organic compounds
Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.01,8.02,6.012,17]octadeca-12(17),13,15-triene-8-carboxylate
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, C34H32N2O8, one of the pyrrolidine rings in the pyrrolizidine ring system adopts a twist conformation, whereas the other ring adopts an (C atom as flap). The five-membered ring in the indene ring system and the fused furan ring also adopt envelope conformations (C and O atoms as flaps, respectively). The β-lactam ring makes dihedral angles of 23.41 (2) and 25.98 (2)°, respectively, with the attached methoxyphenyl and phenoxy rings. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, generating an S(5) motif. In the crystal, molecules are linked into C(12) chains running along the a axis by C—H⋯O hydrogen bonds. The structure is further consolidated by weak intermolecular C—H⋯π and π–π interactions [centroid–centroid distance = 3.7987 (14) Å].
Related literature
For general background to β-lactams, see: Banik & Becker (2000); Brakhage (1998). For a related structure, see: Arun et al. (2003). For hydrogen-bond motifs, see: Bernstein et al. (1995).
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
https://doi.org/10.1107/S1600536812027341/pv2560sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027341/pv2560Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812027341/pv2560Isup3.cml
To a reaction mixture of 2-(hydroxy(1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin -2-yl)methyl)acrylate (1 mmol), ninhydrine (1.1 mmol) and proline (1.1 mmol) were refluxed in methanol 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 and washed with water followed by brine solution. The organic layer was separated and dried over sodium sulfate. Filtering and evaporation of the organic solvent under reduced pressure were carried out. The product was separated by
using hexane and ethyl acetate (3: 7) as an to give colorless solid. The product was dissolved in chloroform and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent resulting in single crystals of the title compound suitable for XRD studies.The H atoms were positioned geometrically with O—H = 0.82 Å and C—H = 0.93, 0.96, 0.97 and 0.98 Å for aryl, methyl, methylene and methyne H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.5Ueq(methyl C/O) or 1.2Ueq(non-methyl C).
The role of β-lactam antibiotics is well known (Banik & Becker, 2000). 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 determination of the title β-lactam derivative was carried out which is reported in this article.
In the title compound (Fig. 1), the β-lactam ring makes dihedral angle of 31.36 (1)° with the indene ring system. The maximum deviation of indene ring system is 0.212 (2) Å for atom C19. The β-lactam ring makes dihedral angles 23.41 (15) and 25.98 (15)°, respectively, with the attached methoxyphenyl and phenoxy rings. The carboxylate group adopts an extended conformation with thetorsion angle C18—C33—O8—C34 = 171.9 (2)°. The five-membered ring (C19/C20/C21/C26/C27) in the inden ring system and the fused furan ring (O4/C17—C20) adopt envelope conformations, with C19 and O4 atoms deviating by 0.135 (2) and -0.221 (2) Å, respectively, from the planes formed by the remaining atoms of the rings. In the pyrrolizidine ring system, the pyrrolidine ring (C18/C19/N2/C31/C32) adopts a C31-envelope conformation, with C31 deviating by 0.216 (2) Å from the remaining ring atoms. The bond lengths and bond angles in the title compound agree with the corresponding bond lengths and angles reported for a closely related compound (Arun et al., (2003).
The molecular structure of the title compound is stabilized by a strong O5—H5A···N2 hydrogen bond, generating an S(5) motif (Bernstein et al., 1995). The H-atom bonded to C15 is involved in hydrogen bonding with atom O6 forming a C(12) chain running along the a axis (Tab. 1 & Fig. 2). A weak intermolecular C—H···π interaction involving the C12—H12 group and the C1—C16 phenoxy ring is also observed.
For general background to β-lactams, see: Banik & Becker (2000); Brakhage (1998). For a related structure, see: Arun et al. (2003). For hydrogen-bond motifs, see: Bernstein et al. (1995).
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).C34H32N2O8 | F(000) = 1256 |
Mr = 596.62 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1035 reflections |
a = 11.4251 (13) Å | θ = 1.3–28.3° |
b = 7.8362 (8) Å | µ = 0.10 mm−1 |
c = 32.041 (4) Å | T = 293 K |
β = 91.313 (8)° | Block, colourless |
V = 2867.9 (6) Å3 | 0.25 × 0.22 × 0.2 mm |
Z = 4 |
Bruker SMART APEXII area-detector diffractometer | 7104 independent reflections |
Radiation source: fine-focus sealed tube | 3251 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
ω and φ scans | θmax = 28.3°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −15→15 |
Tmin = 0.976, Tmax = 0.980 | k = −10→10 |
27667 measured reflections | l = −42→42 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0537P)2] where P = (Fo2 + 2Fc2)/3 |
7104 reflections | (Δ/σ)max < 0.001 |
400 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C34H32N2O8 | V = 2867.9 (6) Å3 |
Mr = 596.62 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.4251 (13) Å | µ = 0.10 mm−1 |
b = 7.8362 (8) Å | T = 293 K |
c = 32.041 (4) Å | 0.25 × 0.22 × 0.2 mm |
β = 91.313 (8)° |
Bruker SMART APEXII area-detector diffractometer | 7104 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 3251 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.980 | Rint = 0.083 |
27667 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.26 e Å−3 |
7104 reflections | Δρmin = −0.20 e Å−3 |
400 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 | 0.5692 (2) | 0.7918 (3) | 0.02316 (7) | 0.0411 (6) | |
C2 | 0.4969 (2) | 0.7168 (3) | −0.00647 (7) | 0.0494 (6) | |
H2 | 0.4337 | 0.6513 | 0.0018 | 0.059* | |
C3 | 0.5175 (2) | 0.7380 (3) | −0.04839 (8) | 0.0523 (7) | |
H3 | 0.4682 | 0.6878 | −0.0683 | 0.063* | |
C4 | 0.6120 (2) | 0.8343 (3) | −0.06043 (7) | 0.0484 (6) | |
C5 | 0.6846 (2) | 0.9091 (3) | −0.03100 (7) | 0.0513 (7) | |
H5 | 0.7482 | 0.9738 | −0.0394 | 0.062* | |
C6 | 0.6638 (2) | 0.8886 (3) | 0.01066 (7) | 0.0469 (6) | |
H6 | 0.7130 | 0.9396 | 0.0305 | 0.056* | |
C7 | 0.5862 (3) | 0.7665 (4) | −0.13225 (9) | 0.0926 (11) | |
H7A | 0.5981 | 0.6474 | −0.1266 | 0.139* | |
H7B | 0.6184 | 0.7943 | −0.1588 | 0.139* | |
H7C | 0.5038 | 0.7911 | −0.1328 | 0.139* | |
C8 | 0.6332 (2) | 0.7868 (3) | 0.10200 (7) | 0.0416 (6) | |
H8 | 0.6557 | 0.9058 | 0.1071 | 0.050* | |
C9 | 0.53063 (19) | 0.7311 (3) | 0.12942 (7) | 0.0420 (6) | |
H9 | 0.5417 | 0.6144 | 0.1397 | 0.050* | |
C10 | 0.4546 (2) | 0.7338 (3) | 0.08915 (8) | 0.0478 (6) | |
C11 | 0.4395 (2) | 0.7776 (3) | 0.19371 (7) | 0.0412 (6) | |
C12 | 0.4698 (2) | 0.8218 (3) | 0.23396 (8) | 0.0511 (6) | |
H12 | 0.5336 | 0.8928 | 0.2394 | 0.061* | |
C13 | 0.4048 (2) | 0.7598 (3) | 0.26613 (8) | 0.0564 (7) | |
H13 | 0.4247 | 0.7892 | 0.2935 | 0.068* | |
C14 | 0.3106 (2) | 0.6547 (3) | 0.25828 (8) | 0.0563 (7) | |
H14 | 0.2671 | 0.6127 | 0.2802 | 0.068* | |
C15 | 0.2813 (2) | 0.6123 (3) | 0.21807 (8) | 0.0542 (7) | |
H15 | 0.2174 | 0.5412 | 0.2127 | 0.065* | |
C16 | 0.3446 (2) | 0.6730 (3) | 0.18552 (7) | 0.0478 (6) | |
H16 | 0.3239 | 0.6441 | 0.1582 | 0.057* | |
C17 | 0.73901 (19) | 0.6701 (3) | 0.10020 (7) | 0.0381 (5) | |
H17 | 0.7718 | 0.6788 | 0.0723 | 0.046* | |
C18 | 0.83833 (19) | 0.7027 (3) | 0.13279 (6) | 0.0355 (5) | |
C19 | 0.88557 (19) | 0.5159 (3) | 0.14320 (6) | 0.0376 (5) | |
C20 | 0.8029 (2) | 0.3992 (3) | 0.11556 (7) | 0.0403 (6) | |
C21 | 0.8728 (2) | 0.3585 (3) | 0.07798 (7) | 0.0412 (6) | |
C22 | 0.8357 (2) | 0.2882 (3) | 0.04033 (8) | 0.0530 (7) | |
H22 | 0.7571 | 0.2629 | 0.0352 | 0.064* | |
C23 | 0.9177 (3) | 0.2571 (3) | 0.01084 (8) | 0.0632 (8) | |
H23 | 0.8940 | 0.2103 | −0.0147 | 0.076* | |
C24 | 1.0348 (3) | 0.2935 (4) | 0.01796 (8) | 0.0647 (8) | |
H24 | 1.0885 | 0.2691 | −0.0026 | 0.078* | |
C25 | 1.0732 (2) | 0.3655 (3) | 0.05511 (8) | 0.0552 (7) | |
H25 | 1.1518 | 0.3913 | 0.0600 | 0.066* | |
C26 | 0.9898 (2) | 0.3977 (3) | 0.08485 (7) | 0.0428 (6) | |
C27 | 1.0082 (2) | 0.4737 (3) | 0.12642 (7) | 0.0446 (6) | |
C28 | 0.9643 (2) | 0.5013 (4) | 0.21783 (7) | 0.0655 (8) | |
H28A | 1.0137 | 0.4006 | 0.2184 | 0.079* | |
H28B | 1.0118 | 0.6001 | 0.2114 | 0.079* | |
C29 | 0.9052 (3) | 0.5235 (4) | 0.25785 (8) | 0.0727 (9) | |
H29A | 0.9546 | 0.5866 | 0.2774 | 0.087* | |
H29B | 0.8869 | 0.4135 | 0.2700 | 0.087* | |
C30 | 0.7948 (2) | 0.6211 (4) | 0.24787 (7) | 0.0576 (7) | |
H30A | 0.8036 | 0.7400 | 0.2558 | 0.069* | |
H30B | 0.7293 | 0.5730 | 0.2626 | 0.069* | |
C31 | 0.7756 (2) | 0.6046 (3) | 0.20060 (6) | 0.0432 (6) | |
H31 | 0.6970 | 0.5608 | 0.1941 | 0.052* | |
C32 | 0.7991 (2) | 0.7655 (3) | 0.17556 (6) | 0.0424 (6) | |
H32A | 0.8600 | 0.8335 | 0.1891 | 0.051* | |
H32B | 0.7287 | 0.8341 | 0.1727 | 0.051* | |
C33 | 0.9311 (2) | 0.8179 (3) | 0.11405 (7) | 0.0413 (6) | |
C34 | 1.1133 (2) | 0.9561 (4) | 0.12607 (8) | 0.0693 (8) | |
H34A | 1.1559 | 0.8824 | 0.1079 | 0.104* | |
H34B | 1.1632 | 0.9908 | 0.1490 | 0.104* | |
H34C | 1.0873 | 1.0551 | 0.1108 | 0.104* | |
N1 | 0.55049 (16) | 0.7704 (3) | 0.06619 (6) | 0.0451 (5) | |
N2 | 0.86574 (17) | 0.4818 (2) | 0.18691 (5) | 0.0433 (5) | |
O1 | 0.64164 (18) | 0.8632 (2) | −0.10114 (5) | 0.0725 (6) | |
O2 | 0.35322 (16) | 0.7067 (2) | 0.07968 (5) | 0.0623 (5) | |
O3 | 0.50681 (14) | 0.8443 (2) | 0.16232 (5) | 0.0511 (4) | |
O4 | 0.70046 (13) | 0.49763 (19) | 0.10630 (4) | 0.0429 (4) | |
O5 | 0.76948 (16) | 0.2530 (2) | 0.13645 (5) | 0.0549 (5) | |
H5A | 0.7789 | 0.2671 | 0.1617 | 0.082* | |
O6 | 1.10093 (16) | 0.4957 (3) | 0.14436 (5) | 0.0694 (6) | |
O7 | 0.93303 (17) | 0.8573 (3) | 0.07831 (5) | 0.0721 (6) | |
O8 | 1.01251 (15) | 0.8656 (2) | 0.14184 (5) | 0.0608 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0358 (14) | 0.0458 (14) | 0.0416 (14) | 0.0071 (11) | −0.0018 (11) | 0.0055 (11) |
C2 | 0.0393 (15) | 0.0575 (16) | 0.0512 (15) | −0.0035 (12) | −0.0038 (12) | 0.0050 (12) |
C3 | 0.0522 (18) | 0.0579 (17) | 0.0462 (15) | −0.0057 (13) | −0.0102 (13) | −0.0054 (12) |
C4 | 0.0559 (18) | 0.0500 (15) | 0.0392 (14) | 0.0028 (13) | 0.0005 (12) | 0.0003 (11) |
C5 | 0.0516 (17) | 0.0559 (16) | 0.0464 (15) | −0.0085 (13) | 0.0000 (13) | 0.0057 (12) |
C6 | 0.0455 (16) | 0.0530 (16) | 0.0419 (14) | −0.0050 (12) | −0.0043 (12) | 0.0017 (12) |
C7 | 0.129 (3) | 0.099 (3) | 0.0503 (18) | −0.027 (2) | −0.0015 (19) | −0.0174 (17) |
C8 | 0.0378 (14) | 0.0492 (15) | 0.0378 (12) | 0.0021 (11) | 0.0012 (11) | 0.0019 (11) |
C9 | 0.0383 (15) | 0.0469 (14) | 0.0410 (13) | 0.0012 (11) | 0.0075 (11) | 0.0005 (11) |
C10 | 0.0393 (17) | 0.0534 (16) | 0.0508 (15) | 0.0046 (12) | 0.0038 (13) | 0.0019 (12) |
C11 | 0.0358 (15) | 0.0427 (14) | 0.0455 (14) | 0.0051 (11) | 0.0087 (11) | 0.0009 (11) |
C12 | 0.0457 (16) | 0.0552 (16) | 0.0524 (16) | −0.0035 (12) | −0.0003 (13) | −0.0113 (13) |
C13 | 0.065 (2) | 0.0616 (18) | 0.0421 (15) | 0.0095 (15) | −0.0004 (14) | −0.0056 (13) |
C14 | 0.0593 (19) | 0.0568 (17) | 0.0535 (17) | 0.0075 (14) | 0.0157 (14) | 0.0056 (13) |
C15 | 0.0406 (16) | 0.0626 (18) | 0.0599 (17) | −0.0058 (13) | 0.0073 (13) | −0.0004 (14) |
C16 | 0.0370 (15) | 0.0630 (16) | 0.0434 (14) | 0.0010 (12) | −0.0007 (12) | −0.0036 (12) |
C17 | 0.0344 (14) | 0.0468 (14) | 0.0331 (12) | 0.0000 (11) | 0.0019 (10) | −0.0011 (10) |
C18 | 0.0333 (13) | 0.0406 (13) | 0.0327 (11) | −0.0010 (10) | 0.0012 (10) | −0.0024 (10) |
C19 | 0.0360 (14) | 0.0441 (14) | 0.0327 (12) | 0.0005 (10) | 0.0012 (10) | −0.0017 (10) |
C20 | 0.0357 (14) | 0.0424 (14) | 0.0428 (13) | −0.0022 (11) | −0.0003 (11) | −0.0013 (11) |
C21 | 0.0464 (16) | 0.0374 (13) | 0.0399 (13) | 0.0038 (11) | 0.0027 (11) | −0.0030 (10) |
C22 | 0.0586 (18) | 0.0508 (16) | 0.0494 (15) | 0.0017 (13) | −0.0016 (14) | −0.0113 (12) |
C23 | 0.072 (2) | 0.070 (2) | 0.0471 (16) | 0.0051 (16) | −0.0005 (15) | −0.0192 (13) |
C24 | 0.069 (2) | 0.078 (2) | 0.0472 (16) | 0.0126 (16) | 0.0133 (15) | −0.0088 (14) |
C25 | 0.0470 (17) | 0.0676 (18) | 0.0515 (16) | 0.0088 (13) | 0.0082 (13) | −0.0012 (13) |
C26 | 0.0430 (16) | 0.0470 (15) | 0.0385 (13) | 0.0078 (11) | 0.0036 (11) | −0.0010 (11) |
C27 | 0.0363 (15) | 0.0523 (15) | 0.0451 (14) | 0.0018 (11) | −0.0019 (12) | −0.0011 (11) |
C28 | 0.0622 (19) | 0.092 (2) | 0.0416 (15) | 0.0089 (16) | −0.0119 (13) | 0.0089 (15) |
C29 | 0.096 (3) | 0.078 (2) | 0.0435 (16) | −0.0044 (18) | −0.0176 (15) | −0.0007 (14) |
C30 | 0.063 (2) | 0.0757 (19) | 0.0339 (13) | −0.0116 (15) | 0.0076 (12) | −0.0020 (13) |
C31 | 0.0398 (15) | 0.0565 (15) | 0.0334 (12) | −0.0062 (12) | 0.0045 (11) | −0.0040 (11) |
C32 | 0.0431 (15) | 0.0503 (15) | 0.0340 (12) | −0.0014 (11) | 0.0034 (10) | −0.0055 (10) |
C33 | 0.0427 (15) | 0.0446 (14) | 0.0364 (13) | −0.0013 (11) | 0.0007 (11) | −0.0020 (11) |
C34 | 0.0558 (19) | 0.088 (2) | 0.0643 (18) | −0.0359 (16) | 0.0021 (14) | 0.0101 (16) |
N1 | 0.0325 (12) | 0.0625 (14) | 0.0403 (11) | 0.0034 (9) | −0.0006 (9) | 0.0083 (9) |
N2 | 0.0451 (13) | 0.0527 (12) | 0.0320 (10) | 0.0002 (10) | −0.0013 (9) | 0.0025 (9) |
O1 | 0.0945 (16) | 0.0825 (14) | 0.0404 (10) | −0.0238 (11) | 0.0005 (10) | −0.0019 (9) |
O2 | 0.0365 (12) | 0.0868 (14) | 0.0636 (12) | −0.0041 (10) | 0.0012 (9) | 0.0034 (10) |
O3 | 0.0526 (11) | 0.0489 (10) | 0.0525 (10) | −0.0027 (8) | 0.0174 (9) | −0.0059 (8) |
O4 | 0.0334 (9) | 0.0449 (10) | 0.0502 (9) | −0.0012 (7) | −0.0027 (7) | −0.0069 (8) |
O5 | 0.0636 (12) | 0.0470 (11) | 0.0543 (10) | −0.0104 (9) | 0.0041 (10) | 0.0032 (8) |
O6 | 0.0409 (12) | 0.1050 (16) | 0.0618 (12) | 0.0020 (11) | −0.0062 (9) | −0.0172 (11) |
O7 | 0.0787 (15) | 0.0973 (15) | 0.0402 (11) | −0.0351 (11) | −0.0028 (9) | 0.0131 (10) |
O8 | 0.0526 (12) | 0.0825 (13) | 0.0471 (10) | −0.0282 (10) | −0.0061 (9) | 0.0101 (9) |
C1—C2 | 1.376 (3) | C18—C19 | 1.593 (3) |
C1—C6 | 1.387 (3) | C19—N2 | 1.449 (3) |
C1—N1 | 1.410 (3) | C19—C27 | 1.547 (3) |
C2—C3 | 1.379 (3) | C19—C20 | 1.572 (3) |
C2—H2 | 0.9300 | C20—O5 | 1.385 (3) |
C3—C4 | 1.379 (3) | C20—O4 | 1.427 (3) |
C3—H3 | 0.9300 | C20—C21 | 1.495 (3) |
C4—C5 | 1.373 (3) | C21—C26 | 1.384 (3) |
C4—O1 | 1.374 (3) | C21—C22 | 1.384 (3) |
C5—C6 | 1.371 (3) | C22—C23 | 1.368 (3) |
C5—H5 | 0.9300 | C22—H22 | 0.9300 |
C6—H6 | 0.9300 | C23—C24 | 1.381 (4) |
C7—O1 | 1.393 (3) | C23—H23 | 0.9300 |
C7—H7A | 0.9600 | C24—C25 | 1.380 (3) |
C7—H7B | 0.9600 | C24—H24 | 0.9300 |
C7—H7C | 0.9600 | C25—C26 | 1.386 (3) |
C8—N1 | 1.475 (3) | C25—H25 | 0.9300 |
C8—C17 | 1.518 (3) | C26—C27 | 1.469 (3) |
C8—C9 | 1.543 (3) | C27—O6 | 1.206 (3) |
C8—H8 | 0.9800 | C28—C29 | 1.474 (4) |
C9—O3 | 1.409 (3) | C28—N2 | 1.491 (3) |
C9—C10 | 1.539 (3) | C28—H28A | 0.9700 |
C9—H9 | 0.9800 | C28—H28B | 0.9700 |
C10—O2 | 1.209 (3) | C29—C30 | 1.503 (4) |
C10—N1 | 1.364 (3) | C29—H29A | 0.9700 |
C11—C12 | 1.372 (3) | C29—H29B | 0.9700 |
C11—C16 | 1.379 (3) | C30—C31 | 1.531 (3) |
C11—O3 | 1.383 (3) | C30—H30A | 0.9700 |
C12—C13 | 1.373 (3) | C30—H30B | 0.9700 |
C12—H12 | 0.9300 | C31—N2 | 1.483 (3) |
C13—C14 | 1.374 (3) | C31—C32 | 1.521 (3) |
C13—H13 | 0.9300 | C31—H31 | 0.9800 |
C14—C15 | 1.365 (3) | C32—H32A | 0.9700 |
C14—H14 | 0.9300 | C32—H32B | 0.9700 |
C15—C16 | 1.368 (3) | C33—O7 | 1.186 (2) |
C15—H15 | 0.9300 | C33—O8 | 1.327 (3) |
C16—H16 | 0.9300 | C34—O8 | 1.453 (3) |
C17—O4 | 1.436 (3) | C34—H34A | 0.9600 |
C17—C18 | 1.546 (3) | C34—H34B | 0.9600 |
C17—H17 | 0.9800 | C34—H34C | 0.9600 |
C18—C33 | 1.526 (3) | O5—H5A | 0.8200 |
C18—C32 | 1.533 (3) | ||
C2—C1—C6 | 119.6 (2) | O5—C20—C21 | 111.76 (19) |
C2—C1—N1 | 121.4 (2) | O4—C20—C21 | 113.51 (18) |
C6—C1—N1 | 119.0 (2) | O5—C20—C19 | 112.18 (17) |
C1—C2—C3 | 120.5 (2) | O4—C20—C19 | 106.39 (17) |
C1—C2—H2 | 119.8 | C21—C20—C19 | 104.65 (18) |
C3—C2—H2 | 119.8 | C26—C21—C22 | 120.2 (2) |
C2—C3—C4 | 119.4 (2) | C26—C21—C20 | 110.86 (19) |
C2—C3—H3 | 120.3 | C22—C21—C20 | 128.9 (2) |
C4—C3—H3 | 120.3 | C23—C22—C21 | 118.2 (3) |
C5—C4—O1 | 115.1 (2) | C23—C22—H22 | 120.9 |
C5—C4—C3 | 120.4 (2) | C21—C22—H22 | 120.9 |
O1—C4—C3 | 124.6 (2) | C22—C23—C24 | 121.7 (2) |
C6—C5—C4 | 120.2 (2) | C22—C23—H23 | 119.2 |
C6—C5—H5 | 119.9 | C24—C23—H23 | 119.2 |
C4—C5—H5 | 119.9 | C25—C24—C23 | 121.0 (3) |
C5—C6—C1 | 120.0 (2) | C25—C24—H24 | 119.5 |
C5—C6—H6 | 120.0 | C23—C24—H24 | 119.5 |
C1—C6—H6 | 120.0 | C24—C25—C26 | 117.2 (3) |
O1—C7—H7A | 109.5 | C24—C25—H25 | 121.4 |
O1—C7—H7B | 109.5 | C26—C25—H25 | 121.4 |
H7A—C7—H7B | 109.5 | C21—C26—C25 | 121.8 (2) |
O1—C7—H7C | 109.5 | C21—C26—C27 | 110.6 (2) |
H7A—C7—H7C | 109.5 | C25—C26—C27 | 127.6 (2) |
H7B—C7—H7C | 109.5 | O6—C27—C26 | 126.5 (2) |
N1—C8—C17 | 114.50 (18) | O6—C27—C19 | 126.6 (2) |
N1—C8—C9 | 86.40 (17) | C26—C27—C19 | 106.85 (19) |
C17—C8—C9 | 117.85 (19) | C29—C28—N2 | 103.6 (2) |
N1—C8—H8 | 111.9 | C29—C28—H28A | 111.0 |
C17—C8—H8 | 111.9 | N2—C28—H28A | 111.0 |
C9—C8—H8 | 111.9 | C29—C28—H28B | 111.0 |
O3—C9—C10 | 120.2 (2) | N2—C28—H28B | 111.0 |
O3—C9—C8 | 114.22 (19) | H28A—C28—H28B | 109.0 |
C10—C9—C8 | 86.58 (17) | C28—C29—C30 | 105.9 (2) |
O3—C9—H9 | 111.2 | C28—C29—H29A | 110.6 |
C10—C9—H9 | 111.2 | C30—C29—H29A | 110.6 |
C8—C9—H9 | 111.2 | C28—C29—H29B | 110.6 |
O2—C10—N1 | 132.7 (2) | C30—C29—H29B | 110.6 |
O2—C10—C9 | 136.7 (2) | H29A—C29—H29B | 108.7 |
N1—C10—C9 | 90.6 (2) | C29—C30—C31 | 105.5 (2) |
C12—C11—C16 | 120.6 (2) | C29—C30—H30A | 110.6 |
C12—C11—O3 | 117.1 (2) | C31—C30—H30A | 110.6 |
C16—C11—O3 | 122.3 (2) | C29—C30—H30B | 110.6 |
C11—C12—C13 | 119.1 (2) | C31—C30—H30B | 110.6 |
C11—C12—H12 | 120.4 | H30A—C30—H30B | 108.8 |
C13—C12—H12 | 120.4 | N2—C31—C32 | 104.47 (18) |
C12—C13—C14 | 120.6 (2) | N2—C31—C30 | 105.24 (19) |
C12—C13—H13 | 119.7 | C32—C31—C30 | 115.39 (19) |
C14—C13—H13 | 119.7 | N2—C31—H31 | 110.5 |
C15—C14—C13 | 119.6 (2) | C32—C31—H31 | 110.5 |
C15—C14—H14 | 120.2 | C30—C31—H31 | 110.5 |
C13—C14—H14 | 120.2 | C31—C32—C18 | 105.32 (17) |
C14—C15—C16 | 120.8 (3) | C31—C32—H32A | 110.7 |
C14—C15—H15 | 119.6 | C18—C32—H32A | 110.7 |
C16—C15—H15 | 119.6 | C31—C32—H32B | 110.7 |
C15—C16—C11 | 119.3 (2) | C18—C32—H32B | 110.7 |
C15—C16—H16 | 120.4 | H32A—C32—H32B | 108.8 |
C11—C16—H16 | 120.4 | O7—C33—O8 | 123.1 (2) |
O4—C17—C8 | 108.33 (18) | O7—C33—C18 | 124.2 (2) |
O4—C17—C18 | 106.63 (16) | O8—C33—C18 | 112.65 (19) |
C8—C17—C18 | 116.62 (18) | O8—C34—H34A | 109.5 |
O4—C17—H17 | 108.3 | O8—C34—H34B | 109.5 |
C8—C17—H17 | 108.3 | H34A—C34—H34B | 109.5 |
C18—C17—H17 | 108.3 | O8—C34—H34C | 109.5 |
C33—C18—C32 | 112.46 (18) | H34A—C34—H34C | 109.5 |
C33—C18—C17 | 109.74 (17) | H34B—C34—H34C | 109.5 |
C32—C18—C17 | 115.58 (18) | C10—N1—C1 | 134.0 (2) |
C33—C18—C19 | 113.03 (18) | C10—N1—C8 | 96.14 (18) |
C32—C18—C19 | 102.27 (16) | C1—N1—C8 | 129.89 (19) |
C17—C18—C19 | 103.27 (16) | C19—N2—C31 | 106.95 (16) |
N2—C19—C27 | 117.35 (18) | C19—N2—C28 | 119.41 (18) |
N2—C19—C20 | 109.40 (17) | C31—N2—C28 | 104.83 (18) |
C27—C19—C20 | 102.52 (17) | C4—O1—C7 | 118.1 (2) |
N2—C19—C18 | 108.18 (17) | C11—O3—C9 | 115.24 (17) |
C27—C19—C18 | 115.38 (18) | C20—O4—C17 | 106.50 (16) |
C20—C19—C18 | 102.71 (16) | C20—O5—H5A | 109.5 |
O5—C20—O4 | 108.25 (18) | C33—O8—C34 | 116.94 (19) |
C6—C1—C2—C3 | −0.3 (4) | C22—C21—C26—C27 | 178.8 (2) |
N1—C1—C2—C3 | −179.3 (2) | C20—C21—C26—C27 | −2.2 (3) |
C1—C2—C3—C4 | 0.5 (4) | C24—C25—C26—C21 | 0.5 (4) |
C2—C3—C4—C5 | −0.3 (4) | C24—C25—C26—C27 | −179.7 (2) |
C2—C3—C4—O1 | 179.5 (2) | C21—C26—C27—O6 | 167.0 (2) |
O1—C4—C5—C6 | −179.8 (2) | C25—C26—C27—O6 | −12.8 (4) |
C3—C4—C5—C6 | 0.0 (4) | C21—C26—C27—C19 | −11.7 (3) |
C4—C5—C6—C1 | 0.2 (4) | C25—C26—C27—C19 | 168.5 (2) |
C2—C1—C6—C5 | 0.0 (4) | N2—C19—C27—O6 | −39.2 (3) |
N1—C1—C6—C5 | 179.1 (2) | C20—C19—C27—O6 | −159.0 (2) |
N1—C8—C9—O3 | −125.71 (19) | C18—C19—C27—O6 | 90.2 (3) |
C17—C8—C9—O3 | 118.4 (2) | N2—C19—C27—C26 | 139.48 (19) |
N1—C8—C9—C10 | −3.95 (16) | C20—C19—C27—C26 | 19.6 (2) |
C17—C8—C9—C10 | −119.8 (2) | C18—C19—C27—C26 | −91.2 (2) |
O3—C9—C10—O2 | −63.1 (4) | N2—C28—C29—C30 | −34.4 (3) |
C8—C9—C10—O2 | −179.2 (3) | C28—C29—C30—C31 | 16.9 (3) |
O3—C9—C10—N1 | 120.4 (2) | C29—C30—C31—N2 | 7.0 (3) |
C8—C9—C10—N1 | 4.26 (18) | C29—C30—C31—C32 | −107.5 (2) |
C16—C11—C12—C13 | 0.4 (4) | N2—C31—C32—C18 | 35.7 (2) |
O3—C11—C12—C13 | 179.4 (2) | C30—C31—C32—C18 | 150.7 (2) |
C11—C12—C13—C14 | 0.1 (4) | C33—C18—C32—C31 | −144.90 (19) |
C12—C13—C14—C15 | −0.3 (4) | C17—C18—C32—C31 | 88.0 (2) |
C13—C14—C15—C16 | 0.1 (4) | C19—C18—C32—C31 | −23.4 (2) |
C14—C15—C16—C11 | 0.3 (4) | C32—C18—C33—O7 | −139.0 (2) |
C12—C11—C16—C15 | −0.6 (4) | C17—C18—C33—O7 | −8.9 (3) |
O3—C11—C16—C15 | −179.6 (2) | C19—C18—C33—O7 | 105.8 (3) |
N1—C8—C17—O4 | −69.7 (2) | C32—C18—C33—O8 | 43.1 (3) |
C9—C8—C17—O4 | 29.6 (3) | C17—C18—C33—O8 | 173.25 (19) |
N1—C8—C17—C18 | 170.06 (18) | C19—C18—C33—O8 | −72.1 (2) |
C9—C8—C17—C18 | −90.6 (2) | O2—C10—N1—C1 | 0.4 (5) |
O4—C17—C18—C33 | 144.22 (17) | C9—C10—N1—C1 | 177.1 (2) |
C8—C17—C18—C33 | −94.7 (2) | O2—C10—N1—C8 | 178.8 (3) |
O4—C17—C18—C32 | −87.3 (2) | C9—C10—N1—C8 | −4.47 (19) |
C8—C17—C18—C32 | 33.8 (3) | C2—C1—N1—C10 | −25.0 (4) |
O4—C17—C18—C19 | 23.5 (2) | C6—C1—N1—C10 | 156.0 (3) |
C8—C17—C18—C19 | 144.57 (18) | C2—C1—N1—C8 | 157.1 (2) |
C33—C18—C19—N2 | 124.31 (19) | C6—C1—N1—C8 | −21.9 (3) |
C32—C18—C19—N2 | 3.2 (2) | C17—C8—N1—C10 | 123.5 (2) |
C17—C18—C19—N2 | −117.18 (18) | C9—C8—N1—C10 | 4.47 (19) |
C33—C18—C19—C27 | −9.4 (2) | C17—C8—N1—C1 | −58.0 (3) |
C32—C18—C19—C27 | −130.54 (19) | C9—C8—N1—C1 | −177.0 (2) |
C17—C18—C19—C27 | 109.1 (2) | C27—C19—N2—C31 | 151.62 (19) |
C33—C18—C19—C20 | −120.06 (19) | C20—C19—N2—C31 | −92.2 (2) |
C32—C18—C19—C20 | 118.79 (17) | C18—C19—N2—C31 | 18.9 (2) |
C17—C18—C19—C20 | −1.6 (2) | C27—C19—N2—C28 | 33.0 (3) |
N2—C19—C20—O5 | −24.3 (3) | C20—C19—N2—C28 | 149.1 (2) |
C27—C19—C20—O5 | 100.9 (2) | C18—C19—N2—C28 | −99.7 (2) |
C18—C19—C20—O5 | −139.07 (18) | C32—C31—N2—C19 | −33.9 (2) |
N2—C19—C20—O4 | 93.87 (19) | C30—C31—N2—C19 | −155.86 (18) |
C27—C19—C20—O4 | −140.89 (17) | C32—C31—N2—C28 | 93.8 (2) |
C18—C19—C20—O4 | −20.9 (2) | C30—C31—N2—C28 | −28.1 (2) |
N2—C19—C20—C21 | −145.69 (18) | C29—C28—N2—C19 | 158.7 (2) |
C27—C19—C20—C21 | −20.4 (2) | C29—C28—N2—C31 | 39.0 (3) |
C18—C19—C20—C21 | 99.57 (19) | C5—C4—O1—C7 | 168.1 (3) |
O5—C20—C21—C26 | −106.8 (2) | C3—C4—O1—C7 | −11.7 (4) |
O4—C20—C21—C26 | 130.4 (2) | C12—C11—O3—C9 | 140.2 (2) |
C19—C20—C21—C26 | 14.8 (2) | C16—C11—O3—C9 | −40.7 (3) |
O5—C20—C21—C22 | 72.0 (3) | C10—C9—O3—C11 | 96.4 (2) |
O4—C20—C21—C22 | −50.8 (3) | C8—C9—O3—C11 | −162.82 (18) |
C19—C20—C21—C22 | −166.4 (2) | O5—C20—O4—C17 | 157.98 (16) |
C26—C21—C22—C23 | 1.0 (4) | C21—C20—O4—C17 | −77.3 (2) |
C20—C21—C22—C23 | −177.8 (2) | C19—C20—O4—C17 | 37.2 (2) |
C21—C22—C23—C24 | 0.2 (4) | C8—C17—O4—C20 | −164.82 (16) |
C22—C23—C24—C25 | −1.0 (4) | C18—C17—O4—C20 | −38.6 (2) |
C23—C24—C25—C26 | 0.6 (4) | O7—C33—O8—C34 | −6.0 (4) |
C22—C21—C26—C25 | −1.3 (4) | C18—C33—O8—C34 | 171.9 (2) |
C20—C21—C26—C25 | 177.6 (2) |
Cg7 is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···N2 | 0.82 | 2.10 | 2.638 (2) | 122 |
C15—H15···O6i | 0.93 | 2.56 | 3.231 (3) | 129 |
C16—H16···O2 | 0.93 | 2.59 | 3.405 (3) | 146 |
C32—H32B···O3 | 0.97 | 2.55 | 3.413 (3) | 148 |
C12—H12···Cg7ii | 0.93 | 2.95 | 3.775 (3) | 149 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C34H32N2O8 |
Mr | 596.62 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.4251 (13), 7.8362 (8), 32.041 (4) |
β (°) | 91.313 (8) |
V (Å3) | 2867.9 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.25 × 0.22 × 0.2 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.976, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27667, 7104, 3251 |
Rint | 0.083 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.141, 0.99 |
No. of reflections | 7104 |
No. of parameters | 400 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.20 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg7 is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···N2 | 0.82 | 2.10 | 2.638 (2) | 122 |
C15—H15···O6i | 0.93 | 2.56 | 3.231 (3) | 129 |
C12—H12···Cg7ii | 0.93 | 2.95 | 3.775 (3) | 149 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2. |
Acknowledgements
SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC & SAP) for financial support.
References
Arun, M., Joshi, S. N., Puranik, V. G., Bhawal, B. M. & Deshmukh, A. R. A. S. (2003). Tetrahedron, 59, 2309–2316. Web of Science CSD CrossRef CAS Google Scholar
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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 role of β-lactam antibiotics is well known (Banik & Becker, 2000). 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 title β-lactam derivative was carried out which is reported in this article.
In the title compound (Fig. 1), the β-lactam ring makes dihedral angle of 31.36 (1)° with the indene ring system. The maximum deviation of indene ring system is 0.212 (2) Å for atom C19. The β-lactam ring makes dihedral angles 23.41 (15) and 25.98 (15)°, respectively, with the attached methoxyphenyl and phenoxy rings. The carboxylate group adopts an extended conformation with thetorsion angle C18—C33—O8—C34 = 171.9 (2)°. The five-membered ring (C19/C20/C21/C26/C27) in the inden ring system and the fused furan ring (O4/C17—C20) adopt envelope conformations, with C19 and O4 atoms deviating by 0.135 (2) and -0.221 (2) Å, respectively, from the planes formed by the remaining atoms of the rings. In the pyrrolizidine ring system, the pyrrolidine ring (C18/C19/N2/C31/C32) adopts a C31-envelope conformation, with C31 deviating by 0.216 (2) Å from the remaining ring atoms. The bond lengths and bond angles in the title compound agree with the corresponding bond lengths and angles reported for a closely related compound (Arun et al., (2003).
The molecular structure of the title compound is stabilized by a strong O5—H5A···N2 hydrogen bond, generating an S(5) motif (Bernstein et al., 1995). The H-atom bonded to C15 is involved in hydrogen bonding with atom O6 forming a C(12) chain running along the a axis (Tab. 1 & Fig. 2). A weak intermolecular C—H···π interaction involving the C12—H12 group and the C1—C16 phenoxy ring is also observed.