(4-Chloro-benzoato)bis(5-methyl-2-pyridylamine)silver(I).

The title compound, [Ag(C(7)H(4)ClO(2))(C(6)H(8)N(2))(2)], is a mononuclear silver(I) complex. The Ag(I) atom is three-coordinated by two pyridine N atoms from two 5-methyl-pyridin-2-ylamine ligands and by one O atom of a 4-chloro-benzoate ligand, forming a distorted T-shaped coordination. In the crystal structure, the mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

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

Experimental

Crystal data

[Ag(C7H4ClO2)(C6H8N2)2]

M = 479.71

Monoclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

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

[Ag(C7H4ClO2)(C6H8N2)2]	F000 = 968
Mr = 479.71	Dx = 1.617 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3734 reflections
a = 15.983 (3) Å	θ = 2.5–24.9º
b = 5.7428 (9) Å	µ = 1.18 mm−1
c = 21.703 (4) Å	T = 298 (2) K
β = 98.460 (2)º	Block, colourless
V = 1970.4 (6) Å3	0.37 × 0.35 × 0.32 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4064 independent reflections
Radiation source: fine-focus sealed tube	3277 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
T = 298(2) K	θmax = 26.5º
ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −19→20
Tmin = 0.669, Tmax = 0.704	k = −7→7
13465 measured reflections	l = −26→27

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)] = 0.036	H 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 reflections	Δρmax = 0.53 e Å−3
258 parameters	Δρmin = −0.34 e Å−3
6 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.291478 (15)	0.09298 (4)	0.077611 (11)	0.05012 (11)
Cl1	0.69700 (7)	0.65902 (19)	0.36548 (5)	0.0793 (3)
O1	0.35007 (14)	0.2179 (4)	0.19330 (10)	0.0573 (6)
O2	0.45197 (17)	0.0110 (5)	0.16007 (13)	0.0760 (8)
N1	0.34955 (14)	0.3452 (4)	0.02193 (11)	0.0388 (5)
N2	0.39194 (19)	0.5847 (5)	0.10583 (14)	0.0556 (7)
N3	0.20646 (14)	−0.2005 (4)	0.08709 (11)	0.0432 (6)
N4	0.2241 (2)	−0.1612 (6)	0.19393 (13)	0.0605 (8)
C1	0.6161 (2)	0.5050 (6)	0.31981 (14)	0.0507 (8)
C2	0.5373 (2)	0.6012 (6)	0.30750 (15)	0.0542 (8)
H2	0.5258	0.7432	0.3251	0.065*
C3	0.4749 (2)	0.4848 (6)	0.26869 (14)	0.0491 (7)
H3	0.4210	0.5489	0.2602	0.059*
C4	0.49170 (19)	0.2737 (5)	0.24224 (13)	0.0427 (7)
C5	0.5713 (2)	0.1802 (6)	0.25682 (16)	0.0554 (8)
H5	0.5831	0.0371	0.2400	0.066*
C6	0.6338 (2)	0.2935 (7)	0.29568 (17)	0.0631 (9)
H6	0.6873	0.2277	0.3054	0.076*
C7	0.4262 (2)	0.1546 (6)	0.19559 (14)	0.0481 (8)
C8	0.38570 (17)	0.5444 (5)	0.04449 (15)	0.0417 (7)
C9	0.41727 (18)	0.7050 (5)	0.00414 (17)	0.0501 (8)
H9	0.4412	0.8445	0.0198	0.060*
C10	0.41269 (19)	0.6557 (6)	−0.05702 (17)	0.0525 (8)
H10	0.4337	0.7613	−0.0834	0.063*
C11	0.37643 (19)	0.4460 (6)	−0.08121 (15)	0.0465 (7)
C12	0.34602 (17)	0.3021 (5)	−0.03981 (13)	0.0414 (7)
H12	0.3209	0.1636	−0.0551	0.050*
C13	0.3731 (2)	0.3791 (7)	−0.14840 (16)	0.0674 (11)
H13A	0.3471	0.2288	−0.1553	0.101*
H13B	0.4295	0.3734	−0.1586	0.101*
H13C	0.3406	0.4923	−0.1743	0.101*
C14	0.19164 (17)	−0.2802 (6)	0.14244 (14)	0.0438 (7)
C15	0.1459 (2)	−0.4866 (6)	0.14600 (16)	0.0535 (8)
H15	0.1354	−0.5405	0.1845	0.064*
C16	0.1171 (2)	−0.6072 (6)	0.09412 (17)	0.0548 (8)
H16	0.0872	−0.7447	0.0970	0.066*
C17	0.13206 (19)	−0.5268 (6)	0.03557 (15)	0.0493 (8)
C18	0.17643 (19)	−0.3242 (6)	0.03562 (15)	0.0477 (7)
H18	0.1868	−0.2669	−0.0026	0.057*
C19	0.1021 (3)	−0.6605 (7)	−0.02362 (18)	0.0726 (11)
H19A	0.1096	−0.5667	−0.0590	0.109*
H19B	0.0433	−0.6984	−0.0253	0.109*
H19C	0.1344	−0.8013	−0.0241	0.109*
H4B	0.209 (2)	−0.185 (6)	0.2308 (9)	0.080*
H4A	0.255 (2)	−0.032 (4)	0.1940 (16)	0.080*
H2B	0.407 (2)	0.720 (3)	0.1241 (14)	0.080*
H2A	0.374 (2)	0.489 (5)	0.1330 (13)	0.080*

	U11	U22	U33	U12	U13	U23
Ag1	0.05372 (17)	0.04898 (17)	0.04972 (16)	−0.01056 (11)	0.01445 (11)	0.00527 (11)
Cl1	0.0798 (7)	0.0821 (7)	0.0669 (6)	−0.0191 (5)	−0.0192 (5)	−0.0079 (5)
O1	0.0522 (13)	0.0746 (17)	0.0462 (13)	−0.0174 (12)	0.0110 (10)	−0.0097 (12)
O2	0.0837 (18)	0.0637 (16)	0.0788 (18)	−0.0047 (14)	0.0062 (14)	−0.0372 (15)
N1	0.0404 (13)	0.0345 (13)	0.0426 (14)	−0.0033 (10)	0.0100 (10)	0.0007 (11)
N2	0.0648 (18)	0.0463 (17)	0.0552 (18)	−0.0051 (14)	0.0075 (14)	−0.0123 (14)
N3	0.0432 (13)	0.0454 (15)	0.0419 (14)	−0.0063 (11)	0.0090 (11)	0.0021 (12)
N4	0.0729 (19)	0.070 (2)	0.0420 (16)	−0.0249 (16)	0.0199 (14)	−0.0044 (15)
C1	0.060 (2)	0.054 (2)	0.0359 (16)	−0.0103 (17)	−0.0015 (14)	0.0007 (15)
C2	0.066 (2)	0.052 (2)	0.0465 (18)	−0.0065 (17)	0.0145 (16)	−0.0162 (15)
C3	0.0491 (18)	0.0522 (19)	0.0472 (18)	−0.0026 (15)	0.0113 (14)	−0.0094 (15)
C4	0.0540 (17)	0.0401 (17)	0.0349 (15)	−0.0079 (14)	0.0098 (13)	0.0005 (13)
C5	0.070 (2)	0.0414 (18)	0.053 (2)	0.0066 (17)	0.0023 (16)	−0.0042 (16)
C6	0.062 (2)	0.057 (2)	0.065 (2)	0.0071 (18)	−0.0105 (17)	0.0010 (19)
C7	0.063 (2)	0.0435 (18)	0.0385 (17)	−0.0144 (15)	0.0093 (15)	−0.0058 (14)
C8	0.0382 (15)	0.0341 (17)	0.0530 (18)	0.0034 (12)	0.0073 (13)	−0.0022 (14)
C9	0.0438 (17)	0.0309 (17)	0.076 (2)	0.0001 (13)	0.0093 (15)	0.0040 (16)
C10	0.0420 (17)	0.049 (2)	0.069 (2)	0.0037 (14)	0.0166 (15)	0.0233 (17)
C11	0.0390 (16)	0.054 (2)	0.0481 (18)	0.0057 (14)	0.0115 (13)	0.0076 (15)
C12	0.0390 (15)	0.0392 (17)	0.0466 (17)	−0.0012 (13)	0.0079 (12)	−0.0022 (14)
C13	0.061 (2)	0.097 (3)	0.046 (2)	0.001 (2)	0.0159 (17)	0.0094 (19)
C14	0.0403 (15)	0.0489 (19)	0.0448 (17)	−0.0016 (14)	0.0147 (13)	0.0035 (15)
C15	0.058 (2)	0.0520 (19)	0.054 (2)	−0.0088 (16)	0.0204 (15)	0.0091 (17)
C16	0.0476 (18)	0.047 (2)	0.072 (2)	−0.0092 (15)	0.0146 (16)	−0.0004 (17)
C17	0.0412 (16)	0.0497 (19)	0.057 (2)	−0.0005 (14)	0.0065 (14)	−0.0085 (16)
C18	0.0474 (17)	0.055 (2)	0.0409 (17)	−0.0020 (15)	0.0085 (13)	0.0045 (15)
C19	0.072 (2)	0.071 (3)	0.071 (3)	−0.008 (2)	−0.001 (2)	−0.021 (2)

Ag1—N1	2.179 (2)	C5—H5	0.93
Ag1—N3	2.193 (2)	C6—H6	0.93
Ag1—O1	2.647 (2)	C8—C9	1.415 (4)
Cl1—C1	1.748 (3)	C9—C10	1.348 (5)
O1—C7	1.263 (4)	C9—H9	0.93
O2—C7	1.240 (4)	C10—C11	1.404 (5)
N1—C8	1.342 (4)	C10—H10	0.93
N1—C12	1.356 (4)	C11—C12	1.362 (4)
N2—C8	1.340 (4)	C11—C13	1.501 (5)
N2—H2B	0.888 (10)	C12—H12	0.93
N2—H2A	0.88 (3)	C13—H13A	0.96
N3—C14	1.339 (4)	C13—H13B	0.96
N3—C18	1.351 (4)	C13—H13C	0.96
N4—C14	1.347 (4)	C14—C15	1.401 (4)
N4—H4B	0.883 (10)	C15—C16	1.344 (5)
N4—H4A	0.88 (3)	C15—H15	0.93
C1—C2	1.366 (5)	C16—C17	1.405 (5)
C1—C6	1.369 (5)	C16—H16	0.93
C2—C3	1.379 (4)	C17—C18	1.363 (5)
C2—H2	0.93	C17—C19	1.513 (5)
C3—C4	1.384 (4)	C18—H18	0.93
C3—H3	0.93	C19—H19A	0.96
C4—C5	1.375 (4)	C19—H19B	0.96
C4—C7	1.510 (4)	C19—H19C	0.96
C5—C6	1.373 (5)
N1—Ag1—N3	151.99 (9)	C10—C9—C8	120.0 (3)
N1—Ag1—O1	103.05 (9)	C10—C9—H9	120.0
N3—Ag1—O1	104.89 (9)	C8—C9—H9	120.0
C8—N1—C12	118.0 (3)	C9—C10—C11	120.5 (3)
C8—N1—Ag1	124.1 (2)	C9—C10—H10	119.7
C12—N1—Ag1	117.89 (19)	C11—C10—H10	119.7
C8—N2—H2B	125 (2)	C12—C11—C10	116.2 (3)
C8—N2—H2A	125 (2)	C12—C11—C13	121.3 (3)
H2B—N2—H2A	110 (2)	C10—C11—C13	122.4 (3)
C14—N3—C18	118.3 (3)	N1—C12—C11	125.1 (3)
C14—N3—Ag1	122.7 (2)	N1—C12—H12	117.5
C18—N3—Ag1	118.44 (19)	C11—C12—H12	117.5
C14—N4—H4B	123 (2)	C11—C13—H13A	109.5
C14—N4—H4A	125 (2)	C11—C13—H13B	109.5
H4B—N4—H4A	111 (2)	H13A—C13—H13B	109.5
C2—C1—C6	121.4 (3)	C11—C13—H13C	109.5
C2—C1—Cl1	119.4 (3)	H13A—C13—H13C	109.5
C6—C1—Cl1	119.2 (3)	H13B—C13—H13C	109.5
C1—C2—C3	119.1 (3)	N3—C14—N4	118.2 (3)
C1—C2—H2	120.4	N3—C14—C15	120.1 (3)
C3—C2—H2	120.4	N4—C14—C15	121.6 (3)
C2—C3—C4	120.7 (3)	C16—C15—C14	120.5 (3)
C2—C3—H3	119.6	C16—C15—H15	119.8
C4—C3—H3	119.6	C14—C15—H15	119.8
C5—C4—C3	118.4 (3)	C15—C16—C17	120.4 (3)
C5—C4—C7	120.3 (3)	C15—C16—H16	119.8
C3—C4—C7	121.2 (3)	C17—C16—H16	119.8
C6—C5—C4	121.4 (3)	C18—C17—C16	115.9 (3)
C6—C5—H5	119.3	C18—C17—C19	122.3 (3)
C4—C5—H5	119.3	C16—C17—C19	121.8 (3)
C1—C6—C5	118.9 (3)	N3—C18—C17	124.8 (3)
C1—C6—H6	120.6	N3—C18—H18	117.6
C5—C6—H6	120.6	C17—C18—H18	117.6
O2—C7—O1	125.0 (3)	C17—C19—H19A	109.5
O2—C7—C4	117.2 (3)	C17—C19—H19B	109.5
O1—C7—C4	117.7 (3)	H19A—C19—H19B	109.5
N2—C8—N1	118.3 (3)	C17—C19—H19C	109.5
N2—C8—C9	121.4 (3)	H19A—C19—H19C	109.5
N1—C8—C9	120.2 (3)	H19B—C19—H19C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.88 (3)	2.11 (3)	2.977 (4)	169 (4)
N2—H2B···O2i	0.89 (1)	1.94 (1)	2.822 (4)	174 (3)
N4—H4A···O1	0.88 (3)	2.09 (3)	2.966 (4)	167 (4)
N4—H4B···O1ii	0.88 (1)	2.09 (3)	2.955 (3)	167 (3)

Ag1—N1	2.179 (2)
Ag1—N3	2.193 (2)
Ag1—O1	2.647 (2)

N1—Ag1—N3	151.99 (9)
N1—Ag1—O1	103.05 (9)
N3—Ag1—O1	104.89 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.88 (3)	2.11 (3)	2.977 (4)	169 (4)
N2—H2B⋯O2i	0.89 (1)	1.94 (1)	2.822 (4)	174 (3)
N4—H4A⋯O1	0.88 (3)	2.09 (3)	2.966 (4)	167 (4)
N4—H4B⋯O1ii	0.88 (1)	2.09 (3)	2.955 (3)	167 (3)

Symmetry codes: (i) ; (ii) .