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Acta Cryst. (2008). E64, o716-o717    [ doi:10.1107/S1600536808006570 ]

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

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

Abstract top

In the title compound, C36H31ClN2O4Se, the four-membered [beta]-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 [pi]-[pi] interactions between benzene rings of tetralone groups in molecules related by an inversion center, with a centroid-centroid separation of 3.8923 (2) Å.

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
C36H31ClN2O4SeF000 = 1376
Mr = 670.04Dx = 1.460 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 37171 reflections
a = 14.4697 (3) Åθ = 1.7–29.8º
b = 10.9493 (3) ŵ = 1.36 mm−1
c = 19.3011 (4) ÅT = 293 (2) K
β = 94.661 (1)ºPrism, 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)
Monochromator: graphiteRint = 0.035
T = 293(2) Kθmax = 29.8º
ω and φ scansθmin = 1.7º
Absorption correction: multi-scan
(Blessing, 1995)		h = −20→19
Tmin = 0.671, Tmax = 0.720k = −15→15
37171 measured reflectionsl = −26→26
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053  w = 1/[σ2(Fo2) + (0.09P)2 + 1.6651P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.176(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.72 e Å−3
8699 reflectionsΔρmin = −0.86 e Å−3
398 parametersExtinction 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)
Secondary atom site location: difference Fourier map
Crystal data top
C36H31ClN2O4SeV = 3047.82 (12) Å3
Mr = 670.04Z = 4
Monoclinic, P21/nMo Kα
a = 14.4697 (3) ŵ = 1.36 mm−1
b = 10.9493 (3) ÅT = 293 (2) K
c = 19.3011 (4) Å0.30 × 0.30 × 0.24 mm
β = 94.661 (1)º
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)] = 0.053398 parameters
wR(F2) = 0.176H-atom parameters constrained
S = 1.02Δρmax = 0.72 e Å−3
8699 reflectionsΔρmin = −0.86 e Å−3
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)
H40.8742−0.02050.83360.046*
C50.77879 (19)0.0276 (2)0.75107 (12)0.0405 (5)
H50.7777−0.05800.73610.049*
C60.85780 (18)0.1320 (2)0.64929 (12)0.0398 (6)
C70.9257 (2)0.0452 (3)0.64583 (14)0.0480 (6)
H70.9233−0.02580.67210.058*
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)
H281.1695−0.00680.78270.116*
C291.0447 (3)0.0594 (4)0.80593 (18)0.0716 (10)
H291.0247−0.01060.82750.086*
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)
H320.4378−0.03980.88780.087*
C330.3252 (3)−0.0167 (4)0.9417 (2)0.0842 (12)
H330.3226−0.09700.95720.101*
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, °) 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—C3−72.1 (4)C14—C13—C23—C2495.7 (3)
N1—C1—C2—C3106.3 (3)O1—C13—C23—C4−23.4 (2)
O4—C1—C2—C5−178.7 (3)C22—C13—C23—C495.2 (2)
N1—C1—C2—C5−0.26 (18)C14—C13—C23—C4−136.9 (2)
