PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2801.
Published online 2010 October 13. doi:  10.1107/S1600536810040171
PMCID: PMC3009035

1′-(4-Bromo­phen­yl)-4′-{4-[(2-oxo-1,2,3,4-tetra­hydro­naphthalen-2-yl­idene)meth­yl]phen­yl}-3′′,4′′-dihydro­acenaphthylene-1-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-2,1′′(1H,2′′H)-dione

Abstract

In the title compound, C47H34BrNO3, the central benzene ring makes a dihedral angle of 42.71 (7)° with the bromo­phenyl ring. The pyrrolidine ring adopts an envelope conformation. The mol­ecular structure is stabilized by weak intra­molecular C—H(...)O inter­actions and the crystal packing is stabilized by weak inter­molecular C—H(...)π inter­actions.

Related literature

For the biological activity of pyrrolidine derivatives, see: Amalraj et al. (2003 [triangle]); Daly et al. (1986 [triangle]). For related structures, see: Aravindan et al. (2004 [triangle]); Kumar et al. (2006 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2801-scheme1.jpg

Experimental

Crystal data

  • C47H34BrNO3
  • M r = 740.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2801-efi1.jpg
  • a = 8.4178 (2) Å
  • b = 13.2352 (3) Å
  • c = 15.9610 (3) Å
  • α = 98.143 (1)°
  • β = 92.744 (2)°
  • γ = 100.944 (1)°
  • V = 1723.17 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.24 mm−1
  • T = 295 K
  • 0.20 × 0.19 × 0.18 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.719, T max = 0.779
  • 30711 measured reflections
  • 6410 independent reflections
  • 4539 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.098
  • S = 1.03
  • 6410 reflections
  • 469 parameters
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.53 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040171/is2611sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040171/is2611Isup2.hkl

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

Acknowledgments

The authors acknowledge the IIT, Madras, for the data collection.

supplementary crystallographic information

Comment

Highly substituted pyrrolidines have gained much prominence since they form the central skeleton of many natural products (Daly et al., 1986). Substituted pyrrolidine compounds possess antimicrobial and antifungal activities against various pathogens (Amalraj et al., 2003).

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Aravindan et al., 2004; Kumar et al., 2006). The benzene ring (C12–C17) makes a dihedral angle of 42.71 (7)° with the bromophenyl ring (C42–C46). The sum of bond angles around N1 [359.9 (2)°] indicates that N1 is sp2-hybridized.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π [C17—H17···Cg1 (-1 + x, y, z) distance of 3.720 (3)Å and C26—H26···Cg2 (2 - x, -y, -z) distance of 3.925 (3)Å (Cg1 and Cg2 are the centroid of the rings defined by the atoms C3–C8 and C12–C17, respectively) interactions. The intramolecular interactions C22—H22B···O3 and C23—H23B···O3 generate S(6) and S(7) graph set motifs, respectively (Bernstein et al., 1995).

Experimental

To the solution of acenaphthequinone (3) (1.1 mmol), N-(p-bromo) phenyl glycine (2) (1.1 mmol) and 1,4-bis(3',4'-dihydro-1'- oxonaphthalen-2'-ylidene)benzene (1) (1.0 mmol) was refluxed in dry toluene. Completion of the reaction was evidenced by TLC analysis. The solvent was then removed in vacuum, diluted in dichloromethane, washed with water, and brine. The organic layer was separated and dried over Na2SO4.The organic solvent was removed and the residue was subjected to column chromatography using hexane/ethyl acetate (6:4) as eluent afforded the cycloadduct.

Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C47H34BrNO3Z = 2
Mr = 740.38F(000) = 764
Triclinic, P1Dx = 1.427 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4178 (2) ÅCell parameters from 8389 reflections
b = 13.2352 (3) Åθ = 2.2–25.3°
c = 15.9610 (3) ŵ = 1.24 mm1
α = 98.143 (1)°T = 295 K
β = 92.744 (2)°Block, colourless
γ = 100.944 (1)°0.20 × 0.19 × 0.18 mm
V = 1723.17 (7) Å3

Data collection

Bruker Kappa APEXII diffractometer6410 independent reflections
Radiation source: fine-focus sealed tube4539 reflections with I > 2σ(I)
graphiteRint = 0.034
ω and [var phi] scanθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.719, Tmax = 0.779k = −16→15
30711 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0431P)2 + 0.5268P] where P = (Fo2 + 2Fc2)/3
6410 reflections(Δ/σ)max < 0.001
469 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = −0.53 e Å3

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

xyzUiso*/Ueq
Br10.15843 (4)0.56227 (3)0.415272 (18)0.09413 (16)
O11.4073 (2)−0.15001 (17)0.50404 (12)0.0809 (6)
O21.06900 (18)0.31498 (12)0.14876 (10)0.0482 (4)
O30.43369 (19)0.21371 (13)0.13308 (10)0.0546 (4)
N10.6591 (2)0.32198 (14)0.27716 (10)0.0445 (5)
C11.3657 (3)−0.08403 (18)0.37579 (14)0.0497 (6)
C21.4467 (3)−0.14275 (19)0.43260 (15)0.0538 (6)
C31.5830 (3)−0.18953 (17)0.39993 (14)0.0485 (6)
C41.6890 (3)−0.2189 (2)0.45546 (16)0.0606 (7)
H41.6733−0.21030.51310.073*
C51.8182 (4)−0.2610 (2)0.42732 (19)0.0724 (8)
H51.8905−0.27930.46560.087*
C61.8381 (4)−0.2753 (2)0.3422 (2)0.0805 (9)
H61.9238−0.30470.32240.097*
C71.7332 (4)−0.2469 (2)0.28582 (18)0.0775 (9)
H71.7483−0.25770.22810.093*
C81.6049 (3)−0.2023 (2)0.31344 (16)0.0605 (7)
C91.4889 (4)−0.1689 (3)0.25318 (17)0.0819 (9)
H9A1.5410−0.15660.20160.098*
H9B1.3942−0.22430.23810.098*
C101.4366 (4)−0.0714 (2)0.29222 (16)0.0660 (7)
H10A1.3564−0.05470.25360.079*
H10B1.5294−0.01400.30090.079*
C111.2418 (3)−0.04406 (19)0.40358 (15)0.0526 (6)
H111.2052−0.06390.45400.063*
C121.1534 (3)0.02685 (17)0.36698 (14)0.0453 (5)
C131.2262 (3)0.10465 (17)0.32291 (14)0.0470 (6)
H131.33420.10910.31110.056*
C141.1411 (3)0.17533 (17)0.29635 (14)0.0436 (5)
H141.19330.22690.26750.052*
C150.9800 (3)0.17107 (16)0.31169 (12)0.0387 (5)
C160.9073 (3)0.09371 (19)0.35579 (15)0.0516 (6)
H160.79910.08900.36730.062*
C170.9932 (3)0.02350 (19)0.38283 (15)0.0527 (6)
H170.9415−0.02730.41250.063*
C180.8906 (3)0.25063 (17)0.28252 (12)0.0383 (5)
H180.96960.31640.28780.046*
C190.8163 (2)0.22580 (15)0.18853 (12)0.0334 (4)
C200.7048 (2)0.31159 (16)0.19066 (12)0.0355 (5)
C210.7503 (3)0.27266 (18)0.33271 (13)0.0455 (5)
H21A0.68490.20870.34530.055*
H21B0.78850.31880.38550.055*
C220.7200 (3)0.11361 (16)0.16731 (13)0.0419 (5)
H22A0.78310.06840.19050.050*
H22B0.62080.10910.19620.050*
C230.6752 (3)0.07172 (18)0.07383 (14)0.0490 (6)
H23A0.6373−0.00310.06730.059*
H23B0.58630.10180.05430.059*
C240.8125 (3)0.09469 (17)0.01929 (13)0.0417 (5)
C250.8106 (3)0.03584 (19)−0.06084 (15)0.0557 (6)
