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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 10| October 2014| Pages o1081-o1082

Crystal structure of (3R)-3-benzyl-4-[(tert-but­­oxy­carbon­yl)amino]­butanoic acid

aInstitute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, Łódź, Poland, and bInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, Łódź, Poland
*Correspondence e-mail: marek.glowka@p.lodz.pl

Edited by M. Gdaniec, Adam Mickiewicz University, Poland (Received 9 June 2014; accepted 28 August 2014; online 3 September 2014)

The characteristic feature of the title mol­ecule, C16H23NO4, is the syn configuration of the partially double amide C—N bond [C—N—C—O torsion angle = −14.8 (2)°]. The crystal packing is determined by inter­molecular O—H⋯O and N—H⋯O hydrogen bonds, which link the mol­ecules into a double-chain structure extending along [010].

1. Related literature

The title enanti­omeric compound was synthesized according to Loukas et al. (2003[Loukas, V., Noula, C. & Kokotos, G. (2003). J. Pept. Sci. 9, 312-319.]) and Felluga et al. (2008[Felluga, F., Pitacco, G., Valentin, E. & Venneri, C. D. (2008). Tetrahedron Asymmetry, 19, 945-955.]). For related structures, see: Pihko & Koskinen (1998[Pihko, P. M. & Koskinen, A. M. P. (1998). J. Org. Chem. 63, 92-98.]); Jimeno et al. (2011[Jimeno, C., Pericas, M. A., Wessel, H. P., Alker, A. & Muller, K. (2011). ChemMedChem, 6, 1792-1795.]). For solution conformation of oligomers based on monosubstituted γ-amino acids, see: Guo et al. (2012[Guo, L., Zhang, W., Guzei, I. A., Spencer, L. C. & Gellman, S. H. (2012). Tetrahedron, 68, 4413-4417.]); Kang & Byun (2012[Kang, Y. K. & Byun, B. J. (2012). Biopolymers, 97, 1018-1025.]). For amino acid analysis by HPLC after derivatization with Marfey's reagent, see: Marfey (1984[Marfey, P. (1984). Carlsberg Res. Commun. 49, 591-596.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C16H23NO4

  • Mr = 293.35

  • Monoclinic, C 2

  • a = 19.5872 (12) Å

  • b = 6.5263 (4) Å

  • c = 14.7598 (9) Å

  • β = 120.846 (2)°

  • V = 1619.89 (17) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.70 mm−1

  • T = 100 K

  • 0.4 × 0.04 × 0.04 mm

2.2. Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.738, Tmax = 0.973

  • 8769 measured reflections

  • 2880 independent reflections

  • 2805 reflections with I > 2σ(I)

  • Rint = 0.036

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.073

  • S = 1.06

  • 2880 reflections

  • 197 parameters

  • 1 restraint

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

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.18 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1138 Friedel pairs

  • Absolute structure parameter: 0.05 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O6i 0.82 1.83 2.6368 (15) 170
N5—H5⋯O2ii 0.846 (18) 2.131 (18) 2.8856 (16) 148.2 (15)
Symmetry codes: (i) -x+2, y+1, -z+1; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

γ-Amino acids are important components of α,γ-peptide hybrids, which are resistant towards enzymatic degradation and, as a result, display useful biological activity, including antibiotic, antiviral and anticancer properties. The acids are also important elements of foldamers. In comparison with the α-amino acids, they show significant flexibility due to the two additional single bonds between the carboxylic and amine functions. Still, their oligomers form well defined conformations in solutions, in particular helical ones in the case of monosubstituted γ-amino acids (Guo et al., 2012, Kang et al., 2012). Thus, the structures and common conformations of γ-amino acids and their derivatives are of interest. The molecular structure is shown in Figure 1. The crystal packing is determined by intermolecular N5—H···O2 and O1—H···O6 hydrogen bonds, which organize the molecules into infinite double chains parallel to the [010] direction (Fig.2). The geometrical parameters of the hydrogen bonds are listed in Table 1.

