Tetra-μ-acetato-bis­{[9-(pyrazin-2-yl)-9H-carbazole]copper(II)}

Li, J.M.

doi:10.1107/S160053680902710X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m932

doi:10.1107/S160053680902710X

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Tetra-μ-acetato-bis{[9-(pyrazin-2-yl)-9H-carbazole]copper(II)}

Jin Min Li ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shanxi Datong University, Datong 037009, People's Republic of China
^*Correspondence e-mail: jinminli1957@yahoo.com.cn

(Received 1 July 2009; accepted 10 July 2009; online 18 July 2009)

The title complex, [Cu₂(CH₃COO)₄(C₁₆H₁₁N₃)₂], lies on an inversion centre, with four acetate ligands bridging two symmetry-related Cu^II ions and two monodentate 9-(pyrazin-2-yl)-9H-carbazole ligands coordinating each Cu^II ion via the N atoms of the pyrazine rings, forming slightly distorted square-pyramidal geometries. There are weak π–π stacking interactions between the pyrrole rings of symmetry-related molecules, with a centroid-to-centroid distance of 3.692 (2) Å.

Related literature

For a related structure, see: Meng et al. (2009 ).

Experimental

Crystal data

[Cu₂(C₂H₃O₂)₄(C₁₆H₁₁N₃)₂]
M_r = 853.81
Triclinic, $[P \overline 1]$
a = 8.2608 (12) Å
b = 9.7181 (15) Å
c = 11.9688 (18) Å
α = 83.002 (2)°
β = 86.756 (2)°
γ = 72.533 (2)°
V = 909.5 (2) Å³
Z = 1
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 298 K
0.35 × 0.34 × 0.23 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.672, T_max = 0.765
4972 measured reflections
3493 independent reflections
3183 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.148
S = 1.05
3493 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 2.11 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902710X/lh2859sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902710X/lh2859Isup2.hkl

checkCIF report

Comment top

9-(pyrazin-2-yl)-9H-carbazole is potentially good ligand for forming complexes with π–π stacking interactions due to the large conjugation plane of carbazole ring system. Interest in synthesizing complexes with π–π stacking interactions motivated us to obtain the title complex and herein the crystal structure of the title compound, (I), is reported.

Figure 1 and Table 1 reveal that the unique Cu^II ion is in a slightly distorted square-pyramidal coordination geometry with N1 atom lying at the apex. Four actate anions bridge two symmetry related Cu^II ions with a Cu···Cu separation of 2.6120 (7) Å, which is shorter than that of the similar binuclear Cu^II complex (Meng et al., 2009). In (I) there is an inversion center in the middle of the two Cu^II ions. There is a weak π–π interaction with Cg1···Cg1ⁱ = 3.692 (2) Å (symmetry code: (i): 1-x, 1-y, 2-z and Cg1···Cg1ⁱ_perp = 3.505 Å; α is 0.00° [Cg1 is the centroid of C5–C8/N3 ring; Cg1···Cg1ⁱ_perp is the perpendicular distance from ring Cg1 to ring Cg1ⁱ; α is the dihedral angle between the Cg1 ring plane and the Cg1ⁱ ring plane]. The dihedral angle between pyrazine ring plane and carbazole ring system plane is 20.01 (14)°.

Related literature top

For a related structure, see: Meng et al. (2009).

Experimental top

9-(pyrazin-2-yl)-9H-carbazole (0.1115 g, 0.455 mmol) was dissolved in 10 ml acetonitrile and copper acetate hydrate (0.0910 g, 0.456 mmol) was added into 10 ml methanol. The solutions were mixed and stirred for a few minutes. Blue single crystals were obtained after the solution had been allowed to stand at room temperature for one month.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of title complex with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Tetra-µ-acetato-bis{[9-(pyrazin-2-yl)-9H-carbazole]copper(II)} top

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₆H₁₁N₃)₂]	Z = 1
M_r = 853.81	F(000) = 438
Triclinic, P1	D_x = 1.559 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2608 (12) Å	Cell parameters from 3057 reflections
b = 9.7181 (15) Å	θ = 2.6–28.0°
c = 11.9688 (18) Å	µ = 1.23 mm⁻¹
α = 83.002 (2)°	T = 298 K
β = 86.756 (2)°	Block, blue
γ = 72.533 (2)°	0.35 × 0.34 × 0.23 mm
V = 909.5 (2) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	3493 independent reflections
Radiation source: fine-focus sealed tube	3183 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
T_min = 0.672, T_max = 0.765	k = −11→11
4972 measured reflections	l = −6→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0986P)² + 0.8758P] where P = (F_o² + 2F_c²)/3
3493 reflections	(Δ/σ)_max = 0.011
255 parameters	Δρ_max = 2.11 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₆H₁₁N₃)₂]	γ = 72.533 (2)°
M_r = 853.81	V = 909.5 (2) Å³
Triclinic, P1	Z = 1
a = 8.2608 (12) Å	Mo Kα radiation
b = 9.7181 (15) Å	µ = 1.23 mm⁻¹
c = 11.9688 (18) Å	T = 298 K
α = 83.002 (2)°	0.35 × 0.34 × 0.23 mm
β = 86.756 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3493 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3183 reflections with I > 2σ(I)
T_min = 0.672, T_max = 0.765	R_int = 0.018
4972 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.05	Δρ_max = 2.11 e Å⁻³
3493 reflections	Δρ_min = −0.42 e Å⁻³
255 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.4087 (6)	0.8536 (5)	1.0557 (4)	0.0503 (10)
H1	0.3442	0.9488	1.0348	0.060*
C2	0.5243 (5)	0.7790 (4)	0.9784 (3)	0.0406 (8)
H2	0.5387	0.8235	0.9068	0.049*
C3	0.3877 (6)	0.7884 (5)	1.1634 (3)	0.0540 (11)
H3	0.3085	0.8399	1.2131	0.065*
C4	0.4827 (5)	0.6489 (5)	1.1969 (3)	0.0453 (9)
H4	0.4690	0.6057	1.2691	0.054*
C5	0.5990 (4)	0.5734 (4)	1.1220 (3)	0.0334 (7)
C6	0.6169 (4)	0.6377 (4)	1.0109 (3)	0.0307 (7)
C7	0.7230 (4)	0.4315 (4)	1.1335 (3)	0.0334 (7)
C8	0.8123 (4)	0.4117 (4)	1.0305 (3)	0.0322 (7)
C9	0.9440 (5)	0.2866 (4)	1.0177 (3)	0.0468 (9)
H9	1.0030	0.2722	0.9495	0.056*
C10	0.9841 (6)	0.1841 (5)	1.1104 (4)	0.0587 (12)
H10	1.0721	0.0992	1.1038	0.070*
C11	0.8984 (6)	0.2028 (5)	1.2130 (4)	0.0545 (11)
H11	0.9308	0.1321	1.2738	0.065*
C12	0.7652 (5)	0.3261 (4)	1.2249 (3)	0.0434 (9)
H12	0.7049	0.3383	1.2928	0.052*
C13	0.7908 (4)	0.5546 (3)	0.8399 (3)	0.0281 (6)
C14	0.6825 (4)	0.6558 (4)	0.7633 (3)	0.0326 (7)
H14	0.5745	0.7071	0.7872	0.039*
C15	0.8839 (4)	0.6001 (4)	0.6240 (3)	0.0358 (7)
H15	0.9228	0.6156	0.5504	0.043*
C16	0.9841 (5)	0.4945 (4)	0.6993 (3)	0.0402 (8)
H16	1.0871	0.4360	0.6735	0.048*
C17	0.3340 (4)	1.0792 (3)	0.6772 (3)	0.0296 (7)
C18	0.2354 (5)	1.1199 (4)	0.7839 (3)	0.0397 (8)
H18A	0.2835	1.1814	0.8195	0.059*
H18B	0.2404	1.0337	0.8338	0.059*
H18C	0.1192	1.1707	0.7663	0.059*
C19	0.2777 (4)	0.8810 (4)	0.4608 (3)	0.0349 (7)
C20	0.1397 (5)	0.8131 (5)	0.4428 (4)	0.0529 (10)
H20A	0.0522	0.8376	0.4996	0.079*
H20B	0.1872	0.7096	0.4475	0.079*
H20C	0.0922	0.8491	0.3698	0.079*
Cu1	0.58853 (4)	0.87807 (4)	0.55418 (3)	0.02722 (17)
N1	0.7313 (4)	0.6801 (3)	0.6565 (2)	0.0305 (6)
N2	0.9401 (4)	0.4724 (3)	0.8071 (2)	0.0363 (6)
N3	0.7439 (4)	0.5373 (3)	0.9538 (2)	0.0315 (6)
O1	0.4480 (3)	0.9594 (3)	0.6823 (2)	0.0384 (6)
O2	0.4057 (3)	0.8024 (3)	0.5140 (2)	0.0423 (6)
O3	0.7047 (3)	0.8328 (3)	0.4096 (2)	0.0385 (6)
O4	0.7467 (3)	0.9890 (3)	0.5768 (2)	0.0416 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.055 (2)	0.040 (2)	0.045 (2)	0.0041 (17)	0.0040 (18)	−0.0097 (18)
C2	0.048 (2)	0.0384 (19)	0.0271 (17)	−0.0019 (16)	0.0018 (15)	0.0000 (15)
C3	0.056 (2)	0.056 (3)	0.042 (2)	−0.003 (2)	0.0116 (19)	−0.014 (2)
C4	0.051 (2)	0.055 (2)	0.0289 (18)	−0.0145 (18)	0.0077 (16)	−0.0053 (17)
C5	0.0367 (18)	0.0358 (18)	0.0281 (17)	−0.0130 (14)	−0.0011 (13)	0.0008 (14)
C6	0.0341 (17)	0.0333 (17)	0.0237 (15)	−0.0089 (13)	−0.0003 (12)	−0.0013 (13)
C7	0.0371 (18)	0.0353 (18)	0.0277 (16)	−0.0124 (14)	−0.0032 (13)	0.0031 (14)
C8	0.0355 (17)	0.0332 (17)	0.0243 (16)	−0.0074 (14)	−0.0038 (13)	0.0055 (13)
C9	0.048 (2)	0.043 (2)	0.035 (2)	0.0024 (17)	0.0051 (16)	0.0082 (16)
C10	0.060 (3)	0.040 (2)	0.054 (3)	0.0091 (19)	0.002 (2)	0.0175 (19)
C11	0.066 (3)	0.047 (2)	0.041 (2)	−0.011 (2)	−0.007 (2)	0.0198 (18)
C12	0.054 (2)	0.047 (2)	0.0280 (18)	−0.0169 (18)	−0.0018 (16)	0.0097 (16)
C13	0.0319 (16)	0.0272 (15)	0.0231 (15)	−0.0077 (12)	−0.0012 (12)	0.0025 (12)
C14	0.0315 (16)	0.0341 (17)	0.0253 (15)	−0.0014 (13)	0.0012 (12)	0.0006 (13)
C15	0.0404 (19)	0.0351 (18)	0.0256 (16)	−0.0049 (14)	0.0057 (13)	0.0016 (13)
C16	0.0349 (18)	0.0380 (19)	0.0354 (19)	0.0035 (14)	0.0057 (14)	0.0040 (15)
C17	0.0301 (16)	0.0306 (16)	0.0256 (15)	−0.0061 (13)	0.0037 (12)	−0.0026 (13)
C18	0.0437 (19)	0.0377 (19)	0.0293 (17)	−0.0010 (15)	0.0068 (14)	−0.0038 (15)
C19	0.0340 (17)	0.044 (2)	0.0286 (16)	−0.0138 (15)	0.0053 (13)	−0.0072 (15)
C20	0.044 (2)	0.065 (3)	0.057 (3)	−0.027 (2)	0.0008 (19)	−0.009 (2)
Cu1	0.0280 (3)	0.0261 (3)	0.0220 (2)	−0.00184 (16)	0.00039 (15)	0.00279 (16)
N1	0.0330 (14)	0.0294 (14)	0.0233 (13)	−0.0030 (11)	−0.0007 (11)	0.0039 (11)
N2	0.0341 (15)	0.0350 (15)	0.0309 (15)	−0.0006 (12)	0.0001 (12)	0.0055 (12)
N3	0.0344 (14)	0.0314 (14)	0.0222 (13)	−0.0038 (11)	−0.0008 (11)	0.0068 (11)
O1	0.0408 (13)	0.0348 (13)	0.0285 (12)	0.0027 (10)	0.0064 (10)	0.0000 (10)
O2	0.0409 (14)	0.0401 (14)	0.0466 (15)	−0.0150 (11)	−0.0051 (11)	0.0024 (12)
O3	0.0397 (13)	0.0364 (13)	0.0273 (12)	0.0039 (10)	0.0039 (10)	0.0024 (10)
O4	0.0364 (13)	0.0433 (15)	0.0440 (15)	−0.0121 (11)	−0.0071 (11)	0.0029 (12)

Geometric parameters (Å, º) top

C1—C3	1.391 (6)	C14—H14	0.9300
C1—C2	1.393 (5)	C15—N1	1.332 (4)
C1—H1	0.9300	C15—C16	1.378 (5)
C2—C6	1.376 (5)	C15—H15	0.9300
C2—H2	0.9300	C16—N2	1.330 (4)
C3—C4	1.371 (6)	C16—H16	0.9300
C3—H3	0.9300	C17—O3ⁱ	1.253 (4)
C4—C5	1.380 (5)	C17—O1	1.256 (4)
C4—H4	0.9300	C17—C18	1.504 (4)
C5—C6	1.419 (5)	C18—H18A	0.9600
C5—C7	1.446 (5)	C18—H18B	0.9600
C6—N3	1.409 (4)	C18—H18C	0.9600
C7—C12	1.386 (5)	C19—O4ⁱ	1.248 (4)
C7—C8	1.405 (5)	C19—O2	1.257 (4)
C8—C9	1.384 (5)	C19—C20	1.516 (5)
C8—N3	1.423 (4)	C20—H20A	0.9600
C9—C10	1.382 (5)	C20—H20B	0.9600
C9—H9	0.9300	C20—H20C	0.9600
C10—C11	1.385 (6)	Cu1—O3	1.963 (2)
C10—H10	0.9300	Cu1—O1	1.967 (2)
C11—C12	1.378 (6)	Cu1—O2	1.972 (3)
C11—H11	0.9300	Cu1—O4	1.975 (3)
C12—H12	0.9300	Cu1—N1	2.196 (3)
C13—N2	1.321 (4)	Cu1—Cu1ⁱ	2.6120 (7)
C13—C14	1.398 (4)	O3—C17ⁱ	1.253 (4)
C13—N3	1.399 (4)	O4—C19ⁱ	1.248 (4)
C14—N1	1.332 (4)

C3—C1—C2	121.2 (4)	N2—C16—H16	118.5
C3—C1—H1	119.4	C15—C16—H16	118.5
C2—C1—H1	119.4	O3ⁱ—C17—O1	125.3 (3)
C6—C2—C1	118.3 (3)	O3ⁱ—C17—C18	117.4 (3)
C6—C2—H2	120.9	O1—C17—C18	117.3 (3)
C1—C2—H2	120.9	C17—C18—H18A	109.5
C4—C3—C1	120.6 (4)	C17—C18—H18B	109.5
C4—C3—H3	119.7	H18A—C18—H18B	109.5
C1—C3—H3	119.7	C17—C18—H18C	109.5
C3—C4—C5	119.1 (4)	H18A—C18—H18C	109.5
C3—C4—H4	120.5	H18B—C18—H18C	109.5
C5—C4—H4	120.5	O4ⁱ—C19—O2	125.6 (3)
C4—C5—C6	120.5 (3)	O4ⁱ—C19—C20	117.2 (3)
C4—C5—C7	132.3 (3)	O2—C19—C20	117.2 (3)
C6—C5—C7	107.1 (3)	C19—C20—H20A	109.5
C2—C6—N3	131.4 (3)	C19—C20—H20B	109.5
C2—C6—C5	120.2 (3)	H20A—C20—H20B	109.5
N3—C6—C5	108.3 (3)	C19—C20—H20C	109.5
C12—C7—C8	120.6 (3)	H20A—C20—H20C	109.5
C12—C7—C5	131.4 (4)	H20B—C20—H20C	109.5
C8—C7—C5	107.9 (3)	O3—Cu1—O1	168.81 (10)
C9—C8—C7	120.9 (3)	O3—Cu1—O2	90.06 (12)
C9—C8—N3	131.0 (3)	O1—Cu1—O2	89.26 (12)
C7—C8—N3	108.1 (3)	O3—Cu1—O4	88.60 (11)
C10—C9—C8	117.2 (4)	O1—Cu1—O4	89.90 (12)
C10—C9—H9	121.4	O2—Cu1—O4	168.78 (10)
C8—C9—H9	121.4	O3—Cu1—N1	97.47 (10)
C9—C10—C11	122.6 (4)	O1—Cu1—N1	93.71 (10)
C9—C10—H10	118.7	O2—Cu1—N1	96.33 (11)
C11—C10—H10	118.7	O4—Cu1—N1	94.88 (11)
C12—C11—C10	120.1 (4)	O3—Cu1—Cu1ⁱ	86.47 (7)
C12—C11—H11	119.9	O1—Cu1—Cu1ⁱ	82.34 (7)
C10—C11—H11	119.9	O2—Cu1—Cu1ⁱ	84.81 (8)
C11—C12—C7	118.6 (4)	O4—Cu1—Cu1ⁱ	83.99 (8)
C11—C12—H12	120.7	N1—Cu1—Cu1ⁱ	175.89 (7)
C7—C12—H12	120.7	C15—N1—C14	117.8 (3)
N2—C13—C14	121.0 (3)	C15—N1—Cu1	121.7 (2)
N2—C13—N3	118.1 (3)	C14—N1—Cu1	118.9 (2)
C14—C13—N3	120.9 (3)	C13—N2—C16	116.8 (3)
N1—C14—C13	121.1 (3)	C13—N3—C6	126.2 (3)
N1—C14—H14	119.4	C13—N3—C8	125.4 (3)
C13—C14—H14	119.4	C6—N3—C8	108.4 (3)
N1—C15—C16	120.0 (3)	C17—O1—Cu1	125.2 (2)
N1—C15—H15	120.0	C19—O2—Cu1	122.3 (2)
C16—C15—H15	120.0	C17ⁱ—O3—Cu1	120.6 (2)
N2—C16—C15	123.0 (3)	C19ⁱ—O4—Cu1	123.3 (2)

C3—C1—C2—C6	0.7 (6)	O4—Cu1—N1—C14	97.6 (3)
C2—C1—C3—C4	0.9 (7)	Cu1ⁱ—Cu1—N1—C14	23.6 (13)
C1—C3—C4—C5	−0.4 (7)	C14—C13—N2—C16	2.4 (5)
C3—C4—C5—C6	−1.7 (6)	N3—C13—N2—C16	−177.8 (3)
C3—C4—C5—C7	175.6 (4)	C15—C16—N2—C13	1.9 (6)
C1—C2—C6—N3	−178.2 (4)	N2—C13—N3—C6	161.2 (3)
C1—C2—C6—C5	−2.8 (6)	C14—C13—N3—C6	−19.0 (5)
C4—C5—C6—C2	3.4 (5)	N2—C13—N3—C8	−21.7 (5)
C7—C5—C6—C2	−174.5 (3)	C14—C13—N3—C8	158.2 (3)
C4—C5—C6—N3	179.8 (3)	C2—C6—N3—C13	−9.3 (6)
C7—C5—C6—N3	1.9 (4)	C5—C6—N3—C13	174.8 (3)
C4—C5—C7—C12	−0.6 (7)	C2—C6—N3—C8	173.2 (4)
C6—C5—C7—C12	176.9 (4)	C5—C6—N3—C8	−2.7 (4)
C4—C5—C7—C8	−177.9 (4)	C9—C8—N3—C13	6.0 (6)
C6—C5—C7—C8	−0.3 (4)	C7—C8—N3—C13	−175.1 (3)
C12—C7—C8—C9	0.2 (6)	C9—C8—N3—C6	−176.5 (4)
C5—C7—C8—C9	177.8 (3)	C7—C8—N3—C6	2.5 (4)
C12—C7—C8—N3	−178.9 (3)	O3ⁱ—C17—O1—Cu1	−2.1 (5)
C5—C7—C8—N3	−1.3 (4)	C18—C17—O1—Cu1	177.6 (2)
C7—C8—C9—C10	−0.7 (6)	O3—Cu1—O1—C17	2.9 (7)
N3—C8—C9—C10	178.1 (4)	O2—Cu1—O1—C17	−83.6 (3)
C8—C9—C10—C11	0.0 (8)	O4—Cu1—O1—C17	85.2 (3)
C9—C10—C11—C12	1.3 (8)	N1—Cu1—O1—C17	−179.9 (3)
C10—C11—C12—C7	−1.8 (7)	Cu1ⁱ—Cu1—O1—C17	1.2 (3)
C8—C7—C12—C11	1.1 (6)	O4ⁱ—C19—O2—Cu1	3.3 (5)
C5—C7—C12—C11	−175.9 (4)	C20—C19—O2—Cu1	−175.5 (2)
N2—C13—C14—N1	−5.0 (5)	O3—Cu1—O2—C19	−88.5 (3)
N3—C13—C14—N1	175.2 (3)	O1—Cu1—O2—C19	80.3 (3)
N1—C15—C16—N2	−3.9 (6)	O4—Cu1—O2—C19	−5.4 (7)
C16—C15—N1—C14	1.2 (5)	N1—Cu1—O2—C19	173.9 (3)
C16—C15—N1—Cu1	166.9 (3)	Cu1ⁱ—Cu1—O2—C19	−2.1 (3)
C13—C14—N1—C15	3.0 (5)	O1—Cu1—O3—C17ⁱ	−1.3 (7)
C13—C14—N1—Cu1	−163.1 (3)	O2—Cu1—O3—C17ⁱ	85.2 (3)
O3—Cu1—N1—C15	21.3 (3)	O4—Cu1—O3—C17ⁱ	−83.7 (3)
O1—Cu1—N1—C15	−158.1 (3)	N1—Cu1—O3—C17ⁱ	−178.4 (3)
O2—Cu1—N1—C15	112.2 (3)	Cu1ⁱ—Cu1—O3—C17ⁱ	0.4 (3)
O4—Cu1—N1—C15	−67.9 (3)	O3—Cu1—O4—C19ⁱ	86.1 (3)
Cu1ⁱ—Cu1—N1—C15	−141.9 (10)	O1—Cu1—O4—C19ⁱ	−82.8 (3)
O3—Cu1—N1—C14	−173.2 (3)	O2—Cu1—O4—C19ⁱ	2.8 (7)
O1—Cu1—N1—C14	7.4 (3)	N1—Cu1—O4—C19ⁱ	−176.6 (3)
O2—Cu1—N1—C14	−82.3 (3)	Cu1ⁱ—Cu1—O4—C19ⁱ	−0.5 (3)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂H₃O₂)₄(C₁₆H₁₁N₃)₂]
M_r	853.81
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.2608 (12), 9.7181 (15), 11.9688 (18)
α, β, γ (°)	83.002 (2), 86.756 (2), 72.533 (2)
V (Å³)	909.5 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.35 × 0.34 × 0.23

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.672, 0.765
No. of measured, independent and observed [I > 2σ(I)] reflections	4972, 3493, 3183
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.148, 1.05
No. of reflections	3493
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.11, −0.42

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Meng, L., Yang, L. Y. & Shi, J. M. (2009). Acta Cryst. E65, m646. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar