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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): m591.
Published online 2008 March 29. doi:  10.1107/S1600536808008064
PMCID: PMC2961039

(4-Chloro­benzoato)bis(5-methyl-2-pyridylamine)silver(I)

Abstract

The title compound, [Ag(C7H4ClO2)(C6H8N2)2], is a mononuclear silver(I) complex. The AgI atom is three-coordinated by two pyridine N atoms from two 5-methyl­pyridin-2-ylamine ligands and by one O atom of a 4-chloro­benzoate ligand, forming a distorted T-shaped coordination. In the crystal structure, the mol­ecules are linked through inter­molecular N—H(...)O hydrogen bonds, forming chains running along the b axis.

Related literature

For related literature, see: Bi et al. (2002 [triangle]); Deng et al. (2004 [triangle]); Jones et al. (2006 [triangle]); Khan et al. (2005 [triangle]); Kristiansson (2000 [triangle]); Li et al. (2007 [triangle]); Odoko et al. (2007 [triangle]); Sailaja et al. (2001 [triangle]); Wang & Okabe (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m591-scheme1.jpg

Experimental

Crystal data

  • [Ag(C7H4ClO2)(C6H8N2)2]
  • M r = 479.71
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m591-efi1.jpg
  • a = 15.983 (3) Å
  • b = 5.7428 (9) Å
  • c = 21.703 (4) Å
  • β = 98.460 (2)°
  • V = 1970.4 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.18 mm−1
  • T = 298 (2) K
  • 0.37 × 0.35 × 0.32 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.669, T max = 0.704
  • 13465 measured reflections
  • 4064 independent reflections
  • 3277 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.087
  • S = 1.03
  • 4064 reflections
  • 258 parameters
  • 6 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008064/ci2572sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008064/ci2572Isup2.hkl

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

Acknowledgments

This work was supported by the Gansu Young Foundation of China (grant No. 20635) and the ‘Qing Lan’ Talent Engineering Funds of Lanzhou Jiaotong University.

supplementary crystallographic information

Comment

Silver(I) complexes with carboxylate ligands and amine compounds have been widely investigated due to their versatile structures (Odoko et al., 2007; Li et al., 2007; Jones et al., 2006; Bi et al., 2002). We report herein the crystal structure of the title silver(I) complex.

The title compound is a mononuclear silver(I) complex (Fig. 1). The AgI atom is three-coordinated by two pyridine N atoms from two 5-methylpyridin-2-ylamine ligands and by one O atom of a 4-chlorobenzoate ligand, forming a distorted T-shaped coordination, the distortion being caused by the weak coordination of the carboxylate O atom (Ag1—O1 = 2.647 (2) Å, Table 1). The Ag—N bond lengths (Table 1) are comparable with the values observed in other silver(I) complexes (Kristiansson, 2000; Wang & Okabe, 2004; Sailaja et al., 2001; Khan et al., 2005; Deng et al., 2004).

In the crystal structure, the molecules are linked through intermolecular N—H···O hydrogen bonds (Table 2), forming chains running along the b axis (Fig. 2).

Experimental

Ag2O (0.1 mmol, 23.2 mg) and 4-chlorobenzoic acid (0.1 mmol, 15.6 mg) were dissolved in an ammonia solution (10 ml, 30%), and the mixture was stirred for 20 min at room temperature. To the above mixture was added with stirring a methanol solution (3 ml) of 5-methylpyridin-2-ylamine (0.2 mmol, 21.6 mg). The final mixture was stirred for 30 min at room temperature. The resulting clear colourless solution was kept in dark for 12 d, yielding colourless block-shaped crystals.

Refinement

Atoms H2A, H2B, H4A and H4B were located in a difference Fourier map and refined isotropically, with N—H and H···H distances restrained to 0.90 (1) Å and 1.43 (2) Å, respectively. Other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.96 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C).

Figures

Fig. 1.
The structure of the title complex, showing 30% probability displacement ellipsoids and the atomic numbering.
Fig. 2.
The crystal packing of the title compound, viewed down the b axis. Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

[Ag(C7H4ClO2)(C6H8N2)2]F000 = 968
Mr = 479.71Dx = 1.617 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3734 reflections
a = 15.983 (3) Åθ = 2.5–24.9º
b = 5.7428 (9) ŵ = 1.18 mm1
c = 21.703 (4) ÅT = 298 (2) K
β = 98.460 (2)ºBlock, colourless
V = 1970.4 (6) Å30.37 × 0.35 × 0.32 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer4064 independent reflections
Radiation source: fine-focus sealed tube3277 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.032
T = 298(2) Kθmax = 26.5º
ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −19→20
Tmin = 0.669, Tmax = 0.704k = −7→7
13465 measured reflectionsl = −26→27

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087  w = 1/[σ2(Fo2) + (0.0422P)2 + 0.4221P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4064 reflectionsΔρmax = 0.53 e Å3
258 parametersΔρmin = −0.34 e Å3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
Ag10.291478 (15)0.09298 (4)0.077611 (11)0.05012 (11)
Cl10.69700 (7)0.65902 (19)0.36548 (5)0.0793 (3)
O10.35007 (14)0.2179 (4)0.19330 (10)0.0573 (6)
O20.45197 (17)0.0110 (5)0.16007 (13)0.0760 (8)
N10.34955 (14)0.3452 (4)0.02193 (11)0.0388 (5)
N20.39194 (19)0.5847 (5)0.10583 (14)0.0556 (7)
N30.20646 (14)−0.2005 (4)0.08709 (11)0.0432 (6)
N40.2241 (2)−0.1612 (6)0.19393 (13)0.0605 (8)
C10.6161 (2)0.5050 (6)0.31981 (14)0.0507 (8)
C20.5373 (2)0.6012 (6)0.30750 (15)0.0542 (8)
H20.52580.74320.32510.065*
C30.4749 (2)0.4848 (6)0.26869 (14)0.0491 (7)
H30.42100.54890.26020.059*
C40.49170 (19)0.2737 (5)0.24224 (13)0.0427 (7)
C50.5713 (2)0.1802 (6)0.25682 (16)0.0554 (8)
H50.58310.03710.24000.066*
C60.6338 (2)0.2935 (7)0.29568 (17)0.0631 (9)
H60.68730.22770.30540.076*
C70.4262 (2)0.1546 (6)0.19559 (14)0.0481 (8)
C80.38570 (17)0.5444 (5)0.04449 (15)0.0417 (7)
C90.41727 (18)0.7050 (5)0.00414 (17)0.0501 (8)
H90.44120.84450.01980.060*
C100.41269 (19)0.6557 (6)−0.05702 (17)0.0525 (8)
H100.43370.7613−0.08340.063*
C110.37643 (19)0.4460 (6)−0.08121 (15)0.0465 (7)
C120.34602 (17)0.3021 (5)−0.03981 (13)0.0414 (7)
H120.32090.1636−0.05510.050*
C130.3731 (2)0.3791 (7)−0.14840 (16)0.0674 (11)
H13A0.34710.2288−0.15530.101*
H13B0.42950.3734−0.15860.101*
H13C0.34060.4923−0.17430.101*
C140.19164 (17)−0.2802 (6)0.14244 (14)0.0438 (7)
C150.1459 (2)−0.4866 (6)0.14600 (16)0.0535 (8)
H150.1354−0.54050.18450.064*
C160.1171 (2)−0.6072 (6)0.09412 (17)0.0548 (8)
H160.0872−0.74470.09700.066*
C170.13206 (19)−0.5268 (6)0.03557 (15)0.0493 (8)
C180.17643 (19)−0.3242 (6)0.03562 (15)0.0477 (7)
H180.1868−0.2669−0.00260.057*
C190.1021 (3)−0.6605 (7)−0.02362 (18)0.0726 (11)
H19A0.1096−0.5667−0.05900.109*
H19B0.0433−0.6984−0.02530.109*
H19C0.1344−0.8013−0.02410.109*
H4B0.209 (2)−0.185 (6)0.2308 (9)0.080*
H4A0.255 (2)−0.032 (4)0.1940 (16)0.080*
H2B0.407 (2)0.720 (3)0.1241 (14)0.080*
H2A0.374 (2)0.489 (5)0.1330 (13)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag10.05372 (17)0.04898 (17)0.04972 (16)−0.01056 (11)0.01445 (11)0.00527 (11)
Cl10.0798 (7)0.0821 (7)0.0669 (6)−0.0191 (5)−0.0192 (5)−0.0079 (5)
O10.0522 (13)0.0746 (17)0.0462 (13)−0.0174 (12)0.0110 (10)−0.0097 (12)
O20.0837 (18)0.0637 (16)0.0788 (18)−0.0047 (14)0.0062 (14)−0.0372 (15)
N10.0404 (13)0.0345 (13)0.0426 (14)−0.0033 (10)0.0100 (10)0.0007 (11)
N20.0648 (18)0.0463 (17)0.0552 (18)−0.0051 (14)0.0075 (14)−0.0123 (14)
N30.0432 (13)0.0454 (15)0.0419 (14)−0.0063 (11)0.0090 (11)0.0021 (12)
N40.0729 (19)0.070 (2)0.0420 (16)−0.0249 (16)0.0199 (14)−0.0044 (15)
C10.060 (2)0.054 (2)0.0359 (16)−0.0103 (17)−0.0015 (14)0.0007 (15)
C20.066 (2)0.052 (2)0.0465 (18)−0.0065 (17)0.0145 (16)−0.0162 (15)
C30.0491 (18)0.0522 (19)0.0472 (18)−0.0026 (15)0.0113 (14)−0.0094 (15)
C40.0540 (17)0.0401 (17)0.0349 (15)−0.0079 (14)0.0098 (13)0.0005 (13)
C50.070 (2)0.0414 (18)0.053 (2)0.0066 (17)0.0023 (16)−0.0042 (16)
C60.062 (2)0.057 (2)0.065 (2)0.0071 (18)−0.0105 (17)0.0010 (19)
C70.063 (2)0.0435 (18)0.0385 (17)−0.0144 (15)0.0093 (15)−0.0058 (14)
C80.0382 (15)0.0341 (17)0.0530 (18)0.0034 (12)0.0073 (13)−0.0022 (14)
C90.0438 (17)0.0309 (17)0.076 (2)0.0001 (13)0.0093 (15)0.0040 (16)
C100.0420 (17)0.049 (2)0.069 (2)0.0037 (14)0.0166 (15)0.0233 (17)
C110.0390 (16)0.054 (2)0.0481 (18)0.0057 (14)0.0115 (13)0.0076 (15)
C120.0390 (15)0.0392 (17)0.0466 (17)−0.0012 (13)0.0079 (12)−0.0022 (14)
C130.061 (2)0.097 (3)0.046 (2)0.001 (2)0.0159 (17)0.0094 (19)
C140.0403 (15)0.0489 (19)0.0448 (17)−0.0016 (14)0.0147 (13)0.0035 (15)
C150.058 (2)0.0520 (19)0.054 (2)−0.0088 (16)0.0204 (15)0.0091 (17)
C160.0476 (18)0.047 (2)0.072 (2)−0.0092 (15)0.0146 (16)−0.0004 (17)
C170.0412 (16)0.0497 (19)0.057 (2)−0.0005 (14)0.0065 (14)−0.0085 (16)
C180.0474 (17)0.055 (2)0.0409 (17)−0.0020 (15)0.0085 (13)0.0045 (15)
C190.072 (2)0.071 (3)0.071 (3)−0.008 (2)−0.001 (2)−0.021 (2)

Geometric parameters (Å, °)

Ag1—N12.179 (2)C5—H50.93
Ag1—N32.193 (2)C6—H60.93
Ag1—O12.647 (2)C8—C91.415 (4)
Cl1—C11.748 (3)C9—C101.348 (5)
O1—C71.263 (4)C9—H90.93
O2—C71.240 (4)C10—C111.404 (5)
N1—C81.342 (4)C10—H100.93
N1—C121.356 (4)C11—C121.362 (4)
N2—C81.340 (4)C11—C131.501 (5)
N2—H2B0.888 (10)C12—H120.93
N2—H2A0.88 (3)C13—H13A0.96
N3—C141.339 (4)C13—H13B0.96
N3—C181.351 (4)C13—H13C0.96
N4—C141.347 (4)C14—C151.401 (4)
N4—H4B0.883 (10)C15—C161.344 (5)
N4—H4A0.88 (3)C15—H150.93
C1—C21.366 (5)C16—C171.405 (5)
C1—C61.369 (5)C16—H160.93
C2—C31.379 (4)C17—C181.363 (5)
C2—H20.93C17—C191.513 (5)
C3—C41.384 (4)C18—H180.93
C3—H30.93C19—H19A0.96
C4—C51.375 (4)C19—H19B0.96
C4—C71.510 (4)C19—H19C0.96
C5—C61.373 (5)
N1—Ag1—N3151.99 (9)C10—C9—C8120.0 (3)
N1—Ag1—O1103.05 (9)C10—C9—H9120.0
N3—Ag1—O1104.89 (9)C8—C9—H9120.0
C8—N1—C12118.0 (3)C9—C10—C11120.5 (3)
C8—N1—Ag1124.1 (2)C9—C10—H10119.7
C12—N1—Ag1117.89 (19)C11—C10—H10119.7
C8—N2—H2B125 (2)C12—C11—C10116.2 (3)
C8—N2—H2A125 (2)C12—C11—C13121.3 (3)
H2B—N2—H2A110 (2)C10—C11—C13122.4 (3)
C14—N3—C18118.3 (3)N1—C12—C11125.1 (3)
C14—N3—Ag1122.7 (2)N1—C12—H12117.5
C18—N3—Ag1118.44 (19)C11—C12—H12117.5
C14—N4—H4B123 (2)C11—C13—H13A109.5
C14—N4—H4A125 (2)C11—C13—H13B109.5
H4B—N4—H4A111 (2)H13A—C13—H13B109.5
C2—C1—C6121.4 (3)C11—C13—H13C109.5
C2—C1—Cl1119.4 (3)H13A—C13—H13C109.5
C6—C1—Cl1119.2 (3)H13B—C13—H13C109.5
C1—C2—C3119.1 (3)N3—C14—N4118.2 (3)
C1—C2—H2120.4N3—C14—C15120.1 (3)
C3—C2—H2120.4N4—C14—C15121.6 (3)
C2—C3—C4120.7 (3)C16—C15—C14120.5 (3)
C2—C3—H3119.6C16—C15—H15119.8
C4—C3—H3119.6C14—C15—H15119.8
C5—C4—C3118.4 (3)C15—C16—C17120.4 (3)
C5—C4—C7120.3 (3)C15—C16—H16119.8
C3—C4—C7121.2 (3)C17—C16—H16119.8
C6—C5—C4121.4 (3)C18—C17—C16115.9 (3)
C6—C5—H5119.3C18—C17—C19122.3 (3)
C4—C5—H5119.3C16—C17—C19121.8 (3)
C1—C6—C5118.9 (3)N3—C18—C17124.8 (3)
C1—C6—H6120.6N3—C18—H18117.6
C5—C6—H6120.6C17—C18—H18117.6
O2—C7—O1125.0 (3)C17—C19—H19A109.5
O2—C7—C4117.2 (3)C17—C19—H19B109.5
O1—C7—C4117.7 (3)H19A—C19—H19B109.5
N2—C8—N1118.3 (3)C17—C19—H19C109.5
N2—C8—C9121.4 (3)H19A—C19—H19C109.5
N1—C8—C9120.2 (3)H19B—C19—H19C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.88 (3)2.11 (3)2.977 (4)169 (4)
N2—H2B···O2i0.89 (1)1.94 (1)2.822 (4)174 (3)
N4—H4A···O10.88 (3)2.09 (3)2.966 (4)167 (4)
N4—H4B···O1ii0.88 (1)2.09 (3)2.955 (3)167 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2572).

References

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