trans-Dipyridine­bis(sulfamerazinato)nickel(II)–pyridine (1/4)

Hossain, G.M.G.; Amoroso, A.J.

doi:10.1107/S1600536806038116

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 62| Part 10| October 2006| Pages m2721-m2722

https://doi.org/10.1107/S1600536806038116

trans-Dipyridinebis(sulfamerazinato)nickel(II)–pyridine (1/4)

G. M. Golzar Hossain ^a ^* and A. J. Amoroso ^a

^aSchool of Chemistry, Cardiff University, Cardiff CF10 3AT, Wales
^*Correspondence e-mail: acsbd@yahoo.com

(Received 23 August 2006; accepted 18 September 2006; online 27 September 2006)

The title compound, [Ni(C₁₁H₁₁N₄O₂S)₂(C₅H₅N)₂]·4C₅H₅N, contains the centrosymmetric octahedral complex trans-[Ni(smr)₂(py)₂] (where smr is the sulfamerazinate anion and py is pyridine) linked to four pyridine molecules via N—H⋯N hydrogen bonds. This is the first crystal structure of a metal complex of sulfamerazine.

Comment

The sulfamerazine molecule was introduced into medical therapy because, like many sulfonamide derivatives, it exhibits antibacterial activity. The presence of several potential donor sites, namely the amino, pyrimidine and sulfonamide N atoms and the sulfonyl O atoms, make this ligand a versatile complexing agent. Here, we report the structure of the title nickel complex, (I), of the sulfamerazinate anion (Fig. 1). This is the first crystal structure of a metal complex of sulfamerazine.

In complex (I), the Ni atom lies on a centre of inversion, and the complex contains two bidentate N-coordinated sulfamerazinate anions and two pyridine molecules occupying the trans sites. In addition, four pyridine molecules are linked via N—H⋯N hydrogen bonds to the terminal amino groups of the sulfamerazinate ligands (Table 1, Fig. 1).

The relative orientations of the sulfamerazinate ligands and the coordinated pyridine molecules are such that they are nearly perpendicular to each other. Such an orientation of the ligands around the Ni atom appears to be dictated more by steric considerations than any other factors.

The Ni—N bond distances involving the sulfonamide atom N11, the pyrimido atom N12 and the pyrimidine atom N1 are very similar, at 2.139 (2), 2.100 (2) and 2.080 (2) Å, respectively. The tetrahedral coordination at S is distorted, as also found in the neutral sulfamerazine molecule. The endocyclic angle at C11 in complex (I) is 125.2 (2)°, which is somewhat smaller than the corresponding values found in the various polymorphs of the free sulfamerazine molecule [127.5 (2) (Hossain, 2006 ), 127.1 (7) (Acharya et al., 1982 ), and 127.1 (4) and 128.2 (4)° (Caria & Mohamed, 1992 )], due to the coordination to the Ni centre.

The S—O bond distances of 1.4460 (15) and 1.4435 (17) Å in (I) are longer than the corresponding bonds in pure sulfamerazine, where the values obtained are 1.4398 (16) and 1.4293 (17) Å (Hossain, 2006), 1.430 (6) and 1.441 (6) Å (Acharya et al., 1982), and 1.424 (4) and 1.435 (3), and 1.414 (4) and 1.431 (3) Å (Caria & Mohamed, 1992).

The H atoms of the amino groups form intermolecular hydrogen bonds with the N atoms of four pyridine molecules (Table 1, Fig. 1).

Figure 1
The molecular structure of (I)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms bonded to C atoms have been omitted for clarity. Hydrogen bonds are shown as dashed lines. Atoms marked with a prime are at the symmetry position (1 − x, 1 − y, 1 − z).

Experimental

Solid sulfamerazine (Hsmr) (0.529 g, 2 mmol) was dissolved in hot methanol (50 ml) and a methanolic solution (10 ml) of NiCl₂·6H₂O (0.238 g, 1 mmol) was added slowly with constant stirring on a hot plate at 333 K. A pink precipitate formed and stirring of the mixture was continued for 6 h. The precipitate was then filtered off and dried over silica gel. The precipitate was dissolved in a mixture of pyridine and water (10 ml, 1:10 v/v) and stirred for 30 min. The solution was then filtered and left for crystallization, and a week later pale-violet block-shaped crystals of (I) were obtained. These were removed by filtration and dried over silica gel.

Crystal data

[Ni(C₁₁H₁₁N₄O₂S)₂(C₅H₅N)₂]·4C₅H₅N
M_r = 1059.91
Triclinic, $[P \overline 1]$
a = 9.9781 (2) Å
b = 10.0610 (2) Å
c = 13.2582 (4) Å
α = 89.744 (1)°
β = 82.238 (1)°
γ = 84.144 (1)°
V = 1311.85 (5) Å³
Z = 1
D_x = 1.342 Mg m⁻³
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 150 (2) K
Block, pale violet
0.18 × 0.16 × 0.06 mm

Data collection

Nonius KappaCCD area-detector diffractometer
ω scans
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.914, T_max = 0.970
24079 measured reflections
5955 independent reflections
4409 reflections with I > 2σ(I)
R_int = 0.159
θ_max = 27.5°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.143
S = 1.01
5955 reflections
332 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0633P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.50 e Å⁻³
Δρ_min = −1.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14B⋯N31	0.88	2.15	3.029 (3)	173
N14—H14A⋯N21	0.88	2.33	3.067 (3)	141

All H atoms were treated as riding atoms, with C—H = 0.95 Å and N—H = 0.88 Å, and with U_iso(H) = 1.2U_eq(C,N), or 1.5U_eq(C) for the methyl groups. The mosaicity of the compound was high, so R_int is 0.159. The deepest hole is located 0.90 Å from atom Ni1.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806038116/gd2006sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806038116/gd2006Isup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

trans-Dipyridinebis(sulfamerazinato)nickel(II)–pyridine (1/4) top

Crystal data top

[Ni(C₁₁H₁₁N₄O₂S)₂(C₅H₅N)₂]·4C₅H₅N	Z = 1
M_r = 1059.91	F(000) = 554
Triclinic, P1	D_x = 1.342 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9781 (2) Å	Cell parameters from 5955 reflections
b = 10.0610 (2) Å	θ = 2.9–27.5°
c = 13.2582 (4) Å	µ = 0.51 mm⁻¹
α = 89.744 (1)°	T = 150 K
β = 82.238 (1)°	Block, pale violet
γ = 84.144 (1)°	0.18 × 0.16 × 0.06 mm
V = 1311.85 (5) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	5955 independent reflections
Radiation source: fine-focus sealed tube	4409 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.159
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (Blessing, 1995)	h = −12→12
T_min = 0.914, T_max = 0.970	k = −13→13
24079 measured reflections	l = −17→17

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0633P)²] where P = (F_o² + 2F_c²)/3
5955 reflections	(Δ/σ)_max = 0.001
332 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −1.13 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.5000	0.5000	0.01886 (14)
S11	0.30067 (5)	0.23831 (5)	0.59767 (4)	0.01937 (16)
O11	0.16033 (14)	0.27796 (16)	0.63779 (13)	0.0278 (4)
O12	0.32609 (16)	0.18289 (16)	0.49588 (13)	0.0284 (4)
N11	0.39181 (17)	0.36225 (17)	0.59441 (15)	0.0192 (4)
N12	0.48660 (17)	0.52862 (18)	0.65801 (15)	0.0212 (4)
N13	0.34288 (18)	0.40324 (18)	0.77429 (15)	0.0229 (4)
N14	0.5484 (2)	−0.11971 (19)	0.89210 (16)	0.0283 (5)
H14A	0.5107	−0.1201	0.9560	0.034*
H14B	0.6271	−0.1666	0.8732	0.034*
C11	0.4035 (2)	0.4301 (2)	0.68068 (18)	0.0189 (5)
C12	0.5123 (2)	0.6010 (2)	0.7359 (2)	0.0267 (5)
H12	0.5694	0.6709	0.7229	0.032*
C13	0.4576 (3)	0.5769 (3)	0.8355 (2)	0.0329 (6)
H13	0.4779	0.6276	0.8907	0.039*
C14	0.3726 (2)	0.4762 (2)	0.85134 (19)	0.0279 (5)
C15	0.3652 (2)	0.1200 (2)	0.68170 (18)	0.0206 (5)
C16	0.3004 (2)	0.1118 (2)	0.78086 (19)	0.0234 (5)
H16	0.2157	0.1629	0.8012	0.028*
C17	0.3597 (2)	0.0289 (2)	0.85028 (19)	0.0248 (5)
H17	0.3146	0.0234	0.9178	0.030*
C18	0.4849 (2)	−0.0465 (2)	0.82228 (18)	0.0217 (5)
C19	0.5467 (2)	−0.0405 (2)	0.72041 (18)	0.0223 (5)
H19	0.6299	−0.0935	0.6988	0.027*
C20	0.4869 (2)	0.0422 (2)	0.65170 (18)	0.0221 (5)
H20	0.5296	0.0457	0.5834	0.026*
C111	0.3049 (3)	0.4424 (3)	0.9551 (2)	0.0413 (7)
H11A	0.2062	0.4623	0.9583	0.062*
H11B	0.3376	0.4956	1.0067	0.062*
H11C	0.3267	0.3471	0.9680	0.062*
N1	0.32122 (17)	0.62698 (18)	0.50398 (15)	0.0208 (4)
C1	0.2067 (2)	0.5820 (2)	0.47984 (19)	0.0260 (5)
H1	0.2090	0.4906	0.4614	0.031*
C2	0.0869 (2)	0.6628 (3)	0.4808 (2)	0.0320 (6)
H2	0.0080	0.6273	0.4640	0.038*
C3	0.0825 (2)	0.7957 (3)	0.5065 (2)	0.0364 (7)
H3	0.0008	0.8534	0.5073	0.044*
C4	0.1997 (2)	0.8441 (2)	0.5313 (2)	0.0327 (6)
H4	0.1996	0.9354	0.5493	0.039*
C5	0.3167 (2)	0.7563 (2)	0.52921 (19)	0.0248 (5)
H5	0.3967	0.7891	0.5464	0.030*
N21	0.3414 (2)	−0.2171 (2)	1.06138 (17)	0.0350 (5)
C21	0.3501 (2)	−0.2256 (2)	1.1609 (2)	0.0293 (6)
H21	0.4374	−0.2268	1.1820	0.035*
C22	0.2408 (3)	−0.2326 (3)	1.2341 (2)	0.0420 (7)
H22	0.2520	−0.2374	1.3041	0.050*
C23	0.1137 (3)	−0.2327 (3)	1.2042 (3)	0.0496 (8)
H23	0.0357	−0.2385	1.2531	0.059*
C24	0.1019 (3)	−0.2243 (3)	1.1022 (3)	0.0455 (7)
H24	0.0156	−0.2236	1.0794	0.055*
C25	0.2177 (3)	−0.2168 (3)	1.0338 (2)	0.0407 (7)
H25	0.2089	−0.2110	0.9634	0.049*
N31	0.8222 (2)	−0.2661 (2)	0.8118 (2)	0.0446 (6)
C31	0.8988 (3)	−0.1658 (3)	0.8132 (3)	0.0470 (8)
H31	0.8547	−0.0790	0.8299	0.056*
C32	1.0387 (3)	−0.1806 (3)	0.7917 (3)	0.0470 (8)
H32	1.0895	−0.1060	0.7942	0.056*
C33	1.1028 (3)	−0.3059 (3)	0.7665 (2)	0.0465 (8)
H33	1.1989	−0.3191	0.7504	0.056*
C34	1.0269 (3)	−0.4113 (3)	0.7651 (2)	0.0431 (7)
H34	1.0688	−0.4991	0.7490	0.052*
C35	0.8869 (3)	−0.3863 (3)	0.7877 (3)	0.0459 (7)
H35	0.8339	−0.4593	0.7858	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0162 (2)	0.0220 (2)	0.0185 (2)	−0.00321 (15)	−0.00240 (16)	0.00663 (16)
S11	0.0182 (3)	0.0227 (3)	0.0185 (3)	−0.0055 (2)	−0.0044 (2)	0.0051 (2)
O11	0.0174 (8)	0.0374 (10)	0.0296 (10)	−0.0051 (7)	−0.0052 (7)	0.0114 (8)
O12	0.0352 (9)	0.0302 (9)	0.0216 (9)	−0.0076 (7)	−0.0079 (7)	0.0003 (7)
N11	0.0180 (9)	0.0217 (9)	0.0186 (10)	−0.0056 (7)	−0.0027 (7)	0.0045 (7)
N12	0.0179 (9)	0.0235 (10)	0.0223 (11)	−0.0025 (7)	−0.0030 (8)	0.0045 (8)
N13	0.0255 (10)	0.0238 (10)	0.0187 (11)	−0.0006 (8)	−0.0021 (8)	0.0034 (8)
N14	0.0291 (11)	0.0323 (11)	0.0211 (11)	0.0028 (8)	0.0001 (9)	0.0103 (9)
C11	0.0158 (10)	0.0206 (11)	0.0199 (12)	0.0012 (8)	−0.0036 (9)	0.0046 (9)
C12	0.0285 (12)	0.0241 (12)	0.0302 (15)	−0.0061 (9)	−0.0111 (11)	0.0012 (10)
C13	0.0409 (15)	0.0335 (14)	0.0263 (15)	−0.0037 (11)	−0.0116 (12)	−0.0059 (11)
C14	0.0345 (13)	0.0292 (13)	0.0196 (13)	0.0022 (10)	−0.0064 (10)	0.0052 (10)
C15	0.0240 (11)	0.0177 (11)	0.0217 (13)	−0.0066 (8)	−0.0059 (9)	0.0049 (9)
C16	0.0188 (11)	0.0247 (12)	0.0262 (14)	−0.0042 (9)	0.0003 (10)	0.0035 (10)
C17	0.0252 (12)	0.0270 (12)	0.0210 (13)	−0.0059 (9)	0.0032 (10)	0.0074 (10)
C18	0.0243 (11)	0.0195 (11)	0.0219 (13)	−0.0062 (9)	−0.0022 (10)	0.0066 (9)
C19	0.0234 (11)	0.0203 (11)	0.0223 (13)	−0.0015 (9)	−0.0003 (9)	0.0031 (9)
C20	0.0270 (12)	0.0214 (11)	0.0179 (12)	−0.0072 (9)	0.0002 (9)	0.0035 (9)
C111	0.0581 (18)	0.0446 (16)	0.0199 (15)	−0.0034 (13)	−0.0016 (13)	0.0037 (12)
N1	0.0171 (9)	0.0264 (10)	0.0193 (10)	−0.0039 (7)	−0.0031 (8)	0.0102 (8)
C1	0.0237 (12)	0.0305 (13)	0.0252 (14)	−0.0070 (9)	−0.0060 (10)	0.0114 (10)
C2	0.0200 (12)	0.0444 (15)	0.0332 (15)	−0.0080 (10)	−0.0067 (10)	0.0186 (12)
C3	0.0261 (13)	0.0399 (15)	0.0393 (17)	0.0095 (11)	0.0000 (12)	0.0130 (12)
C4	0.0322 (13)	0.0274 (13)	0.0368 (16)	0.0007 (10)	−0.0015 (11)	0.0079 (11)
C5	0.0236 (12)	0.0275 (12)	0.0240 (13)	−0.0056 (9)	−0.0031 (10)	0.0059 (10)
N21	0.0359 (12)	0.0426 (13)	0.0261 (13)	−0.0107 (10)	0.0018 (10)	0.0032 (10)
C21	0.0317 (13)	0.0248 (12)	0.0315 (15)	−0.0045 (10)	−0.0036 (11)	0.0038 (11)
C22	0.0467 (17)	0.0500 (17)	0.0277 (16)	−0.0077 (13)	0.0025 (13)	0.0107 (13)
C23	0.0403 (17)	0.0557 (19)	0.049 (2)	−0.0130 (14)	0.0151 (15)	0.0062 (15)
C24	0.0313 (15)	0.0487 (18)	0.058 (2)	−0.0070 (12)	−0.0087 (14)	0.0030 (15)
C25	0.0471 (16)	0.0464 (17)	0.0304 (16)	−0.0096 (13)	−0.0091 (13)	0.0043 (13)
N31	0.0311 (12)	0.0375 (13)	0.0620 (18)	0.0026 (10)	0.0003 (12)	0.0074 (12)
C31	0.0454 (17)	0.0402 (16)	0.052 (2)	0.0053 (13)	−0.0037 (15)	0.0046 (14)
C32	0.0431 (17)	0.0534 (19)	0.048 (2)	−0.0146 (14)	−0.0109 (14)	0.0127 (15)
C33	0.0261 (14)	0.071 (2)	0.0389 (18)	0.0060 (14)	−0.0019 (12)	0.0175 (15)
C34	0.0381 (16)	0.0478 (17)	0.0383 (18)	0.0132 (13)	−0.0008 (13)	0.0035 (13)
C35	0.0433 (16)	0.0387 (16)	0.055 (2)	0.0002 (12)	−0.0061 (14)	0.0058 (14)

Geometric parameters (Å, º) top

Ni1—N1	2.0802 (18)	C111—H11C	0.9800
Ni1—N1ⁱ	2.0802 (18)	N1—C5	1.339 (3)
Ni1—N12ⁱ	2.100 (2)	N1—C1	1.348 (3)
Ni1—N12	2.100 (2)	C1—C2	1.374 (3)
Ni1—N11ⁱ	2.1396 (18)	C1—H1	0.9500
Ni1—N11	2.1396 (18)	C2—C3	1.376 (4)
S11—O12	1.4429 (18)	C2—H2	0.9500
S11—O11	1.4456 (16)	C3—C4	1.390 (4)
S11—N11	1.6137 (18)	C3—H3	0.9500
S11—C15	1.760 (2)	C4—C5	1.388 (3)
N11—C11	1.359 (3)	C4—H4	0.9500
N12—C12	1.334 (3)	C5—H5	0.9500
N12—C11	1.364 (3)	N21—C25	1.334 (4)
N13—C14	1.343 (3)	N21—C21	1.336 (3)
N13—C11	1.344 (3)	C21—C22	1.366 (4)
N14—C18	1.363 (3)	C21—H21	0.9500
N14—H14A	0.8800	C22—C23	1.379 (4)
N14—H14B	0.8800	C22—H22	0.9500
C12—C13	1.389 (4)	C23—C24	1.374 (5)
C12—H12	0.9500	C23—H23	0.9500
C13—C14	1.383 (4)	C24—C25	1.377 (4)
C13—H13	0.9500	C24—H24	0.9500
C14—C111	1.502 (4)	C25—H25	0.9500
C15—C20	1.387 (3)	N31—C31	1.328 (4)
C15—C16	1.390 (3)	N31—C35	1.330 (3)
C16—C17	1.390 (3)	C31—C32	1.380 (4)
C16—H16	0.9500	C31—H31	0.9500
C17—C18	1.399 (3)	C32—C33	1.376 (4)
C17—H17	0.9500	C32—H32	0.9500
C18—C19	1.411 (3)	C33—C34	1.366 (4)
C19—C20	1.384 (3)	C33—H33	0.9500
C19—H19	0.9500	C34—C35	1.386 (4)
C20—H20	0.9500	C34—H34	0.9500
C111—H11A	0.9800	C35—H35	0.9500
C111—H11B	0.9800

N1—Ni1—N1ⁱ	180.000 (1)	C19—C20—H20	119.7
N1—Ni1—N12ⁱ	92.01 (7)	C15—C20—H20	119.7
N1ⁱ—Ni1—N12ⁱ	87.99 (7)	C14—C111—H11A	109.5
N1—Ni1—N12	87.99 (7)	C14—C111—H11B	109.5
N1ⁱ—Ni1—N12	92.01 (7)	H11A—C111—H11B	109.5
N12ⁱ—Ni1—N12	180.000 (16)	C14—C111—H11C	109.5
N1—Ni1—N11ⁱ	90.39 (7)	H11A—C111—H11C	109.5
N1ⁱ—Ni1—N11ⁱ	89.61 (7)	H11B—C111—H11C	109.5
N12ⁱ—Ni1—N11ⁱ	63.36 (7)	C5—N1—C1	117.95 (19)
N12—Ni1—N11ⁱ	116.64 (7)	C5—N1—Ni1	121.08 (15)
N1—Ni1—N11	89.61 (7)	C1—N1—Ni1	120.96 (15)
N1ⁱ—Ni1—N11	90.39 (7)	N1—C1—C2	122.8 (2)
N12ⁱ—Ni1—N11	116.64 (7)	N1—C1—H1	118.6
N12—Ni1—N11	63.36 (7)	C2—C1—H1	118.6
N11ⁱ—Ni1—N11	180.00 (7)	C1—C2—C3	119.2 (2)
O12—S11—O11	116.66 (10)	C1—C2—H2	120.4
O12—S11—N11	104.95 (10)	C3—C2—H2	120.4
O11—S11—N11	111.73 (10)	C2—C3—C4	118.8 (2)
O12—S11—C15	108.81 (10)	C2—C3—H3	120.6
O11—S11—C15	107.21 (10)	C4—C3—H3	120.6
N11—S11—C15	107.11 (10)	C5—C4—C3	118.7 (2)
C11—N11—S11	121.07 (16)	C5—C4—H4	120.7
C11—N11—Ni1	92.33 (13)	C3—C4—H4	120.7
S11—N11—Ni1	146.00 (12)	N1—C5—C4	122.6 (2)
C12—N12—C11	116.8 (2)	N1—C5—H5	118.7
C12—N12—Ni1	148.88 (16)	C4—C5—H5	118.7
C11—N12—Ni1	93.91 (14)	C25—N21—C21	116.8 (2)
C14—N13—C11	116.5 (2)	N21—C21—C22	123.9 (3)
C18—N14—H14A	120.0	N21—C21—H21	118.0
C18—N14—H14B	120.0	C22—C21—H21	118.0
H14A—N14—H14B	120.0	C21—C22—C23	118.5 (3)
N13—C11—N11	125.0 (2)	C21—C22—H22	120.7
N13—C11—N12	125.2 (2)	C23—C22—H22	120.7
N11—C11—N12	109.76 (19)	C24—C23—C22	118.8 (3)
N12—C12—C13	121.6 (2)	C24—C23—H23	120.6
N12—C12—H12	119.2	C22—C23—H23	120.6
C13—C12—H12	119.2	C23—C24—C25	118.7 (3)
C14—C13—C12	117.6 (2)	C23—C24—H24	120.7
C14—C13—H13	121.2	C25—C24—H24	120.7
C12—C13—H13	121.2	N21—C25—C24	123.4 (3)
N13—C14—C13	122.1 (2)	N21—C25—H25	118.3
N13—C14—C111	115.2 (2)	C24—C25—H25	118.3
C13—C14—C111	122.7 (2)	C31—N31—C35	116.7 (2)
C20—C15—C16	119.7 (2)	N31—C31—C32	123.7 (3)
C20—C15—S11	119.92 (17)	N31—C31—H31	118.1
C16—C15—S11	120.13 (16)	C32—C31—H31	118.1
C17—C16—C15	120.0 (2)	C33—C32—C31	118.3 (3)
C17—C16—H16	120.0	C33—C32—H32	120.9
C15—C16—H16	120.0	C31—C32—H32	120.9
C16—C17—C18	121.0 (2)	C34—C33—C32	119.4 (3)
C16—C17—H17	119.5	C34—C33—H33	120.3
C18—C17—H17	119.5	C32—C33—H33	120.3
N14—C18—C17	121.1 (2)	C33—C34—C35	118.0 (3)
N14—C18—C19	120.7 (2)	C33—C34—H34	121.0
C17—C18—C19	118.2 (2)	C35—C34—H34	121.0
C20—C19—C18	120.4 (2)	N31—C35—C34	123.9 (3)
C20—C19—H19	119.8	N31—C35—H35	118.0
C18—C19—H19	119.8	C34—C35—H35	118.0
C19—C20—C15	120.6 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14B···N31	0.88	2.15	3.029 (3)	173
N14—H14A···N21	0.88	2.33	3.067 (3)	141

Acknowledgements

The authors acknowledge the School of Chemistry, Cardiff University, for support.

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