2-[1-(4-Ethoxy-phen-yl)-2-oxo-4-styryl-azetidin-3-yl]isoindoline-1,3-dione.

The title compound, C(27)H(22)N(2)O(4), contains a nearly planar four-membered β-lactam ring, which makes dihedral angles of 74.64 (12), 1.70 (11) and 73.67 (12)° with the nine-membered ring system, the benzene ring and the phenyl ring, respectively. The crystal structure is stabilized by C-H⋯O and C-H⋯π inter-actions and a π-π inter-action [centroid-centroid distance = 3.4505 (19) Å] is also present.

Related literature

For related structures, see: Pınar et al. (2006 ▶); Akkurt et al. (2007 ▶). For background, see: Halve et al. (2007 ▶); Aoyama et al. (2001 ▶). For related literature, see: Jarrahpour & Zarei (2007 ▶).

Experimental

Crystal data

C27H22N2O4

M = 438.47

Monoclinic,

a = 33.7560 (17) Å

b = 7.0403 (2) Å

c = 31.0482 (17) Å

β = 140.454 (3)°

V = 4698.0 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.53 × 0.45 × 0.14 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: none

22562 measured reflections

4934 independent reflections

3071 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.099

S = 0.96

4934 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.11 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: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011586/hb2715sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011586/hb2715Isup2.hkl

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

C27H22N2O4	F000 = 1840
Mr = 438.47	Dx = 1.240 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 19454 reflections
a = 33.7560 (17) Å	θ = 1.3–27.3º
b = 7.0403 (2) Å	µ = 0.08 mm−1
c = 31.0482 (17) Å	T = 293 (2) K
β = 140.454 (3)º	Prism, colourless
V = 4698.0 (5) Å3	0.53 × 0.45 × 0.14 mm
Z = 8

Stoe IPDS-2 diffractometer	3071 reflections with I > 2σ(I)
Monochromator: plane graphite	Rint = 0.052
Detector resolution: 6.67 pixels mm-1	θmax = 26.8º
T = 293(2) K	θmin = 1.4º
ω scans	h = −42→42
Absorption correction: none	k = −8→8
22562 measured reflections	l = −39→39
4934 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max < 0.001
S = 0.97	Δρmax = 0.17 e Å−3
4934 reflections	Δρmin = −0.11 e Å−3
299 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (2)
Secondary atom site location: difference Fourier map

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	0.52753 (6)	0.55052 (15)	0.57556 (7)	0.0765 (5)
O2	0.54065 (6)	1.14698 (16)	0.64241 (7)	0.0887 (5)
O3	0.67821 (7)	0.6142 (2)	0.70712 (8)	0.1034 (6)
O4	0.74347 (5)	−0.13874 (15)	0.89253 (6)	0.0729 (4)
N1	0.54930 (5)	0.83949 (16)	0.62525 (6)	0.0555 (4)
N2	0.64313 (6)	0.53412 (18)	0.74672 (7)	0.0617 (4)
C1	0.51510 (7)	0.7165 (2)	0.57070 (8)	0.0562 (5)
C2	0.46331 (7)	0.8305 (2)	0.50943 (8)	0.0554 (5)
C3	0.41750 (8)	0.7826 (3)	0.44180 (9)	0.0708 (6)
C4	0.37641 (8)	0.9267 (3)	0.39554 (10)	0.0814 (8)
C5	0.38151 (9)	1.1085 (3)	0.41602 (11)	0.0795 (8)
C6	0.42714 (8)	1.1549 (2)	0.48327 (10)	0.0714 (7)
C7	0.46791 (7)	1.0133 (2)	0.52986 (8)	0.0566 (5)
C8	0.52172 (7)	1.0197 (2)	0.60414 (9)	0.0598 (5)
C9	0.60433 (7)	0.7905 (2)	0.69508 (8)	0.0641 (5)
C10	0.64799 (8)	0.6362 (3)	0.71402 (9)	0.0719 (6)
C11	0.59771 (7)	0.6599 (2)	0.72999 (8)	0.0597 (5)
C12	0.67075 (7)	0.3647 (2)	0.78458 (8)	0.0567 (5)
C13	0.71296 (7)	0.2662 (2)	0.79469 (8)	0.0597 (5)
C14	0.73897 (7)	0.0980 (2)	0.83145 (8)	0.0601 (5)
C15	0.72250 (7)	0.0284 (2)	0.85749 (8)	0.0580 (5)
C16	0.68038 (7)	0.1281 (2)	0.84731 (9)	0.0639 (6)
C17	0.65484 (7)	0.2938 (2)	0.81140 (8)	0.0640 (6)
C18	0.79389 (8)	−0.2335 (3)	0.91444 (10)	0.0753 (7)
C19	0.81168 (9)	−0.3978 (3)	0.95687 (10)	0.0799 (7)
C20	0.53523 (7)	0.5771 (2)	0.68565 (8)	0.0564 (5)
C21	0.49520 (7)	0.6482 (2)	0.67920 (9)	0.0672 (6)
C22	0.43110 (8)	0.5844 (2)	0.63340 (9)	0.0655 (6)
C23	0.40642 (9)	0.4242 (3)	0.59366 (12)	0.0936 (8)
C24	0.34510 (11)	0.3722 (3)	0.54989 (13)	0.1084 (10)
C25	0.30869 (9)	0.4779 (3)	0.54607 (12)	0.0919 (8)
C26	0.33206 (9)	0.6339 (3)	0.58488 (10)	0.0815 (7)
C27	0.39250 (8)	0.6879 (3)	0.62798 (9)	0.0726 (6)
H3	0.41420	0.66050	0.42780	0.0850*
H4	0.34460	0.89950	0.34950	0.0980*
H5	0.35350	1.20120	0.38360	0.0950*
H6	0.43060	1.27740	0.49710	0.0860*
H9	0.62800	0.90510	0.72220	0.0770*
H11	0.61500	0.71940	0.77040	0.0720*
H13	0.72390	0.31270	0.77680	0.0720*
H14	0.76750	0.03250	0.83850	0.0720*
H16	0.66940	0.08180	0.86510	0.0770*
H17	0.62660	0.35940	0.80490	0.0770*
H18A	0.82890	−0.14760	0.94060	0.0900*
H18B	0.78150	−0.27720	0.87570	0.0900*
H19A	0.77670	−0.48160	0.93060	0.0960*
H19B	0.82430	−0.35290	0.99530	0.0960*
H19C	0.84560	−0.46500	0.97210	0.0960*
H20	0.52400	0.46840	0.66110	0.0680*
H21	0.50880	0.75120	0.70680	0.0810*
H23	0.43100	0.35050	0.59620	0.1120*
H24	0.32880	0.26450	0.52300	0.1300*
H25	0.26760	0.44230	0.51660	0.1100*
H26	0.30720	0.70510	0.58250	0.0980*
H27	0.40790	0.79670	0.65410	0.0870*

