organic compounds
1-[3-(Morpholin-4-yl)propyl]-4-(3-nitrophenyl)spiro[azetidine-3,9′-xanthen]-2-one
aDepartment of Physics, Faculty of Sciences, Cumhuriyet University, 58140 Sivas, Turkey, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
The β-lactam (azetidin-2-one) ring of the title compound, C28H27N3O5, is nearly planar [maximum deviation = 0.010 (1) Å] and makes dihedral angles of 75.77 (5), 52.78 (9) and 88.72 (5)°, respectively, with the benzene ring, the least-squares plane formed by the four C atoms of the morpholine ring, which adopts a chair conformation, and the xanthene ring system. In the crystal, C—H⋯O hydrogen-bond contacts connect neighbouring molecules into infinite zigzag chains running parallel to the b axis.
CCDC reference: 988430
Related literature
For general background to β-lactams, see: Arumugam et al. (2011); Jarrahpour et al. (2010); Chrysselis et al. (2000); Mehta et al. (2010); Singh (2003); Singh et al. (2011, 2014). For similar structures, see: Akkurt et al. (2008a,b); Yalçın et al. (2009); Çelik et al. (2009a,b). For geometric analysis, see: Cremer & Pople (1975); Nardelli (1995).
Experimental
Crystal data
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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: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 988430
10.1107/S160053681400419X/sj5392sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400419X/sj5392Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681400419X/sj5392Isup3.cml
A mixture of N-(3-nitrobenzylidene)-3-morpholinopropan-1-amine (1.38 g, 5.00 mmol) and triethylamine (2.53 g, 25.00 mmol), 9H-xanthen-9-carboxylic acid (1.69 g, 7.50 mmol) and tosyl chloride (1.43 g, 7.50 mmol) in CH2Cl2 (25 ml) was stirred at room temperature overnight. Then it was washed with HCl 1 M, saturated sodium bicarbonate solution and brine, dried with Na2SO4 and the solvent was evaporated to give the crude product which was purified by β-lactam), 1342, 1527 (NO2). 1H-NMR (CDCl3) δ (p.p.m.): 1.94 (CH2—CH2—CH2–, m, 2H), 2.49 (CH2—CH2—CH2– and CH2—N morpholine ring, m, 6H), 3.18 (CH2—CH2—CH2–, m, 1H), 3.68 (CH2—O, m, 4H), 3.94 (CH2– CH2—CH2–, m, 1H), 4.72 (H-4, s, 1H), 5.43 (H-3, d, J = 4.4 Hz, 1H), 6.79- 7.94 (ArH, m, 12H). 13C-NMR (CDCl3) δ (p.p.m.): 24.9 (CH2—CH2—CH2–), 39.9 (CH2—CH2—CH2–), 53.5 (CH2—N morpholine ring), 56.0 (CH2—CH2—CH2–), 65.2 (C-4), 66.6 (CH2—O morpholine ring), 73.4 (C-3), 116.4, 116.8, 117.1, 121.2, 121.3, 122.9, 123.0, 124.4, 125.1, 127.8, 129.3, 129.4, 129.4, 132.6, 136.9, 147.9, 151.9, 152.1 (aromatic carbons), 168.1 (CO, β-lactam). GC–MS m/z = 485 [M+]. Anal. calcd for C28H27N3O5: C 69.26, H 5.61, N 8.65%. Found: C 69.30, H 5.69, N 8.67%.
(eluent 10:1 EtOAc/EtOH) as light yellow crystalline solid (Yield 59%). mp: 424–426 K. IR (KBr, cm-1): 1751 (CO,H atoms were positioned geometrically and were refined using a riding model with Uiso(H) = 1.2Ueq(C). Reflections (-2 1 2), (-2 0 4) and (0 2 4), were omitted due to the large disagreement between Fobs and Fcalc.
