{4-[(Diphenyl-phosphino)methyl-amino]pyridinium-κP}bis-(nitrato-κO)silver(I).

In the title mononuclear complex, [Ag(C(18)H(18)N(2)P)(NO(3))(2)], the metal centre is coordinated in a slightly distorted trigonal-planar geometry by the P atom of the phosphine ligand and the O atoms of the two monodentate nitrate anions. In the crystal structure, complex mol-ecules are connected by inter-molecular N-H⋯O hydrogen bonds, forming chains running parallel to the b axis.

Related literature

For related structures, see: Song et al. (2002 ▶); Durran et al. (2006 ▶); Jiang et al. (2009 ▶); Wang et al. (2008 ▶).

Experimental

Crystal data

[Ag(C18H18N2P)(NO3)2]

M = 525.20

Triclinic,

a = 7.9760 (9) Å

b = 9.6895 (11) Å

c = 14.1207 (16) Å

α = 86.170 (2)°

β = 89.170 (2)°

γ = 69.439 (2)°

V = 1019.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.11 mm−1

T = 173 K

0.47 × 0.33 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.699, T max = 0.838

8623 measured reflections

4367 independent reflections

3802 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.109

S = 1.15

4367 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.46 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 I, global. DOI: 10.1107/S160053680903178X/rz2347sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903178X/rz2347Isup2.hkl

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

[Ag(C18H18N2P)(NO3)2]	Z = 2
Mr = 525.20	F(000) = 528
Triclinic, P1	Dx = 1.711 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9760 (9) Å	Cell parameters from 5807 reflections
b = 9.6895 (11) Å	θ = 2.7–27.0°
c = 14.1207 (16) Å	µ = 1.11 mm−1
α = 86.170 (2)°	T = 173 K
β = 89.170 (2)°	Block, colourless
γ = 69.439 (2)°	0.47 × 0.33 × 0.16 mm
V = 1019.5 (2) Å3

Bruker SMART CCD area-detector diffractometer	4367 independent reflections
Radiation source: fine-focus sealed tube	3802 reflections with I > 2σ(I)
graphite	Rint = 0.018
ω scans	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→9
Tmin = 0.699, Tmax = 0.838	k = −12→12
8623 measured reflections	l = −18→17

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0737P)2 + 0.0727P] where P = (Fo2 + 2Fc2)/3
4367 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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	0.46577 (3)	0.46190 (2)	0.297716 (16)	0.03069 (11)
P1	0.20209 (10)	0.64942 (8)	0.24168 (5)	0.02155 (16)
O1	0.6827 (3)	0.2456 (3)	0.24276 (18)	0.0391 (5)
O2	0.4738 (3)	0.1861 (3)	0.31211 (19)	0.0429 (6)
O3	0.6975 (3)	0.0183 (2)	0.25015 (18)	0.0428 (6)
O4	0.6546 (3)	0.4154 (2)	0.43169 (15)	0.0311 (5)
O5	0.7902 (3)	0.5171 (2)	0.52073 (17)	0.0381 (6)
O6	0.6328 (4)	0.6441 (3)	0.39968 (18)	0.0481 (7)
N1	0.1753 (3)	1.2090 (3)	0.45460 (18)	0.0283 (5)
H1A	0.1774	1.2963	0.4667	0.034*
N2	0.1655 (3)	0.7994 (2)	0.40482 (16)	0.0219 (5)
H2A	0.2357	0.7271	0.4428	0.026*
N3	0.6180 (4)	0.1481 (3)	0.26837 (18)	0.0288 (5)
N4	0.6919 (3)	0.5284 (3)	0.44974 (17)	0.0265 (5)
C1	0.2731 (4)	1.0885 (3)	0.5089 (2)	0.0269 (6)
H1B	0.3442	1.0991	0.5594	0.032*
C2	0.2720 (4)	0.9528 (3)	0.4930 (2)	0.0256 (6)
H2B	0.3420	0.8693	0.5321	0.031*
C3	0.1658 (3)	0.9348 (3)	0.41738 (19)	0.0204 (5)
C4	0.0664 (4)	1.0632 (3)	0.3620 (2)	0.0231 (6)
H4A	−0.0059	1.0567	0.3108	0.028*
C5	0.0740 (4)	1.1971 (3)	0.3818 (2)	0.0284 (6)
H5A	0.0070	1.2831	0.3438	0.034*
C6	0.0617 (4)	0.7590 (3)	0.33523 (19)	0.0230 (5)
H6A	−0.0272	0.8500	0.3051	0.028*
H6B	−0.0049	0.7010	0.3680	0.028*
C7	0.0424 (4)	0.5829 (3)	0.18720 (19)	0.0229 (5)
C8	0.0942 (4)	0.4339 (3)	0.1700 (2)	0.0325 (7)
H8A	0.2135	0.3697	0.1835	0.039*
C9	−0.0290 (5)	0.3790 (3)	0.1330 (3)	0.0394 (8)
H9A	0.0068	0.2772	0.1217	0.047*
C10	−0.1997 (5)	0.4697 (4)	0.1129 (2)	0.0375 (8)
H10A	−0.2831	0.4310	0.0884	0.045*
C11	−0.2522 (4)	0.6186 (4)	0.1281 (2)	0.0378 (8)
H11A	−0.3711	0.6822	0.1129	0.045*
C12	−0.1322 (4)	0.6748 (3)	0.1652 (2)	0.0335 (7)
H12A	−0.1692	0.7770	0.1758	0.040*
C13	0.2342 (4)	0.7867 (3)	0.15637 (19)	0.0227 (5)
C14	0.1854 (4)	0.7949 (4)	0.0613 (2)	0.0339 (7)
H14A	0.1303	0.7297	0.0404	0.041*
C15	0.2167 (5)	0.8975 (4)	−0.0029 (2)	0.0424 (8)
H15A	0.1858	0.9011	−0.0680	0.051*
C16	0.2934 (5)	0.9955 (4)	0.0282 (3)	0.0414 (8)
H16A	0.3104	1.0689	−0.0150	0.050*
C17	0.3444 (5)	0.9857 (4)	0.1215 (3)	0.0378 (8)
H17A	0.3977	1.0519	0.1425	0.045*
C18	0.3189 (4)	0.8801 (3)	0.1855 (2)	0.0285 (6)
H18A	0.3593	0.8716	0.2493	0.034*

	U11	U22	U33	U12	U13	U23
Ag1	0.03087 (16)	0.02167 (15)	0.03252 (16)	0.00010 (10)	−0.00920 (10)	−0.00312 (9)
P1	0.0243 (4)	0.0165 (3)	0.0215 (3)	−0.0036 (3)	−0.0032 (3)	−0.0036 (3)
O1	0.0364 (13)	0.0254 (12)	0.0523 (15)	−0.0074 (10)	0.0050 (11)	−0.0014 (10)
O2	0.0350 (13)	0.0333 (13)	0.0535 (15)	−0.0049 (10)	0.0092 (11)	0.0023 (11)
O3	0.0476 (14)	0.0205 (11)	0.0509 (15)	0.0013 (10)	−0.0151 (11)	−0.0095 (10)
O4	0.0377 (12)	0.0186 (10)	0.0362 (12)	−0.0080 (9)	−0.0105 (9)	−0.0035 (8)
O5	0.0479 (14)	0.0260 (12)	0.0433 (13)	−0.0169 (11)	−0.0224 (11)	0.0037 (10)
O6	0.0708 (18)	0.0321 (13)	0.0454 (15)	−0.0250 (13)	−0.0217 (13)	0.0142 (11)
N1	0.0319 (13)	0.0239 (13)	0.0343 (14)	−0.0151 (11)	0.0092 (11)	−0.0096 (10)
N2	0.0283 (12)	0.0136 (11)	0.0207 (11)	−0.0034 (9)	−0.0046 (9)	−0.0004 (8)
N3	0.0320 (14)	0.0225 (13)	0.0275 (13)	−0.0035 (11)	−0.0083 (10)	−0.0036 (10)
N4	0.0292 (13)	0.0214 (12)	0.0271 (12)	−0.0068 (10)	−0.0038 (10)	0.0000 (10)
C1	0.0248 (14)	0.0313 (16)	0.0276 (15)	−0.0123 (12)	0.0047 (11)	−0.0092 (12)
C2	0.0234 (14)	0.0331 (16)	0.0205 (13)	−0.0096 (12)	0.0016 (10)	−0.0042 (11)
C3	0.0171 (12)	0.0223 (14)	0.0205 (13)	−0.0049 (10)	0.0035 (10)	−0.0043 (10)
C4	0.0230 (13)	0.0214 (14)	0.0240 (14)	−0.0064 (11)	−0.0002 (10)	−0.0025 (11)
C5	0.0286 (15)	0.0275 (16)	0.0277 (15)	−0.0085 (12)	0.0053 (11)	−0.0001 (11)
C6	0.0243 (13)	0.0240 (14)	0.0202 (13)	−0.0074 (11)	−0.0008 (10)	−0.0039 (10)
C7	0.0267 (14)	0.0198 (13)	0.0229 (13)	−0.0086 (11)	−0.0025 (11)	−0.0024 (10)
C8	0.0340 (17)	0.0243 (16)	0.0362 (17)	−0.0058 (13)	−0.0082 (13)	−0.0045 (12)
C9	0.053 (2)	0.0170 (15)	0.049 (2)	−0.0121 (15)	−0.0120 (16)	−0.0056 (13)
C10	0.0388 (18)	0.0405 (19)	0.0408 (18)	−0.0222 (16)	−0.0018 (14)	−0.0082 (14)
C11	0.0276 (16)	0.043 (2)	0.0406 (19)	−0.0075 (14)	0.0001 (13)	−0.0133 (15)
C12	0.0316 (16)	0.0225 (16)	0.0429 (18)	−0.0033 (13)	−0.0039 (13)	−0.0111 (13)
C13	0.0206 (13)	0.0209 (13)	0.0233 (13)	−0.0030 (11)	0.0012 (10)	−0.0025 (10)
C14	0.0360 (17)	0.0389 (18)	0.0293 (16)	−0.0166 (15)	−0.0054 (13)	0.0011 (13)
C15	0.0381 (19)	0.063 (2)	0.0269 (16)	−0.0213 (18)	−0.0099 (13)	0.0133 (15)
C16	0.0333 (17)	0.0385 (19)	0.049 (2)	−0.0107 (15)	0.0033 (15)	0.0135 (15)
C17	0.0393 (19)	0.0294 (17)	0.048 (2)	−0.0156 (15)	0.0118 (15)	−0.0065 (14)
C18	0.0282 (15)	0.0315 (16)	0.0276 (15)	−0.0118 (13)	0.0031 (12)	−0.0081 (12)

Ag1—P1	2.3500 (8)	C5—H5A	0.9500
Ag1—O4	2.354 (2)	C6—H6A	0.9900
Ag1—O1	2.370 (2)	C6—H6B	0.9900
P1—C7	1.817 (3)	C7—C12	1.391 (4)
P1—C13	1.817 (3)	C7—C8	1.393 (4)
P1—C6	1.854 (3)	C8—C9	1.393 (4)
O1—N3	1.257 (3)	C8—H8A	0.9500
O2—N3	1.246 (3)	C9—C10	1.358 (5)
O3—N3	1.236 (3)	C9—H9A	0.9500
O4—N4	1.273 (3)	C10—C11	1.385 (5)
O5—N4	1.256 (3)	C10—H10A	0.9500
O6—N4	1.229 (3)	C11—C12	1.381 (5)
N1—C1	1.349 (4)	C11—H11A	0.9500
N1—C5	1.352 (4)	C12—H12A	0.9500
N1—H1A	0.8800	C13—C18	1.390 (4)
N2—C3	1.336 (3)	C13—C14	1.393 (4)
N2—C6	1.452 (3)	C14—C15	1.387 (5)
N2—H2A	0.8800	C14—H14A	0.9500
C1—C2	1.351 (4)	C15—C16	1.394 (5)
C1—H1B	0.9500	C15—H15A	0.9500
C2—C3	1.430 (4)	C16—C17	1.371 (5)
C2—H2B	0.9500	C16—H16A	0.9500
C3—C4	1.408 (4)	C17—C18	1.386 (4)
C4—C5	1.368 (4)	C17—H17A	0.9500
C4—H4A	0.9500	C18—H18A	0.9500
P1—Ag1—O4	136.46 (5)	P1—C6—H6A	109.0
P1—Ag1—O1	138.31 (7)	N2—C6—H6B	109.0
O4—Ag1—O1	84.99 (8)	P1—C6—H6B	109.0
C7—P1—C13	105.94 (13)	H6A—C6—H6B	107.8
C7—P1—C6	100.58 (13)	C12—C7—C8	118.8 (3)
C13—P1—C6	104.39 (13)	C12—C7—P1	122.2 (2)
C7—P1—Ag1	114.33 (10)	C8—C7—P1	119.0 (2)
C13—P1—Ag1	115.36 (9)	C7—C8—C9	120.0 (3)
C6—P1—Ag1	114.65 (9)	C7—C8—H8A	120.0
N3—O1—Ag1	102.13 (18)	C9—C8—H8A	120.0
N4—O4—Ag1	111.82 (16)	C10—C9—C8	120.7 (3)
C1—N1—C5	120.7 (3)	C10—C9—H9A	119.7
C1—N1—H1A	119.7	C8—C9—H9A	119.7
C5—N1—H1A	119.7	C9—C10—C11	120.0 (3)
C3—N2—C6	126.9 (2)	C9—C10—H10A	120.0
C3—N2—H2A	116.5	C11—C10—H10A	120.0
C6—N2—H2A	116.5	C12—C11—C10	120.2 (3)
O3—N3—O2	121.7 (3)	C12—C11—H11A	119.9
O3—N3—O1	120.0 (3)	C10—C11—H11A	119.9
O2—N3—O1	118.3 (3)	C11—C12—C7	120.4 (3)
O6—N4—O5	121.6 (2)	C11—C12—H12A	119.8
O6—N4—O4	121.0 (2)	C7—C12—H12A	119.8
O5—N4—O4	117.5 (2)	C18—C13—C14	119.1 (3)
N1—C1—C2	121.3 (3)	C18—C13—P1	119.2 (2)
N1—C1—H1B	119.3	C14—C13—P1	121.5 (2)
C2—C1—H1B	119.3	C15—C14—C13	120.4 (3)
C1—C2—C3	120.1 (3)	C15—C14—H14A	119.8
C1—C2—H2B	120.0	C13—C14—H14A	119.8
C3—C2—H2B	120.0	C14—C15—C16	119.8 (3)
N2—C3—C4	124.7 (2)	C14—C15—H15A	120.1
N2—C3—C2	118.4 (3)	C16—C15—H15A	120.1
C4—C3—C2	116.9 (3)	C17—C16—C15	119.7 (3)
C5—C4—C3	120.0 (3)	C17—C16—H16A	120.1
C5—C4—H4A	120.0	C15—C16—H16A	120.1
C3—C4—H4A	120.0	C16—C17—C18	120.8 (3)
N1—C5—C4	121.0 (3)	C16—C17—H17A	119.6
N1—C5—H5A	119.5	C18—C17—H17A	119.6
C4—C5—H5A	119.5	C17—C18—C13	120.1 (3)
N2—C6—P1	112.86 (19)	C17—C18—H18A	120.0
N2—C6—H6A	109.0	C13—C18—H18A	120.0
O4—Ag1—P1—C7	−139.96 (13)	C13—P1—C7—C12	−63.3 (3)
O1—Ag1—P1—C7	47.87 (14)	C6—P1—C7—C12	45.2 (3)
O4—Ag1—P1—C13	96.81 (13)	Ag1—P1—C7—C12	168.5 (2)
O1—Ag1—P1—C13	−75.36 (13)	C13—P1—C7—C8	119.1 (2)
O4—Ag1—P1—C6	−24.55 (14)	C6—P1—C7—C8	−132.4 (2)
O1—Ag1—P1—C6	163.29 (13)	Ag1—P1—C7—C8	−9.1 (3)
P1—Ag1—O1—N3	−89.92 (19)	C12—C7—C8—C9	−1.1 (5)
O4—Ag1—O1—N3	95.49 (19)	P1—C7—C8—C9	176.6 (3)
P1—Ag1—O4—N4	−46.8 (2)	C7—C8—C9—C10	0.3 (5)
O1—Ag1—O4—N4	128.01 (19)	C8—C9—C10—C11	0.8 (6)
Ag1—O1—N3—O3	179.4 (2)	C9—C10—C11—C12	−1.1 (5)
Ag1—O1—N3—O2	−0.7 (3)	C10—C11—C12—C7	0.3 (5)
Ag1—O4—N4—O6	−0.5 (4)	C8—C7—C12—C11	0.7 (5)
Ag1—O4—N4—O5	179.1 (2)	P1—C7—C12—C11	−176.9 (3)
C5—N1—C1—C2	−0.5 (4)	C7—P1—C13—C18	166.2 (2)
N1—C1—C2—C3	0.0 (4)	C6—P1—C13—C18	60.5 (3)
C6—N2—C3—C4	−1.9 (4)	Ag1—P1—C13—C18	−66.2 (2)
C6—N2—C3—C2	177.3 (2)	C7—P1—C13—C14	−17.5 (3)
C1—C2—C3—N2	−178.8 (3)	C6—P1—C13—C14	−123.2 (3)
C1—C2—C3—C4	0.4 (4)	Ag1—P1—C13—C14	110.0 (2)
N2—C3—C4—C5	178.9 (3)	C18—C13—C14—C15	−1.7 (5)
C2—C3—C4—C5	−0.2 (4)	P1—C13—C14—C15	−177.9 (3)
C1—N1—C5—C4	0.7 (4)	C13—C14—C15—C16	−1.6 (5)
C3—C4—C5—N1	−0.3 (4)	C14—C15—C16—C17	2.7 (6)
C3—N2—C6—P1	111.1 (3)	C15—C16—C17—C18	−0.6 (5)
C7—P1—C6—N2	167.0 (2)	C16—C17—C18—C13	−2.7 (5)
C13—P1—C6—N2	−83.4 (2)	C14—C13—C18—C17	3.8 (4)
Ag1—P1—C6—N2	43.8 (2)	P1—C13—C18—C17	−179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5i	0.88	1.93	2.807 (3)	172
N2—H2A···O4ii	0.88	2.16	3.013 (3)	162
N2—H2A···O5ii	0.88	2.47	3.075 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5i	0.88	1.93	2.807 (3)	172
N2—H2A⋯O4ii	0.88	2.16	3.013 (3)	162
N2—H2A⋯O5ii	0.88	2.47	3.075 (3)	127

Symmetry codes: (i) ; (ii) .