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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 4| April 2008| Pages o716-o717

3-(4-Chloro­phen­yl)-4-(4-methoxyphen­yl)-6-(phenyl­selenylmeth­yl)-2,3,3a,3b,4,5,5a,6,1′′,2′′,3′′,4′′-do­deca­hydro­azeto[2′,3′:3,4]pyrrolo[1,2-b]isoxazole-2-spiro-2′′-naphthalene-5,1′′-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: sudha.rmp@ph.srmuniv.ac.in

(Received 22 January 2008; accepted 9 March 2008; online 14 March 2008)

In the title compound, C36H31ClN2O4Se, the four-membered β-lactam ring is fused to a pyrrolidine ring. The central five-membered ring of the fused tricyclic system exhibits an envelope conformation with the N atom as the flap, while the other five-membered ring exhibits a twist conformation. The chloro­phenyl ring is almost perpendicular to the pyrrolidine ring, making a dihedral angle of 73.45 (1)°. The crystal structure is stabilized by weak inter­molecular C—H⋯O inter­actions and the packing is further enhanced by C—H ⋯N inter­actions and ππ inter­actions between benzene rings of tetra­lone groups in mol­ecules related by an inversion center, with a centroid–centroid separation of 3.8923 (2) Å.

Related literature

For related literature, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]); Amal Raj et al. (2003[Amal Raj, A., Raghunathan, R., Sridevikumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-419.]); Brakhage (1998[Brakhage, A. A. (1998). Microbiol. Mol. Biol. Rev. 62, 547-585.]); Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Kilonda et al. (1995[Kilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820-5824.]); Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C36H31ClN2O4Se

  • Mr = 670.04

  • Monoclinic, P 21 /n

  • a = 14.4697 (3) Å

  • b = 10.9493 (3) Å

  • c = 19.3011 (4) Å

  • β = 94.661 (1)°

  • V = 3047.82 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.36 mm−1

  • T = 293 (2) K

  • 0.30 × 0.30 × 0.24 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.671, Tmax = 0.720

  • 37171 measured reflections

  • 8699 independent reflections

  • 5453 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.176

  • S = 1.02

  • 8699 reflections

  • 398 parameters

  • H-atom parameters constrained

  • Δρmax = 0.72 e Å−3

  • Δρmin = −0.86 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯O4i 0.98 2.57 3.305 (3) 132
C23—H23⋯O2 0.98 2.32 2.803 (3) 109
C23—H23⋯N1 0.98 2.54 2.918 (3) 103
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

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). These derivatives also possess antimicrobial and antifungal activity (Amal Raj et al., 2003). The discovery of β-lactam is very significant in the history of therapeutic medicine as an antibiotic in the form of penicillin and cephalosporin for infectious diseases (Brakhage, 1998). Due to their importance, the crystal structure determination of the title compound, (I), was carried out and the results are presented here.

Figure 1 shows the ORTEP-3 (Farrugia, 1997) plot of compound (I). Bond lengths and angles are comparable with other reported values (Allen et al., 1987).

In the molecule the five membered ring N2/C3/C2/C5/C4 exhibits envelope conformation with envelope on N2 and with an asymmetry parameter (Nardelli, 1983) Δs(N2) = 0.0067 (1) and with the puckering parameters (Cremer & Pople, 1975) q2 = 0.3669 (3) Å and ϕ2 = 70.58 (4)°. Another five membered ring C4/C23/C13/O1/N2 exhibits twist conformation with asymmetry parameters Δs(C4) = 0.0297 (13), Δ2(O1) = 0.0414 (9) and with the puckering parameters q2 = 0.3452 (2) Å and ϕ2 = -173.27 (4)°.

The sum of bond angles around atom N1, 359.8°, and around atom N2, 324.57°, indicate sp2 and sp3 hybridizations, respectively. The chlorobenzene ring is almost perpendicular to the pyrrolidine ring, making a dihedral angle of 73.45 (1)°. The anisole ring makes a dihedral angle of 14.85 (1)° with the central β-lactam ring, while angle between anisole and tetrahydronapthanone is 66.38 (1)°.

