N-Benzyl-9-isopropyl-9H-purin-6-amine

Gergela, D.; Rouchal, M.; Bartoš, P.; Vícha, R.

doi:10.1107/S1600536813013500

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o954-o955

doi:10.1107/S1600536813013500

Open

access

N-Benzyl-9-isopropyl-9H-purin-6-amine

David Gergela,^a Michal Rouchal,^a Peter Bartoš ^b and Robert Vícha ^a ^*

^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, Kamenice 5, Brno-Bohunice 625 00, Czech Republic
^*Correspondence e-mail: rvicha@ft.utb.cz

(Received 6 May 2013; accepted 16 May 2013; online 25 May 2013)

The asymmetric unit of the title compound, C₁₅H₁₇N₅, consists of two molecules in which the dihedral angles between the best planes of the purine ring system (r.m.s. deviations = 0.0060 and 0.0190 Å) and the benzene ring are 89.21 (3) and 82.14 (4)°. The molecules within the asymmetric unit are linked into dimers by pairs of N—H⋯N hydrogen bonds. Weak C—H⋯π contacts and π–π interactions [centroid–centroid = 3.3071 (1) Å] further connect the molecules into a three-dimensional network.

Related literature

The title compound was prepared according to a modified procedure published by Fiorini & Abel (1998 ). For the biological activity of 6,9-disubstituted purines, see: Cappellacci et al. (2011 ); Jorda et al. (2011 ); Tunçbilek et al. (2009 ). For crystallographic data for related compounds, see: Novotná & Trávníček (2013 ); Rouchal et al. (2009a ,b ); Trávníček et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₇N₅
M_r = 267.34
Monoclinic, P 2₁ /c
a = 12.9926 (5) Å
b = 21.1673 (7) Å
c = 11.2622 (6) Å
β = 114.274 (5)°
V = 2823.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 K
0.50 × 0.38 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2) diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.942, T_max = 1.000
21460 measured reflections
4972 independent reflections
3280 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.058
S = 0.83
4972 reflections
373 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are centroids of the C10–C15, C30–C35, N1/N2/C1–C4 and N21/N22/C21–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯N23	0.896 (13)	2.129 (11)	2.9883 (13)	160.2 (12)
N25—H25N⋯N3	0.908 (12)	2.151 (12)	3.0088 (15)	157.2 (12)
C25—H25⋯Cg1	0.95	2.76	3.6413 (14)	156
C5—H5⋯Cg2	0.95	2.72	3.6179 (13)	158
C12—H12⋯Cg3ⁱ	0.95	2.93	3.6703 (17)	135
C15—H15⋯Cg4ⁱⁱ	0.95	2.60	3.5158 (15)	161
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+2, -y+1, -z+2.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813013500/pk2482sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013500/pk2482Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013500/pk2482Isup3.cml

checkCIF report

Comment top

The synthesis of purine derivatives bearing various substituents at C6 and N9 positions is closely related with the eventual biological activity of the final molecule. Recently, several 6,9-disubstituted purines were described as antibacterial (Tunçbilek et al., 2009), antileishmanial (Jorda et al., 2011) and antitumor (Cappellacci et al., 2011) agents. The title molecule, N-benzyl-9-isopropyl-9H-purin-6-amine, was prepared as a part of our ongoing research aimed at preparation of new disubstituted purine series.

The asymmetric unit of the title compound consists of two purine-based molecules slightly different in their geometries (Fig. 1). The dihedral angles between the best planes of the purine and benzene rings are 89.21 (3)° and 82.14 (4)°, respectively. The torsion angles N1—C1—N5—C9, C1—N5—C9—C10, N5—C9—C10—C11 and C5—N4—C6—C7 indicating the mutual orientation of substituents and purine ring are 2.85 (19), -110.7 (14), 33.8 (18) and 31.3 (18)°, respectively. The corresponding values of torsion angles for the second conformer are 0.44 (19), -96.7 (15), 35.5 (17) and 35.9 (18)°, respectively. The molecules within the asymmetric unit are linked by N5—H5N···N23 and N25—H25N···N3 hydrogen bonds (Table 1, Fig. 2) to form dimers with dihedral angles between the best planes of the two purines being 32.53 (3)°. In contrast, the benzene rings are essentially parallel with the dihedral angle of 2.88 (3)°. The crystal packing is further stabilized via short intermolecular non-bonding C—H···π contacts and π···π interactions (Table 1, Fig. 2). The interplanar distance between the adjacent purine best planes of the π···π stacked molecules is of 3.2583 (13) Å.

