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Acta Cryst. (2009). E65, m1631-m1632    [ doi:10.1107/S1600536809048363 ]

Ammonium tris(3-aminopyrazine-2-carboxylato-[kappa]2N1,O)nickelate(II) trihydrate

X.-L. Cheng, S. Gao and S. W. Ng

Abstract top

The NiII atom in the title hydrated salt, (NH4)[Ni(C5H4N3O2)3]·3H2O, is N,O-chelated by the three 3-aminopyrazine-2-carboxylate ligands, resulting in a distorted octahedral mer-NiN3O3 geometry for the metal. In the crystal, the complex anion, ammonium cation and uncoordinated water molecules are linked by extensive N-H...N, N-H...O, O-H...N and O-H...O hydrogen bonds, forming a three-dimensional network.

Related literature top

For the crystal structure of diaquabis(3-aminopyrazine-2-carboxylato)nickel(II), see: Ptasiewicz-Bak & Leciejewicz (1999).

Experimental top

Nickel dichloride hexahydrate (0.48 g, 2 mmol), 3-aminopyrazine-2-carboxylic acid (0.56 g, 4 mmol) and sodium hydroxide (0.16 g 4 mmol) were dissolved in a water/DMF (v/v = 10 ml:1 ml) mixture. The solution was sealed in a 50 ml Teflon-lined stainless steel bomb and held at 443 K for 3 days. The bomb was gradually cooled to room temperature;, and green blocks of (I) were obtained after several days. The presence of the ammonium counterion is explained by the decomposition of DMF.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) = 1.2U(C). The amino and water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H = O–H = 0.85±0.01 Å; their Uiso values were refined.

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, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Ammonium tris(3-aminopyrazine-2-carboxylato-κ2N1,O)nickelate(II) trihydrate top
Crystal data top
(NH4)[Ni(C5H4N3O2)3]·3H2OF(000) = 1128
Mr = 545.14Dx = 1.611 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 17239 reflections
a = 11.2092 (3) Åθ = 3.2–27.5°
b = 14.7061 (4) ŵ = 0.93 mm−1
c = 13.7540 (4) ÅT = 293 K
β = 97.5214 (8)°Block, green
V = 2247.75 (11) Å30.28 × 0.22 × 0.19 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		5114 independent reflections
Radiation source: fine-focus sealed tube4322 reflections with I > 2σ(I)
graphiteRint = 0.028
ω scanθmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −14→14
Tmin = 0.780, Tmax = 0.843k = −19→19
21341 measured reflectionsl = −17→17
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) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.5222P]
where P = (Fo2 + 2Fc2)/3
5114 reflections(Δ/σ)max = 0.001
380 parametersΔρmax = 0.47 e Å−3
25 restraintsΔρmin = −0.26 e Å−3
Crystal data top
(NH4)[Ni(C5H4N3O2)3]·3H2OV = 2247.75 (11) Å3
Mr = 545.14Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.2092 (3) ŵ = 0.93 mm−1
b = 14.7061 (4) ÅT = 293 K
c = 13.7540 (4) Å0.28 × 0.22 × 0.19 mm
β = 97.5214 (8)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		5114 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4322 reflections with I > 2σ(I)
Tmin = 0.780, Tmax = 0.843Rint = 0.028
21341 measured reflectionsθmax = 27.4°
Refinement top
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096Δρmax = 0.47 e Å−3
S = 1.02Δρmin = −0.26 e Å−3
5114 reflectionsAbsolute structure: ?
380 parametersFlack parameter: ?
25 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.31748 (2)0.668273 (15)0.689311 (16)0.03143 (9)
O10.42705 (12)0.74401 (9)0.78914 (10)0.0399 (3)
O20.46912 (13)0.77268 (10)0.94948 (10)0.0483 (3)
O30.37891 (13)0.72843 (9)0.57068 (10)0.0446 (3)
O40.33775 (17)0.83556 (12)0.45711 (12)0.0616 (5)
O50.21564 (11)0.57245 (9)0.60709 (9)0.0391 (3)
O60.22619 (12)0.43404 (11)0.54208 (12)0.0536 (4)
O1W0.5686 (2)0.8674 (2)0.67787 (15)0.0930 (8)
O2W0.53958 (16)1.06663 (15)0.88906 (13)0.0643 (5)
O3W0.3437 (3)0.8148 (3)0.25454 (17)0.0980 (8)
N10.25466 (14)0.62854 (10)0.81904 (11)0.0341 (3)
N20.15754 (17)0.62107 (13)0.99403 (13)0.0500 (4)
N30.2905 (2)0.73064 (15)1.06019 (13)0.0525 (5)
N40.19233 (13)0.77229 (10)0.65903 (10)0.0327 (3)
N50.03798 (15)0.91375 (11)0.59648 (12)0.0410 (4)
N60.14458 (19)0.94291 (14)0.46855 (15)0.0560 (5)
N70.44529 (13)0.56953 (10)0.67977 (10)0.0307 (3)
N80.60635 (14)0.44427 (11)0.62184 (12)0.0389 (4)
N90.45018 (16)0.36067 (12)0.54171 (13)0.0418 (4)
N100.6367 (2)0.88322 (17)0.87878 (16)0.0609 (5)
C10.40689 (16)0.73693 (12)0.87734 (13)0.0352 (4)