In the crystal packing, atoms O2 and O4 are involved in intermolecular and intramolecular C—H···O interactions, along with C—H···N interactions. Weak intermolecular π···π interactions occur within the benzene ring C15···C20 (1 - x, -y, 1 - z), with a centroid-to-centroid separation of 3.8923 (2) Å.

Related literature top

For related literature, see: Allen et al. (1987); Amal Raj et al. (2003); Brakhage (1998); Cremer & Pople (1975); Kilonda et al. (1995); Nardelli (1983).

Experimental top

To a solution of the bicyclic nitrone (1 mmol) in dry acetonitrile (20 ml) was added 4-chlorobenzilidene tetralone (1 mmol) under N2 atmosphere. The mixture was refluxed for 4 h. After completion of the reaction, the solvent was distilled off under reduced pressure. The crude product was purified by column chromatography (hexane:ethyl acetate, 8:2) to give pure β-lactam (I) in good yield. The product was recrystallized from dry benzene by slow evaporation.

Refinement top

H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H bond lengths fixed to 0.93 (aromatic CH), 0.96 (methyl CH3), 0.97 (methylene CH2) or 0.98 Å (methine CH), and Uiso(H) = 1.2–1.5Ueq(carrier C).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The packing of the molecules viewed along c axis.
3-(4-Chlorophenyl)-4-(4-methoxyphenyl)-6-(phenylselenylmethyl)- 2,3,3a,3 b,4,5,5a,6,1'',2'',3'',4''-dodecahydroazeto[2',3':3,4]pyrrolo[1,2-b]isoxazole-2-spiro-2''-naphthalene-5,1''-dione top
Crystal data top
C36H31ClN2O4SeF(000) = 1376
Mr = 670.04Dx = 1.460 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 37171 reflections
a = 14.4697 (3) Åθ = 1.7–29.8°
b = 10.9493 (3) ŵ = 1.36 mm1
c = 19.3011 (4) ÅT = 293 K
β = 94.661 (1)°Prism, colourless
V = 3047.82 (12) Å30.30 × 0.30 × 0.24 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer
8699 independent reflections
Radiation source: fine-focus sealed tube5453 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω and ϕ scansθmax = 29.8°, θmin = 1.7°
Absorption correction: multi-scan
(Blessing, 1995)
h = 2019
Tmin = 0.671, Tmax = 0.720k = 1515
37171 measured reflectionsl = 2626
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)] = 0.053H-atom parameters constrained
wR(F2) = 0.176 w = 1/[σ2(Fo2) + (0.09P)2 + 1.6651P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
8699 reflectionsΔρmax = 0.72 e Å3
398 parametersΔρmin = 0.86 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0037 (6)
Crystal data top
C36H31ClN2O4SeV = 3047.82 (12) Å3
