Crystal structure of catena-poly[silver(I)-μ-l-tyrosinato-κ(2) O:N].

The title compound, [Ag(C9H10NO3)] n , is a polymeric silver(I) complex of l-tyrosine. The Ag(I) atom is connected to N and O atoms of two different l-tyrosine ligands in an almost linear arrangement, with an N(i)-Ag-O1 bond angle of 173.4 (2)° [symmetry code: (i) x + 1, y, z]. The Ag-N(i) 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 inter-actions connect these chains into a double-layer polymeric network in the ab plane.

Related literature

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

Experimental

Crystal data

[Ag(C9H10NO3)]

M = 288.05

Monoclinic,

a = 7.2944 (5) Å

b = 7.1464 (5) Å

c = 9.2736 (7) Å

β = 101.546 (4)°

V = 473.64 (6) Å3

Z = 2

Mo Kα radiation

μ = 2.11 mm−1

T = 296 K

0.34 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.538, T max = 0.701

4086 measured reflections

1816 independent reflections

1752 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.052

S = 1.11

1816 reflections

134 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.48 e Å−3

Absolute structure: Flack x determined using 751 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: 0.04 (2)

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015001905/im2459sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015001905/im2459Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015001905/im2459fig1.tif

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.

Click here for additional data file.

PLATON . DOI: 10.1107/S2056989015001905/im2459fig2.tif

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.

CCDC reference: 1046166

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

[Ag(C9H10NO3)]	F(000) = 284
Mr = 288.05	Dx = 2.020 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.2944 (5) Å	Cell parameters from 1753 reflections
b = 7.1464 (5) Å	θ = 2.9–26.0°
c = 9.2736 (7) Å	µ = 2.11 mm−1
β = 101.546 (4)°	T = 296 K
V = 473.64 (6) Å3	Block, colorless
Z = 2	0.34 × 0.20 × 0.18 mm

Bruker Kappa APEXII CCD diffractometer	1816 independent reflections
Radiation source: fine-focus sealed tube	1752 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 2.9°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.538, Tmax = 0.701	l = −11→11
4086 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022	H 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 reflections	Δρmax = 0.28 e Å−3
134 parameters	Δρmin = −0.48 e Å−3
1 restraint	Absolute structure: Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (2)

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
Ag1	0.95099 (4)	0.57540 (7)	0.87242 (4)	0.04160 (14)
O1	0.6862 (5)	0.4646 (5)	0.9045 (4)	0.0364 (8)
O2	0.5870 (6)	0.7436 (5)	0.8171 (6)	0.0493 (10)
O3	−0.4102 (5)	0.0526 (9)	0.6482 (4)	0.0418 (12)
H3	−0.4074	−0.0285	0.7111	0.063*
N1	0.2293 (6)	0.6694 (6)	0.8634 (6)	0.0367 (10)
H1A	0.219 (9)	0.716 (8)	0.781 (7)	0.044*
H1B	0.282 (9)	0.725 (9)	0.945 (7)	0.044*
C1	0.5594 (5)	0.5852 (11)	0.8581 (4)	0.0270 (9)
C2	0.3595 (7)	0.5138 (6)	0.8509 (5)	0.0265 (11)
H2	0.3601	0.4267	0.9326	0.032*
C3	0.2963 (7)	0.4091 (7)	0.7071 (5)	0.0307 (10)
H3A	0.2921	0.4963	0.6264	0.037*
H3B	0.3892	0.3146	0.6989	0.037*
C4	0.1078 (7)	0.3152 (6)	0.6902 (5)	0.0273 (10)
C5	0.0880 (7)	0.1543 (6)	0.7700 (5)	0.0312 (10)
H5	0.1925	0.1052	0.8327	0.037*
C6	−0.0825 (6)	0.0651 (10)	0.7588 (5)	0.0312 (9)
H6	−0.0914	−0.0417	0.8143	0.037*
C7	−0.2405 (6)	0.1346 (6)	0.6650 (5)	0.0290 (11)
C8	−0.2230 (7)	0.2942 (7)	0.5838 (6)	0.0336 (11)
H8	−0.3272	0.3422	0.5200	0.040*
C9	−0.0515 (7)	0.3826 (7)	0.5972 (5)	0.0324 (11)
H9	−0.0429	0.4900	0.5423	0.039*

	U11	U22	U33	U12	U13	U23
Ag1	0.01769 (18)	0.0458 (2)	0.0638 (3)	−0.0039 (2)	0.01412 (15)	−0.0078 (3)
O1	0.0186 (19)	0.044 (2)	0.047 (2)	0.0018 (16)	0.0080 (16)	0.0041 (17)
O2	0.034 (2)	0.038 (2)	0.077 (3)	−0.0093 (18)	0.015 (2)	0.0112 (19)
O3	0.0268 (16)	0.039 (3)	0.057 (2)	−0.009 (2)	0.0010 (14)	0.004 (2)
N1	0.020 (2)	0.039 (2)	0.052 (3)	−0.0001 (19)	0.010 (2)	−0.006 (2)
C1	0.0209 (19)	0.031 (2)	0.030 (2)	−0.006 (3)	0.0076 (15)	−0.007 (3)
C2	0.019 (3)	0.031 (3)	0.031 (3)	−0.0017 (16)	0.0073 (19)	0.0005 (16)
C3	0.025 (3)	0.037 (3)	0.032 (3)	−0.006 (2)	0.009 (2)	−0.003 (2)
C4	0.027 (2)	0.029 (2)	0.025 (2)	−0.0037 (19)	0.005 (2)	−0.0037 (18)
C5	0.027 (2)	0.027 (2)	0.036 (3)	0.0020 (19)	−0.002 (2)	0.0040 (19)
C6	0.035 (2)	0.024 (2)	0.034 (2)	−0.004 (3)	0.0055 (17)	0.000 (3)
C7	0.024 (2)	0.029 (3)	0.033 (3)	−0.0052 (17)	0.005 (2)	−0.0073 (17)
C8	0.025 (3)	0.038 (3)	0.035 (3)	−0.002 (2)	−0.001 (2)	0.001 (2)
C9	0.034 (3)	0.033 (2)	0.030 (3)	−0.003 (2)	0.004 (2)	0.0053 (19)

Ag1—N1i	2.156 (4)	C3—C4	1.510 (6)
Ag1—O1	2.162 (4)	C3—H3A	0.9700
O1—C1	1.275 (7)	C3—H3B	0.9700
O2—C1	1.224 (9)	C4—C9	1.388 (7)
O3—C7	1.350 (6)	C4—C5	1.390 (6)
O3—H3	0.8200	C5—C6	1.383 (7)
N1—C2	1.482 (6)	C5—H5	0.9300
N1—Ag1ii	2.156 (4)	C6—C7	1.390 (7)
N1—H1A	0.83 (6)	C6—H6	0.9300
N1—H1B	0.87 (7)	C7—C8	1.386 (6)
C1—C2	1.534 (6)	C8—C9	1.385 (7)
C2—C3	1.518 (7)	C8—H8	0.9300
C2—H2	0.9800	C9—H9	0.9300
N1i—Ag1—O1	173.41 (18)	C4—C3—H3B	108.6
C1—O1—Ag1	108.3 (3)	C2—C3—H3B	108.6
C7—O3—H3	109.5	H3A—C3—H3B	107.5
C2—N1—Ag1ii	113.1 (3)	C9—C4—C5	117.0 (4)
C2—N1—H1A	100 (4)	C9—C4—C3	122.8 (4)
Ag1ii—N1—H1A	105 (4)	C5—C4—C3	120.1 (4)
C2—N1—H1B	103 (4)	C6—C5—C4	122.0 (5)
Ag1ii—N1—H1B	111 (4)	C6—C5—H5	119.0
H1A—N1—H1B	124 (6)	C4—C5—H5	119.0
O2—C1—O1	125.2 (4)	C5—C6—C7	120.2 (5)
O2—C1—C2	120.6 (5)	C5—C6—H6	119.9
O1—C1—C2	114.2 (6)	C7—C6—H6	119.9
N1—C2—C3	110.6 (4)	O3—C7—C8	118.5 (5)
N1—C2—C1	111.4 (5)	O3—C7—C6	122.9 (5)
C3—C2—C1	108.7 (4)	C8—C7—C6	118.6 (5)
N1—C2—H2	108.7	C9—C8—C7	120.4 (5)
C3—C2—H2	108.7	C9—C8—H8	119.8
C1—C2—H2	108.7	C7—C8—H8	119.8
C4—C3—C2	114.8 (4)	C8—C9—C4	121.8 (4)
C4—C3—H3A	108.6	C8—C9—H9	119.1
C2—C3—H3A	108.6	C4—C9—H9	119.1
Ag1—O1—C1—O2	−7.0 (6)	C2—C3—C4—C5	−73.4 (6)
Ag1—O1—C1—C2	170.8 (3)	C9—C4—C5—C6	−0.5 (7)
Ag1ii—N1—C2—C3	63.8 (5)	C3—C4—C5—C6	179.3 (5)
Ag1ii—N1—C2—C1	−175.2 (3)	C4—C5—C6—C7	0.6 (7)
O2—C1—C2—N1	−28.0 (7)	C5—C6—C7—O3	179.2 (5)
O1—C1—C2—N1	154.2 (4)	C5—C6—C7—C8	−0.1 (7)
O2—C1—C2—C3	94.2 (6)	O3—C7—C8—C9	−179.8 (5)
O1—C1—C2—C3	−83.6 (5)	C6—C7—C8—C9	−0.4 (7)
N1—C2—C3—C4	−62.6 (5)	C7—C8—C9—C4	0.5 (7)
C1—C2—C3—C4	174.7 (5)	C5—C4—C9—C8	0.0 (7)
C2—C3—C4—C9	106.5 (5)	C3—C4—C9—C8	−179.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2iii	0.82	1.91	2.710 (7)	166
N1—H1B···O1iv	0.87 (7)	2.19 (7)	2.988 (6)	152 (5)
C2—H2···O2v	0.98	2.63	3.589 (7)	168
C3—H3B···O3i	0.97	2.48	3.441 (7)	171

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O3H3O2i	0.82	1.91	2.710(7)	166
N1H1BO1ii	0.87(7)	2.19(7)	2.988(6)	152(5)
C2H2O2iii	0.98	2.63	3.589(7)	168
C3H3BO3iv	0.97	2.48	3.441(7)	171

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