Crystal structure of poly[di-μ-aqua-{5-[(1Z)-2-(4-chloro-phen-yl)-1-cyano-ethenyl]-1,2,3,4-tetra-zol-1-ido-κN (1)}sodium].

In the title compound, [Na(C10H5ClN5)(H2O)2] n , infinite chains of [Na(H2O)2](+) cations having a diamond-shaped cross-section and running parallel to the b axis are formed. O-H⋯N hydrogen bonds to the anions generate layers parallel to (100) which have the chloro-benzene-cyano-ethenyl substituents protruding from both surfaces. The sodium ion makes a short contact of 2.4801 (13) Å with the N atom of the tetra-zolide ring which is syn to the cyano N atom.

Related literature

For chemical behaviour of tetra­zoles, see: Smith et al. (1991 ▸); Duncia et al. (1990 ▸). For various industrial applications of different tetra­zole derivatives, see: Modarresi et al. (2009 ▸); Singh et al. (1980 ▸). For medicinal activities of compounds with a tetra­zole scaffold, see: Myznikov et al. (2007 ▸); Schocken et al. (1989 ▸); Mekni & Bakloiti (2008 ▸); Lim et al. (2007 ▸).

Experimental

Crystal data

[Na(C10H5ClN5)(H2O)2]

M = 289.66

Monoclinic,

a = 22.0438 (4) Å

b = 3.8343 (1) Å

c = 15.0141 (3) Å

β = 92.427 (1)°

V = 1267.89 (5) Å3

Z = 4

Cu Kα radiation

μ = 3.08 mm−1

T = 150 K

0.29 × 0.11 × 0.04 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.73, T max = 0.89

9115 measured reflections

2560 independent reflections

2249 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.03

2560 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015006325/tk5364sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006325/tk5364Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015006325/tk5364fig1.tif

Title compound with numbering scheme and 50% probability ellipsoids.

Click here for additional data file.

2 2 + n x y z x y z x y z x y z x y z x y z . DOI: 10.1107/S2056989015006325/tk5364fig2.tif

A portion of the {[Na(H2O)2]+}n chain (symmetry operations: (i) x, 1 + y, z, (ii) 2 − x,  + y,  − z, (iii) x, −1 + y, z, (iv) 2 − x, − + y,  − z, (v) 2 − x, − + y,  − z, (vi) x, −2 + y, z).

Click here for additional data file.

b . DOI: 10.1107/S2056989015006325/tk5364fig3.tif

Packing viewed along the b axis.

Click here for additional data file.

. DOI: 10.1107/S2056989015006325/tk5364fig4.tif

Elevation view of the chain structure.

CCDC reference: 1056677

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Na(C10H5ClN5)(H2O)2]	F(000) = 592
Mr = 289.66	Dx = 1.517 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 22.0438 (4) Å	Cell parameters from 6311 reflections
b = 3.8343 (1) Å	θ = 4.0–74.5°
c = 15.0141 (3) Å	µ = 3.08 mm−1
β = 92.427 (1)°	T = 150 K
V = 1267.89 (5) Å3	Plate, colourless
Z = 4	0.29 × 0.11 × 0.04 mm

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2560 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2249 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.026
Detector resolution: 10.4167 pixels mm-1	θmax = 74.5°, θmin = 2.0°
ω scans	h = −27→25
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −4→4
Tmin = 0.73, Tmax = 0.89	l = −18→18
9115 measured reflections

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)] = 0.032	Hydrogen site location: mixed
wR(F2) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.4982P] where P = (Fo2 + 2Fc2)/3
2560 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.37 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) while those attached to oxygen were placed in locations derived from a difference map and their parameters adjusted to give O—H = 0.84 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
Cl1	0.49516 (2)	0.10717 (11)	0.35718 (3)	0.03137 (13)
N1	0.86367 (6)	1.0318 (4)	0.43087 (8)	0.0206 (3)
N2	0.91834 (6)	1.1473 (4)	0.46047 (8)	0.0220 (3)
N3	0.92611 (6)	1.0749 (4)	0.54572 (8)	0.0221 (3)
N4	0.87680 (6)	0.9091 (4)	0.57424 (8)	0.0209 (3)
N5	0.74923 (7)	0.5087 (5)	0.65661 (10)	0.0382 (4)
C1	0.83943 (7)	0.8871 (4)	0.50194 (9)	0.0176 (3)
C2	0.77918 (7)	0.7259 (4)	0.50140 (9)	0.0194 (3)
C3	0.76111 (7)	0.6066 (5)	0.58710 (10)	0.0242 (3)
C4	0.74473 (7)	0.6828 (4)	0.42591 (10)	0.0210 (3)
H4	0.7629	0.7579	0.3729	0.025*
C5	0.68365 (7)	0.5378 (4)	0.41324 (10)	0.0204 (3)
C6	0.66615 (7)	0.4117 (4)	0.32820 (10)	0.0240 (3)
H6	0.6941	0.4214	0.2818	0.029*
C7	0.60884 (7)	0.2734 (4)	0.31088 (10)	0.0244 (3)
H7	0.5977	0.1835	0.2535	0.029*
C8	0.56795 (7)	0.2681 (4)	0.37836 (11)	0.0232 (3)
C9	0.58373 (7)	0.3933 (5)	0.46302 (10)	0.0254 (3)
H9	0.5553	0.3870	0.5088	0.030*
C10	0.64131 (7)	0.5273 (4)	0.47993 (10)	0.0243 (3)
H10	0.6523	0.6135	0.5377	0.029*
Na1	0.92711 (3)	0.78850 (17)	0.72191 (4)	0.02362 (16)
O1	0.99226 (5)	0.9704 (3)	0.84267 (6)	0.0211 (2)
H1A	1.0146	0.8147	0.8659	0.025*
H1B	0.9717	1.0768	0.8799	0.025*
O2	0.86926 (5)	0.2859 (3)	0.75583 (7)	0.0251 (3)
H2A	0.8664	0.3340	0.8101	0.030*
H2B	0.8326	0.2395	0.7434	0.030*

	U11	U22	U33	U12	U13	U23
Cl1	0.0220 (2)	0.0323 (2)	0.0393 (2)	−0.00816 (16)	−0.00439 (15)	−0.00037 (17)
N1	0.0179 (6)	0.0247 (7)	0.0192 (6)	−0.0011 (5)	0.0002 (5)	0.0004 (5)
N2	0.0194 (6)	0.0248 (7)	0.0216 (6)	−0.0015 (5)	0.0001 (5)	0.0001 (5)
N3	0.0196 (6)	0.0251 (7)	0.0214 (6)	−0.0024 (5)	−0.0017 (5)	−0.0011 (5)
N4	0.0190 (6)	0.0243 (7)	0.0191 (6)	−0.0017 (5)	−0.0008 (5)	−0.0003 (5)
N5	0.0268 (8)	0.0584 (11)	0.0292 (7)	−0.0056 (8)	−0.0005 (6)	0.0161 (7)
C1	0.0171 (7)	0.0178 (7)	0.0179 (6)	0.0020 (6)	0.0007 (5)	−0.0010 (5)
C2	0.0181 (7)	0.0181 (7)	0.0221 (7)	0.0018 (6)	0.0019 (5)	0.0021 (6)
C3	0.0161 (7)	0.0301 (9)	0.0260 (8)	−0.0015 (6)	−0.0029 (6)	0.0041 (7)
C4	0.0195 (7)	0.0214 (7)	0.0222 (7)	0.0002 (6)	0.0022 (5)	0.0008 (6)
C5	0.0187 (7)	0.0187 (7)	0.0237 (7)	0.0013 (6)	−0.0009 (5)	0.0008 (6)
C6	0.0226 (8)	0.0262 (8)	0.0230 (7)	0.0024 (7)	0.0007 (6)	0.0003 (6)
C7	0.0243 (8)	0.0235 (8)	0.0250 (7)	0.0014 (7)	−0.0049 (6)	−0.0027 (6)
C8	0.0190 (7)	0.0190 (8)	0.0311 (8)	−0.0018 (6)	−0.0039 (6)	0.0020 (6)
C9	0.0201 (8)	0.0300 (9)	0.0263 (7)	0.0005 (7)	0.0028 (6)	0.0013 (7)
C10	0.0232 (8)	0.0262 (8)	0.0233 (7)	0.0001 (7)	−0.0014 (6)	−0.0028 (6)
Na1	0.0246 (3)	0.0255 (3)	0.0205 (3)	0.0022 (3)	−0.0020 (2)	−0.0011 (2)
O1	0.0211 (5)	0.0246 (6)	0.0176 (5)	0.0045 (4)	0.0001 (4)	−0.0001 (4)
O2	0.0252 (6)	0.0323 (6)	0.0175 (5)	0.0033 (5)	−0.0022 (4)	−0.0019 (5)

Cl1—C8	1.7359 (16)	C7—C8	1.384 (2)
N1—C1	1.3343 (19)	C7—H7	0.9500
N1—N2	1.3419 (18)	C8—C9	1.389 (2)
N2—N3	1.3138 (17)	C9—C10	1.383 (2)
N3—N4	1.3449 (18)	C9—H9	0.9500
N4—C1	1.3374 (19)	C10—H10	0.9500
N4—Na1	2.4801 (13)	Na1—O2i	2.3619 (13)
N5—C3	1.150 (2)	Na1—O1	2.3697 (12)
C1—C2	1.465 (2)	Na1—O2	2.3780 (14)
C2—C4	1.348 (2)	Na1—O1ii	2.3941 (12)
C2—C3	1.438 (2)	O1—Na1iii	2.3941 (12)
C4—C5	1.462 (2)	O1—H1A	0.8399
C4—H4	0.9500	O1—H1B	0.8398
C5—C10	1.398 (2)	O2—Na1iv	2.3619 (13)
C5—C6	1.404 (2)	O2—H2A	0.8399
C6—C7	1.385 (2)	O2—H2B	0.8401
C6—H6	0.9500
C1—N1—N2	104.89 (12)	C9—C10—C5	120.98 (15)
N3—N2—N1	109.33 (12)	C9—C10—H10	119.5
N2—N3—N4	109.65 (12)	C5—C10—H10	119.5
C1—N4—N3	104.47 (12)	O2i—Na1—O1	84.99 (4)
C1—N4—Na1	161.92 (11)	O2i—Na1—O2	107.99 (5)
N3—N4—Na1	92.06 (8)	O1—Na1—O2	112.82 (4)
N1—C1—N4	111.66 (13)	O2i—Na1—O1ii	156.29 (5)
N1—C1—C2	124.39 (13)	O1—Na1—O1ii	91.35 (4)
N4—C1—C2	123.95 (13)	O2—Na1—O1ii	95.05 (4)
C4—C2—C3	123.10 (14)	O2i—Na1—N4	79.46 (4)
C4—C2—C1	122.35 (13)	O1—Na1—N4	149.61 (5)
C3—C2—C1	114.51 (13)	O2—Na1—N4	96.83 (4)
N5—C3—C2	177.07 (17)	O1ii—Na1—N4	92.55 (4)
C2—C4—C5	129.74 (14)	O2i—Na1—N3	84.63 (4)
C2—C4—H4	115.1	O1—Na1—N3	125.07 (5)
C5—C4—H4	115.1	O2—Na1—N3	121.70 (4)
C10—C5—C6	118.38 (14)	O1ii—Na1—N3	78.35 (4)
C10—C5—C4	123.85 (14)	N4—Na1—N3	27.99 (4)
C6—C5—C4	117.74 (14)	Na1—O1—Na1iii	106.04 (4)
C7—C6—C5	121.07 (14)	Na1—O1—H1A	115.7
C7—C6—H6	119.5	Na1iii—O1—H1A	95.6
C5—C6—H6	119.5	Na1—O1—H1B	109.0
C8—C7—C6	119.03 (14)	Na1iii—O1—H1B	116.9
C8—C7—H7	120.5	H1A—O1—H1B	113.0
C6—C7—H7	120.5	Na1iv—O2—Na1	107.98 (5)
C7—C8—C9	121.26 (15)	Na1iv—O2—H2A	116.7
C7—C8—Cl1	119.77 (12)	Na1—O2—H2A	95.3
C9—C8—Cl1	118.96 (12)	Na1iv—O2—H2B	107.7
C10—C9—C8	119.26 (15)	Na1—O2—H2B	130.0
C10—C9—H9	120.4	H2A—O2—H2B	98.7
C8—C9—H9	120.4
C1—N1—N2—N3	−0.19 (17)	C3—C2—C4—C5	4.3 (3)
N1—N2—N3—N4	0.17 (17)	C1—C2—C4—C5	−178.16 (15)
N1—N2—N3—Na1	31.8 (5)	C2—C4—C5—C10	23.5 (3)
N2—N3—N4—C1	−0.08 (17)	C2—C4—C5—C6	−158.45 (17)
N2—N3—N4—Na1	172.51 (11)	C10—C5—C6—C7	−1.3 (2)
N2—N1—C1—N4	0.14 (17)	C4—C5—C6—C7	−179.43 (15)
N2—N1—C1—C2	179.72 (14)	C5—C6—C7—C8	1.5 (2)
N3—N4—C1—N1	−0.04 (17)	C6—C7—C8—C9	−1.0 (2)
Na1—N4—C1—N1	−155.5 (3)	C6—C7—C8—Cl1	178.18 (13)
N3—N4—C1—C2	−179.62 (14)	C7—C8—C9—C10	0.3 (3)
Na1—N4—C1—C2	24.9 (4)	Cl1—C8—C9—C10	−178.91 (13)
N1—C1—C2—C4	6.0 (2)	C8—C9—C10—C5	−0.1 (3)
N4—C1—C2—C4	−174.48 (15)	C6—C5—C10—C9	0.6 (2)
N1—C1—C2—C3	−176.27 (15)	C4—C5—C10—C9	178.56 (15)
N4—C1—C2—C3	3.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3ii	0.84	2.04	2.8443 (17)	160
O1—H1B···N2v	0.84	2.02	2.8593 (17)	175
O2—H2B···N5	0.84	2.44	3.1009 (19)	136

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1AN3i	0.84	2.04	2.8443(17)	160
O1H1BN2ii	0.84	2.02	2.8593(17)	175
O2H2BN5	0.84	2.44	3.1009(19)	136

Symmetry codes: (i) ; (ii) .