Aqua­bis[N′-(2-hydroxy­benzyl­idene)isonicotinohydrazide-κN]silver(I) nitrate

Ghammamy, S.; Sahebalzamani, H.; Khaligh, N.; Rahimi, R.

doi:10.1107/S1600536810005027

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m294

doi:10.1107/S1600536810005027

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Aquabis[N′-(2-hydroxybenzylidene)isonicotinohydrazide-κN]silver(I) nitrate

Shahriar Ghammamy,^a ^* Hajar Sahebalzamani,^b Nina Khaligh ^b and Rahmatollah Rahimi ^c

^aDepartment of Chemistry, Faculty of Science, Imom Khomeini International University, Ghazvin, Iran, ^bDepartment of Chemistry, Faculty of Science, Islamic Azad University Ardebil Branch, Ardebil, Iran, and ^cFaculty of Chemistry, Iran University of Science and Technology, Tehran, Iran
^*Correspondence e-mail: shghamamy@yahoo.com

(Received 15 January 2010; accepted 8 February 2010; online 13 February 2010)

In the title compound, [Ag(C₁₃H₁₁N₃O₂)₂(H₂O)]NO₃, two N atoms from two pyridine rings of two N′-(2-hydroxybenzylidene)isonicotinohydrazide ligands coordinate to the Ag^I atom, forming a nearly linear geometry with an N—Ag—N angle of 171.63 (6)°; a water O atom is located at the apical site, completing the T-shaped coordination. The crystal structure is stabilized by extensive O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonding.

Related literature

For factors affecting the coordination geometry of silver, see: Dong et al. (2004 ); Niu et al. (2009a ); Sumby & Hardie (2005 ); Abu-Youssef et al. (2007 ). For related structures, see: Li et al. (2006 ); Näther & Beck (2004 ); Niu et al. (2009b ).

Experimental

Crystal data

[Ag(C₁₃H₁₁N₃O₂)₂(H₂O)]NO₃
M_r = 670.39
Monoclinic, P 2₁ /c
a = 11.7194 (6) Å
b = 12.6459 (6) Å
c = 18.5719 (9) Å
β = 104.738 (1)°
V = 2661.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 120 K
0.55 × 0.45 × 0.30 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.686, T_max = 0.791
26832 measured reflections
6427 independent reflections
5518 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.077
S = 1.07
6427 reflections
403 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.04 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O7ⁱ	0.84 (3)	2.01 (3)	2.844 (2)	171 (3)
O1W—H2W⋯O2ⁱⁱ	0.79 (3)	2.04 (3)	2.821 (2)	172 (3)
N2—H2N⋯O6	0.84 (3)	2.09 (3)	2.880 (2)	157 (2)
N5—H5N⋯O7ⁱⁱⁱ	0.90 (3)	1.97 (3)	2.863 (2)	169 (2)
O2—H2O⋯N3	0.85 (3)	1.79 (3)	2.560 (2)	150 (2)
O4—H4O⋯N6	0.81 (2)	1.86 (2)	2.607 (2)	153 (2)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810005027/pv2256sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005027/pv2256Isup2.hkl

checkCIF report

Comment top

It is noteworthy that the coordination geometry of the silver metal center can be affected by many factors, such as coordination nature of organic ligands, temperature, counteranions, etc. (Dong et al., 2004; Niu et al., 2009a; Sumby & Hardie, 2005; Abu-Youssef et al., 2007). The crystal structures of bis(pyridine-4-carboxylic acid-N)silver(I) nitrate dihydrate (Li et al., 2006), chlorotris(3-methylpyridine-N)silver(I) (Näther & Beck, 2004) and bis[N0-(3-cyanobenzylidene)isonicotinohydrazide]silver(I) trifluoroacetate (Niu et al., 2009b) have been reported. We have synthsized a new coordination complex of silver using N'-(2-hydroxybenzylidene)isonicotinohydrazide ligand, (I), and determined its crystal structure which is presented in this article.

The central Ag atom in (I) is coordinated by two nitrogen atoms from two pyridine rings of two different ligands and a water O atom located at the apical site, defining slightly distorted linear coordination geometry (Fig. 1). The cations, anions and solvent water molecules are linked by O—H···O, O—H···N and N—H···O hydrogen bonds into a three-dimensional network (Table 1).

Related literature top

For factors affecting the coordination geometry of the silver metal center, see: Dong et al. (2004); Niu et al. (2009a); Sumby & Hardie (2005); Abu-Youssef et al. (2007). For related structures, see: Li et al. (2006); Näther & Beck (2004); Niu et al. (2009b).

Experimental top

A solution of N'-(2-hydroxybenzylidene)isonicotinohydrazide (0.14 g, 1 mol) in CH₃OH (10 ml) was added to an aqueous solution of AgNO₃ (0.1 g, 1 mol) in water (5 ml) with stirring at 333 K. A small amount of precipitate was removed from the resulting solution to grow crystals for crystallographic study. Prism shaped colorless crystals of (I) were obtained by slow evaporation of the solvent from a solution of (I) in CCl₄ at room temperature over a period of 3 d.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Aquabis[N'-(2-hydroxybenzylidene)isonicotinohydrazide- κN]silver(I) nitrate top

Crystal data top

[Ag(C₁₃H₁₁N₃O₂)₂(H₂O)]NO₃	F(000) = 1360
M_r = 670.39	D_x = 1.673 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 530 reflections
a = 11.7194 (6) Å	θ = 3–28°
b = 12.6459 (6) Å	µ = 0.82 mm⁻¹
c = 18.5719 (9) Å	T = 120 K
β = 104.738 (1)°	Prism, colourless
V = 2661.8 (2) Å³	0.55 × 0.45 × 0.30 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	6427 independent reflections
Radiation source: normal-focus sealed tube	5518 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 28.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −15→15
T_min = 0.686, T_max = 0.791	k = −16→16
26832 measured reflections	l = −24→24

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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0415P)² + 1.2646P] where P = (F_o² + 2F_c²)/3
6427 reflections	(Δ/σ)_max = 0.002
403 parameters	Δρ_max = 1.04 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

