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In the title compound, {[Cu(C6H3N2O4)2]·2C3H7NO}n, each copper(II) center is surrounded by two N atoms, two bridging carboxylate O atoms from two pyrazine-2,3-dicarboxylate anions, and two bridging carboxylate O atoms of two pyrazine-2,3-dicarboxylate anions from neighboring units, forming an elongated CuN2O4 octahedron. The [Cu(C6H3N2O4)2] blocks, with the copper(II) cation located on a center of inversion, are connected together by four μ-carboxylate bridges, creating a one-dimensional intersecting double chain.
Supporting information
CCDC reference: 239079
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.013 Å
- R factor = 0.096
- wR factor = 0.264
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.264
PLAT084_ALERT_2_C High R2 Value .................................. 0.26
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.51
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... N3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.17
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
bis(hydrogen pyrazine-2,3-dicarboxylate)copper(II)
N,
N'-dimethylformamide disolvate
top
Crystal data top
[Cu(C6H3N2O4)2]·2C3H7NO | Z = 1 |
Mr = 543.94 | F(000) = 279 |
Triclinic, P1 | Dx = 1.609 Mg m−3 |
Hall symbol: -P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.289 (2) Å | Cell parameters from 1209 reflections |
b = 7.679 (3) Å | θ = 2.9–23.3° |
c = 12.686 (5) Å | µ = 1.04 mm−1 |
α = 76.147 (7)° | T = 293 K |
β = 88.002 (7)° | Prism, blue |
γ = 70.902 (7)° | 0.33 × 0.12 × 0.05 mm |
V = 561.5 (4) Å3 | |
Data collection top
Bruker SMART APEX area-detector diffractometer | 2005 independent reflections |
Radiation source: fine-focus sealed tube | 1921 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scan | θmax = 25.2°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −7→7 |
Tmin = 0.861, Tmax = 0.950 | k = −9→9 |
4122 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.096 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.264 | H-atom parameters constrained |
S = 1.23 | w = 1/[σ2(Fo2) + (0.1029P)2 + 3.7409P] where P = (Fo2 + 2Fc2)/3 |
2005 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 1.29 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
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 | Uiso*/Ueq | |
Cu1 | 0.0000 | 1.0000 | 1.0000 | 0.0290 (5) | |
O1 | 0.0967 (11) | 1.2188 (8) | 0.9691 (6) | 0.0465 (18) | |
O2 | 0.3452 (11) | 1.3350 (9) | 0.8725 (6) | 0.0490 (17) | |
O3 | 0.5703 (13) | 1.2231 (11) | 0.6681 (5) | 0.0534 (18) | |
H3 | 0.6400 | 1.2951 | 0.6411 | 0.080* | |
O4 | 0.8282 (12) | 1.1286 (10) | 0.8050 (6) | 0.0558 (19) | |
O5 | 0.7090 (13) | 0.4977 (11) | 0.5917 (6) | 0.061 (2) | |
N1 | 0.2692 (11) | 0.8911 (9) | 0.9220 (5) | 0.0287 (14) | |
N2 | 0.6376 (14) | 0.8056 (11) | 0.7955 (7) | 0.047 (2) | |
N3 | 0.9427 (12) | 0.6665 (11) | 0.5937 (6) | 0.0415 (18) | |
C1 | 0.2624 (14) | 1.2102 (11) | 0.9069 (7) | 0.0343 (19) | |
C2 | 0.3676 (13) | 1.0197 (10) | 0.8793 (6) | 0.0265 (16) | |
C3 | 0.5489 (14) | 0.9786 (12) | 0.8145 (7) | 0.0342 (18) | |
C4 | 0.6645 (15) | 1.1206 (12) | 0.7632 (7) | 0.038 (2) | |
C5 | 0.3548 (15) | 0.7167 (11) | 0.9025 (7) | 0.0365 (19) | |
H5 | 0.2886 | 0.6243 | 0.9305 | 0.044* | |
C6 | 0.5396 (16) | 0.6772 (13) | 0.8411 (8) | 0.046 (2) | |
H6 | 0.6001 | 0.5551 | 0.8305 | 0.055* | |
C7 | 0.8138 (19) | 0.8239 (15) | 0.5074 (10) | 0.063 (3) | |
H7A | 0.7033 | 0.7880 | 0.4755 | 0.094* | |
H7B | 0.9132 | 0.8565 | 0.4529 | 0.094* | |
H7C | 0.7396 | 0.9315 | 0.5368 | 0.094* | |
C8 | 1.130 (2) | 0.6860 (18) | 0.6458 (11) | 0.070 (3) | |
H8A | 1.1839 | 0.5825 | 0.7087 | 0.105* | |
H8B | 1.0831 | 0.8039 | 0.6675 | 0.105* | |
