organic compounds
Ethyl 1-(4-methoxyphenyl)-2-nitro-3-[4-oxo-3-phenyl-1-(4-methoxyphenyl)azetidin-2-yl]-2,3,10,10a-tetrahydro-1H,5H-pyrrolo[1,2-b]isoquinoline-10a-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, C38H37N3O7, the pyrrolidine ring adopts a twist conformation and the six-membered heterocyclic ring has a boat conformation. In the molecules are linked into a three-dimensional framework through intermolecular C—H⋯O hydrogen bonds. One ethyl group is disordered over two positions with occupancies 0.67 (2)/0.33 (2).
Related literature
For related literature, see: Allen et al. (1987); Amal Raj et al. (2003); Borthwick et al. (2003); Brakhage (1998); Cremer & Pople (1975); Fernandes et al. (2004); Kamala et al. (2008); Katritzky et al. (1996); Morin & Gorman (1982); Nardelli (1983); Sundari et al. (2006); Verkman (1990); Weissman et al. (1993); Georg & Ravikumar (1993); LaVoie et al. (1983).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP Bruker, 2004); 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: PLATON (Spek, 2003).
Supporting information
10.1107/S1600536808010428/bt2696sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010428/bt2696Isup2.hkl
To a stirring solution of 1 mmol of 5-[1'-N-(p-methoxy)-phenyl)-3'-phenyl- azetidine-2'-one]-4-nitro-3-(p-methoxy)-phenyl-2-ethoxy carbonyl-2-benzyl -pyrrolidine in 20 ml of dry chloroform was added 1 mmol of paraformaldehyde followed by 0.1 mmol of trifluroacetic acid at room temperature. After completion of the reaction the mixture was washed with water and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was subjected to
with hexane ethylacetate (9:1) to obtain pure cyclized product. The compound was recrystallized from ethylacetae.In the absence of anomalous scatterers, Friedel pairs were merged and the
was arbitrarily set. One ethyl group is disordered over two positions (C36A/C37A and C36B/C37B), with refined occupancies of 0.67 (2) and 0.33 (2). H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C–H = 0.93 or 0.96 Å and Uiso(H)= 1.2–1.5Ueq(C).Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP Bruker, 2004); 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: PLATON (Spek, 2003).Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids. | |
Fig. 2. The packing of the molecules viewed along the c axis. |
C38H37N3O7 | F(000) = 1368 |
Mr = 647.71 | Dx = 1.290 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 68599 reflections |
a = 9.0149 (3) Å | θ = 1.2–26.7° |
b = 11.0865 (4) Å | µ = 0.09 mm−1 |
c = 33.3731 (11) Å | T = 293 K |
V = 3335.4 (2) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.20 × 0.20 mm |
Bruker KappaAPEX2 diffractometer | 3960 independent reflections |
Radiation source: fine-focus sealed tube | 3318 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and ϕ scans | θmax = 26.7°, θmin = 1.2° |
Absorption correction: multi-scan (Blessing, 1995) | h = −11→11 |
Tmin = 0.982, Tmax = 0.982 | k = −13→13 |
68599 measured reflections | l = −42→42 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0606P)2 + 0.4467P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3960 reflections | Δρmax = 0.14 e Å−3 |
453 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0035 (7) |
C38H37N3O7 | V = 3335.4 (2) Å3 |
Mr = 647.71 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.0149 (3) Å | µ = 0.09 mm−1 |
