metal-organic compounds
Dichlorido{8-[2-(dimethylamino)ethylamino]quinoline-κ3N,N′,N′′}zinc
aDepartment of Chemistry, College of Science for Women, Baghdad University, Baghdad, Iraq
*Correspondence e-mail: Alsudani@Uobaghdad.edu.iq
In the title complex, [ZnCl2(C13H17N3)], the coordination sphere of the zinc cation is distorted square pyramidal. The three N atoms of the N,N′,N′′-tridentate 8-[2-(dimethylamino)ethylamino]quinoline ligand and one chloride ion constitute a considerably distorted square base. The apical site is occupied by another chloride ion. The distortion from the ideal square-pyramidal geometry is manifested by the N—Zn—N angle of 133.25 (11)°. Like most square-pyramidal metal complexes, the zinc cation is displaced towards the apical chloride ion. In the crystal, molecules are linked by N—H⋯Cl interactions. This leads to the formation of chains of molecules parallel to the b-axis direction.
CCDC reference: 969762
Related literature
For the role of the zinc cation in biochemical reactions, see: Xu et al. (2010); Jena & Manivannan (2012). For the geometry of five-coordinate zinc complexes, see: Dai & Canary (2007). For a related structure, see: Al-Sudani & Kariuki (2013).
Experimental
Crystal data
|
Data collection: COLLECT (Nonius, 2000); cell SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012) and ACD/Chemsketch (Advanced Chemistry Development, 2008).
Supporting information
CCDC reference: 969762
https://doi.org/10.1107/S1600536813029929/hg5348sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813029929/hg5348Isup2.hkl
To a stirred methanoic solution (30 ml) of zinc dichloride (0.273 g m; 0.002 mol) kept under a positive nitrogen pressure, a methanoic solution (10 ml) containing an equimolar amount of the ligand (NN'N"); (0.43 g m; 0.002 mol) was slowly added. The resulting off white slurry was stirred at R·T. for 3 hrs. Then, the off white solid was collected by filtration, washed with smaller amount of cold methanol (5 ml, twice) followed by diethyl ether (15 ml, twice).the isolated solid was dried under vacuum at 50 °C. The mass of the slightly off white solid was 0.6 g m (yield = 85%), M·P. = 224°C. Mass Spec·(ES+)(CH3CN), m/z = 415.02 (M+CH3CN+Na) +; 374.00 ((M+Na) +; 314.04(M—Cl)+; 216.13(NN'N" + H)+. Anal·Calc. for [(C13H17N3) ZnCl2](M·W.:351.6); C; 44.41, H; 4.87, and N; 11.95. Found: C;44.45, H;4.9, and N;12.0. 1H NMR (d6-DMSO, 400 MHz, p.p.m.): 2.3 (S, 6H, N(CH3)2); 2.65 (t, 2H, CH2–CH2); 3.25 (t, 2H, CH2–CH2); 6.55 (broad s,1H, HN-quin.); the resonances of the other 6H-quin appear at 6.95, 7.3, 7.45, 7.6, 8.35,and 8.85.
Suitable colorless crystalof I were obtained via a slow vapor diffusion of diethyl ether in a smaller amount of acetonitrile solution of the zinc complex kept under the atmosphere of N2 gas.
The N- and C-bound H atoms were geometrically placed (X—H = 0.95–0.99Å where X is N or C atom) and refined using a riding model with Uiso(H) = 1.2–1.5Ueq(X).
Zinc is a biologically important element. Zinc, always present as a divalent cation in biological systems, is the second most abundant d-block metal ion in the human body after iron. The zinc cation; Zn+2, is well known to play diverse roles in many serious biochemical reactions, (Xu et al., 2010; Jena & Manivannan, 2012). The zinc(II) ion, however, provides a number of coordination compounds because of its affinity towards different types of ligands and flexible
ranging from two to eight. In zinc complexes, commonly found geometries are tetrahedral and octahedral. Six-coordinate complexes may be octahedral or trigonal-prismatic. Among the less common five-coordinate complexes, trigonal–bipyramidal geometry predominates over square-pyramidal geometry (Dai & Canary, 2007). Herein, we report the synthesis and characterization of 8-[2-dimethylamino]ethylamino]quinoline ZnCl2]. This complex was characterized by elemental analyses, 1H-NMR, and single-crystal X-ray techniques. The single-crystal structure analysis of the complex reveals that the three nitrogen atoms of the tridentate ligand, N,N',N'', along with two chloride ions form a distorted square-pyramidal geometry around the zinc cation (Fig. 1). The three N atoms of the tridentate ligand, N,N',N'', and one Cl ion constitute a considerably distorted square base. The apical site is occupied by another Cl ion. The distortion from the ideal square-pyramidal geometry is manifested by the N1—Zn—N3 angle of 133.25 (11)°. As in most square-pyramidal metal complexes, the zinc cation is displaced towards the apical Cl ion. Zn—N2 bond [2.274 (3) Å] is longer than the other two Zn—N bonds [2.136 (3) and 2.138 (3) Å] and the Zn—Cl bonds are also differ in length [2.266 (1) for Cl1 and 2.360 (1) Å for Cl2]. The Cl2 ion and N2 atom are trans to each other with an N2—Zn—Cl2 angle of 158.87 (8)°. The molecules are linked by N—H···Cl interactions (Table 1). This leads to the formation of chains of molecules parallel to the b axis (Fig. 2).For the role of the zinc cation in biochemical reactions, see: Xu et al. (2010); Jena & Manivannan (2012). For the geometry of five-coordinate zinc complexes, see: Dai & Canary (2007). For a related structure, see: Al-Sudani & Kariuki (2013).
Data collection: COLLECT (Nonius, 2000); cell
SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012) and ACD/Chemsketch (Advanced Chemistry Development, 2008).Fig. 1. The asymmetric of (I) with atom labels and 50% probability displacement ellipsoids. | |
Fig. 2. A segment of the crystal structure showing the N—H···Cl interactions as dotted lines. |
[ZnCl2(C13H17N3)] | F(000) = 720 |
Mr = 351.57 | Dx = 1.625 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 2422 reflections |
a = 23.6403 (6) Å | θ = 2.8–27.5° |
b = 7.5682 (2) Å | µ = 2.07 mm−1 |
c = 8.0329 (3) Å | T = 150 K |
V = 1437.20 (8) Å3 | Block, colourless |
Z = 4 | 0.17 × 0.05 × 0.04 mm |
Nonius KappaCCD diffractometer | 2638 independent reflections |
Radiation source: fine-focus sealed tube | 2422 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
CCD slices, ω and phi scans | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997) | h = −30→23 |
Tmin = 0.720, Tmax = 0.922 | k = −9→9 |
6701 measured reflections | l = −8→10 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.066 | w = 1/[σ2(Fo2) + (0.0224P)2 + 0.8402P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2638 reflections | Δρmax = 0.31 e Å−3 |
174 parameters | Δρmin = −0.38 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 873 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.002 (15) |
[ZnCl2(C13H17N3)] | V = 1437.20 (8) Å3 |
Mr = 351.57 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 23.6403 (6) Å | µ = 2.07 mm−1 |
b = 7.5682 (2) Å | T = 150 K |
c = 8.0329 (3) Å | 0.17 × 0.05 × 0.04 mm |
Nonius KappaCCD diffractometer | 2638 independent reflections |
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997) | 2422 reflections with I > 2σ(I) |
Tmin = 0.720, Tmax = 0.922 | Rint = 0.043 |
6701 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.066 | Δρmax = 0.31 e Å−3 |
S = 1.07 | Δρmin = −0.38 e Å−3 |
2638 reflections | Absolute structure: Flack (1983), 873 Friedel pairs |
174 parameters | Absolute structure parameter: −0.002 (15) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.97979 (13) | 1.0311 (4) | 0.7265 (6) | 0.0244 (7) | |
H1 | 0.9611 | 1.1329 | 0.7685 | 0.029* | |
C2 | 1.03902 (13) | 1.0354 (5) | 0.7106 (7) | 0.0280 (8) | |
H2 | 1.0595 | 1.1380 | 0.7422 | 0.034* | |
C3 | 1.06704 (15) | 0.8905 (5) | 0.6491 (5) | 0.0267 (9) | |
H3 | 1.1069 | 0.8924 | 0.6350 | 0.032* | |
C4 | 1.03549 (14) | 0.7389 (5) | 0.6071 (5) | 0.0213 (8) | |
C5 | 0.97605 (13) | 0.7445 (5) | 0.6265 (4) | 0.0171 (7) | |
C6 | 0.94322 (14) | 0.5944 (5) | 0.5872 (4) | 0.0188 (7) | |
C7 | 0.96889 (14) | 0.4450 (5) | 0.5276 (5) | 0.0241 (8) | |
H7 | 0.9467 | 0.3448 | 0.4992 | 0.029* | |
C8 | 1.02845 (15) | 0.4391 (5) | 0.5079 (5) | 0.0250 (8) | |
H8 | 1.0458 | 0.3344 | 0.4673 | 0.030* | |
C9 | 1.06105 (15) | 0.5815 (5) | 0.5466 (5) | 0.0232 (8) | |
H9 | 1.1009 | 0.5757 | 0.5332 | 0.028* | |
C10 | 0.84685 (13) | 0.5713 (5) | 0.4719 (5) | 0.0231 (8) | |
H10A | 0.8454 | 0.4428 | 0.4494 | 0.028* | |
H10B | 0.8617 | 0.6319 | 0.3718 | 0.028* | |
C11 | 0.78850 (14) | 0.6401 (4) | 0.5145 (5) | 0.0219 (8) | |
H11A | 0.7627 | 0.6197 | 0.4193 | 0.026* | |
H11B | 0.7735 | 0.5746 | 0.6116 | 0.026* | |
C12 | 0.79589 (17) | 0.9336 (6) | 0.3988 (5) | 0.0331 (9) | |
H12A | 0.8311 | 0.9008 | 0.3425 | 0.050* | |
H12B | 0.7966 | 1.0600 | 0.4252 | 0.050* | |
H12C | 0.7637 | 0.9083 | 0.3255 | 0.050* | |
C13 | 0.73599 (14) | 0.8808 (5) | 0.6338 (5) | 0.0283 (9) | |
H13A | 0.7348 | 1.0091 | 0.6497 | 0.043* | |
H13B | 0.7330 | 0.8219 | 0.7420 | 0.043* | |
H13C | 0.7044 | 0.8443 | 0.5627 | 0.043* | |
Cl1 | 0.83558 (3) | 0.77871 (12) | 0.97688 (12) | 0.02365 (19) | |
Cl2 | 0.84770 (3) | 1.18659 (10) | 0.73045 (17) | 0.02760 (19) | |
N1 | 0.94882 (11) | 0.8923 (3) | 0.6858 (3) | 0.0183 (7) | |
N2 | 0.88348 (11) | 0.6075 (4) | 0.6168 (4) | 0.0179 (6) | |
H2A | 0.8745 | 0.5245 | 0.6980 | 0.021* | |
N3 | 0.79023 (12) | 0.8311 (4) | 0.5534 (4) | 0.0199 (6) | |
Zn1 | 0.859314 (13) | 0.87704 (4) | 0.71978 (6) | 0.01701 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0281 (15) | 0.0196 (16) | 0.0254 (17) | −0.0024 (12) | 0.000 (2) | −0.002 (2) |
C2 | 0.0242 (15) | 0.0246 (18) | 0.035 (2) | −0.0062 (13) | −0.002 (2) | −0.001 (2) |
C3 | 0.0205 (16) | 0.028 (2) | 0.031 (2) | −0.0013 (15) | −0.0014 (16) | −0.0002 (18) |
C4 | 0.0220 (16) | 0.025 (2) | 0.0166 (17) | −0.0018 (15) | 0.0042 (14) | −0.0004 (16) |
C5 | 0.0207 (15) | 0.0140 (17) | 0.0165 (16) | 0.0013 (14) | 0.0012 (14) | 0.0005 (15) |
C6 | 0.0187 (16) | 0.0246 (19) | 0.0131 (17) | 0.0030 (15) | 0.0007 (14) | 0.0003 (14) |
C7 | 0.0251 (18) | 0.021 (2) | 0.026 (2) | 0.0027 (16) | 0.0005 (16) | −0.0024 (16) |
C8 | 0.0277 (18) | 0.0224 (19) | 0.025 (2) | 0.0068 (16) | 0.0032 (16) | −0.0026 (17) |
C9 | 0.0220 (17) | 0.026 (2) | 0.0214 (19) | 0.0028 (16) | 0.0027 (15) | 0.0012 (16) |
C10 | 0.0215 (16) | 0.0243 (19) | 0.0236 (18) | 0.0005 (14) | −0.0021 (17) | −0.0074 (18) |
C11 | 0.0207 (17) | 0.0186 (19) | 0.026 (2) | 0.0013 (14) | −0.0035 (15) | −0.0046 (16) |
C12 | 0.040 (2) | 0.034 (2) | 0.025 (2) | 0.0058 (19) | −0.0013 (19) | 0.0083 (19) |
C13 | 0.0190 (16) | 0.032 (2) | 0.034 (2) | 0.0074 (16) | −0.0038 (16) | −0.0050 (19) |
Cl1 | 0.0250 (4) | 0.0253 (4) | 0.0207 (4) | −0.0014 (4) | 0.0019 (4) | 0.0020 (4) |
Cl2 | 0.0258 (3) | 0.0148 (4) | 0.0422 (5) | 0.0004 (3) | 0.0018 (6) | −0.0004 (6) |
N1 | 0.0180 (12) | 0.0160 (15) | 0.021 (2) | −0.0015 (10) | −0.0003 (12) | 0.0007 (12) |
N2 | 0.0149 (13) | 0.0185 (16) | 0.0203 (15) | −0.0007 (12) | −0.0002 (12) | −0.0002 (12) |
N3 | 0.0216 (14) | 0.0205 (16) | 0.0175 (15) | 0.0039 (12) | 0.0026 (12) | 0.0011 (13) |
Zn1 | 0.01713 (16) | 0.01476 (18) | 0.01915 (18) | 0.00002 (13) | 0.0011 (2) | −0.0008 (2) |
C1—N1 | 1.321 (4) | C10—H10A | 0.9900 |
C1—C2 | 1.406 (4) | C10—H10B | 0.9900 |
C1—H1 | 0.9500 | C11—N3 | 1.480 (4) |
C2—C3 | 1.373 (5) | C11—H11A | 0.9900 |
C2—H2 | 0.9500 | C11—H11B | 0.9900 |
C3—C4 | 1.409 (5) | C12—N3 | 1.470 (5) |
C3—H3 | 0.9500 | C12—H12A | 0.9800 |
C4—C5 | 1.414 (4) | C12—H12B | 0.9800 |
C4—C9 | 1.421 (5) | C12—H12C | 0.9800 |
C5—N1 | 1.376 (4) | C13—N3 | 1.484 (4) |
C5—C6 | 1.412 (5) | C13—H13A | 0.9800 |
C6—C7 | 1.369 (5) | C13—H13B | 0.9800 |
C6—N2 | 1.436 (4) | C13—H13C | 0.9800 |
C7—C8 | 1.418 (5) | Cl1—Zn1 | 2.2659 (11) |
C7—H7 | 0.9500 | Cl2—Zn1 | 2.3604 (8) |
C8—C9 | 1.361 (5) | N1—Zn1 | 2.136 (3) |
C8—H8 | 0.9500 | N2—Zn1 | 2.274 (3) |
C9—H9 | 0.9500 | N2—H2A | 0.9300 |
C10—N2 | 1.476 (5) | N3—Zn1 | 2.139 (3) |
C10—C11 | 1.513 (4) | ||
N1—C1—C2 | 123.2 (3) | H11A—C11—H11B | 108.0 |
N1—C1—H1 | 118.4 | N3—C12—H12A | 109.5 |
C2—C1—H1 | 118.4 | N3—C12—H12B | 109.5 |
C3—C2—C1 | 119.6 (3) | H12A—C12—H12B | 109.5 |
C3—C2—H2 | 120.2 | N3—C12—H12C | 109.5 |
C1—C2—H2 | 120.2 | H12A—C12—H12C | 109.5 |
C2—C3—C4 | 118.7 (3) | H12B—C12—H12C | 109.5 |
C2—C3—H3 | 120.6 | N3—C13—H13A | 109.5 |
C4—C3—H3 | 120.6 | N3—C13—H13B | 109.5 |
C3—C4—C5 | 118.4 (3) | H13A—C13—H13B | 109.5 |
C3—C4—C9 | 122.6 (3) | N3—C13—H13C | 109.5 |
C5—C4—C9 | 119.0 (3) | H13A—C13—H13C | 109.5 |
N1—C5—C6 | 118.3 (3) | H13B—C13—H13C | 109.5 |
N1—C5—C4 | 121.8 (3) | C1—N1—C5 | 118.2 (3) |
C6—C5—C4 | 119.8 (3) | C1—N1—Zn1 | 124.1 (2) |
C7—C6—C5 | 119.9 (3) | C5—N1—Zn1 | 117.6 (2) |
C7—C6—N2 | 123.4 (3) | C6—N2—C10 | 115.7 (3) |
C5—C6—N2 | 116.6 (3) | C6—N2—Zn1 | 111.7 (2) |
C6—C7—C8 | 120.3 (3) | C10—N2—Zn1 | 107.8 (2) |
C6—C7—H7 | 119.8 | C6—N2—H2A | 107.1 |
C8—C7—H7 | 119.8 | C10—N2—H2A | 107.1 |
C9—C8—C7 | 120.8 (3) | Zn1—N2—H2A | 107.1 |
C9—C8—H8 | 119.6 | C12—N3—C11 | 109.8 (3) |
C7—C8—H8 | 119.6 | C12—N3—C13 | 108.2 (3) |
C8—C9—C4 | 120.1 (3) | C11—N3—C13 | 108.4 (3) |
C8—C9—H9 | 120.0 | C12—N3—Zn1 | 111.9 (2) |
C4—C9—H9 | 120.0 | C11—N3—Zn1 | 108.2 (2) |
N2—C10—C11 | 107.0 (3) | C13—N3—Zn1 | 110.3 (2) |
N2—C10—H10A | 110.3 | N1—Zn1—N3 | 133.25 (11) |
C11—C10—H10A | 110.3 | N1—Zn1—Cl1 | 112.30 (8) |
N2—C10—H10B | 110.3 | N3—Zn1—Cl1 | 109.10 (8) |
C11—C10—H10B | 110.3 | N1—Zn1—N2 | 75.72 (10) |
H10A—C10—H10B | 108.6 | N3—Zn1—N2 | 79.56 (10) |
N3—C11—C10 | 111.0 (3) | Cl1—Zn1—N2 | 95.69 (8) |
N3—C11—H11A | 109.4 | N1—Zn1—Cl2 | 93.79 (8) |
C10—C11—H11A | 109.4 | N3—Zn1—Cl2 | 95.46 (8) |
N3—C11—H11B | 109.4 | Cl1—Zn1—Cl2 | 105.31 (4) |
C10—C11—H11B | 109.4 | N2—Zn1—Cl2 | 158.87 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl2i | 0.93 | 2.65 | 3.420 (3) | 141 |
Symmetry code: (i) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl2i | 0.93 | 2.65 | 3.420 (3) | 140.9 |
Symmetry code: (i) x, y−1, z. |
Acknowledgements
I would like to thank Professor P. G. Edwards of Cardiff University, School of Chemistry, for providing me with many opportunities to work in his laboratory as an academic visitor as well as for his invaluable advice and financial support, without which this work as well as others would not have been possible. Furthermore, I would like to thank Dr Benson M. Kariuki for the X-ray
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Zinc is a biologically important element. Zinc, always present as a divalent cation in biological systems, is the second most abundant d-block metal ion in the human body after iron. The zinc cation; Zn+2, is well known to play diverse roles in many serious biochemical reactions, (Xu et al., 2010; Jena & Manivannan, 2012). The zinc(II) ion, however, provides a number of coordination compounds because of its affinity towards different types of ligands and flexible coordination number ranging from two to eight. In zinc complexes, commonly found geometries are tetrahedral and octahedral. Six-coordinate complexes may be octahedral or trigonal-prismatic. Among the less common five-coordinate complexes, trigonal–bipyramidal geometry predominates over square-pyramidal geometry (Dai & Canary, 2007). Herein, we report the synthesis and characterization of 8-[2-dimethylamino]ethylamino]quinoline ZnCl2]. This complex was characterized by elemental analyses, mass spectroscopy, 1H-NMR, and single-crystal X-ray structure determination techniques. The single-crystal structure analysis of the complex reveals that the three nitrogen atoms of the tridentate ligand, N,N',N'', along with two chloride ions form a distorted square-pyramidal geometry around the zinc cation (Fig. 1). The three N atoms of the tridentate ligand, N,N',N'', and one Cl ion constitute a considerably distorted square base. The apical site is occupied by another Cl ion. The distortion from the ideal square-pyramidal geometry is manifested by the N1—Zn—N3 angle of 133.25 (11)°. As in most square-pyramidal metal complexes, the zinc cation is displaced towards the apical Cl ion. Zn—N2 bond [2.274 (3) Å] is longer than the other two Zn—N bonds [2.136 (3) and 2.138 (3) Å] and the Zn—Cl bonds are also differ in length [2.266 (1) for Cl1 and 2.360 (1) Å for Cl2]. The Cl2 ion and N2 atom are trans to each other with an N2—Zn—Cl2 angle of 158.87 (8)°. The molecules are linked by N—H···Cl interactions (Table 1). This leads to the formation of chains of molecules parallel to the b axis (Fig. 2).