Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009249/cv6298sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009249/cv6298Isup2.hkl
Contains datablock I

CCDC reference: 239079

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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]·2C3H7NOZ = 1
Mr = 543.94F(000) = 279
Triclinic, P1Dx = 1.609 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 6.289 (2) ÅCell parameters from 1209 reflections
b = 7.679 (3) Åθ = 2.9–23.3°
c = 12.686 (5) ŵ = 1.04 mm1
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 tube1921 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scanθmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 77
Tmin = 0.861, Tmax = 0.950k = 99
4122 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.096Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.264H-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 parametersΔρmax = 1.29 e Å3
0 restraintsΔρmin = 0.51 e Å3
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
Cu10.00001.00001.00000.0290 (5)
O10.0967 (11)1.2188 (8)0.9691 (6)0.0465 (18)
O20.3452 (11)1.3350 (9)0.8725 (6)0.0490 (17)
O30.5703 (13)1.2231 (11)0.6681 (5)0.0534 (18)
H30.64001.29510.64110.080*
O40.8282 (12)1.1286 (10)0.8050 (6)0.0558 (19)
O50.7090 (13)0.4977 (11)0.5917 (6)0.061 (2)
N10.2692 (11)0.8911 (9)0.9220 (5)0.0287 (14)
N20.6376 (14)0.8056 (11)0.7955 (7)0.047 (2)
N30.9427 (12)0.6665 (11)0.5937 (6)0.0415 (18)
C10.2624 (14)1.2102 (11)0.9069 (7)0.0343 (19)
C20.3676 (13)1.0197 (10)0.8793 (6)0.0265 (16)
C30.5489 (14)0.9786 (12)0.8145 (7)0.0342 (18)
C40.6645 (15)1.1206 (12)0.7632 (7)0.038 (2)
C50.3548 (15)0.7167 (11)0.9025 (7)0.0365 (19)
H50.28860.62430.93050.044*
C60.5396 (16)0.6772 (13)0.8411 (8)0.046 (2)
H60.60010.55510.83050.055*
C70.8138 (19)0.8239 (15)0.5074 (10)0.063 (3)
H7A0.70330.78800.47550.094*
H7B0.91320.85650.45290.094*
H7C0.73960.93150.53680.094*
C81.130 (2)0.6860 (18)0.6458 (11)0.070 (3)
H8A1.18390.58250.70870.105*
H8B1.08310.80390.66750.105*
H8C1.24890.68450.59600.105*
C90.8722 (17)0.5201 (14)0.6298 (8)0.048 (2)
H90.95250.42630.68890.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0306 (8)0.0205 (7)0.0411 (9)0.0138 (6)0.0114 (6)0.0112 (6)
O10.061 (4)0.034 (3)0.069 (4)0.035 (3)0.034 (4)0.034 (3)
O20.057 (4)0.032 (3)0.067 (5)0.025 (3)0.018 (3)0.015 (3)
O30.069 (5)0.062 (5)0.040 (4)0.045 (4)0.003 (3)0.000 (3)
O40.052 (4)0.057 (4)0.063 (5)0.034 (4)0.011 (3)0.004 (4)
O50.067 (5)0.062 (5)0.062 (5)0.038 (4)0.008 (4)0.006 (4)
N10.032 (3)0.023 (3)0.035 (4)0.012 (3)0.004 (3)0.008 (3)
N20.051 (5)0.039 (4)0.060 (5)0.021 (4)0.018 (4)0.022 (4)
N30.038 (4)0.039 (4)0.047 (5)0.011 (3)0.001 (3)0.010 (3)
C10.034 (4)0.026 (4)0.050 (5)0.013 (3)0.000 (4)0.015 (4)
C20.030 (4)0.020 (4)0.033 (4)0.010 (3)0.002 (3)0.008 (3)
C30.034 (4)0.027 (4)0.044 (5)0.013 (3)0.002 (4)0.009 (4)
C40.041 (5)0.031 (5)0.046 (5)0.016 (4)0.009 (4)0.013 (4)
C50.046 (5)0.020 (4)0.046 (5)0.013 (4)0.003 (4)0.010 (4)
C60.054 (6)0.029 (5)0.061 (6)0.015 (4)0.014 (5)0.024 (4)
C70.059 (7)0.044 (6)0.080 (8)0.020 (5)0.011 (6)0.002 (6)
C80.062 (7)0.068 (8)0.082 (9)0.032 (6)0.006 (6)0.006 (7)
C90.051 (6)0.045 (6)0.051 (6)0.021 (5)0.015 (5)0.008 (5)
Geometric parameters (Å, º) top
Cu1—O11.919 (5)N3—C91.317 (12)
Cu1—O1i1.919 (5)N3—C81.438 (13)
Cu1—N11.974 (6)N3—C71.451 (13)
Cu1—N1i1.974 (6)C1—C21.515 (10)
Cu1—O4ii2.565 (5)C2—C31.377 (11)
Cu1—O4iii2.565 (5)C3—C41.512 (12)
O1—C11.279 (10)C5—C61.367 (12)
O2—C11.221 (10)C5—H50.9300
O3—C41.311 (11)C6—H60.9300
O3—H30.8200C7—H7A0.9600
O4—C41.200 (11)C7—H7B0.9600
O5—C91.228 (12)C7—H7C0.9600
N1—C21.332 (10)C8—H8A0.9600
N1—C51.351 (10)C8—H8B0.9600
N2—C61.337 (12)C8—H8C0.9600
N2—C31.339 (11)C9—H90.9300
O1—Cu1—O1i180.000 (2)C2—C3—C4123.1 (7)
O1—Cu1—N183.7 (3)O4—C4—O3125.8 (8)
O1i—Cu1—N196.3 (3)O4—C4—C3122.4 (8)
O1—Cu1—N1i96.3 (3)O3—C4—C3111.7 (7)
O1i—Cu1—N1i83.7 (3)N1—C5—C6119.4 (8)
N1—Cu1—N1i180.000 (2)N1—C5—H5120.3
O4ii—Cu1—O184.8 (3)C6—C5—H5120.3
O4ii—Cu1—N181.1 (3)N2—C6—C5123.2 (8)
C1—O1—Cu1115.3 (5)N2—C6—H6118.4
C4—O3—H3109.5C5—C6—H6118.4
C2—N1—C5118.3 (7)N3—C7—H7A109.5
C2—N1—Cu1111.4 (5)N3—C7—H7B109.5
C5—N1—Cu1130.2 (6)H7A—C7—H7B109.5
C6—N2—C3116.7 (8)N3—C7—H7C109.5
C9—N3—C8121.8 (9)H7A—C7—H7C109.5
C9—N3—C7119.7 (9)H7B—C7—H7C109.5
C8—N3—C7118.1 (9)N3—C8—H8A109.5
O2—C1—O1126.8 (8)N3—C8—H8B109.5
O2—C1—C2118.7 (7)H8A—C8—H8B109.5
O1—C1—C2114.4 (7)N3—C8—H8C109.5
N1—C2—C3121.3 (7)H8A—C8—H8C109.5
N1—C2—C1114.6 (7)H8B—C8—H8C109.5
C3—C2—C1124.2 (7)O5—C9—N3125.2 (10)
N2—C3—C2121.2 (7)O5—C9—H9117.4
N2—C3—C4115.7 (7)N3—C9—H9117.4
Symmetry codes: (i) x, y+2, z+2; (ii) x1, y, z; (iii) x+1, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O5iv0.821.722.512 (9)162
Symmetry code: (iv) x, y+1, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds