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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 1| January 2009| Pages o147-o148

1-Benzyl-4′,5′-di­phenyl­piperidine-3-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-4,2′′-dione

aDepartment of Physics, The Madura College, Madurai 625011, India, bSchool of Chemistry, Madurai Kamaraj University, Madurai 625021, India, and cDepartment of Food Science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
*Correspondence e-mail: nilanthalakshman@yahoo.co.uk

(Received 26 November 2008; accepted 7 December 2008; online 17 December 2008)

The asymmetric unit of the title compound, C34H31N3O2, consists of two independent mol­ecules which differ slightly in the orientations of the phenyl rings with respect to the pyrrolidine ring. In both mol­ecules, the piperidin-4-one ring adopts a chair conformation, whereas the pyrrolidine ring adopts an envelope conformation in one of the mol­ecules and a twisted conformation in the other. An intra­molecular C—H⋯O hydrogen bond is observed. The crystal packing is stabilized by inter­molecular N—H⋯O hydrogen bonds and C—H⋯π inter­actions.

Related literature

For the biological activities of oxindole derivatives, see: Bhattacharya et al. (1982[Bhattacharya, S. K., Glover, V., McIntyre, I., Oxenkrug, G. & Sandler, M. (1982). Neurosci. Lett. 92, 218-221.]); Glover et al. (1998[Glover, V., Halket, J. M., Watkins, P. J., Clow, A., Goodwin, B. L. & Sandler, M. (1998). J. Neurochem. 51, 656-659.]); Govind et al. (2004[Govind, M. M., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sureshbabu, A. R. & Raghunathan, R. (2004). Acta Cryst. E60, o54-o56.]); Hilton et al. (2000[Hilton, S. T., Ho, T. C., Pljevalijcic, G. & Jones, K. (2000). Org. Lett. 2, 17, 2639-2641.]); Jeyabharathi et al. (2001[Jeyabharathi, A., Ponnuswamy, M. N., Amal Raj, A., Raghunathan, R., Razak, I. A., Usman, A., Chantrapromma, S. & Fun, H.-K. (2001). Acta Cryst. E57, o901-o903.]); Kirsch et al. (2004[Kirsch, G., Hesse, S. & Comel, A. (2004). Curr. Org. Chem. 1, 47-63.]); Klumpp et al. (1998[Klumpp, D. A., Yeung, K. Y., Prakash, G. K. S. & Olah, G. A. (1998). J. Org. Chem. 63, 4481-4484.]); Kumar et al. (1993[Kumar, R., Bansal, R. C. & Mahmood, A. (1993). Biogenic Amines, 9, 281-289.], 2006[Kumar, R. G., Gayathri, D., Velmurugan, D., Ravikumar, K. & Poornachandran, M. (2006). Acta Cryst. E62, o4821-o4823.]); Medvedev et al. (1996[Medvedev, A. E., Clow, A., Sandler, M. & Glover, V. (1996). Biochem. Pharmacol. 52, 385-391.]). For bond-length data, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C34H31N3O2

  • Mr = 513.62

  • Triclinic, [P \overline 1]

  • a = 10.8575 (3) Å

  • b = 13.7909 (5) Å

  • c = 20.5053 (9) Å

  • α = 89.767 (6)°

  • β = 75.056 (4)°

  • γ = 71.846 (3)°

  • V = 2809.1 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 (2) K

  • 0.17 × 0.13 × 0.11 mm

Data collection
  • Nonius MACH-3 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.988, Tmax = 0.992

  • 11592 measured reflections

  • 9879 independent reflections

  • 4342 reflections with I > 2σ(I)

  • Rint = 0.026

  • 2 standard reflections frequency: 60 min intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.157

  • S = 0.99

  • 9879 reflections

  • 711 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3⋯O4 0.86 2.03 2.881 (3) 169
N6—H6⋯O2 0.86 2.05 2.896 (3) 170
C40—H40A⋯O4 0.97 2.35 2.925 (4) 118
C12—H12⋯Cg1i 0.93 2.80 3.586 (6) 144
Symmetry code: (i) x+1, y, z. Cg1 is the centroid of the C29–C34 ring.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996[Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The development of new efficient methods to synthesize N-heterocycles with structural diversity is one of the major interests of modern synthetic organic chemists (Kirsch et al., 2004). Oxindole derivatives are known to possess a variety of biological activities (Klumpp et al., 1998) such as (i) a potent inhibitor of monoamine oxidase (MAO) in human urine and rat tissues (Glover et al., 1998) (ii) inhibition of several enzymes such as acetylcholinestrease (AChE) (Kumar et al., 1993) and atrial natriuretic peptide-stimulated guanylate cyclase and (iii) a potent antagonist of in vitro receptor binding by atrial natriuretic peptide (Medvedev et al., 1996) besides possessing a wide range of central nervous system activities (Bhattacharya et al., 1982). The derivatives of spirooxindole ring systems are used as antimicrobial, antitumour agents and as inhibitors of the human NKI receptor besides being found in a number of alkaloids like horsifiline, spirotryprostatin and (+)elacomine (Hilton et al., 2000). Our interest in preparing pharmacologically active pyrrolidines led us to the title compound, and we have undertaken X-ray crystal structure determination of these compounds in order to establish their conformations.

The asymmetric unit of the title compound contains two independent molecules, and these pair has almost identical geometry (Fig. 1 and Fig. 2). In both the molecules, the bond lengths and bond angles show normal values and agree with each other (Allen et al., 1987). The sums of the angles at atoms N2 and N5 of the pyrrolidine rings 342.3 and 333.4°, respectively, are in accordance with sp3-hybridization, and sums of the angles at atoms N3 and N6 of the indolin-2-one moiety 360 and 359.8° confirms the sp2-hybridization (Govind et al., 2004; Kumar et al., 2006; Jeyabharathi et al., 2001). The bond lengths within the indolin-2-one moiety match with those in similar structures (Kumar et al., 2006; Jeyabharathi et al., 2001).

In one of the independent molecules the pyrrolidine ring (in ring N5/C55/C48/C39/C62, C55 is the flap atom) adopts an envelope conformation and in the other it exhibits a twisted conformation. In the indolin-2-one ring systems, the benzene and pyrrole rings are individually planar and make dihedral angles of 3.8 (2) and 1.7 (2)°, while atoms O2 and O4 deviate from the pyrrole ring of the indolin-2-one system by -0.224 (5) and 0.117 (5) Å, respectively, because of the different interactions in which these O atoms are involved (Table 1). The orientations of the phenyl groups with respect to the pyrrolidine ring differ slightly in the two independent molecules.

N—H···O hydrogen bonds between the two molecules in the asymmetric unit generate an R22(8) graph set motif (Table 1 and Fig. 3). In addition, a C—H···π interaction (Table 1) is also found.

Related literature top

For the biological activities of oxindole derivatives, see: Bhattacharya et al. (1982); Glover et al. (1998); Govind et al. (2004); Hilton et al. (2000); Jeyabharathi et al. (2001); Kirsch et al. (2004); Klumpp et al. (1998); Kumar et al. (1993, 2006); Medvedev et al. (1996). For bond-length data, see: Allen et al. (1987). Cg1 is the centroid of the C29–C34 ring.

Experimental top

A mixture of 1-benzyl-4-piperidinone (0.2 g, 0.001 mol), isatin (0.156 g, 0.001 mol) and phenylglycine (0.320 g, 0.002 mol) in methanol-water (2:1, 30 ml) were refluxed in a water bath for 24 h. After completion of the reaction as monitored by TLC, the excess solvent was removed under vacuum and the residue subjected to flash column chromatography using petroleum ether-ethyl acetate mixture (8:2 v/v) as eluent (yield: 0.220 g, 41%; m.p. 464–465 K)

Refinement top

H atoms attached to N2 and N5 are located in a difference map and refined with an N—H distance restraint of 0.82 (2)Å. All other H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93–0.98 Å and N—H = 0.86 Å. Uiso= 1.2Ueq(C,N) for CH2, CH and NH groups.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf-Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecule-1 of the two molecules in the asymmetric unit, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H-atoms have been omitted for clarity.
[Figure 2] Fig. 2. Molecule-2 of the two molecules in the asymmetric unit, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H-atoms have been omitted for clarity.
[Figure 3] Fig. 3. A partial packing view showing the intermolecular N—H···O interactions (dashed lines) generating an R22(8) graph-set motif in the title compound. H atoms are omitted for clarity.
1-Benzyl-4',5'-diphenylpiperidine-3-spiro-3'-pyrrolidine-2'-spiro-3''- indoline-4,2''-dione top
Crystal data top
C34H31N3O2Z = 4
Mr = 513.62F(000) = 1088
Triclinic, P1Dx = 1.214 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.8575 (3) ÅCell parameters from 25 reflections
b = 13.7909 (5) Åθ = 2–25°
c = 20.5053 (9) ŵ = 0.08 mm1
α = 89.767 (6)°T = 293 K
β = 75.056 (4)°Block, colourless
γ = 71.846 (3)°0.17 × 0.13 × 0.11 mm
V = 2809.1 (2) Å3
Data collection top
Nonius MACH-3
diffractometer
4342 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
ω–2θ scansh = 112
Absorption correction: ψ scan
(North et al., 1968)
k = 1516
Tmin = 0.988, Tmax = 0.992l = 2324
11592 measured reflections2 standard reflections every 60 min
9879 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0638P)2 + 0.294P]
where P = (Fo2 + 2Fc2)/3
9879 reflections(Δ/σ)max = 0.001
711 parametersΔρmax = 0.26 e Å3
2 restraintsΔρmin = 0.28 e Å3
Crystal data top
C34H31N3O2γ = 71.846 (3)°
Mr = 513.62V = 2809.1 (2) Å3
Triclinic, P1Z = 4
a = 10.8575 (3) ÅMo Kα radiation
b = 13.7909 (5) ŵ = 0.08 mm1
c = 20.5053 (9) ÅT = 293 K
α = 89.767 (6)°0.17 × 0.13 × 0.11 mm
β = 75.056 (4)°
Data collection top
Nonius MACH-3
diffractometer
4342 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.026
Tmin = 0.988, Tmax = 0.9922 standard reflections every 60 min
11592 measured reflections intensity decay: none
9879 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0532 restraints
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.26 e Å3
9879 reflectionsΔρmin = 0.28 e Å3
711 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
xyzUiso*/Ueq
C20.3213 (3)1.0209 (3)0.22160 (17)0.0653 (10)
H2A0.40420.98390.18810.078*
H2B0.33611.07710.24320.078*
C30.2105 (4)1.0628 (3)0.18704 (16)0.0649 (10)
H3A0.23011.11550.15870.078*
H3B0.20891.00820.15790.078*
C40.0747 (4)1.1068 (3)0.23641 (16)0.0539 (9)
C50.0408 (3)1.0445 (2)0.29616 (14)0.0462 (8)
C60.1645 (3)1.0109 (2)0.32383 (16)0.0548 (9)
H6A0.17831.07090.34120.066*
H6B0.14850.96890.36110.066*
C70.3934 (3)0.9066 (3)0.30452 (18)0.0737 (11)
H7A0.36320.86430.33890.088*
H7B0.41110.96060.32700.088*
C80.5221 (3)0.8422 (3)0.25547 (16)0.0599 (9)
C90.5243 (4)0.7615 (3)0.21722 (19)0.0713 (10)
H90.44470.74710.22070.086*
C100.6414 (5)0.7006 (3)0.1736 (2)0.0855 (12)
H100.64030.64600.14760.103*
C110.7578 (4)0.7192 (4)0.1682 (2)0.0893 (14)
H110.83760.67750.13890.107*
C120.7569 (5)0.7985 (4)0.2055 (3)0.130 (2)
H120.83710.81180.20210.156*
C130.6410 (4)0.8604 (4)0.2487 (3)0.1121 (17)
H130.64300.91560.27370.135*
C140.0888 (3)1.1077 (2)0.35148 (14)0.0497 (8)
H140.15121.14950.32750.060*
C150.0687 (3)1.1807 (2)0.39981 (16)0.0535 (8)
C160.0916 (3)1.2825 (2)0.38747 (17)0.0616 (9)
H160.12381.30600.35050.074*
C170.0682 (4)1.3501 (3)0.4284 (2)0.0759 (11)
H170.08451.41820.41870.091*
C180.0207 (4)1.3173 (3)0.4833 (2)0.0865 (13)
H180.00261.36240.51020.104*
C190.0005 (4)1.2176 (3)0.49794 (19)0.0861 (13)
H190.02961.19510.53560.103*
C200.0247 (4)1.1505 (3)0.45711 (18)0.0716 (11)
H200.01121.08320.46810.086*
C210.1493 (3)1.0263 (2)0.38361 (15)0.0513 (8)
H210.09780.98890.41390.062*
C220.2973 (3)1.0681 (2)0.42099 (16)0.0514 (8)
C230.3386 (4)1.0833 (3)0.49076 (17)0.0702 (10)
H230.27481.06660.51520.084*
C240.4738 (4)1.1231 (3)0.52476 (19)0.0836 (12)
H240.50011.13300.57180.100*
C250.5676 (4)1.1476 (3)0.4899 (2)0.0757 (11)
H250.65851.17380.51290.091*
C260.5290 (4)1.1337 (3)0.42030 (19)0.0681 (10)
H260.59351.15080.39620.082*
C270.3937 (4)1.0941 (2)0.38614 (17)0.0590 (9)
H270.36791.08500.33910.071*
C280.0013 (3)0.9504 (2)0.27379 (15)0.0465 (8)
C290.0114 (3)0.9474 (2)0.20229 (15)0.0515 (8)
C300.0968 (4)1.0131 (3)0.17111 (19)0.0706 (10)
H300.16161.07210.19490.085*
C310.0858 (5)0.9907 (3)0.1039 (2)0.0920 (13)
H310.14251.03550.08210.110*
C320.0089 (5)0.9023 (4)0.0690 (2)0.0883 (13)
H320.01440.88810.02390.106*
C330.0958 (4)0.8342 (3)0.09954 (18)0.0693 (10)
H330.16000.77490.07590.083*
C340.0831 (3)0.8583 (2)0.16613 (16)0.0521 (8)
C350.1075 (3)0.8443 (2)0.27324 (17)0.0473 (8)
C360.1749 (3)0.3551 (3)0.26427 (17)0.0602 (9)
H36A0.16440.30610.23400.072*
H36B0.09180.38060.30010.072*
C370.2893 (3)0.3029 (2)0.29445 (17)0.0611 (9)
H37A0.28650.34750.33160.073*
H37B0.27680.24060.31280.073*
C380.4256 (4)0.2763 (3)0.24421 (16)0.0557 (9)
C390.4477 (3)0.3585 (2)0.19573 (14)0.0443 (8)
C400.3214 (3)0.3985 (2)0.17048 (14)0.0502 (8)
H40A0.33050.45170.14030.060*
H40B0.31200.34320.14510.060*
C410.0853 (3)0.4983 (3)0.20349 (16)0.0645 (10)
H41A0.06520.45340.17440.077*
H41B0.10770.55180.17690.077*
C420.0370 (3)0.5458 (3)0.26163 (17)0.0575 (9)
C430.1500 (4)0.5157 (3)0.27214 (19)0.0707 (10)
H430.15140.46510.24270.085*
C440.2616 (4)0.5601 (3)0.3262 (2)0.0798 (11)
H440.33740.53950.33250.096*
C450.2611 (4)0.6334 (3)0.3699 (2)0.0814 (12)
H450.33650.66360.40580.098*
C460.1486 (4)0.6625 (3)0.3608 (2)0.0901 (13)
H460.14690.71160.39120.108*
C470.0377 (4)0.6192 (3)0.3067 (2)0.0794 (11)
H470.03770.64020.30070.095*
C480.5777 (3)0.3160 (2)0.13665 (15)0.0506 (8)
H480.64180.26310.15440.061*
C490.5631 (3)0.2665 (3)0.07503 (19)0.0653 (10)
C500.5388 (4)0.3202 (3)0.01969 (19)0.0852 (12)
H500.53110.38930.02030.102*
C510.5260 (5)0.2725 (5)0.0363 (2)0.1161 (18)
H510.51050.30940.07310.139*
C520.5360 (7)0.1722 (6)0.0375 (3)0.144 (3)
H520.52480.14100.07470.173*
C530.5628 (6)0.1159 (5)0.0158 (3)0.135 (2)
H530.57150.04660.01420.162*
C540.5769 (4)0.1638 (3)0.0729 (2)0.0968 (14)
H540.59550.12620.10890.116*
C550.6326 (3)0.4065 (2)0.12493 (14)0.0508 (8)
H550.57660.45890.10290.061*
C560.7779 (3)0.3798 (2)0.08585 (16)0.0529 (8)
C570.8154 (4)0.4215 (3)0.02578 (18)0.0745 (11)
H570.74970.46710.00920.089*
C580.9484 (4)0.3968 (4)0.0100 (2)0.0937 (14)
H580.97210.42530.05070.112*
C591.0461 (4)0.3303 (4)0.0142 (2)0.0895 (13)
H591.13600.31320.01020.107*
