Bis[(2S,4S)-4-(2-hy­droxy­eth­yl)-2-methyl­piperazine-1,4-diium] di-μ-chlorido-bis­[trichloridocadmium(II)]

Rong, T.

doi:10.1107/S1600536811006945

metal-organic compounds

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Volume 67| Part 4| April 2011| Page m396

doi:10.1107/S1600536811006945

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Bis[(2S,4S)-4-(2-hydroxyethyl)-2-methylpiperazine-1,4-diium] di-μ-chlorido-bis[trichloridocadmium(II)]

Tao Rong ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: rongtao198806@163.com

(Received 9 December 2010; accepted 23 February 2011; online 2 March 2011)

The asymmetric unit of the title compound, (C₇H₁₈N₂O)₂[Cd₂Cl₈], comprises one 4-(2-hydroxyethyl)-2-methylpiperazine-1,4-diium dication and a half [Cd₂Cl₈]⁴⁻ anion. The two Cd atoms are each coordinated by two bridging Cl atoms and three terminal Cl atoms and the [Cd₂Cl₈]⁴⁻ anion is located on an inversion centre. The crystal structure consists of N—H⋯Cl hydrogen-bonded sheets, which are further linked by C—H⋯Cl contacts, yielding a three-dimensional network.

Related literature

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

Experimental

Crystal data

(C₇H₁₈N₂O)₂[Cd₂Cl₈]
M_r = 800.86
Monoclinic, P 2₁ /n
a = 8.0318 (16) Å
b = 11.144 (2) Å
c = 15.816 (3) Å
β = 97.81 (3)°
V = 1402.6 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.632, T_max = 0.638
14193 measured reflections
3217 independent reflections
3008 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.060
S = 1.19
3217 reflections
136 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.88 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl4ⁱ	0.82	2.68	3.188 (3)	121
N1—H1D⋯Cl3ⁱⁱ	0.91	2.29	3.163 (3)	161
N2—H2D⋯Cl4ⁱⁱⁱ	0.90	2.88	3.405 (3)	119
N2—H2D⋯Cl1^iv	0.90	2.35	3.125 (3)	144
N2—H2A⋯Cl2^v	0.90	2.25	3.119 (3)	164
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y, z; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006945/rn2080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006945/rn2080Isup2.hkl

checkCIF report

Comment top

The study of ferroelectric materials has received much attention. Some materials have predominantly dielectric-ferroelectric performance.The title compound was studied as part of our work to obtain potential ferroelectric phase-change materials [Fu et al.(2009); Ye et al. (2006); Zhang et al. (2008; 2010)] .

As one part of our continuing studies on dielectric-ferroelectric materials, we synthesized the title compound (C₇H₁₈N₂O).CdCl₄ (Fig 1)_.Unfortunately, the study carried out on the title compound indicated that the permittivity is temperature-independent, suggesting that there may be no dielectric disuniformity between 80 K to 350 K [Fu et al. (2010)].

The asymmetric unit of the title compound contains one [C₇H₁₇N₂O] ²⁺ basic ion and half of the [Cd₂Cl₈]^4- complex ion which is situated on an inversion centre. The intermolecular hydrogen bonds (O1—H1A···Cl4, N1—H1D···Cl3, N2—H2D···Cl4, N2—H2D···Cl1 and N2—H2A···Cl2) link the molecules into sheets and stabilize the structure (Fig 2).

Related literature top

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

Experimental top

Ethylene oxide (25 mmol) was added by bubbling of this gas into a solution of rac-2-methyl piperazine (10 mmol) in toluene at 318–323 K. The toluene solvent was then removed under reduced pressure, the rac-2-methyl-4-ethoxyl piperazine was obtained at 376–381 K by reduced pressure distillation of the mixture. A solution of chlorhydric acid (10 mmol) was added to a solution of half equimolar amount of rac-2-methyl-4-ethoxyl piperazine inethanol (20 mL), then cadmium chloride(5 mmol) in water (10 mL) was added. Crystals suitable for structure determination were grown by slow evaporation of the mixture at room temperature

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: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.[The suffix A denotes the symmetry code: -x - y 1 - z]
	Fig. 2. A view of the packing of the title compound, stacking along the a axis. Dashed lines indicate hydrogen bonds.

Bis[(2S,4S)-4-(2-hydroxyethyl)-2-methylpiperazine-1,4-diium] di-µ-chlorido-bis[trichloridocadmium(II)] top

Crystal data top

(C₇H₁₈N₂O)₂[Cd₂Cl₈]	Z = 2
M_r = 800.86	F(000) = 792
Monoclinic, P2₁/n	D_x = 1.896 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.0318 (16) Å	θ = 3.0–27.5°
b = 11.144 (2) Å	µ = 2.30 mm⁻¹
c = 15.816 (3) Å	T = 293 K
β = 97.81 (3)°	Prism, colourless
V = 1402.6 (5) Å³	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	3217 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD_Profile_fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
T_min = 0.632, T_max = 0.638	l = −20→20
14193 measured reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.022P)² + 0.433P] where P = (F_o² + 2F_c²)/3
3217 reflections	(Δ/σ)_max = 0.001
136 parameters	Δρ_max = 0.35 e Å⁻³
2 restraints	Δρ_min = −0.88 e Å⁻³

Crystal data top

(C₇H₁₈N₂O)₂[Cd₂Cl₈]	V = 1402.6 (5) Å³
M_r = 800.86	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0318 (16) Å	µ = 2.30 mm⁻¹
b = 11.144 (2) Å	T = 293 K
c = 15.816 (3) Å	0.20 × 0.20 × 0.20 mm
β = 97.81 (3)°

Data collection top

Rigaku SCXmini diffractometer	3217 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3008 reflections with I > 2σ(I)
T_min = 0.632, T_max = 0.638	R_int = 0.037
14193 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	2 restraints
wR(F²) = 0.060	H-atom parameters constrained
S = 1.19	Δρ_max = 0.35 e Å⁻³
3217 reflections	Δρ_min = −0.88 e Å⁻³
136 parameters

Special details top

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
Cd1	0.07749 (3)	0.14056 (2)	0.435513 (16)	0.02832 (11)
Cl4	0.13747 (12)	0.02958 (8)	0.59105 (5)	0.0299 (2)
Cl2	0.34061 (12)	0.04831 (9)	0.39588 (6)	0.0364 (2)
Cl3	0.13624 (14)	0.33698 (9)	0.51000 (6)	0.0363 (2)
Cl1	−0.02934 (12)	0.23097 (9)	0.28873 (6)	0.0369 (2)
N2	1.0951 (4)	0.3458 (3)	0.78336 (19)	0.0267 (6)
H2A	1.0310	0.3654	0.8237	0.032*
H2D	1.2013	0.3360	0.8091	0.032*
N1	0.8525 (4)	0.3466 (3)	0.63036 (19)	0.0262 (6)
H1D	0.9222	0.3270	0.5917	0.031*
C6	0.8591 (5)	0.2469 (3)	0.6942 (2)	0.0266 (7)
H6A	0.8235	0.1729	0.6649	0.032*
H6B	0.7812	0.2642	0.7344	0.032*
C4	1.0905 (5)	0.4452 (3)	0.7205 (2)	0.0332 (8)
H4A	1.1679	0.4280	0.6800	0.040*
H4B	1.1262	0.5191	0.7499	0.040*
C5	1.0336 (5)	0.2302 (3)	0.7425 (2)	0.0261 (7)
H5A	1.1095	0.2063	0.7019	0.031*
C3	0.9163 (5)	0.4608 (3)	0.6735 (2)	0.0328 (8)
H3A	0.8411	0.4854	0.7134	0.039*
H3B	0.9173	0.5236	0.6311	0.039*
O1	0.7146 (4)	0.2021 (3)	0.49063 (18)	0.0422 (7)
H1A	0.6727	0.1408	0.4683	0.063*
C1	0.6018 (5)	0.2547 (4)	0.5418 (3)	0.0375 (9)
H1B	0.5787	0.1985	0.5857	0.045*
H1C	0.4965	0.2739	0.5068	0.045*
C7	1.0337 (6)	0.1329 (4)	0.8089 (3)	0.0410 (10)
H7A	1.1452	0.1236	0.8388	0.061*
H7B	0.9976	0.0587	0.7815	0.061*
H7C	0.9584	0.1546	0.8486	0.061*
C2	0.6798 (5)	0.3669 (4)	0.5825 (3)	0.0372 (9)
H2B	0.6075	0.3986	0.6215	0.045*
H2C	0.6868	0.4265	0.5384	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.03076 (17)	0.02561 (17)	0.02899 (17)	−0.00180 (10)	0.00547 (12)	0.00126 (10)
Cl4	0.0366 (5)	0.0285 (5)	0.0240 (4)	−0.0056 (4)	0.0020 (3)	0.0008 (3)
Cl2	0.0334 (5)	0.0380 (5)	0.0409 (5)	0.0029 (4)	0.0160 (4)	0.0066 (4)
Cl3	0.0476 (6)	0.0283 (5)	0.0354 (5)	−0.0012 (4)	0.0140 (4)	−0.0020 (4)
Cl1	0.0296 (5)	0.0426 (6)	0.0379 (5)	−0.0037 (4)	0.0026 (4)	0.0134 (4)
N2	0.0242 (15)	0.0290 (16)	0.0268 (15)	0.0015 (12)	0.0028 (12)	−0.0039 (12)
N1	0.0293 (16)	0.0260 (16)	0.0234 (15)	0.0015 (12)	0.0037 (12)	−0.0019 (12)
C6	0.0281 (18)	0.0222 (18)	0.0298 (18)	−0.0016 (14)	0.0056 (14)	0.0004 (14)
C4	0.038 (2)	0.0281 (19)	0.0325 (19)	−0.0086 (16)	0.0027 (16)	0.0004 (16)
C5	0.0274 (18)	0.0234 (18)	0.0279 (17)	0.0014 (14)	0.0049 (14)	−0.0028 (14)
C3	0.043 (2)	0.0246 (19)	0.0294 (19)	−0.0022 (16)	−0.0009 (16)	0.0004 (15)
O1	0.0465 (17)	0.0395 (17)	0.0403 (16)	−0.0039 (13)	0.0052 (13)	−0.0102 (13)
C1	0.031 (2)	0.040 (2)	0.039 (2)	0.0002 (17)	−0.0041 (17)	−0.0033 (18)
C7	0.049 (3)	0.031 (2)	0.042 (2)	0.0033 (18)	0.003 (2)	0.0055 (18)
C2	0.038 (2)	0.034 (2)	0.037 (2)	0.0083 (17)	−0.0064 (18)	−0.0045 (17)

Geometric parameters (Å, º) top

Cd1—Cl3	2.5003 (11)	C4—C3	1.502 (6)
Cd1—Cl2	2.5052 (11)	C4—H4A	0.9700
Cd1—Cl4ⁱ	2.5603 (10)	C4—H4B	0.9700
Cd1—Cl1	2.5690 (11)	C5—C7	1.509 (5)
Cd1—Cl4	2.7371 (10)	C5—H5A	0.9800
Cl4—Cd1ⁱ	2.5603 (10)	C3—H3A	0.9700
N2—C4	1.486 (5)	C3—H3B	0.9700
N2—C5	1.495 (4)	O1—C1	1.421 (5)
N2—H2A	0.9000	O1—H1A	0.8200
N2—H2D	0.9000	C1—C2	1.503 (5)
N1—C6	1.497 (4)	C1—H1B	0.9700
N1—C3	1.501 (5)	C1—H1C	0.9700
N1—C2	1.505 (5)	C7—H7A	0.9600
N1—H1D	0.9100	C7—H7B	0.9600
C6—C5	1.514 (5)	C7—H7C	0.9600
C6—H6A	0.9700	C2—H2B	0.9700
C6—H6B	0.9700	C2—H2C	0.9700

Cl3—Cd1—Cl2	111.44 (4)	C3—C4—H4B	109.5
Cl3—Cd1—Cl4ⁱ	143.67 (4)	H4A—C4—H4B	108.1
Cl2—Cd1—Cl4ⁱ	103.18 (4)	N2—C5—C7	110.4 (3)
Cl3—Cd1—Cl1	95.79 (4)	N2—C5—C6	109.9 (3)
Cl2—Cd1—Cl1	97.14 (4)	C7—C5—C6	110.7 (3)
Cl4ⁱ—Cd1—Cl1	90.41 (4)	N2—C5—H5A	108.6
Cl3—Cd1—Cl4	88.47 (3)	C7—C5—H5A	108.6
Cl2—Cd1—Cl4	89.31 (4)	C6—C5—H5A	108.6
Cl4ⁱ—Cd1—Cl4	81.10 (4)	N1—C3—C4	111.4 (3)
Cl1—Cd1—Cl4	170.34 (3)	N1—C3—H3A	109.4
Cd1ⁱ—Cl4—Cd1	98.90 (4)	C4—C3—H3A	109.4
C4—N2—C5	112.1 (3)	N1—C3—H3B	109.4
C4—N2—H2A	109.2	C4—C3—H3B	109.4
C5—N2—H2A	109.2	H3A—C3—H3B	108.0
C4—N2—H2D	109.2	C1—O1—H1A	109.5
C5—N2—H2D	109.2	O1—C1—C2	109.0 (3)
H2A—N2—H2D	107.9	O1—C1—H1B	109.9
C6—N1—C3	110.1 (3)	C2—C1—H1B	109.9
C6—N1—C2	113.4 (3)	O1—C1—H1C	109.9
C3—N1—C2	109.6 (3)	C2—C1—H1C	109.9
C6—N1—H1D	107.9	H1B—C1—H1C	108.3
C3—N1—H1D	107.9	C5—C7—H7A	109.5
C2—N1—H1D	107.9	C5—C7—H7B	109.5
N1—C6—C5	112.2 (3)	H7A—C7—H7B	109.5
N1—C6—H6A	109.2	C5—C7—H7C	109.5
C5—C6—H6A	109.2	H7A—C7—H7C	109.5
N1—C6—H6B	109.2	H7B—C7—H7C	109.5
C5—C6—H6B	109.2	C1—C2—N1	113.1 (3)
H6A—C6—H6B	107.9	C1—C2—H2B	109.0
N2—C4—C3	110.8 (3)	N1—C2—H2B	109.0
N2—C4—H4A	109.5	C1—C2—H2C	109.0
C3—C4—H4A	109.5	N1—C2—H2C	109.0
N2—C4—H4B	109.5	H2B—C2—H2C	107.8

Cl3—Cd1—Cl4—Cd1ⁱ	145.07 (4)	N1—C6—C5—N2	55.2 (4)
Cl2—Cd1—Cl4—Cd1ⁱ	−103.46 (4)	N1—C6—C5—C7	177.4 (3)
Cl4ⁱ—Cd1—Cl4—Cd1ⁱ	0.0	C6—N1—C3—C4	55.9 (4)
Cl1—Cd1—Cl4—Cd1ⁱ	28.7 (2)	C2—N1—C3—C4	−178.7 (3)
C3—N1—C6—C5	−55.7 (4)	N2—C4—C3—N1	−56.5 (4)
C2—N1—C6—C5	−178.9 (3)	O1—C1—C2—N1	−53.4 (5)
C5—N2—C4—C3	56.5 (4)	C6—N1—C2—C1	−52.8 (5)
C4—N2—C5—C7	−177.7 (3)	C3—N1—C2—C1	−176.3 (3)
C4—N2—C5—C6	−55.3 (4)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl4ⁱⁱ	0.82	2.68	3.188 (3)	121
N1—H1D···Cl3ⁱⁱⁱ	0.91	2.29	3.163 (3)	161
N2—H2D···Cl4^iv	0.90	2.88	3.405 (3)	119
N2—H2D···Cl1^v	0.90	2.35	3.125 (3)	144
N2—H2A···Cl2^vi	0.90	2.25	3.119 (3)	164

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

Experimental details

Crystal data
Chemical formula	(C₇H₁₈N₂O)₂[Cd₂Cl₈]
M_r	800.86
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.0318 (16), 11.144 (2), 15.816 (3)
β (°)	97.81 (3)
V (Å³)	1402.6 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.632, 0.638
No. of measured, independent and observed [I > 2σ(I)] reflections	14193, 3217, 3008
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.060, 1.19
No. of reflections	3217
No. of parameters	136
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.88

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl4ⁱ	0.82	2.68	3.188 (3)	121
N1—H1D···Cl3ⁱⁱ	0.91	2.29	3.163 (3)	161
N2—H2D···Cl4ⁱⁱⁱ	0.90	2.88	3.405 (3)	119
N2—H2D···Cl1^iv	0.90	2.35	3.125 (3)	144
N2—H2A···Cl2^v	0.90	2.25	3.119 (3)	164

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

Acknowledgements

The authors are grateful to the starter fund of Southeast University for financial support to purchase the X-ray diffractometer.

References

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page m396

doi:10.1107/S1600536811006945

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

Bis[(2S,4S)-4-(2-hy­dr­oxy­eth­yl)-2-methyl­piperazine-1,4-diium] di-μ-chlorido-bis­­[tri­chloridocadmium(II)]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[(2S,4S)-4-(2-hydroxyethyl)-2-methylpiperazine-1,4-diium] di-μ-chlorido-bis[trichloridocadmium(II)]