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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 66| Part 11| November 2010| Page o3037
https://doi.org/10.1107/S1600536810044089

N,N′-Bis(3-methyl­phen­yl)propane­di­amide

B. Thimme Gowda,a* Miroslav Tokarčík,b Vinola Z. Rodrigues,a Jozef Kožíšekb and Hartmut Fuessc

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 26 October 2010; accepted 28 October 2010; online 31 October 2010)

The mol­ecular structure of the title compound, C17H18N2O2, is symmetrical around the central C atom. The two halves of the mol­ecule are related by a twofold rotation axis. In each half of the mol­ecule, the structure is stabilized by intra­molecular C—H⋯O hydrogen bonds. Furthermore, each amide group is almost coplanar with the adjacent benzene ring [dihedral angle is 9.2 (2)°]. The planes of the amide groups are inclined at an angle of 68.5 (1)°, while the two benzene rings make a dihedral angle of 70.40 (3)°. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O hydrogen bonds into chains running along the c axis. Neighbouring chains are weakly coupled by π–π stacking inter­actions [centroid–centroid distance = 3.7952 (8) Å].

Related literature

For related compounds, see: Gowda et al. (2007[Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91-100.], 2009[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.], 2010[Gowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010). Acta Cryst. E66, o1363.]).

[Scheme 1]

Experimental

Crystal data

  • C17H18N2O2

  • Mr = 282.33

  • Monoclinic, C 2/c

  • a = 15.3617 (6) Å

  • b = 11.2277 (6) Å

  • c = 8.7316 (5) Å

  • β = 90.370 (4)°

  • V = 1505.97 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 295 K

  • 0.58 × 0.27 × 0.16 mm
Data collection

  • Oxford Diffraction Gemini R CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.970, Tmax = 0.989

  • 11578 measured reflections

  • 1457 independent reflections

  • 1252 reflections with I > 2σ(I)

  • Rint = 0.019
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.096

  • S = 1.05

  • 1457 reflections

  • 101 parameters

  • 1 restraint

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

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C6—H6⋯O1 0.93 2.34 2.9124 (14) 120
N1—H1N⋯O1i 0.86 2.16 2.9932 (12) 162
C8—H8⋯O1i 0.97 (1) 2.54 (1) 3.3981 (9) 149 (1)
Symmetry code: (i) [x, -y+1, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 DIAMOND (Brandenburg, 2002[Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810044089/bq2245sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044089/bq2245Isup2.hkl

checkCIF report


Comment top

The amide moiety is an important constituent of many biologically important compounds. As a part of studying the substituent effects on the structures of this class of compounds (Gowda et al., 2007; 2009; 2010), the crystal structure of N,N-bis(3-methylphenyl)- propanediamide has been determined (I) (Fig. 1).

The molecule of (I) is symmetrical around the central carbon atom C8. The two halves of the molecule are related by the symmetry (-x + 1,y,-z + 1/2), which is a twofold rotation axis. The molecular structure is stabilized by the C–H···O intramolecular hydrogen bond in each half of the molecule (Table 1). In the geometry of the molecule, each amide group is almost coplanar with the adjacent phenyl ring, as indicated by the dihedral angle of 9.2 (2)°. The planes of amide groups are inclined at an angle of 68.5 (1)°, while the two phenyl rings make a dihedral angle of 70.40 (3)°. In the crystal, the molecules are linked by intermolecular N–H···O hydrogen bonds into the chains running along the c axis (Fig. 2). The neighboring chains are weakly coupled by π–π stacking interaction between the phenyl ring centroid Cg1 at the position (x,y,z) and the centroid Cg1 at the position (1/2 - x,1/2 - y,-z). The stacking geometry is such that the interplanar distance of the rings is 3.5290 (5) Å, the centroid-centroid distance is 3.7952 (8)Å and the offset is 1.396 (1) Å.

Related literature top

For literature on related compounds, see: Gowda et al. (2007, 2009, 2010).

