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The title compound, [Ni(C14H16N5O3)2]n or [Ni(ppa)2]n, where ppa is 8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro­pyrido[2,3-d]pyrimidine-6-carboxyl­ate, was synthesized under hydro­thermal conditions. The NiII atom (site symmetry \overline{1}) exhibits a distorted trans-NiN2O4 octa­hedral geometry defined by two monodentate N-bonded and two bidentate O,O′-bonded ppa monoanions. The extended two-dimensional structure is a square grid. An inter­molecular N—H...O hydrogen bond occurs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809055408/hb5292sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536809055408/hb5292Isup2.hkl
Contains datablock I

CCDC reference: 764984

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.066
  • wR factor = 0.199
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.67 Ratio PLAT230_ALERT_2_B Hirshfeld Test Diff for C9 -- C10 .. 13.88 su PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 122.00 A   3 PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density -2.81 eA-3 PLAT924_ALERT_1_B The Reported and Calculated Rho(min) Differ by . 2.43 eA-3 PLAT926_ALERT_1_B Reported and Calculated R1 * 100.0 Differ by . -1.83 PLAT927_ALERT_1_B Reported and Calculated wR2 * 100.0 Differ by . -4.91 PLAT928_ALERT_1_B Reported and Calculated S value Differ by . -0.25
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.30 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.24 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 7 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.597 93
Alert level G PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large.. 0.12 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 8 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Pipemidic acid (Hppa, C14H16N5O3, 8-Ethyl-5,8-dihydro-5-oxo-2- (1-piperazinyl)-pyrido(2,3-d)-pyrimidine-6-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). The manganese, cobalt and zinc complexes of the ppa anion have been reported (Huang et al., 2008; Xu et al. 2009; Qi Xu et al.2009). The title nickel(II) complex, (I), is reported here (Fig. 1).

The nickel(II) atom is coordinated by four oxygen atoms and two N atoms from four ppa ligands (two monodentate-N and two O,O-bidentate) to form a square grid propagating in (Fig. 2).

Related literature top

For manganese, cobalt and zinc complexes of the ppa anion, see: Huang et al. (2008); Xu et al. (2009); Qi et al. (2009), respectively. For background to the medicinal uses of pipemidic acid, see: Mizuki et al. (1996).

Experimental top

A mixture of Ni(CH3COO)2.4H2O (0.063 g, 0.25 mmol), Hppa (0.15 g, 0.5 mmol), sodium hydroxide (0.04 g, 1 mmol) and water (15 ml) was stirred for 30 min in air. The mixture was then transferred to a 25 ml Teflon-lined hydrothermal bomb. The bomb was kept at 443 K for 72 h under autogenous pressure. Upon cooling, green prisms of (I) were obtained from the reaction mixture.

Refinement top

The carbon-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) = 1.2Ueq(C). The H on Nitrogen atoms were located in a difference Fourier map, and were refined with a distance restraint of N—H = 0.86 (1) /%A and with Uiso(H) = 1.2Ueq(N).

Structure description top

Pipemidic acid (Hppa, C14H16N5O3, 8-Ethyl-5,8-dihydro-5-oxo-2- (1-piperazinyl)-pyrido(2,3-d)-pyrimidine-6-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). The manganese, cobalt and zinc complexes of the ppa anion have been reported (Huang et al., 2008; Xu et al. 2009; Qi Xu et al.2009). The title nickel(II) complex, (I), is reported here (Fig. 1).

The nickel(II) atom is coordinated by four oxygen atoms and two N atoms from four ppa ligands (two monodentate-N and two O,O-bidentate) to form a square grid propagating in (Fig. 2).

For manganese, cobalt and zinc complexes of the ppa anion, see: Huang et al. (2008); Xu et al. (2009); Qi et al. (2009), respectively. For background to the medicinal uses of pipemidic acid, see: Mizuki et al. (1996).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), expanded to show the metal atom coordination showing 50% displacement ellipsoids.
[Figure 2] Fig. 2. A view of part of a two-dimensional polymeric sheet in (I) showing the square-grid connectivity.
Poly[bis[µ2-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8- dihydropyrido[2,3-d]pyrimidine-6-carboxylato]nickel(II)] top
Crystal data top
[Ni(C14H16N5O3)2]F(000) = 692
Mr = 663.35Dx = 1.378 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3258 reflections
a = 6.1249 (6) Åθ = 2.5–28.3°
b = 21.250 (2) ŵ = 0.66 mm1
c = 12.5511 (12) ÅT = 296 K
β = 101.846 (2)°Prism, green
V = 1598.8 (3) Å30.43 × 0.28 × 0.22 mm
Z = 2
Data collection top
Bruker APEXII CCD
diffractometer
2762 independent reflections
Radiation source: fine-focus sealed tube2389 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 77
Tmin = 0.764, Tmax = 0.868k = 2523
7593 measured reflectionsl = 149
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199H-atom parameters not refined
S = 1.00 w = 1/[σ2(Fo2) + (0.122P)2 + 2.8827P]
where P = (Fo2 + 2Fc2)/3
2762 reflections(Δ/σ)max = 0.007
209 parametersΔρmax = 0.89 e Å3
1 restraintΔρmin = 0.39 e Å3
Crystal data top
[Ni(C14H16N5O3)2]V = 1598.8 (3) Å3
Mr = 663.35Z = 2
Monoclinic, P21/cMo Kα radiation
a = 6.1249 (6) ŵ = 0.66 mm1
b = 21.250 (2) ÅT = 296 K
c = 12.5511 (12) Å0.43 × 0.28 × 0.22 mm
β = 101.846 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
2762 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
2389 reflections with I > 2σ(I)
Tmin = 0.764, Tmax = 0.868Rint = 0.034
7593 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0661 restraint
wR(F2) = 0.199H-atom parameters not refined
S = 1.00Δρmax = 0.89 e Å3
2762 reflectionsΔρmin = 0.39 e Å3
209 parameters
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
xyzUiso*/Ueq
Ni10.50000.50000.50000.0219 (3)
C10.7141 (7)0.47283 (19)0.3080 (4)0.0293 (9)
C20.5607 (7)0.41749 (19)0.2771 (3)0.0310 (9)
C30.3908 (6)0.39745 (18)0.3348 (3)0.0250 (8)
C40.2685 (7)0.34232 (19)0.2900 (3)0.0287 (9)
C50.0880 (8)0.3175 (2)0.3310 (4)0.0380 (11)
H50.04160.33970.38630.046*
C60.0596 (7)0.2340 (2)0.2186 (4)0.0310 (9)
C70.3168 (7)0.3083 (2)0.2024 (4)0.0333 (10)
C80.5934 (9)0.3829 (2)0.1908 (4)0.0448 (12)
H80.70170.39720.15440.054*
C90.5451 (11)0.2956 (3)0.0587 (6)0.0655 (18)
H9A0.70270.30140.05990.079*
H9B0.51790.25100.06520.079*
C100.4140 (17)0.3190 (6)0.0446 (8)0.0426 (8)
H10A0.26010.30800.05010.168*
H10B0.46810.30050.10390.168*
H10C0.42780.36400.04730.168*
C110.1716 (9)0.1431 (2)0.2519 (4)0.0462 (13)
H11A0.24570.17310.29080.055*
H11B0.07780.11640.30510.055*
C120.3438 (8)0.1034 (2)0.1784 (4)0.0375 (10)
H12A0.42240.07850.22330.045*
H12B0.45170.13110.13430.045*
C130.0646 (7)0.1360 (2)0.1181 (4)0.0330 (10)
H13A0.17110.10800.16220.040*
H13B0.14350.16110.07350.040*
C140.1164 (7)0.0976 (2)0.0452 (4)0.0297 (9)
H14A0.21290.12590.00390.036*
H14B0.04690.06940.00130.036*
H5N0.163 (7)0.035 (2)0.152 (3)0.044*
N10.4839 (7)0.3299 (2)0.1527 (3)0.0454 (11)
N20.2161 (6)0.25401 (17)0.1666 (3)0.0354 (9)
N30.0183 (7)0.26577 (19)0.2969 (4)0.0427 (10)
N40.0326 (6)0.17705 (17)0.1881 (3)0.0327 (8)
N50.2530 (5)0.06053 (15)0.1053 (3)0.0262 (7)
O10.3477 (5)0.42282 (13)0.4188 (2)0.0288 (7)
O20.6982 (5)0.50474 (11)0.3906 (2)0.0270 (7)
O30.8546 (7)0.4840 (2)0.2525 (3)0.0579 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0256 (4)0.0139 (4)0.0257 (4)0.0008 (2)0.0040 (3)0.0028 (3)
C10.032 (2)0.022 (2)0.034 (2)0.0029 (17)0.0055 (18)0.0007 (17)
C20.041 (2)0.022 (2)0.031 (2)0.0069 (17)0.0088 (18)0.0052 (17)
C30.0291 (19)0.0178 (18)0.026 (2)0.0008 (15)0.0020 (16)0.0002 (16)
C40.034 (2)0.023 (2)0.030 (2)0.0027 (17)0.0072 (17)0.0047 (17)
C50.040 (2)0.032 (2)0.046 (3)0.0112 (19)0.019 (2)0.019 (2)
C60.032 (2)0.024 (2)0.038 (2)0.0061 (17)0.0082 (18)0.0090 (18)
C70.041 (2)0.028 (2)0.034 (2)0.0039 (18)0.0117 (19)0.0074 (18)
C80.059 (3)0.037 (3)0.043 (3)0.017 (2)0.022 (2)0.012 (2)
C90.077 (4)0.060 (4)0.068 (4)0.025 (3)0.034 (3)0.018 (3)
C100.0396 (18)0.047 (2)0.0409 (17)0.0122 (15)0.0083 (14)0.0059 (15)
C110.052 (3)0.041 (3)0.053 (3)0.025 (2)0.028 (2)0.021 (2)
C120.039 (2)0.031 (2)0.045 (3)0.0097 (19)0.015 (2)0.011 (2)
C130.029 (2)0.029 (2)0.045 (2)0.0055 (17)0.0152 (19)0.0153 (19)
C140.032 (2)0.0219 (19)0.037 (2)0.0034 (16)0.0120 (18)0.0042 (17)
N10.061 (3)0.040 (2)0.042 (2)0.025 (2)0.026 (2)0.0145 (18)
N20.047 (2)0.0271 (18)0.035 (2)0.0156 (16)0.0169 (17)0.0112 (16)
N30.044 (2)0.030 (2)0.057 (3)0.0140 (17)0.0198 (19)0.0192 (19)
N40.0348 (18)0.0239 (18)0.042 (2)0.0081 (15)0.0143 (16)0.0121 (16)
N50.0275 (17)0.0193 (16)0.0303 (18)0.0026 (13)0.0020 (14)0.0004 (14)
O10.0317 (15)0.0215 (14)0.0351 (16)0.0043 (11)0.0111 (12)0.0069 (12)
O20.0329 (16)0.0184 (14)0.0298 (16)0.0003 (11)0.0066 (12)0.0026 (11)
O30.069 (3)0.061 (2)0.055 (2)0.037 (2)0.040 (2)0.026 (2)
Geometric parameters (Å, º) top
Ni1—O2i2.013 (3)C9—C101.464 (12)
Ni1—O22.013 (3)C9—N11.498 (7)
Ni1—O1i2.051 (3)C9—H9A0.9700
Ni1—O12.051 (3)C9—H9B0.9700
Ni1—N5ii2.207 (3)C10—H10A0.9600
Ni1—N5iii2.207 (3)C10—H10B0.9600
C1—O31.236 (6)C10—H10C0.9600
C1—O21.260 (5)C11—N41.472 (6)
C1—C21.505 (6)C11—C121.509 (6)
C2—C81.358 (6)C11—H11A0.9700
C2—C31.448 (6)C11—H11B0.9700
C3—O11.260 (5)C12—N51.480 (6)
C3—C41.441 (6)C12—H12A0.9700
C4—C71.398 (6)C12—H12B0.9700
C4—C51.413 (6)C13—N41.450 (5)
C5—N31.305 (6)C13—C141.522 (6)
C5—H50.9300C13—H13A0.9700
C6—N21.334 (6)C13—H13B0.9700
C6—N41.357 (5)C14—N51.467 (5)
C6—N31.357 (6)C14—H14A0.9700
C7—N21.341 (6)C14—H14B0.9700
C7—N11.382 (6)N5—Ni1iv2.207 (3)
C8—N11.348 (6)N5—H5N0.90 (4)
C8—H80.9300
O2i—Ni1—O2180.0C9—C10—H10B109.5
O2i—Ni1—O1i88.73 (11)H10A—C10—H10B109.5
O2—Ni1—O1i91.27 (11)C9—C10—H10C109.5
O2i—Ni1—O191.27 (11)H10A—C10—H10C109.5
O2—Ni1—O188.73 (11)H10B—C10—H10C109.5
O1i—Ni1—O1180.0N4—C11—C12110.6 (4)
O2i—Ni1—N5ii90.14 (12)N4—C11—H11A109.5
O2—Ni1—N5ii89.86 (12)C12—C11—H11A109.5
O1i—Ni1—N5ii91.00 (11)N4—C11—H11B109.5
O1—Ni1—N5ii89.00 (11)C12—C11—H11B109.5
O2i—Ni1—N5iii89.86 (12)H11A—C11—H11B108.1
O2—Ni1—N5iii90.14 (12)N5—C12—C11114.8 (4)
O1i—Ni1—N5iii89.00 (11)N5—C12—H12A108.6
O1—Ni1—N5iii91.00 (11)C11—C12—H12A108.6
N5ii—Ni1—N5iii180.0N5—C12—H12B108.6
O3—C1—O2122.8 (4)C11—C12—H12B108.6
O3—C1—C2118.4 (4)H12A—C12—H12B107.6
O2—C1—C2118.9 (4)N4—C13—C14110.4 (3)
C8—C2—C3118.6 (4)N4—C13—H13A109.6
C8—C2—C1116.2 (4)C14—C13—H13A109.6
C3—C2—C1125.1 (4)N4—C13—H13B109.6
O1—C3—C4119.5 (4)C14—C13—H13B109.6
O1—C3—C2126.1 (4)H13A—C13—H13B108.1
C4—C3—C2114.4 (4)N5—C14—C13113.6 (4)
C7—C4—C5113.6 (4)N5—C14—H14A108.8
C7—C4—C3123.4 (4)C13—C14—H14A108.8
C5—C4—C3122.9 (4)N5—C14—H14B108.8
N3—C5—C4124.7 (4)C13—C14—H14B108.8
N3—C5—H5117.6H14A—C14—H14B107.7
C4—C5—H5117.6C8—N1—C7118.6 (4)
N2—C6—N4116.5 (4)C8—N1—C9119.9 (4)
N2—C6—N3126.2 (4)C7—N1—C9121.5 (4)
N4—C6—N3117.4 (4)C6—N2—C7115.9 (4)
N2—C7—N1117.8 (4)C5—N3—C6115.5 (4)
N2—C7—C4123.5 (4)C6—N4—C13120.5 (4)
N1—C7—C4118.6 (4)C6—N4—C11122.5 (4)
N1—C8—C2126.3 (5)C13—N4—C11113.0 (3)
N1—C8—H8116.9C14—N5—C12108.4 (3)
C2—C8—H8116.9C14—N5—Ni1iv113.5 (2)
C10—C9—N1110.6 (7)C12—N5—Ni1iv115.6 (2)
C10—C9—H9A109.5C14—N5—H5N109 (3)
N1—C9—H9A109.5C12—N5—H5N103 (4)
C10—C9—H9B109.5Ni1iv—N5—H5N107 (3)
N1—C9—H9B109.5C3—O1—Ni1127.3 (3)
H9A—C9—H9B108.1C1—O2—Ni1134.0 (3)
C9—C10—H10A109.5
O3—C1—C2—C81.5 (7)N3—C6—N2—C75.9 (7)
O2—C1—C2—C8176.7 (4)N1—C7—N2—C6178.4 (4)
O3—C1—C2—C3178.7 (4)C4—C7—N2—C61.4 (7)
O2—C1—C2—C30.6 (6)C4—C5—N3—C62.0 (8)
C8—C2—C3—O1176.7 (4)N2—C6—N3—C57.5 (8)
C1—C2—C3—O10.5 (7)N4—C6—N3—C5174.0 (4)
C8—C2—C3—C41.8 (6)N2—C6—N4—C1311.1 (6)
C1—C2—C3—C4178.9 (4)N3—C6—N4—C13170.2 (4)
O1—C3—C4—C7174.8 (4)N2—C6—N4—C11167.2 (4)
C2—C3—C4—C73.8 (6)N3—C6—N4—C1114.2 (7)
O1—C3—C4—C55.1 (6)C14—C13—N4—C6147.5 (4)
C2—C3—C4—C5176.4 (4)C14—C13—N4—C1154.4 (5)
C7—C4—C5—N34.1 (7)C12—C11—N4—C6149.6 (4)
C3—C4—C5—N3175.8 (5)C12—C11—N4—C1352.7 (6)
C5—C4—C7—N25.8 (7)C13—C14—N5—C1254.2 (5)
C3—C4—C7—N2174.0 (4)C13—C14—N5—Ni1iv176.1 (3)
C5—C4—C7—N1177.2 (4)C11—C12—N5—C1453.0 (5)
C3—C4—C7—N12.9 (7)C11—C12—N5—Ni1iv178.4 (3)
C3—C2—C8—N11.0 (8)C4—C3—O1—Ni1178.8 (3)
C1—C2—C8—N1176.4 (5)C2—C3—O1—Ni10.4 (6)
N4—C11—C12—N552.7 (6)O2i—Ni1—O1—C3179.7 (3)
N4—C13—C14—N556.3 (5)O2—Ni1—O1—C30.3 (3)
C2—C8—N1—C72.0 (8)N5ii—Ni1—O1—C389.6 (3)
C2—C8—N1—C9177.7 (6)N5iii—Ni1—O1—C390.4 (3)
N2—C7—N1—C8177.2 (5)O3—C1—O2—Ni1178.7 (4)
C4—C7—N1—C80.0 (7)C2—C1—O2—Ni10.7 (6)
N2—C7—N1—C92.6 (8)O1i—Ni1—O2—C1179.5 (4)
C4—C7—N1—C9179.8 (5)O1—Ni1—O2—C10.5 (4)
C10—C9—N1—C889.8 (8)N5ii—Ni1—O2—C188.5 (4)
C10—C9—N1—C790.4 (7)N5iii—Ni1—O2—C191.5 (4)
N4—C6—N2—C7175.6 (4)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1/2, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···O3v0.90 (4)2.29 (4)3.161 (5)163 (5)
Symmetry code: (v) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Ni(C14H16N5O3)2]
Mr663.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)6.1249 (6), 21.250 (2), 12.5511 (12)
β (°) 101.846 (2)
V3)1598.8 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.66
Crystal size (mm)0.43 × 0.28 × 0.22
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.764, 0.868
No. of measured, independent and
observed [I > 2σ(I)] reflections
7593, 2762, 2389
Rint0.034
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.199, 1.00
No. of reflections2762
No. of parameters209
No. of restraints1
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.89, 0.39

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Ni1—O22.013 (3)Ni1—N5i2.207 (3)
Ni1—O12.051 (3)
Symmetry code: (i) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···O3ii0.90 (4)2.29 (4)3.161 (5)163 (5)
Symmetry code: (ii) x+1, y1/2, z+1/2.
 

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