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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o965.
Published online 2009 April 8. doi:  10.1107/S1600536809012112
PMCID: PMC2977665

N-(2,3-Dimethyl­phen­yl)benzamide

Abstract

The conformation of the N—H bond in the structure of the title compound, C15H15NO, is anti to the ortho and meta-methyl substituents in the aniline benzene ring, in contrast to the syn conformation observed with respect to the ortho and meta-chloro substituents in N-(2,3-dichloro­phen­yl)benzamide. Furthermore, the conformations of N—H and C=O bonds in the amide group are anti to each other, similar to those observed in other benzanilides. The dihedral angle between the benzoyl and aniline rings is 84.1 (2)°. The amide group is twisted by 23.0 (3)° out of the plane of the benzoyl ring. The structure exhibits positional disorder over the aniline ring, with site occupancies of 0.80 (1) and 0.20 (1) for the major and minor components, respectively. In the crystal, mol­ecules are connected through N—H(...)O hydrogen bonds into chains running along the b axis. An intra­molecular C—H(...)O close contact occurs.

Related literature

For related structures, see Azumaya et al. (1994 [triangle]); Gowda et al. (2003 [triangle], 2007 [triangle], 2008a [triangle],b [triangle]).

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Object name is e-65-0o965-scheme1.jpg

Experimental

Crystal data

  • C15H15NO
  • M r = 225.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o965-efi2.jpg
  • a = 8.4656 (2) Å
  • b = 9.4848 (2) Å
  • c = 31.0957 (9) Å
  • V = 2496.81 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 K
  • 0.52 × 0.16 × 0.05 mm

Data collection

  • Oxford Diffraction Xcalibur System diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 [triangle]) T min = 0.963, T max = 0.996
  • 48994 measured reflections
  • 2409 independent reflections
  • 1572 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.146
  • S = 1.05
  • 2409 reflections
  • 222 parameters
  • 14 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.10 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 2002 [triangle]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 [triangle]) and WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012112/dn2440sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012112/dn2440Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

MT and JK thank the Grant Agency of the Slovak Republic (grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

supplementary crystallographic information

Comment

As part of our continuing efforts to explore the effect of substituents on the solid state geometries of benzanilides (Gowda et al., 2003, 2007, 2008a,b), in the present work, the structure of N-(2,3-dimethylphenyl)benzamide (N23DMPBA) has been determined. The conformation of the N—H bond in N23DMPBA is anti to both the ortho and meta-methyl substituents in the aniline benzene ring (Fig. 1), in contrast to the syn conformations observed with respect to both the ortho and meta-chloro substituents in N-(2,3-dichlorophenyl)benzamide (N23DCPBA)(Gowda et al., 2007), while the conformations of the N—H and C=O bonds in the amide group of N23DMPBA are anti to each other, similar to that observed in N23DCPBA, N-(2,6-dimethylphenyl)benzamide (Azumaya et al., 1994; Gowda et al., 2008b), N-(3,4-dimethylphenyl)benzamide (Gowda et al., 2008a) and other benzanilides (Gowda et al., 2003). In the crystal structure, the N—H···O hydrogen bonds link the molecules into chains running along the b axis (Table 1 & Fig. 2), while the structure is stabilized by C—H···N intramolecular hydrogen bond with atom C14 as donor and atom N1 as acceptor. The atoms of anilino ring (including the methyl groups) are positionally disordered (Fig. 3) with site occupancy factor 0.80 for major component (atoms C8 to C15) and 0.20 for minor component (C8d to C15d). The disordered orientations of anilino ring are essentially planar, forming a dihedral angle of 1.5 (7)°. The dihedral angle between the benzoyl and anilino ring (major) is 84.1 (2)°. The amido group is twisted by 23.0 (3)° out of the plane of benzoyl ring.

Experimental

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanol solution and used for X-ray diffraction studies at room temperature.

