trans-N,N,N',N'-Tetra-kis(carboxy-meth-yl)cyclo-hexane-1,2-diammonium tetra-chloridocadmium(II) tetra-hydrate.

In the title compound, (C(14)H(24)N(2)O(8))[CdCl(4)]·4H(2)O, the Cd atom in the tetra-hedral [CdCl(4)](2-) anion lies on a twofold rotation axis, and the diprotonated organic mol-ecule, trans-N,N,N',N'-tetra-kis(carb-oxy-meth-yl)cyclo-hexane-1,2-diammon-ium, has 2 symmetry with the twofold rotation axis running through the mid-point of two C-C bonds in the cyclo-hexane unit. In the crystal structure, classical intra-molecular O-H⋯O and N-H⋯O and inter-molecular O-H⋯O, N-H⋯O, O-H⋯Cl and C-H⋯Cl hydrogen bonds are observed.

Related literature

For the structure of 1,2-diamino­cyclo­hexane-N,N′-tetra­acetate ferrate(III), see: Seibig & Van Eldik (1998 ▶). For related tetra­acetate-based Cu(II) dimeric and polymeric complexes, see: Wang et al. (1999 ▶); Ben Amor & Jouini (1999 ▶). For highly stable chiral three-dimensional cadmium 1,2,4-benzene­tricarboxyl­ate structures with NLO and fluorescence properties, see: Wang et al. (2006 ▶). For a flexible multicarboxyl­ate ligand used to form homochiral helical Zn and Cd coordination polymers, see: Zang et al. (2006 ▶).

Experimental

Crystal data

(C14H24N2O8)[CdCl4]·4H2O

M = 674.63

Monoclinic,

a = 11.3772 (14) Å

b = 8.5734 (10) Å

c = 16.2189 (16) Å

β = 124.119 (6)°

V = 1309.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.30 mm−1

T = 291 (2) K

0.68 × 0.54 × 0.28 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.472, T max = 0.712

12160 measured reflections

2400 independent reflections

2319 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.069

S = 1.01

2400 reflections

166 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.59 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680804110X/si2140sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804110X/si2140Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C14H24N2O8)[CdCl4]·4H2O	F(000) = 684
Mr = 674.63	Dx = 1.711 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yc	Cell parameters from 4992 reflections
a = 11.3772 (14) Å	θ = 3.0–25.4°
b = 8.5734 (10) Å	µ = 1.30 mm−1
c = 16.2189 (16) Å	T = 291 K
β = 124.119 (6)°	Block, colorless
V = 1309.7 (3) Å3	0.68 × 0.54 × 0.28 mm
Z = 2

Siemens SMART CCD area-detector diffractometer	2400 independent reflections
Radiation source: fine-focus sealed tube	2319 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 25.4°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.472, Tmax = 0.712	k = −9→10
12160 measured reflections	l = −19→17

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) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.6848P] where P = (Fo2 + 2Fc2)/3
2400 reflections	(Δ/σ)max = 0.002
166 parameters	Δρmax = 0.33 e Å−3
9 restraints	Δρmin = −0.59 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cd1	0.0000	0.53761 (3)	0.2500	0.03615 (11)
Cl1	0.02889 (8)	0.72055 (7)	0.37802 (5)	0.04979 (18)
Cl2	0.21701 (5)	0.38349 (7)	0.32009 (4)	0.03949 (15)
O1	0.4348 (2)	0.2419 (2)	0.94146 (13)	0.0498 (5)
H1C	0.3671	0.1650	0.9099	0.075*
O1W	0.2453 (3)	0.0262 (3)	0.8865 (2)	0.0679 (6)
O2	0.40158 (16)	0.24536 (18)	0.79129 (11)	0.0359 (4)
O2W	−0.0832 (3)	0.9342 (3)	0.8284 (2)	0.0894 (9)
O3	0.75562 (17)	0.18174 (18)	0.96741 (12)	0.0415 (4)
O4	0.96749 (15)	0.3009 (2)	1.05918 (12)	0.0402 (4)
H4C	0.9916	0.2307	1.1010	0.060*
N1	0.62609 (17)	0.44661 (18)	0.85909 (12)	0.0222 (3)
H1B	0.6007	0.3609	0.8194	0.027*
C1	0.5801 (2)	0.5898 (2)	0.79036 (14)	0.0247 (4)
H1A	0.6297	0.5854	0.7568	0.030*
C2	0.6258 (3)	0.7396 (2)	0.85186 (17)	0.0363 (5)
H2A	0.5848	0.7420	0.8905	0.044*
H2B	0.7283	0.7402	0.8980	0.044*
C3	0.5796 (3)	0.8841 (3)	0.78646 (19)	0.0443 (6)
H3A	0.6088	0.9769	0.8277	0.053*
H3B	0.6248	0.8856	0.7505	0.053*
C4	0.5549 (2)	0.4321 (2)	0.91397 (15)	0.0270 (4)
H4A	0.6261	0.4184	0.9846	0.032*
H4B	0.5022	0.5267	0.9052	0.032*
C5	0.4558 (2)	0.2950 (3)	0.87470 (16)	0.0301 (4)
C6	0.7845 (2)	0.4427 (2)	0.92917 (16)	0.0306 (5)
H6A	0.8157	0.5296	0.9752	0.037*
H6B	0.8270	0.4539	0.8917	0.037*
C7	0.8335 (2)	0.2919 (3)	0.98686 (15)	0.0306 (5)
H2WA	−0.126 (7)	0.924 (6)	0.7667 (17)	0.18 (3)*
H2WB	−0.090 (5)	1.020 (3)	0.848 (3)	0.106 (18)*
H1WA	0.271 (5)	−0.061 (4)	0.915 (4)	0.15 (2)*
H1WB	0.189 (5)	0.069 (4)	0.899 (6)	0.29 (5)*

