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The crystal structure of the title complex, [Ni(C8H6NO4)2(H2O)4], consists of discrete NiII complex mol­ecules, which are linked to each other by classical O—H...O hydrogen bonding and offset π–π stacking inter­actions. The NiII atom is octa­hedrally coordinated by four water mol­ecules lying on the equatorial plane and two monodentate carboxyl­ate groups from two 1-carboxyl­atomethyl­pyridinium-4-carboxyl­ate ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023993/dn2051sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023993/dn2051Isup2.hkl
Contains datablock I

CCDC reference: 624199

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.032
  • wR factor = 0.078
  • Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT417_ALERT_2_B Short Inter D-H..H-D H1WA .. H2WA .. 1.41 Ang.
Alert level C PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Ni1 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 28.28 From the CIF: _reflns_number_total 2462 From the CIF: _diffrn_reflns_limit_ max hkl 7. 23. 9. From the CIF: _diffrn_reflns_limit_ min hkl -7. -1. 0. TEST1: Expected hkl limits for theta max Calculated maximum hkl 8. 25. 10. Calculated minimum hkl -8. -25. -10. REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 28.28 From the CIF: _reflns_number_total 2462 Count of symmetry unique reflns 2436 Completeness (_total/calc) 101.07% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 26 Fraction of Friedel pairs measured 0.011 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens,1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

Tetraaquabis(1-carboxylatomethylpyridinium-4-carboxylato)nickel(II) top
Crystal data top
[Ni(C8H6NO4)2(H2O)4]F(000) = 508
Mr = 491.05Dx = 1.714 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2738 reflections
a = 6.4670 (5) Åθ = 2.1–30.0°
b = 19.116 (2) ŵ = 1.09 mm1
c = 7.7037 (16) ÅT = 294 K
β = 92.344 (11)°Block, green
V = 951.6 (2) Å30.23 × 0.22 × 0.19 mm
Z = 2
Data collection top
Siemens P4
diffractometer
2526 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 28.3°, θmin = 2.1°
ω scansh = 77
Absorption correction: ψ scan
(North et al., 1968)
k = 123
Tmin = 0.787, Tmax = 0.819l = 09
3383 measured reflections3 standard reflections every 120 reflections
2738 independent reflections intensity decay: 8%
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0453P)2 + 0.2043P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2738 reflectionsΔρmax = 0.40 e Å3
