Poly[aqua­bis(μ-pyrazine-2-carboxyl­ato)nickel(II)]

Hao, L.-J.; Mu, C.-H.; Liu, T.-T.

doi:10.1107/S1600536806054225

Retracted: Poly[aquabis(μ-pyrazine-2-carboxylato)nickel(II)]

The asymmetric unit of the title compound, [Ni(C₅H₃N₂O2)₂(H₂O)]_n, contains two bidendate pyrazine-2-carboxylate anions bonded to Ni^II in the equatorial plane through one N and one O atom. The Ni^II atoms are linked into chains by the second N atom of one of the pyrazine-2-carboxylate anions bonding to an axial site of a neighbouring Ni^II atom. The slightly distorted octahedral coordination around Ni^II is completed by a water molecule, which forms hydrogen bonds linking the chains into a three-dimensional structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054225/br2022sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054225/br2022Isup2.hkl Contains datablock I

CCDC reference: 1269749

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R factor = 0.034
wR factor = 0.085
Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.462
           From the CIF: _refine_ls_abs_structure_Flack_su    0.018
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.46
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.88
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            N3  -NI1 -N1  -C5    -10.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N3  -NI1 -N1  -C2    162.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         14
            N1  -NI1 -N3  -C7      9.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            N1  -NI1 -N3  -C10  -174.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         21
            O3  -NI1 -O1  -C1    -39.70  1.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         26
            O1  -NI1 -O3  -C6   -133.00  1.60   1.555   1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.50
           From the CIF: _reflns_number_total               2140
           Count of symmetry unique reflns         1263
           Completeness (_total/calc)            169.44%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       877
           Fraction of Friedel pairs measured     0.694
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Poly[aquabis(µ-pyrazine-2-carboxylato)nickel(II)] top

Crystal data top

[Ni(C₅H₃N₂O₂)₂(H₂O)]	F(000) = 656
M_r = 322.91	D_x = 1.866 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2140 reflections
a = 7.8001 (2) Å	θ = 2.5–25.5°
b = 9.8818 (12) Å	µ = 1.72 mm⁻¹
c = 14.9112 (6) Å	T = 298 K
V = 1149.34 (15) Å³	Block, green
Z = 4	0.19 × 0.17 × 0.13 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1969 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 25.5°, θ_min = 2.5°
φ and ω scans	h = −8→9
6209 measured reflections	k = −11→11
2140 independent reflections	l = −14→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters not defined
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0496P)² + 1.048P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2140 reflections	Δρ_max = 1.05 e Å⁻³
175 parameters	Δρ_min = −0.36 e Å⁻³
3 restraints	Absolute structure: Flack (1983), with 987 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.462 (18)

