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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o147–o148.
Published online 2008 December 17. doi:  10.1107/S160053680804141X
PMCID: PMC2968062

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

Abstract

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 [triangle]); Glover et al. (1998 [triangle]); Govind et al. (2004 [triangle]); Hilton et al. (2000 [triangle]); Jeyabharathi et al. (2001 [triangle]); Kirsch et al. (2004 [triangle]); Klumpp et al. (1998 [triangle]); Kumar et al. (1993 [triangle], 2006 [triangle]); Medvedev et al. (1996 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o147-scheme1.jpg

Experimental

Crystal data

  • C34H31N3O2
  • M r = 513.62
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o147-efi1.jpg
  • 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 [triangle]) T min = 0.988, T max = 0.992
  • 11592 measured reflections
  • 9879 independent reflections
  • 4342 reflections with I > 2σ(I)
  • R int = 0.026
  • 2 standard reflections frequency: 60 min intensity decay: none

Refinement

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

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [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/S160053680804141X/ci2737sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804141X/ci2737Isup2.hkl

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

Acknowledgments

SP thanks the CSIR for funding a major research project.

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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.
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.
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.

Crystal data

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

Nonius MACH-3 diffractometer4342 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 25.0°, θmin = 2.0°
ω–2θ scansh = −1→12
Absorption correction: ψ scan (North et al., 1968)k = −15→16
Tmin = 0.988, Tmax = 0.992l = −23→24
11592 measured reflections2 standard reflections every 60 min
9879 independent reflections intensity decay: none

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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 0.99w = 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

Special details

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)

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*
C14−0.0888 (3)1.1077 (2)0.35148 (14)0.0497 (8)
H14−0.15121.14950.32750.060*
C15−0.0687 (3)1.1807 (2)0.39981 (16)0.0535 (8)
C16−0.0916 (3)1.2825 (2)0.38747 (17)0.0616 (9)
H16−0.12381.30600.35050.074*
C17−0.0682 (4)1.3501 (3)0.4284 (2)0.0759 (11)
H17−0.08451.41820.41870.091*
C18−0.0207 (4)1.3173 (3)0.4833 (2)0.0865 (13)
H18−0.00261.36240.51020.104*
C19−0.0005 (4)1.2176 (3)0.49794 (19)0.0861 (13)
H190.02961.19510.53560.103*
C20−0.0247 (4)1.1505 (3)0.45711 (18)0.0716 (11)
H20−0.01121.08320.46810.086*
C21−0.1493 (3)1.0263 (2)0.38361 (15)0.0513 (8)
H21−0.09780.98890.41390.062*
C22−0.2973 (3)1.0681 (2)0.42099 (16)0.0514 (8)
C23−0.3386 (4)1.0833 (3)0.49076 (17)0.0702 (10)
H23−0.27481.06660.51520.084*
C24−0.4738 (4)1.1231 (3)0.52476 (19)0.0836 (12)
H24−0.50011.13300.57180.100*
C25−0.5676 (4)1.1476 (3)0.4899 (2)0.0757 (11)
H25−0.65851.17380.51290.091*
C26−0.5290 (4)1.1337 (3)0.42030 (19)0.0681 (10)
H26−0.59351.15080.39620.082*
C27−0.3937 (4)1.0941 (2)0.38614 (17)0.0590 (9)
H27−0.36791.08500.33910.071*
C280.0013 (3)0.9504 (2)0.27379 (15)0.0465 (8)
C29−0.0114 (3)0.9474 (2)0.20229 (15)0.0515 (8)
C30−0.0968 (4)1.0131 (3)0.17111 (19)0.0706 (10)
H30−0.16161.07210.19490.085*
C31−0.0858 (5)0.9907 (3)0.1039 (2)0.0920 (13)
H31−0.14251.03550.08210.110*
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*
C42−0.0370 (3)0.5458 (3)0.26163 (17)0.0575 (9)
C43−0.1500 (4)0.5157 (3)0.27214 (19)0.0707 (10)
H43−0.15140.46510.24270.085*
C44−0.2616 (4)0.5601 (3)0.3262 (2)0.0798 (11)
H44−0.33740.53950.33250.096*
C45−0.2611 (4)0.6334 (3)0.3699 (2)0.0814 (12)
H45−0.33650.66360.40580.098*
C46−0.1486 (4)0.6625 (3)0.3608 (2)0.0901 (13)
H46−0.14690.71160.39120.108*
C47−0.0377 (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)
H510.51050.3094−0.07310.139*
C520.5360 (7)0.1722 (6)−0.0375 (3)0.144 (3)
H520.52480.1410−0.07470.173*
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)
H580.97210.4253−0.05070.112*
C591.0461 (4)0.3303 (4)0.0142 (2)0.0895 (13)
H591.13600.3132−0.01020.107*
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)
N2−0.1264 (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*
O1−0.0030 (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)
H2−0.144 (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)

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, °)

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—C45−0.5 (6)
C2—C3—C4—C5−44.1 (4)C43—C44—C45—C46−0.7 (6)
O1—C4—C5—C6−132.6 (3)C44—C45—C46—C471.4 (7)
C3—C4—C5—C645.6 (3)C43—C42—C47—C46−0.4 (6)
O1—C4—C5—C14−10.1 (4)C41—C42—C47—C46−179.1 (4)
C3—C4—C5—C14168.1 (3)C45—C46—C47—C42−0.8 (7)
O1—C4—C5—C28104.5 (3)C40—C39—C48—C49−32.7 (4)
C3—C4—C5—C28−77.3 (3)C38—C39—C48—C4987.5 (3)
C4—C5—C6—N1−57.0 (3)C62—C39—C48—C49−154.3 (3)
C14—C5—C6—N1−179.4 (2)C40—C39—C48—C5596.1 (3)
C28—C5—C6—N165.0 (3)C38—C39—C48—C55−143.8 (2)
N1—C7—C8—C9−58.4 (5)C62—C39—C48—C55−25.6 (3)
N1—C7—C8—C13123.3 (4)C55—C48—C49—C54149.9 (3)
C13—C8—C9—C100.1 (6)C39—C48—C49—C54−87.8 (4)
C7—C8—C9—C10−178.3 (3)C55—C48—C49—C50−28.8 (5)
C8—C9—C10—C110.6 (6)C39—C48—C49—C5093.5 (4)
C9—C10—C11—C12−0.6 (7)C54—C49—C50—C511.2 (6)
C10—C11—C12—C130.0 (8)C48—C49—C50—C51179.9 (4)
C9—C8—C13—C12−0.8 (7)C49—C50—C51—C520.5 (7)
C7—C8—C13—C12177.6 (5)C50—C51—C52—C53−1.9 (9)
C11—C12—C13—C80.8 (9)C51—C52—C53—C541.4 (10)
C4—C5—C14—C15−81.1 (3)C50—C49—C54—C53−1.7 (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—C21−90.7 (3)C39—C48—C55—N542.5 (3)
C28—C5—C14—C2130.6 (3)C49—C48—C55—C56−69.2 (4)
C21—C14—C15—C16−142.3 (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—C61−60.4 (4)
C5—C14—C15—C20−83.3 (4)N5—C55—C56—C57−126.0 (3)
C20—C15—C16—C172.0 (5)C48—C55—C56—C57120.6 (3)
C14—C15—C16—C17−176.8 (3)C61—C56—C57—C581.0 (5)
C15—C16—C17—C18−0.1 (5)C55—C56—C57—C58−179.9 (3)
C16—C17—C18—C19−1.7 (6)C56—C57—C58—C59−0.4 (6)
C17—C18—C19—C201.4 (6)C57—C58—C59—C60−0.5 (7)
C18—C19—C20—C150.6 (6)C58—C59—C60—C610.8 (7)
C16—C15—C20—C19−2.3 (5)C59—C60—C61—C56−0.1 (6)
C14—C15—C20—C19176.4 (3)C57—C56—C61—C60−0.7 (5)
C15—C14—C21—N2−168.4 (3)C55—C56—C61—C60−179.8 (3)
C5—C14—C21—N2−40.2 (3)C40—C39—C62—N5−122.1 (3)
C15—C14—C21—C2271.9 (4)C38—C39—C62—N5118.7 (3)
C5—C14—C21—C22−159.8 (3)C48—C39—C62—N5−0.8 (3)
N2—C21—C22—C27−36.7 (4)C40—C39—C62—C63115.3 (3)
C14—C21—C22—C2776.5 (4)C38—C39—C62—C63−3.9 (4)
N2—C21—C22—C23144.9 (3)C48—C39—C62—C63−123.4 (3)
C14—C21—C22—C23−102.0 (4)C40—C39—C62—C69−2.1 (3)
C27—C22—C23—C240.4 (5)C38—C39—C62—C69−121.3 (3)
C21—C22—C23—C24178.9 (3)C48—C39—C62—C69119.1 (3)
C22—C23—C24—C250.1 (6)N5—C62—C63—C64−59.3 (4)
C23—C24—C25—C26−0.5 (6)C69—C62—C63—C64−176.2 (3)
C24—C25—C26—C270.3 (6)C39—C62—C63—C6459.9 (4)
C23—C22—C27—C26−0.6 (5)N5—C62—C63—C68117.7 (3)
C21—C22—C27—C26−179.1 (3)C69—C62—C63—C680.7 (3)
C25—C26—C27—C220.2 (5)C39—C62—C63—C68−123.2 (3)
C4—C5—C28—N2−129.1 (3)C68—C63—C64—C653.4 (5)
C6—C5—C28—N2111.6 (3)C62—C63—C64—C65−179.9 (3)
C14—C5—C28—N2−9.2 (3)C63—C64—C65—C66−1.5 (5)
C4—C5—C28—C29−6.9 (4)C64—C65—C66—C67−1.1 (6)
C6—C5—C28—C29−126.2 (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—N6−178.8 (3)
C6—C5—C28—C35−9.4 (3)C64—C63—C68—C67−2.9 (5)
C14—C5—C28—C35−130.3 (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—N6−1.0 (3)
C5—C28—C29—C30−62.9 (4)N5—C62—C69—O456.2 (4)
N2—C28—C29—C34−123.5 (3)C63—C62—C69—O4173.1 (3)
C35—C28—C29—C34−5.3 (3)C39—C62—C69—O4−59.7 (4)
C5—C28—C29—C34118.5 (3)N5—C62—C69—N6−117.0 (3)
C34—C29—C30—C31−1.4 (5)C63—C62—C69—N6−0.2 (3)
C28—C29—C30—C31−179.8 (4)C39—C62—C69—N6127.0 (3)
C29—C30—C31—C321.0 (6)C3—C2—N1—C6−62.1 (3)
C30—C31—C32—C33−0.6 (7)C3—C2—N1—C7177.2 (3)
C31—C32—C33—C340.4 (6)C5—C6—N1—C268.0 (3)
C32—C33—C34—C29−0.8 (5)C5—C6—N1—C7−169.2 (3)
C32—C33—C34—N3175.9 (3)C8—C7—N1—C2−61.0 (4)
C30—C29—C34—C331.3 (5)C8—C7—N1—C6178.3 (3)
C28—C29—C34—C33−179.9 (3)C29—C28—N2—C21−142.1 (3)
C30—C29—C34—N3−175.9 (3)C35—C28—N2—C21105.7 (3)
C28—C29—C34—N32.8 (3)C5—C28—N2—C21−17.3 (3)
N2—C28—C35—O2−49.5 (4)C22—C21—N2—C28158.1 (3)
C29—C28—C35—O2−168.0 (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—C34−4.8 (3)
C29—C28—C35—N36.0 (3)C33—C34—N3—C35−175.6 (3)
C5—C28—C35—N3−118.7 (3)C29—C34—N3—C351.4 (4)
N4—C36—C37—C38−49.7 (4)C37—C36—N4—C4063.3 (3)
C36—C37—C38—O3−137.5 (3)C37—C36—N4—C41−173.8 (3)
C36—C37—C38—C3942.0 (4)C39—C40—N4—C36−69.9 (3)
O3—C38—C39—C40135.0 (3)C39—C40—N4—C41167.3 (2)
C37—C38—C39—C40−44.5 (3)C42—C41—N4—C3661.8 (3)
O3—C38—C39—C4811.7 (4)C42—C41—N4—C40−176.9 (3)
C37—C38—C39—C48−167.8 (3)C63—C62—N5—C55156.4 (2)
O3—C38—C39—C62−102.3 (3)C69—C62—N5—C55−92.8 (3)
C37—C38—C39—C6278.2 (3)C39—C62—N5—C5528.9 (3)
C38—C39—C40—N457.9 (3)C56—C55—N5—C62−167.9 (3)
C48—C39—C40—N4−179.0 (2)C48—C55—N5—C62−45.3 (3)
C62—C39—C40—N4−63.1 (3)O4—C69—N6—C68−173.7 (3)
N4—C41—C42—C4764.6 (4)C62—C69—N6—C68−0.4 (3)
N4—C41—C42—C43−114.0 (4)C67—C68—N6—C69−179.9 (3)
C47—C42—C43—C441.1 (5)C63—C68—N6—C690.9 (3)

Hydrogen-bond geometry (Å, °)

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 codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2737).

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.
  • Bhattacharya, S. K., Glover, V., McIntyre, I., Oxenkrug, G. & Sandler, M. (1982). Neurosci. Lett.92, 218–221. [PubMed]
  • Enraf-Nonius (1994). CAD-4 EXPRESS Enraf-Nonius, Delft, The Netherlands.
  • Glover, V., Halket, J. M., Watkins, P. J., Clow, A., Goodwin, B. L. & Sandler, M. (1998). J. Neurochem.51, 656–659. [PubMed]
  • Govind, M. M., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sureshbabu, A. R. & Raghunathan, R. (2004). Acta Cryst. E60, o54–o56.
  • Harms, K. & Wocadlo, S. (1996). XCAD4 University of Marburg, Germany.
  • Hilton, S. T., Ho, T. C., Pljevalijcic, G. & Jones, K. (2000). Org. Lett.2, 17, 2639–2641. [PubMed]
  • 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, G., Hesse, S. & Comel, A. (2004). Curr. Org. Chem.1, 47–63.
  • Klumpp, D. A., Yeung, K. Y., Prakash, G. K. S. & Olah, G. A. (1998). J. Org. Chem.63, 4481–4484.
  • Kumar, R., Bansal, R. C. & Mahmood, A. (1993). Biogenic Amines, 9, 281–289.
  • Kumar, R. G., Gayathri, D., Velmurugan, D., Ravikumar, K. & Poornachandran, M. (2006). Acta Cryst. E62, o4821–o4823.
  • Medvedev, A. E., Clow, A., Sandler, M. & Glover, V. (1996). Biochem. Pharmacol.52, 385–391. [PubMed]
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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