Bis(3-methyl­isoquinoline-κN)silver(I) nitrate

In the title compound, [Ag(C₁₀H₉N)₂]NO₃, the Ag^I cation, lying on a twofold rotation axis, is two-coordinated by two N atoms from two different 3-methyl­isoquinoline mol­ecules in a linear coordination. The nitrate anions do not coordinate to the Ag^I cations, but rather act as counter-anions. The title compound forms a two-dimensional supramolecular structure through π–π inter­actions between the 3-methyl­isoquinoline ligands.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.045
• wR factor = 0.165
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.20
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Bis(3-methylisoquinoline-κN)silver(I) nitrate

Crystal data

[Ag(C10H9N)2]NO3	F(000) = 920
Mr = 456.24	Dx = 1.594 Mg m^−3
Monoclinic, C2/c	Melting point: not measured K
Hall symbol: -c 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 10.418 (5) Å	Cell parameters from 3040 reflections
b = 16.043 (5) Å	θ = 2.2–28.3°
c = 11.484 (5) Å	µ = 1.09 mm^−1
β = 98.031 (5)°	T = 292 K
V = 1900.6 (14) Å^3	Block, colorless
Z = 4	0.46 × 0.29 × 0.25 mm

Data collection

Bruker APEX CCD area-detector diffractometer	2213 independent reflections
Radiation source: fine-focus sealed tube	1685 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
Tmin = 0.617, Tmax = 0.764	k = −21→17
5724 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1128P)^2] where P = (Fo^2 + 2Fc^2)/3
2213 reflections	(Δ/σ)max < 0.001
143 parameters	Δρmax = 0.90 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.5000	0.24518 (2)	0.7500	0.0613 (3)
C1	0.7438 (3)	0.1843 (2)	0.6646 (3)	0.0475 (7)
H1	0.7006	0.1341	0.6706	0.057*
C2	0.8640 (3)	0.1821 (2)	0.6242 (3)	0.0429 (7)
C3	0.9243 (3)	0.1071 (2)	0.5985 (3)	0.0581 (8)
H3	0.8834	0.0564	0.6071	0.070*
C4	1.0433 (3)	0.1089 (2)	0.5608 (3)	0.0620 (9)
H4	1.0831	0.0591	0.5447	0.074*
C5	1.1052 (3)	0.1840 (2)	0.5461 (3)	0.0559 (8)
H5	1.1861	0.1840	0.5205	0.067*
C6	1.0485 (4)	0.2579 (2)	0.5690 (3)	0.0499 (9)
H6	1.0902	0.3079	0.5578	0.060*
C7	0.9270 (4)	0.25830 (16)	0.6096 (3)	0.0410 (7)
C8	0.8655 (3)	0.3318 (2)	0.6416 (3)	0.0474 (7)
H8	0.9043	0.3832	0.6334	0.057*
C9	0.7498 (3)	0.3282 (2)	0.6845 (3)	0.0450 (7)
C10	0.6861 (4)	0.4047 (2)	0.7270 (3)	0.0655 (10)
H10A	0.5956	0.4048	0.6959	0.098*
H10B	0.7266	0.4538	0.7009	0.098*
H10C	0.6956	0.4043	0.8114	0.098*
N1	0.6877 (4)	0.25343 (13)	0.6947 (3)	0.0442 (7)
N2	0.5667 (10)	0.0482 (6)	0.9195 (8)	0.097 (3)	0.50
O1	0.4503 (8)	0.0079 (5)	0.9123 (7)	0.115 (2)	0.50
O2	0.6203 (9)	0.0272 (5)	1.0208 (11)	0.129 (3)	0.50
O3	0.5918 (6)	0.0857 (3)	0.8582 (5)	0.0632 (16)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0390 (3)	0.0729 (4)	0.0758 (4)	0.000	0.0220 (2)	0.000
C1	0.0438 (17)	0.0495 (17)	0.0505 (16)	−0.0077 (13)	0.0112 (13)	0.0002 (13)
C2	0.0400 (16)	0.0483 (16)	0.0411 (14)	−0.0055 (12)	0.0076 (12)	−0.0021 (12)
C3	0.056 (2)	0.0479 (17)	0.073 (2)	−0.0044 (14)	0.0190 (17)	−0.0079 (15)
C4	0.059 (2)	0.058 (2)	0.073 (2)	0.0050 (15)	0.0223 (18)	−0.0094 (16)
C5	0.0413 (17)	0.075 (2)	0.0548 (18)	−0.0005 (15)	0.0174 (14)	−0.0038 (15)
C6	0.039 (2)	0.061 (2)	0.0508 (19)	−0.0067 (12)	0.0103 (16)	0.0042 (12)
C7	0.0349 (17)	0.0518 (18)	0.0363 (15)	−0.0031 (10)	0.0051 (13)	0.0055 (10)
C8	0.0444 (17)	0.0456 (16)	0.0525 (16)	−0.0031 (13)	0.0082 (13)	0.0093 (13)
C9	0.0392 (16)	0.0491 (16)	0.0459 (15)	0.0027 (12)	0.0029 (12)	0.0054 (12)
C10	0.061 (2)	0.0522 (19)	0.086 (2)	0.0080 (15)	0.0161 (19)	0.0027 (16)
N1	0.0360 (16)	0.0524 (17)	0.0453 (15)	−0.0016 (9)	0.0094 (13)	0.0020 (9)
N2	0.106 (7)	0.083 (6)	0.088 (6)	0.046 (6)	−0.038 (5)	−0.054 (5)
O1	0.081 (5)	0.099 (5)	0.155 (7)	−0.004 (4)	−0.011 (5)	−0.005 (5)
O2	0.119 (7)	0.079 (5)	0.185 (9)	0.002 (5)	0.007 (7)	−0.017 (5)
O3	0.084 (4)	0.056 (3)	0.059 (3)	−0.013 (2)	0.043 (3)	0.015 (2)

Geometric parameters (Å, º)

Ag1—N1^i	2.142 (4)	C6—H6	0.9300
Ag1—N1	2.142 (4)	C7—C8	1.415 (4)
C1—N1	1.323 (4)	C8—C9	1.365 (5)
C1—C2	1.395 (5)	C8—H8	0.9300
C1—H1	0.9300	C9—N1	1.375 (4)
C2—C3	1.407 (5)	C9—C10	1.510 (5)
C2—C7	1.409 (4)	C10—H10A	0.9600
C3—C4	1.369 (5)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
C4—C5	1.388 (5)	N2—O3	0.988 (12)
C4—H4	0.9300	N2—O2	1.264 (12)
C5—C6	1.366 (5)	N2—O1	1.367 (14)
C5—H5	0.9300	O1—O2^ii	1.267 (11)
C6—C7	1.409 (6)	O2—O1^ii	1.267 (11)
N1^i—Ag1—N1	172.91 (11)	C2—C7—C8	117.2 (4)
N1—C1—C2	124.0 (3)	C9—C8—C7	120.9 (3)
N1—C1—H1	118.0	C9—C8—H8	119.6
C2—C1—H1	118.0	C7—C8—H8	119.6
C1—C2—C3	122.6 (3)	C8—C9—N1	121.2 (3)
C1—C2—C7	118.2 (3)	C8—C9—C10	122.1 (3)
C3—C2—C7	119.2 (3)	N1—C9—C10	116.6 (3)
C4—C3—C2	120.0 (3)	C9—C10—H10A	109.5
C4—C3—H3	120.0	C9—C10—H10B	109.5
C2—C3—H3	120.0	H10A—C10—H10B	109.5
C3—C4—C5	120.9 (3)	C9—C10—H10C	109.5
C3—C4—H4	119.6	H10A—C10—H10C	109.5
C5—C4—H4	119.6	H10B—C10—H10C	109.5
C6—C5—C4	120.6 (3)	C1—N1—C9	118.6 (4)
C6—C5—H5	119.7	C1—N1—Ag1	118.8 (2)
C4—C5—H5	119.7	C9—N1—Ag1	122.6 (2)
C5—C6—C7	120.1 (3)	O3—N2—O2	133.7 (13)
C5—C6—H6	120.0	O3—N2—O1	124.4 (9)
C7—C6—H6	120.0	O2—N2—O1	101.8 (11)
C6—C7—C2	119.3 (3)	O2^ii—O1—N2	139.3 (9)
C6—C7—C8	123.4 (3)	N2—O2—O1^ii	117.3 (10)
N1—C1—C2—C3	176.6 (3)	C2—C7—C8—C9	−0.1 (5)
N1—C1—C2—C7	−2.9 (5)	C7—C8—C9—N1	−1.9 (5)
C1—C2—C3—C4	−179.0 (3)	C7—C8—C9—C10	175.8 (3)
C7—C2—C3—C4	0.5 (5)	C2—C1—N1—C9	0.9 (5)
C2—C3—C4—C5	−0.7 (6)	C2—C1—N1—Ag1	178.2 (2)
C3—C4—C5—C6	−0.1 (5)	C8—C9—N1—C1	1.5 (5)
C4—C5—C6—C7	1.0 (5)	C10—C9—N1—C1	−176.3 (3)
C5—C6—C7—C2	−1.1 (5)	C8—C9—N1—Ag1	−175.6 (2)
C5—C6—C7—C8	176.3 (3)	C10—C9—N1—Ag1	6.6 (4)
C1—C2—C7—C6	180.0 (3)	O3—N2—O1—O2^ii	−160.7 (11)
C3—C2—C7—C6	0.4 (5)	O2—N2—O1—O2^ii	16.2 (16)
C1—C2—C7—C8	2.4 (5)	O3—N2—O2—O1^ii	164.6 (10)
C3—C2—C7—C8	−177.2 (3)	O1—N2—O2—O1^ii	−11.8 (12)
C6—C7—C8—C9	−177.6 (3)

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