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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1521.
Published online 2009 November 7. doi:  10.1107/S1600536809045905
PMCID: PMC2971757

Bis(quinolin-8-ol)silver(I) 2-hydr­oxy-3,5-dinitro­benzoate

Abstract

The title compound, [Ag(C9H7NO)2](C7H3N2O7), was prepared from 3,5-dinitro­salicylic acid (DNS), quinolin-8-ol and AgNO3. The AgI atom is coordinated by two N atoms and two O atoms from two quinolin-8-ols in a roughly planar [maximum deviation = 0.223 (2) Å] environment. The two quinolin-8-ol ligands are bent slightly with respect to each other, making a dihedral angle of 9.55 (9)°. The DNS anion inter­acts with the silver complex through O—H(...)O hydrogen bonds

Related literature

For related structures, see: Smith & Thomasson (1999 [triangle]); Smith et al. (2001 [triangle]); Wu et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1521-scheme1.jpg

Experimental

Crystal data

  • [Ag(C9H7NO)2](C7H3N2O7)
  • M r = 625.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1521-efi1.jpg
  • a = 9.0154 (18) Å
  • b = 7.6122 (15) Å
  • c = 17.138 (3) Å
  • β = 104.38 (3)°
  • V = 1139.3 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.95 mm−1
  • T = 293 K
  • 0.20 × 0.15 × 0.11 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 10841 measured reflections
  • 4602 independent reflections
  • 4356 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.057
  • S = 1.09
  • 4602 reflections
  • 353 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.70 e Å−3
  • Δρmin = −0.30 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1770 Friedel pairs
  • Flack parameter: 0.006 (18)

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]) and ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045905/dn2508sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045905/dn2508Isup2.hkl

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

supplementary crystallographic information

Comment

Quinolin-8-ol [quinolin-8-ol (oxine)] is well known as a particularly versatile ligand for use in metal complex chemistry (G. Smith, et al.,2001). It is also known that most of AgI in biological systems is not in the form of free AgI ions, but is coordinated by the abundance of biological ligands (Wu, et al.,2006). As part of our search for new biologically active compounds the title compound has been synthesized and we report its crystal structure here.

Scheme I

The AgI atom is coordinated by two N atoms and two O atoms from two quinolin-8-ols in a roughly planar environment with the largest deviation from the mean plane of the non H atoms being 0.223 (2)Å at C14 (Fig. 1). However, the two quinolin-8-ols are slightly bent with respect to each other making a dihedral angle of 9.55 (9)°. In the DNS anion, the NO2 and CO2 groups are twisted with respect to the phenyl ring making dihedral angles of of 29.5 (1)° for C21, N4, O6, O7, 10.7 (2)° for C19, N3, O4, 05 and 10.0 (2)° for C23, C25, O8, O9. All of the bond lengths and bond angles are in normal ranges (Smith, et al.,1999; Smith, et al.,2001; Wu, et al., 2006).

There are O—H···O hydrogen-bond interactions between two quinolin-8-ol and DNS which stabilize the crystal structure (Table 1, Fig. 1).

Experimental

The title compound(I) was prepared by the process as following: A mixture of 3,5-Dinitrosalicylic acid (0.01 mol), salt of quinolin-8-ol and sulfuric acid (0.02 mol) was stirred in distilled water (30 ml) for 3 h to obtain yellow deposit. A mixture of the deposit and AgNO3(0.01 mol) was stirred in ethanol (20 ml) at 353 K for 5 h, then afford the title compound (yield 83%). Single crystals suitable for X-ray measurements were obtailed by recrystallization from ethanol at room temperature.

Refinement

H atoms were included in calculated positions, with C—H distances constrained to 0.93Å (aromatic CH) and O—H distances constrained to 0.86Å and with Uiso=1.2–1.5Ueq.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.

Crystal data

[Ag(C9H7NO)2](C7H3N2O7)F(000) = 628
Mr = 625.30Dx = 1.823 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4356 reflections
a = 9.0154 (18) Åθ = 3.6–27.6°
b = 7.6122 (15) ŵ = 0.95 mm1
c = 17.138 (3) ÅT = 293 K
β = 104.38 (3)°Block, yellow
V = 1139.3 (4) Å30.20 × 0.15 × 0.11 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer4356 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
graphiteθmax = 27.6°, θmin = 3.6°
[var phi] and ω scansh = −11→11
10841 measured reflectionsk = −9→8
4602 independent reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.057w = 1/[σ2(Fo2) + (0.028P)2 + 0.3633P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
4602 reflectionsΔρmax = 0.70 e Å3
353 parametersΔρmin = −0.30 e Å3
1 restraintAbsolute structure: Flack (1983), 1770 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.006 (18)

Special details

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 > 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)

xyzUiso*/Ueq
Ag10.062198 (19)0.74284 (3)0.668865 (11)0.01870 (6)
O1−0.0991 (2)0.4624 (3)0.64039 (12)0.0199 (4)
H1AA−0.09500.34500.66700.030*
O20.1744 (2)0.5065 (3)0.77201 (12)0.0217 (4)
H2AA0.14090.41700.77900.033*
N1−0.1155 (2)0.7669 (4)0.55612 (13)0.0174 (5)
N20.2684 (3)0.8371 (3)0.75436 (14)0.0163 (5)
C1−0.1281 (3)0.9178 (4)0.51463 (19)0.0223 (6)
H1A−0.06131.00900.53540.027*
C2−0.2364 (4)0.9449 (4)0.44186 (18)0.0246 (6)
H2A−0.24101.05190.41520.030*
C3−0.3353 (3)0.8132 (4)0.41024 (19)0.0211 (6)
H3A−0.40800.82970.36180.025*
C4−0.3269 (3)0.6506 (4)0.45167 (18)0.0170 (6)
C5−0.4267 (3)0.5080 (4)0.42261 (17)0.0209 (6)
H5A−0.50130.51860.37440.025*
C6−0.4132 (3)0.3552 (4)0.46543 (18)0.0214 (6)
H6A−0.47740.26140.44540.026*
C7−0.3036 (3)0.3371 (4)0.53957 (17)0.0187 (6)
H7A−0.29770.23270.56830.022*
C8−0.2059 (3)0.4719 (4)0.56950 (16)0.0149 (5)
C9−0.2140 (3)0.6332 (4)0.52566 (16)0.0141 (5)
C100.3161 (3)0.9992 (4)0.74638 (17)0.0187 (6)
H10A0.25721.06970.70610.022*
C110.4512 (3)1.0703 (4)0.79573 (19)0.0222 (6)
H11A0.48071.18470.78780.027*
