2-(1-Adamant­yl)-1-(3-amino­phen­yl)ethanol

Rouchal, M.; Kozubková, Z.; Nečas, M.; Vícha, R.

doi:10.1107/S1600536811034763

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2515

doi:10.1107/S1600536811034763

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2-(1-Adamantyl)-1-(3-aminophenyl)ethanol

Michal Rouchal,^a Zuzana Kozubková,^a Marek Nečas ^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 16 August 2011; accepted 24 August 2011; online 27 August 2011)

In the crystal structure of the title compound, C₁₈H₂₅NO, molecules are linked via O—H⋯N hydrogen bonds, forming chains parallel to the c axis. Additional weak N—H⋯O interactions stabilize the crystal packing. The adamantane cage consists of three fused cyclohexane rings in almost ideal chair conformations, with C—C—C angles in the range 107.9 (10)–111.3 (11)°.

Related literature

For the biological activity of adamantane-bearing compounds, see: van der Schyf & Geldenhuys (2009). For related structures, see: Rouchal et al. (2009 , 2010 ).

Experimental

Crystal data

C₁₈H₂₅NO
M_r = 271.39
Orthorhombic, P c c n
a = 16.4467 (7) Å
b = 22.1873 (9) Å
c = 8.1033 (4) Å
V = 2957.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 120 K
0.30 × 0.20 × 0.10 mm

Data collection

Kuma KM-4 CCD 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 = 0.984, T_max = 1.000
30937 measured reflections
2602 independent reflections
1716 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.068
S = 0.85
2602 reflections
190 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1ⁱ	0.84	2.10	2.9400 (14)	176
N1—H1C⋯O1ⁱⁱ	0.930 (15)	2.295 (15)	3.2048 (16)	166.0 (13)
N1—H1B⋯O1ⁱⁱⁱ	0.930 (16)	2.357 (16)	3.2472 (16)	160.1 (14)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y, z+1.

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 (Farrugia, 1997 ) 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/S1600536811034763/pk2344sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034763/pk2344Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034763/pk2344Isup3.cml

checkCIF report

Comment top

It is matter of common knowledge that the well advised introduction of the highly lipophilic adamantane moiety into biologically active compounds might improve some pharmacological properties of the resulting molecule (van der Schyf & Geldenhuys, 2009). The title compound belongs to the series of recently synthesized building blocks for drug modification based on adamantylated aromatic amines.

The asymmetric unit of the title compound consists of a single molecule (Fig. 1). The benzene ring is nearly planar with a maximum deviation from the best plane being 0.006 (13) Å for C13. The torsion angles describing an arrangement of adamantane cage, benzene ring and aliphatic linker C1–C11–C12–C13, C11–C12–C13–C18, and C10–C1–C11–C12 are 158.37 (11), -95.75 (14), and -178.42 (11)°, respectively. The presented structure is linked into pairs by O–H···N hydrogen bonds (Fig. 2, Table 1). The crystal packing is further stabilized via intermolecular N–H···O interactions (Table 1).

Related literature top

For the biological activity of adamantane-bearing compounds, see: van der Schyf & Geldenhuys (2009). For related structures, see: Rouchal et al. (2009, 2010).

Experimental top

2-(1-Adamantyl)-1-(3-nitrophenyl)ethanol (350 mg, 1.16 mmol) was dissolved in methanol (34 cm³) and 7 cm³ of hydrochloric acid/water (1/1, v/v) was added. Into the refluxed and well stirred mixture, portions of an iron powder were added successively. The reaction was stopped when TLC indicated the consumption of all starting material. The mixture was neutralized with 5% solution of NaOH (50 cm³) and extracted with diethyl ether (6 × 10 cm³). Combined organic layers were twice washed with brine, dried over sodium sulfate and evaporated in vacuum. The purification of crude material by washing with hexane provided the desired product as a colourless crystalline powder (258 mg, 82%, mp 415–418 K). The crystal used for data collection was grown by spontaneous evaporation from diethyl ether 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 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Ellipsoid plot of the asymmetric unit with atoms represented as 50% probability ellipsoids. Hydrogen atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure of the title compound showing the H-bonds (dashed lines). H-atoms (except those which are involved in H-bonding) have been omitted for clarity. Symmetry codes: (i) -x+0.5,y,z-0.5; (ii) x,-y+1.5,z+0.5; (iii) x,y,z+1.