Related literature top

The title compound was prepared according to a modified procedure published by Fiorini & Abel (1998). For the biological activity of 6,9-disubstituted purines, see: Cappellacci et al. (2011); Jorda et al. (2011); Tunçbilek et al. (2009). For crystallographic data for related compounds, see: Novotná & Trávníček (2013); Rouchal et al. (2009a,b); Trávníček et al. (2010).

Experimental top

The title compound was prepared according to a slightly modified literature procedure (Fiorini & Abel, 1998). 6-Chloro-9-isopropyl-9H-purine (100 mg, 0.51 mmol) and benzylamine (58 mg, 0.54 mmol) were dissolved in a mixture of DMSO (4 ml) and triethylamine (57 mg, 0.56 mmol). The resulting solution was stirred at 90 °C for 2 h. Subsequently, the mixture was diluted with water and extracted with diethyl ether (7 × 10 ml). The combined organic layers were washed twice with brine, dried over Na₂SO₄ and evaporated in vacuum. The desired product was obtained after the purification of crude material using column chromatography (silica gel; petroleum ether/ethyl acetate, 1/3, v/v) as a colourless crystalline powder (66 mg, 49%, mp 388–391 K). The crystals used for data collection were grown by spontaneous evaporation from deuterochloroform at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. An ellipsoid plot of the asymmetric unit with atoms represented as 50% probability ellipsoids. H-atoms are showed as small spheres of arbitrary radii. H-bonds are denoted with dashed lines.

Fig. 2. A fragment of the molecular packing. H-atoms have been omitted for clarity with exception to those participating in weak interactions. The red dashed lines denote the H-bonds, the green dashed lines denote the π···π interactions and the black dotted lines denote the C—H···π contacts. Cg1, Cg2,Cg3 and Cg4 are respective centers of gravity of C10–C15; C30–C35; C1,N1,C2,N2,C3,C4 and C21,N21,C22,N22,C23,C24 rings. Symmetry codes: i) -x + 1, -y + 1, -z + 2; ii) x, y, z + 1; iii) -x + 2, -y + 1, -z + 2.

N-Benzyl-9-isopropyl-9H-purin-6-amine top

Crystal data top

C₁₅H₁₇N₅	F(000) = 1136
M_r = 267.34	D_x = 1.258 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 390 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.9926 (5) Å	Cell parameters from 6488 reflections
b = 21.1673 (7) Å	θ = 2.9–27.3°
c = 11.2622 (6) Å	µ = 0.08 mm⁻¹
β = 114.274 (5)°	T = 120 K
V = 2823.5 (2) Å³	Pyramid, colourless
Z = 8	0.50 × 0.38 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur (Sapphire2) diffractometer	4972 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3280 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 8.4353 pixels mm^-1	θ_max = 25.0°, θ_min = 3.3°
ω scan	h = −15→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −25→23
T_min = 0.942, T_max = 1.000	l = −13→10
21460 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0275P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.058	(Δ/σ)_max = 0.001
S = 0.83	Δρ_max = 0.13 e Å⁻³
4972 reflections	Δρ_min = −0.16 e Å⁻³
373 parameters

Crystal data top

C₁₅H₁₇N₅	V = 2823.5 (2) Å³
M_r = 267.34	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9926 (5) Å	µ = 0.08 mm⁻¹
b = 21.1673 (7) Å	T = 120 K
c = 11.2622 (6) Å	0.50 × 0.38 × 0.20 mm
β = 114.274 (5)°

Data collection top

Oxford Diffraction Xcalibur (Sapphire2) diffractometer	4972 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3280 reflections with I > 2σ(I)
T_min = 0.942, T_max = 1.000	R_int = 0.035
21460 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 0.83	Δρ_max = 0.13 e Å⁻³
4972 reflections	Δρ_min = −0.16 e Å⁻³
373 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

	x	y	z	U_iso*/U_eq
N1	0.48434 (8)	0.47471 (5)	0.65985 (10)	0.0260 (3)
N2	0.35401 (8)	0.55081 (5)	0.51464 (10)	0.0262 (3)
N3	0.61994 (8)	0.62964 (5)	0.66899 (10)	0.0313 (3)
N4	0.44524 (8)	0.65164 (5)	0.51961 (10)	0.0263 (3)
N5	0.67119 (9)	0.49857 (5)	0.79188 (10)	0.0265 (3)
C1	0.57003 (10)	0.51658 (6)	0.70266 (12)	0.0241 (3)
C2	0.38440 (10)	0.49452 (6)	0.57007 (12)	0.0279 (3)
H2	0.3265	0.4634	0.5419	0.033*
C3	0.44264 (10)	0.59076 (6)	0.55935 (12)	0.0235 (3)
C4	0.54997 (10)	0.57782 (6)	0.65076 (11)	0.0235 (3)
C5	0.55292 (10)	0.67225 (6)	0.58899 (12)	0.0324 (3)
H5	0.5775	0.7136	0.5804	0.039*
C6	0.34853 (10)	0.68646 (6)	0.42406 (12)	0.0264 (3)
H6	0.2996	0.6553	0.3584	0.032*
C7	0.38698 (11)	0.73471 (7)	0.35260 (13)	0.0440 (4)
H7A	0.4339	0.7141	0.3146	0.066*
H7B	0.4310	0.7676	0.4136	0.066*
H7C	0.3210	0.7538	0.2831	0.066*
C8	0.27902 (11)	0.71513 (6)	0.48996 (13)	0.0374 (4)
H8A	0.2602	0.6824	0.5394	0.056*
H8B	0.2093	0.7329	0.4239	0.056*
H8C	0.3224	0.7487	0.5493	0.056*
C9	0.69743 (10)	0.43519 (6)	0.84296 (12)	0.0275 (3)
H9A	0.7664	0.4207	0.8340	0.033*
H9B	0.6349	0.4068	0.7898	0.033*
C10	0.71588 (10)	0.42924 (6)	0.98378 (12)	0.0226 (3)
C11	0.65661 (10)	0.46597 (6)	1.03600 (13)	0.0289 (3)
H11	0.6031	0.4958	0.9824	0.035*
C12	0.67436 (11)	0.45977 (7)	1.16490 (13)	0.0369 (4)
H12	0.6325	0.4850	1.1992	0.044*
C13	0.75233 (11)	0.41715 (7)	1.24409 (14)	0.0381 (4)
H13	0.7646	0.4131	1.3329	0.046*
C14	0.81238 (11)	0.38046 (6)	1.19388 (14)	0.0363 (4)
H14	0.8666	0.3511	1.2481	0.044*
C15	0.79357 (10)	0.38652 (6)	1.06441 (13)	0.0289 (3)
H15	0.8349	0.3608	1.0302	0.035*
N21	1.00117 (8)	0.72864 (5)	0.95195 (10)	0.0239 (3)
N22	1.08432 (8)	0.68113 (5)	1.16590 (9)	0.0236 (3)
N23	0.87221 (8)	0.57374 (5)	0.96305 (10)	0.0279 (3)
N24	0.99893 (8)	0.57966 (5)	1.17200 (10)	0.0256 (3)
N25	0.85603 (9)	0.68204 (5)	0.77541 (10)	0.0260 (3)
C21	0.92837 (9)	0.68029 (6)	0.90160 (12)	0.0220 (3)
C22	1.07258 (10)	0.72557 (6)	1.07788 (12)	0.0252 (3)
H22	1.1224	0.7605	1.1090	0.030*
C23	1.01033 (9)	0.63394 (6)	1.11174 (12)	0.0214 (3)
C24	0.93237 (9)	0.62980 (6)	0.98385 (12)	0.0215 (3)
C25	0.91468 (10)	0.54632 (6)	1.07785 (13)	0.0310 (3)
H25	0.8889	0.5066	1.0940	0.037*
C26	1.05832 (10)	0.56472 (6)	1.31163 (12)	0.0297 (3)
H26	1.1349	0.5846	1.3442	0.036*
C27	1.07405 (11)	0.49430 (6)	1.33211 (13)	0.0417 (4)
H27A	1.1117	0.4776	1.2791	0.063*
H27B	1.0002	0.4740	1.3062	0.063*
H27C	1.1204	0.4856	1.4243	0.063*
C28	0.99545 (12)	0.59390 (7)	1.38523 (14)	0.0486 (4)
H28A	0.9907	0.6397	1.3718	0.073*
H28B	1.0358	0.5847	1.4783	0.073*
H28C	0.9192	0.5761	1.3532	0.073*
C29	0.85268 (10)	0.73381 (6)	0.68906 (12)	0.0278 (3)
H29A	0.8387	0.7163	0.6023	0.033*
H29B	0.9275	0.7546	0.7232	0.033*
C30	0.76355 (10)	0.78312 (6)	0.67322 (12)	0.0246 (3)
C31	0.73658 (10)	0.79940 (6)	0.77588 (13)	0.0307 (3)
H31	0.7761	0.7802	0.8586	0.037*
C32	0.65295 (11)	0.84318 (6)	0.75992 (14)	0.0376 (4)
H32	0.6350	0.8537	0.8312	0.045*
C33	0.59581 (12)	0.87150 (6)	0.64080 (16)	0.0429 (4)
H33	0.5379	0.9013	0.6295	0.051*
C34	0.62262 (11)	0.85664 (6)	0.53779 (15)	0.0405 (4)
H34	0.5840	0.8766	0.4558	0.049*
C35	0.70600 (10)	0.81253 (6)	0.55402 (13)	0.0321 (3)
H35	0.7240	0.8023	0.4827	0.038*
H5N	0.7264 (11)	0.5272 (6)	0.8262 (12)	0.037 (4)*
H25N	0.7954 (10)	0.6558 (6)	0.7491 (12)	0.037 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0217 (6)	0.0304 (6)	0.0255 (6)	−0.0021 (5)	0.0093 (5)	−0.0038 (5)
N2	0.0209 (6)	0.0308 (7)	0.0259 (7)	−0.0027 (5)	0.0087 (5)	−0.0041 (5)
N3	0.0241 (6)	0.0316 (7)	0.0299 (7)	−0.0035 (5)	0.0026 (5)	0.0040 (6)
N4	0.0201 (6)	0.0298 (7)	0.0243 (6)	0.0000 (5)	0.0043 (5)	0.0002 (5)
N5	0.0222 (6)	0.0272 (7)	0.0248 (7)	−0.0012 (5)	0.0045 (5)	0.0000 (5)
C1	0.0220 (7)	0.0327 (8)	0.0194 (8)	−0.0008 (6)	0.0103 (6)	−0.0048 (6)
C2	0.0223 (7)	0.0328 (8)	0.0292 (8)	−0.0045 (6)	0.0114 (6)	−0.0062 (7)
C3	0.0206 (7)	0.0300 (8)	0.0204 (8)	−0.0003 (6)	0.0090 (6)	−0.0034 (6)
C4	0.0213 (7)	0.0280 (8)	0.0198 (8)	−0.0021 (6)	0.0072 (6)	−0.0017 (6)
C5	0.0236 (7)	0.0333 (8)	0.0328 (9)	−0.0048 (6)	0.0042 (6)	0.0021 (7)
C6	0.0214 (7)	0.0328 (8)	0.0201 (8)	0.0026 (6)	0.0036 (6)	−0.0001 (6)
C7	0.0321 (8)	0.0602 (11)	0.0350 (9)	0.0074 (7)	0.0092 (7)	0.0188 (8)
C8	0.0387 (8)	0.0418 (9)	0.0317 (9)	0.0115 (7)	0.0144 (7)	0.0023 (7)
C9	0.0248 (7)	0.0263 (8)	0.0299 (8)	0.0037 (6)	0.0097 (6)	−0.0034 (6)
C10	0.0199 (7)	0.0197 (7)	0.0274 (8)	−0.0027 (6)	0.0089 (6)	−0.0033 (6)
C11	0.0247 (7)	0.0306 (8)	0.0298 (9)	0.0048 (6)	0.0097 (6)	0.0000 (7)
C12	0.0360 (8)	0.0450 (10)	0.0338 (9)	0.0042 (7)	0.0186 (7)	−0.0038 (7)
C13	0.0426 (9)	0.0442 (9)	0.0302 (9)	−0.0042 (7)	0.0176 (7)	0.0040 (7)
C14	0.0370 (8)	0.0307 (9)	0.0387 (10)	0.0045 (7)	0.0132 (7)	0.0126 (7)
C15	0.0289 (7)	0.0216 (8)	0.0379 (9)	0.0034 (6)	0.0154 (7)	0.0014 (6)
N21	0.0202 (6)	0.0243 (6)	0.0270 (7)	0.0002 (5)	0.0094 (5)	−0.0011 (5)
N22	0.0202 (5)	0.0251 (6)	0.0251 (6)	−0.0022 (5)	0.0090 (5)	−0.0015 (5)
N23	0.0248 (6)	0.0261 (6)	0.0273 (7)	−0.0031 (5)	0.0050 (5)	0.0033 (5)
N24	0.0201 (6)	0.0278 (6)	0.0231 (6)	−0.0041 (5)	0.0029 (5)	0.0037 (5)
N25	0.0223 (6)	0.0270 (7)	0.0245 (7)	−0.0016 (5)	0.0054 (5)	0.0042 (5)
C21	0.0164 (6)	0.0249 (7)	0.0256 (8)	0.0030 (6)	0.0097 (6)	−0.0019 (6)
C22	0.0206 (7)	0.0256 (8)	0.0301 (8)	−0.0015 (6)	0.0112 (6)	−0.0043 (7)
C23	0.0168 (6)	0.0228 (7)	0.0246 (8)	0.0011 (5)	0.0086 (6)	0.0005 (6)
C24	0.0173 (6)	0.0224 (7)	0.0235 (8)	0.0001 (5)	0.0071 (6)	0.0006 (6)
C25	0.0251 (7)	0.0281 (8)	0.0323 (9)	−0.0071 (6)	0.0043 (7)	0.0045 (7)
C26	0.0228 (7)	0.0369 (9)	0.0226 (8)	−0.0038 (6)	0.0023 (6)	0.0069 (6)
C27	0.0379 (8)	0.0416 (9)	0.0370 (9)	0.0032 (7)	0.0065 (7)	0.0145 (7)
C28	0.0530 (10)	0.0584 (11)	0.0321 (9)	0.0091 (8)	0.0151 (8)	0.0064 (8)
C29	0.0286 (7)	0.0310 (8)	0.0243 (8)	0.0016 (6)	0.0114 (6)	0.0043 (6)
C30	0.0228 (7)	0.0248 (8)	0.0260 (8)	−0.0036 (6)	0.0099 (6)	0.0011 (6)
C31	0.0299 (7)	0.0313 (8)	0.0298 (8)	−0.0023 (6)	0.0111 (7)	0.0000 (7)
C32	0.0374 (8)	0.0327 (9)	0.0488 (10)	0.0000 (7)	0.0238 (8)	−0.0045 (8)
C33	0.0343 (8)	0.0288 (9)	0.0654 (12)	0.0067 (7)	0.0203 (8)	0.0028 (8)
C34	0.0380 (9)	0.0313 (9)	0.0468 (10)	0.0057 (7)	0.0119 (8)	0.0120 (8)
C35	0.0325 (8)	0.0315 (8)	0.0324 (9)	−0.0007 (6)	0.0136 (7)	0.0053 (7)

Geometric parameters (Å, º) top

N1—C2	1.3434 (15)	N21—C22	1.3396 (14)
N1—C1	1.3476 (15)	N21—C21	1.3500 (14)
N2—C2	1.3276 (15)	N22—C22	1.3291 (14)
N2—C3	1.3482 (14)	N22—C23	1.3460 (14)
N3—C5	1.3185 (15)	N23—C25	1.3138 (14)
N3—C4	1.3851 (14)	N23—C24	1.3869 (14)
N4—C5	1.3635 (14)	N24—C25	1.3661 (14)
N4—C3	1.3693 (15)	N24—C23	1.3730 (14)
N4—C6	1.4725 (14)	N24—C26	1.4733 (14)
N5—C1	1.3404 (15)	N25—C21	1.3440 (15)
N5—C9	1.4441 (14)	N25—C29	1.4539 (15)
N5—H5N	0.897 (12)	N25—H25N	0.908 (12)
C1—C4	1.4017 (16)	C21—C24	1.4012 (16)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.3781 (15)	C23—C24	1.3815 (15)
C5—H5	0.9500	C25—H25	0.9500
C6—C7	1.5069 (17)	C26—C27	1.5093 (17)
C6—C8	1.5119 (16)	C26—C28	1.5141 (18)
C6—H6	1.0000	C26—H26	1.0000
C7—H7A	0.9800	C27—H27A	0.9800
C7—H7B	0.9800	C27—H27B	0.9800
C7—H7C	0.9800	C27—H27C	0.9800
C8—H8A	0.9800	C28—H28A	0.9800
C8—H8B	0.9800	C28—H28B	0.9800
C8—H8C	0.9800	C28—H28C	0.9800
C9—C10	1.5086 (16)	C29—C30	1.5141 (16)
C9—H9A	0.9900	C29—H29A	0.9900
C9—H9B	0.9900	C29—H29B	0.9900
C10—C15	1.3811 (16)	C30—C31	1.3826 (17)
C10—C11	1.3842 (16)	C30—C35	1.3869 (16)
C11—C12	1.3794 (17)	C31—C32	1.3825 (17)
C11—H11	0.9500	C31—H31	0.9500
C12—C13	1.3757 (17)	C32—C33	1.3753 (18)
C12—H12	0.9500	C32—H32	0.9500
C13—C14	1.3764 (18)	C33—C34	1.3778 (19)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.3818 (17)	C34—C35	1.3841 (17)
C14—H14	0.9500	C34—H34	0.9500
C15—H15	0.9500	C35—H35	0.9500

C2—N1—C1	117.70 (11)	C22—N21—C21	117.94 (11)
C2—N2—C3	110.12 (10)	C22—N22—C23	110.22 (10)
C5—N3—C4	103.39 (10)	C25—N23—C24	103.43 (10)
C5—N4—C3	105.74 (10)	C25—N24—C23	105.28 (10)
C5—N4—C6	128.68 (11)	C25—N24—C26	128.21 (11)
C3—N4—C6	125.56 (10)	C23—N24—C26	126.27 (10)
C1—N5—C9	124.12 (11)	C21—N25—C29	122.94 (11)
C1—N5—H5N	119.7 (8)	C21—N25—H25N	117.6 (8)
C9—N5—H5N	116.1 (8)	C29—N25—H25N	117.3 (8)
N5—C1—N1	119.51 (12)	N25—C21—N21	119.20 (12)
N5—C1—C4	122.18 (11)	N25—C21—C24	122.67 (11)
N1—C1—C4	118.31 (11)	N21—C21—C24	118.13 (11)
N2—C2—N1	129.98 (12)	N22—C22—N21	129.88 (11)
N2—C2—H2	115.0	N22—C22—H22	115.1
N1—C2—H2	115.0	N21—C22—H22	115.1
N2—C3—N4	126.89 (11)	N22—C23—N24	126.80 (11)
N2—C3—C4	126.94 (12)	N22—C23—C24	126.90 (12)
N4—C3—C4	106.13 (11)	N24—C23—C24	106.28 (10)
C3—C4—N3	110.75 (11)	C23—C24—N23	110.56 (11)
C3—C4—C1	116.93 (11)	C23—C24—C21	116.92 (11)
N3—C4—C1	132.26 (11)	N23—C24—C21	132.52 (11)
N3—C5—N4	113.99 (12)	N23—C25—N24	114.45 (11)
N3—C5—H5	123.0	N23—C25—H25	122.8
N4—C5—H5	123.0	N24—C25—H25	122.8
N4—C6—C7	111.03 (10)	N24—C26—C27	110.72 (11)
N4—C6—C8	110.17 (10)	N24—C26—C28	109.45 (11)
C7—C6—C8	112.72 (11)	C27—C26—C28	112.88 (12)
N4—C6—H6	107.6	N24—C26—H26	107.9
C7—C6—H6	107.6	C27—C26—H26	107.9
C8—C6—H6	107.6	C28—C26—H26	107.9
C6—C7—H7A	109.5	C26—C27—H27A	109.5
C6—C7—H7B	109.5	C26—C27—H27B	109.5
H7A—C7—H7B	109.5	H27A—C27—H27B	109.5
C6—C7—H7C	109.5	C26—C27—H27C	109.5
H7A—C7—H7C	109.5	H27A—C27—H27C	109.5
H7B—C7—H7C	109.5	H27B—C27—H27C	109.5
C6—C8—H8A	109.5	C26—C28—H28A	109.5
C6—C8—H8B	109.5	C26—C28—H28B	109.5
H8A—C8—H8B	109.5	H28A—C28—H28B	109.5
C6—C8—H8C	109.5	C26—C28—H28C	109.5
H8A—C8—H8C	109.5	H28A—C28—H28C	109.5
H8B—C8—H8C	109.5	H28B—C28—H28C	109.5
N5—C9—C10	113.94 (10)	N25—C29—C30	114.18 (11)
N5—C9—H9A	108.8	N25—C29—H29A	108.7
C10—C9—H9A	108.8	C30—C29—H29A	108.7
N5—C9—H9B	108.8	N25—C29—H29B	108.7
C10—C9—H9B	108.8	C30—C29—H29B	108.7
H9A—C9—H9B	107.7	H29A—C29—H29B	107.6
C15—C10—C11	118.18 (12)	C31—C30—C35	118.45 (12)
C15—C10—C9	120.21 (11)	C31—C30—C29	121.18 (11)
C11—C10—C9	121.60 (11)	C35—C30—C29	120.36 (12)
C12—C11—C10	120.81 (12)	C32—C31—C30	120.95 (13)
C12—C11—H11	119.6	C32—C31—H31	119.5
C10—C11—H11	119.6	C30—C31—H31	119.5
C13—C12—C11	120.31 (13)	C33—C32—C31	119.95 (14)
C13—C12—H12	119.8	C33—C32—H32	120.0
C11—C12—H12	119.8	C31—C32—H32	120.0
C12—C13—C14	119.63 (13)	C32—C33—C34	119.99 (13)
C12—C13—H13	120.2	C32—C33—H33	120.0
C14—C13—H13	120.2	C34—C33—H33	120.0
C13—C14—C15	119.79 (13)	C33—C34—C35	119.86 (14)
C13—C14—H14	120.1	C33—C34—H34	120.1
C15—C14—H14	120.1	C35—C34—H34	120.1
C10—C15—C14	121.27 (12)	C34—C35—C30	120.79 (13)
C10—C15—H15	119.4	C34—C35—H35	119.6
C14—C15—H15	119.4	C30—C35—H35	119.6

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are centroids of the C10–C15, C30–C35, N1/N2/C1–C4 and N21/N22/C21–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N23	0.896 (13)	2.129 (11)	2.9883 (13)	160.2 (12)
N25—H25N···N3	0.908 (12)	2.151 (12)	3.0088 (15)	157.2 (12)
C25—H25···Cg1	0.95	2.76	3.6413 (14)	156
C5—H5···Cg2	0.95	2.72	3.6179 (13)	158
C12—H12···Cg3ⁱ	0.95	2.93	3.6703 (17)	135
C15—H15···Cg4ⁱⁱ	0.95	2.60	3.5158 (15)	161
Cg3···Cg3ⁱⁱⁱ			3.3071 (1)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇N₅
M_r	267.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	12.9926 (5), 21.1673 (7), 11.2622 (6)
β (°)	114.274 (5)
V (Å³)	2823.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.38 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Sapphire2) diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.942, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21460, 4972, 3280
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.058, 0.83
No. of reflections	4972
No. of parameters	373
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.16

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are centroids of the C10–C15, C30–C35, N1/N2/C1–C4 and N21/N22/C21–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N23	0.896 (13)	2.129 (11)	2.9883 (13)	160.2 (12)
N25—H25N···N3	0.908 (12)	2.151 (12)	3.0088 (15)	157.2 (12)
C25—H25···Cg1	0.95	2.76	3.6413 (14)	155.5
C5—H5···Cg2	0.95	2.72	3.6179 (13)	157.9
C12—H12···Cg3ⁱ	0.95	2.93	3.6703 (17)	135.2
C15—H15···Cg4ⁱⁱ	0.95	2.60	3.5158 (15)	161.3

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+1, −z+2.

Acknowledgements

The financial support of this work by the Internal Founding Agency of Tomas Bata University in Zlin (project No. IGA/FT/2013/008) is gratefully acknowledged.

References

Cappellacci, L., Petrelli, R., Franchetti, P., Vita, P., Kusumanchi, P., Kumar, M., Jayram, H. N., Zhou, B., Yen, Y. & Grifantini, M. (2011). Eur. J. Med. Chem. 46, 1499–1504. Web of Science CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fiorini, M. T. & Abel, C. (1998). Tetrahedron Lett. 39, 1827–1830. Web of Science CrossRef CAS Google Scholar
Jorda, R., Sacerdoti-Sierra, N., Volle, J., Havlíček, L., Kráčalíková, K., Nowicki, M. W., Nasereddin, A., Kryštof, V., Strnad, M., Walkinshaw, M. D. & Jaffe, C. L. (2011). Bioorg. Med. Chem. Lett. 21, 4233–4237. Web of Science CrossRef CAS PubMed Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Novotná, R. & Trávníček, Z. (2013). Acta Cryst. E69, o390. CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Rouchal, M., Nečas, M., Carvalho, F. P. de & Vícha, R. (2009a). Acta Cryst. E65, o298–o299. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rouchal, M., Nečas, M. & Vícha, R. (2009b). Acta Cryst. E65, o1268. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Trávníček, Z., Popa, I., Čajan, M., Zbořil, R., Kryštof, V. & Mikulík, J. (2010). J. Inorg. Biochem. 104, 405–417. Web of Science PubMed Google Scholar
Tunçbilek, M., Ateş-Alagöz, Z., Altanlar, N., Karayel, A. & Özbey, S. (2009). Bioorg. Med. Chem. 17, 1693–1700. Web of Science PubMed Google Scholar

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Volume 69| Part 6| June 2013| Pages o954-o955

doi:10.1107/S1600536813013500

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