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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 10| October 2011| Page o2632
https://doi.org/10.1107/S1600536811036464

1-(2-Hy­dr­oxy-2-phenyl­eth­yl)-3-(4-meth­­oxy­phen­yl)urea

Hyeong Choi,a Yong Suk Shim,a Sung Chun Lee,a Sung Kwon Kanga* and Chang Keun Sungb

aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea, and bDepartment of Food Science and Technology, Chungnam National University, Daejeon 305-764, Republic of Korea
*Correspondence e-mail: skkang@cnu.ac.kr

(Received 30 August 2011; accepted 7 September 2011; online 14 September 2011)

In the title compound, C16H18N2O3, the dihedral angle between the 4-meth­oxy­phenyl ring and the urea group is 35.6 (2) °. The H atoms of the urea NH groups are positioned syn to each other. In the crystal, inter­molecular N—H⋯O and O—H⋯O hydrogen bonds link the mol­ecules into a two-dimensional array in the ac plane; the carbonyl-O atom is trifurcated.

Related literature

For general background to melanin, see: Prota (1988[Prota, G. (1988). Med. Res. Rev. 8, 525-556.]). For the development of potent inhibitory agents of tyrosinase, see: Khan et al. (2006[Khan, K. M., Mughal, U. R., Khan, M. T. H., Perveen, S., Ullah, Z. & Choudhary, M. I. (2006). Bioorg. Med. Chem. 14, 344-351.]); Kojima et al. (1995[Kojima, S., Yamaguch, K., Morita, K., Ueno, Y. & Paolo, R. (1995). Biol. Pharm. Bull. 18, 1076-1080.]); Cabanes et al. (1994[Cabanes, J., Chazarra, S. & Garcia-Carmona, F. (1994). J. Pharm. Pharmacol. 46, 982-985.]); Son et al. (2000[Son, S. M., Moon, K. D. & Lee, C. Y. (2000). J. Agric. Food Chem. 48, 2071-2074.]); Iida et al. (1995[Iida, K., Hase, K., Shimomura, K., Sudo, S. & Kadota, S. (1995). Planta Med. 61, 425-428.]).

[Scheme 1]

Experimental

Crystal data

  • C16H18N2O3

  • Mr = 286.32

  • Monoclinic, P 21

  • a = 6.8120 (6) Å

  • b = 8.7659 (7) Å

  • c = 12.1393 (10) Å

  • β = 97.009 (3)°

  • V = 719.46 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.07 × 0.05 × 0.03 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • 5017 measured reflections

  • 1947 independent reflections

  • 1782 reflections with I > 2σ(I)

  • Rint = 0.073
Refinement

  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.166

  • S = 1.05

  • 1947 reflections

  • 201 parameters

  • 1 restraint

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

  • Δρmax = 0.71 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O8—H8⋯O12i 0.86 (7) 2.09 (7) 2.863 (5) 150 (6)
N10—H10⋯O12ii 0.81 (6) 2.35 (6) 3.098 (5) 153 (5)
N13—H13⋯O12ii 0.79 (5) 2.14 (5) 2.898 (5) 161 (4)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z]; (ii) [-x+2, y+{\script{1\over 2}}, -z].

Data collection: SMART (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811036464/tk2785sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036464/tk2785Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811036464/tk2785Isup3.cml

checkCIF report


Comment top

Melanin is one of the most widely distributed pigments and is found in bacteria, fungi, plants and animals. It is a heterogeneous polyphenol-like biopolymer with a complex structure and colour varying from yellow to black (Prota, 1988). Tyrosinase inhibitors are clinically useful for the treatment of some dermatological disorders associated with melanin hyperpigmentation and are also important in the cosmetic industry for whitening and depigmentation after sunburn (Khan et al., 2006). Numerous potential tyrosinase inhibitors have been discovered from natural and synthetic sources, such as ascorbic acid (Kojima et al., 1995), kojic acid (Cabanes et al., 1994), and tropolone (Son et al., 2000; Iida et al., 1995). But some of their individual activities are either not potent enough to be considered of practical use or not compatible with safety regulations for food and cosmetic additives. In our continuing search for tyrosinase inhibitors, we have synthesized the title compound, (I), from the reaction of 2-amino-1-phenylethanol and 4-methoxyphenyl isocyanate under ambient conditions. Herein, the crystal structure of (I) is described (Fig. 1).

The 4-methoxyphenyl unit is almost planar, with an r.m.s. deviation of 0.031 Å from the least-squares plane defined by the eight constituent atoms. The dihedral angle between the 4-methoxyphenyl ring and the urea plane is 35.6 (2) °. The H atoms of the urea NH groups are positioned syn to each other. The presence of intermolecular N—H···O and O—H···O hydrogen bonds link the molecules into a two-dimensional array in the ac plane (Fig. 2, Table 1). The urea-O accepts three hydrogen bonds, one from –OH and two from –NH groups.

Related literature top

For general background to melanin, see: Prota (1988). For the development of potent inhibitory agents of tyrosinase, see: Khan et al. (2006); Kojima et al. (1995); Cabanes et al. (1994); Son et al. (2000); Iida et al. (1995).

Experimental top

2-Amino-1-phenylethanol and 4-methoxyphenyl isocyanate were purchased from Sigma Chemical Co. All other chemicals and solvents were of analytical grade and were used without further purification. The title compound (I) was prepared from the reaction of 2-amino-1-phenylethanol (0.3 g, 1.2 mmol) with 4-methoxyphenyl isocyanate (0.39 g, 1.0 mmol) in acetonitrile (6 ml) with stirring. The reaction was completed within 1 h at room temperature. The solvents were removed under reduced pressure, collected and washed with dichloromethane. Removal of the solvent gave a white solid (84%; M.pt 468 K). Colourless crystals of (I) were obtained from its ethanolic solution by slow evaporation of the solvent at room temperature.

Refinement top

The NH H atoms were located in a difference Fourier map and refined freely. The OH H atom was located in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(O). The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq (C) for aromatic and methylene, and 1.5Ueq(C) for methyl H atoms. In the absence of significant anomalous scattering effects, 578 Friedel pairs were averaged in the final refinement. The maximum and minimum residual electron density peaks of 0.71 and -0.26 eÅ-3, respectively, were located at 0.99 Å and 0.42 Å from the C7 and H7 atoms, respectively.

Structure description top

Melanin is one of the most widely distributed pigments and is found in bacteria, fungi, plants and animals. It is a heterogeneous polyphenol-like biopolymer with a complex structure and colour varying from yellow to black (Prota, 1988). Tyrosinase inhibitors are clinically useful for the treatment of some dermatological disorders associated with melanin hyperpigmentation and are also important in the cosmetic industry for whitening and depigmentation after sunburn (Khan et al., 2006). Numerous potential tyrosinase inhibitors have been discovered from natural and synthetic sources, such as ascorbic acid (Kojima et al., 1995), kojic acid (Cabanes et al., 1994), and tropolone (Son et al., 2000; Iida et al., 1995). But some of their individual activities are either not potent enough to be considered of practical use or not compatible with safety regulations for food and cosmetic additives. In our continuing search for tyrosinase inhibitors, we have synthesized the title compound, (I), from the reaction of 2-amino-1-phenylethanol and 4-methoxyphenyl isocyanate under ambient conditions. Herein, the crystal structure of (I) is described (Fig. 1).

The 4-methoxyphenyl unit is almost planar, with an r.m.s. deviation of 0.031 Å from the least-squares plane defined by the eight constituent atoms. The dihedral angle between the 4-methoxyphenyl ring and the urea plane is 35.6 (2) °. The H atoms of the urea NH groups are positioned syn to each other. The presence of intermolecular N—H···O and O—H···O hydrogen bonds link the molecules into a two-dimensional array in the ac plane (Fig. 2, Table 1). The urea-O accepts three hydrogen bonds, one from –OH and two from –NH groups.

For general background to melanin, see: Prota (1988). For the development of potent inhibitory agents of tyrosinase, see: Khan et al. (2006); Kojima et al. (1995); Cabanes et al. (1994); Son et al. (2000); Iida et al. (1995).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom-numbering scheme and 30% probability ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing 2-D array of molecules linked by intermolecular N—H···O and O—H···O hydrogen bonds (dashed lines).
1-(2-Hydroxy-2-phenylethyl)-3-(4-methoxyphenyl)urea top
Crystal data top
C16H18N2O3F(000) = 304
Mr = 286.32Dx = 1.322 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4535 reflections
a = 6.8120 (6) Åθ = 2.9–28.1°
b = 8.7659 (7) ŵ = 0.09 mm−1
c = 12.1393 (10) ÅT = 296 K
β = 97.009 (3)°Block, colourless
V = 719.46 (10) Å30.07 × 0.05 × 0.03 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer		Rint = 0.073
Graphite monochromatorθmax = 25.5°, θmin = 1.7°
φ and ω scansh = −7→8
5017 measured reflectionsk = −5→10
1947 independent reflectionsl = −7→14
1782 reflections with I > 2σ(I)
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0819P)2 + 0.6912P]
where P = (Fo2 + 2Fc2)/3
1947 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.71 e Å−3
1 restraintΔρmin = −0.26 e Å−3
Crystal data top
C16H18N2O3V = 719.46 (10) Å3
Mr = 286.32Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.8120 (6) ŵ = 0.09 mm−1
b = 8.7659 (7) ÅT = 296 K
c = 12.1393 (10) Å0.07 × 0.05 × 0.03 mm
β = 97.009 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		1782 reflections with I > 2σ(I)
5017 measured reflectionsRint = 0.073
1947 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0601 restraint
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.71 e Å−3
1947 reflectionsΔρmin = −0.26 e Å−3
201 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C10.3090 (6)0.9178 (6)−0.2016 (4)0.0461 (12)
C20.2104 (7)0.7832 (7)−0.1959 (4)0.0533 (14)
H20.24010.7201−0.13450.064*
C30.0666 (8)0.7396 (7)−0.2805 (4)0.0542 (13)
H30.00170.6469−0.27580.065*
C40.0191 (7)0.8310 (7)−0.3707 (4)0.0505 (13)
H4−0.07870.8012−0.42680.061*
C50.1151 (7)0.9660 (7)−0.3783 (4)0.0530 (14)
H50.08381.0293−0.43940.064*
C60.2616 (7)1.0081 (7)−0.2929 (5)0.0571 (14)
H60.32851.0998−0.29830.069*
C70.4712 (7)0.9574 (7)−0.1086 (5)0.0613 (16)
H70.45190.8924−0.04510.074*
O80.4713 (6)1.1060 (5)−0.0726 (3)0.0631 (11)
H80.347 (10)1.118 (8)−0.071 (5)0.076*
C90.6694 (6)0.9180 (6)−0.1428 (3)0.0378 (10)
H9A0.67960.8079−0.14850.045*
H9B0.67820.9604−0.21590.045*
N100.8347 (5)0.9736 (5)−0.0668 (3)0.0369 (9)
H100.876 (8)1.060 (7)−0.072 (4)0.052 (17)*
C110.9310 (5)0.8900 (5)0.0159 (3)0.0309 (9)
O120.8885 (4)0.7545 (3)0.0342 (2)0.0365 (7)
N131.0818 (5)0.9640 (5)0.0765 (3)0.0345 (8)
H131.108 (7)1.048 (7)0.060 (4)0.036 (14)*
C141.2036 (6)0.9091 (5)0.1709 (3)0.0305 (9)
C151.3978 (6)0.9599 (5)0.1905 (3)0.0351 (10)
H151.44821.02230.13870.042*
C161.5166 (6)0.9188 (5)0.2859 (3)0.0349 (10)
H161.64590.95460.29830.042*
C171.4460 (6)0.8252 (5)0.3630 (3)0.0345 (10)
C181.2540 (6)0.7706 (6)0.3442 (3)0.0383 (10)
H181.20690.7050.39510.046*
C191.1310 (6)0.8140 (5)0.2487 (3)0.0369 (10)
H191.0010.77950.2370.044*
O201.5764 (4)0.7926 (4)0.4554 (2)0.0435 (9)
C211.5099 (8)0.6908 (7)0.5350 (4)0.0520 (13)
H21A1.61310.67680.59540.078*
H21B1.47640.59420.50050.078*
H21C1.39540.73310.56260.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.029 (2)0.051 (3)0.057 (3)0.014 (2)0.0003 (18)−0.010 (3)
C20.045 (3)0.067 (4)0.048 (2)0.015 (3)0.010 (2)0.003 (3)
C30.042 (3)0.054 (3)0.069 (3)−0.007 (2)0.016 (2)0.004 (3)
C40.029 (2)0.071 (4)0.049 (2)−0.004 (2)−0.0010 (18)−0.006 (3)
C50.041 (3)0.062 (4)0.056 (3)0.013 (3)0.008 (2)0.014 (3)
C60.035 (3)0.044 (3)0.094 (4)0.000 (2)0.015 (3)−0.002 (3)
C70.044 (3)0.070 (4)0.067 (3)0.006 (3)−0.002 (2)−0.025 (3)
O80.0414 (18)0.065 (3)0.080 (2)0.0104 (19)−0.0049 (17)−0.033 (2)
C90.029 (2)0.040 (3)0.042 (2)0.0025 (19)−0.0037 (16)−0.006 (2)
N100.0314 (19)0.034 (2)0.0427 (19)−0.0011 (17)−0.0043 (14)−0.0009 (18)
C110.0236 (18)0.033 (2)0.0371 (19)0.0026 (17)0.0090 (15)−0.0025 (19)
O120.0340 (15)0.0310 (18)0.0438 (15)−0.0032 (13)0.0016 (11)−0.0008 (13)
N130.0353 (19)0.031 (2)0.0355 (17)−0.0055 (17)−0.0031 (14)0.0057 (17)
C140.030 (2)0.030 (2)0.0311 (18)−0.0019 (18)0.0014 (15)−0.0015 (18)
C150.037 (2)0.037 (3)0.0305 (18)−0.006 (2)0.0044 (15)−0.0015 (19)
C160.031 (2)0.039 (3)0.0342 (19)−0.0056 (19)0.0017 (15)−0.0048 (19)
C170.039 (2)0.035 (2)0.0292 (18)0.004 (2)0.0013 (16)−0.0045 (19)
C180.038 (2)0.043 (3)0.0347 (19)−0.005 (2)0.0052 (16)0.007 (2)
C190.029 (2)0.040 (3)0.041 (2)−0.0039 (19)0.0045 (16)0.000 (2)
O200.0412 (17)0.049 (2)0.0375 (15)−0.0036 (15)−0.0045 (12)0.0146 (15)
C210.049 (3)0.065 (4)0.041 (2)−0.003 (3)−0.001 (2)0.021 (2)
Geometric parameters (Å, º) top
C1—C21.363 (8)N10—H100.81 (6)
C1—C61.369 (7)C11—O121.249 (5)
C1—C71.520 (7)C11—N131.354 (5)
C2—C31.384 (7)N13—C141.415 (5)
C2—H20.93N13—H130.79 (5)
C3—C41.364 (8)C14—C151.389 (5)
C3—H30.93C14—C191.395 (6)
C4—C51.361 (8)C15—C161.377 (6)
C4—H40.93C15—H150.93
C5—C61.398 (7)C16—C171.375 (6)
C5—H50.93C16—H160.93
C6—H60.93C17—O201.374 (4)
C7—O81.374 (7)C17—C181.385 (6)
C7—C91.501 (7)C18—C191.398 (6)
C7—H70.98C18—H180.93
O8—H80.86 (7)C19—H190.93
C9—N101.450 (5)O20—C211.429 (6)
C9—H9A0.97C21—H21A0.96
C9—H9B0.97C21—H21B0.96
N10—C111.347 (5)C21—H21C0.96
C2—C1—C6118.2 (4)C9—N10—H10121 (4)
C2—C1—C7118.5 (5)O12—C11—N10123.2 (4)
C6—C1—C7123.2 (5)O12—C11—N13122.4 (4)
C1—C2—C3120.7 (5)N10—C11—N13114.4 (4)
C1—C2—H2119.7C11—N13—C14127.5 (4)
C3—C2—H2119.7C11—N13—H13119 (3)
C4—C3—C2120.7 (5)C14—N13—H13113 (3)
C4—C3—H3119.6C15—C14—C19119.0 (3)
C2—C3—H3119.6C15—C14—N13118.8 (4)
C5—C4—C3119.8 (5)C19—C14—N13122.0 (3)
C5—C4—H4120.1C16—C15—C14120.7 (4)
C3—C4—H4120.1C16—C15—H15119.7
C4—C5—C6119.0 (5)C14—C15—H15119.7
C4—C5—H5120.5C17—C16—C15120.7 (4)
C6—C5—H5120.5C17—C16—H16119.7
C1—C6—C5121.6 (5)C15—C16—H16119.7
C1—C6—H6119.2O20—C17—C16115.8 (4)
C5—C6—H6119.2O20—C17—C18124.5 (4)
O8—C7—C9109.9 (5)C16—C17—C18119.7 (3)
O8—C7—C1115.1 (4)C17—C18—C19120.1 (4)
C9—C7—C1109.8 (4)C17—C18—H18120
O8—C7—H7107.2C19—C18—H18120
C9—C7—H7107.2C14—C19—C18119.8 (4)
C1—C7—H7107.2C14—C19—H19120.1
C7—O8—H8100 (5)C18—C19—H19120.1
N10—C9—C7113.6 (4)C17—O20—C21117.1 (3)
N10—C9—H9A108.8O20—C21—H21A109.5
C7—C9—H9A108.8O20—C21—H21B109.5
N10—C9—H9B108.8H21A—C21—H21B109.5
C7—C9—H9B108.8O20—C21—H21C109.5
H9A—C9—H9B107.7H21A—C21—H21C109.5
C11—N10—C9124.1 (4)H21B—C21—H21C109.5
C11—N10—H10115 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8···O12i0.86 (7)2.09 (7)2.863 (5)150 (6)
N10—H10···O12ii0.81 (6)2.35 (6)3.098 (5)153 (5)
N13—H13···O12ii0.79 (5)2.14 (5)2.898 (5)161 (4)
Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x+2, y+1/2, −z.

Experimental details

Crystal data
Chemical formulaC16H18N2O3
Mr286.32
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)6.8120 (6), 8.7659 (7), 12.1393 (10)
β (°) 97.009 (3)
V (Å3)719.46 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.07 × 0.05 × 0.03
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		5017, 1947, 1782
Rint0.073
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.166, 1.05
No. of reflections1947
No. of parameters201
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.71, −0.26

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8···O12i0.86 (7)2.09 (7)2.863 (5)150 (6)
N10—H10···O12ii0.81 (6)2.35 (6)3.098 (5)153 (5)
N13—H13···O12ii0.79 (5)2.14 (5)2.898 (5)161 (4)
Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x+2, y+1/2, −z.
 

Acknowledgements

We wish to thank the DBIO company for partial support of this work.

References

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2632
https://doi.org/10.1107/S1600536811036464
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