Poly[3-methyl­pyridinium [(μ2-di­hydrogen phosphito)bis(μ3-hydrogen phosphito)dizinc]]

Love-Jennings, J.G.; McKay, A.P.; Cordes, D.B.; Harrison, W.T.A.

doi:10.1107/S2414314624003456

metal-organic compounds

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ISSN: 2414-3146

Volume 9| Part 4| April 2024| x240345

https://doi.org/10.1107/S2414314624003456

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Poly[3-methylpyridinium [(μ₂-dihydrogen phosphito)bis(μ₃-hydrogen phosphito)dizinc]]

Jago G. Love-Jennings,^a Aidan P. McKay,^b David B. Cordes ^b and William T. A. Harrison ^a ^*

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, United Kingdom, and ^bEaStCHEM, School of Chemistry, University of St Andrews, St Andrews KY16 9ST, Scotland, United Kingdom
^*Correspondence e-mail: w.harrison@abdn.ac.uk

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 17 April 2024; accepted 18 April 2024; online 26 April 2024)

In the title compound, {(C₆H₈N)[Zn₂(HPO₃)₂(H₂PO₃)]}_n, the constituent ZnO₄, HPO₃ and H₂PO₃ polyhedra of the inorganic component are linked into (010) sheets by Zn—O—P bonds (mean angle = 134.4°) and the layers are reinforced by O—H⋯O hydrogen bonds. The protonated templates are anchored to the inorganic sheets via bifurcated N—H⋯(O,O) hydrogen bonds.

Keywords: crystal structure; zincophosphite; layered structure; bifurcated hydrogen bond.

CCDC reference: 2349240

Structure description

The family of zincophosphite (ZnPO) networks templated or ligated by organic species now encompasses well over 200 crystal structures in the Cambridge Structural Database (CSD; Groom et al., 2016 ). In continuation of our ongoing studies of these systems (Holmes et al., 2018 ; Wark et al., 2023 ), we describe the synthesis and structure of the title compound, {(C₆H₈N)[Zn₂(HPO₃)₂(H₂PO₃)]}_n, (I), where C₆H₈N⁺ is the 3-picolinium (or 3-methylpyridinium) cation.

The asymmetric unit of (I) (Fig. 1), which crystallizes in the triclinic space group P $[\overline{1}]$ , consists of two Zn²⁺ ions, two [HPO₃]²⁻ hydrogen phosphite anions, one [H₂PO₃]⁻ dihydrogen phosphite anion and one C₇H₈N⁺ cation. The zinc coordination polyhedra are ZnO₄ tetrahedra, with mean Zn—O separations of 1.934 and 1.942 Å for Zn1 and Zn2, respectively. The spread of bond angles about the metal ions [100.45 (13)–114.37 (14)° for Zn1 and 102.86 (14)–112.73 (14)° for Zn2] indicate modest degrees of distortion, with τ₄′ values (Okuniewski et al., 2015 ) of 0.95 (Zn1) and 0.96 (Zn2), where a value of 1.00 corresponds to a regular tetrahedron. The [HPO₃]²⁻ groups adopt their usual tetrahedral (including the H atom) or pseudo-pyramidal (excluding H) shape and the mean P—O separations are 1.506 Å for P1 and 1.516 Å for P2. The O—P—O bond angles around P1 show a larger than typical range of 107.52 (19)–114.3 (2)°, with the smallest O1—P1—O2 angle associated with the bifurcated hydrogen bond from the protonated template (Fig. 1), whereas the P2 bond angles are tightly clustered [112.38 (19)–112.74 (18)°]. The [H₂PO₃]⁻ dihydrogen phosphite group containing atom P3 includes a notably longer vertex [P3—O9 = 1.543 (3) Å] to the protonated O atom. Apart from O9, each O atom in (I) is bonded to one Zn and one P atom: the Zn—O—P bond angles vary from 128.89 (18) to 138.6 (2)°, with a mean of 134.4°, which is typical for this class of material (Wark et al., 2023). The geometrical parameters for the organic cation are as expected (e.g. Sivakumar et al., 2016 ).

Figure 1
The asymmetric unit of (I), expanded to show the complete zinc-atom coordination spheres, showing 50% displacement ellipsoids. [Symmetry codes: (i) −x, −y + 1, −z; (ii) x − 1, y, z; (iii) −x, −y + 1, −z + 1; (iv) −x + 1, −y + 1, −z + 1.] Hydrogen bonds are indicated by double-dashed lines.

In the extended structure of (I), the constituent ZnO₄, HPO₃ and H₂PO₃ polyhedra are linked by Zn—O—P bonds into infinite (010) sheets (Fig. 2). Polyhedral 4- and 8-rings are present and the zinc and phosphorus nodes strictly alternate. The most distinctive building unit is a centrosymmetric 8-ring incorporating two bifurcated 4-rings reinforced by a pair of O9—H1O⋯O4 intra-layer hydrogen bonds (Fig. 3). These are linked by 4-rings involving the Zn2—O6—P2 bonds into [100] chains and crosslinked in the [001] direction by Zn1—O2—P1 bonds into the (010) sheets. The template interacts with the inorganic layers via an unusual bifurcated N1—H1B⋯(O1,O2) link (Fig. 1): the vast majority of template-to-framework hydrogen bonds are associated with a single acceptor O atom. Some weak nonclassical C—H⋯O interactions occur, as listed in Table 1. As is normal, the P—H unit does not participate in hydrogen bonding (Katinaitė & Harrison, 2017 ). There are no aromatic π–π stacking interactions in (I)>, the shortest centroid–centroid separation being greater than 5.68 Å, and inter-layer cohesion must be largely due to van der Waals forces.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1	0.88	2.20	2.992 (6)	150
N1—H1B⋯O2	0.88	2.24	2.947 (6)	138
O9—H1O⋯O4ⁱ	0.85	1.78	2.630 (4)	177
C1—H1A⋯O5ⁱⁱ	0.95	2.34	3.285 (6)	175
C5—H5⋯O4ⁱⁱⁱ	0.95	2.59	3.368 (6)	140
C5—H5⋯O6ⁱⁱⁱ	0.95	2.52	3.300 (7)	140
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 2
The unit-cell packing in (I), viewed down [100]. Hydrogen bonds are shown as dashed lines.

Figure 3
Detail of an infinite (010) polyhedral layer in (I), showing the bifurcated 8-ring reinforced by pairwise O—H⋯O hydrogen bonds (double-dashed lines). [Symmetry code: (i) x − 1, y, z.]

A survey of the Cambridge Structural Database (Groom et al., 2016; updated to April 2024) revealed 217 crystal structures containing zinc cations and hydrogen phosphite anions based on a search for a Zn—O—P—H fragment. Structures containing zinc and a dihydrogen phosphite unit are uncommon with just three examples found, viz. bis(μ₂-hydrogen phosphito-O,O′)(hydrogen phosphito-O)(2,2′-bipyridyl)zinc(II) (CSD refocde BEJHUU; Lin et al., 2003 ), bis(μ₂-hydrogen phosphito-O,O′)(hydrogen phosphito-O)(4,4′-dimethyl-2,2′-bipyridyl)dizinc(II) (GICCOL; Lin et al., 2007 ) and catena-[1-azonio-4-azabicyclo[2.2.2]octane tris(μ₃-hydrogen phosphito)(μ₂-hydrogen phosphito)(1,4-diazabicyclo[2.2.2]octane-N)trizinc(II)] (XIZJEW; Liu et al., 2008 ). Compounds BEJHUU and GICCOL are closely related `zero-dimensional' bimetallic clusters with bulky chelating ligands, while XIZJEW features the organic species acting both as a ligand (via a Zn—N bond) and a protonated template.

Synthesis and crystallization

Compound (I) was prepared by mixing 0.41 g of ZnO, 0.82 g of H₃PO₃ and 0.47 g of 3-picoline (Zn:P:template molar ratio ≃ 1:2:1), which were placed in a 50 ml polypropylene bottle with 20 ml of water and shaken well to result in a white slurry. The bottle was placed in a 353 K oven for 48 h and then removed and allowed to cool to room temperature over about 2 h. The solids were recovered by vacuum filtration to result in a mass of rod-like colourless crystals accompanied by some white solids. IR (diamond window): 3400–2800 cm⁻¹ (O—H, N—H stretch), 2450 cm⁻¹ (P—H stretch; Ma et al., 2007 ).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The O-bound H atom was located in a difference map and refined as riding in its as-found relative location. The P-, N- and C-bound H atoms were located geometrically (P—H = 1.32, N—H = 0.88 and C—H = 0.95–0.98 Å) and refined as riding atoms. The methyl group was allowed to rotate, but not to tip, to best fit the electron density. The constraint U_iso(H) = 1.2U_eq(N, O or P) or 1.5U_eq(methyl C) was applied in all cases. Two peaks greater than 1 e Å⁻³ were found in the final difference map for (I) in the vicinity of the Zn atoms, but they did not correspond to plausible chemical features.

Table 2
Experimental details

Crystal data
Chemical formula	(C₆H₈N)[Zn₂(HPO₃)₂(H₂PO₃)]
M_r	465.82
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	8.8428 (5), 9.2779 (6), 9.9343 (4)
α, β, γ (°)	79.126 (4), 82.732 (4), 67.279 (6)
V (Å³)	736.99 (8)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	3.62
Crystal size (mm)	0.12 × 0.03 × 0.01

Data collection
Diffractometer	Rigaku XtaLAB P200K
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2024 )
T_min, T_max	0.850, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14787, 3442, 2491
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.695

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.134, 1.02
No. of reflections	3442
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.43, −0.89
Computer programs: CrysAlis PRO (Rigaku OD, 2024), SHELXT (Sheldrick, 2015a ), SHELXL2019 (Sheldrick, 2015b ), ORTEP-3 (Farrugia, 2012 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2349240

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314624003456/tk4104sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624003456/tk4104Isup2.hkl

checkCIF report

Computing details top

Poly[3-methylpyridinium [(µ₂-dihydrogen phosphito)bis(µ₃-hydrogen phosphito)dizinc]] top

Crystal data top

(C₆H₈N)[Zn₂(HPO₃)₂(H₂PO₃)]	Z = 2
M_r = 465.82	F(000) = 464
Triclinic, P1	D_x = 2.099 Mg m⁻³
a = 8.8428 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2779 (6) Å	Cell parameters from 6732 reflections
c = 9.9343 (4) Å	θ = 2.1–29.4°
α = 79.126 (4)°	µ = 3.62 mm⁻¹
β = 82.732 (4)°	T = 173 K
γ = 67.279 (6)°	Bar, colourless
V = 736.99 (8) Å³	0.12 × 0.03 × 0.01 mm

Data collection top

Rigaku XtaLAB P200K diffractometer	2491 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.066
ω scans	θ_max = 29.6°, θ_min = 2.1°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2024)	h = −11→12
T_min = 0.850, T_max = 1.000	k = −12→12
14787 measured reflections	l = −13→12
3442 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.134	w = 1/[σ²(F_o²) + (0.0819P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3442 reflections	Δρ_max = 1.43 e Å⁻³
191 parameters	Δρ_min = −0.89 e Å⁻³
0 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
Zn1	−0.15526 (6)	0.48844 (6)	0.17897 (5)	0.02409 (17)
Zn2	0.24043 (6)	0.62310 (6)	0.40311 (5)	0.02507 (18)
P1	0.12600 (13)	0.63180 (14)	0.10765 (11)	0.0231 (3)
H1	0.096928	0.778451	0.046688	0.028*
P2	0.57579 (14)	0.67732 (15)	0.38453 (12)	0.0249 (3)
H2	0.585406	0.817529	0.343455	0.030*
P3	−0.05587 (14)	0.79747 (15)	0.60236 (12)	0.0268 (3)
H3	−0.092835	0.950694	0.595471	0.032*
O1	0.2488 (4)	0.5969 (4)	0.2136 (3)	0.0339 (8)
O2	0.2100 (4)	0.5268 (4)	−0.0006 (3)	0.0354 (8)
O3	−0.0360 (4)	0.6260 (4)	0.1659 (4)	0.0336 (8)
O4	0.6946 (4)	0.5953 (4)	0.4998 (3)	0.0292 (7)
O5	0.6265 (4)	0.5929 (4)	0.2609 (3)	0.0347 (8)
O6	0.3994 (4)	0.7076 (4)	0.4335 (3)	0.0296 (7)
O7	0.0241 (4)	0.7586 (4)	0.4650 (3)	0.0374 (8)
O8	0.0481 (4)	0.7208 (4)	0.7225 (4)	0.0386 (8)
O9	−0.2216 (4)	0.7747 (5)	0.6275 (4)	0.0495 (10)
H1O	−0.248833	0.714280	0.588686	0.059*
C1	0.5538 (6)	0.2241 (8)	0.0263 (6)	0.0480 (15)
H1A	0.501366	0.270784	−0.057545	0.058*
C2	0.6748 (6)	0.0729 (7)	0.0373 (5)	0.0398 (13)
C3	0.7424 (6)	0.0139 (6)	0.1628 (5)	0.0365 (12)
H3A	0.822779	−0.090250	0.177280	0.044*
C4	0.6958 (7)	0.1029 (7)	0.2676 (5)	0.0424 (13)
H4	0.745714	0.061680	0.352982	0.051*
C5	0.5791 (7)	0.2484 (7)	0.2484 (6)	0.0462 (15)
H5	0.546317	0.311069	0.320035	0.055*
C6	0.7301 (10)	−0.0189 (10)	−0.0812 (7)	0.076 (2)
H6A	0.645693	0.024450	−0.148650	0.113*
H6B	0.747583	−0.130136	−0.047771	0.113*
H6C	0.832992	−0.010706	−0.124466	0.113*
N1	0.5110 (5)	0.3034 (5)	0.1310 (6)	0.0501 (13)
H1B	0.432689	0.397922	0.121074	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0207 (3)	0.0390 (3)	0.0137 (3)	−0.0117 (2)	0.0011 (2)	−0.0071 (2)
Zn2	0.0217 (3)	0.0384 (3)	0.0167 (3)	−0.0109 (2)	0.0002 (2)	−0.0094 (2)
P1	0.0208 (6)	0.0313 (6)	0.0170 (6)	−0.0083 (5)	−0.0011 (4)	−0.0064 (5)
P2	0.0231 (6)	0.0367 (7)	0.0183 (6)	−0.0141 (5)	−0.0002 (5)	−0.0067 (5)
P3	0.0226 (6)	0.0356 (7)	0.0231 (6)	−0.0106 (5)	0.0001 (5)	−0.0079 (5)
O1	0.0318 (18)	0.056 (2)	0.0185 (17)	−0.0173 (16)	−0.0047 (14)	−0.0113 (15)
O2	0.0284 (17)	0.058 (2)	0.0178 (17)	−0.0078 (16)	−0.0033 (14)	−0.0176 (16)
O3	0.0247 (17)	0.0344 (18)	0.044 (2)	−0.0114 (15)	0.0067 (15)	−0.0161 (16)
O4	0.0279 (17)	0.0387 (19)	0.0237 (17)	−0.0145 (15)	−0.0031 (14)	−0.0055 (14)
O5	0.0205 (16)	0.066 (2)	0.0187 (16)	−0.0148 (16)	0.0025 (13)	−0.0153 (16)
O6	0.0215 (16)	0.046 (2)	0.0266 (17)	−0.0132 (15)	0.0041 (13)	−0.0192 (15)
O7	0.0236 (17)	0.054 (2)	0.0286 (19)	−0.0059 (16)	0.0002 (14)	−0.0126 (16)
O8	0.045 (2)	0.043 (2)	0.0290 (19)	−0.0170 (17)	−0.0059 (16)	−0.0032 (16)
O9	0.034 (2)	0.080 (3)	0.052 (2)	−0.033 (2)	0.0135 (17)	−0.038 (2)
C1	0.026 (3)	0.069 (4)	0.040 (3)	−0.017 (3)	−0.007 (2)	0.016 (3)
C2	0.036 (3)	0.057 (4)	0.033 (3)	−0.025 (3)	0.008 (2)	−0.014 (3)
C3	0.025 (2)	0.033 (3)	0.043 (3)	−0.007 (2)	0.000 (2)	0.005 (2)
C4	0.046 (3)	0.057 (4)	0.029 (3)	−0.029 (3)	−0.004 (2)	0.005 (3)
C5	0.054 (4)	0.052 (4)	0.044 (4)	−0.034 (3)	0.029 (3)	−0.021 (3)
C6	0.088 (5)	0.115 (6)	0.053 (4)	−0.062 (5)	0.024 (4)	−0.047 (4)
N1	0.030 (2)	0.033 (2)	0.066 (4)	0.000 (2)	0.024 (2)	−0.001 (2)

Geometric parameters (Å, º) top

Zn1—O3	1.923 (3)	P3—O9	1.543 (3)
Zn1—O8ⁱ	1.930 (4)	P3—H3	1.3200
Zn1—O2ⁱⁱ	1.939 (3)	O9—H1O	0.8542
Zn1—O5ⁱⁱⁱ	1.945 (3)	C1—N1	1.318 (8)
Zn2—O6	1.931 (3)	C1—C2	1.392 (8)
Zn2—O1	1.931 (3)	C1—H1A	0.9500
Zn2—O7	1.938 (3)	C2—C3	1.374 (8)
Zn2—O4^iv	1.967 (3)	C2—C6	1.504 (8)
P1—O3	1.493 (3)	C3—C4	1.375 (8)
P1—O1	1.511 (3)	C3—H3A	0.9500
P1—O2	1.513 (3)	C4—C5	1.341 (8)
P1—H1	1.3200	C4—H4	0.9500
P2—O6	1.507 (3)	C5—N1	1.304 (8)
P2—O5	1.509 (3)	C5—H5	0.9500
P2—O4	1.533 (3)	C6—H6A	0.9800
P2—H2	1.3200	C6—H6B	0.9800
P3—O8	1.492 (4)	C6—H6C	0.9800
P3—O7	1.496 (3)	N1—H1B	0.8800

O3—Zn1—O8ⁱ	114.37 (14)	P1—O3—Zn1	138.2 (2)
O3—Zn1—O2ⁱⁱ	112.19 (15)	P2—O4—Zn2^iv	128.89 (18)
O8ⁱ—Zn1—O2ⁱⁱ	109.65 (15)	P2—O5—Zn1^v	129.60 (18)
O3—Zn1—O5ⁱⁱⁱ	107.88 (14)	P2—O6—Zn2	134.27 (19)
O8ⁱ—Zn1—O5ⁱⁱⁱ	111.45 (15)	P3—O7—Zn2	134.0 (2)
O2ⁱⁱ—Zn1—O5ⁱⁱⁱ	100.45 (13)	P3—O8—Zn1ⁱ	138.6 (2)
O6—Zn2—O1	111.84 (14)	P3—O9—H1O	125.5
O6—Zn2—O7	108.97 (14)	N1—C1—C2	120.7 (5)
O1—Zn2—O7	112.00 (13)	N1—C1—H1A	119.6
O6—Zn2—O4^iv	108.32 (13)	C2—C1—H1A	119.6
O1—Zn2—O4^iv	102.86 (14)	C3—C2—C1	115.7 (5)
O7—Zn2—O4^iv	112.73 (14)	C3—C2—C6	122.1 (6)
O3—P1—O1	114.3 (2)	C1—C2—C6	122.1 (6)
O3—P1—O2	115.04 (19)	C2—C3—C4	121.2 (5)
O1—P1—O2	107.52 (19)	C2—C3—H3A	119.4
O3—P1—H1	106.4	C4—C3—H3A	119.4
O1—P1—H1	106.4	C5—C4—C3	119.5 (5)
O2—P1—H1	106.4	C5—C4—H4	120.3
O6—P2—O5	112.30 (17)	C3—C4—H4	120.3
O6—P2—O4	112.74 (18)	N1—C5—C4	119.7 (5)
O5—P2—O4	112.38 (19)	N1—C5—H5	120.2
O6—P2—H2	106.3	C4—C5—H5	120.2
O5—P2—H2	106.3	C2—C6—H6A	109.5
O4—P2—H2	106.3	C2—C6—H6B	109.5
O8—P3—O7	116.5 (2)	H6A—C6—H6B	109.5
O8—P3—O9	111.5 (2)	C2—C6—H6C	109.5
O7—P3—O9	111.4 (2)	H6A—C6—H6C	109.5
O8—P3—H3	105.5	H6B—C6—H6C	109.5
O7—P3—H3	105.5	C5—N1—C1	123.2 (5)
O9—P3—H3	105.5	C5—N1—H1B	118.4
P1—O1—Zn2	136.5 (2)	C1—N1—H1B	118.4
P1—O2—Zn1ⁱⁱ	135.1 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.88	2.20	2.992 (6)	150
N1—H1B···O2	0.88	2.24	2.947 (6)	138
O9—H1O···O4ⁱⁱⁱ	0.85	1.78	2.630 (4)	177
C1—H1A···O5^vi	0.95	2.34	3.285 (6)	175
C5—H5···O4^iv	0.95	2.59	3.368 (6)	140
C5—H5···O6^iv	0.95	2.52	3.300 (7)	140

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

References

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