H250.7222−0.0173−0.08080.067*
C260.9385 (4)0.0560 (2)−0.11032 (16)0.0628 (7)
H260.93480.0175−0.16410.075*
C271.0711 (3)0.1320 (2)−0.08132 (16)0.0593 (7)
H271.15810.1440−0.11480.071*
C281.0759 (3)0.19022 (17)−0.00322 (14)0.0475 (6)
H281.16710.24110.01680.057*
C290.9446 (3)0.17386 (16)0.04690 (13)0.0379 (5)
C300.9538 (3)0.24389 (16)0.12859 (13)0.0362 (5)
C310.7872 (2)0.41129 (16)0.16111 (13)0.0371 (5)
C320.9035 (3)0.49248 (17)0.19818 (15)0.0489 (6)
H320.94490.49550.25380.059*
C330.9609 (3)0.57258 (18)0.15078 (19)0.0585 (7)
H331.04140.62820.17610.070*
C340.9032 (3)0.57155 (19)0.06981 (18)0.0583 (7)
H340.94720.62460.04030.070*
C350.7779 (3)0.49103 (18)0.03032 (14)0.0465 (6)
C360.6976 (3)0.4798 (2)−0.05085 (16)0.0583 (7)
H360.73090.5287−0.08620.070*
C370.5730 (3)0.3995 (2)−0.07831 (15)0.0603 (7)
H370.52400.3942−0.13270.072*
C380.5143 (3)0.3235 (2)−0.02790 (14)0.0522 (6)
H380.42620.2700−0.04760.063*
C390.5908 (3)0.33051 (17)0.05099 (12)0.0403 (5)
C400.7222 (2)0.41218 (16)0.07868 (13)0.0381 (5)
C410.5557 (3)0.27367 (17)0.12338 (13)0.0391 (5)
C420.5437 (3)0.37730 (16)0.30692 (13)0.0395 (5)
C430.4711 (3)0.43741 (19)0.25804 (14)0.0521 (6)
H430.49990.44090.20280.062*
C440.3572 (3)0.4921 (2)0.28967 (15)0.0557 (6)
H440.31070.53260.25630.067*
C450.3133 (3)0.48635 (19)0.37064 (14)0.0518 (6)
C460.3809 (3)0.42677 (19)0.41970 (14)0.0526 (6)
H460.34950.42270.47440.063*
C470.4956 (3)0.37255 (18)0.38851 (13)0.0468 (6)
H470.54120.33230.42250.056*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0915 (3)0.1514 (3)0.05390 (18)0.0842 (2)−0.00073 (15)−0.01430 (18)
O10.0969 (15)0.1157 (16)0.0604 (12)0.0642 (13)0.0364 (10)0.0481 (11)
O20.0416 (9)0.0476 (9)0.0523 (9)0.0028 (8)0.0088 (7)0.0040 (7)
O30.0396 (9)0.0632 (11)0.0616 (10)0.0055 (8)0.0040 (8)0.0183 (9)
N10.0533 (11)0.0609 (12)0.0302 (9)0.0304 (10)0.0087 (8)0.0161 (8)
C10.0566 (15)0.0559 (14)0.0440 (13)0.0241 (12)0.0071 (11)0.0147 (11)
C20.0626 (16)0.0621 (16)0.0468 (14)0.0263 (13)0.0148 (12)0.0198 (12)
C30.0563 (15)0.0495 (14)0.0478 (13)0.0226 (12)0.0117 (11)0.0162 (11)
C40.0752 (18)0.0665 (17)0.0508 (14)0.0324 (14)0.0112 (13)0.0183 (13)
C50.080 (2)0.080 (2)0.0722 (19)0.0447 (16)0.0110 (15)0.0236 (16)
C60.090 (2)0.091 (2)0.081 (2)0.0588 (18)0.0273 (17)0.0196 (17)
C70.096 (2)0.096 (2)0.0582 (17)0.0569 (19)0.0241 (16)0.0151 (16)
C80.0745 (18)0.0646 (16)0.0513 (15)0.0318 (14)0.0119 (13)0.0119 (13)
C90.104 (2)0.114 (2)0.0448 (15)0.063 (2)0.0106 (15)0.0131 (16)
C100.0779 (19)0.088 (2)0.0482 (14)0.0444 (16)0.0145 (13)0.0246 (14)
C110.0591 (15)0.0617 (15)0.0477 (13)0.0267 (13)0.0123 (11)0.0216 (12)
C120.0500 (14)0.0508 (14)0.0411 (12)0.0211 (11)0.0058 (10)0.0117 (11)
C130.0416 (13)0.0516 (14)0.0523 (13)0.0169 (11)0.0066 (10)0.0118 (11)
C140.0432 (13)0.0448 (13)0.0451 (12)0.0107 (10)0.0042 (10)0.0115 (10)
C150.0436 (13)0.0444 (12)0.0303 (10)0.0145 (10)0.0000 (9)0.0067 (9)
C160.0442 (13)0.0684 (16)0.0517 (14)0.0223 (12)0.0117 (11)0.0240 (12)
C170.0568 (15)0.0588 (15)0.0535 (14)0.0218 (12)0.0141 (12)0.0287 (12)
C180.0408 (12)0.0436 (12)0.0334 (11)0.0142 (10)0.0002 (9)0.0092 (9)
C190.0339 (11)0.0373 (11)0.0311 (10)0.0089 (9)0.0039 (8)0.0086 (9)
C200.0387 (12)0.0416 (12)0.0299 (10)0.0131 (9)0.0048 (9)0.0102 (9)
C210.0543 (14)0.0582 (14)0.0314 (11)0.0267 (11)0.0043 (10)0.0110 (10)
C220.0412 (12)0.0438 (13)0.0432 (12)0.0088 (10)0.0059 (10)0.0134 (10)
C230.0477 (14)0.0438 (13)0.0514 (14)0.0044 (11)−0.0003 (11)0.0010 (11)
C240.0454 (13)0.0430 (13)0.0388 (12)0.0139 (11)0.0004 (10)0.0076 (10)
C250.0597 (16)0.0545 (15)0.0502 (14)0.0137 (12)−0.0052 (12)−0.0008 (12)
C260.082 (2)0.0701 (18)0.0397 (13)0.0290 (16)0.0080 (13)0.0003 (12)
C270.0720 (18)0.0612 (16)0.0499 (14)0.0205 (15)0.0244 (13)0.0098 (13)
C280.0563 (15)0.0430 (13)0.0490 (13)0.0158 (11)0.0153 (11)0.0145 (11)
C290.0454 (13)0.0377 (12)0.0358 (11)0.0163 (10)0.0051 (9)0.0111 (9)
C300.0388 (12)0.0361 (12)0.0373 (11)0.0117 (10)0.0023 (9)0.0126 (9)
C310.0382 (12)0.0397 (12)0.0375 (11)0.0152 (10)0.0072 (9)0.0077 (9)
C320.0509 (14)0.0423 (13)0.0537 (14)0.0135 (11)0.0007 (11)0.0035 (11)
C330.0532 (15)0.0380 (14)0.084 (2)0.0088 (11)0.0119 (14)0.0063 (13)
C340.0606 (16)0.0446 (14)0.0810 (19)0.0212 (13)0.0266 (15)0.0267 (14)
C350.0511 (14)0.0504 (14)0.0496 (13)0.0267 (12)0.0180 (11)0.0202 (11)
C360.0695 (18)0.0729 (18)0.0512 (15)0.0384 (15)0.0252 (13)0.0333 (14)
C370.0707 (18)0.091 (2)0.0339 (12)0.0396 (16)0.0106 (12)0.0251 (13)
C380.0493 (14)0.0738 (17)0.0377 (12)0.0232 (12)0.0017 (10)0.0080 (12)
C390.0406 (13)0.0536 (14)0.0332 (11)0.0214 (11)0.0067 (9)0.0111 (10)
C400.0399 (12)0.0443 (12)0.0375 (11)0.0208 (10)0.0123 (9)0.0116 (10)
C410.0372 (12)0.0443 (13)0.0386 (11)0.0127 (11)0.0049 (9)0.0091 (10)
C420.0412 (12)0.0469 (13)0.0338 (11)0.0153 (10)0.0043 (9)0.0079 (10)
C430.0595 (15)0.0697 (16)0.0389 (12)0.0335 (13)0.0130 (11)0.0174 (11)
C440.0607 (16)0.0712 (17)0.0461 (13)0.0363 (13)0.0054 (11)0.0136 (12)
C450.0482 (14)0.0669 (16)0.0414 (13)0.0256 (12)0.0000 (10)−0.0060 (11)
C460.0576 (15)0.0696 (16)0.0335 (12)0.0217 (13)0.0089 (11)0.0035 (11)
C470.0525 (14)0.0578 (14)0.0353 (12)0.0220 (12)0.0038 (10)0.0103 (10)

Geometric parameters (Å, °)

Br1—C451.898 (2)C21—H21A0.9700
O1—C21.214 (3)C21—H21B0.9700
O2—C301.211 (2)C22—C231.519 (3)
O3—C411.204 (2)C22—H22A0.9700
N1—C421.386 (3)C22—H22B0.9700
N1—C201.446 (2)C23—C241.492 (3)
N1—C211.446 (3)C23—H23A0.9700
C1—C111.323 (3)C23—H23B0.9700
C1—C21.494 (3)C24—C291.382 (3)
C1—C101.505 (3)C24—C251.398 (3)
C2—C31.486 (3)C25—C261.373 (4)
C3—C41.373 (3)C25—H250.9300
C3—C81.392 (3)C26—C271.365 (4)
C4—C51.379 (4)C26—H260.9300
C4—H40.9300C27—C281.364 (3)
C5—C61.368 (4)C27—H270.9300
C5—H50.9300C28—C291.396 (3)
C6—C71.370 (4)C28—H280.9300
C6—H60.9300C29—C301.479 (3)
C7—C81.387 (4)C31—C321.352 (3)
C7—H70.9300C31—C401.403 (3)
C8—C91.506 (4)C32—C331.413 (3)
C9—C101.504 (4)C32—H320.9300
C9—H9A0.9700C33—C341.356 (4)
C9—H9B0.9700C33—H330.9300
C10—H10A0.9700C34—C351.402 (3)
C10—H10B0.9700C34—H340.9300
C11—C121.468 (3)C35—C361.408 (3)
C11—H110.9300C35—C401.408 (3)
C12—C171.378 (3)C36—C371.350 (4)
C12—C131.392 (3)C36—H360.9300
C13—C141.381 (3)C37—C381.408 (3)
C13—H130.9300C37—H370.9300
C14—C151.381 (3)C38—C391.369 (3)
C14—H140.9300C38—H380.9300
C15—C161.388 (3)C39—C401.397 (3)
C15—C181.516 (3)C39—C411.477 (3)
C16—C171.383 (3)C42—C471.389 (3)
C16—H160.9300C42—C431.389 (3)
C17—H170.9300C43—C441.380 (3)
C18—C211.509 (3)C43—H430.9300
C18—C191.563 (3)C44—C451.369 (3)
C18—H180.9800C44—H440.9300
C19—C221.533 (3)C45—C461.364 (3)
C19—C301.542 (3)C46—C471.379 (3)
C19—C201.602 (3)C46—H460.9300
C20—C311.518 (3)C47—H470.9300
C20—C411.568 (3)
C42—N1—C20124.33 (16)C23—C22—C19116.47 (17)
C42—N1—C21121.74 (16)C23—C22—H22A108.2
C20—N1—C21113.88 (16)C19—C22—H22A108.2
C11—C1—C2118.1 (2)C23—C22—H22B108.2
C11—C1—C10125.0 (2)C19—C22—H22B108.2
C2—C1—C10116.9 (2)H22A—C22—H22B107.3
O1—C2—C3120.3 (2)C24—C23—C22113.39 (18)
O1—C2—C1122.0 (2)C24—C23—H23A108.9
C3—C2—C1117.63 (19)C22—C23—H23A108.9
C4—C3—C8120.0 (2)C24—C23—H23B108.9
C4—C3—C2119.8 (2)C22—C23—H23B108.9
C8—C3—C2120.2 (2)H23A—C23—H23B107.7
C3—C4—C5121.2 (2)C29—C24—C25118.5 (2)
C3—C4—H4119.4C29—C24—C23120.92 (19)
C5—C4—H4119.4C25—C24—C23120.5 (2)
C6—C5—C4118.9 (3)C26—C25—C24120.4 (2)
C6—C5—H5120.6C26—C25—H25119.8
C4—C5—H5120.6C24—C25—H25119.8
C5—C6—C7120.7 (3)C27—C26—C25120.6 (2)
C5—C6—H6119.6C27—C26—H26119.7
C7—C6—H6119.6C25—C26—H26119.7
C6—C7—C8121.0 (3)C28—C27—C26120.0 (2)
C6—C7—H7119.5C28—C27—H27120.0
C8—C7—H7119.5C26—C27—H27120.0
C7—C8—C3118.2 (2)C27—C28—C29120.4 (2)
C7—C8—C9122.3 (2)C27—C28—H28119.8
C3—C8—C9119.5 (2)C29—C28—H28119.8
C10—C9—C8111.3 (2)C24—C29—C28119.9 (2)
C10—C9—H9A109.4C24—C29—C30122.51 (19)
C8—C9—H9A109.4C28—C29—C30117.6 (2)
C10—C9—H9B109.4O2—C30—C29120.32 (19)
C8—C9—H9B109.4O2—C30—C19119.93 (18)
H9A—C9—H9B108.0C29—C30—C19119.75 (18)
C9—C10—C1111.5 (2)C32—C31—C40118.9 (2)
C9—C10—H10A109.3C32—C31—C20132.80 (19)
C1—C10—H10A109.3C40—C31—C20108.34 (18)
C9—C10—H10B109.3C31—C32—C33118.7 (2)
C1—C10—H10B109.3C31—C32—H32120.7
H10A—C10—H10B108.0C33—C32—H32120.7
C1—C11—C12129.9 (2)C34—C33—C32122.6 (2)
C1—C11—H11115.1C34—C33—H33118.7
C12—C11—H11115.1C32—C33—H33118.7
C17—C12—C13117.2 (2)C33—C34—C35120.5 (2)
C17—C12—C11119.1 (2)C33—C34—H34119.8
C13—C12—C11123.5 (2)C35—C34—H34119.8
C14—C13—C12121.3 (2)C34—C35—C36128.4 (2)
C14—C13—H13119.4C34—C35—C40116.0 (2)
C12—C13—H13119.4C36—C35—C40115.6 (2)
C13—C14—C15121.4 (2)C37—C36—C35121.2 (2)
C13—C14—H14119.3C37—C36—H36119.4
C15—C14—H14119.3C35—C36—H36119.4
C14—C15—C16117.46 (19)C36—C37—C38122.6 (2)
C14—C15—C18120.05 (19)C36—C37—H37118.7
C16—C15—C18122.48 (19)C38—C37—H37118.7
C17—C16—C15121.0 (2)C39—C38—C37118.1 (2)
C17—C16—H16119.5C39—C38—H38121.0
C15—C16—H16119.5C37—C38—H38121.0
C12—C17—C16121.7 (2)C38—C39—C40119.4 (2)
C12—C17—H17119.1C38—C39—C41133.5 (2)
C16—C17—H17119.1C40—C39—C41106.76 (17)
C21—C18—C15116.01 (17)C39—C40—C31113.52 (18)
C21—C18—C19103.72 (16)C39—C40—C35123.1 (2)
C15—C18—C19115.92 (17)C31—C40—C35123.3 (2)
C21—C18—H18106.9O3—C41—C39127.9 (2)
C15—C18—H18106.9O3—C41—C20124.93 (18)
C19—C18—H18106.9C39—C41—C20107.03 (17)
C22—C19—C30110.14 (16)N1—C42—C47119.58 (18)
C22—C19—C18111.45 (16)N1—C42—C43122.77 (18)
C30—C19—C18109.23 (16)C47—C42—C43117.64 (19)
C22—C19—C20113.50 (16)C44—C43—C42121.4 (2)
C30—C19—C20112.50 (15)C44—C43—H43119.3
C18—C19—C2099.56 (15)C42—C43—H43119.3
N1—C20—C31115.98 (17)C45—C44—C43119.4 (2)
N1—C20—C41113.12 (16)C45—C44—H44120.3
C31—C20—C41101.41 (16)C43—C44—H44120.3
N1—C20—C19102.76 (14)C46—C45—C44120.4 (2)
C31—C20—C19113.35 (16)C46—C45—Br1119.69 (17)
C41—C20—C19110.53 (16)C44—C45—Br1119.87 (18)
N1—C21—C18103.74 (16)C45—C46—C47120.3 (2)
N1—C21—H21A111.0C45—C46—H46119.9
C18—C21—H21A111.0C47—C46—H46119.9
N1—C21—H21B111.0C46—C47—C42120.8 (2)