C601.0116 (4)0.2895 (3)0.0735 (2)0.0828 (12)
H601.07790.24500.09030.099*
C610.8786 (4)0.3141 (3)0.10893 (18)0.0688 (10)
H610.85610.28540.14970.083*
C620.4766 (3)0.4471 (2)0.23407 (14)0.0442 (8)
C630.4689 (3)0.4410 (2)0.30844 (15)0.0471 (8)
C640.5400 (3)0.3672 (2)0.34215 (17)0.0607 (9)
H640.60610.30880.31830.073*
C650.5122 (4)0.3809 (3)0.41216 (19)0.0748 (11)
H650.55810.33090.43570.090*
C660.4165 (4)0.4689 (4)0.44632 (18)0.0811 (12)
H660.39740.47690.49320.097*
C670.3482 (4)0.5453 (3)0.41317 (17)0.0686 (10)
H670.28520.60520.43680.082*
C680.3759 (3)0.5302 (2)0.34428 (15)0.0497 (8)
C690.3734 (3)0.5552 (2)0.23508 (16)0.0455 (8)
N10.2856 (3)0.9529 (2)0.27199 (13)0.0554 (7)
N20.1264 (3)0.9597 (2)0.32336 (15)0.0609 (8)
N30.1525 (3)0.79994 (18)0.20924 (13)0.0540 (7)
H30.21620.74260.19650.065*
N40.2014 (2)0.43952 (18)0.22703 (12)0.0494 (7)
N50.6116 (3)0.4436 (2)0.19536 (13)0.0520 (7)
N60.3222 (2)0.59638 (18)0.29943 (12)0.0523 (7)
H60.26360.65610.31160.063*
O10.0030 (2)1.18932 (17)0.23002 (11)0.0696 (7)
O20.1366 (2)0.80371 (15)0.32311 (11)0.0597 (6)
O30.5124 (2)0.19456 (17)0.24193 (12)0.0717 (7)
O40.3524 (2)0.59973 (14)0.18487 (10)0.0541 (6)
H20.144 (3)0.9069 (16)0.3322 (13)0.045 (10)*
H50.628 (4)0.499 (2)0.197 (2)0.111 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.056 (2)0.062 (2)0.069 (2)0.0212 (19)0.000 (2)0.0134 (19)
C30.074 (3)0.057 (2)0.053 (2)0.023 (2)0.004 (2)0.0023 (17)
C40.064 (2)0.0409 (19)0.054 (2)0.0159 (18)0.0130 (18)0.0044 (16)
C50.048 (2)0.0389 (17)0.0461 (18)0.0118 (15)0.0065 (15)0.0037 (14)
C60.052 (2)0.0500 (19)0.058 (2)0.0133 (17)0.0096 (17)0.0114 (16)
C70.056 (2)0.087 (3)0.073 (2)0.011 (2)0.024 (2)0.018 (2)
C80.045 (2)0.071 (2)0.059 (2)0.0127 (18)0.0118 (17)0.0086 (18)
C90.056 (2)0.066 (2)0.091 (3)0.025 (2)0.009 (2)0.006 (2)
C100.077 (3)0.071 (3)0.093 (3)0.010 (2)0.016 (3)0.020 (2)
C110.057 (3)0.102 (4)0.070 (3)0.007 (3)0.009 (2)0.001 (2)
C120.051 (3)0.137 (5)0.185 (6)0.036 (3)0.006 (3)0.032 (4)
C130.063 (3)0.107 (4)0.167 (5)0.036 (3)0.020 (3)0.052 (3)
C140.050 (2)0.0394 (17)0.0494 (18)0.0040 (15)0.0087 (16)0.0015 (15)
C150.054 (2)0.0416 (19)0.053 (2)0.0054 (16)0.0059 (17)0.0056 (16)
C160.069 (2)0.046 (2)0.058 (2)0.0125 (18)0.0034 (18)0.0045 (17)
C170.088 (3)0.051 (2)0.076 (3)0.023 (2)0.002 (2)0.015 (2)
C180.093 (3)0.081 (3)0.077 (3)0.026 (3)0.010 (3)0.029 (2)
C190.104 (3)0.077 (3)0.069 (3)0.014 (3)0.029 (2)0.019 (2)
C200.088 (3)0.051 (2)0.068 (2)0.009 (2)0.025 (2)0.0033 (19)
C210.052 (2)0.0349 (17)0.055 (2)0.0025 (15)0.0085 (16)0.0010 (15)
C220.052 (2)0.0368 (17)0.052 (2)0.0042 (16)0.0049 (18)0.0002 (15)
C230.065 (3)0.081 (3)0.052 (2)0.012 (2)0.008 (2)0.0028 (19)
C240.077 (3)0.096 (3)0.052 (2)0.007 (3)0.000 (2)0.003 (2)
C250.063 (3)0.071 (3)0.073 (3)0.011 (2)0.004 (2)0.003 (2)
C260.053 (2)0.061 (2)0.081 (3)0.0058 (19)0.017 (2)0.0001 (19)
C270.057 (2)0.050 (2)0.055 (2)0.0056 (18)0.0055 (19)0.0023 (16)
C280.0438 (19)0.0361 (17)0.0529 (19)0.0090 (15)0.0061 (16)0.0026 (14)
C290.052 (2)0.0468 (19)0.053 (2)0.0130 (17)0.0136 (17)0.0023 (16)
C300.072 (3)0.064 (2)0.072 (3)0.009 (2)0.030 (2)0.001 (2)
C310.099 (3)0.094 (3)0.085 (3)0.014 (3)0.049 (3)0.010 (3)
C320.103 (4)0.103 (3)0.063 (3)0.028 (3)0.033 (3)0.003 (2)
C330.068 (3)0.071 (2)0.061 (2)0.016 (2)0.012 (2)0.010 (2)
C340.050 (2)0.052 (2)0.050 (2)0.0125 (17)0.0112 (17)0.0062 (16)
C350.046 (2)0.0347 (17)0.055 (2)0.0107 (15)0.0061 (17)0.0043 (16)
C360.051 (2)0.056 (2)0.072 (2)0.0221 (18)0.0080 (19)0.0040 (18)
C370.066 (3)0.048 (2)0.069 (2)0.0205 (19)0.015 (2)0.0101 (17)
C380.065 (2)0.043 (2)0.061 (2)0.0143 (19)0.0249 (19)0.0048 (17)
C390.0422 (19)0.0377 (17)0.0476 (18)0.0075 (14)0.0096 (15)0.0075 (14)
C400.050 (2)0.0497 (19)0.0470 (18)0.0132 (16)0.0094 (16)0.0059 (15)
C410.053 (2)0.073 (2)0.062 (2)0.0103 (19)0.0188 (19)0.0040 (19)
C420.042 (2)0.058 (2)0.071 (2)0.0112 (17)0.0183 (18)0.0025 (18)
C430.056 (2)0.073 (3)0.081 (3)0.014 (2)0.024 (2)0.007 (2)
C440.050 (2)0.087 (3)0.103 (3)0.029 (2)0.012 (2)0.001 (3)
C450.059 (3)0.072 (3)0.093 (3)0.010 (2)0.002 (2)0.008 (2)
C460.072 (3)0.082 (3)0.106 (3)0.027 (2)0.004 (3)0.030 (2)
C470.053 (2)0.076 (3)0.101 (3)0.020 (2)0.007 (2)0.020 (2)
C480.045 (2)0.0423 (18)0.057 (2)0.0065 (15)0.0105 (16)0.0114 (15)
C490.050 (2)0.068 (2)0.066 (2)0.0079 (19)0.0073 (19)0.025 (2)
C500.088 (3)0.100 (3)0.063 (3)0.026 (3)0.018 (2)0.021 (2)
C510.103 (4)0.173 (6)0.073 (3)0.044 (4)0.023 (3)0.032 (3)
C520.148 (6)0.164 (7)0.121 (5)0.055 (5)0.028 (4)0.068 (5)
C530.145 (5)0.112 (5)0.151 (5)0.047 (4)0.035 (5)0.060 (4)
C540.103 (3)0.072 (3)0.108 (3)0.021 (3)0.026 (3)0.039 (3)
C550.049 (2)0.0474 (19)0.0474 (19)0.0047 (16)0.0108 (16)0.0038 (15)
C560.049 (2)0.052 (2)0.048 (2)0.0090 (17)0.0048 (17)0.0070 (16)
C570.064 (3)0.079 (3)0.067 (2)0.014 (2)0.005 (2)0.005 (2)
C580.073 (3)0.122 (4)0.067 (3)0.028 (3)0.010 (2)0.013 (3)
C590.054 (3)0.119 (4)0.078 (3)0.017 (3)0.002 (2)0.003 (3)
C600.053 (3)0.105 (3)0.073 (3)0.007 (2)0.009 (2)0.007 (2)
C610.053 (2)0.078 (3)0.063 (2)0.012 (2)0.006 (2)0.006 (2)
C620.0436 (19)0.0344 (16)0.0494 (19)0.0074 (14)0.0102 (16)0.0044 (14)
C630.048 (2)0.0404 (18)0.0499 (19)0.0114 (16)0.0127 (16)0.0029 (15)
C640.067 (2)0.050 (2)0.068 (2)0.0169 (18)0.027 (2)0.0008 (18)
C650.097 (3)0.077 (3)0.066 (3)0.034 (3)0.040 (2)0.014 (2)
C660.100 (3)0.106 (3)0.047 (2)0.046 (3)0.021 (2)0.006 (2)
C670.073 (3)0.075 (3)0.049 (2)0.022 (2)0.005 (2)0.0110 (19)
C680.048 (2)0.054 (2)0.047 (2)0.0181 (17)0.0096 (16)0.0044 (16)
C690.046 (2)0.0368 (17)0.049 (2)0.0104 (15)0.0097 (17)0.0003 (16)
N10.0460 (17)0.0561 (17)0.0536 (16)0.0074 (14)0.0061 (14)0.0102 (14)
N20.0555 (19)0.0426 (17)0.073 (2)0.0175 (15)0.0051 (15)0.0155 (15)
N30.0518 (17)0.0404 (15)0.0575 (17)0.0031 (13)0.0077 (14)0.0100 (13)
N40.0428 (16)0.0463 (15)0.0566 (16)0.0145 (13)0.0088 (14)0.0022 (13)
N50.0483 (18)0.0496 (17)0.0535 (17)0.0189 (14)0.0016 (13)0.0118 (14)
N60.0525 (17)0.0390 (15)0.0528 (17)0.0027 (13)0.0072 (14)0.0133 (13)
O10.0806 (18)0.0488 (14)0.0677 (16)0.0108 (13)0.0125 (13)0.0071 (12)
O20.0708 (16)0.0410 (13)0.0555 (14)0.0047 (11)0.0130 (12)0.0010 (11)
O30.0741 (17)0.0416 (13)0.0914 (17)0.0062 (13)0.0239 (14)0.0036 (12)
O40.0583 (15)0.0394 (12)0.0545 (14)0.0060 (11)0.0097 (12)0.0009 (11)
Geometric parameters (Å, º) top
C2—N11.453 (4)C36—H36A0.97
C2—C31.511 (5)C36—H36B0.97
C2—H2A0.97C37—C381.505 (4)
C2—H2B0.97C37—H37A0.97
C3—C41.498 (4)C37—H37B0.97
C3—H3A0.97C38—O31.216 (3)
C3—H3B0.97C38—C391.538 (4)
C4—O11.217 (3)C39—C401.531 (4)
C4—C51.527 (4)C39—C481.553 (4)
C5—C61.531 (4)C39—C621.608 (4)
C5—C141.564 (4)C40—N41.459 (3)
C5—C281.592 (4)C40—H40A0.97
C6—N11.459 (3)C40—H40B0.97
C6—H6A0.97C41—N41.467 (4)
C6—H6B0.97C41—C421.504 (4)
C7—N11.469 (4)C41—H41A0.97
C7—C81.504 (4)C41—H41B0.97
C7—H7A0.97C42—C471.371 (4)
C7—H7B0.97C42—C431.380 (4)
C8—C91.356 (4)C43—C441.386 (5)
C8—C131.362 (5)C43—H430.93
C9—C101.369 (5)C44—C451.357 (5)
C9—H90.93C44—H440.93
C10—C111.344 (5)C45—C461.369 (5)
C10—H100.93C45—H450.93
C11—C121.334 (6)C46—C471.381 (5)
C11—H110.93C46—H460.93
C12—C131.363 (6)C47—H470.93
C12—H120.93C48—C491.505 (4)
C13—H130.93C48—C551.536 (4)
C14—C151.516 (4)C48—H480.98
C14—C211.536 (4)C49—C541.377 (5)
C14—H140.98C49—C501.389 (5)
C15—C161.381 (4)C50—C511.384 (5)
C15—C201.394 (4)C50—H500.93
C16—C171.379 (5)C51—C521.353 (7)
C16—H160.93C51—H510.93
C17—C181.375 (5)C52—C531.379 (8)
C17—H170.93C52—H520.93
C18—C191.368 (5)C53—C541.411 (6)
C18—H180.93C53—H530.93
C19—C201.377 (5)C54—H540.93
C19—H190.93C55—N51.471 (4)
C20—H200.93C55—C561.501 (4)
C21—N21.463 (4)C55—H550.98
C21—C221.514 (4)C56—C611.373 (4)
C21—H210.98C56—C571.377 (4)
C22—C271.373 (4)C57—C581.374 (5)
C22—C231.380 (4)C57—H570.93
C23—C241.384 (5)C58—C591.368 (5)
C23—H230.93C58—H580.93
C24—C251.350 (5)C59—C601.352 (5)
