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In the title compound, [Ni(C4H3N2O2)2(H2O)4] or [Ni(HDHPM)2(H2O)4] (H2DHPM = 4,6-dihydroxy­pyrimidine), the NiII atom, on an inversion centre, is six-coordinated by two N atoms from two HDMPM ligands and four O atoms from four water mol­ecules. A three-dimensional supra­molecular structure is formed through π–π and hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806027243/at2059sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806027243/at2059Isup2.hkl
Contains datablock I

CCDC reference: 275925

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.016
  • wR factor = 0.049
  • Data-to-parameter ratio = 8.9

checkCIF/PLATON results

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Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.91 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O4 .. 7.00 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.

Tetraaquabis(4,6-dioxidopyrimidin-1-ium-κN3)nickel(II) top
Crystal data top
[Ni(C4H3N2O2)2(H2O)4]F(000) = 728
Mr = 352.94Dx = 1.971 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 380 reflections
a = 13.491 (3) Åθ = 2–25.1°
b = 7.1934 (14) ŵ = 1.69 mm1
c = 13.025 (3) ÅT = 291 K
β = 109.79 (3)°Prism, blue
V = 1189.4 (4) Å30.20 × 0.18 × 0.16 mm
Z = 4
Data collection top
Bruker APEX-2 CCD area-detector
diffractometer
1043 independent reflections
Radiation source: fine-focus sealed tube1023 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.010
φ and ω scansθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.729, Tmax = 0.774k = 88
4196 measured reflectionsl = 1515
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)] = 0.016H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.049 w = 1/[σ2(Fo2) + (0.0283P)2 + 1.0265P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
1043 reflectionsΔρmax = 0.26 e Å3
117 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0017 (4)
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
Ni10.50000.53489 (3)0.75000.01570 (13)
N20.26195 (11)0.45911 (18)0.43698 (11)0.0218 (3)
N10.35073 (10)0.53398 (17)0.62103 (10)0.0185 (3)
C10.25357 (11)0.5837 (2)0.63162 (12)0.0186 (3)
C20.16084 (12)0.5546 (2)0.54309 (13)0.0237 (3)
H2A0.09640.57720.55210.028*
C30.16171 (13)0.4929 (2)0.44197 (13)0.0203 (3)
C40.34889 (13)0.4791 (2)0.52416 (13)0.0220 (3)
H4A0.41310.45200.51570.026*
O10.25452 (8)0.65635 (17)0.72167 (8)0.0248 (3)
O20.08360 (9)0.46755 (16)0.35711 (10)0.0274 (3)
O30.44701 (10)0.32668 (17)0.82954 (9)0.0226 (3)
O40.54728 (10)0.73103 (18)0.66087 (9)0.0233 (3)
H4F0.5194 (17)0.826 (3)0.6617 (16)0.032 (6)*
H3F0.4845 (19)0.233 (4)0.8353 (18)0.046 (6)*
H4E0.6059 (18)0.745 (3)0.6933 (16)0.035 (6)*
H2C0.2675 (16)0.430 (3)0.3799 (18)0.028 (5)*
H3E0.3916 (17)0.294 (3)0.8062 (16)0.033 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01363 (17)0.01808 (18)0.01479 (17)0.0000.00403 (11)0.000
N20.0208 (7)0.0289 (8)0.0150 (7)0.0015 (5)0.0051 (5)0.0028 (5)
N10.0144 (6)0.0225 (7)0.0175 (6)0.0007 (5)0.0041 (5)0.0005 (5)
C10.0173 (7)0.0192 (7)0.0202 (7)0.0006 (6)0.0075 (6)0.0022 (6)
C20.0168 (8)0.0297 (8)0.0238 (8)0.0014 (6)0.0059 (6)0.0033 (6)
C30.0182 (8)0.0176 (7)0.0228 (8)0.0002 (6)0.0038 (6)0.0014 (6)
C40.0174 (8)0.0271 (8)0.0218 (8)0.0019 (6)0.0070 (6)0.0009 (6)
O10.0189 (5)0.0379 (6)0.0177 (5)0.0015 (5)0.0062 (4)0.0040 (5)
O20.0201 (6)0.0313 (7)0.0235 (6)0.0002 (5)0.0022 (5)0.0058 (5)
O30.0175 (6)0.0243 (6)0.0250 (6)0.0032 (5)0.0059 (5)0.0023 (5)
O40.0182 (6)0.0244 (7)0.0258 (6)0.0009 (5)0.0056 (5)0.0045 (5)
Geometric parameters (Å, º) top
Ni1—O42.0608 (12)C1—O11.2800 (18)
Ni1—O4i2.0608 (12)C1—C21.401 (2)
Ni1—O3i2.0807 (12)C2—C31.394 (2)
Ni1—O32.0807 (12)C2—H2A0.9300
Ni1—N12.1415 (15)C3—O21.256 (2)
Ni1—N1i2.1415 (15)C4—H4A0.9300
N2—C41.336 (2)O3—H3F0.83 (3)
N2—C31.397 (2)O3—H3E0.74 (2)
N2—H2C0.80 (2)O4—H4F0.78 (2)
N1—C41.314 (2)O4—H4E0.77 (2)
N1—C11.410 (2)
O4—Ni1—O4i93.58 (7)C1—N1—Ni1125.51 (10)
O4—Ni1—O3i89.33 (5)O1—C1—C2123.00 (14)
O4i—Ni1—O3i175.88 (4)O1—C1—N1118.17 (13)
O4—Ni1—O3175.88 (5)C2—C1—N1118.83 (13)
O4i—Ni1—O389.33 (5)C3—C2—C1122.32 (15)
O3i—Ni1—O387.92 (7)C3—C2—H2A118.8
O4—Ni1—N187.04 (5)C1—C2—H2A118.8
O4i—Ni1—N193.20 (5)O2—C3—C2127.22 (15)
O3i—Ni1—N189.86 (5)O2—C3—N2118.10 (15)
O3—Ni1—N189.89 (5)C2—C3—N2114.67 (14)
O4—Ni1—N1i93.20 (5)N1—C4—N2125.04 (15)
O4i—Ni1—N1i87.04 (5)N1—C4—H4A117.5
O3i—Ni1—N1i89.89 (5)N2—C4—H4A117.5
O3—Ni1—N1i89.86 (5)Ni1—O3—H3F109.1 (16)
N1—Ni1—N1i179.65 (7)Ni1—O3—H3E119.3 (16)
C4—N2—C3121.81 (14)H3F—O3—H3E106 (2)
C4—N2—H2C119.1 (15)Ni1—O4—H4F110.4 (15)
C3—N2—H2C119.1 (15)Ni1—O4—H4E103.8 (16)
C4—N1—C1117.02 (13)H4F—O4—H4E107 (2)
C4—N1—Ni1117.45 (10)
O4—Ni1—N1—C463.00 (11)Ni1—N1—C1—C2172.29 (11)
O4i—Ni1—N1—C4156.43 (11)O1—C1—C2—C3173.38 (15)
O3i—Ni1—N1—C426.34 (11)N1—C1—C2—C35.5 (2)
O3—Ni1—N1—C4114.25 (12)C1—C2—C3—O2177.85 (16)
O4—Ni1—N1—C1118.41 (12)C1—C2—C3—N21.2 (2)
O4i—Ni1—N1—C124.98 (12)C4—N2—C3—O2178.62 (14)
O3i—Ni1—N1—C1152.26 (12)C4—N2—C3—C22.2 (2)
O3—Ni1—N1—C164.34 (12)C1—N1—C4—N23.1 (2)
C4—N1—C1—O1172.66 (14)Ni1—N1—C4—N2175.58 (12)
Ni1—N1—C1—O18.75 (19)C3—N2—C4—N11.2 (2)
C4—N1—C1—C26.3 (2)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4F···O2ii0.78 (2)1.99 (2)2.7557 (18)166 (2)
O3—H3F···O2iii0.83 (3)1.92 (3)2.7489 (18)174 (2)
O4—H4E···O1i0.77 (2)1.94 (2)2.6472 (18)153 (2)
N2—H2C···O1iv0.80 (2)2.10 (2)2.8939 (19)170 (2)
O3—H3E···O1v0.74 (2)2.13 (2)2.8479 (17)164 (2)
Symmetry codes: (i) x+1, y, z+3/2; (ii) x+1/2, y+3/2, z+1; (iii) x+1/2, y+1/2, z+1/2; (iv) x, y+1, z1/2; (v) x+1/2, y1/2, z+3/2.
 

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