Bis(2,2-bi­pyridine N,N′-dioxide-κ²O,O′)bis(dicyan­amido-κN¹)copper(II)

In the crystal structure of the title compound, [Cu(C₂N₃)₂(C₁₀H₈N₂O₂)₂], the Cu^II atom adopts a distorted octahedral geometry, with the basal plane formed by two O atoms of two chelating 2,2′-bi­pyridine N,N′-dioxide ligands and two N atoms of the two monodentate dicyan­amido anions [Cu—N/O 1.976 (3)–2.000 (2) Å]. The apical positions are occupied by the two other O atoms [Cu—O 2.288 (2)–2.310 (2) Å] of the chelating ligands.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.054
• wR factor = 0.128
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       3.14 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N53    -   C54      =       5.31 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C54

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 2002); cell refinement: COLLECT; data reduction: COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

[Cu(C10H8N2O2)2(C2N3)]	F(000) = 1164
Mr = 572.01	Dx = 1.616 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.865 (1) Å	Cell parameters from 20133 reflections
b = 21.647 (3) Å	θ = 2.7–27.5°
c = 17.214 (3) Å	µ = 0.99 mm^−1
β = 113.21 (2)°	T = 173 K
V = 2351.1 (6) Å^3	Needle, green
Z = 4	0.22 × 0.05 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer	5330 independent reflections
Radiation source: fine-focus sealed tube	3423 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.091
CCD scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.812, Tmax = 0.971	k = −28→27
20133 measured reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0494P)^2 + 0.5193P] where P = (Fo^2 + 2Fc^2)/3
5330 reflections	(Δ/σ)max = 0.001
352 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.67 e Å^−3

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	0.84283 (6)	0.23956 (2)	0.43474 (3)	0.01678 (14)
N11	1.1944 (4)	0.31564 (14)	0.57347 (16)	0.0173 (7)
C12	1.3790 (5)	0.28725 (17)	0.5815 (2)	0.0177 (8)
C13	1.5577 (5)	0.32309 (18)	0.5945 (2)	0.0219 (8)
H131	1.6881	0.3036	0.6025	0.026*
C14	1.5471 (5)	0.38649 (19)	0.5959 (2)	0.0269 (9)
H141	1.6690	0.4109	0.6049	0.032*
C15	1.3547 (5)	0.41412 (19)	0.5841 (2)	0.0275 (9)
H151	1.3427	0.4579	0.5834	0.033*
C16	1.1814 (5)	0.37760 (17)	0.5731 (2)	0.0228 (8)
H161	1.0501	0.3966	0.5652	0.027*
O17	1.0267 (3)	0.28210 (11)	0.56658 (14)	0.0193 (5)
N21	1.2614 (4)	0.18964 (14)	0.50813 (17)	0.0169 (6)
C22	1.3864 (5)	0.21944 (17)	0.5804 (2)	0.0170 (8)
C23	1.5226 (5)	0.18547 (18)	0.6477 (2)	0.0225 (9)
H231	1.6132	0.2059	0.6978	0.027*
C24	1.5271 (5)	0.12220 (18)	0.6424 (2)	0.0242 (9)
H241	1.6182	0.0987	0.6892	0.029*
