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Acta Cryst. (2008). E64, o851-o852    [ doi:10.1107/S1600536808008829 ]

1-(4-Methoxyphenyl)-7-phenyl-3-(phenylselenylmethyl)perhydroisoxazolo[2',3':1,2]pyrrolo[3,4-b]azetidine-6-spiro-2'-chroman-2,4'-dione

E. T. S. Kamala, S. Nirmala, L. Sudha, N. Arumugam and R. Raghunathan

Abstract top

In the title compound, C35H30N2O5Se, the pyrrolidine ring adopts an envelope conformation 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 crystal structure, intermolecular C-H...O interactions link the molecules into a two-dimensional network.

Comment top

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).

Related literature top

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 top

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 column chromatography. The title compound was crystallized from benzene solution by slow evaporation technique.

Refinement top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. A view of the molecular packing of the title compound.
1-(4-Methoxyphenyl)-7-phenyl-3-\ (phenylselenylmethyl)perhydroisoxazolo[2',3':1,2]pyrrolo[3,4-\ b]azetidine-6-spiro-2'-chroman-2,4'-dione top
Crystal data top
C35H30N2O5SeF000 = 1312
Mr = 637.57Dx = 1.447 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 38750 reflections
a = 14.0886 (5) Åθ = 1.8–31.9º
b = 10.6813 (4) ŵ = 1.33 mm−1
c = 19.4744 (7) ÅT = 293 (2) K
β = 92.721 (2)ºPrism, colourless
V = 2927.29 (18) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker KappaAPEX2
diffractometer		9941 independent reflections
Radiation source: fine-focus sealed tube5805 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 293(2) Kθmax = 31.9º
ω and φ scansθmin = 1.8º
Absorption correction: multi-scan
(Blessing, 1995)		h = −19→20
Tmin = 0.691, Tmax = 0.777k = −15→10
38750 measured reflectionsl = −28→28
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.116  w = 1/[σ2(Fo2) + (0.0444P)2 + 1.2941P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
9941 reflectionsΔρmax = 0.79 e Å−3
389 parametersΔρmin = −0.67 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C35H30N2O5SeV = 2927.29 (18) Å3
Mr = 637.57Z = 4
Monoclinic, P21/nMo Kα
a = 14.0886 (5) ŵ = 1.33 mm−1
b = 10.6813 (4) ÅT = 293 (2) K
c = 19.4744 (7) Å0.30 × 0.20 × 0.20 mm
β = 92.721 (2)º
Data collection top
Bruker KappaAPEX2
diffractometer		9941 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)		5805 reflections with I > 2σ(I)
Tmin = 0.691, Tmax = 0.777Rint = 0.028
38750 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045389 parameters
wR(F2) = 0.116H-atom parameters constrained
S = 1.01Δρmax = 0.79 e Å−3
9941 reflectionsΔρmin = −0.67 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se11.016999 (16)0.19600 (3)0.180072 (11)0.05427 (9)
O10.84548 (10)0.24863 (15)0.33002 (7)0.0499 (4)
O20.69775 (9)0.13919 (14)0.07844 (6)0.0423 (3)
O30.64805 (13)0.40844 (15)0.12826 (7)0.0583 (4)
O40.54329 (11)0.16190 (14)−0.01690 (7)0.0482 (4)
O50.42581 (12)0.20236 (17)0.48343 (9)0.0662 (5)
N10.71402 (11)0.11790 (15)0.30571 (7)0.0353 (3)
N20.74055 (11)0.06570 (15)0.13393 (7)0.0358 (3)
C10.80284 (13)0.16622 (18)0.30008 (9)0.0359 (4)
C20.82270 (13)0.07814 (18)0.24043 (9)0.0357 (4)
H20.87490.01890.24970.043*
C30.72246 (13)0.02471 (18)0.25094 (9)0.0354 (4)
H30.7221−0.06230.26690.042*
C40.81961 (13)0.13643 (18)0.16898 (9)0.0343 (4)
H40.80390.22560.17140.041*
C50.66549 (13)0.04692 (18)0.18298 (9)0.0346 (4)
H50.6280−0.02760.17040.041*
C60.60958 (12)0.19551 (17)0.09998 (9)0.0322 (4)
C70.60343 (12)0.16392 (17)0.17651 (9)0.0324 (4)
H70.63590.23080.20280.039*
C80.62051 (13)0.33430 (18)0.08468 (9)0.0352 (4)
C90.60212 (13)0.36900 (18)0.01199 (9)0.0357 (4)
C100.62385 (15)0.4882 (2)−0.01152 (11)0.0458 (5)
H100.64560.54900.01950.055*
C110.61339 (18)0.5166 (2)−0.08025 (12)0.0552 (6)
H110.62830.5963−0.09570.066*
C120.58075 (18)0.4265 (2)−0.12602 (11)0.0580 (6)
H120.57430.4459−0.17260.070*
C130.55774 (17)0.3095 (2)−0.10459 (11)0.0525 (6)
H130.53550.2498−0.13620.063*
C140.56779 (14)0.27993 (19)−0.03503 (10)0.0396 (4)
C150.52914 (14)0.1432 (2)0.05444 (10)0.0421 (4)
H15A0.52320.05420.06330.051*
H15B0.47020.18300.06610.051*
C160.50369 (13)0.1537 (2)0.20162 (10)0.0412 (4)
C170.45117 (18)0.0450 (3)0.19745 (14)0.0660 (7)
H170.4770−0.02620.17810.079*
C180.3608 (2)0.0404 (4)0.22162 (16)0.0898 (11)
H180.3265−0.03390.21860.108*
C190.3214 (2)0.1434 (5)0.24973 (16)0.0944 (12)
H190.26040.13960.26590.113*
C200.3719 (2)0.2522 (4)0.25400 (15)0.0848 (10)
H200.34500.32290.27300.102*
C210.46266 (16)0.2584 (3)0.23037 (12)0.0561 (6)
H210.49650.33310.23370.067*
C220.64158 (13)0.13740 (18)0.35180 (9)0.0355 (4)
C230.57163 (15)0.0489 (2)0.35695 (10)0.0455 (5)
H230.5739−0.02400.33090.055*
C240.49788 (16)0.0667 (2)0.40035 (11)0.0491 (5)
H240.45070.00630.40350.059*
C250.49483 (14)0.1746 (2)0.43884 (10)0.0448 (5)
C260.56613 (15)0.2627 (2)0.43419 (11)0.0474 (5)
H260.56470.33480.46080.057*
C270.63907 (14)0.2453 (2)0.39089 (10)0.0424 (4)
H270.68640.30550.38790.051*
C280.34568 (18)0.1226 (3)0.48395 (15)0.0736 (8)
H28A0.30160.15440.51580.110*
H28B0.36550.04000.49770.110*
H28C0.31560.11940.43870.110*
C290.90857 (14)0.1174 (2)0.13028 (10)0.0441 (5)
H29A0.90030.15400.08480.053*
H29B0.92050.02860.12500.053*
C301.11387 (14)0.1421 (2)0.12143 (10)0.0423 (4)
C311.12365 (18)0.0189 (2)0.10270 (15)0.0628 (7)
H311.0823−0.04120.11870.075*
C321.19504 (19)−0.0161 (3)0.05994 (17)0.0766 (8)
H321.2007−0.09940.04680.092*
C331.25653 (18)0.0703 (3)0.03718 (14)0.0715 (8)
H331.30500.04610.00920.086*
C341.24733 (17)0.1910 (3)0.05514 (14)0.0641 (7)
H341.28930.25020.03910.077*
C351.17647 (15)0.2283 (2)0.09712 (12)0.0523 (5)
H351.17100.31220.10900.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.04250 (13)0.07341 (18)0.04728 (13)0.00234 (11)0.00606 (9)−0.01202 (11)
O10.0460 (8)0.0529 (9)0.0506 (8)−0.0080 (7)0.0006 (7)−0.0064 (7)
O20.0403 (7)0.0574 (9)0.0294 (6)0.0159 (6)0.0042 (5)−0.0001 (6)
O30.0896 (12)0.0422 (9)0.0416 (8)−0.0170 (8)−0.0122 (8)−0.0078 (7)
O40.0623 (9)0.0430 (8)0.0380 (7)−0.0094 (7)−0.0108 (6)−0.0066 (6)
O50.0488 (9)0.0835 (13)0.0684 (11)−0.0043 (8)0.0253 (8)−0.0200 (9)
N10.0391 (8)0.0353 (9)0.0317 (7)0.0000 (7)0.0052 (6)−0.0020 (6)
N20.0373 (8)0.0384 (9)0.0318 (7)0.0091 (7)0.0030 (6)−0.0002 (6)
C10.0366 (10)0.0386 (11)0.0324 (8)0.0039 (8)0.0002 (7)0.0068 (8)
C20.0367 (9)0.0369 (11)0.0337 (8)0.0093 (8)0.0030 (7)0.0043 (8)
C30.0426 (10)0.0296 (9)0.0343 (8)0.0053 (8)0.0064 (7)0.0023 (7)
C40.0346 (9)0.0366 (10)0.0320 (8)0.0071 (8)0.0037 (7)0.0019 (7)
C50.0356 (9)0.0316 (10)0.0368 (9)0.0018 (7)0.0043 (7)−0.0045 (7)
C60.0291 (8)0.0354 (10)0.0319 (8)0.0033 (7)−0.0003 (6)−0.0067 (7)
C70.0290 (8)0.0338 (10)0.0346 (8)0.0012 (7)0.0026 (7)−0.0051 (7)
C80.0329 (9)0.0366 (10)0.0359 (9)−0.0005 (8)−0.0018 (7)−0.0051 (8)
C90.0328 (9)0.0370 (11)0.0370 (9)0.0044 (8)−0.0031 (7)−0.0028 (8)
C100.0509 (12)0.0403 (12)0.0460 (11)0.0000 (9)−0.0015 (9)−0.0025 (9)
C110.0664 (15)0.0471 (13)0.0518 (12)0.0032 (11)−0.0001 (11)0.0106 (11)
C120.0684 (16)0.0632 (16)0.0415 (11)0.0064 (13)−0.0073 (10)0.0058 (11)
C130.0604 (14)0.0559 (15)0.0397 (10)0.0007 (11)−0.0131 (10)−0.0056 (10)
C140.0369 (10)0.0424 (12)0.0386 (9)0.0031 (8)−0.0077 (8)−0.0047 (8)
C150.0442 (11)0.0393 (11)0.0422 (10)−0.0072 (9)−0.0047 (8)−0.0056 (9)
C160.0327 (10)0.0552 (13)0.0360 (9)0.0011 (9)0.0044 (7)−0.0014 (9)
C170.0502 (14)0.0756 (18)0.0733 (16)−0.0166 (13)0.0132 (12)−0.0070 (14)
C180.0539 (17)0.138 (3)0.0782 (19)−0.0374 (19)0.0110 (15)0.004 (2)
C190.0363 (14)0.181 (4)0.0671 (18)0.004 (2)0.0132 (12)0.010 (2)
C200.0533 (17)0.134 (3)0.0680 (17)0.0316 (19)0.0163 (14)−0.0062 (19)
C210.0462 (13)0.0687 (16)0.0539 (12)0.0178 (11)0.0093 (10)−0.0033 (12)
C220.0382 (10)0.0385 (11)0.0299 (8)0.0018 (8)0.0021 (7)0.0019 (8)
C230.0525 (12)0.0419 (12)0.0431 (10)−0.0058 (9)0.0124 (9)−0.0067 (9)
C240.0471 (12)0.0500 (13)0.0512 (12)−0.0109 (10)0.0115 (9)−0.0024 (10)
C250.0365 (10)0.0601 (14)0.0384 (10)0.0029 (9)0.0075 (8)−0.0040 (9)
C260.0467 (12)0.0502 (13)0.0457 (11)−0.0004 (10)0.0073 (9)−0.0151 (10)
C270.0419 (11)0.0432 (11)0.0424 (10)−0.0050 (9)0.0049 (8)−0.0083 (9)
C280.0448 (14)0.099 (2)0.0793 (18)−0.0042 (14)0.0260 (12)−0.0061 (16)
C290.0366 (10)0.0604 (14)0.0359 (9)0.0025 (9)0.0062 (8)−0.0018 (9)
C300.0331 (10)0.0500 (12)0.0437 (10)0.0037 (9)−0.0003 (8)−0.0039 (9)
C310.0492 (13)0.0477 (14)0.0919 (19)−0.0018 (11)0.0087 (13)−0.0055 (13)
C320.0586 (16)0.0615 (17)0.110 (2)0.0086 (13)0.0066 (15)−0.0344 (16)
C330.0411 (13)0.099 (2)0.0751 (17)−0.0032 (14)0.0079 (12)−0.0348 (16)
C340.0431 (13)0.085 (2)0.0653 (15)−0.0131 (12)0.0090 (11)−0.0100 (14)
C350.0420 (12)0.0548 (14)0.0601 (13)−0.0032 (10)0.0028 (10)−0.0081 (11)
Geometric parameters (Å, °) top
Se1—C301.910 (2)C13—H130.93
Se1—C291.959 (2)C15—H15A0.97
O1—C11.201 (2)C15—H15B0.97
O2—N21.4441 (19)C16—C171.377 (3)
O2—C61.460 (2)C16—C211.389 (3)
O3—C81.211 (2)C17—C181.379 (4)
O4—C141.358 (2)C17—H170.93
O4—C151.427 (2)C18—C191.359 (5)
O5—C251.367 (2)C18—H180.93
O5—C281.414 (3)C19—C201.364 (5)
N1—C11.363 (2)C19—H190.93
N1—C221.406 (2)C20—C211.381 (4)
N1—C31.468 (2)C20—H200.93
N2—C51.472 (2)C21—H210.93
N2—C41.485 (2)C22—C231.373 (3)
C1—C21.531 (3)C22—C271.382 (3)
C2—C41.523 (2)C23—C241.383 (3)
C2—C31.546 (3)C23—H230.93
C2—H20.98C24—C251.376 (3)
C3—C51.533 (3)C24—H240.93
C3—H30.98C25—C261.382 (3)
C4—C291.506 (3)C26—C271.372 (3)
C4—H40.98C26—H260.93
C5—C71.527 (3)C27—H270.93
C5—H50.98C28—H28A0.96
C6—C151.513 (2)C28—H28B0.96
C6—C81.521 (3)C28—H28C0.96
C6—C71.535 (2)C29—H29A0.97
C7—C161.513 (2)C29—H29B0.97
C7—H70.98C30—C311.374 (3)
C8—C91.474 (3)C30—C351.375 (3)
C9—C141.391 (3)C31—C321.387 (4)
C9—C101.392 (3)C31—H310.93
C10—C111.374 (3)C32—C331.354 (4)
C10—H100.93C32—H320.93
C11—C121.376 (3)C33—C341.344 (4)
C11—H110.93C33—H330.93
C12—C131.362 (3)C34—C351.379 (3)
C12—H120.93C34—H340.93
C13—C141.392 (3)C35—H350.93
C30—Se1—C2997.90 (8)O4—C15—H15A109.1
N2—O2—C6109.86 (12)C6—C15—H15A109.1
C14—O4—C15115.61 (15)O4—C15—H15B109.1
C25—O5—C28117.78 (19)C6—C15—H15B109.1
C1—N1—C22133.82 (16)H15A—C15—H15B107.8
C1—N1—C395.27 (14)C17—C16—C21118.0 (2)
C22—N1—C3130.58 (16)C17—C16—C7123.1 (2)
O2—N2—C5105.81 (13)C21—C16—C7118.9 (2)
O2—N2—C4110.17 (14)C16—C17—C18120.8 (3)
C5—N2—C4108.50 (13)C16—C17—H17119.6
O1—C1—N1132.72 (18)C18—C17—H17119.6
O1—C1—C2135.53 (18)C19—C18—C17120.7 (3)
N1—C1—C291.72 (15)C19—C18—H18119.7
C4—C2—C1116.34 (16)C17—C18—H18119.7
C4—C2—C3106.57 (14)C18—C19—C20119.5 (3)
C1—C2—C385.72 (13)C18—C19—H19120.2
C4—C2—H2114.8C20—C19—H19120.2
C1—C2—H2114.8C19—C20—C21120.6 (3)
C3—C2—H2114.8C19—C20—H20119.7
N1—C3—C5117.72 (15)C21—C20—H20119.7
N1—C3—C287.24 (14)C20—C21—C16120.4 (3)
C5—C3—C2105.83 (14)C20—C21—H21119.8
N1—C3—H3114.2C16—C21—H21119.8
C5—C3—H3114.2C23—C22—C27119.77 (18)
C2—C3—H3114.2C23—C22—N1119.34 (17)
N2—C4—C29108.99 (15)C27—C22—N1120.88 (17)
N2—C4—C2101.55 (14)C22—C23—C24120.83 (19)
C29—C4—C2114.43 (15)C22—C23—H23119.6
N2—C4—H4110.5C24—C23—H23119.6
C29—C4—H4110.5C25—C24—C23119.5 (2)
C2—C4—H4110.5C25—C24—H24120.3
N2—C5—C7105.14 (15)C23—C24—H24120.3
N2—C5—C3102.61 (14)O5—C25—C24124.7 (2)
C7—C5—C3118.17 (15)O5—C25—C26115.79 (19)
N2—C5—H5110.1C24—C25—C26119.50 (19)
C7—C5—H5110.1C27—C26—C25121.1 (2)
C3—C5—H5110.1C27—C26—H26119.5
O2—C6—C15107.66 (14)C25—C26—H26119.5
O2—C6—C8104.47 (14)C26—C27—C22119.4 (2)
C15—C6—C8108.99 (15)C26—C27—H27120.3
O2—C6—C7106.06 (13)C22—C27—H27120.3
C15—C6—C7114.39 (15)O5—C28—H28A109.5
C8—C6—C7114.54 (14)O5—C28—H28B109.5
C16—C7—C5116.80 (16)H28A—C28—H28B109.5
C16—C7—C6115.20 (15)O5—C28—H28C109.5
C5—C7—C6101.63 (14)H28A—C28—H28C109.5
C16—C7—H7107.5H28B—C28—H28C109.5
C5—C7—H7107.5C4—C29—Se1110.03 (13)
C6—C7—H7107.5C4—C29—H29A109.7
O3—C8—C9122.98 (18)Se1—C29—H29A109.7
O3—C8—C6122.14 (17)C4—C29—H29B109.7
C9—C8—C6114.72 (15)Se1—C29—H29B109.7
C14—C9—C10118.95 (18)H29A—C29—H29B108.2
C14—C9—C8119.98 (18)C31—C30—C35118.4 (2)
C10—C9—C8120.96 (17)C31—C30—Se1122.08 (17)
C11—C10—C9120.5 (2)C35—C30—Se1119.48 (17)
C11—C10—H10119.7C30—C31—C32120.1 (2)
C9—C10—H10119.7C30—C31—H31119.9
C10—C11—C12119.6 (2)C32—C31—H31119.9
C10—C11—H11120.2C33—C32—C31120.4 (3)
C12—C11—H11120.2C33—C32—H32119.8
C13—C12—C11121.4 (2)C31—C32—H32119.8
C13—C12—H12119.3C34—C33—C32119.8 (2)
C11—C12—H12119.3C34—C33—H33120.1
C12—C13—C14119.5 (2)C32—C33—H33120.1
C12—C13—H13120.3C33—C34—C35120.9 (2)
C14—C13—H13120.3C33—C34—H34119.6
O4—C14—C9123.26 (17)C35—C34—H34119.6
O4—C14—C13116.63 (17)C30—C35—C34120.3 (2)
C9—C14—C13120.1 (2)C30—C35—H35119.8
O4—C15—C6112.56 (16)C34—C35—H35119.8
C6—O2—N2—C515.91 (18)C8—C9—C10—C11174.9 (2)
C6—O2—N2—C4−101.18 (16)C9—C10—C11—C120.3 (3)
C22—N1—C1—O1−6.5 (4)C10—C11—C12—C130.5 (4)
C3—N1—C1—O1179.8 (2)C11—C12—C13—C14−0.3 (4)
C22—N1—C1—C2175.33 (19)C15—O4—C14—C916.9 (3)
C3—N1—C1—C21.69 (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—C4104.78 (17)C8—C9—C14—O44.8 (3)
O1—C1—C2—C3−179.7 (2)C10—C9—C14—C131.5 (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—O4179.7 (2)
C22—N1—C3—C577.9 (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—O457.3 (2)
C1—C2—C3—N11.49 (12)C7—C6—C15—O4−173.07 (16)
C4—C2—C3—C53.32 (19)C5—C7—C16—C17−32.9 (3)
C1—C2—C3—C5119.55 (15)C6—C7—C16—C1786.3 (3)
O2—N2—C4—C29−84.46 (17)C5—C7—C16—C21147.02 (19)
C5—N2—C4—C29160.14 (15)C6—C7—C16—C21−93.8 (2)
O2—N2—C4—C2154.42 (13)C21—C16—C17—C18−0.5 (4)
C5—N2—C4—C239.02 (17)C7—C16—C17—C18179.5 (2)
C1—C2—C4—N2−118.02 (17)C16—C17—C18—C190.4 (5)
C3—C2—C4—N2−24.55 (18)C17—C18—C19—C200.0 (5)
C1—C2—C4—C29124.75 (19)C18—C19—C20—C21−0.3 (5)
C3—C2—C4—C29−141.78 (17)C19—C20—C21—C160.2 (4)
O2—N2—C5—C7−31.16 (17)C17—C16—C21—C200.1 (4)
C4—N2—C5—C787.05 (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—C2311.3 (3)
N1—C3—C5—N2114.86 (17)C1—N1—C22—C2720.8 (3)
C2—C3—C5—N219.55 (18)C3—N1—C22—C27−167.57 (18)
N1—C3—C5—C7−0.2 (2)C27—C22—C23—C240.6 (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—C8127.06 (14)C28—O5—C25—C24−8.2 (3)
N2—O2—C6—C75.68 (18)C28—O5—C25—C26172.7 (2)
N2—C5—C7—C16159.75 (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—C633.51 (17)O5—C25—C26—C27−179.7 (2)
C3—C5—C7—C6147.19 (16)C24—C25—C26—C271.1 (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—C1694.2 (2)N1—C22—C27—C26178.50 (18)
O2—C6—C7—C5−23.81 (18)N2—C4—C29—Se1−174.50 (12)
C15—C6—C7—C594.68 (18)C2—C4—C29—Se1−61.6 (2)
C8—C6—C7—C5−138.47 (15)C30—Se1—C29—C4175.59 (15)
O2—C6—C8—O3−96.2 (2)C29—Se1—C30—C31−50.9 (2)
C15—C6—C8—O3148.92 (19)C29—Se1—C30—C35129.36 (18)
C7—C6—C8—O319.3 (3)C35—C30—C31—C32−0.3 (4)
O2—C6—C8—C979.28 (18)Se1—C30—C31—C32180.0 (2)
C15—C6—C8—C9−35.6 (2)C30—C31—C32—C331.0 (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—C350.6 (4)
C6—C8—C9—C146.5 (2)C31—C30—C35—C34−0.2 (3)
O3—C8—C9—C105.8 (3)Se1—C30—C35—C34179.50 (18)
C6—C8—C9—C10−169.71 (17)C33—C34—C35—C300.1 (4)
C14—C9—C10—C11−1.3 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.982.423.199 (3)136
C29—H29A···O5ii0.972.543.465 (3)160
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.982.423.199 (3)136
C29—H29A···O5ii0.972.543.465 (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 top

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
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