Dichlorido(dimethyl sulfoxide-κO)(1,10-phenanthroline-5,6-dione-κ²N,N′)copper(II) dimethyl sulfoxide monohydrate

The title compound, [CuCl₂(C₁₂H₆N₂O₂)(C₂H₆OS)]·C₂H₆OS·H₂O, was obtained by the reaction of 1,10-phenanthroline-5,6-dione (phendione) and CuCl₂·2H₂O. The copper(II) ion is penta­coordinated in a distorted square-pyramidal environment. The water mol­ecule connects the complex and a dimethyl sulfoxide solvent mol­ecule by O—H...O and O—H...Cl hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.039
• wR factor = 0.121
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.64 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         S1
PLAT333_ALERT_2_B Large Average Benzene C-C Dist.  C4     -C12           1.47 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O4     ..  C5      ..       2.78 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O4     ..  C6      ..       2.78 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O5     ..  C5      ..       2.89 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.654     1.000
            Tmin(prime) and Tmax expected:      0.637     0.814
            RR(prime) =      0.835
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.82
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.81
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.34 Ratio
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C5     -   C6     ...       1.55 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.814
            Tmax scaled      0.814 Tmin scaled      0.532
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       1.96

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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

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S1. Comment

The complexes of 1,10-phenanthroline-5,6-dione (phendione) could intercalate within the base pairs of DNA (Ghosh et al., 2006; Coyle et al., 2003). Based on this finding, the derivatives of phendione are promising in the treatment of many diseases (Deegan et al., 2006; Eshwika et al., 2004), cancer amongst all, and their development is still in progress. Following our interest in biological activity of metal complexes, we decided to focus our attention on the complexes of phendione (Xu et al., 2006).

The asymmetric unit of complex consists of a monomeric copper(II) complex, one dimethyl sulfoxide (DMSO) molecule and one water molecule. The copper(II) ion is in a five-coordinated environment. The phendione acts as bidentate ligand [Cu—N1 = 2.062 (3)Å and Cu—N2 = 2.059 (3) Å], forming with the metal ion a five-membered chelate ring with a bite angle of 80.38 (12)°. A monodentate dimethyl sulfoxide interacts with copper at a distance [Cu—O3 = 2.019 (3) Å]. Addison et al. (1984) have proposed a structural index for five-coordinated geometries of copper(II). This index has been defined as τ = (β-α)/60, with β and α being the two largest angles. For perfect tetragonal geometry τ equals zero, while it becomes unity for perfect trigonal bipyramidal geometry. From the bond lengths and angles it can be concluded that the coordination geometry around copper(II) is clearly square-pyramidal (τ = 0.14) with a CuN₂OCl plane and one chloride ion in the apex. The copper(II) ion is shifted 0.3319 Å out of the plane defined by (N1, N2, O3 and Cl1) and directed towards Cl2.

The water molecule connects the complex and a dimethyl sulfoxide solvent molecule by O—H···O and O—H···Cl hydrogen bonds.

Related literature

For related literature, see: Addison & Rao (1984); Coyle et al. (2003); Deegan et al. (2006); Eshwika et al. (2004); Ghosh et al. (2006); Xu et al. (2006); Yamada et al. (1992).

S2. Experimental

1,10-Phenanthroline-5,6-dione was prepared according to the literature method (Yamada et al., 1992). The complex was prepared by mixing a 10 ml me thanolic solution of copper(II) chloride dihydrate (171 mg, 0.5 mmol) and 1,10-phenanthroline-5,6-dione (105 mg, 0.5 mmol) in methanolic solution (10 ml) was added, and then the solution was stirred for about 3 h at room temperature. The green precipitate was collected by filtration. Crystals of suitable quality for X-ray analysis were obtained by slow evaporation of a dimethyl sulfoxide solution.

S3. Refinement

All H atoms were initially located in a difference Fourier map, but refined using a riding model with with C—H distances in the range 0.95–1.00 Å, O—H = 0.91 and 0.97Å and U_iso(H) = 1.2U_eq(C,O). The methyl H atoms were then constrained to an ideal geometry, with C—H distances of 0.98 Å and U_iso(H) = 1.5U_eq(C), but each group was allowed to rotate freely about its C—C bond.

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. Molecular view of the title complex with the atomic labeling scheme. Displacement ellipsoids are shown at the 30% probability level.

Dichlorido(dimethyl sulfoxide-κO)(1,10-phenanthroline-5,6-dione-κ²N,N')copper(II) dimethyl sulfoxide monohydrate

Crystal data

[CuCl2(C12H6N2O2)(C2H6OS)]·C2H6OS·H2O	Z = 2
Mr = 518.90	F(000) = 530
Triclinic, P1	Dx = 1.588 Mg m^−3
a = 7.213 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.285 (4) Å	Cell parameters from 2461 reflections
c = 13.316 (4) Å	θ = 2.9–27.3°
α = 61.405 (4)°	µ = 1.47 mm^−1
β = 76.169 (5)°	T = 293 K
γ = 86.688 (5)°	Block, green
V = 1085.5 (6) Å^3	0.30 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3809 independent reflections
Radiation source: fine-focus sealed tube	2886 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→8
Tmin = 0.654, Tmax = 1.000	k = −10→15
5536 measured reflections	l = −7→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0706P)^2] where P = (Fo^2 + 2Fc^2)/3
3809 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.50 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	0.68285 (7)	0.20517 (4)	0.11889 (4)	0.02951 (17)
Cl1	0.7899 (2)	0.32022 (10)	−0.08024 (10)	0.0523 (3)
Cl2	0.98176 (15)	0.15681 (9)	0.19795 (9)	0.0395 (3)
O1	0.1728 (5)	−0.2722 (3)	0.5060 (3)	0.0508 (9)
O2	0.3546 (5)	−0.3228 (3)	0.3314 (3)	0.0529 (9)
N1	0.4842 (5)	0.1080 (3)	0.2746 (3)	0.0283 (7)
N2	0.6593 (4)	0.0587 (3)	0.1052 (3)	0.0273 (7)
C1	0.4025 (6)	0.1372 (4)	0.3593 (4)	0.0372 (10)
H1	0.4317	0.2103	0.3465	0.045*
C2	0.2762 (6)	0.0620 (4)	0.4650 (4)	0.0405 (11)
H2	0.2214	0.0852	0.5206	0.049*
C3	0.2336 (6)	−0.0481 (4)	0.4857 (4)	0.0376 (10)
H3	0.1512	−0.0997	0.5559	0.045*
C4	0.3165 (5)	−0.0803 (3)	0.3994 (3)	0.0273 (9)
C5	0.2780 (6)	−0.1980 (4)	0.4167 (4)	0.0347 (10)
C6	0.3800 (6)	−0.2259 (4)	0.3177 (4)	0.0353 (10)
C7	0.5102 (6)	−0.1347 (3)	0.2090 (4)	0.0324 (9)
C8	0.6115 (6)	−0.1544 (4)	0.1163 (4)	0.0384 (10)
H8	0.5950	−0.2248	0.1193	0.046*
C9	0.7360 (6)	−0.0680 (4)	0.0207 (4)	0.0393 (10)
H9	0.8061	−0.0802	−0.0404	0.047*
C10	0.7550 (6)	0.0378 (4)	0.0173 (3)	0.0339 (10)
H10	0.8367	0.0960	−0.0480	0.041*
C11	0.5396 (5)	−0.0261 (3)	0.2003 (3)	0.0252 (8)
C12	0.4413 (5)	0.0007 (3)	0.2951 (3)	0.0252 (8)
S1	0.79906 (15)	0.43275 (9)	0.09613 (9)	0.0335 (3)
O3	0.6295 (4)	0.3409 (2)	0.1482 (3)	0.0374 (7)
C13	0.6938 (8)	0.5662 (4)	0.0314 (6)	0.077 (2)
H13A	0.6706	0.5795	−0.0419	0.115*
H13B	0.7790	0.6269	0.0174	0.115*
H13C	0.5750	0.5642	0.0838	0.115*
C14	0.8440 (11)	0.4352 (6)	0.2211 (5)	0.091 (2)
H14A	0.7293	0.4517	0.2632	0.137*
H14B	0.9432	0.4935	0.1953	0.137*
H14C	0.8837	0.3617	0.2720	0.137*
S2	0.63777 (15)	0.62156 (9)	0.50874 (10)	0.0376 (3)
O4	0.6473 (4)	0.7528 (2)	0.4453 (3)	0.0444 (8)
C15	0.8179 (8)	0.5835 (4)	0.4152 (5)	0.0541 (13)
H15A	0.7891	0.6132	0.3397	0.081*
H15B	0.8198	0.5014	0.4507	0.081*
H15C	0.9409	0.6157	0.4054	0.081*
C16	0.7491 (7)	0.5797 (4)	0.6291 (4)	0.0469 (12)
H16A	0.8742	0.6182	0.5997	0.070*
H16B	0.7600	0.4981	0.6666	0.070*
H16C	0.6725	0.6005	0.6852	0.070*
O5	1.0108 (5)	0.8885 (3)	0.2676 (3)	0.0571 (9)
H5A	0.9228	0.8233	0.3256	0.069*
H5B	0.9671	0.9578	0.2554	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0328 (3)	0.0211 (3)	0.0286 (3)	−0.0039 (2)	−0.0017 (2)	−0.0091 (2)
Cl1	0.0765 (9)	0.0347 (6)	0.0295 (6)	−0.0109 (6)	−0.0054 (6)	−0.0047 (5)
Cl2	0.0376 (6)	0.0404 (6)	0.0410 (6)	0.0036 (5)	−0.0108 (5)	−0.0193 (5)
O1	0.054 (2)	0.0378 (19)	0.0383 (18)	−0.0198 (16)	0.0016 (15)	−0.0044 (15)
O2	0.077 (2)	0.0281 (18)	0.054 (2)	−0.0146 (16)	−0.0163 (18)	−0.0178 (16)
N1	0.0329 (18)	0.0204 (17)	0.0331 (18)	−0.0015 (14)	−0.0035 (15)	−0.0157 (15)
N2	0.0269 (17)	0.0262 (18)	0.0246 (17)	0.0007 (14)	−0.0037 (14)	−0.0099 (15)
C1	0.042 (2)	0.029 (2)	0.040 (2)	−0.0028 (19)	−0.002 (2)	−0.020 (2)
C2	0.038 (2)	0.046 (3)	0.040 (3)	0.001 (2)	0.003 (2)	−0.028 (2)
C3	0.034 (2)	0.039 (3)	0.032 (2)	−0.002 (2)	0.0004 (19)	−0.015 (2)
C4	0.026 (2)	0.025 (2)	0.027 (2)	−0.0021 (16)	−0.0051 (16)	−0.0104 (18)
C5	0.034 (2)	0.031 (2)	0.032 (2)	−0.0051 (19)	−0.0103 (19)	−0.008 (2)
C6	0.040 (2)	0.030 (2)	0.036 (2)	−0.0036 (19)	−0.0139 (19)	−0.013 (2)
C7	0.034 (2)	0.028 (2)	0.036 (2)	−0.0004 (18)	−0.0123 (18)	−0.0138 (19)
C8	0.052 (3)	0.031 (2)	0.042 (3)	0.007 (2)	−0.016 (2)	−0.024 (2)
C9	0.044 (3)	0.043 (3)	0.032 (2)	0.008 (2)	−0.004 (2)	−0.021 (2)
C10	0.033 (2)	0.037 (2)	0.028 (2)	−0.0007 (19)	−0.0020 (18)	−0.015 (2)
C11	0.030 (2)	0.019 (2)	0.026 (2)	0.0039 (16)	−0.0087 (16)	−0.0092 (17)
C12	0.0235 (19)	0.026 (2)	0.025 (2)	0.0014 (16)	−0.0071 (16)	−0.0105 (17)
S1	0.0327 (6)	0.0236 (5)	0.0375 (6)	−0.0054 (4)	−0.0021 (5)	−0.0114 (5)
O3	0.0345 (16)	0.0251 (15)	0.0463 (17)	−0.0071 (12)	0.0030 (13)	−0.0170 (14)
C13	0.051 (3)	0.021 (3)	0.127 (6)	−0.002 (2)	−0.018 (3)	−0.013 (3)
C14	0.115 (6)	0.102 (5)	0.054 (4)	−0.060 (4)	−0.007 (4)	−0.033 (4)
S2	0.0355 (6)	0.0263 (6)	0.0487 (7)	0.0013 (5)	−0.0126 (5)	−0.0151 (5)
O4	0.0537 (19)	0.0255 (16)	0.0522 (19)	0.0075 (14)	−0.0178 (16)	−0.0156 (15)
C15	0.066 (3)	0.039 (3)	0.057 (3)	0.010 (2)	−0.009 (3)	−0.026 (3)
C16	0.050 (3)	0.037 (3)	0.049 (3)	0.004 (2)	−0.017 (2)	−0.015 (2)
O5	0.062 (2)	0.0375 (19)	0.061 (2)	0.0060 (16)	−0.0097 (18)	−0.0177 (17)

Geometric parameters (Å, º)

Cu1—O3	2.019 (3)	C9—C10	1.398 (6)
Cu1—N2	2.059 (3)	C9—H9	0.9300
Cu1—N1	2.062 (3)	C10—H10	0.9300
Cu1—Cl1	2.2894 (13)	C11—C12	1.482 (5)
Cu1—Cl2	2.5390 (13)	S1—O3	1.557 (3)
O1—C5	1.222 (5)	S1—C13	1.776 (5)
O2—C6	1.230 (5)	S1—C14	1.785 (5)
N1—C12	1.356 (5)	C13—H13A	0.9600
N1—C1	1.358 (5)	C13—H13B	0.9600
N2—C10	1.351 (5)	C13—H13C	0.9600
N2—C11	1.357 (5)	C14—H14A	0.9600
C1—C2	1.398 (6)	C14—H14B	0.9600
C1—H1	0.9300	C14—H14C	0.9600
C2—C3	1.390 (6)	S2—O4	1.528 (3)
C2—H2	0.9300	S2—C16	1.798 (5)
C3—C4	1.406 (6)	S2—C15	1.802 (5)
C3—H3	0.9300	C15—H15A	0.9600
C4—C12	1.407 (5)	C15—H15B	0.9600
C4—C5	1.499 (6)	C15—H15C	0.9600
C5—C6	1.547 (6)	C16—H16A	0.9600
C6—C7	1.500 (6)	C16—H16B	0.9600
C7—C8	1.407 (6)	C16—H16C	0.9600
C7—C11	1.416 (5)	O5—H5A	0.9690
C8—C9	1.385 (6)	O5—H5B	0.9055
C8—H8	0.9300
O3—Cu1—N2	164.67 (12)	C10—C9—H9	120.4
O3—Cu1—N1	88.13 (12)	N2—C10—C9	122.5 (4)
N2—Cu1—N1	80.35 (12)	N2—C10—H10	118.7
O3—Cu1—Cl1	92.68 (9)	C9—C10—H10	118.7
N2—Cu1—Cl1	93.81 (9)	N2—C11—C7	121.9 (3)
N1—Cu1—Cl1	156.11 (10)	N2—C11—C12	116.5 (3)
O3—Cu1—Cl2	95.00 (9)	C7—C11—C12	121.6 (3)
N2—Cu1—Cl2	96.66 (9)	N1—C12—C4	122.9 (3)
N1—Cu1—Cl2	98.39 (10)	N1—C12—C11	114.9 (3)
Cl1—Cu1—Cl2	105.31 (5)	C4—C12—C11	122.2 (3)
C12—N1—C1	117.9 (3)	O3—S1—C13	104.4 (2)
C12—N1—Cu1	114.5 (2)	O3—S1—C14	104.6 (2)
C1—N1—Cu1	127.5 (3)	C13—S1—C14	100.2 (4)
C10—N2—C11	118.8 (3)	S1—O3—Cu1	115.78 (16)
C10—N2—Cu1	127.5 (3)	S1—C13—H13A	109.5
C11—N2—Cu1	113.6 (2)	S1—C13—H13B	109.5
N1—C1—C2	122.7 (4)	H13A—C13—H13B	109.5
N1—C1—H1	118.6	S1—C13—H13C	109.5
C2—C1—H1	118.6	H13A—C13—H13C	109.5
C3—C2—C1	119.1 (4)	H13B—C13—H13C	109.5
C3—C2—H2	120.5	S1—C14—H14A	109.5
C1—C2—H2	120.5	S1—C14—H14B	109.5
C2—C3—C4	119.2 (4)	H14A—C14—H14B	109.5
C2—C3—H3	120.4	S1—C14—H14C	109.5
C4—C3—H3	120.4	H14A—C14—H14C	109.5
C3—C4—C12	118.2 (4)	H14B—C14—H14C	109.5
C3—C4—C5	121.9 (4)	O4—S2—C16	106.1 (2)
C12—C4—C5	119.9 (3)	O4—S2—C15	105.4 (2)
O1—C5—C4	122.8 (4)	C16—S2—C15	99.5 (2)
O1—C5—C6	119.3 (4)	S2—C15—H15A	109.5
C4—C5—C6	117.9 (3)	S2—C15—H15B	109.5
O2—C6—C7	122.0 (4)	H15A—C15—H15B	109.5
O2—C6—C5	119.0 (4)	S2—C15—H15C	109.5
C7—C6—C5	118.9 (4)	H15A—C15—H15C	109.5
C8—C7—C11	118.3 (4)	H15B—C15—H15C	109.5
C8—C7—C6	122.3 (4)	S2—C16—H16A	109.5
C11—C7—C6	119.4 (4)	S2—C16—H16B	109.5
C9—C8—C7	119.3 (4)	H16A—C16—H16B	109.5
C9—C8—H8	120.3	S2—C16—H16C	109.5
C7—C8—H8	120.3	H16A—C16—H16C	109.5
C8—C9—C10	119.2 (4)	H16B—C16—H16C	109.5
C8—C9—H9	120.4	H5A—O5—H5B	114.7
O3—Cu1—N1—C12	172.2 (3)	C5—C6—C7—C11	1.1 (6)
N2—Cu1—N1—C12	2.4 (3)	C11—C7—C8—C9	0.2 (6)
Cl1—Cu1—N1—C12	79.8 (4)	C6—C7—C8—C9	−177.2 (4)
Cl2—Cu1—N1—C12	−93.0 (3)	C7—C8—C9—C10	−1.4 (6)
O3—Cu1—N1—C1	−11.7 (3)	C11—N2—C10—C9	−0.2 (6)
N2—Cu1—N1—C1	178.5 (4)	Cu1—N2—C10—C9	176.0 (3)
Cl1—Cu1—N1—C1	−104.1 (4)	C8—C9—C10—N2	1.4 (6)
Cl2—Cu1—N1—C1	83.1 (3)	C10—N2—C11—C7	−1.0 (5)
O3—Cu1—N2—C10	139.4 (4)	Cu1—N2—C11—C7	−177.7 (3)
N1—Cu1—N2—C10	−178.8 (3)	C10—N2—C11—C12	178.8 (3)
Cl1—Cu1—N2—C10	24.6 (3)	Cu1—N2—C11—C12	2.1 (4)
Cl2—Cu1—N2—C10	−81.3 (3)	C8—C7—C11—N2	1.0 (6)
O3—Cu1—N2—C11	−44.2 (6)	C6—C7—C11—N2	178.5 (3)
N1—Cu1—N2—C11	−2.4 (2)	C8—C7—C11—C12	−178.8 (3)
Cl1—Cu1—N2—C11	−159.1 (2)	C6—C7—C11—C12	−1.3 (6)
Cl2—Cu1—N2—C11	95.0 (2)	C1—N1—C12—C4	0.1 (6)
C12—N1—C1—C2	−0.5 (6)	Cu1—N1—C12—C4	176.6 (3)
Cu1—N1—C1—C2	−176.5 (3)	C1—N1—C12—C11	−178.5 (3)
N1—C1—C2—C3	0.9 (7)	Cu1—N1—C12—C11	−2.0 (4)
C1—C2—C3—C4	−0.8 (7)	C3—C4—C12—N1	−0.1 (6)
C2—C3—C4—C12	0.5 (6)	C5—C4—C12—N1	−179.1 (3)
C2—C3—C4—C5	179.4 (4)	C3—C4—C12—C11	178.4 (4)
C3—C4—C5—O1	0.2 (6)	C5—C4—C12—C11	−0.6 (5)
C12—C4—C5—O1	179.1 (4)	N2—C11—C12—N1	−0.1 (5)
C3—C4—C5—C6	−178.6 (4)	C7—C11—C12—N1	179.7 (3)
C12—C4—C5—C6	0.4 (5)	N2—C11—C12—C4	−178.7 (3)
O1—C5—C6—O2	−0.8 (6)	C7—C11—C12—C4	1.1 (6)
C4—C5—C6—O2	178.0 (4)	C13—S1—O3—Cu1	135.8 (3)
O1—C5—C6—C7	−179.4 (4)	C14—S1—O3—Cu1	−119.4 (3)
C4—C5—C6—C7	−0.6 (6)	N2—Cu1—O3—S1	−168.1 (4)
O2—C6—C7—C8	−0.1 (6)	N1—Cu1—O3—S1	150.76 (19)
C5—C6—C7—C8	178.5 (4)	Cl1—Cu1—O3—S1	−53.13 (18)
O2—C6—C7—C11	−177.5 (4)	Cl2—Cu1—O3—S1	52.50 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4	0.97	2.15	3.037 (5)	151
O5—H5B···Cl2^i	0.91	2.38	3.233 (5)	158

Symmetry code: (i) x, y+1, z.