b = 11.0865 (4) Å | T = 293 K |
c = 33.3731 (11) Å | 0.20 × 0.20 × 0.20 mm |
Bruker KappaAPEX2 diffractometer | 3960 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 3318 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.982 | Rint = 0.033 |
68599 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.14 e Å−3 |
3960 reflections | Δρmin = −0.16 e Å−3 |
453 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 | Occ. (<1) | |
C1 | 0.5650 (3) | 0.1895 (2) | 0.11810 (7) | 0.0428 (5) | |
H1 | 0.6078 | 0.1997 | 0.1449 | 0.051* | |
C2 | 0.6846 (3) | 0.2110 (2) | 0.08439 (7) | 0.0465 (5) | |
H2 | 0.7811 | 0.2300 | 0.0964 | 0.056* | |
C3 | 0.6714 (3) | 0.0759 (2) | 0.07673 (7) | 0.0518 (6) | |
C4 | 0.4217 (3) | 0.26005 (18) | 0.11375 (6) | 0.0392 (5) | |
H4 | 0.3956 | 0.2613 | 0.0853 | 0.047* | |
C5 | 0.4352 (3) | 0.3919 (2) | 0.12799 (7) | 0.0441 (5) | |
H5 | 0.4661 | 0.4435 | 0.1057 | 0.053* | |
C6 | 0.2805 (3) | 0.4279 (2) | 0.14202 (7) | 0.0452 (5) | |
H6 | 0.2911 | 0.4792 | 0.1658 | 0.054* | |
C7 | 0.2091 (3) | 0.3061 (2) | 0.15540 (6) | 0.0418 (5) | |
C8 | 0.0419 (3) | 0.2946 (2) | 0.14583 (8) | 0.0509 (6) | |
H8A | −0.0144 | 0.3490 | 0.1628 | 0.061* | |
H8B | 0.0240 | 0.3164 | 0.1181 | 0.061* | |
C9 | −0.0065 (3) | 0.1674 (2) | 0.15306 (7) | 0.0481 (6) | |
C10 | −0.1225 (3) | 0.1330 (3) | 0.17775 (8) | 0.0601 (7) | |
H10 | −0.1790 | 0.1911 | 0.1908 | 0.072* | |
C11 | −0.1538 (4) | 0.0124 (3) | 0.18292 (9) | 0.0702 (8) | |
H11 | −0.2323 | −0.0106 | 0.1993 | 0.084* | |
C12 | −0.0702 (4) | −0.0739 (3) | 0.16414 (10) | 0.0740 (9) | |
H12 | −0.0926 | −0.1551 | 0.1677 | 0.089* | |
C13 | 0.0469 (4) | −0.0409 (3) | 0.13991 (9) | 0.0645 (7) | |
H13 | 0.1039 | −0.0996 | 0.1273 | 0.077* | |
C14 | 0.0792 (3) | 0.0797 (2) | 0.13448 (7) | 0.0505 (6) | |
C15 | 0.2094 (3) | 0.1248 (2) | 0.11103 (7) | 0.0480 (5) | |
H15A | 0.2717 | 0.0576 | 0.1032 | 0.058* | |
H15B | 0.1752 | 0.1650 | 0.0869 | 0.058* | |
C16 | 0.1960 (3) | 0.4982 (2) | 0.11054 (7) | 0.0469 (5) | |
C17 | 0.0909 (3) | 0.5824 (2) | 0.12263 (8) | 0.0601 (7) | |
H17 | 0.0744 | 0.5938 | 0.1499 | 0.072* | |
C18 | 0.0110 (4) | 0.6489 (2) | 0.09578 (9) | 0.0658 (7) | |
H18 | −0.0600 | 0.7033 | 0.1048 | 0.079* | |
C19 | 0.0358 (3) | 0.6354 (2) | 0.05499 (8) | 0.0592 (7) | |
C20 | 0.1387 (3) | 0.5535 (3) | 0.04209 (8) | 0.0598 (7) | |
H20 | 0.1563 | 0.5437 | 0.0148 | 0.072* | |
C21 | 0.2168 (3) | 0.4850 (2) | 0.06968 (7) | 0.0550 (6) | |
H21 | 0.2852 | 0.4286 | 0.0605 | 0.066* | |
C22 | 0.6510 (3) | 0.2965 (2) | 0.05059 (7) | 0.0484 (5) | |
C23 | 0.7102 (4) | 0.4110 (3) | 0.05080 (9) | 0.0628 (7) | |
H23 | 0.7770 | 0.4333 | 0.0707 | 0.075* | |
C24 | 0.6704 (4) | 0.4931 (3) | 0.02139 (11) | 0.0822 (10) | |
H24 | 0.7105 | 0.5704 | 0.0218 | 0.099* | |
C25 | 0.5729 (4) | 0.4619 (3) | −0.00828 (10) | 0.0822 (10) | |
H25 | 0.5448 | 0.5181 | −0.0275 | 0.099* | |
C26 | 0.5175 (4) | 0.3476 (3) | −0.00931 (8) | 0.0732 (9) | |
H26 | 0.4531 | 0.3252 | −0.0298 | 0.088* | |
C27 | 0.5563 (3) | 0.2648 (3) | 0.01987 (7) | 0.0563 (6) | |
H27 | 0.5182 | 0.1869 | 0.0188 | 0.068* | |
C28 | 0.5268 (3) | −0.0417 (2) | 0.12839 (7) | 0.0471 (5) | |
C29 | 0.4518 (3) | −0.0313 (2) | 0.16414 (8) | 0.0549 (6) | |
H29 | 0.4239 | 0.0446 | 0.1733 | 0.066* | |
C30 | 0.4176 (3) | −0.1326 (2) | 0.18659 (8) | 0.0579 (7) | |
H30 | 0.3682 | −0.1244 | 0.2109 | 0.069* | |
C31 | 0.4563 (4) | −0.2445 (2) | 0.17306 (8) | 0.0583 (7) | |
C32 | 0.5345 (4) | −0.2552 (2) | 0.13739 (8) | 0.0698 (8) | |
H32 | 0.5635 | −0.3311 | 0.1286 | 0.084* | |
C33 | 0.5695 (4) | −0.1558 (2) | 0.11504 (8) | 0.0615 (7) | |
H33 | 0.6214 | −0.1642 | 0.0911 | 0.074* | |
C34 | 0.3451 (6) | −0.3423 (3) | 0.22891 (10) | 0.1026 (15) | |
H34A | 0.3317 | −0.4215 | 0.2399 | 0.154* | |
H34B | 0.2500 | −0.3067 | 0.2236 | 0.154* | |
H34C | 0.3984 | −0.2930 | 0.2477 | 0.154* | |
C35 | 0.2155 (3) | 0.2959 (2) | 0.20132 (7) | 0.0509 (6) | |
C36A | 0.227 (2) | 0.1693 (8) | 0.2565 (2) | 0.099 (4) | 0.67 (2) |
H36A | 0.3178 | 0.1371 | 0.2677 | 0.119* | 0.67 (2) |
H36B | 0.2132 | 0.2487 | 0.2681 | 0.119* | 0.67 (2) |
C36B | 0.2763 (18) | 0.166 (2) | 0.2577 (7) | 0.094 (8) | 0.33 (2) |
H36C | 0.2370 | 0.2319 | 0.2737 | 0.113* | 0.33 (2) |
H36D | 0.3801 | 0.1541 | 0.2641 | 0.113* | 0.33 (2) |
C37A | 0.1243 (12) | 0.1053 (17) | 0.2693 (3) | 0.113 (5) | 0.67 (2) |
H37A | 0.1328 | 0.0977 | 0.2978 | 0.170* | 0.67 (2) |
H37B | 0.1300 | 0.0269 | 0.2572 | 0.170* | 0.67 (2) |
H37C | 0.0309 | 0.1419 | 0.2627 | 0.170* | 0.67 (2) |
C37B | 0.182 (4) | 0.0452 (14) | 0.2633 (4) | 0.130 (9) | 0.33 (2) |
H37D | 0.1729 | 0.0272 | 0.2914 | 0.196* | 0.33 (2) |
H37E | 0.2311 | −0.0203 | 0.2500 | 0.196* | 0.33 (2) |
H37F | 0.0849 | 0.0560 | 0.2520 | 0.196* | 0.33 (2) |
C38 | −0.0228 (5) | 0.6993 (3) | −0.01129 (10) | 0.0934 (11) | |
H38A | −0.0871 | 0.7543 | −0.0252 | 0.140* | |
H38B | −0.0431 | 0.6184 | −0.0199 | 0.140* | |
H38C | 0.0786 | 0.7190 | −0.0171 | 0.140* | |
N1 | 0.5645 (2) | 0.06099 (17) | 0.10584 (6) | 0.0476 (5) | |
N2 | 0.2955 (2) | 0.20995 (16) | 0.13575 (5) | 0.0402 (4) | |
N3 | 0.5465 (3) | 0.40018 (18) | 0.16171 (7) | 0.0531 (5) | |
O1 | 0.7299 (3) | 0.00518 (18) | 0.05473 (6) | 0.0730 (6) | |
O2 | 0.4270 (3) | −0.35051 (16) | 0.19254 (5) | 0.0772 (7) | |
O3 | 0.2539 (2) | 0.18744 (16) | 0.21413 (5) | 0.0614 (5) | |
O4 | 0.1785 (3) | 0.37724 (19) | 0.22274 (6) | 0.0777 (6) | |
O5 | −0.0475 (3) | 0.70850 (19) | 0.03026 (7) | 0.0815 (6) | |
O6 | 0.5102 (2) | 0.3667 (2) | 0.19483 (6) | 0.0699 (6) | |
O7 | 0.6700 (2) | 0.4365 (2) | 0.15328 (7) | 0.0782 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0449 (12) | 0.0404 (11) | 0.0429 (11) | −0.0039 (10) | 0.0002 (10) | 0.0047 (9) |
C2 | 0.0392 (11) | 0.0484 (13) | 0.0519 (12) | −0.0036 (10) | 0.0007 (10) | 0.0082 (10) |
C3 | 0.0535 (14) | 0.0512 (13) | 0.0508 (13) | 0.0027 (12) | 0.0079 (11) | 0.0064 (11) |
C4 | 0.0432 (11) | 0.0373 (10) | 0.0371 (10) | −0.0031 (9) | −0.0003 (9) | 0.0023 (9) |
C5 | 0.0466 (12) | 0.0394 (11) | 0.0464 (11) | −0.0039 (10) | −0.0068 (10) | 0.0027 (9) |
C6 | 0.0509 (13) | 0.0396 (11) | 0.0452 (12) | −0.0006 (11) | −0.0026 (10) | −0.0048 (10) |
C7 | 0.0449 (11) | 0.0428 (11) | 0.0377 (10) | 0.0001 (11) | −0.0014 (9) | −0.0024 (9) |
C8 | 0.0424 (12) | 0.0563 (14) | 0.0540 (13) | 0.0024 (12) | −0.0023 (11) | 0.0022 (11) |
C9 | 0.0394 (12) | 0.0631 (15) | 0.0419 (11) | −0.0043 (11) | −0.0057 (10) | 0.0048 (11) |
C10 | 0.0426 (13) | 0.0831 (19) | 0.0546 (14) | −0.0019 (14) | −0.0012 (12) | 0.0051 (14) |
C11 | 0.0568 (16) | 0.091 (2) | 0.0629 (16) | −0.0254 (17) | 0.0044 (14) | 0.0133 (16) |
C12 | 0.074 (2) | 0.0660 (18) | 0.082 (2) | −0.0271 (18) | 0.0046 (17) | 0.0048 (16) |
C13 | 0.0657 (18) | 0.0564 (15) | 0.0716 (17) | −0.0199 (15) | 0.0026 (15) | −0.0070 (13) |
