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organic compounds
Methyl 3-(2-chlorophenyl)-2-(1H-indol-3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-4-nitropyrrolidine-2-carboxylate
aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, bDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India, and cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: sudharose18@gmail.com
In the molecule of the title compound, C37H33ClN4O6, the four-membered β-lactam ring is essentially planar and is oriented at dihedral angles of 30.0 (1), 76.3 (1) and 30.9 (1)° with respect to the methoxyphenyl ring, the phenyl ring and the indole unit, respectively. The pyrrolidine ring adopts a twist conformation. Intramolecular C—H⋯Cl and C—H⋯O hydrogen bonds result in the formation of two five- and one six-membered rings. In the intermolecular C—H⋯O and N—H⋯O hydrogen bonds link the molecules. A weak π⋯π interaction between the pyrrole rings further stabilizes the structure, with a centroid–centroid distance of 3.806 (2) Å.
Related literature
For general background, see: Bruggink (2001); Morin & Gorman (1982
); Katritzky et al. (1996
); Georg (1993
); Coyne et al. (2007
); Dobrowolski et al. (2004
); Cha et al. (2006
). For related literature, see: Bhaskaran et al. (2006
); Kamala et al. (2008
); Ülkü et al. (1997
). For ring puckering parameters, see: Cremer & Pople (1975
). For asymmetry parameters, see: Nardelli (1995
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004
); data reduction: SAINT and XPREP (Bruker, 2004
); program(s) used to solve structure: SIR92 (Altomare et al., 1993
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 (Farrugia, 1997
); software used to prepare material for publication: PLATON (Spek, 2003
).
Supporting information
10.1107/S1600536808013585/hk2460sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808013585/hk2460Isup2.hkl
For the preparation of the title compound, β-Lactam aldehyde (1.0 mol) was treated with tryptophan methylester hydrochloride (1.0 mol) in the presence of Et3N (2.5 mol) and anhydrous MgSO4 (2.0 g) in dry dichloromethane (10 ml) at room temperature for 12 h to give the imine. The imine was washed with water and dried over Na2SO4. The solvent was evaporated under vacuum. The imine (1.0 mol) was then strirred with silver (I) acetate and p-chloro nitrostyrene (1.0 mol) in the presence of Et3N (1.2 mol) and molecular sieves in dry toluene (30 ml) at room temperature for 12 h. The reaction mixture was filtered through a plug celite. The solvent was evaporated under reduced pressure and the residue was subjected to on silica gel (100-200 mesh), with hexane-ethylacetate (7:3) as to give the product. The compound was recrystallized from ethylacetate.
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).C37H33ClN4O6 | Z = 2 |
Mr = 665.12 | F(000) = 696 |
Triclinic, P1 | Dx = 1.345 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.399 (3) Å | Cell parameters from 8315 reflections |
b = 12.500 (3) Å | θ = 2.5–31.6° |
c = 14.211 (3) Å | µ = 0.17 mm−1 |
α = 93.766 (6)° | T = 293 K |
β = 99.962 (6)° | Prism, colourless |
γ = 114.066 (5)° | 0.30 × 0.20 × 0.16 mm |
V = 1642.1 (7) Å3 |
