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The title compound, [Ag(C9H10NO3)]n, is a polymeric silver(I) complex of L-tyrosine. The AgI atom is connected to N and O atoms of two different L-tyrosine ligands in an almost linear arrangement, with an Ni—Ag—O1 bond angle of 173.4 (2)° [symmetry code: (i) x + 1, y, z]. The Ag—Ni and Ag—O bond lengths are 2.156 (5) and 2.162 (4) Å, respectively. The polymeric chains extend along the crystallographic a axis. Strong hydrogen bonds of the N—H...O and O—H...O types and additional C—H...O inter­actions connect these chains into a double-layer polymeric network in the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015001905/im2459sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015001905/im2459Isup2.hkl
Contains datablock I

CCDC reference: 1046166

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.022
  • wR factor = 0.052
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT090_ALERT_3_C Poor Data / Parameter Ratio (Zmax > 18) ........ 7.50 Note PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A .. Please Check PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O2 .. 2.63 Ang.
Alert level G PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension 1 Info PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT791_ALERT_4_G The Model has Chirality at C2 (Chiral SPGR) S Verify PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check

Comment top

Silver(I) complexes of amino acids are important from a medicinal point of view because of their effective biological activities against bacteria, yeasts and moulds (Ahmad et al. 2006; Kasuga et al. 2011; Nomiya et al. 2000; Nomiya & Yokoyama 2002). These complexes usually exist in the form of polymers and the Ag—O and Ag—N bonds play an important role in exhibiting a wide spectrum of antimicrobial activities. The Ag—O bonding complexes can readily undergo ligand replacement with sulfur containing biological ligands such as proteins (Ahmad et al. 2006; Kasuga et al. 2011; Nomiya et al. 2000; Nomiya & Yokoyama, 2002). The crystal structures of these complexes are also characterized by strong hydrogen bonding. The present report is concerned with the crystal structure of a new polymeric silver(I) complex of L-tyrosine (Fig. 1), which has been synthesized for various studies.

In (I) the part of acetate group A (C1/C2/O1/O2) is planar with r. m. s. deviation of 0.0065 Å. The attached N-atom is at a distance of 0.614 (9) Å from the plane A. The 4-methylphenol group B (C3—C9/O3) also attached at the same C-atom is planar with r. m. s. deviation of 0.0032 Å. The dihedral angle between A/B is 21.3 (3)°. Silver atoms are coordinted to L-tyrosine through the deprotonated O atom of the carboxyl group and the amino group of another amino acid residue. The Ag1–N1i [i = x + 1, y, z] and Ag1–O1 bond distances are almost equal and have values of 2.156 (5) and 2.162 (4) Å, respectively. The N1i–Ag1–O1 bond angle is 173.4 (2)° due to which the silver atoms are at a separation of 7.2944 (7) Å in this polymeric complex. The polymeric chains are oriented along the crystallographic a-axis. Polymeric chains are linked to layers in the ab plane by O—H···O hydrogen bonds and two of theses layers are additionally linked to a double layer structure by N—H···O hydrogen bonds. This arrangement is further stabilized by weak C—H···O hydrogen bonds (Table 1, Fig. 2). Additionally, C—H···π interactions between benzene rings are observed. Due to these interactions molecules are arranged in the form of a two-dimensional polymeric network with base vectors [1 0 0], [0 1 0] in the (001) plane.

Related literature top

For related structures and related studies, see: Ahmad et al. (2006); Kasuga et al. (2011); Nomiya et al. (2000); Nomiya & Yokoyama (2002).

Experimental top

L-Tyrosine (0.18 g, 1.0 mmol) was disolved in 10 ml water by adding 10 drops of 1.0 M NaOH. AgNO3 (0.17 g, 1.0 mmol) was disolved in 10 ml of acetonitrile. The L-tyrosine solution was slowly added to the AgNO3 solution and the resulting mixture after filtration was kept in the refrigerator at 0°C for crystallization. After three days, colorless needles of (I) were obtained (yield: 20%, m.p = 547 K).

Refinement top

The coordinates of H-atoms of the NH2 group were obtained from the Fourier map and refined isotropically. The other H-atoms were positioned geometrically (C–H = 0.93–0.98 Å, O—H = 0.82 Å) and refined as riding with Uiso(H) = xUeq(C, N, O) with x = 1.5 for hydroxy and x = 1.2 for other H-atoms.

Computing details top

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the asymmetric unit of the title compound. Thermal ellipsoids are drawn at the 50% probability level. H atoms are shown by small circles of arbitrary radii.
[Figure 2] Fig. 2. The partial packing (PLATON; Spek, 2009) showing the polymeric network due to C—H···O, N—H···O and O—H···O interactions. H atoms not involved in hydrogen-bonding interactions are omitted for clarity.
catena-Poly[silver(I)-µ-L-tyrosinato-κ2O:N] top
Crystal data top
[Ag(C9H10NO3)]F(000) = 284
Mr = 288.05Dx = 2.020 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.2944 (5) ÅCell parameters from 1753 reflections
b = 7.1464 (5) Åθ = 2.9–26.0°
c = 9.2736 (7) ŵ = 2.11 mm1
β = 101.546 (4)°T = 296 K
V = 473.64 (6) Å3Block, colorless
Z = 20.34 × 0.20 × 0.18 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
1816 independent reflections
Radiation source: fine-focus sealed tube1752 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8.00 pixels mm-1θmax = 26.0°, θmin = 2.9°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 88
Tmin = 0.538, Tmax = 0.701l = 1111
4086 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.052 w = 1/[σ2(Fo2) + (0.0222P)2 + 0.0305P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
1816 reflectionsΔρmax = 0.28 e Å3
134 parametersΔρmin = 0.48 e Å3
1 restraintAbsolute structure: Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (2)
Crystal data top
[Ag(C9H10NO3)]V = 473.64 (6) Å3
Mr = 288.05Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.2944 (5) ŵ = 2.11 mm1
b = 7.1464 (5) ÅT = 296 K
c = 9.2736 (7) Å0.34 × 0.20 × 0.18 mm
β = 101.546 (4)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
1816 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
1752 reflections with I > 2σ(I)
Tmin = 0.538, Tmax = 0.701Rint = 0.023
4086 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.022H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.052Δρmax = 0.28 e Å3
S = 1.11Δρmin = 0.48 e Å3
1816 reflectionsAbsolute structure: Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
134 parametersAbsolute structure parameter: 0.04 (2)
1 restraint
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.95099 (4)0.57540 (7)0.87242 (4)0.04160 (14)
O10.6862 (5)0.4646 (5)0.9045 (4)0.0364 (8)
O20.5870 (6)0.7436 (5)0.8171 (6)0.0493 (10)
O30.4102 (5)0.0526 (9)0.6482 (4)0.0418 (12)
H30.40740.02850.71110.063*
N10.2293 (6)0.6694 (6)0.8634 (6)0.0367 (10)
H1A0.219 (9)0.716 (8)0.781 (7)0.044*
H1B0.282 (9)0.725 (9)0.945 (7)0.044*
C10.5594 (5)0.5852 (11)0.8581 (4)0.0270 (9)
C20.3595 (7)0.5138 (6)0.8509 (5)0.0265 (11)
H20.36010.42670.93260.032*
C30.2963 (7)0.4091 (7)0.7071 (5)0.0307 (10)
H3A0.29210.49630.62640.037*
H3B0.38920.31460.69890.037*
C40.1078 (7)0.3152 (6)0.6902 (5)0.0273 (10)
C50.0880 (7)0.1543 (6)0.7700 (5)0.0312 (10)
H50.19250.10520.83270.037*
C60.0825 (6)0.0651 (10)0.7588 (5)0.0312 (9)
H60.09140.04170.81430.037*
C70.2405 (6)0.1346 (6)0.6650 (5)0.0290 (11)
C80.2230 (7)0.2942 (7)0.5838 (6)0.0336 (11)
H80.32720.34220.52000.040*
C90.0515 (7)0.3826 (7)0.5972 (5)0.0324 (11)
H90.04290.49000.54230.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.01769 (18)0.0458 (2)0.0638 (3)0.0039 (2)0.01412 (15)0.0078 (3)
O10.0186 (19)0.044 (2)0.047 (2)0.0018 (16)0.0080 (16)0.0041 (17)
O20.034 (2)0.038 (2)0.077 (3)0.0093 (18)0.015 (2)0.0112 (19)
O30.0268 (16)0.039 (3)0.057 (2)0.009 (2)0.0010 (14)0.004 (2)
N10.020 (2)0.039 (2)0.052 (3)0.0001 (19)0.010 (2)0.006 (2)
C10.0209 (19)0.031 (2)0.030 (2)0.006 (3)0.0076 (15)0.007 (3)
C20.019 (3)0.031 (3)0.031 (3)0.0017 (16)0.0073 (19)0.0005 (16)
C30.025 (3)0.037 (3)0.032 (3)0.006 (2)0.009 (2)0.003 (2)
C40.027 (2)0.029 (2)0.025 (2)0.0037 (19)0.005 (2)0.0037 (18)
C50.027 (2)0.027 (2)0.036 (3)0.0020 (19)0.002 (2)0.0040 (19)
C60.035 (2)0.024 (2)0.034 (2)0.004 (3)0.0055 (17)0.000 (3)
C70.024 (2)0.029 (3)0.033 (3)0.0052 (17)0.005 (2)0.0073 (17)
C80.025 (3)0.038 (3)0.035 (3)0.002 (2)0.001 (2)0.001 (2)
C90.034 (3)0.033 (2)0.030 (3)0.003 (2)0.004 (2)0.0053 (19)
Geometric parameters (Å, º) top
Ag1—N1i2.156 (4)C3—C41.510 (6)
Ag1—O12.162 (4)C3—H3A0.9700
O1—C11.275 (7)C3—H3B0.9700
O2—C11.224 (9)C4—C91.388 (7)
O3—C71.350 (6)C4—C51.390 (6)
O3—H30.8200C5—C61.383 (7)
N1—C21.482 (6)C5—H50.9300
N1—Ag1ii2.156 (4)C6—C71.390 (7)
N1—H1A0.83 (6)C6—H60.9300
N1—H1B0.87 (7)C7—C81.386 (6)
C1—C21.534 (6)C8—C91.385 (7)
C2—C31.518 (7)C8—H80.9300
C2—H20.9800C9—H90.9300
N1i—Ag1—O1173.41 (18)C4—C3—H3B108.6
C1—O1—Ag1108.3 (3)C2—C3—H3B108.6
C7—O3—H3109.5H3A—C3—H3B107.5
C2—N1—Ag1ii113.1 (3)C9—C4—C5117.0 (4)
C2—N1—H1A100 (4)C9—C4—C3122.8 (4)
Ag1ii—N1—H1A105 (4)C5—C4—C3120.1 (4)
C2—N1—H1B103 (4)C6—C5—C4122.0 (5)
Ag1ii—N1—H1B111 (4)C6—C5—H5119.0
H1A—N1—H1B124 (6)C4—C5—H5119.0
O2—C1—O1125.2 (4)C5—C6—C7120.2 (5)
O2—C1—C2120.6 (5)C5—C6—H6119.9
O1—C1—C2114.2 (6)C7—C6—H6119.9
N1—C2—C3110.6 (4)O3—C7—C8118.5 (5)
N1—C2—C1111.4 (5)O3—C7—C6122.9 (5)
C3—C2—C1108.7 (4)C8—C7—C6118.6 (5)
N1—C2—H2108.7C9—C8—C7120.4 (5)
C3—C2—H2108.7C9—C8—H8119.8
C1—C2—H2108.7C7—C8—H8119.8
C4—C3—C2114.8 (4)C8—C9—C4121.8 (4)
C4—C3—H3A108.6C8—C9—H9119.1
C2—C3—H3A108.6C4—C9—H9119.1
Ag1—O1—C1—O27.0 (6)C2—C3—C4—C573.4 (6)
Ag1—O1—C1—C2170.8 (3)C9—C4—C5—C60.5 (7)
Ag1ii—N1—C2—C363.8 (5)C3—C4—C5—C6179.3 (5)
Ag1ii—N1—C2—C1175.2 (3)C4—C5—C6—C70.6 (7)
O2—C1—C2—N128.0 (7)C5—C6—C7—O3179.2 (5)
O1—C1—C2—N1154.2 (4)C5—C6—C7—C80.1 (7)
O2—C1—C2—C394.2 (6)O3—C7—C8—C9179.8 (5)
O1—C1—C2—C383.6 (5)C6—C7—C8—C90.4 (7)
N1—C2—C3—C462.6 (5)C7—C8—C9—C40.5 (7)
C1—C2—C3—C4174.7 (5)C5—C4—C9—C80.0 (7)
C2—C3—C4—C9106.5 (5)C3—C4—C9—C8179.8 (4)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2iii0.821.912.710 (7)166
N1—H1B···O1iv0.87 (7)2.19 (7)2.988 (6)152 (5)
C2—H2···O2v0.982.633.589 (7)168
C3—H3B···O3i0.972.483.441 (7)171
Symmetry codes: (i) x+1, y, z; (iii) x1, y1, z; (iv) x+1, y+1/2, z+2; (v) x+1, y1/2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.821.912.710 (7)166.0
N1—H1B···O1ii0.87 (7)2.19 (7)2.988 (6)152 (5)
C2—H2···O2iii0.982.633.589 (7)167.9
C3—H3B···O3iv0.972.483.441 (7)171.3
Symmetry codes: (i) x1, y1, z; (ii) x+1, y+1/2, z+2; (iii) x+1, y1/2, z+2; (iv) x+1, y, z.
 

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