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

	x	y	z	U_iso*/U_eq
Ni1	0.42689 (6)	0.63417 (5)	0.59075 (3)	0.01866 (14)
N1	0.3355 (4)	0.4817 (3)	0.5070 (2)	0.0225 (7)
N2	0.2667 (5)	0.2971 (4)	0.3716 (3)	0.0419 (10)
N3	0.5059 (4)	0.7909 (3)	0.6755 (2)	0.0226 (7)
N4	0.5493 (4)	0.9951 (3)	0.8012 (2)	0.0221 (7)
O1	0.6530 (4)	0.5647 (3)	0.54116 (19)	0.0256 (6)
O2	0.7628 (4)	0.4201 (4)	0.4413 (2)	0.0397 (7)
O3	0.1945 (3)	0.7028 (3)	0.63108 (18)	0.0231 (6)
O4	0.0688 (4)	0.8695 (3)	0.70907 (18)	0.0323 (6)
O5	0.4184 (4)	0.7646 (3)	0.48297 (18)	0.0305 (6)
H1	0.3392	0.8233	0.4782	0.046*
H2	0.5137	0.8011	0.4694	0.046*
C1	0.6434 (6)	0.4718 (5)	0.4809 (4)	0.0397 (7)
C2	0.4625 (5)	0.4270 (4)	0.4591 (3)	0.0254 (9)
C3	0.4257 (6)	0.3352 (4)	0.3920 (3)	0.0353 (11)
H3	0.5161	0.2983	0.3595	0.042*
C4	0.1414 (6)	0.3508 (4)	0.4212 (3)	0.0338 (10)
H4	0.0285	0.3254	0.4103	0.041*
C5	0.1762 (6)	0.4442 (4)	0.4890 (3)	0.0286 (9)
H5A	0.0862	0.4806	0.5221	0.034*
C6	0.1941 (5)	0.8090 (4)	0.6836 (3)	0.0200 (8)
C7	0.3725 (5)	0.8543 (4)	0.7113 (2)	0.0206 (8)
C8	0.3945 (5)	0.9583 (4)	0.7737 (3)	0.0248 (9)
H8	0.2986	1.0026	0.7963	0.030*
C9	0.6840 (6)	0.9332 (4)	0.7636 (3)	0.0269 (9)
H9	0.7941	0.9590	0.7803	0.032*
C10	0.6637 (6)	0.8312 (4)	0.7001 (3)	0.0274 (10)
H10	0.7597	0.7908	0.6747	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0169 (2)	0.0194 (2)	0.0197 (2)	−0.0002 (2)	−0.0010 (2)	−0.0004 (2)
N1	0.0228 (18)	0.0188 (16)	0.0258 (18)	−0.0001 (14)	−0.0001 (15)	−0.0005 (14)
N2	0.037 (2)	0.044 (2)	0.045 (2)	−0.006 (2)	−0.0046 (19)	−0.0162 (19)
N3	0.0201 (16)	0.0247 (17)	0.0231 (18)	−0.0002 (15)	−0.0013 (14)	0.0017 (14)
N4	0.0214 (18)	0.0220 (15)	0.0228 (16)	0.0010 (15)	0.0005 (14)	−0.0033 (13)
O1	0.0185 (14)	0.0272 (15)	0.0313 (16)	−0.0014 (12)	0.0015 (12)	−0.0022 (13)
O2	0.0238 (14)	0.0487 (16)	0.0467 (16)	0.0040 (12)	0.0044 (12)	−0.0101 (13)
O3	0.0175 (14)	0.0263 (14)	0.0254 (14)	−0.0005 (12)	−0.0021 (11)	−0.0013 (12)
O4	0.0180 (14)	0.0395 (15)	0.0393 (16)	0.0067 (17)	−0.0019 (13)	−0.0090 (14)
O5	0.0264 (15)	0.0323 (15)	0.0329 (15)	0.0109 (15)	0.0047 (14)	0.0131 (12)
C1	0.0238 (14)	0.0487 (16)	0.0467 (16)	0.0040 (12)	0.0044 (12)	−0.0101 (13)
C2	0.026 (3)	0.026 (2)	0.024 (2)	0.0048 (17)	0.0019 (17)	0.0036 (17)
C3	0.028 (2)	0.040 (2)	0.039 (3)	0.003 (2)	0.003 (2)	−0.0149 (18)
C4	0.026 (2)	0.034 (2)	0.042 (2)	−0.0023 (19)	−0.0055 (19)	−0.009 (2)
C5	0.026 (2)	0.028 (2)	0.031 (2)	0.0059 (19)	0.0009 (18)	−0.0015 (17)
C6	0.018 (2)	0.0221 (18)	0.0202 (19)	−0.0023 (16)	−0.0012 (15)	0.0025 (16)
C7	0.0203 (19)	0.0224 (18)	0.0192 (18)	0.0009 (17)	−0.0027 (14)	0.0022 (17)
C8	0.028 (3)	0.0235 (19)	0.023 (2)	0.0011 (17)	−0.0014 (17)	−0.0008 (16)
C9	0.022 (2)	0.027 (2)	0.032 (2)	−0.0024 (18)	0.0009 (18)	−0.0060 (18)
C10	0.019 (2)	0.030 (2)	0.033 (2)	0.0000 (18)	0.0015 (18)	−0.0019 (18)

Geometric parameters (Å, º) top

Ni1—O3	2.026 (3)	O3—C6	1.310 (5)
Ni1—O1	2.032 (3)	O4—C6	1.207 (5)
Ni1—O5	2.061 (3)	O5—H1	0.8504
Ni1—N1	2.083 (3)	O5—H2	0.8506
Ni1—N3	2.092 (3)	C1—C2	1.514 (7)
Ni1—N4ⁱ	2.125 (3)	C2—C3	1.382 (6)
N1—C5	1.324 (6)	C3—H3	0.9300
N1—C2	1.335 (5)	C4—C5	1.395 (6)
N2—C3	1.331 (6)	C4—H4	0.9300
N2—C4	1.336 (6)	C5—H5A	0.9300
N3—C7	1.326 (5)	C6—C7	1.519 (5)
N3—C10	1.345 (5)	C7—C8	1.397 (6)
N4—C8	1.327 (5)	C8—H8	0.9300
N4—C9	1.339 (5)	C9—C10	1.391 (6)
N4—Ni1ⁱⁱ	2.125 (3)	C9—H9	0.9300
O1—C1	1.287 (6)	C10—H10	0.9300
O2—C1	1.215 (6)

O3—Ni1—O1	175.85 (12)	O2—C1—O1	126.5 (5)
O3—Ni1—O5	89.63 (12)	O2—C1—C2	119.2 (4)
O1—Ni1—O5	87.44 (12)	O1—C1—C2	114.3 (4)
O3—Ni1—N1	96.53 (13)	N1—C2—C3	119.9 (4)
O1—Ni1—N1	80.47 (12)	N1—C2—C1	117.3 (3)
O5—Ni1—N1	88.52 (12)	C3—C2—C1	122.7 (4)
O3—Ni1—N3	80.60 (12)	N2—C3—C2	123.0 (4)
O1—Ni1—N3	102.38 (13)	N2—C3—H3	118.5
O5—Ni1—N3	90.98 (12)	C2—C3—H3	118.5
N1—Ni1—N3	177.09 (14)	N2—C4—C5	121.4 (4)
O3—Ni1—N4ⁱ	93.98 (12)	N2—C4—H4	119.3
O1—Ni1—N4ⁱ	88.95 (12)	C5—C4—H4	119.3
O5—Ni1—N4ⁱ	176.39 (14)	N1—C5—C4	120.9 (4)
N1—Ni1—N4ⁱ	90.93 (13)	N1—C5—H5A	119.5
N3—Ni1—N4ⁱ	89.74 (12)	C4—C5—H5A	119.5
C5—N1—C2	118.4 (3)	O4—C6—O3	125.9 (4)
C5—N1—Ni1	130.2 (3)	O4—C6—C7	120.7 (3)
C2—N1—Ni1	111.0 (3)	O3—C6—C7	113.4 (3)
C3—N2—C4	116.3 (4)	N3—C7—C8	121.3 (4)
C7—N3—C10	117.9 (3)	N3—C7—C6	118.0 (3)
C7—N3—Ni1	111.2 (3)	C8—C7—C6	120.7 (3)
C10—N3—Ni1	130.9 (3)	N4—C8—C7	121.3 (4)
C8—N4—C9	117.3 (3)	N4—C8—H8	119.3
C8—N4—Ni1ⁱⁱ	119.4 (3)	C7—C8—H8	119.3
C9—N4—Ni1ⁱⁱ	123.0 (3)	N4—C9—C10	121.8 (4)
C1—O1—Ni1	116.4 (3)	N4—C9—H9	119.1
C6—O3—Ni1	116.6 (2)	C10—C9—H9	119.1
Ni1—O5—H1	121.0	N3—C10—C9	120.3 (4)
Ni1—O5—H2	115.0	N3—C10—H10	119.9
H1—O5—H2	109.0	C9—C10—H10	119.9

O3—Ni1—N1—C5	−0.8 (4)	Ni1—N1—C2—C3	−172.4 (3)
O1—Ni1—N1—C5	−177.9 (4)	C5—N1—C2—C1	179.9 (4)
O5—Ni1—N1—C5	−90.3 (4)	Ni1—N1—C2—C1	6.7 (4)
N3—Ni1—N1—C5	−10 (3)	O2—C1—C2—N1	177.0 (4)
N4ⁱ—Ni1—N1—C5	93.3 (4)	O1—C1—C2—N1	−3.6 (6)
O3—Ni1—N1—C2	171.4 (2)	O2—C1—C2—C3	−4.0 (7)
O1—Ni1—N1—C2	−5.7 (3)	O1—C1—C2—C3	175.5 (4)
O5—Ni1—N1—C2	81.9 (3)	C4—N2—C3—C2	−1.3 (7)
N3—Ni1—N1—C2	162 (2)	N1—C2—C3—N2	0.1 (7)
N4ⁱ—Ni1—N1—C2	−94.5 (3)	C1—C2—C3—N2	−178.9 (5)
O3—Ni1—N3—C7	−0.2 (3)	C3—N2—C4—C5	1.5 (7)
O1—Ni1—N3—C7	176.8 (3)	C2—N1—C5—C4	−0.6 (6)
O5—Ni1—N3—C7	89.2 (3)	Ni1—N1—C5—C4	171.2 (3)
N1—Ni1—N3—C7	9 (3)	N2—C4—C5—N1	−0.7 (7)
N4ⁱ—Ni1—N3—C7	−94.3 (3)	Ni1—O3—C6—O4	174.5 (3)
O3—Ni1—N3—C10	177.0 (4)	Ni1—O3—C6—C7	−5.0 (4)
O1—Ni1—N3—C10	−5.9 (4)	C10—N3—C7—C8	−0.9 (6)
O5—Ni1—N3—C10	−93.5 (4)	Ni1—N3—C7—C8	176.7 (3)
N1—Ni1—N3—C10	−174 (2)	C10—N3—C7—C6	−180.0 (3)
N4ⁱ—Ni1—N3—C10	83.0 (4)	Ni1—N3—C7—C6	−2.3 (4)
O3—Ni1—O1—C1	−39.7 (18)	O4—C6—C7—N3	−174.6 (4)
O5—Ni1—O1—C1	−84.9 (3)	O3—C6—C7—N3	4.9 (5)
N1—Ni1—O1—C1	4.1 (3)	O4—C6—C7—C8	6.3 (6)
N3—Ni1—O1—C1	−175.3 (3)	O3—C6—C7—C8	−174.1 (3)
N4ⁱ—Ni1—O1—C1	95.2 (3)	C9—N4—C8—C7	3.2 (6)
O1—Ni1—O3—C6	−133.0 (16)	Ni1ⁱⁱ—N4—C8—C7	−171.4 (3)
O5—Ni1—O3—C6	−87.9 (3)	N3—C7—C8—N4	−1.8 (6)
N1—Ni1—O3—C6	−176.4 (3)	C6—C7—C8—N4	177.2 (4)
N3—Ni1—O3—C6	3.1 (3)	C8—N4—C9—C10	−2.0 (6)
N4ⁱ—Ni1—O3—C6	92.2 (3)	Ni1ⁱⁱ—N4—C9—C10	172.5 (3)
Ni1—O1—C1—O2	177.7 (4)	C7—N3—C10—C9	2.2 (6)
Ni1—O1—C1—C2	−1.7 (5)	Ni1—N3—C10—C9	−175.0 (3)
C5—N1—C2—C3	0.8 (6)	N4—C9—C10—N3	−0.7 (7)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H2···O3ⁱⁱⁱ	0.85	2.06	2.763 (4)	140
O5—H1···O1^iv	0.85	1.85	2.695 (4)	173

Symmetry codes: (iii) x+1/2, −y+3/2, −z+1; (iv) x−1/2, −y+3/2, −z+1.

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Retracted: Poly[aqua­bis(μ-pyrazine-2-carboxyl­ato)nickel(II)]

Supporting information

Key indicators

checkCIF/PLATON results

Retracted: Poly[aquabis(μ-pyrazine-2-carboxylato)nickel(II)]