Bis[2-(2-pyridylmethyl-eneamino)benzene-sulfonato]-κN,N',O;κN,N'-copper(II).

In the mononuclear title compound, [Cu(C(12)H(9)N(2)O(3)S)(2)], the copper(II) salt of 2-(2-pyridylmethyl-eneamino)benzene-sulfonic acid, the Cu(II) atom is coordinated by one O and two N atoms from a monoanion as well as by two N atoms from another monoanion in a distorted trigonal-bipyramidal environment.

Related literature

For the synthesis of the ligand, see: Casella & Gullotti (1986 ▶). For the structures of analogues, see: Cai et al. (2008 ▶). For related Schiff base complexes, see: Li et al. (2006 ▶, 2007 ▶); Wang et al. (1994 ▶); Jiang et al. (2006 ▶); Zhang et al. (2004 ▶). For a discussion on self-assembly, see: Zheng et al. (2001 ▶).

Experimental

Crystal data

[Cu(C12H9N2O3S)2]

M = 586.08

Orthorhombic,

a = 17.347 (4) Å

b = 14.686 (4) Å

c = 18.830 (5) Å

V = 4797 (2) Å3

Z = 8

Mo Kα radiation

μ = 1.14 mm−1

T = 294 K

0.25 × 0.19 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.762, T max = 0.868

33042 measured reflections

4455 independent reflections

2420 reflections with I > 2σ(I)

R int = 0.128

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.131

S = 1.01

4455 reflections

334 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.64 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035661/ng2628sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035661/ng2628Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C12H9N2O3S)2]	Dx = 1.623 Mg m−3
Mr = 586.08	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1929 reflections
a = 17.347 (4) Å	θ = 2.4–18.1°
b = 14.686 (4) Å	µ = 1.14 mm−1
c = 18.830 (5) Å	T = 294 K
V = 4797 (2) Å3	Block, blue
Z = 8	0.25 × 0.19 × 0.13 mm
F(000) = 2392

Bruker SMART CCD area-detector diffractometer	4455 independent reflections
Radiation source: fine-focus sealed tube	2420 reflections with I > 2σ(I)
graphite	Rint = 0.128
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→21
Tmin = 0.762, Tmax = 0.868	k = −17→17
33042 measured reflections	l = −22→22

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0346P)2 + 8.08P] where P = (Fo2 + 2Fc2)/3
4455 reflections	(Δ/σ)max < 0.001
334 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.64 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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.

	x	y	z	Uiso*/Ueq
Cu1	0.06065 (4)	0.76356 (4)	0.39106 (4)	0.0524 (2)
S1	0.26315 (8)	0.67187 (12)	0.44099 (8)	0.0587 (4)
S2	0.01410 (8)	0.84439 (10)	0.23757 (8)	0.0508 (4)
O1	0.2221 (3)	0.7519 (4)	0.4561 (2)	0.1110 (19)
O2	0.2297 (2)	0.5889 (3)	0.4688 (2)	0.0936 (16)
O3	0.3437 (2)	0.6766 (3)	0.4590 (2)	0.0734 (12)
O4	−0.00046 (19)	0.7751 (3)	0.2916 (2)	0.0664 (11)
O5	−0.0112 (2)	0.9335 (3)	0.2599 (2)	0.0657 (11)
O6	−0.0135 (2)	0.8176 (3)	0.16862 (19)	0.0657 (11)
N1	−0.0138 (2)	0.6688 (3)	0.4184 (2)	0.0470 (11)
N2	0.1189 (2)	0.6475 (3)	0.3528 (2)	0.0389 (10)
N3	0.0584 (2)	0.8399 (3)	0.4808 (2)	0.0417 (10)
N4	0.1258 (2)	0.8652 (3)	0.3585 (2)	0.0426 (10)
C1	−0.0816 (3)	0.6815 (4)	0.4503 (3)	0.0638 (17)
H1	−0.0966	0.7406	0.4614	0.077*
C2	−0.1304 (3)	0.6107 (5)	0.4675 (3)	0.0655 (17)
H2	−0.1770	0.6218	0.4905	0.079*
C3	−0.1092 (3)	0.5243 (5)	0.4501 (3)	0.0678 (18)
H3	−0.1410	0.4754	0.4614	0.081*
C4	−0.0397 (3)	0.5095 (4)	0.4155 (3)	0.0543 (15)
H4	−0.0243	0.4510	0.4030	0.065*
C5	0.0056 (3)	0.5828 (3)	0.4000 (3)	0.0428 (13)
C6	0.0795 (3)	0.5753 (4)	0.3622 (3)	0.0465 (13)
H6	0.0969	0.5193	0.3455	0.056*
C7	0.1900 (3)	0.6409 (3)	0.3139 (3)	0.0392 (12)
C8	0.2598 (3)	0.6566 (3)	0.3484 (3)	0.0429 (13)
C9	0.3270 (3)	0.6531 (4)	0.3078 (3)	0.0574 (16)
H9	0.3741	0.6640	0.3296	0.069*
C10	0.3253 (4)	0.6338 (4)	0.2365 (4)	0.077 (2)
H10	0.3708	0.6312	0.2106	0.092*
C11	0.2559 (4)	0.6184 (5)	0.2040 (4)	0.0780 (19)
H11	0.2543	0.6056	0.1557	0.094*
C12	0.1886 (3)	0.6219 (4)	0.2425 (3)	0.0608 (16)
H12	0.1418	0.6112	0.2199	0.073*
C13	0.0264 (3)	0.8255 (4)	0.5440 (3)	0.0465 (13)
H13	−0.0012	0.7719	0.5508	0.056*
C14	0.0320 (3)	0.8859 (4)	0.6002 (3)	0.0538 (15)
H14	0.0086	0.8727	0.6434	0.065*
C15	0.0722 (3)	0.9648 (4)	0.5915 (3)	0.0595 (16)
H15	0.0753	1.0073	0.6280	0.071*
C16	0.1081 (3)	0.9804 (4)	0.5275 (3)	0.0584 (15)
H16	0.1370	1.0329	0.5206	0.070*
C17	0.1007 (3)	0.9174 (3)	0.4737 (3)	0.0445 (13)
C18	0.1366 (3)	0.9272 (3)	0.4042 (3)	0.0467 (13)
H18	0.1667	0.9778	0.3937	0.056*
C19	0.1617 (3)	0.8674 (3)	0.2902 (3)	0.0420 (13)
C20	0.2410 (3)	0.8767 (4)	0.2847 (3)	0.0550 (15)
H20	0.2707	0.8865	0.3251	0.066*
C21	0.2755 (3)	0.8713 (4)	0.2187 (3)	0.0656 (17)
H21	0.3286	0.8784	0.2147	0.079*
C22	0.2316 (3)	0.8556 (4)	0.1586 (3)	0.0640 (17)
H22	0.2550	0.8516	0.1143	0.077*
C23	0.1524 (3)	0.8457 (4)	0.1651 (3)	0.0544 (15)
H23	0.1229	0.8348	0.1248	0.065*
C24	0.1167 (3)	0.8516 (3)	0.2304 (3)	0.0412 (12)

	U11	U22	U33	U12	U13	U23
Cu1	0.0531 (4)	0.0415 (4)	0.0625 (5)	−0.0138 (3)	0.0194 (4)	−0.0088 (3)
S1	0.0445 (9)	0.0764 (11)	0.0553 (10)	0.0017 (8)	−0.0076 (7)	0.0064 (8)
S2	0.0407 (8)	0.0617 (10)	0.0498 (9)	0.0054 (7)	−0.0020 (7)	0.0020 (8)
O1	0.120 (4)	0.153 (5)	0.060 (3)	0.080 (4)	−0.033 (3)	−0.043 (3)
O2	0.077 (3)	0.132 (4)	0.071 (3)	−0.044 (3)	−0.009 (2)	0.036 (3)
O3	0.053 (2)	0.078 (3)	0.089 (3)	−0.008 (2)	−0.029 (2)	0.003 (2)
O4	0.045 (2)	0.086 (3)	0.068 (3)	−0.014 (2)	−0.0058 (19)	0.028 (2)
O5	0.054 (2)	0.069 (3)	0.074 (3)	0.021 (2)	0.004 (2)	−0.009 (2)
O6	0.057 (2)	0.085 (3)	0.055 (3)	0.001 (2)	−0.008 (2)	−0.007 (2)
N1	0.039 (3)	0.047 (3)	0.055 (3)	−0.008 (2)	0.009 (2)	−0.004 (2)
N2	0.030 (2)	0.041 (3)	0.046 (3)	−0.002 (2)	−0.0006 (19)	−0.008 (2)
N3	0.040 (2)	0.036 (2)	0.050 (3)	−0.001 (2)	0.003 (2)	0.004 (2)
N4	0.042 (3)	0.042 (3)	0.044 (3)	−0.001 (2)	0.001 (2)	0.001 (2)
C1	0.048 (4)	0.066 (4)	0.077 (4)	−0.010 (3)	0.024 (3)	−0.017 (3)
C2	0.049 (4)	0.089 (5)	0.059 (4)	−0.019 (3)	0.017 (3)	−0.014 (4)
C3	0.063 (4)	0.074 (5)	0.067 (4)	−0.034 (4)	0.007 (3)	−0.002 (4)
C4	0.056 (4)	0.045 (3)	0.062 (4)	−0.013 (3)	0.000 (3)	−0.004 (3)
C5	0.041 (3)	0.039 (3)	0.048 (3)	−0.005 (2)	−0.004 (3)	−0.001 (3)
C6	0.041 (3)	0.039 (3)	0.059 (4)	−0.002 (3)	−0.002 (3)	−0.012 (3)
C7	0.032 (3)	0.038 (3)	0.048 (3)	0.003 (2)	0.003 (2)	−0.003 (2)
C8	0.036 (3)	0.037 (3)	0.056 (3)	0.001 (2)	−0.002 (3)	0.009 (3)
C9	0.030 (3)	0.061 (4)	0.081 (5)	−0.004 (3)	0.004 (3)	0.010 (3)
C10	0.061 (5)	0.090 (5)	0.079 (5)	0.012 (4)	0.028 (4)	0.003 (4)
C11	0.069 (5)	0.100 (5)	0.064 (4)	0.007 (4)	0.015 (4)	−0.015 (4)
C12	0.049 (4)	0.073 (4)	0.061 (4)	0.003 (3)	−0.002 (3)	−0.018 (3)
C13	0.043 (3)	0.048 (3)	0.049 (4)	−0.003 (3)	0.003 (3)	0.008 (3)
C14	0.048 (3)	0.072 (4)	0.042 (4)	−0.003 (3)	0.000 (3)	0.003 (3)
C15	0.069 (4)	0.066 (4)	0.044 (4)	−0.005 (3)	−0.009 (3)	−0.010 (3)
C16	0.073 (4)	0.050 (4)	0.052 (4)	−0.008 (3)	−0.009 (3)	−0.007 (3)
C17	0.045 (3)	0.045 (3)	0.043 (3)	0.000 (3)	−0.003 (3)	0.004 (3)
C18	0.052 (3)	0.039 (3)	0.049 (4)	−0.014 (3)	−0.002 (3)	0.004 (3)
C19	0.046 (3)	0.034 (3)	0.047 (3)	−0.001 (2)	0.004 (3)	0.005 (2)
C20	0.047 (4)	0.062 (4)	0.056 (4)	−0.015 (3)	−0.002 (3)	0.015 (3)
C21	0.047 (4)	0.078 (5)	0.071 (5)	−0.005 (3)	0.012 (3)	0.025 (4)
C22	0.057 (4)	0.082 (5)	0.054 (4)	0.014 (3)	0.014 (3)	0.015 (3)
C23	0.056 (4)	0.061 (4)	0.046 (4)	0.009 (3)	−0.004 (3)	0.005 (3)
C24	0.042 (3)	0.040 (3)	0.041 (3)	0.003 (2)	0.003 (3)	0.006 (2)

Cu1—N1	1.967 (4)	C7—C12	1.374 (7)
Cu1—N4	1.970 (4)	C7—C8	1.394 (6)
Cu1—N3	2.028 (4)	C8—C9	1.394 (7)
Cu1—N2	2.108 (4)	C9—C10	1.372 (8)
Cu1—O4	2.158 (4)	C9—H9	0.9300
S1—O1	1.403 (4)	C10—C11	1.368 (8)
S1—O3	1.439 (4)	C10—H10	0.9300
S1—O2	1.447 (4)	C11—C12	1.374 (8)
S1—C8	1.758 (5)	C11—H11	0.9300
S2—O6	1.439 (4)	C12—H12	0.9300
S2—O5	1.443 (4)	C13—C14	1.384 (7)
S2—O4	1.462 (4)	C13—H13	0.9300
S2—C24	1.788 (5)	C14—C15	1.364 (7)
N1—C1	1.334 (6)	C14—H14	0.9300
N1—C5	1.352 (6)	C15—C16	1.375 (7)
N2—C6	1.275 (6)	C15—H15	0.9300
N2—C7	1.438 (6)	C16—C17	1.379 (7)
N3—C13	1.329 (6)	C16—H16	0.9300
N3—C17	1.361 (6)	C17—C18	1.456 (7)
N4—C18	1.267 (6)	C18—H18	0.9300
N4—C19	1.430 (6)	C19—C20	1.387 (7)
C1—C2	1.379 (7)	C19—C24	1.388 (7)
C1—H1	0.9300	C20—C21	1.380 (7)
C2—C3	1.362 (8)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.383 (8)
C3—C4	1.388 (7)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.387 (7)
C4—C5	1.364 (7)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.379 (7)
C5—C6	1.470 (7)	C23—H23	0.9300
C6—H6	0.9300
N1—Cu1—N4	173.80 (17)	C12—C7—N2	119.8 (5)
N1—Cu1—N3	99.20 (17)	C8—C7—N2	119.7 (4)
N4—Cu1—N3	81.47 (17)	C9—C8—C7	117.6 (5)
N1—Cu1—N2	80.34 (16)	C9—C8—S1	121.4 (4)
N4—Cu1—N2	103.36 (16)	C7—C8—S1	120.8 (4)
N3—Cu1—N2	137.83 (15)	C10—C9—C8	121.8 (6)
N1—Cu1—O4	87.73 (15)	C10—C9—H9	119.1
N4—Cu1—O4	87.30 (16)	C8—C9—H9	119.1
N3—Cu1—O4	132.05 (16)	C11—C10—C9	119.3 (6)
N2—Cu1—O4	90.12 (15)	C11—C10—H10	120.3
O1—S1—O3	113.8 (3)	C9—C10—H10	120.3
O1—S1—O2	115.3 (3)	C10—C11—C12	120.4 (6)
O3—S1—O2	110.1 (3)	C10—C11—H11	119.8
O1—S1—C8	107.0 (2)	C12—C11—H11	119.8
O3—S1—C8	105.8 (3)	C7—C12—C11	120.5 (6)
O2—S1—C8	103.8 (3)	C7—C12—H12	119.7
O6—S2—O5	114.2 (2)	C11—C12—H12	119.7
O6—S2—O4	112.4 (2)	N3—C13—C14	123.6 (5)
O5—S2—O4	112.1 (2)	N3—C13—H13	118.2
O6—S2—C24	106.2 (2)	C14—C13—H13	118.2
O5—S2—C24	105.7 (2)	C15—C14—C13	119.3 (5)
O4—S2—C24	105.4 (2)	C15—C14—H14	120.4
S2—O4—Cu1	125.0 (2)	C13—C14—H14	120.4
C1—N1—C5	117.7 (5)	C14—C15—C16	118.5 (5)
C1—N1—Cu1	126.7 (4)	C14—C15—H15	120.7
C5—N1—Cu1	115.5 (3)	C16—C15—H15	120.7
C6—N2—C7	118.3 (4)	C15—C16—C17	119.4 (5)
C6—N2—Cu1	111.6 (3)	C15—C16—H16	120.3
C7—N2—Cu1	129.8 (3)	C17—C16—H16	120.3
C13—N3—C17	116.5 (4)	N3—C17—C16	122.6 (5)
C13—N3—Cu1	131.7 (3)	N3—C17—C18	113.7 (5)
C17—N3—Cu1	111.7 (3)	C16—C17—C18	123.6 (5)
C18—N4—C19	122.1 (4)	N4—C18—C17	118.4 (5)
C18—N4—Cu1	114.7 (3)	N4—C18—H18	120.8
C19—N4—Cu1	123.1 (3)	C17—C18—H18	120.8
N1—C1—C2	122.9 (6)	C20—C19—C24	120.9 (5)
N1—C1—H1	118.6	C20—C19—N4	120.0 (5)
C2—C1—H1	118.6	C24—C19—N4	118.8 (4)
C3—C2—C1	118.6 (6)	C21—C20—C19	119.4 (5)
C3—C2—H2	120.7	C21—C20—H20	120.3
C1—C2—H2	120.7	C19—C20—H20	120.3
C2—C3—C4	119.6 (5)	C20—C21—C22	120.5 (5)
C2—C3—H3	120.2	C20—C21—H21	119.8
C4—C3—H3	120.2	C22—C21—H21	119.8
C5—C4—C3	118.5 (5)	C21—C22—C23	119.4 (5)
C5—C4—H4	120.7	C21—C22—H22	120.3
C3—C4—H4	120.7	C23—C22—H22	120.3
N1—C5—C4	122.6 (5)	C24—C23—C22	121.1 (5)
N1—C5—C6	114.3 (4)	C24—C23—H23	119.4
C4—C5—C6	123.1 (5)	C22—C23—H23	119.4
N2—C6—C5	118.1 (5)	C23—C24—C19	118.7 (5)
N2—C6—H6	120.9	C23—C24—S2	120.7 (4)
C5—C6—H6	120.9	C19—C24—S2	120.5 (4)
C12—C7—C8	120.4 (5)
O6—S2—O4—Cu1	158.9 (3)	C6—N2—C7—C8	−113.4 (5)
O5—S2—O4—Cu1	−70.9 (3)	Cu1—N2—C7—C8	73.1 (6)
C24—S2—O4—Cu1	43.6 (3)	C12—C7—C8—C9	0.6 (7)
N1—Cu1—O4—S2	172.6 (3)	N2—C7—C8—C9	−177.5 (4)
N4—Cu1—O4—S2	−3.7 (3)	C12—C7—C8—S1	−174.8 (4)
N3—Cu1—O4—S2	72.2 (3)	N2—C7—C8—S1	7.2 (6)
N2—Cu1—O4—S2	−107.1 (3)	O1—S1—C8—C9	120.6 (5)
N4—Cu1—N1—C1	−51.2 (18)	O3—S1—C8—C9	−1.1 (5)
N3—Cu1—N1—C1	44.4 (5)	O2—S1—C8—C9	−117.1 (4)
N2—Cu1—N1—C1	−178.3 (5)	O1—S1—C8—C7	−64.3 (5)
O4—Cu1—N1—C1	−87.8 (5)	O3—S1—C8—C7	174.1 (4)
N4—Cu1—N1—C5	126.0 (16)	O2—S1—C8—C7	58.1 (5)
N3—Cu1—N1—C5	−138.4 (4)	C7—C8—C9—C10	−0.8 (8)
N2—Cu1—N1—C5	−1.1 (4)	S1—C8—C9—C10	174.6 (5)
O4—Cu1—N1—C5	89.4 (4)	C8—C9—C10—C11	0.6 (10)
N1—Cu1—N2—C6	2.5 (3)	C9—C10—C11—C12	−0.3 (10)
N4—Cu1—N2—C6	−172.4 (3)	C8—C7—C12—C11	−0.3 (8)
N3—Cu1—N2—C6	95.6 (4)	N2—C7—C12—C11	177.8 (5)
O4—Cu1—N2—C6	−85.1 (4)	C10—C11—C12—C7	0.1 (10)
N1—Cu1—N2—C7	176.4 (4)	C17—N3—C13—C14	2.4 (7)
N4—Cu1—N2—C7	1.5 (4)	Cu1—N3—C13—C14	179.0 (4)
N3—Cu1—N2—C7	−90.5 (4)	N3—C13—C14—C15	0.0 (8)
O4—Cu1—N2—C7	88.8 (4)	C13—C14—C15—C16	−2.1 (8)
N1—Cu1—N3—C13	9.2 (5)	C14—C15—C16—C17	1.7 (8)
N4—Cu1—N3—C13	−177.1 (5)	C13—N3—C17—C16	−2.7 (7)
N2—Cu1—N3—C13	−76.6 (5)	Cu1—N3—C17—C16	−179.9 (4)
O4—Cu1—N3—C13	104.4 (4)	C13—N3—C17—C18	177.6 (4)
N1—Cu1—N3—C17	−174.1 (3)	Cu1—N3—C17—C18	0.4 (5)
N4—Cu1—N3—C17	−0.4 (3)	C15—C16—C17—N3	0.7 (8)
N2—Cu1—N3—C17	100.2 (4)	C15—C16—C17—C18	−179.7 (5)
O4—Cu1—N3—C17	−78.8 (4)	C19—N4—C18—C17	−177.2 (4)
N1—Cu1—N4—C18	96.9 (17)	Cu1—N4—C18—C17	−0.2 (6)
N3—Cu1—N4—C18	0.3 (4)	N3—C17—C18—N4	−0.1 (7)
N2—Cu1—N4—C18	−137.0 (4)	C16—C17—C18—N4	−179.8 (5)
O4—Cu1—N4—C18	133.5 (4)	C18—N4—C19—C20	53.8 (7)
N1—Cu1—N4—C19	−86.1 (17)	Cu1—N4—C19—C20	−122.9 (4)
N3—Cu1—N4—C19	177.3 (4)	C18—N4—C19—C24	−132.0 (5)
N2—Cu1—N4—C19	40.0 (4)	Cu1—N4—C19—C24	51.2 (6)
O4—Cu1—N4—C19	−49.5 (4)	C24—C19—C20—C21	0.8 (8)
C5—N1—C1—C2	2.7 (8)	N4—C19—C20—C21	174.8 (5)
Cu1—N1—C1—C2	179.9 (4)	C19—C20—C21—C22	−0.9 (9)
N1—C1—C2—C3	−1.2 (9)	C20—C21—C22—C23	0.4 (9)
C1—C2—C3—C4	−0.4 (9)	C21—C22—C23—C24	0.2 (9)
C2—C3—C4—C5	0.3 (9)	C22—C23—C24—C19	−0.3 (8)
C1—N1—C5—C4	−2.8 (8)	C22—C23—C24—S2	176.9 (4)
Cu1—N1—C5—C4	179.7 (4)	C20—C19—C24—C23	−0.2 (8)
C1—N1—C5—C6	177.2 (5)	N4—C19—C24—C23	−174.3 (4)
Cu1—N1—C5—C6	−0.3 (6)	C20—C19—C24—S2	−177.4 (4)
C3—C4—C5—N1	1.4 (8)	N4—C19—C24—S2	8.5 (6)
C3—C4—C5—C6	−178.6 (5)	O6—S2—C24—C23	9.3 (5)
C7—N2—C6—C5	−178.1 (4)	O5—S2—C24—C23	−112.4 (4)
Cu1—N2—C6—C5	−3.5 (6)	O4—S2—C24—C23	128.7 (4)
N1—C5—C6—N2	2.6 (7)	O6—S2—C24—C19	−173.6 (4)
C4—C5—C6—N2	−177.3 (5)	O5—S2—C24—C19	64.7 (5)
C6—N2—C7—C12	68.5 (6)	O4—S2—C24—C19	−54.1 (5)
Cu1—N2—C7—C12	−105.0 (5)