Bis[N-(1-naphth­yl)ethyl­enediammonium] hexa­bromidoplumbate(II)

Chen, Y.; Zheng, Y.-Y.; Wu, G.; Wang, M.; Chen, H.-Z.; Yang, H.

doi:10.1107/S1600536810008901

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m417

doi:10.1107/S1600536810008901

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Bis[N-(1-naphthyl)ethylenediammonium] hexabromidoplumbate(II)

Yao Chen,^a Ying-Ying Zheng,^a Gang Wu,^a ^* Mang Wang,^a Hong-Zheng Chen ^a and Hui Yang ^a

^aState Key Laboratory of Silicon Materials, Zhejiang University, Key Laboratory of Macromolecule Synthesis and Functionalization (Zhejiang University), Ministry of Education, Department of Material Science and Engineering, Zhejiang University, Hangzhou 310027, People's Republic of China
^*Correspondence e-mail: wmang@zju.edu.cn

(Received 8 January 2010; accepted 9 March 2010; online 17 March 2010)

The title compound, (C₁₂H₁₆N₂)₂[PbBr₆], is an organic–inorganic salt, with two doubly protonated N-(1-naphthyl)ethylenediammonium cations and one octahedral hexabromidoplumbate(II) anion. The Pb^II atom is located on a centre of inversion. The crystal structure consists of alternating inorganic and organic layers parallel to the bc plane. Face-to-face aromatic stacking interactions [centroid–centroid distance = 3.505 (5) Å] occur between parallel naphthalene systems in the organic layers, and N—H⋯Br hydrogen bonds between the cations and anions stabilize the crystal structure.

Related literature

For the related structure bis[N-(1-naphthyl)ethylenediammonium] hexaiodidoplumbate(II), see: Zheng et al. (2007 ).

Experimental

Crystal data

(C₁₂H₁₆N₂)₂[PbBr₆]
M_r = 1063.19
Triclinic, $[P \overline 1]$
a = 8.1193 (4) Å
b = 8.5598 (4) Å
c = 12.4328 (6) Å
α = 80.4601 (13)°
β = 79.4756 (14)°
γ = 62.8592 (10)°
V = 752.63 (6) Å³
Z = 1
Mo Kα radiation
μ = 13.59 mm⁻¹
T = 296 K
0.39 × 0.33 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.008, T_max = 0.066
6484 measured reflections
2938 independent reflections
2444 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.174
S = 1.00
2938 reflections
162 parameters
H-atom parameters constrained
Δρ_max = 3.73 e Å⁻³
Δρ_min = −3.27 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb1—Br1	3.0749 (8)
Pb1—Br2	2.9944 (10)
Pb1—Br3	3.0118 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1	0.90	2.48	3.364 (8)	168
N1—H1B⋯Br3ⁱ	0.90	2.89	3.618 (7)	139
N2—H2B⋯Br2ⁱⁱ	0.89	2.59	3.339 (9)	143
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+1, -z+1.

Data collection: PROCESS-AUTO (Rigaku, 2006 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ); 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 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008901/xu2718sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810008901/xu2718Isup2.hkl

checkCIF report

Comment top

The title compound is a organic-inorganic compound, its structure is similar to bis(N-(1-naphthyl)ethylenediammonium) hexaiodoplumbate(II) (Zheng et al., 2007). The crystal structure is composed of alternating organic and inorganic sheets nearly parallel to the bc plane (Fig. 1). The Pb^II cation is located on an inversion center and coordinated by six Br^- anions with a distorted octahedral geometry (Fig. 2). The Pb—Br bond lengths (Table 1) are in the range form 2.9944 (10) to 3.0749 (8) Å. The face-to-face distance between adjacent parallel naphthalene ring systems is 3.505 Å, indicating aromatic π-π interaction. The N—H···Br hydrogen bonding is present in the crystal structure (Table 2).

Related literature top

For the related structure bis[N-(1-naphthyl)ethylenediammonium] hexaiodoplumbate(II), see: Zheng et al. (2007).

Experimental top

The N-(1-naphthyl)ethylenediamine hydrobromide and PbBr₂ are used as recieved. Concentrated hydrobromide and acetonitrile were degassed before using. All reactions were carried out under a nitrogen atmosphere. The title compound is prepared by a reaction of 0.1016 g N-(1-naphthyl)ethylenediamine hydrobromide with 0.0719 g PbBr₂ in the mixture solution of 14.6 ml hydrobromide and 1.8 ml acetonitrile at 353 K. The resulting solution was kept at 353 K for 1 h and then slowly cooled down to room temperature. The single crystals were filtered off from the solution.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2007); 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); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular packing of the title compound viewed along the b axis.
	Fig. 2. The structure of the title compound [symmetry code: (i) 1-x,1-y,1-z].

