organic compounds
1-(4-Methoxyphenyl)-7-phenyl-3-(phenylselenylmethyl)perhydroisoxazolo[2′,3′:1,2]pyrrolo[3,4-b]azetidine-6-spiro-2′-chroman-2,4′-dione
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 title compound, C35H30N2O5Se, the pyrrolidine ring adopts an and the oxazolidine ring is in a twist conformation. The tetrahydropyran ring adopts a half-chair conformation. The methoxyphenyl ring is twisted away from the attached azetidinone ring by 15.7 (1)°. In the intermolecular C—H⋯O interactions link the molecules into a two-dimensional network.
Related literature
For general background, see: Brakhage (1998); Chenera et al. (1993); Ellis (1997); Farrugia (1997); Kilonda et al. (1995); Koojiman et al. (1984); Lampronti et al. (2003). For bond-length data, see: Allen et al. (1987). For ring conformation details, see: Cremer & Pople (1975); Nardelli (1983).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2004); cell APEX2; data reduction: SAINT (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/S1600536808008829/ci2571sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008829/ci2571Isup2.hkl
To a solution of the bicyclic nitrone (1 mol) in dry acetonitrile (20 ml) was added 3-arylidene chromanone (1 mol) under a N2 atmosphere. The reaction was refluxed for 4 h. After the completion of the reaction, the solvent was distilled off under reduced pressure and the crude product was purified by
The title compound was crystallized from benzene solution by slow evaporation technique.H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C-H = 0.93-0.98 Å and Uiso(H)= 1.2–1.5Ueq(C).
Data collection: APEX2 (Bruker, 2004); cell
APEX2 (Bruker, 2004); data reduction: SAINT (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 the title compound with 30% probability displacement ellipsoids. | |
Fig. 2. A view of the molecular packing of the title compound. |
C35H30N2O5Se | F(000) = 1312 |
Mr = 637.57 | Dx = 1.447 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 38750 reflections |
a = 14.0886 (5) Å | θ = 1.8–31.9° |
b = 10.6813 (4) Å | µ = 1.33 mm−1 |
c = 19.4744 (7) Å | T = 293 K |
β = 92.721 (2)° | Prism, colourless |
V = 2927.29 (18) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Bruker KappaAPEX2 diffractometer | 9941 independent reflections |
Radiation source: fine-focus sealed tube | 5805 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and ϕ scans | θmax = 31.9°, θmin = 1.8° |
Absorption correction: multi-scan (Blessing, 1995) | h = −19→20 |
Tmin = 0.691, Tmax = 0.777 | k = −15→10 |
38750 measured reflections | l = −28→28 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0444P)2 + 1.2941P] where P = (Fo2 + 2Fc2)/3 |
9941 reflections | (Δ/σ)max = 0.001 |
389 parameters | Δρmax = 0.79 e Å−3 |
0 restraints | Δρmin = −0.67 e Å−3 |
C35H30N2O5Se | V = 2927.29 (18) Å3 |
Mr = 637.57 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.0886 (5) Å | µ = 1.33 mm−1 |
b = 10.6813 (4) Å | T = 293 K |
c = 19.4744 (7) Å | 0.30 × 0.20 × 0.20 mm |
β = 92.721 (2)° |
Bruker KappaAPEX2 diffractometer | 9941 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 5805 reflections with I > 2σ(I) |
Tmin = 0.691, Tmax = 0.777 | Rint = 0.028 |
38750 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.79 e Å−3 |
9941 reflections | Δρmin = −0.67 e Å−3 |
389 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 | ||
Se1 | 1.016999 (16) | 0.19600 (3) | 0.180072 (11) | 0.05427 (9) | |
O1 | 0.84548 (10) | 0.24863 (15) | 0.33002 (7) | 0.0499 (4) | |
O2 | 0.69775 (9) | 0.13919 (14) | 0.07844 (6) | 0.0423 (3) | |
O3 | 0.64805 (13) | 0.40844 (15) | 0.12826 (7) | 0.0583 (4) | |
O4 | 0.54329 (11) | 0.16190 (14) | −0.01690 (7) | 0.0482 (4) | |
O5 | 0.42581 (12) | 0.20236 (17) | 0.48343 (9) | 0.0662 (5) | |
N1 | 0.71402 (11) | 0.11790 (15) | 0.30571 (7) | 0.0353 (3) | |
N2 | 0.74055 (11) | 0.06570 (15) | 0.13393 (7) | 0.0358 (3) | |
C1 | 0.80284 (13) | 0.16622 (18) | 0.30008 (9) | 0.0359 (4) | |
C2 | 0.82270 (13) | 0.07814 (18) | 0.24043 (9) | 0.0357 (4) | |
H2 | 0.8749 | 0.0189 | 0.2497 | 0.043* | |
C3 | 0.72246 (13) | 0.02471 (18) | 0.25094 (9) | 0.0354 (4) | |
H3 | 0.7221 | −0.0623 | 0.2669 | 0.042* | |
C4 | 0.81961 (13) | 0.13643 (18) | 0.16898 (9) | 0.0343 (4) | |
H4 | 0.8039 | 0.2256 | 0.1714 | 0.041* | |
C5 | 0.66549 (13) | 0.04692 (18) | 0.18298 (9) | 0.0346 (4) | |
H5 | 0.6280 | −0.0276 | 0.1704 | 0.041* | |
C6 | 0.60958 (12) | 0.19551 (17) | 0.09998 (9) | 0.0322 (4) | |
C7 | 0.60343 (12) | 0.16392 (17) | 0.17651 (9) | 0.0324 (4) | |
H7 | 0.6359 | 0.2308 | 0.2028 | 0.039* | |
C8 | 0.62051 (13) | 0.33430 (18) | 0.08468 (9) | 0.0352 (4) | |
C9 | 0.60212 (13) | 0.36900 (18) | 0.01199 (9) | 0.0357 (4) | |
C10 | 0.62385 (15) | 0.4882 (2) | −0.01152 (11) | 0.0458 (5) | |
H10 | 0.6456 | 0.5490 | 0.0195 | 0.055* | |
C11 | 0.61339 (18) | 0.5166 (2) | −0.08025 (12) | 0.0552 (6) | |
H11 | 0.6283 | 0.5963 | −0.0957 | 0.066* | |
C12 | 0.58075 (18) | 0.4265 (2) | −0.12602 (11) | 0.0580 (6) | |
H12 | 0.5743 | 0.4459 | −0.1726 | 0.070* | |
C13 | 0.55774 (17) | 0.3095 (2) | −0.10459 (11) | 0.0525 (6) | |
H13 | 0.5355 | 0.2498 | −0.1362 | 0.063* | |
C14 | 0.56779 (14) | 0.27993 (19) | −0.03503 (10) | 0.0396 (4) | |
C15 | 0.52914 (14) | 0.1432 (2) | 0.05444 (10) | 0.0421 (4) | |
H15A | 0.5232 | 0.0542 | 0.0633 | 0.051* | |
H15B | 0.4702 | 0.1830 | 0.0661 | 0.051* | |
C16 | 0.50369 (13) | 0.1537 (2) | 0.20162 (10) | 0.0412 (4) | |
C17 | 0.45117 (18) | 0.0450 (3) | 0.19745 (14) | 0.0660 (7) | |
H17 | 0.4770 | −0.0262 | 0.1781 | 0.079* | |
C18 | 0.3608 (2) | 0.0404 (4) | 0.22162 (16) | 0.0898 (11) | |
H18 | 0.3265 | −0.0339 | 0.2186 | 0.108* | |
C19 | 0.3214 (2) | 0.1434 (5) | 0.24973 (16) | 0.0944 (12) | |
H19 | 0.2604 | 0.1396 | 0.2659 | 0.113* | |
C20 | 0.3719 (2) | 0.2522 (4) | 0.25400 (15) | 0.0848 (10) | |
H20 | 0.3450 | 0.3229 | 0.2730 | 0.102* | |
C21 | 0.46266 (16) | 0.2584 (3) | 0.23037 (12) | 0.0561 (6) | |
H21 | 0.4965 | 0.3331 | 0.2337 | 0.067* | |
