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In the centrosymmetric title compound, [Cu(C2N3)2(C10H8N2O)2], the CuII atom adopts a distorted octa­hedral geometry, with the equatorial plane formed by two O atoms and two N atoms of two chelating 2,2'-bipyridine N-oxide ligands. The axial positions are occupied by N atoms of two monodentate dicyanamide anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047441/sg2077sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047441/sg2077Isup2.hkl
Contains datablock I

CCDC reference: 630450

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.027
  • wR factor = 0.083
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

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Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - N4 .. 16.34 su
Alert level C PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.70 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 5.38 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - N2 .. 5.10 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12
0 ALERT level A = In general: serious problem 1 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 7 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 0 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 (Sheldrick, 1999); software used to prepare material for publication: SHELXTL.

Bis(2,2'-bipyridine N-oxide)bis(dicyanamido)copper(II) top
Crystal data top
[Cu(C2N3)2(C10H8N2O)2]F(000) = 550
Mr = 540.01Dx = 1.595 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p2ybcCell parameters from 25 reflections
a = 10.206 (2) Åθ = 2.1–25.3°
b = 8.0840 (16) ŵ = 1.02 mm1
c = 13.638 (3) ÅT = 298 K
β = 92.56 (3)°Block, green
V = 1124.1 (4) Å30.18 × 0.16 × 0.15 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer
2667 independent reflections
Radiation source: fine-focus sealed tube2376 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.830, Tmax = 0.856k = 1010
9715 measured reflectionsl = 1717
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)] = 0.027H-atom parameters constrained
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0427P)2 + 0.381P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2667 reflectionsΔρmax = 0.32 e Å3
169 parametersΔρmin = 0.38 e Å3
0 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0076 (13)
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
Cu10.50000.00000.50000.02565 (10)
O10.35553 (10)0.04937 (13)0.40476 (8)0.0283 (2)
N10.31695 (12)0.20832 (15)0.40207 (9)0.0256 (3)
N20.60380 (12)0.17285 (15)0.43051 (9)0.0264 (3)
N30.01728 (18)0.1355 (3)0.61789 (18)0.0692 (6)
N40.40599 (15)0.2095 (2)0.61252 (12)0.0430 (3)
N50.18999 (19)0.2576 (3)0.67908 (15)0.0672 (6)
C10.18821 (15)0.2389 (2)0.41171 (12)0.0332 (3)
H1A0.13020.15170.41930.040*
C20.14285 (17)0.3987 (2)0.41028 (14)0.0404 (4)
H2A0.05410.41960.41720.049*
C30.22881 (19)0.5284 (2)0.39855 (15)0.0416 (4)
H3A0.19910.63720.39840.050*
C40.36011 (18)0.49340 (19)0.38702 (14)0.0355 (4)
H4A0.41890.57950.37830.043*
C50.40476 (14)0.33155 (18)0.38841 (11)0.0271 (3)
C60.54419 (14)0.29080 (18)0.37422 (11)0.0265 (3)
C70.61083 (16)0.3791 (2)0.30490 (12)0.0332 (3)
H7A0.56750.45950.26690.040*
