trans-Diaqua-bis-[5-(pyridine-3-carboxamido)-tetra-zolido-κ(2)O,N(1)]zinc dihydrate.

The title compound, [Zn(C(7)H(5)N(6)O)(2)(H(2)O)(2)]·2H(2)O, consists of one Zn(II) ion located on the crystallographic inversion centre, two 5-(pyridine-3-carboxamido)-tetra-zolide ligands, two coordinated water mol-ecules and two free water mol-ecules. The Zn(II) ion adopts a slightly distorted octa-hedral coordination geometry formed by the N,O-chelating ligands and two O water atoms. The pyridine N atoms are not coordinated. In the crystal, complex mol-ecules are connected by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For pharmaceutical applications of amide derivatives, see: Foster et al. (1999 ▶); Rauko et al. (2001 ▶); Rowland et al. (2001 ▶, 2002 ▶). For our recent work on the design and synthesis of amide complexes, see: Wang et al. (2010 ▶). For the use of nicotinoyl­amino in building novel complexes, see: Aakeröy et al. (2001 ▶); Li et al. (2008 ▶); Moncol et al. (2007 ▶); Kumar et al. (2005 ▶). For Zn—N and Zn—O bond lengths in related structures, see: Armstrong et al. (2003 ▶); Liu et al. (2009 ▶).

Experimental

Crystal data

[Zn(C7H5N6O)2(H2O)2]·2H2O

M = 515.79

Monoclinic,

a = 7.2576 (15) Å

b = 12.008 (2) Å

c = 11.917 (2) Å

β = 97.76 (3)°

V = 1029.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.26 mm−1

T = 293 K

0.22 × 0.15 × 0.1 mm

Data collection

Rigaku Saturn 724 CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2002 ▶) T min = 0.819, T max = 1.000

8464 measured reflections

2374 independent reflections

2188 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.100

S = 1.19

2374 reflections

165 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014997/hg5200sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014997/hg5200Isup2.hkl

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

[Zn(C7H5N6O)2(H2O)2]·2H2O	F(000) = 528
Mr = 515.79	Dx = 1.665 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3552 reflections
a = 7.2576 (15) Å	θ = 3.1–27.5°
b = 12.008 (2) Å	µ = 1.26 mm−1
c = 11.917 (2) Å	T = 293 K
β = 97.76 (3)°	Prism, colorless
V = 1029.1 (3) Å3	0.22 × 0.15 × 0.1 mm
Z = 2

Rigaku Saturn 724 CCD area-detector diffractometer	2374 independent reflections
Radiation source: fine-focus sealed tube	2188 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
scintillation counter scans	θmax = 27.6°, θmin = 3.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	h = −9→7
Tmin = 0.819, Tmax = 1.000	k = −15→14
8464 measured reflections	l = −15→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ2(Fo2) + (0.0354P)2 + 0.6596P] where P = (Fo2 + 2Fc2)/3
2374 reflections	(Δ/σ)max = 0.042
165 parameters	Δρmax = 0.24 e Å−3
6 restraints	Δρmin = −0.33 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
Zn1	0.0000	0.0000	0.0000	0.02817 (14)
O1	0.1128 (2)	0.16405 (14)	−0.01319 (16)	0.0348 (4)
C5	0.2633 (3)	0.3319 (2)	0.0481 (2)	0.0274 (5)
C7	0.3943 (3)	0.0364 (2)	0.1181 (2)	0.0259 (5)
C6	0.2446 (3)	0.2086 (2)	0.0460 (2)	0.0281 (5)
N4	0.5071 (3)	−0.12357 (19)	0.1550 (2)	0.0364 (5)
N5	0.5487 (3)	−0.01344 (18)	0.1645 (2)	0.0342 (5)
N6	0.3527 (3)	0.49961 (18)	0.1502 (2)	0.0370 (5)
C4	0.3380 (4)	0.3890 (2)	0.1451 (2)	0.0333 (6)
H12	0.3799	0.3480	0.2097	0.040*
C3	0.1991 (4)	0.3936 (2)	−0.0474 (2)	0.0349 (6)
H13	0.1448	0.3584	−0.1132	0.042*
C1	0.2944 (4)	0.5576 (2)	0.0566 (2)	0.0377 (6)
H15	0.3064	0.6347	0.0586	0.045*
C2	0.2168 (4)	0.5077 (2)	−0.0436 (3)	0.0415 (7)
H16	0.1772	0.5506	−0.1072	0.050*
N1	0.3798 (3)	0.15158 (17)	0.11143 (18)	0.0309 (5)
H6	0.4637	0.1899	0.1523	0.037*
N3	0.3383 (3)	−0.13789 (18)	0.1054 (2)	0.0344 (5)
N2	0.2617 (3)	−0.03656 (18)	0.08075 (18)	0.0279 (4)
O2	0.0833 (3)	−0.05113 (17)	−0.15682 (16)	0.0340 (4)
H2A	0.186 (2)	−0.025 (3)	−0.169 (3)	0.066 (12)*
H2B	0.011 (3)	−0.037 (3)	−0.2160 (16)	0.061 (11)*
O3	0.7255 (3)	0.25284 (18)	0.1891 (2)	0.0517 (6)
H3A	0.801 (4)	0.208 (3)	0.166 (3)	0.078*
H3B	0.787 (4)	0.287 (3)	0.243 (2)	0.078*

	U11	U22	U33	U12	U13	U23
Zn1	0.0224 (2)	0.0244 (2)	0.0352 (2)	−0.00194 (15)	−0.00520 (16)	−0.00004 (16)
O1	0.0314 (10)	0.0247 (9)	0.0444 (11)	−0.0060 (7)	−0.0087 (8)	0.0033 (8)
C5	0.0270 (12)	0.0251 (12)	0.0292 (12)	−0.0025 (9)	0.0006 (10)	−0.0005 (10)
C7	0.0250 (12)	0.0264 (11)	0.0248 (11)	−0.0005 (9)	−0.0015 (9)	0.0007 (9)
C6	0.0298 (13)	0.0257 (12)	0.0284 (12)	−0.0027 (10)	0.0020 (10)	0.0018 (10)
N4	0.0299 (12)	0.0346 (12)	0.0426 (13)	0.0043 (9)	−0.0025 (10)	0.0052 (10)
N5	0.0297 (12)	0.0320 (12)	0.0382 (13)	−0.0006 (9)	−0.0055 (9)	0.0048 (9)
N6	0.0414 (14)	0.0302 (12)	0.0374 (12)	−0.0022 (10)	−0.0019 (10)	−0.0053 (9)
C4	0.0377 (15)	0.0295 (13)	0.0313 (13)	−0.0005 (11)	−0.0007 (11)	−0.0019 (10)
C3	0.0400 (15)	0.0312 (13)	0.0312 (13)	−0.0004 (11)	−0.0030 (11)	−0.0018 (10)
C1	0.0411 (16)	0.0248 (13)	0.0466 (17)	−0.0026 (11)	0.0042 (13)	−0.0005 (11)
C2	0.0529 (18)	0.0323 (15)	0.0372 (15)	0.0014 (12)	−0.0014 (13)	0.0083 (11)
N1	0.0290 (11)	0.0254 (10)	0.0348 (11)	−0.0046 (9)	−0.0083 (9)	−0.0016 (9)
N3	0.0317 (12)	0.0257 (11)	0.0437 (13)	0.0020 (9)	−0.0026 (10)	0.0036 (9)
N2	0.0253 (11)	0.0243 (10)	0.0325 (11)	−0.0001 (8)	−0.0023 (9)	0.0008 (8)
O2	0.0280 (10)	0.0396 (11)	0.0332 (10)	−0.0005 (8)	−0.0005 (8)	−0.0006 (8)
O3	0.0387 (12)	0.0347 (12)	0.0765 (17)	−0.0038 (9)	−0.0109 (11)	−0.0120 (10)

Zn1—N2	2.058 (2)	N4—N5	1.358 (3)
Zn1—N2i	2.058 (2)	N6—C4	1.333 (3)
Zn1—O2i	2.131 (2)	N6—C1	1.334 (4)
Zn1—O2	2.131 (2)	C4—H12	0.9300
Zn1—O1	2.1470 (17)	C3—C2	1.376 (4)
Zn1—O1i	2.1470 (17)	C3—H13	0.9300
O1—C6	1.232 (3)	C1—C2	1.386 (4)
C5—C3	1.385 (4)	C1—H15	0.9300
C5—C4	1.389 (3)	C2—H16	0.9300
C5—C6	1.487 (3)	N1—H6	0.8600
C7—N5	1.323 (3)	N3—N2	1.353 (3)
C7—N2	1.332 (3)	O2—H2A	0.840 (5)
C7—N1	1.389 (3)	O2—H2B	0.839 (5)
C6—N1	1.354 (3)	O3—H3A	0.837 (5)
N4—N3	1.298 (3)	O3—H3B	0.838 (5)
N2—Zn1—N2i	180.00 (16)	C7—N5—N4	103.8 (2)
N2—Zn1—O2i	90.26 (8)	C4—N6—C1	117.9 (2)
N2i—Zn1—O2i	89.74 (8)	N6—C4—C5	123.3 (2)
N2—Zn1—O2	89.74 (8)	N6—C4—H12	118.3
N2i—Zn1—O2	90.26 (8)	C5—C4—H12	118.3
O2i—Zn1—O2	180.0	C2—C3—C5	119.0 (3)
N2—Zn1—O1	83.86 (8)	C2—C3—H13	120.5
N2i—Zn1—O1	96.14 (8)	C5—C3—H13	120.5
O2i—Zn1—O1	87.47 (8)	N6—C1—C2	122.7 (2)
O2—Zn1—O1	92.53 (8)	N6—C1—H15	118.6
N2—Zn1—O1i	96.14 (8)	C2—C1—H15	118.6
N2i—Zn1—O1i	83.86 (8)	C3—C2—C1	119.0 (3)
O2i—Zn1—O1i	92.53 (8)	C3—C2—H16	120.5
O2—Zn1—O1i	87.47 (8)	C1—C2—H16	120.5
O1—Zn1—O1i	180.00 (11)	C6—N1—C7	125.5 (2)
C6—O1—Zn1	129.12 (16)	C6—N1—H6	117.3
C3—C5—C4	118.1 (2)	C7—N1—H6	117.3
C3—C5—C6	120.0 (2)	N4—N3—N2	108.3 (2)
C4—C5—C6	122.0 (2)	C7—N2—N3	105.2 (2)
N5—C7—N2	112.0 (2)	C7—N2—Zn1	126.55 (18)
N5—C7—N1	121.8 (2)	N3—N2—Zn1	128.27 (16)
N2—C7—N1	126.1 (2)	Zn1—O2—H2A	114 (2)
O1—C6—N1	123.8 (2)	Zn1—O2—H2B	117 (2)
O1—C6—C5	120.3 (2)	H2A—O2—H2B	104.1 (12)
N1—C6—C5	115.9 (2)	H3A—O3—H3B	104.7 (13)
N3—N4—N5	110.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H6···O3	0.86	2.04	2.829 (3)	153
O2—H2A···N5ii	0.84 (1)	1.97 (1)	2.795 (3)	165 (3)
O2—H2B···N6iii	0.84 (1)	1.89 (1)	2.727 (3)	178 (3)
O3—H3A···O2ii	0.84 (1)	2.08 (2)	2.843 (3)	152 (4)
O3—H3B···N4iv	0.84 (1)	2.09 (1)	2.907 (3)	164 (4)

Table 1

Selected bond lengths (Å)

Zn1—N2	2.058 (2)
Zn1—O2	2.131 (2)
Zn1—O1	2.1470 (17)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H6⋯O3	0.86	2.04	2.829 (3)	153
O2—H2A⋯N5i	0.84 (1)	1.97 (1)	2.795 (3)	165 (3)
O2—H2B⋯N6ii	0.84 (1)	1.89 (1)	2.727 (3)	178 (3)
O3—H3A⋯O2i	0.84 (1)	2.08 (2)	2.843 (3)	152 (4)
O3—H3B⋯N4iii	0.84 (1)	2.09 (1)	2.907 (3)	164 (4)

Symmetry codes: (i) ; (ii) ; (iii) .