Bruker KAPPA APEX2 CCD diffractometer | 5563 independent reflections |
Radiation source: fine-focus sealed tube | 3770 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ω and ϕ scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (Blessing, 1995) | h = −12→12 |
Tmin = 0.951, Tmax = 0.973 | k = −14→14 |
25481 measured reflections | l = −16→16 |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.317 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
5563 reflections | (Δ/σ)max < 0.001 |
433 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.64 e Å−3 |
C37H33ClN4O6 | γ = 114.066 (5)° |
Mr = 665.12 | V = 1642.1 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.399 (3) Å | Mo Kα radiation |
b = 12.500 (3) Å | µ = 0.17 mm−1 |
c = 14.211 (3) Å | T = 293 K |
α = 93.766 (6)° | 0.30 × 0.20 × 0.16 mm |
β = 99.962 (6)° |
Bruker KAPPA APEX2 CCD diffractometer | 5563 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 3770 reflections with I > 2σ(I) |
Tmin = 0.951, Tmax = 0.973 | Rint = 0.057 |
25481 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.317 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.51 e Å−3 |
5563 reflections | Δρmin = −0.64 e Å−3 |
433 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 > 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 | ||
Cl1 | 0.27147 (16) | 0.62053 (13) | 0.03791 (11) | 0.0912 (5) | |
O1 | 0.4619 (3) | 0.3522 (3) | 0.1048 (2) | 0.0620 (8) | |
O2 | 0.4973 (3) | 0.5325 (3) | 0.16978 (19) | 0.0549 (7) | |
O3 | 0.1219 (3) | 0.2147 (3) | −0.0280 (2) | 0.0690 (9) | |
O4 | −0.0986 (3) | 0.1137 (3) | −0.02304 (19) | 0.0646 (8) | |
O5 | −0.1691 (3) | −0.1217 (3) | 0.3043 (3) | 0.0861 (12) | |
O6 | 0.4562 (3) | −0.1339 (3) | 0.4179 (2) | 0.0647 (9) | |
N1 | 0.5503 (4) | 0.3211 (3) | 0.4608 (2) | 0.0500 (8) | |
H1A | 0.5602 | 0.2674 | 0.4921 | 0.060* | |
N2 | 0.2433 (3) | 0.2437 (2) | 0.19400 (18) | 0.0340 (6) | |
H2 | 0.2943 | 0.2039 | 0.1976 | 0.041* | |
N3 | 0.0198 (3) | 0.1926 (3) | 0.0102 (2) | 0.0441 (8) | |
N4 | 0.0375 (3) | 0.0089 (2) | 0.2561 (2) | 0.0406 (7) | |
C1 | 0.4247 (4) | 0.3105 (3) | 0.4029 (2) | 0.0452 (9) | |
H1 | 0.3372 | 0.2435 | 0.3914 | 0.054* | |
C2 | 0.4455 (3) | 0.4115 (3) | 0.3646 (2) | 0.0344 (7) | |
C3 | 0.5947 (3) | 0.4900 (3) | 0.4004 (2) | 0.0355 (8) | |
C4 | 0.6834 (4) | 0.6067 (3) | 0.3897 (2) | 0.0464 (9) | |
H4 | 0.6465 | 0.6488 | 0.3504 | 0.056* | |
C5 | 0.8251 (4) | 0.6574 (4) | 0.4383 (3) | 0.0614 (11) | |
H5 | 0.8838 | 0.7347 | 0.4320 | 0.074* | |
C6 | 0.8836 (4) | 0.5963 (5) | 0.4969 (3) | 0.0669 (13) | |
H6 | 0.9802 | 0.6335 | 0.5289 | 0.080* | |
C7 | 0.8008 (4) | 0.4815 (5) | 0.5083 (3) | 0.0592 (12) | |
H7 | 0.8402 | 0.4400 | 0.5465 | 0.071* | |
C8 | 0.6570 (4) | 0.4301 (3) | 0.4609 (2) | 0.0411 (8) | |
C9 | 0.3323 (3) | 0.4348 (3) | 0.3002 (2) | 0.0340 (7) | |
H9A | 0.3665 | 0.5194 | 0.2999 | 0.041* | |
H9B | 0.2457 | 0.4079 | 0.3260 | 0.041* | |
C10 | 0.2943 (3) | 0.3712 (3) | 0.1948 (2) | 0.0310 (7) | |
C11 | 0.1669 (3) | 0.3868 (3) | 0.1245 (2) | 0.0335 (7) | |
H11 | 0.1957 | 0.4033 | 0.0630 | 0.040* | |
C12 | 0.0405 (3) | 0.2628 (3) | 0.1066 (2) | 0.0331 (7) | |
H12 | −0.0490 | 0.2678 | 0.1139 | 0.040* | |
C13 | 0.0886 (3) | 0.1980 (3) | 0.1857 (2) | 0.0315 (7) | |
