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

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—H...O and weak C—H...O hydrogen-bonding inter­actions link adjacent mononuclear Ag^I units and perchlorate ions, forming a chain.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.038
• wR factor = 0.088
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        Ag1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              Cl O4

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C19 H18 Ag1 Cl1 N6 O5
            Atom count from _chemical_formula_moiety:
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

In recent years, 3-(2-pyridyl)pyrazole-based ligands have found a wide range of application in the area of coordination chemistry, because they can act as bridging or chelate ligands and exhibit a series of intriguing structures and potential applications as functional materials (Ruben et al., 2004; Steel et al., 2005). Nowadays, much attention has been focused on the synthetic approach and the structural control of coordination architectures (Bell et al., 2003; Paul et al., 2004). We report here the structure of a mononuclear silver complex, {1,3-bis[3-(2-pyridyl)pyrazole]propan-2-ol}silver(I) perchlorate.

In the title compound, the cation and anion both lie on crystallographic twofold rotation axes. In the cation, the twofold axis passes through atoms Ag1 and C1, and as a result the hydroxyl group is disordered. The Ag^I center is four-coordinated by four N donors from a 1,3-bis[3-(2-pyridyl)pyrazole]propan-2-ol ligand (Table 1). The coordination geometry around the Ag^I center can be described as a distorted tetrahedron (Fig. 1).

The Ag^I mononuclear units are linked to the perchlorate ions through O—H···O hydrogen bonds (Table 2) and weak C—H···O interactions (Desiraju et al., 1999; Barberà et al., 2002) leading to the formation of a one-dimensional chain (Fig. 2).

Related literature

For general background, see: Bell et al. (2003); Paul et al. (2004); Ruben et al. (2004); Steel (2005); Zhang et al. (2005). For hydrogen-bonding, see: Barberà et al. (2002); Desiraju & Steiner (1999).

S2. Experimental

The ligand 1,3-bis[3-(2-pyridyl)-1H-pyrazole]propan-2-ol (L) was synthesized according to the method reported in the literature (Zhang et al., 2005). A solution of AgClO₄ (22 mg, 0.1 mmol) in ethanol (10 ml) was added to a solution of L (35 mg, 0.1 mmol) in acetonitrile (20 ml) in a 50 ml beaker and the resulted solution was kept at room temperature in the dark. Single crystals of (I) suitable for X-ray analysis were obtained after 10 d (yield: 45%). Analysis calculated for (C₁₉H₁₈AgClN₆O₅): C 41.18, H 3.25, N 15.17%; found: C 41.36, H 3.64, N 14.91%.

S3. Refinement

H atoms were included in calculated positions and treated in the subsequent refinement as riding atoms, with C—H = 0.93 (aromatic) or 0.97 Å (methylene) and O—H = 0.82 Å, and with U_iso(H) = 1.2U_eq(C) and 1.5U_eq(O).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures

	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.

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

Crystal data

[Ag(C19H18N6O)]ClO4	F(000) = 1112
Mr = 553.71	Dx = 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) Å^3	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection

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

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0393P)^2 + 1.8827P] where P = (Fo^2 + 2Fc^2)/3
2135 reflections	(Δ/σ)max = 0.001
151 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.46 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	0.510403 (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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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, º)

Ag1—N2	2.260 (3)	C2—H2A	0.97
Ag1—N2^i	2.260 (3)	C2—H2B	0.97
Ag1—N1	2.391 (3)	C3—C4	1.346 (5)
Ag1—N1^i	2.391 (3)	C3—H3A	0.93
Cl1—O3	1.395 (3)	C4—C5	1.387 (5)
Cl1—O3^ii	1.395 (3)	C4—H4A	0.93
Cl1—O2^ii	1.397 (3)	C5—C10^i	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—O1^i	1.257 (6)	C10—C5^i	1.460 (5)
C1—C2^i	1.519 (5)	O1—O1^i	1.557 (10)
C1—C2	1.519 (5)	O1—H1A	0.82
C1—H1B	0.96
N2—Ag1—N2^i	134.08 (15)	C1—C2—H2A	108.9
N2—Ag1—N1	148.68 (10)	N3—C2—H2B	108.9
N2^i—Ag1—N1	72.03 (10)	C1—C2—H2B	108.9
N2—Ag1—N1^i	72.03 (10)	H2A—C2—H2B	107.7
N2^i—Ag1—N1^i	148.68 (10)	N3—C3—C4	108.2 (3)
N1—Ag1—N1^i	91.21 (14)	N3—C3—H3A	125.9
O3—Cl1—O3^ii	109.6 (4)	C4—C3—H3A	125.9
O3—Cl1—O2^ii	106.87 (19)	C3—C4—C5	105.1 (4)
O3^ii—Cl1—O2^ii	111.4 (2)	C3—C4—H4A	127.5
O3—Cl1—O2	111.4 (2)	C5—C4—H4A	127.5
O3^ii—Cl1—O2	106.87 (19)	N1—C5—C4	110.7 (3)
O2^ii—Cl1—O2	110.8 (3)	N1—C5—C10^i	119.5 (3)
C5—N1—N3	105.1 (3)	C4—C5—C10^i	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—O1^i	76.5 (6)	C9—C8—H8A	120.2
O1—C1—C2^i	112.5 (3)	C8—C9—C10	119.8 (4)
O1^i—C1—C2^i	118.5 (3)	C8—C9—H9A	120.1
O1—C1—C2	118.5 (3)	C10—C9—H9A	120.1
O1^i—C1—C2	112.5 (3)	N2—C10—C9	120.6 (3)
C2^i—C1—C2	113.6 (5)	N2—C10—C5^i	117.2 (3)
O1—C1—H1B	102.8	C9—C10—C5^i	122.1 (3)
C2^i—C1—H1B	103.5	C1—O1—O1^i	51.7 (3)
C2—C1—H1B	103.5	C1—O1—H1A	109.3
N3—C2—C1	113.2 (3)	O1^i—O1—H1A	127.8
N3—C2—H2A	108.9
N2—Ag1—N1—C5	157.0 (2)	C2—N3—C3—C4	−179.3 (3)
N2^i—Ag1—N1—C5	6.1 (2)	N3—C3—C4—C5	−0.2 (4)
N1^i—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)
N2^i—Ag1—N1—N3	168.0 (3)	N3—N1—C5—C10^i	−179.4 (3)
N1^i—Ag1—N1—N3	14.9 (3)	Ag1—N1—C5—C10^i	−11.1 (4)
N2^i—Ag1—N2—C6	15.6 (3)	C3—C4—C5—N1	−0.1 (4)
N1—Ag1—N2—C6	−124.4 (3)	C3—C4—C5—C10^i	179.6 (3)
N1^i—Ag1—N2—C6	175.0 (3)	C10—N2—C6—C7	−1.5 (6)
N2^i—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)
N1^i—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—C5^i	179.4 (3)
C3—N3—C2—C1	77.9 (5)	Ag1—N2—C10—C5^i	−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—C5^i	−178.1 (3)
O1^i—C1—C2—N3	−155.9 (4)	C2^i—C1—O1—O1^i	115.6 (4)
C2^i—C1—C2—N3	65.9 (2)	C2—C1—O1—O1^i	−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, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3^iii	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.