H8C | 1.2489 | 0.6845 | 0.5960 | 0.105* | |
C9 | 0.8722 (17) | 0.5201 (14) | 0.6298 (8) | 0.048 (2) | |
H9 | 0.9525 | 0.4263 | 0.6889 | 0.058* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0306 (8) | 0.0205 (7) | 0.0411 (9) | −0.0138 (6) | 0.0114 (6) | −0.0112 (6) |
O1 | 0.061 (4) | 0.034 (3) | 0.069 (4) | −0.035 (3) | 0.034 (4) | −0.034 (3) |
O2 | 0.057 (4) | 0.032 (3) | 0.067 (5) | −0.025 (3) | 0.018 (3) | −0.015 (3) |
O3 | 0.069 (5) | 0.062 (5) | 0.040 (4) | −0.045 (4) | −0.003 (3) | 0.000 (3) |
O4 | 0.052 (4) | 0.057 (4) | 0.063 (5) | −0.034 (4) | −0.011 (3) | 0.004 (4) |
O5 | 0.067 (5) | 0.062 (5) | 0.062 (5) | −0.038 (4) | 0.008 (4) | −0.006 (4) |
N1 | 0.032 (3) | 0.023 (3) | 0.035 (4) | −0.012 (3) | 0.004 (3) | −0.008 (3) |
N2 | 0.051 (5) | 0.039 (4) | 0.060 (5) | −0.021 (4) | 0.018 (4) | −0.022 (4) |
N3 | 0.038 (4) | 0.039 (4) | 0.047 (5) | −0.011 (3) | 0.001 (3) | −0.010 (3) |
C1 | 0.034 (4) | 0.026 (4) | 0.050 (5) | −0.013 (3) | 0.000 (4) | −0.015 (4) |
C2 | 0.030 (4) | 0.020 (4) | 0.033 (4) | −0.010 (3) | −0.002 (3) | −0.008 (3) |
C3 | 0.034 (4) | 0.027 (4) | 0.044 (5) | −0.013 (3) | −0.002 (4) | −0.009 (4) |
C4 | 0.041 (5) | 0.031 (5) | 0.046 (5) | −0.016 (4) | 0.009 (4) | −0.013 (4) |
C5 | 0.046 (5) | 0.020 (4) | 0.046 (5) | −0.013 (4) | 0.003 (4) | −0.010 (4) |
C6 | 0.054 (6) | 0.029 (5) | 0.061 (6) | −0.015 (4) | 0.014 (5) | −0.024 (4) |
C7 | 0.059 (7) | 0.044 (6) | 0.080 (8) | −0.020 (5) | −0.011 (6) | −0.002 (6) |
C8 | 0.062 (7) | 0.068 (8) | 0.082 (9) | −0.032 (6) | −0.006 (6) | −0.006 (7) |
C9 | 0.051 (6) | 0.045 (6) | 0.051 (6) | −0.021 (5) | 0.015 (5) | −0.008 (5) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.919 (5) | N3—C9 | 1.317 (12) |
Cu1—O1i | 1.919 (5) | N3—C8 | 1.438 (13) |
Cu1—N1 | 1.974 (6) | N3—C7 | 1.451 (13) |
Cu1—N1i | 1.974 (6) | C1—C2 | 1.515 (10) |
Cu1—O4ii | 2.565 (5) | C2—C3 | 1.377 (11) |
Cu1—O4iii | 2.565 (5) | C3—C4 | 1.512 (12) |
O1—C1 | 1.279 (10) | C5—C6 | 1.367 (12) |
O2—C1 | 1.221 (10) | C5—H5 | 0.9300 |
O3—C4 | 1.311 (11) | C6—H6 | 0.9300 |
O3—H3 | 0.8200 | C7—H7A | 0.9600 |
O4—C4 | 1.200 (11) | C7—H7B | 0.9600 |
O5—C9 | 1.228 (12) | C7—H7C | 0.9600 |
N1—C2 | 1.332 (10) | C8—H8A | 0.9600 |
N1—C5 | 1.351 (10) | C8—H8B | 0.9600 |
N2—C6 | 1.337 (12) | C8—H8C | 0.9600 |
N2—C3 | 1.339 (11) | C9—H9 | 0.9300 |
| | | |
O1—Cu1—O1i | 180.000 (2) | C2—C3—C4 | 123.1 (7) |
O1—Cu1—N1 | 83.7 (3) | O4—C4—O3 | 125.8 (8) |
O1i—Cu1—N1 | 96.3 (3) | O4—C4—C3 | 122.4 (8) |
O1—Cu1—N1i | 96.3 (3) | O3—C4—C3 | 111.7 (7) |
O1i—Cu1—N1i | 83.7 (3) | N1—C5—C6 | 119.4 (8) |
N1—Cu1—N1i | 180.000 (2) | N1—C5—H5 | 120.3 |
O4ii—Cu1—O1 | 84.8 (3) | C6—C5—H5 | 120.3 |
O4ii—Cu1—N1 | 81.1 (3) | N2—C6—C5 | 123.2 (8) |
C1—O1—Cu1 | 115.3 (5) | N2—C6—H6 | 118.4 |
C4—O3—H3 | 109.5 | C5—C6—H6 | 118.4 |
C2—N1—C5 | 118.3 (7) | N3—C7—H7A | 109.5 |
C2—N1—Cu1 | 111.4 (5) | N3—C7—H7B | 109.5 |
C5—N1—Cu1 | 130.2 (6) | H7A—C7—H7B | 109.5 |
C6—N2—C3 | 116.7 (8) | N3—C7—H7C | 109.5 |
C9—N3—C8 | 121.8 (9) | H7A—C7—H7C | 109.5 |
C9—N3—C7 | 119.7 (9) | H7B—C7—H7C | 109.5 |
C8—N3—C7 | 118.1 (9) | N3—C8—H8A | 109.5 |
O2—C1—O1 | 126.8 (8) | N3—C8—H8B | 109.5 |
O2—C1—C2 | 118.7 (7) | H8A—C8—H8B | 109.5 |
O1—C1—C2 | 114.4 (7) | N3—C8—H8C | 109.5 |
N1—C2—C3 | 121.3 (7) | H8A—C8—H8C | 109.5 |
N1—C2—C1 | 114.6 (7) | H8B—C8—H8C | 109.5 |
C3—C2—C1 | 124.2 (7) | O5—C9—N3 | 125.2 (10) |
N2—C3—C2 | 121.2 (7) | O5—C9—H9 | 117.4 |
N2—C3—C4 | 115.7 (7) | N3—C9—H9 | 117.4 |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) x−1, y, z; (iii) −x+1, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O5iv | 0.82 | 1.72 | 2.512 (9) | 162 |
Symmetry code: (iv) x, y+1, z. |
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