H13 | 0.0732 | 0.2268 | 0.2468 | 0.038* | |
C14 | 0.0125 (3) | 0.0649 (3) | 0.1707 (2) | 0.0357 (7) | |
H14 | 0.0309 | 0.0299 | 0.1137 | 0.043* | |
C15 | −0.1531 (3) | 0.0061 (3) | 0.1733 (3) | 0.0458 (9) | |
H15 | −0.2101 | −0.0532 | 0.1159 | 0.055* | |
C16 | −0.1057 (4) | −0.0505 (3) | 0.2560 (3) | 0.0519 (10) | |
C17 | 0.1534 (3) | −0.0169 (3) | 0.2985 (2) | 0.0378 (8) | |
C18 | 0.2642 (3) | −0.0060 (3) | 0.2526 (2) | 0.0393 (8) | |
H18 | 0.2685 | 0.0256 | 0.1952 | 0.047* | |
C19 | 0.3685 (3) | −0.0420 (3) | 0.2917 (3) | 0.0430 (8) | |
H19 | 0.4434 | −0.0337 | 0.2610 | 0.052* | |
C20 | 0.3619 (4) | −0.0899 (3) | 0.3756 (3) | 0.0460 (9) | |
C21 | 0.2550 (4) | −0.0962 (4) | 0.4239 (3) | 0.0544 (10) | |
H21 | 0.2533 | −0.1250 | 0.4826 | 0.065* | |
C22 | 0.1513 (4) | −0.0600 (4) | 0.3857 (3) | 0.0509 (10) | |
H22 | 0.0796 | −0.0645 | 0.4185 | 0.061* | |
C23 | 0.5611 (5) | −0.1357 (5) | 0.3669 (4) | 0.0807 (16) | |
H23A | 0.6198 | −0.1683 | 0.4029 | 0.121* | |
H23B | 0.6208 | −0.0564 | 0.3585 | 0.121* | |
H23C | 0.5137 | −0.1838 | 0.3048 | 0.121* | |
C24 | −0.2264 (3) | 0.0835 (3) | 0.1965 (3) | 0.0418 (9) | |
C25 | −0.1948 (4) | 0.1455 (3) | 0.2876 (3) | 0.0461 (9) | |
H25 | −0.1276 | 0.1389 | 0.3365 | 0.055* | |
C26 | −0.2613 (4) | 0.2174 (4) | 0.3075 (3) | 0.0555 (10) | |
H26 | −0.2388 | 0.2582 | 0.3696 | 0.067* | |
C27 | −0.3605 (4) | 0.2289 (4) | 0.2362 (3) | 0.0605 (11) | |
H27 | −0.4052 | 0.2774 | 0.2495 | 0.073* | |
C28 | −0.3929 (4) | 0.1674 (4) | 0.1442 (3) | 0.0618 (12) | |
H28 | −0.4591 | 0.1752 | 0.0953 | 0.074* | |
C29 | −0.3278 (4) | 0.0951 (4) | 0.1250 (3) | 0.0537 (10) | |
H29 | −0.3517 | 0.0531 | 0.0632 | 0.064* | |
C30 | 0.1230 (3) | 0.4815 (3) | 0.1585 (2) | 0.0386 (8) | |
C31 | 0.0321 (4) | 0.4623 (4) | 0.2234 (3) | 0.0473 (9) | |
H31 | 0.0003 | 0.3906 | 0.2472 | 0.057* | |
C32 | −0.0116 (5) | 0.5464 (4) | 0.2530 (3) | 0.0664 (13) | |
H32 | −0.0731 | 0.5307 | 0.2957 | 0.080* | |
C33 | 0.0349 (7) | 0.6529 (5) | 0.2198 (4) | 0.0842 (18) | |
H33 | 0.0062 | 0.7101 | 0.2406 | 0.101* | |
C34 | 0.1243 (6) | 0.6751 (4) | 0.1557 (4) | 0.0775 (16) | |
H34 | 0.1564 | 0.7477 | 0.1333 | 0.093* | |
C35 | 0.1674 (4) | 0.5889 (3) | 0.1239 (3) | 0.0537 (10) | |
C36 | 0.4283 (3) | 0.4159 (3) | 0.1513 (2) | 0.0384 (8) | |
C37 | 0.6263 (4) | 0.5862 (5) | 0.1315 (3) | 0.0768 (15) | |
H37A | 0.6678 | 0.6708 | 0.1491 | 0.115* | |
H37B | 0.6014 | 0.5664 | 0.0623 | 0.115* | |
H37C | 0.6950 | 0.5570 | 0.1577 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1027 (10) | 0.0749 (10) | 0.1001 (11) | 0.0317 (8) | 0.0319 (8) | 0.0577 (8) |
O1 | 0.0716 (17) | 0.076 (2) | 0.0706 (19) | 0.0510 (17) | 0.0408 (14) | 0.0291 (16) |
O2 | 0.0497 (14) | 0.0547 (19) | 0.0521 (16) | 0.0091 (13) | 0.0214 (11) | 0.0149 (13) |
O3 | 0.081 (2) | 0.083 (2) | 0.0504 (17) | 0.0411 (18) | 0.0232 (15) | −0.0032 (16) |
O4 | 0.0702 (18) | 0.060 (2) | 0.0491 (16) | 0.0255 (16) | −0.0112 (13) | −0.0109 (14) |
O5 | 0.0532 (16) | 0.084 (2) | 0.149 (3) | 0.0374 (16) | 0.0485 (19) | 0.078 (2) |
O6 | 0.0597 (15) | 0.083 (2) | 0.079 (2) | 0.0484 (16) | 0.0245 (14) | 0.0487 (17) |
N1 | 0.0702 (19) | 0.057 (2) | 0.0369 (16) | 0.0401 (18) | 0.0100 (14) | 0.0201 (15) |
N2 | 0.0349 (12) | 0.0346 (16) | 0.0398 (15) | 0.0216 (12) | 0.0076 (10) | 0.0116 (12) |