Bis[N-(1-naphthyl)ethylenediammonium] hexabromidoplumbate(II) top

Crystal data top

(C₁₂H₁₆N₂)₂[PbBr₆]	Z = 1
M_r = 1063.19	F(000) = 496
Triclinic, P1	D_x = 2.346 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1193 (4) Å	Cell parameters from 6259 reflections
b = 8.5598 (4) Å	θ = 3.0–27.4°
c = 12.4328 (6) Å	µ = 13.59 mm⁻¹
α = 80.4601 (13)°	T = 296 K
β = 79.4756 (14)°	Chunk, colourless
γ = 62.8592 (10)°	0.39 × 0.33 × 0.20 mm
V = 752.63 (6) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	2938 independent reflections
Radiation source: rolling anode	2444 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.092
Detector resolution: 10.00 pixels mm^-1	θ_max = 26.0°, θ_min = 3.0°
ω scans	h = −9→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
T_min = 0.008, T_max = 0.066	l = −15→15
6484 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.174	w = 1/[σ²(F_o²) + (0.073P)² + 3P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.002
2938 reflections	Δρ_max = 3.73 e Å⁻³
162 parameters	Δρ_min = −3.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0104 (12)

Crystal data top

(C₁₂H₁₆N₂)₂[PbBr₆]	γ = 62.8592 (10)°
M_r = 1063.19	V = 752.63 (6) Å³
Triclinic, P1	Z = 1
a = 8.1193 (4) Å	Mo Kα radiation
b = 8.5598 (4) Å	µ = 13.59 mm⁻¹
c = 12.4328 (6) Å	T = 296 K
α = 80.4601 (13)°	0.39 × 0.33 × 0.20 mm
β = 79.4756 (14)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2938 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2444 reflections with I > 2σ(I)
T_min = 0.008, T_max = 0.066	R_int = 0.092
6484 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.00	Δρ_max = 3.73 e Å⁻³
2938 reflections	Δρ_min = −3.27 e Å⁻³
162 parameters

Special details top

Experimental. Spectroscopic analysis: IR (KBr, cm^-1): 3008 (N—H asymmatric stretching), 2906 (N—H asymmatric stretching), 1573 (NH₂ bending), 1142 (CH₂ non-planar oscillating). Chemical analysis (calculated): C 27.09%, H 3.01%, N 5.27%; (found): C 27.12%, H 3.04%, N 5.23%.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 2sigma(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
Pb1	0.5000	0.5000	0.5000	0.03697 (12)
Br3	0.69148 (13)	0.55171 (12)	0.66759 (8)	0.0503 (2)
Br2	0.85539 (12)	0.36179 (13)	0.34710 (8)	0.0533 (3)
Br1	0.44025 (12)	0.86889 (11)	0.39152 (8)	0.0482 (2)
N2	0.8772 (11)	0.7533 (10)	0.4518 (7)	0.054 (2)
H2A	0.7695	0.7973	0.4951	0.081*
H2B	0.9659	0.6741	0.4912	0.081*
H2C	0.8658	0.7018	0.3988	0.081*
N1	0.7162 (9)	1.0520 (8)	0.2540 (6)	0.0418 (17)
H1A	0.6464	0.9944	0.2816	0.050*
H1B	0.6673	1.1530	0.2863	0.050*
C1	0.7317 (10)	0.9604 (10)	0.0702 (7)	0.0371 (19)
C6	0.7273 (11)	1.0045 (10)	−0.0447 (8)	0.043 (2)
C10	0.7082 (12)	1.0940 (10)	0.1348 (8)	0.042 (2)
C2	0.7567 (12)	0.7896 (10)	0.1148 (8)	0.042 (2)
H2	0.7528	0.7596	0.1903	0.051*
C11	0.9145 (12)	0.9392 (12)	0.2815 (8)	0.047 (2)
H11A	0.9668	0.8306	0.2465	0.056*
H11B	0.9895	1.0014	0.2513	0.056*
C9	0.6906 (13)	1.2553 (10)	0.0898 (9)	0.050 (2)
H9	0.6822	1.3366	0.1343	0.059*
C5	0.7545 (13)	0.8761 (12)	−0.1131 (9)	0.051 (2)
H5	0.7519	0.9045	−0.1885	0.061*
C12	0.9269 (12)	0.8946 (12)	0.4031 (8)	0.051 (2)
H12A	1.0534	0.8616	0.4159	0.061*
H12B	0.8454	0.9995	0.4402	0.061*
C8	0.6851 (12)	1.2998 (10)	−0.0233 (8)	0.049 (2)
H8	0.6703	1.4115	−0.0540	0.058*
C4	0.7839 (13)	0.7129 (12)	−0.0684 (9)	0.056 (3)
H4	0.8025	0.6291	−0.1141	0.067*
C7	0.7014 (12)	1.1792 (12)	−0.0885 (8)	0.046 (2)
H7	0.6957	1.2109	−0.1635	0.055*
C3	0.7876 (13)	0.6654 (11)	0.0432 (9)	0.052 (3)
H3	0.8106	0.5506	0.0711	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.03482 (19)	0.03828 (18)	0.0450 (3)	−0.02084 (16)	−0.00683 (18)	−0.00605 (16)
Br3	0.0562 (4)	0.0602 (4)	0.0498 (5)	−0.0361 (4)	−0.0112 (4)	−0.0079 (4)
Br2	0.0390 (4)	0.0651 (5)	0.0514 (6)	−0.0190 (4)	−0.0035 (4)	−0.0078 (4)
Br1	0.0429 (4)	0.0463 (4)	0.0596 (6)	−0.0249 (3)	−0.0068 (4)	0.0014 (4)
N2	0.051 (4)	0.055 (4)	0.062 (5)	−0.028 (3)	−0.020 (4)	0.007 (4)
N1	0.040 (3)	0.039 (3)	0.054 (4)	−0.022 (3)	−0.003 (3)	−0.014 (3)
C1	0.029 (3)	0.042 (3)	0.046 (5)	−0.018 (3)	−0.001 (3)	−0.011 (3)
C6	0.029 (3)	0.040 (3)	0.063 (6)	−0.015 (3)	−0.012 (4)	−0.008 (4)
C10	0.041 (4)	0.045 (4)	0.045 (5)	−0.024 (3)	−0.006 (4)	−0.003 (3)
C2	0.049 (4)	0.042 (3)	0.048 (5)	−0.029 (3)	−0.009 (4)	−0.001 (3)
C11	0.039 (4)	0.052 (4)	0.057 (6)	−0.026 (4)	−0.001 (4)	−0.008 (4)
C9	0.055 (5)	0.037 (3)	0.066 (6)	−0.028 (3)	−0.006 (5)	−0.009 (4)
C5	0.046 (4)	0.063 (5)	0.053 (6)	−0.030 (4)	−0.009 (4)	−0.008 (4)
C12	0.051 (4)	0.054 (4)	0.063 (6)	−0.032 (4)	−0.022 (4)	0.000 (4)
C8	0.047 (4)	0.038 (4)	0.063 (6)	−0.025 (3)	−0.002 (4)	0.002 (4)
C4	0.053 (5)	0.055 (4)	0.070 (7)	−0.025 (4)	−0.008 (5)	−0.025 (4)
C7	0.038 (4)	0.058 (4)	0.038 (5)	−0.022 (4)	0.000 (4)	0.004 (4)
C3	0.045 (4)	0.045 (4)	0.071 (7)	−0.020 (4)	−0.009 (5)	−0.011 (4)

Geometric parameters (Å, º) top

Pb1—Br1	3.0749 (8)	C10—C9	1.354 (12)
Pb1—Br1ⁱ	3.0749 (8)	C2—C3	1.405 (13)
Pb1—Br2	2.9944 (10)	C2—H2	0.9300
Pb1—Br2ⁱ	2.9944 (10)	C11—C12	1.506 (13)
Pb1—Br3ⁱ	3.0118 (10)	C11—H11A	0.9700
Pb1—Br3	3.0118 (10)	C11—H11B	0.9700
N2—C12	1.451 (12)	C9—C8	1.399 (14)
N2—H2A	0.8900	C9—H9	0.9300
N2—H2B	0.8900	C5—C4	1.343 (14)
N2—H2C	0.8900	C5—H5	0.9300
N1—C10	1.472 (12)	C12—H12A	0.9700
N1—C11	1.522 (10)	C12—H12B	0.9700
N1—H1A	0.9000	C8—C7	1.361 (14)
N1—H1B	0.9000	C8—H8	0.9300
C1—C2	1.410 (11)	C4—C3	1.382 (15)
C1—C6	1.419 (13)	C4—H4	0.9300
C1—C10	1.428 (12)	C7—H7	0.9300
C6—C5	1.414 (13)	C3—H3	0.9300
C6—C7	1.436 (13)

Br2—Pb1—Br2ⁱ	180.0	C1—C10—N1	119.1 (7)
Br2—Pb1—Br3ⁱ	88.45 (3)	C3—C2—C1	118.9 (9)
Br2ⁱ—Pb1—Br3ⁱ	91.55 (3)	C3—C2—H2	120.6
Br2—Pb1—Br3	91.55 (3)	C1—C2—H2	120.6
Br2ⁱ—Pb1—Br3	88.45 (3)	C12—C11—N1	113.4 (7)
Br3ⁱ—Pb1—Br3	180.0	C12—C11—H11A	108.9
Br2—Pb1—Br1	86.43 (3)	N1—C11—H11A	108.9
Br2ⁱ—Pb1—Br1	93.57 (3)	C12—C11—H11B	108.9
Br3ⁱ—Pb1—Br1	92.47 (3)	N1—C11—H11B	108.9
Br3—Pb1—Br1	87.53 (3)	H11A—C11—H11B	107.7
Br2—Pb1—Br1ⁱ	93.57 (3)	C10—C9—C8	120.1 (9)
Br2ⁱ—Pb1—Br1ⁱ	86.43 (3)	C10—C9—H9	119.9
Br3ⁱ—Pb1—Br1ⁱ	87.53 (3)	C8—C9—H9	119.9
Br3—Pb1—Br1ⁱ	92.47 (3)	C4—C5—C6	119.6 (10)
Br1—Pb1—Br1ⁱ	180.0	C4—C5—H5	120.2
C12—N2—H2A	109.5	C6—C5—H5	120.2
C12—N2—H2B	109.5	N2—C12—C11	114.6 (8)
H2A—N2—H2B	109.5	N2—C12—H12A	108.6
C12—N2—H2C	109.5	C11—C12—H12A	108.6
H2A—N2—H2C	109.5	N2—C12—H12B	108.6
H2B—N2—H2C	109.5	C11—C12—H12B	108.6
C10—N1—C11	112.3 (7)	H12A—C12—H12B	107.6
C10—N1—H1A	109.2	C7—C8—C9	119.8 (8)
C11—N1—H1A	109.2	C7—C8—H8	120.1
C10—N1—H1B	109.2	C9—C8—H8	120.1
C11—N1—H1B	109.2	C5—C4—C3	122.1 (10)
H1A—N1—H1B	107.9	C5—C4—H4	118.9
C2—C1—C6	119.0 (8)	C3—C4—H4	118.9
C2—C1—C10	123.5 (8)	C8—C7—C6	121.8 (9)
C6—C1—C10	117.5 (7)	C8—C7—H7	119.1
C5—C6—C1	120.0 (8)	C6—C7—H7	119.1
C5—C6—C7	121.9 (9)	C4—C3—C2	120.4 (9)
C1—C6—C7	118.1 (8)	C4—C3—H3	119.8
C9—C10—C1	122.5 (9)	C2—C3—H3	119.8
C9—C10—N1	118.2 (8)

C2—C1—C6—C5	−2.2 (12)	C1—C10—C9—C8	3.4 (14)
C10—C1—C6—C5	178.4 (8)	N1—C10—C9—C8	179.1 (8)
C2—C1—C6—C7	179.9 (8)	C1—C6—C5—C4	0.1 (13)
C10—C1—C6—C7	0.5 (11)	C7—C6—C5—C4	177.9 (9)
C2—C1—C10—C9	177.7 (8)	N1—C11—C12—N2	78.7 (10)
C6—C1—C10—C9	−2.9 (12)	C10—C9—C8—C7	−1.4 (14)
C2—C1—C10—N1	2.1 (12)	C6—C5—C4—C3	0.4 (15)
C6—C1—C10—N1	−178.6 (7)	C9—C8—C7—C6	−1.0 (13)
C11—N1—C10—C9	−100.8 (9)	C5—C6—C7—C8	−176.5 (8)
C11—N1—C10—C1	75.0 (10)	C1—C6—C7—C8	1.3 (12)
C6—C1—C2—C3	3.7 (12)	C5—C4—C3—C2	1.2 (15)
C10—C1—C2—C3	−177.0 (8)	C1—C2—C3—C4	−3.2 (13)
C10—N1—C11—C12	179.9 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1	0.90	2.48	3.364 (8)	168
N1—H1B···Br3ⁱⁱ	0.90	2.89	3.618 (7)	139
N2—H2B···Br2ⁱⁱⁱ	0.89	2.59	3.339 (9)	143

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

Experimental details

Crystal data
Chemical formula	(C₁₂H₁₆N₂)₂[PbBr₆]
M_r	1063.19
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.1193 (4), 8.5598 (4), 12.4328 (6)
α, β, γ (°)	80.4601 (13), 79.4756 (14), 62.8592 (10)
V (Å³)	752.63 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	13.59
Crystal size (mm)	0.39 × 0.33 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.008, 0.066
No. of measured, independent and observed [I > 2σ(I)] reflections	6484, 2938, 2444
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.174, 1.00
No. of reflections	2938
No. of parameters	162
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	3.73, −3.27

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Pb1—Br1	3.0749 (8)	Pb1—Br3	3.0118 (10)
Pb1—Br2	2.9944 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1	0.90	2.48	3.364 (8)	168
N1—H1B···Br3ⁱ	0.90	2.89	3.618 (7)	139
N2—H2B···Br2ⁱⁱ	0.89	2.59	3.339 (9)	143

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 50990063, 50773067 and 50503021). The authors are grateful to Professor J.-M. Gu for assistance with the crystal structure analysis.

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