Bis(2-methyl-1H-imidazole-κN3)silver(I) nitrate dihydrate

Cong, F.-D.; Yu, F.-Y.; Wei, Z.; Ng, S.W.

doi:10.1107/S1600536809045838

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1535

doi:10.1107/S1600536809045838

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Bis(2-methyl-1H-imidazole-κN³)silver(I) nitrate dihydrate

Fang-Di Cong,^a ^* Feng-Yang Yu,^a Zhen Wei ^a and Seik Weng Ng ^b

^aDepartment of Basic Science, Tianjin Agricultural University, Tjianjin 300384, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: congfangdi666@yahoo.com.cn

(Received 29 October 2009; accepted 1 November 2009; online 7 November 2009)

The Ag^I atom in the salt, [Ag(C₄H₆N₂)₂]NO₃·2H₂O, shows a nearly linear coordination [N—Ag—N = 178.26 (7)°]. The cation, anion and water molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds into a layer motif extending parallel to (101).

Related literature

For the crystal structure of [Ag(C₄H₆N₂)₂][NO₃]·CH₃OH, see: Liu et al. (2006 ).

Experimental

Crystal data

[Ag(C₄H₆N₂)₂]NO₃·2H₂O
M_r = 370.13
Monoclinic, P 2₁ /n
a = 6.8001 (4) Å
b = 17.0196 (9) Å
c = 12.1453 (7) Å
β = 101.691 (1)°
V = 1376.48 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.49 mm⁻¹
T = 295 K
0.21 × 0.19 × 0.17 mm

Data collection

Bruker APEX2 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.745, T_max = 0.786
7483 measured reflections
2721 independent reflections
2083 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.073
S = 0.99
2721 reflections
198 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1w	0.86 (1)	1.99 (1)	2.838 (3)	169 (3)
N4—H4⋯O1wⁱ	0.84 (1)	1.99 (1)	2.837 (3)	178 (3)
O1w—H11⋯O2w	0.85 (1)	1.89 (1)	2.726 (3)	170 (4)
O1w—H12⋯O1	0.85 (1)	1.99 (1)	2.826 (3)	171 (3)
O2w—H21⋯O1ⁱⁱ	0.84 (1)	2.02 (1)	2.867 (3)	179 (4)
O2w—H22⋯O2ⁱⁱⁱ	0.84 (1)	2.15 (2)	2.955 (3)	159 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045838/bt5122sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045838/bt5122Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of [Ag(C₄H₆N₂)₂][NO₃].CH₃OH, see: Liu et al. (2006).

Experimental top

Silver nitrate (0.5 mmol, 0.085 g) and 2-methyl-1H-imidazole (0.5 mmol, 0.041 g) in water (15 ml) were heated in a Parr bomb at 433 K for three days. Crystals of the adduct were isolated from the cool mixture in 30% yield.

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of [Ag(C₄H₆N₂)₂][NO₃]^.2H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Bis(2-methyl-1H-imidazole-κN³)silver(I) nitrate dihydrate top

Crystal data top

[Ag(C4H6N₂)₂]NO₃·2H₂O	F(000) = 744
M_r = 370.13	D_x = 1.786 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3827 reflections
a = 6.8001 (4) Å	θ = 2.9–26.1°
b = 17.0196 (9) Å	µ = 1.49 mm⁻¹
c = 12.1453 (7) Å	T = 295 K
β = 101.691 (1)°	Block, colorless
V = 1376.48 (13) Å³	0.21 × 0.19 × 0.17 mm
Z = 4

Data collection top

Bruker APEX2 diffractometer	2721 independent reflections
Radiation source: fine-focus sealed tube	2083 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 26.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→8
T_min = 0.745, T_max = 0.786	k = −19→21
7483 measured reflections	l = −15→14

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0441P)² + 0.0379P] where P = (F_o² + 2F_c²)/3
2721 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.54 e Å⁻³
6 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Ag(C4H6N₂)₂]NO₃·2H₂O	V = 1376.48 (13) Å³
M_r = 370.13	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.8001 (4) Å	µ = 1.49 mm⁻¹
b = 17.0196 (9) Å	T = 295 K
c = 12.1453 (7) Å	0.21 × 0.19 × 0.17 mm
β = 101.691 (1)°

Data collection top

Bruker APEX2 diffractometer	2721 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2083 reflections with I > 2σ(I)
T_min = 0.745, T_max = 0.786	R_int = 0.020
7483 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	6 restraints
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.54 e Å⁻³
2721 reflections	Δρ_min = −0.34 e Å⁻³
198 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	0.63346 (3)	0.501978 (10)	0.882866 (16)	0.02240 (9)
O1	−0.1909 (3)	0.26078 (11)	0.44924 (15)	0.0315 (5)
O2	−0.0592 (3)	0.30353 (12)	0.61645 (17)	0.0404 (5)
O3	−0.2399 (3)	0.19831 (13)	0.59642 (18)	0.0458 (6)
O1w	0.1172 (3)	0.35094 (12)	0.38606 (16)	0.0266 (4)
O2w	0.3941 (3)	0.24560 (11)	0.34310 (17)	0.0292 (4)
N1	0.4754 (4)	0.49985 (11)	0.7163 (2)	0.0217 (5)
N2	0.2877 (3)	0.45702 (14)	0.55959 (19)	0.0257 (5)
H2	0.228 (4)	0.4222 (13)	0.514 (2)	0.043 (9)*
N3	0.7904 (3)	0.50045 (10)	1.0498 (2)	0.0201 (5)
N4	0.9606 (3)	0.45734 (13)	1.21030 (19)	0.0219 (5)
H4	1.010 (4)	0.4257 (12)	1.2620 (16)	0.025 (8)*
N5	−0.1639 (3)	0.25410 (13)	0.55457 (19)	0.0275 (5)
C1	0.3998 (4)	0.56352 (16)	0.6500 (2)	0.0242 (6)
H1	0.4245	0.6160	0.6694	0.029*
C2	0.2853 (4)	0.53782 (17)	0.5535 (2)	0.0267 (6)
H2A	0.2177	0.5685	0.4944	0.032*
C3	0.4044 (4)	0.43623 (15)	0.6586 (2)	0.0230 (6)
C4	0.4422 (4)	0.35360 (15)	0.6951 (3)	0.0344 (7)
H4A	0.5512	0.3517	0.7592	0.052*
H4B	0.4764	0.3235	0.6349	0.052*
H4C	0.3236	0.3321	0.7150	0.052*
C5	0.8772 (4)	0.56384 (16)	1.1123 (2)	0.0232 (6)
H5	0.8652	0.6160	1.0893	0.028*
C6	0.9816 (4)	0.53821 (16)	1.2118 (2)	0.0243 (6)
H6	1.0535	0.5687	1.2698	0.029*
C7	0.8427 (3)	0.43705 (16)	1.1119 (2)	0.0206 (6)
C8	0.7814 (4)	0.35502 (14)	1.0811 (2)	0.0318 (7)
H8A	0.6674	0.3552	1.0198	0.048*
H8B	0.7466	0.3290	1.1447	0.048*
H8C	0.8906	0.3277	1.0589	0.048*
H11	0.192 (5)	0.3164 (18)	0.366 (3)	0.089 (16)*
H12	0.029 (4)	0.3258 (17)	0.412 (3)	0.052 (11)*
H21	0.517 (2)	0.2499 (19)	0.374 (3)	0.060 (11)*
H22	0.392 (5)	0.2426 (19)	0.2737 (10)	0.066 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.01779 (13)	0.02855 (14)	0.01956 (14)	−0.00075 (8)	0.00074 (9)	−0.00051 (8)
O1	0.0306 (10)	0.0386 (11)	0.0230 (11)	−0.0041 (9)	0.0001 (8)	−0.0002 (8)
O2	0.0438 (12)	0.0364 (12)	0.0350 (13)	−0.0013 (10)	−0.0064 (10)	−0.0126 (10)
O3	0.0549 (14)	0.0491 (13)	0.0362 (13)	−0.0194 (11)	0.0157 (11)	−0.0026 (10)
O1w	0.0270 (11)	0.0253 (11)	0.0268 (11)	0.0008 (9)	0.0038 (9)	0.0015 (8)
O2w	0.0280 (11)	0.0296 (11)	0.0276 (12)	0.0012 (9)	0.0001 (9)	−0.0027 (9)
N1	0.0174 (11)	0.0250 (12)	0.0218 (12)	−0.0016 (8)	0.0017 (9)	−0.0017 (9)
N2	0.0221 (12)	0.0310 (14)	0.0230 (13)	0.0004 (10)	0.0023 (10)	−0.0050 (11)
N3	0.0196 (12)	0.0203 (11)	0.0203 (12)	0.0006 (8)	0.0036 (9)	−0.0008 (8)
N4	0.0223 (12)	0.0226 (12)	0.0204 (12)	0.0018 (10)	0.0037 (10)	0.0034 (10)
N5	0.0212 (11)	0.0294 (12)	0.0305 (14)	0.0031 (10)	0.0019 (10)	−0.0050 (10)
C1	0.0249 (14)	0.0219 (14)	0.0254 (15)	0.0006 (11)	0.0038 (12)	0.0017 (11)
C2	0.0258 (15)	0.0308 (15)	0.0239 (15)	0.0043 (12)	0.0060 (12)	0.0043 (12)
C3	0.0171 (13)	0.0274 (14)	0.0251 (15)	−0.0001 (11)	0.0056 (11)	−0.0034 (11)
C4	0.0351 (16)	0.0227 (15)	0.0426 (18)	0.0058 (12)	0.0008 (14)	−0.0025 (12)
C5	0.0247 (15)	0.0183 (13)	0.0258 (16)	−0.0015 (10)	0.0033 (12)	−0.0043 (11)
C6	0.0223 (14)	0.0264 (15)	0.0247 (15)	−0.0048 (12)	0.0058 (11)	−0.0056 (12)
C7	0.0167 (13)	0.0229 (14)	0.0242 (15)	0.0025 (10)	0.0088 (11)	0.0005 (11)
C8	0.0326 (15)	0.0213 (14)	0.0416 (18)	−0.0033 (12)	0.0075 (13)	−0.0019 (12)

Geometric parameters (Å, º) top

Ag1—N1	2.090 (2)	N4—C6	1.384 (4)
Ag1—N3	2.091 (2)	N4—H4	0.844 (10)
O1—N5	1.260 (3)	C1—C2	1.342 (4)
O2—N5	1.250 (3)	C1—H1	0.9300
O3—N5	1.238 (3)	C2—H2A	0.9300
O1w—H11	0.845 (10)	C3—C4	1.481 (4)
O1w—H12	0.848 (10)	C4—H4A	0.9600
O2w—H21	0.844 (10)	C4—H4B	0.9600
O2w—H22	0.842 (10)	C4—H4C	0.9600
N1—C3	1.326 (3)	C5—C6	1.344 (4)
N1—C1	1.385 (3)	C5—H5	0.9300
N2—C3	1.347 (4)	C6—H6	0.9300
N2—C2	1.377 (4)	C7—C8	1.483 (3)
N2—H2	0.856 (10)	C8—H8A	0.9600
N3—C7	1.323 (3)	C8—H8B	0.9600
N3—C5	1.381 (3)	C8—H8C	0.9600
N4—C7	1.342 (3)

N1—Ag1—N3	178.27 (7)	N1—C3—N2	110.0 (2)
H11—O1w—H12	106 (4)	N1—C3—C4	126.5 (2)
H21—O2w—H22	105 (3)	N2—C3—C4	123.5 (2)
C3—N1—C1	106.2 (2)	C3—C4—H4A	109.5
C3—N1—Ag1	125.87 (18)	C3—C4—H4B	109.5
C1—N1—Ag1	127.32 (17)	H4A—C4—H4B	109.5
C3—N2—C2	108.0 (2)	C3—C4—H4C	109.5
C3—N2—H2	121 (2)	H4A—C4—H4C	109.5
C2—N2—H2	131 (2)	H4B—C4—H4C	109.5
C7—N3—C5	106.7 (2)	C6—C5—N3	109.3 (2)
C7—N3—Ag1	126.03 (17)	C6—C5—H5	125.4
C5—N3—Ag1	126.92 (16)	N3—C5—H5	125.4
C7—N4—C6	108.0 (2)	C5—C6—N4	106.1 (2)
C7—N4—H4	125.1 (18)	C5—C6—H6	127.0
C6—N4—H4	126.9 (19)	N4—C6—H6	127.0
O3—N5—O2	120.2 (2)	N3—C7—N4	109.9 (2)
O3—N5—O1	119.9 (2)	N3—C7—C8	126.5 (2)
O2—N5—O1	119.9 (2)	N4—C7—C8	123.6 (2)
C2—C1—N1	109.5 (2)	C7—C8—H8A	109.5
C2—C1—H1	125.3	C7—C8—H8B	109.5
N1—C1—H1	125.3	H8A—C8—H8B	109.5
C1—C2—N2	106.3 (2)	C7—C8—H8C	109.5
C1—C2—H2A	126.9	H8A—C8—H8C	109.5
N2—C2—H2A	126.9	H8B—C8—H8C	109.5

C3—N1—C1—C2	−0.2 (3)	C7—N3—C5—C6	0.1 (3)
Ag1—N1—C1—C2	−171.9 (2)	Ag1—N3—C5—C6	−173.71 (19)
N1—C1—C2—N2	0.4 (3)	N3—C5—C6—N4	0.5 (3)
C3—N2—C2—C1	−0.5 (3)	C7—N4—C6—C5	−1.0 (3)
C1—N1—C3—N2	−0.1 (3)	C5—N3—C7—N4	−0.8 (3)
Ag1—N1—C3—N2	171.74 (19)	Ag1—N3—C7—N4	173.13 (18)
C1—N1—C3—C4	−179.5 (3)	C5—N3—C7—C8	178.6 (2)
Ag1—N1—C3—C4	−7.7 (4)	Ag1—N3—C7—C8	−7.5 (4)
C2—N2—C3—N1	0.4 (3)	C6—N4—C7—N3	1.1 (3)
C2—N2—C3—C4	179.8 (2)	C6—N4—C7—C8	−178.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1w	0.86 (1)	1.99 (1)	2.838 (3)	169 (3)
N4—H4···O1wⁱ	0.84 (1)	1.99 (1)	2.837 (3)	178 (3)
O1w—H11···O2w	0.85 (1)	1.89 (1)	2.726 (3)	170 (4)
O1w—H12···O1	0.85 (1)	1.99 (1)	2.826 (3)	171 (3)
O2w—H21···O1ⁱⁱ	0.84 (1)	2.02 (1)	2.867 (3)	179 (4)
O2w—H22···O2ⁱⁱⁱ	0.84 (1)	2.15 (2)	2.955 (3)	159 (3)

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

Experimental details

Crystal data
Chemical formula	[Ag(C4H6N₂)₂]NO₃·2H₂O
M_r	370.13
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	6.8001 (4), 17.0196 (9), 12.1453 (7)
β (°)	101.691 (1)
V (Å³)	1376.48 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.49
Crystal size (mm)	0.21 × 0.19 × 0.17

Data collection
Diffractometer	Bruker APEX2 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.745, 0.786
No. of measured, independent and observed [I > 2σ(I)] reflections	7483, 2721, 2083
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.073, 0.99
No. of reflections	2721
No. of parameters	198
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1w	0.86 (1)	1.99 (1)	2.838 (3)	169 (3)
N4—H4···O1wⁱ	0.84 (1)	1.99 (1)	2.837 (3)	178 (3)
O1w—H11···O2w	0.85 (1)	1.89 (1)	2.726 (3)	170 (4)
O1w—H12···O1	0.85 (1)	1.99 (1)	2.826 (3)	171 (3)
O2w—H21···O1ⁱⁱ	0.84 (1)	2.02 (1)	2.867 (3)	179 (4)
O2w—H22···O2ⁱⁱⁱ	0.84 (1)	2.15 (2)	2.955 (3)	159 (3)

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

Acknowledgements

We thank Tianjin Agricultural University and the University of Malaya for supporting this study.

References

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