	U11	U22	U33	U12	U13	U23
O1	0.0929 (9)	0.0524 (6)	0.0847 (9)	0.0128 (6)	0.0686 (8)	0.0056 (6)
O2	0.0932 (9)	0.0554 (6)	0.0838 (9)	0.0000 (6)	0.0594 (8)	−0.0081 (7)
O3	0.0824 (9)	0.1325 (11)	0.1212 (12)	0.0437 (8)	0.0853 (10)	0.0642 (9)
O4	0.0679 (7)	0.0707 (7)	0.0925 (9)	0.0208 (6)	0.0651 (7)	0.0242 (6)
N1	0.0501 (7)	0.0471 (6)	0.0569 (8)	0.0026 (5)	0.0380 (7)	0.0046 (6)
N2	0.0499 (7)	0.0691 (8)	0.0602 (8)	0.0122 (6)	0.0409 (7)	0.0166 (7)
C1	0.0574 (9)	0.0528 (8)	0.0646 (10)	0.0019 (7)	0.0487 (9)	0.0029 (8)
C2	0.0488 (8)	0.0622 (9)	0.0601 (10)	0.0012 (7)	0.0433 (8)	0.0039 (8)
C3	0.0620 (10)	0.0890 (11)	0.0675 (12)	−0.0043 (9)	0.0515 (10)	−0.0026 (10)
C4	0.0527 (10)	0.1283 (17)	0.0578 (11)	0.0072 (11)	0.0412 (10)	0.0174 (11)
C5	0.0597 (11)	0.0968 (14)	0.0827 (15)	0.0211 (10)	0.0551 (12)	0.0319 (11)
C6	0.0641 (10)	0.0658 (10)	0.0866 (14)	0.0161 (8)	0.0587 (11)	0.0234 (9)
C7	0.0491 (8)	0.0547 (8)	0.0671 (10)	0.0053 (7)	0.0451 (9)	0.0103 (7)
C8	0.0593 (9)	0.0477 (8)	0.0698 (11)	−0.0010 (7)	0.0491 (10)	0.0023 (8)
C9	0.0488 (8)	0.0616 (9)	0.0589 (10)	−0.0025 (7)	0.0355 (8)	0.0039 (8)
C10	0.0504 (9)	0.0870 (12)	0.0687 (11)	0.0113 (8)	0.0434 (9)	0.0225 (9)
C11	0.0522 (8)	0.0608 (8)	0.0548 (9)	0.0044 (7)	0.0383 (8)	0.0025 (7)
C12	0.0421 (7)	0.0642 (9)	0.0496 (9)	0.0026 (7)	0.0316 (7)	0.0061 (7)
C13	0.0462 (8)	0.0729 (9)	0.0568 (9)	0.0006 (7)	0.0389 (8)	0.0050 (8)
C14	0.0456 (8)	0.0676 (9)	0.0649 (10)	0.0045 (7)	0.0420 (8)	0.0050 (8)
C15	0.0477 (8)	0.0627 (9)	0.0574 (10)	0.0050 (7)	0.0389 (8)	0.0057 (7)
C16	0.0607 (9)	0.0717 (10)	0.0670 (11)	0.0111 (8)	0.0513 (9)	0.0141 (8)
C17	0.0562 (9)	0.0744 (10)	0.0639 (10)	0.0152 (8)	0.0470 (9)	0.0130 (8)
C18	0.0659 (10)	0.0775 (11)	0.0890 (13)	0.0206 (9)	0.0614 (11)	0.0174 (10)
C19	0.0763 (12)	0.0824 (11)	0.0857 (13)	0.0266 (9)	0.0637 (12)	0.0206 (10)
C20	0.0555 (9)	0.0539 (8)	0.0560 (9)	0.0039 (7)	0.0420 (8)	0.0030 (7)
C21	0.0574 (9)	0.0721 (10)	0.0643 (11)	−0.0014 (8)	0.0449 (9)	−0.0129 (8)
C22	0.0579 (9)	0.0755 (10)	0.0638 (10)	−0.0002 (8)	0.0471 (9)	−0.0060 (8)
C23	0.0762 (13)	0.0912 (13)	0.1146 (17)	−0.0156 (10)	0.0739 (14)	−0.0352 (12)
C24	0.0876 (15)	0.1084 (16)	0.124 (2)	−0.0347 (13)	0.0802 (16)	−0.0474 (14)
C25	0.0647 (11)	0.1170 (16)	0.0931 (15)	−0.0159 (12)	0.0606 (12)	−0.0111 (13)
C26	0.0662 (11)	0.1067 (14)	0.0831 (13)	0.0048 (11)	0.0606 (11)	0.0017 (12)
C27	0.0659 (11)	0.0863 (11)	0.0715 (11)	0.0024 (9)	0.0545 (10)	−0.0063 (9)

O1—C1	1.211 (2)	C21—C22	1.470 (4)
O2—C8	1.205 (2)	C22—C23	1.380 (3)
O3—C10	1.203 (5)	C22—C27	1.385 (4)
O4—C15	1.3717 (18)	C23—C24	1.388 (5)
O4—C18	1.421 (4)	C24—C25	1.362 (6)
N1—C1	1.3913 (19)	C25—C26	1.347 (3)
N1—C8	1.402 (2)	C26—C27	1.374 (4)
N1—C9	1.435 (2)	C3—H3	0.9300
N2—C10	1.353 (3)	C4—H4	0.9300
N2—C11	1.475 (3)	C5—H5	0.9300
N2—C12	1.408 (2)	C6—H6	0.9300
C1—C2	1.480 (2)	C9—H9	0.9800
C2—C3	1.381 (2)	C11—H11	0.9800
C2—C7	1.390 (2)	C13—H13	0.9300
C3—C4	1.394 (3)	C14—H14	0.9300
C4—C5	1.380 (3)	C16—H16	0.9300
C5—C6	1.371 (3)	C17—H17	0.9300
C6—C7	1.382 (2)	C18—H18A	0.9700
C7—C8	1.470 (2)	C18—H18B	0.9700
C9—C10	1.537 (4)	C19—H19A	0.9600
C9—C11	1.563 (3)	C19—H19B	0.9600
C11—C20	1.485 (3)	C19—H19C	0.9600
C12—C13	1.386 (4)	C20—H20	0.9300
C12—C17	1.386 (4)	C21—H21	0.9300
C13—C14	1.389 (2)	C23—H23	0.9300
C14—C15	1.377 (4)	C24—H24	0.9300
C15—C16	1.386 (4)	C25—H25	0.9300
C16—C17	1.366 (2)	C26—H26	0.9300
C18—C19	1.488 (3)	C27—H27	0.9300
C20—C21	1.304 (4)
C15—O4—C18	118.5 (2)	C24—C25—C26	120.1 (3)
C1—N1—C8	111.45 (13)	C25—C26—C27	120.2 (3)
C1—N1—C9	125.59 (13)	C22—C27—C26	121.6 (2)
C8—N1—C9	122.91 (13)	C2—C3—H3	122.00
C10—N2—C11	96.40 (17)	C4—C3—H3	122.00
C10—N2—C12	133.7 (3)	C3—C4—H4	119.00
C11—N2—C12	129.9 (2)	C5—C4—H4	119.00
O1—C1—N1	124.49 (15)	C4—C5—H5	119.00
O1—C1—C2	129.48 (15)	C6—C5—H5	119.00
N1—C1—C2	106.03 (13)	C5—C6—H6	121.00
C1—C2—C3	130.54 (16)	C7—C6—H6	121.00
C1—C2—C7	108.06 (14)	N1—C9—H9	110.00
C3—C2—C7	121.35 (16)	C10—C9—H9	110.00
C2—C3—C4	116.54 (19)	C11—C9—H9	110.00
C3—C4—C5	121.93 (19)	N2—C11—H11	112.00
C4—C5—C6	121.16 (19)	C9—C11—H11	112.00
C5—C6—C7	117.70 (16)	C20—C11—H11	112.00
C2—C7—C6	121.31 (15)	C12—C13—H13	120.00
C2—C7—C8	108.22 (14)	C14—C13—H13	120.00
C6—C7—C8	130.44 (15)	C13—C14—H14	120.00
O2—C8—N1	123.78 (16)	C15—C14—H14	120.00
O2—C8—C7	130.10 (16)	C15—C16—H16	120.00
N1—C8—C7	106.12 (13)	C17—C16—H16	120.00
N1—C9—C10	119.36 (17)	C12—C17—H17	120.00
N1—C9—C11	118.6 (2)	C16—C17—H17	120.00
C10—C9—C11	85.79 (16)	O4—C18—H18A	110.00
O3—C10—N2	132.5 (2)	O4—C18—H18B	110.00
O3—C10—C9	135.9 (2)	C19—C18—H18A	110.00
N2—C10—C9	91.6 (2)	C19—C18—H18B	110.00
N2—C11—C9	86.09 (19)	H18A—C18—H18B	109.00
N2—C11—C20	115.99 (14)	C18—C19—H19A	109.00
C9—C11—C20	116.63 (14)	C18—C19—H19B	110.00
N2—C12—C13	121.1 (2)	C18—C19—H19C	109.00
N2—C12—C17	119.5 (2)	H19A—C19—H19B	110.00
C13—C12—C17	119.40 (16)	H19A—C19—H19C	109.00
C12—C13—C14	120.1 (2)	H19B—C19—H19C	109.00
C13—C14—C15	120.0 (2)	C11—C20—H20	118.00
O4—C15—C14	125.2 (2)	C21—C20—H20	118.00
O4—C15—C16	115.3 (2)	C20—C21—H21	116.00
C14—C15—C16	119.57 (16)	C22—C21—H21	116.00
C15—C16—C17	120.6 (3)	C22—C23—H23	120.00
C12—C17—C16	120.3 (3)	C24—C23—H23	120.00
O4—C18—C19	107.8 (3)	C23—C24—H24	120.00
C11—C20—C21	123.68 (16)	C25—C24—H24	120.00
C20—C21—C22	127.56 (17)	C24—C25—H25	120.00
C21—C22—C23	122.6 (3)	C26—C25—H25	120.00
C21—C22—C27	120.12 (16)	C25—C26—H26	120.00
C23—C22—C27	117.3 (3)	C27—C26—H26	120.00
C22—C23—C24	120.5 (3)	C22—C27—H27	119.00
C23—C24—C25	120.4 (2)	C26—C27—H27	119.00
C18—O4—C15—C16	−170.02 (15)	C4—C5—C6—C7	0.1 (5)
C18—O4—C15—C14	11.6 (2)	C5—C6—C7—C8	178.3 (3)
C15—O4—C18—C19	174.18 (14)	C5—C6—C7—C2	0.6 (5)
C9—N1—C1—C2	−179.5 (2)	C6—C7—C8—N1	−175.1 (3)
C9—N1—C1—O1	0.5 (5)	C2—C7—C8—N1	2.8 (3)
C1—N1—C9—C10	30.8 (4)	C6—C7—C8—O2	5.8 (6)
C8—N1—C9—C10	−152.3 (2)	C2—C7—C8—O2	−176.3 (3)
C8—N1—C1—C2	3.2 (3)	C10—C9—C11—C20	−114.35 (19)
C1—N1—C8—O2	175.4 (3)	N1—C9—C10—O3	60.1 (3)
C9—N1—C8—O2	−1.9 (5)	N1—C9—C11—C20	7.0 (3)
C1—N1—C8—C7	−3.8 (3)	C11—C9—C10—O3	−179.3 (2)
C9—N1—C8—C7	178.9 (2)	N1—C9—C11—N2	124.16 (17)
C8—N1—C1—O1	−176.8 (3)	C10—C9—C11—N2	2.85 (12)
C8—N1—C9—C11	105.6 (2)	N1—C9—C10—N2	−123.7 (2)
C1—N1—C9—C11	−71.3 (3)	C11—C9—C10—N2	−3.10 (13)
C10—N2—C12—C17	−179.02 (18)	C9—C11—C20—C21	−98.1 (3)
C11—N2—C12—C17	0.9 (3)	N2—C11—C20—C21	162.74 (18)
C12—N2—C11—C9	176.79 (16)	C13—C12—C17—C16	−0.2 (2)
C10—N2—C12—C13	0.1 (3)	N2—C12—C13—C14	−179.13 (15)
C11—N2—C12—C13	−179.98 (15)	N2—C12—C17—C16	178.93 (15)
C12—N2—C10—O3	−0.4 (4)	C17—C12—C13—C14	0.0 (2)
C12—N2—C11—C20	−65.4 (2)	C12—C13—C14—C15	0.4 (2)
C10—N2—C11—C20	114.56 (19)	C13—C14—C15—C16	−0.6 (2)
C10—N2—C11—C9	−3.25 (13)	C13—C14—C15—O4	177.73 (15)
C11—N2—C10—O3	179.7 (2)	C14—C15—C16—C17	0.4 (3)
C11—N2—C10—C9	3.30 (14)	O4—C15—C16—C17	−178.09 (15)
C12—N2—C10—C9	−176.74 (17)	C15—C16—C17—C12	0.0 (3)
N1—C1—C2—C7	−1.4 (3)	C11—C20—C21—C22	175.49 (18)
N1—C1—C2—C3	176.2 (3)	C20—C21—C22—C23	5.4 (3)
O1—C1—C2—C7	178.6 (3)	C20—C21—C22—C27	−173.5 (2)
O1—C1—C2—C3	−3.8 (6)	C21—C22—C23—C24	−178.4 (2)
C3—C2—C7—C6	−0.6 (5)	C27—C22—C23—C24	0.6 (4)
C1—C2—C3—C4	−177.3 (3)	C21—C22—C27—C26	179.0 (2)
C7—C2—C3—C4	−0.1 (5)	C23—C22—C27—C26	0.0 (3)
C3—C2—C7—C8	−178.7 (3)	C22—C23—C24—C25	−0.6 (4)
C1—C2—C7—C8	−0.9 (3)	C23—C24—C25—C26	0.0 (4)
C1—C2—C7—C6	177.2 (3)	C24—C25—C26—C27	0.6 (4)
C2—C3—C4—C5	0.7 (5)	C25—C26—C27—C22	−0.6 (4)
C3—C4—C5—C6	−0.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.53	3.283 (3)	138
C5—H5···O3ii	0.93	2.47	3.257 (3)	142
C13—H13···O3	0.93	2.53	3.139 (2)	123
C20—H20···O2iii	0.93	2.51	3.374 (2)	156
C9—H9···Cg1iv	0.98	2.84	3.7938 (16)	166
C19—H19C···Cg2v	0.96	2.82	3.633 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.53	3.283 (3)	138
C5—H5⋯O3ii	0.93	2.47	3.257 (3)	142
C13—H13⋯O3	0.93	2.53	3.139 (2)	123
C20—H20⋯O2iii	0.93	2.51	3.374 (2)	156
C9—H9⋯Cg1iv	0.98	2.84	3.7938 (16)	166
C19—H19C⋯Cg2v	0.96	2.82	3.633 (4)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is the centroid of atoms C12–C17 and Cg2 is the centroid of atoms C2–C7.