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

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ISSN: 2056-9890

Di­aqua­bis­(5-carb­­oxy-2-propyl-1H-imidazole-4-carboxyl­ato-κ2N3,O4)nickel(II) N,N-di­methyl­formamide disolvate

aCollege of Food Science and Technology, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China, and bCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
*Correspondence e-mail: songwd60@163.com

(Received 22 January 2010; accepted 6 February 2010; online 13 February 2010)

In the title complex, [Ni(C8H9N2O4)2(H2O)2]·2C3H7NO, the NiII atom is six-coordinated by two N,O-bidentate 5-carb­oxy-2-propyl-1H-imidazole-4-carboxyl­ate ligands and two water mol­ecules in a distorted octa­hedral environment. The methyl C and H atoms of the two ligands are disordered over two sets of sites in 0.74 (2):0.26 (2) and 0.57 (8):0.43 (8) ratios. A supra­molecular network is stabilized by intra- and inter­molecular N—H⋯O and O—H⋯O hydrogen bonds involving the ligands, coordinated water mol­ecules and dimethyl­formamide solvent mol­ecules.

Related literature

For the structures of related 2-propyl-1H-imidazole-4,5-dicarboxyl­ate complexes, see: Song et al. (2010[Song, W.-D., Yan, J.-B., Li, S.-J., Miao, D.-L. & Li, X.-F. (2010). Acta Cryst. E66, m53.]); Yan et al. (2010[Yan, J.-B., Li, S.-J., Song, W.-D., Wang, H. & Miao, D.-L. (2010). Acta Cryst. E66, m99.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C8H9N2O4)2(H2O)2]·2C3H7NO

  • Mr = 635.26

  • Orthorhombic, P n a 21

  • a = 16.3574 (12) Å

  • b = 9.5246 (7) Å

  • c = 18.7700 (13) Å

  • V = 2924.3 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.73 mm−1

  • T = 273 K

  • 0.31 × 0.24 × 0.18 mm

Data collection
  • Rigaku/MSC Mercury CCD diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.]) Tmin = 0.805, Tmax = 0.880

  • 14413 measured reflections

  • 5064 independent reflections

  • 3663 reflections with I > 2σ(I)

  • Rint = 0.063

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.133

  • S = 1.03

  • 5064 reflections

  • 403 parameters

  • 1 restraint

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

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.36 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2344 Friedel pairs

  • Flack parameter: 0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H1⋯O2 1.05 (6) 1.42 (6) 2.474 (6) 176 (5)
O7—H7⋯O6 0.82 1.67 2.479 (6) 169
N2—H2⋯O10i 0.86 1.93 2.780 (6) 171
N4—H4⋯O9 0.86 1.94 2.788 (6) 171
O1W—H1W⋯O8ii 0.85 1.96 2.782 (5) 162
O1W—H2W⋯O10iii 0.85 1.92 2.757 (6) 168
O2W—H3W⋯O4iv 0.85 1.96 2.794 (5) 166
O2W—H4W⋯O9v 0.85 1.98 2.800 (6) 163
Symmetry codes: (i) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-1]; (ii) x, y-1, z; (iii) x, y, z-1; (iv) x, y+1, z; (v) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z].

Data collection: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalStructure; data reduction: CrystalStructure; 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

2-Propyl-1H-imidazole-4,5-dicarboxylate ligand with efficient N,O-donors has been used to obtain new metal–organic complexes, such as poly[diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- κ3N3,O4,O5)calcium(II)] (Song et al., 2010) and [diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- κ2N3,O4)manganese(II)] N,N-dimethylformamide (Yan et al., 2010). In this paper, we report the synthesis and structure of a new nickel(II) complex obtained under hydrothermal conditions.

As illustrated in Fig. 1, the title complex molecule is composed of one NiII ion, two mono-deprotonated 2-propyl-1H-imidazole-4,5-dicarboxylate ligands, two coordinated water molecules and two dimethylformamide solvent molecules. The NiII atom exhibits a slightly distorted octahedral coordination geometry, defined by two N,O-bidentate ligands and two water molecules. In the crystal structure, the complex molecules and dimethylformamide solvent molecules are linked by N—H···O and O—H···O hydrogen bonds (Table 1) into a two-dimensional supramolecular structure parallel to (0 0 1) (Fig. 2). The methyl C and H atoms of the two ligands are disordered over two sites in raios of 0.74 (2):0.26 (2) and 0.57 (8):0.43 (8).

Related literature top

For related structures of 2-propyl-1H-imidazole-4,5-dicarboxylate complexes, see: Song et al. (2010); Yan et al. (2010).

Experimental top

A mixture of Ni(CH3CO2)2 (0.5 mmol, 0.06 g) and 2-propyl-1H-imidazole-4,5-dicarboxylic acid (0.5 mmol, 0.99 g) in 15 ml of dimethylformamide solution was sealed in an autoclave equipped with a Teflon liner (20 ml) and then heated at 433 K for 4 d. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Refinement top

C- and N-bound H atoms were placed at calculated positions and treated as riding on the parent atoms, with C—H = 0.93 (CH), 0.97 (CH2) and 0.96 (CH3) Å and N—H = 0.86 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C,N). The water H atoms were located in a difference map and refined as riding, with O—H = 0.85 Å and Uiso(H) = 1.5Ueq(O). H atoms of carboxyl groups were located in a difference map, and one H atom (H3) was refined isotropically and the other (H7) was refined as riding with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: CrystalStructure (Rigaku/MSC, 2002); cell refinement: CrystalStructure (Rigaku/MSC, 2002); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. A view of the two-dimensional network constructed by N—H···O and O—H···O hydrogen bonding interactions (dashed lines).
Diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato-κ2N3,O4)nickel(II) N,N-dimethylformamide disolvate top
Crystal data top
[Ni(C8H9N2O4)2(H2O)2]·2C3H7NOF(000) = 1336
Mr = 635.26Dx = 1.443 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3420 reflections
a = 16.3574 (12) Åθ = 3.3–27.4°
b = 9.5246 (7) ŵ = 0.73 mm1
c = 18.7700 (13) ÅT = 273 K
V = 2924.3 (4) Å3Block, green
Z = 40.31 × 0.24 × 0.18 mm
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
5064 independent reflections
Radiation source: fine-focus sealed tube3663 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ω scansθmax = 25.2°, θmin = 2.2°
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
h = 1519
Tmin = 0.805, Tmax = 0.880k = 1011
14413 measured reflectionsl = 2222
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.0549P)2 + 0.3624P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5064 reflectionsΔρmax = 0.37 e Å3
403 parametersΔρmin = 0.36 e Å3
1 restraintAbsolute structure: Flack (1983), 2344 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (2)
Crystal data top
[Ni(C8H9N2O4)2(H2O)2]·2C3H7NOV = 2924.3 (4) Å3
Mr = 635.26Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 16.3574 (12) ŵ = 0.73 mm1
b = 9.5246 (7) ÅT = 273 K
c = 18.7700 (13) Å0.31 × 0.24 × 0.18 mm
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
5064 independent reflections
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
3663 reflections with I > 2σ(I)
Tmin = 0.805, Tmax = 0.880Rint = 0.063
14413 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133Δρmax = 0.37 e Å3
S = 1.03Δρmin = 0.36 e Å3
5064 reflectionsAbsolute structure: Flack (1983), 2344 Friedel pairs
403 parametersAbsolute structure parameter: 0.01 (2)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni10.10751 (4)0.00168 (7)0.09532 (6)0.03620 (17)
N10.0395 (3)0.1796 (4)0.0878 (2)0.0372 (10)
N20.0320 (3)0.3724 (4)0.0753 (2)0.0406 (12)
H20.06800.43030.05940.049*
N30.1752 (3)0.1835 (4)0.1021 (2)0.0365 (9)
N40.2477 (3)0.3758 (4)0.1143 (2)0.0390 (12)
H40.28330.43400.13060.047*
N50.3912 (3)0.7166 (5)0.2536 (3)0.0498 (12)
N60.3277 (3)0.2034 (5)0.9330 (3)0.0501 (12)
O10.1630 (2)0.1165 (3)0.1768 (2)0.0469 (10)
O20.1603 (3)0.3285 (4)0.2279 (2)0.0554 (11)
O30.0825 (3)0.5493 (4)0.2133 (2)0.0573 (11)
O40.0164 (3)0.6333 (4)0.1436 (3)0.0591 (12)
O50.0526 (2)0.1182 (3)0.0127 (2)0.0468 (10)
O60.0577 (3)0.3260 (4)0.0417 (2)0.0531 (10)
O70.1355 (3)0.5476 (5)0.0274 (2)0.0598 (12)
H70.11490.47040.03450.090*
O80.2317 (3)0.6357 (4)0.0427 (2)0.0569 (11)
O90.3702 (2)0.5395 (4)0.1757 (3)0.0588 (11)
O100.3442 (2)0.0345 (4)1.0158 (3)0.0612 (12)
O1W0.1905 (2)0.0835 (4)0.0234 (2)0.0487 (10)
H1W0.19250.17260.02560.073*
H2W0.23790.05130.01450.073*
O2W0.0247 (2)0.0860 (4)0.1677 (2)0.0487 (10)
H3W0.01870.17120.15530.073*
H4W0.02040.04360.16120.073*
C10.0669 (3)0.2786 (5)0.1358 (3)0.0350 (12)
C20.0221 (3)0.3993 (5)0.1284 (3)0.0342 (12)
C30.0202 (3)0.2402 (5)0.0517 (3)0.0390 (13)
C40.1346 (4)0.2387 (6)0.1836 (3)0.0416 (13)
C50.0282 (4)0.5373 (5)0.1632 (3)0.0469 (14)
C60.0674 (4)0.1725 (6)0.0067 (3)0.0556 (16)
H6A0.07290.07310.00350.067*
H6B0.12180.21260.00810.067*
C70.0265 (6)0.1908 (10)0.0809 (4)0.097 (3)
H7A0.04900.12140.11330.116*0.744 (18)
H7B0.03160.17220.07630.116*0.744 (18)
H7'A0.01130.11250.08430.116*0.256 (18)
H7'B0.00760.27340.07530.116*0.256 (18)
C80.0374 (9)0.3302 (15)0.1122 (7)0.107 (5)0.744 (18)
H8A0.00560.39740.08590.160*0.744 (18)
H8B0.01960.32890.16090.160*0.744 (18)
H8C0.09410.35580.11020.160*0.744 (18)
C8'0.064 (3)0.209 (4)0.154 (2)0.112 (17)0.256 (18)
H8'10.02300.24020.18670.168*0.256 (18)
H8'20.08620.12120.16970.168*0.256 (18)
H8'30.10700.27780.15140.168*0.256 (18)
C90.1496 (3)0.2789 (5)0.0522 (3)0.0341 (12)
C100.1940 (3)0.4013 (5)0.0583 (3)0.0370 (12)
C110.2348 (3)0.2449 (5)0.1388 (3)0.0405 (13)
C120.0820 (4)0.2391 (5)0.0046 (3)0.0397 (12)
C130.1883 (4)0.5381 (5)0.0228 (3)0.0444 (13)
C140.2779 (4)0.1856 (6)0.2005 (3)0.0566 (17)
H14A0.33640.19090.19260.068*
H14B0.26330.08740.20570.068*
C150.2557 (7)0.2659 (11)0.2700 (5)0.108 (3)
H15A0.25230.36570.26020.130*0.43 (8)
H15B0.20290.23480.28720.130*0.43 (8)
H15C0.29220.34590.27350.130*0.57 (8)
H15D0.20060.30240.26540.130*0.57 (8)
C160.320 (4)0.239 (7)0.326 (2)0.110 (14)0.43 (8)
H16A0.31890.14230.34020.165*0.43 (8)
H16B0.30940.29720.36720.165*0.43 (8)
H16C0.37320.26160.30750.165*0.43 (8)
C16'0.280 (3)0.190 (4)0.3375 (17)0.109 (10)0.57 (8)
H16D0.33030.13990.32950.163*0.57 (8)
H16E0.23810.12590.35100.163*0.57 (8)
H16F0.28850.25770.37500.163*0.57 (8)
C170.3560 (4)0.6586 (6)0.1975 (3)0.0492 (15)
H170.31770.71180.17280.059*
C180.3694 (6)0.8590 (7)0.2739 (4)0.084 (3)
H18A0.33380.89850.23860.125*
H18B0.41810.91500.27740.125*
H18C0.34210.85770.31920.125*
C190.4482 (5)0.6426 (9)0.2966 (4)0.080 (2)
H19A0.46470.70080.33580.120*
H19B0.49520.61830.26850.120*
H19C0.42320.55850.31450.120*
C200.3618 (4)0.1489 (6)0.9896 (3)0.0545 (16)
H200.40260.20091.01190.065*
C210.3507 (6)0.3432 (7)0.9072 (4)0.083 (3)
H21A0.38840.38540.94010.125*
H21B0.30270.40070.90340.125*
H21C0.37610.33490.86130.125*
C220.2656 (5)0.1276 (8)0.8942 (4)0.076 (2)
H22A0.26940.02940.90520.113*
H22B0.27340.14120.84400.113*
H22C0.21260.16180.90770.113*
H10.115 (4)0.456 (7)0.222 (3)0.050 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0388 (3)0.0225 (3)0.0473 (3)0.0047 (2)0.0047 (3)0.0025 (2)
N10.036 (2)0.032 (2)0.044 (3)0.0005 (18)0.006 (2)0.005 (2)
N20.040 (3)0.027 (2)0.055 (3)0.007 (2)0.001 (2)0.0057 (19)
N30.039 (2)0.0246 (19)0.046 (2)0.0044 (18)0.004 (2)0.001 (2)
N40.040 (3)0.030 (2)0.048 (3)0.010 (2)0.002 (2)0.0043 (19)
N50.050 (3)0.040 (3)0.059 (3)0.004 (2)0.007 (3)0.009 (2)
N60.051 (3)0.043 (3)0.057 (3)0.003 (2)0.001 (3)0.004 (2)
O10.052 (2)0.030 (2)0.058 (2)0.0088 (18)0.014 (2)0.0028 (19)
O20.065 (3)0.045 (2)0.056 (2)0.000 (2)0.020 (2)0.0156 (19)
O30.067 (3)0.039 (2)0.066 (3)0.002 (2)0.004 (3)0.016 (2)
O40.054 (3)0.028 (2)0.095 (4)0.0086 (19)0.011 (2)0.006 (2)
O50.049 (2)0.033 (2)0.059 (2)0.0060 (17)0.013 (2)0.0011 (19)
O60.062 (3)0.046 (2)0.051 (2)0.001 (2)0.012 (2)0.0124 (19)
O70.068 (3)0.043 (2)0.069 (3)0.002 (2)0.002 (3)0.020 (2)
O80.056 (3)0.028 (2)0.086 (3)0.0050 (19)0.002 (2)0.008 (2)
O90.043 (2)0.053 (3)0.080 (3)0.0041 (19)0.005 (2)0.016 (2)
O100.048 (3)0.048 (2)0.088 (3)0.0001 (19)0.007 (2)0.023 (2)
O1W0.049 (2)0.032 (2)0.066 (3)0.0044 (18)0.006 (2)0.0012 (18)
O2W0.053 (3)0.0281 (19)0.065 (3)0.0043 (18)0.003 (2)0.0001 (18)
C10.037 (3)0.029 (3)0.039 (3)0.002 (2)0.001 (3)0.006 (2)
C20.033 (3)0.027 (2)0.043 (3)0.001 (2)0.009 (2)0.002 (2)
