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

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

doi:10.1107/S1600536808008829

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages o851-o852

doi:10.1107/S1600536808008829

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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. Theboral Sugi Kamala,^a S. Nirmala,^a L. Sudha,^b ^* N. Arumugam ^c and R. Raghunathan ^c

^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

(Received 12 March 2008; accepted 1 April 2008; online 16 April 2008)

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.

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

C₃₅H₃₀N₂O₅Se
M_r = 637.57
Monoclinic, P 2₁ /n
a = 14.0886 (5) Å
b = 10.6813 (4) Å
c = 19.4744 (7) Å
β = 92.721 (2)°
V = 2927.29 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.33 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.691, T_max = 0.777
38750 measured reflections
9941 independent reflections
5805 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.116
S = 1.01
9941 reflections
389 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+{3 \over 2},y-{1 \over 2},-z+{1 \over 2}]$ ; (ii) $[x+{1 \over 2},-y+{1 \over 2},z-{1 \over 2}]$ .

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008829/ci2571sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008829/ci2571Isup2.hkl

checkCIF report

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) ΔC_s(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.

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

	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.

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

C₃₅H₃₀N₂O₅Se	F(000) = 1312
M_r = 637.57	D_x = 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

Data collection top

Bruker KappaAPEX2 diffractometer	9941 independent reflections
Radiation source: fine-focus sealed tube	5805 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and ϕ scans	θ_max = 31.9°, θ_min = 1.8°
Absorption correction: multi-scan (Blessing, 1995)	h = −19→20
T_min = 0.691, T_max = 0.777	k = −15→10
38750 measured reflections	l = −28→28

Refinement top

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(F_o²) + (0.0444P)² + 1.2941P] where P = (F_o² + 2F_c²)/3
9941 reflections	(Δ/σ)_max = 0.001
389 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

C₃₅H₃₀N₂O₅Se	V = 2927.29 (18) Å³
M_r = 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)°

Data collection top

Bruker KappaAPEX2 diffractometer	9941 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	5805 reflections with I > 2σ(I)
T_min = 0.691, T_max = 0.777	R_int = 0.028
38750 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.01	Δρ_max = 0.79 e Å⁻³
9941 reflections	Δρ_min = −0.67 e Å⁻³
389 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.691, 0.777
No. of measured, independent and observed [I > 2σ(I)] reflections	38750, 9941, 5805
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

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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
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Volume 64| Part 5| May 2008| Pages o851-o852

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

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