C20.30163 (16)0.67882 (12)0.89515 (13)0.0331 (4)
C30.25094 (18)0.67630 (13)0.98471 (14)0.0389 (4)
C40.1158 (2)0.56992 (16)0.91715 (16)0.0528 (5)
H40.05210.53070.92290.063*
C50.16254 (19)0.57242 (14)0.82959 (15)0.0429 (4)
H50.13050.53540.77780.052*
C60.31612 (18)0.79401 (13)0.53101 (13)0.0385 (4)
C70.21035 (17)0.82128 (11)0.58056 (13)0.0321 (4)
C80.13109 (17)0.89357 (12)0.54759 (13)0.0368 (4)
C90.02365 (18)0.86309 (14)0.67384 (14)0.0413 (4)
H9−0.04100.87580.70770.050*
C100.09911 (17)0.79277 (14)0.70670 (13)0.0390 (4)
H100.08550.75960.76180.047*
C110.27182 (16)0.50055 (13)0.58777 (13)0.0345 (4)
C120.40521 (15)0.49993 (12)0.62341 (12)0.0294 (3)
C130.48649 (16)0.43358 (12)0.59462 (12)0.0316 (4)
C140.64164 (17)0.51541 (14)0.67792 (15)0.0418 (4)
H140.72370.52350.69700.050*
C150.56347 (16)0.57786 (13)0.70937 (14)0.0379 (4)
H150.59240.62520.75070.045*
H1W10.518 (4)0.826 (3)0.681 (3)0.16 (2)*
H1W20.587 (4)0.871 (3)0.6200 (14)0.138 (16)*
H2W10.4664 (10)1.071 (2)0.8988 (19)0.079 (10)*
H2W20.586 (2)1.078 (3)0.9408 (15)0.123 (15)*
H3W10.366 (6)0.861 (2)0.290 (3)0.20 (3)*
H3W20.325 (6)0.772 (3)0.292 (3)0.21 (3)*
H310.3539 (16)0.7617 (16)1.056 (2)0.064 (8)*
H320.259 (2)0.724 (2)1.1133 (13)0.076 (9)*
H610.2078 (15)0.9305 (16)0.4426 (16)0.054 (7)*
H620.0924 (18)0.9821 (13)0.4466 (18)0.058 (7)*
H910.3745 (10)0.3567 (18)0.5212 (19)0.059 (7)*
H920.5008 (17)0.3270 (13)0.5183 (17)0.048 (7)*
H1010.592 (2)0.8458 (15)0.9058 (17)0.079 (10)*
H1020.627 (3)0.871 (2)0.8169 (8)0.106 (13)*
H1030.612 (3)0.9371 (9)0.887 (2)0.16 (2)*
H1040.7095 (10)0.876 (2)0.902 (2)0.124 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03054 (14)0.03344 (14)0.03110 (13)0.00615 (9)0.00699 (9)0.00153 (9)
O10.0392 (7)0.0421 (7)0.0402 (7)−0.0052 (6)0.0123 (6)−0.0010 (6)
O20.0463 (8)0.0536 (8)0.0440 (7)−0.0107 (7)0.0029 (6)−0.0063 (7)
O30.0452 (8)0.0472 (7)0.0454 (7)0.0188 (6)0.0214 (6)0.0114 (6)
O40.0649 (11)0.0760 (11)0.0496 (9)0.0243 (9)0.0285 (8)0.0262 (8)
O50.0292 (6)0.0472 (7)0.0400 (7)0.0099 (6)0.0012 (5)−0.0059 (6)
O60.0326 (7)0.0540 (9)0.0713 (10)0.0016 (6)−0.0046 (7)−0.0237 (8)
O1W0.0979 (17)0.131 (2)0.0520 (11)−0.0539 (16)0.0174 (11)−0.0013 (12)
O2W0.0414 (9)0.0925 (13)0.0577 (10)−0.0038 (9)0.0021 (8)−0.0103 (10)
O3W0.0917 (18)0.144 (2)0.0590 (12)−0.0021 (17)0.0121 (12)−0.0216 (15)
N10.0345 (8)0.0350 (8)0.0325 (7)0.0019 (6)0.0037 (6)0.0027 (6)
N20.0528 (11)0.0581 (11)0.0419 (9)−0.0058 (9)0.0163 (8)0.0059 (8)
N30.0585 (12)0.0643 (12)0.0360 (9)−0.0039 (10)0.0113 (9)−0.0049 (9)
N40.0335 (8)0.0342 (7)0.0312 (7)0.0067 (6)0.0067 (6)−0.0003 (6)
N50.0408 (9)0.0391 (8)0.0427 (8)0.0131 (7)0.0042 (7)−0.0013 (7)
N60.0556 (12)0.0564 (11)0.0582 (11)0.0224 (10)0.0161 (10)0.0245 (10)
N70.0276 (7)0.0340 (7)0.0303 (7)0.0042 (6)0.0032 (6)0.0011 (6)
N80.0298 (8)0.0432 (8)0.0443 (8)0.0071 (7)0.0074 (7)0.0015 (7)
N90.0349 (9)0.0419 (9)0.0498 (9)0.0042 (7)0.0107 (8)−0.0092 (8)
N100.0507 (12)0.0779 (16)0.0551 (12)−0.0199 (11)0.0108 (10)−0.0007 (11)
C10.0343 (9)0.0340 (9)0.0374 (9)0.0032 (7)0.0053 (7)−0.0006 (8)
C20.0325 (9)0.0349 (9)0.0317 (8)0.0058 (7)0.0037 (7)0.0029 (7)
C30.0408 (10)0.0432 (10)0.0329 (9)0.0067 (8)0.0054 (8)0.0042 (8)
C40.0518 (13)0.0584 (13)0.0501 (12)−0.0145 (11)0.0138 (10)0.0067 (11)
C50.0442 (11)0.0436 (10)0.0407 (10)−0.0084 (9)0.0046 (8)0.0021 (8)
C60.0408 (10)0.0426 (10)0.0335 (9)0.0070 (8)0.0104 (8)0.0023 (8)
C70.0338 (9)0.0319 (8)0.0306 (8)0.0043 (7)0.0039 (7)−0.0011 (7)
C80.0387 (10)0.0340 (9)0.0368 (9)0.0043 (8)0.0014 (8)0.0007 (7)
C90.0376 (10)0.0478 (11)0.0393 (9)0.0113 (9)0.0084 (8)−0.0069 (9)
C100.0387 (10)0.0461 (10)0.0339 (9)0.0089 (8)0.0111 (8)−0.0001 (8)
C110.0280 (8)0.0433 (10)0.0321 (8)0.0044 (7)0.0036 (7)−0.0003 (8)
C120.0269 (8)0.0330 (8)0.0288 (8)0.0038 (7)0.0050 (6)0.0027 (7)
C130.0315 (9)0.0335 (8)0.0306 (8)0.0042 (7)0.0076 (7)0.0037 (7)
C140.0253 (9)0.0500 (11)0.0496 (11)0.0033 (8)0.0027 (8)−0.0003 (9)
C150.0304 (9)0.0412 (10)0.0409 (9)0.0008 (8)0.0006 (7)−0.0029 (8)
Geometric parameters (Å, °) top
Ni1—O12.0476 (13)N6—C81.332 (3)
Ni1—O32.0526 (13)N6—H610.853 (10)
Ni1—O52.0567 (13)N6—H620.849 (10)
Ni1—N72.0561 (14)N7—C121.326 (2)
Ni1—N42.0805 (14)N7—C151.340 (2)
Ni1—N12.0857 (15)N8—C141.329 (3)
O1—C11.267 (2)N8—C131.356 (2)
O2—C11.252 (2)N9—C131.329 (2)
O3—C61.274 (2)N9—H910.860 (10)
O4—C61.237 (2)N9—H920.848 (10)
O5—C111.276 (2)N10—H1010.861 (9)
O6—C111.237 (2)N10—H1020.861 (9)
O1W—H1W10.84 (1)N10—H1030.853 (9)
O1W—H1W20.85 (1)N10—H1040.844 (9)
O2W—H2W10.85 (1)C1—C21.503 (3)
O2W—H2W20.84 (1)C2—C31.423 (3)
O3W—H3W10.85 (1)C4—C51.375 (3)
O3W—H3W20.86 (1)C4—H40.9300
N1—C21.332 (2)C5—H50.9300
N1—C51.345 (3)C6—C71.498 (3)
N2—C41.332 (3)C7—C81.421 (2)
N2—C31.344 (3)C9—C101.374 (3)
N3—C31.339 (3)C9—H90.9300
N3—H310.854 (10)C10—H100.9300
N3—H320.858 (10)C11—C121.511 (2)
N4—C71.335 (2)C12—C131.426 (2)
N4—C101.339 (2)C14—C151.377 (3)
N5—C91.326 (3)C14—H140.9300
N5—C81.347 (3)C15—H150.9300
O1—Ni1—O393.69 (6)H103—N10—H104111.9 (14)
O1—Ni1—O5169.25 (5)O2—C1—O1125.01 (18)
O3—Ni1—O594.48 (6)O2—C1—C2118.53 (16)
O1—Ni1—N793.74 (6)O1—C1—C2116.43 (16)
O3—Ni1—N786.83 (5)N1—C2—C3120.28 (17)
O5—Ni1—N779.76 (5)N1—C2—C1115.18 (16)
O1—Ni1—N493.66 (6)C3—C2—C1124.54 (17)
O3—Ni1—N479.14 (5)N3—C3—N2118.03 (19)
O5—Ni1—N494.73 (6)N3—C3—C2121.75 (19)
N7—Ni1—N4164.51 (6)N2—C3—C2120.16 (18)
O1—Ni1—N179.56 (6)N2—C4—C5123.1 (2)
O3—Ni1—N1170.67 (6)N2—C4—H4118.5
O5—Ni1—N193.05 (6)C5—C4—H4118.5
N7—Ni1—N199.95 (6)N1—C5—C4119.79 (19)
N4—Ni1—N194.76 (6)N1—C5—H5120.1
C1—O1—Ni1115.52 (12)C4—C5—H5120.1
C6—O3—Ni1116.28 (12)O4—C6—O3124.70 (18)
C11—O5—Ni1115.38 (11)O4—C6—C7119.59 (17)
H1W1—O1W—H1W2111 (2)O3—C6—C7115.71 (16)
H2W1—O2W—H2W2111 (2)N4—C7—C8120.49 (17)
H3W1—O3W—H3W2108 (2)N4—C7—C6115.85 (15)
C2—N1—C5119.07 (16)C8—C7—C6123.65 (17)
C2—N1—Ni1111.95 (12)N6—C8—N5117.76 (17)
C5—N1—Ni1127.91 (13)N6—C8—C7122.34 (18)
C4—N2—C3117.56 (18)N5—C8—C7119.90 (17)
C3—N3—H31117.1 (19)N5—C9—C10123.55 (18)
C3—N3—H32118 (2)N5—C9—H9118.2
H31—N3—H32124 (3)C10—C9—H9118.2
C7—N4—C10119.01 (15)N4—C10—C9119.64 (18)
C7—N4—Ni1112.91 (12)N4—C10—H10120.2
C10—N4—Ni1128.06 (13)C9—C10—H10120.2
C9—N5—C8117.40 (16)O6—C11—O5125.35 (17)
C8—N6—H61114.4 (17)O6—C11—C12119.08 (16)
C8—N6—H62120.9 (18)O5—C11—C12115.57 (16)
H61—N6—H62125 (2)N7—C12—C13120.69 (15)
C12—N7—C15119.61 (15)N7—C12—C11115.47 (15)
C12—N7—Ni1113.37 (11)C13—C12—C11123.71 (16)
C15—N7—Ni1125.84 (12)N9—C13—N8117.77 (16)
C14—N8—C13117.41 (16)N9—C13—C12122.88 (16)
C13—N9—H91116.9 (18)N8—C13—C12119.35 (16)
C13—N9—H92120.5 (17)N8—C14—C15123.63 (17)
H91—N9—H92121 (2)N8—C14—H14118.2
H101—N10—H102107.1 (13)C15—C14—H14118.2
H101—N10—H103108.6 (14)N7—C15—C14119.21 (17)
H102—N10—H103108.8 (13)N7—C15—H15120.4
H101—N10—H104110.0 (13)C14—C15—H15120.4
H102—N10—H104110.3 (14)
O3—Ni1—O1—C1170.89 (13)O1—C1—C2—C3−167.48 (17)
O5—Ni1—O1—C1−49.7 (3)C4—N2—C3—N3177.4 (2)
N7—Ni1—O1—C1−102.05 (13)C4—N2—C3—C20.1 (3)
N4—Ni1—O1—C191.56 (13)N1—C2—C3—N3−175.23 (18)
N1—Ni1—O1—C1−2.61 (13)C1—C2—C3—N33.6 (3)
O1—Ni1—O3—C6−96.17 (15)N1—C2—C3—N22.0 (3)
O5—Ni1—O3—C690.82 (15)C1—C2—C3—N2−179.12 (17)
N7—Ni1—O3—C6170.28 (15)C3—N2—C4—C5−1.0 (3)
N4—Ni1—O3—C6−3.15 (14)C2—N1—C5—C42.1 (3)
O1—Ni1—O5—C11−53.7 (3)Ni1—N1—C5—C4−164.99 (16)
O3—Ni1—O5—C1185.68 (13)N2—C4—C5—N10.0 (4)
N7—Ni1—O5—C11−0.27 (13)Ni1—O3—C6—O4−177.33 (18)
N4—Ni1—O5—C11165.13 (13)Ni1—O3—C6—C73.5 (2)
N1—Ni1—O5—C11−99.84 (13)C10—N4—C7—C8−0.6 (3)
O1—Ni1—N1—C28.76 (12)Ni1—N4—C7—C8178.20 (13)
O5—Ni1—N1—C2−179.11 (12)C10—N4—C7—C6−179.78 (17)
N7—Ni1—N1—C2100.76 (12)Ni1—N4—C7—C6−1.0 (2)
N4—Ni1—N1—C2−84.10 (13)O4—C6—C7—N4179.16 (19)
O1—Ni1—N1—C5176.63 (17)O3—C6—C7—N4−1.6 (3)
O5—Ni1—N1—C5−11.24 (17)O4—C6—C7—C80.0 (3)
N7—Ni1—N1—C5−91.37 (17)O3—C6—C7—C8179.19 (17)
N4—Ni1—N1—C583.77 (17)C9—N5—C8—N6178.60 (19)
O1—Ni1—N4—C795.17 (13)C9—N5—C8—C7−1.0 (3)
O3—Ni1—N4—C72.10 (12)N4—C7—C8—N6−178.67 (19)
O5—Ni1—N4—C7−91.56 (13)C6—C7—C8—N60.5 (3)
N7—Ni1—N4—C7−23.2 (3)N4—C7—C8—N50.9 (3)
N1—Ni1—N4—C7174.97 (12)C6—C7—C8—N5−179.97 (17)
O1—Ni1—N4—C10−86.20 (16)C8—N5—C9—C100.8 (3)
O3—Ni1—N4—C10−179.26 (17)C7—N4—C10—C90.4 (3)
O5—Ni1—N4—C1087.08 (16)Ni1—N4—C10—C9−178.17 (14)
N7—Ni1—N4—C10155.4 (2)N5—C9—C10—N4−0.5 (3)
N1—Ni1—N4—C10−6.39 (17)Ni1—O5—C11—O6177.70 (16)
O1—Ni1—N7—C12175.68 (12)Ni1—O5—C11—C12−3.4 (2)
O3—Ni1—N7—C12−90.82 (12)C15—N7—C12—C130.5 (2)
O5—Ni1—N7—C124.31 (12)Ni1—N7—C12—C13168.81 (12)
N4—Ni1—N7—C12−65.9 (3)C15—N7—C12—C11−175.57 (16)
N1—Ni1—N7—C1295.64 (12)Ni1—N7—C12—C11−7.23 (18)
O1—Ni1—N7—C15−16.83 (15)O6—C11—C12—N7−173.77 (17)
O3—Ni1—N7—C1576.67 (15)O5—C11—C12—N77.2 (2)
O5—Ni1—N7—C15171.80 (16)O6—C11—C12—C1310.3 (3)
N4—Ni1—N7—C15101.6 (2)O5—C11—C12—C13−168.66 (16)
N1—Ni1—N7—C15−96.87 (15)C14—N8—C13—N9−177.44 (18)
Ni1—O1—C1—O2174.82 (15)C14—N8—C13—C122.5 (3)
Ni1—O1—C1—C2−3.5 (2)N7—C12—C13—N9177.08 (17)
C5—N1—C2—C3−3.1 (3)C11—C12—C13—N9−7.2 (3)
Ni1—N1—C2—C3166.01 (13)N7—C12—C13—N8−2.9 (2)
C5—N1—C2—C1177.96 (16)C11—C12—C13—N8172.81 (16)
Ni1—N1—C2—C1−12.97 (18)C13—N8—C14—C150.1 (3)
O2—C1—C2—N1−166.99 (16)C12—N7—C15—C142.1 (3)
O1—C1—C2—N111.5 (2)Ni1—N7—C15—C14−164.65 (14)
O2—C1—C2—C314.1 (3)N8—C14—C15—N7−2.5 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H31···O20.85 (1)2.08 (2)2.740 (3)134 (2)
N6—H61···O40.85 (1)2.01 (2)2.701 (3)138 (2)
N6—H62···N5i0.85 (1)2.15 (1)2.992 (2)175 (2)
N9—H91···O60.86 (1)2.07 (2)2.733 (2)134 (2)
N9—H92···O3ii0.85 (1)2.10 (1)2.924 (2)164 (2)
N10—H101···O20.86 (1)1.91 (1)2.756 (3)169 (3)
N10—H102···O1w0.86 (1)1.94 (1)2.779 (3)164 (3)
N10—H103···O2w0.85 (1)2.07 (1)2.919 (3)172 (3)
N10—H104···N8iii0.84 (1)2.36 (2)3.018 (3)135 (2)
O1w—H1w1···O10.84 (1)2.25 (2)2.964 (3)143 (4)
O1w—H1w2···N2iv0.85 (1)2.00 (1)2.842 (3)171 (4)
O2w—H2w1···O5v0.85 (1)2.03 (1)2.869 (2)168 (3)
O2w—H2w2···O6vi0.84 (1)1.96 (1)2.766 (2)159 (3)
O3w—H3w1···O40.85 (1)2.39 (5)2.812 (3)111 (4)
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x+1/2, −y+3/2, z−1/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) x+1/2, −y+3/2, z+1/2.
Table 1
Selected geometric parameters (Å) top
Ni1—O12.0476 (13)Ni1—N72.0561 (14)
Ni1—O32.0526 (13)Ni1—N42.0805 (14)
Ni1—O52.0567 (13)Ni1—N12.0857 (15)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H31···O20.85 (1)2.08 (2)2.740 (3)134 (2)
N6—H61···O40.85 (1)2.01 (2)2.701 (3)138 (2)
N6—H62···N5i0.85 (1)2.15 (1)2.992 (2)175 (2)
N9—H91···O60.86 (1)2.07 (2)2.733 (2)134 (2)
N9—H92···O3ii0.85 (1)2.10 (1)2.924 (2)164 (2)
N10—H101···O20.86 (1)1.91 (1)2.756 (3)169 (3)
N10—H102···O1w0.86 (1)1.94 (1)2.779 (3)164 (3)
N10—H103···O2w0.85 (1)2.07 (1)2.919 (3)172 (3)
N10—H104···N8iii0.84 (1)2.36 (2)3.018 (3)135 (2)
O1w—H1w1···O10.84 (1)2.25 (2)2.964 (3)143 (4)
O1w—H1w2···N2iv0.85 (1)2.00 (1)2.842 (3)171 (4)
O2w—H2w1···O5v0.85 (1)2.03 (1)2.869 (2)168 (3)
O2w—H2w2···O6vi0.84 (1)1.96 (1)2.766 (2)159 (3)
O3w—H3w1···O40.85 (1)2.39 (5)2.812 (3)111 (4)
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x+1/2, −y+3/2, z−1/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) x+1/2, −y+3/2, z+1/2.
Acknowledgements top

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Scientific Fund of Remarkable Teachers of Heilongjiang Province (No. 1054 G036), Heilongjiang University and the University of Malaya for supporting this study.

references
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