[Ag(C₁₃H₁₁N₃O₂)₂(H₂O)]NO₃	V = 2661.8 (2) Å³
M_r = 670.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7194 (6) Å	µ = 0.82 mm⁻¹
b = 12.6459 (6) Å	T = 120 K
c = 18.5719 (9) Å	0.55 × 0.45 × 0.30 mm
β = 104.738 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	6427 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	5518 reflections with I > 2σ(I)
T_min = 0.686, T_max = 0.791	R_int = 0.026
26832 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 1.04 e Å⁻³
6427 reflections	Δρ_min = −0.57 e Å⁻³
403 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Ag1	0.775957 (12)	0.740141 (11)	0.273949 (7)	0.02310 (6)
O1	0.34784 (12)	0.58945 (10)	−0.05478 (8)	0.0300 (3)
O2	0.13029 (13)	0.62068 (10)	−0.23755 (8)	0.0270 (3)
H2O	0.174 (2)	0.642 (2)	−0.1962 (14)	0.039 (7)*
O3	1.18823 (12)	0.93761 (10)	0.59595 (8)	0.0296 (3)
O4	1.41552 (13)	0.91337 (11)	0.78672 (8)	0.0281 (3)
H4O	1.373 (2)	0.8915 (19)	0.7484 (14)	0.036 (7)*
N1	0.64148 (14)	0.72810 (12)	0.17184 (8)	0.0205 (3)
N2	0.31651 (14)	0.76550 (12)	−0.06954 (8)	0.0187 (3)
H2N	0.3355 (19)	0.827 (2)	−0.0542 (12)	0.026 (6)*
N3	0.23344 (14)	0.74841 (11)	−0.13455 (9)	0.0184 (3)
N4	0.91745 (13)	0.77455 (12)	0.37111 (8)	0.0196 (3)
N5	1.23864 (14)	0.76411 (12)	0.61217 (9)	0.0187 (3)
H5N	1.239 (2)	0.700 (2)	0.5912 (15)	0.045 (7)*
N6	1.31761 (13)	0.78524 (12)	0.67872 (8)	0.0197 (3)
C2	0.59564 (16)	0.63071 (15)	0.14847 (10)	0.0246 (4)
H2A	0.6244	0.5710	0.1787	0.030*
C3	0.50945 (16)	0.61508 (14)	0.08293 (10)	0.0235 (4)
H3A	0.4807	0.5460	0.0687	0.028*
C4	0.46537 (15)	0.70135 (14)	0.03811 (9)	0.0194 (3)
C5	0.51035 (16)	0.80089 (14)	0.06191 (10)	0.0216 (3)
H5A	0.4820	0.8618	0.0329	0.026*
C6	0.59588 (16)	0.81041 (15)	0.12748 (10)	0.0229 (4)
H6A	0.6248	0.8792	0.1426	0.027*
C7	0.37251 (15)	0.67941 (14)	−0.03274 (10)	0.0200 (3)
C8	0.17347 (15)	0.82700 (14)	−0.16895 (9)	0.0194 (3)
H8A	0.1879	0.8968	−0.1499	0.023*
C9	0.08375 (15)	0.80705 (14)	−0.23707 (10)	0.0200 (3)
C10	0.06388 (16)	0.70525 (15)	−0.26912 (10)	0.0210 (3)
C11	−0.02388 (17)	0.68925 (17)	−0.33365 (10)	0.0273 (4)
H11A	−0.0355	0.6209	−0.3555	0.033*
C12	−0.09495 (17)	0.77244 (17)	−0.36661 (11)	0.0280 (4)
H12A	−0.1553	0.7608	−0.4109	0.034*
C13	−0.07862 (17)	0.87339 (17)	−0.33525 (10)	0.0281 (4)
H13A	−0.1282	0.9302	−0.3575	0.034*
C14	0.01051 (16)	0.88956 (15)	−0.27153 (10)	0.0241 (4)
H14A	0.0224	0.9584	−0.2506	0.029*
C16	0.96229 (16)	0.87207 (14)	0.38692 (10)	0.0234 (4)
H16A	0.9344	0.9272	0.3522	0.028*
C17	1.04701 (16)	0.89570 (14)	0.45134 (10)	0.0231 (4)
H19B	1.0772	0.9655	0.4602	0.028*
C18	1.08769 (15)	0.81621 (14)	0.50305 (9)	0.0194 (3)
C19	1.04189 (16)	0.71489 (15)	0.48736 (10)	0.0207 (3)
H19A	1.0678	0.6587	0.5215	0.025*
C20	0.95837 (16)	0.69751 (14)	0.42146 (10)	0.0211 (3)
H20A	0.9280	0.6280	0.4109	0.025*
C21	1.17579 (15)	0.84614 (14)	0.57436 (9)	0.0200 (3)
C22	1.38215 (15)	0.70897 (14)	0.71241 (10)	0.0200 (3)
H22A	1.3736	0.6401	0.6913	0.024*
C23	1.46765 (16)	0.72811 (14)	0.78232 (10)	0.0209 (3)
C24	1.48193 (16)	0.82865 (15)	0.81647 (10)	0.0224 (4)
C25	1.56702 (17)	0.84345 (16)	0.88292 (10)	0.0279 (4)
H25A	1.5760	0.9109	0.9062	0.033*
C26	1.63897 (18)	0.76048 (17)	0.91552 (11)	0.0303 (4)
H26A	1.6972	0.7718	0.9608	0.036*
C27	1.62699 (17)	0.66057 (17)	0.88272 (11)	0.0309 (4)
H27A	1.6768	0.6040	0.9052	0.037*
C28	1.54123 (17)	0.64503 (16)	0.81680 (10)	0.0264 (4)
H28A	1.5320	0.5769	0.7945	0.032*