C14 | 0.0469 (13) | 0.0582 (14) | 0.0463 (12) | −0.0132 (12) | −0.0050 (10) | −0.0018 (11) |
C15 | 0.0487 (13) | 0.0488 (12) | 0.0464 (12) | −0.0099 (11) | 0.0007 (11) | −0.0088 (10) |
C16 | 0.0530 (14) | 0.0380 (11) | 0.0498 (12) | −0.0001 (11) | −0.0011 (11) | −0.0026 (10) |
C17 | 0.0734 (18) | 0.0538 (14) | 0.0531 (14) | 0.0148 (14) | −0.0002 (13) | −0.0067 (12) |
C18 | 0.0713 (18) | 0.0537 (15) | 0.0723 (17) | 0.0186 (14) | −0.0074 (15) | −0.0066 (14) |
C19 | 0.0673 (17) | 0.0438 (13) | 0.0665 (15) | 0.0025 (13) | −0.0126 (14) | 0.0081 (12) |
C20 | 0.0722 (17) | 0.0584 (15) | 0.0488 (13) | 0.0083 (15) | −0.0034 (13) | 0.0048 (11) |
C21 | 0.0643 (16) | 0.0488 (13) | 0.0520 (13) | 0.0105 (13) | 0.0008 (12) | 0.0006 (11) |
C22 | 0.0410 (12) | 0.0519 (13) | 0.0524 (13) | −0.0002 (11) | 0.0046 (10) | 0.0104 (11) |
C23 | 0.0612 (16) | 0.0583 (16) | 0.0689 (16) | −0.0106 (14) | −0.0019 (14) | 0.0140 (13) |
C24 | 0.093 (2) | 0.0612 (18) | 0.093 (2) | −0.0071 (18) | 0.005 (2) | 0.0275 (17) |
C25 | 0.085 (2) | 0.089 (2) | 0.0730 (19) | 0.013 (2) | 0.0069 (18) | 0.0370 (18) |
C26 | 0.0676 (18) | 0.102 (2) | 0.0499 (14) | 0.0056 (18) | −0.0012 (13) | 0.0150 (16) |
C27 | 0.0539 (15) | 0.0645 (15) | 0.0506 (13) | −0.0039 (13) | 0.0025 (12) | 0.0048 (12) |
C28 | 0.0497 (13) | 0.0423 (12) | 0.0493 (12) | −0.0023 (11) | 0.0018 (11) | 0.0062 (10) |
C29 | 0.0641 (16) | 0.0421 (12) | 0.0584 (14) | 0.0028 (12) | 0.0105 (13) | 0.0037 (11) |
C30 | 0.0681 (17) | 0.0518 (14) | 0.0537 (14) | −0.0077 (14) | 0.0097 (13) | 0.0072 (11) |
C31 | 0.0806 (19) | 0.0440 (13) | 0.0504 (13) | −0.0154 (14) | −0.0013 (14) | 0.0043 (11) |
C32 | 0.110 (3) | 0.0406 (13) | 0.0590 (15) | −0.0050 (16) | 0.0063 (17) | −0.0015 (12) |
C33 | 0.085 (2) | 0.0484 (14) | 0.0507 (13) | −0.0015 (14) | 0.0103 (14) | 0.0000 (11) |
C34 | 0.168 (4) | 0.074 (2) | 0.0659 (19) | −0.049 (3) | 0.029 (2) | 0.0030 (17) |
C35 | 0.0561 (14) | 0.0558 (14) | 0.0406 (11) | −0.0051 (13) | 0.0009 (11) | −0.0045 (11) |
C36A | 0.185 (11) | 0.086 (5) | 0.027 (3) | −0.057 (6) | −0.007 (5) | 0.006 (3) |
C36B | 0.052 (6) | 0.17 (2) | 0.066 (9) | 0.037 (11) | −0.012 (5) | 0.039 (9) |
C37A | 0.100 (6) | 0.179 (13) | 0.062 (4) | −0.039 (7) | 0.002 (4) | 0.032 (6) |
C37B | 0.26 (3) | 0.073 (9) | 0.056 (6) | 0.017 (12) | 0.060 (12) | 0.022 (6) |
C38 | 0.108 (3) | 0.091 (2) | 0.082 (2) | 0.013 (2) | −0.021 (2) | 0.0345 (18) |
N1 | 0.0521 (11) | 0.0395 (10) | 0.0512 (10) | 0.0007 (9) | 0.0073 (9) | 0.0045 (8) |
N2 | 0.0409 (10) | 0.0394 (9) | 0.0404 (9) | −0.0045 (8) | 0.0009 (8) | −0.0033 (8) |
N3 | 0.0540 (13) | 0.0427 (10) | 0.0625 (13) | −0.0060 (10) | −0.0127 (11) | −0.0022 (10) |
O1 | 0.0886 (15) | 0.0584 (11) | 0.0719 (12) | 0.0103 (11) | 0.0320 (12) | 0.0013 (10) |
O2 | 0.1283 (19) | 0.0457 (10) | 0.0576 (10) | −0.0274 (12) | 0.0074 (12) | 0.0055 (8) |
O3 | 0.0868 (13) | 0.0590 (10) | 0.0386 (8) | −0.0079 (10) | −0.0050 (9) | 0.0070 (8) |
O4 | 0.1063 (18) | 0.0765 (13) | 0.0502 (10) | 0.0096 (13) | 0.0095 (11) | −0.0168 (10) |
O5 | 0.0965 (16) | 0.0656 (12) | 0.0824 (14) | 0.0216 (13) | −0.0214 (13) | 0.0100 (11) |
O6 | 0.0764 (13) | 0.0744 (13) | 0.0590 (11) | −0.0144 (11) | −0.0207 (10) | 0.0107 (10) |
O7 | 0.0528 (12) | 0.0899 (15) | 0.0921 (14) | −0.0189 (12) | −0.0117 (11) | −0.0037 (12) |
C1—N1 | 1.482 (3) | C22—C23 | 1.377 (4) |
C1—C4 | 1.517 (3) | C22—C27 | 1.380 (4) |
C1—C2 | 1.577 (3) | C23—C24 | 1.386 (4) |
C1—H1 | 0.9800 | C23—H23 | 0.9300 |
C2—C22 | 1.504 (3) | C24—C25 | 1.369 (5) |
C2—C3 | 1.524 (4) | C24—H24 | 0.9300 |
C2—H2 | 0.9800 | C25—C26 | 1.362 (5) |
C3—O1 | 1.197 (3) | C25—H25 | 0.9300 |
C3—N1 | 1.378 (3) | C26—C27 | 1.384 (4) |
C4—N2 | 1.464 (3) | C26—H26 | 0.9300 |
C4—C5 | 1.542 (3) | C27—H27 | 0.9300 |
C4—H4 | 0.9800 | C28—C29 | 1.376 (4) |
C5—N3 | 1.511 (3) | C28—C33 | 1.395 (3) |
C5—C6 | 1.524 (3) | C28—N1 | 1.406 (3) |
C5—H5 | 0.9800 | C29—C30 | 1.384 (3) |
C6—C16 | 1.514 (3) | C29—H29 | 0.9300 |
C6—C7 | 1.561 (3) | C30—C31 | 1.366 (4) |
C6—H6 | 0.9800 | C30—H30 | 0.9300 |
C7—N2 | 1.474 (3) | C31—O2 | 1.369 (3) |
C7—C35 | 1.538 (3) | C31—C32 | 1.388 (4) |
C7—C8 | 1.545 (3) | C32—C33 | 1.367 (4) |
C8—C9 | 1.496 (4) | C32—H32 | 0.9300 |
C8—H8A | 0.9700 | C33—H33 | 0.9300 |
C8—H8B | 0.9700 | C34—O2 | 1.424 (4) |
C9—C10 | 1.385 (4) | C34—H34A | 0.9600 |
C9—C14 | 1.388 (4) | C34—H34B | 0.9600 |
C10—C11 | 1.377 (4) | C34—H34C | 0.9600 |
C10—H10 | 0.9300 | C35—O4 | 1.198 (3) |
C11—C12 | 1.370 (5) | C35—O3 | 1.322 (3) |
C11—H11 | 0.9300 | C36A—C37A | 1.240 (17) |
C12—C13 | 1.380 (4) | C36A—O3 | 1.448 (8) |
C12—H12 | 0.9300 | C36A—H36A | 0.9700 |
C13—C14 | 1.380 (4) | C36A—H36B | 0.9700 |
C13—H13 | 0.9300 | C36B—O3 | 1.49 (2) |
C14—C15 | 1.497 (3) | C36B—C37B | 1.60 (3) |
C15—N2 | 1.474 (3) | C36B—H36C | 0.9700 |
C15—H15A | 0.9700 | C36B—H36D | 0.9700 |
C15—H15B | 0.9700 | C37A—H37A | 0.9600 |
C16—C21 | 1.384 (3) | C37A—H37B | 0.9600 |
C16—C17 | 1.390 (3) | C37A—H37C | 0.9600 |
C17—C18 | 1.366 (4) | C37B—H37D | 0.9600 |
C17—H17 | 0.9300 | C37B—H37E | 0.9600 |
C18—C19 | 1.387 (4) | C37B—H37F | 0.9600 |
C18—H18 | 0.9300 | C38—O5 | 1.408 (4) |
C19—C20 | 1.368 (4) | C38—H38A | 0.9600 |
C19—O5 | 1.379 (3) | C38—H38B | 0.9600 |
C20—C21 | 1.385 (4) | C38—H38C | 0.9600 |
C20—H20 | 0.9300 | N3—O6 | 1.211 (3) |
C21—H21 | 0.9300 | N3—O7 | 1.217 (3) |
N1—C1—C4 | 117.82 (19) | C23—C22—C2 | 119.9 (2) |
N1—C1—C2 | 87.16 (17) | C27—C22—C2 | 121.4 (2) |
C4—C1—C2 | 115.87 (17) | C22—C23—C24 | 120.1 (3) |
N1—C1—H1 | 111.3 | C22—C23—H23 | 120.0 |
C4—C1—H1 | 111.3 | C24—C23—H23 | 120.0 |
C2—C1—H1 | 111.3 | C25—C24—C23 | 120.8 (3) |
C22—C2—C3 | 118.6 (2) | C25—C24—H24 | 119.6 |
C22—C2—C1 | 119.5 (2) | C23—C24—H24 | 119.6 |
C3—C2—C1 | 85.25 (17) | C26—C25—C24 | 119.3 (3) |
C22—C2—H2 | 110.4 | C26—C25—H25 | 120.4 |
C3—C2—H2 | 110.4 | C24—C25—H25 | 120.4 |
C1—C2—H2 | 110.4 | C25—C26—C27 | 120.4 (3) |
O1—C3—N1 | 131.5 (2) | C25—C26—H26 | 119.8 |
O1—C3—C2 | 135.4 (2) | C27—C26—H26 | 119.8 |
N1—C3—C2 | 93.13 (19) | C22—C27—C26 | 120.7 (3) |
N2—C4—C1 | 114.74 (16) | C22—C27—H27 | 119.7 |
N2—C4—C5 | 105.44 (17) | C26—C27—H27 | 119.7 |
C1—C4—C5 | 113.11 (18) | C29—C28—C33 | 119.2 (2) |
N2—C4—H4 | 107.7 | C29—C28—N1 | 121.0 (2) |
C1—C4—H4 | 107.7 | C33—C28—N1 | 119.8 (2) |
C5—C4—H4 | 107.7 | C28—C29—C30 | 120.7 (2) |
N3—C5—C6 | 111.29 (19) | C28—C29—H29 | 119.6 |
N3—C5—C4 | 109.85 (18) | C30—C29—H29 | 119.6 |
C6—C5—C4 | 105.74 (18) | C31—C30—C29 | 120.1 (2) |
N3—C5—H5 | 110.0 | C31—C30—H30 | 120.0 |
C6—C5—H5 | 110.0 | C29—C30—H30 | 120.0 |
C4—C5—H5 | 110.0 | C30—C31—O2 | 125.0 (2) |
C16—C6—C5 | 112.48 (19) | C30—C31—C32 | 119.4 (2) |
C16—C6—C7 | 115.8 (2) | O2—C31—C32 | 115.6 (2) |
C5—C6—C7 | 103.80 (18) | C33—C32—C31 | 121.1 (3) |
C16—C6—H6 | 108.1 | C33—C32—H32 | 119.5 |
C5—C6—H6 | 108.1 | C31—C32—H32 | 119.5 |
C7—C6—H6 | 108.1 | C32—C33—C28 | 119.5 (2) |
N2—C7—C35 | 111.71 (19) | C32—C33—H33 | 120.2 |
N2—C7—C8 | 111.33 (19) | C28—C33—H33 | 120.2 |
C35—C7—C8 | 103.68 (19) | O2—C34—H34A | 109.5 |
N2—C7—C6 | 106.29 (17) | O2—C34—H34B | 109.5 |
C35—C7—C6 | 109.46 (19) | H34A—C34—H34B | 109.5 |
C8—C7—C6 | 114.5 (2) | O2—C34—H34C | 109.5 |
C9—C8—C7 | 109.2 (2) | H34A—C34—H34C | 109.5 |
C9—C8—H8A | 109.8 | H34B—C34—H34C | 109.5 |
C7—C8—H8A | 109.8 | O4—C35—O3 | 124.4 (2) |
C9—C8—H8B | 109.8 | O4—C35—C7 | 121.9 (2) |
C7—C8—H8B | 109.8 | O3—C35—C7 | 113.5 (2) |
H8A—C8—H8B | 108.3 | C37A—C36A—O3 | 122.8 (11) |
C10—C9—C14 | 119.5 (3) | C37A—C36A—H36A | 106.6 |
C10—C9—C8 | 125.2 (3) | O3—C36A—H36A | 106.6 |
C14—C9—C8 | 115.2 (2) | C37A—C36A—H36B | 106.6 |
C11—C10—C9 | 119.8 (3) | O3—C36A—H36B | 106.6 |
C11—C10—H10 | 120.1 | H36A—C36A—H36B | 106.6 |
C9—C10—H10 | 120.1 | O3—C36B—C37B | 100.1 (15) |
C12—C11—C10 | 120.6 (3) | O3—C36B—H36C | 111.7 |
C12—C11—H11 | 119.7 | C37B—C36B—H36C | 111.7 |
C10—C11—H11 | 119.7 | O3—C36B—H36D | 111.7 |
C11—C12—C13 | 120.2 (3) | C37B—C36B—H36D | 111.7 |
C11—C12—H12 | 119.9 | H36C—C36B—H36D | 109.5 |
C13—C12—H12 | 119.9 | C36A—C37A—H37A | 109.5 |
C14—C13—C12 | 119.7 (3) | C36A—C37A—H37B | 109.5 |
C14—C13—H13 | 120.2 | H37A—C37A—H37B | 109.5 |
C12—C13—H13 | 120.2 | C36A—C37A—H37C | 109.5 |
C13—C14—C9 | 120.2 (3) | H37A—C37A—H37C | 109.5 |
C13—C14—C15 | 123.9 (3) | H37B—C37A—H37C | 109.5 |
C9—C14—C15 | 115.8 (2) | C36B—C37B—H37D | 109.5 |
N2—C15—C14 | 109.52 (18) | C36B—C37B—H37E | 109.5 |
N2—C15—H15A | 109.8 | H37D—C37B—H37E | 109.5 |
C14—C15—H15A | 109.8 | C36B—C37B—H37F | 109.5 |
N2—C15—H15B | 109.8 | H37D—C37B—H37F | 109.5 |
C14—C15—H15B | 109.8 | H37E—C37B—H37F | 109.5 |
H15A—C15—H15B | 108.2 | O5—C38—H38A | 109.5 |
C21—C16—C17 | 116.7 (2) | O5—C38—H38B | 109.5 |
C21—C16—C6 | 124.1 (2) | H38A—C38—H38B | 109.5 |
C17—C16—C6 | 119.2 (2) | O5—C38—H38C | 109.5 |
C18—C17—C16 | 122.1 (2) | H38A—C38—H38C | 109.5 |
C18—C17—H17 | 118.9 | H38B—C38—H38C | 109.5 |
C16—C17—H17 | 118.9 | C3—N1—C28 | 130.0 (2) |
C17—C18—C19 | 120.0 (3) | C3—N1—C1 | 94.42 (18) |
C17—C18—H18 | 120.0 | C28—N1—C1 | 129.14 (19) |
C19—C18—H18 | 120.0 | C4—N2—C7 | 111.06 (17) |
C20—C19—O5 | 124.8 (3) | C4—N2—C15 | 111.80 (16) |
C20—C19—C18 | 119.3 (2) | C7—N2—C15 | 115.71 (18) |
O5—C19—C18 | 115.9 (3) | O6—N3—O7 | 124.1 (2) |
C19—C20—C21 | 120.0 (2) | O6—N3—C5 | 118.8 (2) |
C19—C20—H20 | 120.0 | O7—N3—C5 | 117.1 (2) |
C21—C20—H20 | 120.0 | C31—O2—C34 | 116.7 (2) |
C16—C21—C20 | 121.9 (3) | C35—O3—C36A | 113.4 (5) |
C16—C21—H21 | 119.1 | C35—O3—C36B | 119.7 (10) |
C20—C21—H21 | 119.1 | C36A—O3—C36B | 17.5 (10) |
C23—C22—C27 | 118.6 (2) | C19—O5—C38 | 117.4 (3) |
N1—C1—C2—C22 | 119.1 (2) | C2—C22—C23—C24 | −175.0 (3) |
C4—C1—C2—C22 | −0.6 (3) | C22—C23—C24—C25 | −0.3 (5) |
N1—C1—C2—C3 | −1.17 (17) | C23—C24—C25—C26 | −1.6 (5) |
C4—C1—C2—C3 | −120.9 (2) | C24—C25—C26—C27 | 1.6 (5) |
C22—C2—C3—O1 | 61.1 (4) | C23—C22—C27—C26 | −2.3 (4) |
C1—C2—C3—O1 | −177.8 (3) | C2—C22—C27—C26 | 174.9 (3) |
C22—C2—C3—N1 | −119.9 (2) | C25—C26—C27—C22 | 0.4 (5) |
C1—C2—C3—N1 | 1.26 (18) | C33—C28—C29—C30 | −0.6 (4) |
N1—C1—C4—N2 | 58.1 (3) | N1—C28—C29—C30 | −178.7 (3) |
C2—C1—C4—N2 | 159.31 (18) | C28—C29—C30—C31 | −0.9 (5) |
N1—C1—C4—C5 | 179.16 (17) | C29—C30—C31—O2 | −179.4 (3) |
C2—C1—C4—C5 | −79.7 (2) | C29—C30—C31—C32 | 2.2 (5) |
N2—C4—C5—N3 | 94.8 (2) | C30—C31—C32—C33 | −1.9 (5) |
C1—C4—C5—N3 | −31.3 (3) | O2—C31—C32—C33 | 179.5 (3) |
N2—C4—C5—C6 | −25.4 (2) | C31—C32—C33—C28 | 0.4 (5) |
C1—C4—C5—C6 | −151.54 (18) | C29—C28—C33—C32 | 0.9 (5) |
N3—C5—C6—C16 | 142.32 (19) | N1—C28—C33—C32 | 179.0 (3) |
C4—C5—C6—C16 | −98.4 (2) | N2—C7—C35—O4 | 164.9 (2) |
N3—C5—C6—C7 | −91.7 (2) | C8—C7—C35—O4 | −75.2 (3) |
C4—C5—C6—C7 | 27.5 (2) | C6—C7—C35—O4 | 47.4 (3) |
C16—C6—C7—N2 | 103.9 (2) | N2—C7—C35—O3 | −20.1 (3) |
C5—C6—C7—N2 | −19.9 (2) | C8—C7—C35—O3 | 99.9 (3) |
C16—C6—C7—C35 | −135.3 (2) | C6—C7—C35—O3 | −137.6 (2) |
C5—C6—C7—C35 | 100.9 (2) | O1—C3—N1—C28 | 24.7 (5) |
C16—C6—C7—C8 | −19.4 (3) | C2—C3—N1—C28 | −154.4 (2) |
C5—C6—C7—C8 | −143.24 (19) | O1—C3—N1—C1 | 177.8 (3) |
N2—C7—C8—C9 | 49.1 (2) | C2—C3—N1—C1 | −1.34 (19) |
C35—C7—C8—C9 | −71.1 (2) | C29—C28—N1—C3 | 159.1 (3) |
C6—C7—C8—C9 | 169.71 (18) | C33—C28—N1—C3 | −19.0 (4) |
C7—C8—C9—C10 | 125.3 (2) | C29—C28—N1—C1 | 14.7 (4) |
C7—C8—C9—C14 | −51.4 (3) | C33—C28—N1—C1 | −163.4 (3) |
C14—C9—C10—C11 | −1.5 (4) | C4—C1—N1—C3 | 119.2 (2) |
C8—C9—C10—C11 | −178.1 (3) | C2—C1—N1—C3 | 1.30 (19) |
C9—C10—C11—C12 | 0.6 (4) | C4—C1—N1—C28 | −87.3 (3) |
C10—C11—C12—C13 | 0.3 (5) | C2—C1—N1—C28 | 154.8 (2) |
C11—C12—C13—C14 | −0.3 (5) | C1—C4—N2—C7 | 138.00 (18) |
C12—C13—C14—C9 | −0.5 (4) | C5—C4—N2—C7 | 12.9 (2) |
C12—C13—C14—C15 | 175.9 (2) | C1—C4—N2—C15 | −91.1 (2) |
C10—C9—C14—C13 | 1.4 (4) | C5—C4—N2—C15 | 143.76 (19) |
C8—C9—C14—C13 | 178.3 (2) | C35—C7—N2—C4 | −114.9 (2) |
C10—C9—C14—C15 | −175.3 (2) | C8—C7—N2—C4 | 129.7 (2) |
C8—C9—C14—C15 | 1.7 (3) | C6—C7—N2—C4 | 4.4 (2) |
C13—C14—C15—N2 | −127.0 (3) | C35—C7—N2—C15 | 116.2 (2) |
C9—C14—C15—N2 | 49.5 (3) | C8—C7—N2—C15 | 0.8 (3) |
C5—C6—C16—C21 | 29.0 (3) | C6—C7—N2—C15 | −124.4 (2) |
C7—C6—C16—C21 | −90.2 (3) | C14—C15—N2—C4 | −178.13 (19) |
C5—C6—C16—C17 | −150.5 (2) | C14—C15—N2—C7 | −49.7 (3) |
C7—C6—C16—C17 | 90.3 (3) | C6—C5—N3—O6 | 40.4 (3) |
C21—C16—C17—C18 | 0.3 (4) | C4—C5—N3—O6 | −76.4 (3) |
C6—C16—C17—C18 | 179.9 (3) | C6—C5—N3—O7 | −142.3 (2) |
C16—C17—C18—C19 | −1.4 (5) | C4—C5—N3—O7 | 101.0 (2) |
C17—C18—C19—C20 | 1.2 (5) | C30—C31—O2—C34 | 2.4 (5) |
C17—C18—C19—O5 | −178.5 (3) | C32—C31—O2—C34 | −179.1 (3) |
O5—C19—C20—C21 | 179.7 (3) | O4—C35—O3—C36A | 8.5 (8) |
C18—C19—C20—C21 | 0.0 (4) | C7—C35—O3—C36A | −166.4 (7) |
C17—C16—C21—C20 | 1.0 (4) | O4—C35—O3—C36B | −9.9 (10) |
C6—C16—C21—C20 | −178.6 (3) | C7—C35—O3—C36B | 175.3 (9) |
C19—C20—C21—C16 | −1.1 (5) | C37A—C36A—O3—C35 | 106.6 (10) |
C3—C2—C22—C23 | −156.6 (3) | C37A—C36A—O3—C36B | −139 (5) |
C1—C2—C22—C23 | 101.9 (3) | C37B—C36B—O3—C35 | 132.2 (15) |
C3—C2—C22—C27 | 26.2 (3) | C37B—C36B—O3—C36A | 59 (4) |
C1—C2—C22—C27 | −75.3 (3) | C20—C19—O5—C38 | −1.1 (5) |
C27—C22—C23—C24 | 2.3 (4) | C18—C19—O5—C38 | 178.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.98 | 2.42 | 3.260 (3) | 143 |
C20—H20···O1ii | 0.93 | 2.47 | 3.397 (3) | 172 |
C29—H29···O3 | 0.93 | 2.59 | 3.442 (3) | 152 |
C29—H29···N2 | 0.93 | 2.50 | 3.168 (3) | 128 |
C33—H33···O1 | 0.93 | 2.44 | 3.054 (4) | 123 |
Symmetry codes: (i) x, y+1, z; (ii) x−1/2, −y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C38H37N3O7 |
Mr | 647.71 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 9.0149 (3), 11.0865 (4), 33.3731 (11) |
V (Å3) | 3335.4 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.20 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker KappaAPEX2 diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.982, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 68599, 3960, 3318 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.632 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.107, 1.06 |
No. of reflections | 3960 |
No. of parameters | 453 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.16 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.98 | 2.42 | 3.260 (3) | 143 |
C20—H20···O1ii | 0.93 | 2.47 | 3.397 (3) | 172 |
C29—H29···O3 | 0.93 | 2.59 | 3.442 (3) | 152 |
C29—H29···N2 | 0.93 | 2.50 | 3.168 (3) | 128 |
C33—H33···O1 | 0.93 | 2.44 | 3.054 (4) | 123 |
Symmetry codes: (i) x, y+1, z; (ii) x−1/2, −y+1/2, −z. |
Acknowledgements
ETSK thanks Professor M. N. Ponnuswamy and Professor D. Velmurugan, Department of Crystallography and Biophysics, University of Madras, India, for their guidance and valuable suggestions. ETSK also thanks SRM Management for their support.
References
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Quinoline is a hepatocarcinogen in mice and rats, a mutagen in Salmonella typhimurium and induces unscheduled DNA synthesis in primary cultures of rat hepatocytes (LaVoie et al., 1983). Quinolinium based chloride sensitive flourescent indicators provide a new approach to study chloride transport mechanisms and regulation (Verkman, 1990). Pyrrole derivatives inhibit cytokine-dependent induction of human immunodeficiency virus (HIV) expression in chronically infected promonocytic cells (Weissman et al., 1993). Pyrroles possess anti inflammatory (Fernandes et al., 2004), anti viral (Borthwick et al., 2003), antifungal and antimicrobial activities (Amal Raj et al., 2003). β lactams are one of the best known and most extensively studied class of compounds due to their biological activity (Morin & Gorman, 1982; Georg & Ravikumar, 1993; Katritzky et al., 1996). The most commonly used β lactam antibiotics for the therapy of infectious diseases are penicillin and cephalosporin (Brakhage, 1998). Due to these importance the crystal structure determination of the title compound (I) was carried out and the results are presented here.
Fig 1 shows a plot of compound (I). Bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable with those of reported structures (Kamala et al., 2008; Sundari et al., 2006).
In the molecule the pyrrolidine ring exhibits a twist conformation with asymetry parameters (Nardelli,1983)ΔCs(C5) = 5.2 (2), ΔC2(C6) = 39.6 (2) and with the puckering parameters (Cremer and Pople, 1975) q2 = 0.274 (3)Å and ϕ2 =267.5 (5)°. The six membered ring C7/C8/C9/C14/C15/N2 exhibits a boat conformation with the puckering parameters Q=0.699 (3) Å, Θ = 88.8 (2)° and ϕ = 120.1 (2)°. The sum of bond angles around N1 [353.59°], and around N3 [359.94°] indicate sp2, those around atom N2 [338.58°] indicate sp3 hybridization. The pyrrolidine ring and the phenyl ring C9—C14 are nearly planar with each other with a dihedral angle of 9.49 (7)° while the phenyl rings are oriented at right angles to each other making an angle of 87.48 (7)°.
In the crystal packing, C—H···O interactions stabilize crystal structure.