C18—C21—H21B111.0C46—C47—H47119.6
H21A—C21—H21B109.0C42—C47—H47119.6
C11—C1—C2—O1−3.7 (4)C23—C24—C25—C26−178.9 (2)
C10—C1—C2—O1173.9 (3)C24—C25—C26—C271.6 (4)
C11—C1—C2—C3178.5 (2)C25—C26—C27—C28−1.4 (4)
C10—C1—C2—C3−3.9 (3)C26—C27—C28—C29−1.1 (4)
O1—C2—C3—C4−15.5 (4)C25—C24—C29—C28−3.1 (3)
C1—C2—C3—C4162.3 (2)C23—C24—C29—C28176.5 (2)
O1—C2—C3—C8165.4 (3)C25—C24—C29—C30176.65 (19)
C1—C2—C3—C8−16.8 (4)C23—C24—C29—C30−3.8 (3)
C8—C3—C4—C50.2 (4)C27—C28—C29—C243.4 (3)
C2—C3—C4—C5−178.9 (2)C27—C28—C29—C30−176.4 (2)
C3—C4—C5—C6−1.3 (4)C24—C29—C30—O2−176.99 (19)
C4—C5—C6—C71.0 (5)C28—C29—C30—O22.8 (3)
C5—C6—C7—C80.4 (5)C24—C29—C30—C193.4 (3)
C6—C7—C8—C3−1.6 (5)C28—C29—C30—C19−176.87 (17)
C6—C7—C8—C9179.1 (3)C22—C19—C30—O2−159.31 (18)
C4—C3—C8—C71.3 (4)C18—C19—C30—O2−36.6 (2)
C2—C3—C8—C7−179.6 (3)C20—C19—C30—O273.0 (2)
C4—C3—C8—C9−179.4 (3)C22—C19—C30—C2920.3 (2)
C2—C3—C8—C9−0.3 (4)C18—C19—C30—C29143.05 (17)
C7—C8—C9—C10−144.1 (3)C20—C19—C30—C29−107.37 (19)
C3—C8—C9—C1036.7 (4)N1—C20—C31—C3242.7 (3)
C8—C9—C10—C1−55.0 (4)C41—C20—C31—C32165.7 (2)
C11—C1—C10—C9−143.1 (3)C19—C20—C31—C32−75.8 (3)
C2—C1—C10—C939.5 (3)N1—C20—C31—C40−137.41 (18)
C2—C1—C11—C12171.6 (2)C41—C20—C31—C40−14.5 (2)
C10—C1—C11—C12−5.7 (5)C19—C20—C31—C40104.02 (18)
C1—C11—C12—C17151.9 (3)C40—C31—C32—C33−3.1 (3)
C1—C11—C12—C13−34.1 (4)C20—C31—C32—C33176.7 (2)
C17—C12—C13—C140.0 (3)C31—C32—C33—C340.4 (4)
C11—C12—C13—C14−174.1 (2)C32—C33—C34—C352.3 (4)
C12—C13—C14—C15−0.6 (3)C33—C34—C35—C36176.4 (2)
C13—C14—C15—C160.8 (3)C33—C34—C35—C40−2.0 (3)
C13—C14—C15—C18179.3 (2)C34—C35—C36—C37−176.8 (2)
C14—C15—C16—C17−0.3 (3)C40—C35—C36—C371.6 (3)
C18—C15—C16—C17−178.8 (2)C35—C36—C37—C380.9 (4)
C13—C12—C17—C160.4 (4)C36—C37—C38—C39−2.0 (4)
C11—C12—C17—C16174.8 (2)C37—C38—C39—C400.3 (3)
C15—C16—C17—C12−0.3 (4)C37—C38—C39—C41172.9 (2)
C14—C15—C18—C21−153.2 (2)C38—C39—C40—C31178.84 (19)
C16—C15—C18—C2125.2 (3)C41—C39—C40—C314.5 (2)
C14—C15—C18—C1984.7 (2)C38—C39—C40—C352.3 (3)
C16—C15—C18—C19−96.8 (2)C41—C39—C40—C35−172.05 (19)
C21—C18—C19—C22−80.1 (2)C32—C31—C40—C39−173.09 (19)
C15—C18—C19—C2248.2 (2)C20—C31—C40—C397.0 (2)
C21—C18—C19—C30157.96 (17)C32—C31—C40—C353.4 (3)
C15—C18—C19—C30−73.7 (2)C20—C31—C40—C35−176.43 (18)
C21—C18—C19—C2039.94 (19)C34—C35—C40—C39175.38 (19)
C15—C18—C19—C20168.29 (17)C36—C35—C40—C39−3.2 (3)
C42—N1—C20—C3165.1 (3)C34—C35—C40—C31−0.8 (3)
C21—N1—C20—C31−112.3 (2)C36—C35—C40—C31−179.42 (19)
C42—N1—C20—C41−51.5 (3)C38—C39—C41—O3−10.8 (4)
C21—N1—C20—C41131.11 (19)C40—C39—C41—O3162.4 (2)
C42—N1—C20—C19−170.68 (19)C38—C39—C41—C20173.1 (2)
C21—N1—C20—C1911.9 (2)C40—C39—C41—C20−13.7 (2)
C22—C19—C20—N187.33 (19)N1—C20—C41—O3−34.4 (3)
C30—C19—C20—N1−146.76 (17)C31—C20—C41—O3−159.3 (2)
C18—C19—C20—N1−31.20 (19)C19—C20—C41—O380.2 (2)
C22—C19—C20—C31−146.72 (17)N1—C20—C41—C39141.88 (17)
C30—C19—C20—C31−20.8 (2)C31—C20—C41—C3917.0 (2)
C18—C19—C20—C3194.75 (18)C19—C20—C41—C39−103.51 (18)
C22—C19—C20—C41−33.6 (2)C20—N1—C42—C47172.7 (2)
C30—C19—C20—C4192.26 (19)C21—N1—C42—C47−10.1 (3)
C18—C19—C20—C41−152.18 (16)C20—N1—C42—C43−6.5 (3)
C42—N1—C21—C18−163.82 (19)C21—N1—C42—C43170.7 (2)
C20—N1—C21—C1813.7 (2)N1—C42—C43—C44−179.6 (2)
C15—C18—C21—N1−162.26 (18)C47—C42—C43—C441.1 (4)
C19—C18—C21—N1−34.0 (2)C42—C43—C44—C45−0.7 (4)
C30—C19—C22—C23−44.8 (2)C43—C44—C45—C46−0.2 (4)
C18—C19—C22—C23−166.22 (18)C43—C44—C45—Br1179.39 (19)
C20—C19—C22—C2382.3 (2)C44—C45—C46—C470.7 (4)
C19—C22—C23—C2445.9 (3)Br1—C45—C46—C47−178.94 (18)
C22—C23—C24—C29−20.2 (3)C45—C46—C47—C42−0.2 (4)
C22—C23—C24—C25159.3 (2)N1—C42—C47—C46−180.0 (2)
C29—C24—C25—C260.7 (3)C43—C42—C47—C46−0.7 (3)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3–C8 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C22—H22B···O30.972.553.026 (3)111
C23—H23B···O30.972.403.113 (3)130
C17—H17···Cg1i0.932.983.720 (3)137
C26—H26···Cg2ii0.933.003.925 (3)178

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2611).

References

  • Amalraj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem.11, 407–419. [PubMed]
  • Aravindan, P. G., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sridhar, G. & Raghunathan, R. (2004). Acta Cryst. E60, o2149–o2151.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Daly, J. W., Spande, T. W., Whittaker, N., Highet, R. J., Feigl, D., Noshimori, N., Tokuyama, T. & Meyers, C. W. (1986). J. Nat. Prod.49, 265–280. [PubMed]
  • Kumar, B. K. S., Gayathri, D., Velmurugan, D., Ravikumar, K. & Periyasami, G. (2006). Acta Cryst. E62, o5075–o5077.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography