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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3198
https://doi.org/10.1107/S1600536811046009

(1-Adamant­yl)(3-amino­phen­yl)methanone

Michal Rouchal,a Marek Nečasb and Robert Víchaa*

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 19 October 2011; accepted 1 November 2011; online 5 November 2011)

In the crystal sructure of the title compound, C17H21NO, the mol­ecular packing is stabilized by inter­molecular N—H⋯O hydrogen bonds and additional weak N—H⋯π inter­actions, forming chains that propagate along the b axis. Conjugation of the carbonyl group and the benzene ring is rather attenuated due to a twisting of the carbonyl group from the plane of the benzene ring [torsion angle = 27.1 (2)°].

Related literature

For recent reviews of the biological activity of some adamantane-bearing compounds, see: Ahrén (2009[Ahrén, B. (2009). Best Pract. Res. Clin. Endoc. Metab. 23, 487-498.]); Ginsberg (2010[Ginsberg, A. M. (2010). Drugs, 70, 2201-2214.]); Lagoja & De Clercq (2008[Lagoja, I. M. & De Clercq, E. (2008). Med. Res. Rev. 28, 1-38.]). For the structures of similar adamantylated aromatic amines, see: Rouchal et al. (2009[Rouchal, M., Nečas, M. & Vícha, R. (2009). Acta Cryst. E65, o1018.], 2011[Rouchal, M., Kozubková, Z., Nečas, M. & Vícha, R. (2011). Acta Cryst. E67, o2515.]).

[Scheme 1]

Experimental

Crystal data

  • C17H21NO

  • Mr = 255.35

  • Orthorhombic, P 21 21 21

  • a = 6.4644 (1) Å

  • b = 8.1978 (3) Å

  • c = 25.1760 (5) Å

  • V = 1334.17 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 120 K

  • 0.30 × 0.30 × 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.]) Tmin = 0.998, Tmax = 1.000

  • 15931 measured reflections

  • 1672 independent reflections

  • 1531 reflections with I > 2σ(I)

  • Rint = 0.016
Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.073

  • S = 1.04

  • 1672 reflections

  • 180 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1B⋯O1i 0.91 (3) 2.10 (3) 3.003 (2) 168 (2)
N1—H1A⋯Cg1ii 0.90 (3) 2.54 (3) 3.316 (18) 144 (2)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811046009/pk2356sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046009/pk2356Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046009/pk2356Isup3.cml

checkCIF report


Comment top

The adamantane cage represents a widely used substituent in medicinal chemistry. A large number of adamantylated biologically active compounds have been described in the literature. For example, they act as tuberculostatics (Ginsberg, 2010), anti-influenza virus agents (Lagoja & De Clercq, 2008) and as type 2 diabetes medications (Ahrén, 2009). The title molecule belongs to the family of newly prepared adamantane-bearing aromatic amines as promising building blocks for drugs modification.

The asymmetric unit of the title compound consists of a single molecule (Fig. 1). The benzene ring is essentially planar with a maximum deviation from the best plane being 0.025 (16) Å for C14. The adamantane cage consists of three fused cyclohexane rings in classical chair conformations, with C—C—C angles varying within the range 107.40 (12)–110.82 (13)°. The torsion angles describing an arrangement of adamantane scaffold, benzene ring and carbonyl bridge C1–C11–C12–C13 and C2–C1–C11–C12 are 151.40 (15) and 78.16 (17)°, respectively. The molecules are linked into chains parallel to the b-axis by N1–H1A···O1 hydrogen bonds (Fig. 2, Table 1). The crystal packing is further stabilized by intermolecular N–H···π interactions.

Related literature top

For recent reviews of the biological activity of some adamantane-bearing compounds, see: Ahrén (2009); Ginsberg (2010); Lagoja & De Clercq (2008). For the structures of similar adamantylated aromatic amines, see: Rouchal et al. (2009, 2011).