C22 | 0.64158 (13) | 0.13740 (18) | 0.35180 (9) | 0.0355 (4) | |
C23 | 0.57163 (15) | 0.0489 (2) | 0.35695 (10) | 0.0455 (5) | |
H23 | 0.5739 | −0.0240 | 0.3309 | 0.055* | |
C24 | 0.49788 (16) | 0.0667 (2) | 0.40035 (11) | 0.0491 (5) | |
H24 | 0.4507 | 0.0063 | 0.4035 | 0.059* | |
C25 | 0.49483 (14) | 0.1746 (2) | 0.43884 (10) | 0.0448 (5) | |
C26 | 0.56613 (15) | 0.2627 (2) | 0.43419 (11) | 0.0474 (5) | |
H26 | 0.5647 | 0.3348 | 0.4608 | 0.057* | |
C27 | 0.63907 (14) | 0.2453 (2) | 0.39089 (10) | 0.0424 (4) | |
H27 | 0.6864 | 0.3055 | 0.3879 | 0.051* | |
C28 | 0.34568 (18) | 0.1226 (3) | 0.48395 (15) | 0.0736 (8) | |
H28A | 0.3016 | 0.1544 | 0.5158 | 0.110* | |
H28B | 0.3655 | 0.0400 | 0.4977 | 0.110* | |
H28C | 0.3156 | 0.1194 | 0.4387 | 0.110* | |
C29 | 0.90857 (14) | 0.1174 (2) | 0.13028 (10) | 0.0441 (5) | |
H29A | 0.9003 | 0.1540 | 0.0848 | 0.053* | |
H29B | 0.9205 | 0.0286 | 0.1250 | 0.053* | |
C30 | 1.11387 (14) | 0.1421 (2) | 0.12143 (10) | 0.0423 (4) | |
C31 | 1.12365 (18) | 0.0189 (2) | 0.10270 (15) | 0.0628 (7) | |
H31 | 1.0823 | −0.0412 | 0.1187 | 0.075* | |
C32 | 1.19504 (19) | −0.0161 (3) | 0.05994 (17) | 0.0766 (8) | |
H32 | 1.2007 | −0.0994 | 0.0468 | 0.092* | |
C33 | 1.25653 (18) | 0.0703 (3) | 0.03718 (14) | 0.0715 (8) | |
H33 | 1.3050 | 0.0461 | 0.0092 | 0.086* | |
C34 | 1.24733 (17) | 0.1910 (3) | 0.05514 (14) | 0.0641 (7) | |
H34 | 1.2893 | 0.2502 | 0.0391 | 0.077* | |
C35 | 1.17647 (15) | 0.2283 (2) | 0.09712 (12) | 0.0523 (5) | |
H35 | 1.1710 | 0.3122 | 0.1090 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.04250 (13) | 0.07341 (18) | 0.04728 (13) | 0.00234 (11) | 0.00606 (9) | −0.01202 (11) |
O1 | 0.0460 (8) | 0.0529 (9) | 0.0506 (8) | −0.0080 (7) | 0.0006 (7) | −0.0064 (7) |
O2 | 0.0403 (7) | 0.0574 (9) | 0.0294 (6) | 0.0159 (6) | 0.0042 (5) | −0.0001 (6) |
O3 | 0.0896 (12) | 0.0422 (9) | 0.0416 (8) | −0.0170 (8) | −0.0122 (8) | −0.0078 (7) |
O4 | 0.0623 (9) | 0.0430 (8) | 0.0380 (7) | −0.0094 (7) | −0.0108 (6) | −0.0066 (6) |
O5 | 0.0488 (9) | 0.0835 (13) | 0.0684 (11) | −0.0043 (8) | 0.0253 (8) | −0.0200 (9) |
N1 | 0.0391 (8) | 0.0353 (9) | 0.0317 (7) | 0.0000 (7) | 0.0052 (6) | −0.0020 (6) |
N2 | 0.0373 (8) | 0.0384 (9) | 0.0318 (7) | 0.0091 (7) | 0.0030 (6) | −0.0002 (6) |
C1 | 0.0366 (10) | 0.0386 (11) | 0.0324 (8) | 0.0039 (8) | 0.0002 (7) | 0.0068 (8) |
C2 | 0.0367 (9) | 0.0369 (11) | 0.0337 (8) | 0.0093 (8) | 0.0030 (7) | 0.0043 (8) |
C3 | 0.0426 (10) | 0.0296 (9) | 0.0343 (8) | 0.0053 (8) | 0.0064 (7) | 0.0023 (7) |
C4 | 0.0346 (9) | 0.0366 (10) | 0.0320 (8) | 0.0071 (8) | 0.0037 (7) | 0.0019 (7) |
C5 | 0.0356 (9) | 0.0316 (10) | 0.0368 (9) | 0.0018 (7) | 0.0043 (7) | −0.0045 (7) |
C6 | 0.0291 (8) | 0.0354 (10) | 0.0319 (8) | 0.0033 (7) | −0.0003 (6) | −0.0067 (7) |
C7 | 0.0290 (8) | 0.0338 (10) | 0.0346 (8) | 0.0012 (7) | 0.0026 (7) | −0.0051 (7) |
C8 | 0.0329 (9) | 0.0366 (10) | 0.0359 (9) | −0.0005 (8) | −0.0018 (7) | −0.0051 (8) |
C9 | 0.0328 (9) | 0.0370 (11) | 0.0370 (9) | 0.0044 (8) | −0.0031 (7) | −0.0028 (8) |
C10 | 0.0509 (12) | 0.0403 (12) | 0.0460 (11) | 0.0000 (9) | −0.0015 (9) | −0.0025 (9) |
C11 | 0.0664 (15) | 0.0471 (13) | 0.0518 (12) | 0.0032 (11) | −0.0001 (11) | 0.0106 (11) |
C12 | 0.0684 (16) | 0.0632 (16) | 0.0415 (11) | 0.0064 (13) | −0.0073 (10) | 0.0058 (11) |
C13 | 0.0604 (14) | 0.0559 (15) | 0.0397 (10) | 0.0007 (11) | −0.0131 (10) | −0.0056 (10) |
C14 | 0.0369 (10) | 0.0424 (12) | 0.0386 (9) | 0.0031 (8) | −0.0077 (8) | −0.0047 (8) |
C15 | 0.0442 (11) | 0.0393 (11) | 0.0422 (10) | −0.0072 (9) | −0.0047 (8) | −0.0056 (9) |
C16 | 0.0327 (10) | 0.0552 (13) | 0.0360 (9) | 0.0011 (9) | 0.0044 (7) | −0.0014 (9) |
C17 | 0.0502 (14) | 0.0756 (18) | 0.0733 (16) | −0.0166 (13) | 0.0132 (12) | −0.0070 (14) |
C18 | 0.0539 (17) | 0.138 (3) | 0.0782 (19) | −0.0374 (19) | 0.0110 (15) | 0.004 (2) |
C19 | 0.0363 (14) | 0.181 (4) | 0.0671 (18) | 0.004 (2) | 0.0132 (12) | 0.010 (2) |
C20 | 0.0533 (17) | 0.134 (3) | 0.0680 (17) | 0.0316 (19) | 0.0163 (14) | −0.0062 (19) |
C21 | 0.0462 (13) | 0.0687 (16) | 0.0539 (12) | 0.0178 (11) | 0.0093 (10) | −0.0033 (12) |
C22 | 0.0382 (10) | 0.0385 (11) | 0.0299 (8) | 0.0018 (8) | 0.0021 (7) | 0.0019 (8) |
C23 | 0.0525 (12) | 0.0419 (12) | 0.0431 (10) | −0.0058 (9) | 0.0124 (9) | −0.0067 (9) |
C24 | 0.0471 (12) | 0.0500 (13) | 0.0512 (12) | −0.0109 (10) | 0.0115 (9) | −0.0024 (10) |
C25 | 0.0365 (10) | 0.0601 (14) | 0.0384 (10) | 0.0029 (9) | 0.0075 (8) | −0.0040 (9) |
C26 | 0.0467 (12) | 0.0502 (13) | 0.0457 (11) | −0.0004 (10) | 0.0073 (9) | −0.0151 (10) |
C27 | 0.0419 (11) | 0.0432 (11) | 0.0424 (10) | −0.0050 (9) | 0.0049 (8) | −0.0083 (9) |
C28 | 0.0448 (14) | 0.099 (2) | 0.0793 (18) | −0.0042 (14) | 0.0260 (12) | −0.0061 (16) |
C29 | 0.0366 (10) | 0.0604 (14) | 0.0359 (9) | 0.0025 (9) | 0.0062 (8) | −0.0018 (9) |
C30 | 0.0331 (10) | 0.0500 (12) | 0.0437 (10) | 0.0037 (9) | −0.0003 (8) | −0.0039 (9) |
C31 | 0.0492 (13) | 0.0477 (14) | 0.0919 (19) | −0.0018 (11) | 0.0087 (13) | −0.0055 (13) |
C32 | 0.0586 (16) | 0.0615 (17) | 0.110 (2) | 0.0086 (13) | 0.0066 (15) | −0.0344 (16) |
C33 | 0.0411 (13) | 0.099 (2) | 0.0751 (17) | −0.0032 (14) | 0.0079 (12) | −0.0348 (16) |
C34 | 0.0431 (13) | 0.085 (2) | 0.0653 (15) | −0.0131 (12) | 0.0090 (11) | −0.0100 (14) |
C35 | 0.0420 (12) | 0.0548 (14) | 0.0601 (13) | −0.0032 (10) | 0.0028 (10) | −0.0081 (11) |
Se1—C30 | 1.910 (2) | C13—H13 | 0.93 |
Se1—C29 | 1.959 (2) | C15—H15A | 0.97 |
O1—C1 | 1.201 (2) | C15—H15B | 0.97 |
O2—N2 | 1.4441 (19) | C16—C17 | 1.377 (3) |
O2—C6 | 1.460 (2) | C16—C21 | 1.389 (3) |
O3—C8 | 1.211 (2) | C17—C18 | 1.379 (4) |
O4—C14 | 1.358 (2) | C17—H17 | 0.93 |
O4—C15 | 1.427 (2) | C18—C19 | 1.359 (5) |
O5—C25 | 1.367 (2) | C18—H18 | 0.93 |
O5—C28 | 1.414 (3) | C19—C20 | 1.364 (5) |
N1—C1 | 1.363 (2) | C19—H19 | 0.93 |
N1—C22 | 1.406 (2) | C20—C21 | 1.381 (4) |
N1—C3 | 1.468 (2) | C20—H20 | 0.93 |
N2—C5 | 1.472 (2) | C21—H21 | 0.93 |
N2—C4 | 1.485 (2) | C22—C23 | 1.373 (3) |
C1—C2 | 1.531 (3) | C22—C27 | 1.382 (3) |
C2—C4 | 1.523 (2) | C23—C24 | 1.383 (3) |
C2—C3 | 1.546 (3) | C23—H23 | 0.93 |
C2—H2 | 0.98 | C24—C25 | 1.376 (3) |
C3—C5 | 1.533 (3) | C24—H24 | 0.93 |
C3—H3 | 0.98 | C25—C26 | 1.382 (3) |
C4—C29 | 1.506 (3) | C26—C27 | 1.372 (3) |
C4—H4 | 0.98 | C26—H26 | 0.93 |
C5—C7 | 1.527 (3) | C27—H27 | 0.93 |
C5—H5 | 0.98 | C28—H28A | 0.96 |
C6—C15 | 1.513 (2) | C28—H28B | 0.96 |
C6—C8 | 1.521 (3) | C28—H28C | 0.96 |
C6—C7 | 1.535 (2) | C29—H29A | 0.97 |
C7—C16 | 1.513 (2) | C29—H29B | 0.97 |
C7—H7 | 0.98 | C30—C31 | 1.374 (3) |
C8—C9 | 1.474 (3) | C30—C35 | 1.375 (3) |
C9—C14 | 1.391 (3) | C31—C32 | 1.387 (4) |
C9—C10 | 1.392 (3) | C31—H31 | 0.93 |
C10—C11 | 1.374 (3) | C32—C33 | 1.354 (4) |
C10—H10 | 0.93 | C32—H32 | 0.93 |
C11—C12 | 1.376 (3) | C33—C34 | 1.344 (4) |
C11—H11 | 0.93 | C33—H33 | 0.93 |
C12—C13 | 1.362 (3) | C34—C35 | 1.379 (3) |
C12—H12 | 0.93 | C34—H34 | 0.93 |
C13—C14 | 1.392 (3) | C35—H35 | 0.93 |
C30—Se1—C29 | 97.90 (8) | O4—C15—H15A | 109.1 |
N2—O2—C6 | 109.86 (12) | C6—C15—H15A | 109.1 |
C14—O4—C15 | 115.61 (15) | O4—C15—H15B | 109.1 |
C25—O5—C28 | 117.78 (19) | C6—C15—H15B | 109.1 |
C1—N1—C22 | 133.82 (16) | H15A—C15—H15B | 107.8 |
C1—N1—C3 | 95.27 (14) | C17—C16—C21 | 118.0 (2) |
C22—N1—C3 | 130.58 (16) | C17—C16—C7 | 123.1 (2) |
O2—N2—C5 | 105.81 (13) | C21—C16—C7 | 118.9 (2) |
O2—N2—C4 | 110.17 (14) | C16—C17—C18 | 120.8 (3) |
C5—N2—C4 | 108.50 (13) | C16—C17—H17 | 119.6 |
O1—C1—N1 | 132.72 (18) | C18—C17—H17 | 119.6 |
O1—C1—C2 | 135.53 (18) | C19—C18—C17 | 120.7 (3) |
N1—C1—C2 | 91.72 (15) | C19—C18—H18 | 119.7 |
C4—C2—C1 | 116.34 (16) | C17—C18—H18 | 119.7 |
C4—C2—C3 | 106.57 (14) | C18—C19—C20 | 119.5 (3) |
C1—C2—C3 | 85.72 (13) | C18—C19—H19 | 120.2 |
C4—C2—H2 | 114.8 | C20—C19—H19 | 120.2 |
C1—C2—H2 | 114.8 | C19—C20—C21 | 120.6 (3) |
C3—C2—H2 | 114.8 | C19—C20—H20 | 119.7 |
N1—C3—C5 | 117.72 (15) | C21—C20—H20 | 119.7 |
N1—C3—C2 | 87.24 (14) | C20—C21—C16 | 120.4 (3) |
C5—C3—C2 | 105.83 (14) | C20—C21—H21 | 119.8 |
N1—C3—H3 | 114.2 | C16—C21—H21 | 119.8 |
C5—C3—H3 | 114.2 | C23—C22—C27 | 119.77 (18) |
C2—C3—H3 | 114.2 | C23—C22—N1 | 119.34 (17) |
N2—C4—C29 | 108.99 (15) | C27—C22—N1 | 120.88 (17) |
N2—C4—C2 | 101.55 (14) | C22—C23—C24 | 120.83 (19) |
C29—C4—C2 | 114.43 (15) | C22—C23—H23 | 119.6 |
N2—C4—H4 | 110.5 | C24—C23—H23 | 119.6 |
C29—C4—H4 | 110.5 | C25—C24—C23 | 119.5 (2) |
C2—C4—H4 | 110.5 | C25—C24—H24 | 120.3 |
N2—C5—C7 | 105.14 (15) | C23—C24—H24 | 120.3 |
N2—C5—C3 | 102.61 (14) | O5—C25—C24 | 124.7 (2) |
C7—C5—C3 | 118.17 (15) | O5—C25—C26 | 115.79 (19) |
N2—C5—H5 | 110.1 | C24—C25—C26 | 119.50 (19) |
C7—C5—H5 | 110.1 | C27—C26—C25 | 121.1 (2) |
C3—C5—H5 | 110.1 | C27—C26—H26 | 119.5 |
O2—C6—C15 | 107.66 (14) | C25—C26—H26 | 119.5 |
O2—C6—C8 | 104.47 (14) | C26—C27—C22 | 119.4 (2) |
C15—C6—C8 | 108.99 (15) | C26—C27—H27 | 120.3 |
O2—C6—C7 | 106.06 (13) | C22—C27—H27 | 120.3 |
C15—C6—C7 | 114.39 (15) | O5—C28—H28A | 109.5 |
C8—C6—C7 | 114.54 (14) | O5—C28—H28B | 109.5 |
C16—C7—C5 | 116.80 (16) | H28A—C28—H28B | 109.5 |
C16—C7—C6 | 115.20 (15) | O5—C28—H28C | 109.5 |
C5—C7—C6 | 101.63 (14) | H28A—C28—H28C | 109.5 |
C16—C7—H7 | 107.5 | H28B—C28—H28C | 109.5 |
C5—C7—H7 | 107.5 | C4—C29—Se1 | 110.03 (13) |
C6—C7—H7 | 107.5 | C4—C29—H29A | 109.7 |
O3—C8—C9 | 122.98 (18) | Se1—C29—H29A | 109.7 |
O3—C8—C6 | 122.14 (17) | C4—C29—H29B | 109.7 |
C9—C8—C6 | 114.72 (15) | Se1—C29—H29B | 109.7 |
C14—C9—C10 | 118.95 (18) | H29A—C29—H29B | 108.2 |
C14—C9—C8 | 119.98 (18) | C31—C30—C35 | 118.4 (2) |
C10—C9—C8 | 120.96 (17) | C31—C30—Se1 | 122.08 (17) |
C11—C10—C9 | 120.5 (2) | C35—C30—Se1 | 119.48 (17) |
C11—C10—H10 | 119.7 | C30—C31—C32 | 120.1 (2) |
C9—C10—H10 | 119.7 | C30—C31—H31 | 119.9 |
C10—C11—C12 | 119.6 (2) | C32—C31—H31 | 119.9 |
C10—C11—H11 | 120.2 | C33—C32—C31 | 120.4 (3) |
C12—C11—H11 | 120.2 | C33—C32—H32 | 119.8 |
C13—C12—C11 | 121.4 (2) | C31—C32—H32 | 119.8 |
C13—C12—H12 | 119.3 | C34—C33—C32 | 119.8 (2) |
C11—C12—H12 | 119.3 | C34—C33—H33 | 120.1 |
C12—C13—C14 | 119.5 (2) | C32—C33—H33 | 120.1 |
C12—C13—H13 | 120.3 | C33—C34—C35 | 120.9 (2) |
C14—C13—H13 | 120.3 | C33—C34—H34 | 119.6 |
O4—C14—C9 | 123.26 (17) | C35—C34—H34 | 119.6 |
O4—C14—C13 | 116.63 (17) | C30—C35—C34 | 120.3 (2) |
C9—C14—C13 | 120.1 (2) | C30—C35—H35 | 119.8 |
O4—C15—C6 | 112.56 (16) | C34—C35—H35 | 119.8 |
C6—O2—N2—C5 | 15.91 (18) | C8—C9—C10—C11 | 174.9 (2) |
C6—O2—N2—C4 | −101.18 (16) | C9—C10—C11—C12 | 0.3 (3) |
C22—N1—C1—O1 | −6.5 (4) | C10—C11—C12—C13 | 0.5 (4) |
C3—N1—C1—O1 | 179.8 (2) | C11—C12—C13—C14 | −0.3 (4) |
C22—N1—C1—C2 | 175.33 (19) | C15—O4—C14—C9 | 16.9 (3) |
C3—N1—C1—C2 | 1.69 (14) | C15—O4—C14—C13 | −163.62 (19) |
O1—C1—C2—C4 | −73.3 (3) | C10—C9—C14—O4 | −178.98 (18) |
N1—C1—C2—C4 | 104.78 (17) | C8—C9—C14—O4 | 4.8 (3) |
O1—C1—C2—C3 | −179.7 (2) | C10—C9—C14—C13 | 1.5 (3) |
N1—C1—C2—C3 | −1.60 (13) | C8—C9—C14—C13 | −174.72 (19) |
C1—N1—C3—C5 | −108.13 (18) | C12—C13—C14—O4 | 179.7 (2) |
C22—N1—C3—C5 | 77.9 (2) | C12—C13—C14—C9 | −0.7 (3) |
C1—N1—C3—C2 | −1.67 (14) | C14—O4—C15—C6 | −48.8 (2) |
C22—N1—C3—C2 | −175.64 (18) | O2—C6—C15—O4 | −55.5 (2) |
C4—C2—C3—N1 | −114.74 (15) | C8—C6—C15—O4 | 57.3 (2) |
C1—C2—C3—N1 | 1.49 (12) | C7—C6—C15—O4 | −173.07 (16) |
C4—C2—C3—C5 | 3.32 (19) | C5—C7—C16—C17 | −32.9 (3) |
C1—C2—C3—C5 | 119.55 (15) | C6—C7—C16—C17 | 86.3 (3) |
O2—N2—C4—C29 | −84.46 (17) | C5—C7—C16—C21 | 147.02 (19) |
C5—N2—C4—C29 | 160.14 (15) | C6—C7—C16—C21 | −93.8 (2) |
O2—N2—C4—C2 | 154.42 (13) | C21—C16—C17—C18 | −0.5 (4) |
C5—N2—C4—C2 | 39.02 (17) | C7—C16—C17—C18 | 179.5 (2) |
C1—C2—C4—N2 | −118.02 (17) | C16—C17—C18—C19 | 0.4 (5) |
C3—C2—C4—N2 | −24.55 (18) | C17—C18—C19—C20 | 0.0 (5) |
C1—C2—C4—C29 | 124.75 (19) | C18—C19—C20—C21 | −0.3 (5) |
C3—C2—C4—C29 | −141.78 (17) | C19—C20—C21—C16 | 0.2 (4) |
O2—N2—C5—C7 | −31.16 (17) | C17—C16—C21—C20 | 0.1 (4) |
C4—N2—C5—C7 | 87.05 (16) | C7—C16—C21—C20 | −179.8 (2) |
O2—N2—C5—C3 | −155.33 (14) | C1—N1—C22—C23 | −160.4 (2) |
C4—N2—C5—C3 | −37.13 (18) | C3—N1—C22—C23 | 11.3 (3) |
N1—C3—C5—N2 | 114.86 (17) | C1—N1—C22—C27 | 20.8 (3) |
C2—C3—C5—N2 | 19.55 (18) | C3—N1—C22—C27 | −167.57 (18) |
N1—C3—C5—C7 | −0.2 (2) | C27—C22—C23—C24 | 0.6 (3) |
C2—C3—C5—C7 | −95.50 (18) | N1—C22—C23—C24 | −178.19 (19) |
N2—O2—C6—C15 | −117.18 (16) | C22—C23—C24—C25 | −0.1 (3) |
N2—O2—C6—C8 | 127.06 (14) | C28—O5—C25—C24 | −8.2 (3) |
N2—O2—C6—C7 | 5.68 (18) | C28—O5—C25—C26 | 172.7 (2) |
N2—C5—C7—C16 | 159.75 (15) | C23—C24—C25—O5 | −179.9 (2) |
C3—C5—C7—C16 | −86.6 (2) | C23—C24—C25—C26 | −0.8 (3) |
N2—C5—C7—C6 | 33.51 (17) | O5—C25—C26—C27 | −179.7 (2) |
C3—C5—C7—C6 | 147.19 (16) | C24—C25—C26—C27 | 1.1 (3) |
O2—C6—C7—C16 | −151.09 (16) | C25—C26—C27—C22 | −0.6 (3) |
C15—C6—C7—C16 | −32.6 (2) | C23—C22—C27—C26 | −0.3 (3) |
C8—C6—C7—C16 | 94.2 (2) | N1—C22—C27—C26 | 178.50 (18) |
O2—C6—C7—C5 | −23.81 (18) | N2—C4—C29—Se1 | −174.50 (12) |
C15—C6—C7—C5 | 94.68 (18) | C2—C4—C29—Se1 | −61.6 (2) |
C8—C6—C7—C5 | −138.47 (15) | C30—Se1—C29—C4 | 175.59 (15) |
O2—C6—C8—O3 | −96.2 (2) | C29—Se1—C30—C31 | −50.9 (2) |
C15—C6—C8—O3 | 148.92 (19) | C29—Se1—C30—C35 | 129.36 (18) |
C7—C6—C8—O3 | 19.3 (3) | C35—C30—C31—C32 | −0.3 (4) |
O2—C6—C8—C9 | 79.28 (18) | Se1—C30—C31—C32 | 180.0 (2) |
C15—C6—C8—C9 | −35.6 (2) | C30—C31—C32—C33 | 1.0 (4) |
C7—C6—C8—C9 | −165.14 (15) | C31—C32—C33—C34 | −1.2 (5) |
O3—C8—C9—C14 | −178.1 (2) | C32—C33—C34—C35 | 0.6 (4) |
C6—C8—C9—C14 | 6.5 (2) | C31—C30—C35—C34 | −0.2 (3) |
O3—C8—C9—C10 | 5.8 (3) | Se1—C30—C35—C34 | 179.50 (18) |
C6—C8—C9—C10 | −169.71 (17) | C33—C34—C35—C30 | 0.1 (4) |
C14—C9—C10—C11 | −1.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.98 | 2.42 | 3.199 (3) | 136 |
C29—H29A···O5ii | 0.97 | 2.54 | 3.465 (3) | 160 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C35H30N2O5Se |
Mr | 637.57 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 14.0886 (5), 10.6813 (4), 19.4744 (7) |
β (°) | 92.721 (2) |
V (Å3) | 2927.29 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.33 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker KappaAPEX2 diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.691, 0.777 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 38750, 9941, 5805 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.744 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.116, 1.01 |
No. of reflections | 9941 |
No. of parameters | 389 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.79, −0.67 |
Computer programs: APEX2 (Bruker, 2004), SAINT (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 |
C5—H5···O1i | 0.98 | 2.42 | 3.199 (3) | 136 |
C29—H29A···O5ii | 0.97 | 2.54 | 3.465 (3) | 160 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, z−1/2. |
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, India, for their support.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, S1–19. CrossRef Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Brakhage, A. A. (1998). Microbiol. Mol. Biol. Rev. 62, 547–585. Web of Science CAS PubMed Google Scholar
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA. Google Scholar
Chenera, P., West, M. L., Finkelstein, J. A. & Dreyer, G. B. J. (1993). J. Org. Chem. 58, 5605–5606. CrossRef CAS Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Ellis, G. P. (1997). Chromenes, Chromanones and Chromones. New York: John Wiley and Sons Inc. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820–5824. CrossRef CAS Web of Science Google Scholar
Koojiman, H., Spek, A. L., Kleijin, H., Van Maanen, H. L., Jastrzelski, J. T. B. H. & Van Kozrkowski, A. P. (1984). Acc. Chem. Res. 17, 410–416. Google Scholar
Lampronti, I., Martello, D., Bianchi, N., Borgatti, M., Lambertini, E., Piva, R., Jabbar, S., Shahabuddin Kabir Choudhuri, M., Tareq Hassan Khan, M. & Gambari, R. (2003). Phytomedicine, 10, 300–308. Web of Science CrossRef PubMed CAS Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science 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. (2003). J. Appl. Cryst. 36, 7–13. Web of Science 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.
Chromanones are found to exhibit strong activity in inhibiting in vitro cell growth of human tumour cells (Lampronti et al., 2003). Many chromanone derivatives are versatile intermediates for the synthesis of natural products such as brazillin, hematoxylin, ripariochromene, clausenin, calonlide A and inophyllum B (Koojiman et al.,1984; Ellis et al., 1997; Chenera et al., 1993). Pyrrolidines and pyrroles are common structural motifs in drugs and drug candidates owing to their ability to act as selective glycosidase inhibitors which are used in the treatment of diabetes, cancer, malaria and viral infections including AIDS (Kilonda et al.,1995). The most commonly used β-lactam antibiotics for the therapy of infectious diseases are penicillin and cephalosporin (Brakhage, 1998). In view of the above, the crystal structure determination of the title compound was carried out and the results are presented here.
Bond lengths of the title compound (Fig. 1) show normal values (Allen et al., 1987). The pyrrolidine ring (N2/C4/C2/C3/C5) adopts an envelope conformation with an asymmetry parameter (Nardelli,1983) ΔCs(N2) of 3.8 (2)° and puckering parameters (Cremer and Pople, 1975) of q2 = 0.366 (2) Å and ϕ2 = 184.9 (3)°. The oxazolidine ring (O2/N2/C5/C7/C6) is in a twist conformation with an asymmetry parameter ΔC2(O2) of 8.9 (2)° and puckering parameters q2 = 0.329 (2) Å and ϕ2 = 262.2 (3)°. The sums of bond angles around atom N1 (359.7°) and N2 (324.5°) indicate sp2 and sp3 hybridization, respectively. The tetrahydropyran ring adopts a half-chair conformation. The dihedral angle between the azetidinone ring and the attached methoxyphenyl ring is 15.7 (1)°.
In the crystal packing, intermolecular C—H···O interactions (Table 1) link the molecules into a two-dimensional network (Fig. 2).