Poly[1,4-bis­(ammonio­meth­yl)cyclo­hexane [di-μ-chlorido-dichloridoplumbate(II)]]

Rayner, M.K.; Billing, D.G.

doi:10.1107/S1600536810016818

metal-organic compounds

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Poly[1,4-bis(ammoniomethyl)cyclohexane [di-μ-chlorido-dichloridoplumbate(II)]]

Matthew Kyle Rayner ^a and David Gordon Billing ^a ^*

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO Wits 2050, South Africa
^*Correspondence e-mail: david.billing@wits.ac.za

(Received 27 April 2010; accepted 7 May 2010; online 15 May 2010)

The title compound, {(C₈H₂₀N₂)[PbCl₄]}_n, crystallizes as an layered inorganic–organic hybrid perovskite-type structure. Corner-sharing PbCl₆ octahedra extend parallel to the ac plane. Adjacent layers are staggered relative to one another, with diammonium cations separating these layers. The cations exhibit $[\overline{1}]$ symmetry and interact with the inorganic sheets via N—H⋯Cl hydrogen bonding in the right-angled halogen sub-type of the terminal halide hydrogen-bonding motif.

Related literature

Similar structures have been reported by Billing & Lemmerer (2006 ) and Dobrzycki & Woźniak (2009 ). Structure–properties relation experiments have been performed by Mitzi et al. (2001 ). For hydrogen-bonding nomenclature for inorganic–organic hybrids, see: Mitzi (1999 ). For the bromido- and iodidoplumbate(II) analogues of the title compound, see: Rayner & Billing (2010a ,b ).

Experimental

Crystal data

(C₈H₂₀N₂)[PbCl₄]
M_r = 493.25
Orthorhombic, P n m a
a = 7.7990 (2) Å
b = 24.0666 (6) Å
c = 7.9348 (2) Å
V = 1489.33 (7) Å³
Z = 4
Mo Kα radiation
μ = 12.02 mm⁻¹
T = 173 K
0.54 × 0.41 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: integration (XPREP; Bruker, 2005 ) T_min = 0.032, T_max = 0.685
13290 measured reflections
1850 independent reflections
1654 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.067
S = 1.16
1850 reflections
73 parameters
H-atom parameters constrained
Δρ_max = 1.47 e Å⁻³
Δρ_min = −3.53 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb1—Cl3ⁱ	2.834 (2)
Pb1—Cl1ⁱⁱ	2.8723 (15)
Pb1—Cl2ⁱⁱⁱ	2.900 (2)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z]$ ; (iii) $[x+{\script{1\over 2}}, y, -z+{\script{5\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯Cl3^iv	0.91	2.40	3.249 (5)	156
N1—H1D⋯Cl1^v	0.91	2.44	3.196 (6)	141
N1—H1E⋯Cl1ⁱⁱⁱ	0.91	2.39	3.212 (5)	150
N1—H1E⋯Cl2ⁱⁱⁱ	0.91	2.84	3.337 (5)	115
Symmetry codes: (iii) $[x+{\script{1\over 2}}, y, -z+{\script{5\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (v) x+1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810016818/wm2339sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016818/wm2339Isup2.hkl

checkCIF report

Comment top

Inorganic-organic hybrid compounds have been investigated for their semiconduting and electronic properties (Mitzi et al., 2001). For literature regarding hydrogen bonding nomenclature for inorganic-organic hybrids, see: Mitzi (1999). The title structure (Fig. 1) is one of three 2-dimensional hybrid structures that we have synthesized encorporating this diammonium cation. The structures differ in terms of their halogen ligands, which include chloride (presented here), bromide (Rayner & Billing, 2010a) and iodide (Rayner & Billing, 2010b). The bromide and iodide hybrids crystallize in the monoclinic system with space group P2₁/c while the chloride hybrid crystallizes in the orthorhombic, Pnma system.

In the title structure the lead-chloride octahedra from alternate layers that are staggered relative to one another (Fig. 2). In all three structures only the trans form of the cation has been observed, giving the cation 1 symmetry (Fig. 3). The ammonium cations interact with the inorganic layer via N—H···X (X = Br, I and Cl) hydrogen bonding in the right-angled halogen subtype of the terminal halide hydrogen bonding motif (Mitzi, 1999). Similar inorganic-organic hybrid structures have been reported (Billing & Lemmerer, 2006; Dobrzycki & Woźniak, 2009), however very few hybrids encorporating diammonium cations have been synthesized.

Related literature top

Similar structures have been reported by Billing & Lemmerer (2006) and Dobrzycki & Woźniak (2009). Structure–properties relation experiments have been performed by Mitzi et al. (2001). For hydrogen-bonding nomenclature for inorganic–organic hybrids, see: Mitzi (1999). For the bromido- and iodidoplumbate(II) analogues of the title compound, see: Rayner & Billing (2010a,b)

Experimental top

A mixture of 0.052 g (0.19 mmol) PbCl₂ and 0.030 g (0.21 mmol) 1,4-bis-(aminomethyl)-cyclohexane (mixture of isomers) was dissolved in 5 ml HCl at 383 K and slow cooled at a rate of 0.069 K/min to yield colourless, plate-shaped single crystals suitable for X-ray analysis.

Structure description top

Similar structures have been reported by Billing & Lemmerer (2006) and Dobrzycki & Woźniak (2009). Structure–properties relation experiments have been performed by Mitzi et al. (2001). For hydrogen-bonding nomenclature for inorganic–organic hybrids, see: Mitzi (1999). For the bromido- and iodidoplumbate(II) analogues of the title compound, see: Rayner & Billing (2010a,b)

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound with atom labels. Displacement ellipsoids were drawn at the 50% probability level. Symmetry codes: (a) -1/2+x, 1/2-y, 3/2-z (b) 1/2+x, 1/2-y, 1/2-z (c) x, 1/2-y, z (d) 1-x, -y, -z.
	Fig. 2. Packing diagram viewed along the b axis. Hydrogen bonds are drawn as dashed red lines.
	Fig. 3. Packing diagram viewed along the c axis. Hydrogen bonds are drawn as dashed red lines.

Poly[1,4-bis(ammoniomethyl)cyclohexane [di-µ-chlorido-dichloridoplumbate(II)]] top

Crystal data top

(C₈H₂₀N₂)[PbCl₄]	F(000) = 928
M_r = 493.25	D_x = 2.200 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 6650 reflections
a = 7.7990 (2) Å	θ = 2.7–28.3°
b = 24.0666 (6) Å	µ = 12.02 mm⁻¹
c = 7.9348 (2) Å	T = 173 K
V = 1489.33 (7) Å³	Plate, colourless
Z = 4	0.54 × 0.41 × 0.04 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1850 independent reflections
Radiation source: fine-focus sealed tube	1654 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 28.0°, θ_min = 1.7°
Absorption correction: integration (XPREP; Bruker, 2005)	h = −10→10
T_min = 0.032, T_max = 0.685	k = −31→31
13290 measured reflections	l = −10→10

Refinement top

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: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.003P)² + 19.9694P] where P = (F_o² + 2F_c²)/3
1850 reflections	(Δ/σ)_max = 0.007
73 parameters	Δρ_max = 1.47 e Å⁻³
0 restraints	Δρ_min = −3.53 e Å⁻³

Crystal data top

(C₈H₂₀N₂)[PbCl₄]	V = 1489.33 (7) Å³
M_r = 493.25	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 7.7990 (2) Å	µ = 12.02 mm⁻¹
b = 24.0666 (6) Å	T = 173 K
c = 7.9348 (2) Å	0.54 × 0.41 × 0.04 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1850 independent reflections
Absorption correction: integration (XPREP; Bruker, 2005)	1654 reflections with I > 2σ(I)
T_min = 0.032, T_max = 0.685	R_int = 0.049
13290 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.003P)² + 19.9694P] where P = (F_o² + 2F_c²)/3
1850 reflections	Δρ_max = 1.47 e Å⁻³
73 parameters	Δρ_min = −3.53 e Å⁻³

Special details top

Experimental. Numerical intergration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2005)

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. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5490 (8)	0.6188 (2)	0.9551 (8)	0.0201 (12)
H1A	0.6135	0.6159	0.8480	0.024*
H1B	0.4429	0.6401	0.9326	0.024*
C2	0.5016 (8)	0.5612 (2)	1.0147 (8)	0.0201 (12)
H2	0.4256	0.5654	1.1154	0.024*
C3	0.3984 (9)	0.5318 (3)	0.8783 (8)	0.0256 (13)
H3A	0.4683	0.5293	0.7744	0.031*
H3B	0.2948	0.5540	0.8521	0.031*
C4	0.6555 (8)	0.5265 (3)	1.0676 (8)	0.0239 (13)
H4A	0.7150	0.5451	1.1623	0.029*
H4B	0.7369	0.5238	0.9723	0.029*
N1	0.6553 (7)	0.6496 (2)	1.0812 (7)	0.0213 (11)
H1C	0.6816	0.6838	1.0400	0.032*
H1D	0.7537	0.6303	1.1013	0.032*
H1E	0.5954	0.6532	1.1789	0.032*
Cl1	0.05791 (19)	0.63163 (6)	1.02923 (19)	0.0229 (3)
Cl2	−0.1125 (3)	0.7500	1.2974 (2)	0.0194 (4)
Cl3	0.2609 (3)	0.7500	0.6719 (3)	0.0238 (4)
Pb1	0.08434 (4)	0.7500	0.99093 (4)	0.01374 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.019 (3)	0.018 (3)	0.023 (3)	0.002 (2)	−0.002 (2)	0.001 (2)
C2	0.020 (3)	0.021 (3)	0.019 (3)	0.000 (2)	−0.003 (2)	−0.001 (3)
C3	0.031 (4)	0.020 (3)	0.026 (3)	−0.004 (3)	−0.009 (3)	0.000 (2)
C4	0.023 (3)	0.021 (3)	0.028 (3)	−0.004 (3)	−0.005 (3)	−0.001 (3)
N1	0.023 (3)	0.018 (2)	0.023 (2)	−0.003 (2)	0.002 (2)	−0.003 (2)
Cl1	0.0202 (7)	0.0229 (7)	0.0257 (7)	0.0021 (5)	0.0001 (6)	−0.0037 (6)
Cl2	0.0170 (10)	0.0221 (9)	0.0192 (9)	0.000	0.0049 (7)	0.000
Cl3	0.0222 (10)	0.0297 (11)	0.0197 (9)	0.000	0.0056 (8)	0.000
Pb1	0.01269 (14)	0.01657 (14)	0.01196 (13)	0.000	0.00002 (12)	0.000

Geometric parameters (Å, º) top

C1—N1	1.495 (8)	C4—H4B	0.9900
C1—C2	1.512 (8)	N1—H1C	0.9100
C1—H1A	0.9900	N1—H1D	0.9100
C1—H1B	0.9900	N1—H1E	0.9100
C2—C3	1.523 (8)	Cl1—Pb1	2.8723 (15)
C2—C4	1.521 (9)	Cl2—Pb1	2.8759 (19)
C2—H2	1.0000	Cl2—Pb1ⁱⁱ	2.9002 (19)
C3—C4ⁱ	1.525 (9)	Cl3—Pb1ⁱⁱⁱ	2.834 (2)
C3—H3A	0.9900	Cl3—Pb1	2.882 (2)
C3—H3B	0.9900	Pb1—Cl3^iv	2.834 (2)
C4—C3ⁱ	1.525 (9)	Pb1—Cl1^v	2.8723 (15)
C4—H4A	0.9900	Pb1—Cl2^vi	2.900 (2)

N1—C1—C2	112.4 (5)	C1—N1—H1C	109.5
N1—C1—H1A	109.1	C1—N1—H1D	109.5
C2—C1—H1A	109.1	H1C—N1—H1D	109.5
N1—C1—H1B	109.1	C1—N1—H1E	109.5
C2—C1—H1B	109.1	H1C—N1—H1E	109.5
H1A—C1—H1B	107.9	H1D—N1—H1E	109.5
C1—C2—C3	109.5 (5)	Pb1—Cl2—Pb1ⁱⁱ	157.64 (8)
C1—C2—C4	113.4 (5)	Pb1ⁱⁱⁱ—Cl3—Pb1	145.68 (9)
C3—C2—C4	111.0 (5)	Cl3^iv—Pb1—Cl1^v	89.10 (3)
C1—C2—H2	107.6	Cl3^iv—Pb1—Cl1	89.10 (3)
C3—C2—H2	107.6	Cl1^v—Pb1—Cl1	165.31 (6)
C4—C2—H2	107.6	Cl3^iv—Pb1—Cl2	84.87 (6)
C2—C3—C4ⁱ	111.8 (5)	Cl1^v—Pb1—Cl2	82.66 (3)
C2—C3—H3A	109.2	Cl1—Pb1—Cl2	82.66 (3)
C4ⁱ—C3—H3A	109.2	Cl3^iv—Pb1—Cl3	91.42 (3)
C2—C3—H3B	109.2	Cl1^v—Pb1—Cl3	97.31 (3)
C4ⁱ—C3—H3B	109.2	Cl1—Pb1—Cl3	97.31 (3)
H3A—C3—H3B	107.9	Cl2—Pb1—Cl3	176.29 (6)
C2—C4—C3ⁱ	111.4 (5)	Cl3^iv—Pb1—Cl2^vi	171.75 (6)
C2—C4—H4A	109.3	Cl1^v—Pb1—Cl2^vi	89.84 (3)
C3ⁱ—C4—H4A	109.3	Cl1—Pb1—Cl2^vi	89.84 (3)
C2—C4—H4B	109.3	Cl2—Pb1—Cl2^vi	86.875 (17)
C3ⁱ—C4—H4B	109.3	Cl3—Pb1—Cl2^vi	96.83 (6)
H4A—C4—H4B	108.0

