Crystal structure of catena-poly[silver(I)-μ-l-tyrosinato-κ2O:N]

Yousaf, A.; Tahir, M.N.; Rauf, A.; Awan, S.A.; Ahmad, S.

doi:10.1107/S2056989015001905

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 3| March 2015| Pages m50-m51

doi:10.1107/S2056989015001905

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Crystal structure of catena-poly[silver(I)-μ-L-tyrosinato-κ²O:N]

Aqsa Yousaf,^a Muhammad Nawaz Tahir,^b ^* Abdul Rauf,^a Shafique Ahmad Awan ^c and Saeed Ahmad ^a

^aDepartment of Chemistry, University of Engineering and Technology, Lahore 54890, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Punjab, Pakistan, and ^cPAEC, PO Box No. 1114, Islamabad GPO 44000, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

Edited by W. Imhof, University Koblenz-Landau, Germany (Received 10 January 2015; accepted 29 January 2015; online 4 February 2015)

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 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.

Keywords: crystal structure; one-dimensional silver(I) coordination polymer; L-tyrosinate; hydrogen bonding.

CCDC reference: 1046166

1. Related literature

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

2. Experimental

2.1. Crystal data

[Ag(C₉H₁₀NO₃)]
M_r = 288.05
Monoclinic, P 2₁
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.052
S = 1.11
1816 reflections
134 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −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)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.82	1.91	2.710 (7)	166
N1—H1B⋯O1ⁱⁱ	0.87 (7)	2.19 (7)	2.988 (6)	152 (5)
C2—H2⋯O2ⁱⁱⁱ	0.98	2.63	3.589 (7)	168
C3—H3B⋯O3^iv	0.97	2.48	3.441 (7)	171
Symmetry codes: (i) x-1, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (iv) x+1, y, z.

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.

Supporting information

CCDC reference: 1046166

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015001905/im2459sup1.cif

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

checkCIF report

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).

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

	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.
	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
M_r = 288.05	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0222P)² + 0.0305P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
1816 reflections	Δρ_max = 0.28 e Å⁻³
134 parameters	Δρ_min = −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)

Crystal data top

[Ag(C₉H₁₀NO₃)]	V = 473.64 (6) Å³
M_r = 288.05	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.2944 (5) Å	µ = 2.11 mm⁻¹
b = 7.1464 (5) Å	T = 296 K
c = 9.2736 (7) Å	0.34 × 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)
T_min = 0.538, T_max = 0.701	R_int = 0.023
4086 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.052	Δρ_max = 0.28 e Å⁻³
S = 1.11	Δρ_min = −0.48 e Å⁻³
1816 reflections	Absolute structure: Flack x determined using 751 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
134 parameters	Absolute 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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

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

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.87 (7)	2.19 (7)	2.988 (6)	152 (5)
C2—H2···O2^v	0.98	2.63	3.589 (7)	168
C3—H3B···O3ⁱ	0.97	2.48	3.441 (7)	171

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	1.91	2.710 (7)	166.0
N1—H1B···O1ⁱⁱ	0.87 (7)	2.19 (7)	2.988 (6)	152 (5)
C2—H2···O2ⁱⁱⁱ	0.98	2.63	3.589 (7)	167.9
C3—H3B···O3^iv	0.97	2.48	3.441 (7)	171.3

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

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