1-Chloro­methyl-1,4-diazo­niabicyclo­[2.2.2]octane bis­(hexa­fluoro­phosphate)

Zhu, R.-Q.

doi:10.1107/S1600536811000390

organic compounds

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Volume 67| Part 2| February 2011| Page o346

doi:10.1107/S1600536811000390

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1-Chloromethyl-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate)

Run-Qiang Zhu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: zhurunqiang@163.com

(Received 13 December 2010; accepted 5 January 2011; online 12 January 2011)

In the crystal structure of the title compound, C₇H₁₅ClN₂²⁺·2PF₆⁻, the cations and anions are linked by intermolecular N—H⋯F hydrogen bonds.

Related literature

For general background to ferroelectric metal-organic frameworks, see: Fu et al. (2009 ); Ye et al. (2006 ); Zhang et al. (2008 , 2010 ).

Experimental

Crystal data

C₇H₁₅ClN₂²⁺·2PF₆⁻
M_r = 452.6
Orthorhombic, P b c a
a = 14.414 (8) Å
b = 12.976 (7) Å
c = 16.115 (9) Å
V = 3014 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.836, T_max = 0.888
30798 measured reflections
3447 independent reflections
3197 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.146
S = 1.24
3447 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2C⋯F3ⁱ	0.91	2.26	2.924 (3)	130
N2—H2C⋯F4ⁱ	0.91	2.40	3.073 (3)	131
N2—H2C⋯F9ⁱ	0.91	2.43	3.055 (3)	126
Symmetry code: (i) x, y-1, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000390/fj2377sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000390/fj2377Isup2.hkl

checkCIF report

Comment top

We synthesized the title compound to find ferroelectric material by dielectric measurements of compound as a function of temperature(Fu et al. 2009;Ye et al.2006; Zhang et al.2008; Zhang et al.2010). In the range from 190 K to near its melting point(m.p. >452 K), no dielectric anomaly was observed.

Single crystal of the title compound suitable for X-ray diffraction analysis were obtained by evaporating an water solution in 123.5 K. As Fig.1, the compound consists of one 1-(chloromethyl)-1,4- diazabicyclo[2.2.2]octane-1,4-diium cations and two hexafluorophosphate anions. The hydrogen bonds linked one 1-(chloromethyl)-1,4- diazabicyclo[2.2.2]octane-1,4-diium cations and two hexafluorophosphate anions of the another cell as showed in the Fig.2.

Related literature top

For general background to ferroelectric metal-organic frameworks, see: Fu et al. (2009); Ye et al. (2006); Zhang et al. (2008, 2010).

Experimental top

1,4-Diazabicyclo[2.2.2]octane(5.6 g,0.05 mol)was dissolved in 20 ml of dichloromethane and the mixture solution was refluxed for 8 h. A white precipitate of 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium chloride were obtained. The title compound was synthesized by the mixed solution of 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium chloride(1.97 g, 10 mmol) and hexafluorophosphoric acid(20 mmol). After a few days, colorless block crystals of the title compound were obtained on slow evaporation of the solvent.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A partial packing diagram of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound, hydrogen bonds are shown as dashed lines.

1-Chloromethyl-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate) top

Crystal data top

C₇H₁₅ClN₂²⁺·2PF₆⁻	F(000) = 1808
M_r = 452.6	D_x = 1.995 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6697 reflections
a = 14.414 (8) Å	θ = 2.5–27.5°
b = 12.976 (7) Å	µ = 0.60 mm⁻¹
c = 16.115 (9) Å	T = 293 K
V = 3014 (3) Å³	Prism, colorless
Z = 8	0.30 × 0.25 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	3447 independent reflections
Radiation source: fine-focus sealed tube	3197 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
CCD Profile fitting scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −18→18
T_min = 0.836, T_max = 0.888	k = −16→16
30798 measured reflections	l = −20→20

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)] = 0.056	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0625P)² + 3.8206P] where P = (F_o² + 2F_c²)/3
S = 1.24	(Δ/σ)_max < 0.001
3447 reflections	Δρ_max = 0.58 e Å⁻³
217 parameters	Δρ_min = −0.46 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (1)

Crystal data top

C₇H₁₅ClN₂²⁺·2PF₆⁻	V = 3014 (3) Å³
M_r = 452.6	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.414 (8) Å	µ = 0.60 mm⁻¹
b = 12.976 (7) Å	T = 293 K
c = 16.115 (9) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	3447 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3197 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.888	R_int = 0.050
30798 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.24	Δρ_max = 0.58 e Å⁻³
3447 reflections	Δρ_min = −0.46 e Å⁻³
217 parameters

Special details top

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 > 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
P1	0.10243 (5)	0.80778 (6)	0.38500 (5)	0.01982 (19)
P2	0.25717 (5)	0.96221 (6)	0.14312 (5)	0.01997 (19)
F8	0.19471 (13)	0.87588 (16)	0.38218 (13)	0.0359 (5)
F9	0.06202 (13)	0.87478 (14)	0.30870 (11)	0.0293 (4)
F11	0.05718 (12)	0.88833 (14)	0.44911 (11)	0.0268 (4)
F10	0.00885 (13)	0.74127 (15)	0.38738 (13)	0.0331 (4)
F7	0.14303 (13)	0.74224 (16)	0.46061 (11)	0.0343 (5)
F12	0.14650 (13)	0.72793 (15)	0.32030 (12)	0.0322 (4)
F3	0.15177 (12)	1.00058 (16)	0.15861 (13)	0.0347 (5)
F1	0.23000 (15)	0.92628 (16)	0.05253 (11)	0.0363 (5)
F4	0.28151 (16)	0.99851 (17)	0.23639 (13)	0.0430 (6)
F2	0.36096 (14)	0.92349 (19)	0.13078 (16)	0.0479 (6)
F5	0.22953 (16)	0.85130 (15)	0.17743 (14)	0.0421 (5)
F6	0.28287 (17)	1.07397 (16)	0.11115 (15)	0.0465 (6)
Cl1	0.09951 (6)	0.45726 (7)	0.44115 (7)	0.0419 (3)
N1	0.05494 (16)	0.26975 (18)	0.37949 (15)	0.0189 (5)
N2	0.11243 (16)	0.10322 (19)	0.31629 (15)	0.0206 (5)
H2C	0.1332	0.0434	0.2933	0.025*
C5	−0.02655 (19)	0.2006 (2)	0.35656 (18)	0.0207 (6)
H5A	−0.0654	0.1896	0.4049	0.025*
H5B	−0.0638	0.2336	0.3141	0.025*
C1	0.1107 (2)	0.2924 (2)	0.30230 (19)	0.0224 (6)
H1A	0.1657	0.3316	0.3168	0.027*
H1B	0.0740	0.3333	0.2641	0.027*
C3	0.1568 (2)	0.1167 (2)	0.39967 (18)	0.0278 (7)
H3A	0.2234	0.1239	0.3935	0.033*
H3B	0.1446	0.0569	0.4341	0.033*
C7	0.0138 (2)	0.3663 (2)	0.4162 (2)	0.0266 (6)
H7A	−0.0207	0.3486	0.4660	0.032*
H7B	−0.0293	0.3964	0.3769	0.032*
C2	0.1390 (2)	0.1914 (2)	0.2609 (2)	0.0280 (7)
H2A	0.1080	0.1847	0.2077	0.034*
H2B	0.2054	0.1908	0.2513	0.034*
C4	0.1162 (2)	0.2138 (2)	0.44068 (18)	0.0232 (6)
H4A	0.0804	0.1946	0.4892	0.028*
H4B	0.1662	0.2588	0.4584	0.028*
C6	0.0090 (2)	0.0978 (3)	0.3247 (3)	0.0364 (8)
H6A	−0.0078	0.0434	0.3631	0.044*
H6B	−0.0188	0.0825	0.2713	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0173 (4)	0.0238 (4)	0.0184 (4)	0.0025 (3)	0.0000 (3)	0.0006 (3)
P2	0.0181 (4)	0.0220 (4)	0.0198 (4)	−0.0001 (3)	0.0000 (3)	−0.0018 (3)
F8	0.0217 (9)	0.0451 (12)	0.0410 (11)	−0.0067 (8)	0.0054 (8)	−0.0014 (9)
F9	0.0340 (10)	0.0322 (10)	0.0218 (9)	0.0108 (8)	−0.0020 (7)	0.0035 (7)
F11	0.0282 (9)	0.0286 (9)	0.0235 (9)	0.0024 (7)	0.0050 (7)	−0.0028 (7)
F10	0.0264 (9)	0.0311 (10)	0.0419 (11)	−0.0074 (8)	0.0020 (8)	−0.0041 (9)
F7	0.0372 (10)	0.0422 (11)	0.0235 (9)	0.0133 (9)	−0.0027 (8)	0.0073 (8)
F12	0.0367 (10)	0.0335 (10)	0.0265 (10)	0.0142 (8)	0.0038 (8)	−0.0031 (8)
F3	0.0199 (9)	0.0403 (11)	0.0440 (11)	0.0016 (8)	0.0030 (8)	−0.0162 (9)
F1	0.0466 (12)	0.0429 (11)	0.0195 (9)	0.0112 (10)	−0.0053 (8)	−0.0082 (8)
F4	0.0560 (14)	0.0420 (12)	0.0310 (11)	0.0127 (10)	−0.0191 (10)	−0.0121 (9)
F2	0.0208 (10)	0.0539 (14)	0.0690 (16)	0.0064 (9)	−0.0004 (10)	−0.0187 (12)
F5	0.0614 (14)	0.0256 (10)	0.0392 (11)	−0.0020 (10)	0.0077 (10)	0.0035 (9)
F6	0.0572 (14)	0.0280 (10)	0.0544 (14)	−0.0099 (10)	0.0148 (11)	0.0055 (10)
Cl1	0.0285 (4)	0.0331 (4)	0.0641 (6)	−0.0071 (3)	0.0121 (4)	−0.0250 (4)
N1	0.0164 (11)	0.0205 (11)	0.0199 (11)	−0.0001 (9)	0.0005 (9)	−0.0011 (9)
N2	0.0191 (12)	0.0200 (11)	0.0227 (12)	0.0001 (9)	0.0003 (9)	−0.0010 (10)
C5	0.0159 (13)	0.0237 (14)	0.0225 (14)	−0.0027 (10)	−0.0020 (10)	−0.0003 (11)
C1	0.0218 (14)	0.0202 (13)	0.0252 (14)	−0.0011 (11)	0.0051 (11)	0.0007 (11)
C3	0.0348 (17)	0.0266 (15)	0.0220 (14)	0.0078 (13)	−0.0052 (12)	0.0007 (12)
C7	0.0204 (14)	0.0213 (14)	0.0382 (17)	0.0025 (11)	0.0046 (12)	−0.0076 (13)
C2	0.0377 (17)	0.0239 (15)	0.0223 (15)	0.0035 (13)	0.0074 (13)	0.0043 (12)
C4	0.0200 (13)	0.0294 (15)	0.0201 (13)	0.0005 (12)	−0.0014 (11)	−0.0014 (11)
C6	0.0190 (15)	0.0282 (16)	0.062 (2)	−0.0040 (13)	−0.0030 (15)	−0.0145 (16)

Geometric parameters (Å, º) top

P1—F7	1.597 (2)	N2—C2	1.501 (4)
P1—F8	1.598 (2)	N2—H2C	0.9100
P1—F12	1.601 (2)	C5—C6	1.518 (4)
P1—F10	1.602 (2)	C5—H5A	0.9700
P1—F11	1.6079 (19)	C5—H5B	0.9700
P1—F9	1.6147 (19)	C1—C2	1.527 (4)
P2—F1	1.582 (2)	C1—H1A	0.9700
P2—F6	1.583 (2)	C1—H1B	0.9700
P2—F2	1.591 (2)	C3—C4	1.538 (4)
P2—F5	1.592 (2)	C3—H3A	0.9700
P2—F4	1.614 (2)	C3—H3B	0.9700
P2—F3	1.618 (2)	C7—H7A	0.9700
Cl1—C7	1.756 (3)	C7—H7B	0.9700
N1—C7	1.507 (4)	C2—H2A	0.9700
N1—C4	1.510 (4)	C2—H2B	0.9700
N1—C1	1.510 (4)	C4—H4A	0.9700
N1—C5	1.524 (3)	C4—H4B	0.9700
N2—C6	1.498 (4)	C6—H6A	0.9700
N2—C3	1.498 (4)	C6—H6B	0.9700

F7—P1—F8	90.65 (12)	C6—C5—N1	109.8 (2)
F7—P1—F12	90.40 (11)	C6—C5—H5A	109.7
F8—P1—F12	90.53 (12)	N1—C5—H5A	109.7
F7—P1—F10	90.19 (12)	C6—C5—H5B	109.7
F8—P1—F10	178.98 (12)	N1—C5—H5B	109.7
F12—P1—F10	90.06 (11)	H5A—C5—H5B	108.2
F7—P1—F11	90.26 (11)	N1—C1—C2	109.6 (2)
F8—P1—F11	89.79 (11)	N1—C1—H1A	109.8
F12—P1—F11	179.26 (11)	C2—C1—H1A	109.8
F10—P1—F11	89.62 (11)	N1—C1—H1B	109.8
F7—P1—F9	179.52 (13)	C2—C1—H1B	109.8
F8—P1—F9	88.90 (11)	H1A—C1—H1B	108.2
F12—P1—F9	89.75 (11)	N2—C3—C4	108.6 (2)
F10—P1—F9	90.26 (11)	N2—C3—H3A	110.0
F11—P1—F9	89.59 (10)	C4—C3—H3A	110.0
F1—P2—F6	91.58 (13)	N2—C3—H3B	110.0
F1—P2—F2	91.39 (12)	C4—C3—H3B	110.0
F6—P2—F2	91.64 (14)	H3A—C3—H3B	108.3
F1—P2—F5	89.54 (12)	N1—C7—Cl1	111.8 (2)
F6—P2—F5	178.30 (13)	N1—C7—H7A	109.3
F2—P2—F5	89.61 (13)	Cl1—C7—H7A	109.3
F1—P2—F4	178.20 (13)	N1—C7—H7B	109.3
F6—P2—F4	89.13 (13)	Cl1—C7—H7B	109.3
F2—P2—F4	90.24 (13)	H7A—C7—H7B	107.9
F5—P2—F4	89.71 (13)	N2—C2—C1	109.1 (2)
F1—P2—F3	90.03 (11)	N2—C2—H2A	109.9
F6—P2—F3	89.32 (13)	C1—C2—H2A	109.9
F2—P2—F3	178.26 (14)	N2—C2—H2B	109.9
F5—P2—F3	89.40 (12)	C1—C2—H2B	109.9
F4—P2—F3	88.32 (11)	H2A—C2—H2B	108.3
C7—N1—C4	111.9 (2)	N1—C4—C3	109.6 (2)
C7—N1—C1	111.8 (2)	N1—C4—H4A	109.8
C4—N1—C1	108.7 (2)	C3—C4—H4A	109.8
C7—N1—C5	106.3 (2)	N1—C4—H4B	109.8
C4—N1—C5	109.0 (2)	C3—C4—H4B	109.8
C1—N1—C5	109.0 (2)	H4A—C4—H4B	108.2
C6—N2—C3	110.4 (3)	N2—C6—C5	109.0 (2)
C6—N2—C2	110.1 (3)	N2—C6—H6A	109.9
C3—N2—C2	109.6 (2)	C5—C6—H6A	109.9
C6—N2—H2C	108.9	N2—C6—H6B	109.9
C3—N2—H2C	108.9	C5—C6—H6B	109.9
C2—N2—H2C	108.9	H6A—C6—H6B	108.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···F3ⁱ	0.91	2.26	2.924 (3)	130
N2—H2C···F4ⁱ	0.91	2.40	3.073 (3)	131
N2—H2C···F9ⁱ	0.91	2.43	3.055 (3)	126

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₇H₁₅ClN₂²⁺·2PF₆⁻
M_r	452.6
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	14.414 (8), 12.976 (7), 16.115 (9)
V (Å³)	3014 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.836, 0.888
No. of measured, independent and observed [I > 2σ(I)] reflections	30798, 3447, 3197
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.146, 1.24
No. of reflections	3447
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.46

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···F3ⁱ	0.91	2.26	2.924 (3)	130
N2—H2C···F4ⁱ	0.91	2.40	3.073 (3)	131
N2—H2C···F9ⁱ	0.91	2.43	3.055 (3)	126

Symmetry code: (i) x, y−1, z.

Acknowledgements

This work was supported by Southeast University.

References

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o346

doi:10.1107/S1600536811000390

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

1-Chloro­methyl-1,4-diazo­niabi­cyclo­[2.2.2]octane bis­­(hexa­fluoro­phosphate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-Chloromethyl-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate)