Aqua-(9,10-dioxoanthracene-1,5-disul-fonato-κO)bis-(1,10-phenanthroline-κN,N')nickel(II).

In the mononuclear title complex, [Ni(C(14)H(6)O(8)S(2))(C(12)H(8)N(2))(2)(H(2)O)], the Ni(II) atom is in a distorted octa-hedral coordination formed by four N atoms from two chelating 1,10-phenanthroline ligands and by two O atoms, one from a 9,10-dioxoanthracene-1,5-disulfonate ligand and the other from a water mol-ecule. An intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, inter-molecular O-H⋯O hydrogen bonds link the mononuclear complexes into chains extending parallel to [010]. Furthermore, π-π stacking inter-actions [centroid-centroid distance = 3.5696 (6) Å] stabilize the crystal structuure.

Related literature

For the structures and applications of organo­sulfonate-based metal complexes, see: Dai et al. (2006 ▶); Cui et al. (2007 ▶); Zhao et al. (2007 ▶); Jia et al. (2009 ▶); Chen et al. (2002 ▶); Yang et al. (2007 ▶). For mol­ecular self-assembly by non-covalent inter­actions in crystal engineering, see: Hunter (1993 ▶).

Experimental

Crystal data

[Ni(C14H6O8S2)(C12H8N2)2(H2O)]

M = 803.44

Triclinic,

a = 8.8784 (19) Å

b = 12.802 (3) Å

c = 14.723 (3) Å

α = 98.016 (3)°

β = 100.520 (3)°

γ = 91.380 (2)°

V = 1627.1 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.79 mm−1

T = 294 K

0.34 × 0.32 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.774, T max = 0.808

8942 measured reflections

5693 independent reflections

4243 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.05

5693 reflections

487 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 ▶) and DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034252/bt5331sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034252/bt5331Isup2.hkl

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

[Ni(C14H6O8S2)(C12H8N2)2(H2O)]	Z = 2
Mr = 803.44	F(000) = 824
Triclinic, P1	Dx = 1.640 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8784 (19) Å	Cell parameters from 2813 reflections
b = 12.802 (3) Å	θ = 2.3–25.2°
c = 14.723 (3) Å	µ = 0.79 mm−1
α = 98.016 (3)°	T = 294 K
β = 100.520 (3)°	Block, yellow
γ = 91.380 (2)°	0.34 × 0.32 × 0.28 mm
V = 1627.1 (6) Å3

Bruker APEXII CCD area-detector diffractometer	5693 independent reflections
Radiation source: fine-focus sealed tube	4243 reflections with I > 2σ(I)
graphite	Rint = 0.020
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.774, Tmax = 0.808	k = −15→12
8942 measured reflections	l = −17→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.3249P] where P = (Fo2 + 2Fc2)/3
5693 reflections	(Δ/σ)max = 0.001
487 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.43 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 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.

	x	y	z	Uiso*/Ueq
Ni1	0.51255 (4)	0.67299 (3)	0.76204 (2)	0.03729 (13)
S1	0.20477 (9)	0.73215 (6)	0.85480 (5)	0.0398 (2)
O1	0.3705 (2)	0.74179 (15)	0.85534 (13)	0.0405 (5)
O2	0.1640 (2)	0.76635 (16)	0.94350 (14)	0.0476 (5)
O3	0.1423 (2)	0.62602 (16)	0.81432 (15)	0.0525 (6)
O4	0.3113 (3)	1.19722 (17)	0.55562 (14)	0.0599 (7)
O5	0.4395 (3)	1.36031 (18)	0.63825 (16)	0.0649 (7)
O6	0.1714 (3)	1.33736 (18)	0.62472 (18)	0.0662 (7)
O7	0.3099 (3)	0.95751 (17)	0.92421 (14)	0.0589 (7)
O8	0.0471 (3)	1.1338 (2)	0.6416 (2)	0.0840 (10)
O9	0.3412 (3)	0.56089 (17)	0.70180 (16)	0.0596 (6)
H9A	0.2799	0.5630	0.7401	0.089*
H9B	0.3718	0.5007	0.6830	0.089*
N1	0.6648 (3)	0.80251 (18)	0.81146 (17)	0.0409 (6)
N2	0.4355 (3)	0.7717 (2)	0.66457 (17)	0.0459 (6)
N3	0.6219 (3)	0.58737 (18)	0.86155 (16)	0.0373 (6)
N4	0.6551 (3)	0.58717 (18)	0.68469 (16)	0.0390 (6)
C1	0.6355 (3)	0.8838 (2)	0.7615 (2)	0.0401 (7)
C2	0.7799 (4)	0.8171 (3)	0.8840 (2)	0.0510 (8)
H2	0.8028	0.7618	0.9182	0.061*
C3	0.8673 (4)	0.9109 (3)	0.9112 (3)	0.0669 (11)
H3	0.9470	0.9176	0.9627	0.080*
C4	0.8372 (4)	0.9926 (3)	0.8631 (3)	0.0687 (11)
H4	0.8940	1.0563	0.8822	0.082*
C5	0.7204 (4)	0.9808 (2)	0.7847 (3)	0.0516 (9)
C6	0.6834 (4)	1.0610 (3)	0.7278 (3)	0.0618 (10)
H6	0.7405	1.1250	0.7418	0.074*
C7	0.5677 (5)	1.0457 (3)	0.6545 (3)	0.0583 (10)
H7	0.5454	1.1000	0.6190	0.070*
C8	0.4773 (4)	0.9488 (3)	0.6291 (2)	0.0501 (9)
C9	0.3536 (4)	0.9285 (3)	0.5550 (2)	0.0595 (10)
H9	0.3231	0.9811	0.5190	0.071*
C10	0.2769 (5)	0.8328 (3)	0.5347 (2)	0.0639 (10)
H10	0.1962	0.8188	0.4840	0.077*
C11	0.3212 (4)	0.7549 (3)	0.5915 (2)	0.0551 (9)
H11	0.2684	0.6893	0.5773	0.066*
C12	0.5131 (4)	0.8670 (2)	0.6827 (2)	0.0422 (7)
C13	0.7236 (3)	0.5218 (2)	0.8298 (2)	0.0358 (7)
C14	0.6111 (4)	0.5946 (2)	0.9512 (2)	0.0462 (8)
H14	0.5416	0.6399	0.9738	0.055*
C15	0.7008 (4)	0.5364 (3)	1.0124 (2)	0.0516 (9)
H15	0.6929	0.5451	1.0751	0.062*
C16	0.7991 (4)	0.4675 (2)	0.9804 (2)	0.0451 (8)
H16	0.8568	0.4273	1.0206	0.054*
C17	0.8134 (3)	0.4573 (2)	0.8862 (2)	0.0408 (7)
C18	0.9110 (4)	0.3856 (2)	0.8449 (2)	0.0495 (8)
H18	0.9665	0.3404	0.8810	0.059*
C19	0.9248 (4)	0.3818 (3)	0.7543 (2)	0.0510 (8)
H19	0.9893	0.3343	0.7293	0.061*
C20	0.8404 (3)	0.4508 (2)	0.6967 (2)	0.0418 (7)
C21	0.8543 (4)	0.4540 (3)	0.6035 (2)	0.0506 (8)
H21	0.9205	0.4104	0.5758	0.061*
C22	0.7691 (4)	0.5223 (3)	0.5541 (2)	0.0515 (8)
H22	0.7775	0.5258	0.4926	0.062*
C23	0.6699 (4)	0.5864 (2)	0.5963 (2)	0.0459 (8)
H23	0.6110	0.6310	0.5611	0.055*
C24	0.7396 (3)	0.5191 (2)	0.73459 (19)	0.0367 (7)
C25	0.2713 (3)	0.9862 (2)	0.84869 (19)	0.0361 (7)
C26	0.1617 (3)	0.9217 (2)	0.77210 (18)	0.0316 (6)
C27	0.1177 (3)	0.8148 (2)	0.77205 (19)	0.0360 (7)
C28	0.0029 (3)	0.7658 (3)	0.7013 (2)	0.0501 (9)
H28	−0.0268	0.6956	0.7012	0.060*
C29	−0.0685 (4)	0.8182 (3)	0.6313 (2)	0.0580 (10)
H29	−0.1466	0.7838	0.5852	0.070*
C30	−0.0244 (3)	0.9214 (2)	0.6293 (2)	0.0448 (8)
H30	−0.0714	0.9564	0.5813	0.054*
C31	0.0898 (3)	0.9730 (2)	0.69854 (19)	0.0365 (7)
C32	0.1328 (3)	1.0862 (2)	0.6930 (2)	0.0409 (7)
C33	0.2762 (3)	1.1352 (2)	0.75234 (18)	0.0326 (6)
C34	0.3511 (3)	1.2275 (2)	0.73629 (19)	0.0348 (6)
S2	0.31237 (9)	1.28400 (6)	0.62861 (5)	0.0406 (2)
C36	0.4761 (4)	1.2716 (2)	0.8016 (2)	0.0437 (8)
H36	0.5253	1.3328	0.7917	0.052*
C37	0.5305 (4)	1.2280 (2)	0.8810 (2)	0.0462 (8)
H37	0.6133	1.2607	0.9245	0.055*
C38	0.4619 (3)	1.1357 (2)	0.8958 (2)	0.0409 (7)
H38	0.4998	1.1050	0.9484	0.049*
C39	0.3358 (3)	1.0890 (2)	0.83153 (18)	0.0338 (6)

	U11	U22	U33	U12	U13	U23
Ni1	0.0464 (2)	0.0297 (2)	0.0329 (2)	0.00424 (16)	−0.00302 (17)	0.00803 (16)
S1	0.0423 (4)	0.0375 (4)	0.0388 (4)	−0.0023 (3)	−0.0022 (3)	0.0168 (3)
O1	0.0382 (12)	0.0387 (11)	0.0413 (12)	0.0021 (9)	−0.0029 (9)	0.0083 (9)
O2	0.0522 (13)	0.0541 (14)	0.0403 (12)	0.0037 (10)	0.0078 (10)	0.0211 (10)
O3	0.0591 (14)	0.0380 (12)	0.0569 (14)	−0.0133 (10)	−0.0046 (11)	0.0179 (10)
O4	0.0929 (18)	0.0480 (14)	0.0317 (12)	0.0215 (12)	−0.0056 (11)	0.0007 (10)
O5	0.0696 (16)	0.0626 (16)	0.0610 (15)	−0.0220 (13)	−0.0017 (13)	0.0266 (13)
O6	0.0672 (16)	0.0620 (16)	0.0826 (18)	0.0345 (13)	0.0226 (13)	0.0398 (14)
O7	0.0852 (17)	0.0502 (14)	0.0338 (12)	−0.0166 (12)	−0.0153 (11)	0.0189 (10)
O8	0.0617 (16)	0.0684 (17)	0.112 (2)	−0.0115 (13)	−0.0398 (15)	0.0560 (16)
O9	0.0673 (16)	0.0399 (13)	0.0631 (15)	−0.0023 (11)	−0.0020 (12)	−0.0025 (11)
N1	0.0456 (15)	0.0353 (14)	0.0424 (15)	0.0039 (11)	0.0067 (12)	0.0098 (11)
N2	0.0568 (17)	0.0450 (16)	0.0339 (14)	0.0126 (13)	0.0004 (12)	0.0078 (12)
N3	0.0424 (14)	0.0345 (14)	0.0342 (14)	0.0002 (11)	0.0022 (11)	0.0094 (11)
N4	0.0491 (15)	0.0313 (13)	0.0349 (14)	0.0028 (11)	−0.0014 (11)	0.0107 (11)
C1	0.0440 (18)	0.0347 (17)	0.0459 (18)	0.0096 (13)	0.0160 (14)	0.0098 (14)
C2	0.050 (2)	0.0425 (19)	0.056 (2)	−0.0013 (15)	−0.0033 (16)	0.0076 (16)
C3	0.063 (2)	0.053 (2)	0.074 (3)	−0.0076 (18)	−0.009 (2)	0.001 (2)
C4	0.057 (2)	0.043 (2)	0.101 (3)	−0.0075 (17)	0.008 (2)	0.003 (2)
C5	0.050 (2)	0.0363 (18)	0.076 (2)	0.0096 (15)	0.0291 (18)	0.0134 (17)
C6	0.065 (2)	0.040 (2)	0.091 (3)	0.0085 (17)	0.035 (2)	0.020 (2)
C7	0.080 (3)	0.039 (2)	0.075 (3)	0.0194 (18)	0.048 (2)	0.0287 (18)
C8	0.064 (2)	0.054 (2)	0.0438 (19)	0.0303 (17)	0.0265 (17)	0.0215 (16)
C9	0.082 (3)	0.062 (2)	0.046 (2)	0.033 (2)	0.0245 (19)	0.0241 (18)
C10	0.073 (3)	0.082 (3)	0.0352 (19)	0.032 (2)	−0.0012 (17)	0.0129 (19)
C11	0.072 (2)	0.052 (2)	0.0368 (18)	0.0181 (17)	−0.0031 (17)	0.0065 (15)
C12	0.0542 (19)	0.0375 (17)	0.0407 (18)	0.0121 (14)	0.0183 (15)	0.0119 (14)
C13	0.0379 (16)	0.0292 (15)	0.0385 (17)	−0.0043 (12)	−0.0022 (13)	0.0119 (13)
C14	0.052 (2)	0.051 (2)	0.0358 (18)	0.0010 (15)	0.0057 (14)	0.0111 (15)
C15	0.055 (2)	0.064 (2)	0.0380 (18)	−0.0036 (17)	0.0037 (15)	0.0222 (16)
C16	0.0443 (18)	0.0462 (19)	0.0455 (19)	−0.0021 (15)	−0.0034 (15)	0.0257 (15)
C17	0.0410 (17)	0.0363 (17)	0.0443 (18)	−0.0039 (13)	−0.0013 (14)	0.0167 (14)
C18	0.0481 (19)	0.0383 (18)	0.061 (2)	0.0087 (15)	−0.0043 (16)	0.0209 (16)
C19	0.0480 (19)	0.0457 (19)	0.060 (2)	0.0142 (15)	0.0047 (16)	0.0141 (17)
C20	0.0421 (17)	0.0362 (17)	0.0460 (19)	0.0029 (13)	0.0036 (14)	0.0081 (14)
C21	0.057 (2)	0.050 (2)	0.0433 (19)	0.0054 (16)	0.0079 (16)	0.0026 (16)
C22	0.067 (2)	0.053 (2)	0.0340 (17)	0.0019 (17)	0.0070 (16)	0.0054 (15)
C23	0.060 (2)	0.0423 (18)	0.0330 (17)	0.0031 (15)	−0.0010 (15)	0.0106 (14)
C24	0.0413 (17)	0.0303 (15)	0.0359 (16)	−0.0041 (13)	−0.0017 (13)	0.0083 (13)
C25	0.0376 (16)	0.0366 (16)	0.0329 (16)	0.0030 (12)	−0.0010 (12)	0.0110 (13)
C26	0.0288 (14)	0.0365 (16)	0.0300 (15)	0.0019 (12)	0.0023 (12)	0.0103 (12)
C27	0.0328 (15)	0.0403 (17)	0.0346 (16)	−0.0023 (12)	0.0000 (12)	0.0135 (13)
C28	0.0462 (19)	0.0463 (19)	0.052 (2)	−0.0137 (15)	−0.0117 (15)	0.0193 (16)
C29	0.0443 (19)	0.067 (2)	0.053 (2)	−0.0188 (16)	−0.0200 (16)	0.0197 (18)
C30	0.0352 (17)	0.055 (2)	0.0425 (18)	−0.0031 (14)	−0.0078 (14)	0.0216 (15)
C31	0.0312 (15)	0.0426 (17)	0.0361 (16)	0.0005 (12)	0.0013 (12)	0.0142 (13)
C32	0.0374 (16)	0.0435 (18)	0.0420 (17)	0.0010 (13)	−0.0030 (14)	0.0207 (14)
C33	0.0372 (16)	0.0306 (15)	0.0297 (15)	0.0062 (12)	0.0031 (12)	0.0061 (12)
C34	0.0412 (17)	0.0287 (15)	0.0331 (16)	0.0018 (12)	0.0030 (13)	0.0051 (12)
S2	0.0494 (5)	0.0337 (4)	0.0392 (4)	0.0050 (3)	0.0030 (3)	0.0133 (3)
C36	0.056 (2)	0.0315 (16)	0.0402 (17)	−0.0077 (14)	0.0010 (15)	0.0055 (13)
C37	0.058 (2)	0.0389 (18)	0.0350 (17)	−0.0071 (15)	−0.0050 (15)	0.0004 (14)
C38	0.0498 (18)	0.0385 (17)	0.0309 (16)	0.0007 (14)	−0.0022 (13)	0.0062 (13)
C39	0.0400 (16)	0.0330 (15)	0.0281 (15)	0.0039 (12)	0.0038 (12)	0.0068 (12)

Ni1—O9	2.051 (2)	C11—H11	0.9300
Ni1—N3	2.066 (2)	C13—C17	1.410 (4)
Ni1—N1	2.074 (2)	C13—C24	1.431 (4)
Ni1—N2	2.077 (2)	C14—C15	1.399 (4)
Ni1—N4	2.086 (3)	C14—H14	0.9300
Ni1—O1	2.145 (2)	C15—C16	1.354 (5)
S1—O2	1.431 (2)	C15—H15	0.9300
S1—O3	1.458 (2)	C16—C17	1.404 (4)
S1—O1	1.472 (2)	C16—H16	0.9300
S1—C27	1.804 (3)	C17—C18	1.427 (5)
O4—S2	1.432 (2)	C18—C19	1.355 (4)
O5—S2	1.449 (2)	C18—H18	0.9300
O6—S2	1.436 (2)	C19—C20	1.439 (4)
O7—C25	1.212 (3)	C19—H19	0.9300
O8—C32	1.209 (3)	C20—C24	1.400 (4)
O9—H9A	0.8501	C20—C21	1.406 (4)
O9—H9B	0.8501	C21—C22	1.369 (4)
N1—C2	1.326 (4)	C21—H21	0.9300
N1—C1	1.359 (3)	C22—C23	1.388 (5)
N2—C11	1.326 (4)	C22—H22	0.9300
N2—C12	1.356 (4)	C23—H23	0.9300
N3—C14	1.331 (4)	C25—C26	1.484 (4)
N3—C13	1.349 (4)	C25—C39	1.494 (4)
N4—C23	1.330 (4)	C26—C31	1.406 (3)
N4—C24	1.367 (3)	C26—C27	1.414 (4)
C1—C5	1.404 (4)	C27—C28	1.384 (4)
C1—C12	1.425 (4)	C28—C29	1.375 (4)
C2—C3	1.383 (5)	C28—H28	0.9300
C2—H2	0.9300	C29—C30	1.374 (4)
C3—C4	1.348 (5)	C29—H29	0.9300
C3—H3	0.9300	C30—C31	1.381 (4)
C4—C5	1.392 (5)	C30—H30	0.9300
C4—H4	0.9300	C31—C32	1.506 (4)
C5—C6	1.421 (5)	C32—C33	1.477 (4)
C6—C7	1.335 (5)	C33—C39	1.404 (3)
C6—H6	0.9300	C33—C34	1.411 (4)
C7—C8	1.428 (5)	C34—C36	1.380 (4)
C7—H7	0.9300	C34—S2	1.813 (3)
C8—C9	1.390 (5)	C36—C37	1.379 (4)
C8—C12	1.405 (4)	C36—H36	0.9300
C9—C10	1.355 (5)	C37—C38	1.377 (4)
C9—H9	0.9300	C37—H37	0.9300
C10—C11	1.407 (4)	C38—C39	1.389 (4)
C10—H10	0.9300	C38—H38	0.9300
O9—Ni1—N3	96.61 (9)	C16—C15—C14	120.0 (3)
O9—Ni1—N1	170.98 (9)	C16—C15—H15	120.0
N3—Ni1—N1	92.15 (9)	C14—C15—H15	120.0
O9—Ni1—N2	91.57 (10)	C15—C16—C17	119.5 (3)
N3—Ni1—N2	171.08 (10)	C15—C16—H16	120.2
N1—Ni1—N2	79.83 (10)	C17—C16—H16	120.2
O9—Ni1—N4	87.47 (10)	C16—C17—C13	117.0 (3)
N3—Ni1—N4	80.16 (9)	C16—C17—C18	124.2 (3)
N1—Ni1—N4	96.19 (10)	C13—C17—C18	118.9 (3)
N2—Ni1—N4	96.71 (9)	C19—C18—C17	121.7 (3)
O9—Ni1—O1	90.17 (9)	C19—C18—H18	119.2
N3—Ni1—O1	91.38 (9)	C17—C18—H18	119.2
N1—Ni1—O1	87.44 (9)	C18—C19—C20	120.4 (3)
N2—Ni1—O1	92.15 (9)	C18—C19—H19	119.8
N4—Ni1—O1	170.88 (8)	C20—C19—H19	119.8
O2—S1—O3	112.60 (13)	C24—C20—C21	117.7 (3)
O2—S1—O1	113.95 (12)	C24—C20—C19	119.0 (3)
O3—S1—O1	110.91 (13)	C21—C20—C19	123.3 (3)
O2—S1—C27	109.11 (13)	C22—C21—C20	119.1 (3)
O3—S1—C27	104.16 (13)	C22—C21—H21	120.5
O1—S1—C27	105.37 (12)	C20—C21—H21	120.5
S1—O1—Ni1	133.04 (12)	C21—C22—C23	119.7 (3)
Ni1—O9—H9A	105.1	C21—C22—H22	120.1
Ni1—O9—H9B	114.9	C23—C22—H22	120.1
H9A—O9—H9B	117.0	N4—C23—C22	123.1 (3)
C2—N1—C1	117.4 (3)	N4—C23—H23	118.5
C2—N1—Ni1	129.7 (2)	C22—C23—H23	118.5
C1—N1—Ni1	112.88 (19)	N4—C24—C20	122.7 (3)
C11—N2—C12	117.8 (3)	N4—C24—C13	116.9 (3)
C11—N2—Ni1	129.2 (2)	C20—C24—C13	120.4 (3)
C12—N2—Ni1	112.95 (19)	O7—C25—C26	121.8 (2)
C14—N3—C13	118.3 (3)	O7—C25—C39	119.5 (2)
C14—N3—Ni1	128.4 (2)	C26—C25—C39	118.7 (2)
C13—N3—Ni1	113.18 (18)	C31—C26—C27	118.5 (2)
C23—N4—C24	117.6 (3)	C31—C26—C25	117.3 (2)
C23—N4—Ni1	130.2 (2)	C27—C26—C25	124.1 (2)
C24—N4—Ni1	112.18 (19)	C28—C27—C26	118.9 (2)
N1—C1—C5	122.7 (3)	C28—C27—S1	115.7 (2)
N1—C1—C12	117.1 (3)	C26—C27—S1	125.4 (2)
C5—C1—C12	120.2 (3)	C29—C28—C27	121.7 (3)
N1—C2—C3	122.9 (3)	C29—C28—H28	119.1
N1—C2—H2	118.5	C27—C28—H28	119.1
C3—C2—H2	118.5	C30—C29—C28	120.0 (3)
C4—C3—C2	120.0 (3)	C30—C29—H29	120.0
C4—C3—H3	120.0	C28—C29—H29	120.0
C2—C3—H3	120.0	C29—C30—C31	120.0 (3)
C3—C4—C5	119.6 (3)	C29—C30—H30	120.0
C3—C4—H4	120.2	C31—C30—H30	120.0
C5—C4—H4	120.2	C30—C31—C26	120.9 (3)
C4—C5—C1	117.3 (3)	C30—C31—C32	117.6 (2)
C4—C5—C6	123.7 (3)	C26—C31—C32	121.5 (2)
C1—C5—C6	118.9 (3)	O8—C32—C33	122.7 (3)
C7—C6—C5	120.9 (3)	O8—C32—C31	118.8 (3)
C7—C6—H6	119.5	C33—C32—C31	118.5 (2)
C5—C6—H6	119.5	C39—C33—C34	119.0 (2)
C6—C7—C8	122.0 (3)	C39—C33—C32	117.1 (2)
C6—C7—H7	119.0	C34—C33—C32	123.8 (2)
C8—C7—H7	119.0	C36—C34—C33	118.5 (2)
C9—C8—C12	116.6 (3)	C36—C34—S2	116.2 (2)
C9—C8—C7	125.0 (3)	C33—C34—S2	124.8 (2)
C12—C8—C7	118.5 (3)	O4—S2—O6	115.06 (15)
C10—C9—C8	120.7 (3)	O4—S2—O5	113.50 (16)
C10—C9—H9	119.7	O6—S2—O5	109.79 (15)
C8—C9—H9	119.7	O4—S2—C34	105.34 (13)
C9—C10—C11	119.1 (3)	O6—S2—C34	108.66 (14)
C9—C10—H10	120.5	O5—S2—C34	103.64 (13)
C11—C10—H10	120.5	C37—C36—C34	122.2 (3)
N2—C11—C10	122.3 (3)	C37—C36—H36	118.9
N2—C11—H11	118.8	C34—C36—H36	118.9
C10—C11—H11	118.8	C38—C37—C36	119.8 (3)
N2—C12—C8	123.4 (3)	C38—C37—H37	120.1
N2—C12—C1	117.1 (2)	C36—C37—H37	120.1
C8—C12—C1	119.5 (3)	C37—C38—C39	119.6 (3)
N3—C13—C17	122.9 (3)	C37—C38—H38	120.2
N3—C13—C24	117.5 (2)	C39—C38—H38	120.2
C17—C13—C24	119.5 (3)	C38—C39—C33	120.8 (2)
N3—C14—C15	122.1 (3)	C38—C39—C25	117.1 (2)
N3—C14—H14	118.9	C33—C39—C25	122.0 (2)
C15—C14—H14	118.9
O2—S1—O1—Ni1	162.23 (13)	C13—N3—C14—C15	−0.3 (4)
O3—S1—O1—Ni1	33.92 (19)	Ni1—N3—C14—C15	−175.3 (2)
C27—S1—O1—Ni1	−78.20 (17)	N3—C14—C15—C16	−2.1 (5)
O9—Ni1—O1—S1	−16.47 (16)	C14—C15—C16—C17	1.8 (5)
N3—Ni1—O1—S1	−113.08 (16)	C15—C16—C17—C13	0.7 (4)
N1—Ni1—O1—S1	154.83 (16)	C15—C16—C17—C18	−178.7 (3)
N2—Ni1—O1—S1	75.11 (16)	N3—C13—C17—C16	−3.3 (4)
N4—Ni1—O1—S1	−91.4 (5)	C24—C13—C17—C16	176.5 (3)
O9—Ni1—N1—C2	163.0 (6)	N3—C13—C17—C18	176.2 (3)
N3—Ni1—N1—C2	−3.1 (3)	C24—C13—C17—C18	−4.0 (4)
N2—Ni1—N1—C2	−179.2 (3)	C16—C17—C18—C19	−177.4 (3)
N4—Ni1—N1—C2	−83.4 (3)	C13—C17—C18—C19	3.2 (4)
O1—Ni1—N1—C2	88.2 (3)	C17—C18—C19—C20	0.0 (5)
O9—Ni1—N1—C1	−15.1 (7)	C18—C19—C20—C24	−2.3 (5)
N3—Ni1—N1—C1	178.8 (2)	C18—C19—C20—C21	177.3 (3)
N2—Ni1—N1—C1	2.8 (2)	C24—C20—C21—C22	−0.4 (5)
N4—Ni1—N1—C1	98.5 (2)	C19—C20—C21—C22	179.9 (3)
O1—Ni1—N1—C1	−89.9 (2)	C20—C21—C22—C23	−0.5 (5)
O9—Ni1—N2—C11	−3.0 (3)	C24—N4—C23—C22	−1.7 (4)
N3—Ni1—N2—C11	153.5 (6)	Ni1—N4—C23—C22	−178.6 (2)
N1—Ni1—N2—C11	179.8 (3)	C21—C22—C23—N4	1.6 (5)
N4—Ni1—N2—C11	84.6 (3)	C23—N4—C24—C20	0.7 (4)
O1—Ni1—N2—C11	−93.2 (3)	Ni1—N4—C24—C20	178.1 (2)
O9—Ni1—N2—C12	174.7 (2)	C23—N4—C24—C13	179.3 (2)
N3—Ni1—N2—C12	−28.8 (7)	Ni1—N4—C24—C13	−3.2 (3)
N1—Ni1—N2—C12	−2.6 (2)	C21—C20—C24—N4	0.4 (4)
N4—Ni1—N2—C12	−97.7 (2)	C19—C20—C24—N4	180.0 (3)
O1—Ni1—N2—C12	84.4 (2)	C21—C20—C24—C13	−178.2 (3)
O9—Ni1—N3—C14	−99.1 (3)	C19—C20—C24—C13	1.4 (4)
N1—Ni1—N3—C14	78.7 (3)	N3—C13—C24—N4	2.9 (4)
N2—Ni1—N3—C14	104.6 (7)	C17—C13—C24—N4	−176.9 (2)
N4—Ni1—N3—C14	174.6 (3)	N3—C13—C24—C20	−178.4 (3)
O1—Ni1—N3—C14	−8.8 (2)	C17—C13—C24—C20	1.8 (4)
O9—Ni1—N3—C13	85.70 (19)	O7—C25—C26—C31	161.8 (3)
N1—Ni1—N3—C13	−96.47 (19)	C39—C25—C26—C31	−18.4 (4)
N2—Ni1—N3—C13	−70.6 (7)	O7—C25—C26—C27	−13.5 (5)
N4—Ni1—N3—C13	−0.56 (18)	C39—C25—C26—C27	166.2 (3)
O1—Ni1—N3—C13	176.04 (18)	C31—C26—C27—C28	−1.8 (4)
O9—Ni1—N4—C23	81.9 (3)	C25—C26—C27—C28	173.5 (3)
N3—Ni1—N4—C23	179.1 (3)	C31—C26—C27—S1	175.3 (2)
N1—Ni1—N4—C23	−89.8 (3)	C25—C26—C27—S1	−9.4 (4)
N2—Ni1—N4—C23	−9.4 (3)	O2—S1—C27—C28	−111.8 (3)
O1—Ni1—N4—C23	157.1 (4)	O3—S1—C27—C28	8.6 (3)
O9—Ni1—N4—C24	−95.10 (19)	O1—S1—C27—C28	125.4 (2)
N3—Ni1—N4—C24	2.06 (18)	O2—S1—C27—C26	71.0 (3)
N1—Ni1—N4—C24	93.17 (19)	O3—S1—C27—C26	−168.6 (3)
N2—Ni1—N4—C24	173.62 (18)	O1—S1—C27—C26	−51.8 (3)
O1—Ni1—N4—C24	−20.0 (6)	C26—C27—C28—C29	0.3 (5)
C2—N1—C1—C5	−0.8 (5)	S1—C27—C28—C29	−177.1 (3)
Ni1—N1—C1—C5	177.5 (2)	C27—C28—C29—C30	1.2 (6)
C2—N1—C1—C12	179.1 (3)	C28—C29—C30—C31	−1.1 (5)
Ni1—N1—C1—C12	−2.6 (3)	C29—C30—C31—C26	−0.4 (5)
C1—N1—C2—C3	1.3 (5)	C29—C30—C31—C32	−179.7 (3)
Ni1—N1—C2—C3	−176.7 (3)	C27—C26—C31—C30	1.9 (4)
N1—C2—C3—C4	−0.1 (6)	C25—C26—C31—C30	−173.7 (3)
C2—C3—C4—C5	−1.7 (6)	C27—C26—C31—C32	−178.9 (3)
C3—C4—C5—C1	2.1 (6)	C25—C26—C31—C32	5.5 (4)
C3—C4—C5—C6	−177.9 (4)	C30—C31—C32—O8	15.4 (5)
N1—C1—C5—C4	−0.9 (5)	C26—C31—C32—O8	−163.9 (3)
C12—C1—C5—C4	179.2 (3)	C30—C31—C32—C33	−166.1 (3)
N1—C1—C5—C6	179.1 (3)	C26—C31—C32—C33	14.7 (4)
C12—C1—C5—C6	−0.8 (5)	O8—C32—C33—C39	157.1 (3)
C4—C5—C6—C7	−178.5 (4)	C31—C32—C33—C39	−21.4 (4)
C1—C5—C6—C7	1.5 (5)	O8—C32—C33—C34	−19.8 (5)
C5—C6—C7—C8	−0.8 (5)	C31—C32—C33—C34	161.8 (3)
C6—C7—C8—C9	178.6 (3)	C39—C33—C34—C36	−3.0 (4)
C6—C7—C8—C12	−0.6 (5)	C32—C33—C34—C36	173.8 (3)
C12—C8—C9—C10	−2.4 (5)	C39—C33—C34—S2	168.3 (2)
C7—C8—C9—C10	178.3 (3)	C32—C33—C34—S2	−14.9 (4)
C8—C9—C10—C11	1.9 (5)	C36—C34—S2—O4	124.0 (3)
C12—N2—C11—C10	−1.5 (5)	C33—C34—S2—O4	−47.4 (3)
Ni1—N2—C11—C10	176.1 (2)	C36—C34—S2—O6	−112.2 (3)
C9—C10—C11—N2	0.1 (6)	C33—C34—S2—O6	76.3 (3)
C11—N2—C12—C8	0.9 (5)	C36—C34—S2—O5	4.5 (3)
Ni1—N2—C12—C8	−177.1 (2)	C33—C34—S2—O5	−166.9 (3)
C11—N2—C12—C1	180.0 (3)	C33—C34—C36—C37	0.6 (5)
Ni1—N2—C12—C1	2.0 (3)	S2—C34—C36—C37	−171.4 (3)
C9—C8—C12—N2	1.0 (5)	C34—C36—C37—C38	1.8 (5)
C7—C8—C12—N2	−179.7 (3)	C36—C37—C38—C39	−1.7 (5)
C9—C8—C12—C1	−178.0 (3)	C37—C38—C39—C33	−0.7 (5)
C7—C8—C12—C1	1.3 (4)	C37—C38—C39—C25	176.9 (3)
N1—C1—C12—N2	0.4 (4)	C34—C33—C39—C38	3.1 (4)
C5—C1—C12—N2	−179.7 (3)	C32—C33—C39—C38	−173.9 (3)
N1—C1—C12—C8	179.5 (3)	C34—C33—C39—C25	−174.4 (3)
C5—C1—C12—C8	−0.6 (5)	C32—C33—C39—C25	8.5 (4)
C14—N3—C13—C17	3.1 (4)	O7—C25—C39—C38	13.8 (4)
Ni1—N3—C13—C17	178.8 (2)	C26—C25—C39—C38	−166.0 (3)
C14—N3—C13—C24	−176.8 (2)	O7—C25—C39—C33	−168.6 (3)
Ni1—N3—C13—C24	−1.0 (3)	C26—C25—C39—C33	11.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O3	0.85	1.90	2.704 (3)	156
O9—H9B···O5i	0.85	1.97	2.823 (3)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9A⋯O3	0.85	1.90	2.704 (3)	156
O9—H9B⋯O5i	0.85	1.97	2.823 (3)	179

Symmetry code: (i) .