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In the title complex, [Cu(C8H4NO2)2(C5H6N2)2]n, the two crystallographically distinct Cu atoms each lie on an inversion centre and are coordinated by N atoms from four 3-amino­pyridine ligands, two from the amino groups and two from the pyridine rings. The octa­hedral coordination about each Cu atom is completed by two carboxyl­ate O atoms from different 4-cyano­benzoate ligands. The 3-amino­pyridines serve as bridging ligands, linking adjacent Cu atoms into one-dimensional chains. In the crystal structure, weak N—H...O hydrogen-bonding inter­actions form a two-dimensional layer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042820/sj6192sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042820/sj6192Isup2.hkl
Contains datablock I

CCDC reference: 298546

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.057
  • wR factor = 0.132
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 3.26 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C13 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C23 - C26 ... 1.46 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2B ... ?
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 5 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 0 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

catena-Poly[[bis(4-cyanobenzoato-κO)copper(II)]-di-µ-3-aminopyridine- κ2N1:N3;κ2N3:N1] top
Crystal data top
[Cu(C8H4NO2)2(C5H6N2)2]Z = 2
Mr = 544.02F(000) = 558
Triclinic, P1Dx = 1.521 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3906 (9) ÅCell parameters from 1217 reflections
b = 13.613 (2) Åθ = 5.3–44.8°
c = 15.466 (3) ŵ = 0.97 mm1
α = 63.894 (3)°T = 295 K
β = 81.922 (4)°Plate, green
γ = 80.455 (3)°0.46 × 0.22 × 0.05 mm
V = 1188.0 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4151 independent reflections
Radiation source: fine-focus sealed tube2697 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
φ and ω scansθmax = 25.1°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 77
Tmin = 0.666, Tmax = 0.951k = 1613
6040 measured reflectionsl = 1818
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0398P)2]
where P = (Fo2 + 2Fc2)/3
4151 reflections(Δ/σ)max < 0.001
349 parametersΔρmax = 0.53 e Å3
4 restraintsΔρmin = 0.47 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
Cu11.00000.50000.00000.0304 (3)
Cu21.00000.50000.50000.0371 (3)
O10.8449 (5)0.5883 (3)0.0641 (2)0.0345 (8)
O21.0703 (5)0.5976 (3)0.1580 (2)0.0434 (9)
O30.8420 (5)0.6445 (3)0.4728 (2)0.0391 (9)
O41.0792 (6)0.7606 (3)0.3809 (3)0.0547 (11)
N10.7909 (6)0.3868 (3)0.0707 (3)0.0284 (9)
N20.2262 (7)0.3897 (4)0.1482 (3)0.0367 (10)
N30.1805 (9)1.0372 (5)0.1629 (5)0.093 (2)
N40.8073 (6)0.4805 (3)0.4135 (3)0.0309 (10)
N50.2657 (6)0.5773 (4)0.3400 (3)0.0353 (10)
N60.1252 (9)1.1718 (4)0.3588 (4)0.0771 (18)
C10.5913 (7)0.4173 (4)0.0951 (3)0.0289 (11)
H10.55610.48950.08770.035*
C20.4325 (8)0.3484 (4)0.1310 (3)0.0305 (12)
C30.4885 (8)0.2411 (4)0.1439 (4)0.0391 (13)
H30.38680.19200.16640.047*
C40.6966 (8)0.2072 (4)0.1231 (4)0.0414 (13)
H40.73810.13410.13420.050*
C50.8413 (8)0.2810 (4)0.0861 (3)0.0407 (13)
H50.98070.25730.07100.049*
C60.9015 (8)0.6259 (4)0.1192 (3)0.0312 (12)
C70.7412 (8)0.7130 (4)0.1323 (3)0.0317 (12)
C80.7876 (9)0.7730 (4)0.1772 (4)0.0500 (15)
H80.91900.75690.20270.060*
C90.6438 (10)0.8570 (5)0.1855 (4)0.0534 (16)
H90.68030.89750.21530.064*
C100.4502 (10)0.8803 (5)0.1504 (4)0.0518 (16)
C110.3944 (9)0.8192 (5)0.1067 (5)0.0607 (18)
H110.26050.83360.08370.073*
C120.5419 (9)0.7367 (4)0.0979 (4)0.0501 (15)
H120.50610.69620.06810.060*
C130.2973 (11)0.9673 (5)0.1583 (5)0.0653 (18)
C140.6158 (7)0.5384 (4)0.3964 (3)0.0278 (11)
H140.57980.59370.41750.033*
C150.4658 (7)0.5211 (4)0.3485 (3)0.0275 (11)
C160.5280 (8)0.4418 (4)0.3135 (4)0.0391 (13)
H160.43480.42680.28100.047*
C170.7306 (8)0.3854 (4)0.3277 (3)0.0380 (13)
H170.77550.33340.30310.046*
C180.8654 (8)0.4060 (4)0.3780 (3)0.0361 (13)
H181.00060.36700.38760.043*
C190.9046 (9)0.7393 (4)0.4229 (4)0.0358 (13)
C200.7325 (8)0.8335 (4)0.4158 (3)0.0316 (12)
C210.7837 (8)0.9408 (4)0.3729 (4)0.0372 (13)
H210.92360.95450.35070.045*
C220.6272 (9)1.0269 (4)0.3631 (4)0.0434 (14)
H220.66251.09860.33600.052*
C230.4204 (8)1.0077 (4)0.3930 (4)0.0382 (13)
C240.3656 (8)0.9016 (4)0.4375 (4)0.0423 (14)
H240.22530.88840.45910.051*
C250.5256 (8)0.8154 (4)0.4490 (4)0.0403 (13)
H250.49150.74350.48000.048*
C260.2536 (10)1.0996 (5)0.3767 (4)0.0496 (15)
H2A0.205 (9)0.456 (2)0.149 (4)0.080*
H2B0.138 (8)0.339 (4)0.183 (3)0.080*
H5A0.187 (8)0.585 (5)0.294 (3)0.080*
H5B0.232 (9)0.635 (3)0.354 (4)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0265 (5)0.0345 (5)0.0386 (5)0.0018 (4)0.0011 (4)0.0248 (5)
Cu20.0319 (6)0.0241 (5)0.0595 (6)0.0063 (4)0.0225 (5)0.0194 (5)
O10.031 (2)0.038 (2)0.046 (2)0.0014 (16)0.0024 (16)0.0303 (18)
O20.040 (2)0.047 (2)0.056 (2)0.0099 (18)0.0182 (19)0.034 (2)
O30.033 (2)0.024 (2)0.061 (2)0.0082 (16)0.0188 (18)0.0178 (19)
O40.037 (2)0.039 (2)0.088 (3)0.0035 (19)0.004 (2)0.032 (2)
N10.029 (2)0.027 (2)0.032 (2)0.0053 (19)0.0056 (19)0.017 (2)
N20.023 (2)0.040 (3)0.050 (3)0.001 (2)0.000 (2)0.024 (3)
N30.079 (5)0.062 (4)0.147 (6)0.015 (4)0.007 (4)0.065 (4)
N40.026 (2)0.029 (2)0.039 (2)0.0046 (19)0.0097 (19)0.016 (2)
N50.021 (2)0.042 (3)0.049 (3)0.009 (2)0.011 (2)0.028 (2)
N60.078 (4)0.057 (4)0.090 (4)0.036 (3)0.018 (3)0.037 (3)
C10.033 (3)0.024 (3)0.027 (3)0.008 (2)0.008 (2)0.011 (2)
C20.030 (3)0.036 (3)0.034 (3)0.001 (2)0.008 (2)0.022 (3)
C30.038 (3)0.030 (3)0.047 (3)0.009 (3)0.001 (3)0.015 (3)
C40.049 (4)0.023 (3)0.045 (3)0.003 (3)0.002 (3)0.011 (3)
C50.036 (3)0.042 (4)0.037 (3)0.007 (3)0.010 (3)0.012 (3)
C60.038 (3)0.027 (3)0.029 (3)0.005 (2)0.001 (2)0.013 (2)
C70.033 (3)0.032 (3)0.032 (3)0.000 (2)0.002 (2)0.017 (2)
C80.059 (4)0.047 (4)0.054 (4)0.005 (3)0.019 (3)0.030 (3)
C90.074 (5)0.042 (4)0.060 (4)0.008 (3)0.018 (4)0.038 (3)
C100.064 (4)0.039 (4)0.056 (4)0.006 (3)0.002 (3)0.029 (3)
C110.038 (4)0.061 (4)0.099 (5)0.008 (3)0.019 (4)0.050 (4)
C120.052 (4)0.047 (4)0.071 (4)0.008 (3)0.014 (3)0.045 (3)
C130.069 (5)0.048 (4)0.079 (5)0.006 (4)0.000 (4)0.034 (4)
C140.025 (3)0.025 (3)0.035 (3)0.002 (2)0.006 (2)0.015 (2)
C150.028 (3)0.027 (3)0.026 (3)0.006 (2)0.009 (2)0.011 (2)
C160.037 (3)0.047 (4)0.042 (3)0.004 (3)0.012 (3)0.028 (3)
C170.040 (3)0.041 (3)0.041 (3)0.007 (3)0.007 (3)0.027 (3)
C180.028 (3)0.040 (3)0.035 (3)0.008 (2)0.004 (2)0.016 (3)
C190.045 (4)0.028 (3)0.041 (3)0.007 (3)0.020 (3)0.020 (3)
C200.033 (3)0.028 (3)0.036 (3)0.002 (2)0.012 (2)0.015 (2)
C210.035 (3)0.032 (3)0.042 (3)0.003 (2)0.011 (3)0.014 (3)
C220.058 (4)0.026 (3)0.040 (3)0.001 (3)0.006 (3)0.010 (3)
C230.042 (4)0.033 (3)0.039 (3)0.011 (3)0.010 (3)0.018 (3)
C240.035 (3)0.037 (3)0.053 (3)0.004 (3)0.005 (3)0.020 (3)
C250.048 (4)0.024 (3)0.046 (3)0.001 (3)0.009 (3)0.012 (3)
C260.058 (4)0.041 (4)0.044 (3)0.011 (3)0.002 (3)0.020 (3)
Geometric parameters (Å, º) top
Cu1—O11.945 (3)C5—H50.9300
Cu1—O1i1.945 (3)C6—C71.499 (6)
Cu1—N12.036 (4)C7—C81.369 (6)
Cu1—N1i2.036 (4)C7—C121.383 (7)
Cu1—N2ii2.604 (4)C8—C91.385 (7)
Cu2—O31.949 (3)C8—H80.9300
Cu2—O3iii1.949 (3)C9—C101.354 (7)
Cu2—N42.063 (4)C9—H90.9300
Cu2—N4iii2.063 (4)C10—C111.393 (7)
Cu2—N5ii2.689 (5)C10—C131.442 (8)
O1—C61.286 (5)C11—C121.384 (7)
O2—C61.230 (5)C11—H110.9300
O3—C191.277 (6)C12—H120.9300
O4—C191.220 (6)C14—C151.397 (6)
N1—C11.330 (6)C14—H140.9300
N1—C51.341 (6)C15—C161.387 (6)
N2—C21.383 (6)C16—C171.384 (7)
N2—H2A0.90 (4)C16—H160.9300
N2—H2B0.90 (5)C17—C181.374 (6)
N3—C131.131 (7)C17—H170.9300
N4—C141.333 (5)C18—H180.9300
N4—C181.333 (6)C19—C201.520 (7)
N5—C151.369 (6)C20—C251.370 (7)
N5—H5A0.89 (5)C20—C211.387 (6)
N5—H5B0.89 (5)C21—C221.377 (7)
N6—C261.128 (7)C21—H210.9300
C1—C21.384 (6)C22—C231.366 (7)
C1—H10.9300C22—H220.9300
C2—C31.376 (6)C23—C241.381 (7)
C3—C41.376 (7)C23—C261.456 (7)
C3—H30.9300C24—C251.387 (7)
C4—C51.359 (6)C24—H240.9300
C4—H40.9300C25—H250.9300
O1—Cu1—O1i180.00 (15)C12—C7—C6121.0 (4)
O1—Cu1—N188.41 (14)C7—C8—C9121.6 (5)
O1i—Cu1—N191.59 (14)C7—C8—H8119.2
O1—Cu1—N1i91.59 (14)C9—C8—H8119.2
O1i—Cu1—N1i88.41 (14)C10—C9—C8120.1 (5)
N1—Cu1—N1i180.00 (18)C10—C9—H9120.0
O1—Cu1—N2ii89.92 (13)C8—C9—H9120.0
O1i—Cu1—N2ii90.08 (13)C9—C10—C11120.1 (5)
N1—Cu1—N2ii86.04 (14)C9—C10—C13121.2 (6)
N1i—Cu1—N2ii93.96 (14)C11—C10—C13118.7 (6)
O3—Cu2—O3iii180.0 (2)C12—C11—C10118.8 (5)
O3—Cu2—N488.82 (14)C12—C11—H11120.6
O3iii—Cu2—N491.18 (14)C10—C11—H11120.6
O3—Cu2—N4iii91.18 (14)C7—C12—C11121.7 (5)
O3iii—Cu2—N4iii88.82 (14)C7—C12—H12119.1
N4—Cu2—N4iii180.0 (2)C11—C12—H12119.1
O3—Cu2—N5ii93.43 (14)N3—C13—C10178.3 (9)
O3iii—Cu2—N5ii86.57 (14)N4—C14—C15124.0 (4)
N4—Cu2—N5ii85.57 (14)N4—C14—H14118.0
N4iii—Cu2—N5ii94.43 (14)C15—C14—H14118.0
C6—O1—Cu1132.7 (3)N5—C15—C16122.3 (4)
C19—O3—Cu2128.6 (3)N5—C15—C14121.0 (4)
C1—N1—C5117.1 (4)C16—C15—C14116.6 (4)
C1—N1—Cu1120.9 (3)C17—C16—C15119.2 (4)
C5—N1—Cu1121.7 (3)C17—C16—H16120.4
C2—N2—H2A118 (4)C15—C16—H16120.4
C2—N2—H2B115 (4)C18—C17—C16120.0 (5)
H2A—N2—H2B121 (5)C18—C17—H17120.0
C14—N4—C18118.4 (4)C16—C17—H17120.0
C14—N4—Cu2120.4 (3)N4—C18—C17121.7 (5)
C18—N4—Cu2121.2 (3)N4—C18—H18119.2
C15—N5—H5A121 (4)C17—C18—H18119.2
C15—N5—H5B122 (4)O4—C19—O3127.9 (5)
H5A—N5—H5B110 (5)O4—C19—C20118.9 (5)
N1—C1—C2124.2 (4)O3—C19—C20113.2 (5)
N1—C1—H1117.9C25—C20—C21118.9 (5)
C2—C1—H1117.9C25—C20—C19121.5 (5)
C3—C2—N2122.8 (5)C21—C20—C19119.6 (5)
C3—C2—C1117.1 (5)C22—C21—C20120.0 (5)
N2—C2—C1120.0 (4)C22—C21—H21120.0
C4—C3—C2119.2 (5)C20—C21—H21120.0
C4—C3—H3120.4C23—C22—C21120.3 (5)
C2—C3—H3120.4C23—C22—H22119.8
C5—C4—C3119.7 (5)C21—C22—H22119.8
C5—C4—H4120.1C22—C23—C24120.9 (5)
C3—C4—H4120.1C22—C23—C26120.1 (5)
N1—C5—C4122.5 (5)C24—C23—C26119.0 (5)
N1—C5—H5118.7C23—C24—C25118.2 (5)
C4—C5—H5118.7C23—C24—H24120.9
O2—C6—O1125.7 (5)C25—C24—H24120.9
O2—C6—C7120.7 (4)C20—C25—C24121.7 (5)
O1—C6—C7113.6 (4)C20—C25—H25119.1
C8—C7—C12117.6 (5)C24—C25—H25119.1
C8—C7—C6121.4 (4)N6—C26—C23176.1 (6)
N1—Cu1—O1—C6122.5 (4)C6—C7—C8—C9176.9 (5)
N1i—Cu1—O1—C657.5 (4)C7—C8—C9—C101.2 (9)
N2ii—Cu1—O1—C636.5 (4)C8—C9—C10—C110.6 (9)
N4—Cu2—O3—C19110.7 (4)C8—C9—C10—C13179.9 (6)
N4iii—Cu2—O3—C1969.3 (4)C9—C10—C11—C121.5 (10)
N5ii—Cu2—O3—C1925.2 (4)C13—C10—C11—C12179.2 (6)
O1—Cu1—N1—C129.7 (3)C8—C7—C12—C111.0 (9)
O1i—Cu1—N1—C1150.3 (3)C6—C7—C12—C11177.9 (5)
N2ii—Cu1—N1—C1119.7 (3)C10—C11—C12—C70.7 (10)
O1—Cu1—N1—C5156.8 (4)C18—N4—C14—C154.2 (7)
O1i—Cu1—N1—C523.2 (4)Cu2—N4—C14—C15172.1 (3)
N2ii—Cu1—N1—C566.8 (4)N4—C14—C15—N5174.6 (5)
O3—Cu2—N4—C1422.3 (4)N4—C14—C15—C163.1 (7)
O3iii—Cu2—N4—C14157.7 (4)N5—C15—C16—C17177.7 (5)
N5ii—Cu2—N4—C14115.8 (4)C14—C15—C16—C170.0 (7)
O3—Cu2—N4—C18161.5 (4)C15—C16—C17—C181.7 (8)
O3iii—Cu2—N4—C1818.5 (4)C14—N4—C18—C172.3 (7)
N5ii—Cu2—N4—C1868.0 (4)Cu2—N4—C18—C17174.0 (3)
C5—N1—C1—C23.1 (7)C16—C17—C18—N40.6 (8)
Cu1—N1—C1—C2170.7 (3)Cu2—O3—C19—O40.2 (7)
N1—C1—C2—C31.6 (7)Cu2—O3—C19—C20178.4 (3)
N1—C1—C2—N2175.6 (4)O4—C19—C20—C25170.2 (5)
N2—C2—C3—C4178.5 (4)O3—C19—C20—C258.6 (6)
C1—C2—C3—C41.5 (7)O4—C19—C20—C218.2 (7)
C2—C3—C4—C53.0 (8)O3—C19—C20—C21173.0 (4)
C1—N1—C5—C41.5 (7)C25—C20—C21—C220.8 (7)
Cu1—N1—C5—C4172.2 (4)C19—C20—C21—C22177.7 (4)
C3—C4—C5—N11.5 (8)C20—C21—C22—C231.9 (7)
Cu1—O1—C6—O213.2 (7)C21—C22—C23—C243.0 (8)
Cu1—O1—C6—C7165.7 (3)C21—C22—C23—C26175.9 (5)
O2—C6—C7—C88.3 (7)C22—C23—C24—C251.4 (8)
O1—C6—C7—C8170.6 (4)C26—C23—C24—C25177.5 (5)
O2—C6—C7—C12172.8 (5)C21—C20—C25—C242.4 (7)
O1—C6—C7—C128.2 (7)C19—C20—C25—C24176.0 (5)
C12—C7—C8—C92.0 (8)C23—C24—C25—C201.3 (8)
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y, z; (iii) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2iv0.90 (4)2.03 (2)2.903 (5)164 (5)
N5—H5A···O2iv0.89 (5)2.26 (5)3.122 (5)165 (5)
N5—H5B···O4iv0.89 (5)2.00 (5)2.871 (5)165 (5)
Symmetry code: (iv) x1, y, z.
 

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