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organic compounds
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
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 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). 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
Crystal data
|
Refinement
|
|
|
Data collection: Xcalibur (Oxford Diffraction, 2006); cell Xcalibur; data reduction: Xcalibur; 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.
Supporting information
10.1107/S160053680900052X/pk2141sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680900052X/pk2141Isup2.hkl
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
(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.Data collection: Xcalibur (Oxford Diffraction, 2006); cell
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).C27H32ClN5O | F(000) = 2032 |
Mr = 478.03 | Dx = 1.337 Mg m−3 |
Monoclinic, P21/c | Melting point: 148 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.8778 (5) Å | Cell parameters from 8353 reflections |
b = 20.2779 (5) Å | θ = 2.8–25.0° |
c = 15.2225 (5) Å | µ = 0.19 mm−1 |
β = 104.233 (3)° | T = 120 K |
V = 4750.7 (3) Å3 | Block, yellow |
Z = 8 | 0.50 × 0.40 × 0.30 mm |
Kuma KM-4 CCD diffractometer | 8353 independent reflections |
Radiation source: fine-focus sealed tube | 5567 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 0.06 pixels mm-1 | θmax = 25.0°, θmin = 2.8° |
ω scans | h = −16→18 |
Absorption correction: multi-scan (Xcalibur; Oxford Diffraction, 2006) | k = −24→23 |
Tmin = 0.872, Tmax = 0.944 | l = −18→18 |
47831 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-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 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C27H32ClN5O | V = 4750.7 (3) Å3 |
Mr = 478.03 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.8778 (5) Å | µ = 0.19 mm−1 |
b = 20.2779 (5) Å | T = 120 K |
c = 15.2225 (5) Å | 0.50 × 0.40 × 0.30 mm |
β = 104.233 (3)° |
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 = 0.944 | Rint = 0.026 |
47831 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.35 e Å−3 |
8353 reflections | Δρmin = −0.29 e Å−3 |
617 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 1.54371 (4) | 0.16850 (4) | 1.01111 (5) | 0.0416 (2) | |
O1 | 1.15991 (12) | 0.38506 (9) | 0.65047 (14) | 0.0418 (5) | |
N1 | 1.39808 (13) | 0.11570 (10) | 0.92710 (14) | 0.0265 (5) | |
N2 | 1.53027 (13) | 0.05913 (10) | 0.92127 (14) | 0.0278 (5) | |
N4 | 1.50180 (14) | −0.04121 (10) | 0.83228 (14) | 0.0289 (5) | |
N3 | 1.35644 (14) | −0.03462 (10) | 0.78459 (15) | 0.0306 (5) | |
N5 | 1.26108 (13) | 0.07666 (10) | 0.85571 (14) | 0.0261 (5) | |
H5A | 1.2293 | 0.0495 | 0.8159 | 0.031* | |
C1 | 0.95337 (16) | 0.38700 (11) | 0.59602 (15) | 0.0222 (5) | |
C2 | 0.98831 (16) | 0.39531 (12) | 0.51181 (17) | 0.0269 (6) | |
H2B | 1.0340 | 0.3620 | 0.5123 | 0.032* | |
H2C | 1.0147 | 0.4396 | 0.5122 | 0.032* | |
C3 | 0.91501 (17) | 0.38722 (12) | 0.42610 (17) | 0.0281 (6) | |
H3A | 0.9391 | 0.3929 | 0.3717 | 0.034* | |
C4 | 0.84508 (17) | 0.43886 (13) | 0.42383 (18) | 0.0321 (6) | |
H4B | 0.7976 | 0.4333 | 0.3684 | 0.038* | |
H4C | 0.8699 | 0.4836 | 0.4228 | 0.038* | |
C5 | 0.80936 (17) | 0.43108 (13) | 0.50779 (17) | 0.0285 (6) | |
H5B | 0.7636 | 0.4651 | 0.5070 | 0.034* | |
C6 | 0.77037 (17) | 0.36252 (13) | 0.50670 (17) | 0.0302 (6) | |
H6A | 0.7225 | 0.3571 | 0.4516 | 0.036* | |
H6B | 0.7461 | 0.3569 | 0.5602 | 0.036* | |
C7 | 0.83958 (17) | 0.31037 (13) | 0.50795 (17) | 0.0282 (6) | |
H7A | 0.8132 | 0.2656 | 0.5074 | 0.034* | |
C8 | 0.91320 (16) | 0.31812 (12) | 0.59364 (16) | 0.0254 (6) | |
H8A | 0.9583 | 0.2842 | 0.5944 | 0.030* | |
H8B | 0.8902 | 0.3117 | 0.6479 | 0.030* | |
C9 | 0.87618 (17) | 0.31819 (13) | 0.42455 (17) | 0.0308 (6) | |
H9A | 0.9215 | 0.2845 | 0.4253 | 0.037* | |
H9B | 0.8294 | 0.3121 | 0.3687 | 0.037* | |
C10 | 0.88214 (17) | 0.43880 (12) | 0.59306 (17) | 0.0284 (6) | |
H10A | 0.8584 | 0.4338 | 0.6470 | 0.034* | |
H10B | 0.9075 | 0.4835 | 0.5946 | 0.034* | |
C11 | 1.02429 (17) | 0.39841 (12) | 0.68438 (17) | 0.0291 (6) | |
H11A | 1.0369 | 0.4462 | 0.6908 | 0.035* | |
H11B | 1.0011 | 0.3847 | 0.7363 | 0.035* | |
C12 | 1.10835 (17) | 0.36200 (13) | 0.68945 (17) | 0.0287 (6) | |
C13 | 1.12982 (16) | 0.29932 (12) | 0.74137 (16) | 0.0258 (6) | |
C14 | 1.20554 (18) | 0.26697 (13) | 0.73665 (18) | 0.0331 (6) | |
H14A | 1.2396 | 0.2843 | 0.6987 | 0.040* | |
C15 | 1.23249 (17) | 0.21078 (13) | 0.78510 (18) | 0.0327 (6) | |
H15A | 1.2847 | 0.1898 | 0.7804 | 0.039* | |
C16 | 1.18432 (16) | 0.18431 (12) | 0.84080 (16) | 0.0240 (5) | |
C17 | 1.10862 (16) | 0.21535 (13) | 0.84536 (17) | 0.0279 (6) | |
H17A | 1.0745 | 0.1974 | 0.8828 | 0.033* | |
C18 | 1.08111 (16) | 0.27234 (12) | 0.79635 (17) | 0.0280 (6) | |
H18A | 1.0285 | 0.2930 | 0.8005 | 0.034* | |
C19 | 1.21638 (16) | 0.12463 (12) | 0.89844 (17) | 0.0263 (6) | |
H19A | 1.2563 | 0.1394 | 0.9557 | 0.032* | |
H19B | 1.1662 | 0.1029 | 0.9140 | 0.032* | |
C20 | 1.34751 (16) | 0.07103 (12) | 0.87280 (15) | 0.0228 (5) | |
C21 | 1.48320 (16) | 0.10626 (13) | 0.94474 (16) | 0.0275 (6) | |
C22 | 1.47769 (16) | 0.01555 (12) | 0.86771 (16) | 0.0246 (6) | |
C23 | 1.38849 (16) | 0.01919 (12) | 0.83828 (17) | 0.0255 (6) | |
C24 | 1.42650 (18) | −0.06881 (13) | 0.78385 (19) | 0.0333 (6) | |
H24A | 1.4248 | −0.1094 | 0.7522 | 0.040* | |
C25 | 1.59119 (17) | −0.06731 (13) | 0.84933 (18) | 0.0326 (6) | |
H25A | 1.6181 | −0.0638 | 0.9158 | 0.039* | |
C26 | 1.64435 (18) | −0.02650 (14) | 0.8010 (2) | 0.0389 (7) | |
H26A | 1.6197 | −0.0295 | 0.7355 | 0.058* | |
H26B | 1.7043 | −0.0428 | 0.8157 | 0.058* | |
H26C | 1.6438 | 0.0196 | 0.8202 | 0.058* | |
C27 | 1.5911 (2) | −0.13913 (15) | 0.8235 (3) | 0.0566 (10) | |
H27A | 1.5524 | −0.1637 | 0.8528 | 0.085* | |
H27B | 1.6502 | −0.1568 | 0.8433 | 0.085* | |
H27C | 1.5706 | −0.1435 | 0.7575 | 0.085* | |
Cl51 | 1.06711 (4) | 0.32556 (3) | 1.02370 (4) | 0.03138 (18) | |
O51 | 0.65672 (14) | 0.16100 (11) | 0.55786 (14) | 0.0508 (6) | |
N51 | 0.92396 (13) | 0.37756 (10) | 0.93336 (13) | 0.0251 (5) | |
N52 | 1.05595 (13) | 0.43726 (10) | 0.93901 (13) | 0.0231 (5) | |
N53 | 0.88368 (13) | 0.53117 (10) | 0.79834 (13) | 0.0237 (5) | |
N54 | 1.02812 (13) | 0.53960 (10) | 0.85313 (13) | 0.0223 (5) | |
N55 | 0.78821 (13) | 0.41714 (10) | 0.86172 (13) | 0.0264 (5) | |
H55A | 0.7566 | 0.4474 | 0.8274 | 0.032* | |
C51 | 0.47184 (16) | 0.11567 (12) | 0.58865 (16) | 0.0259 (6) | |
C52 | 0.43209 (18) | 0.16706 (13) | 0.63953 (18) | 0.0326 (6) | |
H52B | 0.4403 | 0.1533 | 0.7035 | 0.039* | |
H52C | 0.4618 | 0.2099 | 0.6388 | 0.039* | |
C53 | 0.33568 (18) | 0.17478 (14) | 0.5956 (2) | 0.0370 (7) | |
H53B | 0.3103 | 0.2083 | 0.6298 | 0.044* | |
C54 | 0.2906 (2) | 0.10865 (16) | 0.5982 (2) | 0.0478 (8) | |
H54A | 0.2991 | 0.0938 | 0.6617 | 0.057* | |
H54B | 0.2274 | 0.1133 | 0.5712 | 0.057* | |
C55 | 0.3289 (2) | 0.05839 (15) | 0.5449 (2) | 0.0496 (8) | |
H55B | 0.2988 | 0.0151 | 0.5453 | 0.060* | |
C56 | 0.3168 (2) | 0.08135 (18) | 0.4476 (2) | 0.0605 (10) | |
H56A | 0.3407 | 0.0479 | 0.4129 | 0.073* | |
H56B | 0.2541 | 0.0867 | 0.4188 | 0.073* | |
C57 | 0.3632 (2) | 0.14650 (17) | 0.44614 (19) | 0.0457 (8) | |
H57A | 0.3556 | 0.1613 | 0.3820 | 0.055* | |
C58 | 0.45957 (18) | 0.13811 (15) | 0.49055 (18) | 0.0373 (7) | |
H58A | 0.4901 | 0.1805 | 0.4890 | 0.045* | |
H58B | 0.4849 | 0.1050 | 0.4567 | 0.045* | |
C59 | 0.3243 (2) | 0.19791 (16) | 0.49812 (19) | 0.0437 (8) | |
H59A | 0.3539 | 0.2408 | 0.4973 | 0.052* | |
H59B | 0.2618 | 0.2039 | 0.4690 | 0.052* | |
C60 | 0.42482 (18) | 0.05001 (13) | 0.5893 (2) | 0.0380 (7) | |
H60A | 0.4500 | 0.0164 | 0.5560 | 0.046* | |
H60B | 0.4324 | 0.0347 | 0.6525 | 0.046* | |
C61 | 0.56868 (17) | 0.10361 (13) | 0.63550 (19) | 0.0329 (6) | |
H61A | 0.5739 | 0.0958 | 0.7008 | 0.039* | |
H61B | 0.5877 | 0.0629 | 0.6101 | 0.039* | |
C62 | 0.62922 (17) | 0.15816 (14) | 0.62633 (19) | 0.0344 (7) | |
C63 | 0.65636 (16) | 0.20984 (13) | 0.69797 (17) | 0.0279 (6) | |
C68 | 0.62858 (17) | 0.21168 (13) | 0.77775 (17) | 0.0311 (6) | |
H68A | 0.5905 | 0.1786 | 0.7895 | 0.037* | |
C67 | 0.65643 (17) | 0.26183 (13) | 0.84013 (17) | 0.0294 (6) | |
H67A | 0.6364 | 0.2632 | 0.8940 | 0.035* | |
C66 | 0.71300 (16) | 0.30974 (12) | 0.82460 (16) | 0.0247 (6) | |
C65 | 0.74072 (16) | 0.30712 (13) | 0.74527 (17) | 0.0281 (6) | |
H65A | 0.7795 | 0.3399 | 0.7339 | 0.034* | |
C64 | 0.71310 (17) | 0.25799 (13) | 0.68273 (17) | 0.0295 (6) | |
H64A | 0.7330 | 0.2570 | 0.6288 | 0.035* | |
C69 | 0.74333 (17) | 0.36378 (13) | 0.89382 (16) | 0.0276 (6) | |
H69A | 0.6923 | 0.3819 | 0.9120 | 0.033* | |
H69B | 0.7826 | 0.3443 | 0.9484 | 0.033* | |
C70 | 0.87432 (15) | 0.42347 (11) | 0.88074 (15) | 0.0218 (5) | |
C71 | 1.00903 (16) | 0.38826 (12) | 0.95686 (15) | 0.0230 (5) | |
C72 | 1.00400 (16) | 0.48160 (11) | 0.88524 (15) | 0.0216 (5) | |
C73 | 0.91542 (16) | 0.47738 (11) | 0.85193 (15) | 0.0214 (5) | |
C74 | 0.95342 (16) | 0.56661 (12) | 0.80151 (16) | 0.0259 (6) | |
H74A | 0.9521 | 0.6075 | 0.7706 | 0.031* | |
C75 | 1.11732 (16) | 0.56615 (12) | 0.87100 (16) | 0.0250 (6) | |
H75A | 1.1462 | 0.5577 | 0.9362 | 0.030* | |
C76 | 1.11638 (17) | 0.63973 (12) | 0.85592 (18) | 0.0311 (6) | |
H76A | 1.0919 | 0.6492 | 0.7916 | 0.047* | |
H76B | 1.1759 | 0.6568 | 0.8743 | 0.047* | |
H76C | 1.0808 | 0.6609 | 0.8921 | 0.047* | |
C77 | 1.16747 (17) | 0.52945 (13) | 0.81434 (18) | 0.0308 (6) | |
H77A | 1.1671 | 0.4822 | 0.8277 | 0.046* | |
H77B | 1.2275 | 0.5455 | 0.8285 | 0.046* | |
H77C | 1.1404 | 0.5368 | 0.7500 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0251 (4) | 0.0477 (4) | 0.0511 (4) | −0.0055 (3) | 0.0075 (3) | −0.0211 (3) |
O1 | 0.0265 (11) | 0.0396 (12) | 0.0568 (13) | −0.0032 (9) | 0.0051 (10) | 0.0171 (10) |
N1 | 0.0216 (12) | 0.0287 (12) | 0.0294 (11) | 0.0004 (9) | 0.0067 (9) | 0.0004 (9) |
N2 | 0.0225 (12) | 0.0299 (12) | 0.0305 (11) | 0.0001 (9) | 0.0057 (9) | 0.0000 (9) |
N4 | 0.0235 (12) | 0.0237 (11) | 0.0394 (12) | 0.0046 (9) | 0.0079 (10) | 0.0022 (9) |
N3 | 0.0285 (13) | 0.0233 (12) | 0.0387 (12) | 0.0021 (9) | 0.0055 (10) | 0.0002 (10) |
N5 | 0.0201 (12) | 0.0246 (11) | 0.0319 (11) | 0.0002 (9) | 0.0030 (9) | −0.0023 (9) |
C1 | 0.0228 (13) | 0.0199 (12) | 0.0232 (12) | 0.0009 (10) | 0.0045 (10) | −0.0027 (10) |
C2 | 0.0238 (14) | 0.0245 (14) | 0.0326 (14) | −0.0020 (11) | 0.0074 (11) | 0.0031 (11) |
C3 | 0.0293 (15) | 0.0328 (15) | 0.0232 (12) | −0.0005 (11) | 0.0081 (11) | 0.0013 (11) |
C4 | 0.0291 (15) | 0.0322 (15) | 0.0337 (14) | −0.0007 (12) | 0.0055 (12) | 0.0043 (12) |
C5 | 0.0252 (14) | 0.0265 (14) | 0.0324 (14) | 0.0075 (11) | 0.0043 (11) | −0.0013 (11) |
C6 | 0.0226 (14) | 0.0416 (16) | 0.0271 (13) | −0.0001 (12) | 0.0072 (11) | 0.0015 (12) |
C7 | 0.0285 (15) | 0.0241 (13) | 0.0314 (14) | −0.0054 (11) | 0.0061 (11) | −0.0007 (11) |
C8 | 0.0265 (14) | 0.0230 (13) | 0.0277 (13) | 0.0006 (11) | 0.0088 (11) | 0.0028 (10) |
C9 | 0.0271 (15) | 0.0347 (15) | 0.0276 (13) | 0.0001 (12) | 0.0010 (11) | −0.0084 (11) |
C10 | 0.0310 (15) | 0.0253 (14) | 0.0281 (13) | 0.0049 (11) | 0.0060 (11) | −0.0057 (11) |
C11 | 0.0306 (15) | 0.0243 (13) | 0.0285 (13) | 0.0017 (11) | 0.0000 (11) | −0.0031 (11) |
C12 | 0.0242 (14) | 0.0283 (14) | 0.0297 (13) | −0.0047 (11) | −0.0007 (11) | −0.0025 (11) |
C13 | 0.0252 (14) | 0.0241 (13) | 0.0263 (13) | −0.0019 (11) | 0.0027 (11) | −0.0048 (10) |
C14 | 0.0313 (16) | 0.0327 (15) | 0.0393 (15) | −0.0010 (12) | 0.0165 (12) | 0.0056 (12) |
C15 | 0.0236 (14) | 0.0309 (15) | 0.0462 (16) | 0.0043 (11) | 0.0137 (12) | 0.0078 (12) |
C16 | 0.0202 (13) | 0.0271 (13) | 0.0237 (12) | −0.0045 (10) | 0.0034 (10) | −0.0063 (10) |
C17 | 0.0248 (14) | 0.0332 (15) | 0.0286 (13) | 0.0004 (11) | 0.0122 (11) | 0.0025 (11) |
C18 | 0.0206 (13) | 0.0294 (14) | 0.0336 (14) | 0.0041 (11) | 0.0061 (11) | −0.0032 (11) |
C19 | 0.0218 (14) | 0.0282 (14) | 0.0296 (13) | 0.0033 (11) | 0.0074 (11) | 0.0003 (11) |
C20 | 0.0247 (14) | 0.0213 (13) | 0.0220 (12) | 0.0000 (10) | 0.0051 (10) | 0.0034 (10) |
C21 | 0.0226 (14) | 0.0333 (15) | 0.0256 (13) | −0.0025 (11) | 0.0039 (11) | −0.0014 (11) |
C22 | 0.0268 (15) | 0.0218 (13) | 0.0254 (12) | 0.0033 (11) | 0.0066 (11) | 0.0032 (10) |
C23 | 0.0219 (14) | 0.0245 (13) | 0.0307 (13) | 0.0008 (10) | 0.0073 (11) | 0.0058 (11) |
C24 | 0.0314 (16) | 0.0229 (14) | 0.0441 (16) | 0.0010 (12) | 0.0063 (13) | −0.0036 (12) |
C25 | 0.0267 (15) | 0.0363 (15) | 0.0357 (14) | 0.0108 (12) | 0.0097 (12) | 0.0078 (12) |
C26 | 0.0286 (16) | 0.0364 (16) | 0.0519 (18) | 0.0054 (12) | 0.0101 (13) | 0.0125 (13) |
C27 | 0.047 (2) | 0.0323 (17) | 0.104 (3) | 0.0129 (15) | 0.044 (2) | 0.0069 (17) |
Cl51 | 0.0289 (4) | 0.0282 (4) | 0.0354 (4) | 0.0007 (3) | 0.0048 (3) | 0.0088 (3) |
O51 | 0.0413 (13) | 0.0690 (15) | 0.0482 (13) | −0.0183 (11) | 0.0224 (11) | −0.0241 (11) |
N51 | 0.0265 (12) | 0.0255 (11) | 0.0229 (10) | −0.0025 (9) | 0.0055 (9) | 0.0000 (9) |
N52 | 0.0223 (11) | 0.0235 (11) | 0.0227 (10) | −0.0015 (9) | 0.0042 (9) | −0.0004 (8) |
N53 | 0.0227 (12) | 0.0232 (11) | 0.0243 (10) | −0.0024 (9) | 0.0041 (9) | 0.0010 (8) |
N54 | 0.0200 (11) | 0.0224 (11) | 0.0240 (10) | −0.0027 (8) | 0.0044 (9) | 0.0007 (8) |
N55 | 0.0247 (12) | 0.0270 (12) | 0.0273 (11) | −0.0024 (9) | 0.0060 (9) | 0.0043 (9) |
C51 | 0.0247 (14) | 0.0229 (13) | 0.0295 (13) | −0.0003 (10) | 0.0053 (11) | −0.0010 (10) |
C52 | 0.0335 (16) | 0.0294 (15) | 0.0335 (14) | 0.0035 (12) | 0.0057 (12) | −0.0011 (11) |
C53 | 0.0293 (16) | 0.0377 (16) | 0.0448 (16) | 0.0082 (12) | 0.0106 (13) | −0.0017 (13) |
C54 | 0.0282 (17) | 0.056 (2) | 0.061 (2) | 0.0011 (14) | 0.0141 (15) | 0.0089 (16) |
C55 | 0.0321 (18) | 0.0376 (18) | 0.079 (2) | −0.0115 (14) | 0.0124 (16) | −0.0095 (16) |
C56 | 0.039 (2) | 0.074 (3) | 0.057 (2) | 0.0038 (17) | −0.0099 (16) | −0.0293 (18) |
C57 | 0.0411 (18) | 0.066 (2) | 0.0263 (14) | 0.0110 (16) | 0.0002 (13) | 0.0028 (14) |
C58 | 0.0352 (17) | 0.0457 (18) | 0.0331 (15) | 0.0060 (13) | 0.0123 (13) | 0.0005 (13) |
C59 | 0.0400 (18) | 0.0469 (18) | 0.0419 (17) | 0.0134 (14) | 0.0056 (14) | 0.0094 (14) |
C60 | 0.0375 (17) | 0.0240 (14) | 0.0537 (18) | −0.0033 (12) | 0.0132 (14) | −0.0003 (13) |
C61 | 0.0313 (16) | 0.0275 (14) | 0.0383 (15) | 0.0053 (12) | 0.0054 (12) | −0.0024 (12) |
C62 | 0.0217 (15) | 0.0425 (17) | 0.0372 (16) | 0.0028 (12) | 0.0038 (12) | −0.0049 (12) |
C63 | 0.0238 (14) | 0.0313 (14) | 0.0272 (13) | 0.0070 (11) | 0.0037 (11) | 0.0027 (11) |
C68 | 0.0257 (14) | 0.0309 (15) | 0.0338 (14) | −0.0035 (11) | 0.0018 (11) | 0.0078 (12) |
C67 | 0.0257 (14) | 0.0353 (15) | 0.0266 (13) | −0.0043 (11) | 0.0051 (11) | 0.0058 (11) |
C66 | 0.0206 (13) | 0.0250 (13) | 0.0253 (12) | 0.0034 (10) | −0.0008 (10) | 0.0060 (10) |
C65 | 0.0245 (14) | 0.0282 (14) | 0.0336 (14) | 0.0004 (11) | 0.0108 (11) | 0.0031 (11) |
C64 | 0.0280 (15) | 0.0327 (15) | 0.0302 (14) | 0.0014 (11) | 0.0116 (12) | 0.0020 (11) |
C69 | 0.0245 (14) | 0.0345 (15) | 0.0238 (12) | −0.0065 (11) | 0.0058 (11) | 0.0051 (11) |
C70 | 0.0215 (14) | 0.0234 (13) | 0.0212 (12) | −0.0024 (10) | 0.0066 (10) | −0.0054 (10) |
C71 | 0.0253 (14) | 0.0236 (13) | 0.0200 (12) | −0.0011 (10) | 0.0051 (10) | −0.0001 (10) |
C72 | 0.0254 (14) | 0.0221 (13) | 0.0184 (11) | −0.0007 (10) | 0.0073 (10) | −0.0032 (10) |
C73 | 0.0242 (14) | 0.0222 (13) | 0.0188 (11) | −0.0017 (10) | 0.0069 (10) | −0.0023 (10) |
C74 | 0.0261 (14) | 0.0246 (13) | 0.0266 (13) | −0.0002 (11) | 0.0056 (11) | 0.0002 (10) |
C75 | 0.0211 (14) | 0.0286 (14) | 0.0245 (12) | −0.0043 (10) | 0.0038 (10) | 0.0029 (10) |
C76 | 0.0277 (15) | 0.0275 (14) | 0.0384 (15) | −0.0088 (11) | 0.0087 (12) | −0.0009 (12) |
C77 | 0.0246 (15) | 0.0313 (15) | 0.0363 (15) | −0.0017 (11) | 0.0069 (12) | 0.0018 (11) |
Cl1—C21 | 1.749 (3) | Cl51—C71 | 1.744 (2) |
O1—C12 | 1.217 (3) | O51—C62 | 1.226 (3) |
N1—C21 | 1.326 (3) | N51—C71 | 1.327 (3) |
N1—C20 | 1.350 (3) | N51—C70 | 1.349 (3) |
N2—C21 | 1.316 (3) | N52—C71 | 1.310 (3) |
N2—C22 | 1.345 (3) | N52—C72 | 1.351 (3) |
N4—C24 | 1.361 (3) | N53—C74 | 1.311 (3) |
N4—C22 | 1.365 (3) | N53—C73 | 1.381 (3) |
N4—C25 | 1.477 (3) | N54—C72 | 1.364 (3) |
N3—C24 | 1.313 (3) | N54—C74 | 1.366 (3) |
N3—C23 | 1.383 (3) | N54—C75 | 1.477 (3) |
N5—C20 | 1.337 (3) | N55—C70 | 1.332 (3) |
N5—C19 | 1.449 (3) | N55—C69 | 1.445 (3) |
N5—H5A | 0.8800 | N55—H55A | 0.8800 |
C1—C2 | 1.526 (3) | C51—C52 | 1.525 (4) |
C1—C8 | 1.532 (3) | C51—C58 | 1.527 (4) |
C1—C10 | 1.536 (3) | C51—C60 | 1.528 (4) |
C1—C11 | 1.545 (3) | C51—C61 | 1.547 (4) |
C2—C3 | 1.529 (3) | C52—C53 | 1.521 (4) |
C2—H2B | 0.9900 | C52—H52B | 0.9900 |
C2—H2C | 0.9900 | C52—H52C | 0.9900 |
C3—C4 | 1.520 (4) | C53—C59 | 1.524 (4) |
C3—C9 | 1.527 (4) | C53—C54 | 1.525 (4) |
C3—H3A | 1.0000 | C53—H53B | 1.0000 |
C4—C5 | 1.528 (4) | C54—C55 | 1.520 (4) |
C4—H4B | 0.9900 | C54—H54A | 0.9900 |
C4—H4C | 0.9900 | C54—H54B | 0.9900 |
C5—C10 | 1.519 (3) | C55—C60 | 1.516 (4) |
C5—C6 | 1.520 (4) | C55—C56 | 1.518 (5) |
C5—H5B | 1.0000 | C55—H55B | 1.0000 |
C6—C7 | 1.522 (4) | C56—C57 | 1.515 (5) |
C6—H6A | 0.9900 | C56—H56A | 0.9900 |
C6—H6B | 0.9900 | C56—H56B | 0.9900 |
C7—C9 | 1.529 (4) | C57—C58 | 1.523 (4) |
C7—C8 | 1.531 (3) | C57—C59 | 1.528 (4) |
C7—H7A | 1.0000 | C57—H57A | 1.0000 |
C8—H8A | 0.9900 | C58—H58A | 0.9900 |
C8—H8B | 0.9900 | C58—H58B | 0.9900 |
C9—H9A | 0.9900 | C59—H59A | 0.9900 |
C9—H9B | 0.9900 | C59—H59B | 0.9900 |
C10—H10A | 0.9900 | C60—H60A | 0.9900 |
C10—H10B | 0.9900 | C60—H60B | 0.9900 |
C11—C12 | 1.511 (4) | C61—C62 | 1.494 (4) |
C11—H11A | 0.9900 | C61—H61A | 0.9900 |
C11—H11B | 0.9900 | C61—H61B | 0.9900 |
C12—C13 | 1.491 (4) | C62—C63 | 1.497 (4) |
C13—C18 | 1.384 (4) | C63—C64 | 1.386 (4) |
C13—C14 | 1.387 (4) | C63—C68 | 1.391 (4) |
C14—C15 | 1.368 (4) | C68—C67 | 1.387 (4) |
C14—H14A | 0.9500 | C68—H68A | 0.9500 |
C15—C16 | 1.382 (4) | C67—C66 | 1.383 (3) |
C15—H15A | 0.9500 | C67—H67A | 0.9500 |
C16—C17 | 1.374 (3) | C66—C65 | 1.384 (4) |
C16—C19 | 1.508 (3) | C66—C69 | 1.514 (3) |
C17—C18 | 1.386 (4) | C65—C64 | 1.373 (4) |
C17—H17A | 0.9500 | C65—H65A | 0.9500 |
C18—H18A | 0.9500 | C64—H64A | 0.9500 |
C19—H19A | 0.9900 | C69—H69A | 0.9900 |
C19—H19B | 0.9900 | C69—H69B | 0.9900 |
C20—C23 | 1.405 (3) | C70—C73 | 1.398 (3) |
C22—C23 | 1.378 (4) | C72—C73 | 1.375 (3) |
C24—H24A | 0.9500 | C74—H74A | 0.9500 |
C25—C26 | 1.498 (4) | C75—C77 | 1.507 (4) |
C25—C27 | 1.508 (4) | C75—C76 | 1.509 (3) |
C25—H25A | 1.0000 | C75—H75A | 1.0000 |
C26—H26A | 0.9800 | C76—H76A | 0.9800 |
C26—H26B | 0.9800 | C76—H76B | 0.9800 |
C26—H26C | 0.9800 | C76—H76C | 0.9800 |
C27—H27A | 0.9800 | C77—H77A | 0.9800 |
C27—H27B | 0.9800 | C77—H77B | 0.9800 |
C27—H27C | 0.9800 | C77—H77C | 0.9800 |
C21—N1—C20 | 116.8 (2) | C71—N51—C70 | 117.0 (2) |
C21—N2—C22 | 109.4 (2) | C71—N52—C72 | 109.7 (2) |
C24—N4—C22 | 105.5 (2) | C74—N53—C73 | 103.2 (2) |
C24—N4—C25 | 128.8 (2) | C72—N54—C74 | 105.7 (2) |
C22—N4—C25 | 125.7 (2) | C72—N54—C75 | 126.1 (2) |
C24—N3—C23 | 103.4 (2) | C74—N54—C75 | 128.1 (2) |
C20—N5—C19 | 124.2 (2) | C70—N55—C69 | 124.3 (2) |
C20—N5—H5A | 117.9 | C70—N55—H55A | 117.8 |
C19—N5—H5A | 117.9 | C69—N55—H55A | 117.8 |
C2—C1—C8 | 108.42 (19) | C52—C51—C58 | 108.9 (2) |
C2—C1—C10 | 108.5 (2) | C52—C51—C60 | 109.2 (2) |
C8—C1—C10 | 108.9 (2) | C58—C51—C60 | 108.7 (2) |
C2—C1—C11 | 112.2 (2) | C52—C51—C61 | 111.3 (2) |
C8—C1—C11 | 111.55 (19) | C58—C51—C61 | 111.8 (2) |
C10—C1—C11 | 107.27 (19) | C60—C51—C61 | 106.9 (2) |
C1—C2—C3 | 110.3 (2) | C53—C52—C51 | 110.2 (2) |
C1—C2—H2B | 109.6 | C53—C52—H52B | 109.6 |
C3—C2—H2B | 109.6 | C51—C52—H52B | 109.6 |
C1—C2—H2C | 109.6 | C53—C52—H52C | 109.6 |
C3—C2—H2C | 109.6 | C51—C52—H52C | 109.6 |
H2B—C2—H2C | 108.1 | H52B—C52—H52C | 108.1 |
C4—C3—C9 | 109.9 (2) | C52—C53—C59 | 109.0 (2) |
C4—C3—C2 | 110.1 (2) | C52—C53—C54 | 109.1 (2) |
C9—C3—C2 | 109.3 (2) | C59—C53—C54 | 110.6 (3) |
C4—C3—H3A | 109.1 | C52—C53—H53B | 109.4 |
C9—C3—H3A | 109.1 | C59—C53—H53B | 109.4 |
C2—C3—H3A | 109.1 | C54—C53—H53B | 109.4 |
C3—C4—C5 | 109.2 (2) | C55—C54—C53 | 108.9 (2) |
C3—C4—H4B | 109.8 | C55—C54—H54A | 109.9 |
C5—C4—H4B | 109.8 | C53—C54—H54A | 109.9 |
C3—C4—H4C | 109.8 | C55—C54—H54B | 109.9 |
C5—C4—H4C | 109.8 | C53—C54—H54B | 109.9 |
H4B—C4—H4C | 108.3 | H54A—C54—H54B | 108.3 |
C10—C5—C6 | 109.0 (2) | C60—C55—C56 | 110.0 (3) |
C10—C5—C4 | 110.1 (2) | C60—C55—C54 | 109.1 (3) |
C6—C5—C4 | 108.6 (2) | C56—C55—C54 | 110.1 (3) |
C10—C5—H5B | 109.7 | C60—C55—H55B | 109.2 |
C6—C5—H5B | 109.7 | C56—C55—H55B | 109.2 |
C4—C5—H5B | 109.7 | C54—C55—H55B | 109.2 |
C5—C6—C7 | 110.1 (2) | C57—C56—C55 | 109.7 (2) |
C5—C6—H6A | 109.6 | C57—C56—H56A | 109.7 |
C7—C6—H6A | 109.6 | C55—C56—H56A | 109.7 |
C5—C6—H6B | 109.6 | C57—C56—H56B | 109.7 |
C7—C6—H6B | 109.6 | C55—C56—H56B | 109.7 |
H6A—C6—H6B | 108.1 | H56A—C56—H56B | 108.2 |
C6—C7—C9 | 109.8 (2) | C56—C57—C58 | 109.6 (3) |
C6—C7—C8 | 109.7 (2) | C56—C57—C59 | 109.1 (3) |
C9—C7—C8 | 109.3 (2) | C58—C57—C59 | 109.6 (2) |
C6—C7—H7A | 109.4 | C56—C57—H57A | 109.5 |
C9—C7—H7A | 109.4 | C58—C57—H57A | 109.5 |
C8—C7—H7A | 109.4 | C59—C57—H57A | 109.5 |
C7—C8—C1 | 109.88 (19) | C57—C58—C51 | 109.9 (2) |
C7—C8—H8A | 109.7 | C57—C58—H58A | 109.7 |
C1—C8—H8A | 109.7 | C51—C58—H58A | 109.7 |
C7—C8—H8B | 109.7 | C57—C58—H58B | 109.7 |
C1—C8—H8B | 109.7 | C51—C58—H58B | 109.7 |
H8A—C8—H8B | 108.2 | H58A—C58—H58B | 108.2 |
C3—C9—C7 | 108.5 (2) | C53—C59—C57 | 109.1 (2) |
C3—C9—H9A | 110.0 | C53—C59—H59A | 109.9 |
C7—C9—H9A | 110.0 | C57—C59—H59A | 109.9 |
C3—C9—H9B | 110.0 | C53—C59—H59B | 109.9 |
C7—C9—H9B | 110.0 | C57—C59—H59B | 109.9 |
H9A—C9—H9B | 108.4 | H59A—C59—H59B | 108.3 |
C5—C10—C1 | 110.76 (19) | C55—C60—C51 | 109.8 (2) |
C5—C10—H10A | 109.5 | C55—C60—H60A | 109.7 |
C1—C10—H10A | 109.5 | C51—C60—H60A | 109.7 |
C5—C10—H10B | 109.5 | C55—C60—H60B | 109.7 |
C1—C10—H10B | 109.5 | C51—C60—H60B | 109.7 |
H10A—C10—H10B | 108.1 | H60A—C60—H60B | 108.2 |
C12—C11—C1 | 114.6 (2) | C62—C61—C51 | 115.4 (2) |
C12—C11—H11A | 108.6 | C62—C61—H61A | 108.4 |
C1—C11—H11A | 108.6 | C51—C61—H61A | 108.4 |
C12—C11—H11B | 108.6 | C62—C61—H61B | 108.4 |
C1—C11—H11B | 108.6 | C51—C61—H61B | 108.4 |
H11A—C11—H11B | 107.6 | H61A—C61—H61B | 107.5 |
O1—C12—C13 | 119.5 (2) | O51—C62—C61 | 119.1 (2) |
O1—C12—C11 | 118.6 (2) | O51—C62—C63 | 119.2 (3) |
C13—C12—C11 | 121.8 (2) | C61—C62—C63 | 121.8 (2) |
C18—C13—C14 | 117.7 (2) | C64—C63—C68 | 119.1 (2) |
C18—C13—C12 | 124.6 (2) | C64—C63—C62 | 117.0 (2) |
C14—C13—C12 | 117.6 (2) | C68—C63—C62 | 124.0 (2) |
C15—C14—C13 | 121.8 (2) | C67—C68—C63 | 120.1 (2) |
C15—C14—H14A | 119.1 | C67—C68—H68A | 120.0 |
C13—C14—H14A | 119.1 | C63—C68—H68A | 120.0 |
C14—C15—C16 | 120.5 (2) | C66—C67—C68 | 120.6 (2) |
C14—C15—H15A | 119.8 | C66—C67—H67A | 119.7 |
C16—C15—H15A | 119.8 | C68—C67—H67A | 119.7 |
C17—C16—C15 | 118.4 (2) | C67—C66—C65 | 118.8 (2) |
C17—C16—C19 | 120.8 (2) | C67—C66—C69 | 119.9 (2) |
C15—C16—C19 | 120.7 (2) | C65—C66—C69 | 121.3 (2) |
C16—C17—C18 | 121.2 (2) | C64—C65—C66 | 121.1 (2) |
C16—C17—H17A | 119.4 | C64—C65—H65A | 119.4 |
C18—C17—H17A | 119.4 | C66—C65—H65A | 119.4 |
C13—C18—C17 | 120.4 (2) | C65—C64—C63 | 120.3 (2) |
C13—C18—H18A | 119.8 | C65—C64—H64A | 119.8 |
C17—C18—H18A | 119.8 | C63—C64—H64A | 119.8 |
N5—C19—C16 | 114.2 (2) | N55—C69—C66 | 113.9 (2) |
N5—C19—H19A | 108.7 | N55—C69—H69A | 108.8 |
C16—C19—H19A | 108.7 | C66—C69—H69A | 108.8 |
N5—C19—H19B | 108.7 | N55—C69—H69B | 108.8 |
C16—C19—H19B | 108.7 | C66—C69—H69B | 108.8 |
H19A—C19—H19B | 107.6 | H69A—C69—H69B | 107.7 |
N5—C20—N1 | 119.3 (2) | N55—C70—N51 | 118.8 (2) |
N5—C20—C23 | 122.6 (2) | N55—C70—C73 | 122.7 (2) |
N1—C20—C23 | 118.1 (2) | N51—C70—C73 | 118.4 (2) |
N2—C21—N1 | 132.0 (2) | N52—C71—N51 | 131.4 (2) |
N2—C21—Cl1 | 114.40 (19) | N52—C71—Cl51 | 115.34 (18) |
N1—C21—Cl1 | 113.63 (19) | N51—C71—Cl51 | 113.28 (18) |
N2—C22—N4 | 126.9 (2) | N52—C72—N54 | 127.4 (2) |
N2—C22—C23 | 126.7 (2) | N52—C72—C73 | 126.8 (2) |
N4—C22—C23 | 106.4 (2) | N54—C72—C73 | 105.9 (2) |
C22—C23—N3 | 110.4 (2) | C72—C73—N53 | 111.1 (2) |
C22—C23—C20 | 116.9 (2) | C72—C73—C70 | 116.5 (2) |
N3—C23—C20 | 132.4 (2) | N53—C73—C70 | 132.3 (2) |
N3—C24—N4 | 114.3 (2) | N53—C74—N54 | 114.0 (2) |
N3—C24—H24A | 122.9 | N53—C74—H74A | 123.0 |
N4—C24—H24A | 122.9 | N54—C74—H74A | 123.0 |
N4—C25—C26 | 110.4 (2) | N54—C75—C77 | 109.4 (2) |
N4—C25—C27 | 111.2 (2) | N54—C75—C76 | 111.1 (2) |
C26—C25—C27 | 111.7 (2) | C77—C75—C76 | 112.8 (2) |
N4—C25—H25A | 107.8 | N54—C75—H75A | 107.8 |
C26—C25—H25A | 107.8 | C77—C75—H75A | 107.8 |
C27—C25—H25A | 107.8 | C76—C75—H75A | 107.8 |
C25—C26—H26A | 109.5 | C75—C76—H76A | 109.5 |
C25—C26—H26B | 109.5 | C75—C76—H76B | 109.5 |
H26A—C26—H26B | 109.5 | H76A—C76—H76B | 109.5 |
C25—C26—H26C | 109.5 | C75—C76—H76C | 109.5 |
H26A—C26—H26C | 109.5 | H76A—C76—H76C | 109.5 |
H26B—C26—H26C | 109.5 | H76B—C76—H76C | 109.5 |
C25—C27—H27A | 109.5 | C75—C77—H77A | 109.5 |
C25—C27—H27B | 109.5 | C75—C77—H77B | 109.5 |
H27A—C27—H27B | 109.5 | H77A—C77—H77B | 109.5 |
C25—C27—H27C | 109.5 | C75—C77—H77C | 109.5 |
H27A—C27—H27C | 109.5 | H77A—C77—H77C | 109.5 |
H27B—C27—H27C | 109.5 | H77B—C77—H77C | 109.5 |
C8—C1—C2—C3 | 59.4 (3) | C58—C51—C52—C53 | 59.9 (3) |
C10—C1—C2—C3 | −58.7 (3) | C60—C51—C52—C53 | −58.6 (3) |
C11—C1—C2—C3 | −177.0 (2) | C61—C51—C52—C53 | −176.4 (2) |
C1—C2—C3—C4 | 60.1 (3) | C51—C52—C53—C59 | −60.9 (3) |
C1—C2—C3—C9 | −60.8 (3) | C51—C52—C53—C54 | 59.9 (3) |
C9—C3—C4—C5 | 61.4 (3) | C52—C53—C54—C55 | −61.1 (3) |
C2—C3—C4—C5 | −59.2 (3) | C59—C53—C54—C55 | 58.7 (3) |
C3—C4—C5—C10 | 58.8 (3) | C53—C54—C55—C60 | 61.8 (3) |
C3—C4—C5—C6 | −60.5 (3) | C53—C54—C55—C56 | −59.0 (3) |
C10—C5—C6—C7 | −59.8 (3) | C60—C55—C56—C57 | −59.5 (3) |
C4—C5—C6—C7 | 60.1 (3) | C54—C55—C56—C57 | 60.7 (3) |
C5—C6—C7—C9 | −60.2 (3) | C55—C56—C57—C58 | 59.4 (3) |
C5—C6—C7—C8 | 59.9 (3) | C55—C56—C57—C59 | −60.7 (3) |
C6—C7—C8—C1 | −59.3 (3) | C56—C57—C58—C51 | −60.0 (3) |
C9—C7—C8—C1 | 61.1 (3) | C59—C57—C58—C51 | 59.7 (3) |
C2—C1—C8—C7 | −59.5 (3) | C52—C51—C58—C57 | −59.1 (3) |
C10—C1—C8—C7 | 58.3 (3) | C60—C51—C58—C57 | 59.8 (3) |
C11—C1—C8—C7 | 176.5 (2) | C61—C51—C58—C57 | 177.6 (2) |
C4—C3—C9—C7 | −60.3 (3) | C52—C53—C59—C57 | 60.5 (3) |
C2—C3—C9—C7 | 60.7 (3) | C54—C53—C59—C57 | −59.4 (3) |
C6—C7—C9—C3 | 59.3 (3) | C56—C57—C59—C53 | 59.8 (3) |
C8—C7—C9—C3 | −61.1 (3) | C58—C57—C59—C53 | −60.2 (3) |
C6—C5—C10—C1 | 59.7 (3) | C56—C55—C60—C51 | 59.9 (3) |
C4—C5—C10—C1 | −59.3 (3) | C54—C55—C60—C51 | −61.0 (3) |
C2—C1—C10—C5 | 58.6 (3) | C52—C51—C60—C55 | 59.0 (3) |
C8—C1—C10—C5 | −59.2 (3) | C58—C51—C60—C55 | −59.6 (3) |
C11—C1—C10—C5 | 180.0 (2) | C61—C51—C60—C55 | 179.5 (2) |
C2—C1—C11—C12 | −48.3 (3) | C52—C51—C61—C62 | −72.2 (3) |
C8—C1—C11—C12 | 73.5 (3) | C58—C51—C61—C62 | 49.8 (3) |
C10—C1—C11—C12 | −167.4 (2) | C60—C51—C61—C62 | 168.7 (2) |
C1—C11—C12—O1 | 80.4 (3) | C51—C61—C62—O51 | −83.7 (3) |
C1—C11—C12—C13 | −100.2 (3) | C51—C61—C62—C63 | 95.6 (3) |
O1—C12—C13—C18 | 172.5 (2) | O51—C62—C63—C64 | −1.0 (4) |
C11—C12—C13—C18 | −6.9 (4) | C61—C62—C63—C64 | 179.7 (2) |
O1—C12—C13—C14 | −5.2 (4) | O51—C62—C63—C68 | 179.4 (3) |
C11—C12—C13—C14 | 175.4 (2) | C61—C62—C63—C68 | 0.2 (4) |
C18—C13—C14—C15 | −0.8 (4) | C64—C63—C68—C67 | 1.1 (4) |
C12—C13—C14—C15 | 177.1 (2) | C62—C63—C68—C67 | −179.4 (2) |
C13—C14—C15—C16 | 0.0 (4) | C63—C68—C67—C66 | −1.1 (4) |
C14—C15—C16—C17 | 0.7 (4) | C68—C67—C66—C65 | 0.6 (4) |
C14—C15—C16—C19 | −176.5 (2) | C68—C67—C66—C69 | −179.5 (2) |
C15—C16—C17—C18 | −0.7 (4) | C67—C66—C65—C64 | −0.1 (4) |
C19—C16—C17—C18 | 176.4 (2) | C69—C66—C65—C64 | 179.9 (2) |
C14—C13—C18—C17 | 0.8 (4) | C66—C65—C64—C63 | 0.1 (4) |
C12—C13—C18—C17 | −176.9 (2) | C68—C63—C64—C65 | −0.6 (4) |
C16—C17—C18—C13 | 0.0 (4) | C62—C63—C64—C65 | 179.8 (2) |
C20—N5—C19—C16 | 100.3 (3) | C70—N55—C69—C66 | −99.6 (3) |
C17—C16—C19—N5 | 146.3 (2) | C67—C66—C69—N55 | −168.7 (2) |
C15—C16—C19—N5 | −36.6 (3) | C65—C66—C69—N55 | 11.3 (3) |
C19—N5—C20—N1 | −6.0 (3) | C69—N55—C70—N51 | 0.0 (3) |
C19—N5—C20—C23 | 172.3 (2) | C69—N55—C70—C73 | −177.0 (2) |
C21—N1—C20—N5 | 177.3 (2) | C71—N51—C70—N55 | −174.7 (2) |
C21—N1—C20—C23 | −1.1 (3) | C71—N51—C70—C73 | 2.3 (3) |
C22—N2—C21—N1 | 2.1 (4) | C72—N52—C71—N51 | −1.8 (4) |
C22—N2—C21—Cl1 | −177.54 (17) | C72—N52—C71—Cl51 | 178.53 (16) |
C20—N1—C21—N2 | −2.5 (4) | C70—N51—C71—N52 | 1.0 (4) |
C20—N1—C21—Cl1 | 177.14 (17) | C70—N51—C71—Cl51 | −179.33 (16) |
C21—N2—C22—N4 | −177.5 (2) | C71—N52—C72—N54 | 178.9 (2) |
C21—N2—C22—C23 | 1.9 (3) | C71—N52—C72—C73 | −0.8 (3) |
C24—N4—C22—N2 | 179.4 (2) | C74—N54—C72—N52 | 179.4 (2) |
C25—N4—C22—N2 | 2.7 (4) | C75—N54—C72—N52 | −0.1 (4) |
C24—N4—C22—C23 | −0.2 (3) | C74—N54—C72—C73 | −0.8 (2) |
C25—N4—C22—C23 | −176.9 (2) | C75—N54—C72—C73 | 179.7 (2) |
N2—C22—C23—N3 | −179.7 (2) | N52—C72—C73—N53 | −179.3 (2) |
N4—C22—C23—N3 | −0.1 (3) | N54—C72—C73—N53 | 1.0 (3) |
N2—C22—C23—C20 | −5.0 (4) | N52—C72—C73—C70 | 3.8 (3) |
N4—C22—C23—C20 | 174.6 (2) | N54—C72—C73—C70 | −176.0 (2) |
C24—N3—C23—C22 | 0.4 (3) | C74—N53—C73—C72 | −0.7 (3) |
C24—N3—C23—C20 | −173.2 (3) | C74—N53—C73—C70 | 175.6 (2) |
N5—C20—C23—C22 | −174.1 (2) | N55—C70—C73—C72 | 172.5 (2) |
N1—C20—C23—C22 | 4.2 (3) | N51—C70—C73—C72 | −4.4 (3) |
N5—C20—C23—N3 | −0.8 (4) | N55—C70—C73—N53 | −3.6 (4) |
N1—C20—C23—N3 | 177.5 (2) | N51—C70—C73—N53 | 179.5 (2) |
C23—N3—C24—N4 | −0.5 (3) | C73—N53—C74—N54 | 0.1 (3) |
C22—N4—C24—N3 | 0.4 (3) | C72—N54—C74—N53 | 0.4 (3) |
C25—N4—C24—N3 | 177.0 (2) | C75—N54—C74—N53 | 179.9 (2) |
C24—N4—C25—C26 | 111.6 (3) | C72—N54—C75—C77 | 76.2 (3) |
C22—N4—C25—C26 | −72.5 (3) | C74—N54—C75—C77 | −103.2 (3) |
C24—N4—C25—C27 | −13.0 (4) | C72—N54—C75—C76 | −158.6 (2) |
C22—N4—C25—C27 | 162.9 (3) | C74—N54—C75—C76 | 22.0 (3) |
D—H···A | D—H | H···A | D···A | 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−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+3, −y, −z+2; (iv) x−1, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C27H32ClN5O |
Mr | 478.03 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 15.8778 (5), 20.2779 (5), 15.2225 (5) |
β (°) | 104.233 (3) |
V (Å3) | 4750.7 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.50 × 0.40 × 0.30 |
Data collection | |
Diffractometer | Kuma KM-4 CCD diffractometer |
Absorption correction | Multi-scan (Xcalibur; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.872, 0.944 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 47831, 8353, 5567 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.150, 1.09 |
No. of reflections | 8353 |
No. of parameters | 617 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.29 |
Computer programs: Xcalibur (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···N53i | 0.88 | 2.20 | 2.997 (3) | 150.1 |
N55—H55A···N3ii | 0.88 | 2.18 | 2.946 (3) | 145.2 |
C27—H27A···Cl1iii | 0.98 | 2.86 | 3.732 (3) | 148.5 |
C54—H54B···Cl51iv | 0.99 | 2.76 | 3.698 (3) | 157.6 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+3, −y, −z+2; (iv) x−1, −y+1/2, z−1/2. |
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), 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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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.