N3 | 0.0589 (18) | 0.0459 (19) | 0.0339 (16) | 0.0323 (16) | 0.0013 (13) | 0.0045 (14) |
N4 | 0.0355 (13) | 0.0350 (17) | 0.0586 (18) | 0.0193 (12) | 0.0137 (12) | 0.0177 (14) |
C1 | 0.0529 (18) | 0.047 (2) | 0.0362 (18) | 0.0206 (17) | 0.0092 (14) | 0.0129 (17) |
C2 | 0.0423 (16) | 0.040 (2) | 0.0277 (16) | 0.0230 (15) | 0.0104 (12) | 0.0111 (14) |
C3 | 0.0443 (16) | 0.044 (2) | 0.0240 (15) | 0.0256 (15) | 0.0068 (12) | 0.0030 (14) |
C4 | 0.0500 (18) | 0.048 (2) | 0.0393 (19) | 0.0186 (17) | 0.0110 (15) | 0.0044 (17) |
C5 | 0.049 (2) | 0.058 (3) | 0.061 (3) | 0.0101 (19) | 0.0095 (17) | −0.003 (2) |
C6 | 0.0400 (18) | 0.100 (4) | 0.050 (2) | 0.025 (2) | −0.0003 (16) | −0.003 (2) |
C7 | 0.058 (2) | 0.098 (4) | 0.037 (2) | 0.053 (3) | 0.0016 (16) | 0.006 (2) |
C8 | 0.0518 (18) | 0.050 (2) | 0.0278 (16) | 0.0287 (18) | 0.0060 (13) | 0.0033 (15) |
C9 | 0.0360 (14) | 0.0389 (19) | 0.0332 (17) | 0.0213 (14) | 0.0092 (12) | 0.0071 (14) |
C10 | 0.0329 (14) | 0.0348 (19) | 0.0317 (16) | 0.0195 (13) | 0.0082 (11) | 0.0103 (14) |
C11 | 0.0425 (15) | 0.0373 (19) | 0.0281 (16) | 0.0229 (14) | 0.0091 (12) | 0.0115 (14) |
C12 | 0.0384 (15) | 0.0376 (19) | 0.0307 (16) | 0.0239 (14) | 0.0069 (12) | 0.0046 (14) |
C13 | 0.0357 (14) | 0.0324 (18) | 0.0315 (16) | 0.0196 (13) | 0.0070 (11) | 0.0055 (13) |
C14 | 0.0412 (15) | 0.0311 (18) | 0.0406 (18) | 0.0221 (14) | 0.0070 (12) | 0.0050 (14) |
C15 | 0.0375 (16) | 0.039 (2) | 0.064 (2) | 0.0211 (15) | 0.0078 (14) | 0.0087 (17) |
C16 | 0.0438 (18) | 0.042 (2) | 0.080 (3) | 0.0235 (17) | 0.0197 (18) | 0.025 (2) |
C17 | 0.0420 (16) | 0.0296 (18) | 0.0468 (19) | 0.0188 (14) | 0.0109 (14) | 0.0120 (15) |
C18 | 0.0402 (15) | 0.037 (2) | 0.0451 (19) | 0.0187 (15) | 0.0109 (13) | 0.0159 (16) |
C19 | 0.0431 (17) | 0.043 (2) | 0.051 (2) | 0.0214 (16) | 0.0180 (14) | 0.0179 (17) |
C20 | 0.0457 (17) | 0.044 (2) | 0.054 (2) | 0.0232 (16) | 0.0111 (15) | 0.0234 (18) |
C21 | 0.060 (2) | 0.070 (3) | 0.049 (2) | 0.037 (2) | 0.0207 (17) | 0.033 (2) |
C22 | 0.0537 (19) | 0.061 (3) | 0.052 (2) | 0.0312 (19) | 0.0237 (16) | 0.0249 (19) |
C23 | 0.070 (3) | 0.103 (4) | 0.116 (4) | 0.066 (3) | 0.043 (3) | 0.063 (3) |
C24 | 0.0356 (15) | 0.038 (2) | 0.057 (2) | 0.0193 (14) | 0.0119 (14) | 0.0158 (17) |
C25 | 0.0439 (17) | 0.047 (2) | 0.050 (2) | 0.0210 (16) | 0.0104 (15) | 0.0155 (18) |
C26 | 0.057 (2) | 0.062 (3) | 0.060 (2) | 0.032 (2) | 0.0248 (18) | 0.017 (2) |
C27 | 0.059 (2) | 0.064 (3) | 0.085 (3) | 0.044 (2) | 0.032 (2) | 0.027 (2) |
C28 | 0.057 (2) | 0.080 (3) | 0.071 (3) | 0.047 (2) | 0.0166 (19) | 0.031 (2) |
C29 | 0.0485 (18) | 0.064 (3) | 0.056 (2) | 0.0327 (19) | 0.0065 (16) | 0.013 (2) |
C30 | 0.0435 (16) | 0.041 (2) | 0.0355 (17) | 0.0263 (15) | −0.0031 (13) | 0.0077 (15) |
C31 | 0.057 (2) | 0.052 (2) | 0.045 (2) | 0.0381 (19) | 0.0046 (15) | 0.0036 (17) |
C32 | 0.074 (3) | 0.080 (3) | 0.059 (3) | 0.056 (3) | −0.004 (2) | −0.008 (2) |
C33 | 0.106 (4) | 0.064 (3) | 0.090 (4) | 0.067 (3) | −0.025 (3) | −0.019 (3) |
C34 | 0.093 (3) | 0.041 (3) | 0.093 (4) | 0.039 (3) | −0.020 (3) | 0.007 (2) |
C35 | 0.057 (2) | 0.037 (2) | 0.062 (2) | 0.0219 (17) | −0.0066 (17) | 0.0126 (18) |
C36 | 0.0404 (16) | 0.053 (2) | 0.0320 (17) | 0.0278 (17) | 0.0102 (13) | 0.0177 (16) |
C37 | 0.052 (2) | 0.097 (4) | 0.061 (3) | 0.004 (2) | 0.024 (2) | 0.027 (3) |
N1—H1A | 0.8600 | C17—C18 | 1.384 (5) |
N2—H2 | 0.8600 | C17—N4 | 1.418 (4) |
N3—O4 | 1.208 (4) | C18—C19 | 1.382 (4) |
N3—O3 | 1.215 (4) | C18—H18 | 0.9300 |
C1—C2 | 1.358 (5) | C19—C20 | 1.368 (5) |
C1—N1 | 1.369 (4) | C19—H19 | 0.9300 |
C1—H1 | 0.9300 | C20—O6 | 1.380 (4) |
C2—C3 | 1.431 (5) | C20—C21 | 1.383 (5) |
C2—C9 | 1.501 (4) | C21—C22 | 1.375 (5) |
C3—C4 | 1.408 (5) | C21—H21 | 0.9300 |
C3—C8 | 1.417 (4) | C22—H22 | 0.9300 |
C4—C5 | 1.371 (5) | C23—O6 | 1.417 (5) |
C4—H4 | 0.9300 | C23—H23A | 0.9600 |
C5—C6 | 1.390 (7) | C23—H23B | 0.9600 |
C5—H5 | 0.9300 | C23—H23C | 0.9600 |
C6—C7 | 1.377 (7) | C24—C25 | 1.378 (5) |
C6—H6 | 0.9300 | C24—C29 | 1.392 (4) |
C7—C8 | 1.383 (5) | C25—C26 | 1.380 (5) |
C7—H7 | 0.9300 | C25—H25 | 0.9300 |
C8—N1 | 1.362 (5) | C26—C27 | 1.376 (5) |
C9—C10 | 1.553 (4) | C26—H26 | 0.9300 |
C9—H9A | 0.9700 | C27—C28 | 1.384 (6) |
C9—H9B | 0.9700 | C27—H27 | 0.9300 |
C10—N2 | 1.459 (4) | C28—C29 | 1.373 (5) |
C10—C36 | 1.531 (4) | C28—H28 | 0.9300 |
C10—C11 | 1.603 (3) | C29—H29 | 0.9300 |
C11—C30 | 1.511 (4) | C30—C35 | 1.385 (5) |
C11—C12 | 1.538 (5) | C30—C31 | 1.395 (5) |
C11—H11 | 0.9800 | C31—C32 | 1.374 (5) |
C12—N3 | 1.511 (4) | C31—H31 | 0.9300 |
C12—C13 | 1.558 (4) | C32—C33 | 1.365 (8) |
C12—H12 | 0.9800 | C32—H32 | 0.9300 |
C13—N2 | 1.451 (4) | C33—C34 | 1.374 (8) |
C13—C14 | 1.503 (4) | C33—H33 | 0.9300 |
C13—H13 | 0.9800 | C34—C35 | 1.402 (6) |
C14—N4 | 1.478 (4) | C34—H34 | 0.9300 |
C14—C15 | 1.581 (4) | C35—Cl1 | 1.730 (5) |
C14—H14 | 0.9800 | C36—O1 | 1.197 (4) |
C15—C24 | 1.507 (4) | C36—O2 | 1.319 (4) |
C15—C16 | 1.523 (5) | C37—O2 | 1.454 (4) |
C15—H15 | 0.9800 | C37—H37A | 0.9600 |
C16—O5 | 1.206 (5) | C37—H37B | 0.9600 |
C16—N4 | 1.365 (4) | C37—H37C | 0.9600 |
C17—C22 | 1.383 (5) | ||
C36—O2—C37 | 116.4 (3) | C16—C15—C14 | 84.6 (2) |
C20—O6—C23 | 116.9 (3) | C24—C15—H15 | 111.2 |
C8—N1—C1 | 109.2 (3) | C16—C15—H15 | 111.2 |
C8—N1—H1A | 125.4 | C14—C15—H15 | 111.2 |
C1—N1—H1A | 125.4 | O5—C16—N4 | 132.5 (3) |
C13—N2—C10 | 105.6 (2) | O5—C16—C15 | 133.9 (3) |
C13—N2—H2 | 127.2 | N4—C16—C15 | 93.6 (3) |
C10—N2—H2 | 127.2 | C22—C17—C18 | 119.3 (3) |
O4—N3—O3 | 123.6 (3) | C22—C17—N4 | 118.8 (3) |
O4—N3—C12 | 116.9 (3) | C18—C17—N4 | 121.8 (3) |
O3—N3—C12 | 119.5 (3) | C19—C18—C17 | 120.2 (3) |
C16—N4—C17 | 128.4 (3) | C19—C18—H18 | 119.9 |
C16—N4—C14 | 94.5 (3) | C17—C18—H18 | 119.9 |
C17—N4—C14 | 132.7 (3) | C20—C19—C18 | 120.1 (3) |
C2—C1—N1 | 110.6 (3) | C20—C19—H19 | 119.9 |
C2—C1—H1 | 124.7 | C18—C19—H19 | 119.9 |
N1—C1—H1 | 124.7 | C19—C20—O6 | 124.7 (3) |
C1—C2—C3 | 106.0 (3) | C19—C20—C21 | 119.7 (3) |
C1—C2—C9 | 126.1 (3) | O6—C20—C21 | 115.6 (3) |
C3—C2—C9 | 127.9 (3) | C22—C21—C20 | 120.4 (3) |
C4—C3—C8 | 118.1 (3) | C22—C21—H21 | 119.8 |
C4—C3—C2 | 134.6 (3) | C20—C21—H21 | 119.8 |
C8—C3—C2 | 107.3 (3) | C21—C22—C17 | 120.0 (3) |
C5—C4—C3 | 118.9 (4) | C21—C22—H22 | 120.0 |
C5—C4—H4 | 120.6 | C17—C22—H22 | 120.0 |
C3—C4—H4 | 120.6 | O6—C23—H23A | 109.5 |
C4—C5—C6 | 121.8 (4) | O6—C23—H23B | 109.5 |
C4—C5—H5 | 119.1 | H23A—C23—H23B | 109.5 |
C6—C5—H5 | 119.1 | O6—C23—H23C | 109.5 |
C7—C6—C5 | 121.1 (4) | H23A—C23—H23C | 109.5 |
C7—C6—H6 | 119.5 | H23B—C23—H23C | 109.5 |
C5—C6—H6 | 119.5 | C25—C24—C29 | 118.1 (3) |
C6—C7—C8 | 117.7 (3) | C25—C24—C15 | 121.7 (3) |
C6—C7—H7 | 121.2 | C29—C24—C15 | 120.3 (3) |
C8—C7—H7 | 121.2 | C24—C25—C26 | 121.1 (3) |
N1—C8—C7 | 130.5 (3) | C24—C25—H25 | 119.4 |
N1—C8—C3 | 107.0 (3) | C26—C25—H25 | 119.4 |
C7—C8—C3 | 122.5 (4) | C27—C26—C25 | 120.4 (4) |
C2—C9—C10 | 112.3 (2) | C27—C26—H26 | 119.8 |
C2—C9—H9A | 109.1 | C25—C26—H26 | 119.8 |
C10—C9—H9A | 109.1 | C26—C27—C28 | 119.1 (3) |
C2—C9—H9B | 109.1 | C26—C27—H27 | 120.4 |
C10—C9—H9B | 109.1 | C28—C27—H27 | 120.4 |
H9A—C9—H9B | 107.9 | C29—C28—C27 | 120.3 (3) |
N2—C10—C36 | 108.6 (2) | C29—C28—H28 | 119.8 |
N2—C10—C9 | 109.8 (2) | C27—C28—H28 | 119.8 |
C36—C10—C9 | 110.0 (2) | C28—C29—C24 | 121.0 (4) |
N2—C10—C11 | 105.2 (2) | C28—C29—H29 | 119.5 |
C36—C10—C11 | 108.7 (2) | C24—C29—H29 | 119.5 |
C9—C10—C11 | 114.2 (2) | C35—C30—C31 | 117.5 (3) |
C30—C11—C12 | 111.5 (2) | C35—C30—C11 | 121.3 (3) |
C30—C11—C10 | 117.8 (2) | C31—C30—C11 | 121.2 (3) |
C12—C11—C10 | 103.5 (2) | C32—C31—C30 | 121.9 (4) |
C30—C11—H11 | 107.8 | C32—C31—H31 | 119.1 |
C12—C11—H11 | 107.8 | C30—C31—H31 | 119.1 |
C10—C11—H11 | 107.8 | C33—C32—C31 | 120.2 (5) |
N3—C12—C11 | 113.1 (3) | C33—C32—H32 | 119.9 |
N3—C12—C13 | 106.7 (2) | C31—C32—H32 | 119.9 |
C11—C12—C13 | 103.8 (2) | C32—C33—C34 | 119.7 (4) |
N3—C12—H12 | 111.0 | C32—C33—H33 | 120.2 |
C11—C12—H12 | 111.0 | C34—C33—H33 | 120.2 |
C13—C12—H12 | 111.0 | C33—C34—C35 | 120.4 (4) |
N2—C13—C14 | 113.7 (2) | C33—C34—H34 | 119.8 |
N2—C13—C12 | 103.5 (2) | C35—C34—H34 | 119.8 |
C14—C13—C12 | 117.3 (2) | C30—C35—C34 | 120.3 (4) |
N2—C13—H13 | 107.3 | C30—C35—Cl1 | 122.1 (3) |
C14—C13—H13 | 107.3 | C34—C35—Cl1 | 117.5 (4) |
C12—C13—H13 | 107.3 | O1—C36—O2 | 125.4 (3) |
N4—C14—C13 | 115.3 (3) | O1—C36—C10 | 123.6 (3) |
N4—C14—C15 | 87.1 (2) | O2—C36—C10 | 111.0 (3) |
C13—C14—C15 | 117.8 (2) | O2—C37—H37A | 109.5 |
N4—C14—H14 | 111.5 | O2—C37—H37B | 109.5 |
C13—C14—H14 | 111.5 | H37A—C37—H37B | 109.5 |
C15—C14—H14 | 111.5 | O2—C37—H37C | 109.5 |
C24—C15—C16 | 116.4 (3) | H37A—C37—H37C | 109.5 |
C24—C15—C14 | 119.7 (3) | H37B—C37—H37C | 109.5 |
N1—C1—C2—C3 | 0.6 (4) | C16—C15—C24—C29 | −150.9 (3) |
N1—C1—C2—C9 | −178.0 (3) | C14—C15—C24—C29 | 109.9 (4) |
C1—C2—C3—C4 | −178.8 (3) | C29—C24—C25—C26 | −0.2 (5) |
C9—C2—C3—C4 | −0.3 (6) | C15—C24—C25—C26 | 179.1 (3) |
C1—C2—C3—C8 | −0.5 (4) | C24—C25—C26—C27 | −0.3 (6) |
C9—C2—C3—C8 | 178.1 (3) | C25—C26—C27—C28 | 0.1 (6) |
C8—C3—C4—C5 | −0.3 (5) | C26—C27—C28—C29 | 0.6 (6) |
C2—C3—C4—C5 | 177.9 (4) | C27—C28—C29—C24 | −1.1 (6) |
C3—C4—C5—C6 | 0.6 (6) | C25—C24—C29—C28 | 0.9 (6) |
C4—C5—C6—C7 | 0.1 (7) | C15—C24—C29—C28 | −178.4 (4) |
C5—C6—C7—C8 | −1.2 (6) | C12—C11—C30—C35 | −138.3 (3) |
C6—C7—C8—N1 | −178.1 (4) | C10—C11—C30—C35 | 102.2 (3) |
C6—C7—C8—C3 | 1.5 (5) | C12—C11—C30—C31 | 39.4 (4) |
C4—C3—C8—N1 | 178.9 (3) | C10—C11—C30—C31 | −80.1 (4) |
C2—C3—C8—N1 | 0.2 (3) | C35—C30—C31—C32 | −0.5 (5) |
C4—C3—C8—C7 | −0.7 (5) | C11—C30—C31—C32 | −178.3 (3) |
C2—C3—C8—C7 | −179.4 (3) | C30—C31—C32—C33 | −0.7 (6) |
C1—C2—C9—C10 | −76.9 (4) | C31—C32—C33—C34 | 0.8 (7) |
C3—C2—C9—C10 | 104.8 (4) | C32—C33—C34—C35 | 0.3 (7) |
C2—C9—C10—N2 | 58.5 (3) | C31—C30—C35—C34 | 1.6 (5) |
C2—C9—C10—C36 | −61.0 (3) | C11—C30—C35—C34 | 179.4 (3) |
C2—C9—C10—C11 | 176.5 (2) | C31—C30—C35—Cl1 | −176.2 (2) |
N2—C10—C11—C30 | 134.8 (3) | C11—C30—C35—Cl1 | 1.6 (5) |
C36—C10—C11—C30 | −109.0 (3) | C33—C34—C35—C30 | −1.5 (6) |
C9—C10—C11—C30 | 14.2 (4) | C33—C34—C35—Cl1 | 176.4 (4) |
N2—C10—C11—C12 | 11.2 (3) | N2—C10—C36—O1 | 16.0 (4) |
C36—C10—C11—C12 | 127.4 (3) | C9—C10—C36—O1 | 136.2 (3) |
C9—C10—C11—C12 | −109.4 (3) | C11—C10—C36—O1 | −98.0 (3) |
C30—C11—C12—N3 | 131.4 (2) | N2—C10—C36—O2 | −165.9 (2) |
C10—C11—C12—N3 | −101.0 (2) | C9—C10—C36—O2 | −45.6 (3) |
C30—C11—C12—C13 | −113.4 (3) | C11—C10—C36—O2 | 80.1 (3) |
C10—C11—C12—C13 | 14.3 (3) | C7—C8—N1—C1 | 179.7 (4) |
N3—C12—C13—N2 | 84.1 (3) | C3—C8—N1—C1 | 0.1 (4) |
C11—C12—C13—N2 | −35.6 (3) | C2—C1—N1—C8 | −0.4 (4) |
N3—C12—C13—C14 | −42.0 (3) | C14—C13—N2—C10 | 172.5 (2) |
C11—C12—C13—C14 | −161.7 (2) | C12—C13—N2—C10 | 44.1 (3) |
N2—C13—C14—N4 | 72.2 (3) | C36—C10—N2—C13 | −150.8 (2) |
C12—C13—C14—N4 | −166.9 (2) | C9—C10—N2—C13 | 88.8 (2) |
N2—C13—C14—C15 | 172.8 (3) | C11—C10—N2—C13 | −34.6 (3) |
C12—C13—C14—C15 | −66.3 (4) | C11—C12—N3—O4 | −157.2 (3) |
N4—C14—C15—C24 | 113.5 (3) | C13—C12—N3—O4 | 89.3 (3) |
C13—C14—C15—C24 | −3.7 (5) | C11—C12—N3—O3 | 25.3 (4) |
N4—C14—C15—C16 | −3.9 (3) | C13—C12—N3—O3 | −88.2 (3) |
C13—C14—C15—C16 | −121.1 (3) | O5—C16—N4—C17 | 16.9 (7) |
C24—C15—C16—O5 | 63.8 (6) | C15—C16—N4—C17 | −163.0 (3) |
C14—C15—C16—O5 | −175.6 (5) | O5—C16—N4—C14 | 175.3 (5) |
C24—C15—C16—N4 | −116.3 (3) | C15—C16—N4—C14 | −4.5 (3) |
C14—C15—C16—N4 | 4.2 (3) | C22—C17—N4—C16 | −36.5 (5) |
C22—C17—C18—C19 | 2.4 (5) | C18—C17—N4—C16 | 140.0 (4) |
N4—C17—C18—C19 | −174.1 (3) | C22—C17—N4—C14 | 173.4 (3) |
C17—C18—C19—C20 | 0.8 (6) | C18—C17—N4—C14 | −10.1 (6) |
C18—C19—C20—O6 | 176.6 (4) | C13—C14—N4—C16 | 123.8 (3) |
C18—C19—C20—C21 | −3.5 (6) | C15—C14—N4—C16 | 4.4 (3) |
C19—C20—C21—C22 | 3.2 (6) | C13—C14—N4—C17 | −79.3 (4) |
O6—C20—C21—C22 | −176.9 (4) | C15—C14—N4—C17 | 161.3 (4) |
C20—C21—C22—C17 | −0.1 (7) | O1—C36—O2—C37 | −1.3 (5) |
C18—C17—C22—C21 | −2.7 (6) | C10—C36—O2—C37 | −179.4 (3) |
N4—C17—C22—C21 | 173.9 (4) | C19—C20—O6—C23 | −4.1 (6) |
C16—C15—C24—C25 | 29.9 (5) | C21—C20—O6—C23 | 176.0 (4) |
C14—C15—C24—C25 | −69.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···Cl1 | 0.98 | 2.57 | 3.095 (4) | 114 |
C11—H11···O3 | 0.98 | 2.37 | 2.786 (4) | 105 |
C22—H22···O5 | 0.93 | 2.59 | 3.080 (6) | 113 |
C14—H14···O4i | 0.98 | 2.53 | 3.443 (5) | 154 |
C34—H34···O4ii | 0.93 | 2.59 | 3.414 (6) | 148 |
N1—H1A···O6iii | 0.86 | 2.14 | 2.982 (5) | 167 |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z; (iii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C37H33ClN4O6 |
Mr | 665.12 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.399 (3), 12.500 (3), 14.211 (3) |
α, β, γ (°) | 93.766 (6), 99.962 (6), 114.066 (5) |
V (Å3) | 1642.1 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.17 |
