(1-Adamant-yl){4-[(2-chloro-9-isopropyl-9H-purin-6-yl)aminometh-yl]phen-yl}methanone trichloro-methane solvate.

In the title compound, C(26)H(30)ClN(5)O·CHCl(3), the purine mol-ecule consists of essentially planar benzene and purine ring systems [maximum deviation 0.010 (4) Å for both ring systems] forming a dihedral angle of 85.52 (9)°. Inter-molecular N-H⋯N hydrogen bonds link adjacent mol-ecules into centrosymmetric dimers. The structure also contains inter-molecular C-H⋯O and C-H⋯N inter-actions. The benzene rings form offset face-to-face π-π stacking inter-actions with an inter-planar distance of 3.541 (4) Å and a centroid-to-centroid distance of 4.022 (4) Å.

Related literature

The title compound was prepared according to a modified literature procedure (Fiorini & Abel, 1998 ▶). For the synthesis and/or biological activity of related compounds, see: Legraverend & Grierson (2006 ▶); Long et al. (2007 ▶). For related structures, see: Trávníček & Kryštof (2004 ▶); Trávníček & Zatloukal (2004 ▶); Trávníček & Popa (2007a ▶,b ▶) Rouchal et al. (2009 ▶).

Experimental

Crystal data

C26H30ClN5O·CHCl3

M = 583.39

Orthorhombic,

a = 19.434 (12) Å

b = 13.186 (7) Å

c = 22.149 (11) Å

V = 5676 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.45 mm−1

T = 120 K

0.45 × 0.40 × 0.20 mm

Data collection

Kuma KM4 CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.738, T max = 0.917

32219 measured reflections

4984 independent reflections

2981 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.177

S = 1.12

4984 reflections

334 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016596/bi2361sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016596/bi2361Isup2.hkl

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

C26H30ClN5O·CHCl3	Dx = 1.365 Mg m−3
Mr = 583.39	Melting point: 191 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4984 reflections
a = 19.434 (12) Å	θ = 2.6–25.0°
b = 13.186 (7) Å	µ = 0.45 mm−1
c = 22.149 (11) Å	T = 120 K
V = 5676 (5) Å3	Block, colourless
Z = 8	0.45 × 0.40 × 0.20 mm
F(000) = 2432

Kuma KM4 CCD diffractometer	4984 independent reflections
Radiation source: fine-focus sealed tube	2981 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 0.06 pixels mm-1	θmax = 25.0°, θmin = 2.6°
ω scans	h = −23→21
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −15→15
Tmin = 0.738, Tmax = 0.917	l = −26→21
32219 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0729P)2 + 9.6676P] where P = (Fo2 + 2Fc2)/3
4984 reflections	(Δ/σ)max < 0.001
334 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

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	0.15090 (5)	0.68048 (7)	0.25476 (4)	0.0305 (3)
O1	0.13811 (13)	1.1399 (2)	0.50691 (13)	0.0320 (7)
N1	0.00385 (14)	0.6307 (2)	0.43338 (14)	0.0230 (7)
H1A	−0.0135	0.5931	0.4625	0.028*
N2	0.07497 (15)	0.6451 (2)	0.34920 (14)	0.0226 (7)
N3	0.15847 (14)	0.5170 (2)	0.32042 (13)	0.0217 (7)
N4	0.15553 (15)	0.3704 (2)	0.38744 (13)	0.0233 (7)
N5	0.07206 (15)	0.4204 (2)	0.45195 (14)	0.0256 (7)
C1	0.21373 (18)	1.0428 (3)	0.56796 (17)	0.0254 (9)
C2	0.2555 (2)	1.1416 (3)	0.56949 (19)	0.0307 (9)
H2B	0.2251	1.1982	0.5819	0.037*
H2C	0.2729	1.1566	0.5284	0.037*
C3	0.3165 (2)	1.1347 (3)	0.61349 (18)	0.0322 (10)
H3B	0.3428	1.2000	0.6132	0.039*
C4	0.2899 (2)	1.1132 (3)	0.67731 (19)	0.0355 (10)
H4A	0.2600	1.1696	0.6908	0.043*
H4B	0.3292	1.1080	0.7056	0.043*
C5	0.2487 (2)	1.0128 (3)	0.67746 (18)	0.0322 (10)
H5B	0.2315	0.9988	0.7192	0.039*
C6	0.2956 (2)	0.9260 (3)	0.65710 (19)	0.0361 (10)
H6A	0.2695	0.8615	0.6572	0.043*
H6B	0.3346	0.9192	0.6856	0.043*
C7	0.3232 (2)	0.9470 (3)	0.59318 (18)	0.0299 (9)
H7A	0.3539	0.8901	0.5805	0.036*
C8	0.26304 (19)	0.9563 (3)	0.54841 (17)	0.0270 (9)
H8A	0.2375	0.8914	0.5469	0.032*
H8B	0.2811	0.9705	0.5075	0.032*
C9	0.18688 (19)	1.0227 (3)	0.63391 (17)	0.0282 (9)
H9A	0.1570	1.0794	0.6469	0.034*
H9B	0.1593	0.9596	0.6347	0.034*
C10	0.3642 (2)	1.0465 (3)	0.59343 (19)	0.0340 (10)
H10A	0.3824	1.0603	0.5525	0.041*
H10B	0.4036	1.0408	0.6216	0.041*
C11	0.15273 (18)	1.0551 (3)	0.52472 (17)	0.0239 (9)
C12	0.10965 (18)	0.9675 (3)	0.50235 (17)	0.0243 (9)
C13	0.07214 (18)	0.9841 (3)	0.44859 (17)	0.0271 (9)
H13A	0.0749	1.0479	0.4288	0.033*
C14	0.03137 (19)	0.9082 (3)	0.42450 (18)	0.0300 (9)
H14A	0.0066	0.9209	0.3883	0.036*
C15	0.02571 (18)	0.8139 (3)	0.45191 (17)	0.0241 (8)
C16	0.06142 (19)	0.7977 (3)	0.50545 (18)	0.0282 (9)
H16A	0.0571	0.7345	0.5256	0.034*
C17	0.10368 (19)	0.8731 (3)	0.53013 (18)	0.0266 (9)
H17A	0.1285	0.8598	0.5662	0.032*
C18	−0.02097 (19)	0.7331 (3)	0.42573 (17)	0.0248 (9)
H18A	−0.0668	0.7388	0.4450	0.030*
H18B	−0.0270	0.7465	0.3821	0.030*
C19	0.05284 (17)	0.5906 (3)	0.39739 (16)	0.0206 (8)
C20	0.12500 (18)	0.6035 (3)	0.31567 (16)	0.0242 (9)
C21	0.13385 (17)	0.4650 (3)	0.36843 (16)	0.0213 (8)
C22	0.08232 (17)	0.4945 (3)	0.40833 (16)	0.0203 (8)
C23	0.11642 (19)	0.3486 (3)	0.43759 (17)	0.0251 (9)
H23A	0.1209	0.2874	0.4599	0.030*
C24	0.21277 (18)	0.3110 (3)	0.35970 (18)	0.0279 (9)
H24A	0.2129	0.3250	0.3153	0.033*
C25	0.2812 (2)	0.3476 (4)	0.3856 (2)	0.0502 (13)
H25A	0.2864	0.4203	0.3779	0.075*
H25B	0.3191	0.3106	0.3664	0.075*
H25C	0.2821	0.3352	0.4292	0.075*
C26	0.2007 (2)	0.1985 (3)	0.3687 (2)	0.0460 (12)
H26A	0.1564	0.1796	0.3508	0.069*
H26B	0.2001	0.1831	0.4120	0.069*
H26C	0.2377	0.1602	0.3491	0.069*
C27	0.5087 (2)	1.1979 (4)	0.7415 (2)	0.0520 (14)
H27A	0.4751	1.2334	0.7683	0.062*
Cl11	0.49438 (8)	1.06661 (13)	0.74624 (7)	0.0720 (5)
Cl12	0.49582 (6)	1.23926 (13)	0.66603 (5)	0.0630 (4)
Cl13	0.59279 (6)	1.22798 (13)	0.76534 (6)	0.0635 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0316 (5)	0.0309 (6)	0.0291 (5)	0.0028 (4)	0.0083 (4)	0.0085 (4)
O1	0.0316 (15)	0.0228 (15)	0.0416 (18)	0.0013 (12)	−0.0007 (12)	0.0059 (13)
N1	0.0249 (16)	0.0199 (17)	0.0242 (17)	−0.0002 (13)	0.0038 (13)	0.0003 (14)
N2	0.0203 (15)	0.0249 (17)	0.0224 (17)	0.0011 (13)	0.0007 (13)	0.0029 (14)
N3	0.0206 (15)	0.0228 (17)	0.0216 (17)	0.0001 (13)	0.0018 (13)	−0.0025 (14)
N4	0.0219 (16)	0.0286 (19)	0.0194 (17)	0.0041 (13)	0.0006 (13)	−0.0001 (14)
N5	0.0247 (16)	0.0278 (19)	0.0243 (18)	0.0027 (14)	−0.0008 (14)	−0.0014 (15)
C1	0.025 (2)	0.025 (2)	0.026 (2)	0.0004 (16)	0.0031 (16)	−0.0034 (17)
C2	0.033 (2)	0.026 (2)	0.033 (2)	−0.0035 (18)	0.0026 (18)	0.0040 (18)
C3	0.032 (2)	0.029 (2)	0.035 (2)	−0.0052 (18)	−0.0028 (18)	−0.0020 (19)
C4	0.040 (2)	0.035 (3)	0.031 (2)	−0.0030 (19)	0.0001 (19)	−0.0044 (19)
C5	0.038 (2)	0.031 (2)	0.027 (2)	−0.0051 (19)	0.0010 (18)	−0.0044 (19)
C6	0.041 (2)	0.032 (2)	0.035 (3)	−0.0031 (19)	−0.0089 (19)	0.000 (2)
C7	0.026 (2)	0.030 (2)	0.034 (2)	0.0021 (17)	0.0001 (17)	−0.0043 (18)
C8	0.027 (2)	0.027 (2)	0.027 (2)	0.0045 (17)	0.0045 (16)	−0.0048 (17)
C9	0.029 (2)	0.027 (2)	0.029 (2)	−0.0016 (17)	0.0082 (17)	−0.0007 (18)
C10	0.025 (2)	0.043 (3)	0.034 (2)	−0.0083 (19)	0.0008 (18)	−0.003 (2)
C11	0.0235 (19)	0.021 (2)	0.028 (2)	0.0037 (16)	0.0087 (16)	0.0004 (17)
C12	0.0178 (18)	0.021 (2)	0.034 (2)	0.0045 (15)	0.0049 (16)	−0.0014 (18)
C13	0.0251 (19)	0.026 (2)	0.030 (2)	0.0045 (17)	0.0018 (17)	0.0063 (18)
C14	0.025 (2)	0.037 (3)	0.029 (2)	0.0029 (18)	−0.0020 (17)	0.0032 (19)
C15	0.0221 (19)	0.025 (2)	0.025 (2)	0.0013 (16)	0.0078 (15)	−0.0009 (17)
C16	0.029 (2)	0.029 (2)	0.027 (2)	−0.0014 (17)	0.0030 (17)	0.0037 (18)
C17	0.029 (2)	0.022 (2)	0.029 (2)	−0.0009 (16)	−0.0039 (17)	0.0028 (17)
C18	0.0267 (19)	0.025 (2)	0.023 (2)	0.0044 (16)	0.0016 (16)	0.0000 (17)
C19	0.0153 (17)	0.021 (2)	0.025 (2)	−0.0035 (15)	−0.0049 (15)	−0.0059 (17)
C20	0.0238 (19)	0.028 (2)	0.021 (2)	0.0000 (16)	0.0008 (16)	0.0018 (17)
C21	0.0197 (18)	0.025 (2)	0.020 (2)	−0.0020 (15)	−0.0032 (15)	−0.0002 (17)
C22	0.0219 (18)	0.021 (2)	0.0178 (19)	−0.0035 (15)	−0.0017 (14)	−0.0018 (16)
C23	0.030 (2)	0.026 (2)	0.020 (2)	0.0019 (16)	0.0021 (16)	0.0025 (17)
C24	0.0207 (19)	0.037 (2)	0.026 (2)	0.0063 (17)	0.0015 (16)	−0.0011 (18)
C25	0.028 (2)	0.070 (4)	0.053 (3)	0.012 (2)	−0.006 (2)	−0.027 (3)
C26	0.048 (3)	0.036 (3)	0.054 (3)	0.011 (2)	0.023 (2)	0.007 (2)
C27	0.035 (2)	0.087 (4)	0.034 (3)	0.009 (3)	−0.003 (2)	−0.013 (3)
Cl11	0.0769 (10)	0.0811 (11)	0.0581 (9)	0.0080 (8)	0.0082 (7)	−0.0164 (8)
Cl12	0.0379 (7)	0.1163 (13)	0.0348 (7)	0.0103 (7)	−0.0040 (5)	−0.0052 (7)
Cl13	0.0324 (6)	0.1206 (13)	0.0377 (7)	0.0056 (7)	−0.0026 (5)	−0.0095 (7)

Cl1—C20	1.762 (4)	C8—H8A	0.990
O1—C11	1.219 (4)	C8—H8B	0.990
N1—C19	1.349 (5)	C9—H9A	0.990
N1—C18	1.445 (5)	C9—H9B	0.990
N1—H1A	0.880	C10—H10A	0.990
N2—C20	1.341 (5)	C10—H10B	0.990
N2—C19	1.357 (5)	C11—C12	1.511 (5)
N3—C20	1.316 (5)	C12—C17	1.392 (5)
N3—C21	1.353 (5)	C12—C13	1.413 (5)
N4—C23	1.376 (5)	C13—C14	1.384 (5)
N4—C21	1.383 (5)	C13—H13A	0.950
N4—C24	1.493 (5)	C14—C15	1.388 (5)
N5—C23	1.320 (5)	C14—H14A	0.950
N5—C22	1.388 (5)	C15—C16	1.390 (5)
C1—C11	1.532 (5)	C15—C18	1.515 (5)
C1—C2	1.535 (5)	C16—C17	1.401 (5)
C1—C8	1.552 (5)	C16—H16A	0.950
C1—C9	1.574 (5)	C17—H17A	0.950
C2—C3	1.538 (6)	C18—H18A	0.990
C2—H2B	0.990	C18—H18B	0.990
C2—H2C	0.990	C19—C22	1.411 (5)
C3—C4	1.531 (6)	C21—C22	1.391 (5)
C3—C10	1.551 (6)	C23—H23A	0.950
C3—H3B	1.000	C24—C26	1.515 (6)
C4—C5	1.548 (6)	C24—C25	1.526 (6)
C4—H4A	0.990	C24—H24A	1.000
C4—H4B	0.990	C25—H25A	0.980
C5—C6	1.531 (6)	C25—H25B	0.980
C5—C9	1.546 (6)	C25—H25C	0.980
C5—H5B	1.000	C26—H26A	0.980
C6—C7	1.539 (6)	C26—H26B	0.980
C6—H6A	0.990	C26—H26C	0.980
C6—H6B	0.990	C27—Cl11	1.756 (6)
C7—C10	1.535 (6)	C27—Cl13	1.763 (5)
C7—C8	1.537 (5)	C27—Cl12	1.775 (5)
C7—H7A	1.000	C27—H27A	1.000
C19—N1—C18	122.2 (3)	H10A—C10—H10B	108.2
C19—N1—H1A	118.9	O1—C11—C12	117.8 (3)
C18—N1—H1A	118.9	O1—C11—C1	118.7 (3)
C20—N2—C19	116.7 (3)	C12—C11—C1	123.5 (3)
C20—N3—C21	109.1 (3)	C17—C12—C13	117.9 (3)
C23—N4—C21	105.4 (3)	C17—C12—C11	125.8 (3)
C23—N4—C24	129.4 (3)	C13—C12—C11	116.3 (3)
C21—N4—C24	125.1 (3)	C14—C13—C12	120.5 (4)
C23—N5—C22	104.1 (3)	C14—C13—H13A	119.7
C11—C1—C2	109.4 (3)	C12—C13—H13A	119.7
C11—C1—C8	112.4 (3)	C13—C14—C15	121.7 (4)
C2—C1—C8	107.7 (3)	C13—C14—H14A	119.2
C11—C1—C9	110.0 (3)	C15—C14—H14A	119.2
C2—C1—C9	107.3 (3)	C14—C15—C16	118.1 (4)
C8—C1—C9	109.9 (3)	C14—C15—C18	120.7 (3)
C1—C2—C3	111.8 (3)	C16—C15—C18	121.2 (3)
C1—C2—H2B	109.3	C15—C16—C17	121.1 (4)
C3—C2—H2B	109.3	C15—C16—H16A	119.4
C1—C2—H2C	109.3	C17—C16—H16A	119.4
C3—C2—H2C	109.3	C12—C17—C16	120.7 (4)
H2B—C2—H2C	107.9	C12—C17—H17A	119.7
C4—C3—C2	109.6 (3)	C16—C17—H17A	119.7
C4—C3—C10	109.1 (3)	N1—C18—C15	114.4 (3)
C2—C3—C10	108.9 (3)	N1—C18—H18A	108.7
C4—C3—H3B	109.8	C15—C18—H18A	108.7
C2—C3—H3B	109.8	N1—C18—H18B	108.7
C10—C3—H3B	109.8	C15—C18—H18B	108.7
C3—C4—C5	109.6 (3)	H18A—C18—H18B	107.6
C3—C4—H4A	109.8	N1—C19—N2	118.8 (3)
C5—C4—H4A	109.8	N1—C19—C22	122.5 (3)
C3—C4—H4B	109.8	N2—C19—C22	118.8 (3)
C5—C4—H4B	109.8	N3—C20—N2	131.9 (3)
H4A—C4—H4B	108.2	N3—C20—Cl1	114.8 (3)
C6—C5—C9	110.0 (3)	N2—C20—Cl1	113.3 (3)
C6—C5—C4	109.3 (3)	N3—C21—N4	126.1 (3)
C9—C5—C4	109.2 (3)	N3—C21—C22	127.8 (3)
C6—C5—H5B	109.4	N4—C21—C22	106.1 (3)
C9—C5—H5B	109.4	N5—C22—C21	110.4 (3)
C4—C5—H5B	109.4	N5—C22—C19	133.8 (3)
C5—C6—C7	110.1 (3)	C21—C22—C19	115.7 (3)
C5—C6—H6A	109.6	N5—C23—N4	113.9 (3)
C7—C6—H6A	109.6	N5—C23—H23A	123.0
C5—C6—H6B	109.6	N4—C23—H23A	123.0
C7—C6—H6B	109.6	N4—C24—C26	110.1 (3)
H6A—C6—H6B	108.2	N4—C24—C25	109.2 (3)
C10—C7—C8	109.2 (3)	C26—C24—C25	113.3 (4)
C10—C7—C6	109.4 (3)	N4—C24—H24A	108.0
C8—C7—C6	110.0 (3)	C26—C24—H24A	108.0
C10—C7—H7A	109.4	C25—C24—H24A	108.0
C8—C7—H7A	109.4	C24—C25—H25A	109.5
C6—C7—H7A	109.4	C24—C25—H25B	109.5
C7—C8—C1	110.4 (3)	H25A—C25—H25B	109.5
C7—C8—H8A	109.6	C24—C25—H25C	109.5
C1—C8—H8A	109.6	H25A—C25—H25C	109.5
C7—C8—H8B	109.6	H25B—C25—H25C	109.5
C1—C8—H8B	109.6	C24—C26—H26A	109.5
H8A—C8—H8B	108.1	C24—C26—H26B	109.5
C5—C9—C1	109.6 (3)	H26A—C26—H26B	109.5
C5—C9—H9A	109.7	C24—C26—H26C	109.5
C1—C9—H9A	109.7	H26A—C26—H26C	109.5
C5—C9—H9B	109.7	H26B—C26—H26C	109.5
C1—C9—H9B	109.7	Cl11—C27—Cl13	110.5 (3)
H9A—C9—H9B	108.2	Cl11—C27—Cl12	109.7 (3)
C7—C10—C3	109.4 (3)	Cl13—C27—Cl12	110.1 (3)
C7—C10—H10A	109.8	Cl11—C27—H27A	108.8
C3—C10—H10A	109.8	Cl13—C27—H27A	108.8
C7—C10—H10B	109.8	Cl12—C27—H27A	108.8
C3—C10—H10B	109.8

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N5i	0.88	2.22	3.013 (5)	150
C27—H27A···N2ii	1.00	2.59	3.553 (6)	161
C5—H5B···N3iii	1.00	2.66	3.641 (5)	166
C23—H23A···O1iv	0.95	2.23	3.179 (5)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N5i	0.88	2.22	3.013 (5)	150
C27—H27A⋯N2ii	1.00	2.59	3.553 (6)	161
C5—H5B⋯N3iii	1.00	2.66	3.641 (5)	166
C23—H23A⋯O1iv	0.95	2.23	3.179 (5)	175

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .