catena-Poly[[copper(II)-bis­[μ-bis­(pyridin-3-yl)methanone-κ2N:N′]] bis­(tetra­fluorido­borate)]

Liu, B.

doi:10.1107/S1600536811050628

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1888-m1889

https://doi.org/10.1107/S1600536811050628

Open

access

catena-Poly[[copper(II)-bis[μ-bis(pyridin-3-yl)methanone-κ²N:N′]] bis(tetrafluoridoborate)]

Bin Liu ^a ^*

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
^*Correspondence e-mail: binliu92@yahoo.cn

(Received 19 November 2011; accepted 25 November 2011; online 30 November 2011)

In the title complex, {[Cu(C₁₁H₈N₂O)₂](BF₄)₂}_n, the Cu^II ion is situated on an inversion centre and adopts an N₄F₂ octahedral coordination geometry with four N atoms from four different bis(pyridin-3-yl)methanone ligands at the equatorial sites and two independent tetrafluoridoborate anions weakly bonded at the axial sites via two F atoms [Cu⋯F = 2.613 (3) Å]. Chains with the bridging ligands are formed along the a axis. C—H⋯F interactions stabilize the structure. C—O⋯π interactions also occur.

Related literature

For background to coordination chemistry based on pyridylmethanone derivatives, see: Dendrinou-Samara et al. (2003 ); Boudalis et al. (2003 ). For transition metal complexes of di-3-pyridinylmethanone, see: Chen et al. (2005 ); Chen & Mak (2005 ); Chen et al. (2009 ). For a comparable structure, see: Wan et al. (2008 ).

Experimental

Crystal data

[Cu(C₁₁H₈N₂O)₂](BF₄)₂
M_r = 605.55
Triclinic, $[P \overline 1]$
a = 7.5542 (13) Å
b = 8.7861 (15) Å
c = 10.3389 (17) Å
α = 101.280 (2)°
β = 109.236 (2)°
γ = 108.869 (2)°
V = 576.96 (17) Å³
Z = 1
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 296 K
0.31 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.756, T_max = 1.000
4090 measured reflections
2857 independent reflections
2638 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.135
S = 1.05
2857 reflections
178 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N1	2.017 (2)
Cu1—N2ⁱ	2.039 (2)
Symmetry codes: (i) x-1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F2ⁱⁱ	0.93	2.32	3.182 (3)	154
C10—H10A⋯F4ⁱⁱⁱ	0.93	2.41	3.228 (2)	147
Symmetry codes: (ii) x-1, y-1, z-1; (iii) -x+3, -y+2, -z+2.

Table 3
C=O⋯π-electron ring interactions (Å, °)

Cg1 and Cg2, are the centroids of the N1/C1–C5 and N2/C7–C11 rings, respectively.

C=O⋯Cg	O⋯Cg	C⋯Cg	C=O⋯Cg
C6=O1⋯Cg1^iv	3.123 (4)	4.019 (3)	130.79 (2)
C6=O1⋯Cg2^v	3.237 (3)	4.123 (2)	130.20 (1)
Symmetry codes: (iv) 1-x, 1-y, 1-z; (v) 2-x, 1-y, 1-z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050628/bt5715sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050628/bt5715Isup2.hkl

checkCIF report

Comment top

The transition metal complexes of di-2-pyridinylmethanone (di-2-pyridyl ketone) have been widely studied in the passed decade (Dendrinou-Samara et al., 2003; Boudalis et al., 2003). The positional isomer di-3-pyridinylmethanone (di-3-pyridyl ketone) was mostly used as a flexible linker in construction various coordination frameworks. The angular C(sp²)-CO-C(sp²) moiety and the rotatable C-C σ bond exhibit subtile tuning on the ligand conformation and subsequent on the formation of various coordination frameworks, such as one-dimensional helical and zigzag chains (Chen & Mak, 2005), two-dimensional nets (Chen et al., 2005) as well as honeycomb-like three-dimensional frameworks (Chen et al., 2009) were constructed. Here we report a new structure derived from di-3-pyridinylmethanone, namely poly{[µ₂-(bis(3-pyridyl)methanone-κ²N:N')] copper(II)}ditetrafluoridoborate.

In the title complex, C₂₂H₁₆B₂CuF₈N₄O₂, the Cu^II ion adopts an N4F2-octahedral coordination geometry with four separate di-3-pyridinylmethanone ligands providing four N atoms at the equatorial sites, while two independent tetrafluoridoborate weakly bonding at the axial sites via two F atoms (Fig. 1). The Cu1···F1 distance is 2.613 (2) Å, comparable to that 2.677 (3) Å in [(CuL₂)(BF₄)₂]_∞ (L = di-3-pyridinylmethanone, Chen et al. 2005), wherein the Cu^II adopts a similar N4F2-octahedral geometry. Along the a axis, one double bridged chain with the bidentate bridging ligands is formed in the title complex, which is remarkable different from the (4,4) net in [(CuL₂)(BF₄)₂]_∞ (L = di-3-pyridinylmethanone, Chen et al. 2005). The chains are arranged in a shoulder-to-shoulder mode and interconnected through C═O···π(pyridyl) interaction, forming a layer in the ac plane (Fig. 2). For the C═O···π(pyridyl) interaction, each C6═O1 points to the opposite chain and is embraced by two pyridyl rings. The O1···Cg(pyridyl) distances lie within the 3.123 (4)-3.237 (3) Å range (Table 1), well comparable to that 2.916-3.125 Å in Cu(L)₂(BF₄)₂ (L = 2,6-pyridinediylbis(3-pyridinyl)methanone) reported by Wan et al. (Wan et al. 2008). The formed layers are almost parallel and stacked along the b direction to furnish a three-dimensional framework, with the tetrafluoridoborate anions embedded among the interstices (Fig. 3). C—H(pyridyl)···F interactions is also found to stabilize the full framework (Table 1).

Related literature top

For the background on the coordination chemistry based on pyridylmethanone derivatives,see: Dendrinou-Samara et al. (2003); Boudalis et al. (2003). For the transition metal complexes of di-3-pyridinylmethanone, see: Chen et al.(2005); Chen & Mak (2005); Chen et al.(2009). For a comparable structure, see: Wan et al. (2008).

Experimental top

Di-3-pyridinylmethanone was prepared according to the previously reported procedure (Chen & Mak 2005). Cu(BF₄)₂.xH₂O (40 mg) and di-3-pyridylmethanone (19mg, 0.1 mmol) were mixed and dissolved in 4 ml acetonitrile with stirring at room temperature. To the solution 1 ml methanol was subsequently dropped, obtaining a clear solution. Filtration was conducted the filtrate was left to evaporate in air. The needle-like crystals were deposited after one week (15.4 mg, 51% yield based on ligand).

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Figures top

	Fig. 1. The title complex showing the atom-numbering scheme, with displacement ellipsoids shown at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius. Symmetry codes: (i) x–1, y, z;(ii)–x+1, –y+1, –z+2; (iii)–x+2, –y+1, –z+2.
	Fig. 2. The C═O···π interaction between the infinite cationic chain structure along the a axial direction. The BF₄^- anions are omitted for clarity.
	Fig. 3. The packing structure of the title complex viewed the a direction.

catena-Poly[[copper(II)-bis[µ-bis(pyridin-3-yl)methanone- κ²N:N']] bis(tetrafluoridoborate)] top

Crystal data top

[Cu(C₁₁H₈N₂O)₂](BF₄)₂	Z = 1
M_r = 605.55	F(000) = 303
Triclinic, P1	D_x = 1.743 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5542 (13) Å	Cell parameters from 202 reflections
b = 8.7861 (15) Å	θ = 2.2–28.6°
c = 10.3389 (17) Å	µ = 1.04 mm⁻¹
α = 101.280 (2)°	T = 296 K
β = 109.236 (2)°	Needle, blue
γ = 108.869 (2)°	0.31 × 0.20 × 0.12 mm
V = 576.96 (17) Å³

Data collection top

'Bruker ApEXII CCD area-detector' diffractometer	2857 independent reflections
Radiation source: fine-focus sealed tube	2638 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 28.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
T_min = 0.756, T_max = 1.000	k = −11→6
4090 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.076P)² + 0.4634P] P = (F_o² + 2F_c²)/3
2857 reflections	(Δ/σ)_max < 0.001
178 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Cu(C₁₁H₈N₂O)₂](BF₄)₂	γ = 108.869 (2)°
M_r = 605.55	V = 576.96 (17) Å³
Triclinic, P1	Z = 1
a = 7.5542 (13) Å	Mo Kα radiation
b = 8.7861 (15) Å	µ = 1.04 mm⁻¹
c = 10.3389 (17) Å	T = 296 K
α = 101.280 (2)°	0.31 × 0.20 × 0.12 mm
β = 109.236 (2)°

Data collection top

'Bruker ApEXII CCD area-detector' diffractometer	2857 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2638 reflections with I > 2σ(I)
T_min = 0.756, T_max = 1.000	R_int = 0.023
4090 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.05	Δρ_max = 0.85 e Å⁻³
2857 reflections	Δρ_min = −0.67 e Å⁻³
178 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
Cu1	0.5000	0.5000	1.0000	0.02531 (15)
O1	0.7976 (3)	0.5511 (3)	0.4912 (2)	0.0449 (5)
N1	0.5354 (3)	0.4065 (3)	0.8203 (2)	0.0275 (4)
N2	1.3670 (3)	0.6359 (3)	0.8959 (2)	0.0282 (4)
C1	0.3910 (4)	0.2547 (3)	0.7229 (3)	0.0339 (5)
H1A	0.2892	0.1911	0.7467	0.041*
C2	0.3863 (5)	0.1881 (4)	0.5887 (3)	0.0403 (6)
H2A	0.2844	0.0816	0.5242	0.048*
C3	0.5354 (4)	0.2825 (4)	0.5519 (3)	0.0375 (6)
H3A	0.5326	0.2430	0.4607	0.045*
C4	0.6901 (4)	0.4379 (3)	0.6541 (3)	0.0284 (5)
C5	0.6860 (4)	0.4953 (3)	0.7873 (3)	0.0288 (5)
H5A	0.7905	0.5985	0.8559	0.035*
C6	0.8475 (4)	0.5442 (4)	0.6130 (3)	0.0316 (5)
C7	1.0686 (4)	0.6398 (3)	0.7218 (3)	0.0293 (5)
C8	1.1621 (4)	0.5673 (3)	0.8150 (3)	0.0287 (5)
H8A	1.0798	0.4672	0.8220	0.034*
C9	1.4820 (4)	0.7852 (4)	0.8909 (3)	0.0358 (6)
H9A	1.6237	0.8348	0.9476	0.043*
C10	1.3982 (5)	0.8686 (4)	0.8047 (4)	0.0431 (7)
H10A	1.4818	0.9739	0.8063	0.052*
C11	1.1897 (5)	0.7938 (4)	0.7166 (3)	0.0389 (6)
H11A	1.1310	0.8453	0.6548	0.047*
F1	0.8566 (3)	0.7588 (3)	1.0928 (2)	0.0494 (5)
F2	1.1230 (5)	0.8509 (4)	1.3095 (3)	0.1019 (11)
F3	1.1012 (6)	1.0340 (3)	1.1893 (4)	0.0985 (10)
F4	1.1711 (4)	0.8119 (4)	1.1061 (5)	0.1179 (14)
B1	1.0679 (5)	0.8698 (5)	1.1734 (5)	0.0480 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0249 (2)	0.0327 (2)	0.0226 (2)	0.01406 (17)	0.01259 (16)	0.01010 (16)
O1	0.0428 (11)	0.0707 (15)	0.0306 (10)	0.0272 (11)	0.0183 (9)	0.0254 (10)
N1	0.0273 (10)	0.0341 (10)	0.0255 (9)	0.0152 (8)	0.0134 (8)	0.0110 (8)
N2	0.0275 (10)	0.0348 (10)	0.0260 (9)	0.0152 (8)	0.0132 (8)	0.0106 (8)
C1	0.0329 (13)	0.0357 (13)	0.0342 (13)	0.0135 (10)	0.0171 (10)	0.0105 (10)
C2	0.0357 (14)	0.0396 (14)	0.0314 (13)	0.0089 (11)	0.0113 (11)	0.0003 (11)
C3	0.0373 (14)	0.0460 (15)	0.0252 (12)	0.0169 (12)	0.0136 (10)	0.0045 (10)
C4	0.0247 (11)	0.0402 (13)	0.0252 (11)	0.0177 (10)	0.0118 (9)	0.0116 (10)
C5	0.0262 (11)	0.0363 (12)	0.0237 (11)	0.0133 (10)	0.0112 (9)	0.0083 (9)
C6	0.0306 (12)	0.0444 (14)	0.0299 (12)	0.0214 (11)	0.0170 (10)	0.0156 (10)
C7	0.0286 (11)	0.0379 (13)	0.0281 (11)	0.0164 (10)	0.0159 (9)	0.0133 (10)
C8	0.0271 (11)	0.0343 (12)	0.0287 (11)	0.0131 (9)	0.0152 (9)	0.0128 (9)
C9	0.0275 (12)	0.0361 (13)	0.0412 (14)	0.0109 (10)	0.0139 (11)	0.0133 (11)
C10	0.0384 (15)	0.0359 (14)	0.0604 (19)	0.0145 (12)	0.0226 (14)	0.0259 (13)
C11	0.0398 (14)	0.0434 (15)	0.0468 (15)	0.0227 (12)	0.0223 (12)	0.0262 (13)
F1	0.0304 (8)	0.0654 (12)	0.0413 (10)	0.0127 (8)	0.0117 (7)	0.0142 (9)
F2	0.101 (2)	0.0750 (17)	0.0580 (15)	0.0260 (16)	−0.0246 (15)	−0.0022 (13)
F3	0.116 (3)	0.0466 (13)	0.127 (3)	0.0285 (15)	0.053 (2)	0.0236 (15)
F4	0.0569 (16)	0.099 (2)	0.167 (3)	0.0172 (15)	0.064 (2)	−0.018 (2)
B1	0.0310 (15)	0.0391 (17)	0.057 (2)	0.0095 (13)	0.0122 (14)	0.0016 (15)

Geometric parameters (Å, º) top

Cu1—N1ⁱ	2.017 (2)	C4—C5	1.385 (3)
Cu1—N1	2.017 (2)	C4—C6	1.496 (3)
Cu1—N2ⁱⁱ	2.039 (2)	C5—H5A	0.9300
Cu1—N2ⁱⁱⁱ	2.039 (2)	C6—C7	1.498 (4)
O1—C6	1.210 (3)	C7—C8	1.384 (4)
N1—C1	1.339 (3)	C7—C11	1.390 (4)
N1—C5	1.344 (3)	C8—H8A	0.9300
N2—C9	1.341 (3)	C9—C10	1.384 (4)
N2—C8	1.344 (3)	C9—H9A	0.9300
N2—Cu1^iv	2.039 (2)	C10—C11	1.376 (4)
C1—C2	1.380 (4)	C10—H10A	0.9300
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.379 (4)	F1—B1	1.411 (4)
C2—H2A	0.9300	F2—B1	1.390 (5)
C3—C4	1.391 (4)	F3—B1	1.348 (5)
C3—H3A	0.9300	F4—B1	1.352 (5)

N1ⁱ—Cu1—N1	180.000 (1)	C4—C5—H5A	119.0
N1ⁱ—Cu1—N2ⁱⁱ	91.68 (8)	O1—C6—C4	120.2 (2)
N1—Cu1—N2ⁱⁱ	88.32 (8)	O1—C6—C7	119.8 (2)
N1ⁱ—Cu1—N2ⁱⁱⁱ	88.32 (8)	C4—C6—C7	120.0 (2)
N1—Cu1—N2ⁱⁱⁱ	91.68 (8)	C8—C7—C11	118.9 (2)
N2ⁱⁱ—Cu1—N2ⁱⁱⁱ	180.000 (1)	C8—C7—C6	121.1 (2)
C1—N1—C5	118.2 (2)	C11—C7—C6	119.5 (2)
C1—N1—Cu1	118.20 (17)	N2—C8—C7	122.6 (2)
C5—N1—Cu1	123.27 (17)	N2—C8—H8A	118.7
C9—N2—C8	117.9 (2)	C7—C8—H8A	118.7
C9—N2—Cu1^iv	121.30 (18)	N2—C9—C10	122.7 (3)
C8—N2—Cu1^iv	120.26 (17)	N2—C9—H9A	118.7
N1—C1—C2	123.0 (2)	C10—C9—H9A	118.7
N1—C1—H1A	118.5	C11—C10—C9	119.2 (3)
C2—C1—H1A	118.5	C11—C10—H10A	120.4
C3—C2—C1	118.8 (3)	C9—C10—H10A	120.4
C3—C2—H2A	120.6	C10—C11—C7	118.6 (3)
C1—C2—H2A	120.6	C10—C11—H11A	120.7
C2—C3—C4	118.7 (2)	C7—C11—H11A	120.7
C2—C3—H3A	120.7	F3—B1—F4	114.2 (4)
C4—C3—H3A	120.7	F3—B1—F2	109.2 (3)
C5—C4—C3	119.1 (2)	F4—B1—F2	108.9 (4)
C5—C4—C6	121.7 (2)	F3—B1—F1	111.6 (3)
C3—C4—C6	119.0 (2)	F4—B1—F1	106.8 (3)
N1—C5—C4	122.0 (2)	F2—B1—F1	105.8 (3)
N1—C5—H5A	119.0

N1ⁱ—Cu1—N1—C1	−85 (100)	C3—C4—C6—O1	37.1 (4)
N2ⁱⁱ—Cu1—N1—C1	−95.5 (2)	C5—C4—C6—C7	42.9 (4)
N2ⁱⁱⁱ—Cu1—N1—C1	84.5 (2)	C3—C4—C6—C7	−141.6 (3)
N1ⁱ—Cu1—N1—C5	89 (100)	O1—C6—C7—C8	−138.8 (3)
N2ⁱⁱ—Cu1—N1—C5	78.4 (2)	C4—C6—C7—C8	39.9 (3)
N2ⁱⁱⁱ—Cu1—N1—C5	−101.6 (2)	O1—C6—C7—C11	32.6 (4)
C5—N1—C1—C2	−2.1 (4)	C4—C6—C7—C11	−148.6 (3)
Cu1—N1—C1—C2	172.0 (2)	C9—N2—C8—C7	3.7 (4)
N1—C1—C2—C3	−0.7 (5)	Cu1^iv—N2—C8—C7	−168.10 (19)
C1—C2—C3—C4	2.8 (5)	C11—C7—C8—N2	−3.2 (4)
C2—C3—C4—C5	−2.0 (4)	C6—C7—C8—N2	168.3 (2)
C2—C3—C4—C6	−177.6 (3)	C8—N2—C9—C10	−1.0 (4)
C1—N1—C5—C4	2.9 (4)	Cu1^iv—N2—C9—C10	170.7 (2)
Cu1—N1—C5—C4	−170.93 (18)	N2—C9—C10—C11	−2.2 (5)
C3—C4—C5—N1	−0.9 (4)	C9—C10—C11—C7	2.7 (5)
C6—C4—C5—N1	174.6 (2)	C8—C7—C11—C10	−0.1 (4)
C5—C4—C6—O1	−138.3 (3)	C6—C7—C11—C10	−171.7 (3)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+2; (iv) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F2^v	0.93	2.32	3.182 (3)	154
C10—H10A···F4^vi	0.93	2.41	3.228 (2)	147

Symmetry codes: (v) x−1, y−1, z−1; (vi) −x+3, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₁H₈N₂O)₂](BF₄)₂
M_r	605.55
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.5542 (13), 8.7861 (15), 10.3389 (17)
α, β, γ (°)	101.280 (2), 109.236 (2), 108.869 (2)
V (Å³)	576.96 (17)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.31 × 0.20 × 0.12

Data collection
Diffractometer	'Bruker ApEXII CCD area-detector'
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.756, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4090, 2857, 2638
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.673

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.135, 1.05
No. of reflections	2857
No. of parameters	178
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.67

Computer programs: APEX2 (Bruker, 2007), APEX2 and SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Cu1—N1ⁱ	2.017 (2)	Cu1—N2ⁱⁱ	2.039 (2)
Cu1—N1	2.017 (2)	Cu1—N2ⁱⁱⁱ	2.039 (2)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F2^iv	0.93	2.32	3.182 (3)	154
C10—H10A···F4^v	0.93	2.41	3.228 (2)	147

Symmetry codes: (iv) x−1, y−1, z−1; (v) −x+3, −y+2, −z+2.

C═O···π-electron ring interactions (Å, °) top

Cg1 and Cg2, are the centroids of the N1/C1–C5 and N2/C7–C11 rings, respectively.

C═O···Cg	O···Cg	C···Cg	C═O···Cg
C6═O1···Cg1^iv	3.123 (4)	4.019 (3)	130.79 (2)
C6═O1···Cg2^v	3.237 (3)	4.123 (2)	130.20 (1)

Symmetry codes: (iv) -x+1, -y+1, -z+1; (v) -x+2, -y+1, -z+1.

Acknowledgements

The authors are grateful for financial support from Beijing Municipal Education Commission.

References

Boudalis, A. K., Dahan, F., Bousseksou, A., Tuchagues, J. P. & Perlepes, J. P. (2003). Dalton Trans. pp. 3411-3418. Web of Science CSD CrossRef Google Scholar
Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, X. D., Guo, J. H., Du, M. & Mak, T. C. W. (2005). Inorg. Chem. Commun. 8, 766–768. Web of Science CSD CrossRef CAS Google Scholar
Chen, X. D. & Mak, T. C. W. (2005). J. Mol. Struct. 743, 1–6. Web of Science CSD CrossRef CAS Google Scholar
Chen, X. D., Wan, C. Q., Sung, H. H. Y., Williams, I. D. & Mak, T. C. W. (2009). Chem. Eur. J. 15, 6518–6528. Web of Science CSD CrossRef PubMed CAS Google Scholar
Dendrinou-Samara, C., Alexiou, M., Zaleski, C. M., Kampf, J. W., Kirk, M. L., Kessissoglou, D. P. & Pecoraro, V. L. (2003). Angew. Chem. Int. Ed. 42, 3763-3766. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wan, C. Q., Chen, X. D. & Mak, T. C. W. (2008). CrstEngComm, 10, 475-478. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.