Refinement

During the refinement of (I) the atoms of anilino ring revealed unusual anisotropic displacement parameters, so we introduced two sets of split sites for this part of molecule. The positions of methyl groups were carefully localized (Fig.3). Final cycles of refinement were done with fixed site occupancy factors (0.80 and 1/5) and the following restraints: The major component of the disorder (atoms C8 to C15) was refined free, except for DELU restraint imposed on the atoms C8, C10. The minor component was subject to restraint on the geometry of the ring (rigid planar hexagon) and restraint on the anisotropic displacement parameters - using DELU instruction for ring atoms. As to the hydrogen atoms, the amido H atom was seen in difference maps and its positional parameters were refined with the restraint on N—H distance, set at 0.86 (2) Å. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances in the range 0.93–0.96 Å and with displacement parameters Uiso(H) set at 1.2 Ueq(C-aromatic,N) or 1.5 Ueq(C-methyl).

Figures

Fig. 1.
Molecular structure of (I) showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. For the sake of clarity, only the major component is represented. ...
Fig. 2.
Part of the crystal structure of (I). Molecular chains running along the b axis are generated by N—H···O(i) hydrogen bonds (shown as dashed lines). Symmetry code (i): -x + 1/2,y + 1/2,z. H atoms not involved in intermolecular ...
Fig. 3.
The disorder of the anilino ring in (I). The major component (C8 to C15) has site occupancy factor 0.80. The minor component atoms (C8d to C15d) with site occupancy factor 0.20 has their bonds shown as dashed lines.

Crystal data

C15H15NOF(000) = 960
Mr = 225.28Dx = 1.199 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 12625 reflections
a = 8.4656 (2) Åθ = 3.1–29.2°
b = 9.4848 (2) ŵ = 0.08 mm1
c = 31.0957 (9) ÅT = 295 K
V = 2496.81 (11) Å3Rod, colourless
Z = 80.52 × 0.16 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer2409 independent reflections
graphite1572 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1Rint = 0.052
ω scans with κ offsetsθmax = 25.9°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)h = −10→10
Tmin = 0.963, Tmax = 0.996k = −11→11
48994 measured reflectionsl = −38→38

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0655P)2 + 0.6303P] where P = (Fo2 + 2Fc2)/3
2409 reflections(Δ/σ)max < 0.001
222 parametersΔρmax = 0.10 e Å3
14 restraintsΔρmin = −0.14 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
N10.2585 (2)0.60702 (17)0.37113 (6)0.0562 (5)
H1N0.273 (3)0.6973 (18)0.3654 (7)0.067*
O10.1702 (2)0.39655 (14)0.34744 (5)0.0676 (5)
C10.1605 (2)0.52512 (19)0.34747 (6)0.0496 (5)
C20.0397 (2)0.59716 (19)0.32076 (6)0.0461 (5)
C3−0.0200 (2)0.5254 (2)0.28599 (7)0.0549 (5)
H30.01470.43420.28040.066*
C4−0.1302 (3)0.5859 (2)0.25935 (7)0.0635 (6)
H4−0.16780.53690.23560.076*
C5−0.1844 (3)0.7196 (2)0.26811 (8)0.0701 (7)
H5−0.25970.76090.25040.084*
C6−0.1277 (3)0.7913 (2)0.30275 (8)0.0729 (7)
H6−0.16570.88120.30870.087*
C7−0.0153 (3)0.7326 (2)0.32897 (7)0.0581 (6)
H70.02420.78330.35220.07*
C80.3938 (5)0.5547 (4)0.39290 (14)0.0517 (10)0.8
C90.3754 (4)0.4635 (4)0.42634 (13)0.0567 (8)0.8
C100.5108 (6)0.4031 (5)0.44545 (16)0.0718 (10)0.8
C110.6555 (6)0.4480 (7)0.4303 (2)0.0842 (13)0.8
H110.74580.40960.44270.101*0.8
C120.6745 (5)0.5444 (5)0.39867 (14)0.0910 (11)0.8
H120.77540.57180.39030.109*0.8
C130.5457 (5)0.6012 (5)0.37902 (16)0.0713 (12)0.8
H130.55630.6680.35730.086*0.8
C140.2156 (5)0.4279 (4)0.44389 (12)0.0748 (10)0.8
H14A0.21220.45020.4740.112*0.8
H14B0.19550.32920.43990.112*0.8
H14C0.13670.48170.4290.112*0.8
C150.4970 (6)0.2939 (4)0.48009 (12)0.1080 (14)0.8
H15A0.43260.21740.47010.162*0.8
H15B0.44930.33520.50510.162*0.8
H15C0.60020.25930.48730.162*0.8
C8D0.3513 (13)0.5282 (12)0.4010 (3)0.051 (4)0.2
C9D0.5124 (14)0.5487 (12)0.3951 (3)0.053 (3)0.2
C10D0.6201 (10)0.4779 (17)0.4211 (5)0.082 (5)0.2
C11D0.5667 (12)0.3865 (16)0.4528 (5)0.078 (5)0.2
H11D0.63870.33920.47020.094*0.2
C12D0.4055 (14)0.3660 (9)0.4587 (3)0.067 (3)0.2
H12D0.36980.30480.47990.081*0.2
C13D0.2978 (10)0.4368 (12)0.4328 (3)0.048 (3)0.2
H13D0.190.4230.43670.057*0.2
C14D0.5865 (19)0.648 (2)0.3617 (7)0.090 (6)0.2