N7	0.23978 (14)	0.99376 (11)	−0.00096 (8)	0.0240 (3)
O5	0.14711 (16)	1.04260 (14)	−0.02193 (9)	0.0520 (5)
O6	0.31228 (13)	0.98880 (11)	−0.03995 (8)	0.0314 (3)
O7	0.26376 (13)	0.94629 (10)	0.06137 (7)	0.0284 (3)
O1W	0.76685 (14)	0.54006 (11)	0.30562 (9)	0.0308 (3)
H1W	0.759 (2)	0.519 (2)	0.3471 (15)	0.039 (7)*
H2W	0.801 (3)	0.496 (2)	0.2897 (16)	0.055 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.01855 (9)	0.03073 (9)	0.01712 (8)	0.00154 (5)	−0.00076 (6)	0.00185 (5)
O1	0.0320 (7)	0.0221 (7)	0.0302 (7)	0.0029 (5)	−0.0025 (6)	−0.0047 (5)
O2	0.0318 (7)	0.0214 (6)	0.0253 (7)	−0.0001 (5)	0.0029 (6)	−0.0062 (5)
O3	0.0332 (7)	0.0218 (7)	0.0290 (7)	0.0022 (5)	−0.0009 (6)	−0.0058 (5)
O4	0.0323 (7)	0.0235 (7)	0.0249 (7)	−0.0031 (5)	0.0005 (6)	−0.0050 (5)
N1	0.0221 (8)	0.0266 (8)	0.0132 (7)	0.0085 (6)	0.0052 (6)	0.0035 (6)
N2	0.0184 (7)	0.0197 (7)	0.0154 (7)	−0.0004 (5)	−0.0008 (6)	−0.0019 (5)
N3	0.0173 (7)	0.0232 (7)	0.0146 (7)	−0.0013 (5)	0.0037 (6)	−0.0008 (5)
N4	0.0150 (7)	0.0264 (8)	0.0164 (7)	0.0022 (6)	0.0021 (6)	0.0014 (6)
N5	0.0191 (7)	0.0195 (7)	0.0159 (7)	−0.0015 (5)	0.0013 (6)	−0.0021 (5)
N6	0.0180 (7)	0.0246 (7)	0.0152 (7)	−0.0021 (6)	0.0020 (6)	−0.0019 (6)
C2	0.0235 (9)	0.0239 (9)	0.0252 (9)	0.0064 (7)	0.0039 (7)	0.0050 (7)
C3	0.0244 (9)	0.0212 (8)	0.0238 (9)	0.0037 (7)	0.0040 (7)	0.0011 (7)
C4	0.0196 (8)	0.0206 (8)	0.0185 (8)	0.0033 (6)	0.0057 (7)	0.0011 (6)
C5	0.0213 (9)	0.0209 (9)	0.0219 (9)	0.0012 (7)	0.0038 (7)	0.0013 (7)
C6	0.0219 (9)	0.0231 (9)	0.0223 (9)	−0.0023 (7)	0.0029 (7)	0.0010 (7)
C7	0.0171 (8)	0.0233 (8)	0.0190 (8)	0.0028 (6)	0.0037 (6)	−0.0002 (6)
C8	0.0198 (8)	0.0198 (8)	0.0178 (8)	−0.0020 (6)	0.0034 (6)	−0.0018 (6)
C9	0.0202 (8)	0.0222 (8)	0.0183 (8)	−0.0035 (7)	0.0057 (7)	−0.0006 (6)
C10	0.0201 (8)	0.0241 (9)	0.0200 (8)	−0.0031 (7)	0.0071 (7)	−0.0011 (7)
C11	0.0253 (9)	0.0357 (11)	0.0205 (9)	−0.0067 (8)	0.0054 (7)	−0.0057 (8)
C12	0.0178 (9)	0.0488 (12)	0.0149 (8)	−0.0055 (8)	−0.0005 (7)	0.0011 (8)
C13	0.0230 (9)	0.0377 (11)	0.0226 (9)	0.0023 (8)	0.0039 (7)	0.0087 (8)
C14	0.0269 (9)	0.0248 (9)	0.0206 (9)	−0.0011 (7)	0.0062 (7)	0.0024 (7)
C16	0.0252 (9)	0.0213 (8)	0.0234 (9)	0.0046 (7)	0.0059 (7)	0.0044 (7)
C17	0.0263 (9)	0.0190 (8)	0.0237 (9)	0.0006 (7)	0.0054 (7)	−0.0001 (7)
C18	0.0192 (8)	0.0207 (8)	0.0189 (8)	0.0020 (6)	0.0060 (7)	−0.0010 (6)
C19	0.0197 (8)	0.0217 (8)	0.0197 (8)	−0.0001 (7)	0.0034 (7)	0.0030 (7)
C20	0.0222 (8)	0.0200 (8)	0.0188 (8)	−0.0012 (7)	0.0014 (7)	0.0012 (6)
C21	0.0196 (8)	0.0213 (8)	0.0192 (8)	0.0003 (6)	0.0053 (7)	−0.0006 (6)
C22	0.0214 (8)	0.0198 (8)	0.0183 (8)	−0.0023 (7)	0.0040 (7)	−0.0009 (6)
C23	0.0191 (8)	0.0260 (9)	0.0174 (8)	−0.0034 (7)	0.0042 (7)	0.0009 (7)
C24	0.0203 (8)	0.0262 (9)	0.0208 (8)	−0.0057 (7)	0.0056 (7)	0.0002 (7)
C25	0.0262 (10)	0.0348 (10)	0.0219 (9)	−0.0109 (8)	0.0046 (7)	−0.0032 (8)
C26	0.0202 (9)	0.0496 (13)	0.0180 (9)	−0.0098 (8)	−0.0006 (7)	0.0044 (8)
C27	0.0241 (10)	0.0411 (11)	0.0261 (10)	0.0006 (8)	0.0036 (8)	0.0104 (8)
C28	0.0261 (9)	0.0283 (9)	0.0242 (9)	0.0001 (7)	0.0052 (7)	0.0046 (7)
N7	0.0332 (8)	0.0160 (7)	0.0185 (7)	0.0010 (6)	−0.0012 (6)	−0.0018 (5)
O5	0.0536 (11)	0.0551 (11)	0.0430 (9)	0.0335 (9)	0.0045 (8)	0.0096 (8)
O6	0.0413 (8)	0.0264 (7)	0.0276 (7)	−0.0055 (6)	0.0108 (6)	−0.0014 (5)
O7	0.0404 (8)	0.0210 (6)	0.0192 (6)	−0.0051 (6)	−0.0007 (6)	0.0023 (5)
O1W	0.0431 (9)	0.0238 (7)	0.0281 (8)	0.0042 (6)	0.0138 (7)	0.0015 (6)

Geometric parameters (Å, º) top

Ag1—N1	2.1406 (16)	C10—C11	1.381 (3)
Ag1—N4	2.1616 (15)	C11—C12	1.384 (3)
Ag1—O1W	2.6059 (14)	C11—H11A	0.9500
O1—C7	1.219 (2)	C12—C13	1.396 (3)
O2—C10	1.364 (2)	C12—H12A	0.9500
O2—H2O	0.85 (3)	C13—C14	1.380 (3)
O3—C21	1.221 (2)	C13—H13A	0.9500
O4—C24	1.356 (2)	C14—H14A	0.9500
O4—H4O	0.81 (3)	C16—C17	1.379 (3)
N1—C6	1.350 (2)	C16—H16A	0.9500
N1—C2	1.369 (2)	C17—C18	1.388 (2)
N2—N3	1.362 (2)	C17—H19B	0.9500
N2—C7	1.362 (2)	C18—C19	1.391 (3)
N2—H2N	0.83 (2)	C18—C21	1.506 (2)
N3—C8	1.289 (2)	C19—C20	1.377 (2)
N4—C16	1.343 (2)	C19—H19A	0.9500
N4—C20	1.351 (2)	C20—H20A	0.9500
N5—C21	1.360 (2)	C22—C23	1.444 (3)
N5—N6	1.369 (2)	C22—H22A	0.9500
N5—H5N	0.90 (3)	C23—C28	1.406 (3)
N6—C22	1.286 (2)	C23—C24	1.412 (3)
C2—C3	1.384 (3)	C24—C25	1.388 (3)
C2—H2A	0.9500	C25—C26	1.385 (3)
C3—C4	1.390 (2)	C25—H25A	0.9500
C3—H3A	0.9500	C26—C27	1.394 (3)
C4—C5	1.393 (3)	C26—H26A	0.9500
C4—C7	1.505 (2)	C27—C28	1.386 (3)
C5—C6	1.372 (2)	C27—H27A	0.9500
C5—H5A	0.9500	C28—H28A	0.9500
C6—H6A	0.9500	N7—O5	1.224 (2)
C8—C9	1.447 (2)	N7—O6	1.250 (2)
C8—H8A	0.9500	N7—O7	1.2705 (19)
C9—C14	1.398 (2)	O1W—H1W	0.84 (3)
C9—C10	1.412 (3)	O1W—H2W	0.79 (3)

N1—Ag1—N4	171.63 (6)	C13—C12—H12A	119.8
N1—Ag1—O1W	93.88 (5)	C14—C13—C12	119.12 (18)
N4—Ag1—O1W	94.23 (5)	C14—C13—H13A	120.4
C10—O2—H2O	106.6 (17)	C12—C13—H13A	120.4
C24—O4—H4O	104.5 (18)	C13—C14—C9	121.63 (18)
C6—N1—C2	115.94 (16)	C13—C14—H14A	119.2
C6—N1—Ag1	125.00 (13)	C9—C14—H14A	119.2
C2—N1—Ag1	119.07 (11)	N4—C16—C17	122.94 (16)
N3—N2—C7	117.57 (15)	N4—C16—H16A	118.5
N3—N2—H2N	121.2 (15)	C17—C16—H16A	118.5
C7—N2—H2N	121.1 (15)	C16—C17—C18	119.21 (17)
C8—N3—N2	119.60 (14)	C16—C17—H19B	120.4
C16—N4—C20	117.42 (16)	C18—C17—H19B	120.4
C16—N4—Ag1	122.79 (12)	C17—C18—C19	118.41 (16)
C20—N4—Ag1	119.63 (12)	C17—C18—C21	117.67 (16)
C21—N5—N6	118.07 (15)	C19—C18—C21	123.88 (16)
C21—N5—H5N	121.6 (17)	C20—C19—C18	118.85 (17)
N6—N5—H5N	119.4 (17)	C20—C19—H19A	120.6
C22—N6—N5	118.16 (15)	C18—C19—H19A	120.6
N1—C2—C3	123.16 (16)	N4—C20—C19	123.17 (17)
N1—C2—H2A	118.4	N4—C20—H20A	118.4
C3—C2—H2A	118.4	C19—C20—H20A	118.4
C2—C3—C4	119.45 (17)	O3—C21—N5	123.33 (16)
C2—C3—H3A	120.3	O3—C21—C18	121.66 (16)
C4—C3—H3A	120.3	N5—C21—C18	115.00 (15)
C3—C4—C5	117.81 (17)	N6—C22—C23	119.96 (16)
C3—C4—C7	117.06 (16)	N6—C22—H22A	120.0
C5—C4—C7	125.13 (16)	C23—C22—H22A	120.0
C6—C5—C4	119.55 (17)	C28—C23—C24	118.66 (17)
C6—C5—H5A	120.2	C28—C23—C22	119.27 (17)
C4—C5—H5A	120.2	C24—C23—C22	122.05 (17)
N1—C6—C5	124.09 (17)	O4—C24—C25	117.62 (17)
N1—C6—H6A	118.0	O4—C24—C23	122.56 (16)
C5—C6—H6A	118.0	C25—C24—C23	119.82 (18)
O1—C7—N2	122.33 (16)	C26—C25—C24	120.42 (19)
O1—C7—C4	121.53 (16)	C26—C25—H25A	119.8
N2—C7—C4	116.13 (15)	C24—C25—H25A	119.8
N3—C8—C9	118.84 (16)	C25—C26—C27	120.87 (19)
N3—C8—H8A	120.6	C25—C26—H26A	119.6
C9—C8—H8A	120.6	C27—C26—H26A	119.6
C14—C9—C10	118.10 (16)	C28—C27—C26	118.96 (19)
C14—C9—C8	119.67 (16)	C28—C27—H27A	120.5
C10—C9—C8	122.18 (16)	C26—C27—H27A	120.5
O2—C10—C11	118.38 (17)	C27—C28—C23	121.28 (19)
O2—C10—C9	121.24 (16)	C27—C28—H28A	119.4
C11—C10—C9	120.38 (18)	C23—C28—H28A	119.4
C10—C11—C12	120.25 (19)	O5—N7—O6	121.33 (16)
C10—C11—H11A	119.9	O5—N7—O7	120.08 (17)
C12—C11—H11A	119.9	O6—N7—O7	118.59 (15)
C11—C12—C13	120.50 (18)	H1W—O1W—H2W	108 (3)
C11—C12—H12A	119.8

O1W—Ag1—N1—C6	175.36 (14)	C12—C13—C14—C9	−0.9 (3)
O1W—Ag1—N1—C2	−4.07 (14)	C10—C9—C14—C13	−0.3 (3)
O1W—Ag1—N4—C16	−178.91 (14)	C8—C9—C14—C13	−177.92 (17)
O1W—Ag1—N4—C20	−3.61 (14)	C20—N4—C16—C17	0.1 (3)
C7—N2—N3—C8	175.98 (16)	Ag1—N4—C16—C17	175.52 (14)
C21—N5—N6—C22	−175.93 (16)	N4—C16—C17—C18	−0.7 (3)
C6—N1—C2—C3	1.2 (3)	C16—C17—C18—C19	0.6 (3)
Ag1—N1—C2—C3	−179.31 (14)	C16—C17—C18—C21	−177.08 (16)
N1—C2—C3—C4	−0.5 (3)	C17—C18—C19—C20	0.0 (3)
C2—C3—C4—C5	−0.3 (3)	C21—C18—C19—C20	177.56 (17)
C2—C3—C4—C7	179.53 (16)	C16—N4—C20—C19	0.6 (3)
C3—C4—C5—C6	0.4 (3)	Ag1—N4—C20—C19	−174.99 (14)
C7—C4—C5—C6	−179.42 (17)	C18—C19—C20—N4	−0.6 (3)
C2—N1—C6—C5	−1.1 (3)	N6—N5—C21—O3	1.7 (3)
Ag1—N1—C6—C5	179.44 (14)	N6—N5—C21—C18	−177.92 (14)
C4—C5—C6—N1	0.3 (3)	C17—C18—C21—O3	19.3 (3)
N3—N2—C7—O1	−2.5 (3)	C19—C18—C21—O3	−158.27 (18)
N3—N2—C7—C4	178.87 (15)	C17—C18—C21—N5	−161.04 (16)
C3—C4—C7—O1	−9.2 (3)	C19—C18—C21—N5	21.4 (2)
C5—C4—C7—O1	170.63 (17)	N5—N6—C22—C23	179.24 (16)
C3—C4—C7—N2	169.47 (16)	N6—C22—C23—C28	−177.15 (17)
C5—C4—C7—N2	−10.7 (3)	N6—C22—C23—C24	1.2 (3)
N2—N3—C8—C9	−178.63 (15)	C28—C23—C24—O4	179.40 (17)
N3—C8—C9—C14	174.16 (16)	C22—C23—C24—O4	1.0 (3)
N3—C8—C9—C10	−3.3 (3)	C28—C23—C24—C25	−0.3 (3)
C14—C9—C10—O2	−178.56 (16)	C22—C23—C24—C25	−178.70 (17)
C8—C9—C10—O2	−1.0 (3)	O4—C24—C25—C26	−178.97 (17)
C14—C9—C10—C11	1.5 (3)	C23—C24—C25—C26	0.8 (3)
C8—C9—C10—C11	179.04 (17)	C24—C25—C26—C27	−0.4 (3)
O2—C10—C11—C12	178.61 (16)	C25—C26—C27—C28	−0.3 (3)
C9—C10—C11—C12	−1.5 (3)	C26—C27—C28—C23	0.8 (3)
C10—C11—C12—C13	0.2 (3)	C24—C23—C28—C27	−0.4 (3)
C11—C12—C13—C14	1.0 (3)	C22—C23—C28—C27	177.98 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O7ⁱ	0.84 (3)	2.01 (3)	2.844 (2)	171 (3)
O1W—H2W···O2ⁱⁱ	0.79 (3)	2.04 (3)	2.821 (2)	172 (3)
N2—H2N···O6	0.84 (3)	2.09 (3)	2.880 (2)	157 (2)
N5—H5N···O7ⁱⁱⁱ	0.90 (3)	1.97 (3)	2.863 (2)	169 (2)
O2—H2O···N3	0.85 (3)	1.79 (3)	2.560 (2)	150 (2)
O4—H4O···N6	0.81 (2)	1.86 (2)	2.607 (2)	153 (2)

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₃H₁₁N₃O₂)₂(H₂O)]NO₃
M_r	670.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	11.7194 (6), 12.6459 (6), 18.5719 (9)
β (°)	104.738 (1)
V (Å³)	2661.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.55 × 0.45 × 0.30

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.686, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	26832, 6427, 5518
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.077, 1.07
No. of reflections	6427
No. of parameters	403
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.04, −0.57

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O7ⁱ	0.84 (3)	2.01 (3)	2.844 (2)	171 (3)
O1W—H2W···O2ⁱⁱ	0.79 (3)	2.04 (3)	2.821 (2)	172 (3)
N2—H2N···O6	0.84 (3)	2.09 (3)	2.880 (2)	157 (2)
N5—H5N···O7ⁱⁱⁱ	0.90 (3)	1.97 (3)	2.863 (2)	169 (2)
O2—H2O···N3	0.85 (3)	1.79 (3)	2.560 (2)	150 (2)
O4—H4O···N6	0.81 (2)	1.86 (2)	2.607 (2)	153 (2)

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

Acknowledgements

The authors thank Dr M. Amirnasr, Dr A R. Mahjoub and Dr N. Safari for valuable discussions.

References

Abu-Youssef, M. A. M., Dey, R., Gohar, Y., Massoud, A. A., Ohrstrom, L. & Langer, V. (2007). Inorg. Chem. 46, 5893–5903. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2007). SMART and SAINT-Plus. Bruker AXS, Madison, Wisconsin, USA. Google Scholar
Dong, Y.-B., Zhao, X., Huang, R.-Q., Smith, M. D. & zur Loye, H.-C. (2004). Inorg. Chem. 43, 5603–5612. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, B., Gao, P., Ye, L., Yang, G.-D. & Wu, L.-X. (2006). Acta Cryst. E62, m3238–m3239. Web of Science CSD CrossRef IUCr Journals Google Scholar
Näther, C. & Beck, A. (2004). Acta Cryst. E60, m1678–m1680. Web of Science CSD CrossRef IUCr Journals Google Scholar
Niu, C.-Y., Wu, B.-L., Zheng, X.-F., Wan, X.-S., Zhang, H.-Y., Niu, Y.-Y. & Meng, L.-Y. (2009a). CrystEngComm, 11, 1373–1382. Web of Science CSD CrossRef CAS Google Scholar
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Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Aqua­bis­[N′-(2-hy­droxy­benzyl­­idene)isonicotinohydrazide-κN]silver(I) nitrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Aquabis[N′-(2-hydroxybenzylidene)isonicotinohydrazide-κN]silver(I) nitrate