C120.5375 (3)0.9694 (4)0.85498 (18)0.0210 (6)
H12A0.62771.01400.88780.025*
C130.4907 (3)0.7962 (4)0.86706 (17)0.0172 (6)
C140.5745 (3)0.6843 (4)0.92847 (17)0.0199 (6)
H14A0.66550.72350.96260.024*
C150.5225 (3)0.5197 (4)0.93780 (17)0.0206 (6)
H15A0.57760.44790.97880.025*
C160.3864 (3)0.4567 (4)0.88625 (17)0.0177 (6)
H16A0.35200.34430.89370.021*
C170.3044 (3)0.5596 (4)0.82523 (16)0.0144 (5)
C180.3541 (2)0.7342 (6)0.81437 (14)0.0140 (4)
O30.1402 (2)−0.0140 (3)0.92529 (13)0.0260 (5)
H3B0.14050.07930.90150.039*
O4−0.4152 (2)−0.3754 (3)0.69128 (14)0.0284 (5)
O5−0.3271 (2)−0.5962 (3)0.76855 (13)0.0273 (5)
O60.1239 (2)−0.5246 (3)0.98348 (12)0.0211 (4)
O70.1678 (2)−0.2656 (4)1.03550 (11)0.0289 (4)
O8−0.0981 (2)0.1498 (3)0.70194 (12)0.0242 (5)
O90.0667 (2)0.2136 (3)0.81890 (12)0.0198 (5)
N3−0.3217 (2)−0.4436 (3)0.74770 (14)0.0173 (5)
N40.1088 (2)−0.3646 (3)0.98082 (14)0.0151 (5)
C19−0.1971 (3)−0.3338 (4)0.79249 (18)0.0131 (6)
C20−0.1028 (3)−0.3990 (3)0.86303 (16)0.0128 (5)
H20A−0.1152−0.51270.88030.015*
C210.0095 (3)−0.2909 (3)0.90660 (15)0.0118 (6)
C220.0328 (3)−0.1188 (4)0.88193 (16)0.0131 (5)
C23−0.0605 (3)−0.0602 (3)0.80700 (16)0.0130 (5)
C24−0.1769 (3)−0.1677 (4)0.76339 (18)0.0137 (6)
H24A−0.2405−0.12860.71520.016*
C25−0.0306 (3)0.1145 (4)0.77252 (16)0.0150 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag10.01624 (8)0.01725 (9)0.01946 (9)−0.00342 (12)−0.00152 (6)0.00022 (11)
O10.0213 (10)0.0127 (9)0.0199 (10)−0.0063 (8)−0.0062 (8)0.0045 (7)
O20.0185 (9)0.0169 (10)0.0244 (11)−0.0079 (8)−0.0046 (8)0.0028 (8)
N10.0194 (9)0.0143 (15)0.0179 (10)−0.0003 (11)0.0034 (8)0.0009 (10)
N20.0138 (10)0.0164 (12)0.0191 (12)−0.0018 (9)0.0047 (9)0.0005 (9)
C10.0256 (14)0.0145 (13)0.0262 (16)−0.0040 (13)0.0053 (12)0.0045 (11)
C20.0331 (16)0.0181 (15)0.0238 (16)0.0071 (14)0.0092 (13)0.0106 (12)
C30.0216 (13)0.0248 (14)0.0156 (15)0.0061 (12)0.0021 (11)0.0024 (11)
C40.0139 (12)0.0219 (15)0.0152 (14)0.0027 (11)0.0036 (10)0.0011 (12)
C50.0161 (13)0.0293 (16)0.0149 (14)0.0008 (13)−0.0007 (10)−0.0035 (12)
C60.0154 (13)0.0245 (15)0.0215 (15)−0.0088 (12)−0.0008 (10)−0.0052 (12)
C70.0181 (13)0.0179 (15)0.0188 (14)−0.0042 (11)0.0023 (10)0.0014 (11)
C80.0142 (12)0.0145 (13)0.0143 (13)0.0003 (11)0.0002 (10)0.0000 (10)
C90.0142 (12)0.0143 (13)0.0135 (13)−0.0007 (11)0.0030 (9)0.0009 (10)
C100.0208 (13)0.0172 (14)0.0199 (15)−0.0023 (12)0.0082 (11)0.0027 (11)
C110.0261 (14)0.0167 (14)0.0257 (16)−0.0085 (13)0.0098 (12)−0.0039 (12)
C120.0182 (13)0.0228 (15)0.0231 (15)−0.0110 (12)0.0071 (11)−0.0096 (12)
C130.0141 (11)0.0225 (15)0.0162 (13)−0.0030 (10)0.0064 (10)−0.0058 (10)
C140.0112 (11)0.0293 (15)0.0177 (14)−0.0033 (11)0.0005 (10)−0.0069 (10)
C150.0138 (12)0.0278 (16)0.0181 (14)0.0033 (12)0.0000 (10)0.0019 (11)
C160.0162 (12)0.0153 (13)0.0207 (14)−0.0018 (11)0.0032 (10)−0.0002 (10)
C170.0111 (11)0.0143 (13)0.0172 (14)−0.0019 (11)0.0028 (10)−0.0028 (10)
C180.0113 (9)0.0151 (11)0.0166 (11)0.0013 (17)0.0052 (8)0.0003 (15)
O30.0224 (10)0.0222 (11)0.0283 (12)−0.0065 (9)−0.0032 (9)0.0033 (9)
O40.0209 (10)0.0281 (12)0.0268 (12)−0.0043 (9)−0.0115 (8)−0.0011 (9)
O50.0294 (11)0.0195 (11)0.0293 (12)−0.0131 (10)0.0006 (9)0.0017 (9)
O60.0213 (10)0.0160 (10)0.0235 (11)0.0028 (8)0.0008 (8)0.0058 (8)
O70.0344 (9)0.0225 (10)0.0200 (9)0.0054 (15)−0.0118 (7)−0.0024 (13)
O80.0317 (11)0.0166 (11)0.0195 (11)−0.0060 (9)−0.0027 (8)0.0065 (8)
O90.0211 (8)0.0132 (14)0.0224 (9)−0.0063 (9)0.0004 (7)0.0004 (8)
N30.0140 (10)0.0190 (12)0.0169 (12)−0.0061 (10)0.0004 (9)−0.0041 (9)
N40.0115 (10)0.0166 (12)0.0153 (11)0.0017 (9)−0.0004 (8)0.0023 (9)
C190.0078 (11)0.0166 (13)0.0139 (14)−0.0039 (10)0.0007 (10)−0.0040 (11)
C200.0160 (12)0.0084 (12)0.0140 (13)−0.0004 (10)0.0034 (9)0.0006 (9)
C210.0095 (9)0.0131 (18)0.0109 (11)0.0044 (10)−0.0009 (8)0.0026 (9)
C220.0084 (11)0.0151 (14)0.0147 (13)−0.0009 (10)0.0011 (9)−0.0027 (10)
C230.0130 (11)0.0110 (13)0.0139 (12)−0.0003 (11)0.0013 (9)−0.0003 (10)
C240.0122 (12)0.0145 (14)0.0142 (14)0.0023 (11)0.0028 (10)0.0010 (11)
C250.0151 (12)0.0110 (12)0.0182 (14)0.0005 (11)0.0030 (10)0.0009 (10)

Geometric parameters (Å, °)

Ag1—N22.183 (2)C12—C131.415 (4)
Ag1—N12.190 (2)C12—H12A0.9300
Ag1—O22.549 (2)C13—C181.415 (4)
Ag1—O12.561 (2)C13—C141.417 (4)
O1—C81.352 (3)C14—C151.361 (4)
O1—H1AA0.9999C14—H14A0.9300
O2—C171.355 (3)C15—C161.406 (4)
O2—H2AA0.7666C15—H15A0.9300
N1—C11.341 (4)C16—C171.367 (4)
N1—C91.366 (4)C16—H16A0.9300
N2—C101.325 (4)C17—C181.430 (5)
N2—C181.368 (4)O3—C221.330 (3)
C1—C21.395 (4)O3—H3B0.8193
C1—H1A0.9300O4—N31.229 (3)
C2—C31.361 (5)O5—N31.220 (3)
C2—H2A0.9300O6—N41.225 (3)
C3—C41.420 (4)O7—N41.217 (3)
C3—H3A0.9300O8—C251.241 (3)
C4—C51.419 (4)O9—C251.274 (3)
C4—C91.422 (4)N3—C191.457 (3)
C5—C61.364 (4)N4—C211.472 (3)
C5—H5A0.9300C19—C201.386 (4)
C6—C71.409 (4)C19—C241.387 (4)
C6—H6A0.9300C20—C211.373 (4)
C7—C81.366 (4)C20—H20A0.9300
C7—H7A0.9300C21—C221.409 (4)
C8—C91.432 (4)C22—C231.421 (4)
C10—C111.407 (4)C23—C241.393 (4)
C10—H10A0.9300C23—C251.507 (4)
C11—C121.354 (4)C24—H24A0.9300
C11—H11A0.9300
N2—Ag1—N1151.54 (9)C10—C11—H11A120.6
N2—Ag1—O268.97 (8)C11—C12—C13120.1 (3)
N1—Ag1—O2138.45 (9)C11—C12—H12A119.9
N2—Ag1—O1138.63 (8)C13—C12—H12A119.9
N1—Ag1—O169.23 (8)C18—C13—C12117.5 (3)
O2—Ag1—O169.67 (6)C18—C13—C14119.5 (3)
C8—O1—Ag1111.74 (16)C12—C13—C14123.0 (3)
C8—O1—H1AA113.3C15—C14—C13120.3 (2)
Ag1—O1—H1AA134.7C15—C14—H14A119.8
C17—O2—Ag1112.59 (16)C13—C14—H14A119.8
C17—O2—H2AA117.9C14—C15—C16120.8 (3)
Ag1—O2—H2AA129.2C14—C15—H15A119.6
C1—N1—C9118.3 (2)C16—C15—H15A119.6
C1—N1—Ag1119.1 (2)C17—C16—C15120.5 (3)
C9—N1—Ag1122.58 (19)C17—C16—H16A119.7
C10—N2—C18118.3 (3)C15—C16—H16A119.7
C10—N2—Ag1118.73 (19)O2—C17—C16123.9 (3)
C18—N2—Ag1123.0 (2)O2—C17—C18115.9 (2)
N1—C1—C2123.3 (3)C16—C17—C18120.3 (2)
N1—C1—H1A118.4N2—C18—C13121.9 (3)
C2—C1—H1A118.4N2—C18—C17119.6 (2)
C3—C2—C1119.4 (3)C13—C18—C17118.6 (3)
C3—C2—H2A120.3C22—O3—H3B109.5
C1—C2—H2A120.3O5—N3—O4124.3 (2)
C2—C3—C4119.6 (3)O5—N3—C19118.3 (2)
C2—C3—H3A120.2O4—N3—C19117.4 (2)
C4—C3—H3A120.2O7—N4—O6124.3 (2)
C5—C4—C3122.8 (3)O7—N4—C21119.0 (2)
C5—C4—C9119.6 (3)O6—N4—C21116.7 (2)
C3—C4—C9117.7 (3)C20—C19—C24122.2 (3)
C6—C5—C4119.9 (3)C20—C19—N3118.7 (3)
C6—C5—H5A120.0C24—C19—N3119.1 (3)
C4—C5—H5A120.0C21—C20—C19118.0 (2)
C5—C6—C7121.2 (3)C21—C20—H20A121.0
C5—C6—H6A119.4C19—C20—H20A121.0
C7—C6—H6A119.4C20—C21—C22122.6 (2)
C8—C7—C6120.5 (3)C20—C21—N4116.7 (2)
C8—C7—H7A119.8C22—C21—N4120.7 (2)
C6—C7—H7A119.8O3—C22—C21122.2 (2)
O1—C8—C7123.1 (2)O3—C22—C23120.1 (3)
O1—C8—C9116.7 (2)C21—C22—C23117.7 (2)
C7—C8—C9120.2 (2)C24—C23—C22119.9 (3)
N1—C9—C4121.7 (2)C24—C23—C25119.5 (2)
N1—C9—C8119.7 (2)C22—C23—C25120.5 (2)
C4—C9—C8118.6 (2)C19—C24—C23119.4 (3)
N2—C10—C11123.4 (3)C19—C24—H24A120.3
N2—C10—H10A118.3C23—C24—H24A120.3
C11—C10—H10A118.3O8—C25—O9125.1 (3)
C12—C11—C10118.9 (3)O8—C25—C23118.7 (2)
C12—C11—H11A120.6O9—C25—C23116.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1AA···O81.001.602.602 (3)175
O2—H2AA···O90.771.882.636 (3)168
O3—H3B···O90.821.742.483 (3)150

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2508).

References

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