Di-μ-thio­cyanato-κ⁴N:N-bis­({5-meth­oxy-2-[3-(methyl­amino)propyl­imino­meth­yl]phenolato-κ³O¹,N,N′}copper(II))

The title thio­cyanate-bridged dinuclear copper(II) complex, [Cu₂(C₁₂H₁₇N₂O₂)₂(NCS)₂], possesses crystallographic inversion symmetry. Each Cu^II atom is five-coordinated by one imine N, one amine N and one phenolate O atom of the Schiff base ligand, and by two N atoms from two bridging thio­cyanate ligands, forming a square-pyramidal geometry. Beside the two thio­cyanate bridges, there are two intra­molecular N—H...O hydrogen bonds, which further link the two Cu(C₁₂H₁₇N₂O₂)(NCS) units. The Cu...Cu separation is 3.261 (2) Å. Parts of the methylaminopropylimino segment are disordered over two sites with occupancies of 0.669(9) and 0.331(9).

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.040
• wR factor = 0.108
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu1    --  N3_a    ..      14.28 su

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.46
           From the CIF: _diffrn_reflns_theta_full          28.46
           From the CIF: _reflns_number_total               3544
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3759
           Completeness (_total/calc)             94.28%
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    --  N3      ..       5.06 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        215

Alert level G
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................      13.00 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         50
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          !

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

S1. Comment

An extensive effort has been made to prepare and characterize a variety of coordination complexes in an attempt to model the physical and chemical behaviour of copper-containing enzymes (Reddy et al., 2000). The peculiarity of copper lies in its ability to form complexes with coordination numbers of four, five, and six (Ray et al. 2003; Arnold et al., 2003; Raptopoulou et al., 1998). As a continuation of our own work in this area (Wang & Li, 2005; Wang et al., 2006), the title compound, a new copper(II) complex, is reported here.

The title compound is a thiocyanate-bridged dinuclear copper(II) complex (Fig. 1), with a Cu···Cu separation of 3.2608 (7) Å. The complex possesses a crystallographic inversion centre symmetry. Each Cu^II atom is five-coordinated by one imine N, one amine N, and one phenolate O atom of the Schiff base ligand, and by two N atoms from two thiocyanate ligands, forming a square-pyramidal geometry. The bond lengths and angles (Table 1) are typical and comparable with those in other copper(II) complexes with Schiff bases and thiocyanate ligands (Elmali et al., 2000; You & Zhu, 2005; Liu et al., 2004; Datta et al., 2008; Habibi et al., 2007). Beside the two thiocyanate bridges, there exist two N—H···O hydrogen bonds (Table 2) in the complex, which further link the two [Cu(C₁₂H₁₇N₂O₂)(NCS)] units together (Fig. 2).

Related literature

For general background to copper complexes, see: Reddy et al. (2000); Ray et al. (2003); Arnold et al. (2003); Raptopoulou et al. (1998). For our previous reports of copper(II) complexes, see: Wang & Li (2005); Wang et al. (2006). For related structures, see: Elmali et al. (2000); You & Zhu (2005); Liu et al. (2004); Datta et al. (2008); Habibi et al. (2007).

S2. Experimental

4-Methoxysalicylaldehyde (0.1 mmol, 15.2 mg), N-methylpropane-1,3-diamine (0.1 mmol, 8.8 mg), NH₄NCS (0.1 mmol, 7.6 mg) and Cu(CH₃COO)₂.H₂O (0.1 mmol, 19.9 mg) were dissolved in methanol (20 ml). The mixture was stirred at room temperature for 1 h to give a blue solution. The resulting solution was allowed to stand in air for a few days, and blue block-shaped crystals were formed.

S3. Refinement

Atoms C9, C10 and C11 of the methylaminopropylimino segment are disordered over two sites with occupancies of 0.669 (9) and 0.331 (9). The N—C and also the C—C distances involving the disordered atoms were restrained to be equal. The U^ij parameters of the disordered atoms, and atom C12 were restrained to an approximate isotropic behaviour. H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93-0.97 Å, N—H distances in the range 0.90-0.91 Å and with U_iso(H) = 1.2U_eq(C,N) and 1.5U_eq(methyl C).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title compound, showing 30% displacement ellipsoids (arbitrary spheres for the H atoms). Unlabelled atoms are at the symmetry position (1 - x, - y, - z). Only the major disorder component is shown.
	Fig. 2. The crystal packing of the title compound. Intramolecular N—H···O hydrogen bonds are shown as dashed lines.

Di-µ-thiocyanato-κ⁴N:N-bis({5-methoxy-2-[3- (methylamino)propyliminomethyl]phenolato- κ³O¹,N,N'}copper(II))

Crystal data

[Cu2(C12H17N2O2)2(NCS)2]	F(000) = 708
Mr = 685.79	Dx = 1.531 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2304 reflections
a = 11.8003 (18) Å	θ = 2.5–25.1°
b = 15.373 (2) Å	µ = 1.61 mm^−1
c = 8.6740 (13) Å	T = 298 K
β = 108.972 (7)°	Block, blue
V = 1488.0 (4) Å^3	0.20 × 0.20 × 0.18 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	3544 independent reflections
Radiation source: fine-focus sealed tube	2496 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 28.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.739, Tmax = 0.760	k = −20→19
9297 measured reflections	l = −11→10

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0508P)^2 + 0.2175P] where P = (Fo^2 + 2Fc^2)/3
3544 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.48 e Å^−3
50 restraints	Δρmin = −0.41 e Å^−3

Special details

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 > 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	Occ. (<1)
Cu1	0.44981 (3)	0.09693 (2)	0.01842 (4)	0.04380 (14)
S1	0.77288 (9)	0.09042 (7)	−0.17937 (13)	0.0751 (3)
O1	0.33324 (18)	0.07895 (14)	−0.1912 (2)	0.0557 (6)
O2	−0.03088 (19)	0.11364 (15)	−0.6308 (3)	0.0612 (6)
N1	0.3347 (2)	0.14948 (17)	0.1093 (3)	0.0578 (7)
N2	0.5877 (3)	0.1033 (2)	0.2257 (4)	0.0775 (10)
H2A	0.6321	0.0548	0.2262	0.093*	0.669 (9)
H2B	0.6324	0.0572	0.2174	0.093*	0.331 (9)
N3	0.5707 (2)	0.06534 (19)	−0.0884 (3)	0.0608 (7)
C1	0.1697 (2)	0.15468 (16)	−0.1467 (3)	0.0412 (6)
C2	0.2230 (2)	0.10933 (17)	−0.2462 (4)	0.0433 (7)
C3	0.1564 (3)	0.09443 (17)	−0.4110 (4)	0.0447 (7)
H3	0.1906	0.0638	−0.4774	0.054*
C4	0.0408 (2)	0.12515 (19)	−0.4741 (4)	0.0458 (7)
C5	−0.0121 (3)	0.1713 (2)	−0.3762 (4)	0.0558 (8)
H5	−0.0897	0.1925	−0.4201	0.067*
C6	0.0507 (3)	0.18466 (18)	−0.2176 (4)	0.0516 (7)
H6	0.0145	0.2146	−0.1528	0.062*
C7	0.0149 (3)	0.0685 (2)	−0.7408 (4)	0.0664 (9)
H7A	0.0827	0.0993	−0.7513	0.080*
H7B	−0.0461	0.0646	−0.8454	0.080*
H7C	0.0391	0.0110	−0.6998	0.080*
C8	0.2262 (3)	0.16936 (18)	0.0221 (4)	0.0516 (7)
H8	0.1799	0.1965	0.0768	0.062*
C9	0.3506 (5)	0.1469 (5)	0.2885 (6)	0.0633 (17)	0.669 (9)
H9A	0.3322	0.0889	0.3178	0.076*	0.669 (9)
H9B	0.2951	0.1872	0.3117	0.076*	0.669 (9)
C10	0.4770 (5)	0.1705 (5)	0.3900 (8)	0.068 (2)	0.669 (9)
H10A	0.4972	0.2259	0.3522	0.082*	0.669 (9)
H10B	0.4798	0.1780	0.5022	0.082*	0.669 (9)
C11	0.5706 (8)	0.1048 (6)	0.3857 (7)	0.080 (3)	0.669 (9)
H11A	0.6459	0.1191	0.4689	0.096*	0.669 (9)
H11B	0.5462	0.0475	0.4098	0.096*	0.669 (9)
C9A	0.3884 (12)	0.1980 (8)	0.2722 (11)	0.068 (4)	0.331 (9)
H9AA	0.4489	0.2391	0.2655	0.082*	0.331 (9)
H9AB	0.3265	0.2293	0.3004	0.082*	0.331 (9)
C10A	0.4432 (15)	0.1287 (10)	0.397 (2)	0.086 (5)	0.331 (9)
H10C	0.3808	0.0888	0.4019	0.103*	0.331 (9)
H10D	0.4758	0.1559	0.5033	0.103*	0.331 (9)
C11A	0.5414 (14)	0.0777 (10)	0.3617 (15)	0.085 (6)	0.331 (9)
H11C	0.6096	0.0773	0.4613	0.102*	0.331 (9)
H11D	0.5137	0.0181	0.3414	0.102*	0.331 (9)
C12	0.6695 (4)	0.1786 (3)	0.2263 (7)	0.1234 (19)
H12A	0.6282	0.2323	0.2276	0.148*
H12B	0.6930	0.1762	0.1303	0.148*
H12C	0.7394	0.1753	0.3214	0.148*
C13	0.6548 (3)	0.07722 (19)	−0.1263 (4)	0.0500 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0406 (2)	0.0484 (2)	0.0408 (2)	0.00958 (15)	0.01100 (16)	−0.00055 (14)
S1	0.0543 (5)	0.1109 (8)	0.0669 (6)	−0.0065 (5)	0.0290 (5)	0.0033 (5)
O1	0.0440 (12)	0.0789 (15)	0.0409 (11)	0.0279 (10)	0.0095 (9)	−0.0046 (10)
O2	0.0424 (12)	0.0714 (15)	0.0598 (15)	0.0034 (10)	0.0026 (11)	−0.0030 (11)
N1	0.0597 (16)	0.0727 (18)	0.0399 (14)	0.0239 (14)	0.0149 (13)	−0.0057 (12)
N2	0.0566 (18)	0.093 (2)	0.063 (2)	0.0254 (16)	−0.0074 (15)	−0.0285 (16)
N3	0.0474 (15)	0.0776 (18)	0.0592 (17)	0.0080 (14)	0.0195 (14)	0.0049 (14)
C1	0.0389 (14)	0.0394 (14)	0.0484 (16)	0.0053 (12)	0.0185 (13)	0.0028 (12)
C2	0.0404 (15)	0.0425 (16)	0.0472 (17)	0.0080 (12)	0.0146 (13)	0.0073 (12)
C3	0.0411 (15)	0.0495 (16)	0.0435 (16)	0.0043 (12)	0.0140 (13)	0.0037 (12)
C4	0.0387 (16)	0.0446 (15)	0.0500 (17)	0.0000 (12)	0.0088 (14)	0.0074 (13)
C5	0.0328 (15)	0.0577 (19)	0.073 (2)	0.0075 (13)	0.0113 (16)	0.0021 (16)
C6	0.0410 (16)	0.0481 (17)	0.070 (2)	0.0043 (13)	0.0239 (16)	−0.0047 (14)
C7	0.061 (2)	0.079 (2)	0.0491 (19)	−0.0022 (18)	0.0044 (17)	0.0007 (17)
C8	0.0577 (19)	0.0498 (17)	0.0539 (18)	0.0126 (14)	0.0271 (16)	0.0011 (14)
C9	0.072 (4)	0.075 (4)	0.044 (3)	0.013 (3)	0.021 (3)	−0.004 (3)
C10	0.080 (4)	0.073 (4)	0.042 (3)	0.010 (3)	0.007 (3)	−0.021 (3)
C11	0.104 (5)	0.086 (5)	0.030 (3)	0.029 (4)	−0.007 (3)	−0.017 (3)
C9A	0.070 (7)	0.080 (7)	0.053 (6)	0.028 (6)	0.018 (5)	−0.008 (5)
C10A	0.089 (9)	0.106 (9)	0.062 (7)	0.005 (7)	0.024 (7)	0.018 (7)
C11A	0.100 (9)	0.085 (8)	0.038 (7)	0.041 (7)	−0.022 (6)	−0.032 (6)
C12	0.066 (3)	0.138 (4)	0.148 (4)	−0.020 (3)	0.010 (3)	−0.070 (3)
C13	0.0459 (17)	0.0568 (18)	0.0452 (17)	0.0038 (14)	0.0118 (15)	0.0024 (13)

Geometric parameters (Å, º)

Cu1—O1	1.910 (2)	C5—H5	0.93
Cu1—N1	1.953 (2)	C6—H6	0.93
Cu1—N2	1.997 (3)	C7—H7A	0.96
Cu1—N3	1.998 (3)	C7—H7B	0.96
Cu1—N3^i	2.598 (4)	C7—H7C	0.96
S1—C13	1.616 (3)	C8—H8	0.93
O1—C2	1.317 (3)	C9—C10	1.509 (6)
O2—C4	1.359 (3)	C9—H9A	0.97
O2—C7	1.421 (4)	C9—H9B	0.97
N1—C8	1.294 (4)	C10—C11	1.506 (6)
N1—C9	1.504 (5)	C10—H10A	0.97
N1—C9A	1.540 (8)	C10—H10B	0.97
N2—C11	1.467 (6)	C11—H11A	0.97
N2—C12	1.505 (5)	C11—H11B	0.97
N2—C11A	1.506 (9)	C9A—C10A	1.507 (8)
N2—H2A	0.91	C9A—H9AA	0.97
N2—H2B	0.90	C9A—H9AB	0.97
N3—C13	1.157 (4)	C10A—C11A	1.510 (8)
C1—C2	1.407 (4)	C10A—H10C	0.97
C1—C6	1.415 (4)	C10A—H10D	0.97
C1—C8	1.416 (4)	C11A—H11C	0.97
C2—C3	1.408 (4)	C11A—H11D	0.97
C3—C4	1.378 (4)	C12—H12A	0.96
C3—H3	0.93	C12—H12B	0.96
C4—C5	1.399 (4)	C12—H12C	0.96
C5—C6	1.350 (4)
O1—Cu1—N1	93.67 (10)	H7A—C7—H7B	109.5
O1—Cu1—N2	171.12 (10)	O2—C7—H7C	109.5
N1—Cu1—N2	94.96 (12)	H7A—C7—H7C	109.5
O1—Cu1—N3	85.70 (10)	H7B—C7—H7C	109.5
N1—Cu1—N3	169.45 (12)	N1—C8—C1	127.6 (3)
N2—Cu1—N3	86.20 (12)	N1—C8—H8	116.2
N3^i—Cu1—N1	99.91 (15)	C1—C8—H8	116.2
N3^i—Cu1—N2	87.06 (15)	N1—C9—C10	111.3 (5)
N3^i—Cu1—N3	90.57 (15)	N1—C9—H9A	109.4
N3^i—Cu1—O1	89.50 (15)	C10—C9—H9A	109.4
C2—O1—Cu1	127.91 (18)	N1—C9—H9B	109.4
C4—O2—C7	119.1 (2)	C10—C9—H9B	109.4
C8—N1—C9	112.2 (3)	H9A—C9—H9B	108.0
C8—N1—C9A	117.1 (5)	C11—C10—C9	114.7 (6)
C8—N1—Cu1	123.2 (2)	C11—C10—H10A	108.6
C9—N1—Cu1	122.4 (3)	C9—C10—H10A	108.6
C9A—N1—Cu1	116.0 (5)	C11—C10—H10B	108.6
C11—N2—C12	105.7 (5)	C9—C10—H10B	108.6
C12—N2—C11A	126.4 (7)	H10A—C10—H10B	107.6
C11—N2—Cu1	122.0 (4)	N2—C11—C10	111.2 (5)
C12—N2—Cu1	112.0 (3)	N2—C11—H11A	109.4
C11A—N2—Cu1	107.2 (7)	C10—C11—H11A	109.4
C11—N2—H2A	105.3	N2—C11—H11B	109.4
C12—N2—H2A	105.3	C10—C11—H11B	109.4
C11A—N2—H2A	97.8	H11A—C11—H11B	108.0
Cu1—N2—H2A	105.3	C10A—C9A—N1	105.7 (11)
C11—N2—H2B	110.6	C10A—C9A—H9AA	110.6
C12—N2—H2B	102.4	N1—C9A—H9AA	110.6
C11A—N2—H2B	103.1	C10A—C9A—H9AB	110.6
Cu1—N2—H2B	102.5	N1—C9A—H9AB	110.6
C13—N3—Cu1	154.3 (3)	H9AA—C9A—H9AB	108.7
C2—C1—C6	118.3 (3)	C9A—C10A—C11A	113.5 (12)
C2—C1—C8	124.0 (3)	C9A—C10A—H10C	108.9
C6—C1—C8	117.7 (3)	C11A—C10A—H10C	108.9
O1—C2—C1	122.6 (3)	C9A—C10A—H10D	108.9
O1—C2—C3	118.0 (3)	C11A—C10A—H10D	108.9
C1—C2—C3	119.3 (3)	H10C—C10A—H10D	107.7
C4—C3—C2	120.1 (3)	N2—C11A—C10A	121.4 (11)
C4—C3—H3	120.0	N2—C11A—H11C	107.0
C2—C3—H3	120.0	C10A—C11A—H11C	107.0
O2—C4—C3	124.5 (3)	N2—C11A—H11D	107.0
O2—C4—C5	114.7 (2)	C10A—C11A—H11D	107.0
C3—C4—C5	120.8 (3)	H11C—C11A—H11D	106.7
C6—C5—C4	119.4 (3)	N2—C12—H12A	109.5
C6—C5—H5	120.3	N2—C12—H12B	109.5
C4—C5—H5	120.3	H12A—C12—H12B	109.5
C5—C6—C1	122.1 (3)	N2—C12—H12C	109.5
C5—C6—H6	118.9	H12A—C12—H12C	109.5
C1—C6—H6	118.9	H12B—C12—H12C	109.5
O2—C7—H7A	109.5	N3—C13—S1	178.1 (3)
O2—C7—H7B	109.5
N1—Cu1—O1—C2	10.5 (3)	C7—O2—C4—C5	179.3 (3)
N3—Cu1—O1—C2	−159.0 (3)	C2—C3—C4—O2	−179.5 (3)
O1—Cu1—N1—C8	−8.2 (3)	C2—C3—C4—C5	0.0 (4)
N2—Cu1—N1—C8	173.9 (3)	O2—C4—C5—C6	178.6 (3)
N3—Cu1—N1—C8	78.0 (7)	C3—C4—C5—C6	−0.9 (4)
O1—Cu1—N1—C9	153.7 (4)	C4—C5—C6—C1	1.0 (5)
N2—Cu1—N1—C9	−24.2 (4)	C2—C1—C6—C5	−0.2 (4)
N3—Cu1—N1—C9	−120.1 (6)	C8—C1—C6—C5	−177.8 (3)
O1—Cu1—N1—C9A	−165.8 (6)	C9—N1—C8—C1	−160.8 (4)
N2—Cu1—N1—C9A	16.3 (6)	C9A—N1—C8—C1	160.1 (7)
N3—Cu1—N1—C9A	−79.5 (8)	Cu1—N1—C8—C1	2.8 (5)
N1—Cu1—N2—C11	25.6 (5)	C2—C1—C8—N1	4.5 (5)
N3—Cu1—N2—C11	−164.9 (5)	C6—C1—C8—N1	−178.0 (3)
N1—Cu1—N2—C12	−101.1 (3)	C8—N1—C9—C10	−150.3 (5)
N3—Cu1—N2—C12	68.4 (3)	C9A—N1—C9—C10	−44.3 (8)
N1—Cu1—N2—C11A	41.7 (6)	Cu1—N1—C9—C10	46.0 (7)
N3—Cu1—N2—C11A	−148.9 (6)	N1—C9—C10—C11	−68.3 (9)
O1—Cu1—N3—C13	123.7 (6)	C12—N2—C11—C10	81.1 (7)
N1—Cu1—N3—C13	36.7 (10)	C11A—N2—C11—C10	−97 (2)
N2—Cu1—N3—C13	−60.0 (6)	Cu1—N2—C11—C10	−48.3 (8)
Cu1—O1—C2—C1	−6.7 (4)	C9—C10—C11—N2	69.8 (9)
Cu1—O1—C2—C3	174.05 (19)	C8—N1—C9A—C10A	132.2 (9)
C6—C1—C2—O1	−180.0 (2)	C9—N1—C9A—C10A	41.3 (8)
C8—C1—C2—O1	−2.5 (4)	Cu1—N1—C9A—C10A	−68.8 (12)
C6—C1—C2—C3	−0.8 (4)	N1—C9A—C10A—C11A	60.8 (18)
C8—C1—C2—C3	176.7 (3)	C11—N2—C11A—C10A	78 (2)
O1—C2—C3—C4	−179.9 (2)	C12—N2—C11A—C10A	75.1 (16)
C1—C2—C3—C4	0.9 (4)	Cu1—N2—C11A—C10A	−60.6 (15)
C7—O2—C4—C3	−1.2 (4)	C9A—C10A—C11A—N2	7 (2)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1^i	0.91	2.14	2.999 (3)	157

Symmetry code: (i) −x+1, −y, −z.