Experimental top

(1-Adamantyl)(3-nitrophenyl)methanone (450 mg, 1.65 mmol) was dissolved in 47 cm3 of warm methanol and 7 cm3 of hydrochloric acid/water (1/1, v/v) was carefully added. Into the refluxed and well stirred mixture, portions of an iron powder (207 mg, 3.71 mmol) were added successively. The reaction was stopped when TLC indicated the consumption of all starting material. The mixture was diluted with 5% solution of sodium hydroxide (40 cm3) and extracted several times with diethyl ether. Combined organic layers were washed with brine, dried over sodium sulfate and evaporated in vacuum. The desired product was obtained after the purification of crude material using column chromatography (silica gel; petroleum ether/ethyl acetate, 1/1, v/v) as a colourless crystalline powder (371 mg, 88%, mp 370–373 K). The crystal used for data collection was grown by spontaneous evaporation from deuterochloroform at room temperature.

Refinement top

All carbon bound H atoms were placed at calculated positions with distances of 1.00 Å (R3CH), 0.99 Å (R2CH2) and 0.95 Å (Csp2H), and were refined as riding with their Uiso set to 1.2Ueq of the respective carrier atoms. Nitrogen bound H atoms were located in a difference Fourier map and refined isotropically. In the absence of anomalous scattering, Friedel pairs were merged.

Structure description top

The adamantane cage represents a widely used substituent in medicinal chemistry. A large number of adamantylated biologically active compounds have been described in the literature. For example, they act as tuberculostatics (Ginsberg, 2010), anti-influenza virus agents (Lagoja & De Clercq, 2008) and as type 2 diabetes medications (Ahrén, 2009). The title molecule belongs to the family of newly prepared adamantane-bearing aromatic amines as promising building blocks for drugs modification.

The asymmetric unit of the title compound consists of a single molecule (Fig. 1). The benzene ring is essentially planar with a maximum deviation from the best plane being 0.025 (16) Å for C14. The adamantane cage consists of three fused cyclohexane rings in classical chair conformations, with C—C—C angles varying within the range 107.40 (12)–110.82 (13)°. The torsion angles describing an arrangement of adamantane scaffold, benzene ring and carbonyl bridge C1–C11–C12–C13 and C2–C1–C11–C12 are 151.40 (15) and 78.16 (17)°, respectively. The molecules are linked into chains parallel to the b-axis by N1–H1A···O1 hydrogen bonds (Fig. 2, Table 1). The crystal packing is further stabilized by intermolecular N–H···π interactions.

For recent reviews of the biological activity of some adamantane-bearing compounds, see: Ahrén (2009); Ginsberg (2010); Lagoja & De Clercq (2008). For the structures of similar adamantylated aromatic amines, see: Rouchal et al. (2009, 2011).