Experimental top

Malonic acid (0.3 mol) in dichloromethane (30 ml) was treated with m-toluidine (0.6 mol) in dichloromethane (30 ml), dropwise with stirring. The resulting mixture was stirred for 3 hrs and kept aside for 12 hrs for the completion of reaction and evaporation of the solvent, dichloromethane. The product obtained was added to crushed ice to obtain the precipitate. The latter was thoroughly washed with water and then with saturated sodium bicarbonate solution and washed again with water. It was then given a wash with 2 N HCl. It was again washed with water, filtered, dried and recrystallized to the constant melting point from ethanol.

Prism like colorless single crystals of the title compound used in X-ray diffraction studies were obtained by a slow evaporation of its ehanolic solution at room temperature.

Refinement top

All hydrogen atoms, except for H atoms attached to C8, were positioned geometrically and refined using a riding model with C–H = 0.93 or 0.96 Å and N–H = 0.86 Å. The Uiso(H) values were set at 1.2Ueq(C, N) or 1.5Ueq(C-methyl). The hydrogen atom attached to the central C8 atom was refined freely with the bond length restrained to 0.93 (3) Å. The second hydrogen atom attached to C8 is positioned via the symmetry operator (ii): -x + 1,y,-z + 1/2. The C9-methyl group was treated as orientational disordered in the positions of H atoms. Two sets of methyl hydrogen atoms were refined with equal occupancies of 0.50.

Structure description top

The amide moiety is an important constituent of many biologically important compounds. As a part of studying the substituent effects on the structures of this class of compounds (Gowda et al., 2007; 2009; 2010), the crystal structure of N,N-bis(3-methylphenyl)- propanediamide has been determined (I) (Fig. 1).

The molecule of (I) is symmetrical around the central carbon atom C8. The two halves of the molecule are related by the symmetry (-x + 1,y,-z + 1/2), which is a twofold rotation axis. The molecular structure is stabilized by the C–H···O intramolecular hydrogen bond in each half of the molecule (Table 1). In the geometry of the molecule, each amide group is almost coplanar with the adjacent phenyl ring, as indicated by the dihedral angle of 9.2 (2)°. The planes of amide groups are inclined at an angle of 68.5 (1)°, while the two phenyl rings make a dihedral angle of 70.40 (3)°. In the crystal, the molecules are linked by intermolecular N–H···O hydrogen bonds into the chains running along the c axis (Fig. 2). The neighboring chains are weakly coupled by π–π stacking interaction between the phenyl ring centroid Cg1 at the position (x,y,z) and the centroid Cg1 at the position (1/2 - x,1/2 - y,-z). The stacking geometry is such that the interplanar distance of the rings is 3.5290 (5) Å, the centroid-centroid distance is 3.7952 (8)Å and the offset is 1.396 (1) Å.

For literature on related compounds, see: Gowda et al. (2007, 2009, 2010).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (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 DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. The molecule consists of two identical parts related by the symmetry operator (ii): -x + 1, y, -z + 1/2 with C8 atom as the center. Two intramolecular hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Crystal structure of (I) showing infinite molecular chain running along the c axis, generated by intermolecular N—H···O(i) hydrogen bonds shown as dashed lines. H atoms not participating in hydrogen bonding have been omitted. Symmetry operators (i): x, -y + 1, z - 1/2; (ii): -x + 1, y, -z + 1/2.
N,N'-Bis(3-methylphenyl)propanediamide top
Crystal data top
C17H18N2O2F(000) = 600
Mr = 282.33Dx = 1.245 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7458 reflections
a = 15.3617 (6) Åθ = 3.5–29.5°
b = 11.2277 (6) ŵ = 0.08 mm−1
c = 8.7316 (5) ÅT = 295 K
β = 90.370 (4)°Prism, colorless
V = 1505.97 (13) Å30.58 × 0.27 × 0.16 mm
Z = 4
Data collection top
Oxford Diffraction Gemini R CCD
diffractometer		1457 independent reflections
Graphite monochromator1252 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1Rint = 0.019
ω scansθmax = 25.8°, θmin = 3.2°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		h = −18→18
Tmin = 0.970, Tmax = 0.989k = −13→13
11578 measured reflectionsl = −10→10
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0517P)2 + 0.487P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1457 reflectionsΔρmax = 0.15 e Å−3
101 parametersΔρmin = −0.13 e Å−3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (2)
Crystal data top
C17H18N2O2V = 1505.97 (13) Å3
Mr = 282.33Z = 4
Monoclinic, C2/cMo Kα radiation
a = 15.3617 (6) ŵ = 0.08 mm−1
b = 11.2277 (6) ÅT = 295 K
c = 8.7316 (5) Å0.58 × 0.27 × 0.16 mm
β = 90.370 (4)°
Data collection top
Oxford Diffraction Gemini R CCD
diffractometer		1457 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		1252 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.989Rint = 0.019
11578 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0321 restraint
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.15 e Å−3
1457 reflectionsΔρmin = −0.13 e Å−3
101 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 > 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*/UeqOcc. (<1)
C10.27806 (7)0.38760 (10)0.16427 (12)0.0365 (3)
C20.22710 (7)0.41256 (11)0.03724 (13)0.0419 (3)
H20.24980.4597−0.04040.05*
C30.14287 (8)0.36894 (12)0.02273 (14)0.0475 (3)
C40.11069 (8)0.29958 (13)0.14029 (16)0.0559 (4)
H40.05420.270.13390.067*
C50.16120 (9)0.27374 (14)0.26661 (16)0.0583 (4)
H50.13830.22680.34430.07*
C60.24561 (8)0.31628 (12)0.28041 (13)0.0478 (3)
H60.27970.29750.36550.057*
C70.42002 (7)0.44614 (9)0.28233 (11)0.0334 (3)
C80.50.52114 (14)0.250.0364 (4)
H80.4902 (8)0.5697 (12)0.1602 (13)0.044*
C90.08888 (10)0.39539 (16)−0.11743 (19)0.0696 (5)
H9A0.1070.4699−0.16080.104*0.5
H9B0.02860.4002−0.08970.104*0.5
H9C0.09660.333−0.19130.104*0.5
H9D0.04780.3322−0.13370.104*0.5
H9E0.12620.4019−0.20480.104*0.5
H9F0.05820.469−0.10320.104*0.5
N10.36255 (6)0.43945 (9)0.16717 (10)0.0382 (3)
H1N0.3790.47110.08250.046*
O10.41040 (5)0.39905 (8)0.40829 (8)0.0475 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0337 (6)0.0422 (6)0.0337 (5)−0.0052 (4)−0.0007 (4)−0.0028 (4)
C20.0378 (6)0.0485 (7)0.0394 (6)−0.0059 (5)−0.0026 (5)0.0048 (5)
C30.0382 (6)0.0509 (7)0.0532 (7)−0.0035 (5)−0.0085 (5)−0.0028 (6)
C40.0394 (7)0.0619 (8)0.0663 (8)−0.0177 (6)−0.0014 (6)−0.0012 (7)
C50.0561 (8)0.0647 (9)0.0541 (8)−0.0246 (7)0.0036 (6)0.0089 (6)
C60.0487 (7)0.0555 (7)0.0390 (6)−0.0129 (6)−0.0034 (5)0.0060 (5)
C70.0326 (6)0.0384 (6)0.0292 (5)0.0024 (4)−0.0010 (4)−0.0029 (4)
C80.0322 (8)0.0390 (8)0.0380 (8)0−0.0048 (6)0
C90.0491 (8)0.0836 (11)0.0758 (10)−0.0062 (7)−0.0254 (7)0.0075 (8)
N10.0341 (5)0.0513 (6)0.0292 (5)−0.0086 (4)−0.0016 (4)0.0051 (4)
O10.0478 (5)0.0633 (6)0.0313 (4)−0.0085 (4)−0.0044 (3)0.0060 (4)
Geometric parameters (Å, º) top
C1—C21.3821 (16)C7—O11.2301 (13)
C1—C61.3873 (16)C7—N11.3359 (14)
C1—N11.4226 (14)C7—C81.5176 (14)
C2—C31.3886 (16)C8—C7i1.5176 (14)
C2—H20.93C8—H80.966 (12)
C3—C41.3824 (19)C9—H9A0.96
C3—C91.5035 (18)C9—H9B0.96
C4—C51.3754 (19)C9—H9C0.96
C4—H40.93C9—H9D0.96
C5—C61.3863 (17)C9—H9E0.96
C5—H50.93C9—H9F0.96
C6—H60.93N1—H1N0.86
C2—C1—C6119.96 (10)C3—C9—H9A109.5
C2—C1—N1116.31 (10)C3—C9—H9B109.5
C6—C1—N1123.73 (10)H9A—C9—H9B109.5
C1—C2—C3121.62 (11)C3—C9—H9C109.5
C1—C2—H2119.2H9A—C9—H9C109.5
C3—C2—H2119.2H9B—C9—H9C109.5
C4—C3—C2117.93 (11)C3—C9—H9D109.5
C4—C3—C9121.18 (12)H9A—C9—H9D141.1
C2—C3—C9120.89 (12)H9B—C9—H9D56.3
C5—C4—C3120.78 (11)H9C—C9—H9D56.3
C5—C4—H4119.6C3—C9—H9E109.5
C3—C4—H4119.6H9A—C9—H9E56.3
C4—C5—C6121.30 (12)H9B—C9—H9E141.1
C4—C5—H5119.3H9C—C9—H9E56.3
C6—C5—H5119.3H9D—C9—H9E109.5
C5—C6—C1118.40 (11)C3—C9—H9F109.5
C5—C6—H6120.8H9A—C9—H9F56.3
C1—C6—H6120.8H9B—C9—H9F56.3
O1—C7—N1124.49 (10)H9C—C9—H9F141.1
O1—C7—C8120.45 (8)H9D—C9—H9F109.5
N1—C7—C8115.03 (8)H9E—C9—H9F109.5
C7—C8—C7i112.59 (13)C7—N1—C1129.41 (9)
C7—C8—H8110.0 (7)C7—N1—H1N115.3
C7i—C8—H8106.5 (7)C1—N1—H1N115.3
C6—C1—C2—C30.73 (19)C2—C1—C6—C5−1.35 (19)
N1—C1—C2—C3−178.75 (11)N1—C1—C6—C5178.09 (12)
C1—C2—C3—C40.32 (19)O1—C7—C8—C7i78.05 (10)
C1—C2—C3—C9−179.02 (13)N1—C7—C8—C7i−103.70 (9)
C2—C3—C4—C5−0.7 (2)O1—C7—N1—C15.17 (19)
C9—C3—C4—C5178.61 (15)C8—C7—N1—C1−173.01 (11)
C3—C4—C5—C60.1 (2)C2—C1—N1—C7168.77 (11)
C4—C5—C6—C10.9 (2)C6—C1—N1—C7−10.69 (19)
Symmetry code: (i) −x+1, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.342.9124 (14)120
N1—H1N···O1ii0.862.162.9932 (12)162
C8—H8···O1ii0.97 (1)2.54 (1)3.3981 (9)149 (1)
Symmetry code: (ii) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formulaC17H18N2O2
Mr282.33
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)15.3617 (6), 11.2277 (6), 8.7316 (5)
β (°) 90.370 (4)
V (Å3)1505.97 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.58 × 0.27 × 0.16
Data collection
DiffractometerOxford Diffraction Gemini R CCD
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.970, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		11578, 1457, 1252
Rint0.019
(sin θ/λ)max (Å−1)0.612
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.096, 1.05
No. of reflections1457
No. of parameters101
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.15, −0.13

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.342.9124 (14)120
N1—H1N···O1i0.862.162.9932 (12)162
C8—H8···O1i0.966 (12)2.536 (11)3.3981 (9)148.6 (10)
Symmetry code: (i) x, −y+1, z−1/2.
 

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds, Inter­reg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi for the award of a research fellowship.

References

First citationBrandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91–100.  CAS Google Scholar
 First citationGowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010). Acta Cryst. E66, o1363.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o3037
https://doi.org/10.1107/S1600536810044089
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