1,4,8,11-Tetra­kis(carboxy­meth­yl)-5,5,7,12,12,14-hexa­methyl-4,11-diaza-1,8-diazo­niacyclo­tetra­decane dichloride dihydrate

Wang, S.-F.; Liu, H.-Q.; Yao, X.-M.; Yang, K.; Li, X.-H.

doi:10.1107/S1600536808010532

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o885

doi:10.1107/S1600536808010532

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1,4,8,11-Tetrakis(carboxymethyl)-5,5,7,12,12,14-hexamethyl-4,11-diaza-1,8-diazoniacyclotetradecane dichloride dihydrate

Shi-Fan Wang,^a ^* Hai-Qing Liu,^b Xue-Mei Yao,^b Kai Yang ^b and Xiao-Hong Li ^b

^aKey Laboratory of Tropical Biological Resources of the Ministry of Education, Hainan University, Haikou 570228, People's Republic of China, and Hainan Provincial Key Laboratory for Tropical Hydrobiology and Biotechnology, School of Ocean, Hainan University, Haikou 570228, People's Republic of China, and ^bDepartment of Pharmaceutical Engineering, School of Ocean, Hainan University, Haikou 570228, People's Republic of China
^*Correspondence e-mail: wangsf777@gmail.com

(Received 6 April 2008; accepted 16 April 2008; online 23 April 2008)

The title compound, C₂₄H₄₆N₄O₈²⁺·2Cl⁻·2H₂O, was synthesized by the hydrolysis of tetraethyl 2,2′,2′′,2′′′-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetrayl) tetraacetate in hydrochloric acid solution. The crystal structure of the title compound consists of a 14-membered C₁₀N₄ centrosymmetric cationic macrocycle which interacts with the chloride ions and water molecules of crystallization to give a three-dimensional hydrogen-bonded network.

Related literature

For related literature, see: Marinelli et al. (2002 ); Wang (2001 ); Xu et al. (1988 ).

Experimental

Crystal data

C₂₄H₄₆N₄O₈²⁺·2Cl⁻·2H₂O
M_r = 625.58
Monoclinic, P 2₁ /n
a = 9.977 (5) Å
b = 13.475 (7) Å
c = 11.572 (6) Å
β = 104.220 (9)°
V = 1508.1 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 (2) K
0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
15242 measured reflections
2946 independent reflections
2036 reflections with I > 2σ(I)
R_int = 0.143

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.141
S = 0.98
2946 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯Cl1ⁱ	0.82	2.24	3.012 (3)	158
O2—H2A⋯O1Wⁱⁱ	0.82	1.82	2.610 (3)	162
O1W—H2W⋯Cl1ⁱⁱⁱ	0.76 (3)	2.40 (3)	3.152 (3)	169 (3)
Symmetry codes: (i) x+1, y, z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010532/wn2251sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010532/wn2251Isup2.hkl

checkCIF report

Comment top

N-functionalized macrocyclic acids are an important class of compounds for their utility as MRI contrast agents (Marinelli et al., 2002) and their strong chelating ability (Xu et al., 1988). For this reason, we have synthesized the title compound by the hydrolysis of tetraethyl 2,2',2'',2'''-(5,5,7,12,12,14-hexamethyl- 1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetrayl) tetraacetate (Wang et al., 2001) in hydrochloric acid solution.

The bond lengths and angles in the title compound are within normal ranges. The structural data confirm that the 14-membered macrocycle lies on a center of inversion and each N atom is linked to a carboxymethyl group. The macrocycle carries two positive charges arising from the protonation of N atoms. The net charge is balanced by two chloride ions. The cations and anions interact with each other and with the water molecules of crystallization to furnish a hydrogen-bonded network structure (Table 1). The structure of the title compound, showing 50% probability displacement ellipsoids is shown in Fig. 1 and a view of the hydrogen bonding in Fig. 2.

Related literature top

For related literature, see: Marinelli et al. (2002); Wang (2001); Xu et al. (1988).

Experimental top

Tetraethyl 2,2',2'',2'''-(5,5,7,12,12,14-hexamethyl- 1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetrayl)tetraacetate (0.625 g, 1 mmol) was dissolved in 200 ml of hydrochloric acid solution (v:v, 1:1) and allowed to stand in air at room temperature over a period of three weeks. Colourless block crystals suitable for X-ray diffraction analysis were formed at the bottom of the vessel (yield 87%).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: (a) 1-x, 2-y, -z.
	Fig. 2. A view of the hydrogen bonding. Dashed lines indicate hydrogen bonds.

1,4,8,11-Tetrakis(carboxymethyl)-5,5,7,12,12,14-hexamethyl- 4,11-diaza-1,8-diazoniacyclotetradecane dichloride dihydrate top

Crystal data top

C₂₄H₄₆N₄O₈²⁺·2Cl⁻·2H₂O	F(000) = 672
M_r = 625.58	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 17651 reflections
a = 9.977 (5) Å	θ = 2.4–24.9°
b = 13.475 (7) Å	µ = 0.27 mm⁻¹
c = 11.572 (6) Å	T = 293 K
β = 104.220 (9)°	BLOCK, colorless
V = 1508.1 (13) Å³	0.10 × 0.10 × 0.08 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2036 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.143
Graphite monochromator	θ_max = 26.0°, θ_min = 2.4°
ϕ and ω scans	h = −12→12
15242 measured reflections	k = −16→16
2946 independent reflections	l = −14→14

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0715P)²] where P = (F_o² + 2F_c²)/3
2946 reflections	(Δ/σ)_max = 0.032
194 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₄H₄₆N₄O₈²⁺·2Cl⁻·2H₂O	V = 1508.1 (13) Å³
M_r = 625.58	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.977 (5) Å	µ = 0.27 mm⁻¹
b = 13.475 (7) Å	T = 293 K
c = 11.572 (6) Å	0.10 × 0.10 × 0.08 mm
β = 104.220 (9)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2036 reflections with I > 2σ(I)
15242 measured reflections	R_int = 0.143
2946 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.63 e Å⁻³
2946 reflections	Δρ_min = −0.37 e Å⁻³
194 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
C1	0.5351 (3)	0.98193 (17)	−0.1532 (2)	0.0292 (6)
H1A	0.4667	0.9400	−0.1306	0.035*
H1B	0.5360	0.9664	−0.2348	0.035*
C2	0.7189 (3)	0.85672 (17)	−0.0818 (2)	0.0335 (6)
H2	0.8150	0.8530	−0.0349	0.040*
C3	0.6370 (3)	0.78525 (17)	−0.0239 (2)	0.0323 (6)
H3A	0.6485	0.7189	−0.0525	0.039*
H3B	0.5398	0.8021	−0.0511	0.039*
C4	0.6741 (3)	0.78252 (17)	0.1120 (2)	0.0319 (6)
C5	0.5034 (2)	0.90943 (16)	0.1443 (2)	0.0285 (6)
H5A	0.4752	0.8726	0.2064	0.034*
H5B	0.4516	0.8836	0.0682	0.034*
C6	0.7192 (4)	0.8235 (2)	−0.2076 (3)	0.0495 (8)
H6A	0.6257	0.8156	−0.2537	0.074*
H6B	0.7673	0.7614	−0.2041	0.074*
H6C	0.7649	0.8726	−0.2444	0.074*
C7	0.8226 (3)	0.7482 (2)	0.1616 (3)	0.0422 (7)
H7A	0.8371	0.6866	0.1248	0.063*
H7B	0.8394	0.7391	0.2462	0.063*
H7C	0.8850	0.7974	0.1450	0.063*
C8	0.5799 (3)	0.70891 (19)	0.1556 (3)	0.0442 (7)
H8A	0.6022	0.6425	0.1369	0.066*
H8B	0.4851	0.7228	0.1169	0.066*
H8C	0.5933	0.7154	0.2403	0.066*
C9	0.7378 (2)	0.91341 (19)	0.2780 (2)	0.0328 (6)
H9A	0.7422	0.8550	0.3278	0.039*
H9B	0.6935	0.9660	0.3121	0.039*
C10	0.8828 (3)	0.94509 (17)	0.2765 (2)	0.0303 (6)
C11	0.7806 (3)	1.03008 (17)	−0.0922 (2)	0.0338 (6)
H11A	0.7562	1.0512	−0.1749	0.041*
H11B	0.8669	0.9937	−0.0793	0.041*
C12	0.8052 (3)	1.12186 (18)	−0.0142 (2)	0.0319 (6)
Cl1	0.27157 (7)	0.97170 (5)	0.43440 (7)	0.0480 (3)
N1	0.6734 (2)	0.96203 (13)	−0.07355 (18)	0.0270 (5)
H1N	0.6660	0.9714	0.0025	0.032*
N2	0.6540 (2)	0.89074 (14)	0.15548 (17)	0.0275 (5)
O1	0.74179 (19)	1.14840 (14)	0.05549 (17)	0.0405 (5)
O2	0.9133 (2)	1.17039 (15)	−0.0337 (2)	0.0572 (6)
H2A	0.9260	1.2212	0.0065	0.086*
O3	0.9143 (2)	0.97572 (14)	0.19069 (18)	0.0449 (5)
O4	0.96439 (19)	0.93712 (15)	0.38441 (16)	0.0434 (5)
H4	1.0409	0.9596	0.3849	0.065*
O1W	0.5390 (3)	0.84981 (16)	0.4486 (2)	0.0519 (6)
H2W	0.594 (4)	0.887 (2)	0.479 (3)	0.042 (10)*
H1W	0.457 (5)	0.877 (3)	0.443 (4)	0.092 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0262 (13)	0.0260 (12)	0.0318 (13)	0.0029 (10)	0.0005 (11)	0.0006 (10)
C2	0.0304 (14)	0.0251 (12)	0.0417 (15)	0.0084 (11)	0.0026 (12)	−0.0014 (11)
C3	0.0336 (14)	0.0220 (12)	0.0357 (14)	0.0030 (11)	−0.0019 (11)	−0.0050 (10)
C4	0.0332 (14)	0.0217 (12)	0.0356 (14)	0.0055 (10)	−0.0012 (11)	−0.0029 (10)
C5	0.0218 (12)	0.0263 (12)	0.0340 (14)	−0.0011 (10)	0.0002 (11)	0.0031 (10)
C6	0.070 (2)	0.0378 (15)	0.0471 (18)	0.0086 (15)	0.0258 (16)	−0.0046 (13)
C7	0.0435 (17)	0.0368 (14)	0.0398 (15)	0.0101 (13)	−0.0021 (13)	−0.0001 (12)
C8	0.0569 (19)	0.0261 (13)	0.0446 (16)	−0.0013 (13)	0.0031 (14)	0.0076 (12)
C9	0.0271 (13)	0.0387 (14)	0.0279 (13)	0.0018 (11)	−0.0022 (11)	−0.0041 (11)
C10	0.0298 (14)	0.0239 (12)	0.0324 (14)	0.0020 (10)	−0.0017 (11)	−0.0037 (10)
C11	0.0292 (13)	0.0320 (13)	0.0405 (15)	−0.0007 (11)	0.0094 (12)	−0.0045 (11)
C12	0.0279 (14)	0.0287 (13)	0.0365 (14)	−0.0008 (11)	0.0029 (12)	0.0030 (11)
Cl1	0.0331 (4)	0.0426 (4)	0.0634 (5)	−0.0038 (3)	0.0023 (3)	0.0034 (3)
N1	0.0249 (11)	0.0246 (10)	0.0298 (11)	0.0013 (8)	0.0036 (9)	−0.0025 (8)
N2	0.0248 (11)	0.0229 (10)	0.0298 (11)	0.0027 (8)	−0.0025 (9)	−0.0029 (8)
O1	0.0330 (10)	0.0486 (11)	0.0384 (11)	−0.0090 (9)	0.0060 (9)	−0.0126 (9)
O2	0.0537 (14)	0.0430 (12)	0.0839 (17)	−0.0206 (10)	0.0339 (13)	−0.0177 (11)
O3	0.0393 (12)	0.0501 (12)	0.0415 (12)	−0.0057 (9)	0.0023 (9)	0.0060 (9)
O4	0.0286 (10)	0.0547 (12)	0.0392 (11)	−0.0042 (9)	−0.0065 (9)	−0.0003 (9)
O1W	0.0484 (15)	0.0327 (11)	0.0759 (17)	0.0025 (11)	0.0176 (13)	0.0018 (11)

Geometric parameters (Å, º) top

C1—N1	1.483 (3)	C7—H7B	0.9600
C1—C5ⁱ	1.523 (3)	C7—H7C	0.9600
C1—H1A	0.9700	C8—H8A	0.9600
C1—H1B	0.9700	C8—H8B	0.9600
C2—N1	1.500 (3)	C8—H8C	0.9600
C2—C3	1.521 (4)	C9—N2	1.490 (3)
C2—C6	1.524 (4)	C9—C10	1.513 (4)
C2—H2	0.9800	C9—H9A	0.9700
C3—C4	1.525 (4)	C9—H9B	0.9700
C3—H3A	0.9700	C10—O3	1.186 (3)
C3—H3B	0.9700	C10—O4	1.317 (3)
C4—C7	1.523 (4)	C11—N1	1.465 (3)
C4—C8	1.535 (4)	C11—C12	1.515 (4)
C4—N2	1.571 (3)	C11—H11A	0.9700
C5—N2	1.497 (3)	C11—H11B	0.9700
C5—C1ⁱ	1.523 (3)	C12—O1	1.196 (3)
C5—H5A	0.9700	C12—O2	1.327 (3)
C5—H5B	0.9700	N1—H1N	0.9100
C6—H6A	0.9600	O2—H2A	0.8200
C6—H6B	0.9600	O4—H4	0.8200
C6—H6C	0.9600	O1W—H2W	0.76 (3)
C7—H7A	0.9600	O1W—H1W	0.88 (5)

N1—C1—C5ⁱ	110.10 (18)	C4—C7—H7C	109.5
N1—C1—H1A	109.6	H7A—C7—H7C	109.5
C5ⁱ—C1—H1A	109.6	H7B—C7—H7C	109.5
N1—C1—H1B	109.6	C4—C8—H8A	109.5
C5ⁱ—C1—H1B	109.6	C4—C8—H8B	109.5
H1A—C1—H1B	108.2	H8A—C8—H8B	109.5
N1—C2—C3	111.5 (2)	C4—C8—H8C	109.5
N1—C2—C6	114.2 (2)	H8A—C8—H8C	109.5
C3—C2—C6	111.3 (2)	H8B—C8—H8C	109.5
N1—C2—H2	106.4	N2—C9—C10	111.2 (2)
C3—C2—H2	106.4	N2—C9—H9A	109.4
C6—C2—H2	106.4	C10—C9—H9A	109.4
C2—C3—C4	116.7 (2)	N2—C9—H9B	109.4
C2—C3—H3A	108.1	C10—C9—H9B	109.4
C4—C3—H3A	108.1	H9A—C9—H9B	108.0
C2—C3—H3B	108.1	O3—C10—O4	126.4 (3)
C4—C3—H3B	108.1	O3—C10—C9	123.9 (2)
H3A—C3—H3B	107.3	O4—C10—C9	109.6 (2)
C7—C4—C3	111.3 (2)	N1—C11—C12	116.1 (2)
C7—C4—C8	107.3 (2)	N1—C11—H11A	108.3
C3—C4—C8	110.0 (2)	C12—C11—H11A	108.3
C7—C4—N2	110.47 (19)	N1—C11—H11B	108.3
C3—C4—N2	106.86 (18)	C12—C11—H11B	108.3
C8—C4—N2	111.0 (2)	H11A—C11—H11B	107.4
N2—C5—C1ⁱ	114.86 (19)	O1—C12—O2	123.7 (2)
N2—C5—H5A	108.6	O1—C12—C11	127.7 (2)
C1ⁱ—C5—H5A	108.6	O2—C12—C11	108.7 (2)
N2—C5—H5B	108.6	C11—N1—C1	113.39 (19)
C1ⁱ—C5—H5B	108.6	C11—N1—C2	109.8 (2)
H5A—C5—H5B	107.5	C1—N1—C2	112.43 (18)
C2—C6—H6A	109.5	C11—N1—H1N	106.9
C2—C6—H6B	109.5	C1—N1—H1N	106.9
H6A—C6—H6B	109.5	C2—N1—H1N	106.9
C2—C6—H6C	109.5	C9—N2—C5	111.37 (19)
H6A—C6—H6C	109.5	C9—N2—C4	114.14 (17)
H6B—C6—H6C	109.5	C5—N2—C4	109.45 (17)
C4—C7—H7A	109.5	C12—O2—H2A	109.5
C4—C7—H7B	109.5	C10—O4—H4	109.5
H7A—C7—H7B	109.5	H2W—O1W—H1W	107 (3)

N1—C2—C3—C4	−75.6 (3)	C6—C2—N1—C11	−71.7 (3)
C6—C2—C3—C4	155.6 (2)	C3—C2—N1—C1	−71.7 (3)
C2—C3—C4—C7	−62.6 (3)	C6—C2—N1—C1	55.5 (3)
C2—C3—C4—C8	178.6 (2)	C10—C9—N2—C5	−151.36 (19)
C2—C3—C4—N2	58.1 (3)	C10—C9—N2—C4	84.1 (2)
N2—C9—C10—O3	20.5 (3)	C1ⁱ—C5—N2—C9	67.6 (3)
N2—C9—C10—O4	−162.1 (2)	C1ⁱ—C5—N2—C4	−165.3 (2)
N1—C11—C12—O1	−5.1 (4)	C7—C4—N2—C9	−34.3 (3)
N1—C11—C12—O2	174.1 (2)	C3—C4—N2—C9	−155.5 (2)
C12—C11—N1—C1	92.6 (3)	C8—C4—N2—C9	84.6 (2)
C12—C11—N1—C2	−140.7 (2)	C7—C4—N2—C5	−159.9 (2)
C5ⁱ—C1—N1—C11	−52.7 (3)	C3—C4—N2—C5	78.9 (2)
C5ⁱ—C1—N1—C2	−178.0 (2)	C8—C4—N2—C5	−41.0 (2)
C3—C2—N1—C11	161.1 (2)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···Cl1ⁱⁱ	0.82	2.24	3.012 (3)	158
O2—H2A···O1Wⁱⁱⁱ	0.82	1.82	2.610 (3)	162
O1W—H2W···Cl1^iv	0.76 (3)	2.40 (3)	3.152 (3)	169 (3)

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

Experimental details

Crystal data
Chemical formula	C₂₄H₄₆N₄O₈²⁺·2Cl⁻·2H₂O
M_r	625.58
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.977 (5), 13.475 (7), 11.572 (6)
β (°)	104.220 (9)
V (Å³)	1508.1 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.10 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15242, 2946, 2036
R_int	0.143
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.141, 0.99
No. of reflections	2946
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.37

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···Cl1ⁱ	0.82	2.24	3.012 (3)	158
O2—H2A···O1Wⁱⁱ	0.82	1.82	2.610 (3)	162
O1W—H2W···Cl1ⁱⁱⁱ	0.76 (3)	2.40 (3)	3.152 (3)	169 (3)

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

Acknowledgements

The work was supported by a Key Grant (No. 206118) from the Ministry of Education and the Natural Science Foundation of Hainan Province (No. 80619).

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Marinelli, E. R., Neubeck, R., Song, B., Wagler, T., Ranganathan, R. S., Sukumaran, K., Wedeking, P., Nunn, A., Runge, V. & Tweedle, M. (2002). Acad. Radiol. 9, s251–s254. Web of Science CrossRef PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S. F. (2001). Chin. J. Syn. Chem. 9, 223–226, 231. Google Scholar
Xu, J. D., Ni, S. S. & Lin, Y. J. (1988). Inorg. Chem. , 4651–4657. CrossRef Google Scholar

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Volume 64| Part 5| May 2008| Page o885

doi:10.1107/S1600536808010532

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

1,4,8,11-Tetra­kis(carb­oxy­meth­yl)-5,5,7,12,12,14-hexa­methyl-4,11-di­aza-1,8-diazo­nia­cyclo­tetra­decane dichloride dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,4,8,11-Tetrakis(carboxymethyl)-5,5,7,12,12,14-hexamethyl-4,11-diaza-1,8-diazoniacyclotetradecane dichloride dihydrate