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
[Figure 1] Fig. 1. A thermal ellipsoid plot (50% probability) of the asymmetric unit. H-Atoms are shown as small spheres at arbitrary radii.
[Figure 2] Fig. 2. The H-bonded chains of the molecules of title compound arranged parallel to the b-axis. H-atoms have been omitted (except for those participating in H-bonds) for clarity. Cg1 is centre of gravity of C12—C17. Symmetry codes: (i) -x + 1, y - 1/2, -z + 1/2; (ii) -x, y - 1/2, -z + 1/2.
(1-Adamantyl)(3-aminophenyl)methanone top
Crystal data top
C17H21NODx = 1.271 Mg m−3
Mr = 255.35Melting point: 372 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 10578 reflections
a = 6.4644 (1) Åθ = 3.2–27.2°
b = 8.1978 (3) ŵ = 0.08 mm−1
c = 25.1760 (5) ÅT = 120 K
V = 1334.17 (6) Å3Block, colourless
Z = 40.30 × 0.30 × 0.20 mm
F(000) = 552
Data collection top
Oxford Diffraction Xcalibur Sapphire2
diffractometer		1672 independent reflections
Radiation source: fine-focus sealed tube1531 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 8.4353 pixels mm-1θmax = 27.3°, θmin = 3.2°
ω scanh = −8→8
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		k = −10→5
Tmin = 0.998, Tmax = 1.000l = −32→32
15931 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0342P)2 + 0.3516P]
where P = (Fo2 + 2Fc2)/3
1672 reflections(Δ/σ)max < 0.001
180 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C17H21NOV = 1334.17 (6) Å3
Mr = 255.35Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.4644 (1) ŵ = 0.08 mm−1
b = 8.1978 (3) ÅT = 120 K
c = 25.1760 (5) Å0.30 × 0.30 × 0.20 mm
Data collection top
Oxford Diffraction Xcalibur Sapphire2
diffractometer		1672 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1531 reflections with I > 2σ(I)
Tmin = 0.998, Tmax = 1.000Rint = 0.016
15931 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.21 e Å−3
1672 reflectionsΔρmin = −0.17 e Å−3
180 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
xyzUiso*/Ueq
O10.4200 (2)0.29596 (16)0.21048 (4)0.0309 (3)
N10.1688 (3)−0.2699 (2)0.23832 (7)0.0344 (4)
C10.3647 (2)0.3819 (2)0.12126 (6)0.0170 (3)
C20.1811 (2)0.5018 (2)0.11371 (6)0.0190 (3)
H2A0.05250.43960.10690.023*
H2B0.16130.56670.14650.023*
C30.2246 (2)0.6165 (2)0.06674 (6)0.0214 (4)
H30.10480.69220.06190.026*
C40.2554 (3)0.5155 (2)0.01592 (6)0.0220 (4)
H4A0.12850.45220.00830.026*
H4B0.28180.5892−0.01450.026*
C50.4390 (2)0.3989 (2)0.02303 (6)0.0202 (3)
H50.45850.3339−0.01020.024*
C60.6351 (2)0.4984 (2)0.03404 (6)0.0226 (4)
H6A0.66380.57180.00370.027*
H6B0.75470.42420.03850.027*
C70.6041 (3)0.5995 (2)0.08489 (6)0.0213 (4)
H70.73230.66380.09230.026*
C80.5599 (2)0.4852 (2)0.13178 (6)0.0204 (3)
H8A0.54010.55040.16450.025*
H8B0.67990.41210.13740.025*
C90.4214 (3)0.7162 (2)0.07774 (7)0.0234 (4)
H9A0.44880.79110.04770.028*
H9B0.40280.78250.11030.028*
C100.3976 (3)0.2828 (2)0.06965 (6)0.0184 (3)
H10A0.51640.20780.07410.022*
H10B0.27300.21640.06210.022*
C110.3283 (2)0.2699 (2)0.16894 (6)0.0193 (3)
C120.1869 (2)0.1237 (2)0.16726 (6)0.0190 (3)
C130.2376 (3)−0.0037 (2)0.20158 (6)0.0215 (3)
H130.36200.00230.22160.026*
C140.1096 (3)−0.1401 (2)0.20729 (6)0.0232 (4)
C15−0.0785 (3)−0.1424 (2)0.17955 (6)0.0252 (4)
H15−0.1727−0.22990.18470.030*
C16−0.1272 (3)−0.0174 (2)0.14471 (6)0.0246 (4)
H16−0.2532−0.02200.12540.030*
C170.0044 (3)0.1143 (2)0.13749 (6)0.0217 (3)
H17−0.02900.19730.11260.026*
H1A0.068 (4)−0.338 (3)0.2494 (10)0.058 (8)*
H1B0.286 (4)−0.257 (3)0.2582 (9)0.048 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0383 (7)0.0326 (7)0.0219 (6)−0.0106 (7)−0.0096 (6)0.0026 (5)
N10.0409 (10)0.0300 (9)0.0324 (8)−0.0094 (9)−0.0087 (8)0.0115 (8)
C10.0158 (7)0.0174 (7)0.0177 (7)−0.0016 (7)−0.0002 (6)−0.0010 (7)
C20.0167 (7)0.0182 (8)0.0221 (7)0.0007 (8)0.0027 (6)−0.0010 (7)
C30.0161 (8)0.0194 (8)0.0287 (8)0.0030 (7)0.0011 (6)0.0047 (7)
C40.0187 (7)0.0246 (9)0.0226 (8)−0.0025 (8)−0.0022 (6)0.0061 (7)
C50.0191 (8)0.0233 (8)0.0181 (7)0.0000 (8)0.0009 (6)−0.0015 (7)
C60.0164 (7)0.0259 (9)0.0255 (8)−0.0009 (8)0.0035 (6)0.0041 (7)
C70.0164 (7)0.0220 (9)0.0254 (8)−0.0046 (8)0.0003 (6)0.0002 (7)
C80.0176 (7)0.0222 (8)0.0215 (7)−0.0026 (8)−0.0016 (6)0.0000 (7)
C90.0235 (9)0.0186 (8)0.0283 (8)−0.0039 (8)0.0042 (7)0.0017 (7)
C100.0183 (8)0.0179 (8)0.0191 (7)0.0001 (7)−0.0008 (7)−0.0019 (6)
C110.0192 (7)0.0204 (8)0.0183 (7)0.0023 (7)−0.0005 (6)−0.0011 (7)
C120.0211 (7)0.0199 (8)0.0160 (7)−0.0014 (7)0.0026 (6)0.0000 (7)
C130.0214 (7)0.0244 (8)0.0186 (7)0.0002 (8)−0.0007 (6)−0.0013 (7)
C140.0300 (9)0.0221 (9)0.0174 (7)−0.0010 (8)0.0022 (7)0.0005 (7)
C150.0288 (9)0.0225 (9)0.0245 (8)−0.0081 (8)0.0027 (7)−0.0014 (7)
C160.0238 (8)0.0270 (9)0.0230 (8)−0.0053 (8)−0.0035 (7)−0.0026 (7)
C170.0250 (8)0.0209 (8)0.0193 (7)−0.0004 (8)−0.0026 (6)0.0009 (7)
Geometric parameters (Å, º) top
O1—C111.2208 (19)C6—H6B0.9900
N1—C141.375 (2)C7—C91.530 (2)
N1—H1A0.90 (3)C7—C81.534 (2)
N1—H1B0.91 (2)C7—H71.0000
C1—C111.529 (2)C8—H8A0.9900
C1—C81.543 (2)C8—H8B0.9900
C1—C101.547 (2)C9—H9A0.9900
C1—C21.553 (2)C9—H9B0.9900
C2—C31.537 (2)C10—H10A0.9900
C2—H2A0.9900C10—H10B0.9900
C2—H2B0.9900C11—C121.508 (2)
C3—C41.537 (2)C12—C131.395 (2)
C3—C91.538 (2)C12—C171.400 (2)
C3—H31.0000C13—C141.398 (2)
C4—C51.535 (2)C13—H130.9500
C4—H4A0.9900C14—C151.402 (2)
C4—H4B0.9900C15—C161.385 (2)
C5—C61.532 (2)C15—H150.9500
C5—C101.535 (2)C16—C171.386 (2)
C5—H51.0000C16—H160.9500
C6—C71.538 (2)C17—H170.9500
C6—H6A0.9900
C14—N1—H1A117.0 (16)C9—C7—H7109.4
C14—N1—H1B117.0 (15)C8—C7—H7109.4
H1A—N1—H1B120 (2)C6—C7—H7109.4
C11—C1—C8108.68 (12)C7—C8—C1110.82 (13)
C11—C1—C10111.41 (13)C7—C8—H8A109.5
C8—C1—C10108.66 (12)C1—C8—H8A109.5
C11—C1—C2111.02 (12)C7—C8—H8B109.5
C8—C1—C2107.40 (12)C1—C8—H8B109.5
C10—C1—C2109.56 (12)H8A—C8—H8B108.1
C3—C2—C1109.96 (12)C7—C9—C3109.08 (13)
C3—C2—H2A109.7C7—C9—H9A109.9
C1—C2—H2A109.7C3—C9—H9A109.9
C3—C2—H2B109.7C7—C9—H9B109.9
C1—C2—H2B109.7C3—C9—H9B109.9
H2A—C2—H2B108.2H9A—C9—H9B108.3
C2—C3—C4109.58 (14)C5—C10—C1109.89 (13)
C2—C3—C9109.77 (13)C5—C10—H10A109.7
C4—C3—C9109.22 (13)C1—C10—H10A109.7
C2—C3—H3109.4C5—C10—H10B109.7
C4—C3—H3109.4C1—C10—H10B109.7
C9—C3—H3109.4H10A—C10—H10B108.2
C5—C4—C3109.79 (13)O1—C11—C12117.21 (14)
C5—C4—H4A109.7O1—C11—C1119.54 (15)
C3—C4—H4A109.7C12—C11—C1123.23 (13)
C5—C4—H4B109.7C13—C12—C17119.21 (15)
C3—C4—H4B109.7C13—C12—C11115.82 (14)
H4A—C4—H4B108.2C17—C12—C11124.75 (15)
C6—C5—C4109.22 (13)C12—C13—C14121.58 (15)
C6—C5—C10109.66 (13)C12—C13—H13119.2
C4—C5—C10109.91 (13)C14—C13—H13119.2
C6—C5—H5109.3N1—C14—C13120.85 (16)
C4—C5—H5109.3N1—C14—C15120.94 (17)
C10—C5—H5109.3C13—C14—C15118.19 (15)
C5—C6—C7109.25 (13)C16—C15—C14120.17 (16)
C5—C6—H6A109.8C16—C15—H15119.9
C7—C6—H6A109.8C14—C15—H15119.9
C5—C6—H6B109.8C15—C16—C17121.31 (16)
C7—C6—H6B109.8C15—C16—H16119.3
H6A—C6—H6B108.3C17—C16—H16119.3
C9—C7—C8109.21 (13)C16—C17—C12119.34 (15)
C9—C7—C6109.85 (13)C16—C17—H17120.3
C8—C7—C6109.60 (14)C12—C17—H17120.3
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i0.91 (3)2.10 (3)3.003 (2)168 (2)
N1—H1A···Cg1ii0.90 (3)2.54 (3)3.316 (18)144 (2)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC17H21NO
Mr255.35
Crystal system, space groupOrthorhombic, P212121
Temperature (K)120
a, b, c (Å)6.4644 (1), 8.1978 (3), 25.1760 (5)
V (Å3)1334.17 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.30 × 0.30 × 0.20
Data collection
DiffractometerOxford Diffraction Xcalibur Sapphire2
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.998, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		15931, 1672, 1531
Rint0.016
(sin θ/λ)max (Å−1)0.645
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.073, 1.04
No. of reflections1672
No. of parameters180
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.21, −0.17

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
Cg1 is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i0.91 (3)2.10 (3)3.003 (2)168 (2)
N1—H1A···Cg1ii0.90 (3)2.54 (3)3.316 (18)144 (2)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2.
 

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

First citationAhrén, B. (2009). Best Pract. Res. Clin. Endoc. Metab. 23, 487–498.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGinsberg, A. M. (2010). Drugs, 70, 2201–2214.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationLagoja, I. M. & De Clercq, E. (2008). Med. Res. Rev. 28, 1–38.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationMacrae, 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 CSD CrossRef CAS IUCr Journals Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationRouchal, M., Kozubková, Z., Nečas, M. & Vícha, R. (2011). Acta Cryst. E67, o2515.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationRouchal, M., Nečas, M. & Vícha, R. (2009). Acta Cryst. E65, o1018.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3198
https://doi.org/10.1107/S1600536811046009
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