C80.74220 (17)0.3468 (2)0.29267 (13)0.0381 (4)
H8A0.78790.40290.24540.046*
C90.80396 (16)0.2300 (2)0.35186 (14)0.0374 (4)
H9A0.89260.20710.34600.045*
C100.73232 (15)0.1473 (2)0.42005 (12)0.0325 (3)
H10A0.77520.07020.46070.039*
C110.08167 (18)0.1897 (2)0.64381 (14)0.0430 (4)
C120.30223 (18)0.2282 (2)0.64098 (12)0.0374 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02130 (15)0.02481 (15)0.03060 (15)0.00318 (9)0.00179 (10)0.00596 (9)
O10.0269 (5)0.0231 (5)0.0345 (5)0.0011 (4)0.0047 (4)0.0001 (4)
N10.0253 (6)0.0259 (6)0.0254 (6)0.0005 (5)0.0022 (5)0.0015 (5)
N20.0232 (6)0.0251 (6)0.0309 (6)0.0019 (5)0.0003 (5)0.0024 (5)
N30.0352 (9)0.0729 (13)0.1003 (16)0.0014 (9)0.0110 (10)0.0118 (12)
N40.0370 (8)0.0441 (9)0.0474 (8)0.0061 (6)0.0023 (7)0.0022 (7)
N50.0530 (11)0.0876 (15)0.0627 (11)0.0182 (10)0.0208 (9)0.0339 (11)
C10.0235 (7)0.0392 (9)0.0366 (8)0.0018 (6)0.0006 (6)0.0009 (7)
C20.0285 (8)0.0444 (10)0.0483 (9)0.0078 (7)0.0015 (7)0.0025 (8)
C30.0402 (10)0.0328 (9)0.0516 (11)0.0105 (7)0.0015 (8)0.0023 (7)
C40.0345 (9)0.0274 (8)0.0443 (9)0.0003 (6)0.0003 (7)0.0024 (6)
C50.0262 (7)0.0270 (7)0.0278 (7)0.0008 (5)0.0005 (5)0.0023 (5)
C60.0266 (7)0.0248 (7)0.0280 (7)0.0029 (5)0.0006 (5)0.0002 (5)
C70.0348 (8)0.0307 (8)0.0342 (8)0.0021 (6)0.0033 (6)0.0063 (6)
C80.0361 (9)0.0379 (9)0.0411 (9)0.0075 (7)0.0114 (7)0.0036 (7)
C90.0265 (8)0.0356 (9)0.0508 (10)0.0034 (6)0.0082 (7)0.0004 (7)
C100.0256 (7)0.0295 (8)0.0422 (8)0.0012 (6)0.0004 (6)0.0030 (6)
C110.0390 (10)0.0425 (10)0.0486 (10)0.0055 (8)0.0141 (8)0.0004 (8)
C120.0435 (10)0.0376 (9)0.0308 (8)0.0084 (7)0.0018 (7)0.0021 (7)
Geometric parameters (Å, º) top
Cu1—O11.9620 (12)C2—C31.381 (3)
Cu1—O1i1.9620 (12)C2—H2A0.9300
Cu1—N22.0156 (13)C3—C41.385 (3)
Cu1—N2i2.0156 (13)C3—H3A0.9300
Cu1—N42.5052 (17)C4—C51.385 (2)
O1—N11.3439 (16)C4—H4A0.9300
N1—C11.3492 (19)C5—C61.482 (2)
N1—C51.3584 (19)C6—C71.387 (2)
N2—C101.3417 (19)C7—C81.383 (2)
N2—C61.3516 (19)C7—H7A0.9300
N3—C111.142 (3)C8—C91.377 (3)
N4—C121.154 (2)C8—H8A0.9300
N5—C121.301 (3)C9—C101.381 (2)
N5—C111.307 (3)C9—H9A0.9300
C1—C21.372 (2)C10—H10A0.9300
C1—H1A0.9300
O1—Cu1—O1i180.00 (5)C2—C3—H3A120.6
O1—Cu1—N286.73 (5)C4—C3—H3A120.6
O1i—Cu1—N293.27 (5)C5—C4—C3120.71 (16)
O1—Cu1—N2i93.27 (5)C5—C4—H4A119.6
O1i—Cu1—N2i86.73 (5)C3—C4—H4A119.6
N2—Cu1—N2i180.0N1—C5—C4118.41 (14)
O1—Cu1—N488.34 (5)N1—C5—C6119.88 (13)
O1i—Cu1—N491.66 (5)C4—C5—C6121.70 (14)
N2—Cu1—N492.46 (6)N2—C6—C7121.89 (14)
N2i—Cu1—N487.54 (6)N2—C6—C5119.56 (13)
N1—O1—Cu1115.04 (8)C7—C6—C5118.52 (14)
O1—N1—C1117.27 (12)C8—C7—C6119.49 (15)
O1—N1—C5120.70 (12)C8—C7—H7A120.3
C1—N1—C5122.02 (13)C6—C7—H7A120.3
C10—N2—C6117.77 (13)C9—C8—C7118.67 (15)
C10—N2—Cu1118.68 (10)C9—C8—H8A120.7
C6—N2—Cu1121.56 (10)C7—C8—H8A120.7
C12—N4—Cu1132.57 (13)C8—C9—C10118.99 (15)
C12—N5—C11121.47 (18)C8—C9—H9A120.5
N1—C1—C2120.06 (15)C10—C9—H9A120.5
N1—C1—H1A120.0N2—C10—C9123.12 (15)
C2—C1—H1A120.0N2—C10—H10A118.4
C1—C2—C3120.05 (16)C9—C10—H10A118.4
C1—C2—H2A120.0N3—C11—N5175.4 (2)
C3—C2—H2A120.0N4—C12—N5174.90 (19)
C2—C3—C4118.73 (16)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···N4ii0.932.473.386 (2)169
Symmetry code: (ii) x+1, y+1, z+1.
 

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