H14D0.51120.66710.33930.135*0.2
H14E0.67860.60490.34960.135*0.2
H14F0.61570.73520.37540.135*0.2
C15D0.7999 (14)0.4840 (15)0.4207 (5)0.081 (4)0.2
H15D0.83750.47180.39180.121*0.2
H15E0.84140.41020.43860.121*0.2
H15F0.83430.57370.43150.121*0.2

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0656 (11)0.0354 (8)0.0678 (11)−0.0015 (8)−0.0083 (9)0.0018 (8)
O10.0834 (11)0.0337 (8)0.0856 (11)0.0058 (7)−0.0171 (9)−0.0005 (7)
C10.0582 (12)0.0324 (10)0.0582 (12)0.0000 (9)0.0030 (10)0.0016 (9)
C20.0481 (11)0.0361 (10)0.0540 (11)−0.0031 (8)0.0055 (9)0.0046 (9)
C30.0558 (12)0.0377 (10)0.0711 (14)−0.0031 (9)−0.0009 (11)−0.0025 (10)
C40.0614 (14)0.0581 (13)0.0710 (15)−0.0079 (11)−0.0129 (11)−0.0011 (11)
C50.0702 (15)0.0527 (13)0.0874 (17)−0.0020 (11)−0.0219 (13)0.0114 (13)
C60.0815 (16)0.0444 (12)0.0928 (18)0.0126 (12)−0.0174 (14)0.0009 (12)
C70.0700 (14)0.0386 (11)0.0659 (13)0.0030 (10)−0.0054 (11)−0.0014 (10)
C80.053 (3)0.0387 (15)0.063 (2)0.0004 (17)−0.0032 (18)−0.0055 (14)
C90.067 (2)0.0446 (18)0.059 (2)−0.0009 (18)−0.005 (2)−0.0083 (15)
C100.076 (3)0.064 (2)0.076 (3)0.003 (2)−0.015 (2)−0.0052 (19)
C110.081 (3)0.088 (3)0.083 (3)0.015 (3)−0.023 (3)−0.006 (2)
C120.060 (2)0.101 (3)0.112 (3)−0.012 (2)0.003 (2)−0.009 (2)
C130.057 (3)0.070 (3)0.088 (4)−0.014 (2)−0.003 (3)−0.006 (2)
C140.094 (3)0.066 (2)0.064 (2)−0.009 (2)0.008 (2)0.0078 (17)
C150.150 (4)0.085 (3)0.088 (3)0.019 (3)−0.035 (2)0.018 (2)
C8D0.050 (7)0.067 (10)0.037 (7)−0.007 (7)−0.002 (6)0.006 (6)
C9D0.053 (7)0.053 (9)0.052 (8)−0.020 (6)0.018 (5)−0.025 (5)
C10D0.052 (8)0.085 (16)0.108 (17)−0.008 (7)−0.015 (7)−0.031 (9)
C11D0.061 (7)0.090 (12)0.083 (12)0.029 (9)−0.026 (9)−0.020 (7)
C12D0.082 (8)0.061 (7)0.059 (7)0.005 (6)−0.019 (6)0.013 (5)
C13D0.037 (7)0.052 (8)0.054 (9)−0.001 (7)0.002 (7)0.012 (5)
C14D0.051 (9)0.083 (12)0.135 (16)−0.009 (7)0.029 (9)0.033 (10)
C15D0.046 (7)0.101 (10)0.096 (10)−0.004 (6)−0.009 (7)0.022 (8)

Geometric parameters (Å, °)

N1—C11.354 (3)C12—H120.93
N1—C81.419 (4)C13—H130.93
N1—C8D1.428 (4)C14—H14A0.96
N1—H1N0.883 (16)C14—H14B0.96
O1—C11.222 (2)C14—H14C0.96
C1—C21.484 (3)C15—H15A0.96
C2—C31.374 (3)C15—H15B0.96
C2—C71.390 (3)C15—H15C0.96
C3—C41.373 (3)C8D—C9D1.39
C3—H30.93C8D—C13D1.39
C4—C51.376 (3)C9D—C10D1.39
C4—H40.93C9D—C14D1.538 (16)
C5—C61.361 (3)C10D—C11D1.39
C5—H50.93C10D—C15D1.523 (15)
C6—C71.372 (3)C11D—C12D1.39
C6—H60.93C11D—H11D0.93
C7—H70.93C12D—C13D1.39
C8—C91.361 (4)C12D—H12D0.93
C8—C131.426 (6)C13D—H13D0.93
C9—C101.412 (6)C14D—H14D0.96
C9—C141.497 (5)C14D—H14E0.96
C10—C111.379 (7)C14D—H14F0.96
C10—C151.499 (5)C15D—H15D0.96
C11—C121.353 (6)C15D—H15E0.96
C11—H110.93C15D—H15F0.96
C12—C131.361 (6)
C1—N1—C8123.6 (2)C10—C11—H11117.9
C1—N1—C8D113.0 (6)C11—C12—C13119.9 (4)
C1—N1—H1N122.1 (14)C11—C12—H12120
C8—N1—H1N108.8 (15)C13—C12—H12120
C8D—N1—H1N124.2 (15)C12—C13—C8117.6 (4)
O1—C1—N1122.11 (19)C12—C13—H13121.2
O1—C1—C2120.35 (18)C8—C13—H13121.2
N1—C1—C2117.54 (16)C9D—C8D—C13D120
C3—C2—C7118.64 (19)C9D—C8D—N1112.4 (8)
C3—C2—C1117.75 (17)C13D—C8D—N1127.6 (8)
C7—C2—C1123.60 (18)C10D—C9D—C8D120
C4—C3—C2121.16 (19)C10D—C9D—C14D114.9 (11)
C4—C3—H3119.4C8D—C9D—C14D125.1 (11)
C2—C3—H3119.4C9D—C10D—C11D120
C3—C4—C5119.5 (2)C9D—C10D—C15D129.3 (10)
C3—C4—H4120.3C11D—C10D—C15D110.7 (10)
C5—C4—H4120.3C12D—C11D—C10D120
C6—C5—C4120.0 (2)C12D—C11D—H11D120
C6—C5—H5120C10D—C11D—H11D120
C4—C5—H5120C11D—C12D—C13D120
C5—C6—C7120.8 (2)C11D—C12D—H12D120
C5—C6—H6119.6C13D—C12D—H12D120
C7—C6—H6119.6C12D—C13D—C8D120
C6—C7—C2119.9 (2)C12D—C13D—H13D120
C6—C7—H7120.1C8D—C13D—H13D120
C2—C7—H7120.1C9D—C14D—H14D109.5
C9—C8—N1119.6 (4)C9D—C14D—H14E109.5
C9—C8—C13122.0 (3)H14D—C14D—H14E109.5
N1—C8—C13118.3 (3)C9D—C14D—H14F109.5
C8—C9—C10119.1 (4)H14D—C14D—H14F109.5
C8—C9—C14121.6 (4)H14E—C14D—H14F109.5
C10—C9—C14119.2 (4)C10D—C15D—H15D109.5
C11—C10—C9116.9 (4)C10D—C15D—H15E109.5
C11—C10—C15121.8 (5)H15D—C15D—H15E109.5
C9—C10—C15121.3 (4)C10D—C15D—H15F109.5
C12—C11—C10124.2 (4)H15D—C15D—H15F109.5
C12—C11—H11117.9H15E—C15D—H15F109.5
C8—N1—C1—O19.3 (4)C8—C9—C10—C15−175.3 (4)
C8D—N1—C1—O1−10.7 (6)C14—C9—C10—C155.9 (7)
C8—N1—C1—C2−170.1 (3)C9—C10—C11—C12−0.4 (8)
C8D—N1—C1—C2169.9 (6)C15—C10—C11—C12178.8 (6)
O1—C1—C2—C3−22.5 (3)C10—C11—C12—C13−1.4 (9)
N1—C1—C2—C3156.95 (19)C11—C12—C13—C8−0.4 (8)
O1—C1—C2—C7157.7 (2)C9—C8—C13—C124.0 (6)
N1—C1—C2—C7−22.8 (3)N1—C8—C13—C12−176.6 (4)
C7—C2—C3—C40.9 (3)C1—N1—C8D—C9D122.9 (7)
C1—C2—C3—C4−178.90 (19)C8—N1—C8D—C9D−2.8 (14)
C2—C3—C4—C5−1.5 (3)C1—N1—C8D—C13D−55.9 (9)
C3—C4—C5—C60.6 (4)C8—N1—C8D—C13D178 (3)
C4—C5—C6—C70.8 (4)C13D—C8D—C9D—C10D0
C5—C6—C7—C2−1.3 (4)N1—C8D—C9D—C10D−178.9 (12)
C3—C2—C7—C60.5 (3)C13D—C8D—C9D—C14D−179.0 (17)
C1—C2—C7—C6−179.7 (2)N1—C8D—C9D—C14D2.1 (18)
C1—N1—C8—C9−66.2 (4)C8D—C9D—C10D—C11D0
C8D—N1—C8—C9−2.2 (18)C14D—C9D—C10D—C11D179.1 (15)
C1—N1—C8—C13114.4 (4)C8D—C9D—C10D—C15D−179.8 (18)
C8D—N1—C8—C13178 (2)C14D—C9D—C10D—C15D−0.7 (19)
N1—C8—C9—C10174.8 (4)C9D—C10D—C11D—C12D0
C13—C8—C9—C10−5.8 (6)C15D—C10D—C11D—C12D179.8 (15)
N1—C8—C9—C14−6.4 (6)C10D—C11D—C12D—C13D0
C13—C8—C9—C14173.0 (4)C11D—C12D—C13D—C8D0
C8—C9—C10—C113.9 (6)C9D—C8D—C13D—C12D0
C14—C9—C10—C11−174.9 (4)N1—C8D—C13D—C12D178.7 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.88 (2)2.03 (2)2.907 (2)173 (2)
C14—H14C···N10.962.392.852 (4)109

Symmetry codes: (i) −x+1/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2440).

References

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