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The title complex, [Ni(C6H6N4S2)(C3H2O4)(H2O)2], has a distorted octahedral coordination geometry with the malonate dianion and di­amino­bi­thia­zole chelating to the NiII atom in the equatorial plane, and two water mol­ecules in the axial positions. Both the malonate and di­amino­bi­thia­zole are planar, and are tilted out of the equatorial plane, with dihedral angles of 9.87 (5) and 11.65 (5)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008013/cv6294sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008013/cv6294Isup2.hkl
Contains datablock I

CCDC reference: 239043

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.024
  • wR factor = 0.059
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni - N1 .. 6.33 su PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
[Ni(C6H6N4S2)(C3H2O4)(H2O)2]F(000) = 1616
Mr = 395.06Dx = 1.872 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 22240 reflections
a = 11.0826 (3) Åθ = 2.4–25.5°
b = 12.1879 (3) ŵ = 1.72 mm1
c = 20.7505 (5) ÅT = 296 K
V = 2802.85 (12) Å3Prism, green
Z = 80.34 × 0.32 × 0.24 mm
Data collection top
Rigaku RAXIS-RAPID
diffractometer
3207 independent reflections
Radiation source: fine-focus sealed tube2983 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 10.00 pixels mm-1θmax = 27.4°, θmin = 2.0°
ω scansh = 1314
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1515
Tmin = 0.57, Tmax = 0.66l = 2626
25652 measured reflections
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)] = 0.024H-atom parameters constrained
wR(F2) = 0.059 w = 1/[σ2(Fo2) + (0.0275P)2 + 1.626P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
3207 reflectionsΔρmax = 0.35 e Å3
200 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0057 (2)
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
Ni0.616061 (17)0.111305 (16)0.196716 (9)0.02183 (7)
S10.39416 (4)0.25537 (4)0.02758 (2)0.04072 (12)
S20.85593 (4)0.06153 (4)0.04664 (2)0.03830 (12)
O10.70536 (11)0.03453 (10)0.26728 (5)0.0324 (3)
O20.77401 (12)0.00514 (11)0.36483 (6)0.0386 (3)
O30.50515 (10)0.18304 (10)0.26022 (5)0.0320 (3)
O40.45240 (12)0.25488 (11)0.35341 (6)0.0380 (3)
O50.49697 (11)0.02570 (10)0.19092 (6)0.0329 (3)
O60.73349 (11)0.24476 (10)0.20980 (6)0.0337 (3)
N10.52995 (12)0.17718 (11)0.11638 (6)0.0256 (3)
N20.38621 (14)0.30151 (13)0.15571 (8)0.0407 (4)
N30.72090 (12)0.04556 (10)0.12433 (6)0.0238 (3)
N40.87995 (13)0.04735 (12)0.17625 (7)0.0322 (3)
C10.43803 (15)0.24375 (13)0.10759 (8)0.0304 (3)
C20.50783 (17)0.16631 (15)0.00569 (8)0.0359 (4)
H20.52420.14420.03630.043*
C30.56952 (15)0.13332 (13)0.05825 (8)0.0274 (3)
C40.67449 (14)0.06075 (13)0.06266 (7)0.0257 (3)
C50.73475 (17)0.00887 (15)0.01536 (8)0.0340 (4)
H50.71390.01080.02800.041*
C60.81786 (14)0.01612 (12)0.12310 (7)0.0251 (3)
C70.70499 (14)0.05370 (13)0.32639 (7)0.0244 (3)
C80.61903 (15)0.13594 (16)0.35683 (9)0.0355 (4)
H8A0.66900.19270.37590.043*
H8B0.58000.09820.39230.043*
C90.51934 (14)0.19486 (12)0.31992 (7)0.0250 (3)
H2A0.39700.27870.19440.050*
H2B0.32130.33930.14880.050*
H4A0.86070.01950.21080.050*
H4B0.95430.07400.17050.050*
H5A0.42890.01870.17200.050*
H5B0.52420.08950.17800.050*
H6A0.70430.30220.19840.050*
H6B0.79680.24980.18860.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.02345 (11)0.02362 (11)0.01843 (11)0.00394 (7)0.00040 (7)0.00033 (7)
S10.0414 (2)0.0357 (2)0.0451 (3)0.00052 (18)0.0216 (2)0.00831 (19)
S20.0411 (2)0.0438 (3)0.0300 (2)0.0092 (2)0.00877 (18)0.00787 (18)
O10.0401 (6)0.0360 (6)0.0210 (5)0.0149 (5)0.0028 (5)0.0002 (4)
O20.0391 (7)0.0524 (8)0.0243 (5)0.0116 (6)0.0047 (5)0.0045 (5)
O30.0311 (6)0.0384 (6)0.0264 (6)0.0111 (5)0.0018 (5)0.0021 (5)
O40.0383 (7)0.0417 (7)0.0340 (6)0.0107 (6)0.0039 (5)0.0100 (5)
O50.0295 (6)0.0276 (6)0.0415 (7)0.0012 (5)0.0008 (5)0.0003 (5)
O60.0286 (6)0.0275 (6)0.0450 (7)0.0007 (5)0.0026 (5)0.0004 (5)
N10.0260 (6)0.0248 (6)0.0260 (6)0.0007 (5)0.0033 (5)0.0016 (5)
N20.0355 (8)0.0388 (8)0.0477 (9)0.0138 (7)0.0069 (7)0.0045 (7)
N30.0260 (6)0.0250 (6)0.0204 (6)0.0010 (5)0.0007 (5)0.0007 (5)
N40.0306 (7)0.0344 (7)0.0316 (7)0.0091 (6)0.0020 (6)0.0039 (6)
C10.0275 (8)0.0252 (7)0.0385 (8)0.0028 (6)0.0106 (7)0.0031 (7)
C20.0432 (10)0.0368 (9)0.0277 (8)0.0030 (8)0.0102 (7)0.0039 (7)
C30.0318 (8)0.0266 (7)0.0239 (7)0.0048 (6)0.0039 (6)0.0028 (6)
C40.0295 (8)0.0276 (7)0.0201 (7)0.0041 (6)0.0003 (6)0.0017 (6)
C50.0416 (10)0.0389 (9)0.0214 (7)0.0009 (7)0.0015 (7)0.0018 (7)
C60.0267 (7)0.0238 (7)0.0249 (7)0.0016 (6)0.0036 (6)0.0025 (6)
C70.0238 (7)0.0268 (7)0.0224 (7)0.0028 (6)0.0003 (6)0.0028 (6)
C80.0298 (8)0.0478 (10)0.0289 (8)0.0062 (7)0.0040 (7)0.0110 (7)
C90.0233 (7)0.0236 (7)0.0282 (7)0.0032 (6)0.0035 (6)0.0035 (6)
Geometric parameters (Å, º) top
Ni—O11.9997 (11)N1—C31.390 (2)
Ni—O32.0029 (11)N2—C11.350 (2)
Ni—N32.0612 (12)N2—H2A0.858
Ni—N12.0818 (13)N2—H2B0.866
Ni—O62.1007 (12)N3—C61.312 (2)
Ni—O52.1318 (12)N3—C41.3914 (19)
S1—C21.724 (2)N4—C61.355 (2)
S1—C11.7357 (17)N4—H4A0.821
S2—C51.7208 (19)N4—H4B0.894
S2—C61.7326 (15)C2—C31.348 (2)
O1—C71.2487 (19)C2—H20.9300
O2—C71.2536 (19)C3—C41.464 (2)
O3—C91.2572 (19)C4—C51.345 (2)
O4—C91.2523 (19)C5—H50.9300
O5—H5A0.855C7—C81.520 (2)
O5—H5B0.876C8—C91.524 (2)
O6—H6A0.807C8—H8A0.9700
O6—H6B0.830C8—H8B0.9700
N1—C11.315 (2)
O1—Ni—O391.50 (5)C6—N4—H4A117.55
O1—Ni—N394.17 (5)C6—N4—H4B117.51
O3—Ni—N3174.33 (5)H4A—N4—H4B120.41
O1—Ni—N1173.52 (5)N1—C1—N2123.27 (15)
O3—Ni—N194.42 (5)N1—C1—S1113.58 (13)
N3—Ni—N179.91 (5)N2—C1—S1123.08 (13)
O1—Ni—O687.77 (5)C3—C2—S1110.19 (14)
O3—Ni—O687.54 (5)C3—C2—H2124.9
N3—Ni—O692.63 (5)S1—C2—H2124.9
N1—Ni—O695.10 (5)C2—C3—N1115.29 (15)
O1—Ni—O588.92 (5)C2—C3—C4129.31 (16)
O3—Ni—O589.95 (5)N1—C3—C4115.37 (13)
N3—Ni—O590.20 (5)C5—C4—N3115.15 (15)
N1—Ni—O588.46 (5)C5—C4—C3129.25 (15)
O6—Ni—O5175.79 (5)N3—C4—C3115.57 (13)
C2—S1—C189.77 (8)C4—C5—S2110.28 (12)
C5—S2—C689.77 (8)C4—C5—H5124.9
C7—O1—Ni129.06 (10)S2—C5—H5124.9
C9—O3—Ni128.44 (10)N3—C6—N4124.16 (14)
Ni—O5—H5A119.62N3—C6—S2113.60 (12)
Ni—O5—H5B119.95N4—C6—S2122.14 (12)
H5A—O5—H5B104.60O1—C7—O2122.32 (15)
Ni—O6—H6A112.68O1—C7—C8122.24 (14)
Ni—O6—H6B120.81O2—C7—C8115.42 (14)
H6A—O6—H6B96.85C7—C8—C9123.79 (14)
C1—N1—C3111.16 (14)C7—C8—H8A106.4
C1—N1—Ni134.77 (12)C9—C8—H8A106.4
C3—N1—Ni113.70 (10)C7—C8—H8B106.4
C1—N2—H2A117.64C9—C8—H8B106.4
C1—N2—H2B120.54H8A—C8—H8B106.5
H2A—N2—H2B116.29O4—C9—O3122.66 (15)
C6—N3—C4111.18 (13)O4—C9—C8115.20 (14)
C6—N3—Ni134.33 (11)O3—C9—C8122.13 (14)
C4—N3—Ni114.21 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.862.162.920 (2)148
N2—H2B···O2i0.872.303.081 (2)150
N4—H4A···O10.822.182.8823 (18)143
N4—H4B···N2ii0.892.353.208 (2)161
O5—H5A···O2iii0.861.902.7541 (18)175
O5—H5B···O4iv0.882.022.8832 (18)167
O6—H6A···N4v0.812.112.9129 (19)175
O6—H6B···O4vi0.831.932.7607 (18)174
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+3/2, y1/2, z; (iii) x1/2, y, z+1/2; (iv) x+1, y1/2, z+1/2; (v) x+3/2, y+1/2, z; (vi) x+1/2, y, z+1/2.
 

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