	U11	U22	U33	U12	U13	U23
Cd1	0.03114 (15)	0.04045 (17)	0.03324 (15)	0.000	0.01584 (12)	0.000
Cl1	0.0697 (4)	0.0412 (3)	0.0407 (3)	0.0038 (3)	0.0323 (3)	−0.0005 (3)
Cl2	0.0280 (3)	0.0544 (4)	0.0334 (3)	0.0020 (2)	0.0156 (2)	−0.0005 (2)
O1	0.0634 (11)	0.0554 (11)	0.0410 (10)	−0.0215 (9)	0.0357 (9)	−0.0021 (8)
O1W	0.0683 (14)	0.0591 (14)	0.0808 (16)	−0.0126 (11)	0.0445 (14)	0.0116 (12)
O2	0.0398 (8)	0.0370 (8)	0.0317 (8)	−0.0104 (7)	0.0205 (7)	−0.0036 (7)
O2W	0.0851 (18)	0.0461 (13)	0.0653 (16)	0.0025 (13)	−0.0017 (14)	0.0128 (12)
O3	0.0376 (9)	0.0303 (8)	0.0397 (9)	−0.0023 (7)	0.0113 (7)	0.0016 (7)
O4	0.0262 (8)	0.0442 (9)	0.0355 (9)	0.0021 (7)	0.0083 (7)	0.0114 (7)
N1	0.0222 (8)	0.0239 (8)	0.0187 (8)	−0.0013 (6)	0.0103 (7)	−0.0016 (6)
C1	0.0271 (10)	0.0240 (9)	0.0206 (9)	−0.0011 (8)	0.0120 (9)	0.0022 (8)
C2	0.0394 (12)	0.0262 (11)	0.0295 (11)	−0.0050 (9)	0.0109 (10)	−0.0033 (9)
C3	0.0488 (14)	0.0257 (11)	0.0440 (13)	−0.0060 (10)	0.0174 (12)	−0.0003 (10)
C4	0.0297 (10)	0.0328 (10)	0.0213 (10)	0.0010 (9)	0.0161 (9)	0.0015 (8)
C5	0.0303 (11)	0.0328 (11)	0.0300 (11)	0.0018 (9)	0.0185 (9)	0.0054 (9)
C6	0.0207 (10)	0.0348 (11)	0.0297 (11)	−0.0005 (8)	0.0101 (9)	0.0033 (9)
C7	0.0288 (11)	0.0341 (11)	0.0241 (10)	0.0006 (9)	0.0119 (9)	−0.0013 (9)

