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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 2| February 2009| Pages o298-o299

2-(1-Adamant­yl)-1-{4-[(2-chloro-9-iso­propyl-9H-purin-6-yl)amino­meth­yl]phen­yl}ethanone

aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic, and bDepartment of Chemistry, Faculty of Science, Masaryk University in Brno, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
*Correspondence e-mail: rvicha@ft.utb.cz

(Received 10 December 2008; accepted 6 January 2009; online 14 January 2009)

The structure of the title compound, C27H32ClN5O, consists of two crystallographically independent conformers differing slightly in all geometric parameters. Both contain nearly planar purine and benzene ring systems [maximum deviations of 0.046 (3) and 0.005 (2) Å, respectively], the dihedral angles between them being 76.44 (6) and 82.39 (6)°, and an adamantane cage consisting of three fused cyclo­hexane rings in almost ideal chair conformations, with C—C—C angles in the range 108.7 (2)–110.6 (2)°. The carbonyl plane and the benzene ring are almost coplanar [dihedral angles of 6.43 (9) and 0.64 (8)° in the two conformers]. The crystal structure is stabilized by inter­molecular N—H⋯N inter­actions that link adjacent mol­ecules into dimers and by some non-bonding contacts of the C—H⋯Cl type.

Related literature

The title compound was prepared according to a modified procedure published by Fiorini & Abel (1989[Fiorini, M. T. & Abel, Ch. (1989). Tetrahedron Lett. 39, 1827-1830.]). For the synthesis and/or biological activity of related compounds, see: Veselý et al. (1994[Veselý, J., Havlíček, L., Strnad, M., Blow, J. J., Donnella-Deana, A., Pinna, L., Letham, D. S., Kato, J., Detivaud, L., Leclerc, S. & Meijer, L. (1994). Eur. J. Biochem. 224, 771-786.]); Havlíček et al. (1997[Havlíček, L., Hanuš, J., Veselý, J., Leclerc, S., Meijer, L., Shaw, G. & Strnad, M. (1997). J. Med. Chem. 40, 408-412.]); de Azevedo et al. (1997[Azevedo, W. F. de, Leclerc, S., Meijer, L., Havlíček, L., Strnad, M. & Kim, S.-H. (1997). Eur. J. Biochem. 243, 518-526.]); Kryštof et al. (2002[Kryštof, V., Lenobel, R., Havlíček, L., Kuzma, M. & Strnad, M. (2002). Bioorg. Med. Chem. Lett. 12, 3283-3286.]); Kryštof et al. (2005[Kryštof, V., McNae, I. W., Walkinshaw, M. D., Fischer, P. M., Muller, P., Vojtěšek, B., Orság, M., Havlíček, L. & Strnad, M. (2005). Cell. Mol. Life Sci. 62, 1763-1771.]); Legraverend & Grierson (2006[Legraverend, M. & Grierson, D. S. (2006). Bioorg. Med. Chem. 14, 3987-4006.]). For some important properties of adamantane-bearing compounds, see: van Bommel et al. (2001[Bommel, K. J. C. van, Metselaar, G. A., Verboom, W. & Reinhoudt, D. N. (2001). J. Org. Chem. 66, 5405-5412.]); Cromwell et al. (1985[Cromwell, W. C., Bystrom, K. & Eftink, M. R. (1985). J. Phys. Chem. 89, 326-332.]). For related structures, see: Wang et al. (2001[Wang, S., McClue, S. J., Ferguson, J. R., Hull, J. D., Stokes, S., Parsons, S., Westwood, R. & Fischer, P. M. (2001). Tetrahedron Asymmetry, 12, 2891-2894.]); Trávníček & Zatloukal (2004[Trávníček, Z. & Zatloukal, M. (2004). Acta Cryst. E60, o924-o926.]); Trávníček & Popa (2007a[Trávníček, Z. & Popa, I. (2007a). Acta Cryst. E63, o629-o631.],b[Trávníček, Z. & Popa, I. (2007b). Acta Cryst. E63, o728-o730.]).

[Scheme 1]

Experimental

Crystal data
  • C27H32ClN5O

  • Mr = 478.03

  • Monoclinic, P 21 /c

  • a = 15.8778 (5) Å

  • b = 20.2779 (5) Å

  • c = 15.2225 (5) Å

  • β = 104.233 (3)°

  • V = 4750.7 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 120 (2) K

  • 0.50 × 0.40 × 0.30 mm

Data collection
  • Kuma KM-4 CCD diffractometer

  • Absorption correction: multi-scan (Xcalibur; Oxford Diffraction, 2006[Oxford Diffraction (2006). Xcalibur. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.872, Tmax = 0.944

  • 47831 measured reflections

  • 8353 independent reflections

  • 5567 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.150

  • S = 1.09

  • 8353 reflections

  • 617 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N5—H5A⋯N53i 0.88 2.20 2.997 (3) 150
N55—H55A⋯N3ii 0.88 2.18 2.946 (3) 145
C27—H27A⋯Cl1iii 0.98 2.86 3.732 (3) 149
C54—H54B⋯Cl51iv 0.99 2.76 3.698 (3) 158
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+3, -y, -z+2; (iv) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Table 2
Comparative torsion angles (°) for selected 2,6,9-trisubstituted purines containing the 2-chloro 6-benzylamino and 9-isopropyl unit

Compound angle value angle value
NG38a C6—N6—C9—C10 115.22 (13) H17—C17—N9—C4 −13.38 (18)
CIBAP1b C6—N6—C9—C10 178.97 (15) H16—C16—N9—C4 −63.03 (2)
CIBAP2c C6—N6—C9—C10 −117.35 (2) H16—C16—N9—C4 30.35 (3)
CIABAPd C20—N5—C19—C16 100.28 (3) H25—C25—N4—C22 45.01 (3)
CIABAPd C70—N55—C69—C66 −99.62 (3) H75—C75—N54—C72 −40.79 (3)
Notes: (a) Trávníček & Zatloukal (2004[Trávníček, Z. & Zatloukal, M. (2004). Acta Cryst. E60, o924-o926.]), where NG38 is N-[(2-azepan-1-yl)-9-isopropyl-9H-purin-6-yl]-4-methoxybenzylamine; (b) Trávníček & Popa (2007a[Trávníček, Z. & Popa, I. (2007a). Acta Cryst. E63, o629-o631.]), where CIBAP1 is 2-chloro-6-[(2,6-dimethoxybenzyl)amino]-9-isopropylpurine; (c) Trávníček & Popa (2007b[Trávníček, Z. & Popa, I. (2007b). Acta Cryst. E63, o728-o730.]), where CIBAP2 is 2-chloro-6-[(4-hydroxy-3,5-dimethoxybenzyl)amino]-9-isopropylpurine; (d) this work, where CIABAP is the title compound (the structure consists of two crystallographically independent molecules).

Data collection: Xcalibur (Oxford Diffraction, 2006[Oxford Diffraction (2006). Xcalibur. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: Xcalibur; data reduction: Xcalibur; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title molecule is related to the family of 2,6,9-trisubstituted purines that behave as potent inhibitors of cyclin-dependent kinases and show anticancer activity. The antiproliferative and proapoptotic effects of these drugs have been studied extensively with both an important and a promising result (Veselý et al., 1994; Havlíček et al., 1997; de Azevedo et al., 1997; Kryštof et al., 2002; Kryštof et al., 2005; Legraverend & Grierson, 2006). The adamantane group is frequently used to improve the pharmacological properties of potential drugs. Whereas the lipophilic adamantane cage itself may increase solubility in non-polar systems (e.g. cell membranes), the non-covalent complex of adamantane with cyclodextrins can enhance solubility in water based media (Cromwell et al., 1985; van Bommel et al., 2001). Both these facilities have considerable importance in drug design and formulation. To the best of our knowledge, the title compound is the first described derivative of a 2,6,9-trisubstituted purine with an adamantyl group linked to 6-benzylamino substituent.

The structure consists of two crystallographically independent molecules slightly variant in geometry. Each ring is essentially planar, the maximum deviations from the best planes being 0.026 (2) Å for atom C23 (pyrimidine rings), 0.0050 (10) Å for atoms C72 and C73 (imidazole rings) and 0.005 (2) Å for atoms C13, C16 and C68 (benzene rings). The dihedral angles between purine and benzene rings are 76.44 (6)° and 82.39 (6)° respectively. The torsion angles C19–N5–C20–C23, C20–N5–C19–C16, N5–C19–C16–C17, C18–C13–C12–C11 and C13–C12–C11–C1 are 172.35 (2), 100.28 (3), 146.27 (2), -6.92 (4) and -100.18 (3)° respectively. The corresponding values of torsion angles for the second distinct conformer are -176.98 (2), -99.62 (3), -168.68 (2), 0.16 (4) and 95.57 (3) respectively. Comparative torsion angles for selected related molecules are shown in Table 2. The crystal structure is stabilized by intermolecular N–H···N interactions that link the molecules into pairs (Fig. 2 and Table 1), the N···N distances being 2.997 (3) and 2.946 (3) Å. respectively. There are also some additional intermolecular non-bonding contacts of the type C–H···Cl (Table 1). One from the two conformers is linked by C27–H27A···Cl1 interaction into pairs and the second conformer is linked by C54–H54B···Cl51 into linear chains. No other short intermolecular interactions were found.

Related literature top

The title compound was prepared according to a modified procedure published by Fiorini & Abel (1989). For the synthesis and/or biological activity of related compounds, see: Veselý et al. (1994); Havlíček et al. (1997); de Azevedo et al. (1997); Kryštof et al. (2002); Kryštof et al. (2005); Legraverend & Grierson (2006). For some important properties of adamantane-bearing compounds, see: van Bommel et al. (2001); Cromwell et al. (1985). For related structures, see: Wang et al. (2001); Trávníček & Zatloukal (2004); Trávníček & Popa (2007a,b).

Experimental top

The title compound was prepared according to a slightly modified literature procedure (Fiorini & Abel, 1989). 2,6-Dichloro-9-(propan-2-yl)-9H-purine (0.65 mmol, 150 mg) and 1-[4-(aminoethyl)phenyl)]-2-(1-adamantyl)ethanone hydrochloride (0.68 mmol, 218 mg) were dissolved in the mixture of DMF (2 cm3) and triethylamine (1.30 mmol, 0.18 cm3). The resulting solution was stirred and refluxed for 2.5 h. After the starting material had all reacted (according to TLC), the mixture was diluted with water and extracted five times with 15 cm3 of diethyl ether. The combined organic layers were washed twice with brine, dried over sodium sulfate and evaporated in vacuum. The crude product was purified by column chromatography (silica gel; petroleum ether/ethyl acetate, v/v, 1/1). The desired product was obtained as pale yellow crystalline powder (228 mg, 74%, mp 146–150°C). The crystal used for data collection was grown by liquid diffusion (acetone/hexane, v/v, 1/3) at -18°C within 48 h.

