Tetra-μ-acetato-κ⁸O:O′-bis­[(2-amino-1,3-benzothia­zole-κN)copper(II)] butanol disolvate

The title compound, [Cu₂(C₂H₃O₂)₄(C₇H₆N₂S)₂]·2C₄H₁₀O, exhibits distorted square-pyramidal coordination geometry around each Cu^II atom, with the basal plane comprising O atoms from four bridging acetate ligands and the apical position occupied by the thia­zole N atom of 2-amino­benzothia­zole. The dinuclear complex lies on a crystallographic centre of inversion and has a Cu...Cu distance of 2.6850 (14) Å. Complexes are linked into one-dimensional chains by a combination of inter­molecular O—H...O and N—H...O hydrogen bonds involving the butanol solvent mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.020 Å
• R factor = 0.084
• wR factor = 0.249
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         20

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.13 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
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         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C14
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C12
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C11
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         25
            CU1 -CU1 -N2  -C1    143.00  4.00   3.777   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         30
            CU1 -CU1 -N2  -C2    -40.00  5.00   3.777   1.555   1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.49(3), Rep   1.487(10) ......       3.00 su-Ra
              C12  -C13     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.49(3), Rep   1.482(10) ......       3.00 su-Ra
              C13  -C14     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.48(3), Rep   1.483(10) ......       3.00 su-Ra
              C14  -C15     1.555   1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.11
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          5

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

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

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S1. Comment

Interest in the study of compounds containing the benzothiazole group has increased on account of their broad spectrum of biological activities (Rana et al., 2007), and also their potential applications in the areas of sensors (Kim et al., 2005), non-linear optics, laser dyes, electroluminescent devices (Costa et al., 2006) and as chelating agents (Usman et al., 2003). A large number of copper compounds with diverse ligands have been synthesized and studied as potential therapeutic agents (Wu et al., 2003) and catalysts (Marko et al., 1996).

In the title compound (Fig. 1), each Cu^II ion is five-coordinated, with a coordination geometry that is best described as distorted square pyramidal. Four O atoms of bridging acetate ligands construct the basal plane of the square pyramid. The 2-aminobenzothiazole molecules are coordinated to Cu^II through their thiazole N atom and occupy the axial position. Four acetate ligands act as bridges to connect the two Cu^II centers into a dinuclear complex across a crystallographic centre of inversion. All the geometrical parameters lie within expected ranges.

The complexes are linked into one-dimensional chains by a combination of intermolecular O—H···O and N—H···O hydrogen bonds involving the butane solvent molecules (Fig. 2).

Related literature

For general literature concerning applications of benzothiazole compounds, see: Rana et al. (2007); Kim et al. (2005); Costa et al. (2006); Wu et al. (2003); Marko et al. (1996). Similar coordination geometry has been observed for a related dinuclear Cu^II complex containing 2-amino-5-chloropyridine (Liu et al., 2003). Other reported 2-aminobenzothiazole complexes with Cu^II contain either six-coordinate (Sieroń & Bukowska-Strżyzewska, 1999, 2000; Sieroń, 2007) or four-coordinate Cu^II (Usman et al., 2003).

S2. Experimental

A solution of 2-aminobenzothiazole (2 mmol) in butanol (10 ml) was added dropwise to Cu(OAc)₂.2H₂O (1 mmol in 10 ml of butanol) with stirring. The resulting solution was left to stand at room temperature and black crystals were obtained after several days.

S3. Refinement

All H atoms were visible in a difference Fourier map. The methyl H atoms were constrained to an ideal geometry with C—H distances of 0.96 Å and U_iso(H) = 1.5U_eq(C). The hydroxyl H atoms were treated as riding atoms with O—H distances normalized to 0.85 Å and with U_iso(H) = 1.5U_eq(O). All other H atoms were placed geometrically and constrained to ride on their parent atoms with C—H distances of 0.93–0.97 Å and N—H distances of 0.90 Å, and with U_iso(H) = 1.2U_eq(C/N). The C—C bonds and 1,3-distances in the butanol molecule were restrained to 1.50 (1) and 2.45 (2) Å, respectively.

Computing details

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

Figures

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 50% probability level. H atoms are omitted.
	Fig. 2. The chain structure in the title compound formed via hydrogen bonds (dashed lines). H atoms are omitted.

Tetra-µ-acetato-κ⁸O:O'-bis[(2-amino-1,3-benzothiazole-κN)copper(II)] butanol disolvate

Crystal data

[Cu2(C2H3O2)4(C7H6N2S)2]·2C4H10O	F(000) = 844
Mr = 811.89	Dx = 1.410 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8320 reflections
a = 10.0998 (17) Å	θ = 2.2–25.7°
b = 11.465 (2) Å	µ = 1.28 mm^−1
c = 16.514 (3) Å	T = 273 K
β = 91.242 (7)°	Block, black
V = 1911.8 (6) Å^3	0.32 × 0.21 × 0.12 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	3353 independent reflections
Radiation source: fine-focus sealed tube	3000 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.686, Tmax = 0.862	k = −13→13
20441 measured reflections	l = −19→19

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.249	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0643P)^2 + 21.2639P] where P = (Fo^2 + 2Fc^2)/3
3353 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.97 e Å^−3
5 restraints	Δρmin = −1.00 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	0.93063 (11)	0.90286 (8)	0.98271 (6)	0.0418 (4)
S1	0.7442 (3)	0.5375 (2)	0.9140 (2)	0.0706 (8)
O1	1.0552 (7)	0.8231 (6)	1.0602 (4)	0.0611 (18)
O2	1.0644 (7)	0.8793 (6)	0.8988 (4)	0.0616 (18)
O3	0.8344 (7)	1.0149 (6)	0.9128 (4)	0.0620 (18)
O4	0.8287 (7)	0.9547 (6)	1.0754 (4)	0.0624 (18)
O5	0.0282 (10)	0.3940 (7)	0.8688 (6)	0.088 (3)
H5	0.0037	0.3299	0.8896	0.131*
N1	0.9877 (9)	0.6283 (8)	0.9201 (7)	0.074 (3)
H1A	1.0440	0.6891	0.9240	0.111*
H1B	1.0208	0.5571	0.9100	0.111*
N2	0.8107 (7)	0.7502 (6)	0.9518 (5)	0.0491 (18)
C1	0.8607 (10)	0.6475 (8)	0.9296 (6)	0.050 (2)
C2	0.6731 (9)	0.7435 (8)	0.9545 (6)	0.051 (2)
C3	0.6197 (11)	0.6342 (9)	0.9356 (7)	0.060 (3)
C4	0.4832 (12)	0.6167 (12)	0.9369 (9)	0.085 (4)
H4A	0.4472	0.5442	0.9239	0.102*
C5	0.4020 (12)	0.7085 (12)	0.9576 (10)	0.092 (4)
H5A	0.3108	0.6977	0.9596	0.110*
C6	0.4558 (12)	0.8154 (11)	0.9753 (9)	0.081 (4)
H6A	0.3999	0.8771	0.9875	0.097*
C7	0.5897 (11)	0.8339 (9)	0.9754 (7)	0.063 (3)
H7A	0.6243	0.9065	0.9893	0.076*
C8	0.8556 (10)	1.1205 (8)	0.9024 (6)	0.051 (2)
C9	0.7718 (14)	1.1838 (11)	0.8413 (9)	0.093 (5)
H9A	0.7082	1.1310	0.8176	0.139*
H9B	0.8268	1.2147	0.7998	0.139*
H9C	0.7263	1.2466	0.8673	0.139*
C10	0.8488 (10)	1.0437 (9)	1.1167 (6)	0.054 (2)
C11	0.7607 (14)	1.0663 (13)	1.1869 (8)	0.089 (4)
H11A	0.6998	1.0027	1.1923	0.134*
H11B	0.7121	1.1373	1.1777	0.134*
H11C	0.8136	1.0736	1.2356	0.134*
C12	0.0949 (18)	0.3587 (19)	0.7984 (11)	0.129 (6)
H12A	0.0785	0.4125	0.7540	0.154*
H12B	0.0684	0.2809	0.7817	0.154*
C13	0.236 (2)	0.361 (3)	0.8257 (12)	0.220 (15)
H13A	0.2570	0.4376	0.8482	0.264*
H13B	0.2509	0.3038	0.8678	0.264*
C14	0.325 (2)	0.337 (3)	0.7572 (13)	0.30 (3)
H14A	0.3449	0.4091	0.7293	0.359*
H14B	0.2805	0.2851	0.7189	0.359*
C15	0.449 (2)	0.282 (3)	0.7884 (18)	0.27 (2)
H15A	0.5061	0.2671	0.7442	0.410*
H15B	0.4279	0.2104	0.8151	0.410*
H15C	0.4918	0.3342	0.8262	0.410*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0566 (7)	0.0260 (5)	0.0427 (6)	−0.0058 (4)	−0.0026 (4)	−0.0019 (4)
S1	0.0751 (18)	0.0379 (13)	0.099 (2)	−0.0159 (12)	0.0041 (15)	−0.0175 (13)
O1	0.079 (5)	0.036 (3)	0.067 (4)	−0.003 (3)	−0.016 (4)	0.011 (3)
O2	0.078 (5)	0.049 (4)	0.059 (4)	−0.011 (3)	0.015 (3)	−0.013 (3)
O3	0.070 (4)	0.046 (4)	0.069 (4)	−0.005 (3)	−0.020 (4)	0.009 (3)
O4	0.068 (4)	0.057 (4)	0.063 (4)	−0.016 (3)	0.011 (3)	−0.006 (4)
O5	0.127 (7)	0.041 (4)	0.095 (6)	0.004 (4)	0.022 (6)	−0.004 (4)
N1	0.065 (6)	0.039 (5)	0.117 (8)	−0.001 (4)	0.014 (5)	−0.014 (5)
N2	0.052 (4)	0.032 (4)	0.063 (5)	−0.004 (3)	−0.002 (4)	−0.001 (3)
C1	0.064 (6)	0.032 (4)	0.054 (5)	−0.004 (4)	0.003 (4)	−0.006 (4)
C2	0.055 (5)	0.038 (5)	0.058 (5)	−0.007 (4)	−0.006 (4)	0.007 (4)
C3	0.068 (6)	0.042 (5)	0.069 (6)	−0.016 (5)	−0.005 (5)	0.006 (5)
C4	0.072 (8)	0.068 (8)	0.112 (11)	−0.027 (7)	−0.015 (7)	0.002 (7)
C5	0.056 (7)	0.080 (9)	0.139 (13)	−0.008 (6)	−0.004 (7)	0.014 (9)
C6	0.067 (7)	0.054 (7)	0.123 (11)	0.000 (6)	0.002 (7)	0.003 (7)
C7	0.072 (7)	0.033 (5)	0.086 (8)	−0.003 (5)	−0.001 (6)	−0.007 (5)
C8	0.062 (6)	0.039 (5)	0.051 (5)	0.001 (4)	−0.006 (4)	0.011 (4)
C9	0.110 (10)	0.059 (7)	0.107 (10)	0.002 (7)	−0.048 (8)	0.026 (7)
C10	0.061 (6)	0.054 (6)	0.048 (5)	−0.003 (5)	0.003 (4)	−0.008 (4)
C11	0.101 (10)	0.103 (10)	0.066 (7)	−0.016 (8)	0.030 (7)	−0.013 (7)
C12	0.145 (16)	0.131 (16)	0.111 (13)	−0.019 (13)	0.019 (12)	−0.008 (12)
C13	0.20 (3)	0.31 (4)	0.15 (2)	0.05 (3)	0.02 (2)	0.09 (3)
C14	0.38 (5)	0.37 (6)	0.14 (2)	0.19 (5)	−0.06 (3)	−0.06 (3)
C15	0.14 (2)	0.44 (6)	0.24 (4)	0.03 (3)	0.00 (2)	0.12 (4)

Geometric parameters (Å, º)

Cu1—O4	1.956 (7)	C6—C7	1.369 (15)
Cu1—O3	1.970 (7)	C6—H6A	0.930
Cu1—O2	1.975 (7)	C7—H7A	0.930
Cu1—O1	1.996 (7)	C8—O1^i	1.260 (11)
Cu1—N2	2.183 (7)	C8—C9	1.491 (13)
Cu1—Cu1^i	2.6862 (19)	C9—H9A	0.960
S1—C3	1.720 (12)	C9—H9B	0.960
S1—C1	1.740 (9)	C9—H9C	0.960
O1—C8^i	1.260 (11)	C10—O2^i	1.274 (12)
O2—C10^i	1.274 (12)	C10—C11	1.499 (15)
O3—C8	1.242 (11)	C11—H11A	0.960
O4—C10	1.241 (12)	C11—H11B	0.960
O5—C12	1.415 (18)	C11—H11C	0.960
O5—H5	0.850	C12—C13	1.487 (10)
N1—C1	1.314 (12)	C12—H12A	0.970
N1—H1A	0.900	C12—H12B	0.970
N1—H1B	0.900	C13—C14	1.482 (10)
N2—C1	1.336 (11)	C13—H13A	0.970
N2—C2	1.394 (12)	C13—H13B	0.970
C2—C7	1.383 (14)	C14—C15	1.483 (10)
C2—C3	1.397 (13)	C14—H14A	0.970
C3—C4	1.394 (15)	C14—H14B	0.970
C4—C5	1.383 (19)	C15—H15A	0.960
C4—H4A	0.930	C15—H15B	0.960
C5—C6	1.370 (18)	C15—H15C	0.960
C5—H5A	0.930
O4—Cu1—O3	90.0 (3)	C6—C7—C2	119.4 (10)
O4—Cu1—O2	166.1 (3)	C6—C7—H7A	120.3
O3—Cu1—O2	90.8 (3)	C2—C7—H7A	120.3
O4—Cu1—O1	88.4 (3)	O3—C8—O1^i	123.8 (8)
O3—Cu1—O1	166.1 (3)	O3—C8—C9	118.1 (9)
O2—Cu1—O1	87.4 (3)	O1^i—C8—C9	118.1 (9)
O4—Cu1—N2	97.4 (3)	C8—C9—H9A	109.5
O3—Cu1—N2	97.0 (3)	C8—C9—H9B	109.5
O2—Cu1—N2	96.4 (3)	H9A—C9—H9B	109.5
O1—Cu1—N2	97.0 (3)	C8—C9—H9C	109.5
O4—Cu1—Cu1^i	82.1 (2)	H9A—C9—H9C	109.5
O3—Cu1—Cu1^i	80.4 (2)	H9B—C9—H9C	109.5
O2—Cu1—Cu1^i	84.3 (2)	O4—C10—O2^i	124.3 (9)
O1—Cu1—Cu1^i	85.7 (2)	O4—C10—C11	118.3 (10)
N2—Cu1—Cu1^i	177.3 (2)	O2^i—C10—C11	117.3 (9)
C3—S1—C1	89.8 (5)	C10—C11—H11A	109.5
C8^i—O1—Cu1	120.9 (6)	C10—C11—H11B	109.5
C10^i—O2—Cu1	122.0 (6)	H11A—C11—H11B	109.5
C8—O3—Cu1	129.2 (6)	C10—C11—H11C	109.5
C10—O4—Cu1	126.7 (7)	H11A—C11—H11C	109.5
C12—O5—H5	103.5	H11B—C11—H11C	109.5
C1—N1—H1A	118.6	O5—C12—C13	102.5 (14)
C1—N1—H1B	122.8	O5—C12—H12A	111.3
H1A—N1—H1B	118.6	C13—C12—H12A	111.3
C1—N2—C2	110.1 (8)	O5—C12—H12B	111.3
C1—N2—Cu1	124.0 (6)	C13—C12—H12B	111.3
C2—N2—Cu1	125.8 (6)	H12A—C12—H12B	109.2
N1—C1—N2	123.8 (8)	C14—C13—C12	110.8 (14)
N1—C1—S1	121.3 (7)	C14—C13—H13A	109.5
N2—C1—S1	114.9 (7)	C12—C13—H13A	109.5
C7—C2—N2	125.4 (8)	C14—C13—H13B	109.5
C7—C2—C3	119.6 (9)	C12—C13—H13B	109.5
N2—C2—C3	115.0 (9)	H13A—C13—H13B	108.1
C4—C3—C2	120.2 (11)	C13—C14—C15	109.4 (14)
C4—C3—S1	129.6 (9)	C13—C14—H14A	109.8
C2—C3—S1	110.1 (8)	C15—C14—H14A	109.8
C5—C4—C3	119.1 (11)	C13—C14—H14B	109.8
C5—C4—H4A	120.5	C15—C14—H14B	109.8
C3—C4—H4A	120.5	H14A—C14—H14B	108.2
C6—C5—C4	120.0 (11)	C14—C15—H15A	109.5
C6—C5—H5A	120.0	C14—C15—H15B	109.5
C4—C5—H5A	120.0	H15A—C15—H15B	109.5
C7—C6—C5	121.7 (12)	C14—C15—H15C	109.5
C7—C6—H6A	119.1	H15A—C15—H15C	109.5
C5—C6—H6A	119.1	H15B—C15—H15C	109.5
O4—Cu1—O1—C8^i	−80.3 (8)	C2—N2—C1—N1	178.5 (10)
O3—Cu1—O1—C8^i	3.3 (18)	Cu1—N2—C1—N1	−3.5 (14)
O2—Cu1—O1—C8^i	86.3 (8)	C2—N2—C1—S1	−1.7 (10)
N2—Cu1—O1—C8^i	−177.6 (8)	Cu1—N2—C1—S1	176.4 (4)
Cu1^i—Cu1—O1—C8^i	1.9 (8)	C3—S1—C1—N1	−178.7 (10)
O4—Cu1—O2—C10^i	−20.0 (18)	C3—S1—C1—N2	1.5 (8)
O3—Cu1—O2—C10^i	73.2 (8)	C1—N2—C2—C7	179.9 (10)
O1—Cu1—O2—C10^i	−92.9 (8)	Cu1—N2—C2—C7	1.9 (14)
N2—Cu1—O2—C10^i	170.3 (8)	C1—N2—C2—C3	1.0 (12)
Cu1^i—Cu1—O2—C10^i	−7.0 (8)	Cu1—N2—C2—C3	−177.0 (7)
O4—Cu1—O3—C8	83.1 (9)	C7—C2—C3—C4	0.7 (16)
O2—Cu1—O3—C8	−82.9 (9)	N2—C2—C3—C4	179.6 (10)
O1—Cu1—O3—C8	0 (2)	C7—C2—C3—S1	−178.8 (8)
N2—Cu1—O3—C8	−179.4 (9)	N2—C2—C3—S1	0.1 (11)
Cu1^i—Cu1—O3—C8	1.2 (9)	C1—S1—C3—C4	179.7 (12)
O3—Cu1—O4—C10	−79.9 (9)	C1—S1—C3—C2	−0.8 (8)
O2—Cu1—O4—C10	13.4 (19)	C2—C3—C4—C5	−0.5 (19)
O1—Cu1—O4—C10	86.3 (9)	S1—C3—C4—C5	179.0 (11)
N2—Cu1—O4—C10	−176.9 (9)	C3—C4—C5—C6	1 (2)
Cu1^i—Cu1—O4—C10	0.4 (8)	C4—C5—C6—C7	−2 (2)
O4—Cu1—N2—C1	−138.9 (8)	C5—C6—C7—C2	2 (2)
O3—Cu1—N2—C1	130.2 (8)	N2—C2—C7—C6	179.7 (11)
O2—Cu1—N2—C1	38.6 (8)	C3—C2—C7—C6	−1.5 (17)
O1—Cu1—N2—C1	−49.6 (8)	Cu1—O3—C8—O1^i	−3.1 (16)
Cu1^i—Cu1—N2—C1	143 (4)	Cu1—O3—C8—C9	176.2 (9)
O4—Cu1—N2—C2	38.9 (8)	Cu1—O4—C10—O2^i	5.0 (16)
O3—Cu1—N2—C2	−52.0 (8)	Cu1—O4—C10—C11	−178.6 (8)
O2—Cu1—N2—C2	−143.6 (7)	O5—C12—C13—C14	−175 (2)
O1—Cu1—N2—C2	128.2 (7)	C12—C13—C14—C15	−152 (3)
Cu1^i—Cu1—N2—C2	−40 (5)

Symmetry code: (i) −x+2, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.90	2.23	3.002 (11)	144
N1—H1B···O5^ii	0.90	1.99	2.850 (12)	159
O5—H5···O1^iii	0.85	2.04	2.885 (10)	180

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