Bis(4,4′-methyl­enedicyclo­hexyl­aminium) μ-benzene-1,4-dicarboxyl­ato-bis­[tri­chlorido­zinc(II)] tetra­hydrate

Hsu, C.-Y.; Yeh, C.-W.; Wu, C.-P.; Lin, C.-H.; Chen, J.-D.

doi:10.1107/S1600536808033011

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1412

doi:10.1107/S1600536808033011

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Bis(4,4′-methylenedicyclohexylaminium) μ-benzene-1,4-dicarboxylato-bis[trichloridozinc(II)] tetrahydrate

Chen-Yen Hsu,^a Chun-Wei Yeh,^a Chi-Phi Wu,^a Chia-Her Lin ^a ^* and Jhy-Der Chen ^a

^aDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li 320, Taiwan
^*Correspondence e-mail: chiaher@cycu.edu.tw

(Received 15 September 2008; accepted 12 October 2008; online 15 October 2008)

The title compound, (C₁₃H₂₈N₂)₂[Zn₂(C₈H₄O₄)Cl₆]·4H₂O, was prepared by the reaction of ZnCl₂·6H₂O, benzene-1,4-dicarboxylic acid and 4,4′-diaminodicyclohexylmethane in methanol. The [Zn₂Cl₆(C₈H₄O₄)]⁴⁻ anions lie on centres of inversion and comprise two ZnCl₃ groups bridged by benzene-1,4-dicarboxylate. In addition to N—H⋯Cl and N—H⋯O hydrogen bonds between the cations and anions, solvent water molecules form O—H⋯O and O—H⋯Cl hydrogen bonds to give a three-dimensional network.

Related literature

For related structures, see: Clausen et al. (2005 ); Thirumurugan & Rao (2005 ); Li et al. (1998 , 1999 ).

Experimental

Crystal data

(C₁₃H₂₈N₂)₂[Zn₂(C₈H₄O₄)Cl₆]·4H₂O
M_r = 1004.36
Monoclinic, P 2₁ /c
a = 14.264 (3) Å
b = 14.202 (2) Å
c = 11.712 (2) Å
β = 100.498 (16)°
V = 2333.0 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.42 mm⁻¹
T = 295 (2) K
0.70 × 0.40 × 0.10 mm

Data collection

Bruker P4 diffractometer
Absorption correction: ψ scan (XSCANS; Siemens, 1995 ) T_min = 0.694, T_max = 0.868
5093 measured reflections
4071 independent reflections
3405 reflections with I > 2σ(I)
R_int = 0.027
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.132
S = 1.05
4071 reflections
244 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.10 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl3	0.89	2.41	3.252 (4)	159
N1—H1B⋯Cl2ⁱ	0.89	2.51	3.290 (4)	147
N1—H1C⋯O3ⁱ	0.89	1.94	2.828 (5)	178
N2—H2A⋯Cl1ⁱⁱ	0.89	2.95	3.725 (5)	146
N2—H2A⋯Cl2ⁱⁱ	0.89	2.67	3.321 (4)	131
N2—H2B⋯O2ⁱⁱⁱ	0.89	2.06	2.928 (4)	166
N2—H2C⋯O4^iv	0.89	1.95	2.813 (4)	164
O3—H3B⋯O2	1.00	1.81	2.798 (4)	167.8
O3—H3C⋯Cl1^v	1.06	2.24	3.262 (4)	160.3
O4—H4B⋯Cl3	0.98	2.21	3.172 (4)	164.9
O4—H4C⋯Cl2^vi	0.94	2.38	3.258 (3)	154.9
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) -x, -y+1, -z; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x+1, -y+1, -z; (vi) -x+1, -y+1, -z+1.

Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033011/bi2304sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033011/bi2304Isup2.hkl

checkCIF report

Comment top

The dianion of benzene-1,4-dicarboxylic acid is an important linker to bridge metal atoms which show significant chemical and physical properties (Clausen et al., 2005; Thirumurugan & Rao, 2005; Li et al., 1998, 1999). Since the anions contain four O atoms which are good hydrogen-bond acceptors, co-crystallization with organic cations would be expected to result in extensive hydrogen-bond networks. The title compound (Fig. 1) contains N—H···Cl and N—H···O hydrogen bonds between the cations and the anions, as well as O—H···O and O—H···Cl interactions formed by the lattice water molecules.

Related literature top

For related structures, see: Clausen et al. (2005); Thirumurugan & Rao (2005); Li et al. (1998, 1999).

Experimental top

ZnCl₂.6H₂O (0.49 g, 2.00 mmol) was added to a solution of 4,4'-diaminodicyclohexylmethane (0.21 g,1.00 mmol) and benzene-1,4-dicarboxylic acid (0.17 g, 1.00 mmol) in 30 ml MeOH. The mixture was refluxed for 24 h to yield a colorless solution with some white solid. The solution was filtered and then diethyl ether was added to induce precipitation. The precipitate was filtered and washed by ether (3 × 10 ml), then dried under reduced pressure to give a white powder. Colourless crystals were obtained by slow diffusion of ether into a methanol solution of the white powder over several weeks.

Computing details top

Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS (Siemens, 1995); data reduction: SHELXTL (Sheldrick, 2008); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level for non-H atoms. The [Zn₂Cl₆(C₈H₄O₄)]^4- anion lies on a centre of inversion. Symmetry code: -x, 1 - y, -z.

Bis(4,4'-methylenedicyclohexylaminium) µ-benzene-1,4-dicarboxylato-bis[trichloridozinc(II)] tetrahydrate top

Crystal data top

(C₁₃H₂₈N₂)₂[Zn₂(C₈H₄O₄)Cl₆]·4H₂O	F(000) = 1052
M_r = 1004.36	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 33 reflections
a = 14.264 (3) Å	θ = 5.7–12.5°
b = 14.202 (2) Å	µ = 1.42 mm⁻¹
c = 11.712 (2) Å	T = 295 K
β = 100.498 (16)°	Plate, colourless
V = 2333.0 (7) Å³	0.70 × 0.40 × 0.10 mm
Z = 2

Data collection top

Bruker P4 diffractometer	3405 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ω scans	h = −16→16
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	k = −1→16
T_min = 0.694, T_max = 0.868	l = −1→13
5093 measured reflections	3 standard reflections every 97 reflections
4071 independent reflections	intensity decay: none

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0344P)² + 8.1458P] where P = (F_o² + 2F_c²)/3
4071 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 1.10 e Å⁻³
2 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

(C₁₃H₂₈N₂)₂[Zn₂(C₈H₄O₄)Cl₆]·4H₂O	V = 2333.0 (7) Å³
M_r = 1004.36	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.264 (3) Å	µ = 1.42 mm⁻¹
b = 14.202 (2) Å	T = 295 K
c = 11.712 (2) Å	0.70 × 0.40 × 0.10 mm
β = 100.498 (16)°

Data collection top

Bruker P4 diffractometer	3405 reflections with I > 2σ(I)
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	R_int = 0.027
T_min = 0.694, T_max = 0.868	3 standard reflections every 97 reflections
5093 measured reflections	intensity decay: none
4071 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	2 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.05	Δρ_max = 1.10 e Å⁻³
4071 reflections	Δρ_min = −0.83 e Å⁻³
244 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
Zn	0.37495 (3)	0.50908 (4)	0.23918 (5)	0.04083 (17)
Cl1	0.48147 (11)	0.41661 (13)	0.17455 (16)	0.0807 (5)
Cl2	0.41895 (9)	0.66231 (9)	0.22022 (11)	0.0522 (3)
Cl3	0.37246 (11)	0.48512 (10)	0.42863 (12)	0.0611 (4)
O1	0.2401 (2)	0.4944 (3)	0.1703 (3)	0.0528 (9)
O2	0.2553 (2)	0.4968 (3)	−0.0161 (3)	0.0515 (8)
O3	0.3060 (3)	0.6499 (3)	−0.1424 (4)	0.0829 (14)
H3B	0.2830	0.5919	−0.1077	0.124*
H3C	0.3735	0.6415	−0.1668	0.124*
O4	0.4724 (3)	0.2921 (3)	0.5161 (3)	0.0663 (11)
H4B	0.4531	0.3555	0.4871	0.099*
H4C	0.4917	0.2894	0.5972	0.099*
N1	0.3214 (3)	0.6947 (3)	0.5109 (4)	0.0624 (12)
H1A	0.3470	0.6458	0.4802	0.094*
H1B	0.3575	0.7097	0.5787	0.094*
H1C	0.3179	0.7437	0.4629	0.094*
N2	−0.3906 (3)	0.6298 (3)	0.0987 (4)	0.0495 (10)
H2A	−0.4399	0.6000	0.1193	0.074*
H2B	−0.3577	0.5897	0.0629	0.074*
H2C	−0.4119	0.6769	0.0508	0.074*
C1	0.2069 (3)	0.4959 (3)	0.0619 (4)	0.0392 (10)
C2	0.0992 (3)	0.4974 (3)	0.0298 (4)	0.0365 (9)
C3	0.0434 (3)	0.4915 (4)	0.1146 (4)	0.0447 (11)
H3A	0.0724	0.4857	0.1922	0.054*
C4	−0.0549 (3)	0.4940 (3)	0.0853 (4)	0.0425 (11)
H4A	−0.0915	0.4900	0.1432	0.051*
C5	0.2238 (3)	0.6694 (4)	0.5292 (5)	0.0494 (12)
H5A	0.2286	0.6161	0.5831	0.059*
C6	0.1788 (4)	0.7515 (4)	0.5812 (5)	0.0599 (14)
H6A	0.2171	0.7677	0.6558	0.072*
H6B	0.1766	0.8058	0.5306	0.072*
C7	0.0792 (4)	0.7268 (6)	0.5970 (6)	0.087 (2)
H7A	0.0504	0.7796	0.6301	0.104*
H7B	0.0806	0.6733	0.6487	0.104*
C8	0.0217 (4)	0.7026 (8)	0.4758 (9)	0.153 (5)
H8A	0.0323	0.7544	0.4244	0.183*
C9	0.0658 (4)	0.6144 (7)	0.4308 (9)	0.144 (5)
H9A	0.0680	0.5633	0.4862	0.173*
H9B	0.0278	0.5943	0.3576	0.173*
C10	0.1653 (4)	0.6397 (5)	0.4146 (6)	0.084 (2)
H10A	0.1949	0.5858	0.3845	0.101*
H10B	0.1626	0.6907	0.3590	0.101*
C11	−0.0777 (4)	0.6972 (7)	0.4707 (7)	0.129 (4)
H11A	−0.0985	0.7584	0.4932	0.154*
H11B	−0.0886	0.6529	0.5299	0.154*
C12	−0.1428 (5)	0.6698 (5)	0.3598 (5)	0.082 (2)
H12A	−0.1106	0.6224	0.3200	0.099*
C13	−0.2310 (6)	0.6253 (5)	0.3937 (6)	0.086 (2)
H13A	−0.2119	0.5736	0.4470	0.104*
H13B	−0.2637	0.6716	0.4331	0.104*
C14	−0.2979 (5)	0.5892 (4)	0.2885 (5)	0.0648 (16)
H14A	−0.2665	0.5405	0.2512	0.078*
H14B	−0.3538	0.5619	0.3119	0.078*
C15	−0.3274 (3)	0.6681 (3)	0.2049 (4)	0.0448 (11)
H15A	−0.3640	0.7138	0.2416	0.054*
C16	−0.2440 (4)	0.7187 (4)	0.1693 (5)	0.0568 (14)
H16A	−0.2669	0.7726	0.1214	0.068*
H16B	−0.2118	0.6767	0.1237	0.068*
C17	−0.1739 (4)	0.7515 (4)	0.2759 (5)	0.0657 (16)
H17A	−0.2035	0.8001	0.3155	0.079*
H17B	−0.1182	0.7786	0.2516	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.0279 (3)	0.0487 (3)	0.0448 (3)	0.0002 (2)	0.0038 (2)	−0.0039 (2)
Cl1	0.0513 (8)	0.0921 (12)	0.0964 (12)	0.0202 (8)	0.0077 (8)	−0.0412 (10)
Cl2	0.0443 (6)	0.0524 (7)	0.0572 (7)	−0.0055 (5)	0.0023 (5)	0.0085 (6)
Cl3	0.0727 (9)	0.0612 (8)	0.0493 (7)	0.0159 (7)	0.0108 (6)	0.0109 (6)
O1	0.0318 (16)	0.074 (2)	0.050 (2)	−0.0063 (17)	−0.0002 (14)	−0.0007 (18)
O2	0.0348 (17)	0.063 (2)	0.060 (2)	0.0050 (16)	0.0154 (15)	0.0004 (17)
O3	0.086 (3)	0.063 (3)	0.112 (4)	0.007 (2)	0.051 (3)	0.012 (2)
O4	0.074 (3)	0.052 (2)	0.065 (2)	0.0020 (19)	−0.010 (2)	0.0026 (18)
N1	0.059 (3)	0.057 (3)	0.074 (3)	−0.014 (2)	0.020 (2)	−0.018 (2)
N2	0.034 (2)	0.059 (3)	0.056 (2)	−0.0009 (19)	0.0076 (18)	−0.004 (2)
C1	0.032 (2)	0.030 (2)	0.055 (3)	0.0004 (18)	0.006 (2)	−0.005 (2)
C2	0.028 (2)	0.035 (2)	0.046 (2)	−0.0022 (18)	0.0072 (18)	−0.0064 (19)
C3	0.036 (2)	0.059 (3)	0.038 (2)	−0.001 (2)	0.0023 (19)	−0.002 (2)
C4	0.035 (2)	0.054 (3)	0.040 (2)	0.000 (2)	0.0110 (19)	−0.003 (2)
C5	0.041 (3)	0.044 (3)	0.060 (3)	−0.001 (2)	0.001 (2)	−0.006 (2)
C6	0.057 (3)	0.064 (3)	0.056 (3)	0.001 (3)	0.003 (3)	−0.022 (3)
C7	0.042 (3)	0.116 (6)	0.097 (5)	0.002 (3)	−0.001 (3)	−0.063 (5)
C8	0.044 (4)	0.219 (11)	0.181 (9)	0.025 (5)	−0.015 (5)	−0.162 (9)
C9	0.038 (3)	0.181 (9)	0.198 (10)	0.017 (5)	−0.018 (5)	−0.149 (8)
C10	0.065 (4)	0.097 (5)	0.081 (4)	0.030 (4)	−0.013 (3)	−0.049 (4)
C11	0.084 (5)	0.167 (9)	0.113 (6)	0.057 (6)	−0.042 (5)	−0.090 (6)
C12	0.077 (4)	0.090 (5)	0.066 (4)	0.044 (4)	−0.024 (3)	−0.038 (4)
C13	0.120 (6)	0.074 (4)	0.054 (4)	−0.001 (4)	−0.013 (4)	−0.001 (3)
C14	0.089 (4)	0.052 (3)	0.049 (3)	−0.010 (3)	0.003 (3)	−0.001 (3)
C15	0.040 (2)	0.048 (3)	0.047 (3)	0.000 (2)	0.011 (2)	−0.004 (2)
C16	0.046 (3)	0.063 (3)	0.059 (3)	−0.011 (3)	0.005 (2)	0.012 (3)
C17	0.046 (3)	0.071 (4)	0.079 (4)	−0.011 (3)	0.009 (3)	−0.011 (3)

Geometric parameters (Å, º) top

Zn—O1	1.956 (3)	C7—C8	1.543 (9)
Zn—Cl1	2.2418 (15)	C7—H7A	0.97
Zn—Cl3	2.2514 (15)	C7—H7B	0.97
Zn—Cl2	2.2869 (14)	C8—C11	1.410 (7)
O1—C1	1.272 (6)	C8—C9	1.537 (10)
O2—C1	1.243 (6)	C8—H8A	0.98
O3—H3B	1.00	C9—C10	1.510 (11)
O3—H3C	1.06	C9—H9A	0.97
O4—H4B	0.98	C9—H9B	0.97
O4—H4C	0.94	C10—H10A	0.97
N1—C5	1.491 (6)	C10—H10B	0.97
N1—H1A	0.89	C11—C12	1.503 (6)
N1—H1B	0.89	C11—H11A	0.97
N1—H1C	0.89	C11—H11B	0.97
N2—C15	1.500 (6)	C12—C13	1.524 (11)
N2—H2A	0.89	C12—C17	1.534 (9)
N2—H2B	0.89	C12—H12A	0.98
N2—H2C	0.89	C13—C14	1.503 (8)
C1—C2	1.513 (6)	C13—H13A	0.97
C2—C3	1.385 (6)	C13—H13B	0.97
C2—C4ⁱ	1.386 (6)	C14—C15	1.497 (7)
C3—C4	1.382 (6)	C14—H14A	0.97
C3—H3A	0.93	C14—H14B	0.97
C4—C2ⁱ	1.386 (6)	C15—C16	1.512 (7)
C4—H4A	0.93	C15—H15A	0.98
C5—C10	1.505 (7)	C16—C17	1.523 (8)
C5—C6	1.512 (7)	C16—H16A	0.97
C5—H5A	0.98	C16—H16B	0.97
C6—C7	1.506 (8)	C17—H17A	0.97
C6—H6A	0.97	C17—H17B	0.97
C6—H6B	0.97

O1—Zn—Cl1	118.31 (12)	C7—C8—H8A	106.4
O1—Zn—Cl3	101.50 (11)	C10—C9—C8	107.6 (7)
Cl1—Zn—Cl3	112.19 (7)	C10—C9—H9A	110.2
O1—Zn—Cl2	109.14 (12)	C8—C9—H9A	110.2
Cl1—Zn—Cl2	108.05 (7)	C10—C9—H9B	110.2
Cl3—Zn—Cl2	107.06 (6)	C8—C9—H9B	110.2
C1—O1—Zn	124.7 (3)	H9A—C9—H9B	108.5
H3B—O3—H3C	113.5	C5—C10—C9	109.6 (6)
H4B—O4—H4C	113.5	C5—C10—H10A	109.8
C5—N1—H1A	109.5	C9—C10—H10A	109.8
C5—N1—H1B	109.5	C5—C10—H10B	109.8
H1A—N1—H1B	109.5	C9—C10—H10B	109.8
C5—N1—H1C	109.5	H10A—C10—H10B	108.2
H1A—N1—H1C	109.5	C8—C11—C12	120.6 (7)
H1B—N1—H1C	109.5	C8—C11—H11A	107.2
C15—N2—H2A	109.5	C12—C11—H11A	107.2
C15—N2—H2B	109.5	C8—C11—H11B	107.2
H2A—N2—H2B	109.5	C12—C11—H11B	107.2
C15—N2—H2C	109.5	H11A—C11—H11B	106.8
H2A—N2—H2C	109.5	C11—C12—C13	107.0 (6)
H2B—N2—H2C	109.5	C11—C12—C17	114.7 (7)
O2—C1—O1	125.4 (4)	C13—C12—C17	109.0 (5)
O2—C1—C2	119.5 (4)	C11—C12—H12A	108.6
O1—C1—C2	115.2 (4)	C13—C12—H12A	108.6
C3—C2—C4ⁱ	118.9 (4)	C17—C12—H12A	108.6
C3—C2—C1	120.7 (4)	C14—C13—C12	111.0 (6)
C4ⁱ—C2—C1	120.4 (4)	C14—C13—H13A	109.4
C4—C3—C2	120.7 (4)	C12—C13—H13A	109.4
C4—C3—H3A	119.7	C14—C13—H13B	109.4
C2—C3—H3A	119.7	C12—C13—H13B	109.4
C3—C4—C2ⁱ	120.4 (4)	H13A—C13—H13B	108.0
C3—C4—H4A	119.8	C15—C14—C13	110.0 (5)
C2ⁱ—C4—H4A	119.8	C15—C14—H14A	109.7
N1—C5—C10	108.6 (5)	C13—C14—H14A	109.7
N1—C5—C6	110.4 (4)	C15—C14—H14B	109.7
C10—C5—C6	111.6 (4)	C13—C14—H14B	109.7
N1—C5—H5A	108.7	H14A—C14—H14B	108.2
C10—C5—H5A	108.7	C14—C15—N2	109.0 (4)
C6—C5—H5A	108.7	C14—C15—C16	113.2 (4)
C7—C6—C5	110.4 (5)	N2—C15—C16	109.2 (4)
C7—C6—H6A	109.6	C14—C15—H15A	108.4
C5—C6—H6A	109.6	N2—C15—H15A	108.4
C7—C6—H6B	109.6	C16—C15—H15A	108.4
C5—C6—H6B	109.6	C15—C16—C17	110.6 (5)
H6A—C6—H6B	108.1	C15—C16—H16A	109.5
C6—C7—C8	107.2 (6)	C17—C16—H16A	109.5
C6—C7—H7A	110.3	C15—C16—H16B	109.5
C8—C7—H7A	110.3	C17—C16—H16B	109.5
C6—C7—H7B	110.3	H16A—C16—H16B	108.1
C8—C7—H7B	110.3	C16—C17—C12	111.3 (5)
H7A—C7—H7B	108.5	C16—C17—H17A	109.4
C11—C8—C9	114.4 (7)	C12—C17—H17A	109.4
C11—C8—C7	114.4 (7)	C16—C17—H17B	109.4
C9—C8—C7	108.3 (7)	C12—C17—H17B	109.4
C11—C8—H8A	106.4	H17A—C17—H17B	108.0
C9—C8—H8A	106.4

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl3	0.89	2.41	3.252 (4)	159
N1—H1B···Cl2ⁱⁱ	0.89	2.51	3.290 (4)	147
N1—H1C···O3ⁱⁱ	0.89	1.94	2.828 (5)	178
N2—H2A···Cl1ⁱⁱⁱ	0.89	2.95	3.725 (5)	146
N2—H2A···Cl2ⁱⁱⁱ	0.89	2.67	3.321 (4)	131
N2—H2B···O2ⁱ	0.89	2.06	2.928 (4)	166
N2—H2C···O4^iv	0.89	1.95	2.813 (4)	164
O3—H3B···O2	1.00	1.81	2.798 (4)	167.8
O3—H3C···Cl1^v	1.06	2.24	3.262 (4)	160.3
O4—H4B···Cl3	0.98	2.21	3.172 (4)	164.9
O4—H4C···Cl2^vi	0.94	2.38	3.258 (3)	154.9

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

Experimental details

Crystal data
Chemical formula	(C₁₃H₂₈N₂)₂[Zn₂(C₈H₄O₄)Cl₆]·4H₂O
M_r	1004.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	14.264 (3), 14.202 (2), 11.712 (2)
β (°)	100.498 (16)
V (Å³)	2333.0 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.42
Crystal size (mm)	0.70 × 0.40 × 0.10

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	ψ scan (XSCANS; Siemens, 1995)
T_min, T_max	0.694, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	5093, 4071, 3405
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.132, 1.05
No. of reflections	4071
No. of parameters	244
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.10, −0.83

Computer programs: XSCANS (Siemens, 1995), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl3	0.89	2.41	3.252 (4)	159.0
N1—H1B···Cl2ⁱ	0.89	2.51	3.290 (4)	147.0
N1—H1C···O3ⁱ	0.89	1.94	2.828 (5)	178.2
N2—H2A···Cl1ⁱⁱ	0.89	2.95	3.725 (5)	145.9
N2—H2A···Cl2ⁱⁱ	0.89	2.67	3.321 (4)	131.3
N2—H2B···O2ⁱⁱⁱ	0.89	2.06	2.928 (4)	165.5
N2—H2C···O4^iv	0.89	1.95	2.813 (4)	163.9
O3—H3B···O2	1.00	1.81	2.798 (4)	167.8
O3—H3C···Cl1^v	1.06	2.24	3.262 (4)	160.3
O4—H4B···Cl3	0.98	2.21	3.172 (4)	164.9
O4—H4C···Cl2^vi	0.94	2.38	3.258 (3)	154.9

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

Acknowledgements

The authors are grateful to the National Science Council of Taiwan for support. This research was also supported by the Project of the Specific Research Fields in Chung Yuan Christian University, Taiwan, under grant No. CYCU-97-CR-CH.

References

Clausen, H. F., Poulsen, R. D., Bond, A. D., Chevallier, M.-A. S. & Iversen, B. B. (2005). J. Solid State Chem. 178, 3342–3351. Web of Science CSD CrossRef CAS Google Scholar
Li, H., Eddaoudi, M., Groy, T. L. & Yaghi, O. M. (1998). J. Am. Chem. Soc. 120, 8571–8572. Web of Science CSD CrossRef CAS Google Scholar
Li, H., Eddaoudi, M., O'Keeffe, M. & Yaghi, O. M. (1999). Nature (London), 402, 276–279. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Thirumurugan, A. & Rao, C. N. R. (2005). J. Mater. Chem. 15, 3852–3858. Web of Science CSD CrossRef CAS Google Scholar

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Volume 64| Part 11| November 2008| Page m1412

doi:10.1107/S1600536808033011

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

Bis(4,4′-methyl­enedi­cyclo­hexyl­aminium) μ-benzene-1,4-di­carboxyl­ato-bis­­[tri­chlorido­zinc(II)] tetra­hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(4,4′-methylenedicyclohexylaminium) μ-benzene-1,4-dicarboxylato-bis[trichloridozinc(II)] tetrahydrate