120.17 (14)
C5—C4—H4	119.7	C10—C15—H15	119.9
C6—C5—C4	120.3 (2)	C14—C15—H15	119.9
C6—C5—H5	119.8	O2—C16—H16A	109.5
C4—C5—H5	119.8	O2—C16—H16B	109.5
C1—C6—C5	119.6 (2)	H16A—C16—H16B	109.5
C1—C6—H6	120.2	O2—C16—H16C	109.5
C5—C6—H6	120.2	H16A—C16—H16C	109.5
N1—C7—C17	113.52 (12)	H16B—C16—H16C	109.5
N1—C7—C9	87.60 (10)	O3—C17—C18	109.23 (12)
C17—C7—C9	114.72 (12)	O3—C17—C7	110.82 (13)
N1—C7—H7	112.9	C18—C17—C7	108.52 (12)
C17—C7—H7	112.9	O3—C17—H17	109.4
C9—C7—H7	112.9	C18—C17—H17	109.4
O1—C8—N1	131.25 (14)	C7—C17—H17	109.4
O1—C8—C9	135.95 (14)	C19—C18—C20	120.90 (16)
N1—C8—C9	92.80 (11)	C19—C18—C17	124.13 (16)
C3—C9—C8	117.38 (13)	C20—C18—C17	114.94 (15)
C3—C9—C7	115.56 (12)	C18—C19—H19A	120.0
C8—C9—C7	84.78 (11)	C18—C19—H19B	120.0
C3—C9—H9	112.2	H19A—C19—H19B	120.0
C8—C9—H9	112.2	N2—C20—C18	176.8 (2)
C7—C9—H9	112.2	C8—N1—C10	135.24 (12)
C15—C10—C11	119.48 (14)	C8—N1—C7	94.46 (11)
C15—C10—N1	121.69 (13)	C10—N1—C7	129.77 (11)
C11—C10—N1	118.83 (13)	C13—O2—C16	117.93 (14)
C12—C11—C10	120.40 (14)	C17—O3—H3	109.5
C12—C11—H11	119.8
C6—C1—C2—C3	−0.2 (4)	C12—C13—C14—C15	0.7 (2)
C1—C2—C3—C4	0.9 (3)	C11—C10—C15—C14	−2.3 (2)
C1—C2—C3—C9	−176.48 (18)	N1—C10—C15—C14	176.76 (14)
C2—C3—C4—C5	−1.0 (3)	C13—C14—C15—C10	0.9 (2)
C9—C3—C4—C5	176.35 (18)	N1—C7—C17—O3	52.33 (16)
C3—C4—C5—C6	0.5 (3)	C9—C7—C17—O3	−46.30 (16)
C2—C1—C6—C5	−0.3 (4)	N1—C7—C17—C18	172.26 (12)
C4—C5—C6—C1	0.2 (4)	C9—C7—C17—C18	73.64 (15)
C2—C3—C9—C8	−146.86 (16)	O3—C17—C18—C19	8.0 (2)
C4—C3—C9—C8	35.9 (2)	C7—C17—C18—C19	−112.87 (19)
C2—C3—C9—C7	115.42 (18)	O3—C17—C18—C20	−173.48 (15)
C4—C3—C9—C7	−61.8 (2)	C7—C17—C18—C20	65.61 (19)
O1—C8—C9—C3	68.9 (2)	O1—C8—N1—C10	2.8 (3)
N1—C8—C9—C3	−111.64 (14)	C9—C8—N1—C10	−176.66 (16)
O1—C8—C9—C7	−174.95 (18)	O1—C8—N1—C7	174.71 (17)
N1—C8—C9—C7	4.50 (11)	C9—C8—N1—C7	−4.78 (12)
N1—C7—C9—C3	113.74 (13)	C15—C10—N1—C8	9.6 (3)
C17—C7—C9—C3	−131.40 (14)	C11—C10—N1—C8	−171.31 (17)
N1—C7—C9—C8	−4.18 (11)	C15—C10—N1—C7	−159.80 (15)
C17—C7—C9—C8	110.68 (13)	C11—C10—N1—C7	19.2 (2)
C15—C10—C11—C12	2.1 (2)	C17—C7—N1—C8	−111.32 (13)
N1—C10—C11—C12	−177.01 (15)	C9—C7—N1—C8	4.67 (12)
C10—C11—C12—C13	−0.4 (3)	C17—C7—N1—C10	61.25 (19)
C11—C12—C13—O2	179.40 (16)	C9—C7—N1—C10	177.24 (14)
C11—C12—C13—C14	−1.0 (3)	C12—C13—O2—C16	−172.56 (17)
O2—C13—C14—C15	−179.66 (15)	C14—C13—O2—C16	7.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1i	0.82	1.90	2.716 (2)	172
C9—H9···O2ii	0.98	2.50	3.467 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1i	0.82	1.90	2.716 (2)	172
C9—H9⋯O2ii	0.98	2.50	3.467 (2)	169

Symmetry codes: (i) ; (ii) .