2-(1-Adamantyl)-1-(3-aminophenyl)ethanol top

Crystal data top

C₁₈H₂₅NO	D_x = 1.219 Mg m⁻³
M_r = 271.39	Melting point: 417 K
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 6715 reflections
a = 16.4467 (7) Å	θ = 2.9–27.3°
b = 22.1873 (9) Å	µ = 0.07 mm⁻¹
c = 8.1033 (4) Å	T = 120 K
V = 2957.0 (2) Å³	Block, colourless
Z = 8	0.30 × 0.20 × 0.10 mm
F(000) = 1184

Data collection top

Kuma KM-4 CCD diffractometer	2602 independent reflections
Radiation source: fine-focus sealed tube	1716 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 0.06 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scans	h = −18→19
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −26→26
T_min = 0.984, T_max = 1.000	l = −8→9
30937 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ²(F_o²) + (0.0369P)²] where P = (F_o² + 2F_c²)/3
2602 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₂₅NO	V = 2957.0 (2) Å³
M_r = 271.39	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 16.4467 (7) Å	µ = 0.07 mm⁻¹
b = 22.1873 (9) Å	T = 120 K
c = 8.1033 (4) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Kuma KM-4 CCD diffractometer	2602 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1716 reflections with I > 2σ(I)
T_min = 0.984, T_max = 1.000	R_int = 0.053
30937 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	Δρ_max = 0.14 e Å⁻³
2602 reflections	Δρ_min = −0.15 e Å⁻³
190 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
O1	0.36193 (5)	0.68130 (4)	0.21617 (11)	0.0266 (2)
H1A	0.3139	0.6810	0.2513	0.040*
N1	0.30745 (7)	0.68654 (6)	0.83127 (16)	0.0257 (3)
C1	0.54376 (8)	0.63700 (5)	0.11634 (15)	0.0185 (3)
C2	0.53840 (8)	0.57371 (6)	0.04034 (16)	0.0240 (3)
H2A	0.5560	0.5434	0.1227	0.029*
H2B	0.4813	0.5649	0.0102	0.029*
C3	0.59193 (8)	0.56895 (6)	−0.11291 (17)	0.0271 (4)
H3	0.5875	0.5274	−0.1599	0.033*
C4	0.68033 (8)	0.58181 (6)	−0.06886 (18)	0.0290 (4)
H4A	0.6998	0.5519	0.0127	0.035*
H4B	0.7147	0.5785	−0.1688	0.035*
C5	0.68711 (8)	0.64514 (6)	0.00313 (17)	0.0258 (3)
H5	0.7450	0.6536	0.0332	0.031*
C6	0.65776 (8)	0.69158 (6)	−0.12231 (18)	0.0281 (4)
H6A	0.6923	0.6900	−0.2222	0.034*
H6B	0.6619	0.7326	−0.0746	0.034*
C7	0.56932 (8)	0.67818 (6)	−0.16850 (17)	0.0254 (3)
H7	0.5503	0.7082	−0.2519	0.030*
C8	0.51604 (8)	0.68229 (6)	−0.01404 (15)	0.0228 (3)
H8A	0.5191	0.7236	0.0319	0.027*
H8B	0.4587	0.6741	−0.0440	0.027*
C9	0.56360 (8)	0.61470 (6)	−0.24141 (16)	0.0282 (4)
H9A	0.5067	0.6060	−0.2737	0.034*
H9B	0.5981	0.6118	−0.3412	0.034*
C10	0.63360 (8)	0.64953 (6)	0.15736 (17)	0.0242 (3)
H10A	0.6387	0.6904	0.2056	0.029*
H10B	0.6527	0.6201	0.2405	0.029*
C11	0.49559 (8)	0.64112 (6)	0.27851 (16)	0.0226 (3)
H11A	0.5205	0.6125	0.3574	0.027*
H11B	0.5039	0.6821	0.3238	0.027*
C12	0.40426 (8)	0.62906 (6)	0.27706 (16)	0.0221 (3)
H12	0.3932	0.5945	0.2009	0.027*
C13	0.37566 (8)	0.61198 (6)	0.44839 (16)	0.0197 (3)
C14	0.35838 (7)	0.65598 (6)	0.56444 (16)	0.0199 (3)
H14	0.3645	0.6972	0.5356	0.024*
C15	0.33224 (7)	0.64093 (6)	0.72247 (17)	0.0209 (3)
C16	0.32485 (8)	0.58040 (6)	0.76474 (17)	0.0250 (3)
H16	0.3071	0.5694	0.8721	0.030*
C17	0.34335 (8)	0.53647 (6)	0.65039 (18)	0.0277 (4)
H17	0.3390	0.4952	0.6804	0.033*
C18	0.36811 (8)	0.55162 (6)	0.49282 (17)	0.0259 (3)
H18	0.3800	0.5209	0.4149	0.031*
H1B	0.3144 (9)	0.6768 (6)	0.942 (2)	0.045 (5)*
H1C	0.3315 (8)	0.7235 (7)	0.8081 (17)	0.033 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0216 (5)	0.0341 (5)	0.0241 (6)	0.0052 (4)	0.0027 (5)	0.0062 (5)
N1	0.0280 (7)	0.0324 (8)	0.0166 (8)	0.0026 (6)	0.0010 (6)	0.0003 (6)
C1	0.0189 (8)	0.0208 (7)	0.0158 (8)	0.0003 (6)	0.0010 (6)	−0.0002 (6)
C2	0.0250 (8)	0.0223 (7)	0.0247 (8)	−0.0017 (6)	0.0019 (6)	0.0005 (6)
C3	0.0303 (8)	0.0224 (7)	0.0286 (9)	−0.0005 (6)	0.0046 (7)	−0.0073 (7)
C4	0.0272 (9)	0.0322 (8)	0.0276 (9)	0.0082 (6)	0.0086 (7)	0.0036 (7)
C5	0.0160 (7)	0.0359 (8)	0.0257 (9)	−0.0040 (6)	−0.0009 (6)	0.0016 (7)
C6	0.0296 (9)	0.0280 (8)	0.0268 (9)	−0.0056 (6)	0.0071 (7)	0.0018 (7)
C7	0.0270 (8)	0.0281 (8)	0.0210 (8)	0.0034 (6)	0.0015 (6)	0.0073 (7)
C8	0.0212 (7)	0.0241 (7)	0.0230 (8)	0.0027 (6)	−0.0003 (6)	0.0011 (6)
C9	0.0255 (8)	0.0403 (9)	0.0188 (8)	−0.0011 (7)	0.0026 (7)	−0.0045 (7)
C10	0.0239 (8)	0.0267 (8)	0.0221 (8)	0.0004 (6)	−0.0040 (7)	0.0005 (6)
C11	0.0252 (8)	0.0241 (7)	0.0185 (8)	−0.0008 (6)	−0.0023 (6)	0.0001 (6)
C12	0.0229 (8)	0.0232 (7)	0.0202 (8)	0.0023 (6)	0.0005 (7)	−0.0006 (6)
C13	0.0157 (7)	0.0256 (7)	0.0177 (8)	−0.0003 (6)	−0.0007 (6)	0.0008 (6)
C14	0.0174 (7)	0.0217 (7)	0.0206 (8)	−0.0004 (6)	−0.0006 (6)	0.0044 (6)
C15	0.0153 (7)	0.0291 (8)	0.0182 (8)	0.0010 (6)	−0.0018 (6)	0.0001 (6)
C16	0.0214 (8)	0.0331 (8)	0.0205 (9)	−0.0026 (6)	0.0009 (6)	0.0081 (7)
C17	0.0279 (9)	0.0239 (8)	0.0315 (10)	−0.0037 (6)	−0.0023 (7)	0.0070 (7)
C18	0.0277 (8)	0.0244 (7)	0.0255 (9)	0.0005 (6)	−0.0004 (7)	−0.0022 (7)

Geometric parameters (Å, º) top

O1—C12	1.4393 (14)	C7—C9	1.5302 (18)
O1—H1A	0.8400	C7—C8	1.5305 (17)
N1—C15	1.4027 (17)	C7—H7	1.0000
N1—H1C	0.930 (14)	C8—H8A	0.9900
N1—H1B	0.934 (16)	C8—H8B	0.9900
C1—C8	1.5277 (16)	C9—H9A	0.9900
C1—C2	1.5360 (16)	C9—H9B	0.9900
C1—C11	1.5373 (17)	C10—H10A	0.9900
C1—C10	1.5397 (18)	C10—H10B	0.9900
C2—C3	1.5258 (17)	C11—C12	1.5257 (18)
C2—H2A	0.9900	C11—H11A	0.9900
C2—H2B	0.9900	C11—H11B	0.9900
C3—C4	1.5240 (18)	C12—C13	1.5141 (17)
C3—C9	1.5271 (18)	C12—H12	1.0000
C3—H3	1.0000	C13—C14	1.3850 (17)
C4—C5	1.5254 (18)	C13—C18	1.3923 (17)
C4—H4A	0.9900	C14—C15	1.3915 (18)
C4—H4B	0.9900	C14—H14	0.9500
C5—C6	1.5258 (18)	C15—C16	1.3912 (17)
C5—C10	1.5317 (18)	C16—C17	1.3789 (19)
C5—H5	1.0000	C16—H16	0.9500
C6—C7	1.5311 (18)	C17—C18	1.3817 (18)
C6—H6A	0.9900	C17—H17	0.9500
C6—H6B	0.9900	C18—H18	0.9500

C12—O1—H1A	109.5	C1—C8—H8A	109.5
C15—N1—H1C	112.7 (9)	C7—C8—H8A	109.5
C15—N1—H1B	113.8 (9)	C1—C8—H8B	109.5
H1C—N1—H1B	110.3 (13)	C7—C8—H8B	109.5
C8—C1—C2	107.88 (10)	H8A—C8—H8B	108.1
C8—C1—C11	113.47 (10)	C3—C9—C7	109.26 (11)
C2—C1—C11	111.57 (10)	C3—C9—H9A	109.8
C8—C1—C10	108.48 (10)	C7—C9—H9A	109.8
C2—C1—C10	107.86 (10)	C3—C9—H9B	109.8
C11—C1—C10	107.42 (10)	C7—C9—H9B	109.8
C3—C2—C1	110.89 (10)	H9A—C9—H9B	108.3
C3—C2—H2A	109.5	C5—C10—C1	111.33 (11)
C1—C2—H2A	109.5	C5—C10—H10A	109.4
C3—C2—H2B	109.5	C1—C10—H10A	109.4
C1—C2—H2B	109.5	C5—C10—H10B	109.4
H2A—C2—H2B	108.1	C1—C10—H10B	109.4
C2—C3—C4	110.29 (11)	H10A—C10—H10B	108.0
C2—C3—C9	109.45 (11)	C12—C11—C1	119.36 (11)
C4—C3—C9	109.04 (11)	C12—C11—H11A	107.5
C2—C3—H3	109.3	C1—C11—H11A	107.5
C4—C3—H3	109.3	C12—C11—H11B	107.5
C9—C3—H3	109.3	C1—C11—H11B	107.5
C5—C4—C3	109.38 (11)	H11A—C11—H11B	107.0
C5—C4—H4A	109.8	O1—C12—C13	111.45 (10)
C3—C4—H4A	109.8	O1—C12—C11	109.72 (10)
C5—C4—H4B	109.8	C13—C12—C11	110.04 (11)
C3—C4—H4B	109.8	O1—C12—H12	108.5
H4A—C4—H4B	108.2	C13—C12—H12	108.5
C6—C5—C4	110.13 (11)	C11—C12—H12	108.5
C6—C5—C10	108.59 (11)	C14—C13—C18	118.96 (12)
C4—C5—C10	109.19 (11)	C14—C13—C12	120.66 (11)
C6—C5—H5	109.6	C18—C13—C12	120.37 (12)
C4—C5—H5	109.6	C13—C14—C15	121.27 (12)
C10—C5—H5	109.6	C13—C14—H14	119.4
C5—C6—C7	109.41 (11)	C15—C14—H14	119.4
C5—C6—H6A	109.8	C14—C15—C16	119.03 (12)
C7—C6—H6A	109.8	C14—C15—N1	119.67 (12)
C5—C6—H6B	109.8	C16—C15—N1	121.08 (13)
C7—C6—H6B	109.8	C17—C16—C15	119.84 (13)
H6A—C6—H6B	108.2	C17—C16—H16	120.1
C6—C7—C9	109.36 (11)	C15—C16—H16	120.1
C6—C7—C8	109.41 (11)	C16—C17—C18	120.94 (13)
C9—C7—C8	109.60 (10)	C16—C17—H17	119.5
C6—C7—H7	109.5	C18—C17—H17	119.5
C9—C7—H7	109.5	C17—C18—C13	119.95 (13)
C8—C7—H7	109.5	C17—C18—H18	120.0
C1—C8—C7	110.82 (10)	C13—C18—H18	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.84	2.10	2.9400 (14)	176
N1—H1C···O1ⁱⁱ	0.930 (15)	2.295 (15)	3.2048 (16)	166.0 (13)
N1—H1B···O1ⁱⁱⁱ	0.930 (16)	2.357 (16)	3.2472 (16)	160.1 (14)

Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₅NO
M_r	271.39
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	120
a, b, c (Å)	16.4467 (7), 22.1873 (9), 8.1033 (4)
V (Å³)	2957.0 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Kuma KM-4 CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.984, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	30937, 2602, 1716
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.068, 0.85
No. of reflections	2602
No. of parameters	190
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.84	2.10	2.9400 (14)	175.8
N1—H1C···O1ⁱⁱ	0.930 (15)	2.295 (15)	3.2048 (16)	166.0 (13)
N1—H1B···O1ⁱⁱⁱ	0.930 (16)	2.357 (16)	3.2472 (16)	160.1 (14)

Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) x, y, z+1.

Acknowledgements

Financial support of this work by the Tomas Bata Foundation, the Czech Ministry of Education (project No. MSM 7088352101) and the Internal Funding Agency of Tomas Bata University in Zlin (project No. IGA/6/FT/11/D) is gratefully acknowledged.

References

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