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

Journal logoIUCrDATA
ISSN: 2414-3146

trans-Di­chlorido­{3,4-dimeth­­oxy-2-[(2,3-η)-prop-2-en-1-yl]benzene}(pyridine-κN)platinum(II)

aChemistry Department, Hanoi National University of Education, 136 - Xuan Thuy - Cau Giay, Hanoi, Vietnam, and bChemistry Department, KU Leuven, Celestijnenlaan 200F, B-3001, Leuven (Heverlee), Belgium
*Correspondence e-mail: luc.vanmeervelt@chem.kuleuven.be

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 4 November 2015; accepted 16 November 2015; online 1 January 2016)

In the title organoplatinum(II) complex, [PtCl2(C5H5N)(C11H14O2)], the methyl­eugenol ligand only coordinates to the PtII atom through the ethyl­enic double bond. The coordination is completed by the N atom of the pyridine ligand and two Cl atoms positioned trans with respect to each other. The pyridine and benzene rings are inclined to one another by 68.6 (2)°. In the crystal, mol­ecules are linked via a number of C—H⋯Cl and C—H⋯O hydrogen bonds, forming sheets parallel to the bc plane.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The crystal structure of the title complex was determined in order to clarify the PtII coordination to the ligand methyl­eugenol. It was found that it only coordinates to PtII through the ethyl­enic double bond (Fig. 1[link]). The coordination is completed by the N atom of the pyridine ligand and two Cl atoms positioned trans with respect to each other. The pyridine and benzene rings are inclined to one another by 68.6 (2)°. In the crystal, mol­ecules are linked via a number of C—H⋯Cl and C—H⋯O hydrogen bonds (Table 1[link]), forming sheets parallel to the bc plane.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯Cl3Bi 0.95 2.76 3.54 (2) 140
C12—H12A⋯O21ii 0.99 2.57 3.397 (6) 141
C12—H12B⋯Cl3A 0.99 2.68 3.371 (13) 127
C17—H17⋯Cl2Aiii 0.95 2.78 3.671 (14) 156
C17—H17⋯Cl2Biii 0.95 2.70 3.59 (2) 156
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]; (iii) x, y-1, z.
[Figure 1]
Figure 1
A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Both the major and minor components (A/B) of the disordered Pt and Cl atoms are shown.

The activities of the title compound on HepG2 and Lu cell lines show IC50 values of 9.7 and 7.8 µg/ml, respectively. The synthesis and anti­tumor activity on the human cancer cell lines KB and MCF7 of the title compound and other organoplatinum(II) complexes containing methyl­eugenol and amines have been reported (Da, Chi et al., 2015[Da, T. T., Chi, N. T. T., Meervelt, L. V., Kimpende, P. M. & Dinh, N. H. (2015). Polyhedron, 85, 104-109.]; Da, Hai et al., 2015[Da, T. T., Hong Hai, L. T., Meervelt, L. V. & Dinh, N. H. (2015). J. Coord. Chem. 68, 3525-3536.]), as have the structures of organoplatinum(II) complexes containing eugenol (Da et al., 2008[Da, T. T., Kim, Y.-M., Chi, N. T. T., Chien, L. X., Minh, N. V. & Dinh, N. H. (2008). Organometallics, 27, 3611-3613.]; Da, Chi et al., 2015[Da, T. T., Chi, N. T. T., Meervelt, L. V., Kimpende, P. M. & Dinh, N. H. (2015). Polyhedron, 85, 104-109.]; Mangwala Kimpende et al., 2014[Mangwala Kimpende, P., Thi Da, T., Nguyen Huu, D. & Van Meervelt, L. (2014). Acta Cryst. E70, 435-437.]).

Synthesis and crystallization

The synthesis of the title complex has been reported elsewhere (Da, Chi et al., 2015[Da, T. T., Chi, N. T. T., Meervelt, L. V., Kimpende, P. M. & Dinh, N. H. (2015). Polyhedron, 85, 104-109.]).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Atoms Pt1, Cl2 and Cl3 are disordered over two sets of sites (A/B) with final occupancies of 0.59 (4) and 0.41 (4).

Table 2
Experimental details

Crystal data
Chemical formula [PtCl2(C5H5N)(C11H14O2)]
Mr 523.31
Crystal system, space group Monoclinic, P21/n
Temperature (K) 95
a, b, c (Å) 15.1282 (5), 7.25666 (17), 16.3038 (5)
β (°) 108.013 (3)
V3) 1702.11 (9)
Z 4
Radiation type Mo Kα
μ (mm−1) 8.56
Crystal size (mm) 0.24 × 0.19 × 0.14
 
Data collection
Diffractometer Agilent SuperNova (single source at offset, Eos CCD detector) diffractometer
Absorption correction Gaussian (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.])
Tmin, Tmax 0.771, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 6822, 3459, 3165
Rint 0.023
(sin θ/λ)max−1) 0.625
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.051, 1.11
No. of reflections 3459
No. of parameters 229
No. of restraints 219
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.13, −1.01
Computer programs: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), SHELXS2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

trans-Dichlorido{3,4-dimethoxy-2-[(2,3-η)-prop-2-en-1-yl]benzene}(pyridine-κN)platinum(II) top
Crystal data top
[PtCl2(C5H5N)(C11H14O2)]F(000) = 1000
Mr = 523.31Dx = 2.042 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 15.1282 (5) ÅCell parameters from 4267 reflections
b = 7.25666 (17) Åθ = 3.1–29.0°
c = 16.3038 (5) ŵ = 8.56 mm1
β = 108.013 (3)°T = 95 K
V = 1702.11 (9) Å3Block, yellow
Z = 40.24 × 0.19 × 0.14 mm
Data collection top
Agilent SuperNova (single source at offset, Eos CCD detector)
diffractometer
3459 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3165 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 26.4°, θmin = 2.6°
Absorption correction: gaussian
(CrysAlisPro; Agilent, 2012)
h = 1814
Tmin = 0.771, Tmax = 1.000k = 89
6822 measured reflectionsl = 1320
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)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0139P)2 + 1.1858P]
where P = (Fo2 + 2Fc2)/3
3459 reflections(Δ/σ)max = 0.001
229 parametersΔρmax = 1.13 e Å3
219 restraintsΔρmin = 1.01 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Pt1A0.23303 (17)0.9480 (4)0.06520 (17)0.0122 (5)0.59 (4)
Cl2A0.3517 (9)1.1609 (16)0.0976 (9)0.0165 (12)0.59 (4)
Cl3A0.1127 (6)0.7382 (17)0.0436 (8)0.0171 (12)0.59 (4)
Pt1B0.2283 (4)0.9392 (8)0.0651 (3)0.0269 (9)0.41 (4)
Cl2B0.3413 (14)1.155 (3)0.0861 (15)0.031 (3)0.41 (4)
Cl3B0.1121 (11)0.724 (3)0.0542 (15)0.036 (3)0.41 (4)
N40.3057 (2)0.8103 (4)0.1768 (2)0.0176 (7)
C50.3352 (3)0.9011 (6)0.2524 (3)0.0208 (9)
H50.31971.02760.25430.025*
C60.3873 (3)0.8148 (6)0.3270 (3)0.0241 (10)
H60.40630.88040.38000.029*
C70.4116 (3)0.6320 (6)0.3240 (3)0.0265 (10)
H70.44750.57030.37480.032*
C80.3832 (3)0.5414 (6)0.2467 (3)0.0248 (10)
H80.40020.41630.24320.030*
C90.3296 (3)0.6326 (6)0.1737 (3)0.0216 (9)
H90.30930.56840.12040.026*
C100.1398 (3)1.1197 (6)0.0314 (3)0.0246 (10)
H10A0.07711.08160.04250.030*0.59 (4)
H10B0.16361.21960.00670.030*0.59 (4)
H10C0.07711.08160.04250.030*0.41 (4)
H10D0.16361.21960.00670.030*0.41 (4)
C110.1977 (3)1.0276 (6)0.0715 (3)0.0294 (10)
H110.24501.10960.08420.035*0.59 (4)
H11A0.24681.10750.08240.035*0.41 (4)
C120.1693 (3)0.8703 (7)0.1320 (3)0.0314 (11)
H12A0.14020.91770.19120.038*
H12B0.12240.79560.11600.038*
C130.2522 (3)0.7484 (6)0.1306 (3)0.0287 (10)
C140.3107 (3)0.7908 (6)0.1809 (3)0.0262 (10)
H140.29920.89860.21560.031*
C150.3841 (3)0.6785 (6)0.1803 (3)0.0212 (9)
C160.4019 (3)0.5190 (6)0.1278 (3)0.0198 (9)
C170.3454 (3)0.4820 (6)0.0781 (3)0.0236 (9)
H170.35720.37600.04220.028*
C180.2717 (3)0.5960 (6)0.0793 (3)0.0271 (10)
H180.23410.56760.04390.033*
O190.4741 (2)0.4120 (4)0.1327 (2)0.0257 (7)
C200.4890 (3)0.2442 (6)0.0832 (3)0.0275 (10)
H20A0.43320.16720.10230.041*
H20B0.50220.27380.02190.041*
H20C0.54180.17740.09160.041*
O210.4432 (2)0.7041 (4)0.22853 (19)0.0261 (7)
C220.4344 (3)0.8716 (6)0.2759 (3)0.0307 (11)
H22A0.37150.88040.31670.046*
H22B0.47990.87330.30750.046*
H22C0.44570.97620.23590.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt1A0.0117 (9)0.0113 (7)0.0146 (6)0.0012 (5)0.0055 (4)0.0006 (4)
Cl2A0.0166 (19)0.015 (2)0.015 (3)0.0052 (15)0.001 (2)0.0019 (16)
Cl3A0.014 (2)0.019 (2)0.019 (2)0.0040 (15)0.0064 (14)0.0013 (16)
Pt1B0.0369 (17)0.0252 (13)0.0143 (9)0.0112 (10)0.0015 (9)0.0011 (7)
Cl2B0.036 (6)0.032 (4)0.021 (5)0.002 (3)0.002 (4)0.005 (3)
Cl3B0.043 (4)0.030 (4)0.030 (6)0.003 (3)0.003 (3)0.001 (3)
N40.0177 (17)0.0185 (16)0.0178 (17)0.0009 (14)0.0071 (13)0.0022 (13)
C50.019 (2)0.024 (2)0.019 (2)0.0004 (18)0.0072 (16)0.0001 (17)
C60.023 (2)0.031 (2)0.019 (2)0.0027 (19)0.0084 (17)0.0051 (18)
C70.018 (2)0.035 (2)0.027 (2)0.0013 (19)0.0075 (18)0.0119 (19)
C80.021 (2)0.024 (2)0.033 (2)0.0042 (18)0.0142 (19)0.0074 (18)
C90.020 (2)0.025 (2)0.021 (2)0.0021 (18)0.0071 (17)0.0002 (17)
C100.026 (2)0.026 (2)0.018 (2)0.0064 (19)0.0004 (17)0.0005 (18)
C110.038 (3)0.028 (2)0.018 (2)0.007 (2)0.0011 (18)0.0062 (18)
C120.033 (3)0.039 (3)0.021 (2)0.005 (2)0.0056 (19)0.000 (2)
C130.032 (2)0.035 (2)0.017 (2)0.007 (2)0.0061 (18)0.0026 (19)
C140.032 (2)0.029 (2)0.014 (2)0.0071 (19)0.0021 (17)0.0033 (18)
C150.020 (2)0.024 (2)0.017 (2)0.0048 (17)0.0016 (16)0.0041 (17)
C160.017 (2)0.0201 (19)0.021 (2)0.0011 (16)0.0038 (16)0.0059 (17)
C170.024 (2)0.028 (2)0.017 (2)0.0036 (18)0.0027 (17)0.0058 (18)
C180.026 (2)0.037 (2)0.019 (2)0.0065 (19)0.0082 (18)0.0017 (19)
O190.0245 (16)0.0247 (15)0.0306 (18)0.0074 (13)0.0122 (14)0.0065 (14)
C200.032 (3)0.019 (2)0.033 (3)0.0033 (19)0.012 (2)0.0002 (19)
O210.0265 (16)0.0245 (16)0.0274 (17)0.0024 (13)0.0083 (13)0.0021 (13)
C220.043 (3)0.028 (2)0.019 (2)0.007 (2)0.006 (2)0.0016 (19)
Geometric parameters (Å, º) top
Pt1A—Cl2A2.303 (10)C11—H111.0000
Pt1A—Cl3A2.315 (9)C11—H11A1.0000
Pt1A—N42.069 (4)C11—C121.483 (6)
Pt1A—C102.156 (5)C12—H12A0.9900
Pt1A—C112.203 (5)C12—H12B0.9900
Pt1B—Cl2B2.265 (17)C12—C131.530 (6)
Pt1B—Cl3B2.316 (16)C13—C141.414 (6)
Pt1B—N42.061 (5)C13—C181.363 (6)
Pt1B—C102.163 (6)C14—H140.9500
Pt1B—C112.225 (6)C14—C151.375 (6)
N4—C51.346 (5)C15—C161.415 (6)
N4—C91.344 (5)C15—O211.375 (5)
C5—H50.9500C16—C171.373 (6)
C5—C61.379 (6)C16—O191.362 (5)
C6—H60.9500C17—H170.9500
C6—C71.381 (6)C17—C181.384 (6)
C7—H70.9500C18—H180.9500
C7—C81.367 (6)O19—C201.440 (5)
C8—H80.9500C20—H20A0.9800
C8—C91.384 (6)C20—H20B0.9800
C9—H90.9500C20—H20C0.9800
C10—H10A0.9500O21—C221.423 (5)
C10—H10B0.9500C22—H22A0.9800
C10—H10C0.9500C22—H22B0.9800
C10—H10D0.9500C22—H22C0.9800
C10—C111.413 (6)
Cl2A—Pt1A—Cl3A175.4 (5)C11—C10—H10D120.0
N4—Pt1A—Cl2A87.6 (4)Pt1A—C11—H11113.6
N4—Pt1A—Cl3A89.7 (3)Pt1B—C11—H11A114.1
N4—Pt1A—C10166.24 (19)C10—C11—Pt1A69.3 (3)
N4—Pt1A—C11156.0 (2)C10—C11—Pt1B68.9 (3)
C10—Pt1A—Cl2A93.9 (4)C10—C11—H11113.6
C10—Pt1A—Cl3A87.9 (4)C10—C11—H11A114.1
C10—Pt1A—C1137.81 (17)C10—C11—C12125.3 (4)
C11—Pt1A—Cl2A89.1 (4)C12—C11—Pt1A113.6 (3)
C11—Pt1A—Cl3A94.9 (4)C12—C11—Pt1B111.8 (3)
Cl2B—Pt1B—Cl3B175.5 (8)C12—C11—H11113.6
N4—Pt1B—Cl2B89.1 (6)C12—C11—H11A114.1
N4—Pt1B—Cl3B88.4 (5)C11—C12—H12A109.3
N4—Pt1B—C10166.5 (3)C11—C12—H12B109.3
N4—Pt1B—C11154.4 (3)C11—C12—C13111.6 (4)
C10—Pt1B—Cl2B87.7 (7)H12A—C12—H12B108.0
C10—Pt1B—Cl3B93.9 (6)C13—C12—H12A109.3
C10—Pt1B—C1137.53 (17)C13—C12—H12B109.3
C11—Pt1B—Cl2B82.3 (7)C14—C13—C12121.6 (4)
C11—Pt1B—Cl3B101.5 (7)C18—C13—C12119.9 (4)
C5—N4—Pt1A120.2 (3)C18—C13—C14118.5 (4)
C5—N4—Pt1B121.6 (3)C13—C14—H14119.5
C9—N4—Pt1A120.4 (3)C15—C14—C13121.0 (4)
C9—N4—Pt1B119.2 (3)C15—C14—H14119.5
C9—N4—C5119.2 (4)C14—C15—C16119.4 (4)
N4—C5—H5119.3O21—C15—C14125.6 (4)
N4—C5—C6121.5 (4)O21—C15—C16114.9 (4)
C6—C5—H5119.3C17—C16—C15118.7 (4)
C5—C6—H6120.3O19—C16—C15115.9 (4)
C5—C6—C7119.4 (4)O19—C16—C17125.4 (4)
C7—C6—H6120.3C16—C17—H17119.3
C6—C7—H7120.6C16—C17—C18121.4 (4)
C8—C7—C6118.9 (4)C18—C17—H17119.3
C8—C7—H7120.6C13—C18—C17120.9 (4)
C7—C8—H8120.1C13—C18—H18119.5
C7—C8—C9119.8 (4)C17—C18—H18119.5
C9—C8—H8120.1C16—O19—C20116.0 (3)
N4—C9—C8121.3 (4)O19—C20—H20A109.5
N4—C9—H9119.4O19—C20—H20B109.5
C8—C9—H9119.4O19—C20—H20C109.5
Pt1A—C10—H10A111.1H20A—C20—H20B109.5
Pt1A—C10—H10B86.2H20A—C20—H20C109.5
Pt1B—C10—H10C108.6H20B—C20—H20C109.5
Pt1B—C10—H10D87.9C15—O21—C22117.2 (3)
H10A—C10—H10B120.0O21—C22—H22A109.5
H10C—C10—H10D120.0O21—C22—H22B109.5
C11—C10—Pt1A72.9 (2)O21—C22—H22C109.5
C11—C10—Pt1B73.6 (3)H22A—C22—H22B109.5
C11—C10—H10A120.0H22A—C22—H22C109.5
C11—C10—H10B120.0H22B—C22—H22C109.5
C11—C10—H10C120.0
Pt1A—N4—C5—C6177.1 (3)C12—C13—C14—C15178.9 (4)
Pt1A—N4—C9—C8175.9 (3)C12—C13—C18—C17178.9 (4)
Pt1A—C10—C11—C12104.9 (4)C13—C14—C15—C160.7 (6)
Pt1A—C11—C12—C1372.6 (5)C13—C14—C15—O21177.9 (4)
Pt1B—N4—C5—C6179.7 (3)C14—C13—C18—C171.8 (7)
Pt1B—N4—C9—C8178.6 (4)C14—C15—C16—C170.6 (6)
Pt1B—C10—C11—C12102.4 (5)C14—C15—C16—O19178.1 (4)
Pt1B—C11—C12—C1374.3 (5)C14—C15—O21—C227.4 (6)
N4—C5—C6—C71.4 (6)C15—C16—C17—C180.7 (6)
C5—N4—C9—C80.4 (6)C15—C16—O19—C20176.6 (3)
C5—C6—C7—C80.0 (6)C16—C15—O21—C22173.9 (3)
C6—C7—C8—C91.2 (6)C16—C17—C18—C130.6 (7)
C7—C8—C9—N41.0 (6)C17—C16—O19—C202.1 (6)
C9—N4—C5—C61.6 (6)C18—C13—C14—C151.9 (7)
C10—C11—C12—C13153.2 (4)O19—C16—C17—C18177.9 (4)
C11—C12—C13—C1484.2 (5)O21—C15—C16—C17179.3 (4)
C11—C12—C13—C1895.0 (5)O21—C15—C16—O190.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···Cl3Bi0.952.763.54 (2)140
C12—H12A···O21ii0.992.573.397 (6)141
C12—H12B···Cl3A0.992.683.371 (13)127
C17—H17···Cl2Aiii0.952.783.671 (14)156
C17—H17···Cl2Biii0.952.703.59 (2)156
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2; (iii) x, y1, z.
 

Acknowledgements

The authors thank VLIR–UOS for financial support through project ZEIN2014Z182 and the Hercules Foundation for supporting the purchase of the diffractometer through project AKUL/09/0035.

References

First citationAgilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
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