C24—H240.93C59—H590.93
C25—C261.375 (5)C60—C611.373 (5)
C25—H250.93C60—H600.93
C26—C271.385 (4)C61—H610.93
C26—H260.93C62—N51.463 (4)
C27—H270.93C62—C631.509 (4)
C28—N21.461 (4)C62—C691.558 (4)
C28—C291.509 (4)C63—C641.375 (4)
C28—C351.553 (4)C63—C681.386 (4)
C29—C301.366 (4)C64—C651.390 (4)
C29—C341.394 (4)C64—H640.93
C30—C311.379 (5)C65—C661.374 (5)
C30—H300.93C65—H650.93
C31—C321.380 (5)C66—C671.375 (5)
C31—H310.93C66—H660.93
C32—C331.382 (5)C67—C681.369 (4)
C32—H320.93C67—H670.93
C33—C341.368 (4)C68—N61.399 (4)
C33—H330.93C69—O41.232 (3)
C34—N31.399 (4)C69—N61.343 (3)
C35—O21.229 (3)N2—H20.817 (17)
C35—N31.351 (4)N3—H30.86
C36—N41.453 (4)N5—H50.835 (18)
C36—C371.510 (4)N6—H60.86
N1—C2—C3110.5 (3)C38—C37—H37B108.9
N1—C2—H2A109.5C36—C37—H37B108.9
C3—C2—H2A109.5H37A—C37—H37B107.7
N1—C2—H2B109.5O3—C38—C37121.8 (3)
C3—C2—H2B109.5O3—C38—C39122.2 (3)
H2A—C2—H2B108.1C37—C38—C39116.0 (3)
C4—C3—C2112.6 (3)C40—C39—C38106.9 (2)
C4—C3—H3A109.1C40—C39—C48112.3 (2)
C2—C3—H3A109.1C38—C39—C48111.9 (2)
C4—C3—H3B109.1C40—C39—C62112.8 (2)
C2—C3—H3B109.1C38—C39—C62110.0 (2)
H3A—C3—H3B107.8C48—C39—C62103.1 (2)
O1—C4—C3121.6 (3)N4—C40—C39110.9 (2)
O1—C4—C5121.8 (3)N4—C40—H40A109.5
C3—C4—C5116.6 (3)C39—C40—H40A109.5
C4—C5—C6106.4 (3)N4—C40—H40B109.5
C4—C5—C14111.8 (2)C39—C40—H40B109.5
C6—C5—C14112.0 (2)H40A—C40—H40B108.0
C4—C5—C28111.2 (2)N4—C41—C42111.7 (3)
C6—C5—C28112.6 (2)N4—C41—H41A109.3
C14—C5—C28103.1 (2)C42—C41—H41A109.3
N1—C6—C5111.9 (2)N4—C41—H41B109.3
N1—C6—H6A109.2C42—C41—H41B109.3
C5—C6—H6A109.2H41A—C41—H41B107.9
N1—C6—H6B109.2C47—C42—C43118.1 (3)
C5—C6—H6B109.2C47—C42—C41120.4 (3)
H6A—C6—H6B107.9C43—C42—C41121.5 (3)
N1—C7—C8113.1 (3)C42—C43—C44120.6 (3)
N1—C7—H7A109.0C42—C43—H43119.7
C8—C7—H7A109.0C44—C43—H43119.7
N1—C7—H7B109.0C45—C44—C43120.5 (4)
C8—C7—H7B109.0C45—C44—H44119.7
H7A—C7—H7B107.8C43—C44—H44119.7
C9—C8—C13117.3 (3)C44—C45—C46119.4 (4)
C9—C8—C7120.6 (3)C44—C45—H45120.3
C13—C8—C7122.1 (3)C46—C45—H45120.3
C8—C9—C10121.2 (4)C45—C46—C47120.3 (4)
C8—C9—H9119.4C45—C46—H46119.9
C10—C9—H9119.4C47—C46—H46119.9
C11—C10—C9120.5 (4)C42—C47—C46121.0 (4)
C11—C10—H10119.7C42—C47—H47119.5
C9—C10—H10119.7C46—C47—H47119.5
C12—C11—C10118.8 (4)C49—C48—C55116.2 (3)
C12—C11—H11120.6C49—C48—C39116.1 (3)
C10—C11—H11120.6C55—C48—C39103.6 (2)
C11—C12—C13121.4 (4)C49—C48—H48106.7
C11—C12—H12119.3C55—C48—H48106.7
C13—C12—H12119.3C39—C48—H48106.7
C8—C13—C12120.8 (4)C54—C49—C50118.8 (4)
C8—C13—H13119.6C54—C49—C48118.7 (4)
C12—C13—H13119.6C50—C49—C48122.5 (3)
C15—C14—C21116.4 (3)C51—C50—C49121.2 (5)
C15—C14—C5115.6 (3)C51—C50—H50119.4
C21—C14—C5103.8 (2)C49—C50—H50119.4
C15—C14—H14106.8C52—C51—C50119.9 (6)
C21—C14—H14106.8C52—C51—H51120.0
C5—C14—H14106.8C50—C51—H51120.0
C16—C15—C20116.5 (3)C51—C52—C53120.6 (6)
C16—C15—C14120.1 (3)C51—C52—H52119.7
C20—C15—C14123.4 (3)C53—C52—H52119.7
C17—C16—C15121.9 (4)C52—C53—C54119.7 (6)
C17—C16—H16119.1C52—C53—H53120.2
C15—C16—H16119.1C54—C53—H53120.2
C18—C17—C16120.3 (4)C49—C54—C53119.8 (5)
C18—C17—H17119.9C49—C54—H54120.1
C16—C17—H17119.9C53—C54—H54120.1
C19—C18—C17119.2 (4)N5—C55—C56111.2 (3)
C19—C18—H18120.4N5—C55—C48100.3 (2)
C17—C18—H18120.4C56—C55—C48115.5 (2)
C18—C19—C20120.2 (4)N5—C55—H55109.8
C18—C19—H19119.9C56—C55—H55109.8
C20—C19—H19119.9C48—C55—H55109.8
C19—C20—C15121.9 (3)C61—C56—C57117.4 (3)
C19—C20—H20119.1C61—C56—C55121.5 (3)
C15—C20—H20119.1C57—C56—C55121.1 (3)
N2—C21—C22111.6 (3)C58—C57—C56121.1 (4)
N2—C21—C14100.5 (2)C58—C57—H57119.5
C22—C21—C14114.2 (2)C56—C57—H57119.5
N2—C21—H21110.0C59—C58—C57120.0 (4)
C22—C21—H21110.0C59—C58—H58120.0
C14—C21—H21110.0C57—C58—H58120.0
C27—C22—C23118.3 (3)C60—C59—C58119.9 (4)
C27—C22—C21120.7 (3)C60—C59—H59120.1
C23—C22—C21120.9 (3)C58—C59—H59120.1
C22—C23—C24120.9 (4)C59—C60—C61119.9 (4)
C22—C23—H23119.6C59—C60—H60120.0
C24—C23—H23119.6C61—C60—H60120.0
C25—C24—C23120.2 (4)C60—C61—C56121.7 (3)
C25—C24—H24119.9C60—C61—H61119.1
C23—C24—H24119.9C56—C61—H61119.1
C24—C25—C26120.0 (4)N5—C62—C63110.5 (2)
C24—C25—H25120.0N5—C62—C69110.6 (2)
C26—C25—H25120.0C63—C62—C69100.8 (2)
C25—C26—C27119.9 (4)N5—C62—C39103.8 (2)
C25—C26—H26120.1C63—C62—C39118.1 (2)
C27—C26—H26120.1C69—C62—C39113.2 (2)
C22—C27—C26120.7 (3)C64—C63—C68119.5 (3)
C22—C27—H27119.6C64—C63—C62131.1 (3)
C26—C27—H27119.6C68—C63—C62109.3 (3)
N2—C28—C29111.4 (3)C63—C64—C65119.3 (3)
N2—C28—C35111.1 (2)C63—C64—H64120.3
C29—C28—C35101.3 (2)C65—C64—H64120.3
N2—C28—C5103.7 (2)C66—C65—C64119.5 (4)
C29—C28—C5115.4 (2)C66—C65—H65120.2
C35—C28—C5114.1 (2)C64—C65—H65120.2
C30—C29—C34119.5 (3)C65—C66—C67121.9 (3)
C30—C29—C28131.6 (3)C65—C66—H66119.0
C34—C29—C28108.9 (3)C67—C66—H66119.0
C29—C30—C31119.2 (4)C68—C67—C66117.8 (3)
C29—C30—H30120.4C68—C67—H67121.1
C31—C30—H30120.4C66—C67—H67121.1
C30—C31—C32120.3 (4)C67—C68—C63121.8 (3)
C30—C31—H31119.8C67—C68—N6128.6 (3)
C32—C31—H31119.8C63—C68—N6109.6 (3)
C31—C32—C33121.6 (4)O4—C69—N6125.5 (3)
C31—C32—H32119.2O4—C69—C62125.7 (3)
C33—C32—H32119.2N6—C69—C62108.5 (3)
C34—C33—C32116.9 (3)C2—N1—C6109.0 (3)
C34—C33—H33121.5C2—N1—C7112.3 (3)
C32—C33—H33121.5C6—N1—C7108.9 (2)
C33—C34—C29122.5 (3)C28—N2—C21112.3 (3)
C33—C34—N3128.1 (3)C28—N2—H2117 (2)
C29—C34—N3109.4 (3)C21—N2—H2113 (2)
O2—C35—N3125.7 (3)C35—N3—C34112.0 (3)
O2—C35—C28126.1 (3)C35—N3—H3124.0
N3—C35—C28108.0 (3)C34—N3—H3124.0
N4—C36—C37110.3 (3)C36—N4—C40108.6 (2)
N4—C36—H36A109.6C36—N4—C41111.3 (3)
C37—C36—H36A109.6C40—N4—C41111.3 (2)
N4—C36—H36B109.6C62—N5—C55108.4 (2)
C37—C36—H36B109.6C62—N5—H5115 (3)
H36A—C36—H36B108.1C55—N5—H5110 (3)
C38—C37—C36113.3 (3)C69—N6—C68111.8 (2)
C38—C37—H37A108.9C69—N6—H6124.1
C36—C37—H37A108.9C68—N6—H6124.1
N1—C2—C3—C450.3 (4)C41—C42—C43—C44179.7 (3)
C2—C3—C4—O1134.1 (3)C42—C43—C44—C450.5 (6)
C2—C3—C4—C544.1 (4)C43—C44—C45—C460.7 (6)
O1—C4—C5—C6132.6 (3)C44—C45—C46—C471.4 (7)
C3—C4—C5—C645.6 (3)C43—C42—C47—C460.4 (6)
O1—C4—C5—C1410.1 (4)C41—C42—C47—C46179.1 (4)
C3—C4—C5—C14168.1 (3)C45—C46—C47—C420.8 (7)
O1—C4—C5—C28104.5 (3)C40—C39—C48—C4932.7 (4)
C3—C4—C5—C2877.3 (3)C38—C39—C48—C4987.5 (3)
C4—C5—C6—N157.0 (3)C62—C39—C48—C49154.3 (3)
C14—C5—C6—N1179.4 (2)C40—C39—C48—C5596.1 (3)
C28—C5—C6—N165.0 (3)C38—C39—C48—C55143.8 (2)
N1—C7—C8—C958.4 (5)C62—C39—C48—C5525.6 (3)
N1—C7—C8—C13123.3 (4)C55—C48—C49—C54149.9 (3)
C13—C8—C9—C100.1 (6)C39—C48—C49—C5487.8 (4)
C7—C8—C9—C10178.3 (3)C55—C48—C49—C5028.8 (5)
C8—C9—C10—C110.6 (6)C39—C48—C49—C5093.5 (4)
C9—C10—C11—C120.6 (7)C54—C49—C50—C511.2 (6)
C10—C11—C12—C130.0 (8)C48—C49—C50—C51179.9 (4)
C9—C8—C13—C120.8 (7)C49—C50—C51—C520.5 (7)
C7—C8—C13—C12177.6 (5)C50—C51—C52—C531.9 (9)
C11—C12—C13—C80.8 (9)C51—C52—C53—C541.4 (10)
C4—C5—C14—C1581.1 (3)C50—C49—C54—C531.7 (6)
C6—C5—C14—C1538.1 (4)C48—C49—C54—C53179.6 (4)
C28—C5—C14—C15159.4 (3)C52—C53—C54—C490.4 (8)
C4—C5—C14—C21150.1 (3)C49—C48—C55—N5171.2 (3)
C6—C5—C14—C2190.7 (3)C39—C48—C55—N542.5 (3)
C28—C5—C14—C2130.6 (3)C49—C48—C55—C5669.2 (4)
C21—C14—C15—C16142.3 (3)C39—C48—C55—C56162.1 (3)
C5—C14—C15—C1695.4 (3)N5—C55—C56—C6153.0 (4)
C21—C14—C15—C2039.0 (4)C48—C55—C56—C6160.4 (4)
C5—C14—C15—C2083.3 (4)N5—C55—C56—C57126.0 (3)
C20—C15—C16—C172.0 (5)C48—C55—C56—C57120.6 (3)
C14—C15—C16—C17176.8 (3)C61—C56—C57—C581.0 (5)
C15—C16—C17—C180.1 (5)C55—C56—C57—C58179.9 (3)
C16—C17—C18—C191.7 (6)C56—C57—C58—C590.4 (6)
C17—C18—C19—C201.4 (6)C57—C58—C59—C600.5 (7)
C18—C19—C20—C150.6 (6)C58—C59—C60—C610.8 (7)
C16—C15—C20—C192.3 (5)C59—C60—C61—C560.1 (6)
C14—C15—C20—C19176.4 (3)C57—C56—C61—C600.7 (5)
C15—C14—C21—N2168.4 (3)C55—C56—C61—C60179.8 (3)
C5—C14—C21—N240.2 (3)C40—C39—C62—N5122.1 (3)
C15—C14—C21—C2271.9 (4)C38—C39—C62—N5118.7 (3)
C5—C14—C21—C22159.8 (3)C48—C39—C62—N50.8 (3)
N2—C21—C22—C2736.7 (4)C40—C39—C62—C63115.3 (3)
C14—C21—C22—C2776.5 (4)C38—C39—C62—C633.9 (4)
N2—C21—C22—C23144.9 (3)C48—C39—C62—C63123.4 (3)
C14—C21—C22—C23102.0 (4)C40—C39—C62—C692.1 (3)
C27—C22—C23—C240.4 (5)C38—C39—C62—C69121.3 (3)
C21—C22—C23—C24178.9 (3)C48—C39—C62—C69119.1 (3)
C22—C23—C24—C250.1 (6)N5—C62—C63—C6459.3 (4)
C23—C24—C25—C260.5 (6)C69—C62—C63—C64176.2 (3)
C24—C25—C26—C270.3 (6)C39—C62—C63—C6459.9 (4)
C23—C22—C27—C260.6 (5)N5—C62—C63—C68117.7 (3)
C21—C22—C27—C26179.1 (3)C69—C62—C63—C680.7 (3)
C25—C26—C27—C220.2 (5)C39—C62—C63—C68123.2 (3)
C4—C5—C28—N2129.1 (3)C68—C63—C64—C653.4 (5)
C6—C5—C28—N2111.6 (3)C62—C63—C64—C65179.9 (3)
C14—C5—C28—N29.2 (3)C63—C64—C65—C661.5 (5)
C4—C5—C28—C296.9 (4)C64—C65—C66—C671.1 (6)
C6—C5—C28—C29126.2 (3)C65—C66—C67—C681.6 (6)
C14—C5—C28—C29113.0 (3)C66—C67—C68—C630.4 (5)
C4—C5—C28—C35109.9 (3)C66—C67—C68—N6178.8 (3)
C6—C5—C28—C359.4 (3)C64—C63—C68—C672.9 (5)
C14—C5—C28—C35130.3 (3)C62—C63—C68—C67179.7 (3)
N2—C28—C29—C3055.0 (4)C64—C63—C68—N6176.4 (3)
C35—C28—C29—C30173.3 (3)C62—C63—C68—N61.0 (3)
C5—C28—C29—C3062.9 (4)N5—C62—C69—O456.2 (4)
N2—C28—C29—C34123.5 (3)C63—C62—C69—O4173.1 (3)
C35—C28—C29—C345.3 (3)C39—C62—C69—O459.7 (4)
C5—C28—C29—C34118.5 (3)N5—C62—C69—N6117.0 (3)
C34—C29—C30—C311.4 (5)C63—C62—C69—N60.2 (3)
C28—C29—C30—C31179.8 (4)C39—C62—C69—N6127.0 (3)
C29—C30—C31—C321.0 (6)C3—C2—N1—C662.1 (3)
C30—C31—C32—C330.6 (7)C3—C2—N1—C7177.2 (3)
C31—C32—C33—C340.4 (6)C5—C6—N1—C268.0 (3)
C32—C33—C34—C290.8 (5)C5—C6—N1—C7169.2 (3)
C32—C33—C34—N3175.9 (3)C8—C7—N1—C261.0 (4)
C30—C29—C34—C331.3 (5)C8—C7—N1—C6178.3 (3)
C28—C29—C34—C33179.9 (3)C29—C28—N2—C21142.1 (3)
C30—C29—C34—N3175.9 (3)C35—C28—N2—C21105.7 (3)
C28—C29—C34—N32.8 (3)C5—C28—N2—C2117.3 (3)
N2—C28—C35—O249.5 (4)C22—C21—N2—C28158.1 (3)
C29—C28—C35—O2168.0 (3)C14—C21—N2—C2836.6 (3)
C5—C28—C35—O267.3 (4)O2—C35—N3—C34169.2 (3)
N2—C28—C35—N3124.5 (3)C28—C35—N3—C344.8 (3)
C29—C28—C35—N36.0 (3)C33—C34—N3—C35175.6 (3)
C5—C28—C35—N3118.7 (3)C29—C34—N3—C351.4 (4)
N4—C36—C37—C3849.7 (4)C37—C36—N4—C4063.3 (3)
C36—C37—C38—O3137.5 (3)C37—C36—N4—C41173.8 (3)
C36—C37—C38—C3942.0 (4)C39—C40—N4—C3669.9 (3)
O3—C38—C39—C40135.0 (3)C39—C40—N4—C41167.3 (2)
C37—C38—C39—C4044.5 (3)C42—C41—N4—C3661.8 (3)
O3—C38—C39—C4811.7 (4)C42—C41—N4—C40176.9 (3)
C37—C38—C39—C48167.8 (3)C63—C62—N5—C55156.4 (2)
O3—C38—C39—C62102.3 (3)C69—C62—N5—C5592.8 (3)
C37—C38—C39—C6278.2 (3)C39—C62—N5—C5528.9 (3)
C38—C39—C40—N457.9 (3)C56—C55—N5—C62167.9 (3)
C48—C39—C40—N4179.0 (2)C48—C55—N5—C6245.3 (3)
C62—C39—C40—N463.1 (3)O4—C69—N6—C68173.7 (3)
N4—C41—C42—C4764.6 (4)C62—C69—N6—C680.4 (3)
N4—C41—C42—C43114.0 (4)C67—C68—N6—C69179.9 (3)
C47—C42—C43—C441.1 (5)C63—C68—N6—C690.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O40.862.032.881 (3)169
N6—H6···O20.862.052.896 (3)170
C40—H40A···O40.972.352.925 (4)118
C12—H12···Cg1i0.932.803.586 (6)144
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC34H31N3O2
Mr513.62
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.8575 (3), 13.7909 (5), 20.5053 (9)
α, β, γ (°)89.767 (6), 75.056 (4), 71.846 (3)
V3)2809.1 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.17 × 0.13 × 0.11
Data collection
DiffractometerNonius MACH-3
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.988, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
11592, 9879, 4342
Rint0.026
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.157, 0.99
No. of reflections9879
No. of parameters711
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.26, 0.28

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O40.862.032.881 (3)169
N6—H6···O20.862.052.896 (3)170
C40—H40A···O40.972.352.925 (4)118
C12—H12···Cg1i0.932.803.586 (6)144
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

SP thanks the CSIR for funding a major research project.

References

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Volume 65| Part 1| January 2009| Pages o147-o148
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