Mr = 670.04Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.4697 (3) ŵ = 1.36 mm1
b = 10.9493 (3) ÅT = 293 K
c = 19.3011 (4) Å0.30 × 0.30 × 0.24 mm
β = 94.661 (1)°
Data collection top
Bruker APEXII
diffractometer
8699 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
5453 reflections with I > 2σ(I)
Tmin = 0.671, Tmax = 0.720Rint = 0.035
37171 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.176H-atom parameters constrained
S = 1.02Δρmax = 0.72 e Å3
8699 reflectionsΔρmin = 0.86 e Å3
398 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.70233 (19)0.1671 (3)0.69974 (13)0.0414 (6)
C20.68196 (19)0.0826 (2)0.75936 (13)0.0419 (6)
H20.63030.02610.74860.050*
C30.68566 (18)0.1382 (3)0.83223 (12)0.0416 (6)
H30.70070.22540.83070.050*
C40.83576 (18)0.0507 (2)0.82017 (12)0.0383 (5)
H40.87420.02050.83360.046*
C50.77879 (19)0.0276 (2)0.75107 (12)0.0405 (5)
H50.77770.05800.73610.049*
C60.85780 (18)0.1320 (2)0.64929 (12)0.0398 (6)
C70.9257 (2)0.0452 (3)0.64583 (14)0.0480 (6)
H70.92330.02580.67210.058*
C80.9979 (2)0.0618 (3)0.60390 (15)0.0534 (7)
H81.04370.00250.60210.064*
C91.0015 (2)0.1668 (3)0.56475 (15)0.0520 (7)
C100.9323 (2)0.2523 (3)0.56705 (16)0.0556 (7)
H100.93370.32200.53960.067*
C110.8610 (2)0.2368 (3)0.60915 (15)0.0487 (6)
H110.81520.29620.61070.058*
C121.1467 (3)0.1143 (5)0.5225 (2)0.0798 (11)
H12A1.18830.14300.48970.120*
H12B1.12660.03310.51000.120*
H12C1.17810.11350.56820.120*
C130.89041 (17)0.1991 (2)0.90386 (12)0.0330 (5)
C140.87399 (17)0.3350 (2)0.91654 (13)0.0371 (5)
C150.89318 (17)0.3797 (2)0.98876 (13)0.0371 (5)
C160.8704 (2)0.5000 (3)1.00480 (17)0.0519 (7)
H160.84410.55160.97040.062*
C170.8873 (3)0.5414 (3)1.07230 (19)0.0643 (9)
H170.87130.62091.08330.077*
C180.9270 (2)0.4672 (3)1.12289 (17)0.0623 (9)
H180.93810.49661.16800.075*
C190.9505 (2)0.3509 (3)1.10802 (14)0.0495 (7)
H190.97830.30131.14290.059*
C200.93320 (17)0.3050 (2)1.04094 (13)0.0389 (5)
C210.9594 (2)0.1759 (3)1.02692 (14)0.0494 (7)
H21A0.91140.12191.04130.059*
H21B1.01650.15631.05450.059*
C220.9726 (2)0.1536 (2)0.95051 (13)0.0425 (6)
H22A1.02830.19500.93840.051*
H22B0.98070.06680.94290.051*
C230.89336 (16)0.1679 (2)0.82651 (12)0.0337 (5)
H230.85840.23130.79990.040*
C240.98856 (18)0.1624 (3)0.80023 (13)0.0444 (6)
C251.0212 (2)0.2641 (3)0.76751 (15)0.0563 (8)
H250.98430.33370.76300.068*
C261.1072 (3)0.2648 (5)0.74137 (19)0.0852 (14)
H261.12810.33450.71990.102*
C271.1604 (3)0.1645 (6)0.74713 (19)0.0958 (18)
C281.1314 (3)0.0618 (6)0.7789 (2)0.0966 (17)
H281.16950.00680.78270.116*
C291.0447 (3)0.0594 (4)0.80593 (18)0.0716 (10)
H291.02470.01060.82750.086*
C300.5995 (2)0.1179 (4)0.87015 (15)0.0565 (8)
H30A0.60750.15520.91580.068*
H30B0.58980.03100.87620.068*
C310.4002 (2)0.1351 (3)0.87652 (14)0.0495 (7)
C320.3946 (3)0.0177 (4)0.9000 (2)0.0728 (10)
H320.43780.03980.88780.087*
C330.3252 (3)0.0167 (4)0.9417 (2)0.0842 (12)
H330.32260.09700.95720.101*
C340.2633 (3)0.0623 (5)0.9598 (2)0.0851 (13)
H340.21680.03750.98730.102*
C350.2670 (3)0.1785 (5)0.9386 (2)0.0879 (14)
H350.22370.23440.95250.106*
C360.3345 (2)0.2166 (4)0.8964 (2)0.0695 (10)
H360.33560.29730.88150.083*
N10.78743 (16)0.1158 (2)0.69470 (10)0.0394 (5)
N20.76374 (16)0.0684 (2)0.86869 (10)0.0419 (5)
O10.80695 (13)0.13881 (18)0.92556 (9)0.0450 (4)
O20.84345 (18)0.4012 (2)0.87024 (11)0.0628 (6)
O31.06894 (17)0.1926 (3)0.52152 (14)0.0757 (8)
O40.66189 (15)0.2495 (2)0.66906 (11)0.0575 (5)
Cl11.26648 (8)0.1614 (3)0.71137 (7)0.1700 (10)
Se10.49162 (2)0.18861 (4)0.817879 (17)0.06640 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0462 (14)0.0452 (15)0.0319 (11)0.0076 (12)0.0014 (10)0.0051 (10)
C20.0448 (14)0.0466 (15)0.0340 (11)0.0163 (11)0.0019 (10)0.0054 (10)
C30.0449 (14)0.0480 (15)0.0320 (11)0.0129 (12)0.0034 (10)0.0024 (10)
C40.0470 (14)0.0354 (12)0.0322 (11)0.0041 (11)0.0013 (10)0.0024 (9)
C50.0547 (15)0.0331 (12)0.0335 (11)0.0091 (11)0.0020 (10)0.0037 (9)
C60.0450 (14)0.0462 (15)0.0277 (11)0.0069 (11)0.0004 (9)0.0052 (10)
C70.0613 (17)0.0437 (15)0.0395 (13)0.0033 (13)0.0065 (12)0.0004 (11)
C80.0556 (17)0.0597 (18)0.0456 (15)0.0111 (14)0.0082 (12)0.0044 (13)
C90.0452 (15)0.069 (2)0.0419 (14)0.0051 (14)0.0051 (11)0.0015 (13)
C100.0513 (17)0.0624 (19)0.0534 (16)0.0034 (15)0.0055 (13)0.0174 (15)
C110.0461 (15)0.0539 (17)0.0461 (14)0.0023 (13)0.0037 (11)0.0076 (13)
C120.0520 (19)0.116 (3)0.073 (2)0.006 (2)0.0159 (17)0.004 (2)
C130.0358 (11)0.0332 (12)0.0295 (10)0.0023 (9)0.0003 (8)0.0025 (9)
C140.0349 (12)0.0385 (13)0.0370 (12)0.0038 (10)0.0020 (9)0.0025 (10)
C150.0344 (12)0.0364 (13)0.0407 (12)0.0044 (10)0.0051 (9)0.0012 (10)
C160.0573 (17)0.0390 (15)0.0604 (17)0.0009 (13)0.0109 (14)0.0014 (13)
C170.076 (2)0.0462 (17)0.072 (2)0.0042 (16)0.0178 (18)0.0197 (16)
C180.069 (2)0.069 (2)0.0504 (17)0.0174 (17)0.0099 (15)0.0185 (15)
C190.0516 (16)0.0585 (18)0.0381 (13)0.0102 (13)0.0011 (11)0.0052 (12)
C200.0362 (12)0.0446 (14)0.0353 (12)0.0061 (10)0.0003 (9)0.0025 (10)
C210.0636 (18)0.0473 (16)0.0347 (12)0.0094 (13)0.0108 (12)0.0033 (11)
C220.0509 (15)0.0379 (13)0.0371 (12)0.0117 (11)0.0074 (11)0.0010 (10)
C230.0351 (11)0.0353 (12)0.0303 (10)0.0016 (9)0.0003 (9)0.0023 (9)
C240.0381 (13)0.0622 (17)0.0325 (11)0.0017 (12)0.0002 (10)0.0039 (11)
C250.0518 (17)0.074 (2)0.0443 (15)0.0194 (15)0.0074 (12)0.0075 (14)
C260.053 (2)0.152 (4)0.0524 (19)0.036 (3)0.0117 (16)0.008 (2)
C270.0392 (18)0.209 (6)0.0390 (17)0.001 (3)0.0041 (13)0.014 (3)
C280.063 (2)0.169 (5)0.057 (2)0.057 (3)0.0006 (18)0.007 (3)
C290.065 (2)0.098 (3)0.0516 (18)0.032 (2)0.0041 (15)0.0042 (18)
C300.0450 (15)0.086 (2)0.0392 (14)0.0098 (15)0.0051 (11)0.0036 (14)
C310.0432 (14)0.0645 (19)0.0400 (13)0.0064 (13)0.0017 (11)0.0043 (12)
C320.070 (2)0.064 (2)0.086 (3)0.0009 (18)0.0116 (19)0.0029 (19)
C330.087 (3)0.077 (3)0.087 (3)0.023 (2)0.004 (2)0.027 (2)
C340.051 (2)0.128 (4)0.077 (3)0.011 (2)0.0054 (17)0.030 (3)
C350.050 (2)0.125 (4)0.090 (3)0.015 (2)0.0159 (19)0.022 (3)
C360.0545 (19)0.075 (2)0.079 (2)0.0053 (17)0.0061 (17)0.0215 (19)
N10.0482 (12)0.0390 (11)0.0307 (9)0.0051 (9)0.0012 (8)0.0010 (8)
N20.0487 (12)0.0452 (12)0.0316 (10)0.0131 (10)0.0020 (8)0.0011 (9)
O10.0508 (11)0.0568 (11)0.0272 (8)0.0179 (9)0.0031 (7)0.0000 (7)
O20.0903 (17)0.0478 (12)0.0468 (11)0.0209 (11)0.0156 (11)0.0064 (9)
O30.0550 (14)0.102 (2)0.0736 (16)0.0021 (13)0.0258 (12)0.0183 (14)
O40.0554 (12)0.0655 (14)0.0514 (11)0.0061 (11)0.0031 (9)0.0103 (11)
Cl10.0433 (5)0.398 (3)0.0709 (7)0.0147 (10)0.0161 (5)0.0191 (12)
Se10.0518 (2)0.0977 (3)0.0502 (2)0.00495 (17)0.00749 (14)0.01801 (17)
Geometric parameters (Å, º) top
C1—O41.204 (3)C17—C181.361 (5)
C1—N11.364 (4)C17—H170.9300
C1—C21.523 (4)C18—C191.355 (5)
C2—C31.529 (3)C18—H180.9300
C2—C51.546 (4)C19—C201.392 (4)
C2—H20.9800C19—H190.9300
C3—N21.492 (4)C20—C211.494 (4)
C3—C301.513 (4)C21—C221.522 (4)
C3—H30.9800C21—H21A0.9700
C4—N21.469 (3)C21—H21B0.9700
C4—C231.529 (3)C22—H22A0.9700
C4—C51.531 (3)C22—H22B0.9700
C4—H40.9800C23—C241.507 (4)
C5—N11.468 (3)C23—H230.9800
C5—H50.9800C24—C251.382 (4)
C6—C71.373 (4)C24—C291.389 (5)
C6—C111.388 (4)C25—C261.380 (5)
C6—N11.408 (3)C25—H250.9300
C7—C81.384 (4)C26—C271.341 (8)
C7—H70.9300C26—H260.9300
C8—C91.379 (4)C27—C281.363 (7)
C8—H80.9300C27—Cl11.734 (4)
C9—O31.364 (4)C28—C291.398 (6)
C9—C101.374 (5)C28—H280.9300
C10—C111.375 (4)C29—H290.9300
C10—H100.9300C30—Se11.949 (3)
C11—H110.9300C30—H30A0.9700
C12—O31.414 (5)C30—H30B0.9700
C12—H12A0.9600C31—C321.368 (5)
C12—H12B0.9600C31—C361.381 (5)
C12—H12C0.9600C31—Se11.902 (3)
C13—O11.467 (3)C32—C331.389 (6)
C13—C221.516 (3)C32—H320.9300
C13—C141.529 (3)C33—C341.313 (7)
C13—C231.536 (3)C33—H330.9300
C14—O21.206 (3)C34—C351.339 (6)
C14—C151.482 (3)C34—H340.9300
C15—C201.387 (4)C35—C361.386 (6)
C15—C161.399 (4)C35—H350.9300
C16—C171.382 (5)C36—H360.9300
C16—H160.9300N2—O11.442 (3)
O4—C1—N1132.7 (3)C20—C19—H19119.8
O4—C1—C2135.2 (3)C15—C20—C19119.7 (3)
N1—C1—C292.0 (2)C15—C20—C21121.6 (2)
C1—C2—C3117.3 (2)C19—C20—C21118.7 (2)
C1—C2—C585.76 (19)C20—C21—C22112.4 (2)
C3—C2—C5106.6 (2)C20—C21—H21A109.1
C1—C2—H2114.5C22—C21—H21A109.1
C3—C2—H2114.5C20—C21—H21B109.1
C5—C2—H2114.5C22—C21—H21B109.1
N2—C3—C30108.6 (2)H21A—C21—H21B107.9
N2—C3—C2101.5 (2)C13—C22—C21111.6 (2)
C30—C3—C2114.7 (2)C13—C22—H22A109.3
N2—C3—H3110.6C21—C22—H22A109.3
C30—C3—H3110.6C13—C22—H22B109.3
C2—C3—H3110.6C21—C22—H22B109.3
N2—C4—C23104.4 (2)H22A—C22—H22B108.0
N2—C4—C5102.6 (2)C24—C23—C4116.5 (2)
C23—C4—C5117.4 (2)C24—C23—C13115.8 (2)
N2—C4—H4110.6C4—C23—C13101.93 (18)
C23—C4—H4110.6C24—C23—H23107.4
C5—C4—H4110.6C4—C23—H23107.4
N1—C5—C4117.7 (2)C13—C23—H23107.4
N1—C5—C287.3 (2)C25—C24—C29118.1 (3)
C4—C5—C2105.9 (2)C25—C24—C23118.5 (3)
N1—C5—H5114.2C29—C24—C23123.4 (3)
C4—C5—H5114.2C26—C25—C24121.5 (4)
C2—C5—H5114.2C26—C25—H25119.2
C7—C6—C11119.3 (3)C24—C25—H25119.2
C7—C6—N1120.0 (2)C27—C26—C25119.6 (5)
C11—C6—N1120.7 (2)C27—C26—H26120.2
C6—C7—C8121.0 (3)C25—C26—H26120.2
C6—C7—H7119.5C26—C27—C28121.2 (4)
C8—C7—H7119.5C26—C27—Cl1120.3 (5)
C9—C8—C7119.6 (3)C28—C27—Cl1118.5 (4)
C9—C8—H8120.2C27—C28—C29120.1 (4)
C7—C8—H8120.2C27—C28—H28120.0
O3—C9—C10116.0 (3)C29—C28—H28120.0
O3—C9—C8124.6 (3)C24—C29—C28119.5 (4)
C10—C9—C8119.4 (3)C24—C29—H29120.2
C9—C10—C11121.3 (3)C28—C29—H29120.2
C9—C10—H10119.4C3—C30—Se1110.4 (2)
C11—C10—H10119.4C3—C30—H30A109.6
C10—C11—C6119.5 (3)Se1—C30—H30A109.6
C10—C11—H11120.2C3—C30—H30B109.6
C6—C11—H11120.2Se1—C30—H30B109.6
O3—C12—H12A109.5H30A—C30—H30B108.1
O3—C12—H12B109.5C32—C31—C36117.1 (3)
H12A—C12—H12B109.5C32—C31—Se1123.3 (3)
O3—C12—H12C109.5C36—C31—Se1119.6 (3)
H12A—C12—H12C109.5C31—C32—C33120.7 (4)
H12B—C12—H12C109.5C31—C32—H32119.6
O1—C13—C22107.84 (19)C33—C32—H32119.6
O1—C13—C14104.49 (19)C34—C33—C32121.1 (4)
C22—C13—C14110.4 (2)C34—C33—H33119.4
O1—C13—C23105.42 (18)C32—C33—H33119.4
C22—C13—C23114.9 (2)C33—C34—C35120.0 (4)
C14—C13—C23112.90 (19)C33—C34—H34120.0
O2—C14—C15121.9 (2)C35—C34—H34120.0
O2—C14—C13121.2 (2)C34—C35—C36120.9 (4)
C15—C14—C13116.9 (2)C34—C35—H35119.6
C20—C15—C16119.1 (2)C36—C35—H35119.6
C20—C15—C14121.6 (2)C31—C36—C35120.2 (4)
C16—C15—C14119.3 (2)C31—C36—H36119.9
C17—C16—C15119.4 (3)C35—C36—H36119.9
C17—C16—H16120.3C1—N1—C6134.1 (2)
C15—C16—H16120.3C1—N1—C594.9 (2)
C18—C17—C16120.9 (3)C6—N1—C5130.8 (2)
C18—C17—H17119.6O1—N2—C4105.64 (18)
C16—C17—H17119.6O1—N2—C3110.5 (2)
C19—C18—C17120.5 (3)C4—N2—C3108.43 (19)
C19—C18—H18119.8N2—O1—C13109.84 (17)
C17—C18—H18119.8C9—O3—C12118.3 (3)
C18—C19—C20120.5 (3)C31—Se1—C3097.81 (12)
C18—C19—H19119.8
O4—C1—C2—C372.1 (4)C14—C13—C23—C2495.7 (3)
N1—C1—C2—C3106.3 (3)O1—C13—C23—C423.4 (2)
O4—C1—C2—C5178.7 (3)C22—C13—C23—C495.2 (2)
N1—C1—C2—C50.26 (18)C14—C13—C23—C4136.9 (2)
C1—C2—C3—N2116.6 (2)C4—C23—C24—C25143.3 (2)
C5—C2—C3—N222.8 (2)C13—C23—C24—C2596.9 (3)
C1—C2—C3—C30126.5 (3)C4—C23—C24—C2935.4 (4)
C5—C2—C3—C30139.6 (3)C13—C23—C24—C2984.4 (3)
N2—C4—C5—N1117.0 (2)C29—C24—C25—C260.4 (4)
C23—C4—C5—N13.3 (4)C23—C24—C25—C26179.1 (3)
N2—C4—C5—C221.6 (2)C24—C25—C26—C270.6 (5)
C23—C4—C5—C292.1 (3)C25—C26—C27—C280.6 (6)
C1—C2—C5—N10.25 (17)C25—C26—C27—Cl1177.2 (3)
C3—C2—C5—N1117.0 (2)C26—C27—C28—C290.4 (6)
C1—C2—C5—C4118.3 (2)Cl1—C27—C28—C29177.5 (3)
C3—C2—C5—C41.0 (3)C25—C24—C29—C280.2 (5)
C11—C6—C7—C81.1 (4)C23—C24—C29—C28178.9 (3)
N1—C6—C7—C8177.1 (3)C27—C28—C29—C240.2 (6)
C6—C7—C8—C90.3 (5)N2—C3—C30—Se1172.35 (18)
C7—C8—C9—O3179.8 (3)C2—C3—C30—Se159.6 (3)
C7—C8—C9—C101.2 (5)C36—C31—C32—C330.3 (6)
O3—C9—C10—C11179.4 (3)Se1—C31—C32—C33178.8 (3)
C8—C9—C10—C111.9 (5)C31—C32—C33—C340.0 (7)
C9—C10—C11—C61.1 (5)C32—C33—C34—C350.8 (7)
C7—C6—C11—C100.4 (4)C33—C34—C35—C361.4 (7)
N1—C6—C11—C10177.7 (3)C32—C31—C36—C350.3 (5)
O1—C13—C14—O296.4 (3)Se1—C31—C36—C35179.4 (3)
C22—C13—C14—O2147.9 (3)C34—C35—C36—C311.1 (7)
C23—C13—C14—O217.7 (4)O4—C1—N1—C65.6 (5)
O1—C13—C14—C1580.9 (2)C2—C1—N1—C6176.0 (3)
C22—C13—C14—C1534.9 (3)O4—C1—N1—C5178.7 (3)
C23—C13—C14—C15165.1 (2)C2—C1—N1—C50.28 (19)
O2—C14—C15—C20176.3 (3)C7—C6—N1—C1162.9 (3)
C13—C14—C15—C206.5 (3)C11—C6—N1—C119.0 (4)
O2—C14—C15—C163.8 (4)C7—C6—N1—C511.4 (4)
C13—C14—C15—C16173.4 (2)C11—C6—N1—C5166.7 (2)
C20—C15—C16—C170.7 (4)C4—C5—N1—C1106.8 (3)
C14—C15—C16—C17179.3 (3)C2—C5—N1—C10.28 (19)
C15—C16—C17—C181.0 (5)C4—C5—N1—C677.3 (3)
C16—C17—C18—C190.3 (5)C2—C5—N1—C6176.2 (2)
C17—C18—C19—C200.8 (5)C23—C4—N2—O133.7 (2)
C16—C15—C20—C190.4 (4)C5—C4—N2—O1156.62 (19)
C14—C15—C20—C19179.7 (2)C23—C4—N2—C384.8 (2)
C16—C15—C20—C21179.8 (3)C5—C4—N2—C338.1 (2)
C14—C15—C20—C210.3 (4)C30—C3—N2—O184.9 (3)
C18—C19—C20—C151.1 (4)C2—C3—N2—O1153.83 (18)
C18—C19—C20—C21179.5 (3)C30—C3—N2—C4159.7 (2)