Computing details top

Data collection: Xcalibur (Oxford Diffraction, 2006); cell refinement: Xcalibur (Oxford Diffraction, 2006); data reduction: Xcalibur (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP of the asymmetric unit with atoms represented as 50% probability ellipsoids. H-atoms have been omitted to enhance clarity.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound, showing the hydrogen bonding (dashed lines).
2-(1-Adamantyl)-1-{4-[(2-chloro-9-isopropyl-9H-purin-6- yl)aminomethyl]phenyl}ethanone top
Crystal data top
C27H32ClN5OF(000) = 2032
Mr = 478.03Dx = 1.337 Mg m3
Monoclinic, P21/cMelting point: 148 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.8778 (5) ÅCell parameters from 8353 reflections
b = 20.2779 (5) Åθ = 2.8–25.0°
c = 15.2225 (5) ŵ = 0.19 mm1
β = 104.233 (3)°T = 120 K
V = 4750.7 (3) Å3Block, yellow
Z = 80.50 × 0.40 × 0.30 mm
Data collection top
Kuma KM-4 CCD
diffractometer
8353 independent reflections
Radiation source: fine-focus sealed tube5567 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 0.06 pixels mm-1θmax = 25.0°, θmin = 2.8°
ω scansh = 1618
Absorption correction: multi-scan
(Xcalibur; Oxford Diffraction, 2006)
k = 2423
Tmin = 0.872, Tmax = 0.944l = 1818
47831 measured reflections
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0761P)2 + 2.6597P]
where P = (Fo2 + 2Fc2)/3
8353 reflections(Δ/σ)max = 0.005
617 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C27H32ClN5OV = 4750.7 (3) Å3
Mr = 478.03Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.8778 (5) ŵ = 0.19 mm1
b = 20.2779 (5) ÅT = 120 K
c = 15.2225 (5) Å0.50 × 0.40 × 0.30 mm
β = 104.233 (3)°
Data collection top
Kuma KM-4 CCD
diffractometer
8353 independent reflections
Absorption correction: multi-scan
(Xcalibur; Oxford Diffraction, 2006)
5567 reflections with I > 2σ(I)
Tmin = 0.872, Tmax = 0.944Rint = 0.026
47831 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.150H-atom parameters constrained
S = 1.09Δρmax = 0.35 e Å3
8353 reflectionsΔρmin = 0.29 e Å3
617 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 > 2σ(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
Cl11.54371 (4)0.16850 (4)1.01111 (5)0.0416 (2)
O11.15991 (12)0.38506 (9)0.65047 (14)0.0418 (5)
N11.39808 (13)0.11570 (10)0.92710 (14)0.0265 (5)
N21.53027 (13)0.05913 (10)0.92127 (14)0.0278 (5)
N41.50180 (14)0.04121 (10)0.83228 (14)0.0289 (5)
N31.35644 (14)0.03462 (10)0.78459 (15)0.0306 (5)
N51.26108 (13)0.07666 (10)0.85571 (14)0.0261 (5)
H5A1.22930.04950.81590.031*
C10.95337 (16)0.38700 (11)0.59602 (15)0.0222 (5)
C20.98831 (16)0.39531 (12)0.51181 (17)0.0269 (6)
H2B1.03400.36200.51230.032*
H2C1.01470.43960.51220.032*
C30.91501 (17)0.38722 (12)0.42610 (17)0.0281 (6)
H3A0.93910.39290.37170.034*
C40.84508 (17)0.43886 (13)0.42383 (18)0.0321 (6)
H4B0.79760.43330.36840.038*
H4C0.86990.48360.42280.038*
C50.80936 (17)0.43108 (13)0.50779 (17)0.0285 (6)
H5B0.76360.46510.50700.034*
C60.77037 (17)0.36252 (13)0.50670 (17)0.0302 (6)
H6A0.72250.35710.45160.036*
H6B0.74610.35690.56020.036*
C70.83958 (17)0.31037 (13)0.50795 (17)0.0282 (6)
H7A0.81320.26560.50740.034*
C80.91320 (16)0.31812 (12)0.59364 (16)0.0254 (6)
H8A0.95830.28420.59440.030*
H8B0.89020.31170.64790.030*
C90.87618 (17)0.31819 (13)0.42455 (17)0.0308 (6)
H9A0.92150.28450.42530.037*
H9B0.82940.31210.36870.037*
C100.88214 (17)0.43880 (12)0.59306 (17)0.0284 (6)
H10A0.85840.43380.64700.034*
H10B0.90750.48350.59460.034*
C111.02429 (17)0.39841 (12)0.68438 (17)0.0291 (6)
H11A1.03690.44620.69080.035*
H11B1.00110.38470.73630.035*
C121.10835 (17)0.36200 (13)0.68945 (17)0.0287 (6)
C131.12982 (16)0.29932 (12)0.74137 (16)0.0258 (6)
C141.20554 (18)0.26697 (13)0.73665 (18)0.0331 (6)
H14A1.23960.28430.69870.040*
C151.23249 (17)0.21078 (13)0.78510 (18)0.0327 (6)
H15A1.28470.18980.78040.039*
C161.18432 (16)0.18431 (12)0.84080 (16)0.0240 (5)
C171.10862 (16)0.21535 (13)0.84536 (17)0.0279 (6)
H17A1.07450.19740.88280.033*
C181.08111 (16)0.27234 (12)0.79635 (17)0.0280 (6)
H18A1.02850.29300.80050.034*
C191.21638 (16)0.12463 (12)0.89844 (17)0.0263 (6)
H19A1.25630.13940.95570.032*
H19B1.16620.10290.91400.032*
C201.34751 (16)0.07103 (12)0.87280 (15)0.0228 (5)
C211.48320 (16)0.10626 (13)0.94474 (16)0.0275 (6)
C221.47769 (16)0.01555 (12)0.86771 (16)0.0246 (6)
C231.38849 (16)0.01919 (12)0.83828 (17)0.0255 (6)
C241.42650 (18)0.06881 (13)0.78385 (19)0.0333 (6)
H24A1.42480.10940.75220.040*
C251.59119 (17)0.06731 (13)0.84933 (18)0.0326 (6)
H25A1.61810.06380.91580.039*
C261.64435 (18)0.02650 (14)0.8010 (2)0.0389 (7)
H26A1.61970.02950.73550.058*
H26B1.70430.04280.81570.058*
H26C1.64380.01960.82020.058*
C271.5911 (2)0.13913 (15)0.8235 (3)0.0566 (10)
H27A1.55240.16370.85280.085*
H27B1.65020.15680.84330.085*
H27C1.57060.14350.75750.085*
Cl511.06711 (4)0.32556 (3)1.02370 (4)0.03138 (18)
O510.65672 (14)0.16100 (11)0.55786 (14)0.0508 (6)
N510.92396 (13)0.37756 (10)0.93336 (13)0.0251 (5)
N521.05595 (13)0.43726 (10)0.93901 (13)0.0231 (5)
N530.88368 (13)0.53117 (10)0.79834 (13)0.0237 (5)
N541.02812 (13)0.53960 (10)0.85313 (13)0.0223 (5)
N550.78821 (13)0.41714 (10)0.86172 (13)0.0264 (5)
H55A0.75660.44740.82740.032*
C510.47184 (16)0.11567 (12)0.58865 (16)0.0259 (6)
C520.43209 (18)0.16706 (13)0.63953 (18)0.0326 (6)
H52B0.44030.15330.70350.039*
H52C0.46180.20990.63880.039*
C530.33568 (18)0.17478 (14)0.5956 (2)0.0370 (7)
H53B0.31030.20830.62980.044*
C540.2906 (2)0.10865 (16)0.5982 (2)0.0478 (8)
H54A0.29910.09380.66170.057*
H54B0.22740.11330.57120.057*
C550.3289 (2)0.05839 (15)0.5449 (2)0.0496 (8)
H55B0.29880.01510.54530.060*
C560.3168 (2)0.08135 (18)0.4476 (2)0.0605 (10)
H56A0.34070.04790.41290.073*
H56B0.25410.08670.41880.073*
C570.3632 (2)0.14650 (17)0.44614 (19)0.0457 (8)
H57A0.35560.16130.38200.055*
C580.45957 (18)0.13811 (15)0.49055 (18)0.0373 (7)
H58A0.49010.18050.48900.045*
H58B0.48490.10500.45670.045*
C590.3243 (2)0.19791 (16)0.49812 (19)0.0437 (8)
H59A0.35390.24080.49730.052*
H59B0.26180.20390.46900.052*
C600.42482 (18)0.05001 (13)0.5893 (2)0.0380 (7)
H60A0.45000.01640.55600.046*
H60B0.43240.03470.65250.046*
C610.56868 (17)0.10361 (13)0.63550 (19)0.0329 (6)
H61A0.57390.09580.70080.039*
H61B0.58770.06290.61010.039*
C620.62922 (17)0.15816 (14)0.62633 (19)0.0344 (7)
C630.65636 (16)0.20984 (13)0.69797 (17)0.0279 (6)
C680.62858 (17)0.21168 (13)0.77775 (17)0.0311 (6)
H68A0.59050.17860.78950.037*
C670.65643 (17)0.26183 (13)0.84013 (17)0.0294 (6)
H67A0.63640.26320.89400.035*
C660.71300 (16)0.30974 (12)0.82460 (16)0.0247 (6)
C650.74072 (16)0.30712 (13)0.74527 (17)0.0281 (6)
H65A0.77950.33990.73390.034*
C640.71310 (17)0.25799 (13)0.68273 (17)0.0295 (6)
H64A0.73300.25700.62880.035*
C690.74333 (17)0.36378 (13)0.89382 (16)0.0276 (6)
H69A0.69230.38190.91200.033*
H69B0.78260.34430.94840.033*
C700.87432 (15)0.42347 (11)0.88074 (15)0.0218 (5)
C711.00903 (16)0.38826 (12)0.95686 (15)0.0230 (5)
C721.00400 (16)0.48160 (11)0.88524 (15)0.0216 (5)
C730.91542 (16)0.47738 (11)0.85193 (15)0.0214 (5)
C740.95342 (16)0.56661 (12)0.80151 (16)0.0259 (6)
H74A0.95210.60750.77060.031*
C751.11732 (16)0.56615 (12)0.87100 (16)0.0250 (6)
H75A1.14620.55770.93620.030*
C761.11638 (17)0.63973 (12)0.85592 (18)0.0311 (6)
H76A1.09190.64920.79160.047*
H76B1.17590.65680.87430.047*
H76C1.08080.66090.89210.047*
C771.16747 (17)0.52945 (13)0.81434 (18)0.0308 (6)
H77A1.16710.48220.82770.046*
H77B1.22750.54550.82850.046*
H77C1.14040.53680.75000.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0251 (4)0.0477 (4)0.0511 (4)0.0055 (3)0.0075 (3)0.0211 (3)
O10.0265 (11)0.0396 (12)0.0568 (13)0.0032 (9)0.0051 (10)0.0171 (10)
N10.0216 (12)0.0287 (12)0.0294 (11)0.0004 (9)0.0067 (9)0.0004 (9)
N20.0225 (12)0.0299 (12)0.0305 (11)0.0001 (9)0.0057 (9)0.0000 (9)
N40.0235 (12)0.0237 (11)0.0394 (12)0.0046 (9)0.0079 (10)0.0022 (9)
N30.0285 (13)0.0233 (12)0.0387 (12)0.0021 (9)0.0055 (10)0.0002 (10)
N50.0201 (12)0.0246 (11)0.0319 (11)0.0002 (9)0.0030 (9)0.0023 (9)
C10.0228 (13)0.0199 (12)0.0232 (12)0.0009 (10)0.0045 (10)0.0027 (10)
C20.0238 (14)0.0245 (14)0.0326 (14)0.0020 (11)0.0074 (11)0.0031 (11)
C30.0293 (15)0.0328 (15)0.0232 (12)0.0005 (11)0.0081 (11)0.0013 (11)
C40.0291 (15)0.0322 (15)0.0337 (14)0.0007 (12)0.0055 (12)0.0043 (12)
C50.0252 (14)0.0265 (14)0.0324 (14)0.0075 (11)0.0043 (11)0.0013 (11)
C60.0226 (14)0.0416 (16)0.0271 (13)0.0001 (12)0.0072 (11)0.0015 (12)
C70.0285 (15)0.0241 (13)0.0314 (14)0.0054 (11)0.0061 (11)0.0007 (11)
C80.0265 (14)0.0230 (13)0.0277 (13)0.0006 (11)0.0088 (11)0.0028 (10)
C90.0271 (15)0.0347 (15)0.0276 (13)0.0001 (12)0.0010 (11)0.0084 (11)
C100.0310 (15)0.0253 (14)0.0281 (13)0.0049 (11)0.0060 (11)0.0057 (11)
C110.0306 (15)0.0243 (13)0.0285 (13)0.0017 (11)0.0000 (11)0.0031 (11)
C120.0242 (14)0.0283 (14)0.0297 (13)0.0047 (11)0.0007 (11)0.0025 (11)
C130.0252 (14)0.0241 (13)0.0263 (13)0.0019 (11)0.0027 (11)0.0048 (10)
C140.0313 (16)0.0327 (15)0.0393 (15)0.0010 (12)0.0165 (12)0.0056 (12)
C150.0236 (14)0.0309 (15)0.0462 (16)0.0043 (11)0.0137 (12)0.0078 (12)
C160.0202 (13)0.0271 (13)0.0237 (12)0.0045 (10)0.0034 (10)0.0063 (10)
C170.0248 (14)0.0332 (15)0.0286 (13)0.0004 (11)0.0122 (11)0.0025 (11)
C180.0206 (13)0.0294 (14)0.0336 (14)0.0041 (11)0.0061 (11)0.0032 (11)
C190.0218 (14)0.0282 (14)0.0296 (13)0.0033 (11)0.0074 (11)0.0003 (11)
C200.0247 (14)0.0213 (13)0.0220 (12)0.0000 (10)0.0051 (10)0.0034 (10)
C210.0226 (14)0.0333 (15)0.0256 (13)0.0025 (11)0.0039 (11)0.0014 (11)
C220.0268 (15)0.0218 (13)0.0254 (12)0.0033 (11)0.0066 (11)0.0032 (10)
C230.0219 (14)0.0245 (13)0.0307 (13)0.0008 (10)0.0073 (11)0.0058 (11)
C240.0314 (16)0.0229 (14)0.0441 (16)0.0010 (12)0.0063 (13)0.0036 (12)
C250.0267 (15)0.0363 (15)0.0357 (14)0.0108 (12)0.0097 (12)0.0078 (12)
C260.0286 (16)0.0364 (16)0.0519 (18)0.0054 (12)0.0101 (13)0.0125 (13)
C270.047 (2)0.0323 (17)0.104 (3)0.0129 (15)0.044 (2)0.0069 (17)
Cl510.0289 (4)0.0282 (4)0.0354 (4)0.0007 (3)0.0048 (3)0.0088 (3)
O510.0413 (13)0.0690 (15)0.0482 (13)0.0183 (11)0.0224 (11)0.0241 (11)
N510.0265 (12)0.0255 (11)0.0229 (10)0.0025 (9)0.0055 (9)0.0000 (9)
N520.0223 (11)0.0235 (11)0.0227 (10)0.0015 (9)0.0042 (9)0.0004 (8)
N530.0227 (12)0.0232 (11)0.0243 (10)0.0024 (9)0.0041 (9)0.0010 (8)
N540.0200 (11)0.0224 (11)0.0240 (10)0.0027 (8)0.0044 (9)0.0007 (8)
N550.0247 (12)0.0270 (12)0.0273 (11)0.0024 (9)0.0060 (9)0.0043 (9)
C510.0247 (14)0.0229 (13)0.0295 (13)0.0003 (10)0.0053 (11)0.0010 (10)
C520.0335 (16)0.0294 (15)0.0335 (14)0.0035 (12)0.0057 (12)0.0011 (11)
C530.0293 (16)0.0377 (16)0.0448 (16)0.0082 (12)0.0106 (13)0.0017 (13)
C540.0282 (17)0.056 (2)0.061 (2)0.0011 (14)0.0141 (15)0.0089 (16)
C550.0321 (18)0.0376 (18)0.079 (2)0.0115 (14)0.0124 (16)0.0095 (16)
C560.039 (2)0.074 (3)0.057 (2)0.0038 (17)0.0099 (16)0.0293 (18)
C570.0411 (18)0.066 (2)0.0263 (14)0.0110 (16)0.0002 (13)0.0028 (14)
C580.0352 (17)0.0457 (18)0.0331 (15)0.0060 (13)0.0123 (13)0.0005 (13)
C590.0400 (18)0.0469 (18)0.0419 (17)0.0134 (14)0.0056 (14)0.0094 (14)
C600.0375 (17)0.0240 (14)0.0537 (18)0.0033 (12)0.0132 (14)0.0003 (13)
C610.0313 (16)0.0275 (14)0.0383 (15)0.0053 (12)0.0054 (12)0.0024 (12)
C620.0217 (15)0.0425 (17)0.0372 (16)0.0028 (12)0.0038 (12)0.0049 (12)
C630.0238 (14)0.0313 (14)0.0272 (13)0.0070 (11)0.0037 (11)0.0027 (11)
C680.0257 (14)0.0309 (15)0.0338 (14)0.0035 (11)0.0018 (11)0.0078 (12)
C670.0257 (14)0.0353 (15)0.0266 (13)0.0043 (11)0.0051 (11)0.0058 (11)
C660.0206 (13)0.0250 (13)0.0253 (12)0.0034 (10)0.0008 (10)0.0060 (10)
C650.0245 (14)0.0282 (14)0.0336 (14)0.0004 (11)0.0108 (11)0.0031 (11)
C640.0280 (15)0.0327 (15)0.0302 (14)0.0014 (11)0.0116 (12)0.0020 (11)
C690.0245 (14)0.0345 (15)0.0238 (12)0.0065 (11)0.0058 (11)0.0051 (11)
C700.0215 (14)0.0234 (13)0.0212 (12)0.0024 (10)0.0066 (10)0.0054 (10)
C710.0253 (14)0.0236 (13)0.0200 (12)0.0011 (10)0.0051 (10)0.0001 (10)
C720.0254 (14)0.0221 (13)0.0184 (11)0.0007 (10)0.0073 (10)0.0032 (10)
C730.0242 (14)0.0222 (13)0.0188 (11)0.0017 (10)0.0069 (10)0.0023 (10)
C740.0261 (14)0.0246 (13)0.0266 (13)0.0002 (11)0.0056 (11)0.0002 (10)
C750.0211 (14)0.0286 (14)0.0245 (12)0.0043 (10)0.0038 (10)0.0029 (10)
C760.0277 (15)0.0275 (14)0.0384 (15)0.0088 (11)0.0087 (12)0.0009 (12)
C770.0246 (15)0.0313 (15)0.0363 (15)0.0017 (11)0.0069 (12)0.0018 (11)
Geometric parameters (Å, º) top
Cl1—C211.749 (3)Cl51—C711.744 (2)
O1—C121.217 (3)O51—C621.226 (3)
N1—C211.326 (3)N51—C711.327 (3)
N1—C201.350 (3)N51—C701.349 (3)
N2—C211.316 (3)N52—C711.310 (3)
N2—C221.345 (3)N52—C721.351 (3)
N4—C241.361 (3)N53—C741.311 (3)
N4—C221.365 (3)N53—C731.381 (3)
N4—C251.477 (3)N54—C721.364 (3)
N3—C241.313 (3)N54—C741.366 (3)
N3—C231.383 (3)N54—C751.477 (3)
N5—C201.337 (3)N55—C701.332 (3)
N5—C191.449 (3)N55—C691.445 (3)
N5—H5A0.8800N55—H55A0.8800
C1—C21.526 (3)C51—C521.525 (4)
C1—C81.532 (3)C51—C581.527 (4)
C1—C101.536 (3)C51—C601.528 (4)
C1—C111.545 (3)C51—C611.547 (4)
C2—C31.529 (3)C52—C531.521 (4)
C2—H2B0.9900C52—H52B0.9900
C2—H2C0.9900C52—H52C0.9900
C3—C41.520 (4)C53—C591.524 (4)
C3—C91.527 (4)C53—C541.525 (4)
C3—H3A1.0000C53—H53B1.0000
C4—C51.528 (4)C54—C551.520 (4)
C4—H4B0.9900C54—H54A0.9900
C4—H4C0.9900C54—H54B0.9900
C5—C101.519 (3)C55—C601.516 (4)
C5—C61.520 (4)C55—C561.518 (5)
C5—H5B1.0000C55—H55B1.0000
C6—C71.522 (4)C56—C571.515 (5)
C6—H6A0.9900C56—H56A0.9900
C6—H6B0.9900C56—H56B0.9900
C7—C91.529 (4)C57—C581.523 (4)
C7—C81.531 (3)C57—C591.528 (4)
C7—H7A1.0000C57—H57A1.0000
C8—H8A0.9900C58—H58A0.9900
C8—H8B0.9900C58—H58B0.9900
C9—H9A0.9900C59—H59A0.9900
C9—H9B0.9900C59—H59B0.9900
C10—H10A0.9900C60—H60A0.9900
C10—H10B0.9900C60—H60B0.9900
C11—C121.511 (4)C61—C621.494 (4)
C11—H11A0.9900C61—H61A0.9900
C11—H11B0.9900C61—H61B0.9900
C12—C131.491 (4)C62—C631.497 (4)
C13—C181.384 (4)C63—C641.386 (4)
C13—C141.387 (4)C63—C681.391 (4)
C14—C151.368 (4)C68—C671.387 (4)
C14—H14A0.9500C68—H68A0.9500
C15—C161.382 (4)C67—C661.383 (3)
C15—H15A0.9500C67—H67A0.9500
C16—C171.374 (3)C66—C651.384 (4)
C16—C191.508 (3)C66—C691.514 (3)
C17—C181.386 (4)C65—C641.373 (4)
C17—H17A0.9500C65—H65A0.9500
C18—H18A0.9500C64—H64A0.9500
C19—H19A0.9900C69—H69A0.9900
C19—H19B0.9900C69—H69B0.9900
C20—C231.405 (3)C70—C731.398 (3)
C22—C231.378 (4)C72—C731.375 (3)
C24—H24A0.9500C74—H74A0.9500
C25—C261.498 (4)C75—C771.507 (4)
C25—C271.508 (4)C75—C761.509 (3)
C25—H25A1.0000C75—H75A1.0000
C26—H26A0.9800C76—H76A0.9800
C26—H26B0.9800C76—H76B0.9800
C26—H26C0.9800C76—H76C0.9800
C27—H27A0.9800C77—H77A0.9800
C27—H27B0.9800C77—H77B0.9800
C27—H27C0.9800C77—H77C0.9800
C21—N1—C20116.8 (2)C71—N51—C70117.0 (2)
C21—N2—C22109.4 (2)C71—N52—C72109.7 (2)
C24—N4—C22105.5 (2)C74—N53—C73103.2 (2)
C24—N4—C25128.8 (2)C72—N54—C74105.7 (2)
C22—N4—C25125.7 (2)C72—N54—C75126.1 (2)
C24—N3—C23103.4 (2)C74—N54—C75128.1 (2)
C20—N5—C19124.2 (2)C70—N55—C69124.3 (2)
C20—N5—H5A117.9C70—N55—H55A117.8
C19—N5—H5A117.9C69—N55—H55A117.8
C2—C1—C8108.42 (19)C52—C51—C58108.9 (2)
C2—C1—C10108.5 (2)C52—C51—C60109.2 (2)
C8—C1—C10108.9 (2)C58—C51—C60108.7 (2)
C2—C1—C11112.2 (2)C52—C51—C61111.3 (2)
C8—C1—C11111.55 (19)C58—C51—C61111.8 (2)
C10—C1—C11107.27 (19)C60—C51—C61106.9 (2)
C1—C2—C3110.3 (2)C53—C52—C51110.2 (2)
C1—C2—H2B109.6C53—C52—H52B109.6
C3—C2—H2B109.6C51—C52—H52B109.6
C1—C2—H2C109.6C53—C52—H52C109.6
C3—C2—H2C109.6C51—C52—H52C109.6
H2B—C2—H2C108.1H52B—C52—H52C108.1
C4—C3—C9109.9 (2)C52—C53—C59109.0 (2)
C4—C3—C2110.1 (2)C52—C53—C54109.1 (2)
C9—C3—C2109.3 (2)C59—C53—C54110.6 (3)
C4—C3—H3A109.1C52—C53—H53B109.4
C9—C3—H3A109.1C59—C53—H53B109.4
C2—C3—H3A109.1C54—C53—H53B109.4
C3—C4—C5109.2 (2)C55—C54—C53108.9 (2)
C3—C4—H4B109.8C55—C54—H54A109.9
C5—C4—H4B109.8C53—C54—H54A109.9
C3—C4—H4C109.8C55—C54—H54B109.9
C5—C4—H4C109.8C53—C54—H54B109.9
H4B—C4—H4C108.3H54A—C54—H54B108.3
C10—C5—C6109.0 (2)C60—C55—C56110.0 (3)
C10—C5—C4110.1 (2)C60—C55—C54109.1 (3)
C6—C5—C4108.6 (2)C56—C55—C54110.1 (3)
C10—C5—H5B109.7C60—C55—H55B109.2
C6—C5—H5B109.7C56—C55—H55B109.2
C4—C5—H5B109.7C54—C55—H55B109.2
C5—C6—C7110.1 (2)C57—C56—C55109.7 (2)
C5—C6—H6A109.6C57—C56—H56A109.7
C7—C6—H6A109.6C55—C56—H56A109.7
C5—C6—H6B109.6C57—C56—H56B109.7
C7—C6—H6B109.6C55—C56—H56B109.7
H6A—C6—H6B108.1H56A—C56—H56B108.2
C6—C7—C9109.8 (2)C56—C57—C58109.6 (3)
C6—C7—C8109.7 (2)C56—C57—C59109.1 (3)
C9—C7—C8109.3 (2)C58—C57—C59109.6 (2)
C6—C7—H7A109.4C56—C57—H57A109.5
C9—C7—H7A109.4C58—C57—H57A109.5
C8—C7—H7A109.4C59—C57—H57A109.5
C7—C8—C1109.88 (19)C57—C58—C51109.9 (2)
C7—C8—H8A109.7C57—C58—H58A109.7
C1—C8—H8A109.7C51—C58—H58A109.7
C7—C8—H8B109.7C57—C58—H58B109.7
C1—C8—H8B109.7C51—C58—H58B109.7
H8A—C8—H8B108.2H58A—C58—H58B108.2
C3—C9—C7108.5 (2)C53—C59—C57109.1 (2)
C3—C9—H9A110.0C53—C59—H59A109.9
C7—C9—H9A110.0C57—C59—H59A109.9
C3—C9—H9B110.0C53—C59—H59B109.9
C7—C9—H9B110.0C57—C59—H59B109.9
H9A—C9—H9B108.4H59A—C59—H59B108.3
C5—C10—C1110.76 (19)C55—C60—C51109.8 (2)
C5—C10—H10A109.5C55—C60—H60A109.7
C1—C10—H10A109.5C51—C60—H60A109.7
C5—C10—H10B109.5C55—C60—H60B109.7
C1—C10—H10B109.5C51—C60—H60B109.7
H10A—C10—H10B108.1H60A—C60—H60B108.2
C12—C11—C1114.6 (2)C62—C61—C51115.4 (2)
C12—C11—H11A108.6C62—C61—H61A108.4
C1—C11—H11A108.6C51—C61—H61A108.4
C12—C11—H11B108.6C62—C61—H61B108.4
C1—C11—H11B108.6C51—C61—H61B108.4
H11A—C11—H11B107.6H61A—C61—H61B107.5
O1—C12—C13119.5 (2)O51—C62—C61119.1 (2)
O1—C12—C11118.6 (2)O51—C62—C63119.2 (3)
C13—C12—C11121.8 (2)C61—C62—C63121.8 (2)
C18—C13—C14117.7 (2)C64—C63—C68119.1 (2)
C18—C13—C12124.6 (2)C64—C63—C62117.0 (2)
C14—C13—C12117.6 (2)C68—C63—C62124.0 (2)
C15—C14—C13121.8 (2)C67—C68—C63120.1 (2)
C15—C14—H14A119.1C67—C68—H68A120.0
C13—C14—H14A119.1C63—C68—H68A120.0
C14—C15—C16120.5 (2)C66—C67—C68120.6 (2)
C14—C15—H15A119.8C66—C67—H67A119.7
C16—C15—H15A119.8C68—C67—H67A119.7
C17—C16—C15118.4 (2)C67—C66—C65118.8 (2)
C17—C16—C19120.8 (2)C67—C66—C69119.9 (2)
C15—C16—C19120.7 (2)C65—C66—C69121.3 (2)
C16—C17—C18121.2 (2)C64—C65—C66121.1 (2)
C16—C17—H17A119.4C64—C65—H65A119.4
C18—C17—H17A119.4C66—C65—H65A119.4
C13—C18—C17120.4 (2)C65—C64—C63120.3 (2)
C13—C18—H18A119.8C65—C64—H64A119.8
C17—C18—H18A119.8C63—C64—H64A119.8
N5—C19—C16114.2 (2)N55—C69—C66113.9 (2)
N5—C19—H19A108.7N55—C69—H69A108.8
C16—C19—H19A108.7C66—C69—H69A108.8
N5—C19—H19B108.7N55—C69—H69B108.8
C16—C19—H19B108.7C66—C69—H69B108.8
H19A—C19—H19B107.6H69A—C69—H69B107.7
N5—C20—N1119.3 (2)N55—C70—N51118.8 (2)
N5—C20—C23122.6 (2)N55—C70—C73122.7 (2)
N1—C20—C23118.1 (2)N51—C70—C73118.4 (2)
N2—C21—N1132.0 (2)N52—C71—N51131.4 (2)
N2—C21—Cl1114.40 (19)N52—C71—Cl51115.34 (18)
N1—C21—Cl1113.63 (19)N51—C71—Cl51113.28 (18)
N2—C22—N4126.9 (2)N52—C72—N54127.4 (2)
N2—C22—C23126.7 (2)N52—C72—C73126.8 (2)
N4—C22—C23106.4 (2)N54—C72—C73105.9 (2)
C22—C23—N3110.4 (2)C72—C73—N53111.1 (2)
C22—C23—C20116.9 (2)C72—C73—C70116.5 (2)
N3—C23—C20132.4 (2)N53—C73—C70132.3 (2)
N3—C24—N4114.3 (2)N53—C74—N54114.0 (2)
N3—C24—H24A122.9N53—C74—H74A123.0
N4—C24—H24A122.9N54—C74—H74A123.0
N4—C25—C26110.4 (2)N54—C75—C77109.4 (2)
N4—C25—C27111.2 (2)N54—C75—C76111.1 (2)
C26—C25—C27111.7 (2)C77—C75—C76112.8 (2)
N4—C25—H25A107.8N54—C75—H75A107.8
C26—C25—H25A107.8C77—C75—H75A107.8
C27—C25—H25A107.8C76—C75—H75A107.8
C25—C26—H26A109.5C75—C76—H76A109.5
C25—C26—H26B109.5C75—C76—H76B109.5
H26A—C26—H26B109.5H76A—C76—H76B109.5
C25—C26—H26C109.5C75—C76—H76C109.5
H26A—C26—H26C109.5H76A—C76—H76C109.5
H26B—C26—H26C109.5H76B—C76—H76C109.5
C25—C27—H27A109.5C75—C77—H77A109.5