Cd1—Cl2i	2.4465 (6)	N1—H1B	0.9105
Cd1—Cl2	2.4465 (6)	C1—C2	1.527 (3)
Cd1—Cl1	2.4725 (7)	C1—C1ii	1.536 (4)
Cd1—Cl1i	2.4725 (7)	C1—H1A	0.9800
O1—C5	1.314 (3)	C2—C3	1.520 (3)
O1—H1C	0.9209	C2—H2A	0.9700
O1W—H1WA	0.84 (4)	C2—H2B	0.9700
O1W—H1WB	0.86 (7)	C3—C3ii	1.508 (5)
O2—C5	1.207 (3)	C3—H3A	0.9700
O2W—H2WA	0.84 (3)	C3—H3B	0.9700
O2W—H2WB	0.82 (3)	C4—C5	1.501 (3)
O3—C7	1.209 (3)	C4—H4A	0.9700
O4—C7	1.304 (3)	C4—H4B	0.9700
O4—H4C	0.8305	C6—C7	1.508 (3)
N1—C6	1.497 (3)	C6—H6A	0.9700
N1—C4	1.508 (2)	C6—H6B	0.9700
N1—C1	1.539 (2)
Cl2i—Cd1—Cl2	114.62 (3)	C1—C2—H2B	109.2
Cl2i—Cd1—Cl1	110.91 (2)	H2A—C2—H2B	107.9
Cl2—Cd1—Cl1	109.16 (2)	C3ii—C3—C2	109.91 (19)
Cl2i—Cd1—Cl1i	109.16 (2)	C3ii—C3—H3A	109.7
Cl2—Cd1—Cl1i	110.91 (2)	C2—C3—H3A	109.7
Cl1—Cd1—Cl1i	101.26 (3)	C3ii—C3—H3B	109.7
C5—O1—H1C	105.8	C2—C3—H3B	109.7
H1WA—O1W—H1WB	110 (3)	H3A—C3—H3B	108.2
H2WA—O2W—H2WB	116 (3)	C5—C4—N1	109.79 (16)
C7—O4—H4C	112.1	C5—C4—H4A	109.7
C6—N1—C4	111.50 (15)	N1—C4—H4A	109.7
C6—N1—C1	110.05 (15)	C5—C4—H4B	109.7
C4—N1—C1	114.62 (15)	N1—C4—H4B	109.7
C6—N1—H1B	106.8	H4A—C4—H4B	108.2
C4—N1—H1B	106.7	O2—C5—O1	125.9 (2)
C1—N1—H1B	106.7	O2—C5—C4	122.82 (18)
C2—C1—C1ii	111.29 (14)	O1—C5—C4	111.22 (18)
C2—C1—N1	110.17 (15)	N1—C6—C7	111.04 (17)
C1ii—C1—N1	112.08 (13)	N1—C6—H6A	109.4
C2—C1—H1A	107.7	C7—C6—H6A	109.4
C1ii—C1—H1A	107.7	N1—C6—H6B	109.4
N1—C1—H1A	107.7	C7—C6—H6B	109.4
C3—C2—C1	111.84 (18)	H6A—C6—H6B	108.0
C3—C2—H2A	109.2	O3—C7—O4	126.6 (2)
C1—C2—H2A	109.2	O3—C7—C6	123.08 (19)
C3—C2—H2B	109.2	O4—C7—C6	110.27 (18)
C6—N1—C1—C2	−61.6 (2)	C1—N1—C4—C5	111.04 (18)
C4—N1—C1—C2	65.0 (2)	N1—C4—C5—O2	−26.1 (3)
C6—N1—C1—C1ii	173.88 (18)	N1—C4—C5—O1	155.57 (17)
C4—N1—C1—C1ii	−59.5 (2)	C4—N1—C6—C7	60.0 (2)
C1ii—C1—C2—C3	−53.8 (3)	C1—N1—C6—C7	−171.67 (16)
N1—C1—C2—C3	−178.77 (19)	N1—C6—C7—O3	10.0 (3)
C1—C2—C3—C3ii	58.3 (3)	N1—C6—C7—O4	−168.89 (18)
C6—N1—C4—C5	−123.10 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3iii	0.84 (4)	2.34 (4)	2.970 (3)	132 (5)
N1—H1B···O2	0.91	2.27	2.750 (3)	112
N1—H1B···O2ii	0.91	2.04	2.857 (2)	149
O1—H1C···O1W	0.92	1.70	2.590 (4)	162
O2W—H2WA···O1Wiv	0.84 (3)	2.24 (3)	2.993 (4)	151 (5)
O2W—H2WB···Cl1v	0.82 (3)	2.51 (4)	3.144 (3)	136 (4)
O1W—H1WB···Cl1vi	0.86 (7)	2.45 (3)	3.227 (3)	152 (6)
O4—H4C···O2Wvii	0.83	1.75	2.535 (3)	157
C1—H1A···Cl2viii	0.98	2.67	3.637 (3)	171
C4—H4A···Cl2ii	0.97	2.64	3.600 (2)	170
C4—H4B···Cl2vi	0.97	2.83	3.610 (3)	138
C6—H6A···Cl1ii	0.97	2.60	3.537 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3i	0.84 (4)	2.34 (4)	2.970 (3)	132 (5)
N1—H1B⋯O2	0.91	2.27	2.750 (3)	112
N1—H1B⋯O2ii	0.91	2.04	2.857 (2)	149
O1—H1C⋯O1W	0.92	1.70	2.590 (4)	162
O2W—H2WA⋯O1Wiii	0.84 (3)	2.24 (3)	2.993 (4)	151 (5)
O2W—H2WB⋯Cl1iv	0.82 (3)	2.51 (4)	3.144 (3)	136 (4)
O1W—H1WB⋯Cl1v	0.86 (7)	2.45 (3)	3.227 (3)	152 (6)
O4—H4C⋯O2Wvi	0.83	1.75	2.535 (3)	157
C1—H1A⋯Cl2vii	0.98	2.67	3.637 (3)	171
C4—H4A⋯Cl2ii	0.97	2.64	3.600 (2)	170
C4—H4B⋯Cl2v	0.97	2.83	3.610 (3)	138
C6—H6A⋯Cl1ii	0.97	2.60	3.537 (2)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .