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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o716–o717.
Published online 2008 March 14. doi:  10.1107/S1600536808006570
PMCID: PMC2960925

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

Abstract

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 π–π 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 [triangle]); Amal Raj et al. (2003 [triangle]); Brakhage (1998 [triangle]); Cremer & Pople (1975 [triangle]); Kilonda et al. (1995 [triangle]); Nardelli (1983 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o716-scheme1.jpg

Experimental

Crystal data

  • C36H31ClN2O4Se
  • M r = 670.04
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o716-efi1.jpg
  • 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 [triangle]) T min = 0.671, T max = 0.720
  • 37171 measured reflections
  • 8699 independent reflections
  • 5453 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 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

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006570/bh2162sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006570/bh2162Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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 [var phi]2 = 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 [var phi]2 = -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.

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of (I) with 30% probability displacement ellipsoids.
Fig. 2.
The packing of the molecules viewed along c axis.

Crystal data

C36H31ClN2O4SeF000 = 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 = 1.7–29.8º
b = 10.9493 (3) ŵ = 1.36 mm1
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

Bruker APEXII diffractometer8699 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 [var phi] 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

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 Å3
8699 reflectionsΔρmin = −0.86 e Å3
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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2162).

References

  • 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.
  • Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst.26, 343–350.
  • Amal Raj, A., Raghunathan, R., Sridevikumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem.11, 407–419. [PubMed]
  • Blessing, R. H. (1995). Acta Cryst. A51, 33–38. [PubMed]
  • Brakhage, A. A. (1998). Microbiol. Mol. Biol. Rev.62, 547–585. [PMC free article] [PubMed]
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison,Wisconsin, USA.
  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Kilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem.60, 5820–5824.
  • Nardelli, M. (1983). Acta Cryst. C39, 1141–1142.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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