organic compounds
Methyl 12-hydroxy-10-[1-(4-methoxyphenyl)-2-oxo-3-phenoxyazetidin-4-yl]-11-oxa-3-azahexacyclo[11.7.1.02,9.02,12.03,7.017,21]henicosa-1(20),13,15,17(21),18-pentaene-9-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, C37H34N2O7, both pyrrolidine rings adopt envelope conformations. The β-lactam ring is close to planar (r.m.s. deviation = 0.0395 Å) and makes a dihedral angle of 83.35 (15)° with the furan ring. The O atom attached to the β-lactam ring deviates by 0.187 (2) Å from the mean plane of the ring. The β-lactam ring makes dihedral angles of 14.90 (15) and 27.72 (17)° with the methoxyphenyl and phenyl rings, respectively. The crystal packing features C—H⋯O hydrogen bonds.
Related literature
For general background and therapeutic applications of β-lactams, see: Banik & Becker (2000); Brakhage (1998). For a related structure, see: Sundaramoorthy et al. (2012).
Experimental
Crystal data
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Refinement
|
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, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812045795/pv2604sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045795/pv2604Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812045795/pv2604Isup3.cml
A solution of methyl 2-(hydroxy(1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin -2-yl)methyl)acrylate (1.0 equiv.), acenaphthequinone (1.1 equiv.) and proline (1.1 equiv.) were refluxed in dry methanol. Completion of the reaction was evidenced by TLC analysis. The solvent was then removed under vacuum, diluted in dichloromethane and washed with brine and water. The organic layer was separated and removed and the residue subjected to
using ethyl acetate and hexane as an (1:4) afforded the cycloadduct. The product was dissolved in chloroform and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent for 48 hours resulting in the formation of single crystals.The hydrogen atoms were placed in calculated positions with C—H = 0.93 Å to 0.98 Å and refined in the riding model with fixed isotropic displacement parameters:Uiso(H) = 1.5Ueq(methyl-C) and 1.2Ueq(non-methyl C). The hydroxyl H-atom was located from a difference map and was allowed to refine freely.
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, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C37H34N2O7 | F(000) = 2608 |
Mr = 618.66 | Dx = 1.314 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5614 reflections |
a = 9.6545 (11) Å | θ = 1.3–25.3° |
b = 20.363 (2) Å | µ = 0.09 mm−1 |
c = 31.804 (3) Å | T = 293 K |
V = 6252.5 (11) Å3 | Block, colourless |
Z = 8 | 0.35 × 0.30 × 0.25 mm |
Bruker SMART APEXII area-detector diffractometer | 5614 independent reflections |
Radiation source: fine-focus sealed tube | 3210 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ω and ϕ scans | θmax = 25.3°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −11→11 |
Tmin = 0.969, Tmax = 0.978 | k = −22→24 |
26528 measured reflections | l = −32→38 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0503P)2 + 1.3234P] where P = (Fo2 + 2Fc2)/3 |
5614 reflections | (Δ/σ)max < 0.001 |
421 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C37H34N2O7 | V = 6252.5 (11) Å3 |
Mr = 618.66 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 9.6545 (11) Å | µ = 0.09 mm−1 |
b = 20.363 (2) Å | T = 293 K |
c = 31.804 (3) Å | 0.35 × 0.30 × 0.25 mm |
Bruker SMART APEXII area-detector diffractometer | 5614 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 3210 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.978 | Rint = 0.062 |
26528 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.14 e Å−3 |
5614 reflections | Δρmin = −0.21 e Å−3 |
421 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 | −0.1844 (4) | −0.29414 (16) | 0.45652 (10) | 0.0994 (11) | |
H1A | −0.2716 | −0.2931 | 0.4710 | 0.149* | |
H1B | −0.1945 | −0.3182 | 0.4307 | 0.149* | |
H1C | −0.1553 | −0.2501 | 0.4504 | 0.149* | |
C2 | −0.0580 (3) | −0.29816 (14) | 0.52120 (9) | 0.0668 (7) | |
C3 | −0.1206 (3) | −0.24169 (13) | 0.53561 (8) | 0.0614 (7) | |
H3 | −0.1869 | −0.2206 | 0.5192 | 0.074* | |
C4 | −0.0846 (3) | −0.21631 (12) | 0.57455 (7) | 0.0580 (7) | |
H4 | −0.1261 | −0.1778 | 0.5840 | 0.070* | |
C5 | 0.0121 (3) | −0.24757 (12) | 0.59942 (8) | 0.0559 (6) | |
C6 | 0.0725 (3) | −0.30568 (13) | 0.58544 (9) | 0.0688 (7) | |
H6 | 0.1362 | −0.3278 | 0.6022 | 0.083* | |
C7 | 0.0370 (3) | −0.33014 (14) | 0.54648 (9) | 0.0742 (8) | |
H7 | 0.0777 | −0.3688 | 0.5370 | 0.089* | |
C8 | 0.0036 (2) | −0.15872 (11) | 0.65931 (7) | 0.0531 (6) | |
H8 | −0.0971 | −0.1585 | 0.6633 | 0.064* | |
C9 | 0.0769 (2) | −0.18432 (12) | 0.69942 (7) | 0.0566 (6) | |
H9 | 0.1632 | −0.1609 | 0.7056 | 0.068* | |
C10 | 0.1001 (3) | −0.24787 (14) | 0.67485 (8) | 0.0656 (7) | |
C11 | 0.0410 (3) | −0.19644 (13) | 0.77364 (7) | 0.0569 (6) | |
C12 | 0.1496 (3) | −0.23813 (13) | 0.78101 (8) | 0.0663 (7) | |
H12 | 0.1945 | −0.2591 | 0.7589 | 0.080* | |
C13 | 0.1909 (3) | −0.24834 (16) | 0.82211 (11) | 0.0823 (9) | |
H13 | 0.2639 | −0.2768 | 0.8278 | 0.099* | |
C14 | 0.1255 (4) | −0.2170 (2) | 0.85429 (11) | 0.1028 (13) | |
H14 | 0.1525 | −0.2250 | 0.8819 | 0.123* | |
C15 | 0.0202 (4) | −0.1739 (2) | 0.84622 (10) | 0.1091 (13) | |
H15 | −0.0224 | −0.1517 | 0.8683 | 0.131* | |
C16 | −0.0224 (3) | −0.16324 (17) | 0.80586 (9) | 0.0832 (9) | |
H16 | −0.0936 | −0.1338 | 0.8003 | 0.100* | |
C17 | 0.0505 (2) | −0.09544 (11) | 0.63905 (7) | 0.0465 (6) | |
H17 | 0.0342 | −0.0988 | 0.6087 | 0.056* | |
C18 | −0.0236 (2) | −0.03335 (11) | 0.65529 (6) | 0.0431 (5) | |
C19 | −0.0432 (2) | −0.02920 (12) | 0.70346 (6) | 0.0513 (6) | |
H19A | −0.1280 | −0.0060 | 0.7103 | 0.062* | |
H19B | −0.0472 | −0.0728 | 0.7157 | 0.062* | |
C20 | 0.0831 (2) | 0.00838 (13) | 0.71975 (7) | 0.0563 (6) | |
H20 | 0.1602 | −0.0219 | 0.7248 | 0.068* | |
C21 | 0.0590 (3) | 0.05173 (16) | 0.75843 (8) | 0.0771 (8) | |
H21A | −0.0354 | 0.0472 | 0.7685 | 0.093* | |
H21B | 0.1220 | 0.0399 | 0.7809 | 0.093* | |
C22 | 0.0859 (4) | 0.12086 (16) | 0.74376 (9) | 0.0889 (9) | |
H22A | 0.1813 | 0.1334 | 0.7489 | 0.107* | |
H22B | 0.0251 | 0.1518 | 0.7579 | 0.107* | |
C23 | 0.0555 (3) | 0.11824 (13) | 0.69729 (8) | 0.0680 (7) | |
H23A | −0.0433 | 0.1184 | 0.6918 | 0.082* | |
H23B | 0.0986 | 0.1545 | 0.6824 | 0.082* | |
C24 | 0.0864 (2) | 0.02290 (11) | 0.64621 (6) | 0.0433 (5) | |
C25 | 0.2212 (2) | −0.01860 (12) | 0.63326 (7) | 0.0484 (6) | |
C26 | 0.2334 (2) | −0.00885 (12) | 0.58636 (7) | 0.0523 (6) | |
C27 | 0.1370 (2) | 0.03869 (12) | 0.57417 (7) | 0.0516 (6) | |
C28 | 0.0569 (2) | 0.06374 (12) | 0.60742 (7) | 0.0486 (6) | |
C29 | −0.0358 (3) | 0.11284 (13) | 0.59889 (8) | 0.0661 (7) | |
H29 | −0.0874 | 0.1318 | 0.6204 | 0.079* | |
C30 | −0.0519 (3) | 0.13415 (15) | 0.55704 (10) | 0.0826 (9) | |
H30 | −0.1154 | 0.1673 | 0.5513 | 0.099* | |
C31 | 0.0218 (4) | 0.10812 (16) | 0.52475 (9) | 0.0859 (10) | |
H31 | 0.0052 | 0.1223 | 0.4974 | 0.103* | |
C32 | 0.1232 (3) | 0.05987 (14) | 0.53230 (8) | 0.0669 (7) | |
C33 | 0.2122 (4) | 0.03017 (17) | 0.50266 (9) | 0.0858 (10) | |
H33 | 0.2063 | 0.0419 | 0.4745 | 0.103* | |
C34 | 0.3064 (4) | −0.01533 (17) | 0.51499 (9) | 0.0887 (10) | |
H34 | 0.3646 | −0.0337 | 0.4949 | 0.106* | |
C35 | 0.3196 (3) | −0.03595 (14) | 0.55723 (8) | 0.0725 (8) | |
H35 | 0.3853 | −0.0671 | 0.5649 | 0.087* | |
C36 | −0.1586 (2) | −0.02405 (13) | 0.63177 (7) | 0.0500 (6) | |
C37 | −0.3568 (3) | 0.04349 (18) | 0.62279 (9) | 0.0912 (10) | |
H37A | −0.3327 | 0.0532 | 0.5942 | 0.137* | |
H37B | −0.3997 | 0.0812 | 0.6353 | 0.137* | |
H37C | −0.4200 | 0.0071 | 0.6235 | 0.137* | |
N1 | 0.0482 (2) | −0.22067 (10) | 0.63899 (6) | 0.0595 (5) | |
N2 | 0.11888 (18) | 0.05505 (10) | 0.68586 (5) | 0.0501 (5) | |
O1 | −0.0823 (2) | −0.32569 (10) | 0.48259 (6) | 0.0937 (7) | |
O2 | 0.1430 (2) | −0.30229 (10) | 0.68253 (6) | 0.0899 (6) | |
O3 | −0.01484 (17) | −0.18640 (9) | 0.73418 (5) | 0.0636 (5) | |
O4 | −0.19583 (18) | −0.05791 (10) | 0.60292 (6) | 0.0740 (5) | |
O5 | −0.23191 (15) | 0.02664 (9) | 0.64624 (5) | 0.0635 (5) | |
O6 | 0.19453 (14) | −0.08459 (8) | 0.64559 (4) | 0.0525 (4) | |
O7 | 0.33797 (16) | 0.00319 (10) | 0.65408 (6) | 0.0655 (5) | |
H7A | 0.303 (3) | 0.0308 (14) | 0.6745 (9) | 0.090 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.118 (3) | 0.105 (3) | 0.075 (2) | 0.008 (2) | −0.029 (2) | −0.0208 (19) |
C2 | 0.0727 (18) | 0.0621 (18) | 0.0657 (18) | −0.0071 (15) | −0.0012 (15) | −0.0129 (15) |
C3 | 0.0669 (17) | 0.0586 (17) | 0.0587 (17) | −0.0053 (13) | −0.0017 (13) | −0.0016 (14) |
C4 | 0.0671 (17) | 0.0539 (16) | 0.0529 (16) | −0.0033 (13) | 0.0057 (13) | −0.0004 (13) |
C5 | 0.0663 (16) | 0.0493 (15) | 0.0522 (16) | −0.0063 (13) | 0.0047 (13) | 0.0030 (12) |
C6 | 0.0727 (18) | 0.0570 (17) | 0.077 (2) | 0.0029 (14) | −0.0052 (15) | 0.0009 (15) |
C7 | 0.0778 (19) | 0.0606 (18) | 0.084 (2) | 0.0053 (15) | −0.0018 (16) | −0.0166 (16) |
C8 | 0.0601 (15) | 0.0522 (15) | 0.0469 (14) | −0.0038 (12) | −0.0009 (12) | 0.0028 (12) |
C9 | 0.0569 (15) | 0.0662 (17) | 0.0465 (15) | −0.0052 (12) | 0.0012 (12) | 0.0110 (13) |
C10 | 0.0746 (18) | 0.0639 (19) | 0.0583 (18) | 0.0046 (14) | 0.0042 (14) | 0.0121 (15) |
C11 | 0.0588 (16) | 0.0667 (17) | 0.0451 (16) | −0.0158 (13) | −0.0017 (12) | 0.0117 (13) |
C12 | 0.0731 (18) | 0.0641 (18) | 0.0616 (18) | −0.0048 (14) | −0.0088 (14) | 0.0124 (14) |
C13 | 0.081 (2) | 0.087 (2) | 0.079 (2) | −0.0211 (17) | −0.0233 (18) | 0.0271 (19) |
C14 | 0.097 (3) | 0.157 (4) | 0.054 (2) | −0.048 (3) | −0.019 (2) | 0.027 (2) |
C15 | 0.094 (3) | 0.179 (4) | 0.055 (2) | −0.011 (3) | 0.0026 (18) | −0.012 (2) |
C16 | 0.0722 (19) | 0.120 (3) | 0.0577 (19) | 0.0013 (18) | 0.0054 (15) | 0.0031 (18) |
C17 | 0.0484 (13) | 0.0535 (14) | 0.0375 (13) | −0.0039 (11) | −0.0004 (10) | 0.0025 (11) |
C18 | 0.0391 (12) | 0.0570 (14) | 0.0330 (12) | −0.0001 (10) | 0.0016 (9) | 0.0036 (10) |
C19 | 0.0510 (13) | 0.0648 (16) | 0.0382 (13) | 0.0031 (11) | 0.0058 (10) | 0.0045 (11) |
C20 | 0.0524 (14) | 0.0747 (17) | 0.0418 (14) | 0.0066 (12) | −0.0042 (11) | −0.0020 (13) |
C21 | 0.0775 (19) | 0.113 (3) | 0.0409 (16) | 0.0027 (17) | −0.0011 (13) | −0.0145 (16) |
C22 | 0.103 (2) | 0.097 (2) | 0.067 (2) | 0.0008 (19) | 0.0008 (17) | −0.0316 (18) |
C23 | 0.0772 (18) | 0.0650 (18) | 0.0617 (17) | 0.0004 (14) | 0.0044 (14) | −0.0175 (14) |
C24 | 0.0404 (12) | 0.0527 (14) | 0.0368 (13) | −0.0028 (10) | 0.0015 (9) | −0.0021 (10) |
C25 | 0.0416 (13) | 0.0571 (16) | 0.0465 (14) | −0.0047 (11) | 0.0058 (10) | −0.0030 (12) |
C26 | 0.0561 (14) | 0.0570 (16) | 0.0438 (14) | −0.0146 (12) | 0.0117 (11) | −0.0082 (12) |
C27 | 0.0610 (15) | 0.0563 (16) | 0.0373 (14) | −0.0198 (12) | 0.0040 (11) | 0.0013 (11) |
C28 | 0.0492 (13) | 0.0526 (15) | 0.0439 (14) | −0.0098 (11) | −0.0004 (11) | 0.0045 (11) |
C29 | 0.0676 (17) | 0.0652 (18) | 0.0654 (18) | 0.0000 (14) | 0.0000 (14) | 0.0128 (14) |
C30 | 0.091 (2) | 0.081 (2) | 0.076 (2) | −0.0044 (17) | −0.0112 (18) | 0.0299 (18) |
C31 | 0.109 (3) | 0.091 (2) | 0.057 (2) | −0.029 (2) | −0.0130 (18) | 0.0294 (17) |
C32 | 0.085 (2) | 0.0700 (19) | 0.0459 (17) | −0.0277 (16) | 0.0024 (15) | 0.0067 (14) |
C33 | 0.125 (3) | 0.092 (3) | 0.0404 (17) | −0.040 (2) | 0.0145 (18) | −0.0012 (17) |
C34 | 0.117 (3) | 0.094 (3) | 0.055 (2) | −0.027 (2) | 0.0365 (18) | −0.0206 (18) |
C35 | 0.0842 (19) | 0.0754 (19) | 0.0578 (18) | −0.0144 (15) | 0.0238 (15) | −0.0135 (15) |
C36 | 0.0443 (13) | 0.0619 (17) | 0.0439 (15) | −0.0061 (12) | 0.0046 (11) | 0.0079 (13) |
C37 | 0.0504 (16) | 0.142 (3) | 0.081 (2) | 0.0219 (17) | −0.0102 (14) | 0.012 (2) |
N1 | 0.0763 (14) | 0.0545 (13) | 0.0477 (13) | 0.0003 (11) | −0.0036 (11) | 0.0061 (11) |
N2 | 0.0485 (11) | 0.0630 (13) | 0.0387 (11) | −0.0008 (9) | 0.0011 (9) | −0.0083 (10) |
O1 | 0.1088 (17) | 0.0879 (15) | 0.0843 (15) | 0.0127 (12) | −0.0236 (12) | −0.0371 (12) |
O2 | 0.1236 (17) | 0.0733 (14) | 0.0729 (14) | 0.0277 (13) | −0.0007 (12) | 0.0158 (11) |
O3 | 0.0584 (10) | 0.0863 (13) | 0.0459 (10) | −0.0035 (9) | −0.0015 (8) | 0.0165 (9) |
O4 | 0.0688 (12) | 0.0918 (14) | 0.0613 (12) | −0.0018 (10) | −0.0224 (9) | −0.0095 (10) |
O5 | 0.0418 (9) | 0.0909 (13) | 0.0579 (10) | 0.0123 (9) | −0.0013 (8) | 0.0041 (9) |
O6 | 0.0442 (9) | 0.0612 (11) | 0.0520 (10) | 0.0042 (8) | 0.0053 (7) | 0.0041 (8) |
O7 | 0.0386 (9) | 0.0956 (14) | 0.0622 (12) | −0.0063 (9) | 0.0009 (8) | −0.0150 (11) |
C1—O1 | 1.440 (3) | C19—H19A | 0.9700 |
C1—H1A | 0.9600 | C19—H19B | 0.9700 |
C1—H1B | 0.9600 | C20—N2 | 1.478 (3) |
C1—H1C | 0.9600 | C20—C21 | 1.532 (3) |
C2—O1 | 1.370 (3) | C20—H20 | 0.9800 |
C2—C3 | 1.378 (4) | C21—C22 | 1.506 (4) |
C2—C7 | 1.383 (4) | C21—H21A | 0.9700 |
C3—C4 | 1.386 (3) | C21—H21B | 0.9700 |
C3—H3 | 0.9300 | C22—C23 | 1.508 (4) |
C4—C5 | 1.380 (3) | C22—H22A | 0.9700 |
C4—H4 | 0.9300 | C22—H22B | 0.9700 |
C5—C6 | 1.392 (3) | C23—N2 | 1.470 (3) |
C5—N1 | 1.416 (3) | C23—H23A | 0.9700 |
C6—C7 | 1.379 (4) | C23—H23B | 0.9700 |
C6—H6 | 0.9300 | C24—N2 | 1.455 (3) |
C7—H7 | 0.9300 | C24—C28 | 1.515 (3) |
C8—N1 | 1.482 (3) | C24—C25 | 1.605 (3) |
C8—C17 | 1.510 (3) | C25—O7 | 1.381 (3) |
C8—C9 | 1.549 (3) | C25—O6 | 1.423 (3) |
C8—H8 | 0.9800 | C25—C26 | 1.509 (3) |
C9—O3 | 1.417 (3) | C26—C35 | 1.362 (3) |
C9—C10 | 1.528 (4) | C26—C27 | 1.397 (3) |
C9—H9 | 0.9800 | C27—C28 | 1.406 (3) |
C10—O2 | 1.208 (3) | C27—C32 | 1.406 (3) |
C10—N1 | 1.363 (3) | C28—C29 | 1.369 (3) |
C11—C12 | 1.369 (4) | C29—C30 | 1.408 (4) |
C11—C16 | 1.372 (4) | C29—H29 | 0.9300 |
C11—O3 | 1.381 (3) | C30—C31 | 1.357 (4) |
C12—C13 | 1.383 (4) | C30—H30 | 0.9300 |
C12—H12 | 0.9300 | C31—C32 | 1.408 (4) |
C13—C14 | 1.362 (5) | C31—H31 | 0.9300 |
C13—H13 | 0.9300 | C32—C33 | 1.412 (4) |
C14—C15 | 1.367 (5) | C33—C34 | 1.356 (4) |
C14—H14 | 0.9300 | C33—H33 | 0.9300 |
C15—C16 | 1.365 (4) | C34—C35 | 1.413 (4) |
C15—H15 | 0.9300 | C34—H34 | 0.9300 |
C16—H16 | 0.9300 | C35—H35 | 0.9300 |
C17—O6 | 1.423 (2) | C36—O4 | 1.203 (3) |
C17—C18 | 1.542 (3) | C36—O5 | 1.334 (3) |
C17—H17 | 0.9800 | C37—O5 | 1.458 (3) |
C18—C36 | 1.514 (3) | C37—H37A | 0.9600 |
C18—C19 | 1.546 (3) | C37—H37B | 0.9600 |
C18—C24 | 1.589 (3) | C37—H37C | 0.9600 |
C19—C20 | 1.530 (3) | O7—H7A | 0.92 (3) |
O1—C1—H1A | 109.5 | C22—C21—C20 | 105.3 (2) |
O1—C1—H1B | 109.5 | C22—C21—H21A | 110.7 |
H1A—C1—H1B | 109.5 | C20—C21—H21A | 110.7 |
O1—C1—H1C | 109.5 | C22—C21—H21B | 110.7 |
H1A—C1—H1C | 109.5 | C20—C21—H21B | 110.7 |
H1B—C1—H1C | 109.5 | H21A—C21—H21B | 108.8 |
O1—C2—C3 | 124.4 (3) | C21—C22—C23 | 103.7 (2) |
O1—C2—C7 | 116.2 (3) | C21—C22—H22A | 111.0 |
C3—C2—C7 | 119.4 (3) | C23—C22—H22A | 111.0 |
C2—C3—C4 | 119.9 (3) | C21—C22—H22B | 111.0 |
C2—C3—H3 | 120.0 | C23—C22—H22B | 111.0 |
C4—C3—H3 | 120.0 | H22A—C22—H22B | 109.0 |
C5—C4—C3 | 120.7 (2) | N2—C23—C22 | 101.1 (2) |
C5—C4—H4 | 119.7 | N2—C23—H23A | 111.6 |
C3—C4—H4 | 119.7 | C22—C23—H23A | 111.6 |
C4—C5—C6 | 119.5 (2) | N2—C23—H23B | 111.6 |
C4—C5—N1 | 119.8 (2) | C22—C23—H23B | 111.6 |
C6—C5—N1 | 120.6 (2) | H23A—C23—H23B | 109.4 |
C7—C6—C5 | 119.3 (3) | N2—C24—C28 | 119.95 (19) |
C7—C6—H6 | 120.3 | N2—C24—C18 | 108.12 (16) |
C5—C6—H6 | 120.3 | C28—C24—C18 | 114.73 (16) |
C6—C7—C2 | 121.2 (3) | N2—C24—C25 | 106.54 (16) |
C6—C7—H7 | 119.4 | C28—C24—C25 | 103.42 (16) |
C2—C7—H7 | 119.4 | C18—C24—C25 | 102.06 (16) |
N1—C8—C17 | 116.94 (19) | O7—C25—O6 | 108.61 (18) |
N1—C8—C9 | 86.55 (17) | O7—C25—C26 | 111.61 (18) |
C17—C8—C9 | 120.1 (2) | O6—C25—C26 | 114.24 (18) |
N1—C8—H8 | 110.4 | O7—C25—C24 | 111.69 (18) |
C17—C8—H8 | 110.4 | O6—C25—C24 | 106.23 (16) |
C9—C8—H8 | 110.4 | C26—C25—C24 | 104.32 (18) |
O3—C9—C10 | 117.7 (2) | C35—C26—C27 | 119.9 (2) |
O3—C9—C8 | 111.53 (19) | C35—C26—C25 | 131.8 (2) |
C10—C9—C8 | 86.05 (18) | C27—C26—C25 | 108.28 (19) |
O3—C9—H9 | 112.9 | C26—C27—C28 | 114.1 (2) |
C10—C9—H9 | 112.9 | C26—C27—C32 | 122.6 (2) |
C8—C9—H9 | 112.9 | C28—C27—C32 | 123.3 (3) |
O2—C10—N1 | 131.9 (3) | C29—C28—C27 | 118.4 (2) |
O2—C10—C9 | 136.4 (3) | C29—C28—C24 | 133.2 (2) |
N1—C10—C9 | 91.7 (2) | C27—C28—C24 | 108.1 (2) |
C12—C11—C16 | 121.3 (2) | C28—C29—C30 | 119.0 (3) |
C12—C11—O3 | 123.1 (2) | C28—C29—H29 | 120.5 |
C16—C11—O3 | 115.6 (2) | C30—C29—H29 | 120.5 |
C11—C12—C13 | 118.4 (3) | C31—C30—C29 | 122.5 (3) |
C11—C12—H12 | 120.8 | C31—C30—H30 | 118.8 |
C13—C12—H12 | 120.8 | C29—C30—H30 | 118.8 |
C14—C13—C12 | 120.4 (3) | C30—C31—C32 | 120.5 (3) |
C14—C13—H13 | 119.8 | C30—C31—H31 | 119.7 |
C12—C13—H13 | 119.8 | C32—C31—H31 | 119.7 |
C13—C14—C15 | 120.3 (3) | C27—C32—C31 | 116.2 (3) |
C13—C14—H14 | 119.8 | C27—C32—C33 | 116.3 (3) |
C15—C14—H14 | 119.8 | C31—C32—C33 | 127.5 (3) |
C16—C15—C14 | 120.2 (3) | C34—C33—C32 | 120.5 (3) |
C16—C15—H15 | 119.9 | C34—C33—H33 | 119.7 |
C14—C15—H15 | 119.9 | C32—C33—H33 | 119.7 |
C15—C16—C11 | 119.3 (3) | C33—C34—C35 | 122.6 (3) |
C15—C16—H16 | 120.3 | C33—C34—H34 | 118.7 |
C11—C16—H16 | 120.3 | C35—C34—H34 | 118.7 |
O6—C17—C8 | 111.30 (18) | C26—C35—C34 | 118.1 (3) |
O6—C17—C18 | 106.09 (17) | C26—C35—H35 | 121.0 |
C8—C17—C18 | 114.68 (18) | C34—C35—H35 | 121.0 |
O6—C17—H17 | 108.2 | O4—C36—O5 | 123.2 (2) |
C8—C17—H17 | 108.2 | O4—C36—C18 | 124.2 (2) |
C18—C17—H17 | 108.2 | O5—C36—C18 | 112.5 (2) |
C36—C18—C17 | 109.66 (18) | O5—C37—H37A | 109.5 |
C36—C18—C19 | 112.16 (17) | O5—C37—H37B | 109.5 |
C17—C18—C19 | 115.70 (18) | H37A—C37—H37B | 109.5 |
C36—C18—C24 | 113.28 (17) | O5—C37—H37C | 109.5 |
C17—C18—C24 | 102.72 (16) | H37A—C37—H37C | 109.5 |
C19—C18—C24 | 102.86 (16) | H37B—C37—H37C | 109.5 |
C20—C19—C18 | 105.37 (17) | C10—N1—C5 | 132.6 (2) |
C20—C19—H19A | 110.7 | C10—N1—C8 | 95.04 (19) |
C18—C19—H19A | 110.7 | C5—N1—C8 | 130.2 (2) |
C20—C19—H19B | 110.7 | C24—N2—C23 | 121.23 (18) |
C18—C19—H19B | 110.7 | C24—N2—C20 | 107.00 (17) |
H19A—C19—H19B | 108.8 | C23—N2—C20 | 106.56 (18) |
N2—C20—C19 | 105.13 (17) | C2—O1—C1 | 116.8 (2) |
N2—C20—C21 | 104.5 (2) | C11—O3—C9 | 118.00 (18) |
C19—C20—C21 | 116.0 (2) | C36—O5—C37 | 116.4 (2) |
N2—C20—H20 | 110.3 | C17—O6—C25 | 106.45 (16) |
C19—C20—H20 | 110.3 | C25—O7—H7A | 103.4 (17) |
C21—C20—H20 | 110.3 | ||
O1—C2—C3—C4 | −177.3 (2) | C35—C26—C27—C32 | 0.8 (4) |
C7—C2—C3—C4 | 2.1 (4) | C25—C26—C27—C32 | 179.1 (2) |
C2—C3—C4—C5 | −0.9 (4) | C26—C27—C28—C29 | 176.9 (2) |
C3—C4—C5—C6 | −0.9 (4) | C32—C27—C28—C29 | −2.3 (3) |
C3—C4—C5—N1 | 179.6 (2) | C26—C27—C28—C24 | −8.5 (3) |
C4—C5—C6—C7 | 1.6 (4) | C32—C27—C28—C24 | 172.2 (2) |
N1—C5—C6—C7 | −179.0 (2) | N2—C24—C28—C29 | −55.5 (3) |
C5—C6—C7—C2 | −0.3 (4) | C18—C24—C28—C29 | 75.9 (3) |
O1—C2—C7—C6 | 178.0 (2) | C25—C24—C28—C29 | −173.8 (3) |
C3—C2—C7—C6 | −1.5 (4) | N2—C24—C28—C27 | 131.1 (2) |
N1—C8—C9—O3 | −124.0 (2) | C18—C24—C28—C27 | −97.5 (2) |
C17—C8—C9—O3 | 116.7 (2) | C25—C24—C28—C27 | 12.8 (2) |
N1—C8—C9—C10 | −5.66 (17) | C27—C28—C29—C30 | 2.9 (4) |
C17—C8—C9—C10 | −125.0 (2) | C24—C28—C29—C30 | −170.0 (2) |
O3—C9—C10—O2 | −59.7 (4) | C28—C29—C30—C31 | −0.4 (4) |
C8—C9—C10—O2 | −172.0 (4) | C29—C30—C31—C32 | −2.8 (5) |
O3—C9—C10—N1 | 118.4 (2) | C26—C27—C32—C31 | −179.9 (2) |
C8—C9—C10—N1 | 6.14 (19) | C28—C27—C32—C31 | −0.7 (4) |
C16—C11—C12—C13 | 2.7 (4) | C26—C27—C32—C33 | 0.3 (4) |
O3—C11—C12—C13 | −175.3 (2) | C28—C27—C32—C33 | 179.5 (2) |
C11—C12—C13—C14 | −0.6 (4) | C30—C31—C32—C27 | 3.2 (4) |
C12—C13—C14—C15 | −1.6 (5) | C30—C31—C32—C33 | −177.0 (3) |
C13—C14—C15—C16 | 1.7 (6) | C27—C32—C33—C34 | −1.1 (4) |
C14—C15—C16—C11 | 0.3 (5) | C31—C32—C33—C34 | 179.2 (3) |
C12—C11—C16—C15 | −2.5 (4) | C32—C33—C34—C35 | 0.8 (5) |
O3—C11—C16—C15 | 175.6 (3) | C27—C26—C35—C34 | −1.0 (4) |
N1—C8—C17—O6 | −72.3 (2) | C25—C26—C35—C34 | −178.8 (2) |
C9—C8—C17—O6 | 30.2 (3) | C33—C34—C35—C26 | 0.3 (4) |
N1—C8—C17—C18 | 167.29 (18) | C17—C18—C36—O4 | −4.7 (3) |
C9—C8—C17—C18 | −90.2 (3) | C19—C18—C36—O4 | −134.7 (2) |
O6—C17—C18—C36 | 152.17 (16) | C24—C18—C36—O4 | 109.4 (3) |
C8—C17—C18—C36 | −84.6 (2) | C17—C18—C36—O5 | 176.02 (17) |
O6—C17—C18—C19 | −79.8 (2) | C19—C18—C36—O5 | 46.0 (3) |
C8—C17—C18—C19 | 43.5 (3) | C24—C18—C36—O5 | −69.9 (2) |
O6—C17—C18—C24 | 31.4 (2) | O2—C10—N1—C5 | 7.8 (5) |
C8—C17—C18—C24 | 154.71 (18) | C9—C10—N1—C5 | −170.5 (2) |
C36—C18—C19—C20 | −140.6 (2) | O2—C10—N1—C8 | 171.8 (3) |
C17—C18—C19—C20 | 92.5 (2) | C9—C10—N1—C8 | −6.4 (2) |
C24—C18—C19—C20 | −18.6 (2) | C4—C5—N1—C10 | 155.1 (3) |
C18—C19—C20—N2 | 32.5 (2) | C6—C5—N1—C10 | −24.4 (4) |
C18—C19—C20—C21 | 147.4 (2) | C4—C5—N1—C8 | −3.9 (4) |
N2—C20—C21—C22 | −1.1 (3) | C6—C5—N1—C8 | 176.7 (2) |
C19—C20—C21—C22 | −116.3 (3) | C17—C8—N1—C10 | 128.5 (2) |
C20—C21—C22—C23 | 26.2 (3) | C9—C8—N1—C10 | 6.35 (19) |
C21—C22—C23—N2 | −41.4 (3) | C17—C8—N1—C5 | −66.8 (3) |
C36—C18—C24—N2 | 119.8 (2) | C9—C8—N1—C5 | 171.0 (2) |
C17—C18—C24—N2 | −121.96 (17) | C28—C24—N2—C23 | 33.7 (3) |
C19—C18—C24—N2 | −1.5 (2) | C18—C24—N2—C23 | −100.4 (2) |
C36—C18—C24—C28 | −17.0 (3) | C25—C24—N2—C23 | 150.5 (2) |
C17—C18—C24—C28 | 101.2 (2) | C28—C24—N2—C20 | 156.03 (18) |
C19—C18—C24—C28 | −138.27 (19) | C18—C24—N2—C20 | 21.9 (2) |
C36—C18—C24—C25 | −128.07 (19) | C25—C24—N2—C20 | −87.19 (19) |
C17—C18—C24—C25 | −9.86 (19) | C22—C23—N2—C24 | 164.2 (2) |
C19—C18—C24—C25 | 110.64 (17) | C22—C23—N2—C20 | 41.8 (2) |
N2—C24—C25—O7 | −19.2 (2) | C19—C20—N2—C24 | −33.9 (2) |
C28—C24—C25—O7 | 108.2 (2) | C21—C20—N2—C24 | −156.53 (18) |
C18—C24—C25—O7 | −132.45 (18) | C19—C20—N2—C23 | 97.2 (2) |
N2—C24—C25—O6 | 99.09 (18) | C21—C20—N2—C23 | −25.5 (2) |
C28—C24—C25—O6 | −133.58 (17) | C3—C2—O1—C1 | −2.6 (4) |
C18—C24—C25—O6 | −14.2 (2) | C7—C2—O1—C1 | 178.0 (3) |
N2—C24—C25—C26 | −139.87 (18) | C12—C11—O3—C9 | −38.0 (3) |
C28—C24—C25—C26 | −12.5 (2) | C16—C11—O3—C9 | 144.0 (2) |
C18—C24—C25—C26 | 106.85 (18) | C10—C9—O3—C11 | 94.6 (3) |
O7—C25—C26—C35 | 65.5 (3) | C8—C9—O3—C11 | −168.2 (2) |
O6—C25—C26—C35 | −58.2 (3) | O4—C36—O5—C37 | −5.3 (3) |
C24—C25—C26—C35 | −173.8 (2) | C18—C36—O5—C37 | 174.0 (2) |
O7—C25—C26—C27 | −112.5 (2) | C8—C17—O6—C25 | −168.15 (17) |
O6—C25—C26—C27 | 123.8 (2) | C18—C17—O6—C25 | −42.8 (2) |
C24—C25—C26—C27 | 8.2 (2) | O7—C25—O6—C17 | 155.54 (17) |
C35—C26—C27—C28 | −178.5 (2) | C26—C25—O6—C17 | −79.2 (2) |
C25—C26—C27—C28 | −0.2 (3) | C24—C25—O6—C17 | 35.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C33—H33···O4i | 0.93 | 2.49 | 3.409 (3) | 173 |
C37—H37C···O7ii | 0.96 | 2.53 | 3.217 (3) | 128 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C37H34N2O7 |
Mr | 618.66 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 9.6545 (11), 20.363 (2), 31.804 (3) |
V (Å3) | 6252.5 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.969, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26528, 5614, 3210 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.127, 1.00 |
No. of reflections | 5614 |
No. of parameters | 421 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.21 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C33—H33···O4i | 0.93 | 2.49 | 3.409 (3) | 173 |
C37—H37C···O7ii | 0.96 | 2.53 | 3.217 (3) | 128 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x−1, y, z. |
Acknowledgements
The authors thank the TBI X–ray facility, CAS in Crystallography and Biophysics, University of Madras, India for the data collection. TS thanks the DST for an Inspire fellowship.
References
Banik, B. K. & Becker, F. F. (2000). Tetrahedron Lett. 41, 6551–6554. Web of Science CrossRef CAS Google Scholar
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. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS 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 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 of β-lactam derivatives, we have determined the crystal structure of the title compound and report it in this article.
In the title compound (Fig. 1), both pyrrolidine rings N2/C18–C20/C24 and N2/C20–C23 adopt C20- and C23-envelope conformations, respectively. The β lactam ring (N1/C8–C10) is essentially planar (rmsd = 0.0395 Å) and the O2 atom attached to it deviates by -0.187 (2)Å from its least-squares plane. The β lactam ring makes dihedral angles 14.90 (15)° and 27.72 (17)° with the methoxy phenyl and unsubstitued phenyl rings, respectively. The dihedral angle between the β lactam ring and the furan ring (O6/C17/C18/C24/C25) is 83.35 (15)°. The furan ring makes dihedral angles 81.84 (12)° and 72.24 (15)° with the two pyrrolidine rings. The dihedral angle between the furan ring and the cyclopentane ring (C24/C25/C26/C27/C28) is 71.56 (12)°. The bond distances and angles in the title compound agree very well with the corresponding bond distances and angles reported in a closely related compound (Sundaramoorthy et al., 2012). The packing of the crystal structure is stabilised by intermolecular C—H···O hydrogen bonds (Tab. 1 & Fig. 2).