2-Chloro-6-[(2,4-dimeth­oxy­benz­yl)amino]-9-isopropyl-9H-purine

Novotná, R.; Trávníček, Z.

doi:10.1107/S1600536813004121

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o390

doi:10.1107/S1600536813004121

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2-Chloro-6-[(2,4-dimethoxybenzyl)amino]-9-isopropyl-9H-purine

Radka Novotná ^a and Zdeněk Trávníček ^a ^*

^aDepartment of Inorganic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, CZ-771 46 Olomouc, Czech Republic
^*Correspondence e-mail: zdenek.travnicek@upol.cz

(Received 9 February 2013; accepted 11 February 2013; online 16 February 2013)

In the title compound, C₁₇H₂₀ClN₅O₂, the benzene ring and the purine ring system make a dihedral angle of 78.56 (4)°. In the crystal, molecules are linked by pairs of N—H⋯N hydrogen bonds, forming inversion dimers. C—H⋯O and C—H⋯Cl contacts further link the molecules, forming a three-dimensional network.

Related literature

For the synthesis, see: Oh et al. (1999 ). For related structures, see: Trávníček & Popa (2007a ,b ); Trávníček et al. (2010 ); Čajan & Trávníček (2011 ). For the cytotoxic activity of related compounds, see: Benson et al. (2005 ); Meijer et al. (1997 ); Štarha et al. (2010 ); Vrzal et al. (2010 ).

Experimental

Crystal data

C₁₇H₂₀ClN₅O₂
M_r = 361.83
Triclinic, $[P \overline 1]$
a = 7.8620 (2) Å
b = 9.20164 (18) Å
c = 13.3027 (3) Å
α = 82.4472 (18)°
β = 74.803 (2)°
γ = 66.012 (2)°
V = 848.16 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.40 × 0.35 × 0.30 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.908, T_max = 0.930
7228 measured reflections
2965 independent reflections
2704 reflections with I > 2σ(I)
R_int = 0.009

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.079
S = 1.10
2965 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯N7ⁱ	0.88	2.16	2.9465 (15)	148
C16—H16C⋯Cl1ⁱⁱ	0.98	2.78	3.4607 (15)	127
C19—H19A⋯O2ⁱⁱⁱ	0.98	2.57	3.4709 (17)	154
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z; (iii) x, y, 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: Mercury (Macrae et al., 2006 ) and DIAMOND (Brandenburg, 2011 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813004121/ng5316sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004121/ng5316Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004121/ng5316Isup3.cml

checkCIF report

Comment top

The title compound (I) is derived from 6-benzylaminopurine, which is along with its derivatives classified among plant growth hormones called cytokinins, which influence crucial biochemical processes, such as cell cycle and division, in plant tissues. Suitable substitutions on the 6-benzylaminopurine skeleton, particularly in the C2 and N9 positions, lead to the formation of compounds that can act as inhibitors of enzymes cyclin dependent kinases in various phases of the human cell cycle (Meijer et al., 1997). One representative of such derivatives, (R)-Roscovitine, i.e. 2-[(R)-(1-ethyl-2-hydroxyethylamino)]-6-(benzylamino)-9-isopropylpurine (Seliciclib or CYC202), has entered the IIb phase of clinical trials in patients with nonsmall cell lung cancer (Benson et al., 2005). Moreover, 6-benzylaminopurine derivatives have been successfully used as N-donor ligands in transition metal complexes exhibiting varied types of biological activity. Even the title compound (I) has been employed as a ligand in the preparation of highly anticancer active platinum(II) oxalato complexes whose in vitro cytotoxic activity against various human cancer cells exceeded the commercially applied drug cisplatin (Štarha et al., 2010; Vrzal et al., 2010).

The molecular structure of (I) consists of discrete molecules of a three-substituted adenine derivative, 2-chloro-6-[(2,4-dimethoxybenzyl)amino]-9-isopropylpurine (Fig. 1). It is basically derived from the 6-benzylaminopurine skeleton by substitutions of H atoms by the methoxy groups in the positions 2 and 4 on the benzene ring, by chlorine, and the isopropyl group in the position C2, and N9, of purine, respectively. The molecule contains two heterocyclic rings pyrimidine and imidazole, which are almost coplanar, since they form a dihedral angle of 2.02 (5)°. Additionally, there is also a benzene ring present in the structure of (I) which is similarly to the other two rings essentially planar. The maximum deviations from the least-square planes fitted through the non-hydrogen atoms for each of the rings are as follows: 0.0102 (14) Å for C4 in pyrimidine, 0.0025 (14) Å for C8 in imidazole and 0.007 (2) Å for C14 in benzene. The benzene and purine ring systems form a dihedral angle of 78.56 (4)°.

The crystal structure of (I) consists of the molecules of 2-chloro-6-[(2,4-dimethoxybenzyl)amino]-9-isopropylpurine organized into centrosymmetric dimers connected by N—H···N hydrogen bonds (Table 1, Fig. 2). Additionally, varied types of non-covalent contacts are present in the structure of (I), namely C—H···O [d(C19···O2ⁱⁱⁱ) = 3.471 (2) Å; d(C17···O1^iv) = 3.358 (2) Å; symmetry codes: (iii) x, y, 1 + z; (iv) 1 - x, 1 - y, -z], C—H···Cl [d(C16···Cl1ⁱⁱ) = 3.820 (2) Å; d(C20···Cl1^v) = 3.461 (2) Å; symmetry codes: (ii) 1 - x, 2 - y, -z; (v) 2 - x, 2 - y, 1 - z], C—H···N [d(C17···N1^vi) = 3.435 (2) Å], C—H···C [d(C17···C2^vi) = 3.603 (2) Å; symmetry code: (vi) 2 - x, 1 - y, -z] as well as C···Cl contacts [d(C8···Cl1^vii) = 3.3888 (11) Å; symmetry code: (vii) 1 - x, 2 - y, 1 - z] (Fig. 3 and 4), forming an extended three-dimensional network.

Related literature top

For the synthesis, see: Oh et al. (1999). For related structures, see: Trávníček & Popa (2007a,b); Trávníček et al. (2010); Čajan & Trávníček (2011). For the cytotoxic activity of related compounds, see: Benson et al. (2005); Meijer et al. (1997); Štarha et al. (2010); Vrzal et al. (2010).

Experimental top

Compound (I) was prepared, as a prospective ligand for syntheses of transition metal complexes, by the procedure described previously (Oh et al., 1999). The resulting product was recrystallized from hot ethanol and crystals suitable for X-ray analysis were formed after several days of slow evaporation at room temperature. The crystals were characterized by elemental analysis, NMR spectroscopy and single-crystal X-ray analysis. ¹H NMR (DMF-d₇, TMS, 298 K, p.p.m.): 8.28 (s, 1H, C8H), 8.23 (t, 6.8, N6H, 1H), 7.23 (d, 8.2, C15H, 1H), 6.62 (d, 2.4, C12H, 1H), 6.49 (dd, 8.2, 2.4, C14H, 1H), 4.76 (sep, 6.8, C18H, 1H), 4.72 (d, 5.9, C9H, 2H), 3.89 (s, C16H, 3H), 3.80 (s, C17H, 3H), 1.58 (d, 6.8, C19H, C20H, 6H). ¹³C NMR (DMF-d₇, TMS, 298 K, p.p.m.): δ 161.03 (C13), 158.99 (C11), 156.27 (C6), 154.01 (C2), 150.49 (C4), 139.96 (C8), 129.37 (C15), 120.32 (C10), 119.71 (C5), 104.90 (C14), 98.93 (C12), 55.88 (C16), 55.65 (C17), 47.90 (C18), 39.36 (C9), 22.42 (C19, C20). ¹⁵N NMR (DMF-d₇, relative to DMF, 298 K, p.p.m.): δ 241.1 (N7), 228.5 (N1), 224.1 (N3), 179.6 (N9), 91.8 (N6). Analysis calculated for C₁₇H₂₀ClN₅O₂: C, 56.4; H, 5.6; N, 19.4. Found: C, 56.4; H, 5.9; N, 19.0%. Elemental analysis (C, H, N) was performed on a Thermo Scientific Flash 2000 CHNO-S Analyzer. The ¹H, ¹³C and ¹⁵N NMR spectra of the DMF-d₇ solutions were obtained at 300 K on a Varian 400 spectrometer at 400.00 MHz, 100.58 MHz and 40.53 MHz respectively. ¹H and ¹³C spectra were calibrated using tetramethylsilane (TMS) as a reference. The ¹⁵N NMR spectrum was measured relative to the DMF signals.

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: Mercury (Macrae et al., 2006) and DIAMOND (Brandenburg, 2011); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound (I) with the non-hydrogen atoms depicted as thermal ellipsoids at the 50% probability level shown with the atom numbering.
	Fig. 2. A part of the crystal structure of (I) showing the N—H···N hydrogen bonds connecting the individual molecules into centrosymmetric dimers (symmetry code: (i) -x + 1, -y + 1, -z + 1). Hydrogen atoms not involved in the contacts were omitted for clarity.
	Fig. 3. A part of the crystal structure of (I) showing the centrosymmetric dimers connected by C···Cl non-covalent contacts (symmetry codes: (i) -x + 1, -y + 1, -z + 1; (vii) 1 - x, 2 - y, 1 - z). Hydrogen atoms not involved in the contacts were omitted for clarity.
	Fig. 4. A part of the crystal structure of (I) showing the present non-covalent interactions of the C—H···O, C—H···Cl, C—H···N, C—H···C types (symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 - x, 2 - y, -z; (iii) x, y, 1 + z; (iv) 1 - x, 1 - y, -z; (v) 2 - x, 2 - y, 1 - z; (vi) 2 - x, 1 - y, -z). Hydrogen atoms not involved in the contacts were omitted for clarity.

2-Chloro-6-[(2,4-dimethoxybenzyl)amino]-9-isopropyl-9H-purine top

Crystal data top

C₁₇H₂₀ClN₅O₂	Z = 2
M_r = 361.83	F(000) = 380
Triclinic, P1	D_x = 1.417 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8620 (2) Å	Cell parameters from 7872 reflections
b = 9.20164 (18) Å	θ = 3.0–31.9°
c = 13.3027 (3) Å	µ = 0.25 mm⁻¹
α = 82.4472 (18)°	T = 100 K
β = 74.803 (2)°	Prism, colourless
γ = 66.012 (2)°	0.40 × 0.35 × 0.30 mm
V = 848.16 (3) Å³

Data collection top

Agilent Xcalibur Sapphire2 diffractometer	2965 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2704 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.009
Detector resolution: 8.3611 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→8
T_min = 0.908, T_max = 0.930	l = −15→15
7228 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0452P)² + 0.2812P] where P = (F_o² + 2F_c²)/3
2965 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₇H₂₀ClN₅O₂	γ = 66.012 (2)°
M_r = 361.83	V = 848.16 (3) Å³
Triclinic, P1	Z = 2
a = 7.8620 (2) Å	Mo Kα radiation
b = 9.20164 (18) Å	µ = 0.25 mm⁻¹
c = 13.3027 (3) Å	T = 100 K
α = 82.4472 (18)°	0.40 × 0.35 × 0.30 mm
β = 74.803 (2)°

Data collection top

Agilent Xcalibur Sapphire2 diffractometer	2965 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2704 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.930	R_int = 0.009
7228 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.10	Δρ_max = 0.28 e Å⁻³
2965 reflections	Δρ_min = −0.19 e Å⁻³
230 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
Cl1	0.70269 (5)	1.09303 (4)	0.25218 (2)	0.02037 (12)
O1	0.32700 (14)	0.87203 (11)	0.09283 (7)	0.0211 (2)
O2	0.83383 (14)	0.47675 (11)	−0.12752 (7)	0.0219 (2)
N1	0.58970 (15)	0.86255 (13)	0.31864 (8)	0.0154 (2)
N3	0.75392 (16)	0.92987 (13)	0.42340 (8)	0.0158 (2)
N6	0.48258 (16)	0.65791 (13)	0.35975 (8)	0.0157 (2)
H6	0.4819	0.5716	0.3970	0.019*
N7	0.63884 (16)	0.60705 (13)	0.55906 (8)	0.0164 (2)
N9	0.77924 (15)	0.76630 (13)	0.58170 (8)	0.0149 (2)
C2	0.67876 (18)	0.94292 (15)	0.34373 (10)	0.0151 (3)
C4	0.72769 (18)	0.81144 (15)	0.48852 (10)	0.0143 (3)
C5	0.64099 (18)	0.71309 (15)	0.47514 (10)	0.0145 (3)
C6	0.56932 (18)	0.74185 (15)	0.38453 (10)	0.0142 (3)
C8	0.72325 (19)	0.64331 (15)	0.62003 (10)	0.0170 (3)
H8	0.7432	0.5891	0.6844	0.020*
C9	0.38927 (19)	0.70512 (16)	0.27300 (10)	0.0157 (3)
H9A	0.3342	0.8228	0.2670	0.019*
H9B	0.2820	0.6692	0.2888	0.019*
C10	0.51862 (18)	0.64023 (15)	0.16885 (10)	0.0148 (3)
C11	0.47845 (18)	0.72793 (15)	0.07743 (10)	0.0156 (3)
C12	0.58604 (19)	0.67038 (16)	−0.01979 (10)	0.0171 (3)
H12	0.5559	0.7309	−0.0809	0.021*
C13	0.73911 (19)	0.52284 (16)	−0.02749 (10)	0.0173 (3)
C14	0.7841 (2)	0.43487 (16)	0.06153 (11)	0.0187 (3)
H14	0.8896	0.3352	0.0566	0.022*
C15	0.67172 (19)	0.49520 (15)	0.15851 (10)	0.0178 (3)
H15	0.7016	0.4343	0.2196	0.021*
C16	0.2745 (2)	0.96545 (17)	0.00354 (11)	0.0259 (3)
H16A	0.3842	0.9866	−0.0399	0.039*
H16B	0.1682	1.0665	0.0256	0.039*
H16C	0.2350	0.9077	−0.0367	0.039*
C17	0.9907 (2)	0.32597 (17)	−0.14131 (12)	0.0253 (3)
H17A	1.0488	0.3093	−0.2158	0.038*
H17B	0.9447	0.2416	−0.1120	0.038*
H17C	1.0861	0.3235	−0.1056	0.038*
C18	0.89162 (19)	0.83166 (15)	0.62220 (10)	0.0161 (3)
H18	0.8547	0.9460	0.5990	0.019*
C19	0.8456 (2)	0.82494 (17)	0.74010 (10)	0.0199 (3)
H19A	0.8871	0.7136	0.7649	0.030*
H19B	0.7073	0.8793	0.7669	0.030*
H19C	0.9125	0.8776	0.7649	0.030*
C20	1.1021 (2)	0.74454 (19)	0.57366 (12)	0.0267 (3)
H20A	1.1445	0.6337	0.5995	0.040*
H20B	1.1762	0.7962	0.5925	0.040*
H20C	1.1219	0.7474	0.4977	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0287 (2)	0.02086 (19)	0.01726 (18)	−0.01511 (15)	−0.00878 (14)	0.00570 (13)
O1	0.0227 (5)	0.0188 (5)	0.0140 (5)	0.0003 (4)	−0.0057 (4)	0.0005 (4)
O2	0.0223 (5)	0.0198 (5)	0.0176 (5)	−0.0041 (4)	0.0001 (4)	−0.0037 (4)
N1	0.0163 (5)	0.0155 (6)	0.0139 (5)	−0.0065 (5)	−0.0019 (4)	−0.0005 (4)
N3	0.0176 (6)	0.0145 (5)	0.0153 (6)	−0.0066 (5)	−0.0037 (4)	0.0000 (4)
N6	0.0220 (6)	0.0169 (6)	0.0122 (5)	−0.0109 (5)	−0.0061 (5)	0.0024 (4)
N7	0.0208 (6)	0.0163 (6)	0.0131 (5)	−0.0085 (5)	−0.0038 (4)	0.0003 (4)
N9	0.0184 (6)	0.0153 (5)	0.0130 (5)	−0.0078 (5)	−0.0050 (4)	−0.0005 (4)
C2	0.0158 (6)	0.0134 (6)	0.0139 (6)	−0.0049 (5)	−0.0012 (5)	−0.0003 (5)
C4	0.0141 (6)	0.0132 (6)	0.0127 (6)	−0.0031 (5)	−0.0012 (5)	−0.0022 (5)
C5	0.0144 (6)	0.0145 (6)	0.0134 (6)	−0.0048 (5)	−0.0016 (5)	−0.0027 (5)
C6	0.0123 (6)	0.0133 (6)	0.0142 (6)	−0.0033 (5)	−0.0003 (5)	−0.0029 (5)
C8	0.0223 (7)	0.0160 (6)	0.0144 (6)	−0.0098 (6)	−0.0030 (5)	−0.0002 (5)
C9	0.0180 (6)	0.0178 (7)	0.0141 (6)	−0.0087 (5)	−0.0062 (5)	0.0012 (5)
C10	0.0178 (7)	0.0164 (7)	0.0153 (6)	−0.0108 (5)	−0.0054 (5)	0.0004 (5)
C11	0.0153 (6)	0.0150 (6)	0.0182 (7)	−0.0068 (5)	−0.0049 (5)	−0.0004 (5)
C12	0.0206 (7)	0.0174 (7)	0.0146 (6)	−0.0084 (6)	−0.0058 (5)	0.0024 (5)
C13	0.0178 (7)	0.0190 (7)	0.0173 (7)	−0.0098 (6)	−0.0022 (5)	−0.0032 (5)
C14	0.0195 (7)	0.0131 (6)	0.0228 (7)	−0.0045 (5)	−0.0068 (6)	−0.0012 (5)
C15	0.0231 (7)	0.0163 (7)	0.0179 (7)	−0.0098 (6)	−0.0094 (6)	0.0031 (5)
C16	0.0278 (8)	0.0227 (7)	0.0181 (7)	0.0001 (6)	−0.0084 (6)	0.0033 (6)
C17	0.0223 (7)	0.0218 (7)	0.0265 (8)	−0.0052 (6)	0.0006 (6)	−0.0071 (6)
C18	0.0198 (7)	0.0155 (6)	0.0168 (7)	−0.0091 (5)	−0.0063 (5)	−0.0012 (5)
C19	0.0240 (7)	0.0232 (7)	0.0162 (7)	−0.0114 (6)	−0.0065 (6)	−0.0013 (5)
C20	0.0212 (8)	0.0354 (9)	0.0258 (8)	−0.0124 (7)	−0.0010 (6)	−0.0129 (6)

Geometric parameters (Å, º) top

Cl1—C2	1.7537 (13)	C10—C11	1.4021 (18)
O1—C11	1.3703 (16)	C11—C12	1.3824 (19)
O1—C16	1.4213 (16)	C12—C13	1.3948 (19)
O2—C13	1.3700 (16)	C12—H12	0.9500
O2—C17	1.4270 (17)	C13—C14	1.3847 (19)
N1—C2	1.3256 (17)	C14—C15	1.3947 (19)
N1—C6	1.3574 (17)	C14—H14	0.9500
N3—C2	1.3130 (17)	C15—H15	0.9500
N3—C4	1.3496 (17)	C16—H16A	0.9800
N6—C6	1.3353 (17)	C16—H16B	0.9800
N6—C9	1.4532 (16)	C16—H16C	0.9800
N6—H6	0.8800	C17—H17A	0.9800
N7—C8	1.3201 (17)	C17—H17B	0.9800
N7—C5	1.3841 (17)	C17—H17C	0.9800
N9—C4	1.3655 (16)	C18—C19	1.5131 (18)
N9—C8	1.3676 (17)	C18—C20	1.5153 (19)
N9—C18	1.4831 (16)	C18—H18	1.0000
C4—C5	1.3866 (18)	C19—H19A	0.9800
C5—C6	1.4113 (18)	C19—H19B	0.9800
C8—H8	0.9500	C19—H19C	0.9800
C9—C10	1.5151 (18)	C20—H20A	0.9800
C9—H9A	0.9900	C20—H20B	0.9800
C9—H9B	0.9900	C20—H20C	0.9800
C10—C15	1.3799 (19)

C11—O1—C16	117.98 (10)	C13—C12—H12	120.2
C13—O2—C17	117.58 (11)	O2—C13—C14	125.13 (12)
C2—N1—C6	117.18 (11)	O2—C13—C12	114.52 (12)
C2—N3—C4	109.33 (11)	C14—C13—C12	120.35 (12)
C6—N6—C9	121.82 (11)	C13—C14—C15	118.82 (12)
C6—N6—H6	119.1	C13—C14—H14	120.6
C9—N6—H6	119.1	C15—C14—H14	120.6
C8—N7—C5	103.89 (11)	C10—C15—C14	122.29 (12)
C4—N9—C8	105.86 (10)	C10—C15—H15	118.9
C4—N9—C18	124.22 (11)	C14—C15—H15	118.9
C8—N9—C18	129.61 (11)	O1—C16—H16A	109.5
N3—C2—N1	132.07 (12)	O1—C16—H16B	109.5
N3—C2—Cl1	114.30 (10)	H16A—C16—H16B	109.5
N1—C2—Cl1	113.62 (9)	O1—C16—H16C	109.5
N3—C4—N9	126.58 (12)	H16A—C16—H16C	109.5
N3—C4—C5	127.06 (12)	H16B—C16—H16C	109.5
N9—C4—C5	106.35 (11)	O2—C17—H17A	109.5
N7—C5—C4	110.24 (11)	O2—C17—H17B	109.5
N7—C5—C6	133.27 (12)	H17A—C17—H17B	109.5
C4—C5—C6	116.46 (12)	O2—C17—H17C	109.5
N6—C6—N1	118.06 (11)	H17A—C17—H17C	109.5
N6—C6—C5	124.07 (12)	H17B—C17—H17C	109.5
N1—C6—C5	117.87 (11)	N9—C18—C19	111.14 (10)
N7—C8—N9	113.66 (12)	N9—C18—C20	108.83 (10)
N7—C8—H8	123.2	C19—C18—C20	113.22 (12)
N9—C8—H8	123.2	N9—C18—H18	107.8
N6—C9—C10	114.74 (11)	C19—C18—H18	107.8
N6—C9—H9A	108.6	C20—C18—H18	107.8
C10—C9—H9A	108.6	C18—C19—H19A	109.5
N6—C9—H9B	108.6	C18—C19—H19B	109.5
C10—C9—H9B	108.6	H19A—C19—H19B	109.5
H9A—C9—H9B	107.6	C18—C19—H19C	109.5
C15—C10—C11	117.63 (12)	H19A—C19—H19C	109.5
C15—C10—C9	123.29 (12)	H19B—C19—H19C	109.5
C11—C10—C9	119.04 (11)	C18—C20—H20A	109.5
O1—C11—C12	123.76 (11)	C18—C20—H20B	109.5
O1—C11—C10	114.88 (11)	H20A—C20—H20B	109.5
C12—C11—C10	121.36 (12)	C18—C20—H20C	109.5
C11—C12—C13	119.54 (12)	H20A—C20—H20C	109.5
C11—C12—H12	120.2	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N7ⁱ	0.88	2.16	2.9465 (15)	148
C16—H16C···Cl1ⁱⁱ	0.98	2.78	3.4607 (15)	127
C19—H19A···O2ⁱⁱⁱ	0.98	2.57	3.4709 (17)	154

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀ClN₅O₂
M_r	361.83
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.8620 (2), 9.20164 (18), 13.3027 (3)
α, β, γ (°)	82.4472 (18), 74.803 (2), 66.012 (2)
V (Å³)	848.16 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.40 × 0.35 × 0.30

Data collection
Diffractometer	Agilent Xcalibur Sapphire2 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.908, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	7228, 2965, 2704
R_int	0.009

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.079, 1.10
No. of reflections	2965
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.19

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006) and DIAMOND (Brandenburg, 2011), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N7ⁱ	0.88	2.16	2.9465 (15)	148.3
C16—H16C···Cl1ⁱⁱ	0.98	2.78	3.4607 (15)	127
C19—H19A···O2ⁱⁱⁱ	0.98	2.57	3.4709 (17)	154

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

Acknowledgements

This work was supported financially by Palacký University (PrF_2012_009). The authors wish to thank Dr Igor Popa for carrying out the NMR spectroscopy measurements and Mr Tomáš Šilha for performing the CHN elemental analyses.

References

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