Poly[1,4-bis­(ammonio­meth­yl)cyclo­hexane [di-μ-bromido-dibromido­plumbate(II)]]

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

doi:10.1107/S1600536810016806

metal-organic compounds

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Poly[1,4-bis(ammoniomethyl)cyclohexane [di-μ-bromido-dibromidoplumbate(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)[PbBr₄]}_n, crystallizes as an inorganic–organic hybrid with alternating layers of diammonium cations and two-dimensional corner-sharing PbBr₆ octahedra extending parallel to the bc plane, which are eclipsed relative to one another. Both PbBr₆ octahedra and the organic cation exhibit $[\overline{1}]$ symmetry. The cations interact via N—H⋯Br hydrogen bonding in the right-angled halogen sub-type of the terminal halide hydrogen-bonding motif.

Related literature

For hydrogen-bonding nomenclature for inorganic–organic hybrids, see: Mitzi (1999 ). Hybrid structures containing diammonium cations have been synthesized by Dobrzycki & Woźniak (2008 ) and Zhu et al. (2003 ). The semiconducting properties of similar hybrids were demonstrated by Mitzi (2004 ). For the related chloridoplumbate(II), see: Rayner & Billing (2010a ) and for the isotypic iodidoplumbate(II), see: Rayner & Billing (2010b ).

Experimental

Crystal data

(C₈H₂₀N₂)[PbBr₄]
M_r = 671.09
Monoclinic, P 2₁ /c
a = 12.1042 (6) Å
b = 8.1955 (4) Å
c = 8.2160 (4) Å
β = 95.693 (1)°
V = 811.01 (7) Å³
Z = 2
Mo Kα radiation
μ = 20.23 mm⁻¹
T = 173 K
0.20 × 0.14 × 0.02 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: integration (XPREP; Bruker, 2005 ) T_min = 0.091, T_max = 0.656
10495 measured reflections
1966 independent reflections
1742 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.047
S = 0.81
1966 reflections
70 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −2.31 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb1—Br2ⁱ	2.9821 (3)
Pb1—Br2ⁱⁱ	2.9886 (3)
Pb1—Br1ⁱ	3.0054 (4)
Symmetry codes: (i) -x+1, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯Br2ⁱ	0.91	2.54	3.387 (3)	154
N1—H1D⋯Br1ⁱⁱ	0.91	2.57	3.378 (3)	148
N1—H1D⋯Br2ⁱⁱⁱ	0.91	2.94	3.446 (3)	117
N1—H1E⋯Br1	0.91	2.60	3.357 (3)	141
Symmetry codes: (i) -x+1, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y, z+1.

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/S1600536810016806/wm2338sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016806/wm2338Isup2.hkl

checkCIF report

Comment top

Inorganic-organic hybrid materials are of interest due to their electronic and fluorescent properties (Mitzi, 2004). 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 bromide (presented here), chloride (Rayner & Billing, 2010a) and iodide (Rayner & Billing, 2010b). The bromide and iodide hybrids crystallize in the monoclinic crystal system in space group P2₁/c while the chloride compound crystallizes in the orthorhombic Pnma system.

In the title structure the lead atoms in the PbBr₆ octahedra occupy inversion centers, giving the octahedra 1 symmetry. The PbBr₆ octahedra share corners to form layers extending parallel to the bc plane. Octahedra from alternate layers are eclipsed 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). Very few inorganic-organic hybrid structures encorporating diammonium cations have been reported (Dobrzycki & Woźniak, 2008; Zhu et al., 2003). 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).

Related literature top

For hydrogen-bonding nomenclature for inorganic–organic hybrids, see: Mitzi (1999). Hybrid structures containing diammonium cations have been synthesized by Dobrzycki & Woźniak (2008) and Zhu et al. (2003). The semiconducting properties of similar hybrids were demonstrated by Mitzi (2004). For the related chloridoplumbate(II), see: Rayner & Billing (2010a) and for the isotypic iodidoplumbate(II), see: Rayner & Billing (2010b).

Experimental top

A mixture of 0.050 g (0.14 mmol) PbBr₂ and 0.021 g (0.15 mmol) 1,4-bis-(aminomethyl)-cyclohexane (mixture of isomers) was dissolved in 5 ml HBr at 383 K and slowly cooled at a rate of 0.069 K/min to yield colourless, plate-shaped single crystals suitable for X-ray analysis.

Structure description top

For hydrogen-bonding nomenclature for inorganic–organic hybrids, see: Mitzi (1999). Hybrid structures containing diammonium cations have been synthesized by Dobrzycki & Woźniak (2008) and Zhu et al. (2003). The semiconducting properties of similar hybrids were demonstrated by Mitzi (2004). For the related chloridoplumbate(II), see: Rayner & Billing (2010a) and for the isotypic iodidoplumbate(II), see: Rayner & Billing (2010b).

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-x, 1/2+y, 1/2-z (b) 1-x, 1-y, 1-z (c) x, 1/2-y, 1/2+z (d) -x, 1-y, 2-z.
	Fig. 2. Packing diagram viewed along the a axis. Hydrogen bonds are drawn as dashed red lines.
	Fig. 3. Packing diagram viewed along the b axis. Hydrogen bonds are drawn as dashed red lines.

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

Crystal data top

(C₈H₂₀N₂)[PbBr₄]	F(000) = 608
M_r = 671.09	D_x = 2.748 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5293 reflections
a = 12.1042 (6) Å	θ = 3.0–28.2°
b = 8.1955 (4) Å	µ = 20.23 mm⁻¹
c = 8.2160 (4) Å	T = 173 K
β = 95.693 (1)°	Plate, colourless
V = 811.01 (7) Å³	0.20 × 0.14 × 0.02 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	1966 independent reflections
Radiation source: fine-focus sealed tube	1742 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
φ and ω scans	θ_max = 28.0°, θ_min = 1.7°
Absorption correction: integration (XPREP; Bruker, 2005)	h = −15→15
T_min = 0.091, T_max = 0.656	k = −10→10
10495 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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.047	H-atom parameters constrained
S = 0.81	w = 1/[σ²(F_o²) + (0.0349P)² + 0.0549P] where P = (F_o² + 2F_c²)/3
1966 reflections	(Δ/σ)_max = 0.011
70 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −2.31 e Å⁻³

Crystal data top

(C₈H₂₀N₂)[PbBr₄]	V = 811.01 (7) Å³
M_r = 671.09	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1042 (6) Å	µ = 20.23 mm⁻¹
b = 8.1955 (4) Å	T = 173 K
c = 8.2160 (4) Å	0.20 × 0.14 × 0.02 mm
β = 95.693 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1966 independent reflections
Absorption correction: integration (XPREP; Bruker, 2005)	1742 reflections with I > 2σ(I)
T_min = 0.091, T_max = 0.656	R_int = 0.063
10495 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.047	H-atom parameters constrained
S = 0.81	Δρ_max = 0.78 e Å⁻³
1966 reflections	Δρ_min = −2.31 e Å⁻³
70 parameters

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	0.2360 (3)	−0.0472 (4)	0.4803 (5)	0.0262 (8)
H1A	0.2798	−0.0711	0.5858	0.031*
H1B	0.2282	−0.1498	0.4166	0.031*
C2	0.1224 (3)	0.0131 (4)	0.5124 (4)	0.0216 (8)
H2	0.1325	0.1095	0.5871	0.026*
C3	0.0636 (3)	−0.1206 (4)	0.6011 (4)	0.0257 (8)
H3A	0.0558	−0.2192	0.5312	0.031*
H3B	0.1093	−0.1499	0.7035	0.031*
C4	0.0501 (3)	0.0661 (5)	0.3589 (4)	0.0247 (7)
H4A	0.0869	0.1569	0.3058	0.030*
H4B	0.0419	−0.0261	0.2807	0.030*
N1	0.2966 (2)	0.0758 (4)	0.3879 (4)	0.0230 (6)
H1C	0.3644	0.0356	0.3700	0.035*
H1D	0.3054	0.1695	0.4473	0.035*
H1E	0.2569	0.0972	0.2904	0.035*
Br1	0.25157 (3)	0.02969 (4)	−0.01928 (4)	0.02426 (9)
Br2	0.50023 (3)	0.18890 (4)	−0.31018 (4)	0.02370 (9)
Pb1	0.5000	0.0000	0.0000	0.01590 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.024 (2)	0.0232 (17)	0.0322 (19)	0.0000 (15)	0.0076 (16)	0.0042 (14)
C2	0.024 (2)	0.0206 (17)	0.0210 (17)	−0.0015 (13)	0.0039 (15)	−0.0010 (12)
C3	0.0206 (19)	0.0285 (18)	0.0277 (18)	0.0035 (15)	0.0011 (15)	0.0101 (14)
C4	0.0213 (19)	0.0285 (18)	0.0246 (17)	−0.0011 (15)	0.0040 (14)	0.0042 (14)
N1	0.0203 (16)	0.0229 (15)	0.0267 (15)	−0.0014 (12)	0.0065 (12)	−0.0019 (12)
Br1	0.0241 (2)	0.02380 (17)	0.02478 (17)	−0.00282 (13)	0.00175 (14)	−0.00035 (12)
Br2	0.0311 (2)	0.02090 (17)	0.01975 (16)	0.00481 (13)	0.00579 (13)	0.00695 (12)
Pb1	0.02093 (10)	0.01395 (9)	0.01320 (9)	0.00121 (6)	0.00358 (6)	0.00007 (5)

Geometric parameters (Å, º) top

C1—N1	1.497 (4)	C4—H4B	0.9900
C1—C2	1.509 (5)	N1—H1C	0.9100
C1—H1A	0.9900	N1—H1D	0.9100
C1—H1B	0.9900	N1—H1E	0.9100
C2—C3	1.531 (4)	Br1—Pb1	3.0054 (4)
C2—C4	1.526 (5)	Br2—Pb1	2.9821 (3)
C2—H2	1.0000	Br2—Pb1ⁱⁱ	2.9886 (3)
C3—C4ⁱ	1.514 (5)	Pb1—Br2ⁱⁱⁱ	2.9821 (3)
C3—H3A	0.9900	Pb1—Br2^iv	2.9886 (3)
C3—H3B	0.9900	Pb1—Br2^v	2.9886 (3)
C4—C3ⁱ	1.514 (5)	Pb1—Br1ⁱⁱⁱ	3.0054 (4)
C4—H4A	0.9900

N1—C1—C2	111.7 (3)	H4A—C4—H4B	108.0
N1—C1—H1A	109.3	C1—N1—H1C	109.5
C2—C1—H1A	109.3	C1—N1—H1D	109.5
N1—C1—H1B	109.3	H1C—N1—H1D	109.5
C2—C1—H1B	109.3	C1—N1—H1E	109.5
H1A—C1—H1B	108.0	H1C—N1—H1E	109.5
C1—C2—C3	108.9 (3)	H1D—N1—H1E	109.5
C1—C2—C4	114.0 (3)	Pb1—Br2—Pb1ⁱⁱ	152.724 (12)
C3—C2—C4	110.0 (3)	Br2ⁱⁱⁱ—Pb1—Br2	180.000 (11)
C1—C2—H2	107.9	Br2ⁱⁱⁱ—Pb1—Br2^iv	89.827 (4)
C3—C2—H2	107.9	Br2—Pb1—Br2^iv	90.173 (4)
C4—C2—H2	107.9	Br2ⁱⁱⁱ—Pb1—Br2^v	90.173 (4)
C4ⁱ—C3—C2	111.6 (3)	Br2—Pb1—Br2^v	89.827 (4)
C4ⁱ—C3—H3A	109.3	Br2^iv—Pb1—Br2^v	180.000 (15)
C2—C3—H3A	109.3	Br2ⁱⁱⁱ—Pb1—Br1	90.075 (10)
C4ⁱ—C3—H3B	109.3	Br2—Pb1—Br1	89.925 (10)
C2—C3—H3B	109.3	Br2^iv—Pb1—Br1	84.697 (10)
H3A—C3—H3B	108.0	Br2^v—Pb1—Br1	95.303 (10)
C3ⁱ—C4—C2	111.3 (3)	Br2ⁱⁱⁱ—Pb1—Br1ⁱⁱⁱ	89.925 (10)
C3ⁱ—C4—H4A	109.4	Br2—Pb1—Br1ⁱⁱⁱ	90.075 (10)
C2—C4—H4A	109.4	Br2^iv—Pb1—Br1ⁱⁱⁱ	95.303 (10)
C3ⁱ—C4—H4B	109.4	Br2^v—Pb1—Br1ⁱⁱⁱ	84.697 (10)
C2—C4—H4B	109.4	Br1—Pb1—Br1ⁱⁱⁱ	180.000 (13)

N1—C1—C2—C3	177.9 (3)	C3—C2—C4—C3ⁱ	55.8 (4)
N1—C1—C2—C4	54.7 (4)	Pb1ⁱⁱ—Br2—Pb1—Br2^iv	−0.28 (4)
C1—C2—C3—C4ⁱ	178.5 (3)	Pb1ⁱⁱ—Br2—Pb1—Br2^v	179.72 (4)
C4—C2—C3—C4ⁱ	−56.0 (4)	Pb1ⁱⁱ—Br2—Pb1—Br1	84.42 (3)
C1—C2—C4—C3ⁱ	178.4 (3)	Pb1ⁱⁱ—Br2—Pb1—Br1ⁱⁱⁱ	−95.58 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Br2ⁱⁱⁱ	0.91	2.54	3.387 (3)	154
N1—H1D···Br1^iv	0.91	2.57	3.378 (3)	148
N1—H1D···Br2^vi	0.91	2.94	3.446 (3)	117
N1—H1E···Br1	0.91	2.60	3.357 (3)	141

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

Experimental details

Crystal data
Chemical formula	(C₈H₂₀N₂)[PbBr₄]
M_r	671.09
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.1042 (6), 8.1955 (4), 8.2160 (4)
β (°)	95.693 (1)
V (Å³)	811.01 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	20.23
Crystal size (mm)	0.20 × 0.14 × 0.02

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Integration (XPREP; Bruker, 2005)
T_min, T_max	0.091, 0.656
No. of measured, independent and observed [I > 2σ(I)] reflections	10495, 1966, 1742
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.047, 0.81
No. of reflections	1966
No. of parameters	70
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −2.31

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—Br2ⁱ	2.9821 (3)	Pb1—Br1ⁱ	3.0054 (4)
Pb1—Br2ⁱⁱ	2.9886 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Br2ⁱ	0.91	2.54	3.387 (3)	154.4
N1—H1D···Br1ⁱⁱ	0.91	2.57	3.378 (3)	148.0
N1—H1D···Br2ⁱⁱⁱ	0.91	2.94	3.446 (3)	116.9
N1—H1E···Br1	0.91	2.60	3.357 (3)	141.3

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

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-bromido-di­bromido­plumbate(II)]]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Poly[1,4-bis(ammoniomethyl)cyclohexane [di-μ-bromido-dibromidoplumbate(II)]]