N1—C1—C2—C3	−178.3 (5)	Pb1ⁱⁱ—Cl2—Pb1—Cl1^v	89.76 (3)
N1—C1—C2—C4	−53.7 (7)	Pb1ⁱⁱ—Cl2—Pb1—Cl1	−89.76 (3)
C1—C2—C3—C4ⁱ	−179.2 (5)	Pb1ⁱⁱ—Cl2—Pb1—Cl2^vi	180.0
C4—C2—C3—C4ⁱ	54.9 (8)	Pb1ⁱⁱⁱ—Cl3—Pb1—Cl3^iv	180.0
C1—C2—C4—C3ⁱ	−178.3 (5)	Pb1ⁱⁱⁱ—Cl3—Pb1—Cl1^v	90.72 (3)
C3—C2—C4—C3ⁱ	−54.6 (8)	Pb1ⁱⁱⁱ—Cl3—Pb1—Cl1	−90.72 (3)
Pb1ⁱⁱ—Cl2—Pb1—Cl3^iv	0.0	Pb1ⁱⁱⁱ—Cl3—Pb1—Cl2^vi	0.0

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x−1/2, y, −z+5/2; (iii) x+1/2, y, −z+3/2; (iv) x−1/2, y, −z+3/2; (v) x, −y+3/2, z; (vi) x+1/2, y, −z+5/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Cl3ⁱⁱⁱ	0.91	2.40	3.249 (5)	156
N1—H1D···Cl1^vii	0.91	2.44	3.196 (6)	141
N1—H1E···Cl1^vi	0.91	2.39	3.212 (5)	150
N1—H1E···Cl2^vi	0.91	2.84	3.337 (5)	115

Symmetry codes: (iii) x+1/2, y, −z+3/2; (vi) x+1/2, y, −z+5/2; (vii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	(C₈H₂₀N₂)[PbCl₄]
M_r	493.25
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	173
a, b, c (Å)	7.7990 (2), 24.0666 (6), 7.9348 (2)
V (Å³)	1489.33 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	12.02
Crystal size (mm)	0.54 × 0.41 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Integration (XPREP; Bruker, 2005)
T_min, T_max	0.032, 0.685
No. of measured, independent and observed [I > 2σ(I)] reflections	13290, 1850, 1654
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.067, 1.16
No. of reflections	1850
No. of parameters	73
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.003P)² + 19.9694P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.47, −3.53

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Pb1—Cl3ⁱ	2.834 (2)	Pb1—Cl2ⁱⁱⁱ	2.900 (2)
Pb1—Cl1ⁱⁱ	2.8723 (15)

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x, −y+3/2, z; (iii) x+1/2, y, −z+5/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Cl3^iv	0.91	2.40	3.249 (5)	156
N1—H1D···Cl1^v	0.91	2.44	3.196 (6)	141
N1—H1E···Cl1ⁱⁱⁱ	0.91	2.39	3.212 (5)	150
N1—H1E···Cl2ⁱⁱⁱ	0.91	2.84	3.337 (5)	115

Symmetry codes: (iii) x+1/2, y, −z+5/2; (iv) x+1/2, y, −z+3/2; (v) x+1, y, z.

Acknowledgements

The University of the Witwatersrand and the National Research Fund (GUN: 2069064) are acknowledged for the funding and infrastructure required to perform the experiment.

References

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Poly[1,4-bis­­(ammonio­meth­yl)cyclo­hexane [di-μ-chlorido-di­chloridoplumbate(II)]]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Poly[1,4-bis(ammoniomethyl)cyclohexane [di-μ-chlorido-dichloridoplumbate(II)]]