4-(4-Pyrid­yl)pyridinium penta­aqua(pyridazine-4,5-dicarboxyl­ato)praseodymate(III)

Zhang, Z.-Q.; Xue, X.-D.; Yao, B.-X.; Ji, X.; Jiang, H.-J.

doi:10.1107/S1600536810033477

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1288

doi:10.1107/S1600536810033477

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4-(4-Pyridyl)pyridinium pentaaqua(pyridazine-4,5-dicarboxylato)praseodymate(III)

Zhen-Qin Zhang,^a Xiao-Dong Xue,^b Bi-Xia Yao,^a Xing Ji ^a and Hui-Jun Jiang ^a ^*

^aSchool of Pharmacy, Nanjing Medical University, Nanjing, People's Republic of China, and ^bThe Scientific and Technological Information Research Department of Jiangsu, Nanjing, People's Republic of China
^*Correspondence e-mail: huijun_jiang@263.net

(Received 9 August 2010; accepted 19 August 2010; online 25 September 2010)

In the title complex, (C₁₀H₉N₂)[Pr(C₆H₂N₂O₄)₂(H₂O)₅], the Pr atom is nine-coordinated by nine O atoms from two pyridazine-4,5-dicarboxylate anions and five water molecules. It is noteworthy that there is a protonated bipyridine molecule in the structure. Intermolecular O—H⋯O, O—H⋯N and N—H⋯N hydrogen bonds are present, resulting in a three-dimensional network.

Related literature

For general background to metal carboxylate coordination compounds, see: Escuer et al. (1997 ). For pyridazine dicarboxylic metal complexes, see: Gryz et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

(C₁₀H₉N₂)[Pr(C₆H₂N₂O₄)₂(H₂O)₅]
M_r = 720.37
Orthorhombic, P 2₁ 2₁ 2
a = 11.2726 (17) Å
b = 12.0023 (18) Å
c = 9.5266 (14) Å
V = 1288.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.97 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.22 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.454, T_max = 0.649
12497 measured reflections
2358 independent reflections
2280 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.052
S = 1.09
2358 reflections
216 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.25 e Å⁻³
Δρ_min = −0.43 e Å⁻³
Absolute structure: Flack (1983 ), 981 Friedel pairs
Flack parameter: −0.014 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O4ⁱ	0.82 (4)	1.85 (4)	2.662 (3)	171 (5)
O6—H6B⋯O3ⁱ	0.82 (5)	1.93 (5)	2.749 (4)	178 (7)
O6—H6A⋯N1ⁱⁱ	0.82 (7)	2.07 (6)	2.881 (5)	172 (8)
O5—H5B⋯N2ⁱⁱⁱ	0.82 (3)	2.14 (4)	2.953 (4)	172 (6)
O5—H5A⋯O3	0.82 (4)	2.00 (4)	2.809 (4)	173 (5)
N3—H3A⋯N4^iv	0.91 (1)	1.65 (1)	2.555 (6)	180
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+2]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+1]$ ; (iii) x, y, z+1; (iv) x, y, z-1.

Data collection: CrystalClear (Rigaku, 1999 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033477/bq2230sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810033477/bq2230Isup2.hkl

checkCIF report

Comment top

In the past few years, investigations on metal carboxylate coordination compounds have become of increasing interest (Escuer et al.(1997); Gryz et al. 2006). As part of our ongoing investigations in this field we report here the crystal structure of the title compound. In the crystal structure of (I) the Pr atom is coordinated by five oxygen atoms of five water molecules and four oxygen atoms from two pyridazine-4,5-dicarboxylate anions within a distorted orthorhombic coordination symmetry (Figure 1). The bond lengths (Allen et al., 1987) and angles are within normal ranges. The crystal structure contain additional bipyridine molecule that is linked to the complexes via O—H···N hydrogen bonding (Figure 2). The complexes are additionally connected by intermolecular O—H···O hydrogen bonding between the carboxyl O atoms and the water H atoms (Table 1 and Figure 2).

