catena-Poly[[(5-carb­oxy-2H-1,2,3-triazole-4-carboxyl­ato-κ2N3,O4)sodium]-di-μ-aqua-κ4O:O]

Liu, H.-Y.; Liu, L.-X.; Sha, J.-Q.; Yu, L.-S.

doi:10.1107/S1600536810037384

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages m1336-m1337

doi:10.1107/S1600536810037384

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catena-Poly[[(5-carboxy-2H-1,2,3-triazole-4-carboxylato-κ²N³,O⁴)sodium]-di-μ-aqua-κ⁴O:O]

Hai-Yan Liu,^a Li-Xin Liu,^a Jing-Quan Sha ^a ^* and Lian-Sheng Yu ^a

^aThe Provincial Key Laboratory of Biological Medicine Formulation, School of Pharmacy, Jiamusi University, Jiamusi 154007, People's Republic of China
^*Correspondence e-mail: shajq2002@126.com

(Received 1 September 2010; accepted 18 September 2010; online 30 September 2010)

In the title coordination polymer, [Na(C₄H₂N₃O₄)(H₂O)₂]_n, the Na^I atom is six-coordinated by one O atom and one N atom from a 2H-1,2,3-triazole-4-carboxy-5-carboxylate ligand and four O atoms from four water molecules, forming a distorted octahedal geometry. The Na^I atoms are bridged by water molecules into a chain structure along [100]. Intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds connect the chains. An intramolecular O—H⋯O hydrogen bond between the carboxylate groups is observed.

Related literature

For general background to the design and synthesis of metal–organic frameworks (MOFs), see: Chen et al. (2009 ); Rosi et al. (2003 ); Su et al. (2004 ); Xiao et al. (2006 ). For the use of heterocyclic dicarboxylic acids in MOFs, see: Gao et al. (2006 ); Mukherjee et al. (2004 ); Shi et al. (2006 ); Sun et al. (2005 ). For metal complexes with 2H-1,2,3-triazole-4,5-dicarboxylic acid, see: Liu et al. (2008 ); Yue et al. (2008 ); Zheng et al. (2009 ).

Experimental

Crystal data

[Na(C₄H₂N₃O₄)(H₂O)₂]
M_r = 215.11
Monoclinic, P 2₁ /n
a = 6.8706 (9) Å
b = 10.6280 (13) Å
c = 11.5585 (14) Å
β = 95.647 (1)°
V = 839.91 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.23 × 0.22 × 0.18 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.955, T_max = 0.965
4453 measured reflections
1658 independent reflections
1509 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.102
S = 1.00
1658 reflections
148 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.95 (2)	1.74 (2)	2.652 (2)	158 (2)
O3—H3⋯O1	0.82	1.65	2.468 (2)	177
O5—H5A⋯N3ⁱⁱ	0.85 (2)	2.15 (2)	2.949 (2)	155 (2)
O5—H5B⋯O3ⁱⁱⁱ	0.82 (2)	2.13 (2)	2.923 (2)	163 (2)
O6—H6A⋯O1ⁱ	0.84 (2)	2.07 (2)	2.902 (2)	173 (2)
O6—H6B⋯O4ⁱⁱⁱ	0.80 (2)	2.03 (2)	2.819 (2)	173 (2)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037384/hy2351sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037384/hy2351Isup2.hkl

checkCIF report

Comment top

Currently, there has been intense research effort on the design and synthesis of metal-organic frameworks (MOFs) owing to their intriguing variety of architectures and their tremendous potential applications in many fields (Chen et al., 2009; Rosi et al., 2003; Su et al., 2004; Xiao et al., 2006). As one kind of well known ligands, heterocyclic dicarboxylic acids have been used to prepare MOFs with multi-dimensional structures because of the hetero atoms may serve as potential coordinating sites (Gao et al., 2006; Mukherjee et al., 2004; Shi et al., 2006; Sun et al., 2005), such as 2H-1,2,3-triazole-4,5-dicarboxylic acid (H₂tda). The three triazole N atoms of H₂tda can coordinate to various metals (such as Mn, Cd and K), resulting in the formation of intriguing multi-dimensional structures with complicated topologies (Liu et al., 2008; Yue et al., 2008; Zheng et al., 2009).

In the title coordination polymer (Fig. 1), the Na^I atom is six-coordinated by one O atom and one N atom from one Htda ligand, and four O atoms from water molecules, with a slightly distorted octahedral geometry. Furthermore, the Na^I atoms are bridged by the water molecules, leading to a one-dimensional chain structure, as shown in Fig. 2. Intermolecular N—H···O, O—H···N and O—H···O hydrogen bonds connect the chains (Table 1).

Related literature top

For general background to the design and synthesis of metal–organic frameworks (MOFs), see: Chen et al. (2009); Rosi et al. (2003); Su et al. (2004); Xiao et al. (2006). For the use of heterocyclic dicarboxylic acids in MOFs, see: Gao et al. (2006); Mukherjee et al. (2004); Shi et al. (2006); Sun et al. (2005). For metal complexes with 2H-1,2,3-triazole-4,5-dicarboxylic acid, see: Liu et al. (2008); Yue et al. (2008); Zheng et al. (2009).

Experimental top

All chemicals were purchased from commercial sources and used without further purification. A mixture of H₂tda and NaOH in a molar ratio of 1:1 was dissolved in water. Colorless block crystals of the title compound were obtained by slow evaporation of the filtrate over a period of 3 d.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound with symmetry-related atoms to complete the Na coordination. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) -x, 2-y, 2-z; (ii) 1-x, 2-y, 2-z.]
	Fig. 2. View of the one-dimensional chain in the title compound.

catena-Poly[[(5-carboxy-2H-1,2,3-triazole-4-carboxylato- κ²N³,O⁴)sodium]-di-µ-aqua-κ⁴O:O] top

Crystal data top

[Na(C₄H₂N₃O₄)(H₂O)₂]	F(000) = 440
M_r = 215.11	D_x = 1.701 Mg m⁻³ D_m = 1.701 Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2984 reflections
a = 6.8706 (9) Å	θ = 2.6–28.2°
b = 10.6280 (13) Å	µ = 0.20 mm⁻¹
c = 11.5585 (14) Å	T = 293 K
β = 95.647 (1)°	Block, colorless
V = 839.91 (18) Å³	0.23 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	1658 independent reflections
Radiation source: fine-focus sealed tube	1509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.955, T_max = 0.965	k = −9→13
4453 measured 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0608P)² + 0.3697P] where P = (F_o² + 2F_c²)/3
1658 reflections	(Δ/σ)_max = 0.001
148 parameters	Δρ_max = 0.47 e Å⁻³
4 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Na(C₄H₂N₃O₄)(H₂O)₂]	V = 839.91 (18) Å³
M_r = 215.11	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.8706 (9) Å	µ = 0.20 mm⁻¹
b = 10.6280 (13) Å	T = 293 K
c = 11.5585 (14) Å	0.23 × 0.22 × 0.18 mm
β = 95.647 (1)°

Data collection top

Bruker APEX CCD diffractometer	1658 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1509 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.965	R_int = 0.026
4453 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	4 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.47 e Å⁻³
1658 reflections	Δρ_min = −0.59 e Å⁻³
148 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
H5B	0.091 (4)	1.1695 (18)	0.910 (3)	0.081 (10)*
H5A	0.028 (4)	1.076 (3)	0.8361 (16)	0.071 (8)*
H6A	0.503 (3)	1.018 (2)	1.1923 (15)	0.054 (7)*
H6B	0.433 (4)	1.1154 (18)	1.136 (2)	0.056 (7)*
Na1	0.25079 (9)	0.92974 (6)	0.99461 (6)	0.0348 (2)
O1	0.11703 (17)	0.54042 (11)	0.85612 (9)	0.0331 (3)
O2	0.15004 (18)	0.74783 (11)	0.87493 (10)	0.0347 (3)
N1	0.34905 (19)	0.72021 (12)	1.09099 (11)	0.0260 (3)
O6	0.4709 (2)	1.04572 (12)	1.12560 (11)	0.0364 (3)
O3	0.20462 (18)	0.34772 (11)	0.96846 (10)	0.0348 (3)
H3	0.1733	0.4126	0.9330	0.042*
O5	0.0576 (2)	1.09590 (12)	0.90710 (11)	0.0388 (3)
N3	0.42462 (19)	0.54647 (13)	1.19491 (11)	0.0276 (3)
O4	0.3474 (2)	0.29745 (11)	1.14248 (11)	0.0420 (3)
N2	0.4322 (2)	0.67011 (13)	1.18801 (11)	0.0282 (3)
C2	0.3282 (2)	0.51189 (14)	1.09393 (12)	0.0225 (3)
C4	0.2933 (2)	0.37598 (15)	1.06997 (14)	0.0279 (3)
C3	0.2809 (2)	0.62053 (14)	1.02900 (12)	0.0216 (3)
C1	0.1755 (2)	0.63899 (14)	0.91084 (12)	0.0243 (3)
H2	0.499 (3)	0.719 (2)	1.2488 (19)	0.045 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0355 (4)	0.0270 (4)	0.0401 (4)	−0.0001 (3)	−0.0051 (3)	0.0002 (3)
O1	0.0393 (6)	0.0318 (6)	0.0254 (6)	−0.0025 (5)	−0.0109 (5)	−0.0054 (5)
O2	0.0422 (7)	0.0302 (6)	0.0280 (6)	−0.0002 (5)	−0.0147 (5)	0.0058 (5)
N1	0.0289 (7)	0.0246 (7)	0.0226 (6)	0.0010 (5)	−0.0072 (5)	−0.0012 (5)
O6	0.0493 (8)	0.0284 (7)	0.0300 (6)	0.0013 (5)	−0.0030 (5)	−0.0014 (5)
O3	0.0438 (7)	0.0226 (6)	0.0366 (6)	−0.0034 (5)	−0.0025 (5)	−0.0036 (5)
O5	0.0505 (8)	0.0310 (7)	0.0327 (7)	0.0001 (6)	−0.0066 (6)	−0.0020 (5)
N3	0.0309 (7)	0.0281 (7)	0.0226 (6)	0.0028 (5)	−0.0042 (5)	0.0021 (5)
O4	0.0553 (8)	0.0258 (6)	0.0443 (7)	0.0062 (5)	0.0022 (6)	0.0097 (5)
N2	0.0334 (7)	0.0278 (7)	0.0212 (6)	0.0014 (6)	−0.0088 (5)	−0.0025 (5)
C2	0.0216 (7)	0.0241 (8)	0.0215 (7)	0.0018 (5)	−0.0003 (5)	0.0006 (6)
C4	0.0274 (8)	0.0241 (8)	0.0323 (8)	0.0011 (6)	0.0040 (6)	0.0001 (6)
C3	0.0206 (7)	0.0233 (7)	0.0198 (7)	0.0008 (5)	−0.0035 (5)	−0.0007 (5)
C1	0.0221 (7)	0.0292 (8)	0.0204 (7)	0.0004 (6)	−0.0050 (5)	0.0006 (6)

Geometric parameters (Å, º) top

Na1—O5	2.3747 (15)	O3—C4	1.303 (2)
Na1—O6	2.3765 (14)	O3—H3	0.8200
Na1—O2	2.4377 (13)	O5—H5B	0.82 (2)
Na1—O6ⁱ	2.4855 (15)	O5—H5A	0.85 (2)
Na1—O5ⁱⁱ	2.5157 (16)	N3—N2	1.3178 (19)
Na1—N1	2.5510 (14)	N3—C2	1.336 (2)
O1—C1	1.2683 (19)	O4—C4	1.215 (2)
O2—C1	1.2356 (19)	N2—H2	0.95 (2)
N1—N2	1.3196 (18)	C2—C3	1.398 (2)
N1—C3	1.3375 (19)	C2—C4	1.486 (2)
O6—H6A	0.84 (2)	C3—C1	1.4946 (19)
O6—H6B	0.80 (2)

O5—Na1—O6	100.34 (5)	C3—N1—Na1	113.19 (9)
O5—Na1—O2	103.44 (5)	Na1—O6—Na1ⁱ	100.06 (5)
O6—Na1—O2	154.19 (5)	Na1—O6—H6A	120.0 (17)
O5—Na1—O6ⁱ	96.45 (5)	Na1ⁱ—O6—H6A	113.8 (17)
O6—Na1—O6ⁱ	79.94 (5)	Na1—O6—H6B	112.2 (18)
O2—Na1—O6ⁱ	87.54 (5)	Na1ⁱ—O6—H6B	105.3 (19)
O5—Na1—O5ⁱⁱ	79.20 (5)	H6A—O6—H6B	105 (2)
O6—Na1—O5ⁱⁱ	106.25 (5)	C4—O3—H3	109.5
O2—Na1—O5ⁱⁱ	88.03 (5)	Na1—O5—Na1ⁱⁱ	100.80 (5)
O6ⁱ—Na1—O5ⁱⁱ	172.90 (5)	Na1—O5—H5B	124 (2)
O5—Na1—N1	161.44 (5)	Na1ⁱⁱ—O5—H5B	109 (2)
O6—Na1—N1	92.87 (5)	Na1—O5—H5A	107.1 (19)
O2—Na1—N1	66.65 (4)	Na1ⁱⁱ—O5—H5A	105.9 (19)
O6ⁱ—Na1—N1	98.66 (5)	H5B—O5—H5A	109 (3)
O5ⁱⁱ—Na1—N1	84.65 (5)	N2—N3—C2	103.92 (12)
O5—Na1—Na1ⁱ	100.92 (4)	N3—N2—N1	115.94 (12)
O6—Na1—Na1ⁱ	41.05 (3)	N3—N2—H2	121.2 (13)
O2—Na1—Na1ⁱ	123.06 (4)	N1—N2—H2	122.8 (13)
O6ⁱ—Na1—Na1ⁱ	38.90 (3)	N3—C2—C3	108.12 (13)
O5ⁱⁱ—Na1—Na1ⁱ	147.18 (5)	N3—C2—C4	119.18 (13)
N1—Na1—Na1ⁱ	97.61 (4)	C3—C2—C4	132.70 (14)
O5—Na1—Na1ⁱⁱ	40.97 (4)	O4—C4—O3	123.18 (15)
O6—Na1—Na1ⁱⁱ	107.45 (5)	O4—C4—C2	120.42 (15)
O2—Na1—Na1ⁱⁱ	97.09 (4)	O3—C4—C2	116.40 (13)
O6ⁱ—Na1—Na1ⁱⁱ	137.15 (4)	N1—C3—C2	108.42 (12)
O5ⁱⁱ—Na1—Na1ⁱⁱ	38.23 (3)	N1—C3—C1	119.88 (13)
N1—Na1—Na1ⁱⁱ	122.34 (4)	C2—C3—C1	131.70 (13)
Na1ⁱ—Na1—Na1ⁱⁱ	132.86 (4)	O2—C1—O1	125.34 (14)
C1—O2—Na1	121.94 (9)	O2—C1—C3	118.01 (13)
N2—N1—C3	103.59 (12)	O1—C1—C3	116.64 (13)
N2—N1—Na1	142.86 (10)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱⁱⁱ	0.95 (2)	1.74 (2)	2.652 (2)	158 (2)
O3—H3···O1	0.82	1.65	2.468 (2)	177
O5—H5A···N3^iv	0.85 (2)	2.15 (2)	2.949 (2)	155 (2)
O5—H5B···O3^v	0.82 (2)	2.13 (2)	2.923 (2)	163 (2)
O6—H6A···O1ⁱⁱⁱ	0.84 (2)	2.07 (2)	2.902 (2)	173 (2)
O6—H6B···O4^v	0.80 (2)	2.03 (2)	2.819 (2)	173 (2)

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

Experimental details

Crystal data
Chemical formula	[Na(C₄H₂N₃O₄)(H₂O)₂]
M_r	215.11
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	6.8706 (9), 10.6280 (13), 11.5585 (14)
β (°)	95.647 (1)
V (Å³)	839.91 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.23 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.955, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	4453, 1658, 1509
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.102, 1.00
No. of reflections	1658
No. of parameters	148
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.59

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.95 (2)	1.74 (2)	2.652 (2)	158 (2)
O3—H3···O1	0.82	1.65	2.468 (2)	177
O5—H5A···N3ⁱⁱ	0.85 (2)	2.15 (2)	2.949 (2)	155 (2)
O5—H5B···O3ⁱⁱⁱ	0.82 (2)	2.13 (2)	2.923 (2)	163 (2)
O6—H6A···O1ⁱ	0.84 (2)	2.07 (2)	2.902 (2)	173 (2)
O6—H6B···O4ⁱⁱⁱ	0.80 (2)	2.03 (2)	2.819 (2)	173 (2)

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

Acknowledgements

This work was supported financially by the National Natural Science Foundation (grant No. 20901031), the Natural Science Foundation (No. B200916) and the Education Ministry Key Teachers Foundation (1155 G53) of Heilongjiang Province and the Talent Training Fund of Jiamusi University (No. RC2009–034).

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