trans-Dichloridobis{2-chloro-6-[(3-fluoro­benz­yl)amino]-9-isopropyl-9H-purine-κN7}platinum(II)

Trávníček, Z.; Štarha, P.

doi:10.1107/S1600536813013202

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page m331

doi:10.1107/S1600536813013202

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trans-Dichloridobis{2-chloro-6-[(3-fluorobenzyl)amino]-9-isopropyl-9H-purine-κN⁷}platinum(II)

Zdeněk Trávníček ^a ^* and Pavel Štarha ^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 10 April 2013; accepted 14 May 2013; online 18 May 2013)

In the title compound, trans-[PtCl₂(C₁₅H₁₅ClFN₅)₂], the Pt^II atom, located on an inversion centre, is coordinated by the purine N atoms of the 2-chloro-6-[(3-fluorobenzyl)amino]-9-isopropyl-9H-purine ligands and two Cl atoms in a slightly distorted trans-square-planar coordination geometry [N—Pt—Cl angles = 89.91 (5) and 90.09 (5)°]. Weak intramolecular N—H⋯Cl contacts occur. In the crystal, C—H⋯Cl and C—H⋯F contacts, as well as weak π–π stacking interactions [centroid–centroid distances = 3.5000 (11) and 3.6495 (12) Å] connect the molecules into a three-dimensional architecture.

Related literature

For the structures of platinum(II) dichlorido complexes involving different 2-chloro-6-[(substituted-benzyl)amino]-9-isopropyl-9H-purine derivatives, see: Trávníček et al. (2006 ); Szüčová et al. (2008 ). For the synthesis of 2-chloro-6-[(substituted-benzyl)amino]-9-isopropyl-9H-purine derivatives, see: Štarha et al. (2009 ).

Experimental

Crystal data

[PtCl₂(C₁₅H₁₅ClFN₅)₂]
M_r = 905.53
Monoclinic, P 2₁ /c
a = 9.37786 (13) Å
b = 12.86530 (17) Å
c = 14.2891 (2) Å
β = 107.9165 (16)°
V = 1640.36 (4) Å³
Z = 2
Mo Kα radiation
μ = 4.65 mm⁻¹
T = 105 K
0.35 × 0.35 × 0.35 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.293, T_max = 0.293
13582 measured reflections
2881 independent reflections
2726 reflections with I > 2σ(I)
R_int = 0.010

Refinement

R[F² > 2σ(F²)] = 0.015
wR(F²) = 0.037
S = 1.10
2881 reflections
216 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯Cl2ⁱ	0.88	2.53	3.222 (2)	136
C13—H13A⋯Cl2ⁱⁱ	0.95	2.86	3.492 (2)	125
C18—H18A⋯F1ⁱⁱⁱ	0.98	2.49	3.450 (3)	166
Symmetry codes: (i) -x, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z.

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/S1600536813013202/jj2166sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013202/jj2166Isup2.hkl

checkCIF report

Comment top

In the title compound, the Pt^II atom is located on an inversion centre and thus, the asymmetric unit contains one-half of the described platinum(II) complex (Fig. 1). The central Pt^II atom is four-coordinated by two chloride anions [Pt—Cl = 2.2940 (5) Å] and two 2-chloro-6-[(3-fluorobenzyl)amino]-9-isopropyl-9H-purine molecules [Pt—N = 2.011 (2) Å], which are bonded to platinum through their N7 atoms of the purine moieties. The geometry of the complex is slightly distorted square-planar with the N—Pt—Cl angles in the vicinity of the central metal atom of 89.91 (5)° and 90.09 (5)°, and the mean plane fitted through the PtCl₂N₂ unit (r.m.s. deviation = 0.000 Å) being planar. Both the essentially planar purine moieties [with the maximum deviation of 0.050 (2) Å for the C5 atom] are mutually coplanar and each of them forms the dihedral angle of 62.04 (3)° and 49.58 (5)° with the PtCl₂N₂ unit, and the benzene ring, respectively (Fig. 1). The molecular structure involves weak N6—H6A···Cl2 intramolecular interactions (Table 1, Fig. 1). In the crystal, the molecules are connected together through weak C13—H13A···Cl2, C18—H18A···F1 and π···π (between the six-membered pyrimidine and benzene rings) intermolecular interactions into a three-dimensional architecture (Fig. 2 and 3, Table 1).

Related literature top

For the structures of platinum(II) dichlorido complexes involving different 2-chloro-6-[(substituted-benzyl)amino]-9-isopropyl-9H-purine derivatives, see: Trávníček et al. (2006); Szüčová et al. (2008). For the synthesis, see: Štarha et al. (2009).

Experimental top

The solution of 2-chloro-6-[(3-fluorobenzyl)amino]-9-isopropyl-9H-purine (0.5 mmol; prepared according to the previously described procedure, (Štarha et al., 2009) in acetone (10 ml) was slowly poured into the distilled water solution of K₂PtCl₄ (0.25 mmol). The reaction mixture was stirred at laboratory temperature, until the initial orange colour turned to yellow. The solid was collected by filtration and washed with distilled water and acetone. Part of the product was recrystallized from N,N`-dimethylformamide. The crystals suitable for a single-crystal X-ray analysis formed after two weeks. Analysis calculated for C₃₀H₃₀N₁₀Cl₄F₂Pt₁: C 39.8, H 3.3, N 15.5%; found: C 39.9, H 3.3, N 15.3%. 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 atom numbering scheme and the non-hydrogen atoms at the 50% probability level. Dashed lines indicate weak N6—H6A···Cl2ⁱ intramolecular interactions (symmetry code: i) -x, -y, -z).
	Fig. 2. Packing diagram of the title compound viewed along the a axis. Dashed lines indicate weak C13—H13A^iv···Cl2 intermolecular and π···π stacking interactions (Cg···Cg = 3.5001 Å) (symmetry code: iv) x, -y+1/2, z + 1/2).
	Fig. 3. Packing diagram of the title compound viewed along the b axis. Dashed lines indicate weak C18—H18A···F1ⁱⁱⁱ intermolecular interactions (symmetry code: iii) -x+1, -y, -z).

trans-Dichloridobis{2-chloro-6-[(3-fluorobenzyl)amino]-9-isopropyl-9H-purine-κN⁷}platinum(II) top

Crystal data top

[PtCl₂(C₁₅H₁₅ClFN₅)₂]	F(000) = 888
M_r = 905.53	D_x = 1.833 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15658 reflections
a = 9.37786 (13) Å	θ = 3.0–31.7°
b = 12.86530 (17) Å	µ = 4.65 mm⁻¹
c = 14.2891 (2) Å	T = 105 K
β = 107.9165 (16)°	Prism, yellow-orange
V = 1640.36 (4) Å³	0.35 × 0.35 × 0.35 mm
Z = 2

Data collection top

Agilent Xcalibur Sapphire2 diffractometer	2881 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2726 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 = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −15→13
T_min = 0.293, T_max = 0.293	l = −16→16
13582 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)] = 0.015	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.037	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0204P)² + 1.5464P] where P = (F_o² + 2F_c²)/3
2881 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[PtCl₂(C₁₅H₁₅ClFN₅)₂]	V = 1640.36 (4) Å³
M_r = 905.53	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.37786 (13) Å	µ = 4.65 mm⁻¹
b = 12.86530 (17) Å	T = 105 K
c = 14.2891 (2) Å	0.35 × 0.35 × 0.35 mm
β = 107.9165 (16)°

Data collection top

Agilent Xcalibur Sapphire2 diffractometer	2881 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2726 reflections with I > 2σ(I)
T_min = 0.293, T_max = 0.293	R_int = 0.010
13582 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.015	0 restraints
wR(F²) = 0.037	H-atom parameters constrained
S = 1.10	Δρ_max = 0.52 e Å⁻³
2881 reflections	Δρ_min = −0.32 e Å⁻³
216 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
Pt1	0.0000	0.0000	0.0000	0.01222 (5)
Cl1	0.73503 (6)	0.18413 (6)	0.31702 (4)	0.03616 (16)
Cl2	−0.15533 (5)	0.11059 (4)	0.04896 (4)	0.02297 (12)
F1	0.32167 (15)	0.15374 (11)	−0.40416 (9)	0.0297 (3)
N1	0.52347 (19)	0.13487 (14)	0.15853 (12)	0.0174 (4)
N3	0.49172 (18)	0.08828 (14)	0.31434 (12)	0.0164 (4)
N6	0.34612 (19)	0.10095 (14)	0.00859 (12)	0.0176 (4)
H6A	0.2599	0.0723	−0.0239	0.021*
N7	0.1537 (2)	0.01264 (12)	0.13330 (14)	0.0145 (4)
N9	0.2482 (2)	0.01119 (12)	0.29616 (14)	0.0148 (4)
C2	0.5616 (2)	0.12816 (17)	0.25559 (15)	0.0189 (4)
C4	0.3566 (2)	0.05155 (15)	0.26050 (14)	0.0137 (4)
C5	0.2990 (2)	0.05145 (15)	0.15906 (14)	0.0137 (4)
C6	0.3894 (2)	0.09529 (15)	0.10649 (14)	0.0140 (4)
C8	0.1290 (3)	−0.01030 (15)	0.21725 (17)	0.0160 (4)
H8A	0.0377	−0.0387	0.2215	0.019*
C9	0.4310 (2)	0.15101 (17)	−0.04837 (15)	0.0187 (4)
H9A	0.5135	0.1049	−0.0524	0.022*
H9B	0.4755	0.2165	−0.0159	0.022*
C10	0.3281 (2)	0.17380 (15)	−0.15035 (15)	0.0157 (4)
C11	0.3731 (2)	0.15135 (16)	−0.23221 (15)	0.0179 (4)
H11A	0.4677	0.1201	−0.2251	0.021*
C12	0.2768 (2)	0.17560 (16)	−0.32396 (15)	0.0179 (4)
C13	0.1394 (2)	0.22057 (16)	−0.33922 (15)	0.0205 (4)
H13A	0.0766	0.2364	−0.4037	0.025*
C14	0.0949 (2)	0.24231 (17)	−0.25725 (16)	0.0209 (4)
H14A	0.0000	0.2733	−0.2652	0.025*
C15	0.1886 (2)	0.21895 (16)	−0.16387 (15)	0.0191 (4)
H15A	0.1569	0.2340	−0.1083	0.023*
C16	0.2665 (3)	−0.01102 (16)	0.40122 (16)	0.0181 (5)
H16A	0.3434	0.0378	0.4424	0.022*
C17	0.1208 (3)	0.00727 (17)	0.42384 (19)	0.0238 (5)
H17A	0.0852	0.0780	0.4042	0.036*
H17B	0.1375	−0.0014	0.4945	0.036*
H17C	0.0455	−0.0429	0.3874	0.036*
C18	0.3242 (3)	−0.1208 (2)	0.42492 (17)	0.0307 (5)
H18A	0.4155	−0.1299	0.4062	0.046*
H18B	0.2477	−0.1702	0.3883	0.046*
H18C	0.3466	−0.1333	0.4956	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.00955 (7)	0.01405 (7)	0.01116 (7)	−0.00130 (4)	0.00039 (5)	−0.00091 (4)
Cl1	0.0192 (3)	0.0674 (5)	0.0179 (3)	−0.0222 (3)	−0.0002 (2)	0.0010 (3)
Cl2	0.0140 (2)	0.0248 (3)	0.0274 (3)	0.0009 (2)	0.0023 (2)	−0.0114 (2)
F1	0.0371 (8)	0.0390 (8)	0.0154 (6)	0.0029 (6)	0.0115 (6)	−0.0034 (6)
N1	0.0135 (8)	0.0234 (9)	0.0147 (8)	−0.0018 (7)	0.0034 (7)	0.0004 (7)
N3	0.0122 (8)	0.0219 (9)	0.0140 (8)	−0.0012 (7)	0.0022 (7)	−0.0011 (7)
N6	0.0149 (8)	0.0232 (9)	0.0123 (8)	−0.0060 (7)	0.0008 (7)	0.0012 (7)
N7	0.0133 (9)	0.0159 (9)	0.0130 (9)	−0.0009 (6)	0.0022 (7)	−0.0001 (6)
N9	0.0141 (9)	0.0180 (9)	0.0112 (9)	−0.0013 (6)	0.0024 (7)	0.0007 (6)
C2	0.0112 (9)	0.0260 (12)	0.0174 (10)	−0.0028 (8)	0.0010 (8)	−0.0011 (9)
C4	0.0133 (9)	0.0137 (10)	0.0140 (10)	0.0016 (8)	0.0039 (8)	0.0006 (8)
C5	0.0124 (9)	0.0125 (10)	0.0145 (9)	0.0013 (8)	0.0015 (8)	−0.0010 (8)
C6	0.0128 (9)	0.0133 (10)	0.0148 (10)	0.0016 (8)	0.0026 (8)	−0.0006 (8)
C8	0.0125 (11)	0.0189 (11)	0.0155 (11)	−0.0032 (8)	0.0024 (9)	−0.0003 (8)
C9	0.0155 (10)	0.0247 (11)	0.0158 (10)	−0.0026 (9)	0.0046 (8)	0.0018 (9)
C10	0.0166 (10)	0.0139 (10)	0.0163 (10)	−0.0030 (8)	0.0046 (8)	0.0005 (8)
C11	0.0177 (10)	0.0170 (10)	0.0192 (10)	0.0007 (8)	0.0059 (8)	0.0010 (8)
C12	0.0247 (11)	0.0170 (10)	0.0138 (10)	−0.0026 (9)	0.0085 (9)	−0.0006 (8)
C13	0.0222 (11)	0.0191 (11)	0.0169 (10)	−0.0020 (9)	0.0009 (8)	0.0044 (8)
C14	0.0148 (10)	0.0200 (11)	0.0268 (11)	0.0022 (8)	0.0050 (9)	0.0051 (9)
C15	0.0214 (11)	0.0196 (11)	0.0187 (10)	0.0007 (9)	0.0098 (9)	0.0009 (9)
C16	0.0164 (11)	0.0283 (12)	0.0097 (10)	−0.0043 (8)	0.0039 (9)	−0.0014 (8)
C17	0.0232 (13)	0.0290 (13)	0.0227 (13)	−0.0019 (9)	0.0121 (10)	−0.0015 (9)
C18	0.0334 (13)	0.0408 (14)	0.0195 (11)	0.0122 (11)	0.0103 (10)	0.0117 (10)

Geometric parameters (Å, º) top

Pt1—N7	2.0108 (18)	C9—H9A	0.9900
Pt1—N7ⁱ	2.0109 (18)	C9—H9B	0.9900
Pt1—Cl2	2.2940 (5)	C10—C15	1.390 (3)
Pt1—Cl2ⁱ	2.2940 (5)	C10—C11	1.390 (3)
Cl1—C2	1.748 (2)	C11—C12	1.380 (3)
F1—C12	1.366 (2)	C11—H11A	0.9500
N1—C2	1.324 (3)	C12—C13	1.368 (3)
N1—C6	1.348 (3)	C13—C14	1.387 (3)
N3—C2	1.317 (3)	C13—H13A	0.9500
N3—C4	1.349 (3)	C14—C15	1.386 (3)
N6—C6	1.333 (3)	C14—H14A	0.9500
N6—C9	1.453 (3)	C15—H15A	0.9500
N6—H6A	0.8800	C16—C18	1.513 (3)
N7—C8	1.323 (3)	C16—C17	1.516 (3)
N7—C5	1.390 (3)	C16—H16A	1.0000
N9—C8	1.350 (3)	C17—H17A	0.9800
N9—C4	1.372 (3)	C17—H17B	0.9800
N9—C16	1.485 (3)	C17—H17C	0.9800
C4—C5	1.382 (3)	C18—H18A	0.9800
C5—C6	1.412 (3)	C18—H18B	0.9800
C8—H8A	0.9500	C18—H18C	0.9800
C9—C10	1.508 (3)

N7—Pt1—N7ⁱ	180.0	H9A—C9—H9B	108.3
N7—Pt1—Cl2	89.91 (5)	C15—C10—C11	119.10 (19)
N7ⁱ—Pt1—Cl2	90.09 (5)	C15—C10—C9	120.70 (18)
N7—Pt1—Cl2ⁱ	90.09 (5)	C11—C10—C9	120.19 (18)
N7ⁱ—Pt1—Cl2ⁱ	89.91 (5)	C12—C11—C10	118.25 (19)
Cl2—Pt1—Cl2ⁱ	180.00 (3)	C12—C11—H11A	120.9
C2—N1—C6	117.27 (17)	C10—C11—H11A	120.9
C2—N3—C4	109.68 (17)	C13—C12—F1	118.13 (19)
C6—N6—C9	124.74 (17)	C13—C12—C11	123.80 (19)
C6—N6—H6A	117.6	F1—C12—C11	118.06 (19)
C9—N6—H6A	117.6	C12—C13—C14	117.65 (19)
C8—N7—C5	105.71 (18)	C12—C13—H13A	121.2
C8—N7—Pt1	124.49 (15)	C14—C13—H13A	121.2
C5—N7—Pt1	129.68 (14)	C15—C14—C13	120.2 (2)
C8—N9—C4	106.56 (18)	C15—C14—H14A	119.9
C8—N9—C16	127.83 (19)	C13—C14—H14A	119.9
C4—N9—C16	125.45 (18)	C14—C15—C10	121.01 (19)
N3—C2—N1	131.76 (19)	C14—C15—H15A	119.5
N3—C2—Cl1	114.12 (15)	C10—C15—H15A	119.5
N1—C2—Cl1	114.11 (15)	N9—C16—C18	109.15 (17)
N3—C4—N9	126.44 (18)	N9—C16—C17	110.76 (19)
N3—C4—C5	126.43 (18)	C18—C16—C17	112.39 (19)
N9—C4—C5	107.08 (17)	N9—C16—H16A	108.1
C4—C5—N7	108.25 (17)	C18—C16—H16A	108.1
C4—C5—C6	116.90 (17)	C17—C16—H16A	108.1
N7—C5—C6	134.64 (18)	C16—C17—H17A	109.5
N6—C6—N1	119.28 (18)	C16—C17—H17B	109.5
N6—C6—C5	122.78 (18)	H17A—C17—H17B	109.5
N1—C6—C5	117.92 (17)	C16—C17—H17C	109.5
N7—C8—N9	112.38 (19)	H17A—C17—H17C	109.5
N7—C8—H8A	123.8	H17B—C17—H17C	109.5
N9—C8—H8A	123.8	C16—C18—H18A	109.5
N6—C9—C10	109.24 (16)	C16—C18—H18B	109.5
N6—C9—H9A	109.8	H18A—C18—H18B	109.5
C10—C9—H9A	109.8	C16—C18—H18C	109.5
N6—C9—H9B	109.8	H18A—C18—H18C	109.5
C10—C9—H9B	109.8	H18B—C18—H18C	109.5

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···Cl2ⁱ	0.88	2.53	3.222 (2)	136
C13—H13A···Cl2ⁱⁱ	0.95	2.86	3.492 (2)	125
C18—H18A···F1ⁱⁱⁱ	0.98	2.49	3.450 (3)	166

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

Experimental details

Crystal data
Chemical formula	[PtCl₂(C₁₅H₁₅ClFN₅)₂]
M_r	905.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	105
a, b, c (Å)	9.37786 (13), 12.86530 (17), 14.2891 (2)
β (°)	107.9165 (16)
V (Å³)	1640.36 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.65
Crystal size (mm)	0.35 × 0.35 × 0.35

Data collection
Diffractometer	Agilent Xcalibur Sapphire2 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.293, 0.293
No. of measured, independent and observed [I > 2σ(I)] reflections	13582, 2881, 2726
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.037, 1.10
No. of reflections	2881
No. of parameters	216
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.32

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), 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—H6A···Cl2ⁱ	0.88	2.53	3.222 (2)	136
C13—H13A···Cl2ⁱⁱ	0.95	2.86	3.492 (2)	125
C18—H18A···F1ⁱⁱⁱ	0.98	2.49	3.450 (3)	166

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

Acknowledgements

This work was supported by Palacký University (grant No. PrF_2013_015). The authors wish to thank Mr Tomáš Šilha for performing the CHN elemental analysis.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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