Bis(2-methyl-1H-imidazole-κN ³)silver(I) nitrate dihydrate

Abstract

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,

• a = 6.8001 (4) Å

• b = 17.0196 (9) Å

• c = 12.1453 (7) Å

• β = 101.691 (1)°

• V = 1376.48 (13) ų

• 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[F ² > 2σ(F ²)] = 0.024

• wR(F ²) = 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

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 ▶).

Supplementary Material

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

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⋯O1w i	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) ; (ii) ; (iii) .

supplementary crystallographic information

Experimental

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.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The amino and water H atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H = O–H = 0.85±0.01 Å; their displacement parameters were refined.

The final difference Fourier map had a peak that was displaced by 0.5 along y relative to Ag1. Thus, for the reflections with k odd a scale factor was refined to 1.035 (2) with respect to the reflections with k even. Although the refinement was not significantly improved, the final difference Fourier map now did not have any large peaks.

Figures

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.

Crystal data

[Ag(C4H6N2)2]NO3·2H2O	F(000) = 744
Mr = 370.13	Dx = 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

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

Refinement

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(Fo2) + (0.0441P)2 + 0.0379P] where P = (Fo2 + 2Fc2)/3
2721 reflections	(Δ/σ)max = 0.001
198 parameters	Δρmax = 0.54 e Å−3
6 restraints	Δρmin = −0.33 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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.