Crystal size (mm) | 0.30 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker KAPPA APEX2 CCD diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.951, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25481, 5563, 3770 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.317, 1.10 |
No. of reflections | 5563 |
No. of parameters | 433 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.51, −0.64 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···Cl1 | 0.98 | 2.57 | 3.095 (4) | 114 |
C11—H11···O3 | 0.98 | 2.37 | 2.786 (4) | 105 |
C22—H22···O5 | 0.93 | 2.59 | 3.080 (6) | 113 |
C14—H14···O4i | 0.98 | 2.53 | 3.443 (5) | 154 |
C34—H34···O4ii | 0.93 | 2.59 | 3.414 (6) | 148 |
N1—H1A···O6iii | 0.86 | 2.14 | 2.982 (5) | 167 |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z; (iii) −x+1, −y, −z+1. |
Acknowledgements
SN thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions. SN thanks SRM management, India, for their support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
β-Lactams are one of the best known and most extensively studied class of compounds due to their biological activity (Bruggink, 2001; Morin & Gorman, 1982; Katritzky et al., 1996; Georg, 1993). The β-lactam class of drugs have revolutionized treatment in medicine (Coyne et al., 2007). In the late 1970's and early 1980's, the first class of the monocyclic β-lactam antibacterial agents were found in natural sources (Dobrowolski et al., 2004). All β-lactams are based on a β-lactam ring responsible for the antibacterial activity and variable side chains that account for the major differences in their chemical and pharmocological properties (Cha et al., 2006). We report herein the crystal structure of the title compound, (I).
In the title compound, (I), (Fig. 1) the four-membered β-lactam ring A (N4/C14-C16) is nearly planar, with a maximum deviation of 0.038 (4) Å for atom N1. The C14-C15 [1.581 (4) Å] and C15-C16 [1.523 (5) Å] bonds agree with those observed in similar structures (Bhaskaran et al., 2006; Kamala et al., 2008). The C14-C15-C16 [84.6 (2)°] bond angle is comparable to the corresponding value [87.0 (3)°)] in a related structure (Ülkü et al., 1997). The sum of the bond angles around atom N4 [355.6 (3)°] indicates sp2 hybridization. The planar rings A, B (C17-C22) and C (C24-C29) are oriented at dihedral angles of A/B = 30.0 (1)°, A/C = 76.3 (1)° and B/C = 50.2 (1)°. The planar indole moiety is oriented with respect to rings A, C and D (C30-C35) at dihedral angles of 30.9 (1)°, 73.0 (1)° and 70.7 (1)°, respectively. The pyrrolidine ring E (N2/C10-C13) adopts a twisted conformation, with asymmetry [ΔC2 (C11) = 0.011 (1), ΔCs (C13) = 0.085 (2)] (Nardelli, 1995) and puckering [q2 = 0.402 (3) Å and ϕ = -21.1 (4)°] (Cremer & Pople, 1975) parameters. Atom N2 deviates from the mean plane of (N2/C10-C12) by 0.553 (7) Å.
The intramolecular C-H···Cl and C-H···O hydrogen bonds (Table 1) result in the formation of two five- and one six-membered rings: F (O3/N3/C11/H11A/C12), G (Cl1/C11/H11/C30/C39) and H (O5/N4/C16/C17/C22/H22), respectively. In the crystal structure, intermolecular C-H···O and N-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. A weak π—π interaction between (N1/C1-C3/C8) rings at x, y, z and 1 - x, 1 - y, 1 - z further stabilize the structure, with a centroid-centroid distance of 3.806 (2) Å.