Bis(2,2'-bipyridine N-oxide)bis­(dicyanamido)copper(II)

In the centrosymmetric title compound, [Cu(C₂N₃)₂(C₁₀H₈N₂O)₂], the Cu^II 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.

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

No syntax errors found



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

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)

Crystal data

[Cu(C2N3)2(C10H8N2O)2]	F(000) = 550
Mr = 540.01	Dx = 1.595 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p2ybc	Cell parameters from 25 reflections
a = 10.206 (2) Å	θ = 2.1–25.3°
b = 8.0840 (16) Å	µ = 1.02 mm^−1
c = 13.638 (3) Å	T = 298 K
β = 92.56 (3)°	Block, green
V = 1124.1 (4) Å^3	0.18 × 0.16 × 0.15 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer	2667 independent reflections
Radiation source: fine-focus sealed tube	2376 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.830, Tmax = 0.856	k = −10→10
9715 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0427P)^2 + 0.381P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2667 reflections	Δρmax = 0.32 e Å^−3
169 parameters	Δρmin = −0.38 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0076 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.0000	0.5000	0.02565 (10)
O1	0.35553 (10)	0.04937 (13)	0.40476 (8)	0.0283 (2)
N1	0.31695 (12)	0.20832 (15)	0.40207 (9)	0.0256 (3)
N2	0.60380 (12)	0.17285 (15)	0.43051 (9)	0.0264 (3)
N3	−0.01728 (18)	0.1355 (3)	0.61789 (18)	0.0692 (6)
N4	0.40599 (15)	0.2095 (2)	0.61252 (12)	0.0430 (3)
N5	0.18999 (19)	0.2576 (3)	0.67908 (15)	0.0672 (6)
C1	0.18821 (15)	0.2389 (2)	0.41171 (12)	0.0332 (3)
H1A	0.1302	0.1517	0.4193	0.040*
C2	0.14285 (17)	0.3987 (2)	0.41028 (14)	0.0404 (4)
H2A	0.0541	0.4196	0.4172	0.049*
C3	0.22881 (19)	0.5284 (2)	0.39855 (15)	0.0416 (4)
H3A	0.1991	0.6372	0.3984	0.050*
C4	0.36011 (18)	0.49340 (19)	0.38702 (14)	0.0355 (4)
H4A	0.4189	0.5795	0.3783	0.043*
C5	0.40476 (14)	0.33155 (18)	0.38841 (11)	0.0271 (3)
C6	0.54419 (14)	0.29080 (18)	0.37422 (11)	0.0265 (3)
C7	0.61083 (16)	0.3791 (2)	0.30490 (12)	0.0332 (3)
H7A	0.5675	0.4595	0.2669	0.040*
C8	0.74220 (17)	0.3468 (2)	0.29267 (13)	0.0381 (4)
H8A	0.7879	0.4029	0.2454	0.046*
C9	0.80396 (16)	0.2300 (2)	0.35186 (14)	0.0374 (4)
H9A	0.8926	0.2071	0.3460	0.045*
C10	0.73232 (15)	0.1473 (2)	0.42005 (12)	0.0325 (3)
H10A	0.7752	0.0702	0.4607	0.039*
C11	0.08167 (18)	0.1897 (2)	0.64381 (14)	0.0430 (4)
C12	0.30223 (18)	0.2282 (2)	0.64098 (12)	0.0374 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.02130 (15)	0.02481 (15)	0.03060 (15)	−0.00318 (9)	−0.00179 (10)	0.00596 (9)
O1	0.0269 (5)	0.0231 (5)	0.0345 (5)	−0.0011 (4)	−0.0047 (4)	−0.0001 (4)
N1	0.0253 (6)	0.0259 (6)	0.0254 (6)	0.0005 (5)	−0.0022 (5)	0.0015 (5)
N2	0.0232 (6)	0.0251 (6)	0.0309 (6)	−0.0019 (5)	0.0003 (5)	0.0024 (5)
N3	0.0352 (9)	0.0729 (13)	0.1003 (16)	0.0014 (9)	0.0110 (10)	−0.0118 (12)
N4	0.0370 (8)	0.0441 (9)	0.0474 (8)	−0.0061 (6)	−0.0023 (7)	−0.0022 (7)
N5	0.0530 (11)	0.0876 (15)	0.0627 (11)	−0.0182 (10)	0.0208 (9)	−0.0339 (11)
C1	0.0235 (7)	0.0392 (9)	0.0366 (8)	−0.0018 (6)	−0.0006 (6)	0.0009 (7)
C2	0.0285 (8)	0.0444 (10)	0.0483 (9)	0.0078 (7)	0.0015 (7)	−0.0025 (8)
C3	0.0402 (10)	0.0328 (9)	0.0516 (11)	0.0105 (7)	−0.0015 (8)	−0.0023 (7)
C4	0.0345 (9)	0.0274 (8)	0.0443 (9)	−0.0003 (6)	−0.0003 (7)	0.0024 (6)
C5	0.0262 (7)	0.0270 (7)	0.0278 (7)	−0.0008 (5)	−0.0005 (5)	0.0023 (5)
C6	0.0266 (7)	0.0248 (7)	0.0280 (7)	−0.0029 (5)	0.0006 (5)	0.0002 (5)
C7	0.0348 (8)	0.0307 (8)	0.0342 (8)	−0.0021 (6)	0.0033 (6)	0.0063 (6)
C8	0.0361 (9)	0.0379 (9)	0.0411 (9)	−0.0075 (7)	0.0114 (7)	0.0036 (7)
C9	0.0265 (8)	0.0356 (9)	0.0508 (10)	−0.0034 (6)	0.0082 (7)	0.0004 (7)
C10	0.0256 (7)	0.0295 (8)	0.0422 (8)	−0.0012 (6)	−0.0004 (6)	0.0030 (6)
C11	0.0390 (10)	0.0425 (10)	0.0486 (10)	0.0055 (8)	0.0141 (8)	0.0004 (8)
C12	0.0435 (10)	0.0376 (9)	0.0308 (8)	−0.0084 (7)	−0.0018 (7)	−0.0021 (7)

Geometric parameters (Å, º)

Cu1—O1	1.9620 (12)	C2—C3	1.381 (3)
Cu1—O1^i	1.9620 (12)	C2—H2A	0.9300
Cu1—N2	2.0156 (13)	C3—C4	1.385 (3)
Cu1—N2^i	2.0156 (13)	C3—H3A	0.9300
Cu1—N4	2.5052 (17)	C4—C5	1.385 (2)
O1—N1	1.3439 (16)	C4—H4A	0.9300
N1—C1	1.3492 (19)	C5—C6	1.482 (2)
N1—C5	1.3584 (19)	C6—C7	1.387 (2)
N2—C10	1.3417 (19)	C7—C8	1.383 (2)
N2—C6	1.3516 (19)	C7—H7A	0.9300
N3—C11	1.142 (3)	C8—C9	1.377 (3)
N4—C12	1.154 (2)	C8—H8A	0.9300
N5—C12	1.301 (3)	C9—C10	1.381 (2)
N5—C11	1.307 (3)	C9—H9A	0.9300
C1—C2	1.372 (2)	C10—H10A	0.9300
C1—H1A	0.9300
O1—Cu1—O1^i	180.00 (5)	C2—C3—H3A	120.6
O1—Cu1—N2	86.73 (5)	C4—C3—H3A	120.6
O1^i—Cu1—N2	93.27 (5)	C5—C4—C3	120.71 (16)
O1—Cu1—N2^i	93.27 (5)	C5—C4—H4A	119.6
O1^i—Cu1—N2^i	86.73 (5)	C3—C4—H4A	119.6
N2—Cu1—N2^i	180.0	N1—C5—C4	118.41 (14)
O1—Cu1—N4	88.34 (5)	N1—C5—C6	119.88 (13)
O1^i—Cu1—N4	91.66 (5)	C4—C5—C6	121.70 (14)
N2—Cu1—N4	92.46 (6)	N2—C6—C7	121.89 (14)
N2^i—Cu1—N4	87.54 (6)	N2—C6—C5	119.56 (13)
N1—O1—Cu1	115.04 (8)	C7—C6—C5	118.52 (14)
O1—N1—C1	117.27 (12)	C8—C7—C6	119.49 (15)
O1—N1—C5	120.70 (12)	C8—C7—H7A	120.3
C1—N1—C5	122.02 (13)	C6—C7—H7A	120.3
C10—N2—C6	117.77 (13)	C9—C8—C7	118.67 (15)
C10—N2—Cu1	118.68 (10)	C9—C8—H8A	120.7
C6—N2—Cu1	121.56 (10)	C7—C8—H8A	120.7
C12—N4—Cu1	132.57 (13)	C8—C9—C10	118.99 (15)
C12—N5—C11	121.47 (18)	C8—C9—H9A	120.5
N1—C1—C2	120.06 (15)	C10—C9—H9A	120.5
N1—C1—H1A	120.0	N2—C10—C9	123.12 (15)
C2—C1—H1A	120.0	N2—C10—H10A	118.4
C1—C2—C3	120.05 (16)	C9—C10—H10A	118.4
C1—C2—H2A	120.0	N3—C11—N5	175.4 (2)
C3—C2—H2A	120.0	N4—C12—N5	174.90 (19)
C2—C3—C4	118.73 (16)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···N4^ii	0.93	2.47	3.386 (2)	169

Symmetry code: (ii) −x+1, −y+1, −z+1.