catena-Poly[[(4-amino­benzoato)aqua­silver(I)]-μ-hexa­methyl­enetetramine]

Han, J.-J.; Zhang, T.-Y.; Geng, L.

doi:10.1107/S1600536809055044

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m111

https://doi.org/10.1107/S1600536809055044

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catena-Poly[[(4-aminobenzoato)aquasilver(I)]-μ-hexamethylenetetramine]

Jia-Jun Han,^a ^* Tian-Yun Zhang ^a and Lin Geng ^b

^aSchool of the Ocean, Harbin Institute of Technology, Weihai 264209, People's Republic of China, and ^bSchool of Materials Science and Engineering, Harbin Institute of Technology, Harbin 150001, People's Republic of China
^*Correspondence e-mail: hanjiajunhit@yahoo.com.cn

(Received 13 December 2009; accepted 22 December 2009; online 9 January 2010)

In the title coordination polymer, [Ag(C₇H₆NO₂)(C₆H₁₂N₄)(H₂O)]_n, the Ag^I ion is five-coordinated by two carboxylate O atoms from one 4-aminobenzoate anion (L), two N atoms from two different hexamethylenetetramine (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 molecule 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)(H₂O)]
M_r = 402.21
Orthorhombic, P n m a
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[F² > 2σ(F²)] = 0.019
wR(F²) = 0.048
S = 1.08
1557 reflections
123 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809055044/ci2988sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055044/ci2988Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

An aqueous solution (10 ml) of HL (0.104 g, 0.5 mmol) was added to solid Ag₂CO₃ (0.25 mmol) and stirred for several minutes until no further CO₂ was given off. A solution of hmt (0.5 mmol) in acetonitrile (10 ml) was then added and a white precipitate formed. The precipitate was dissolved by dropwise addition of an aqueous solution of NH₃ (14 M). Colourless blocks of the title compound were obtained by evaporation of the solution for several days at room temperature (33% yield).

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the local coordination of the Ag^I centre in the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) x, 3/2 - y, z; (ii) x, 1/2 - y, z.
	Fig. 2. Part of the polymeric chain in the title compound.

catena-Poly[[(4-aminobenzoato)aquasilver(I)]-µ-hexamethylenetetramine] top

Crystal data top

[Ag(C₇H₆NO₂)(C₆H₁₂N₄)(H₂O)]	F(000) = 816
M_r = 402.21	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0211P)² + 0.5726P] where P = (F_o² + 2F_c²)/3
1557 reflections	(Δ/σ)_max = 0.001
123 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Ag(C₇H₆NO₂)(C₆H₁₂N₄)(H₂O)]	V = 1455.65 (13) Å³
M_r = 402.21	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 19.8107 (11) Å	µ = 1.41 mm⁻¹
b = 6.4877 (3) Å	T = 293 K
c = 11.3257 (6) Å	0.31 × 0.27 × 0.22 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	1557 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1373 reflections with I > 2σ(I)
T_min = 0.66, T_max = 0.87	R_int = 0.029
7757 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.37 e Å⁻³
1557 reflections	Δρ_min = −0.26 e Å⁻³
123 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) x, −y+1/2, z; (ii) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.84 (2)	2.27 (2)	3.072 (2)	159 (2)

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

Experimental details

Crystal data
Chemical formula	[Ag(C₇H₆NO₂)(C₆H₁₂N₄)(H₂O)]
M_r	402.21
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	293
a, b, c (Å)	19.8107 (11), 6.4877 (3), 11.3257 (6)
V (Å³)	1455.65 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.41
Crystal size (mm)	0.31 × 0.27 × 0.22

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.66, 0.87
No. of measured, independent and observed [I > 2σ(I)] reflections	7757, 1557, 1373
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.048, 1.08
No. of reflections	1557
No. of parameters	123
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.26

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x+1/2, −y+1, z−1/2.

Acknowledgements

The authors thank Harbin Institute of Technology for financial support.

References

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