organic compounds
11-Hydroxy-9-[1-(4-methylphenyl)-4-oxo-3-phenylazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.01,8.02,6.012,17]octadeca-12,14,16-triene-8-carbonitrile
aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: shirai2011@gmail.com
In the title compound, C33H29N3O5, the four-membered ring of the β-lactam fragment is essentially planar (r.m.s. deviation = 0.0122 Å), with the carbonyl O atom displaced from this ring by 0.856 (9) Å. The mean planes of the methoxyphenyl and phenyl rings are inclined at dihedral angles 85.10 (7) and 21.56 (14)°, respectively, with respect to the mean plane of the four-membered ring. The pyrrolidine rings adopt envelope conformations with C atoms lying 0.535 (4) and 0.519 (4) Å out of the planes formed by the remaining ring atoms. The furan ring also adopts an with a C atom 0.560 (3) Å out of the plane formed by the remaining ring atoms. The nine-membered indene ring is almost planar (r.m.s. deviation = 0.0240 Å), with the carbonyl O atom displaced by 0.145 (3) Å from this ring. The molecular structure is stabilized by a strong intramolecular O—H⋯N hydrogen bond and the is consolidated by C—H⋯O hydrogen bonds.
Related literature
For general background to β-lactams, see: Brakhage (1998). For a related structure, see: Sundaramoorthy et al. (2012).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); 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).
Supporting information
10.1107/S1600536812044479/pv2596sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044479/pv2596Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812044479/pv2596Isup3.cml
A reaction mixture of 2-(hydroxy(1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin -2-yl)methyl)acrylonitrile (1.0 mmol), ninhydrine (1.1 mmol) and proline (1.1 mmol) was refluxed in methanol (20 ml) until completion of the reaction was evidenced by TLC analysis. After completion of the reaction the solvent was evaporated under reduced pressure. The crude reaction mixture was dissolved in dichloromethane (2 x 50 ml) and washed with water followed by brine solution. The organic layer was separated and dried over sodium sulfate. After filteration and evaporation of the organic solvent was carried out under reduced pressure. The product was separated by
using hexane and ethyl acetate (4:6) as an to give a colorless solid. The product was dissolved in chloroform (3 ml) and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent resulting in single crystals suitable for X-ray crystallographic studies.All H atoms bonded to C-atoms were positioned geometrically and refined using a riding model, with C—H = 0.93, 0.96, 0.97 and 0.98 Å, for aryl, methyl, methylene and methine H-atoms, respectively. The Uiso(H) were allowed at 1.5Ueq(C methyl) or 1.2Ueq(C non-methyl). The hydroxy H-atom was located from a difference map and was alloewed to refine freely. An
was not established due to insufficient effects. Therefore, 2699 Friedel pairs of reflections were merged.Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).C33H29N3O5 | F(000) = 1152 |
Mr = 547.59 | Dx = 1.326 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6406 reflections |
a = 10.2874 (16) Å | θ = 1.8–28.0° |
b = 14.138 (3) Å | µ = 0.09 mm−1 |
c = 18.866 (3) Å | T = 293 K |
V = 2743.9 (8) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Bruker SMART APEXII area-detector diffractometer | 6406 independent reflections |
Radiation source: fine-focus sealed tube | 4551 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω and ϕ scans | θmax = 28.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −7→13 |
Tmin = 0.973, Tmax = 0.982 | k = −18→18 |
14810 measured reflections | l = −24→23 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0605P)2 + 0.2909P] where P = (Fo2 + 2Fc2)/3 |
6406 reflections | (Δ/σ)max < 0.001 |
375 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C33H29N3O5 | V = 2743.9 (8) Å3 |
Mr = 547.59 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.2874 (16) Å | µ = 0.09 mm−1 |
b = 14.138 (3) Å | T = 293 K |
c = 18.866 (3) Å | 0.30 × 0.25 × 0.20 mm |
Bruker SMART APEXII area-detector diffractometer | 6406 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 4551 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.982 | Rint = 0.034 |
14810 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.25 e Å−3 |
6406 reflections | Δρmin = −0.16 e Å−3 |
375 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.5616 (4) | 0.7130 (2) | 0.3845 (2) | 0.1143 (16) | |
H1A | 0.6495 | 0.7115 | 0.4016 | 0.171* | |
H1B | 0.5356 | 0.7775 | 0.3770 | 0.171* | |
H1C | 0.5562 | 0.6789 | 0.3407 | 0.171* | |
C2 | 0.4988 (2) | 0.57555 (16) | 0.45053 (11) | 0.0485 (6) | |
C3 | 0.6029 (2) | 0.52399 (16) | 0.42370 (12) | 0.0491 (5) | |
H3 | 0.6624 | 0.5527 | 0.3935 | 0.059* | |
C4 | 0.6177 (2) | 0.42957 (16) | 0.44211 (12) | 0.0456 (5) | |
H4 | 0.6874 | 0.3951 | 0.4243 | 0.055* | |
C5 | 0.5287 (2) | 0.38631 (14) | 0.48714 (9) | 0.0364 (4) | |
C6 | 0.4241 (2) | 0.43760 (16) | 0.51336 (11) | 0.0461 (5) | |
H6 | 0.3636 | 0.4087 | 0.5429 | 0.055* | |
C7 | 0.4105 (3) | 0.53205 (17) | 0.49536 (13) | 0.0538 (6) | |
H7 | 0.3412 | 0.5667 | 0.5136 | 0.065* | |
C8 | 0.6046 (2) | 0.21567 (16) | 0.47055 (11) | 0.0394 (5) | |
C9 | 0.5463 (2) | 0.14150 (15) | 0.52086 (10) | 0.0386 (5) | |
H9 | 0.6120 | 0.1086 | 0.5493 | 0.046* | |
C10 | 0.4835 (2) | 0.22795 (14) | 0.56050 (10) | 0.0363 (4) | |
H10 | 0.3884 | 0.2277 | 0.5571 | 0.044* | |
C11 | 0.5303 (2) | 0.25097 (16) | 0.63567 (10) | 0.0394 (5) | |
H11 | 0.5225 | 0.3194 | 0.6429 | 0.047* | |
C12 | 0.4597 (2) | 0.19991 (15) | 0.69836 (10) | 0.0384 (5) | |
C13 | 0.3429 (2) | 0.25415 (18) | 0.72944 (12) | 0.0486 (6) | |
H13A | 0.2913 | 0.2827 | 0.6921 | 0.058* | |
H13B | 0.2880 | 0.2125 | 0.7572 | 0.058* | |
C14 | 0.4057 (2) | 0.32998 (17) | 0.77630 (12) | 0.0510 (6) | |
H14 | 0.4282 | 0.3856 | 0.7478 | 0.061* | |
C15 | 0.3287 (3) | 0.3600 (2) | 0.84225 (15) | 0.0708 (8) | |
H15A | 0.3489 | 0.4247 | 0.8553 | 0.085* | |
H15B | 0.2359 | 0.3547 | 0.8340 | 0.085* | |
C16 | 0.3722 (4) | 0.2922 (2) | 0.89897 (15) | 0.0761 (9) | |
H16A | 0.3232 | 0.2336 | 0.8967 | 0.091* | |
H16B | 0.3619 | 0.3197 | 0.9457 | 0.091* | |
C17 | 0.5135 (4) | 0.2754 (2) | 0.88228 (13) | 0.0788 (10) | |
H17A | 0.5675 | 0.3220 | 0.9060 | 0.095* | |
H17B | 0.5398 | 0.2129 | 0.8978 | 0.095* | |
C18 | 0.5657 (2) | 0.20575 (15) | 0.75882 (10) | 0.0402 (5) | |
C19 | 0.6952 (2) | 0.22920 (17) | 0.71836 (11) | 0.0452 (5) | |
C20 | 0.5949 (2) | 0.11036 (17) | 0.79611 (10) | 0.0456 (5) | |
C21 | 0.7328 (2) | 0.08641 (17) | 0.78283 (11) | 0.0482 (6) | |
C22 | 0.7901 (2) | 0.15161 (18) | 0.73715 (12) | 0.0491 (6) | |
C23 | 0.9189 (3) | 0.1410 (2) | 0.71638 (14) | 0.0692 (8) | |
H23 | 0.9576 | 0.1838 | 0.6855 | 0.083* | |
C24 | 0.9880 (3) | 0.0645 (3) | 0.74306 (16) | 0.0816 (9) | |
H24 | 1.0744 | 0.0563 | 0.7299 | 0.098* | |
C25 | 0.9311 (3) | 0.0003 (3) | 0.78893 (17) | 0.0795 (9) | |
H25 | 0.9800 | −0.0500 | 0.8061 | 0.095* | |
C26 | 0.8033 (3) | 0.00942 (19) | 0.80953 (14) | 0.0639 (7) | |
H26 | 0.7651 | −0.0340 | 0.8401 | 0.077* | |
C27 | 0.4551 (2) | 0.07495 (14) | 0.48296 (10) | 0.0392 (5) | |
C28 | 0.3612 (2) | 0.10843 (16) | 0.43596 (11) | 0.0434 (5) | |
H28 | 0.3541 | 0.1732 | 0.4284 | 0.052* | |
C29 | 0.2783 (2) | 0.04784 (17) | 0.40026 (12) | 0.0515 (6) | |
H29 | 0.2163 | 0.0718 | 0.3692 | 0.062* | |
C30 | 0.2885 (3) | −0.04835 (18) | 0.41119 (14) | 0.0614 (7) | |
H30 | 0.2332 | −0.0895 | 0.3873 | 0.074* | |
C31 | 0.3803 (3) | −0.08373 (18) | 0.45731 (14) | 0.0678 (8) | |
H31 | 0.3862 | −0.1486 | 0.4648 | 0.081* | |
C32 | 0.4644 (3) | −0.02266 (16) | 0.49279 (12) | 0.0546 (6) | |
H32 | 0.5272 | −0.0471 | 0.5232 | 0.066* | |
C33 | 0.4248 (2) | 0.10128 (17) | 0.67921 (11) | 0.0453 (5) | |
N1 | 0.54457 (16) | 0.28914 (12) | 0.50512 (8) | 0.0385 (4) | |
N2 | 0.5264 (2) | 0.28416 (13) | 0.80428 (10) | 0.0507 (5) | |
N3 | 0.3949 (2) | 0.02553 (16) | 0.66654 (12) | 0.0653 (6) | |
O1 | 0.4773 (2) | 0.67002 (12) | 0.43580 (11) | 0.0735 (6) | |
O2 | 0.67202 (16) | 0.21280 (12) | 0.41786 (9) | 0.0542 (4) | |
O3 | 0.66478 (15) | 0.22531 (11) | 0.64393 (7) | 0.0463 (4) | |
O4 | 0.7423 (2) | 0.31898 (13) | 0.73731 (10) | 0.0601 (5) | |
O5 | 0.51536 (18) | 0.06443 (13) | 0.82903 (9) | 0.0626 (5) | |
H4A | 0.679 (3) | 0.335 (2) | 0.7702 (17) | 0.076 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.151 (4) | 0.0565 (19) | 0.136 (3) | 0.018 (2) | 0.072 (3) | 0.040 (2) |
C2 | 0.0609 (15) | 0.0398 (11) | 0.0449 (12) | −0.0010 (11) | 0.0029 (11) | 0.0046 (9) |
C3 | 0.0504 (14) | 0.0484 (13) | 0.0483 (12) | −0.0070 (11) | 0.0073 (11) | 0.0095 (10) |
C4 | 0.0416 (13) | 0.0462 (12) | 0.0490 (12) | 0.0032 (10) | 0.0024 (10) | 0.0061 (10) |
C5 | 0.0401 (11) | 0.0389 (10) | 0.0302 (9) | −0.0009 (9) | −0.0017 (9) | 0.0016 (8) |
C6 | 0.0495 (14) | 0.0436 (12) | 0.0453 (11) | −0.0018 (10) | 0.0096 (10) | 0.0053 (10) |
C7 | 0.0576 (15) | 0.0469 (13) | 0.0569 (14) | 0.0086 (11) | 0.0116 (12) | 0.0016 (11) |
C8 | 0.0322 (10) | 0.0483 (12) | 0.0378 (10) | 0.0010 (10) | 0.0003 (9) | −0.0014 (9) |
C9 | 0.0412 (11) | 0.0396 (11) | 0.0351 (10) | 0.0050 (9) | −0.0026 (9) | 0.0026 (8) |
C10 | 0.0394 (11) | 0.0368 (10) | 0.0327 (9) | −0.0013 (9) | 0.0003 (8) | 0.0035 (8) |
C11 | 0.0420 (12) | 0.0413 (11) | 0.0348 (10) | −0.0033 (9) | −0.0035 (9) | 0.0030 (8) |
C12 | 0.0450 (12) | 0.0366 (11) | 0.0336 (9) | −0.0028 (9) | −0.0017 (9) | −0.0003 (8) |
C13 | 0.0480 (14) | 0.0573 (14) | 0.0406 (11) | 0.0020 (11) | 0.0004 (10) | −0.0001 (10) |
C14 | 0.0569 (15) | 0.0469 (13) | 0.0491 (12) | 0.0064 (11) | −0.0008 (11) | −0.0037 (10) |
C15 | 0.0767 (19) | 0.0723 (18) | 0.0634 (16) | 0.0013 (16) | 0.0074 (14) | −0.0204 (15) |
C16 | 0.114 (3) | 0.0599 (17) | 0.0547 (15) | −0.0283 (17) | 0.0223 (16) | −0.0133 (13) |
C17 | 0.121 (3) | 0.075 (2) | 0.0403 (13) | 0.0251 (19) | −0.0113 (16) | −0.0136 (13) |
C18 | 0.0483 (13) | 0.0414 (11) | 0.0311 (9) | −0.0035 (10) | −0.0034 (9) | 0.0005 (9) |
C19 | 0.0500 (13) | 0.0498 (13) | 0.0357 (10) | −0.0089 (11) | −0.0074 (10) | 0.0028 (9) |
C20 | 0.0567 (15) | 0.0481 (13) | 0.0319 (10) | −0.0025 (11) | −0.0041 (10) | 0.0023 (9) |
C21 | 0.0567 (15) | 0.0495 (13) | 0.0386 (11) | 0.0023 (11) | −0.0093 (10) | −0.0012 (10) |
C22 | 0.0466 (14) | 0.0635 (15) | 0.0371 (10) | 0.0009 (11) | −0.0088 (10) | −0.0039 (10) |
C23 | 0.0532 (17) | 0.101 (2) | 0.0531 (14) | 0.0014 (16) | −0.0042 (13) | 0.0038 (15) |
C24 | 0.0574 (18) | 0.121 (3) | 0.0660 (17) | 0.0263 (19) | −0.0088 (15) | −0.0056 (19) |
C25 | 0.076 (2) | 0.084 (2) | 0.0776 (19) | 0.0295 (18) | −0.0236 (17) | −0.0081 (17) |
C26 | 0.077 (2) | 0.0542 (15) | 0.0610 (15) | 0.0083 (14) | −0.0172 (15) | 0.0064 (13) |
C27 | 0.0474 (12) | 0.0361 (10) | 0.0342 (10) | 0.0048 (9) | 0.0024 (9) | 0.0014 (8) |
C28 | 0.0452 (13) | 0.0392 (11) | 0.0459 (11) | 0.0036 (10) | −0.0009 (10) | 0.0013 (10) |
C29 | 0.0522 (14) | 0.0528 (14) | 0.0494 (13) | 0.0003 (11) | −0.0089 (11) | 0.0015 (11) |
C30 | 0.0813 (19) | 0.0471 (14) | 0.0558 (14) | −0.0145 (13) | −0.0054 (14) | −0.0070 (11) |
C31 | 0.109 (2) | 0.0323 (12) | 0.0621 (15) | −0.0002 (14) | −0.0115 (16) | 0.0003 (11) |
C32 | 0.0758 (17) | 0.0388 (12) | 0.0491 (12) | 0.0119 (12) | −0.0102 (12) | 0.0030 (10) |
C33 | 0.0511 (14) | 0.0466 (13) | 0.0382 (10) | −0.0049 (10) | −0.0031 (10) | 0.0017 (10) |
N1 | 0.0413 (10) | 0.0396 (9) | 0.0345 (8) | 0.0001 (8) | 0.0041 (7) | 0.0040 (7) |
N2 | 0.0653 (13) | 0.0451 (10) | 0.0416 (9) | 0.0050 (10) | −0.0082 (9) | −0.0075 (8) |
N3 | 0.0829 (17) | 0.0497 (13) | 0.0633 (13) | −0.0155 (12) | −0.0078 (12) | −0.0038 (11) |
O1 | 0.0946 (15) | 0.0422 (9) | 0.0838 (12) | 0.0107 (10) | 0.0267 (12) | 0.0173 (9) |
O2 | 0.0499 (10) | 0.0567 (10) | 0.0560 (10) | −0.0011 (8) | 0.0167 (8) | −0.0038 (8) |
O3 | 0.0413 (9) | 0.0605 (10) | 0.0371 (8) | −0.0055 (7) | −0.0031 (6) | 0.0063 (7) |
O4 | 0.0670 (12) | 0.0543 (10) | 0.0590 (10) | −0.0237 (9) | −0.0130 (10) | 0.0045 (9) |
O5 | 0.0707 (12) | 0.0609 (11) | 0.0563 (9) | −0.0074 (10) | 0.0027 (9) | 0.0211 (8) |
C1—O1 | 1.434 (4) | C15—H15B | 0.9700 |
C1—H1A | 0.9600 | C16—C17 | 1.506 (5) |
C1—H1B | 0.9600 | C16—H16A | 0.9700 |
C1—H1C | 0.9600 | C16—H16B | 0.9700 |
C2—O1 | 1.382 (3) | C17—N2 | 1.483 (3) |
C2—C7 | 1.385 (3) | C17—H17A | 0.9700 |
C2—C3 | 1.391 (3) | C17—H17B | 0.9700 |
C3—C4 | 1.388 (3) | C18—N2 | 1.459 (3) |
C3—H3 | 0.9300 | C18—C20 | 1.550 (3) |
C4—C5 | 1.391 (3) | C18—C19 | 1.571 (3) |
C4—H4 | 0.9300 | C19—O4 | 1.405 (3) |
C5—C6 | 1.388 (3) | C19—O3 | 1.440 (2) |
C5—N1 | 1.424 (3) | C19—C22 | 1.511 (3) |
C6—C7 | 1.385 (3) | C20—O5 | 1.215 (3) |
C6—H6 | 0.9300 | C20—C21 | 1.480 (4) |
C7—H7 | 0.9300 | C21—C22 | 1.393 (3) |
C8—O2 | 1.213 (2) | C21—C26 | 1.402 (3) |
C8—N1 | 1.373 (3) | C22—C23 | 1.390 (4) |
C8—C9 | 1.536 (3) | C23—C24 | 1.388 (4) |
C9—C27 | 1.509 (3) | C23—H23 | 0.9300 |
C9—C10 | 1.572 (3) | C24—C25 | 1.385 (5) |
C9—H9 | 0.9800 | C24—H24 | 0.9300 |
C10—N1 | 1.495 (2) | C25—C26 | 1.377 (4) |
C10—C11 | 1.533 (3) | C25—H25 | 0.9300 |
C10—H10 | 0.9800 | C26—H26 | 0.9300 |
C11—O3 | 1.439 (3) | C27—C28 | 1.394 (3) |
C11—C12 | 1.564 (3) | C27—C32 | 1.396 (3) |
C11—H11 | 0.9800 | C28—C29 | 1.384 (3) |
C12—C33 | 1.484 (3) | C28—H28 | 0.9300 |
C12—C13 | 1.541 (3) | C29—C30 | 1.380 (3) |
C12—C18 | 1.581 (3) | C29—H29 | 0.9300 |
C13—C14 | 1.532 (3) | C30—C31 | 1.378 (4) |
C13—H13A | 0.9700 | C30—H30 | 0.9300 |
C13—H13B | 0.9700 | C31—C32 | 1.394 (4) |
C14—N2 | 1.497 (3) | C31—H31 | 0.9300 |
C14—C15 | 1.535 (4) | C32—H32 | 0.9300 |
C14—H14 | 0.9800 | C33—N3 | 1.140 (3) |
C15—C16 | 1.505 (4) | O4—H4A | 0.93 (3) |
C15—H15A | 0.9700 | ||
O1—C1—H1A | 109.5 | C17—C16—H16A | 111.0 |
O1—C1—H1B | 109.5 | C15—C16—H16B | 111.0 |
H1A—C1—H1B | 109.5 | C17—C16—H16B | 111.0 |
O1—C1—H1C | 109.5 | H16A—C16—H16B | 109.0 |
H1A—C1—H1C | 109.5 | N2—C17—C16 | 106.3 (2) |
H1B—C1—H1C | 109.5 | N2—C17—H17A | 110.5 |
O1—C2—C7 | 116.5 (2) | C16—C17—H17A | 110.5 |
O1—C2—C3 | 123.8 (2) | N2—C17—H17B | 110.5 |
C7—C2—C3 | 119.6 (2) | C16—C17—H17B | 110.5 |
C4—C3—C2 | 119.8 (2) | H17A—C17—H17B | 108.7 |
C4—C3—H3 | 120.1 | N2—C18—C20 | 116.61 (16) |
C2—C3—H3 | 120.1 | N2—C18—C19 | 111.12 (18) |
C3—C4—C5 | 120.2 (2) | C20—C18—C19 | 103.89 (18) |
C3—C4—H4 | 119.9 | N2—C18—C12 | 105.82 (17) |
C5—C4—H4 | 119.9 | C20—C18—C12 | 114.56 (17) |
C6—C5—C4 | 119.87 (19) | C19—C18—C12 | 104.23 (15) |
C6—C5—N1 | 120.51 (18) | O4—C19—O3 | 110.96 (17) |
C4—C5—N1 | 119.61 (18) | O4—C19—C22 | 111.93 (19) |
C7—C6—C5 | 119.7 (2) | O3—C19—C22 | 109.98 (19) |
C7—C6—H6 | 120.2 | O4—C19—C18 | 111.07 (19) |
C5—C6—H6 | 120.2 | O3—C19—C18 | 106.35 (17) |
C6—C7—C2 | 120.7 (2) | C22—C19—C18 | 106.31 (18) |
C6—C7—H7 | 119.6 | O5—C20—C21 | 127.6 (2) |
C2—C7—H7 | 119.6 | O5—C20—C18 | 124.5 (2) |
O2—C8—N1 | 132.2 (2) | C21—C20—C18 | 107.93 (19) |
O2—C8—C9 | 135.0 (2) | C22—C21—C26 | 121.1 (2) |
N1—C8—C9 | 92.72 (15) | C22—C21—C20 | 111.0 (2) |
C27—C9—C8 | 112.06 (16) | C26—C21—C20 | 127.8 (2) |
C27—C9—C10 | 117.04 (18) | C23—C22—C21 | 120.4 (2) |
C8—C9—C10 | 85.62 (15) | C23—C22—C19 | 128.9 (2) |
C27—C9—H9 | 113.1 | C21—C22—C19 | 110.6 (2) |
C8—C9—H9 | 113.1 | C24—C23—C22 | 118.1 (3) |
C10—C9—H9 | 113.1 | C24—C23—H23 | 121.0 |
N1—C10—C11 | 113.07 (16) | C22—C23—H23 | 121.0 |
N1—C10—C9 | 86.83 (14) | C25—C24—C23 | 121.4 (3) |
C11—C10—C9 | 118.45 (17) | C25—C24—H24 | 119.3 |
N1—C10—H10 | 112.1 | C23—C24—H24 | 119.3 |
C11—C10—H10 | 112.1 | C26—C25—C24 | 121.2 (3) |
C9—C10—H10 | 112.1 | C26—C25—H25 | 119.4 |
O3—C11—C10 | 110.40 (17) | C24—C25—H25 | 119.4 |
O3—C11—C12 | 104.37 (16) | C25—C26—C21 | 117.7 (3) |
C10—C11—C12 | 117.12 (17) | C25—C26—H26 | 121.1 |
O3—C11—H11 | 108.2 | C21—C26—H26 | 121.1 |
C10—C11—H11 | 108.2 | C28—C27—C32 | 117.9 (2) |
C12—C11—H11 | 108.2 | C28—C27—C9 | 121.37 (18) |
C33—C12—C13 | 111.82 (19) | C32—C27—C9 | 120.69 (19) |
C33—C12—C11 | 111.20 (17) | C29—C28—C27 | 121.8 (2) |
C13—C12—C11 | 114.83 (18) | C29—C28—H28 | 119.1 |
C33—C12—C18 | 113.06 (18) | C27—C28—H28 | 119.1 |
C13—C12—C18 | 103.73 (16) | C30—C29—C28 | 119.4 (2) |
C11—C12—C18 | 101.59 (16) | C30—C29—H29 | 120.3 |
C14—C13—C12 | 103.85 (19) | C28—C29—H29 | 120.3 |
C14—C13—H13A | 111.0 | C31—C30—C29 | 120.3 (2) |
C12—C13—H13A | 111.0 | C31—C30—H30 | 119.9 |
C14—C13—H13B | 111.0 | C29—C30—H30 | 119.9 |
C12—C13—H13B | 111.0 | C30—C31—C32 | 120.3 (2) |
H13A—C13—H13B | 109.0 | C30—C31—H31 | 119.9 |
N2—C14—C13 | 104.49 (18) | C32—C31—H31 | 119.9 |
N2—C14—C15 | 105.2 (2) | C31—C32—C27 | 120.4 (2) |
C13—C14—C15 | 116.4 (2) | C31—C32—H32 | 119.8 |
N2—C14—H14 | 110.1 | C27—C32—H32 | 119.8 |
C13—C14—H14 | 110.1 | N3—C33—C12 | 177.5 (3) |
C15—C14—H14 | 110.1 | C8—N1—C5 | 131.91 (16) |
C16—C15—C14 | 104.3 (2) | C8—N1—C10 | 94.77 (16) |
C16—C15—H15A | 110.9 | C5—N1—C10 | 132.56 (16) |
C14—C15—H15A | 110.9 | C18—N2—C17 | 123.04 (19) |
C16—C15—H15B | 110.9 | C18—N2—C14 | 110.58 (16) |
C14—C15—H15B | 110.9 | C17—N2—C14 | 108.1 (2) |
H15A—C15—H15B | 108.9 | C2—O1—C1 | 116.7 (2) |
C15—C16—C17 | 103.8 (2) | C11—O3—C19 | 107.76 (16) |
C15—C16—H16A | 111.0 | C19—O4—H4A | 98 (2) |
O1—C2—C3—C4 | 179.2 (2) | O5—C20—C21—C26 | −5.0 (4) |
C7—C2—C3—C4 | −0.2 (4) | C18—C20—C21—C26 | 176.2 (2) |
C2—C3—C4—C5 | 0.2 (4) | C26—C21—C22—C23 | 0.7 (4) |
C3—C4—C5—C6 | 0.4 (3) | C20—C21—C22—C23 | −178.5 (2) |
C3—C4—C5—N1 | 179.5 (2) | C26—C21—C22—C19 | −178.0 (2) |
C4—C5—C6—C7 | −1.1 (3) | C20—C21—C22—C19 | 2.8 (3) |
N1—C5—C6—C7 | 179.9 (2) | O4—C19—C22—C23 | −56.9 (3) |
C5—C6—C7—C2 | 1.1 (4) | O3—C19—C22—C23 | 66.9 (3) |
O1—C2—C7—C6 | −179.8 (2) | C18—C19—C22—C23 | −178.4 (2) |
C3—C2—C7—C6 | −0.5 (4) | O4—C19—C22—C21 | 121.6 (2) |
O2—C8—C9—C27 | −60.9 (3) | O3—C19—C22—C21 | −114.6 (2) |
N1—C8—C9—C27 | 115.56 (18) | C18—C19—C22—C21 | 0.2 (2) |
O2—C8—C9—C10 | −178.4 (3) | C21—C22—C23—C24 | −0.7 (4) |
N1—C8—C9—C10 | −1.89 (15) | C19—C22—C23—C24 | 177.7 (2) |
C27—C9—C10—N1 | −110.83 (17) | C22—C23—C24—C25 | 0.2 (4) |
C8—C9—C10—N1 | 1.73 (14) | C23—C24—C25—C26 | 0.4 (5) |
C27—C9—C10—C11 | 134.57 (19) | C24—C25—C26—C21 | −0.4 (4) |
C8—C9—C10—C11 | −112.87 (18) | C22—C21—C26—C25 | −0.2 (4) |
N1—C10—C11—O3 | −68.3 (2) | C20—C21—C26—C25 | 178.9 (2) |
C9—C10—C11—O3 | 31.1 (2) | C8—C9—C27—C28 | −46.0 (3) |
N1—C10—C11—C12 | 172.52 (17) | C10—C9—C27—C28 | 50.6 (3) |
C9—C10—C11—C12 | −88.1 (2) | C8—C9—C27—C32 | 132.5 (2) |
O3—C11—C12—C33 | −85.7 (2) | C10—C9—C27—C32 | −130.9 (2) |
C10—C11—C12—C33 | 36.7 (3) | C32—C27—C28—C29 | 0.6 (3) |
O3—C11—C12—C13 | 146.07 (18) | C9—C27—C28—C29 | 179.1 (2) |
C10—C11—C12—C13 | −91.5 (2) | C27—C28—C29—C30 | −0.1 (4) |
O3—C11—C12—C18 | 34.9 (2) | C28—C29—C30—C31 | 0.1 (4) |
C10—C11—C12—C18 | 157.24 (18) | C29—C30—C31—C32 | −0.6 (4) |
C33—C12—C13—C14 | 154.06 (18) | C30—C31—C32—C27 | 1.1 (4) |
C11—C12—C13—C14 | −78.0 (2) | C28—C27—C32—C31 | −1.1 (4) |
C18—C12—C13—C14 | 31.9 (2) | C9—C27—C32—C31 | −179.6 (2) |
C12—C13—C14—N2 | −33.1 (2) | O2—C8—N1—C5 | 7.9 (4) |
C12—C13—C14—C15 | −148.5 (2) | C9—C8—N1—C5 | −168.7 (2) |
N2—C14—C15—C16 | −26.4 (3) | O2—C8—N1—C10 | 178.6 (2) |
C13—C14—C15—C16 | 88.7 (3) | C9—C8—N1—C10 | 1.98 (16) |
C14—C15—C16—C17 | 35.1 (3) | C6—C5—N1—C8 | 153.4 (2) |
C15—C16—C17—N2 | −31.0 (3) | C4—C5—N1—C8 | −25.6 (3) |
C33—C12—C18—N2 | −140.51 (18) | C6—C5—N1—C10 | −14.0 (3) |
C13—C12—C18—N2 | −19.2 (2) | C4—C5—N1—C10 | 167.0 (2) |
C11—C12—C18—N2 | 100.25 (19) | C11—C10—N1—C8 | 117.73 (19) |
C33—C12—C18—C20 | −10.6 (3) | C9—C10—N1—C8 | −1.94 (15) |
C13—C12—C18—C20 | 110.7 (2) | C11—C10—N1—C5 | −71.6 (3) |
C11—C12—C18—C20 | −129.86 (18) | C9—C10—N1—C5 | 168.7 (2) |
C33—C12—C18—C19 | 102.2 (2) | C20—C18—N2—C17 | −0.3 (3) |
C13—C12—C18—C19 | −136.46 (18) | C19—C18—N2—C17 | −119.0 (3) |
C11—C12—C18—C19 | −17.0 (2) | C12—C18—N2—C17 | 128.4 (2) |
N2—C18—C19—O4 | 1.3 (2) | C20—C18—N2—C14 | −130.1 (2) |
C20—C18—C19—O4 | −124.83 (18) | C19—C18—N2—C14 | 111.1 (2) |
C12—C18—C19—O4 | 114.88 (18) | C12—C18—N2—C14 | −1.5 (2) |
N2—C18—C19—O3 | −119.50 (18) | C16—C17—N2—C18 | −116.3 (3) |
C20—C18—C19—O3 | 114.33 (18) | C16—C17—N2—C14 | 14.6 (3) |
C12—C18—C19—O3 | −6.0 (2) | C13—C14—N2—C18 | 21.7 (2) |
N2—C18—C19—C22 | 123.32 (19) | C15—C14—N2—C18 | 144.8 (2) |
C20—C18—C19—C22 | −2.8 (2) | C13—C14—N2—C17 | −115.7 (2) |
C12—C18—C19—C22 | −123.13 (17) | C15—C14—N2—C17 | 7.4 (3) |
N2—C18—C20—O5 | 63.0 (3) | C7—C2—O1—C1 | −174.6 (3) |
C19—C18—C20—O5 | −174.4 (2) | C3—C2—O1—C1 | 6.1 (4) |
C12—C18—C20—O5 | −61.4 (3) | C10—C11—O3—C19 | −167.85 (16) |
N2—C18—C20—C21 | −118.1 (2) | C12—C11—O3—C19 | −41.2 (2) |
C19—C18—C20—C21 | 4.5 (2) | O4—C19—O3—C11 | −91.4 (2) |
C12—C18—C20—C21 | 117.51 (19) | C22—C19—O3—C11 | 144.18 (19) |
O5—C20—C21—C22 | 174.1 (2) | C18—C19—O3—C11 | 29.5 (2) |
C18—C20—C21—C22 | −4.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O2i | 0.98 | 2.43 | 3.337 (3) | 154 |
C13—H13A···O2i | 0.97 | 2.41 | 3.321 (3) | 156 |
C29—H29···O4i | 0.93 | 2.55 | 3.228 (3) | 130 |
O4—H4A···N2 | 0.93 (3) | 1.84 (3) | 2.602 (3) | 137 (3) |
Symmetry code: (i) x−1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C33H29N3O5 |
Mr | 547.59 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 10.2874 (16), 14.138 (3), 18.866 (3) |
V (Å3) | 2743.9 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.973, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14810, 6406, 4551 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.123, 1.00 |
No. of reflections | 6406 |
No. of parameters | 375 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.16 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O2i | 0.98 | 2.43 | 3.337 (3) | 154 |
C13—H13A···O2i | 0.97 | 2.41 | 3.321 (3) | 156 |
C29—H29···O4i | 0.93 | 2.55 | 3.228 (3) | 130 |
O4—H4A···N2 | 0.93 (3) | 1.84 (3) | 2.602 (3) | 137 (3) |
Symmetry code: (i) x−1/2, −y+1/2, −z+1. |
Acknowledgements
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and TS thanks the DST for an Inspire fellowship.
References
Brakhage, A. A. (1998). Microbiol. Mol. Biol. Rev. 62, 547–585. Web of Science CAS PubMed Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sundaramoorthy, S., Rajesh, R., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o2200–o2201. CSD CrossRef CAS 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.
The most commonly used β-lactam antibiotics for the therapy of infectious diseases are penicillin and cephalosporin (Brakhage, 1998). In view of potential applications, the crystal structure determination of the titled β-lactam derivative was carried out that is reported in this artiucle.
In the title compound (Fig. 1), the four membered ring of the β-lactam fragment (N1/C8–C10) is essentially planar (rmsd = 0.0122 Å) with O1 displaced from this ring by 0.856 (9) Å. The mean-planes of the benzene rings C2–C7 and C27–C32 are inclined at dihedral angles 85.10 (7) and 21.56 (14)°, respectively, with respect to the mean-plane of the four membered ring (N1/C8–C10).
The pyrrolidine rings (N1/C14–C17) and (N2/C12–C14/C18) adopt C16- and C13-envelope conformations with C16 and C13 atoms lying 0.535 (4) and 0.519 (4) Å, respectively, out of the planes formed by the remaining ring atoms. The furan ring (O3/C11/C12/C18/C19) also adopts a C11-envelope conformation with C11 atom 0.560 (3) Å out of the plane formed by the remaining ring atoms. The nine membered indene ring (C18–C26) is almost planar (rmsd = 0.0240 Å) with O5 displaced by 0.145 (3)Å from this ring.
The molecular structure of the title compound is stabilized by a strong intramolecular hydrogen bond O4—H4A···N2 (Table 1). The crystal structure is consolidated by intermolecular C—H···O hydrogen bonds (Tab. 1 & Fig. 2).