304 parametersΔρmin = 0.52 e Å3
13 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.096 (14)
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 > 2σ(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
Ni10.00772 (6)0.18227 (2)0.21455 (5)0.02276 (9)
O1W0.3022 (4)0.22259 (14)0.1897 (3)0.0305 (5)
H1WA0.365 (6)0.1840 (12)0.201 (5)0.046*
H1WB0.330 (6)0.2454 (18)0.096 (3)0.046*
O2W0.3126 (4)0.15108 (15)0.2565 (4)0.0383 (6)
H2WA0.425 (4)0.170 (2)0.230 (6)0.057*
H2WB0.334 (6)0.123 (2)0.341 (5)0.057*
O3W0.0508 (4)0.21005 (17)0.0362 (3)0.0410 (6)
H3WA0.139 (5)0.187 (3)0.095 (5)0.061*
H3WB0.066 (4)0.217 (3)0.091 (5)0.061*
O4W0.0502 (4)0.15839 (16)0.4650 (3)0.0388 (6)
H4WA0.063 (4)0.154 (3)0.525 (5)0.058*
H4WB0.132 (5)0.190 (2)0.503 (5)0.058*
O10.1093 (4)0.28212 (14)0.2814 (4)0.0418 (7)
O20.1723 (4)0.34817 (15)0.3100 (4)0.0439 (7)
C10.0148 (5)0.33918 (18)0.2826 (5)0.0293 (7)
C20.1431 (5)0.40332 (17)0.2487 (4)0.0256 (6)
C30.3358 (5)0.39619 (19)0.1755 (5)0.0316 (7)
H30.38670.35200.15020.038*
C40.4492 (5)0.45450 (19)0.1412 (5)0.0314 (7)
H40.57860.44980.09400.038*
N10.3748 (4)0.51914 (14)0.1753 (4)0.0268 (6)
C50.1895 (6)0.52706 (19)0.2476 (5)0.0323 (7)
H50.14220.57170.27330.039*
C60.0700 (6)0.46981 (18)0.2835 (5)0.0312 (7)
H60.05890.47560.33080.037*
C70.5031 (6)0.5812 (2)0.1457 (5)0.0329 (8)
H7A0.41530.62000.10840.039*
H7B0.59800.57150.05440.039*
C80.6254 (6)0.6010 (2)0.3127 (5)0.0320 (7)
O30.6055 (6)0.56695 (19)0.4455 (4)0.0564 (9)
O40.7423 (5)0.65332 (17)0.2947 (4)0.0466 (7)
O50.0843 (5)0.08411 (14)0.1494 (4)0.0431 (7)
O60.1830 (5)0.01121 (17)0.1247 (6)0.0586 (9)
C90.0070 (6)0.02624 (19)0.1630 (6)0.0329 (7)
C100.1252 (5)0.03282 (17)0.2321 (4)0.0264 (6)
C110.0568 (6)0.10181 (19)0.2289 (5)0.0318 (7)
H110.07160.11230.18530.038*
C120.1779 (6)0.15432 (19)0.2898 (5)0.0325 (7)
H120.13200.20040.28700.039*
N20.3633 (5)0.13944 (16)0.3537 (4)0.0294 (6)
C130.4339 (6)0.0737 (2)0.3567 (5)0.0343 (8)
H130.56370.06470.39950.041*
C140.3174 (6)0.01931 (19)0.2974 (5)0.0337 (8)
H140.36720.02630.30110.040*
C150.4956 (6)0.1979 (2)0.4053 (4)0.0336 (8)
H15A0.59420.18120.48730.040*
H15B0.41060.23350.46290.040*
C160.6132 (5)0.2305 (2)0.2480 (5)0.0330 (7)
O70.7421 (4)0.27600 (19)0.2839 (4)0.0474 (7)
O80.5730 (6)0.2097 (2)0.1026 (4)0.0572 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02346 (16)0.01989 (15)0.02502 (16)0.00099 (18)0.00199 (11)0.00212 (18)
O1W0.0254 (11)0.0317 (13)0.0344 (13)0.0025 (10)0.0023 (9)0.0052 (10)
O2W0.0257 (12)0.0369 (14)0.0526 (17)0.0012 (11)0.0038 (11)0.0116 (12)
O3W0.0384 (14)0.0542 (16)0.0310 (13)0.0152 (13)0.0094 (10)0.0110 (12)
O4W0.0380 (14)0.0496 (16)0.0291 (13)0.0101 (12)0.0052 (10)0.0063 (11)
O10.0368 (14)0.0240 (13)0.0635 (19)0.0058 (11)0.0111 (12)0.0015 (12)
O20.0329 (14)0.0327 (14)0.0669 (19)0.0074 (12)0.0134 (13)0.0042 (13)
C10.035 (2)0.0229 (15)0.0295 (19)0.0062 (13)0.0016 (13)0.0008 (13)
C20.0283 (16)0.0224 (15)0.0257 (15)0.0043 (12)0.0018 (12)0.0017 (11)
C30.0318 (18)0.0245 (16)0.0384 (19)0.0035 (13)0.0004 (14)0.0030 (13)
C40.0266 (17)0.0321 (17)0.0358 (19)0.0002 (13)0.0049 (13)0.0032 (13)
N10.0289 (14)0.0243 (13)0.0270 (14)0.0044 (11)0.0018 (10)0.0005 (10)
C50.0330 (18)0.0228 (15)0.041 (2)0.0013 (13)0.0032 (14)0.0045 (13)
C60.0266 (18)0.0284 (17)0.0389 (19)0.0005 (13)0.0042 (14)0.0053 (14)
C70.034 (2)0.0308 (18)0.0336 (19)0.0121 (15)0.0010 (14)0.0024 (14)
C80.0319 (17)0.0371 (19)0.0271 (16)0.0103 (15)0.0035 (13)0.0019 (14)
O30.073 (2)0.061 (2)0.0342 (16)0.0357 (18)0.0050 (14)0.0071 (14)
O40.0472 (16)0.0529 (17)0.0394 (15)0.0267 (14)0.0027 (12)0.0006 (12)
O50.0437 (16)0.0234 (13)0.0612 (19)0.0012 (11)0.0072 (13)0.0006 (12)
O60.0436 (18)0.0403 (17)0.093 (3)0.0037 (14)0.0233 (17)0.0110 (17)
C90.0346 (19)0.0261 (17)0.038 (2)0.0056 (14)0.0046 (14)0.0021 (14)
C100.0303 (17)0.0240 (15)0.0248 (15)0.0005 (12)0.0016 (12)0.0021 (12)
C110.0260 (17)0.0272 (17)0.043 (2)0.0025 (14)0.0062 (14)0.0038 (14)
C120.0342 (18)0.0221 (16)0.041 (2)0.0000 (13)0.0043 (14)0.0025 (13)
N20.0314 (15)0.0304 (14)0.0266 (13)0.0079 (11)0.0022 (11)0.0036 (11)
C130.0284 (18)0.0390 (19)0.036 (2)0.0045 (14)0.0063 (14)0.0055 (15)
C140.0362 (19)0.0269 (17)0.0384 (19)0.0040 (14)0.0051 (14)0.0051 (14)
C150.0387 (19)0.0380 (19)0.0247 (16)0.0156 (16)0.0069 (14)0.0006 (14)
C160.0288 (17)0.0403 (19)0.0299 (16)0.0087 (15)0.0016 (13)0.0040 (15)
O70.0453 (15)0.0618 (19)0.0354 (14)0.0303 (15)0.0045 (11)0.0013 (13)
O80.069 (2)0.075 (2)0.0270 (14)0.041 (2)0.0002 (14)0.0015 (15)
Geometric parameters (Å, º) top
Ni1—O52.026 (3)C5—H50.9300
Ni1—O4W2.033 (3)C6—H60.9300
Ni1—O3W2.033 (3)C7—C81.530 (5)
Ni1—O2W2.072 (3)C7—H7A0.9700
Ni1—O12.076 (3)C7—H7B0.9700
Ni1—O1W2.148 (2)C8—O31.224 (5)
O1W—H1WA0.85 (3)C8—O41.264 (5)
O1W—H1WB0.86 (3)O5—C91.257 (5)
O2W—H2WA0.84 (3)O6—C91.221 (5)
O2W—H2WB0.85 (4)C9—C101.525 (5)
O3W—H3WA0.86 (4)C10—C141.384 (5)
O3W—H3WB0.86 (3)C10—C111.392 (5)
O4W—H4WA0.85 (3)C11—C121.368 (5)
O4W—H4WB0.86 (4)C11—H110.9300
O1—C11.250 (4)C12—N21.345 (5)
O2—C11.249 (4)C12—H120.9300
C1—C21.509 (5)N2—C131.339 (5)
C2—C61.386 (5)N2—C151.472 (4)
C2—C31.396 (5)C13—C141.373 (6)
C3—C41.366 (5)C13—H130.9300
C3—H30.9300C14—H140.9300
C4—N11.356 (5)C15—C161.535 (5)
C4—H40.9300C15—H15A0.9700
N1—C51.351 (5)C15—H15B0.9700
N1—C71.471 (4)C16—O81.227 (5)
C5—C61.374 (5)C16—O71.243 (5)
O5—Ni1—O4W87.89 (13)C6—C5—H5119.7
O5—Ni1—O3W93.27 (13)C5—C6—C2119.5 (3)
O4W—Ni1—O3W176.58 (12)C5—C6—H6120.2
O5—Ni1—O2W92.30 (12)C2—C6—H6120.2
O4W—Ni1—O2W89.91 (11)N1—C7—C8110.1 (3)
O3W—Ni1—O2W93.25 (11)N1—C7—H7A109.6
O5—Ni1—O1178.65 (13)C8—C7—H7A109.6
O4W—Ni1—O192.29 (13)N1—C7—H7B109.6
O3W—Ni1—O186.63 (13)C8—C7—H7B109.6
O2W—Ni1—O186.36 (11)H7A—C7—H7B108.1
O5—Ni1—O1W92.67 (11)O3—C8—O4126.6 (4)
O4W—Ni1—O1W87.58 (10)O3—C8—C7120.2 (3)
O3W—Ni1—O1W89.15 (10)O4—C8—C7113.2 (3)
O2W—Ni1—O1W174.35 (12)C9—O5—Ni1131.5 (2)
O1—Ni1—O1W88.67 (11)O6—C9—O5128.8 (4)
Ni1—O1W—H1WA97 (3)O6—C9—C10116.8 (3)
Ni1—O1W—H1WB115 (3)O5—C9—C10114.3 (3)
H1WA—O1W—H1WB116 (2)C14—C10—C11118.3 (3)
Ni1—O2W—H2WA131 (3)C14—C10—C9120.9 (3)
Ni1—O2W—H2WB115 (3)C11—C10—C9120.8 (3)
H2WA—O2W—H2WB110 (4)C12—C11—C10120.2 (3)
Ni1—O3W—H3WA119 (3)C12—C11—H11119.9
Ni1—O3W—H3WB111 (3)C10—C11—H11119.9
H3WA—O3W—H3WB114 (4)N2—C12—C11120.1 (3)
Ni1—O4W—H4WA110 (3)N2—C12—H12119.9
Ni1—O4W—H4WB108 (3)C11—C12—H12119.9
H4WA—O4W—H4WB114 (4)C13—N2—C12121.0 (3)
C1—O1—Ni1130.8 (2)C13—N2—C15120.4 (3)
O2—C1—O1126.8 (3)C12—N2—C15118.3 (3)
O2—C1—C2117.4 (3)N2—C13—C14120.9 (3)
O1—C1—C2115.8 (3)N2—C13—H13119.6
C6—C2—C3119.0 (3)C14—C13—H13119.6
C6—C2—C1121.2 (3)C13—C14—C10119.6 (3)
C3—C2—C1119.8 (3)C13—C14—H14120.2
C4—C3—C2119.6 (3)C10—C14—H14120.2
C4—C3—H3120.2N2—C15—C16111.7 (3)
C2—C3—H3120.2N2—C15—H15A109.3
N1—C4—C3120.6 (3)C16—C15—H15A109.3
N1—C4—H4119.7N2—C15—H15B109.3
C3—C4—H4119.7C16—C15—H15B109.3
C5—N1—C4120.7 (3)H15A—C15—H15B107.9
C5—N1—C7119.3 (3)O8—C16—O7126.8 (3)
C4—N1—C7119.9 (3)O8—C16—C15118.2 (3)
N1—C5—C6120.6 (3)O7—C16—C15115.0 (3)
N1—C5—H5119.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O2Wi0.85 (3)2.24 (3)2.906 (3)136 (4)
O1W—H1WB···O8ii0.86 (3)1.84 (3)2.692 (4)172 (4)
O2W—H2WA···O1Wiii0.84 (3)2.07 (3)2.906 (3)174 (5)
O2W—H2WB···O3iv0.85 (4)1.99 (4)2.835 (4)173 (5)
O3W—H3WA···O4v0.86 (4)1.86 (2)2.674 (4)156 (4)
O3W—H3WB···O7ii0.86 (3)1.90 (2)2.718 (4)158 (4)
O4W—H4WA···O4iv0.85 (3)1.84 (2)2.665 (4)163 (4)
O4W—H4WB···O7vi0.86 (4)1.97 (3)2.707 (4)143 (4)
Symmetry codes: (i) x1, y, z; (ii) x1, y+1/2, z; (iii) x+1, y, z; (iv) x+1, y1/2, z+1; (v) x+1, y1/2, z; (vi) x1, y+1/2, z+1.
 

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