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Abstract top

In the title compound, [Ag(C₁₉H₁₈N₆O)]ClO₄, the cation and anion both lie on crystallographic twofold rotation axes. The hydroxyl group of the cation is disordered across the twofold rotation axis. The Ag^I centre is four-coordinated by four N atoms from the 1,3-bis[3-(2-pyridyl)-1H-pyrazole]propan-2-ol ligand in a distorted tetrahedral coordination environment. O-HO and weak C-HO hydrogen-bonding interactions link adjacent mononuclear Ag^I units and perchlorate ions, forming a chain.

{1,3-Bis[3-(2-pyridyl)-1H-pyrazol-1-yl]propan-2-ol}silver(I) perchlorate top

Crystal data top

[Ag(C₁₉H₁₈N₆O)]ClO₄	F(000) = 1112
M_r = 553.71	D_x = 1.784 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 946 reflections
a = 8.687 (3) Å	θ = 2.6–22.8°
b = 21.863 (9) Å	µ = 1.15 mm⁻¹
c = 10.904 (4) Å	T = 293 K
β = 95.482 (7)°	Block, colourless
V = 2061.4 (14) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2135 independent reflections
Radiation source: fine-focus sealed tube	1497 reflections with I > 2σ(I)
graphite	R_int = 0.031
φ and ω scans	θ_max = 26.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −6→10
T_min = 0.802, T_max = 0.819	k = −27→24
5960 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0393P)² + 1.8827P] where P = (F_o² + 2F_c²)/3
2135 reflections	(Δ/σ)_max = 0.001
151 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Ag(C₁₉H₁₈N₆O)]ClO₄	V = 2061.4 (14) Å³
M_r = 553.71	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 8.687 (3) Å	µ = 1.15 mm⁻¹
b = 21.863 (9) Å	T = 293 K
c = 10.904 (4) Å	0.20 × 0.20 × 0.18 mm
β = 95.482 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2135 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1497 reflections with I > 2σ(I)
T_min = 0.802, T_max = 0.819	R_int = 0.031
5960 measured reflections	θ_max = 26.5°

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.53 e Å⁻³
S = 1.00	Δρ_min = −0.46 e Å⁻³
2135 reflections	Absolute structure: ?
151 parameters	Flack parameter: ?
0 restraints	Rogers parameter: ?

Special details top

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.

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.5000	0.510403 (19)	0.7500	0.0676 (2)
Cl1	0.5000	0.76495 (5)	1.2500	0.0524 (3)
N1	0.5693 (3)	0.58693 (12)	0.9020 (2)	0.0499 (7)
N2	0.3199 (3)	0.47008 (13)	0.6097 (3)	0.0523 (7)
N3	0.5527 (3)	0.64717 (13)	0.9227 (3)	0.0550 (7)
C1	0.5000	0.7204 (3)	0.7500	0.0764 (18)
H1B	0.4098	0.7391	0.7082	0.092*	0.50
C2	0.4355 (4)	0.68233 (16)	0.8498 (4)	0.0610 (10)
H2A	0.3847	0.7093	0.9040	0.073*
H2B	0.3581	0.6545	0.8117	0.073*
C3	0.6549 (5)	0.66635 (19)	1.0135 (4)	0.0652 (11)
H3A	0.6642	0.7061	1.0438	0.078*
C4	0.7424 (5)	0.61826 (18)	1.0539 (3)	0.0626 (10)
H4A	0.8231	0.6179	1.1164	0.075*
C5	0.6859 (4)	0.56931 (16)	0.9822 (3)	0.0494 (8)
C6	0.2745 (5)	0.41184 (17)	0.6109 (3)	0.0629 (10)
H6A	0.3154	0.3869	0.6750	0.075*
C7	0.1708 (5)	0.38710 (19)	0.5223 (4)	0.0716 (11)
H7A	0.1399	0.3465	0.5271	0.086*
C8	0.1142 (5)	0.4230 (2)	0.4277 (4)	0.0732 (12)
H8A	0.0438	0.4073	0.3662	0.088*
C9	0.1609 (4)	0.48229 (19)	0.4231 (4)	0.0648 (10)
H9A	0.1238	0.5071	0.3576	0.078*
C10	0.2638 (4)	0.50556 (15)	0.5161 (3)	0.0474 (8)
O1	0.5842 (6)	0.7655 (2)	0.7817 (5)	0.0669 (14)	0.50
H1A	0.6650	0.7632	0.7489	0.100*	0.50
O2	0.5854 (3)	0.80126 (13)	1.1757 (3)	0.0911 (10)
O3	0.3944 (4)	0.72815 (17)	1.1794 (4)	0.1176 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0799 (3)	0.0611 (3)	0.0565 (3)	0.000	−0.0203 (2)	0.000
Cl1	0.0450 (7)	0.0449 (7)	0.0679 (8)	0.000	0.0082 (6)	0.000
N1	0.0484 (17)	0.0463 (16)	0.0551 (17)	0.0007 (12)	0.0061 (14)	−0.0066 (13)
N2	0.0617 (19)	0.0466 (17)	0.0474 (17)	−0.0030 (13)	−0.0007 (14)	−0.0032 (13)
N3	0.0512 (18)	0.0479 (17)	0.068 (2)	−0.0006 (13)	0.0166 (15)	−0.0087 (14)
C1	0.079 (4)	0.051 (3)	0.105 (5)	0.000	0.040 (4)	0.000
C2	0.056 (2)	0.048 (2)	0.082 (3)	0.0067 (17)	0.023 (2)	−0.0028 (19)
C3	0.070 (3)	0.061 (2)	0.067 (3)	−0.015 (2)	0.019 (2)	−0.027 (2)
C4	0.064 (2)	0.072 (3)	0.052 (2)	−0.010 (2)	0.0030 (18)	−0.0135 (19)
C5	0.047 (2)	0.059 (2)	0.0423 (19)	−0.0041 (16)	0.0093 (16)	−0.0089 (16)
C6	0.078 (3)	0.051 (2)	0.059 (2)	−0.0030 (19)	0.006 (2)	−0.0029 (18)
C7	0.077 (3)	0.061 (3)	0.078 (3)	−0.013 (2)	0.013 (2)	−0.020 (2)
C8	0.068 (3)	0.079 (3)	0.069 (3)	−0.007 (2)	−0.007 (2)	−0.027 (2)
C9	0.062 (2)	0.079 (3)	0.051 (2)	0.006 (2)	−0.0058 (18)	−0.008 (2)
C10	0.0418 (18)	0.058 (2)	0.0427 (18)	0.0064 (15)	0.0079 (14)	−0.0030 (16)
O1	0.067 (3)	0.052 (3)	0.082 (4)	−0.020 (2)	0.009 (3)	−0.020 (3)
O2	0.086 (2)	0.080 (2)	0.113 (3)	0.0011 (16)	0.0363 (18)	0.0338 (18)
O3	0.077 (2)	0.118 (3)	0.156 (3)	−0.0239 (19)	0.006 (2)	−0.072 (3)

Geometric parameters (Å, °) top

Ag1—N2	2.260 (3)	C2—H2A	0.97
Ag1—N2ⁱ	2.260 (3)	C2—H2B	0.97
Ag1—N1	2.391 (3)	C3—C4	1.346 (5)
Ag1—N1ⁱ	2.391 (3)	C3—H3A	0.93
Cl1—O3	1.395 (3)	C4—C5	1.387 (5)
Cl1—O3ⁱⁱ	1.395 (3)	C4—H4A	0.93
Cl1—O2ⁱⁱ	1.397 (3)	C5—C10ⁱ	1.460 (5)
Cl1—O2	1.397 (3)	C6—C7	1.368 (5)
N1—C5	1.330 (4)	C6—H6A	0.93
N1—N3	1.346 (4)	C7—C8	1.351 (6)
N2—C6	1.333 (4)	C7—H7A	0.93
N2—C10	1.337 (4)	C8—C9	1.361 (6)
N3—C3	1.333 (5)	C8—H8A	0.93
N3—C2	1.451 (5)	C9—C10	1.383 (5)
C1—O1	1.257 (6)	C9—H9A	0.93
C1—O1ⁱ	1.257 (6)	C10—C5ⁱ	1.460 (5)
C1—C2ⁱ	1.519 (5)	O1—O1ⁱ	1.557 (10)
C1—C2	1.519 (5)	O1—H1A	0.82
C1—H1B	0.96

N2—Ag1—N2ⁱ	134.08 (15)	C1—C2—H2A	108.9
N2—Ag1—N1	148.68 (10)	N3—C2—H2B	108.9
N2ⁱ—Ag1—N1	72.03 (10)	C1—C2—H2B	108.9
N2—Ag1—N1ⁱ	72.03 (10)	H2A—C2—H2B	107.7
N2ⁱ—Ag1—N1ⁱ	148.68 (10)	N3—C3—C4	108.2 (3)
N1—Ag1—N1ⁱ	91.21 (14)	N3—C3—H3A	125.9
O3—Cl1—O3ⁱⁱ	109.6 (4)	C4—C3—H3A	125.9
O3—Cl1—O2ⁱⁱ	106.87 (19)	C3—C4—C5	105.1 (4)
O3ⁱⁱ—Cl1—O2ⁱⁱ	111.4 (2)	C3—C4—H4A	127.5
O3—Cl1—O2	111.4 (2)	C5—C4—H4A	127.5
O3ⁱⁱ—Cl1—O2	106.87 (19)	N1—C5—C4	110.7 (3)
O2ⁱⁱ—Cl1—O2	110.8 (3)	N1—C5—C10ⁱ	119.5 (3)
C5—N1—N3	105.1 (3)	C4—C5—C10ⁱ	129.8 (3)
C5—N1—Ag1	112.2 (2)	N2—C6—C7	123.1 (4)
N3—N1—Ag1	140.9 (2)	N2—C6—H6A	118.4
C6—N2—C10	118.4 (3)	C7—C6—H6A	118.4
C6—N2—Ag1	123.5 (2)	C8—C7—C6	118.4 (4)
C10—N2—Ag1	118.0 (2)	C8—C7—H7A	120.8
C3—N3—N1	111.0 (3)	C6—C7—H7A	120.8
C3—N3—C2	128.6 (3)	C7—C8—C9	119.6 (4)
N1—N3—C2	120.5 (3)	C7—C8—H8A	120.2
O1—C1—O1ⁱ	76.5 (6)	C9—C8—H8A	120.2
O1—C1—C2ⁱ	112.5 (3)	C8—C9—C10	119.8 (4)
O1ⁱ—C1—C2ⁱ	118.5 (3)	C8—C9—H9A	120.1
O1—C1—C2	118.5 (3)	C10—C9—H9A	120.1
O1ⁱ—C1—C2	112.5 (3)	N2—C10—C9	120.6 (3)
C2ⁱ—C1—C2	113.6 (5)	N2—C10—C5ⁱ	117.2 (3)
O1—C1—H1B	102.8	C9—C10—C5ⁱ	122.1 (3)
C2ⁱ—C1—H1B	103.5	C1—O1—O1ⁱ	51.7 (3)
C2—C1—H1B	103.5	C1—O1—H1A	109.3
N3—C2—C1	113.2 (3)	O1ⁱ—O1—H1A	127.8
N3—C2—H2A	108.9

N2—Ag1—N1—C5	157.0 (2)	C2—N3—C3—C4	−179.3 (3)
N2ⁱ—Ag1—N1—C5	6.1 (2)	N3—C3—C4—C5	−0.2 (4)
N1ⁱ—Ag1—N1—C5	−147.0 (3)	N3—N1—C5—C4	0.3 (4)
N2—Ag1—N1—N3	−41.1 (4)	Ag1—N1—C5—C4	168.6 (2)
N2ⁱ—Ag1—N1—N3	168.0 (3)	N3—N1—C5—C10ⁱ	−179.4 (3)
N1ⁱ—Ag1—N1—N3	14.9 (3)	Ag1—N1—C5—C10ⁱ	−11.1 (4)
N2ⁱ—Ag1—N2—C6	15.6 (3)	C3—C4—C5—N1	−0.1 (4)
N1—Ag1—N2—C6	−124.4 (3)	C3—C4—C5—C10ⁱ	179.6 (3)
N1ⁱ—Ag1—N2—C6	175.0 (3)	C10—N2—C6—C7	−1.5 (6)
N2ⁱ—Ag1—N2—C10	−159.8 (3)	Ag1—N2—C6—C7	−176.8 (3)
N1—Ag1—N2—C10	60.2 (3)	N2—C6—C7—C8	1.5 (6)
N1ⁱ—Ag1—N2—C10	−0.4 (2)	C6—C7—C8—C9	−0.2 (6)
C5—N1—N3—C3	−0.5 (4)	C7—C8—C9—C10	−1.0 (6)
Ag1—N1—N3—C3	−163.1 (3)	C6—N2—C10—C9	0.1 (5)
C5—N1—N3—C2	179.3 (3)	Ag1—N2—C10—C9	175.8 (3)
Ag1—N1—N3—C2	16.7 (5)	C6—N2—C10—C5ⁱ	179.4 (3)
C3—N3—C2—C1	77.9 (5)	Ag1—N2—C10—C5ⁱ	−5.0 (4)
N1—N3—C2—C1	−101.9 (4)	C8—C9—C10—N2	1.1 (5)
O1—C1—C2—N3	−69.5 (5)	C8—C9—C10—C5ⁱ	−178.1 (3)
O1ⁱ—C1—C2—N3	−155.9 (4)	C2ⁱ—C1—O1—O1ⁱ	115.6 (4)
C2ⁱ—C1—C2—N3	65.9 (2)	C2—C1—O1—O1ⁱ	−108.5 (4)
N1—N3—C3—C4	0.5 (4)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, y, −z+5/2.

Hydrogen-bond geometry (Å, °) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱⁱⁱ	0.82	2.21	3.017 (7)	170
C8—H8A···O2^iv	0.93	2.60	3.315 (5)	134

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

Table 1
Selected geometric parameters (Å, °) top

Ag1—N2	2.260 (3)	Ag1—N1	2.391 (3)

N2—Ag1—N2ⁱ	134.08 (15)	N2—Ag1—N1ⁱ	72.03 (10)
N2—Ag1—N1	148.68 (10)	N1—Ag1—N1ⁱ	91.21 (14)

Symmetry codes: (i) −x+1, y, −z+3/2.

Table 2
Hydrogen-bond geometry (Å, °) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱⁱ	0.82	2.21	3.017 (7)	170
C8—H8A···O2ⁱⁱⁱ	0.93	2.60	3.315 (5)	134

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

supplementary materials

{1,3-Bis[3-(2-pyridyl)-1H-pyrazol-1-yl]propan-2-ol}silver(I) perchlorate

C.-S. Liu and X.-S. Shi

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Unlabelled atoms in the cation are related to labelled atoms by (1 − x, y, 3/2 − z). Unlabelled atoms in the anion are related to labelled atoms by (1 − x, y, 5/2 − z). For clarity only one disorder component is shown.
	Fig. 2. Part of the crystal packing in the title compound, showing a C—H···O hydrogen-bonded (dashed) chain. The atom labelled with the suffix B is generated by the symmetry operation (1/2 − x, y − 1/2, 3/2 − z). For clarity only one disorder component is shown.