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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages m1221-m1222

catena-Poly[[[bis­­(3-amino­pyrazine-2-carboxyl­ato)tri­aqua­praseodymium(III)]-μ-3-amino­pyrazine-2-carboxyl­ato-[(3-amino­pyrazine-2-carboxyl­ato)di­aqua­formatopraseodymium(III)]-μ-3-amino­pyrazine-2-carboxyl­ato] hexa­hydrate]

aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 31 July 2011; accepted 3 August 2011; online 11 August 2011)

The asymmetric unit of the polymeric title compound, {[Pr2(C5H4N3O2)5(CHO2)(H2O)5]·6H2O}n, has two independent PrIII atoms; one is coordinated by two water mol­ecules and the other by three water mol­ecules. The first is N,O-chelated by three 3-amino­pyrazine-2-carboxyl­ate ions, whereas the second is chelated by two carboxyl­ate ions; both exist in a monocapped square-anti­prismatic geometry. The polymeric chains that run along the a axis inter­act with the lattice water mol­ecules, generating a three-dimensional hydrogen-bonded network. The formate ion is disordered over two positions with respect to the non-coordinated atoms in a 1:1 ratio.

Related literature

3-Amino­pyrazine­carb­oxy­lic acid decomposition with subsequent oxalate formation has been documented in a related lanthanum system; see: Gao & Ng (2011[Gao, S. & Ng, S. W. (2011). Acta Cryst. E67, m1301.]).

[Scheme 1]

Experimental

Crystal data
  • [Pr2(C5H4N3O2)5(CHO2)(H2O)5]·6H2O

  • Mr = 1215.58

  • Triclinic, [P \overline 1]

  • a = 9.7213 (3) Å

  • b = 14.2113 (6) Å

  • c = 17.6228 (6) Å

  • α = 68.801 (1)°

  • β = 76.291 (1)°

  • γ = 79.349 (1)°

  • V = 2191.97 (14) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.30 mm−1

  • T = 293 K

  • 0.14 × 0.12 × 0.07 mm

Data collection
  • Rigaku R-AXIS RAPID IP diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.739, Tmax = 0.856

  • 21572 measured reflections

  • 9906 independent reflections

  • 8214 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.088

  • S = 1.06

  • 9906 reflections

  • 679 parameters

  • 69 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.34 e Å−3

  • Δρmin = −1.03 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1w—H11⋯O7i 0.84 (1) 2.34 (2) 3.115 (4) 155 (5)
O1w—H12⋯O2ii 0.84 (1) 1.80 (1) 2.635 (5) 179 (5)
O2w—H21⋯O6w 0.84 (1) 2.02 (2) 2.839 (5) 164 (5)
O2w—H22⋯O6 0.84 (1) 1.99 (3) 2.771 (4) 153 (5)
O3w—H31⋯O7i 0.84 (1) 2.05 (2) 2.829 (4) 155 (4)
O3w—H32⋯O7w 0.84 (1) 1.89 (1) 2.721 (5) 174 (4)
O4w—H41⋯O8wiii 0.84 (1) 1.93 (1) 2.769 (5) 176 (6)
O4w—H42⋯O12iv 0.84 (1) 2.07 (5) 2.649 (7) 126 (5)
O5w—H51⋯O6wiii 0.84 (1) 1.97 (1) 2.803 (5) 174 (5)
O5w—H52⋯O11wv 0.84 (1) 1.84 (1) 2.673 (5) 173 (6)
O6w—H61⋯N11vi 0.84 (1) 2.02 (2) 2.842 (5) 169 (6)
O6w—H62⋯O10 0.84 (1) 2.02 (2) 2.833 (5) 164 (6)
O7w—H71⋯O9 0.84 (1) 2.41 (4) 3.135 (6) 146 (7)
O7w—H72⋯O12′ 0.84 (1) 1.99 (5) 2.688 (10) 141 (8)
O8w—H81⋯O7w 0.84 (1) 2.01 (3) 2.782 (6) 154 (7)
O8w—H82⋯N2vii 0.84 (1) 2.03 (2) 2.861 (6) 168 (7)
O9w—H91⋯O10wviii 0.84 (1) 2.40 (6) 3.074 (8) 138 (7)
O10w—H102⋯N5ix 0.84 (1) 2.11 (3) 2.893 (6) 155 (7)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) x+1, y, z; (iv) -x+2, -y+2, -z+1; (v) -x+1, -y+2, -z+2; (vi) -x+1, -y+1, -z+2; (vii) x, y+1, z; (viii) -x, -y+2, -z+2; (ix) x-1, y+1, z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The chelating ability of the 3-aminopyrazine-2-carboxylate anion is probably similar to that of the pyrazine-2-carboxylate anion, and the crystal structures of a number of lanthanum carboxylates have been reported. The additional amino substitution in the 3-aminopyrazine-2-carboxylate should be expected to consolidate the crystal structure of the praeseodymium derivative through extensive hydrogen bonding. The synthesis of the praseodymium analog under hydrothermal conditions yielded instead the polymeric chain compound, Pr2(H2O)5(CHO2)(C5H4N3O2)5.6H2O; a formate group is (Scheme I, Fig. 1). In a previous synthesis, the carboxylic acid was found to decompose to an oxalate (Gao & Ng, 2011).

Adjacent chains interact with the lattice water molecules to generate a three-dimensional hydrogen-bonded network (Table 1).

Related literature top

3-Aminopyrazinecarboxylic acid decomposition with subsequent oxalate formation has been documented in anotherother lanthanum system; see: Gao et al. (2011).

Experimental top

Praeseodymium(III) nitrate hexahydrate (0.5 mmol), 3-aminopyrazine-2-carboxylic acid (2 mmol) and sodium hydroxide (2 mmol) were dissolved in water (12 ml). The solution was placed in a 23-ml, Teflon-lined Parr bomb. The bomb was heated at 433 K for 3 days. It was cooled to room temperature; colorless prismatic crystals were isolated by hand.

Refinement top

Carbon- and nitrogen-bound H-atoms were placed in calculated positions (C–H 0.93 Å, N–H 0.88 Å were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C,N). The water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O—H 0.84–0.01 Å and H···H 1.37±0.01 Å; their temperature factors were tied by a factor of 1.5 times.

The formate ion is disordered with respect to the C and uncoordinated O atoms in a 1:1 ratio; the occupancy was assumed as it could not be refined.

The final difference Fourier map had a peak/hole in the vicinity of Pr1.

Omitted from the refinement were (-1 1 12), (-1 0 3), (3 4 10), (-7 13 2), (-2 4 11), (3 3 9), (1 3 10), (-4 - 3 6), (2 4 11), (12 6 9), (-1 3 9), (1 10 13), (6 8 4), (5 7 5) and (-4 5 00.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the asymmetric unit of polymeric Pr2(H2O)5(CHO2)(C5H4N3O2)5.6H2O at the 50% probability level; hydrogen toms are drawn as spheres of arbitrary radius. Carbon atoms are not labeled. Symmetry code: i = x – 1, y, z.
[Figure 2] Fig. 2. Monocapped square-antiprismatic geometry of the PrIII atoms.
catena-Poly[[[bis(3-aminopyrazine-2- carboxylato)triaquapraseodymium(III)]-µ-3-aminopyrazine-2-carboxylato- [(3-aminopyrazine-2-carboxylato)diaquaformatopraseodymium(III)]- µ-3-aminopyrazine-2-carboxylato] hexahydrate] top
Crystal data top
[Pr2(C5H4N3O2)5(CHO2)(H2O)5]·6H2OZ = 2
Mr = 1215.58F(000) = 1212
Triclinic, P1Dx = 1.842 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7213 (3) ÅCell parameters from 16800 reflections
b = 14.2113 (6) Åθ = 3.0–27.5°
c = 17.6228 (6) ŵ = 2.30 mm1
α = 68.801 (1)°T = 293 K
β = 76.291 (1)°Prism, colorless
γ = 79.349 (1)°0.14 × 0.12 × 0.07 mm
V = 2191.97 (14) Å3
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
9906 independent reflections
Radiation source: fine-focus sealed tube8214 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1112
Tmin = 0.739, Tmax = 0.856k = 1818
21572 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0227P)2 + 4.2692P]
where P = (Fo2 + 2Fc2)/3
9906 reflections(Δ/σ)max = 0.001
679 parametersΔρmax = 1.34 e Å3
69 restraintsΔρmin = 1.03 e Å3
Crystal data top
[Pr2(C5H4N3O2)5(CHO2)(H2O)5]·6H2Oγ = 79.349 (1)°
Mr = 1215.58V = 2191.97 (14) Å3
Triclinic, P1Z = 2
a = 9.7213 (3) ÅMo Kα radiation
b = 14.2113 (6) ŵ = 2.30 mm1
c = 17.6228 (6) ÅT = 293 K
α = 68.801 (1)°0.14 × 0.12 × 0.07 mm
β = 76.291 (1)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
9906 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
8214 reflections with I > 2σ(I)
Tmin = 0.739, Tmax = 0.856Rint = 0.041
21572 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03569 restraints
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 1.34 e Å3
9906 reflectionsΔρmin = 1.03 e Å3
679 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Pr10.41603 (2)0.502827 (16)0.710959 (12)0.02425 (6)
Pr20.83609 (2)0.788695 (16)0.719791 (12)0.02408 (6)
O10.5494 (3)0.4496 (2)0.59541 (18)0.0380 (7)
O20.6256 (4)0.3460 (3)0.5212 (2)0.0495 (9)
O30.3840 (3)0.3776 (2)0.84899 (17)0.0343 (7)
O40.4534 (4)0.2648 (3)0.9623 (2)0.0555 (10)
O50.6159 (3)0.6033 (2)0.63160 (17)0.0330 (7)
O60.6980 (3)0.6774 (2)0.70017 (17)0.0345 (7)
O71.0367 (3)0.6542 (2)0.72776 (17)0.0362 (7)
O81.1707 (3)0.5181 (2)0.79033 (18)0.0379 (7)
O90.5965 (3)0.8007 (2)0.79749 (19)0.0378 (7)
O100.4025 (4)0.8696 (3)0.8612 (2)0.0519 (9)
O110.7239 (4)0.9123 (3)0.6086 (2)0.0474 (8)
O120.8772 (8)1.0092 (6)0.5192 (4)0.056 (2)0.50
O12'0.5902 (9)0.9751 (6)0.5161 (5)0.059 (2)0.50
O1W0.2309 (3)0.5361 (2)0.61620 (19)0.0372 (7)
H110.162 (4)0.571 (3)0.635 (3)0.056*
H120.277 (4)0.573 (3)0.5723 (18)0.056*
O2W0.4608 (3)0.5895 (2)0.8054 (2)0.0387 (7)
H210.392 (3)0.634 (3)0.812 (3)0.058*
H220.537 (3)0.617 (3)0.788 (3)0.058*
O3W0.3224 (3)0.6911 (2)0.6547 (2)0.0406 (7)
H310.2358 (17)0.699 (4)0.675 (3)0.061*
H320.362 (4)0.740 (3)0.652 (3)0.061*
O4W1.0343 (4)0.8931 (3)0.6399 (2)0.0480 (9)
H411.087 (5)0.917 (4)0.659 (3)0.072*
H421.005 (6)0.939 (3)0.600 (3)0.072*
O5W0.9665 (4)0.8011 (3)0.82261 (19)0.0446 (8)
H511.050 (2)0.780 (4)0.830 (3)0.067*
H520.914 (4)0.801 (5)0.8676 (17)0.067*
O6W0.2393 (4)0.7251 (3)0.85899 (19)0.0440 (8)
H610.211 (6)0.683 (3)0.9056 (15)0.066*
H620.272 (6)0.772 (3)0.865 (3)0.066*
O7W0.4322 (4)0.8556 (4)0.6513 (4)0.0823 (14)
H710.504 (5)0.836 (6)0.673 (4)0.124*
H720.457 (7)0.881 (7)0.5998 (9)0.124*
O8W0.1955 (4)0.9725 (3)0.7077 (3)0.0617 (10)
H810.266 (4)0.928 (3)0.707 (4)0.093*
H820.224 (6)1.0301 (19)0.691 (4)0.093*
O9W0.0929 (6)0.9679 (5)0.8854 (4)0.0950 (16)
H910.018 (6)0.944 (7)0.916 (4)0.142*
H920.107 (9)0.956 (7)0.841 (3)0.142*
O10W0.0689 (6)1.1357 (4)0.9393 (3)0.0792 (13)
H1010.082 (9)1.0757 (19)0.939 (5)0.119*
H1020.031 (8)1.174 (4)0.899 (3)0.119*
O11W0.2027 (5)1.1827 (4)1.0380 (2)0.0652 (11)
H1110.176 (6)1.161 (5)1.006 (3)0.098*
H1120.279 (4)1.208 (5)1.015 (3)0.098*
N10.3688 (4)0.3253 (3)0.7031 (2)0.0330 (8)
N20.3064 (5)0.1593 (4)0.6744 (3)0.0570 (12)
N30.4764 (6)0.1887 (4)0.5559 (3)0.0726 (16)
H3A0.45450.13530.54900.087*
H3B0.54340.22400.51970.087*
N40.6502 (4)0.3927 (3)0.7672 (2)0.0341 (8)
N50.8834 (4)0.2900 (3)0.8402 (3)0.0437 (10)
N60.7344 (5)0.2209 (4)0.9634 (3)0.0573 (12)
H6A0.80950.18920.98550.069*
H6B0.64840.21340.99350.069*
N70.9158 (4)0.7375 (3)0.5762 (2)0.0309 (7)
N80.9749 (4)0.6727 (3)0.4391 (2)0.0447 (10)
N90.7825 (4)0.5828 (3)0.4898 (2)0.0444 (10)
H9A0.80630.56350.44590.053*
H9B0.70700.56180.52740.053*
N100.8203 (3)0.6149 (3)0.85557 (19)0.0276 (7)
N110.8290 (4)0.4378 (3)0.9913 (2)0.0364 (8)
N121.0622 (4)0.3924 (3)0.9406 (2)0.0389 (9)
H12A1.06120.33810.98520.047*
H12B1.14000.40310.90250.047*
N130.7367 (4)0.9580 (3)0.7629 (2)0.0417 (9)
N140.6270 (7)1.1151 (4)0.8261 (4)0.0830 (18)
N150.4277 (6)1.0373 (4)0.8961 (4)0.0872 (19)
H15A0.39871.08710.91670.105*
H15B0.37460.98770.90990.105*
C10.2705 (5)0.2673 (4)0.7555 (3)0.0450 (11)
H10.22200.28180.80290.054*
C20.2400 (6)0.1856 (4)0.7402 (3)0.0564 (14)
H20.16960.14720.77750.068*
C30.4077 (6)0.2163 (4)0.6214 (3)0.0457 (12)
C40.4399 (4)0.3005 (3)0.6368 (3)0.0335 (9)
C50.5461 (4)0.3707 (3)0.5795 (3)0.0330 (9)
C60.7837 (5)0.3997 (4)0.7244 (3)0.0414 (11)
H60.79930.43980.66880.050*
C70.8968 (5)0.3491 (4)0.7610 (3)0.0472 (12)
H70.98790.35610.72920.057*
C80.7509 (5)0.2801 (4)0.8845 (3)0.0374 (10)
C90.6311 (4)0.3337 (3)0.8464 (2)0.0313 (9)
C100.4781 (5)0.3237 (3)0.8901 (3)0.0337 (9)
C111.0286 (5)0.7640 (4)0.5170 (3)0.0418 (11)
H11A1.08950.80480.52070.050*
C121.0555 (5)0.7305 (4)0.4495 (3)0.0475 (12)
H12C1.13540.75020.40900.057*
C130.8612 (4)0.6441 (4)0.4995 (3)0.0341 (9)
C140.8306 (4)0.6788 (3)0.5689 (2)0.0278 (8)
C150.7060 (4)0.6513 (3)0.6374 (2)0.0270 (8)
C160.7085 (4)0.5945 (4)0.9177 (3)0.0363 (10)
H160.62650.64040.91620.044*
C170.7145 (5)0.5055 (4)0.9841 (3)0.0394 (10)
H170.63440.49231.02590.047*
C180.9451 (4)0.4587 (3)0.9306 (2)0.0290 (8)
C190.9370 (4)0.5484 (3)0.8608 (2)0.0257 (8)
C201.0576 (4)0.5752 (3)0.7884 (2)0.0283 (8)
C210.8085 (7)1.0364 (5)0.7454 (4)0.0672 (17)
H21A0.89791.03910.71130.081*
C220.7522 (9)1.1138 (5)0.7769 (5)0.087 (2)
H22A0.80521.16780.76290.105*
C230.5516 (7)1.0371 (4)0.8444 (4)0.0566 (14)
C240.6070 (5)0.9575 (3)0.8110 (3)0.0353 (9)
C250.5288 (4)0.8702 (3)0.8248 (2)0.0331 (9)
C260.757 (2)0.9797 (17)0.5430 (14)0.052 (4)0.50
H260.68891.01000.50950.063*0.50
C26'0.705 (2)0.9658 (19)0.5407 (16)0.056 (5)0.50
H26'0.77911.00190.50450.067*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pr10.02117 (11)0.02774 (12)0.02498 (11)0.00649 (8)0.00251 (8)0.01252 (9)
Pr20.02275 (11)0.02509 (12)0.02534 (11)0.00591 (8)0.00256 (9)0.00912 (9)
O10.0382 (16)0.0429 (19)0.0378 (16)0.0160 (14)0.0080 (14)0.0232 (14)
O20.054 (2)0.050 (2)0.0449 (18)0.0100 (17)0.0141 (16)0.0288 (16)
O30.0248 (14)0.0406 (18)0.0325 (15)0.0043 (13)0.0009 (13)0.0087 (13)
O40.0380 (18)0.073 (3)0.0322 (17)0.0019 (17)0.0029 (15)0.0001 (17)
O50.0327 (15)0.0402 (18)0.0332 (15)0.0181 (13)0.0041 (13)0.0201 (13)
O60.0353 (16)0.0464 (19)0.0287 (14)0.0200 (14)0.0080 (13)0.0220 (13)
O70.0266 (14)0.0380 (18)0.0297 (14)0.0021 (13)0.0053 (12)0.0038 (13)
O80.0238 (14)0.0392 (18)0.0336 (15)0.0044 (13)0.0094 (13)0.0052 (13)
O90.0328 (16)0.0338 (17)0.0467 (17)0.0052 (13)0.0029 (14)0.0191 (14)
O100.0379 (18)0.054 (2)0.058 (2)0.0023 (16)0.0099 (17)0.0246 (18)
O110.055 (2)0.044 (2)0.0390 (18)0.0019 (16)0.0176 (17)0.0048 (15)
O120.065 (5)0.062 (5)0.037 (4)0.035 (4)0.009 (4)0.002 (3)
O12'0.063 (5)0.056 (5)0.061 (5)0.006 (4)0.030 (4)0.012 (4)
O1W0.0369 (17)0.0442 (19)0.0350 (16)0.0078 (14)0.0023 (14)0.0196 (14)
O2W0.0364 (16)0.044 (2)0.0383 (16)0.0151 (14)0.0091 (15)0.0215 (15)
O3W0.0319 (16)0.0350 (18)0.0537 (19)0.0069 (14)0.0018 (15)0.0179 (15)
O4W0.060 (2)0.053 (2)0.0325 (16)0.0346 (19)0.0015 (16)0.0069 (15)
O5W0.0425 (18)0.063 (2)0.0362 (16)0.0103 (17)0.0137 (15)0.0200 (17)
O6W0.0495 (19)0.045 (2)0.0339 (16)0.0131 (16)0.0001 (15)0.0102 (14)
O7W0.046 (2)0.075 (3)0.148 (4)0.012 (2)0.013 (3)0.063 (3)
O8W0.052 (2)0.050 (2)0.091 (3)0.0163 (18)0.009 (2)0.030 (2)
O9W0.100 (4)0.092 (4)0.097 (4)0.031 (3)0.006 (3)0.042 (3)
O10W0.079 (3)0.092 (4)0.077 (3)0.000 (3)0.028 (3)0.036 (3)
O11W0.067 (3)0.085 (3)0.0409 (19)0.018 (2)0.0025 (19)0.018 (2)
N10.0340 (18)0.0287 (19)0.0367 (18)0.0070 (15)0.0010 (16)0.0131 (15)
N20.068 (3)0.044 (3)0.064 (3)0.020 (2)0.005 (2)0.028 (2)
N30.092 (4)0.061 (3)0.078 (3)0.029 (3)0.019 (3)0.051 (3)
N40.0280 (17)0.035 (2)0.0351 (18)0.0045 (15)0.0030 (15)0.0122 (16)
N50.0284 (19)0.058 (3)0.048 (2)0.0006 (18)0.0078 (18)0.023 (2)
N60.044 (2)0.078 (4)0.039 (2)0.006 (2)0.011 (2)0.011 (2)
N70.0278 (17)0.035 (2)0.0302 (17)0.0095 (15)0.0007 (15)0.0108 (15)
N80.039 (2)0.065 (3)0.0334 (19)0.017 (2)0.0096 (17)0.0248 (19)
N90.046 (2)0.064 (3)0.0352 (19)0.023 (2)0.0076 (18)0.032 (2)
N100.0255 (16)0.0295 (19)0.0240 (15)0.0035 (14)0.0032 (14)0.0090 (14)
N110.0316 (19)0.039 (2)0.0300 (18)0.0096 (16)0.0036 (15)0.0047 (16)
N120.035 (2)0.036 (2)0.0333 (18)0.0001 (16)0.0006 (17)0.0027 (16)
N130.048 (2)0.034 (2)0.048 (2)0.0094 (18)0.0072 (19)0.0193 (18)
N140.110 (5)0.053 (3)0.096 (4)0.016 (3)0.009 (4)0.050 (3)
N150.092 (4)0.066 (4)0.100 (4)0.002 (3)0.029 (4)0.056 (3)
C10.045 (3)0.044 (3)0.045 (3)0.017 (2)0.008 (2)0.017 (2)
C20.063 (3)0.049 (3)0.057 (3)0.031 (3)0.005 (3)0.016 (3)
C30.053 (3)0.033 (3)0.057 (3)0.005 (2)0.005 (2)0.025 (2)
C40.033 (2)0.032 (2)0.037 (2)0.0006 (18)0.0041 (19)0.0166 (18)
C50.031 (2)0.037 (2)0.034 (2)0.0028 (18)0.0015 (18)0.0181 (18)
C60.029 (2)0.044 (3)0.040 (2)0.002 (2)0.008 (2)0.011 (2)
C70.027 (2)0.056 (3)0.054 (3)0.008 (2)0.006 (2)0.019 (2)
C80.035 (2)0.044 (3)0.037 (2)0.001 (2)0.008 (2)0.020 (2)
C90.027 (2)0.040 (2)0.030 (2)0.0026 (18)0.0006 (17)0.0192 (18)
C100.032 (2)0.038 (3)0.031 (2)0.0029 (19)0.0026 (18)0.0164 (18)
C110.032 (2)0.053 (3)0.040 (2)0.018 (2)0.003 (2)0.015 (2)
C120.039 (3)0.064 (4)0.033 (2)0.020 (2)0.014 (2)0.014 (2)
C130.031 (2)0.045 (3)0.029 (2)0.0048 (19)0.0029 (18)0.0161 (19)
C140.0260 (19)0.033 (2)0.0241 (18)0.0094 (16)0.0033 (16)0.0110 (16)
C150.0259 (19)0.028 (2)0.0272 (18)0.0037 (16)0.0007 (16)0.0117 (16)
C160.0233 (19)0.044 (3)0.033 (2)0.0043 (18)0.0073 (18)0.0101 (19)
C170.032 (2)0.047 (3)0.029 (2)0.007 (2)0.0076 (19)0.0084 (19)
C180.032 (2)0.029 (2)0.0247 (18)0.0069 (17)0.0006 (17)0.0093 (16)
C190.0243 (18)0.027 (2)0.0237 (18)0.0042 (15)0.0003 (16)0.0087 (15)
C200.0265 (19)0.032 (2)0.0232 (18)0.0046 (17)0.0041 (16)0.0102 (16)
C210.067 (4)0.054 (4)0.088 (4)0.025 (3)0.013 (3)0.041 (3)
C220.112 (6)0.054 (4)0.110 (6)0.040 (4)0.016 (5)0.052 (4)
C230.072 (4)0.042 (3)0.058 (3)0.002 (3)0.005 (3)0.028 (3)
C240.041 (2)0.033 (2)0.032 (2)0.0028 (19)0.005 (2)0.0150 (18)
C250.033 (2)0.036 (2)0.029 (2)0.0024 (18)0.0067 (18)0.0108 (18)
C260.066 (13)0.042 (8)0.035 (6)0.014 (8)0.010 (10)0.006 (6)
C26'0.054 (11)0.055 (10)0.042 (8)0.015 (8)0.012 (9)0.006 (6)
Geometric parameters (Å, º) top
Pr1—O32.428 (3)N3—C31.342 (6)
Pr1—O12.429 (3)N3—H3A0.8800
Pr1—O52.462 (3)N3—H3B0.8800
Pr1—O8i2.478 (3)N4—C91.331 (5)
Pr1—O2W2.549 (3)N4—C61.338 (5)
Pr1—O3W2.564 (3)N5—C71.333 (6)
Pr1—O1W2.605 (3)N5—C81.341 (6)
Pr1—N42.692 (4)N6—C81.328 (6)
Pr1—N12.703 (4)N6—H6A0.8800
Pr2—O62.413 (3)N6—H6B0.8800
Pr2—O92.417 (3)N7—C111.326 (5)
Pr2—O112.435 (3)N7—C141.335 (5)
Pr2—O72.456 (3)N8—C121.318 (6)
Pr2—O4W2.482 (3)N8—C131.348 (5)
Pr2—O5W2.515 (3)N9—C131.337 (5)
Pr2—N132.723 (4)N9—H9A0.8800
Pr2—N102.746 (3)N9—H9B0.8800
Pr2—N72.780 (3)N10—C191.334 (5)
O1—C51.256 (5)N10—C161.337 (5)
O2—C51.250 (5)N11—C171.328 (6)
O3—C101.266 (5)N11—C181.352 (5)
O4—C101.240 (5)N12—C181.339 (5)
O5—C151.248 (5)N12—H12A0.8800
O6—C151.270 (5)N12—H12B0.8800
O7—C201.263 (5)N13—C211.327 (6)
O8—C201.239 (5)N13—C241.342 (6)
O8—Pr1ii2.478 (3)N14—C221.318 (9)
O9—C251.263 (5)N14—C231.342 (8)
O10—C251.244 (5)N15—C231.327 (7)
O11—C26'1.20 (3)N15—H15A0.8800
O11—C261.22 (2)N15—H15B0.8800
O12—C261.243 (17)C1—C21.378 (7)
O12'—C26'1.262 (19)C1—H10.9300
O1W—H110.84 (1)C2—H20.9300
O1W—H120.84 (1)C3—C41.420 (6)
O2W—H210.84 (1)C4—C51.497 (6)
O2W—H220.84 (1)C6—C71.361 (7)
O3W—H310.84 (1)C6—H60.9300
O3W—H320.84 (1)C7—H70.9300
O4W—H410.84 (1)C8—C91.436 (6)
O4W—H420.84 (1)C9—C101.510 (6)
O5W—H510.84 (1)C11—C121.387 (7)
O5W—H520.84 (1)C11—H11A0.9300
O6W—H610.84 (1)C12—H12C0.9300
O6W—H620.84 (1)C13—C141.427 (5)
O7W—H710.84 (1)C14—C151.489 (5)
O7W—H720.84 (1)C16—C171.382 (6)
O8W—H810.84 (1)C16—H160.9300
O8W—H820.84 (1)C17—H170.9300
O9W—H910.84 (1)C18—C191.421 (5)
O9W—H920.84 (1)C19—C201.500 (5)
O10W—H1010.84 (1)C21—C221.376 (8)
O10W—H1020.84 (1)C21—H21A0.9300
O11W—H1110.84 (1)C22—H22A0.9300
O11W—H1120.84 (1)C23—C241.422 (7)
N1—C11.330 (6)C24—C251.489 (6)
N1—C41.339 (5)C26—H260.9300
N2—C21.330 (7)C26'—H26'0.9300
N2—C31.345 (7)
O3—Pr1—O1118.90 (11)C9—N4—C6118.2 (4)
O3—Pr1—O5130.60 (9)C9—N4—Pr1116.4 (3)
O1—Pr1—O567.17 (9)C6—N4—Pr1125.2 (3)
O3—Pr1—O8i67.07 (9)C7—N5—C8117.3 (4)
O1—Pr1—O8i141.05 (10)C8—N6—H6A120.0
O5—Pr1—O8i141.66 (10)C8—N6—H6B120.0
O3—Pr1—O2W74.58 (10)H6A—N6—H6B120.0
O1—Pr1—O2W137.75 (10)C11—N7—C14118.6 (4)
O5—Pr1—O2W74.37 (9)C11—N7—Pr2126.7 (3)
O8i—Pr1—O2W81.00 (10)C14—N7—Pr2114.7 (2)
O3—Pr1—O3W132.45 (10)C12—N8—C13116.5 (4)
O1—Pr1—O3W108.56 (11)C13—N9—H9A120.0
O5—Pr1—O3W70.21 (10)C13—N9—H9B120.0
O8i—Pr1—O3W74.64 (10)H9A—N9—H9B120.0
O2W—Pr1—O3W72.50 (11)C19—N10—C16118.2 (4)
O3—Pr1—O1W120.40 (10)C19—N10—Pr2116.4 (2)
O1—Pr1—O1W75.93 (10)C16—N10—Pr2125.3 (3)
O5—Pr1—O1W108.77 (10)C17—N11—C18117.6 (4)
O8i—Pr1—O1W69.75 (10)C18—N12—H12A120.0
O2W—Pr1—O1W134.93 (10)C18—N12—H12B120.0
O3W—Pr1—O1W67.22 (10)H12A—N12—H12B120.0
O3—Pr1—N462.15 (10)C21—N13—C24118.0 (5)
O1—Pr1—N476.64 (11)C21—N13—Pr2125.9 (4)
O5—Pr1—N473.83 (10)C24—N13—Pr2116.0 (3)
O8i—Pr1—N4128.16 (10)C22—N14—C23117.2 (5)
O2W—Pr1—N476.48 (11)C23—N15—H15A120.0
O3W—Pr1—N4137.40 (11)C23—N15—H15B120.0
O1W—Pr1—N4148.53 (10)H15A—N15—H15B120.0
O3—Pr1—N170.33 (11)N1—C1—C2120.5 (5)
O1—Pr1—N161.54 (10)N1—C1—H1119.7
O5—Pr1—N1127.33 (10)C2—C1—H1119.7
O8i—Pr1—N189.24 (11)N2—C2—C1123.1 (5)
O2W—Pr1—N1144.65 (11)N2—C2—H2118.5
O3W—Pr1—N1137.23 (11)C1—C2—H2118.5
O1W—Pr1—N170.05 (10)N3—C3—N2117.2 (5)
N4—Pr1—N183.46 (11)N3—C3—C4122.7 (5)
O6—Pr2—O970.23 (10)N2—C3—C4120.0 (4)
O6—Pr2—O1181.60 (11)N1—C4—C3120.8 (4)
O9—Pr2—O1181.77 (11)N1—C4—C5115.3 (4)
O6—Pr2—O787.91 (11)C3—C4—C5123.8 (4)
O9—Pr2—O7134.68 (10)O2—C5—O1125.3 (4)
O11—Pr2—O7135.14 (11)O2—C5—C4118.1 (4)
O6—Pr2—O4W138.28 (10)O1—C5—C4116.6 (4)
O9—Pr2—O4W141.47 (12)N4—C6—C7121.0 (4)
O11—Pr2—O4W79.38 (12)N4—C6—H6119.5
O7—Pr2—O4W80.18 (12)C7—C6—H6119.5
O6—Pr2—O5W141.67 (11)N5—C7—C6123.2 (4)
O9—Pr2—O5W98.21 (11)N5—C7—H7118.4
O11—Pr2—O5W134.30 (12)C6—C7—H7118.4
O7—Pr2—O5W74.59 (12)N6—C8—N5118.6 (4)
O4W—Pr2—O5W72.72 (11)N6—C8—C9121.6 (4)
O6—Pr2—N13127.32 (11)N5—C8—C9119.8 (4)
O9—Pr2—N1361.50 (11)N4—C9—C8120.6 (4)
O11—Pr2—N1372.21 (12)N4—C9—C10115.8 (4)
O7—Pr2—N13141.75 (11)C8—C9—C10123.5 (4)
O4W—Pr2—N1380.77 (13)O4—C10—O3124.9 (4)
O5W—Pr2—N1368.18 (12)O4—C10—C9118.8 (4)
O6—Pr2—N1071.21 (10)O3—C10—C9116.2 (4)
O9—Pr2—N1074.03 (10)N7—C11—C12119.8 (4)
O11—Pr2—N10148.30 (11)N7—C11—H11A120.1
O7—Pr2—N1061.27 (9)C12—C11—H11A120.1
O4W—Pr2—N10132.06 (11)N8—C12—C11124.2 (4)
O5W—Pr2—N1070.47 (11)N8—C12—H12C117.9
N13—Pr2—N10111.80 (11)C11—C12—H12C117.9
O6—Pr2—N761.32 (9)N9—C13—N8116.2 (4)
O9—Pr2—N7125.75 (10)N9—C13—C14123.7 (4)
O11—Pr2—N768.92 (11)N8—C13—C14120.2 (4)
O7—Pr2—N767.81 (10)N7—C14—C13120.8 (4)
O4W—Pr2—N777.21 (10)N7—C14—C15116.1 (3)
O5W—Pr2—N7134.98 (11)C13—C14—C15123.1 (4)
N13—Pr2—N7138.04 (11)O5—C15—O6123.0 (4)
N10—Pr2—N7109.50 (10)O5—C15—C14119.5 (3)
C5—O1—Pr1129.5 (3)O6—C15—C14117.5 (3)
C10—O3—Pr1128.6 (3)N10—C16—C17120.1 (4)
C15—O5—Pr1143.6 (3)N10—C16—H16120.0
C15—O6—Pr2129.7 (2)C17—C16—H16120.0
C20—O7—Pr2128.3 (2)N11—C17—C16123.2 (4)
C20—O8—Pr1ii141.7 (3)N11—C17—H17118.4
C25—O9—Pr2129.8 (3)C16—C17—H17118.4
C26'—O11—Pr2161.0 (11)N12—C18—N11117.1 (4)
C26—O11—Pr2139.1 (9)N12—C18—C19123.9 (4)
Pr1—O1W—H11104 (4)N11—C18—C19119.1 (4)
Pr1—O1W—H1298 (4)N10—C19—C18121.7 (3)
H11—O1W—H12110 (4)N10—C19—C20115.4 (3)
Pr1—O2W—H21110 (4)C18—C19—C20122.9 (4)
Pr1—O2W—H22114 (4)O8—C20—O7123.6 (4)
H21—O2W—H22109 (4)O8—C20—C19118.7 (4)
Pr1—O3W—H31109 (3)O7—C20—C19117.7 (3)
Pr1—O3W—H32126 (4)N13—C21—C22120.8 (6)
H31—O3W—H32109 (4)N13—C21—H21A119.6
Pr2—O4W—H41127 (4)C22—C21—H21A119.6
Pr2—O4W—H42108 (4)N14—C22—C21123.3 (6)
H41—O4W—H42109 (4)N14—C22—H22A118.4
Pr2—O5W—H51131 (4)C21—C22—H22A118.4
Pr2—O5W—H52113 (3)N15—C23—N14116.8 (5)
H51—O5W—H52110 (4)N15—C23—C24122.9 (5)
H61—O6W—H62110 (4)N14—C23—C24120.2 (5)
H71—O7W—H72110 (4)N13—C24—C23120.5 (5)
H81—O8W—H82110 (4)N13—C24—C25115.4 (4)
H91—O9W—H92109 (4)C23—C24—C25124.1 (4)
H101—O10W—H102110 (4)O10—C25—O9123.7 (4)
H111—O11W—H112110 (4)O10—C25—C24119.4 (4)
C1—N1—C4118.3 (4)O9—C25—C24116.9 (4)
C1—N1—Pr1124.5 (3)O11—C26—O12122.6 (18)
C4—N1—Pr1116.8 (3)O11—C26—H26118.7
C2—N2—C3117.2 (4)O12—C26—H26118.7
C3—N3—H3A120.0O11—C26'—O12'122.8 (16)
C3—N3—H3B120.0O11—C26'—H26'118.6
H3A—N3—H3B120.0O12'—C26'—H26'118.6
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H11···O7i0.84 (1)2.34 (2)3.115 (4)155 (5)
O1w—H12···O2iii0.84 (1)1.80 (1)2.635 (5)179 (5)
O2w—H21···O6w0.84 (1)2.02 (2)2.839 (5)164 (5)
O2w—H22···O60.84 (1)1.99 (3)2.771 (4)153 (5)
O3w—H31···O7i0.84 (1)2.05 (2)2.829 (4)155 (4)
O3w—H32···O7w0.84 (1)1.89 (1)2.721 (5)174 (4)
O4w—H41···O8wii0.84 (1)1.93 (1)2.769 (5)176 (6)
O4w—H42···O12iv0.84 (1)2.07 (5)2.649 (7)126 (5)
O5w—H51···O6wii0.84 (1)1.97 (1)2.803 (5)174 (5)
O5w—H52···O11wv0.84 (1)1.84 (1)2.673 (5)173 (6)
O6w—H61···N11vi0.84 (1)2.02 (2)2.842 (5)169 (6)
O6w—H62···O100.84 (1)2.02 (2)2.833 (5)164 (6)
O7w—H71···O90.84 (1)2.41 (4)3.135 (6)146 (7)
O7w—H72···O120.84 (1)1.99 (5)2.688 (10)141 (8)
O8w—H81···O7w0.84 (1)2.01 (3)2.782 (6)154 (7)
O8w—H82···N2vii0.84 (1)2.03 (2)2.861 (6)168 (7)
O9w—H91···O10wviii0.84 (1)2.40 (6)3.074 (8)138 (7)
O10w—H102···N5ix0.84 (1)2.11 (3)2.893 (6)155 (7)
O11w—H112···O4vii0.84 (1)1.90 (1)2.732 (5)180 (7)
N6—H6b···O40.882.032.690 (5)131
N9—H9a···O1wiii0.882.202.974 (5)147
N9—H9b···O10.882.233.037 (5)152
N9—H9b···O50.882.082.718 (5)129
N12—H12a···O11wx0.882.373.099 (6)140
N12—H12b···O80.882.062.695 (5)129
N15—H15b···O100.882.102.733 (7)129
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y+1, z+1; (iv) x+2, y+2, z+1; (v) x+1, y+2, z+2; (vi) x+1, y+1, z+2; (vii) x, y+1, z; (viii) x, y+2, z+2; (ix) x1, y+1, z; (x) x+1, y1, z.

Experimental details

Crystal data
Chemical formula[Pr2(C5H4N3O2)5(CHO2)(H2O)5]·6H2O
Mr1215.58
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.7213 (3), 14.2113 (6), 17.6228 (6)
α, β, γ (°)68.801 (1), 76.291 (1), 79.349 (1)
V3)2191.97 (14)
Z2
Radiation typeMo Kα
µ (mm1)2.30
Crystal size (mm)0.14 × 0.12 × 0.07
Data collection
DiffractometerRigaku R-AXIS RAPID IP
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.739, 0.856
No. of measured, independent and
observed [I > 2σ(I)] reflections
21572, 9906, 8214
Rint0.041
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.088, 1.06
No. of reflections9906
No. of parameters679
No. of restraints69
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.34, 1.03

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H11···O7i0.84 (1)2.34 (2)3.115 (4)155 (5)
O1w—H12···O2ii0.84 (1)1.80 (1)2.635 (5)179 (5)
O2w—H21···O6w0.84 (1)2.02 (2)2.839 (5)164 (5)
O2w—H22···O60.84 (1)1.99 (3)2.771 (4)153 (5)
O3w—H31···O7i0.84 (1)2.05 (2)2.829 (4)155 (4)
O3w—H32···O7w0.84 (1)1.89 (1)2.721 (5)174 (4)
O4w—H41···O8wiii0.84 (1)1.93 (1)2.769 (5)176 (6)
O4w—H42···O12iv0.84 (1)2.07 (5)2.649 (7)126 (5)
O5w—H51···O6wiii0.84 (1)1.97 (1)2.803 (5)174 (5)
O5w—H52···O11wv0.84 (1)1.84 (1)2.673 (5)173 (6)
O6w—H61···N11vi0.84 (1)2.02 (2)2.842 (5)169 (6)
O6w—H62···O100.84 (1)2.02 (2)2.833 (5)164 (6)
O7w—H71···O90.84 (1)2.41 (4)3.135 (6)146 (7)
O7w—H72···O12'0.84 (1)1.99 (5)2.688 (10)141 (8)
O8w—H81···O7w0.84 (1)2.01 (3)2.782 (6)154 (7)
O8w—H82···N2vii0.84 (1)2.03 (2)2.861 (6)168 (7)
O9w—H91···O10wviii0.84 (1)2.40 (6)3.074 (8)138 (7)
O10w—H102···N5ix0.84 (1)2.11 (3)2.893 (6)155 (7)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+1; (iii) x+1, y, z; (iv) x+2, y+2, z+1; (v) x+1, y+2, z+2; (vi) x+1, y+1, z+2; (vii) x, y+1, z; (viii) x, y+2, z+2; (ix) x1, y+1, z.
 

Acknowledgements

This work was supported by the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 t d03), the Key Project of the Education Bureau of Heilongjiang Province (No. 12511z023) and the University of Malaya.

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Volume 67| Part 9| September 2011| Pages m1221-m1222
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