6-(3,5-Dimeth­oxy­benzyl­amino)-9-(oxan-2-yl)-9H-purine

Štarha, P.; Popa, I.; Dvořák, Z.; Trávníček, Z.

doi:10.1107/S1600536813006697

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o533

doi:10.1107/S1600536813006697

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6-(3,5-Dimethoxybenzylamino)-9-(oxan-2-yl)-9H-purine

Pavel Štarha,^a Igor Popa,^a Zdeněk Dvořák ^b and Zdeněk Trávníček ^a ^*

^aDepartment of Inorganic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, CZ-771 46 Olomouc, Czech Republic, and ^bDepartment of Cell Biology and Genetics, Faculty of Science, Palacký University, Šlechtitelů 11, CZ-783 71 Olomouc, Czech Republic
^*Correspondence e-mail: zdenek.travnicek@upol.cz

(Received 22 February 2013; accepted 8 March 2013; online 13 March 2013)

The molecule of the title compound, C₁₉H₂₃N₅O₃, contains six-membered pyrimidine and five-membered imidazole rings merged into the essentially planar purine skeleton (r.m.s. deviation = 0.01 Å). In the crystal, pairs of N—H⋯N hydrogen bonds link molecules into inversion dimers. The dimers are linked via C—H⋯O hydrogen bonds, forming double-stranded chains propagating along [001]. These chains are linked via C—H⋯π and parallel slipped π–π interactions [centroid–centroid distance = 3.467 (1) Å; slippage 0.519 Å], forming a three-dimensional network.

Related literature

For the alternative synthetic procedure and biological activity of the title compound, see: Szüčová et al. (2009 ). For the structures of similar compounds, see: Soriano-Garcia et al. (2003 ); Taddei et al. (2004 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₉H₂₃N₅O₃
M_r = 369.42
Triclinic, $[P \overline 1]$
a = 8.6978 (3) Å
b = 8.8318 (3) Å
c = 12.1517 (4) Å
α = 84.808 (3)°
β = 78.674 (3)°
γ = 82.039 (3)°
V = 904.53 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 110 K
0.40 × 0.40 × 0.35 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ). T_min = 0.963, T_max = 0.968
6684 measured reflections
3177 independent reflections
2784 reflections with I > 2σ(I)
R_int = 0.010

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.116
S = 1.07
3177 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯N7ⁱ	0.88	2.38	3.155 (2)	147
C17—H17A⋯O3ⁱⁱ	0.98	2.44	3.216 (3)	136
C8—H8⋯Cgⁱ	0.95	2.72	3.506 (2)	142
C21—H21B⋯Cgⁱⁱⁱ	0.99	2.93	3.904 (3)	169
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y, z-1; (iii) -x+2, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2011 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813006697/zq2196sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006697/zq2196Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006697/zq2196Isup3.cml

checkCIF report

Comment top

The title compound, 6-(3,5-dimethoxybenzylamino)-9-(tetrahydropyran-2-yl)-9H-purine (Fig. 1), is formed by the essentially planar purine moiety substituted by 3,5-dimethoxybenzylamine and tetrahydropyran-2-yl at the C6, and N9 position, respectively (for related structures, see: Soriano-Garcia et al., 2003; Taddei et al., 2004). The six-membered pyrimidine and five-membered imidazole rings of the purine moiety form the dihedral angle of 1.50 (6)° (Fig. 2), while the planes fitted through all the non-hydrogen atoms of purine and benzene rings form the dihedral angle of 63.87 (4)° (Fig. 3). The most deviated atoms from the planes created through the pyrimidine, imidazole, purine and benzene rings are C5 (0.006 (2) Å), C8 (-0.005 (2) Å), C5 (0.021 (2) Å), and C12 (0.011 (2) Å), respectively. The crystal structure is stabilized by the N6—H6···N7 hydrogen bonds (see Table 1 for parameters) and C—H···O, C—H···π and parallel slipped π–π interactions [centroid–centroid distance = 3.467 (1) Å; slippage 0.519 Å] (Fig. 4 and Fig. 5). The tetrahydropyranyl ring adopts a chair conformation. The Cremer-Pople puckering parameters (Cremer & Pople, 1975) are Q_T = 0.691 (2) Å, Θ₂ = 89.4 (2)°, q₂ = 0.691 (2)°, q₃ = 0.007 (2)° and ϕ₂ = 148.8 (2)°.

Related literature top

For the alternative synthetic procedure and biological activity of the title compound, see: Szüčová et al. (2009). For the structures of similar compounds, see: Soriano-Garcia et al. (2003); Taddei et al. (2004). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound, synthesized with the aim of its possible utilization as a suitable ligand in coordination chemistry of transition metals, was prepared by a slightly modified method reported by Szüčová et al., 2009. The starting compounds 6-chloropurine and 3,4-dihydro-2H-pyrane (a molar ratio of 1:2) were stirred in a minimum volume of ethanol (15 min, laboratory temperature) and then CF₃COOH (1.30 molar equivalent of 6-chloropurine) was slowly poured. The reaction mixture was neutralized by 10% NH₄OH after 24 h of stirring at laboratory temperature. The solvents were evaporated and yellowish product was washed (distilled water, methanol, diethyl ether) and dried in desiccator over P₄O₁₀. The obtained 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine was dissolved in a minimum volume of N,N`-dimethylformamide and 3,5-dimethoxybenzylamine (1.33 molar equivalent) and triethylamine (1.67 molar equivalent) were poured in. The reaction mixture was stirred at 90 °C for 150 min and then it was evaporated to dryness. The solid was suspended in cold distilled water, filtered off, washed (distilled water, methanol, diethyl ether) and dried in desiccator over P₄O₁₀. The powder product was recrystallized from ethanol and the obtained microcrystals, suitable for single-crystal X-ray analysis, were collected by filtration. Analysis calculated for C₁₉H₂₃N₅O₃: C 61.8, H 6.3, N 19.0%; found: C 61.7, H 6.4, N 18.8%. Elemental analysis (C, H, N) was performed on a Thermo Scientific Flash 2000 CHNO-S Analyzer.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2011); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with the non-hydrogen atoms depicted as thermal ellipsoids at the 50% probability level and given with the atom numbering scheme.
	Fig. 2. The model of the title compound, showing the mutual orientation of the six-membered pyrimidine (least-squares plane created through the N1, C2, N3, C4, C5 and C6 atoms; in blue) and five-membered imidazole rings (least-squares plane created through the C4, C5, N7, C8 and N9 atoms; in red). The planes are nearly coplanar forming the dihedral angle of 1.50 (6)°.
	Fig. 3. The model of the title compound, showing the mutual orientation of the purine skeleton (least-squares plane created through the N1, C2, N3, C4, C5, C6, N7, C8 and N9 atoms; in red) and benzene ring (least-squares plane created through the C10, C11, C12, C13, C14 and C15 atoms; in blue). The planes form the dihedral angle of 63.87 (4)°.
	Fig. 4. Part of the crystal structure of the title compound (Ball-and-stick model), showing the N6—H6···N7 hydrogen bonds (dashed green lines; see Table 1 for parameters) and C8—H8···π, C21—H21···π and π···π interactions (dashed orange lines; see Table 1 for C8—H8···Cg and C21—H21···Cg parameters). Cg···Cgⁱⁱⁱ parameters: d(D···A) = 3.46700 (10) Å. Symmetry codes: (i) –x+2, –y+1, –z+1; (iii) –x+2, –y+2, –z+1; (iv) x, y+1, z.
	Fig. 5. Part of the crystal structure of the title compound (Ball-and-stick model), showing two molecules connected through C16—H16C···N6 non-covalent contacts (dashed orange lines; see Table 1 for parameters). Symmetry code: (v) –x+1, –y+1, –z+1.

6-(3,5-Dimethoxybenzylamino)-9-(oxan-2-yl)-9H-purine top

Crystal data top

C₁₉H₂₃N₅O₃	Z = 2
M_r = 369.42	F(000) = 392
Triclinic, P1	D_x = 1.356 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6978 (3) Å	Cell parameters from 6498 reflections
b = 8.8318 (3) Å	θ = 3.0–31.7°
c = 12.1517 (4) Å	µ = 0.10 mm⁻¹
α = 84.808 (3)°	T = 110 K
β = 78.674 (3)°	Prism, colourless
γ = 82.039 (3)°	0.40 × 0.40 × 0.35 mm
V = 904.53 (5) Å³

Data collection top

Agilent Xcalibur Sapphire2 diffractometer	3177 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2784 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.010
Detector resolution: 8.3611 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012).	k = −10→9
T_min = 0.963, T_max = 0.968	l = −14→14
6684 measured reflections

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0525P)² + 0.5406P] where P = (F_o² + 2F_c²)/3
3177 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₂₃N₅O₃	γ = 82.039 (3)°
M_r = 369.42	V = 904.53 (5) Å³
Triclinic, P1	Z = 2
a = 8.6978 (3) Å	Mo Kα radiation
b = 8.8318 (3) Å	µ = 0.10 mm⁻¹
c = 12.1517 (4) Å	T = 110 K
α = 84.808 (3)°	0.40 × 0.40 × 0.35 mm
β = 78.674 (3)°

Data collection top

Agilent Xcalibur Sapphire2 diffractometer	3177 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012).	2784 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.968	R_int = 0.010
6684 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.07	Δρ_max = 0.45 e Å⁻³
3177 reflections	Δρ_min = −0.22 e Å⁻³
246 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 > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.34333 (13)	0.54945 (15)	0.18751 (10)	0.0325 (3)
N1	0.74662 (17)	0.93176 (17)	0.56497 (14)	0.0343 (4)
O2	0.86794 (14)	0.66871 (15)	0.06254 (11)	0.0348 (3)
C2	0.7939 (2)	1.0254 (2)	0.62854 (19)	0.0393 (5)
H2	0.7252	1.1178	0.6431	0.047*
N3	0.92245 (18)	1.00924 (17)	0.67466 (14)	0.0347 (4)
O3	1.14994 (17)	0.82537 (18)	0.87030 (12)	0.0457 (4)
C4	1.01114 (19)	0.87587 (19)	0.64793 (14)	0.0253 (4)
C5	0.98030 (19)	0.76782 (18)	0.58273 (14)	0.0240 (4)
N6	0.79042 (16)	0.70162 (17)	0.47898 (12)	0.0289 (3)
H6	0.8574	0.6235	0.4525	0.035*
C6	0.83853 (19)	0.79912 (19)	0.54048 (14)	0.0260 (4)
N7	1.09793 (16)	0.64320 (16)	0.57585 (12)	0.0269 (3)
C8	1.19489 (19)	0.67977 (19)	0.63655 (15)	0.0265 (4)
H8	1.2878	0.6148	0.6480	0.032*
N9	1.15153 (16)	0.81862 (15)	0.68192 (12)	0.0250 (3)
C9	0.6313 (2)	0.7216 (2)	0.45512 (15)	0.0302 (4)
H9A	0.5858	0.8299	0.4635	0.036*
H9B	0.5652	0.6577	0.5113	0.036*
C10	0.62444 (19)	0.67918 (18)	0.33892 (14)	0.0245 (4)
C11	0.48482 (19)	0.63085 (18)	0.32182 (14)	0.0244 (4)
H11	0.3985	0.6226	0.3826	0.029*
C12	0.47421 (19)	0.59515 (18)	0.21484 (15)	0.0251 (4)
C13	0.6021 (2)	0.60276 (19)	0.12598 (15)	0.0270 (4)
H13	0.5954	0.5746	0.0536	0.032*
C14	0.73869 (19)	0.65179 (19)	0.14429 (15)	0.0262 (4)
C15	0.75085 (19)	0.69009 (18)	0.25110 (14)	0.0255 (4)
H15	0.8452	0.7233	0.2632	0.031*
C16	0.2009 (2)	0.5642 (2)	0.26940 (16)	0.0374 (5)
H16A	0.1155	0.5309	0.2391	0.056*
H16B	0.1729	0.6716	0.2877	0.056*
H16C	0.2164	0.5004	0.3375	0.056*
C17	0.8598 (2)	0.6274 (3)	−0.04723 (16)	0.0421 (5)
H17A	0.9599	0.6404	−0.0984	0.063*
H17B	0.7734	0.6933	−0.0751	0.063*
H17C	0.8403	0.5202	−0.0433	0.063*
C18	1.2218 (2)	0.88515 (19)	0.76217 (15)	0.0278 (4)
H18	1.1926	0.9988	0.7569	0.033*
C19	1.2010 (3)	0.8915 (3)	0.95875 (19)	0.0599 (7)
H19A	1.1479	0.8498	1.0327	0.072*
H19B	1.1712	1.0039	0.9541	0.072*
C20	1.3771 (3)	0.8561 (3)	0.9489 (2)	0.0600 (7)
H20A	1.4064	0.7439	0.9578	0.072*
H20B	1.4112	0.9037	1.0093	0.072*
C21	1.4591 (3)	0.9167 (3)	0.8360 (2)	0.0486 (6)
H21A	1.5746	0.8868	0.8279	0.058*
H21B	1.4389	1.0300	0.8302	0.058*
C22	1.3974 (2)	0.8509 (2)	0.74142 (18)	0.0381 (5)
H22A	1.4431	0.8983	0.6674	0.046*
H22B	1.4289	0.7388	0.7412	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0209 (6)	0.0443 (8)	0.0359 (7)	−0.0083 (5)	−0.0071 (5)	−0.0122 (6)
N1	0.0259 (8)	0.0266 (8)	0.0536 (10)	0.0034 (6)	−0.0173 (7)	−0.0084 (7)
O2	0.0270 (7)	0.0448 (8)	0.0353 (7)	−0.0124 (6)	−0.0040 (5)	−0.0088 (6)
C2	0.0283 (10)	0.0256 (9)	0.0678 (14)	0.0061 (7)	−0.0193 (9)	−0.0143 (9)
N3	0.0269 (8)	0.0245 (8)	0.0561 (10)	0.0023 (6)	−0.0157 (7)	−0.0123 (7)
O3	0.0487 (9)	0.0562 (9)	0.0373 (8)	−0.0194 (7)	−0.0102 (6)	−0.0057 (7)
C4	0.0207 (8)	0.0224 (8)	0.0341 (9)	−0.0019 (6)	−0.0082 (7)	−0.0033 (7)
C5	0.0209 (8)	0.0224 (8)	0.0295 (9)	−0.0012 (6)	−0.0070 (7)	−0.0029 (7)
N6	0.0231 (7)	0.0306 (8)	0.0360 (8)	0.0043 (6)	−0.0145 (6)	−0.0101 (6)
C6	0.0225 (8)	0.0257 (9)	0.0310 (9)	−0.0008 (7)	−0.0084 (7)	−0.0031 (7)
N7	0.0221 (7)	0.0256 (7)	0.0347 (8)	0.0019 (6)	−0.0109 (6)	−0.0068 (6)
C8	0.0227 (8)	0.0219 (8)	0.0367 (9)	0.0018 (6)	−0.0115 (7)	−0.0054 (7)
N9	0.0221 (7)	0.0213 (7)	0.0344 (8)	−0.0014 (5)	−0.0118 (6)	−0.0046 (6)
C9	0.0217 (8)	0.0357 (10)	0.0352 (10)	0.0016 (7)	−0.0116 (7)	−0.0069 (8)
C10	0.0233 (8)	0.0177 (8)	0.0340 (9)	0.0040 (6)	−0.0132 (7)	−0.0034 (7)
C11	0.0214 (8)	0.0205 (8)	0.0316 (9)	0.0022 (6)	−0.0078 (7)	−0.0039 (7)
C12	0.0215 (8)	0.0202 (8)	0.0363 (9)	−0.0013 (6)	−0.0119 (7)	−0.0044 (7)
C13	0.0264 (9)	0.0259 (9)	0.0312 (9)	−0.0017 (7)	−0.0104 (7)	−0.0059 (7)
C14	0.0224 (8)	0.0223 (8)	0.0341 (9)	−0.0014 (6)	−0.0064 (7)	−0.0026 (7)
C15	0.0214 (8)	0.0200 (8)	0.0378 (10)	−0.0006 (6)	−0.0131 (7)	−0.0027 (7)
C16	0.0238 (9)	0.0543 (12)	0.0373 (10)	−0.0112 (8)	−0.0048 (8)	−0.0116 (9)
C17	0.0347 (10)	0.0602 (13)	0.0348 (10)	−0.0167 (9)	−0.0037 (8)	−0.0096 (9)
C18	0.0311 (9)	0.0207 (8)	0.0360 (10)	−0.0055 (7)	−0.0144 (8)	−0.0031 (7)
C19	0.0812 (18)	0.0688 (16)	0.0379 (12)	−0.0238 (14)	−0.0180 (12)	−0.0101 (11)
C20	0.0923 (19)	0.0450 (13)	0.0620 (15)	−0.0279 (13)	−0.0523 (14)	0.0076 (11)
C21	0.0400 (12)	0.0424 (12)	0.0728 (16)	−0.0082 (9)	−0.0319 (11)	−0.0014 (11)
C22	0.0238 (9)	0.0453 (11)	0.0477 (12)	−0.0038 (8)	−0.0140 (8)	−0.0015 (9)

Geometric parameters (Å, º) top

O1—C12	1.3672 (19)	C11—C12	1.388 (2)
O1—C16	1.427 (2)	C11—H11	0.9500
N1—C2	1.336 (2)	C12—C13	1.394 (2)
N1—C6	1.345 (2)	C13—C14	1.383 (2)
O2—C14	1.362 (2)	C13—H13	0.9500
O2—C17	1.432 (2)	C14—C15	1.398 (2)
C2—N3	1.331 (2)	C15—H15	0.9500
C2—H2	0.9500	C16—H16A	0.9800
N3—C4	1.344 (2)	C16—H16B	0.9800
O3—C18	1.428 (2)	C16—H16C	0.9800
O3—C19	1.438 (2)	C17—H17A	0.9800
C4—C5	1.379 (2)	C17—H17B	0.9800
C4—N9	1.381 (2)	C17—H17C	0.9800
C5—N7	1.392 (2)	C18—C22	1.491 (2)
C5—C6	1.410 (2)	C18—H18	1.0000
N6—C6	1.347 (2)	C19—C20	1.503 (4)
N6—C9	1.453 (2)	C19—H19A	0.9900
N6—H6	0.8800	C19—H19B	0.9900
N7—C8	1.312 (2)	C20—C21	1.504 (3)
C8—N9	1.365 (2)	C20—H20A	0.9900
C8—H8	0.9500	C20—H20B	0.9900
N9—C18	1.451 (2)	C21—C22	1.548 (3)
C9—C10	1.508 (2)	C21—H21A	0.9900
C9—H9A	0.9900	C21—H21B	0.9900
C9—H9B	0.9900	C22—H22A	0.9900
C10—C15	1.381 (2)	C22—H22B	0.9900
C10—C11	1.400 (2)

C12—O1—C16	117.27 (13)	C13—C14—C15	120.74 (16)
C2—N1—C6	118.32 (15)	C10—C15—C14	119.37 (15)
C14—O2—C17	116.38 (13)	C10—C15—H15	120.3
N3—C2—N1	129.90 (16)	C14—C15—H15	120.3
N3—C2—H2	115.0	O1—C16—H16A	109.5
N1—C2—H2	115.0	O1—C16—H16B	109.5
C2—N3—C4	109.91 (15)	H16A—C16—H16B	109.5
C18—O3—C19	111.26 (15)	O1—C16—H16C	109.5
N3—C4—C5	127.40 (15)	H16A—C16—H16C	109.5
N3—C4—N9	126.56 (15)	H16B—C16—H16C	109.5
C5—C4—N9	106.04 (14)	O2—C17—H17A	109.5
C4—C5—N7	110.73 (14)	O2—C17—H17B	109.5
C4—C5—C6	116.57 (15)	H17A—C17—H17B	109.5
N7—C5—C6	132.65 (15)	O2—C17—H17C	109.5
C6—N6—C9	121.98 (14)	H17A—C17—H17C	109.5
C6—N6—H6	119.0	H17B—C17—H17C	109.5
C9—N6—H6	119.0	O3—C18—N9	105.55 (13)
N1—C6—N6	119.01 (15)	O3—C18—C22	112.37 (15)
N1—C6—C5	117.88 (15)	N9—C18—C22	112.58 (15)
N6—C6—C5	123.10 (15)	O3—C18—H18	108.7
C8—N7—C5	103.34 (14)	N9—C18—H18	108.7
N7—C8—N9	114.60 (14)	C22—C18—H18	108.7
N7—C8—H8	122.7	O3—C19—C20	110.3 (2)
N9—C8—H8	122.7	O3—C19—H19A	109.6
C8—N9—C4	105.29 (13)	C20—C19—H19A	109.6
C8—N9—C18	128.47 (14)	O3—C19—H19B	109.6
C4—N9—C18	125.68 (14)	C20—C19—H19B	109.6
N6—C9—C10	113.44 (14)	H19A—C19—H19B	108.1
N6—C9—H9A	108.9	C19—C20—C21	110.10 (18)
C10—C9—H9A	108.9	C19—C20—H20A	109.6
N6—C9—H9B	108.9	C21—C20—H20A	109.6
C10—C9—H9B	108.9	C19—C20—H20B	109.6
H9A—C9—H9B	107.7	C21—C20—H20B	109.6
C15—C10—C11	120.70 (15)	H20A—C20—H20B	108.2
C15—C10—C9	121.21 (15)	C20—C21—C22	109.71 (17)
C11—C10—C9	118.08 (15)	C20—C21—H21A	109.7
C12—C11—C10	119.11 (16)	C22—C21—H21A	109.7
C12—C11—H11	120.4	C20—C21—H21B	109.7
C10—C11—H11	120.4	C22—C21—H21B	109.7
O1—C12—C11	124.41 (15)	H21A—C21—H21B	108.2
O1—C12—C13	114.85 (15)	C18—C22—C21	108.40 (16)
C11—C12—C13	120.74 (15)	C18—C22—H22A	110.0
C14—C13—C12	119.31 (16)	C21—C22—H22A	110.0
C14—C13—H13	120.3	C18—C22—H22B	110.0
C12—C13—H13	120.3	C21—C22—H22B	110.0
O2—C14—C13	124.00 (16)	H22A—C22—H22B	108.4
O2—C14—C15	115.25 (14)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N7ⁱ	0.88	2.38	3.155 (2)	147
C17—H17A···O3ⁱⁱ	0.98	2.44	3.216 (3)	136
C8—H8···Cgⁱ	0.95	2.72	3.506 (2)	142
C21—H21B···Cgⁱⁱⁱ	0.99	2.93	3.904 (3)	169

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₃N₅O₃
M_r	369.42
Crystal system, space group	Triclinic, P1
Temperature (K)	110
a, b, c (Å)	8.6978 (3), 8.8318 (3), 12.1517 (4)
α, β, γ (°)	84.808 (3), 78.674 (3), 82.039 (3)
V (Å³)	904.53 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.40 × 0.35

Data collection
Diffractometer	Agilent Xcalibur Sapphire2 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012).
T_min, T_max	0.963, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	6684, 3177, 2784
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.116, 1.07
No. of reflections	3177
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.22

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2011), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N7ⁱ	0.88	2.38	3.155 (2)	147
C17—H17A···O3ⁱⁱ	0.98	2.44	3.216 (3)	136
C8—H8···Cgⁱ	0.95	2.72	3.506 (2)	142
C21—H21B···Cgⁱⁱⁱ	0.99	2.93	3.904 (3)	169

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

Acknowledgements

This work was supported by Palacký University (grant No. PrF_2012_009). The authors thank Mr Tomáš Šilha for performing the CHN elemental analyses.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England. Google Scholar
Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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Volume 69| Part 4| April 2013| Page o533

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