C1—C2—C3—N2−116.6 (2)C4—C23—C24—C25143.3 (2)
C5—C2—C3—N2−22.8 (2)C13—C23—C24—C25−96.9 (3)
C1—C2—C3—C30126.5 (3)C4—C23—C24—C29−35.4 (4)
C5—C2—C3—C30−139.6 (3)C13—C23—C24—C2984.4 (3)
N2—C4—C5—N1117.0 (2)C29—C24—C25—C26−0.4 (4)
C23—C4—C5—N13.3 (4)C23—C24—C25—C26−179.1 (3)
N2—C4—C5—C221.6 (2)C24—C25—C26—C270.6 (5)
C23—C4—C5—C2−92.1 (3)C25—C26—C27—C28−0.6 (6)
C1—C2—C5—N10.25 (17)C25—C26—C27—Cl1177.2 (3)
C3—C2—C5—N1−117.0 (2)C26—C27—C28—C290.4 (6)
C1—C2—C5—C4118.3 (2)Cl1—C27—C28—C29−177.5 (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—C8−177.1 (3)C27—C28—C29—C24−0.2 (6)
C6—C7—C8—C9−0.3 (5)N2—C3—C30—Se1−172.35 (18)
C7—C8—C9—O3−179.8 (3)C2—C3—C30—Se1−59.6 (3)
C7—C8—C9—C10−1.2 (5)C36—C31—C32—C330.3 (6)
O3—C9—C10—C11−179.4 (3)Se1—C31—C32—C33−178.8 (3)
C8—C9—C10—C111.9 (5)C31—C32—C33—C340.0 (7)
C9—C10—C11—C6−1.1 (5)C32—C33—C34—C35−0.8 (7)
C7—C6—C11—C10−0.4 (4)C33—C34—C35—C361.4 (7)
N1—C6—C11—C10177.7 (3)C32—C31—C36—C350.3 (5)
O1—C13—C14—O2−96.4 (3)Se1—C31—C36—C35179.4 (3)
C22—C13—C14—O2147.9 (3)C34—C35—C36—C31−1.1 (7)
C23—C13—C14—O217.7 (4)O4—C1—N1—C6−5.6 (5)
O1—C13—C14—C1580.9 (2)C2—C1—N1—C6176.0 (3)
C22—C13—C14—C15−34.9 (3)O4—C1—N1—C5178.7 (3)
C23—C13—C14—C15−165.1 (2)C2—C1—N1—C50.28 (19)
O2—C14—C15—C20−176.3 (3)C7—C6—N1—C1−162.9 (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—C16−173.4 (2)C11—C6—N1—C5−166.7 (2)
C20—C15—C16—C17−0.7 (4)C4—C5—N1—C1−106.8 (3)
C14—C15—C16—C17179.3 (3)C2—C5—N1—C1−0.28 (19)
C15—C16—C17—C181.0 (5)C4—C5—N1—C677.3 (3)
C16—C17—C18—C19−0.3 (5)C2—C5—N1—C6−176.2 (2)
C17—C18—C19—C20−0.8 (5)C23—C4—N2—O1−33.7 (2)
C16—C15—C20—C19−0.4 (4)C5—C4—N2—O1−156.62 (19)
C14—C15—C20—C19179.7 (2)C23—C4—N2—C384.8 (2)
C16—C15—C20—C21−179.8 (3)C5—C4—N2—C3−38.1 (2)
C14—C15—C20—C210.3 (4)C30—C3—N2—O1−84.9 (3)
C18—C19—C20—C151.1 (4)C2—C3—N2—O1153.83 (18)
C18—C19—C20—C21−179.5 (3)C30—C3—N2—C4159.7 (2)
C15—C20—C21—C2222.0 (4)C2—C3—N2—C438.5 (2)
C19—C20—C21—C22−157.4 (3)C4—N2—O1—C1318.9 (2)
O1—C13—C22—C21−56.5 (3)C3—N2—O1—C13−98.2 (2)
C14—C13—C22—C2157.1 (3)C22—C13—O1—N2−119.7 (2)
C23—C13—C22—C21−173.8 (2)C14—C13—O1—N2122.8 (2)
C20—C21—C22—C13−50.9 (3)C23—C13—O1—N23.6 (2)
N2—C4—C23—C24161.9 (2)C10—C9—O3—C12173.6 (3)
C5—C4—C23—C24−85.5 (3)C8—C9—O3—C12−7.8 (5)
N2—C4—C23—C1334.9 (2)C32—C31—Se1—C30−48.0 (3)
C5—C4—C23—C13147.6 (2)C36—C31—Se1—C30132.9 (3)
O1—C13—C23—C24−150.9 (2)C3—C30—Se1—C31175.9 (2)
C22—C13—C23—C24−32.3 (3)
Hydrogen-bond geometry (Å, °) 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 codes: (i) −x+3/2, y−1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) 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 codes: (i) −x+3/2, y−1/2, −z+3/2.
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 for their support.

references
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