organic compounds
Benzene-1,2-diaminium bis(4-methylbenzene-1-sulfonate)
aSchool of Chemical Sciences, Goa University PO, Goa 403206, India
*Correspondence e-mail: srini@unigoa.ac.in
The structure of the title salt, C6H10N22+·2C7H7O3S−, consists of a unique benzene-1,2-diaminium dication charge balanced by a pair of crystallographically independent 4-methylbenzene-1-sulfonate anions. The cations and anions are interlinked by several N—H⋯O hydrogen bonds.
Keywords: crystal structure; benzene-1,2-diaminium dication; 4-methylbenzene-1-sulfonate anion; organic salt.
CCDC reference: 1979912
Structure description
The aromatic diamine, benzene-1,2-diamine also known as o-phenylenediamine, can function as a neutral ligand and bind to a metal via both amine N atoms (Koizumi & Fukuju, 2011; Guillén et al., 2018) or by a single nitrogen in a monodentate fashion (Nelson et al., 1982; Dickman, 2000). In addition, benzene-1,2-diamine can function as a charge-balancing dication in which both the amine N atoms are protonated (Raghavaiah et al., 2006; Powers & Geiger, 2019) or as a monocation (Raghavaiah et al., 2005; Mishra & Pallepogu, 2018). The structural diversity of the compounds of benzene-1,2-diamine in neutral or cationic form is highlighted by the results of a survey of the Cambridge Structural Database (CSD; Groom et al., 2016), which had more than 220 hits for the above three types of compounds. Of these, a total of 79 deposits do not contain any metal ions and correspond to crystal structures containing only diprotonated benzene-1,2-diaminium cations (47 hits) and monoprotonated 2-aminoanilinium cations (55 hits). An example of a molecular salt of 4-methylbenzene-1-sulfonic acid containing both mono and diprotonated cations, namely 2-aminoanilinium benzene-1,2-diaminium tris(4-methylbenzene-1-sulfonate) (2) has been reported recently (Amirthakumar et al., 2018).
In this report, we describe the 2, which was isolated from a 1:1 reaction. The of the title compound consists of an unique benzene-1,2-diaminium dication charge-balanced by a pair of crystallographically independent 4-methylbenzene-1-sulfonate anions (Fig. 1) with all atoms located on general positions. The geometric parameters of the unique dication and the crystallographically independent anions are in normal ranges and are in agreement with reported data (Powers & Geiger, 2019).
of the title compound, which was obtained by an aqueous reaction of the aromatic diamine with 4-methylbenzene-1-sulfonic acid in a 1:2 molar ratio, unlikeAll six oxygen atoms attached to the sulfur atom of the sulfonate moiety of the anion function as hydrogen-bond acceptors while the H atoms attached to the N atoms of the dication function as hydrogen-bond donors, resulting in a total of eight N—H⋯O hydrogen bonds of which six are intermolecular (Table 1). It is interesting to note that the dications and the unique anions are interlinked only via N—H⋯O hydrogen bonds, unlike in 2 for which both N—H⋯O and C—H⋯O hydrogen bonds were reported. Each anion is linked to three symmetry-related dications (Fig. 2) while each dication is hydrogen-bonded to six symmetry-related anions. The net result of the hydrogen-bonding interactions is the interlinking of the cations with the anions, resulting in alternating layers of cations and anions parallel to [010] (Fig. 3).
Synthesis and crystallization
Freshly recrystallized benzene-1,2-diamine (108 mg, 1 mmol) was dissolved in double-distilled water (10–15 ml) by heating the mixture. Into this, an aqueous solution of 4-methylbenzene-1-sulfonic acid (380 mg, 2 mmol) was added. The reaction mixture was heated to boiling and a pinch of 1 slowly separated. The crystals were filtered and air dried. Yield 50%.
was added. The hot solution was filtered and the clear filtrate was left aside for crystallization. After a few days, crystals of the title compoundRefinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1979912
https://doi.org/10.1107/S2414314620001005/bv4029sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620001005/bv4029Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620001005/bv4029Isup3.cml
Data collection: APEX3 (Bruker, 2018); cell
SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: shelXle (Hübschle et al., 2011).C6H10N22+·2C7H7O3S− | F(000) = 1904 |
Mr = 452.53 | Dx = 1.396 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 29.1537 (9) Å | Cell parameters from 9968 reflections |
b = 8.8739 (3) Å | θ = 2.9–29.9° |
c = 19.9919 (6) Å | µ = 0.29 mm−1 |
β = 123.621 (1)° | T = 293 K |
V = 4306.9 (2) Å3 | Block, colourless |
Z = 8 | 0.56 × 0.14 × 0.12 mm |
Bruker D8 Quest ECO diffractometer | 4705 reflections with I > 2σ(I) |
Radiation source: Sealed Tube | Rint = 0.046 |
φ and ω scans | θmax = 30.5°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2018) | h = −41→41 |
Tmin = 0.696, Tmax = 0.746 | k = −12→12 |
59056 measured reflections | l = −28→28 |
6568 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0525P)2 + 2.9966P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.126 | (Δ/σ)max = 0.001 |
S = 1.07 | Δρmax = 0.34 e Å−3 |
6568 reflections | Δρmin = −0.39 e Å−3 |
276 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0026 (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. All hydrogen atoms were located in appropriate positions and were included in calculated positions and refined with a riding model for both C—H and N—H protons. C–H distances ranged from = 0.93 and 0.96 Å for aromatic and methyl H atoms, respectively, and 0.89 for NH3+ H atoms with Uiso(H) = 1.2 Ueq(C-aromatic) and Uiso(H) = 1.5 Ueq(C-methyl, NH3+). |
x | y | z | Uiso*/Ueq | ||
N1 | 0.52597 (6) | 0.42385 (15) | 0.43447 (8) | 0.0399 (3) | |
H1A | 0.516000 | 0.511465 | 0.408451 | 0.060* | |
H1B | 0.552390 | 0.439398 | 0.485886 | 0.060* | |
H1C | 0.497014 | 0.381592 | 0.430938 | 0.060* | |
N2 | 0.54019 (6) | 0.10069 (15) | 0.46813 (8) | 0.0374 (3) | |
H2A | 0.505767 | 0.066255 | 0.439229 | 0.056* | |
H2B | 0.543473 | 0.168126 | 0.503495 | 0.056* | |
H2C | 0.563230 | 0.024462 | 0.494094 | 0.056* | |
C1 | 0.54643 (6) | 0.32416 (17) | 0.39869 (9) | 0.0349 (3) | |
C2 | 0.55343 (6) | 0.17140 (17) | 0.41510 (9) | 0.0344 (3) | |
C3 | 0.57224 (8) | 0.0796 (2) | 0.37927 (12) | 0.0505 (4) | |
H3 | 0.576521 | −0.023317 | 0.389900 | 0.061* | |
C4 | 0.58462 (11) | 0.1411 (3) | 0.32770 (14) | 0.0661 (6) | |
H4 | 0.597256 | 0.079592 | 0.303508 | 0.079* | |
C5 | 0.57830 (11) | 0.2935 (3) | 0.31201 (15) | 0.0664 (6) | |
H5 | 0.586983 | 0.334936 | 0.277609 | 0.080* | |
C6 | 0.55909 (9) | 0.3848 (2) | 0.34726 (12) | 0.0529 (4) | |
H6 | 0.554660 | 0.487571 | 0.336310 | 0.064* | |
S11 | 0.60971 (2) | −0.26457 (4) | 0.57918 (2) | 0.03904 (11) | |
O11 | 0.61408 (5) | −0.40103 (15) | 0.54362 (8) | 0.0562 (3) | |
O12 | 0.61358 (6) | −0.12891 (15) | 0.54200 (8) | 0.0563 (3) | |
O13 | 0.56134 (5) | −0.26132 (16) | 0.58310 (9) | 0.0573 (4) | |
C11 | 0.81185 (11) | −0.2503 (3) | 0.92035 (15) | 0.0827 (8) | |
H11A | 0.833550 | −0.338591 | 0.929269 | 0.124* | |
H11B | 0.801302 | −0.248348 | 0.958103 | 0.124* | |
H11C | 0.833111 | −0.161970 | 0.927333 | 0.124* | |
C12 | 0.76068 (8) | −0.2532 (2) | 0.83564 (12) | 0.0540 (5) | |
C13 | 0.71405 (8) | −0.1716 (2) | 0.81418 (11) | 0.0541 (5) | |
H13 | 0.713844 | −0.113580 | 0.852757 | 0.065* | |
C14 | 0.66758 (7) | −0.1744 (2) | 0.73639 (11) | 0.0460 (4) | |
H14 | 0.636634 | −0.118206 | 0.722766 | 0.055* | |
C15 | 0.66778 (6) | −0.26174 (17) | 0.67934 (10) | 0.0363 (3) | |
C16 | 0.71387 (7) | −0.3444 (2) | 0.69966 (12) | 0.0523 (4) | |
H16 | 0.713945 | −0.403424 | 0.661270 | 0.063* | |
C17 | 0.76014 (8) | −0.3390 (3) | 0.77780 (13) | 0.0616 (5) | |
H17 | 0.791258 | −0.394165 | 0.791294 | 0.074* | |
S21 | 0.45059 (2) | 0.76496 (4) | 0.35286 (2) | 0.03714 (11) | |
O21 | 0.49995 (5) | 0.70837 (16) | 0.36096 (8) | 0.0547 (3) | |
O22 | 0.44084 (6) | 0.69248 (16) | 0.40921 (7) | 0.0559 (3) | |
O23 | 0.44971 (6) | 0.92776 (14) | 0.35764 (8) | 0.0565 (4) | |
C21 | 0.26881 (15) | 0.5602 (4) | 0.01997 (17) | 0.1233 (14) | |
H21A | 0.233080 | 0.582893 | 0.009049 | 0.185* | |
H21B | 0.272805 | 0.452969 | 0.018852 | 0.185* | |
H21C | 0.272661 | 0.606499 | −0.020056 | 0.185* | |
C22 | 0.31300 (11) | 0.6205 (3) | 0.10249 (13) | 0.0742 (7) | |
C23 | 0.30782 (11) | 0.6004 (3) | 0.16652 (16) | 0.0813 (7) | |
H23 | 0.275944 | 0.556751 | 0.157815 | 0.098* | |
C24 | 0.34940 (9) | 0.6443 (3) | 0.24375 (13) | 0.0609 (5) | |
H24 | 0.345911 | 0.627550 | 0.286660 | 0.073* | |
C25 | 0.39576 (7) | 0.71265 (18) | 0.25587 (9) | 0.0387 (3) | |
C26 | 0.40091 (9) | 0.7360 (2) | 0.19192 (11) | 0.0496 (4) | |
H26 | 0.432285 | 0.782254 | 0.200184 | 0.060* | |
C27 | 0.35939 (11) | 0.6905 (3) | 0.11584 (12) | 0.0665 (6) | |
H27 | 0.362871 | 0.707427 | 0.072940 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0434 (7) | 0.0323 (6) | 0.0424 (7) | 0.0035 (5) | 0.0229 (6) | −0.0005 (5) |
