Synthesis and crystal structure determination of aluminium hydroxide methane­sulfonate, Al(OH)(CH3SO3)2

Gabilondo, E.; Halasyamani, P.S.

doi:10.1107/S2056989026005578

early career research

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Volume 82| Part 7| July 2026|

https://doi.org/10.1107/S2056989026005578

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Synthesis and crystal structure determination of aluminium hydroxide methanesulfonate, Al(OH)(CH₃SO₃)₂

Eric Gabilondo ^a ^* and P. Shiv Halasyamani ^b

^aSchool of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland, and ^bDepartment of Chemistry, University of Houston, 3585 Cullen Blvd, Room 112, Houston, TX, 77204-5003, USA
^*Correspondence e-mail: [email protected]

Edited by T. Akitsu, Tokyo University of Science, Japan (Received 1 May 2026; accepted 26 May 2026; online 5 June 2026)

This article is part of the collection Early Career Scientists in Structural Science.

catena-Poly[aluminium(III)-μ-hydroxido-κ²O:O-di-μ-methanesulfonato-κ⁴O:O′], [Al(OH)(CH₃SO₃)₂]_n, was prepared by mild hydrothermal synthesis at 523 K and crystallizes as millimetre-sized clear and colourless needles. The asymmetric unit contains half of the repeating structure, one-dimensional (AlO₆)_∞ chains corner sharing through the axial hydroxyl group with a bend of ∼137^ο. The extended structure shows the chains are connected through weak methyl–hydrogen bonding in the [001] direction and strong hydroxyl–hydrogen bonding in the [100] direction. This is the second aluminium-based methanesulfonate salt reported to date.

Keywords: crystal structure; methanesulfonic acid; aluminium; hydroxide; crystal growth.

CCDC reference: 2541524

1. Chemical context

Crystals containing the methanesulfonate anion, CH₃SO₃⁻, have attracted interest as potential linear and non-linear optical crystals (Tian et al., 2023 ; Gabilondo & Halasyamani, 2025 ). However, there are relatively few crystal structures reported compared to other anionic groups such as Cl⁻, F⁻, SO₄²⁻, or PO₄³⁻, to name a few, rendering structure prediction a challenge. Herein, we report an aluminium-based methanesulfonate salt, Al(OH)(CH₃SO₃)₂ (I). The title compound is the second Al-based methanesulfonate to be discovered alongside Al(CH₃SO₃)₃(H₂O)₆, (II; Trella & Frank, 2012 ).

2. Structural commentary

Compound I crystallizes in the triclinic space group P $[\overline{1}]$ . The asymmetric unit, shown in Fig. 1, contains half of the two repeating AlO₆ octahedra, which are corner sharing at the axial positions through a hydroxyl bridge (O3—H3). Each octahedron is additionally bridged at the equatorial positions by two methanesulfonate anion groups (O6/S1/O2 and O5/S2/O4). The two Al atoms differ by Wyckoff position 1f and 1h, for Al1 and Al2, respectively. The AlO₆ octahedra have a small axial compression (∼4%) with an average bond length of (axial) 1.8394 (14) Å and (equatorial) 1.9165 (15) Å. There is little angular distortion from the ideal values of 90 (1) and 180°. The methanesulfonate groups are largely undistorted and have similar geometries to those in previous reports (Wei & Hingerty, 1981 ). For example, the average S—O single bond length is 1.473 (1) Å, S=O is 1.439 (3) Å, and S—C is 1.734 (2) Å, compared to literature values of 1.461 (1), 1.452 (1) and 1.754 (2) Å, respectively. One methanesulfonate group (S2) is disordered with refined occupancies of 0.68 (3)/0.32 (3). There is a minor rotation of the O7—S2—C2 angle of 11.7 (12)° between the two residues with S2 unaffected. The cause is likely weak interlayer hydrogen bonding, discussed below and not uncommon in metal methanesulfonates (Singh et al., 2020 ; Wickleder & Müller, 2004 ). The structure of I is in contrast to the known II that has isolated Al(OH₂)₆ octahedra bridged via hydrogen bonding to CH₃SO₃⁻ anions, with no direct coordination of the octahedra nor the CH₃SO₃⁻ groups. The bond-valence sum for each atom (Brown 2009 ) is consistent with the expected oxidation states of Al^III, S^VI, O²⁻, and C^IV, with average experimental values of 3.155 (5), 5.83 (4), 2.0 (1), and 4.136 (3), respectively, and supports reasonable hydrogen-atom assignments.

Figure 1
The asymmetric unit of I with displacement ellipsoids shown at the 50% probability level. The terminal oxygen (O7) and methyl (C2, H2A, H2B, H2C) groups are disordered with refined occupancies of 0.68 (3)/0.32 (3). The minor residue is shown in green.

3. Supramolecular features

The unit cell and packing diagram of I is shown in Fig. 2a with primary supramolecular structural motifs in Fig. 2b–d. As shown in Fig. 2a, the unit cell contains two asymmetric units to complete a one-dimensional chain of AlO₆ octahedra. The chains are corner-sharing through the OH group at the axial positions and rotate by an Al—O—Al angle of 134.57 (7)°. Fig. 2b highlights the extended structure as isolated one-dimensional chains connected via hydrogen bonding (Table 1). The chains are connected weakly in the [001] direction through hydrogen bonding (Fig. 2c) between the terminal S2=O7 group and the methyl group on C2. The weak hydrogen bonding is likely responsible for the disorder of C2, S2, and O7, with weak interactions not ‘locking' the terminal groups in place. Meanwhile, stronger and more traditional hydrogen bonding connects the chains in the [100] direction through the hydroxyl group from O3—H3⋯O1 (Fig. 2d). The relative strength of the interchain hydrogen bonding is exemplified by the Al⋯Al distances of 9.7677 (15) Å in the [001] direction and 6.5099 (11) Å in the [100] direction, corresponding to the unit-cell parameters c and a, respectively. The extended structure of I again contrasts with the structure of II by having direct connectivity through one-dimensional chains of AlO₆ octahedra rather than the 0D structure of II held together by a hydrogen-bonding network.

Table 1
Hydrogen-bond geometry (Å, °)

Hydrogen-bonding distances refer to the major residue.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O7ⁱ	0.96	2.62	3.304 (15)	129
C2—H2B⋯O7	0.96	2.72	3.641 (16)	162
O3—H3⋯O1ⁱⁱ	0.94 (1)	1.87 (1)	2.802 (3)	171 (2)
Symmetry codes: (i) ; (ii) .

Figure 2
(a) Packing diagram and unit cell for I and (b) polyhedral extended structure of one-dimensional chains. AlO₆ chains are connected via (c) weak hydrogen bonding (C2—H2B⋯O7) bonding in the [001] direction and (d) with traditional hydrogen bonding (O3—H3⋯O1) in the [100] direction. Disorder is removed for clarity.

4. Database survey

The Cambridge Structural Database (CSD, accessed May 2026; Groom et al., 2016 ) contains 54 metal–methanesulfonates and the Inorganic Crystalline Structure Database (ICSD; Zagorac et al., 2019 ) contains 21. Only one of these contains Al, as highlighted earlier: II Al(CH₃SO₃)₃(H₂O)₆ (LEHREX; Trella & Frank, 2012). Compound I is the first reported hydroxide-bridged aluminium methanesulfonate containing one-dimensional, corner-sharing AlO₆ chains. Compound I is not isostructural with other reported metal–methanesulfonate hydroxides, even the empirically similar Sc(OH)(CH₃SO₃)₂ (ESARAR; Wickleder & Müller, 2004).

5. Synthesis and crystallization

Compound I was synthesized by a hydrothermal route. 1.322 g (3.5 mmol) of aluminium nitrate nonahydrate [Al(NO₃)₃(H₂O)₉, Alfa Aesar, 98%] were added to 1 mL of methanesulfonic acid (4.9 mmol, 70 w/w% in H₂O, Thermo Fisher) inside a Teflon-lined autoclave prior to sealing and placing in a muffle furnace. The furnace was heated to 523 K at a rate of 1 K min⁻¹, held for 72 h, then radiatively cooled to room temperature. Solid products were collected via vacuum filtration followed by rinsing with acetonitrile to remove solvent. Millimetre-sized, clear and colourless needle-shaped crystals were separated mechanically from the other insoluble and amorphous solid products. Crystals were dried overnight in a vacuum desiccator prior to further analysis. Yield was ∼56% with respect to Al. The crystals are slightly hygroscopic and slowly decompose to II in air over the course of several weeks or rapidly upon grinding.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Methyl-H atoms were refined using a riding model with ideal tetrahedral angles once identified using difference maps. The hydroxyl-H atom (H3) was similarly identified by both difference maps and a low bond-valence sum around O3 of 1.2 v.u. (Brown 2009). The O3—H3 bond was restrained to 0.97 (1) Å [U_iso(H) = 1.5U_eq(O)] and restrained to be equidistant from Al1 and Al2 to maintain the ideal OH geometry. Restraints were adopted because the O3—H3 bond became unusually short unrestrained (∼0.73 Å). The terminal methanesulfonate unit was treated as a disordered residue due to unusually large anisotropic displacement parameters on C2 and O7, with refined occupancies of 0.68 (3)/0.32 (3).

Table 2
Experimental details

Crystal data
Chemical formula	[Al(OH)(CH₃SO₃)₂]
M_r	234.18
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	301
a, b, c (Å)	6.5099 (10), 6.7869 (10), 9.7677 (15)
α, β, γ (°)	94.712 (6), 109.253 (6), 90.177 (6)
V (Å³)	405.83 (11)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.76
Crystal size (mm)	0.25 × 0.03 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.674, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	15679, 2007, 1707
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.087, 1.07
No. of reflections	2007
No. of parameters	125
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.41
Computer programs: APEX5 (Bruker, 2023 ), SAINT (Bruker, 2008 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ) and Mercury (Macrae et al., 2020 ).

Supporting information

CCDC reference: 2541524

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026005578/jp2028sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026005578/jp2028Isup2.hkl

checkCIF report

Computing details top

catena-Poly[aluminium(III)-µ-hydroxido-κ²O:O-di-µ-methanesulfonato-κ⁴O:O'] top

Crystal data top

[Al(OH)(CH₃SO₃)₂]	Z = 2
M_r = 234.18	F(000) = 240
Triclinic, P1	D_x = 1.916 Mg m⁻³
a = 6.5099 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.7869 (10) Å	Cell parameters from 4784 reflections
c = 9.7677 (15) Å	θ = 2.2–27.8°
α = 94.712 (6)°	µ = 0.76 mm⁻¹
β = 109.253 (6)°	T = 301 K
γ = 90.177 (6)°	Needle, colourless
V = 405.83 (11) Å³	0.25 × 0.03 × 0.03 mm

Data collection top

Bruker APEXII CCD diffractometer	1707 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.050
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 28.3°, θ_min = 2.2°
T_min = 0.674, T_max = 0.746	h = −8→8
15679 measured reflections	k = −9→9
2007 independent reflections	l = −12→13

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0417P)² + 0.2379P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2007 reflections	Δρ_max = 0.43 e Å⁻³
125 parameters	Δρ_min = −0.41 e Å⁻³
2 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.26117 (8)	0.76941 (7)	0.66932 (5)	0.01853 (14)
S2	0.77597 (9)	0.28304 (7)	0.77275 (5)	0.02129 (15)
Al1	0.500000	0.000000	0.500000	0.0166 (2)
Al2	0.500000	0.500000	0.500000	0.0165 (2)
O1	0.0586 (3)	0.7731 (2)	0.69736 (18)	0.0284 (4)
O2	0.2868 (3)	0.9380 (2)	0.58889 (17)	0.0235 (3)
O3	0.3839 (2)	0.24615 (19)	0.47067 (15)	0.0171 (3)
H3	0.2321 (17)	0.2411 (18)	0.424 (2)	0.026*
O4	0.7021 (3)	0.4503 (2)	0.68421 (16)	0.0247 (4)
O5	0.6994 (3)	0.0937 (2)	0.68568 (16)	0.0242 (3)
O6	0.2883 (2)	0.5812 (2)	0.59119 (16)	0.0229 (3)
C1	0.4736 (4)	0.7916 (4)	0.8366 (2)	0.0319 (5)
H1A	0.610534	0.780972	0.819857	0.048*
H1B	0.457894	0.688125	0.894139	0.048*
H1C	0.468552	0.917766	0.887359	0.048*
O7	0.740 (3)	0.3028 (15)	0.9115 (14)	0.0442 (18)	0.68 (3)
C2	1.070 (2)	0.2877 (18)	0.8079 (14)	0.0376 (19)	0.68 (3)
H2A	1.131846	0.175313	0.858649	0.056*	0.68 (3)
H2B	1.134113	0.406980	0.866437	0.056*	0.68 (3)
H2C	1.097876	0.283080	0.717226	0.056*	0.68 (3)
C2A	1.035 (4)	0.287 (4)	0.837 (3)	0.0376 (19)	0.32 (3)
H2AA	1.092830	0.265748	0.758451	0.056*	0.32 (3)
H2AB	1.081138	0.184014	0.901309	0.056*	0.32 (3)
H2AC	1.087015	0.412787	0.889476	0.056*	0.32 (3)
O7A	0.683 (4)	0.294 (4)	0.881 (2)	0.0442 (18)	0.32 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0180 (3)	0.0142 (2)	0.0248 (3)	−0.00089 (18)	0.00896 (19)	0.00137 (19)
S2	0.0278 (3)	0.0128 (2)	0.0201 (3)	−0.0013 (2)	0.0036 (2)	0.00119 (18)
Al1	0.0182 (4)	0.0076 (4)	0.0228 (4)	−0.0012 (3)	0.0052 (3)	0.0016 (3)
Al2	0.0181 (4)	0.0077 (4)	0.0228 (4)	−0.0012 (3)	0.0057 (3)	0.0011 (3)
O1	0.0230 (8)	0.0260 (8)	0.0422 (9)	0.0011 (6)	0.0183 (7)	0.0042 (7)
O2	0.0246 (8)	0.0143 (7)	0.0356 (8)	0.0023 (6)	0.0145 (7)	0.0064 (6)
O3	0.0154 (7)	0.0090 (6)	0.0255 (7)	0.0000 (5)	0.0044 (6)	0.0021 (5)
O4	0.0286 (8)	0.0114 (7)	0.0276 (8)	−0.0017 (6)	0.0002 (6)	0.0026 (6)
O5	0.0277 (8)	0.0116 (7)	0.0266 (7)	−0.0010 (6)	−0.0002 (6)	0.0015 (6)
O6	0.0239 (8)	0.0132 (7)	0.0337 (8)	−0.0031 (6)	0.0132 (6)	−0.0008 (6)
C1	0.0322 (13)	0.0359 (13)	0.0244 (11)	−0.0011 (10)	0.0053 (9)	0.0013 (9)
O7	0.078 (6)	0.0363 (14)	0.018 (4)	−0.010 (3)	0.017 (3)	−0.003 (2)
C2	0.017 (4)	0.0316 (15)	0.060 (5)	−0.003 (2)	0.007 (2)	0.002 (3)
C2A	0.017 (4)	0.0316 (15)	0.060 (5)	−0.003 (2)	0.007 (2)	0.002 (3)
O7A	0.078 (6)	0.0363 (14)	0.018 (4)	−0.010 (3)	0.017 (3)	−0.003 (2)

Geometric parameters (Å, º) top

S1—O1	1.4324 (16)	Al2—O3	1.8411 (13)
S1—O6	1.4749 (15)	Al2—O3ⁱⁱ	1.8411 (13)
S1—O2	1.4790 (15)	Al2—O4ⁱⁱ	1.9037 (14)
S1—C1	1.753 (2)	Al2—O4	1.9037 (14)
S2—O7A	1.38 (3)	Al2—O6	1.9315 (15)
S2—O7	1.444 (10)	Al2—O6ⁱⁱ	1.9315 (15)
S2—O4	1.4691 (15)	O3—H3	0.941 (10)
S2—O5	1.4696 (15)	C1—H1A	0.9600
S2—C2A	1.59 (2)	C1—H1B	0.9600
S2—C2	1.828 (14)	C1—H1C	0.9600
Al1—O3	1.8407 (13)	C2—H2A	0.9600
Al1—O3ⁱ	1.8407 (13)	C2—H2B	0.9600
Al1—O5	1.9056 (14)	C2—H2C	0.9600
Al1—O5ⁱ	1.9056 (14)	C2A—H2AA	0.9600
Al1—O2ⁱⁱ	1.9259 (15)	C2A—H2AB	0.9600
Al1—O2ⁱⁱⁱ	1.9259 (15)	C2A—H2AC	0.9600

O1—S1—O6	112.13 (9)	O3ⁱⁱ—Al2—O4	88.31 (6)
O1—S1—O2	111.68 (10)	O4ⁱⁱ—Al2—O4	180.0
O6—S1—O2	110.27 (9)	O3—Al2—O6	88.99 (6)
O1—S1—C1	108.41 (11)	O3ⁱⁱ—Al2—O6	91.01 (6)
O6—S1—C1	107.00 (11)	O4ⁱⁱ—Al2—O6	89.59 (7)
O2—S1—C1	107.08 (11)	O4—Al2—O6	90.41 (7)
O7A—S2—O4	108.2 (11)	O3—Al2—O6ⁱⁱ	91.01 (6)
O7—S2—O4	114.4 (5)	O3ⁱⁱ—Al2—O6ⁱⁱ	88.99 (6)
O7A—S2—O5	106.5 (9)	O4ⁱⁱ—Al2—O6ⁱⁱ	90.41 (7)
O7—S2—O5	115.1 (5)	O4—Al2—O6ⁱⁱ	89.59 (7)
O4—S2—O5	110.97 (9)	O6—Al2—O6ⁱⁱ	180.0
O7A—S2—C2A	112.1 (11)	S1—O2—Al1^iv	132.00 (10)
O4—S2—C2A	110.1 (11)	Al1—O3—Al2	134.34 (8)
O5—S2—C2A	108.8 (10)	Al1—O3—H3	113.1 (8)
O7—S2—C2	107.9 (5)	Al2—O3—H3	112.3 (8)
O4—S2—C2	103.3 (4)	S2—O4—Al2	138.91 (9)
O5—S2—C2	103.9 (4)	S2—O5—Al1	138.67 (9)
O3—Al1—O3ⁱ	180.0	S1—O6—Al2	131.92 (9)
O3—Al1—O5	91.67 (6)	S1—C1—H1A	109.5
O3ⁱ—Al1—O5	88.33 (6)	S1—C1—H1B	109.5
O3—Al1—O5ⁱ	88.33 (6)	H1A—C1—H1B	109.5
O3ⁱ—Al1—O5ⁱ	91.67 (6)	S1—C1—H1C	109.5
O5—Al1—O5ⁱ	180.0	H1A—C1—H1C	109.5
O3—Al1—O2ⁱⁱ	90.97 (6)	H1B—C1—H1C	109.5
O3ⁱ—Al1—O2ⁱⁱ	89.03 (6)	S2—C2—H2A	109.5
O5—Al1—O2ⁱⁱ	89.78 (7)	S2—C2—H2B	109.5
O5ⁱ—Al1—O2ⁱⁱ	90.22 (7)	H2A—C2—H2B	109.5
O3—Al1—O2ⁱⁱⁱ	89.03 (6)	S2—C2—H2C	109.5
O3ⁱ—Al1—O2ⁱⁱⁱ	90.98 (6)	H2A—C2—H2C	109.5
O5—Al1—O2ⁱⁱⁱ	90.22 (7)	H2B—C2—H2C	109.5
O5ⁱ—Al1—O2ⁱⁱⁱ	89.78 (7)	S2—C2A—H2AA	109.5
O2ⁱⁱ—Al1—O2ⁱⁱⁱ	180.0	S2—C2A—H2AB	109.5
O3—Al2—O3ⁱⁱ	180.0	H2AA—C2A—H2AB	109.5
O3—Al2—O4ⁱⁱ	88.31 (6)	S2—C2A—H2AC	109.5
O3ⁱⁱ—Al2—O4ⁱⁱ	91.69 (6)	H2AA—C2A—H2AC	109.5
O3—Al2—O4	91.69 (6)	H2AB—C2A—H2AC	109.5

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z; (iv) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

H-bonding distances refer to the major residue.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O7^v	0.96	2.62	3.304 (15)	129
C2—H2B···O7	0.96	2.72	3.641 (16)	162
O3—H3···O1^vi	0.94 (1)	1.87 (1)	2.802 (3)	171 (2)

Symmetry codes: (v) −x+1, −y+1, −z+2; (vi) −x, −y+1, −z+1.

Funding information

EAG and PSH thank the Welch Foundation (grant E-1457) for their support.

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