catena-Poly[[(4-amino-benzoato)aqua-silver(I)]-μ-hexa-methyl-enetetramine].

In the title coordination polymer, [Ag(C(7)H(6)NO(2))(C(6)H(12)N(4))(H(2)O)](n), the Ag(I) ion is five-coordinated by two carboxyl-ate O atoms from one 4-amino-benzoate anion (L), two N atoms from two different hexa-methyl-enetetramine (hmt) ligands, and one water O atom in a distorted square-pyramidal geometry. The metal atom lies on a mirror plane and the L anion, hmt ligand and water mol-ecule all lie across crystallographic mirror planes. Each hmt ligand bridges two neighboring Ag(I) ions, resulting in the formation of a chain structure along the b axis. The chains are linked into a three-dimensional framework by N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the applications and structures of silver(I) coordination polymers, see: Yang et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

[Ag(C7H6NO2)(C6H12N4)(n class="Chemical">H2O)]

M = 402.21

Orthorhombic,

a = 19.8107 (11) Å

b = 6.4877 (3) Å

c = 11.3257 (6) Å

V = 1455.65 (13) Å3

Z = 4

Mo Kα radiation

μ = 1.41 mm−1

T = 293 K

0.31 × 0.27 × 0.22 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.66, T max = 0.87

7757 measured reflections

1557 independent reflections

1373 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.048

S = 1.08

1557 reflections

123 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536809055044/ci2988sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055044/ci2988Isup2.hkl

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

[Ag(C7H6NO2)(C6H12N4)(H2O)]	F(000) = 816
Mr = 402.21	Dx = 1.835 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1557 reflections
a = 19.8107 (11) Å	θ = 3.0–26.0°
b = 6.4877 (3) Å	µ = 1.41 mm−1
c = 11.3257 (6) Å	T = 293 K
V = 1455.65 (13) Å3	Block, colourless
Z = 4	0.31 × 0.27 × 0.22 mm

Bruker APEX CCD area-detector diffractometer	1557 independent reflections
Radiation source: fine-focus sealed tube	1373 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→23
Tmin = 0.66, Tmax = 0.87	k = −7→7
7757 measured reflections	l = −13→9

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0211P)2 + 0.5726P] where P = (Fo2 + 2Fc2)/3
1557 reflections	(Δ/σ)max = 0.001
123 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Ag1	0.425226 (10)	0.2500	0.638361 (18)	0.02218 (9)
O1W	0.54862 (12)	0.2500	0.6362 (2)	0.0324 (5)
H1W1	0.5643 (11)	0.352 (4)	0.606 (2)	0.036 (7)*
O1	0.38093 (7)	0.4203 (2)	0.45173 (12)	0.0306 (4)
N1	0.42059 (7)	0.5604 (3)	0.75114 (14)	0.0198 (4)
N2	0.23019 (13)	0.2500	−0.0371 (2)	0.0261 (6)
H2A	0.2075 (11)	0.358 (3)	−0.0497 (19)	0.033 (7)*
N3	0.47738 (11)	0.7500	0.9101 (2)	0.0186 (5)
N4	0.35383 (11)	0.7500	0.8979 (2)	0.0228 (5)
C1	0.26785 (13)	0.2500	0.0657 (2)	0.0182 (6)
C2	0.28812 (9)	0.4347 (3)	0.11800 (16)	0.0206 (4)
H2	0.2781	0.5594	0.0814	0.025*
C3	0.32294 (9)	0.4339 (3)	0.22365 (16)	0.0196 (4)
H3	0.3357	0.5585	0.2576	0.024*
C4	0.33924 (13)	0.2500	0.2803 (2)	0.0178 (6)
C5	0.36952 (13)	0.2500	0.4018 (2)	0.0222 (6)
C6	0.35759 (9)	0.5670 (3)	0.82288 (17)	0.0235 (5)
H6A	0.3189	0.5649	0.7704	0.028*
H6B	0.3554	0.4448	0.8721	0.028*
C7	0.47854 (9)	0.5664 (3)	0.83436 (16)	0.0214 (4)
H7A	0.4776	0.4440	0.8836	0.026*
H7B	0.5203	0.5647	0.7897	0.026*
C8	0.41317 (12)	0.7500	0.9761 (2)	0.0223 (6)
H8A	0.4115	0.6292	1.0264	0.027*	0.50
H8B	0.4115	0.8708	1.0264	0.027*	0.50
C9	0.42303 (13)	0.7500	0.6783 (2)	0.0200 (6)
H9A	0.4642	0.7500	0.6321	0.024*
H9B	0.3852	0.7500	0.6240	0.024*

	U11	U22	U33	U12	U13	U23
Ag1	0.02328 (13)	0.02679 (14)	0.01649 (13)	0.000	−0.00302 (9)	0.000
O1W	0.0240 (12)	0.0378 (15)	0.0352 (14)	0.000	0.0073 (10)	0.000
O1	0.0353 (8)	0.0378 (9)	0.0187 (7)	−0.0053 (8)	−0.0049 (6)	−0.0054 (7)
N1	0.0170 (8)	0.0292 (10)	0.0130 (8)	−0.0014 (7)	−0.0024 (6)	0.0004 (7)
N2	0.0244 (14)	0.0349 (17)	0.0189 (13)	0.000	−0.0072 (11)	0.000
N3	0.0137 (11)	0.0288 (14)	0.0134 (11)	0.000	0.0003 (9)	0.000
N4	0.0140 (11)	0.0378 (15)	0.0165 (12)	0.000	−0.0014 (9)	0.000
C1	0.0126 (12)	0.0283 (15)	0.0137 (14)	0.000	0.0039 (11)	0.000
C2	0.0208 (10)	0.0229 (11)	0.0179 (10)	0.0016 (8)	0.0010 (8)	0.0035 (8)
C3	0.0200 (10)	0.0210 (11)	0.0179 (10)	−0.0011 (8)	0.0041 (8)	−0.0020 (8)
C4	0.0112 (12)	0.0279 (16)	0.0143 (13)	0.000	0.0024 (10)	0.000
C5	0.0145 (13)	0.0355 (18)	0.0168 (14)	0.000	0.0022 (11)	0.000
C6	0.0159 (9)	0.0355 (13)	0.0192 (10)	−0.0040 (9)	−0.0024 (8)	0.0019 (9)
C7	0.0167 (10)	0.0308 (12)	0.0167 (10)	0.0015 (9)	−0.0025 (8)	0.0019 (8)
C8	0.0152 (14)	0.0377 (18)	0.0139 (14)	0.000	−0.0018 (11)	0.000
C9	0.0168 (13)	0.0301 (17)	0.0132 (13)	0.000	−0.0041 (11)	0.000

Ag1—N1	2.3862 (17)	C1—C2	1.396 (2)
Ag1—N1i	2.3862 (17)	C1—C2i	1.396 (2)
Ag1—O1W	2.445 (2)	C2—C3	1.381 (3)
Ag1—O1	2.5413 (14)	C2—H2	0.93
Ag1—O1i	2.5413 (14)	C3—C4	1.393 (2)
O1W—H1W1	0.81 (2)	C3—H3	0.93
O1—C5	1.2615 (19)	C4—C3i	1.393 (2)
N1—C9	1.482 (2)	C4—C5	1.500 (4)
N1—C7	1.486 (2)	C5—O1i	1.2615 (19)
N1—C6	1.490 (2)	C6—H6A	0.97
N2—C1	1.383 (4)	C6—H6B	0.97
N2—H2A	0.84 (2)	C7—H7A	0.97
N3—C7	1.468 (2)	C7—H7B	0.97
N3—C7ii	1.468 (2)	C8—H8A	0.97
N3—C8	1.475 (3)	C8—H8B	0.97
N4—C6	1.462 (2)	C9—N1ii	1.482 (2)
N4—C6ii	1.462 (2)	C9—H9A	0.97
N4—C8	1.472 (3)	C9—H9B	0.97
N1—Ag1—N1i	115.09 (8)	C2—C3—H3	119.4
N1—Ag1—O1W	92.52 (5)	C4—C3—H3	119.4
N1i—Ag1—O1W	92.52 (5)	C3i—C4—C3	117.9 (2)
N1—Ag1—O1	93.74 (5)	C3i—C4—C5	121.01 (12)
N1i—Ag1—O1	143.00 (5)	C3—C4—C5	121.01 (12)
O1W—Ag1—O1	109.69 (6)	O1i—C5—O1	122.2 (3)
N1—Ag1—O1i	143.00 (5)	O1i—C5—C4	118.87 (13)
N1i—Ag1—O1i	93.74 (5)	O1—C5—C4	118.87 (13)
O1W—Ag1—O1i	109.69 (6)	N4—C6—N1	112.52 (17)
O1—Ag1—O1i	51.53 (7)	N4—C6—H6A	109.1
Ag1—O1W—H1W1	112.9 (17)	N1—C6—H6A	109.1
C5—O1—Ag1	93.12 (14)	N4—C6—H6B	109.1
C9—N1—C7	107.80 (16)	N1—C6—H6B	109.1
C9—N1—C6	107.87 (17)	H6A—C6—H6B	107.8
C7—N1—C6	107.49 (15)	N3—C7—N1	112.34 (17)
C9—N1—Ag1	113.67 (12)	N3—C7—H7A	109.1
C7—N1—Ag1	109.39 (12)	N1—C7—H7A	109.1
C6—N1—Ag1	110.39 (12)	N3—C7—H7B	109.1
C1—N2—H2A	115.4 (16)	N1—C7—H7B	109.1
C7—N3—C7ii	108.4 (2)	H7A—C7—H7B	107.9
C7—N3—C8	108.02 (14)	N4—C8—N3	112.6 (2)
C7ii—N3—C8	108.02 (14)	N4—C8—H8A	109.1
C6—N4—C6ii	108.6 (2)	N3—C8—H8A	109.1
C6—N4—C8	107.99 (14)	N4—C8—H8B	109.1
C6ii—N4—C8	107.99 (14)	N3—C8—H8B	109.1
N2—C1—C2	120.83 (12)	H8A—C8—H8B	107.8
N2—C1—C2i	120.83 (12)	N1ii—C9—N1	112.3 (2)
C2—C1—C2i	118.3 (2)	N1ii—C9—H9A	109.2
C3—C2—C1	120.53 (19)	N1—C9—H9A	109.2
C3—C2—H2	119.7	N1ii—C9—H9B	109.2
C1—C2—H2	119.7	N1—C9—H9B	109.2
C2—C3—C4	121.23 (19)	H9A—C9—H9B	107.9
N1—Ag1—O1—C5	−166.41 (14)	Ag1—O1—C5—C4	178.7 (2)
N1i—Ag1—O1—C5	−23.97 (18)	C3i—C4—C5—O1i	0.9 (4)
O1W—Ag1—O1—C5	99.57 (14)	C3—C4—C5—O1i	177.1 (2)
O1i—Ag1—O1—C5	−0.38 (15)	C3i—C4—C5—O1	−177.1 (2)
N1i—Ag1—N1—C9	−179.54 (11)	C3—C4—C5—O1	−0.9 (4)
O1W—Ag1—N1—C9	86.50 (15)	C6ii—N4—C6—N1	58.4 (3)
O1—Ag1—N1—C9	−23.43 (14)	C8—N4—C6—N1	−58.5 (2)
O1i—Ag1—N1—C9	−41.73 (17)	C9—N1—C6—N4	−57.9 (2)
N1i—Ag1—N1—C7	59.91 (14)	C7—N1—C6—N4	58.1 (2)
O1W—Ag1—N1—C7	−34.05 (13)	Ag1—N1—C6—N4	177.33 (13)
O1—Ag1—N1—C7	−143.98 (12)	C7ii—N3—C7—N1	−58.6 (2)
O1i—Ag1—N1—C7	−162.28 (10)	C8—N3—C7—N1	58.2 (2)
N1i—Ag1—N1—C6	−58.17 (14)	C9—N1—C7—N3	58.2 (2)
O1W—Ag1—N1—C6	−152.14 (12)	C6—N1—C7—N3	−57.8 (2)
O1—Ag1—N1—C6	97.94 (12)	Ag1—N1—C7—N3	−177.73 (13)
O1i—Ag1—N1—C6	79.64 (15)	C6—N4—C8—N3	58.64 (14)
N2—C1—C2—C3	176.9 (2)	C6ii—N4—C8—N3	−58.64 (14)
C2i—C1—C2—C3	−4.8 (4)	C7—N3—C8—N4	−58.54 (13)
C1—C2—C3—C4	0.5 (3)	C7ii—N3—C8—N4	58.54 (13)
C2—C3—C4—C3i	3.8 (4)	C7—N1—C9—N1ii	−58.1 (2)
C2—C3—C4—C5	−172.5 (2)	C6—N1—C9—N1ii	57.7 (2)
Ag1—O1—C5—O1i	0.7 (3)	Ag1—N1—C9—N1ii	−179.56 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1iii	0.81 (2)	1.95 (2)	2.742 (2)	168 (2)
N2—H2A···O1iv	0.84 (2)	2.27 (2)	3.072 (2)	159 (2)

Table 1

Selected bond lengths (Å)

Ag1—N1	2.3862 (17)
Ag1—O1W	2.445 (2)
Ag1—O1	2.5413 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O1i	0.81 (2)	1.95 (2)	2.742 (2)	168 (2)
N2—H2A⋯O1ii	0.84 (2)	2.27 (2)	3.072 (2)	159 (2)

Symmetry codes: (i) ; (ii) .