N2 | 0.0435 (7) | 0.0346 (6) | 0.0376 (7) | 0.0003 (5) | 0.0246 (6) | 0.0022 (5) |
C1 | 0.0357 (7) | 0.0340 (7) | 0.0356 (7) | −0.0015 (6) | 0.0202 (6) | −0.0014 (6) |
C2 | 0.0390 (8) | 0.0329 (7) | 0.0352 (7) | −0.0019 (6) | 0.0230 (6) | −0.0009 (6) |
C3 | 0.0707 (12) | 0.0390 (9) | 0.0597 (11) | 0.0038 (8) | 0.0473 (10) | −0.0019 (8) |
C4 | 0.0979 (17) | 0.0598 (12) | 0.0792 (15) | 0.0033 (11) | 0.0732 (14) | −0.0036 (11) |
C5 | 0.0924 (16) | 0.0672 (13) | 0.0737 (14) | −0.0001 (12) | 0.0673 (14) | 0.0091 (11) |
C6 | 0.0669 (12) | 0.0435 (9) | 0.0623 (11) | −0.0018 (8) | 0.0444 (10) | 0.0082 (8) |
S11 | 0.03285 (19) | 0.0358 (2) | 0.0398 (2) | 0.00174 (14) | 0.01463 (16) | −0.00139 (15) |
O11 | 0.0498 (7) | 0.0493 (7) | 0.0513 (7) | 0.0054 (6) | 0.0165 (6) | −0.0134 (6) |
O12 | 0.0558 (8) | 0.0497 (7) | 0.0522 (7) | 0.0056 (6) | 0.0227 (6) | 0.0147 (6) |
O13 | 0.0324 (6) | 0.0628 (9) | 0.0694 (9) | −0.0034 (5) | 0.0237 (6) | −0.0094 (7) |
C11 | 0.0602 (14) | 0.095 (2) | 0.0504 (12) | 0.0003 (12) | 0.0039 (11) | −0.0007 (12) |
C12 | 0.0433 (9) | 0.0557 (11) | 0.0440 (10) | −0.0025 (8) | 0.0122 (8) | 0.0027 (8) |
C13 | 0.0534 (11) | 0.0615 (12) | 0.0427 (9) | −0.0035 (9) | 0.0236 (8) | −0.0089 (8) |
C14 | 0.0403 (8) | 0.0516 (10) | 0.0449 (9) | 0.0032 (7) | 0.0229 (7) | −0.0038 (7) |
C15 | 0.0320 (7) | 0.0356 (7) | 0.0390 (8) | −0.0009 (6) | 0.0182 (6) | 0.0017 (6) |
C16 | 0.0413 (9) | 0.0563 (11) | 0.0504 (10) | 0.0096 (8) | 0.0199 (8) | −0.0063 (8) |
C17 | 0.0403 (10) | 0.0659 (13) | 0.0586 (12) | 0.0134 (9) | 0.0149 (9) | −0.0009 (10) |
S21 | 0.0452 (2) | 0.03159 (19) | 0.03394 (19) | 0.00202 (14) | 0.02151 (17) | 0.00074 (13) |
O21 | 0.0502 (7) | 0.0599 (8) | 0.0523 (7) | 0.0147 (6) | 0.0274 (6) | 0.0096 (6) |
O22 | 0.0741 (9) | 0.0606 (8) | 0.0383 (6) | −0.0077 (7) | 0.0345 (7) | −0.0003 (6) |
O23 | 0.0581 (8) | 0.0318 (6) | 0.0582 (8) | 0.0003 (5) | 0.0188 (7) | −0.0062 (5) |
C21 | 0.131 (3) | 0.089 (2) | 0.0642 (16) | −0.005 (2) | 0.0007 (17) | −0.0314 (16) |
C22 | 0.0841 (16) | 0.0541 (12) | 0.0475 (11) | 0.0005 (11) | 0.0132 (11) | −0.0131 (9) |
C23 | 0.0700 (15) | 0.0772 (17) | 0.0764 (16) | −0.0281 (13) | 0.0279 (13) | −0.0191 (13) |
C24 | 0.0641 (12) | 0.0657 (13) | 0.0564 (11) | −0.0176 (10) | 0.0355 (10) | −0.0091 (10) |
C25 | 0.0486 (9) | 0.0326 (7) | 0.0356 (7) | 0.0005 (6) | 0.0237 (7) | −0.0019 (6) |
C26 | 0.0659 (12) | 0.0465 (10) | 0.0406 (9) | 0.0041 (8) | 0.0320 (9) | 0.0042 (7) |
C27 | 0.0919 (17) | 0.0610 (12) | 0.0383 (9) | 0.0128 (12) | 0.0309 (11) | 0.0004 (9) |
N1—C1 | 1.4570 (19) | C13—C14 | 1.386 (3) |
N2—C2 | 1.4561 (18) | C14—C15 | 1.382 (2) |
C1—C6 | 1.380 (2) | C15—C16 | 1.380 (2) |
C1—C2 | 1.383 (2) | C16—C17 | 1.389 (3) |
C2—C3 | 1.383 (2) | S21—O21 | 1.4462 (14) |
C3—C4 | 1.380 (3) | S21—O23 | 1.4490 (13) |
C4—C5 | 1.378 (3) | S21—O22 | 1.4554 (13) |
C5—C6 | 1.380 (3) | S21—C25 | 1.7602 (17) |
S11—O11 | 1.4451 (13) | C21—C22 | 1.521 (3) |
S11—O12 | 1.4517 (14) | C22—C27 | 1.373 (4) |
S11—O13 | 1.4553 (14) | C22—C23 | 1.381 (4) |
S11—C15 | 1.7671 (16) | C23—C24 | 1.390 (3) |
C11—C12 | 1.515 (3) | C24—C25 | 1.375 (3) |
C12—C17 | 1.377 (3) | C25—C26 | 1.383 (2) |
C12—C13 | 1.382 (3) | C26—C27 | 1.379 (3) |
C6—C1—C2 | 119.60 (15) | C16—C15—C14 | 120.25 (16) |
C6—C1—N1 | 118.71 (15) | C16—C15—S11 | 119.46 (13) |
C2—C1—N1 | 121.69 (13) | C14—C15—S11 | 120.27 (12) |
C3—C2—C1 | 120.23 (14) | C15—C16—C17 | 119.57 (18) |
C3—C2—N2 | 117.66 (14) | C12—C17—C16 | 121.09 (18) |
C1—C2—N2 | 122.10 (13) | O21—S21—O23 | 113.06 (9) |
C4—C3—C2 | 119.78 (17) | O21—S21—O22 | 111.63 (9) |
C5—C4—C3 | 120.09 (18) | O23—S21—O22 | 111.81 (9) |
C4—C5—C6 | 120.07 (18) | O21—S21—C25 | 105.80 (8) |
C5—C6—C1 | 120.23 (18) | O23—S21—C25 | 107.28 (8) |
O11—S11—O12 | 112.95 (9) | O22—S21—C25 | 106.77 (8) |
O11—S11—O13 | 113.27 (8) | C27—C22—C23 | 118.7 (2) |
O12—S11—O13 | 111.32 (8) | C27—C22—C21 | 121.4 (3) |
O11—S11—C15 | 106.21 (7) | C23—C22—C21 | 119.9 (3) |
O12—S11—C15 | 105.73 (8) | C22—C23—C24 | 121.2 (2) |
O13—S11—C15 | 106.72 (8) | C25—C24—C23 | 119.1 (2) |
C17—C12—C13 | 118.48 (17) | C24—C25—C26 | 120.16 (17) |
C17—C12—C11 | 119.6 (2) | C24—C25—S21 | 121.00 (14) |
C13—C12—C11 | 121.9 (2) | C26—C25—S21 | 118.79 (14) |
C12—C13—C14 | 121.40 (18) | C27—C26—C25 | 119.8 (2) |
C15—C14—C13 | 119.22 (17) | C22—C27—C26 | 121.0 (2) |
C6—C1—C2—C3 | −0.9 (2) | C14—C15—C16—C17 | −0.2 (3) |
N1—C1—C2—C3 | 179.13 (16) | S11—C15—C16—C17 | 178.16 (16) |
C6—C1—C2—N2 | −179.29 (16) | C13—C12—C17—C16 | −0.2 (3) |
N1—C1—C2—N2 | 0.8 (2) | C11—C12—C17—C16 | 179.8 (2) |
C1—C2—C3—C4 | 0.7 (3) | C15—C16—C17—C12 | 0.5 (3) |
N2—C2—C3—C4 | 179.15 (19) | C27—C22—C23—C24 | −2.5 (4) |
C2—C3—C4—C5 | 0.0 (4) | C21—C22—C23—C24 | 175.2 (3) |
C3—C4—C5—C6 | −0.6 (4) | C22—C23—C24—C25 | 1.8 (4) |
C4—C5—C6—C1 | 0.4 (4) | C23—C24—C25—C26 | −0.6 (3) |
C2—C1—C6—C5 | 0.4 (3) | C23—C24—C25—S21 | −177.95 (19) |
N1—C1—C6—C5 | −179.68 (19) | O21—S21—C25—C24 | 131.47 (17) |
C17—C12—C13—C14 | −0.3 (3) | O23—S21—C25—C24 | −107.57 (17) |
C11—C12—C13—C14 | 179.6 (2) | O22—S21—C25—C24 | 12.44 (18) |
C12—C13—C14—C15 | 0.6 (3) | O21—S21—C25—C26 | −45.95 (16) |
C13—C14—C15—C16 | −0.3 (3) | O23—S21—C25—C26 | 75.00 (16) |
C13—C14—C15—S11 | −178.67 (15) | O22—S21—C25—C26 | −164.99 (14) |
O11—S11—C15—C16 | 22.07 (17) | C24—C25—C26—C27 | 0.0 (3) |
O12—S11—C15—C16 | −98.17 (16) | S21—C25—C26—C27 | 177.46 (15) |
O13—S11—C15—C16 | 143.20 (15) | C23—C22—C27—C26 | 1.9 (4) |
O11—S11—C15—C14 | −159.58 (14) | C21—C22—C27—C26 | −175.7 (2) |
O12—S11—C15—C14 | 80.18 (15) | C25—C26—C27—C22 | −0.7 (3) |
O13—S11—C15—C14 | −38.45 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O21 | 0.89 | 1.92 | 2.8062 (19) | 175 |
N1—H1B···O11i | 0.89 | 2.07 | 2.7509 (19) | 133 |
N1—H1B···O22ii | 0.89 | 2.31 | 2.9017 (18) | 124 |
N1—H1C···O13iii | 0.89 | 1.89 | 2.7733 (19) | 170 |
N2—H2A···O13iii | 0.89 | 2.46 | 2.9128 (19) | 112 |
N2—H2A···O23iv | 0.89 | 1.97 | 2.7820 (18) | 151 |
N2—H2B···O22ii | 0.89 | 1.98 | 2.8611 (19) | 173 |
N2—H2C···O12 | 0.89 | 1.84 | 2.7224 (19) | 175 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) x, y−1, z. |
Acknowledgements
The authors acknowledge the Department of Science & Technology (DST) New Delhi, for the sanction of a Bruker D8 Quest Eco single-crystal X-ray diffractometer under the DST–FIST program.
References
Amirthakumar, C., Pandi, P., Kumar, R. M. & Chakkaravarthi, G. (2018). IUCrData, 3, x180437. Google Scholar
Bruker (2018). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dickman, M. H. (2000). Acta Cryst. C56, 58–60. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
González Guillén, A., Oszajca, M., Luberda-Durnaś, K., Gryl, M., Bartkiewicz, S., Miniewicz, A. & Lasocha, W. (2018). Cryst. Growth Des. 18, 5029–5037. Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281–1284. Web of Science CrossRef IUCr Journals Google Scholar
Koizumi, T. & Fukuju, K. (2011). J. Organomet. Chem. 696, 232–1235. CrossRef Google Scholar
Mishra, R. & Pallepogu, R. (2018). Acta Cryst. B74, 32–41. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nelson, S. M., Esho, F. S. & Drew, M. G. B. (1982). J. Chem. Soc. Dalton Trans. pp. 407–415. CSD CrossRef Web of Science Google Scholar
Powers, K. A. & Geiger, D. K. (2019). Acta Cryst. C75, 329–335. CrossRef IUCr Journals Google Scholar
Raghavaiah, P., Supriya, S. & Das, S. K. (2005). CrystEngComm, 7, 167–170. Web of Science CSD CrossRef CAS Google Scholar
Raghavaiah, P., Supriya, S. & Das, S. K. (2006). Chem. Commun. pp. 2762–2764. CrossRef Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.