organic compounds
2-[1-(4-Ethoxyphenyl)-2-oxo-4-styrylazetidin-3-yl]isoindoline-1,3-dione
aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
The title compound, C27H22N2O4, 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 is stabilized by C—H⋯O and C—H⋯π interactions and a π–π interaction [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
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Data collection
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell 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).
Supporting information
10.1107/S1600536808011586/hb2715sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011586/hb2715Isup2.hkl
A solution of Schiff base (4-cinnamylidene)-(4-ethoxyphenyl)amine (1.0 eq.) was stirred with Phthaloylglycine (1.5 eq.), p-toluenesulfonyl chloride (1.5 eq.) and triethylamine (5 eq.) in dry CH2Cl2 at room temperature. After 10 h, the mixture was washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate and the solvent was evaporated to give the crude product which was then purified by recrystalization from EtOAc (Jarrahpour & Zarei, 2007) [mp: 434 -436 K]. IR (CHCl3) cm-1: 1724.2, 1758.5 (CO, phth), 1774.7 (CO, β-lactam); 1H NMR (250 MHz, CDCl3) δ 1.37 (Me, t, 3H), 2.33 (Me, s, 3H), 3.97 (OCH2, q, 2H), 5.03 (H-4, dd, 1H, J=5.5, 8.5), 5.68 (H-3, d, 1H, J=5.5), 6.32 (H-5, dd, J=8.5, 16.0), 6.85 (H-6, d, 1H, J=9.0), 7.19-7.82 (ArH, m, 13H); 13C NMR (62.9 MHz, CDCl3) δ 14.78 (Me), 57.69 (OCH2), 61.04 (C-4), 63.67 (C-3), 114.99-155.82 (C=C, aromatic carbons), 160.56 (CO, phth), 167.28 (CO, β-lactam); GC-MS m/z = 438 [M+]. Analysis calculated for C27H22N2O4: C 73.96, H 5.06, N 6.39%. Found: C 74.02, H 5.09, N 6.33%.
All the H atoms were geometrically generated (C–H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); 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).Fig. 1. View of the molecular structure of (I), with 30% probability displacement ellipsoids for the non-hydrogen atoms. | |
Fig. 2. View of the packing and hydrogen bonding interactions for (I). H atoms not involved in hydrogen bonding have been omitted for clarity. |
C27H22N2O4 | F(000) = 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 = 1.3–27.3° |
b = 7.0403 (2) Å | µ = 0.08 mm−1 |
c = 31.0482 (17) Å | T = 293 K |
β = 140.454 (3)° | 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) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.052 |
Plane graphite monochromator | θmax = 26.8°, θmin = 1.4° |
Detector resolution: 6.67 pixels mm-1 | h = −42→42 |
ω scans | k = −8→8 |
22562 measured reflections | l = −39→39 |
4934 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
4934 reflections | Δρmax = 0.17 e Å−3 |
299 parameters | Δρmin = −0.11 e Å−3 |
0 restraints | 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) |
C27H22N2O4 | V = 4698.0 (5) Å3 |
Mr = 438.47 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 33.7560 (17) Å | µ = 0.08 mm−1 |
b = 7.0403 (2) Å | T = 293 K |
c = 31.0482 (17) Å | 0.53 × 0.45 × 0.14 mm |
β = 140.454 (3)° |
Stoe IPDS-2 diffractometer | 3071 reflections with I > 2σ(I) |
22562 measured reflections | Rint = 0.052 |
4934 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.17 e Å−3 |
4934 reflections | Δρmin = −0.11 e Å−3 |
299 parameters |
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 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z; (iv) x, y+1, z; (v) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C27H22N2O4 |
Mr | 438.47 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 33.7560 (17), 7.0403 (2), 31.0482 (17) |
β (°) | 140.454 (3) |
V (Å3) | 4698.0 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.53 × 0.45 × 0.14 |
Data collection | |
Diffractometer | Stoe IPDS2 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22562, 4934, 3071 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.634 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.099, 0.97 |
No. of reflections | 4934 |
No. of parameters | 299 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.11 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
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) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z; (iv) x, y+1, z; (v) x+1/2, −y+1/2, z+1/2. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-2 diffractometer (purchased under grant F.279 of the University Research Fund).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The 2-azetidinone ring system is the common structural feature of a number of broad spectrum β-lactam antibiotics (Halve et al., 2007) and also possesses other pharmalogical properties (Aoyama et al., 2001). As part of our onging studies of such materials (Pınar et al., 2006; Akkurt et al., 2007), we now report the synthesis and structure of the title compound, (I), (Fig. 1).
The four-membered β-lactam ring in (I) is nearly planar, with maximum deviations of 0.022 (1) Å for N2 and -0.021 (2) Å for C10. Within the lactam ring, the bond lengths are similar to those observed in our previous studies (Pınar et al., 2006; Akkurt et al., 2007).
The four-membered β-lactam ring (N2/C9–C11) in (I) makes dihedral angles of 74.64 (12), 1.70 (11) and 73.67 (12)° with the nine-membered ring system (A: N1/C1–C8) {max. deviations from planarity = 0.048 (2) for N1 and -0.029 (3) Å for C2 and C7}, the benzene ring (B: C12–C17) and the phenyl ring (C: C22–C27), respectively. The other dihedral angles are A/B = 74.74 (9), A/C = 55.97 (11) and B/C = 74.84 (10)°. The sum of the bond angles about atom N2 is 360.0°.
The packing and hydrogen bonding of the title compound is shown in Fig. 2. The crystal structure is stabilized by inter- and intramolecular C—H···O interactions and C—H···π contacts (Table 1). Finally, an aromatic π—π stacking interaction {Cg3···Cg2(1 – x, 2 – y,1 – z) = 3.4505 (19)Å, where Cg3 is the centroid of the N1/C1/C2/C7/C8 five-membered ring} is observed in the crystal structure.