Related literature top

The title enantiomeric compound was synthesized according to Loukas et al. (2003) and Felluga et al. (2008). For related structures, see: Pihko & Koskinen (1998); Jimeno et al. (2011). For solution conformation of oligomers based on monosubstituted γ-amino acids, see: Guo et al. (2012); Kang & Byun (2012). For amino acid analysis by HPLC after derivatization with Marfey's reagent, see: Marfey (1984).

Experimental top

(3R)-4-((tert-Butoxycarbonyl)amino-)-3-benzyl-butanoic acid was obtained from racemic (±)-3-aminomethyl-4-phenylbutanoic acid hydrochloride, which was synthesized following earlier published procedure (Felluga et al., 2008), with some modifications. Ethyl (±)-3-nitromethyl-4-phenylbutanoate was hydrolyzed and then hydrogenated using 10% Pd/C to get acid, which was transformed into Boc-derivative and purified by crystallization from ethyl acetate/hexane.

Enantiomeric resolution of racemic (±)-3-aminomethyl-4-phenylbutanoic acid (1 g) was achieved by crystallization from ethyl acetate (110 mL) in the presence of (S)-(-)-methylbenzylamine (0.41 g). The solution was left for 24 h at +5°C for crystallization, which was repeated four times to obtain (3S)-4-((tert-butoxycarbonyl)amino-)-3-benzyl-butanoic acid (0.151 g) with ee = 97.4 %. (R)-(+)-Methylbenzylamine (0.17 g) was applied to the mother liquor after the first crystallization of (3S)-4-((tert-butoxycarbonyl)amino-)-3-benzyl-butanoic acid ammonium salt. Three subsequent crystallizations led to (3R)-(-)-4-((tert-butoxycarbonyl)amino-)-3-phenyl-pentanoic acid (0.196 g) with ee = 98.1 %. Acids were recovered from ethyl acetate solution using 1M NaHSO4 solution.

The enantiomeric purity was determined according to the known procedure using Nα-(2,4-dinitro-5-fluorophenyl)-L-valinamide as derivating reagent (Marfey, 1984). Sample of enantiomer (5 mg) was dissolved in TFA – dichloromethane (1:1), the solution was shaken for 10 min, then solvents were removed by evaporation. The residue was dissolved in CH2Cl2 and the solvent was removed again. This procedure was repeated five times to remove TFA completely. The dry residue was dissolved in 0.2 M NaHCO3 to obtain 0.05 M solutions (0.5 mL) of (3R)-4-amino–3-benzyl-butanoic acid. Mixture of 0.05 M aqueous solution of deprotected amino acid (25 µL), 0.2 N NaHCO3 (50 µL), 1% solution of Nα-(2,4-dinitro-5-fluorophenyl)-L-valine amide in acetone (50 µL) and 75 µL of acetone was shaken for 1 minute and then placed in a water bath for 45 min at 45°C. Then mixture was shaken again for 30 sec, 0.1M HCl (170 µL) and acetone (75 µL) were added. A yellowish solution was analysed by HPLC (Vydac column C8 (4.6 x 25 cm), gradient 40 - 80, detection at 340 nm), diastereomeric derivative of (3R)-4-amino-3-benzyl-butanoic acid was detected at 12.67 min retention time.

Single crystals were obtained by recrystallization from acetonitrile at room temperatute.

Refinement top

All H atoms were located in difference Fourier maps but finally their positions were determined geometrically, except H5 that was freely refined. H atoms were refined as riding on their carriers with C—H= 0.95 Å for aromatic CH groups, 0.97 Å for CH2 groups, 0.96 Å for methyl groups and N—H = 0.86 Å for the amide group, and with Uiso(H) = 1.2Ueq(C,N), except for methyl group where Uiso(H) = 1.5Ueq(C). The absolute structure was known from the synthetic procedure and is confirmed by the Flack parameter of 0.05 (15).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing of the title compound viewed along the [101] direction.
(3R)-3-Benzyl-4-[(tert-butoxycarbonyl)amino]butanoic acid top
Crystal data top
C16H23NO4F(000) = 632
Mr = 293.35Dx = 1.203 Mg m3
Monoclinic, C2Cu Kα radiation, λ = 1.54178 Å
Hall symbol: C 2yCell parameters from 3858 reflections
a = 19.5872 (12) Åθ = 3.5–64.2°
b = 6.5263 (4) ŵ = 0.70 mm1
c = 14.7598 (9) ÅT = 100 K
β = 120.846 (2)°Needle, colourless
V = 1619.89 (17) Å30.4 × 0.04 × 0.04 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
2880 independent reflections
Radiation source: fine-focus sealed tube2805 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scanθmax = 72.4°, θmin = 3.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2424
Tmin = 0.738, Tmax = 0.973k = 78
8769 measured reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0236P)2 + 0.6631P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2880 reflectionsΔρmax = 0.16 e Å3
197 parametersΔρmin = 0.18 e Å3
1 restraintAbsolute structure: Flack (1983), 1138 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (15)
Crystal data top
C16H23NO4V = 1619.89 (17) Å3
Mr = 293.35Z = 4
Monoclinic, C2Cu Kα radiation
a = 19.5872 (12) ŵ = 0.70 mm1
b = 6.5263 (4) ÅT = 100 K
c = 14.7598 (9) Å0.4 × 0.04 × 0.04 mm
β = 120.846 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer
2880 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2805 reflections with I > 2σ(I)
Tmin = 0.738, Tmax = 0.973Rint = 0.036
8769 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073Δρmax = 0.16 e Å3
S = 1.06Δρmin = 0.18 e Å3
2880 reflectionsAbsolute structure: Flack (1983), 1138 Friedel pairs
197 parametersAbsolute structure parameter: 0.05 (15)
1 restraint
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
xyzUiso*/Ueq
C10.89784 (7)0.5954 (2)0.40885 (10)0.0213 (3)
C20.88937 (8)0.3833 (2)0.44237 (10)0.0220 (3)
H2A0.93090.29660.44590.026*
H2B0.83860.32680.38910.026*
C30.89425 (7)0.3775 (2)0.54933 (10)0.0211 (3)
H30.94050.45740.60050.025*
C40.90258 (7)0.1581 (2)0.58971 (10)0.0226 (3)
H4A0.89360.15820.64850.027*
H4B0.86120.07530.53410.027*
C61.04195 (8)0.0711 (2)0.72350 (10)0.0215 (3)
C81.08942 (8)0.2534 (2)0.89211 (11)0.0285 (3)
C91.05139 (13)0.4342 (4)0.91403 (14)0.0596 (6)
H9A1.05020.54990.87310.089*
H9B1.08180.46800.98770.089*
H9C0.99810.39920.89520.089*
C101.09383 (10)0.0664 (3)0.95540 (12)0.0392 (4)
H10A1.04130.03020.93950.059*
H10B1.12650.09601.02930.059*
H10C1.11650.04570.93750.059*
C111.17061 (10)0.3096 (3)0.90952 (12)0.0390 (4)
H11A1.19380.19180.89670.058*
H11B1.20450.35490.98090.058*
H11C1.16490.41760.86190.058*
C300.81864 (8)0.4716 (2)0.53904 (10)0.0234 (3)
H30A0.80380.59000.49300.028*
H30B0.77600.37230.50480.028*
C310.82452 (7)0.5377 (2)0.64118 (10)0.0212 (3)
C320.86972 (9)0.7077 (2)0.69501 (12)0.0290 (3)
H320.90030.77200.67170.035*
C330.86995 (9)0.7831 (3)0.78276 (13)0.0346 (3)
H330.90000.89850.81710.041*
C340.82581 (9)0.6883 (3)0.81985 (11)0.0318 (3)
H340.82540.74050.87820.038*
C350.78253 (9)0.5154 (3)0.76924 (12)0.0348 (4)
H350.75370.44840.79440.042*
C360.78199 (8)0.4414 (3)0.68080 (11)0.0297 (3)
H360.75250.32470.64730.036*
N50.97942 (6)0.06104 (18)0.62403 (9)0.0218 (2)
H50.9795 (9)0.034 (3)0.5849 (12)0.026*
O10.88632 (7)0.59996 (17)0.31251 (8)0.0335 (3)
H10.89150.71770.29760.050*
O20.91355 (6)0.74770 (16)0.46349 (8)0.0286 (2)
O61.10102 (6)0.03990 (16)0.75856 (7)0.0281 (2)
O71.03178 (5)0.21689 (15)0.77878 (7)0.0261 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0191 (6)0.0193 (7)0.0236 (6)0.0012 (5)0.0095 (5)0.0024 (5)
C20.0246 (6)0.0160 (6)0.0247 (6)0.0011 (5)0.0121 (5)0.0020 (5)
C30.0216 (6)0.0175 (7)0.0217 (6)0.0008 (5)0.0093 (5)0.0006 (5)
C40.0227 (6)0.0170 (7)0.0256 (6)0.0016 (5)0.0106 (5)0.0009 (5)
C60.0293 (7)0.0125 (6)0.0242 (6)0.0002 (5)0.0147 (5)0.0012 (5)
C80.0341 (7)0.0233 (8)0.0208 (6)0.0009 (6)0.0088 (6)0.0044 (6)
C90.0666 (12)0.0553 (13)0.0349 (9)0.0212 (10)0.0103 (8)0.0206 (9)
C100.0449 (9)0.0405 (10)0.0286 (7)0.0090 (8)0.0163 (7)0.0027 (7)
C110.0421 (9)0.0372 (10)0.0275 (7)0.0131 (7)0.0105 (7)0.0005 (7)
C300.0237 (6)0.0215 (7)0.0233 (6)0.0016 (5)0.0107 (5)0.0007 (5)
C310.0203 (6)0.0167 (7)0.0240 (6)0.0037 (5)0.0095 (5)0.0021 (5)
C320.0345 (7)0.0156 (7)0.0400 (8)0.0024 (6)0.0214 (7)0.0001 (6)
C330.0384 (8)0.0207 (8)0.0414 (8)0.0041 (6)0.0181 (7)0.0102 (6)
C340.0327 (7)0.0338 (9)0.0268 (7)0.0042 (6)0.0137 (6)0.0057 (6)
C350.0343 (7)0.0409 (10)0.0330 (8)0.0079 (7)0.0201 (6)0.0033 (7)
C360.0296 (7)0.0290 (8)0.0308 (7)0.0097 (6)0.0156 (6)0.0069 (6)
N50.0270 (6)0.0122 (6)0.0244 (5)0.0004 (4)0.0117 (5)0.0030 (4)
O10.0551 (7)0.0190 (6)0.0296 (5)0.0092 (5)0.0241 (5)0.0031 (4)
O20.0384 (5)0.0164 (5)0.0290 (5)0.0035 (4)0.0159 (4)0.0049 (4)
O60.0299 (5)0.0220 (5)0.0292 (5)0.0074 (4)0.0129 (4)0.0008 (4)
O70.0302 (5)0.0195 (5)0.0227 (5)0.0052 (4)0.0094 (4)0.0039 (4)
Geometric parameters (Å, º) top
C1—O21.2159 (17)C10—H10A0.9600
C1—O11.3209 (16)C10—H10B0.9600
C1—C21.507 (2)C10—H10C0.9600
C2—C31.5322 (17)C11—H11A0.9600
C2—H2A0.9700C11—H11B0.9600
C2—H2B0.9700C11—H11C0.9600
C3—C41.5272 (19)C30—C311.5144 (18)
C3—C301.5373 (18)C30—H30A0.9700
C3—H30.9800C30—H30B0.9700
C4—N51.4634 (17)C31—C321.388 (2)
C4—H4A0.9700C31—C361.3894 (19)
C4—H4B0.9700C32—C331.383 (2)
C6—O61.2318 (16)C32—H320.9300
C6—O71.3332 (16)C33—C341.384 (2)
C6—N51.3476 (17)C33—H330.9300
C8—O71.4809 (16)C34—C351.379 (2)
C8—C101.512 (2)C34—H340.9300
C8—C91.516 (2)C35—C361.387 (2)
C8—C111.520 (2)C35—H350.9300
C9—H9A0.9600C36—H360.9300
C9—H9B0.9600N5—H50.846 (18)
C9—H9C0.9600O1—H10.8200
O2—C1—O1122.74 (13)C8—C10—H10C109.5
O2—C1—C2124.47 (11)H10A—C10—H10C109.5
O1—C1—C2112.79 (11)H10B—C10—H10C109.5
C1—C2—C3113.68 (11)C8—C11—H11A109.5
C1—C2—H2A108.8C8—C11—H11B109.5
C3—C2—H2A108.8H11A—C11—H11B109.5
C1—C2—H2B108.8C8—C11—H11C109.5
C3—C2—H2B108.8H11A—C11—H11C109.5
H2A—C2—H2B107.7H11B—C11—H11C109.5
C4—C3—C2111.29 (11)C31—C30—C3115.96 (10)
C4—C3—C30108.53 (11)C31—C30—H30A108.3
C2—C3—C30109.89 (10)C3—C30—H30A108.3
C4—C3—H3109.0C31—C30—H30B108.3
C2—C3—H3109.0C3—C30—H30B108.3
C30—C3—H3109.0H30A—C30—H30B107.4
N5—C4—C3115.21 (11)C32—C31—C36117.71 (13)
N5—C4—H4A108.5C32—C31—C30119.88 (12)
C3—C4—H4A108.5C36—C31—C30122.28 (12)
N5—C4—H4B108.5C33—C32—C31121.01 (14)
C3—C4—H4B108.5C33—C32—H32119.5
H4A—C4—H4B107.5C31—C32—H32119.5
O6—C6—O7124.44 (12)C32—C33—C34120.58 (14)
O6—C6—N5124.22 (12)C32—C33—H33119.7
O7—C6—N5111.34 (11)C34—C33—H33119.7
O7—C8—C10109.69 (12)C35—C34—C33119.14 (14)
O7—C8—C9101.12 (11)C35—C34—H34120.4
C10—C8—C9112.02 (15)C33—C34—H34120.4
O7—C8—C11110.82 (12)C34—C35—C36120.05 (14)
C10—C8—C11111.52 (13)C34—C35—H35120.0
C9—C8—C11111.23 (16)C36—C35—H35120.0
C8—C9—H9A109.5C35—C36—C31121.45 (14)
C8—C9—H9B109.5C35—C36—H36119.3
H9A—C9—H9B109.5C31—C36—H36119.3
C8—C9—H9C109.5C6—N5—C4123.71 (11)
H9A—C9—H9C109.5C6—N5—H5117.4 (11)
H9B—C9—H9C109.5C4—N5—H5116.2 (11)
C8—C10—H10A109.5C1—O1—H1109.5
C8—C10—H10B109.5C6—O7—C8122.65 (10)
H10A—C10—H10B109.5
O2—C1—C2—C35.74 (18)C32—C33—C34—C351.1 (2)
O1—C1—C2—C3174.26 (11)C33—C34—C35—C361.6 (2)
C1—C2—C3—C4168.26 (10)C34—C35—C36—C310.1 (2)
C1—C2—C3—C3071.50 (14)C32—C31—C36—C351.9 (2)
C2—C3—C4—N570.78 (14)C30—C31—C36—C35174.09 (13)
C30—C3—C4—N5168.17 (11)O6—C6—N5—C4165.44 (13)
C4—C3—C30—C3176.50 (15)O7—C6—N5—C414.81 (18)
C2—C3—C30—C31161.60 (11)C3—C4—N5—C689.89 (15)
C3—C30—C31—C3270.93 (17)O6—C6—O7—C83.7 (2)
C3—C30—C31—C36113.17 (15)N5—C6—O7—C8176.54 (11)
C36—C31—C32—C332.4 (2)C10—C8—O7—C663.08 (17)
C30—C31—C32—C33173.69 (14)C9—C8—O7—C6178.48 (15)
C31—C32—C33—C341.0 (2)C11—C8—O7—C660.48 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O6i0.821.832.6368 (15)170
N5—H5···O2ii0.846 (18)2.131 (18)2.8856 (16)148.2 (15)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O6i0.821.832.6368 (15)170
N5—H5···O2ii0.846 (18)2.131 (18)2.8856 (16)148.2 (15)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y1, z.
 

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Volume 70| Part 10| October 2014| Pages o1081-o1082
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