research communications
E)-2-{[(2-iodophenyl)imino]methyl}-6-methylphenol
and Hirshfeld surface analysis of (aSamsun University, Faculty of Engineering, Department of Fundamental Sciences, 55420, Samsun, Turkey, bYeditepe University, Department of Chemical Engineering, 34755, İstanbul, Turkey, cOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey, dOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Chemistry, 55139, Samsun, Turkey, eDepartment of Applied Chemistry, ZHCET, Aligarh Muslim University, Aligarh, 202002, UP, India, and fDepartment of Computer and Electronic Engineering Technology, Sana'a Community, College, Sana'a, Yemen
*Correspondence e-mail: sevgi.kansiz@samsun.edu.tr, eiad.saif@scc.edu.ye
The title compound, C14H12INO, was synthesized by condensation of 2-hydroxy-3-methylbenzaldehyde and 2-iodoaniline, and crystallizes in the orthorhombic P212121. The 2-iodophenyl and benzene rings are twisted with respect to each other, making a dihedral angle of 31.38 (2)°. The molecular structure is stabilized by an O—H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by C—H⋯π interactions, resulting in the formation of sheets along the a-axis direction. Within the sheets, very weak π–π stacking interactions lead to additional stabilization. The Hirshfeld surface analysis and fingerprint plots reveal that the is dominated by H⋯H (37.1%) and C⋯H (30.1%) contacts. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. The crystal studied was refined as a two-component inversion twin.
Keywords: crystal structure; 2-iodophenyl; Schiff base; Hirshfeld surface analysis.
CCDC reference: 2026445
1. Chemical context
o-hydroxy aromatic carbonyls are of interest because of their ability to form an asymmetric intramolecular hydrogen bond between the oxygen atom of the hydroxyl group and the nitrogen atom of the imine moiety (Dominiak et al., 2003). This ability has a decisive impact on the biological and thermo- or photochromic properties of o-hydroxy aromatic and makes them very useful compounds in chemistry, biochemistry, medicine, and technology (Vlad et al., 2018; Bouhidel et al., 2018; Faizi et al., 2020a,b). A very important issue is determining the positions of tautomeric equilibria in these compounds and various instrumental research techniques are used to provide insight into the structure of molecules of studied o-hydroxy (Wojciechowski et al., 2003; Faizi et al., 2020c,d).
derived fromIn the present study, a new Schiff base, (E)-2-{[(2-iodophenyl)imino]methyl}-6-methylphenol, was obtained in crystalline form from the reaction of 2-hydroxy-3-methylbenzaldehyde with 2-iodoaniline. We report here the synthesis and the crystal and molecular structures of the title compound, along with the results of a Hirshfeld surface analysis.
2. Structural commentary
Depending on the tautomers, two types of intramolecular hydrogen bonds are observed in , is a Schiff base derivative from 2-hydroxy-3-methylbenzaldehyde, which crystallizes in the phenol–imine tautomeric form with an E configurationfor the imine functionality. The of (I) contains one molecule (Fig. 1). The molecule is non-planar with the 2-iodophenyl and benzene rings twisted with respect to each other at a dihedral angle of 31.38 (2)°. The hydroxyl H atom is involved in a strong intramolecular O—H⋯N hydrogen bond, forming an S(6) ring motif, which stabilizes the molecular structure and induces the Schiff base atoms (N1, C7) to be coplanar with the methylphenol moiety. Of this planar unit (r.m.s deviation = 0.0274 Å), atoms O1 and N1 show the largest deviations from planarity in positive and negative directions [O1 = 0.035 (4) Å and N1 = −0.060 (4) Å]. The C7—N1 and C13—O1 bonds of the title compound are the most important indicators of the tautomeric type. The C13—O1 bond is of double-bond character for the keto–amine tautomer, whereas this bond displays single-bond character in the enol–imine tautomer. In addition, the C7—N1 bond is also a double bond in the enol–imine tautomer and a single bond length in the keto–amine tautomer. In the title compound, the enol–imine form is favored over the keto-amine form, as indicated by the C13—O1 [1.352 (6) Å] and C7—N1 [1.286 (8) Å] bonds, whose lengths indicate a high degree of single-bond and double-bond character, respectively. The shortest C—C distance (C3—C4) is 1.344 (11) Å in the C1–C6 ring with the weighted average ring bond distance being 1.376 (11) Å for this ring.
O—H⋯N in enol–imine and N—H⋯O in keto–amine tautomers. Most of these compounds are non-planar. The title compound, (I)3. Supramolecular features
In the a-axis direction by C2—H2⋯Cg2i interactions (Table 1; Fig. 2). Within the sheets, very weak π–π stacking interactions are observed with a centroid-to-centroid distance Cg1⋯Cg2ii of 4.093 (2) Å (Fig. 3), where Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.
the molecules are connected into sheets extending along the4. Hirshfeld surface analysis
A Hirshfeld surface analysis (Spackman & Jayatilaka, 2009) was carried out using CrystalExplorer17.5 (Turner et al., 2017). The Hirshfeld surfaces and the associated two-dimensional fingerprint plots were used to quantify the various intermolecular interactions in the structure. The Hirshfeld surfaces (dnorm and shape-index) of the title compound are illustrated in Fig. 4. There are no prominent red spots on the surface, hence most of the interactions are weak non-covalent interactions. The diffuse white areas identified in Fig. 4a and red areas on phenyl rings mapped with shape-index (Fig. 4b) correspond to the H⋯π contacts resulting from hydrogen bond C—H⋯π(ring) (Table 1) and π–π stacking interactions. The major intermolecular interactions in the are H⋯H, H⋯C and H⋯I interactions, which make individual contributions of 37.1%, 30.1% and 18%, respectively. The fingerprint plots are shown in Fig. 5. There are also O⋯H (6.4%), N⋯H (3.6%) and C⋯C (23.3%) contacts. The Hirshfeld surface analysis confirms the importance of H-atom contacts in establishing the packing. The large number of H⋯H and C⋯H interactions suggest that van der Waals interactions play the major role in the crystal packing.
5. Database survey
A search of the Cambridge Structural Database (CSD, version 5.41, update of November 2019; Groom et al., 2016) for the (E)-2-[(2-iodophenylimino)methyl]phenol gave six hits: bis[N-(2-iodophenyl)-2-oxynaphthaldiminato-N,O]copper(II) (HABFIA; Unver, 2002), bis(m-methanolato)bis(2-{[(5,7-diiodoquinolin-8-yl)imino]methyl}phenolato)bis(isothiocyanato)diiron(III) methanol solvate (HIDJOW; Sahadevan et al., 2018), bis(m-oxo)bis(m-methanolato)tetrakis(2-{[(5,7-diiodoquinolin-8-yl)imino]methyl}phenolato)bis(isothiocyanato)tetrairon(III) dichloromethane solvate (HIDJUC; Sahadevan et al., 2018), 2-{[(5,7-diiodoquinolin-8-yl)imino]methyl}phenol (HIDKAJ; Sahadevan et al., 2018), 2-iodo-salicylideneaniline (QQQANJ; Bernstein, 1967) and 2-[(2-iodophenyl)iminomethyl]phenol (RAVTIR; Elmali & Elerman, 1997). In HABFIA, the C—O bond length is 1.293 (3) Å, compared to 1.339 (5) Å for this bond in RAVTIR. Similar values are observed in the crystal of the title compound. The C—N bond lengths are 1.306 (3) and 1.267 (5) Å in HABFIA and RAVTIR, respectively. The molecules of HABFIA and RAVTIR have the same configuration as the title compound, while the other compounds listed above have different configurations.
6. Synthesis and crystallization
The title compound was prepared by refluxing mixed solutions of 2-hydroxy-3-methylbenzaldehyde (34.0 mg, 0.25 mmol) in ethanol (20 ml) and 2-iodoaniline (54.7 mg, 0.25 mmol) in ethanol (20 ml). The reaction mixture was stirred for 4 h under reflux. Single crystals of the title compound for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield 72%, m.p. 410–412 K).
7. Refinement
Crystal data, data collection and structure . The C-bound H atoms were placed according to the difference-Fourier map and refined using a riding model: C—H = 0.93–0.96 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms. Hydroxyl H atoms were placed according to a difference-Fourier map and were freely refined. The crystal studied was refined as a two-component This reflection file contains the non-overlapping reflections of the two twin components as well as the overlapping reflections. The BASF parameter for this two-component twin refined to −0.03242 (8).
details are summarized in Table 2Supporting information
CCDC reference: 2026445
https://doi.org/10.1107/S2056989020011974/zl2795sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020011974/zl2795Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989020011974/zl2795Isup3.cml
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: WinGX (Farrugia, 2012).C14H12INO | Dx = 1.761 Mg m−3 |
Mr = 337.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 6431 reflections |
a = 8.1730 (4) Å | θ = 2.5–32.6° |
b = 11.8143 (9) Å | µ = 2.50 mm−1 |
c = 13.1721 (8) Å | T = 296 K |
V = 1271.88 (14) Å3 | Rod, orange |
Z = 4 | 0.66 × 0.34 × 0.13 mm |
F(000) = 656 |
Stoe IPDS 2 diffractometer | 2482 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1949 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.033 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.9° |
rotation method scans | h = −8→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −14→14 |
Tmin = 0.365, Tmax = 0.784 | l = −12→16 |
5163 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: mixed |
wR(F2) = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0304P)2] where P = (Fo2 + 2Fc2)/3 |
2482 reflections | (Δ/σ)max = 0.001 |
160 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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. |
Refinement. Refined as a two-component inversion twin. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5327 (7) | 0.7863 (4) | 0.8238 (6) | 0.0512 (13) | |
C2 | 0.6359 (10) | 0.8192 (5) | 0.9003 (6) | 0.0664 (19) | |
H2 | 0.598522 | 0.866780 | 0.951494 | 0.080* | |
C3 | 0.7966 (11) | 0.7810 (6) | 0.9008 (6) | 0.076 (2) | |
H3 | 0.867715 | 0.803861 | 0.951899 | 0.092* | |
C4 | 0.8492 (8) | 0.7109 (5) | 0.8273 (7) | 0.0720 (18) | |
H4 | 0.956517 | 0.684703 | 0.828468 | 0.086* | |
C5 | 0.7452 (7) | 0.6773 (5) | 0.7497 (6) | 0.0632 (17) | |
H5 | 0.783507 | 0.629118 | 0.699235 | 0.076* | |
C6 | 0.5849 (7) | 0.7150 (5) | 0.7469 (5) | 0.0508 (14) | |
C7 | 0.5196 (7) | 0.6589 (5) | 0.5815 (5) | 0.0523 (13) | |
H7 | 0.628176 | 0.672300 | 0.564200 | 0.063* | |
C8 | 0.4100 (7) | 0.6148 (4) | 0.5043 (5) | 0.0475 (14) | |
C9 | 0.4719 (8) | 0.5869 (5) | 0.4092 (5) | 0.0599 (17) | |
H9 | 0.582202 | 0.598902 | 0.395435 | 0.072* | |
C10 | 0.3738 (9) | 0.5425 (5) | 0.3361 (6) | 0.0661 (17) | |
H10 | 0.416758 | 0.523217 | 0.273023 | 0.079* | |
C11 | 0.2093 (10) | 0.5262 (5) | 0.3564 (5) | 0.0624 (17) | |
H11 | 0.142297 | 0.496373 | 0.305986 | 0.075* | |
C12 | 0.1420 (8) | 0.5532 (5) | 0.4495 (5) | 0.0535 (15) | |
C13 | 0.2432 (7) | 0.5988 (4) | 0.5232 (5) | 0.0486 (15) | |
C14 | −0.0374 (8) | 0.5358 (6) | 0.4703 (7) | 0.075 (2) | |
H14A | −0.050482 | 0.493780 | 0.532175 | 0.113* | |
H14B | −0.085832 | 0.494527 | 0.415201 | 0.113* | |
H14C | −0.090242 | 0.607994 | 0.476842 | 0.113* | |
I1 | 0.29233 (6) | 0.84637 (4) | 0.82323 (4) | 0.07511 (17) | |
O1 | 0.1754 (5) | 0.6247 (4) | 0.6139 (4) | 0.0648 (12) | |
N1 | 0.4728 (6) | 0.6802 (3) | 0.6727 (5) | 0.0507 (11) | |
H1 | 0.254 (8) | 0.660 (5) | 0.654 (6) | 0.08 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.050 (3) | 0.050 (3) | 0.053 (3) | −0.005 (2) | 0.002 (4) | 0.002 (3) |
C2 | 0.074 (5) | 0.058 (4) | 0.067 (5) | −0.010 (3) | −0.003 (4) | −0.005 (3) |
C3 | 0.073 (5) | 0.075 (4) | 0.081 (5) | −0.014 (4) | −0.025 (5) | −0.001 (4) |
C4 | 0.058 (4) | 0.068 (3) | 0.090 (5) | −0.005 (3) | −0.015 (5) | −0.004 (5) |
C5 | 0.050 (4) | 0.057 (4) | 0.083 (5) | 0.002 (3) | −0.002 (3) | −0.007 (3) |
C6 | 0.049 (4) | 0.047 (3) | 0.057 (4) | −0.002 (3) | −0.007 (3) | 0.001 (3) |
C7 | 0.049 (3) | 0.050 (3) | 0.058 (4) | 0.002 (3) | 0.008 (3) | 0.001 (3) |
C8 | 0.046 (3) | 0.050 (3) | 0.046 (3) | 0.003 (2) | 0.002 (3) | 0.003 (2) |
C9 | 0.054 (4) | 0.070 (4) | 0.056 (4) | −0.001 (3) | 0.015 (3) | −0.003 (3) |
C10 | 0.074 (5) | 0.073 (4) | 0.051 (4) | 0.006 (4) | 0.008 (4) | −0.012 (4) |
C11 | 0.072 (4) | 0.061 (3) | 0.054 (4) | −0.001 (4) | −0.018 (4) | 0.000 (3) |
C12 | 0.049 (3) | 0.057 (3) | 0.055 (4) | −0.001 (3) | −0.006 (3) | 0.005 (3) |
C13 | 0.045 (4) | 0.048 (3) | 0.053 (3) | 0.004 (2) | 0.004 (3) | 0.004 (3) |
C14 | 0.053 (4) | 0.089 (4) | 0.084 (5) | −0.008 (4) | −0.009 (4) | 0.006 (4) |
I1 | 0.0656 (3) | 0.0895 (3) | 0.0703 (3) | 0.0186 (2) | 0.0053 (3) | −0.0094 (3) |
O1 | 0.049 (3) | 0.088 (3) | 0.057 (3) | −0.002 (2) | 0.009 (2) | −0.007 (2) |
N1 | 0.047 (2) | 0.050 (2) | 0.055 (3) | −0.0006 (18) | −0.001 (3) | 0.002 (3) |
C1—C2 | 1.370 (10) | C8—C9 | 1.390 (9) |
C1—C6 | 1.385 (9) | C8—C13 | 1.399 (8) |
C1—I1 | 2.089 (6) | C9—C10 | 1.359 (10) |
C2—C3 | 1.389 (11) | C9—H9 | 0.9300 |
C2—H2 | 0.9300 | C10—C11 | 1.384 (10) |
C3—C4 | 1.344 (11) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | C11—C12 | 1.382 (9) |
C4—C5 | 1.387 (10) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C12—C13 | 1.384 (8) |
C5—C6 | 1.384 (8) | C12—C14 | 1.505 (9) |
C5—H5 | 0.9300 | C13—O1 | 1.352 (7) |
C6—N1 | 1.401 (8) | C14—H14A | 0.9600 |
C7—N1 | 1.286 (8) | C14—H14B | 0.9600 |
C7—C8 | 1.451 (9) | C14—H14C | 0.9600 |
C7—H7 | 0.9300 | O1—H1 | 0.93 (7) |
C2—C1—C6 | 121.4 (6) | C10—C9—C8 | 121.0 (6) |
C2—C1—I1 | 119.0 (5) | C10—C9—H9 | 119.5 |
C6—C1—I1 | 119.6 (5) | C8—C9—H9 | 119.5 |
C1—C2—C3 | 119.6 (7) | C9—C10—C11 | 119.3 (7) |
C1—C2—H2 | 120.2 | C9—C10—H10 | 120.3 |
C3—C2—H2 | 120.2 | C11—C10—H10 | 120.3 |
C4—C3—C2 | 120.0 (7) | C12—C11—C10 | 121.8 (7) |
C4—C3—H3 | 120.0 | C12—C11—H11 | 119.1 |
C2—C3—H3 | 120.0 | C10—C11—H11 | 119.1 |
C3—C4—C5 | 120.7 (7) | C11—C12—C13 | 118.3 (6) |
C3—C4—H4 | 119.7 | C11—C12—C14 | 121.2 (6) |
C5—C4—H4 | 119.7 | C13—C12—C14 | 120.5 (6) |
C6—C5—C4 | 120.5 (6) | O1—C13—C12 | 117.6 (5) |
C6—C5—H5 | 119.7 | O1—C13—C8 | 121.7 (6) |
C4—C5—H5 | 119.7 | C12—C13—C8 | 120.7 (6) |
C5—C6—C1 | 117.8 (6) | C12—C14—H14A | 109.5 |
C5—C6—N1 | 122.9 (6) | C12—C14—H14B | 109.5 |
C1—C6—N1 | 119.2 (5) | H14A—C14—H14B | 109.5 |
N1—C7—C8 | 122.8 (6) | C12—C14—H14C | 109.5 |
N1—C7—H7 | 118.6 | H14A—C14—H14C | 109.5 |
C8—C7—H7 | 118.6 | H14B—C14—H14C | 109.5 |
C9—C8—C13 | 118.9 (6) | C13—O1—H1 | 109 (4) |
C9—C8—C7 | 119.4 (6) | C7—N1—C6 | 121.0 (5) |
C13—C8—C7 | 121.7 (6) | ||
C6—C1—C2—C3 | 0.4 (10) | C8—C9—C10—C11 | 0.9 (10) |
I1—C1—C2—C3 | −179.2 (5) | C9—C10—C11—C12 | −0.5 (10) |
C1—C2—C3—C4 | −0.9 (11) | C10—C11—C12—C13 | 0.8 (9) |
C2—C3—C4—C5 | 0.9 (11) | C10—C11—C12—C14 | 179.6 (6) |
C3—C4—C5—C6 | −0.3 (11) | C11—C12—C13—O1 | 180.0 (5) |
C4—C5—C6—C1 | −0.3 (9) | C14—C12—C13—O1 | 1.2 (8) |
C4—C5—C6—N1 | −177.3 (6) | C11—C12—C13—C8 | −1.4 (8) |
C2—C1—C6—C5 | 0.2 (9) | C14—C12—C13—C8 | 179.8 (5) |
I1—C1—C6—C5 | 179.8 (5) | C9—C8—C13—O1 | −179.7 (5) |
C2—C1—C6—N1 | 177.4 (5) | C7—C8—C13—O1 | 0.7 (8) |
I1—C1—C6—N1 | −3.1 (8) | C9—C8—C13—C12 | 1.7 (8) |
N1—C7—C8—C9 | −175.8 (6) | C7—C8—C13—C12 | −177.9 (5) |
N1—C7—C8—C13 | 3.8 (9) | C8—C7—N1—C6 | 175.4 (5) |
C13—C8—C9—C10 | −1.5 (9) | C5—C6—N1—C7 | −33.7 (9) |
C7—C8—C9—C10 | 178.2 (6) | C1—C6—N1—C7 | 149.2 (5) |
Cg2 is the centroid of the C8–C13 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.93 (7) | 1.82 (7) | 2.634 (6) | 144 (6) |
C2—H2···Cg2i | 0.93 | 2.97 (6) | 3.7445 (4) | 142 (4) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
Acknowledgements
This study was supported by Ondokuz Mayıs University under project No. PYO·FEN.1906.19.001.
Funding information
Funding for this research was provided by: Ondokuz Mayıs University (award No. PYO.FEN.1906.19.001).
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