Related literature top

For general background to metal carboxylate coordination compounds, see: Escuer et al. (1997). For pyridazine dicarboxylic complexes, see: Gryz et al. (2006).

For related literature, see: Allen et al. (1987).

Experimental top

A mixture of pyridazine-4,5-dicarboxylic acid (84 mg, 0.5 mmol), NaOH (40 mg, 1.0 mmol), PrCl₃.6H₂O (177.7 mg, 0.5 mmol) and 4,4'-bipyridine (78 mg, 0.5 mmol) in warer (10 ml) was placed in a Teflon-lined stainless steel Parr bomb. The bomb was heated at 433 K for 4 d. The bomb was cooled naturally to room temperature, and yellow block crystals of (I) were obtained after several days. Analysis calculated for C₂₂H₂₃N₆O₁₃Pr: C 36.68, H 3.22, N 11.67%; found: C 36.64, H 3.30, N 11.62%.

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalStructure (Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure (Rigaku, 1999).

Figures top

	Fig. 1. Crystal structure and atom numbering of the title compound, shown with 20% probability displacement ellipsoids. Symmetry code for atoms labelled with A: 1-x, 1-y, z.
	Fig. 2. The packing digram of the title compound.

4-(4-Pyridyl)pyridinium pentaaqua(pyridazine-4,5-dicarboxylato)praseodymate(III) top

Crystal data top

(C₁₀H₉N₂)[Pr(C₆H₂N₂O₄)₂(H₂O)₅]	F(000) = 720
M_r = 720.37	D_x = 1.856 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2 2ab	Cell parameters from 5385 reflections
a = 11.2726 (17) Å	θ = 3.3–25.3°
b = 12.0023 (18) Å	µ = 1.97 mm⁻¹
c = 9.5266 (14) Å	T = 293 K
V = 1288.9 (3) Å³	Block, yellow
Z = 2	0.40 × 0.30 × 0.22 mm

Data collection top

Rigaku Mercury diffractometer	2358 independent reflections
Radiation source: fine-focus sealed tube	2280 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.3°, θ_min = 3.3°
ω scans	h = −13→13
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −14→13
T_min = 0.454, T_max = 0.649	l = −11→10
12497 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.052	w = 1/[σ²(F_o²) + (0.0271P)² + 0.6051P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
2358 reflections	Δρ_max = 1.25 e Å⁻³
216 parameters	Δρ_min = −0.43 e Å⁻³
6 restraints	Absolute structure: Flack (1983), 981 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.014 (18)

Crystal data top

(C₁₀H₉N₂)[Pr(C₆H₂N₂O₄)₂(H₂O)₅]	V = 1288.9 (3) Å³
M_r = 720.37	Z = 2
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 11.2726 (17) Å	µ = 1.97 mm⁻¹
b = 12.0023 (18) Å	T = 293 K
c = 9.5266 (14) Å	0.40 × 0.30 × 0.22 mm

Data collection top

Rigaku Mercury diffractometer	2358 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2280 reflections with I > 2σ(I)
T_min = 0.454, T_max = 0.649	R_int = 0.030
12497 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.052	Δρ_max = 1.25 e Å⁻³
S = 1.09	Δρ_min = −0.43 e Å⁻³
2358 reflections	Absolute structure: Flack (1983), 981 Friedel pairs
216 parameters	Absolute structure parameter: −0.014 (18)
6 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Pr1	0.5000	0.5000	0.89791 (2)	0.01750 (8)
O1	0.4932 (4)	0.32723 (19)	0.7261 (2)	0.0323 (6)
O2	0.6434 (3)	0.4430 (2)	0.7086 (3)	0.0351 (7)
O3	0.7353 (3)	0.2019 (3)	0.8030 (3)	0.0471 (8)
O4	0.8272 (3)	0.0738 (3)	0.6792 (3)	0.0552 (10)
O5	0.6242 (4)	0.3454 (3)	0.9953 (3)	0.0490 (10)
H5A	0.651 (4)	0.303 (3)	0.936 (4)	0.049 (15)*
H5B	0.629 (5)	0.322 (5)	1.076 (2)	0.070 (19)*
O6	0.6757 (3)	0.6135 (3)	0.9524 (3)	0.0405 (8)
H6A	0.708 (7)	0.643 (7)	0.885 (5)	0.14 (3)*
H6B	0.701 (6)	0.640 (5)	1.026 (4)	0.09 (2)*
O7	0.5000	0.5000	1.1547 (3)	0.0276 (7)
H7A	0.558 (3)	0.522 (4)	1.198 (4)	0.059 (16)*
N1	0.7159 (3)	0.1957 (3)	0.3012 (3)	0.0281 (7)
N2	0.6400 (3)	0.2828 (3)	0.2946 (3)	0.0298 (7)
N3	1.0000	0.5000	0.3965 (5)	0.0465 (11)
H3A	1.0000	0.5000	0.3016 (12)	0.042 (14)*
N4	1.0000	0.5000	1.1284 (5)	0.0510 (12)
C1	0.6374 (3)	0.2932 (3)	0.5471 (4)	0.0216 (8)
C2	0.7136 (3)	0.2042 (3)	0.5549 (4)	0.0207 (8)
C3	0.7492 (3)	0.1586 (3)	0.4262 (4)	0.0258 (8)
H3B	0.8002	0.0977	0.4287	0.031*
C4	0.6030 (4)	0.3280 (3)	0.4125 (4)	0.0291 (9)
H4	0.5502	0.3873	0.4062	0.035*
C5	0.5883 (3)	0.3579 (3)	0.6721 (4)	0.0233 (8)
C6	0.7630 (3)	0.1562 (3)	0.6912 (4)	0.0257 (8)
C7	0.9297 (4)	0.4314 (4)	0.4686 (6)	0.0479 (12)
H7B	0.8806	0.3830	0.4193	0.058*
C8	0.9268 (4)	0.4292 (4)	0.6114 (5)	0.0458 (11)
H8	0.8763	0.3807	0.6584	0.055*
C9	1.0000	0.5000	0.6851 (6)	0.0367 (11)
C10	0.9720 (8)	0.4083 (5)	1.0594 (6)	0.081 (3)
H10	0.9534	0.3437	1.1088	0.097*
C11	0.9700 (7)	0.4073 (5)	0.9169 (5)	0.073 (2)
H11	0.9480	0.3427	0.8698	0.087*
C12	1.0000	0.5000	0.8421 (5)	0.0373 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pr1	0.02098 (13)	0.01818 (12)	0.01336 (12)	0.0006 (2)	0.000	0.000
O1	0.0269 (14)	0.0402 (13)	0.0298 (12)	−0.001 (2)	0.010 (2)	−0.0098 (10)
O2	0.0478 (18)	0.0265 (13)	0.0310 (16)	−0.0096 (13)	0.0152 (13)	−0.0092 (12)
O3	0.072 (2)	0.0531 (19)	0.0159 (14)	0.0347 (16)	−0.0059 (15)	−0.0025 (14)
O4	0.077 (2)	0.059 (2)	0.0293 (17)	0.0450 (19)	−0.0121 (17)	−0.0020 (16)
O5	0.079 (3)	0.049 (2)	0.0189 (18)	0.0398 (19)	−0.0008 (17)	−0.0046 (16)
O6	0.042 (2)	0.058 (2)	0.0207 (16)	−0.0254 (17)	−0.0008 (15)	0.0003 (16)
O7	0.0284 (18)	0.0378 (18)	0.0167 (15)	−0.003 (4)	0.000	0.000
N1	0.0346 (19)	0.0321 (18)	0.0176 (16)	0.0084 (14)	0.0010 (14)	−0.0026 (14)
N2	0.042 (2)	0.0306 (17)	0.0165 (16)	0.0100 (16)	−0.0005 (15)	−0.0023 (14)
N3	0.053 (3)	0.049 (3)	0.038 (3)	0.007 (6)	0.000	0.000
N4	0.061 (3)	0.051 (3)	0.041 (3)	0.015 (8)	0.000	0.000
C1	0.026 (2)	0.0207 (19)	0.0184 (18)	−0.0002 (15)	−0.0018 (15)	−0.0006 (15)
C2	0.0216 (19)	0.0222 (19)	0.0183 (18)	−0.0001 (15)	−0.0010 (14)	−0.0017 (15)
C3	0.029 (2)	0.027 (2)	0.022 (2)	0.0063 (17)	0.0017 (15)	−0.0021 (16)
C4	0.040 (2)	0.025 (2)	0.022 (2)	0.0088 (17)	0.0001 (17)	−0.0015 (16)
C5	0.027 (2)	0.026 (2)	0.0165 (18)	0.0067 (16)	−0.0017 (15)	0.0037 (16)
C6	0.032 (2)	0.026 (2)	0.0188 (19)	0.0056 (17)	−0.0008 (16)	0.0028 (17)
C7	0.042 (3)	0.043 (3)	0.058 (3)	−0.009 (2)	−0.005 (2)	0.002 (2)
C8	0.045 (3)	0.048 (3)	0.044 (3)	−0.011 (2)	0.000 (2)	−0.003 (2)
C9	0.032 (3)	0.031 (2)	0.048 (3)	−0.008 (7)	0.000	0.000
C10	0.143 (9)	0.050 (3)	0.048 (3)	−0.022 (4)	0.007 (4)	0.003 (2)
C11	0.118 (8)	0.056 (3)	0.044 (3)	−0.028 (4)	0.001 (3)	−0.001 (2)
C12	0.034 (3)	0.033 (3)	0.045 (3)	0.001 (7)	0.000	0.000

Geometric parameters (Å, º) top

Pr1—O7	2.446 (3)	N3—C7ⁱⁱ	1.333 (5)
Pr1—O6	2.459 (3)	N3—C7	1.333 (5)
Pr1—O6ⁱ	2.459 (3)	N3—H3A	0.905 (10)
Pr1—O5	2.503 (3)	N4—C10	1.321 (6)
Pr1—O5ⁱ	2.503 (3)	N4—C10ⁱⁱ	1.321 (6)
Pr1—O2ⁱ	2.516 (3)	C1—C2	1.373 (5)
Pr1—O2	2.516 (3)	C1—C4	1.403 (5)
Pr1—O1	2.643 (2)	C1—C5	1.525 (5)
Pr1—O1ⁱ	2.643 (2)	C2—C3	1.401 (5)
Pr1—C5	2.921 (4)	C2—C6	1.526 (5)
Pr1—C5ⁱ	2.921 (4)	C3—H3B	0.9300
O1—C5	1.245 (5)	C4—H4	0.9300
O2—C5	1.246 (4)	C7—C8	1.361 (7)
O3—C6	1.238 (5)	C7—H7B	0.9300
O4—C6	1.231 (4)	C8—C9	1.377 (5)
O5—H5A	0.82 (4)	C8—H8	0.9300
O5—H5B	0.82 (3)	C9—C8ⁱⁱ	1.377 (5)
O6—H6A	0.82 (7)	C9—C12	1.496 (7)
O6—H6B	0.82 (5)	C10—C11	1.357 (7)
O7—H7A	0.82 (4)	C10—H10	0.9300
N1—C3	1.326 (5)	C11—C12	1.363 (6)
N1—N2	1.354 (4)	C11—H11	0.9300
N2—C4	1.315 (5)	C12—C11ⁱⁱ	1.363 (6)

O7—Pr1—O6	77.81 (8)	C5—O1—Pr1	90.0 (2)
O7—Pr1—O6ⁱ	77.81 (8)	C5—O2—Pr1	95.9 (2)
O6—Pr1—O6ⁱ	155.63 (15)	Pr1—O5—H5A	115 (4)
O7—Pr1—O5	68.24 (7)	Pr1—O5—H5B	130 (4)
O6—Pr1—O5	83.23 (14)	H5A—O5—H5B	114 (5)
O6ⁱ—Pr1—O5	87.78 (16)	Pr1—O6—H6A	115 (6)
O7—Pr1—O5ⁱ	68.24 (7)	Pr1—O6—H6B	132 (5)
O6—Pr1—O5ⁱ	87.78 (16)	H6A—O6—H6B	111 (7)
O6ⁱ—Pr1—O5ⁱ	83.23 (14)	Pr1—O7—H7A	120 (3)
O5—Pr1—O5ⁱ	136.47 (14)	C3—N1—N2	118.7 (3)
O7—Pr1—O2ⁱ	135.77 (7)	C4—N2—N1	118.6 (3)
O6—Pr1—O2ⁱ	121.20 (10)	C7ⁱⁱ—N3—C7	118.0 (6)
O6ⁱ—Pr1—O2ⁱ	77.56 (11)	C7ⁱⁱ—N3—H3A	121.0 (3)
O5—Pr1—O2ⁱ	145.74 (10)	C7—N3—H3A	121.0 (3)
O5ⁱ—Pr1—O2ⁱ	72.84 (10)	C10—N4—C10ⁱⁱ	120.3 (6)
O7—Pr1—O2	135.77 (7)	C2—C1—C4	117.0 (3)
O6—Pr1—O2	77.56 (11)	C2—C1—C5	125.5 (3)
O6ⁱ—Pr1—O2	121.20 (10)	C4—C1—C5	117.5 (3)
O5—Pr1—O2	72.84 (10)	C1—C2—C3	115.8 (3)
O5ⁱ—Pr1—O2	145.74 (10)	C1—C2—C6	124.7 (3)
O2ⁱ—Pr1—O2	88.45 (14)	C3—C2—C6	119.5 (3)
O7—Pr1—O1	128.27 (5)	N1—C3—C2	125.0 (3)
O6—Pr1—O1	126.08 (14)	N1—C3—H3B	117.5
O6ⁱ—Pr1—O1	70.89 (12)	C2—C3—H3B	117.5
O5—Pr1—O1	70.39 (11)	N2—C4—C1	124.8 (3)
O5ⁱ—Pr1—O1	142.66 (14)	N2—C4—H4	117.6
O2ⁱ—Pr1—O1	75.56 (10)	C1—C4—H4	117.6
O2—Pr1—O1	50.33 (10)	O2—C5—O1	123.8 (3)
O7—Pr1—O1ⁱ	128.27 (5)	O2—C5—C1	117.1 (3)
O6—Pr1—O1ⁱ	70.89 (12)	O1—C5—C1	119.0 (3)
O6ⁱ—Pr1—O1ⁱ	126.08 (14)	O2—C5—Pr1	58.96 (19)
O5—Pr1—O1ⁱ	142.66 (14)	O1—C5—Pr1	64.81 (18)
O5ⁱ—Pr1—O1ⁱ	70.39 (11)	C1—C5—Pr1	174.8 (3)
O2ⁱ—Pr1—O1ⁱ	50.33 (10)	O4—C6—O3	125.7 (4)
O2—Pr1—O1ⁱ	75.56 (10)	O4—C6—C2	116.0 (3)
O1—Pr1—O1ⁱ	103.45 (10)	O3—C6—C2	118.2 (3)
O7—Pr1—C5	137.44 (7)	N3—C7—C8	122.8 (5)
O6—Pr1—C5	101.81 (12)	N3—C7—H7B	118.6
O6ⁱ—Pr1—C5	96.11 (11)	C8—C7—H7B	118.6
O5—Pr1—C5	69.47 (9)	C7—C8—C9	118.9 (5)
O5ⁱ—Pr1—C5	153.75 (10)	C7—C8—H8	120.5
O2ⁱ—Pr1—C5	81.37 (9)	C9—C8—H8	120.5
O2—Pr1—C5	25.10 (9)	C8—C9—C8ⁱⁱ	118.7 (6)
O1—Pr1—C5	25.24 (11)	C8—C9—C12	120.7 (3)
O1ⁱ—Pr1—C5	89.54 (9)	C8ⁱⁱ—C9—C12	120.7 (3)
O7—Pr1—C5ⁱ	137.44 (7)	N4—C10—C11	120.5 (6)
O6—Pr1—C5ⁱ	96.11 (11)	N4—C10—H10	119.7
O6ⁱ—Pr1—C5ⁱ	101.81 (12)	C11—C10—H10	119.7
O5—Pr1—C5ⁱ	153.75 (10)	C10—C11—C12	120.8 (5)
O5ⁱ—Pr1—C5ⁱ	69.47 (9)	C10—C11—H11	119.6
O2ⁱ—Pr1—C5ⁱ	25.10 (9)	C12—C11—H11	119.6
O2—Pr1—C5ⁱ	81.37 (9)	C11—C12—C11ⁱⁱ	117.0 (6)
O1—Pr1—C5ⁱ	89.54 (9)	C11—C12—C9	121.5 (3)
O1ⁱ—Pr1—C5ⁱ	25.24 (11)	C11ⁱⁱ—C12—C9	121.5 (3)
C5—Pr1—C5ⁱ	85.11 (13)

O7—Pr1—O1—C5	−121.79 (19)	C4—C1—C5—O1	90.2 (4)
O6—Pr1—O1—C5	−17.8 (3)	O7—Pr1—C5—O2	−99.9 (2)
O6ⁱ—Pr1—O1—C5	−177.9 (3)	O6—Pr1—C5—O2	−15.2 (2)
O5—Pr1—O1—C5	−83.3 (2)	O6ⁱ—Pr1—C5—O2	−178.6 (2)
O5ⁱ—Pr1—O1—C5	133.4 (3)	O5—Pr1—C5—O2	−93.2 (3)
O2ⁱ—Pr1—O1—C5	100.5 (2)	O5ⁱ—Pr1—C5—O2	94.4 (4)
O2—Pr1—O1—C5	0.3 (2)	O2ⁱ—Pr1—C5—O2	105.1 (2)
O1ⁱ—Pr1—O1—C5	58.21 (19)	O1—Pr1—C5—O2	179.4 (4)
C5ⁱ—Pr1—O1—C5	79.5 (3)	O1ⁱ—Pr1—C5—O2	55.2 (2)
O7—Pr1—O2—C5	107.2 (2)	C5ⁱ—Pr1—C5—O2	80.1 (2)
O6—Pr1—O2—C5	164.8 (2)	O7—Pr1—C5—O1	80.6 (2)
O6ⁱ—Pr1—O2—C5	1.7 (3)	O6—Pr1—C5—O1	165.4 (2)
O5—Pr1—O2—C5	78.1 (2)	O6ⁱ—Pr1—C5—O1	2.0 (2)
O5ⁱ—Pr1—O2—C5	−128.4 (3)	O5—Pr1—C5—O1	87.3 (2)
O2ⁱ—Pr1—O2—C5	−72.8 (2)	O5ⁱ—Pr1—C5—O1	−85.1 (4)
O1—Pr1—O2—C5	−0.3 (2)	O2ⁱ—Pr1—C5—O1	−74.4 (2)
O1ⁱ—Pr1—O2—C5	−122.0 (2)	O2—Pr1—C5—O1	−179.4 (4)
C5ⁱ—Pr1—O2—C5	−97.0 (2)	O1ⁱ—Pr1—C5—O1	−124.24 (19)
C3—N1—N2—C4	0.6 (5)	C5ⁱ—Pr1—C5—O1	−99.4 (2)
C4—C1—C2—C3	0.5 (5)	C1—C2—C6—O4	177.7 (4)
C5—C1—C2—C3	−178.8 (3)	C3—C2—C6—O4	−4.3 (6)
C4—C1—C2—C6	178.6 (4)	C1—C2—C6—O3	−1.9 (6)
C5—C1—C2—C6	−0.8 (6)	C3—C2—C6—O3	176.0 (4)
N2—N1—C3—C2	−1.3 (6)	C7ⁱⁱ—N3—C7—C8	0.3 (4)
C1—C2—C3—N1	0.7 (6)	N3—C7—C8—C9	−0.5 (7)
C6—C2—C3—N1	−177.5 (4)	C7—C8—C9—C8ⁱⁱ	0.2 (4)
N1—N2—C4—C1	0.7 (6)	C7—C8—C9—C12	−179.8 (4)
C2—C1—C4—N2	−1.2 (6)	C10ⁱⁱ—N4—C10—C11	−0.9 (6)
C5—C1—C4—N2	178.2 (4)	N4—C10—C11—C12	1.8 (13)
Pr1—O2—C5—O1	0.6 (4)	C10—C11—C12—C11ⁱⁱ	−0.9 (6)
Pr1—O2—C5—C1	176.2 (3)	C10—C11—C12—C9	179.1 (6)
Pr1—O1—C5—O2	−0.6 (4)	C8—C9—C12—C11	27.2 (4)
Pr1—O1—C5—C1	−176.1 (3)	C8ⁱⁱ—C9—C12—C11	−152.8 (4)
C2—C1—C5—O2	93.8 (5)	C8—C9—C12—C11ⁱⁱ	−152.8 (4)
C4—C1—C5—O2	−85.6 (4)	C8ⁱⁱ—C9—C12—C11ⁱⁱ	27.2 (4)
C2—C1—C5—O1	−90.4 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱⁱⁱ	0.82 (4)	1.85 (4)	2.662 (3)	171 (5)
O6—H6B···O3ⁱⁱⁱ	0.82 (5)	1.93 (5)	2.749 (4)	178 (7)
O6—H6A···N1^iv	0.82 (7)	2.07 (6)	2.881 (5)	172 (8)
O5—H5B···N2^v	0.82 (3)	2.14 (4)	2.953 (4)	172 (6)
O5—H5A···O3	0.82 (4)	2.00 (4)	2.809 (4)	173 (5)
N3—H3A···N4^vi	0.91 (1)	1.65 (1)	2.555 (6)	180

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

Experimental details

Crystal data
Chemical formula	(C₁₀H₉N₂)[Pr(C₆H₂N₂O₄)₂(H₂O)₅]
M_r	720.37
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	293
a, b, c (Å)	11.2726 (17), 12.0023 (18), 9.5266 (14)
V (Å³)	1288.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.97
Crystal size (mm)	0.40 × 0.30 × 0.22

Data collection
Diffractometer	Rigaku Mercury diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.454, 0.649
No. of measured, independent and observed [I > 2σ(I)] reflections	12497, 2358, 2280
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.052, 1.09
No. of reflections	2358
No. of parameters	216
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.25, −0.43
Absolute structure	Flack (1983), 981 Friedel pairs
Absolute structure parameter	−0.014 (18)

Computer programs: CrystalClear (Rigaku, 1999), CrystalStructure (Rigaku, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱ	0.82 (4)	1.85 (4)	2.662 (3)	171 (5)
O6—H6B···O3ⁱ	0.82 (5)	1.93 (5)	2.749 (4)	178 (7)
O6—H6A···N1ⁱⁱ	0.82 (7)	2.07 (6)	2.881 (5)	172 (8)
O5—H5B···N2ⁱⁱⁱ	0.82 (3)	2.14 (4)	2.953 (4)	172 (6)
O5—H5A···O3	0.82 (4)	2.00 (4)	2.809 (4)	173 (5)
N3—H3A···N4^iv	0.91 (1)	1.65 (1)	2.555 (6)	180

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

Acknowledgements

Financial support from the Science Foundation of Nangjing Medical University (Reference: 8651) is gratefully acknowledged.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Burnett, M. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Escuer, A., Vicente, R., Mernari, B., Gueddi, A. & Pierrot, M. (1997). Inorg. Chem. 36, 2511–2516. CSD CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gryz, M., Starosta, W. & Leciejewicz, J. (2006). Acta Cryst. E62, m3470–m3472. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1999). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page m1288

doi:10.1107/S1600536810033477

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-(4-Pyrid­yl)pyridinium penta­aqua(pyridazine-4,5-di­carboxyl­ato)praseodymate(III)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

4-(4-Pyridyl)pyridinium pentaaqua(pyridazine-4,5-dicarboxylato)praseodymate(III)