4,11-Diaza-1,8-diazo­niacyclo­tetra­decane bis­(pyridine-2-carboxyl­ate) dihydrate

Kim, N.-H.; Ha, K.

doi:10.1107/S1600536809037258

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2504

doi:10.1107/S1600536809037258

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4,11-Diaza-1,8-diazoniacyclotetradecane bis(pyridine-2-carboxylate) dihydrate

Nam-Ho Kim ^a and Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 10 September 2009; accepted 15 September 2009; online 19 September 2009)

The asymmetric unit of the title compound, C₁₀H₂₆N₄²⁺·2C₆H₄NO₂⁻·2H₂O, consists of half of a doubly protonated 1,4,8,11-tetraazacyclotetradecane (cyclam) dication, a pyridine-2-carboxylate anion and a solvent water molecule. The complete dication is generated by a crystallographic centre and adopts an endodentate conformation which may be influenced by intramolecular N—H⋯N hydrogen bonding. The carboxylate group of the anion appears to be delocalized on the basis of the C—O bond lengths [1.257 (2) and 1.250 (2) Å]. In the crystal structure, the components are linked by intermolecular N—H⋯O, N—H⋯N and O—H⋯O hydrogen bonds.

Related literature

For the crystal structures of [H₂(cyclam)]X [X = (ClO₄)₂ or Cl₂], see: Nave & Truter (1974 ); Kim et al. (2009 ). For the crystal structures of [H₄(cyclam)]X·nH₂O [X = Cl₄, Br₄, (ClO₄)₄, (SCN)₄, (SO₄)₂ or (p-CH₃C₆H₄SO₃)₄], see: Robinson et al. (1989 ); Subramanian & Zaworotko (1995 ). For the structure of pyridine-2-carboxylic acid, see: Hamazaki et al. (1998 ). For the crystal structures of pyridine-2-carboxylate compounds, see: Kim & Ha (2009a ,b ).

Experimental

Crystal data

C₁₀H₂₆N₄²⁺·2C₆H₄NO₂⁻·2H₂O
M_r = 482.58
Monoclinic, P 2₁ /c
a = 10.2746 (8) Å
b = 12.0551 (9) Å
c = 10.3244 (8) Å
β = 93.104 (2)°
V = 1276.92 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.22 × 0.17 × 0.11 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS: Sheldrick, 1996 ) T_min = 0.868, T_max = 1.000
9364 measured reflections
3152 independent reflections
1540 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.123
S = 1.02
3152 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O3	0.92	2.02	2.932 (2)	170
N3—H32⋯N2	0.92	2.53	2.926 (3)	106
N3—H32⋯N2ⁱ	0.92	2.08	2.846 (3)	139
N3—H31⋯O1ⁱⁱ	0.92	1.86	2.749 (2)	161
N3—H31⋯N1ⁱⁱ	0.92	2.46	3.039 (2)	121
O3—H3A⋯O1ⁱⁱⁱ	0.84	1.99	2.808 (2)	165
O3—H3B⋯O2^iv	0.84	1.91	2.739 (2)	168
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y, -z; (iii) x-1, y, z; (iv) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037258/nk2004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037258/nk2004Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound, C₁₀H₂₆N₄²⁺.2C₆H₄NO₂^-.2H₂O, (I), consists of half of a doubly protonated 1,4,8,11-tetraazacyclotetradecane (cyclam) dication, a pyridine-2-carboxylate anion and a solvent water molecule (Fig. 1). The macrocyclic dication contains two protonated N atoms and two secondary amine N atoms, and is located on a centre of inversion. The dication adopts an endodentate conformation with the N atoms oriented towards the centre of the macrocyclic cavity. The conformation may be stabilized by intramolecular N—H···N hydrogen bonding (Table 1 and Fig. 2). The N2—C9—C10—N3 torsion angle of 66.5 (2)° displays the gauche conformation for the group within the dication. A similar conformation is also observed in the structures cyclam (Robinson et al., 1989) and [H₂(cyclam)]X [X = (ClO₄)₂ or Cl₂] (Nave & Truter, 1974; Kim et al., 2009). Unlike cyclam and the dication, the tetracation, [H₄(cyclam)]⁴⁺, adopts an exodentate conformation, in which all four N atoms are oriented away from the ring cavity, occupying positions as far away as possible from each other on the ring periphery (Robinson et al., 1989; Subramanian & Zaworotko, 1995). The protonated N—C bond lengths (N3—C10/C11: 1.482 (3)/1.487 (3) Å) are longer than unprotonated N—C bond lengths (N2—C8/C9: 1.468 (3)/1.459 (3) Å). The carboxylate group of the anion appears to be delocalized on the basis of the C—O bond lengths (C—O: 1.250 (2) and 1.257 (2) Å). The components of the crystal structure are linked by intermolecular N—H···O, N—H···N and O—H···O hydrogen bonds into one-dimensional chains along [001] (Table 1 and Fig. 2).

Related literature top

For the crystal structures of [H₂(cyclam)]X [X = (ClO₄)₂ or Cl₂], see: Nave & Truter (1974); Kim et al. (2009). For the crystal structures of [H₄(cyclam)]X.nH₂O [X = Cl₄, Br₄, (ClO₄)₄, (SCN)₄, (SO₄)₂ or (p-CH₃C₆H₄SO₃)₄], see: Robinson et al. (1989); Subramanian & Zaworotko (1995). For the structure of pyridine-2-carboxylic acid, see: Hamazaki et al. (1998). For the crystal structures of pyridine-2-carboxylate compounds, see: Kim & Ha (2009a,b).

Experimental top

A solution of 1,4,8,11-tetraazacyclotetradecane (0.100 g, 0.50 mmol) and pyridine-2-carboxylic acid (0.123 g, 1.00 mmol) in H₂O (10 ml) was stirred for 3 h at 60 °C. The solvent was removed under vacuum and the residue was washed with acetone/ether, to give a white powder (0.221 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from an acetone solution.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), with displacement ellipsoids drawn at the 40% probability level for non-H atoms [Symmetry code: (a) -x, -y, -z].
	Fig. 2. View of the unit-cell contents of (I). Hydrogen bonding interactions are drawn with dashed lines.

4,11-Diaza-1,8-diazoniacyclotetradecane bis(pyridine-2-carboxylate) dihydrate top

Crystal data top

C₁₀H₂₆N₄²⁺·2C₆H₄NO₂⁻·2(H₂O)	F(000) = 520
M_r = 482.58	D_x = 1.255 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1456 reflections
a = 10.2746 (8) Å	θ = 2.6–24.3°
b = 12.0551 (9) Å	µ = 0.09 mm⁻¹
c = 10.3244 (8) Å	T = 200 K
β = 93.104 (2)°	Block, colourless
V = 1276.92 (17) Å³	0.22 × 0.17 × 0.11 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD diffractometer	3152 independent reflections
Radiation source: fine-focus sealed tube	1540 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS: Sheldrick, 1996)	h = −11→13
T_min = 0.868, T_max = 1.000	k = −16→15
9364 measured reflections	l = −13→13

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0315P)²] where P = (F_o² + 2F_c²)/3
3152 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₀H₂₆N₄²⁺·2C₆H₄NO₂⁻·2(H₂O)	V = 1276.92 (17) Å³
M_r = 482.58	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2746 (8) Å	µ = 0.09 mm⁻¹
b = 12.0551 (9) Å	T = 200 K
c = 10.3244 (8) Å	0.22 × 0.17 × 0.11 mm
β = 93.104 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3152 independent reflections
Absorption correction: multi-scan (SADABS: Sheldrick, 1996)	1540 reflections with I > 2σ(I)
T_min = 0.868, T_max = 1.000	R_int = 0.070
9364 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.02	Δρ_max = 0.22 e Å⁻³
3152 reflections	Δρ_min = −0.25 e Å⁻³
154 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
O1	0.84295 (15)	0.05500 (12)	0.30790 (13)	0.0377 (4)
O2	0.71238 (16)	0.00216 (13)	0.46269 (15)	0.0433 (5)
N1	0.67291 (18)	0.21986 (15)	0.23751 (17)	0.0333 (5)
C1	0.5839 (2)	0.29517 (19)	0.1972 (2)	0.0383 (6)
H1	0.6109	0.3538	0.1434	0.046*
C2	0.4558 (2)	0.2926 (2)	0.2290 (2)	0.0434 (6)
H2	0.3960	0.3481	0.1984	0.052*
C3	0.4166 (2)	0.2074 (2)	0.3066 (2)	0.0449 (7)
H3	0.3282	0.2017	0.3283	0.054*
C4	0.5066 (2)	0.1306 (2)	0.3524 (2)	0.0384 (6)
H4	0.4818	0.0725	0.4082	0.046*
C5	0.6339 (2)	0.13915 (18)	0.31597 (19)	0.0278 (5)
C6	0.7385 (2)	0.05841 (18)	0.3658 (2)	0.0312 (5)
N2	0.14631 (18)	0.09306 (16)	0.05713 (17)	0.0374 (5)
H21	0.1475	0.0811	0.1452	0.045*
N3	0.12754 (18)	−0.12813 (15)	−0.05896 (17)	0.0360 (5)
H31	0.1456	−0.1194	−0.1447	0.043*
H32	0.0565	−0.0845	−0.0438	0.043*
C7	0.0412 (3)	0.2719 (2)	0.0986 (3)	0.0510 (7)
H7A	0.0561	0.3529	0.0946	0.061*
H7B	0.0435	0.2503	0.1912	0.061*
C8	0.1501 (2)	0.2132 (2)	0.0340 (2)	0.0446 (7)
H8A	0.1424	0.2276	−0.0605	0.054*
H8B	0.2349	0.2430	0.0681	0.054*
C9	0.2570 (2)	0.0350 (2)	0.0057 (2)	0.0459 (7)
H9A	0.3388	0.0598	0.0519	0.055*
H9B	0.2625	0.0525	−0.0875	0.055*
C10	0.2406 (2)	−0.0876 (2)	0.0229 (2)	0.0485 (7)
H10A	0.3206	−0.1264	−0.0015	0.058*
H10B	0.2270	−0.1042	0.1151	0.058*
C11	0.0922 (3)	−0.24601 (19)	−0.0372 (3)	0.0487 (7)
H11A	0.0928	−0.2609	0.0571	0.058*
H11B	0.1577	−0.2949	−0.0748	0.058*
O3	0.11622 (16)	0.04470 (16)	0.33220 (14)	0.0609 (6)
H3A	0.0351	0.0418	0.3385	0.091*
H3B	0.1593	0.0314	0.4019	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0313 (10)	0.0450 (11)	0.0374 (9)	0.0095 (8)	0.0064 (8)	0.0074 (8)
O2	0.0425 (11)	0.0484 (11)	0.0389 (9)	−0.0014 (8)	0.0010 (8)	0.0163 (8)
N1	0.0335 (12)	0.0338 (11)	0.0327 (10)	0.0028 (9)	0.0026 (9)	0.0033 (9)
C1	0.0439 (16)	0.0346 (14)	0.0361 (13)	0.0048 (12)	−0.0003 (12)	0.0055 (11)
C2	0.0398 (16)	0.0423 (16)	0.0476 (15)	0.0118 (13)	−0.0042 (13)	−0.0027 (13)
C3	0.0305 (15)	0.0573 (18)	0.0473 (15)	0.0062 (13)	0.0050 (12)	0.0018 (14)
C4	0.0377 (15)	0.0464 (15)	0.0314 (13)	−0.0027 (13)	0.0038 (11)	0.0052 (12)
C5	0.0289 (13)	0.0303 (13)	0.0239 (11)	−0.0024 (11)	−0.0012 (10)	−0.0007 (10)
C6	0.0365 (15)	0.0284 (13)	0.0281 (12)	−0.0041 (11)	−0.0045 (11)	−0.0015 (11)
N2	0.0427 (13)	0.0406 (12)	0.0296 (10)	0.0016 (10)	0.0071 (9)	−0.0003 (9)
N3	0.0392 (12)	0.0361 (12)	0.0333 (10)	0.0082 (10)	0.0086 (9)	0.0035 (9)
C7	0.074 (2)	0.0301 (14)	0.0499 (16)	−0.0049 (14)	0.0144 (16)	0.0006 (12)
C8	0.0459 (17)	0.0431 (16)	0.0448 (15)	−0.0104 (13)	0.0036 (13)	0.0033 (13)
C9	0.0392 (16)	0.0610 (18)	0.0377 (14)	−0.0040 (14)	0.0035 (12)	−0.0116 (13)
C10	0.0424 (16)	0.0643 (19)	0.0383 (14)	0.0160 (14)	−0.0020 (13)	−0.0044 (13)
C11	0.0565 (18)	0.0364 (16)	0.0554 (17)	0.0108 (13)	0.0231 (15)	0.0159 (13)
O3	0.0392 (11)	0.1048 (16)	0.0385 (10)	−0.0009 (11)	0.0012 (9)	0.0222 (10)

Geometric parameters (Å, º) top

O1—C6	1.257 (2)	N3—H31	0.9200
O2—C6	1.250 (2)	N3—H32	0.9200
N1—C1	1.339 (3)	C7—C8	1.509 (3)
N1—C5	1.341 (2)	C7—C11ⁱ	1.511 (4)
C1—C2	1.374 (3)	C7—H7A	0.9900
C1—H1	0.9500	C7—H7B	0.9900
C2—C3	1.377 (3)	C8—H8A	0.9900
C2—H2	0.9500	C8—H8B	0.9900
C3—C4	1.374 (3)	C9—C10	1.499 (3)
C3—H3	0.9500	C9—H9A	0.9900
C4—C5	1.385 (3)	C9—H9B	0.9900
C4—H4	0.9500	C10—H10A	0.9900
C5—C6	1.519 (3)	C10—H10B	0.9900
N2—C9	1.459 (3)	C11—C7ⁱ	1.511 (4)
N2—C8	1.468 (3)	C11—H11A	0.9900
N2—H21	0.9200	C11—H11B	0.9900
N3—C10	1.482 (3)	O3—H3A	0.8400
N3—C11	1.487 (3)	O3—H3B	0.8400

C1—N1—C5	117.3 (2)	C11ⁱ—C7—H7A	108.9
N1—C1—C2	123.9 (2)	C8—C7—H7B	108.9
N1—C1—H1	118.1	C11ⁱ—C7—H7B	108.9
C2—C1—H1	118.1	H7A—C7—H7B	107.7
C1—C2—C3	118.0 (2)	N2—C8—C7	111.34 (19)
C1—C2—H2	121.0	N2—C8—H8A	109.4
C3—C2—H2	121.0	C7—C8—H8A	109.4
C4—C3—C2	119.4 (2)	N2—C8—H8B	109.4
C4—C3—H3	120.3	C7—C8—H8B	109.4
C2—C3—H3	120.3	H8A—C8—H8B	108.0
C3—C4—C5	119.0 (2)	N2—C9—C10	109.6 (2)
C3—C4—H4	120.5	N2—C9—H9A	109.8
C5—C4—H4	120.5	C10—C9—H9A	109.8
N1—C5—C4	122.4 (2)	N2—C9—H9B	109.8
N1—C5—C6	116.15 (19)	C10—C9—H9B	109.8
C4—C5—C6	121.4 (2)	H9A—C9—H9B	108.2
O2—C6—O1	126.1 (2)	N3—C10—C9	110.3 (2)
O2—C6—C5	116.1 (2)	N3—C10—H10A	109.6
O1—C6—C5	117.80 (19)	C9—C10—H10A	109.6
C9—N2—C8	112.69 (19)	N3—C10—H10B	109.6
C9—N2—H21	108.4	C9—C10—H10B	109.6
C8—N2—H21	108.5	H10A—C10—H10B	108.1
C10—N3—C11	114.79 (19)	N3—C11—C7ⁱ	110.9 (2)
C10—N3—H31	108.6	N3—C11—H11A	109.5
C11—N3—H31	108.6	C7ⁱ—C11—H11A	109.5
C10—N3—H32	108.6	N3—C11—H11B	109.5
C11—N3—H32	108.6	C7ⁱ—C11—H11B	109.5
H31—N3—H32	107.5	H11A—C11—H11B	108.0
C8—C7—C11ⁱ	113.3 (2)	H3A—O3—H3B	113.9
C8—C7—H7A	108.9

C5—N1—C1—C2	−1.6 (3)	C4—C5—C6—O2	−16.4 (3)
N1—C1—C2—C3	−0.2 (4)	N1—C5—C6—O1	−17.0 (3)
C1—C2—C3—C4	2.0 (4)	C4—C5—C6—O1	164.4 (2)
C2—C3—C4—C5	−1.9 (3)	C9—N2—C8—C7	−174.9 (2)
C1—N1—C5—C4	1.7 (3)	C11ⁱ—C7—C8—N2	−68.7 (3)
C1—N1—C5—C6	−176.94 (19)	C8—N2—C9—C10	−175.26 (19)
C3—C4—C5—N1	0.0 (3)	C11—N3—C10—C9	−172.71 (19)
C3—C4—C5—C6	178.6 (2)	N2—C9—C10—N3	66.5 (2)
N1—C5—C6—O2	162.19 (18)	C10—N3—C11—C7ⁱ	165.97 (19)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O3	0.92	2.02	2.932 (2)	170
N3—H32···N2	0.92	2.53	2.926 (3)	106
N3—H32···N2ⁱ	0.92	2.08	2.846 (3)	139
N3—H31···O1ⁱⁱ	0.92	1.86	2.749 (2)	161
N3—H31···N1ⁱⁱ	0.92	2.46	3.039 (2)	121
O3—H3A···O1ⁱⁱⁱ	0.84	1.99	2.808 (2)	165
O3—H3B···O2^iv	0.84	1.91	2.739 (2)	168

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

Experimental details

Crystal data
Chemical formula	C₁₀H₂₆N₄²⁺·2C₆H₄NO₂⁻·2(H₂O)
M_r	482.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	10.2746 (8), 12.0551 (9), 10.3244 (8)
β (°)	93.104 (2)
V (Å³)	1276.92 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.17 × 0.11

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS: Sheldrick, 1996)
T_min, T_max	0.868, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9364, 3152, 1540
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.123, 1.02
No. of reflections	3152
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.25

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O3	0.92	2.02	2.932 (2)	169.5
N3—H32···N2	0.92	2.53	2.926 (3)	106.2
N3—H32···N2ⁱ	0.92	2.08	2.846 (3)	139.4
N3—H31···O1ⁱⁱ	0.92	1.86	2.749 (2)	160.5
N3—H31···N1ⁱⁱ	0.92	2.46	3.039 (2)	121.0
O3—H3A···O1ⁱⁱⁱ	0.84	1.99	2.808 (2)	164.8
O3—H3B···O2^iv	0.84	1.91	2.739 (2)	167.9

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

Acknowledgements

This work was supported by a Korea Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2007–412-J02001).

References

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

4,11-Di­aza-1,8-diazo­nia­cyclo­tetra­decane bis­­(pyridine-2-carboxyl­ate) dihydrate

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Experimental

Crystal data

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Refinement

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organic compounds

4,11-Diaza-1,8-diazoniacyclotetradecane bis(pyridine-2-carboxylate) dihydrate