Bis­[2-(benzyl­amino)­pyridine-κN]silver(I) perchlorate

The title compound, [Ag(C₁₂H₁₂N₂)₂]ClO₄, is a mononuclear silver(I) complex. The Ag^I atom is coordinated by two pyridine N atoms from two benzyl­amino­pyridine ligands. In the crystal structure, the mol­ecules are linked by N—H...O intermolecular hydrogen bonds, forming chains along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.017 Å
• Disorder in solvent or counterion
• R factor = 0.067
• wR factor = 0.200
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         39 Perc.

Alert level C
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          4
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        Ag1
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         C2
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         C6
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        C14
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N3
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         C7
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C19
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      44.00 Perc.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C7     -C12           1.36 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C19    -C24           1.36 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         17

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 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
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(2-benzylaminopyridine)silver(I) perchlorate

Crystal data

[Ag(C12H12N2)2]ClO4	F(000) = 1168
Mr = 575.79	Dx = 1.558 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 784 reflections
a = 23.594 (7) Å	θ = 2.3–22.5°
b = 5.7205 (16) Å	µ = 0.97 mm^−1
c = 18.223 (5) Å	T = 293 K
β = 93.308 (6)°	Monoclinic, colourless
V = 2455.4 (12) Å^3	0.25 × 0.15 × 0.05 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4327 independent reflections
Radiation source: fine-focus sealed tube	1674 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.096
φ and ω scans	θmax = 25.0°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→27
Tmin = 0.763, Tmax = 0.953	k = −6→6
9722 measured reflections	l = −11→21

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.200	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0844P)^2] where P = (Fo^2 + 2Fc^2)/3
4327 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 0.73 e Å^−3
38 restraints	Δρmin = −0.69 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	0.25013 (3)	0.24275 (15)	0.02384 (6)	0.0816 (4)
N1	0.3038 (3)	−0.0616 (13)	0.0340 (5)	0.056 (2)
N2	0.3304 (3)	−0.0337 (14)	−0.0867 (5)	0.061 (2)
H2A	0.3109	0.0933	−0.0904	0.073*
N3	0.1999 (3)	0.5531 (13)	0.0052 (5)	0.054 (2)
N4	0.1630 (3)	0.5454 (14)	0.1188 (5)	0.064 (2)
H4A	0.1832	0.4222	0.1273	0.077*
Cl1	0.24223 (15)	0.3744 (5)	0.76226 (18)	0.0955 (11)
O1	0.2479 (6)	0.6200 (14)	0.7552 (8)	0.072 (6)*	0.572 (13)
O2	0.1819 (4)	0.324 (3)	0.7739 (9)	0.140 (8)*	0.572 (13)
O3	0.2746 (6)	0.305 (2)	0.8278 (6)	0.118 (7)*	0.572 (13)
O4	0.2579 (5)	0.246 (2)	0.7001 (6)	0.088 (5)*	0.572 (13)
O1'	0.2338 (8)	0.6178 (17)	0.7700 (10)	0.081 (8)*	0.428 (13)
O2'	0.2318 (8)	0.236 (3)	0.8220 (7)	0.099 (7)*	0.428 (13)
O3'	0.3061 (4)	0.355 (4)	0.7557 (12)	0.181 (13)*	0.428 (13)
O4'	0.2215 (8)	0.301 (3)	0.6910 (6)	0.117 (9)*	0.428 (13)
C1	0.3057 (5)	−0.184 (2)	0.0978 (7)	0.075 (4)
H1	0.2854	−0.1256	0.1361	0.091*
C2	0.3355 (5)	−0.387 (3)	0.1093 (8)	0.089 (4)
H2	0.3356	−0.4661	0.1539	0.106*
C3	0.3649 (4)	−0.4677 (19)	0.0528 (8)	0.070 (3)
H3	0.3858	−0.6046	0.0593	0.083*
C4	0.3649 (4)	−0.3572 (16)	−0.0123 (6)	0.056 (3)
H4	0.3855	−0.4153	−0.0503	0.067*
C5	0.3328 (4)	−0.1516 (17)	−0.0210 (6)	0.052 (3)
C6	0.3587 (4)	−0.113 (2)	−0.1494 (6)	0.070 (3)
H6A	0.3442	−0.0244	−0.1918	0.084*
H6B	0.3487	−0.2753	−0.1580	0.084*
C7	0.4220 (4)	−0.0939 (16)	−0.1450 (5)	0.048 (2)
C8	0.4485 (5)	0.082 (2)	−0.1064 (7)	0.083 (4)
H8	0.4272	0.1867	−0.0805	0.100*
C9	0.5070 (6)	0.106 (2)	−0.1052 (8)	0.104 (5)
H9	0.5245	0.2319	−0.0807	0.125*
C10	0.5383 (5)	−0.051 (3)	−0.1393 (9)	0.099 (5)
H10	0.5777	−0.0377	−0.1368	0.119*
C11	0.5127 (6)	−0.228 (3)	−0.1775 (8)	0.101 (4)
H11	0.5345	−0.3339	−0.2022	0.121*
C12	0.4545 (5)	−0.252 (2)	−0.1799 (6)	0.082 (3)
H12	0.4372	−0.3759	−0.2054	0.098*
C13	0.2044 (5)	0.651 (3)	−0.0592 (8)	0.079 (4)
H13	0.2280	0.5810	−0.0919	0.095*
C14	0.1763 (6)	0.853 (3)	−0.0812 (8)	0.097 (5)
H14	0.1800	0.9175	−0.1275	0.117*
C15	0.1426 (5)	0.9540 (19)	−0.0311 (8)	0.077 (4)
H15	0.1235	1.0919	−0.0437	0.092*
C16	0.1361 (4)	0.8604 (16)	0.0353 (7)	0.058 (3)
H16	0.1125	0.9294	0.0682	0.070*
C17	0.1666 (4)	0.6520 (17)	0.0537 (6)	0.053 (3)
C18	0.1278 (4)	0.624 (2)	0.1749 (6)	0.070 (3)
H18A	0.1362	0.7868	0.1852	0.085*
H18B	0.1374	0.5358	0.2194	0.085*
C19	0.0647 (4)	0.5996 (16)	0.1564 (5)	0.051 (3)
C20	0.0436 (5)	0.421 (2)	0.1151 (7)	0.086 (4)
H20	0.0681	0.3138	0.0954	0.103*
C21	−0.0150 (6)	0.397 (2)	0.1017 (7)	0.095 (4)
H21	−0.0288	0.2713	0.0738	0.114*
C22	−0.0518 (5)	0.550 (3)	0.1281 (8)	0.089 (4)
H22	−0.0907	0.5325	0.1184	0.107*
C23	−0.0312 (5)	0.725 (3)	0.1679 (8)	0.089 (4)
H23	−0.0564	0.8305	0.1870	0.106*
C24	0.0264 (5)	0.7580 (19)	0.1826 (6)	0.072 (3)
H24	0.0394	0.8864	0.2100	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0545 (5)	0.0591 (5)	0.1330 (9)	0.0030 (4)	0.0201 (5)	−0.0312 (6)
N1	0.048 (5)	0.054 (5)	0.067 (7)	−0.010 (4)	0.010 (5)	−0.017 (5)
N2	0.052 (5)	0.062 (5)	0.069 (7)	0.015 (4)	0.009 (5)	0.008 (5)
N3	0.049 (5)	0.052 (5)	0.063 (7)	−0.007 (4)	0.009 (5)	−0.015 (5)
N4	0.053 (5)	0.075 (6)	0.066 (7)	0.023 (4)	0.012 (5)	0.017 (5)
Cl1	0.156 (3)	0.0666 (18)	0.063 (2)	−0.002 (2)	0.002 (2)	0.0016 (17)
C1	0.066 (8)	0.097 (10)	0.066 (9)	−0.034 (7)	0.023 (7)	−0.018 (8)
C2	0.089 (10)	0.096 (11)	0.079 (11)	−0.027 (8)	−0.015 (9)	0.035 (9)
C3	0.055 (7)	0.063 (7)	0.089 (10)	−0.012 (6)	−0.006 (7)	0.015 (8)
C4	0.054 (6)	0.034 (5)	0.079 (9)	0.003 (5)	0.007 (6)	0.007 (6)
C5	0.049 (6)	0.046 (5)	0.061 (8)	−0.009 (5)	−0.001 (6)	0.000 (6)
C6	0.054 (7)	0.100 (8)	0.055 (8)	0.001 (6)	−0.003 (6)	−0.002 (7)
C7	0.062 (6)	0.054 (6)	0.028 (6)	0.000 (5)	0.007 (5)	0.004 (5)
C8	0.079 (8)	0.073 (8)	0.100 (11)	−0.004 (7)	0.023 (8)	−0.025 (7)
C9	0.077 (9)	0.093 (10)	0.142 (15)	−0.025 (8)	−0.004 (10)	0.002 (10)
C10	0.068 (9)	0.095 (11)	0.136 (15)	−0.007 (8)	0.009 (9)	0.057 (10)
C11	0.079 (9)	0.100 (10)	0.127 (13)	0.020 (9)	0.037 (9)	0.011 (10)
C12	0.078 (8)	0.091 (8)	0.078 (9)	0.002 (8)	0.017 (7)	−0.031 (8)
C13	0.060 (8)	0.100 (10)	0.076 (11)	−0.022 (7)	0.000 (8)	−0.019 (8)
C14	0.096 (11)	0.139 (13)	0.054 (10)	−0.050 (10)	−0.012 (9)	0.015 (10)
C15	0.074 (8)	0.063 (7)	0.087 (10)	−0.026 (7)	−0.046 (8)	0.034 (8)
C16	0.060 (7)	0.034 (5)	0.078 (9)	0.009 (5)	−0.013 (6)	−0.005 (6)
C17	0.047 (6)	0.049 (6)	0.063 (8)	−0.007 (5)	−0.003 (6)	−0.012 (6)
C18	0.059 (7)	0.106 (9)	0.046 (7)	−0.003 (6)	−0.003 (6)	0.003 (7)
C19	0.065 (7)	0.047 (6)	0.039 (7)	0.000 (5)	−0.002 (6)	−0.011 (5)
C20	0.074 (8)	0.072 (8)	0.109 (11)	0.013 (7)	−0.006 (8)	−0.017 (8)
C21	0.096 (10)	0.067 (8)	0.119 (13)	−0.028 (8)	−0.014 (9)	−0.024 (8)
C22	0.073 (9)	0.080 (9)	0.112 (13)	−0.017 (8)	−0.018 (9)	0.029 (9)
C23	0.058 (7)	0.109 (11)	0.100 (11)	0.013 (9)	0.023 (7)	0.013 (10)
C24	0.081 (8)	0.077 (7)	0.058 (8)	0.001 (7)	0.004 (6)	−0.025 (7)

Geometric parameters (Å, º)

Ag1—N3	2.150 (8)	C7—C12	1.364 (12)
Ag1—N1	2.155 (8)	C8—C9	1.386 (14)
N1—C5	1.349 (11)	C8—H8	0.93
N1—C1	1.354 (14)	C9—C10	1.338 (18)
N2—C5	1.373 (12)	C9—H9	0.93
N2—C6	1.429 (11)	C10—C11	1.351 (17)
N2—H2A	0.86	C10—H10	0.93
N3—C13	1.311 (14)	C11—C12	1.379 (15)
N3—C17	1.341 (11)	C11—H11	0.93
N4—C17	1.341 (12)	C12—H12	0.93
N4—C18	1.426 (11)	C13—C14	1.380 (18)
N4—H4A	0.86	C13—H13	0.93
Cl1—O2'	1.380 (9)	C14—C15	1.371 (16)
Cl1—O1'	1.414 (9)	C14—H14	0.93
Cl1—O4	1.417 (8)	C15—C16	1.340 (14)
Cl1—O1	1.418 (8)	C15—H15	0.93
Cl1—O4'	1.425 (9)	C16—C17	1.422 (13)
Cl1—O3	1.437 (9)	C16—H16	0.93
Cl1—O2	1.479 (9)	C18—C19	1.514 (12)
Cl1—O3'	1.522 (9)	C18—H18A	0.97
C1—C2	1.371 (16)	C18—H18B	0.97
C1—H1	0.93	C19—C20	1.347 (14)
C2—C3	1.354 (15)	C19—C24	1.383 (12)
C2—H2	0.93	C20—C21	1.395 (14)
C3—C4	1.344 (13)	C20—H20	0.93
C3—H3	0.93	C21—C22	1.341 (16)
C4—C5	1.402 (12)	C21—H21	0.93
C4—H4	0.93	C22—C23	1.313 (16)
C6—C7	1.494 (12)	C22—H22	0.93
C6—H6A	0.97	C23—C24	1.385 (15)
C6—H6B	0.97	C23—H23	0.93
C7—C8	1.358 (13)	C24—H24	0.93
N3—Ag1—N1	175.1 (4)	C10—C9—C8	120.0 (13)
C5—N1—C1	116.6 (9)	C10—C9—H9	120.0
C5—N1—Ag1	124.5 (8)	C8—C9—H9	120.0
C1—N1—Ag1	118.7 (8)	C9—C10—C11	119.9 (13)
C5—N2—C6	122.9 (9)	C9—C10—H10	120.0
C5—N2—H2A	118.5	C11—C10—H10	120.0
C6—N2—H2A	118.5	C10—C11—C12	120.4 (13)
C13—N3—C17	119.3 (10)	C10—C11—H11	119.8
C13—N3—Ag1	115.0 (9)	C12—C11—H11	119.8
C17—N3—Ag1	125.6 (8)	C7—C12—C11	120.3 (12)
C17—N4—C18	124.1 (9)	C7—C12—H12	119.9
C17—N4—H4A	118.0	C11—C12—H12	119.9
C18—N4—H4A	118.0	N3—C13—C14	123.8 (13)
O2'—Cl1—O1'	117.0 (9)	N3—C13—H13	118.1
O4—Cl1—O1	114.3 (7)	C14—C13—H13	118.1
O2'—Cl1—O4'	118.9 (9)	C15—C14—C13	116.5 (13)
O1'—Cl1—O4'	109.7 (8)	C15—C14—H14	121.7
O4—Cl1—O3	111.7 (7)	C13—C14—H14	121.7
O1—Cl1—O3	107.6 (7)	C16—C15—C14	122.2 (12)
O4—Cl1—O2	108.1 (7)	C16—C15—H15	118.9
O1—Cl1—O2	107.7 (7)	C14—C15—H15	118.9
O3—Cl1—O2	107.2 (8)	C15—C16—C17	117.7 (11)
O2'—Cl1—O3'	104.0 (8)	C15—C16—H16	121.1
O1'—Cl1—O3'	103.0 (9)	C17—C16—H16	121.1
O4'—Cl1—O3'	101.3 (8)	N3—C17—N4	117.4 (10)
N1—C1—C2	124.1 (11)	N3—C17—C16	120.4 (11)
N1—C1—H1	118.0	N4—C17—C16	122.2 (10)
C2—C1—H1	118.0	N4—C18—C19	114.7 (8)
C3—C2—C1	117.0 (12)	N4—C18—H18A	108.6
C3—C2—H2	121.5	C19—C18—H18A	108.6
C1—C2—H2	121.5	N4—C18—H18B	108.6
C4—C3—C2	122.4 (12)	C19—C18—H18B	108.6
C4—C3—H3	118.8	H18A—C18—H18B	107.6
C2—C3—H3	118.8	C20—C19—C24	117.5 (10)
C3—C4—C5	117.8 (11)	C20—C19—C18	121.4 (10)
C3—C4—H4	121.1	C24—C19—C18	121.1 (9)
C5—C4—H4	121.1	C19—C20—C21	120.2 (11)
N1—C5—N2	117.6 (10)	C19—C20—H20	119.9
N1—C5—C4	122.0 (10)	C21—C20—H20	119.9
N2—C5—C4	120.4 (10)	C22—C21—C20	121.9 (12)
N2—C6—C7	116.5 (9)	C22—C21—H21	119.0
N2—C6—H6A	108.2	C20—C21—H21	119.0
C7—C6—H6A	108.2	C23—C22—C21	117.9 (12)
N2—C6—H6B	108.2	C23—C22—H22	121.1
C7—C6—H6B	108.2	C21—C22—H22	121.1
H6A—C6—H6B	107.3	C22—C23—C24	122.7 (12)
C8—C7—C12	118.5 (10)	C22—C23—H23	118.6
C8—C7—C6	120.6 (10)	C24—C23—H23	118.6
C12—C7—C6	120.9 (10)	C19—C24—C23	119.7 (11)
C7—C8—C9	120.8 (11)	C19—C24—H24	120.1
C7—C8—H8	119.6	C23—C24—H24	120.1
C9—C8—H8	119.6
C5—N1—C1—C2	1.0 (15)	C17—N3—C13—C14	−0.5 (16)
Ag1—N1—C1—C2	176.1 (8)	Ag1—N3—C13—C14	−179.1 (9)
N1—C1—C2—C3	0.3 (17)	N3—C13—C14—C15	0.9 (17)
C1—C2—C3—C4	−0.6 (17)	C13—C14—C15—C16	−1.2 (17)
C2—C3—C4—C5	−0.3 (15)	C14—C15—C16—C17	1.2 (15)
C1—N1—C5—N2	178.4 (8)	C13—N3—C17—N4	179.8 (9)
Ag1—N1—C5—N2	3.7 (12)	Ag1—N3—C17—N4	−1.8 (12)
C1—N1—C5—C4	−1.9 (13)	C13—N3—C17—C16	0.4 (13)
Ag1—N1—C5—C4	−176.7 (6)	Ag1—N3—C17—C16	178.9 (6)
C6—N2—C5—N1	−179.3 (8)	C18—N4—C17—N3	−177.5 (8)
C6—N2—C5—C4	1.1 (13)	C18—N4—C17—C16	1.8 (14)
C3—C4—C5—N1	1.6 (14)	C15—C16—C17—N3	−0.8 (13)
C3—C4—C5—N2	−178.8 (9)	C15—C16—C17—N4	179.9 (9)
C5—N2—C6—C7	−70.9 (13)	C17—N4—C18—C19	68.2 (13)
N2—C6—C7—C8	−32.0 (15)	N4—C18—C19—C20	33.8 (15)
N2—C6—C7—C12	148.3 (10)	N4—C18—C19—C24	−147.5 (10)
C12—C7—C8—C9	2.8 (18)	C24—C19—C20—C21	−1.8 (17)
C6—C7—C8—C9	−176.8 (11)	C18—C19—C20—C21	177.0 (11)
C7—C8—C9—C10	−3 (2)	C19—C20—C21—C22	1 (2)
C8—C9—C10—C11	3 (2)	C20—C21—C22—C23	−1 (2)
C9—C10—C11—C12	−2 (2)	C21—C22—C23—C24	1 (2)
C8—C7—C12—C11	−1.9 (17)	C20—C19—C24—C23	2.1 (16)
C6—C7—C12—C11	177.8 (11)	C18—C19—C24—C23	−176.7 (10)
C10—C11—C12—C7	1 (2)	C22—C23—C24—C19	−1.7 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3^i	0.86	2.07	2.770 (13)	138
N4—H4A···O4^ii	0.86	2.35	3.098 (15)	146

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