(4,4'-Di-tert-butyl-2,2'-bipyridine-κN,N')bis-(nitrato-κO,O')copper(II).

In the crystal of the title compound, [Cu(NO(3))(2)(C(18)H(24)N(2))], the Cu(II) ion is coordinated by two N atoms of the bipyridine ligand and four O atoms from the two nitrate anions in a distorted octahedral fashion. The dihedral angle between the planes of the two pyridine rings is 11.52 (10)°. In the crystal structure, weak C-H⋯O inter-actions may help to establish the packing.

Related literature

For general background, see: Noro et al. (2000 ▶); Yaghi et al. (1998 ▶); Huertas et al. (2001 ▶); Qin et al. (2002 ▶).

Experimental

Crystal data

[Cu(NO3)2(C18H24N2)]

M = 455.96

Orthorhombic,

a = 9.8265 (16) Å

b = 13.247 (2) Å

c = 16.138 (3) Å

V = 2100.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.08 mm−1

T = 173 (2) K

0.27 × 0.25 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.759, T max = 0.837

11065 measured reflections

3642 independent reflections

3450 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.074

S = 1.05

3642 reflections

258 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.81 e Å−3

Absolute structure: Flack (1983 ▶), 1522 Friedel pairs

Flack parameter: 0.012 (13)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001457/at2708sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001457/at2708Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(NO3)2(C18H24N2)]	F(000) = 948
Mr = 455.96	Dx = 1.442 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2120 reflections
a = 9.8265 (16) Å	θ = 2.0–25.0°
b = 13.247 (2) Å	µ = 1.08 mm−1
c = 16.138 (3) Å	T = 173 K
V = 2100.7 (6) Å3	Block, blue
Z = 4	0.27 × 0.25 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	3642 independent reflections
Radiation source: fine-focus sealed tube	3450 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.759, Tmax = 0.837	k = −15→15
11065 measured reflections	l = −19→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0386P)2 + 0.8717P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3642 reflections	Δρmax = 0.64 e Å−3
258 parameters	Δρmin = −0.81 e Å−3
1 restraint	Absolute structure: Flack (1983), 1522 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.012 (13)

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.

	x	y	z	Uiso*/Ueq
Cu1	0.58577 (3)	0.98172 (2)	0.72968 (2)	0.02515 (10)
O2	0.3672 (2)	1.0193 (2)	0.66313 (14)	0.0434 (6)
O1	0.4195 (2)	0.89792 (15)	0.74670 (14)	0.0387 (5)
O4	0.5221 (2)	1.08313 (16)	0.81065 (13)	0.0328 (5)
N2	0.7365 (2)	1.06673 (17)	0.68765 (15)	0.0243 (5)
N4	0.5626 (2)	1.05068 (18)	0.88143 (15)	0.0300 (6)
O5	0.6358 (2)	0.97414 (17)	0.88213 (13)	0.035
N1	0.6896 (2)	0.87411 (17)	0.67467 (15)	0.0242 (5)
N3	0.3281 (3)	0.9442 (2)	0.70369 (17)	0.0381 (6)
O6	0.5273 (3)	1.0950 (2)	0.94430 (15)	0.0558 (7)
C15	1.0722 (3)	1.2220 (2)	0.56813 (19)	0.0308 (7)
C6	0.8337 (3)	1.0146 (2)	0.64671 (16)	0.0225 (6)
C11	0.9809 (3)	0.6535 (2)	0.58589 (19)	0.0279 (6)
O3	0.2114 (2)	0.9132 (2)	0.7046 (2)	0.0649 (9)
C2	0.7514 (3)	0.7040 (2)	0.64459 (18)	0.0275 (6)
H2	0.7265	0.6363	0.6436	0.033*
C3	0.8801 (3)	0.7323 (2)	0.61767 (18)	0.0233 (6)
C8	0.9527 (3)	1.1675 (2)	0.61021 (18)	0.0253 (6)
C7	0.9411 (3)	1.0624 (2)	0.60741 (17)	0.0252 (6)
H7	1.0057	1.0245	0.5791	0.030*
C5	0.8133 (3)	0.9040 (2)	0.64572 (17)	0.0225 (6)
C4	0.9100 (3)	0.83539 (19)	0.61865 (16)	0.0223 (5)
H4	0.9948	0.8580	0.6011	0.027*
C1	0.6602 (3)	0.7753 (2)	0.67289 (19)	0.0281 (6)
H1	0.5752	0.7541	0.6914	0.034*
C10	0.7481 (3)	1.1682 (2)	0.69174 (19)	0.0290 (6)
H10	0.6821	1.2047	0.7202	0.035*
C17	1.1679 (4)	1.2577 (3)	0.6369 (2)	0.0507 (10)
H17A	1.2445	1.2919	0.6128	0.076*
H17B	1.1993	1.2006	0.6681	0.076*
H17C	1.1202	1.3032	0.6730	0.076*
C9	0.8536 (3)	1.2190 (2)	0.65550 (19)	0.0302 (7)
H9	0.8594	1.2888	0.6611	0.036*
C14	1.1222 (3)	0.6979 (3)	0.5698 (2)	0.0400 (8)
H14A	1.1817	0.6459	0.5498	0.060*
H14B	1.1580	0.7251	0.6205	0.060*
H14C	1.1155	0.7507	0.5292	0.060*
C13	0.9948 (3)	0.5689 (2)	0.6509 (2)	0.0397 (8)
H13A	1.0577	0.5189	0.6312	0.060*
H13B	0.9076	0.5381	0.6600	0.060*
H13C	1.0276	0.5969	0.7020	0.060*
C16	1.1495 (3)	1.1522 (3)	0.5092 (2)	0.0410 (8)
H16A	1.2235	1.1885	0.4844	0.062*
H16B	1.0890	1.1287	0.4667	0.062*
H16C	1.1845	1.0955	0.5396	0.062*
C12	0.9251 (4)	0.6105 (3)	0.5041 (2)	0.0440 (8)
H12A	0.9871	0.5607	0.4829	0.066*
H12B	0.9154	0.6641	0.4645	0.066*
H12C	0.8380	0.5798	0.5139	0.066*
C18	1.0207 (4)	1.3135 (3)	0.5182 (3)	0.0512 (10)
H18A	1.0965	1.3467	0.4923	0.077*
H18B	0.9755	1.3598	0.5547	0.077*
H18C	0.9581	1.2910	0.4764	0.077*

	U11	U22	U33	U12	U13	U23
Cu1	0.02290 (16)	0.02379 (17)	0.02875 (18)	0.00229 (14)	0.00540 (15)	−0.00019 (15)
O2	0.021	0.0581 (15)	0.0509 (13)	0.0047 (11)	−0.0042 (9)	0.0038 (14)
O1	0.0287 (10)	0.0327 (11)	0.0548 (15)	−0.0013 (9)	0.0091 (10)	0.0042 (9)
O4	0.0379 (11)	0.0321 (12)	0.0285 (11)	0.0100 (9)	0.0039 (10)	0.0011 (10)
N2	0.0264 (12)	0.0209 (12)	0.0256 (12)	0.0016 (10)	0.0028 (10)	0.0006 (10)
N4	0.0287 (13)	0.0328 (14)	0.0283 (13)	0.0002 (11)	0.0005 (11)	−0.0032 (11)
O5	0.033	0.034	0.038	0.0127 (10)	−0.0048 (9)	0.0036 (10)
N1	0.0248 (11)	0.0220 (13)	0.0260 (13)	−0.0020 (10)	0.0038 (10)	0.0000 (10)
N3	0.0263 (13)	0.0424 (16)	0.0455 (17)	0.0029 (11)	0.0057 (10)	−0.0132 (13)
O6	0.0737 (18)	0.0623 (17)	0.0313 (14)	0.0154 (14)	0.0022 (13)	−0.0100 (12)
C15	0.0309 (16)	0.0254 (15)	0.0361 (17)	−0.0065 (14)	−0.0001 (15)	0.0046 (12)
C6	0.0253 (13)	0.0220 (14)	0.0201 (13)	0.0005 (12)	0.0013 (11)	0.0000 (12)
C11	0.0330 (15)	0.0207 (15)	0.0299 (16)	0.0024 (13)	0.0008 (13)	−0.0045 (12)
O3	0.0275 (13)	0.0736 (19)	0.094 (2)	−0.0068 (12)	−0.0036 (13)	−0.0171 (17)
C2	0.0291 (14)	0.0201 (14)	0.0332 (17)	−0.0039 (12)	0.0012 (13)	−0.0010 (12)
C3	0.0286 (16)	0.0214 (14)	0.0200 (14)	0.0008 (11)	−0.0055 (12)	0.0007 (11)
C8	0.0287 (15)	0.0230 (15)	0.0242 (16)	−0.0037 (11)	−0.0047 (12)	0.0036 (12)
C7	0.0239 (15)	0.0255 (14)	0.0262 (15)	−0.0011 (11)	0.0027 (12)	−0.0024 (12)
C5	0.0246 (13)	0.0227 (15)	0.0202 (14)	−0.0013 (11)	0.0003 (12)	−0.0016 (12)
C4	0.0206 (12)	0.0243 (14)	0.0218 (13)	−0.0023 (12)	0.0018 (13)	−0.0016 (11)
C1	0.0258 (15)	0.0240 (15)	0.0344 (17)	−0.0039 (12)	0.0010 (13)	−0.0002 (13)
C10	0.0345 (15)	0.0232 (15)	0.0295 (16)	0.0059 (13)	0.0041 (13)	−0.0012 (12)
C17	0.045 (2)	0.056 (2)	0.051 (2)	−0.0223 (18)	−0.0037 (18)	−0.0033 (19)
C9	0.0381 (16)	0.0187 (15)	0.0339 (17)	−0.0004 (12)	−0.0017 (14)	−0.0016 (13)
C14	0.0333 (18)	0.0337 (18)	0.053 (2)	0.0072 (14)	0.0107 (15)	−0.0022 (16)
C13	0.0459 (19)	0.0285 (17)	0.045 (2)	0.0100 (15)	−0.0019 (16)	0.0064 (15)
C16	0.0365 (17)	0.0393 (19)	0.047 (2)	−0.0091 (15)	0.0115 (16)	0.0047 (16)
C12	0.051 (2)	0.043 (2)	0.0384 (18)	0.0096 (18)	−0.0011 (17)	−0.0151 (14)
C18	0.047 (2)	0.040 (2)	0.067 (3)	−0.0033 (17)	0.0112 (19)	0.0231 (19)

Cu1—N1	1.965 (2)	C8—C9	1.396 (4)
Cu1—O4	1.976 (2)	C8—C7	1.398 (4)
Cu1—N2	1.980 (2)	C7—H7	0.9300
Cu1—O1	1.994 (2)	C5—C4	1.385 (4)
O2—N3	1.251 (4)	C4—H4	0.9300
O1—N3	1.290 (3)	C1—H1	0.9300
O4—N4	1.284 (3)	C10—C9	1.368 (4)
N2—C6	1.351 (3)	C10—H10	0.9300
N2—C10	1.350 (4)	C17—H17A	0.9600
N4—O6	1.223 (3)	C17—H17B	0.9600
N4—O5	1.243 (3)	C17—H17C	0.9600
N1—C1	1.340 (4)	C9—H9	0.9300
N1—C5	1.360 (4)	C14—H14A	0.9600
N3—O3	1.218 (3)	C14—H14B	0.9600
C15—C16	1.528 (4)	C14—H14C	0.9600
C15—C17	1.531 (5)	C13—H13A	0.9600
C15—C8	1.536 (4)	C13—H13B	0.9600
C15—C18	1.541 (4)	C13—H13C	0.9600
C6—C7	1.385 (4)	C16—H16A	0.9600
C6—C5	1.479 (4)	C16—H16B	0.9600
C11—C3	1.528 (4)	C16—H16C	0.9600
C11—C14	1.530 (4)	C12—H12A	0.9600
C11—C12	1.539 (4)	C12—H12B	0.9600
C11—C13	1.541 (4)	C12—H12C	0.9600
C2—C1	1.380 (4)	C18—H18A	0.9600
C2—C3	1.389 (4)	C18—H18B	0.9600
C2—H2	0.9300	C18—H18C	0.9600
C3—C4	1.396 (4)
N1—Cu1—O4	163.03 (9)	C4—C5—C6	124.1 (2)
N1—Cu1—N2	82.49 (9)	C5—C4—C3	120.0 (3)
O4—Cu1—N2	94.41 (9)	C5—C4—H4	120.0
N1—Cu1—O1	94.82 (9)	C3—C4—H4	120.0
O4—Cu1—O1	91.59 (9)	N1—C1—C2	122.4 (3)
N2—Cu1—O1	167.53 (10)	N1—C1—H1	118.8
N3—O1—Cu1	103.37 (17)	C2—C1—H1	118.8
N4—O4—Cu1	105.23 (16)	N2—C10—C9	122.2 (3)
C6—N2—C10	118.2 (2)	N2—C10—H10	118.9
C6—N2—Cu1	113.90 (18)	C9—C10—H10	118.9
C10—N2—Cu1	127.8 (2)	C15—C17—H17A	109.5
O6—N4—O5	123.3 (3)	C15—C17—H17B	109.5
O6—N4—O4	119.3 (2)	H17A—C17—H17B	109.5
O5—N4—O4	117.4 (2)	C15—C17—H17C	109.5
C1—N1—C5	118.0 (2)	H17A—C17—H17C	109.5
C1—N1—Cu1	127.3 (2)	H17B—C17—H17C	109.5
C5—N1—Cu1	114.09 (18)	C10—C9—C8	120.8 (3)
O3—N3—O2	124.3 (3)	C10—C9—H9	119.6
O3—N3—O1	119.2 (3)	C8—C9—H9	119.6
O2—N3—O1	116.5 (2)	C11—C14—H14A	109.5
C16—C15—C17	109.4 (3)	C11—C14—H14B	109.5
C16—C15—C8	111.8 (2)	H14A—C14—H14B	109.5
C17—C15—C8	107.1 (3)	C11—C14—H14C	109.5
C16—C15—C18	108.3 (3)	H14A—C14—H14C	109.5
C17—C15—C18	109.7 (3)	H14B—C14—H14C	109.5
C8—C15—C18	110.5 (3)	C11—C13—H13A	109.5
N2—C6—C7	121.9 (3)	C11—C13—H13B	109.5
N2—C6—C5	114.6 (2)	H13A—C13—H13B	109.5
C7—C6—C5	123.5 (3)	C11—C13—H13C	109.5
C3—C11—C14	112.4 (2)	H13A—C13—H13C	109.5
C3—C11—C12	108.1 (3)	H13B—C13—H13C	109.5
C14—C11—C12	108.7 (3)	C15—C16—H16A	109.5
C3—C11—C13	109.0 (2)	C15—C16—H16B	109.5
C14—C11—C13	108.4 (3)	H16A—C16—H16B	109.5
C12—C11—C13	110.3 (3)	C15—C16—H16C	109.5
C1—C2—C3	120.6 (3)	H16A—C16—H16C	109.5
C1—C2—H2	119.7	H16B—C16—H16C	109.5
C3—C2—H2	119.7	C11—C12—H12A	109.5
C2—C3—C4	116.9 (3)	C11—C12—H12B	109.5
C2—C3—C11	120.7 (2)	H12A—C12—H12B	109.5
C4—C3—C11	122.4 (3)	C11—C12—H12C	109.5
C9—C8—C7	116.5 (3)	H12A—C12—H12C	109.5
C9—C8—C15	122.4 (3)	H12B—C12—H12C	109.5
C7—C8—C15	121.0 (3)	C15—C18—H18A	109.5
C6—C7—C8	120.2 (3)	C15—C18—H18B	109.5
C6—C7—H7	119.9	H18A—C18—H18B	109.5
C8—C7—H7	119.9	C15—C18—H18C	109.5
N1—C5—C4	122.0 (3)	H18A—C18—H18C	109.5
N1—C5—C6	113.9 (2)	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4i	0.93	2.46	3.124 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4i	0.93	2.46	3.124 (3)	129

Symmetry code: (i) .