C25—C27—H27B109.5C75—C77—H77B109.5
H27A—C27—H27B109.5H77A—C77—H77B109.5
C25—C27—H27C109.5C75—C77—H77C109.5
H27A—C27—H27C109.5H77A—C77—H77C109.5
H27B—C27—H27C109.5H77B—C77—H77C109.5
C8—C1—C2—C359.4 (3)C58—C51—C52—C5359.9 (3)
C10—C1—C2—C358.7 (3)C60—C51—C52—C5358.6 (3)
C11—C1—C2—C3177.0 (2)C61—C51—C52—C53176.4 (2)
C1—C2—C3—C460.1 (3)C51—C52—C53—C5960.9 (3)
C1—C2—C3—C960.8 (3)C51—C52—C53—C5459.9 (3)
C9—C3—C4—C561.4 (3)C52—C53—C54—C5561.1 (3)
C2—C3—C4—C559.2 (3)C59—C53—C54—C5558.7 (3)
C3—C4—C5—C1058.8 (3)C53—C54—C55—C6061.8 (3)
C3—C4—C5—C660.5 (3)C53—C54—C55—C5659.0 (3)
C10—C5—C6—C759.8 (3)C60—C55—C56—C5759.5 (3)
C4—C5—C6—C760.1 (3)C54—C55—C56—C5760.7 (3)
C5—C6—C7—C960.2 (3)C55—C56—C57—C5859.4 (3)
C5—C6—C7—C859.9 (3)C55—C56—C57—C5960.7 (3)
C6—C7—C8—C159.3 (3)C56—C57—C58—C5160.0 (3)
C9—C7—C8—C161.1 (3)C59—C57—C58—C5159.7 (3)
C2—C1—C8—C759.5 (3)C52—C51—C58—C5759.1 (3)
C10—C1—C8—C758.3 (3)C60—C51—C58—C5759.8 (3)
C11—C1—C8—C7176.5 (2)C61—C51—C58—C57177.6 (2)
C4—C3—C9—C760.3 (3)C52—C53—C59—C5760.5 (3)
C2—C3—C9—C760.7 (3)C54—C53—C59—C5759.4 (3)
C6—C7—C9—C359.3 (3)C56—C57—C59—C5359.8 (3)
C8—C7—C9—C361.1 (3)C58—C57—C59—C5360.2 (3)
C6—C5—C10—C159.7 (3)C56—C55—C60—C5159.9 (3)
C4—C5—C10—C159.3 (3)C54—C55—C60—C5161.0 (3)
C2—C1—C10—C558.6 (3)C52—C51—C60—C5559.0 (3)
C8—C1—C10—C559.2 (3)C58—C51—C60—C5559.6 (3)
C11—C1—C10—C5180.0 (2)C61—C51—C60—C55179.5 (2)
C2—C1—C11—C1248.3 (3)C52—C51—C61—C6272.2 (3)
C8—C1—C11—C1273.5 (3)C58—C51—C61—C6249.8 (3)
C10—C1—C11—C12167.4 (2)C60—C51—C61—C62168.7 (2)
C1—C11—C12—O180.4 (3)C51—C61—C62—O5183.7 (3)
C1—C11—C12—C13100.2 (3)C51—C61—C62—C6395.6 (3)
O1—C12—C13—C18172.5 (2)O51—C62—C63—C641.0 (4)
C11—C12—C13—C186.9 (4)C61—C62—C63—C64179.7 (2)
O1—C12—C13—C145.2 (4)O51—C62—C63—C68179.4 (3)
C11—C12—C13—C14175.4 (2)C61—C62—C63—C680.2 (4)
C18—C13—C14—C150.8 (4)C64—C63—C68—C671.1 (4)
C12—C13—C14—C15177.1 (2)C62—C63—C68—C67179.4 (2)
C13—C14—C15—C160.0 (4)C63—C68—C67—C661.1 (4)
C14—C15—C16—C170.7 (4)C68—C67—C66—C650.6 (4)
C14—C15—C16—C19176.5 (2)C68—C67—C66—C69179.5 (2)
C15—C16—C17—C180.7 (4)C67—C66—C65—C640.1 (4)
C19—C16—C17—C18176.4 (2)C69—C66—C65—C64179.9 (2)
C14—C13—C18—C170.8 (4)C66—C65—C64—C630.1 (4)
C12—C13—C18—C17176.9 (2)C68—C63—C64—C650.6 (4)
C16—C17—C18—C130.0 (4)C62—C63—C64—C65179.8 (2)
C20—N5—C19—C16100.3 (3)C70—N55—C69—C6699.6 (3)
C17—C16—C19—N5146.3 (2)C67—C66—C69—N55168.7 (2)
C15—C16—C19—N536.6 (3)C65—C66—C69—N5511.3 (3)
C19—N5—C20—N16.0 (3)C69—N55—C70—N510.0 (3)
C19—N5—C20—C23172.3 (2)C69—N55—C70—C73177.0 (2)
C21—N1—C20—N5177.3 (2)C71—N51—C70—N55174.7 (2)
C21—N1—C20—C231.1 (3)C71—N51—C70—C732.3 (3)
C22—N2—C21—N12.1 (4)C72—N52—C71—N511.8 (4)
C22—N2—C21—Cl1177.54 (17)C72—N52—C71—Cl51178.53 (16)
C20—N1—C21—N22.5 (4)C70—N51—C71—N521.0 (4)
C20—N1—C21—Cl1177.14 (17)C70—N51—C71—Cl51179.33 (16)
C21—N2—C22—N4177.5 (2)C71—N52—C72—N54178.9 (2)
C21—N2—C22—C231.9 (3)C71—N52—C72—C730.8 (3)
C24—N4—C22—N2179.4 (2)C74—N54—C72—N52179.4 (2)
C25—N4—C22—N22.7 (4)C75—N54—C72—N520.1 (4)
C24—N4—C22—C230.2 (3)C74—N54—C72—C730.8 (2)
C25—N4—C22—C23176.9 (2)C75—N54—C72—C73179.7 (2)
N2—C22—C23—N3179.7 (2)N52—C72—C73—N53179.3 (2)
N4—C22—C23—N30.1 (3)N54—C72—C73—N531.0 (3)
N2—C22—C23—C205.0 (4)N52—C72—C73—C703.8 (3)
N4—C22—C23—C20174.6 (2)N54—C72—C73—C70176.0 (2)
C24—N3—C23—C220.4 (3)C74—N53—C73—C720.7 (3)
C24—N3—C23—C20173.2 (3)C74—N53—C73—C70175.6 (2)
N5—C20—C23—C22174.1 (2)N55—C70—C73—C72172.5 (2)
N1—C20—C23—C224.2 (3)N51—C70—C73—C724.4 (3)
N5—C20—C23—N30.8 (4)N55—C70—C73—N533.6 (4)
N1—C20—C23—N3177.5 (2)N51—C70—C73—N53179.5 (2)
C23—N3—C24—N40.5 (3)C73—N53—C74—N540.1 (3)
C22—N4—C24—N30.4 (3)C72—N54—C74—N530.4 (3)
C25—N4—C24—N3177.0 (2)C75—N54—C74—N53179.9 (2)
C24—N4—C25—C26111.6 (3)C72—N54—C75—C7776.2 (3)
C22—N4—C25—C2672.5 (3)C74—N54—C75—C77103.2 (3)
C24—N4—C25—C2713.0 (4)C72—N54—C75—C76158.6 (2)
C22—N4—C25—C27162.9 (3)C74—N54—C75—C7622.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N53i0.882.202.997 (3)150
N55—H55A···N3ii0.882.182.946 (3)145
C27—H27A···Cl1iii0.982.863.732 (3)149
C54—H54B···Cl51iv0.992.763.698 (3)158
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x+2, y+1/2, z+3/2; (iii) x+3, y, z+2; (iv) x1, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC27H32ClN5O
Mr478.03
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)15.8778 (5), 20.2779 (5), 15.2225 (5)
β (°) 104.233 (3)
V3)4750.7 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.50 × 0.40 × 0.30
Data collection
DiffractometerKuma KM-4 CCD
diffractometer
Absorption correctionMulti-scan
(Xcalibur; Oxford Diffraction, 2006)
Tmin, Tmax0.872, 0.944
No. of measured, independent and
observed [I > 2σ(I)] reflections
47831, 8353, 5567
Rint0.026
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.150, 1.09
No. of reflections8353
No. of parameters617
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.29

Computer programs: Xcalibur (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N53i0.882.202.997 (3)150.1
N55—H55A···N3ii0.882.182.946 (3)145.2
C27—H27A···Cl1iii0.982.863.732 (3)148.5
C54—H54B···Cl51iv0.992.763.698 (3)157.6
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x+2, y+1/2, z+3/2; (iii) x+3, y, z+2; (iv) x1, y+1/2, z1/2.
Comparative torsion angles (°) for selected 2,6,9-trisubstituted purines containing the 2-chloro 6-benzylamino and 9-isopropyl unit top
Compoundanglevalue(°)anglevalue(°)
NG38aC6—N6—C9—C10115.22 (13)H17—C17—N9—C4-13.38 (18)
CIBAP1bC6—N6—C9—C10178.97 (15)H16—C16—N9—C4-63.03 (2)
CIBAP2cC6—N6—C9—C10-117.35 (2)H16—C16—N9—C430.35 (3)
CIABAPdC20—N5—C19—C16100.28 (3)H25—C25—N4—C2245.01 (3)
CIABAPdC70—N55—C69—C66-99.62 (3)H75—C75—N54—C72-40.79 (3)
Notes: (a) Trávníček & Zatloukal (2004), where NG38 is N-[(2-azepan-1-yl)-9-isopropyl-9H-purin-6-yl]-4- methoxybenzylamine; (b) Trávníček & Popa (2007a), where CIBAP1 is 2-chloro-6-[(2,6-dimethoxybenzyl)amino]-9-isopropylpurine; (c) Trávníček & Popa (2007b), where CIBAP2 is 2-chloro-6-[(4-hydroxy-3,5-dimethoxybenzyl)amino]-9-isopropylpurine; (d) this work, where CIABAP is title compound (the structure consists of two crystallographically independent molecules).
 

Acknowledgements

The financial support of this work by the Science Foundation of the Czech Republic (grant No. 203/06/P362) and by the Czech Ministry of Education (project No. MSM 7088352101) is gratefully acknowledged.

References

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Volume 65| Part 2| February 2009| Pages o298-o299
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