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: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).C28H27N3O5 | F(000) = 1024 |
Mr = 485.53 | Dx = 1.317 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 16797 reflections |
a = 9.2637 (6) Å | θ = 1.8–27.6° |
b = 11.4091 (5) Å | µ = 0.09 mm−1 |
c = 23.3310 (15) Å | T = 296 K |
β = 96.930 (5)° | Block, light yellow |
V = 2447.9 (2) Å3 | 0.55 × 0.38 × 0.22 mm |
Z = 4 |
Stoe IPDS 2 diffractometer | 5393 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3044 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.041 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.2°, θmin = 1.8° |
ω scans | h = −11→11 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −14→14 |
Tmin = 0.957, Tmax = 0.983 | l = −29→29 |
19036 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0457P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.88 | (Δ/σ)max < 0.001 |
5393 reflections | Δρmax = 0.15 e Å−3 |
325 parameters | Δρmin = −0.21 e Å−3 |
C28H27N3O5 | V = 2447.9 (2) Å3 |
Mr = 485.53 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.2637 (6) Å | µ = 0.09 mm−1 |
b = 11.4091 (5) Å | T = 296 K |
c = 23.3310 (15) Å | 0.55 × 0.38 × 0.22 mm |
β = 96.930 (5)° |
Stoe IPDS 2 diffractometer | 5393 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 3044 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.983 | Rint = 0.041 |
19036 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 0.88 | Δρmax = 0.15 e Å−3 |
5393 reflections | Δρmin = −0.21 e Å−3 |
325 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 | 0.84675 (13) | 0.41791 (9) | 0.23520 (5) | 0.0578 (4) | |
O2 | 0.49859 (13) | 0.68567 (11) | 0.32597 (5) | 0.0642 (5) | |
O3 | 0.21884 (16) | 0.55524 (13) | 0.00379 (6) | 0.0903 (6) | |
O4 | 0.39138 (19) | 0.44168 (14) | 0.03770 (8) | 0.1073 (7) | |
O5 | 0.76395 (16) | 0.93149 (14) | −0.03119 (7) | 0.0914 (6) | |
N1 | 0.80288 (13) | 0.58505 (10) | 0.17769 (5) | 0.0425 (4) | |
N2 | 0.33075 (18) | 0.53649 (15) | 0.03527 (6) | 0.0641 (6) | |
N3 | 0.86873 (15) | 0.81179 (12) | 0.07346 (6) | 0.0539 (5) | |
C1 | 0.78855 (17) | 0.51133 (13) | 0.22163 (6) | 0.0424 (5) | |
C2 | 0.67968 (16) | 0.59013 (12) | 0.24776 (6) | 0.0406 (5) | |
C3 | 0.69833 (16) | 0.67310 (12) | 0.19331 (6) | 0.0405 (4) | |
C4 | 0.74121 (18) | 0.64401 (13) | 0.30441 (6) | 0.0447 (5) | |
C5 | 0.88946 (19) | 0.65055 (15) | 0.32229 (7) | 0.0566 (6) | |
C6 | 0.9422 (2) | 0.70557 (18) | 0.37322 (8) | 0.0727 (7) | |
C7 | 0.8472 (3) | 0.75553 (18) | 0.40659 (8) | 0.0746 (8) | |
C8 | 0.6998 (2) | 0.74905 (16) | 0.39060 (7) | 0.0667 (7) | |
C9 | 0.64771 (19) | 0.69209 (14) | 0.33962 (7) | 0.0512 (5) | |
C10 | 0.44594 (19) | 0.59521 (15) | 0.28968 (7) | 0.0533 (6) | |
C11 | 0.3044 (2) | 0.55984 (18) | 0.29314 (9) | 0.0704 (8) | |
C12 | 0.2471 (2) | 0.4687 (2) | 0.25963 (10) | 0.0783 (8) | |
C13 | 0.3315 (2) | 0.41067 (18) | 0.22397 (9) | 0.0729 (8) | |
C14 | 0.4725 (2) | 0.44662 (15) | 0.22061 (7) | 0.0588 (6) | |
C15 | 0.53121 (18) | 0.54190 (14) | 0.25249 (6) | 0.0465 (5) | |
C16 | 0.57100 (16) | 0.69479 (13) | 0.14871 (6) | 0.0405 (4) | |
C17 | 0.50680 (17) | 0.80495 (14) | 0.14408 (6) | 0.0484 (5) | |
C18 | 0.39007 (18) | 0.82805 (15) | 0.10310 (7) | 0.0557 (6) | |
C19 | 0.33281 (18) | 0.74088 (16) | 0.06655 (7) | 0.0535 (6) | |
C20 | 0.39514 (17) | 0.63143 (14) | 0.07194 (6) | 0.0462 (5) | |
C21 | 0.51418 (17) | 0.60747 (13) | 0.11139 (6) | 0.0454 (5) | |
C22 | 0.89002 (19) | 0.57752 (15) | 0.13018 (7) | 0.0534 (6) | |
C23 | 1.0149 (2) | 0.66323 (17) | 0.13299 (8) | 0.0672 (7) | |
C24 | 0.9716 (2) | 0.79100 (17) | 0.12441 (8) | 0.0637 (7) | |
C25 | 0.8098 (3) | 0.93061 (16) | 0.07274 (10) | 0.0799 (8) | |
C26 | 0.7015 (3) | 0.9490 (2) | 0.02030 (12) | 0.0950 (10) | |
C27 | 0.8214 (2) | 0.8171 (2) | −0.03121 (9) | 0.0820 (8) | |
C28 | 0.9321 (2) | 0.79517 (17) | 0.02015 (7) | 0.0643 (7) | |
H3 | 0.74730 | 0.74660 | 0.20560 | 0.0490* | |
H5 | 0.95440 | 0.61730 | 0.29950 | 0.0680* | |
H6 | 1.04170 | 0.70870 | 0.38480 | 0.0870* | |
H7 | 0.88280 | 0.79430 | 0.44040 | 0.0900* | |
H8 | 0.63560 | 0.78240 | 0.41360 | 0.0800* | |
H11 | 0.24860 | 0.59770 | 0.31810 | 0.0850* | |
H12 | 0.15120 | 0.44600 | 0.26090 | 0.0940* | |
H13 | 0.29340 | 0.34720 | 0.20210 | 0.0870* | |
H14 | 0.52900 | 0.40660 | 0.19670 | 0.0710* | |
H17 | 0.54320 | 0.86430 | 0.16910 | 0.0580* | |
H18 | 0.35000 | 0.90290 | 0.10020 | 0.0670* | |
H19 | 0.25390 | 0.75550 | 0.03890 | 0.0640* | |
H21 | 0.55610 | 0.53330 | 0.11300 | 0.0550* | |
H22A | 0.82710 | 0.59030 | 0.09440 | 0.0640* | |
H22B | 0.92870 | 0.49870 | 0.12900 | 0.0640* | |
H23A | 1.07620 | 0.64180 | 0.10370 | 0.0810* | |
H23B | 1.07290 | 0.65530 | 0.17030 | 0.0810* | |
H24A | 0.92910 | 0.81780 | 0.15810 | 0.0760* | |
H24B | 1.05830 | 0.83720 | 0.12160 | 0.0760* | |
H25A | 0.88840 | 0.98680 | 0.07270 | 0.0960* | |
H25B | 0.76320 | 0.94350 | 0.10730 | 0.0960* | |
H26A | 0.62100 | 0.89510 | 0.02140 | 0.1140* | |
H26B | 0.66330 | 1.02810 | 0.02080 | 0.1140* | |
H27A | 0.86620 | 0.80520 | −0.06630 | 0.0980* | |
H27B | 0.74280 | 0.76090 | −0.03110 | 0.0980* | |
H28A | 0.96870 | 0.71570 | 0.01860 | 0.0770* | |
H28B | 1.01330 | 0.84850 | 0.01920 | 0.0770* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0719 (8) | 0.0442 (6) | 0.0557 (6) | 0.0105 (6) | 0.0012 (6) | 0.0086 (5) |
O2 | 0.0646 (8) | 0.0644 (8) | 0.0658 (8) | −0.0010 (7) | 0.0172 (6) | −0.0135 (6) |
O3 | 0.0830 (10) | 0.1006 (11) | 0.0769 (9) | −0.0037 (8) | −0.0333 (8) | −0.0132 (8) |
O4 | 0.1157 (13) | 0.0641 (10) | 0.1279 (13) | 0.0029 (9) | −0.0430 (11) | −0.0246 (9) |
O5 | 0.0794 (10) | 0.0904 (11) | 0.1034 (12) | 0.0183 (9) | 0.0075 (9) | 0.0388 (9) |
N1 | 0.0466 (7) | 0.0417 (7) | 0.0391 (6) | 0.0052 (6) | 0.0044 (6) | 0.0046 (6) |
N2 | 0.0675 (10) | 0.0654 (10) | 0.0551 (9) | −0.0072 (8) | −0.0104 (8) | −0.0034 (8) |
N3 | 0.0539 (8) | 0.0478 (8) | 0.0602 (8) | 0.0011 (7) | 0.0082 (7) | 0.0008 (7) |
C1 | 0.0474 (9) | 0.0388 (8) | 0.0382 (8) | −0.0011 (7) | −0.0061 (7) | 0.0026 (7) |
C2 | 0.0480 (9) | 0.0383 (8) | 0.0347 (7) | −0.0009 (7) | 0.0023 (6) | 0.0033 (6) |
C3 | 0.0447 (8) | 0.0374 (8) | 0.0386 (7) | −0.0003 (7) | 0.0022 (6) | 0.0009 (6) |
C4 | 0.0565 (10) | 0.0429 (8) | 0.0339 (7) | −0.0037 (8) | 0.0020 (7) | 0.0043 (6) |
C5 | 0.0568 (11) | 0.0641 (11) | 0.0469 (9) | −0.0088 (9) | −0.0017 (8) | 0.0006 (8) |
C6 | 0.0737 (13) | 0.0866 (14) | 0.0534 (10) | −0.0198 (12) | −0.0102 (10) | −0.0017 (10) |
C7 | 0.0998 (17) | 0.0782 (14) | 0.0435 (10) | −0.0289 (12) | −0.0012 (11) | −0.0078 (9) |
C8 | 0.0974 (16) | 0.0619 (11) | 0.0433 (9) | −0.0142 (11) | 0.0190 (10) | −0.0082 (8) |
C9 | 0.0609 (11) | 0.0491 (9) | 0.0438 (8) | −0.0065 (8) | 0.0076 (8) | 0.0029 (8) |
C10 | 0.0532 (10) | 0.0551 (10) | 0.0514 (9) | −0.0036 (9) | 0.0054 (8) | 0.0052 (8) |
C11 | 0.0551 (12) | 0.0800 (14) | 0.0777 (13) | −0.0019 (10) | 0.0146 (10) | 0.0084 (11) |
C12 | 0.0570 (12) | 0.0886 (15) | 0.0886 (15) | −0.0207 (12) | 0.0055 (11) | 0.0157 (13) |
C13 | 0.0721 (14) | 0.0705 (13) | 0.0738 (13) | −0.0266 (11) | 0.0000 (11) | 0.0004 (11) |
C14 | 0.0647 (12) | 0.0560 (10) | 0.0551 (10) | −0.0142 (9) | 0.0045 (9) | −0.0001 (8) |
C15 | 0.0517 (10) | 0.0458 (9) | 0.0407 (8) | −0.0045 (8) | 0.0009 (7) | 0.0075 (7) |
C16 | 0.0445 (8) | 0.0419 (8) | 0.0353 (7) | 0.0014 (7) | 0.0053 (6) | 0.0033 (7) |
C17 | 0.0565 (10) | 0.0451 (9) | 0.0433 (8) | 0.0069 (8) | 0.0045 (8) | −0.0021 (7) |
C18 | 0.0584 (11) | 0.0520 (10) | 0.0556 (10) | 0.0184 (8) | 0.0020 (8) | 0.0012 (8) |
C19 | 0.0456 (9) | 0.0694 (11) | 0.0444 (9) | 0.0093 (9) | 0.0005 (8) | 0.0059 (8) |
C20 | 0.0476 (9) | 0.0521 (9) | 0.0385 (8) | −0.0022 (8) | 0.0031 (7) | 0.0006 (7) |
C21 | 0.0517 (9) | 0.0416 (9) | 0.0420 (8) | 0.0032 (7) | 0.0015 (7) | 0.0038 (7) |
C22 | 0.0622 (11) | 0.0526 (10) | 0.0472 (9) | 0.0087 (9) | 0.0145 (8) | 0.0023 (8) |
C23 | 0.0517 (10) | 0.0897 (15) | 0.0603 (11) | 0.0010 (10) | 0.0072 (9) | 0.0204 (10) |
C24 | 0.0626 (12) | 0.0716 (12) | 0.0571 (10) | −0.0203 (10) | 0.0085 (9) | 0.0010 (9) |
C25 | 0.0907 (15) | 0.0502 (11) | 0.1043 (16) | 0.0055 (11) | 0.0337 (14) | −0.0014 (11) |
C26 | 0.0768 (15) | 0.0736 (15) | 0.136 (2) | 0.0262 (12) | 0.0188 (16) | 0.0281 (15) |
C27 | 0.0839 (15) | 0.0882 (16) | 0.0705 (13) | 0.0121 (12) | −0.0048 (11) | 0.0079 (12) |
C28 | 0.0641 (12) | 0.0697 (12) | 0.0586 (10) | 0.0146 (10) | 0.0059 (9) | 0.0062 (9) |
O1—C1 | 1.2189 (18) | C18—C19 | 1.374 (2) |
O2—C9 | 1.382 (2) | C19—C20 | 1.375 (2) |
O2—C10 | 1.386 (2) | C20—C21 | 1.376 (2) |
O3—N2 | 1.215 (2) | C22—C23 | 1.510 (3) |
O4—N2 | 1.217 (2) | C23—C24 | 1.519 (3) |
O5—C26 | 1.409 (3) | C25—C26 | 1.500 (4) |
O5—C27 | 1.410 (3) | C27—C28 | 1.501 (3) |
N1—C1 | 1.3449 (18) | C3—H3 | 0.9800 |
N1—C3 | 1.4715 (19) | C5—H5 | 0.9300 |
N1—C22 | 1.450 (2) | C6—H6 | 0.9300 |
N2—C20 | 1.462 (2) | C7—H7 | 0.9300 |
N3—C24 | 1.451 (2) | C8—H8 | 0.9300 |
N3—C25 | 1.461 (2) | C11—H11 | 0.9300 |
N3—C28 | 1.450 (2) | C12—H12 | 0.9300 |
C1—C2 | 1.532 (2) | C13—H13 | 0.9300 |
C2—C3 | 1.610 (2) | C14—H14 | 0.9300 |
C2—C4 | 1.506 (2) | C17—H17 | 0.9300 |
C2—C15 | 1.498 (2) | C18—H18 | 0.9300 |
C3—C16 | 1.496 (2) | C19—H19 | 0.9300 |
C4—C5 | 1.388 (2) | C21—H21 | 0.9300 |
C4—C9 | 1.378 (2) | C22—H22A | 0.9700 |
C5—C6 | 1.380 (3) | C22—H22B | 0.9700 |
C6—C7 | 1.368 (3) | C23—H23A | 0.9700 |
C7—C8 | 1.373 (3) | C23—H23B | 0.9700 |
C8—C9 | 1.390 (2) | C24—H24A | 0.9700 |
C10—C11 | 1.384 (3) | C24—H24B | 0.9700 |
C10—C15 | 1.383 (2) | C25—H25A | 0.9700 |
C11—C12 | 1.369 (3) | C25—H25B | 0.9700 |
C12—C13 | 1.378 (3) | C26—H26A | 0.9700 |
C13—C14 | 1.380 (3) | C26—H26B | 0.9700 |
C14—C15 | 1.390 (2) | C27—H27A | 0.9700 |
C16—C17 | 1.389 (2) | C27—H27B | 0.9700 |
C16—C21 | 1.385 (2) | C28—H28A | 0.9700 |
C17—C18 | 1.380 (2) | C28—H28B | 0.9700 |
C9—O2—C10 | 116.66 (13) | C2—C3—H3 | 111.00 |
C26—O5—C27 | 108.99 (17) | C16—C3—H3 | 111.00 |
C1—N1—C3 | 96.30 (11) | C4—C5—H5 | 119.00 |
C1—N1—C22 | 131.36 (13) | C6—C5—H5 | 119.00 |
C3—N1—C22 | 132.33 (12) | C5—C6—H6 | 120.00 |
O3—N2—O4 | 122.68 (17) | C7—C6—H6 | 120.00 |
O3—N2—C20 | 118.78 (16) | C6—C7—H7 | 120.00 |
O4—N2—C20 | 118.54 (16) | C8—C7—H7 | 120.00 |
C24—N3—C25 | 111.64 (15) | C7—C8—H8 | 120.00 |
C24—N3—C28 | 112.80 (14) | C9—C8—H8 | 120.00 |
C25—N3—C28 | 107.51 (15) | C10—C11—H11 | 120.00 |
O1—C1—N1 | 131.57 (14) | C12—C11—H11 | 120.00 |
O1—C1—C2 | 134.57 (14) | C11—C12—H12 | 120.00 |
N1—C1—C2 | 93.82 (11) | C13—C12—H12 | 120.00 |
C1—C2—C3 | 83.83 (10) | C12—C13—H13 | 120.00 |
C1—C2—C4 | 113.04 (12) | C14—C13—H13 | 120.00 |
C1—C2—C15 | 117.93 (12) | C13—C14—H14 | 120.00 |
C3—C2—C4 | 112.78 (11) | C15—C14—H14 | 120.00 |
C3—C2—C15 | 117.45 (12) | C16—C17—H17 | 119.00 |
C4—C2—C15 | 109.82 (12) | C18—C17—H17 | 119.00 |
N1—C3—C2 | 86.02 (10) | C17—C18—H18 | 120.00 |
N1—C3—C16 | 115.33 (12) | C19—C18—H18 | 120.00 |
C2—C3—C16 | 119.69 (12) | C18—C19—H19 | 121.00 |
C2—C4—C5 | 122.79 (14) | C20—C19—H19 | 121.00 |
C2—C4—C9 | 119.16 (15) | C16—C21—H21 | 120.00 |
C5—C4—C9 | 118.02 (14) | C20—C21—H21 | 120.00 |
C4—C5—C6 | 121.18 (16) | N1—C22—H22A | 108.00 |
C5—C6—C7 | 119.63 (18) | N1—C22—H22B | 109.00 |
C6—C7—C8 | 120.65 (18) | C23—C22—H22A | 109.00 |
C7—C8—C9 | 119.26 (17) | C23—C22—H22B | 109.00 |
O2—C9—C4 | 121.64 (14) | H22A—C22—H22B | 108.00 |
O2—C9—C8 | 117.15 (15) | C22—C23—H23A | 108.00 |
C4—C9—C8 | 121.21 (16) | C22—C23—H23B | 108.00 |
O2—C10—C11 | 116.60 (16) | C24—C23—H23A | 108.00 |
O2—C10—C15 | 121.69 (15) | C24—C23—H23B | 108.00 |
C11—C10—C15 | 121.70 (16) | H23A—C23—H23B | 107.00 |
C10—C11—C12 | 119.55 (18) | N3—C24—H24A | 109.00 |
C11—C12—C13 | 120.04 (18) | N3—C24—H24B | 109.00 |
C12—C13—C14 | 120.09 (18) | C23—C24—H24A | 109.00 |
C13—C14—C15 | 120.91 (17) | C23—C24—H24B | 109.00 |
C2—C15—C10 | 118.93 (14) | H24A—C24—H24B | 108.00 |
C2—C15—C14 | 123.45 (14) | N3—C25—H25A | 109.00 |
C10—C15—C14 | 117.61 (16) | N3—C25—H25B | 110.00 |
C3—C16—C17 | 119.86 (13) | C26—C25—H25A | 110.00 |
C3—C16—C21 | 121.75 (13) | C26—C25—H25B | 110.00 |
C17—C16—C21 | 118.39 (13) | H25A—C25—H25B | 108.00 |
C16—C17—C18 | 121.28 (14) | O5—C26—H26A | 109.00 |
C17—C18—C19 | 120.22 (16) | O5—C26—H26B | 109.00 |
C18—C19—C20 | 118.30 (15) | C25—C26—H26A | 109.00 |
N2—C20—C19 | 118.82 (14) | C25—C26—H26B | 109.00 |
N2—C20—C21 | 118.80 (14) | H26A—C26—H26B | 108.00 |
C19—C20—C21 | 122.37 (14) | O5—C27—H27A | 109.00 |
C16—C21—C20 | 119.40 (14) | O5—C27—H27B | 109.00 |
N1—C22—C23 | 115.00 (14) | C28—C27—H27A | 109.00 |
C22—C23—C24 | 115.28 (15) | C28—C27—H27B | 109.00 |
N3—C24—C23 | 113.70 (15) | H27A—C27—H27B | 108.00 |
N3—C25—C26 | 110.57 (17) | N3—C28—H28A | 109.00 |
O5—C26—C25 | 111.9 (2) | N3—C28—H28B | 109.00 |
O5—C27—C28 | 112.07 (17) | C27—C28—H28A | 110.00 |
N3—C28—C27 | 110.76 (15) | C27—C28—H28B | 110.00 |
N1—C3—H3 | 111.00 | H28A—C28—H28B | 108.00 |
C9—O2—C10—C11 | 155.89 (16) | C1—C2—C15—C14 | −19.2 (2) |
C10—O2—C9—C4 | 23.8 (2) | C15—C2—C3—N1 | −119.59 (13) |
C10—O2—C9—C8 | −156.04 (15) | C1—C2—C15—C10 | 161.87 (14) |
C9—O2—C10—C15 | −23.2 (2) | C3—C2—C15—C14 | 78.76 (19) |
C27—O5—C26—C25 | 57.9 (2) | C1—C2—C4—C9 | −163.90 (14) |
C26—O5—C27—C28 | −57.7 (2) | C2—C3—C16—C17 | 110.27 (15) |
C1—N1—C22—C23 | −110.50 (18) | C2—C3—C16—C21 | −69.70 (18) |
C3—N1—C1—O1 | −179.56 (17) | N1—C3—C16—C21 | 30.8 (2) |
C22—N1—C1—C2 | 179.91 (15) | N1—C3—C16—C17 | −149.28 (13) |
C22—N1—C1—O1 | 1.9 (3) | C5—C4—C9—O2 | −177.71 (14) |
C3—N1—C1—C2 | −1.50 (12) | C9—C4—C5—C6 | −1.3 (2) |
C3—N1—C22—C23 | 71.4 (2) | C2—C4—C5—C6 | 176.86 (16) |
C1—N1—C3—C16 | −119.66 (13) | C2—C4—C9—O2 | 4.1 (2) |
C22—N1—C3—C2 | 180.00 (15) | C5—C4—C9—C8 | 2.2 (2) |
C22—N1—C3—C16 | 58.9 (2) | C2—C4—C9—C8 | −176.06 (15) |
C1—N1—C3—C2 | 1.43 (11) | C4—C5—C6—C7 | −0.6 (3) |
O3—N2—C20—C21 | 174.10 (15) | C5—C6—C7—C8 | 1.6 (3) |
O4—N2—C20—C19 | 175.60 (17) | C6—C7—C8—C9 | −0.7 (3) |
O4—N2—C20—C21 | −5.7 (2) | C7—C8—C9—O2 | 178.67 (16) |
O3—N2—C20—C19 | −4.6 (2) | C7—C8—C9—C4 | −1.2 (3) |
C24—N3—C25—C26 | −178.81 (18) | C11—C10—C15—C14 | −3.4 (2) |
C28—N3—C24—C23 | −69.47 (19) | O2—C10—C15—C2 | −5.3 (2) |
C25—N3—C24—C23 | 169.34 (17) | C11—C10—C15—C2 | 175.60 (16) |
C28—N3—C25—C26 | 57.0 (2) | C15—C10—C11—C12 | 0.9 (3) |
C25—N3—C28—C27 | −56.8 (2) | O2—C10—C11—C12 | −178.17 (18) |
C24—N3—C28—C27 | 179.73 (16) | O2—C10—C15—C14 | 175.66 (15) |
O1—C1—C2—C15 | −62.8 (2) | C10—C11—C12—C13 | 1.8 (3) |
O1—C1—C2—C3 | 179.33 (19) | C11—C12—C13—C14 | −2.0 (3) |
O1—C1—C2—C4 | 67.2 (2) | C12—C13—C14—C15 | −0.6 (3) |
N1—C1—C2—C15 | 119.25 (13) | C13—C14—C15—C10 | 3.2 (2) |
N1—C1—C2—C4 | −110.79 (13) | C13—C14—C15—C2 | −175.76 (16) |
N1—C1—C2—C3 | 1.37 (11) | C21—C16—C17—C18 | −0.6 (2) |
C1—C2—C4—C5 | 18.0 (2) | C3—C16—C17—C18 | 179.44 (14) |
C15—C2—C3—C16 | −2.59 (19) | C3—C16—C21—C20 | 178.70 (14) |
C4—C2—C15—C14 | −150.62 (15) | C17—C16—C21—C20 | −1.3 (2) |
C15—C2—C4—C9 | −29.94 (19) | C16—C17—C18—C19 | 1.4 (2) |
C3—C2—C4—C9 | 103.12 (16) | C17—C18—C19—C20 | −0.2 (2) |
C15—C2—C4—C5 | 151.94 (15) | C18—C19—C20—C21 | −1.7 (2) |
C4—C2—C3—C16 | −131.83 (14) | C18—C19—C20—N2 | 176.99 (15) |
C3—C2—C15—C10 | −100.18 (16) | C19—C20—C21—C16 | 2.5 (2) |
C4—C2—C3—N1 | 111.17 (13) | N2—C20—C21—C16 | −176.22 (14) |
C1—C2—C3—C16 | 115.75 (13) | N1—C22—C23—C24 | −68.6 (2) |
C1—C2—C3—N1 | −1.25 (10) | C22—C23—C24—N3 | −50.6 (2) |
C4—C2—C15—C10 | 30.44 (19) | N3—C25—C26—O5 | −59.3 (2) |
C3—C2—C4—C5 | −75.00 (18) | O5—C27—C28—N3 | 59.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O1i | 0.93 | 2.42 | 3.2423 (19) | 148 |
C22—H22A···N3 | 0.97 | 2.61 | 2.978 (2) | 103 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O1i | 0.93 | 2.42 | 3.2423 (19) | 148 |
Symmetry code: (i) −x+3/2, 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
Akkurt, M., Jarrahpour, A., Ebrahimi, E., Gençaslan, M. & Büyükgüngör, O. (2008a). Acta Cryst. E64, o2466–o2467. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Akkurt, M., Karaca, S., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2008b). Acta Cryst. E64, o902–o903. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Arumugam, N., Periyasami, G., Raghunathan, R., Kamalraj, S. & Muthumary, J. (2011). Eur. J. Med. Chem. 46, 600–607. Web of Science CrossRef CAS PubMed Google Scholar
Çelik, Í., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009a). Acta Cryst. E65, o501–o502. Web of Science CSD CrossRef IUCr Journals Google Scholar
Çelik, Í., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009b). Acta Cryst. E65, o2522–o2523. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chrysselis, M. C., Rekka, E. A. & Kourounakis, P. N. (2000). J. Med. Chem. 43, 609–612. Web of Science CrossRef PubMed CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jarrahpour, A., Eskandari, M., Zomorodian, K., Barati, E., Ashori, R., Salehi Vaziri, M. & Pakshir, K. (2010). Anti-Infective Agents Med. Chem. 9, 205–219. CrossRef CAS Google Scholar
Mehta, P. D., Sengar, N. P. S. & Pathak, A. K. (2010). Eur. J. Med. Chem. 45, 5541–5560. Web of Science CrossRef CAS PubMed Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, G. S. (2003). Tetrahedron, 59, 7631–7649. Web of Science CrossRef CAS Google Scholar
Singh, G. S., D'hooghe, M. & De Kimpe, N. (2011). Tetrahedron, 67, 1989–2012. Web of Science CrossRef CAS Google Scholar
Singh, P., Raj, R., Singh, P., Gut, J., Rosenthal, P. J. & Kumar, V. (2014). Eur. J. Med. Chem. 71, 128–134. Web of Science CrossRef CAS PubMed Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Yalçın, Ş. P., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009). Acta Cryst. E65, o626–o627. Web of Science CSD CrossRef IUCr Journals Google Scholar
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.
2-Azetidinones, commonly known as β-lactams, occupy a central place among medicinally important compounds due to their unique structure and their antibacterial activities (Arumugam et al., 2011; Jarrahpour et al., 2010; Singh, 2003; Singh et al., 2011, 2014). β-Lactams have shown many interesting biological properties, such as acting as cholesterol absorption inhibitors, and applications as antimicrobial, antifungal, antitubercular, anticancer, anti HIV and antiparkinsonian agents (Mehta et al. 2010). Moreover the morpholine moiety is present in many heterocyclic compounds with hypocholesterolemic and hypolipidemic activity (Chrysselis et al. 2000).
The β-lactam unit in (I, Fig. 1) is nearly planar, with a maximum deviation of 0.010 (1) Å from the mean plane. Atom O1 lies almost in the β-lactam plane, with a deviation of -0.001 (1) Å. The β-lactam ring makes a dihedral angle of 75.77 (5)° with the benzene ring C16—C21.
The xanthene ring system is V-shaped, with a dihedral angle between the (C4–C9) and (C10–C15) benzene rings of 27.82 (5)°. Its central ring, C2/C4/C9/O2/C10/C15, is not planar, with puckering parameters: QT = 0.3640 (16) Å, θ = 81.6 (3)° and φ = 181.0 (3)° (Cremer & Pople, 1975). The mean plane of the xanthene ring system forms dihedral angles of 88.72 (5), 55.87 (4) and 44.54 (7)° (Nardelli, 1995), with the β-lactam ring, the benzene ring (C16–C21) and the least-squares plane formed by the four C atoms of the morpholine ring (N3/O5/C25–C28), respectively.
The bond lengths and angles in (I) are comparable with similar compounds that we have reported previously (Akkurt et al., 2008a,b; Çelik et al., 2009a,b; Yalçın et al., 2009).
In the crystal, molecules are linked by C—H···O hydrogen contacts (Table 1) into infinite zigzag chains running parallel to [010]. Fig. 2 shows a view down the a axis of the crystal packing of (I).