C30.041 (3)0.027 (3)0.049 (3)0.000 (2)0.003 (3)0.001 (2)
C40.042 (4)0.036 (3)0.046 (3)0.000 (3)0.005 (3)0.003 (3)
C50.054 (4)0.029 (3)0.058 (4)0.001 (3)0.013 (3)0.006 (3)
C60.057 (4)0.048 (3)0.062 (4)0.010 (3)0.014 (3)0.007 (3)
C70.111 (7)0.105 (7)0.074 (6)0.009 (5)0.011 (5)0.011 (5)
C80.118 (11)0.112 (11)0.090 (9)0.029 (8)0.025 (8)0.022 (8)
C8'0.14 (4)0.10 (3)0.10 (3)0.01 (3)0.03 (3)0.00 (2)
C90.035 (3)0.026 (3)0.041 (3)0.002 (2)0.004 (2)0.003 (2)
C100.039 (3)0.027 (3)0.044 (3)0.000 (2)0.002 (3)0.002 (2)
C110.042 (4)0.033 (3)0.046 (3)0.002 (2)0.004 (3)0.004 (3)
C120.043 (3)0.031 (3)0.045 (3)0.004 (3)0.001 (3)0.002 (3)
C130.040 (3)0.033 (3)0.061 (4)0.002 (3)0.010 (3)0.004 (3)
C140.065 (4)0.042 (3)0.063 (4)0.009 (3)0.016 (3)0.010 (3)
C150.124 (8)0.124 (8)0.077 (6)0.011 (7)0.019 (6)0.022 (6)
C160.13 (3)0.12 (3)0.081 (18)0.00 (2)0.03 (2)0.026 (18)
C16'0.13 (3)0.11 (2)0.081 (14)0.005 (15)0.005 (16)0.001 (13)
C170.041 (3)0.041 (3)0.066 (4)0.005 (3)0.001 (3)0.001 (3)
C180.119 (7)0.047 (4)0.084 (5)0.002 (4)0.009 (5)0.012 (4)
C190.071 (5)0.092 (6)0.078 (5)0.013 (5)0.000 (5)0.021 (4)
C200.039 (3)0.057 (4)0.068 (4)0.003 (3)0.006 (3)0.001 (3)
C210.119 (8)0.051 (4)0.081 (5)0.008 (4)0.009 (5)0.018 (4)
C220.080 (5)0.093 (5)0.054 (4)0.027 (4)0.014 (4)0.021 (4)
Geometric parameters (Å, º) top
Ni1—N12.059 (4)C7—C8'1.51 (4)
Ni1—N32.059 (4)C7—H7A0.9700
Ni1—O1W2.079 (4)C7—H7B0.9700
Ni1—O2W2.080 (4)C7—H7'A0.9700
Ni1—O12.104 (4)C7—H7'B0.9700
Ni1—O52.109 (4)C8—H7'B1.1455
N1—C31.321 (7)C8—H8A0.9600
N1—C11.379 (6)C8—H8B0.9600
N2—C31.349 (7)C8—H8C0.9600
N2—C21.357 (7)C8'—H8'10.9600
N2—H20.8600C8'—H8'20.9600
N3—C111.331 (7)C8'—H8'30.9600
N3—C91.371 (6)C9—C101.378 (7)
N4—C111.345 (6)C9—C121.471 (8)
N4—C101.391 (7)C10—C131.467 (7)
N4—H40.8600C11—C141.468 (8)
N5—C171.321 (8)C14—C151.555 (11)
N5—C191.420 (9)C14—H14A0.9700
N5—C181.454 (8)C14—H14B0.9700
N6—C201.307 (7)C15—C16'1.51 (3)
N6—C221.443 (8)C15—C161.52 (4)
N6—C211.466 (8)C15—H15A0.9700
O1—C41.259 (6)C15—H15B0.9700
O2—C41.265 (6)C15—H15C0.9700
O3—C51.300 (7)C15—H15D0.9700
O3—H11.05 (6)C16—H16A0.9600
O4—C51.226 (7)C16—H16B0.9600
O5—C121.258 (6)C16—H16C0.9600
O6—C121.263 (6)C16'—H16D0.9600
O7—C131.281 (7)C16'—H16E0.9600
O7—H70.8200C16'—H16F0.9600
O8—C131.229 (7)C17—H170.9300
O9—C171.228 (6)C18—H18A0.9600
O10—C201.230 (7)C18—H18B0.9600
O1W—H1W0.8500C18—H18C0.9600
O1W—H2W0.8500C19—H19A0.9600
O2W—H3W0.8501C19—H19B0.9600
O2W—H4W0.8500C19—H19C0.9600
C1—C21.370 (7)C20—H200.9300
C1—C41.474 (8)C21—H21A0.9600
C2—C51.471 (7)C21—H21B0.9600
C3—C61.487 (7)C21—H21C0.9600
C6—C71.555 (10)C22—H22A0.9600
C6—H6A0.9700C22—H22B0.9600
C6—H6B0.9700C22—H22C0.9600
C7—C81.463 (14)
N1—Ni1—N3179.6 (2)C7—C8—H8C109.5
N1—Ni1—O1W88.90 (16)C7—C8'—H8'1109.5
N3—Ni1—O1W91.00 (16)C7—C8'—H8'2109.5
N1—Ni1—O2W90.96 (16)H8'1—C8'—H8'2109.5
N3—Ni1—O2W89.13 (16)C7—C8'—H8'3109.5
O1W—Ni1—O2W179.68 (18)H8'1—C8'—H8'3109.5
N1—Ni1—O180.44 (15)H8'2—C8'—H8'3109.5
N3—Ni1—O199.99 (16)N3—C9—C10110.0 (5)
O1W—Ni1—O188.97 (14)N3—C9—C12118.2 (4)
O2W—Ni1—O190.72 (16)C10—C9—C12131.7 (5)
N1—Ni1—O599.23 (15)C9—C10—N4104.4 (4)
N3—Ni1—O580.33 (15)C9—C10—C13132.8 (5)
O1W—Ni1—O590.31 (16)N4—C10—C13122.6 (5)
O2W—Ni1—O590.00 (15)N3—C11—N4110.2 (5)
O1—Ni1—O5179.21 (17)N3—C11—C14126.3 (5)
C3—N1—C1106.1 (4)N4—C11—C14123.4 (5)
C3—N1—Ni1143.2 (4)O5—C12—O6124.2 (5)
C1—N1—Ni1110.7 (3)O5—C12—C9116.8 (5)
C3—N2—C2108.9 (4)O6—C12—C9119.0 (5)
C3—N2—H2125.6O8—C13—O7124.1 (5)
C2—N2—H2125.6O8—C13—C10119.8 (5)
C11—N3—C9106.7 (4)O7—C13—C10116.1 (5)
C11—N3—Ni1142.7 (4)C11—C14—C15111.1 (5)
C9—N3—Ni1110.6 (3)C11—C14—H14A109.4
C11—N4—C10108.7 (4)C15—C14—H14A109.4
C11—N4—H4125.6C11—C14—H14B109.4
C10—N4—H4125.6C15—C14—H14B109.4
C17—N5—C19122.1 (5)H14A—C14—H14B108.0
C17—N5—C18119.5 (6)C16'—C15—C14114.0 (14)
C19—N5—C18118.4 (6)C16—C15—C14109.9 (19)
C20—N6—C22120.8 (5)C16'—C15—H15A129.8
C20—N6—C21121.3 (6)C16—C15—H15A109.7
C22—N6—C21117.9 (6)C14—C15—H15A109.7
C4—O1—Ni1114.2 (3)C16—C15—H15B109.7
C4—O2—H1111 (2)C14—C15—H15B109.7
C5—O3—H1113 (3)H15A—C15—H15B108.2
C12—O5—Ni1114.0 (4)C16'—C15—H15C98.8
C13—O7—H7109.5C14—C15—H15C107.5
Ni1—O1W—H1W112.5C16'—C15—H15D119.5
Ni1—O1W—H2W125.5C14—C15—H15D108.6
H1W—O1W—H2W109.5H15C—C15—H15D107.2
Ni1—O2W—H3W105.4C15—C16—H16A109.5
Ni1—O2W—H4W106.7C15—C16—H16B109.5
H3W—O2W—H4W108.3C15—C16—H16C109.5
C2—C1—N1109.5 (5)C15—C16'—H16D109.5
C2—C1—C4132.8 (5)C15—C16'—H16E109.5
N1—C1—C4117.7 (4)H16D—C16'—H16E109.5
N2—C2—C1105.4 (4)C15—C16'—H16F109.5
N2—C2—C5122.6 (5)H16D—C16'—H16F109.5
C1—C2—C5131.9 (5)H16E—C16'—H16F109.5
N1—C3—N2110.2 (5)O9—C17—N5124.7 (6)
N1—C3—C6124.9 (5)O9—C17—H17117.7
N2—C3—C6124.9 (5)N5—C17—H17117.7
O1—C4—O2124.6 (5)N5—C18—H18A109.5
O1—C4—C1116.9 (5)N5—C18—H18B109.5
O2—C4—C1118.4 (5)H18A—C18—H18B109.5
O4—C5—O3123.9 (5)N5—C18—H18C109.5
O4—C5—C2119.6 (6)H18A—C18—H18C109.5
O3—C5—C2116.5 (5)H18B—C18—H18C109.5
C3—C6—C7112.9 (6)N5—C19—H19A109.5
C3—C6—H6A109.0N5—C19—H19B109.5
C7—C6—H6A109.0H19A—C19—H19B109.5
C3—C6—H6B109.0N5—C19—H19C109.5
C7—C6—H6B109.0H19A—C19—H19C109.5
H6A—C6—H6B107.8H19B—C19—H19C109.5
C8—C7—C6114.1 (9)O10—C20—N6125.2 (6)
C8'—C7—C6130.5 (19)O10—C20—H20117.4
C8—C7—H7A108.7N6—C20—H20117.4
C6—C7—H7A108.7N6—C21—H21A109.5
C8—C7—H7B108.7N6—C21—H21B109.5
C8'—C7—H7B120.0H21A—C21—H21B109.5
C6—C7—H7B108.7N6—C21—H21C109.5
H7A—C7—H7B107.6H21A—C21—H21C109.5
C8'—C7—H7'A106.8H21B—C21—H21C109.5
C6—C7—H7'A104.3N6—C22—H22A109.5
C8'—C7—H7'B103.8N6—C22—H22B109.5
C6—C7—H7'B104.0H22A—C22—H22B109.5
H7A—C7—H7'B147.0N6—C22—H22C109.5
H7'A—C7—H7'B105.4H22A—C22—H22C109.5
C7—C8—H8A109.5H22B—C22—H22C109.5
C7—C8—H8B109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1···O21.05 (6)1.42 (6)2.474 (6)176 (5)
O7—H7···O60.821.672.479 (6)169
N2—H2···O10i0.861.932.780 (6)171
N4—H4···O90.861.942.788 (6)171
O1W—H1W···O8ii0.851.962.782 (5)162
O1W—H2W···O10iii0.851.922.757 (6)168
O2W—H3W···O4iv0.851.962.794 (5)166
O2W—H4W···O9v0.851.982.800 (6)163
Symmetry codes: (i) x1/2, y1/2, z1; (ii) x, y1, z; (iii) x, y, z1; (iv) x, y+1, z; (v) x1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula[Ni(C8H9N2O4)2(H2O)2]·2C3H7NO
Mr635.26
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)273
a, b, c (Å)16.3574 (12), 9.5246 (7), 18.7700 (13)
V3)2924.3 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.73
Crystal size (mm)0.31 × 0.24 × 0.18
Data collection
DiffractometerRigaku/MSC Mercury CCD
diffractometer
Absorption correctionMulti-scan
(REQAB; Jacobson, 1998)
Tmin, Tmax0.805, 0.880
No. of measured, independent and
observed [I > 2σ(I)] reflections
14413, 5064, 3663
Rint0.063
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.133, 1.03
No. of reflections5064
No. of parameters403
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.36
Absolute structureFlack (1983), 2344 Friedel pairs
Absolute structure parameter0.01 (2)

Computer programs: CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1···O21.05 (6)1.42 (6)2.474 (6)176 (5)
O7—H7···O60.821.672.479 (6)169
N2—H2···O10i0.861.932.780 (6)170.9
N4—H4···O90.861.942.788 (6)170.7
O1W—H1W···O8ii0.851.962.782 (5)162
O1W—H2W···O10iii0.851.922.757 (6)168
O2W—H3W···O4iv0.851.962.794 (5)166
O2W—H4W···O9v0.851.982.800 (6)163
Symmetry codes: (i) x1/2, y1/2, z1; (ii) x, y1, z; (iii) x, y, z1; (iv) x, y+1, z; (v) x1/2, y+1/2, z.
 

Acknowledgements

The authors acknowledge Guang Dong Ocean University for supporting this work.

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationJacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.  Google Scholar
First citationJohnson, C. K. (1976). ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSong, W.-D., Yan, J.-B., Li, S.-J., Miao, D.-L. & Li, X.-F. (2010). Acta Cryst. E66, m53.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYan, J.-B., Li, S.-J., Song, W.-D., Wang, H. & Miao, D.-L. (2010). Acta Cryst. E66, m99.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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