C25	1.3987 (5)	0.09304 (18)	0.5687 (2)	0.0230 (8)
H251	1.4008	0.0493	0.5644	0.028*
C26	1.2677 (5)	0.12777 (17)	0.5016 (2)	0.0213 (8)
H261	1.1811	0.1080	0.4503	0.026*
O27	1.1355 (3)	0.22215 (11)	0.44180 (14)	0.0199 (6)
N31	0.4211 (4)	0.29046 (14)	0.36616 (17)	0.0179 (7)
C32	0.2882 (5)	0.26057 (17)	0.2950 (2)	0.0178 (8)
C33	0.1381 (5)	0.29506 (19)	0.2311 (2)	0.0228 (9)
H331	0.0396	0.2749	0.1825	0.027*
C34	0.1319 (5)	0.35817 (19)	0.2380 (2)	0.0281 (9)
H341	0.0314	0.3817	0.1938	0.034*
C35	0.2727 (5)	0.38725 (19)	0.3097 (2)	0.0281 (9)
H351	0.2710	0.4309	0.3148	0.034*
C36	0.4154 (5)	0.35222 (17)	0.3738 (2)	0.0227 (8)
H361	0.5105	0.3718	0.4237	0.027*
O37	0.5542 (3)	0.25760 (11)	0.43090 (14)	0.0191 (5)
N51	0.8216 (4)	0.16003 (15)	0.48721 (19)	0.0240 (7)
C52	0.8226 (5)	0.11017 (19)	0.5107 (2)	0.0210 (8)
N53	0.8012 (5)	0.05413 (15)	0.5337 (2)	0.0350 (9)
C54	0.9621 (6)	0.02392 (18)	0.5886 (3)	0.0286 (9)
N55	1.0880 (6)	−0.00625 (19)	0.6370 (3)	0.0533 (11)
N61	0.8607 (4)	0.31964 (15)	0.38200 (18)	0.0221 (7)
C62	0.8618 (5)	0.37227 (18)	0.3705 (2)	0.0202 (8)
N63	0.8372 (4)	0.43000 (15)	0.3488 (2)	0.0321 (8)
C64	0.9911 (5)	0.46978 (18)	0.3870 (2)	0.0224 (8)
N65	1.1151 (5)	0.50820 (16)	0.4155 (2)	0.0362 (9)
N41	0.4904 (4)	0.16799 (14)	0.29630 (17)	0.0180 (7)
C42	0.3018 (5)	0.19322 (17)	0.2907 (2)	0.0186 (8)
C43	0.1292 (5)	0.15503 (19)	0.2771 (2)	0.0260 (9)
H431	−0.0035	0.1726	0.2702	0.031*
C44	0.1487 (6)	0.0923 (2)	0.2736 (2)	0.0299 (10)
H441	0.0300	0.0662	0.2634	0.036*
C45	0.3459 (6)	0.06740 (19)	0.2852 (2)	0.0320 (10)
H451	0.3634	0.0239	0.2853	0.038*
C46	0.5149 (6)	0.10573 (18)	0.2966 (2)	0.0262 (9)
H461	0.6489	0.0886	0.3047	0.031*
O47	0.6505 (3)	0.20413 (11)	0.30105 (13)	0.0200 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0147 (2)	0.0145 (2)	0.0201 (2)	−0.00113 (17)	0.00573 (15)	0.00279 (19)
N11	0.0161 (14)	0.0173 (18)	0.0190 (15)	−0.0006 (12)	0.0074 (11)	0.0000 (13)
C12	0.0181 (16)	0.018 (2)	0.0156 (18)	−0.0002 (14)	0.0056 (13)	−0.0011 (15)
C13	0.0224 (17)	0.025 (2)	0.0180 (18)	−0.0021 (15)	0.0074 (14)	−0.0008 (16)
C14	0.0295 (19)	0.025 (3)	0.028 (2)	−0.0120 (17)	0.0123 (16)	−0.0035 (18)
C15	0.037 (2)	0.017 (2)	0.026 (2)	−0.0034 (17)	0.0101 (16)	0.0010 (17)
C16	0.0265 (18)	0.016 (2)	0.024 (2)	0.0045 (16)	0.0083 (15)	−0.0003 (17)
O17	0.0175 (11)	0.0186 (15)	0.0230 (13)	−0.0036 (10)	0.0093 (10)	0.0002 (11)
N21	0.0139 (13)	0.0182 (19)	0.0198 (16)	0.0011 (12)	0.0078 (11)	0.0027 (13)
C22	0.0149 (16)	0.017 (2)	0.0194 (18)	−0.0016 (14)	0.0071 (13)	−0.0020 (15)
C23	0.0156 (16)	0.026 (3)	0.024 (2)	0.0038 (15)	0.0054 (14)	0.0004 (17)
C24	0.0188 (17)	0.023 (2)	0.030 (2)	0.0077 (15)	0.0091 (15)	0.0086 (18)
C25	0.0199 (17)	0.015 (2)	0.037 (2)	0.0044 (15)	0.0149 (16)	0.0034 (17)
C26	0.0180 (16)	0.019 (2)	0.027 (2)	−0.0035 (15)	0.0090 (14)	−0.0041 (17)
O27	0.0184 (11)	0.0215 (16)	0.0188 (12)	−0.0002 (10)	0.0062 (9)	0.0025 (11)
N31	0.0150 (13)	0.0190 (19)	0.0206 (16)	0.0024 (12)	0.0081 (11)	0.0005 (13)
C32	0.0135 (15)	0.019 (2)	0.0238 (19)	0.0010 (14)	0.0105 (13)	−0.0002 (16)
C33	0.0169 (16)	0.030 (3)	0.0219 (19)	0.0054 (15)	0.0085 (14)	0.0046 (17)
C34	0.0279 (19)	0.032 (3)	0.028 (2)	0.0146 (17)	0.0150 (16)	0.0116 (19)
C35	0.035 (2)	0.020 (2)	0.038 (2)	0.0085 (17)	0.0231 (18)	0.0031 (19)
C36	0.0230 (17)	0.021 (2)	0.028 (2)	0.0002 (15)	0.0135 (15)	−0.0043 (17)
O37	0.0171 (11)	0.0222 (15)	0.0163 (12)	0.0011 (10)	0.0047 (9)	0.0037 (11)
N51	0.0158 (14)	0.020 (2)	0.0314 (18)	−0.0034 (13)	0.0047 (12)	0.0061 (15)
C52	0.0175 (16)	0.024 (2)	0.022 (2)	0.0019 (15)	0.0090 (14)	0.0008 (17)
N53	0.0353 (18)	0.018 (2)	0.050 (2)	−0.0048 (15)	0.0147 (16)	0.0118 (17)
C54	0.043 (2)	0.012 (2)	0.044 (3)	−0.0062 (18)	0.032 (2)	−0.0022 (19)
N55	0.049 (2)	0.037 (3)	0.081 (3)	0.0129 (19)	0.034 (2)	0.030 (2)
N61	0.0187 (14)	0.019 (2)	0.0268 (17)	−0.0022 (13)	0.0071 (12)	0.0023 (14)
C62	0.0163 (16)	0.021 (2)	0.0210 (19)	−0.0025 (15)	0.0050 (14)	0.0016 (17)
N63	0.0288 (16)	0.017 (2)	0.041 (2)	−0.0004 (14)	0.0037 (14)	0.0044 (16)
C64	0.0277 (18)	0.015 (2)	0.030 (2)	0.0046 (17)	0.0177 (16)	0.0073 (17)
N65	0.0370 (19)	0.018 (2)	0.060 (2)	−0.0001 (15)	0.0251 (17)	0.0024 (18)
N41	0.0223 (14)	0.0158 (18)	0.0139 (15)	−0.0008 (12)	0.0049 (11)	0.0005 (13)
C42	0.0200 (16)	0.020 (2)	0.0170 (18)	0.0022 (15)	0.0081 (13)	0.0011 (15)
C43	0.0264 (18)	0.029 (3)	0.022 (2)	−0.0096 (17)	0.0098 (15)	−0.0063 (18)
C44	0.035 (2)	0.032 (3)	0.023 (2)	−0.0161 (18)	0.0111 (16)	−0.0037 (18)
C45	0.052 (2)	0.016 (2)	0.023 (2)	−0.0115 (19)	0.0096 (18)	−0.0009 (17)
C46	0.034 (2)	0.022 (2)	0.0189 (19)	0.0067 (17)	0.0065 (15)	−0.0005 (17)
O47	0.0173 (11)	0.0179 (16)	0.0246 (13)	−0.0027 (10)	0.0081 (10)	0.0012 (11)

Geometric parameters (Å, º)

Cu1—N51	1.976 (3)	N31—C36	1.345 (4)
Cu1—N61	1.983 (3)	N31—C32	1.368 (4)
Cu1—O37	1.995 (2)	C32—C33	1.391 (5)
Cu1—O27	2.000 (2)	C32—C42	1.465 (5)
Cu1—O47	2.288 (2)	C33—C34	1.373 (5)
Cu1—O17	2.309 (2)	C33—H331	0.9500
N11—O17	1.326 (3)	C34—C35	1.383 (5)
N11—C16	1.344 (4)	C34—H341	0.9500
N11—C12	1.366 (4)	C35—C36	1.378 (5)
C12—C13	1.393 (5)	C35—H351	0.9500
C12—C22	1.469 (5)	C36—H361	0.9500
C13—C14	1.375 (5)	N51—C52	1.152 (4)
C13—H131	0.9500	C52—N53	1.302 (5)
C14—C15	1.389 (5)	N53—C54	1.310 (5)
C14—H141	0.9500	C54—N55	1.141 (5)
C15—C16	1.378 (5)	N61—C62	1.157 (4)
C15—H151	0.9500	C62—N63	1.296 (5)
C16—H161	0.9500	N63—C64	1.320 (5)
N21—O27	1.330 (3)	C64—N65	1.152 (5)
N21—C26	1.346 (4)	N41—O47	1.325 (3)
N21—C22	1.363 (4)	N41—C46	1.358 (4)
C22—C23	1.380 (5)	N41—C42	1.373 (4)
C23—C24	1.374 (5)	C42—C43	1.387 (5)
C23—H231	0.9500	C43—C44	1.367 (5)
C24—C25	1.380 (5)	C43—H431	0.9500
C24—H241	0.9500	C44—C45	1.397 (5)
C25—C26	1.375 (5)	C44—H441	0.9500
C25—H251	0.9500	C45—C46	1.376 (5)
C26—H261	0.9500	C45—H451	0.9500
N31—O37	1.334 (3)	C46—H461	0.9500
N51—Cu1—N61	179.31 (11)	N21—C26—H261	119.8
N51—Cu1—O37	86.24 (10)	C25—C26—H261	119.8
N61—Cu1—O37	93.07 (10)	N21—O27—Cu1	116.71 (18)
N51—Cu1—O27	93.52 (11)	O37—N31—C36	119.0 (3)
N61—Cu1—O27	87.17 (10)	O37—N31—C32	119.4 (3)
O37—Cu1—O27	178.49 (9)	C36—N31—C32	121.5 (3)
N51—Cu1—O47	92.89 (11)	N31—C32—C33	118.6 (3)
N61—Cu1—O47	87.01 (10)	N31—C32—C42	118.9 (3)
O37—Cu1—O47	81.97 (8)	C33—C32—C42	122.4 (3)
O27—Cu1—O47	99.53 (9)	C34—C33—C32	120.3 (3)
N51—Cu1—O17	90.48 (11)	C34—C33—H331	119.9
N61—Cu1—O17	89.59 (10)	C32—C33—H331	119.9
O37—Cu1—O17	96.07 (8)	C33—C34—C35	119.7 (3)
O27—Cu1—O17	82.44 (9)	C33—C34—H341	120.2
O47—Cu1—O17	175.98 (9)	C35—C34—H341	120.2
O17—N11—C16	119.5 (3)	C36—C35—C34	119.3 (4)
O17—N11—C12	120.1 (3)	C36—C35—H351	120.3
C16—N11—C12	120.5 (3)	C34—C35—H351	120.3
N11—C12—C13	119.3 (3)	N31—C36—C35	120.5 (3)
N11—C12—C22	118.9 (3)	N31—C36—H361	119.7
C13—C12—C22	121.8 (3)	C35—C36—H361	119.7
C14—C13—C12	120.6 (3)	N31—O37—Cu1	118.45 (18)
C14—C13—H131	119.7	C52—N51—Cu1	170.3 (3)
C12—C13—H131	119.7	N51—C52—N53	173.7 (3)
C13—C14—C15	118.8 (3)	C52—N53—C54	121.3 (3)
C13—C14—H141	120.6	N55—C54—N53	173.4 (4)
C15—C14—H141	120.6	C62—N61—Cu1	160.9 (3)
C16—C15—C14	119.5 (4)	N61—C62—N63	171.8 (4)
C16—C15—H151	120.3	C62—N63—C64	119.8 (3)
C14—C15—H151	120.3	N65—C64—N63	174.2 (4)
N11—C16—C15	121.3 (3)	O47—N41—C46	119.2 (3)
N11—C16—H161	119.4	O47—N41—C42	120.4 (3)
C15—C16—H161	119.4	C46—N41—C42	120.4 (3)
N11—O17—Cu1	115.17 (17)	N41—C42—C43	119.6 (3)
O27—N21—C26	119.1 (3)	N41—C42—C32	118.0 (3)
O27—N21—C22	119.7 (3)	C43—C42—C32	122.3 (3)
C26—N21—C22	121.2 (3)	C44—C43—C42	120.4 (3)
N21—C22—C23	119.3 (3)	C44—C43—H431	119.8
N21—C22—C12	118.1 (3)	C42—C43—H431	119.8
C23—C22—C12	122.5 (3)	C43—C44—C45	118.9 (3)
C24—C23—C22	120.1 (3)	C43—C44—H441	120.5
C24—C23—H231	120.0	C45—C44—H441	120.5
C22—C23—H231	120.0	C46—C45—C44	120.2 (4)
C23—C24—C25	119.6 (3)	C46—C45—H451	119.9
C23—C24—H241	120.2	C44—C45—H451	119.9
C25—C24—H241	120.2	N41—C46—C45	120.1 (3)
C26—C25—C24	119.5 (4)	N41—C46—H461	119.9
C26—C25—H251	120.3	C45—C46—H461	119.9
C24—C25—H251	120.3	N41—O47—Cu1	113.32 (17)
N21—C26—C25	120.4 (3)