C15—C20—C21—C2222.0 (4)C2—C3—N2—C438.5 (2)
C19—C20—C21—C22157.4 (3)C4—N2—O1—C1318.9 (2)
O1—C13—C22—C2156.5 (3)C3—N2—O1—C1398.2 (2)
C14—C13—C22—C2157.1 (3)C22—C13—O1—N2119.7 (2)
C23—C13—C22—C21173.8 (2)C14—C13—O1—N2122.8 (2)
C20—C21—C22—C1350.9 (3)C23—C13—O1—N23.6 (2)
N2—C4—C23—C24161.9 (2)C10—C9—O3—C12173.6 (3)
C5—C4—C23—C2485.5 (3)C8—C9—O3—C127.8 (5)
N2—C4—C23—C1334.9 (2)C32—C31—Se1—C3048.0 (3)
C5—C4—C23—C13147.6 (2)C36—C31—Se1—C30132.9 (3)
O1—C13—C23—C24150.9 (2)C3—C30—Se1—C31175.9 (2)
C22—C13—C23—C2432.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O4i0.982.573.305 (3)132
C23—H23···O20.982.322.803 (3)109
C23—H23···N10.982.542.918 (3)103
Symmetry code: (i) x+3/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC36H31ClN2O4Se
Mr670.04
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)14.4697 (3), 10.9493 (3), 19.3011 (4)
β (°) 94.661 (1)
V3)3047.82 (12)
Z4
Radiation typeMo Kα
µ (mm1)1.36
Crystal size (mm)0.30 × 0.30 × 0.24
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.671, 0.720
No. of measured, independent and
observed [I > 2σ(I)] reflections
37171, 8699, 5453
Rint0.035
(sin θ/λ)max1)0.699
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.176, 1.02
No. of reflections8699
No. of parameters398
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.72, 0.86

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O4i0.982.573.305 (3)132
C23—H23···O20.982.322.803 (3)109
C23—H23···N10.982.542.918 (3)103
Symmetry code: (i) x+3/2, y1/2, z+3/2.
 

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 for their support.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationAltomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350.  CrossRef Web of Science IUCr Journals Google Scholar
First citationAmal Raj, A., Raghunathan, R., Sridevikumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407–419.  Web of Science PubMed Google Scholar
First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationBrakhage, A. A. (1998). Microbiol. Mol. Biol. Rev. 62, 547–585.  Web of Science CAS PubMed Google Scholar
First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA.  Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationKilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820–5824.  CrossRef CAS Web of Science Google Scholar
First citationNardelli, M. (1983). Acta Cryst. C39, 1141–1142.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 4| April 2008| Pages o716-o717
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds