{2-[(2-Carbamothiol­ylhydrazin-1-yl­idene-κ2N1,S)meth­yl]-6-hy­droxy­phenolato-κO1}(triphenyl­phosphine-κP)nickel(II) chloride

Shawish, H.B.; Tan, K.W.; Maah, M.J.; Ng, S.W.

doi:10.1107/S1600536810031065

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1074

https://doi.org/10.1107/S1600536810031065

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{2-[(2-Carbamothiolylhydrazin-1-ylidene-κ²N¹,S)methyl]-6-hydroxyphenolato-κO¹}(triphenylphosphine-κP)nickel(II) chloride

Hana Bashir Shawish,^a Kong Wai Tan,^a M. Jamil Maah ^a ^* and Seik Weng Ng ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: mjamil@um.edu.my

(Received 29 July 2010; accepted 3 August 2010; online 11 August 2010)

The deprotonated Schiff base ligand in the title compound, [Ni(C₈H₈N₃O₂S)(C₁₈H₁₅P)]Cl, functions as an N,O,S-chelating anion to the phosphine-coordinated Ni atom, which exists in a distorted square-planar geometry. The hydroxy group forms an intramolecular O—H⋯O hydrogen bond. The two amino groups of the cation are hydrogen-bond donors to the chloride anion; the hydrogen bonds generate a chain structure running along the b axis.

Related literature

For the crystal structure of 2,3-dihydroxybenzaldehyde thiosemicarbazone hemihydrate, see: Swesi et al. (2006 ). For similar crystal structures containing a nickel(II) atom, see: García-Reynaldos et al. (2007 ).

Experimental

Crystal data

[Ni(C₈H₈N₃O₂S)(C₁₈H₁₅P)]Cl
M_r = 566.66
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.7902 (4) Å
b = 14.6791 (7) Å
c = 21.7410 (11) Å
V = 2486.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.07 mm⁻¹
T = 100 K
0.35 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.707, T_max = 0.815
24072 measured reflections
5703 independent reflections
5490 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.054
S = 1.02
5703 reflections
332 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 2468 Friedel pairs
Flack parameter: −0.011 (7)

Table 1
Selected bond lengths (Å)

Ni1—O1	1.847 (1)
Ni1—N1	1.897 (1)
Ni1—P1	2.1998 (4)
Ni1—S1	2.1416 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1	0.84 (1)	2.11 (3)	2.636 (2)	120 (2)
N2—H2⋯Cl1	0.86 (1)	2.17 (1)	3.016 (2)	167 (2)
N3—H3⋯Cl1ⁱ	0.85 (1)	2.46 (1)	3.275 (2)	161 (2)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810031065/bt5315sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031065/bt5315Isup2.hkl

checkCIF report

Comment top

Substituted 2-hydroxybenzaldehyde thiosemicarbazones are generally doubly-deprotonated in their nickel complexes, the dianion chelating to the metal atom through its nitrogen, oxygen and sulfur atoms. However, with the triphenylphosphine adducts of nickel 2-hydroxybenzaldehyde thiosemicarbonates, the Schiff base is only mono-deprotonated; the positive charge of the cation is balanced by a chloride counterion (García-Reynaldos et al., 2007). The reaction of the 3-hydroxy substituted Schiff base with nickel chloride affords the analogous salt, 3-hydroxy-2-oxidobenzaldehydethiosemicarbazone)(triphenylphosphine)nickel(II) chloride (Scheme I). The coordination environment of nickel is a square plane made up of nitrogen, oxygen, phosphorus and sulfur atoms (Fig. 1). Adjacent ions are linked by N–H···Cl hydrogen bonds to generate a chain structure (Fig. 2).

Related literature top

For the crystal structure of 2,3-dihydroxybenzaldehyde thiosemicarbazone hemihydrate, see: Swesi et al. (2006). For similar nickel crystal structures, see: García-Reynaldos et al. (2007).

Experimental top

2,3-Dihydroxybenzaldehyde thiosemicarbazone hemihydrate (Swesi et al., 2006) (0.22 g, 1 mmol), triphenylphosphine (0.26, 1 mmol) and nickel chloride (0.13 g, 1 mmol) were heated in a methanol/ethanol (50 ml) for an hour. The brown solution was then set aside for the growth of crystals.

Structure description top

For the crystal structure of 2,3-dihydroxybenzaldehyde thiosemicarbazone hemihydrate, see: Swesi et al. (2006). For similar nickel crystal structures, see: García-Reynaldos et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain motif.

{2-[(2-Carbamothiolylhydrazin-1-ylidene-κ²N¹,S)methyl]-6- hydroxyphenolato-κO¹}(triphenylphosphine-κP)nickel(II) chloride top

Crystal data top

[Ni(C₈H₈N₃O₂S)(C₁₈H₁₅P)]Cl	F(000) = 1168
M_r = 566.66	D_x = 1.514 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9879 reflections
a = 7.7902 (4) Å	θ = 2.8–28.3°
b = 14.6791 (7) Å	µ = 1.07 mm⁻¹
c = 21.7410 (11) Å	T = 100 K
V = 2486.2 (2) Å³	Block, brown
Z = 4	0.35 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	5703 independent reflections
Radiation source: fine-focus sealed tube	5490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.707, T_max = 0.815	k = −19→19
24072 measured reflections	l = −28→28

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.054	w = 1/[σ²(F_o²) + (0.032P)² + 0.4343P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5703 reflections	Δρ_max = 0.29 e Å⁻³
332 parameters	Δρ_min = −0.21 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 2468 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.011 (7)

Crystal data top

[Ni(C₈H₈N₃O₂S)(C₁₈H₁₅P)]Cl	V = 2486.2 (2) Å³
M_r = 566.66	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.7902 (4) Å	µ = 1.07 mm⁻¹
b = 14.6791 (7) Å	T = 100 K
c = 21.7410 (11) Å	0.35 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	5703 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5490 reflections with I > 2σ(I)
T_min = 0.707, T_max = 0.815	R_int = 0.028
24072 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.054	Δρ_max = 0.29 e Å⁻³
S = 1.02	Δρ_min = −0.21 e Å⁻³
5703 reflections	Absolute structure: Flack (1983), 2468 Friedel pairs
332 parameters	Absolute structure parameter: −0.011 (7)
4 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	1.20955 (2)	0.505537 (13)	0.401439 (8)	0.01255 (5)
Cl1	1.73655 (6)	0.39315 (3)	0.57199 (2)	0.02565 (10)
S1	1.17398 (5)	0.36636 (3)	0.42809 (2)	0.01724 (9)
P1	1.03089 (5)	0.49177 (3)	0.323635 (17)	0.01239 (8)
O1	1.24123 (15)	0.62350 (7)	0.37422 (5)	0.0187 (2)
O2	1.19946 (19)	0.78945 (8)	0.33035 (6)	0.0287 (3)
N1	1.37566 (17)	0.51529 (9)	0.46493 (6)	0.0149 (3)
N2	1.42733 (19)	0.43510 (10)	0.49349 (7)	0.0185 (3)
N3	1.3866 (2)	0.28145 (11)	0.50486 (8)	0.0241 (3)
C1	1.31436 (19)	0.68926 (10)	0.40627 (7)	0.0142 (3)
C2	1.2891 (2)	0.77878 (11)	0.38354 (8)	0.0176 (3)
C3	1.3508 (2)	0.85370 (11)	0.41499 (8)	0.0190 (3)
H3A	1.3282	0.9134	0.4002	0.023*
C4	1.4466 (3)	0.84135 (12)	0.46872 (8)	0.0240 (4)
H4A	1.4888	0.8928	0.4904	0.029*
C5	1.4800 (2)	0.75525 (13)	0.49031 (8)	0.0214 (4)
H5	1.5483	0.7476	0.5261	0.026*
C6	1.4135 (2)	0.67776 (11)	0.45966 (7)	0.0155 (3)
C7	1.4512 (2)	0.58908 (11)	0.48329 (8)	0.0170 (3)
H7	1.5366	0.5840	0.5143	0.020*
C8	1.3423 (2)	0.35953 (11)	0.47936 (8)	0.0178 (3)
C9	0.8816 (2)	0.39672 (11)	0.32651 (8)	0.0148 (3)
C10	0.9418 (2)	0.30780 (11)	0.31890 (8)	0.0185 (3)
H10	1.0577	0.2979	0.3071	0.022*
C11	0.8346 (2)	0.23421 (12)	0.32831 (8)	0.0217 (4)
H11	0.8771	0.1740	0.3234	0.026*
C12	0.6650 (2)	0.24820 (12)	0.34488 (8)	0.0233 (4)
H12	0.5919	0.1977	0.3525	0.028*
C13	0.6022 (2)	0.33652 (13)	0.35029 (9)	0.0243 (4)
H13	0.4846	0.3460	0.3599	0.029*
C14	0.7092 (2)	0.41065 (11)	0.34182 (8)	0.0201 (3)
H14	0.6658	0.4708	0.3464	0.024*
C15	1.1516 (2)	0.47966 (10)	0.25280 (7)	0.0137 (3)
C16	1.0725 (2)	0.44338 (11)	0.20070 (8)	0.0186 (3)
H16	0.9612	0.4172	0.2037	0.022*
C17	1.1566 (3)	0.44565 (12)	0.14459 (8)	0.0243 (4)
H17	1.1017	0.4219	0.1090	0.029*
C18	1.3205 (2)	0.48240 (12)	0.13991 (8)	0.0235 (4)
H18	1.3763	0.4851	0.1011	0.028*
C19	1.4021 (2)	0.51502 (12)	0.19194 (8)	0.0216 (3)
H19	1.5158	0.5380	0.1891	0.026*
C20	1.3182 (2)	0.51420 (11)	0.24836 (7)	0.0179 (3)
H20	1.3742	0.5372	0.2839	0.021*
C21	0.8940 (2)	0.59074 (10)	0.31157 (8)	0.0137 (3)
C22	0.8430 (2)	0.64323 (11)	0.36199 (8)	0.0174 (3)
H22	0.8851	0.6291	0.4019	0.021*
C23	0.7311 (2)	0.71597 (12)	0.35396 (8)	0.0205 (4)
H23	0.6977	0.7517	0.3884	0.025*
C24	0.6678 (2)	0.73673 (11)	0.29596 (8)	0.0212 (4)
H24	0.5907	0.7862	0.2907	0.025*
C25	0.7181 (2)	0.68466 (11)	0.24565 (8)	0.0188 (3)
H25	0.6748	0.6986	0.2059	0.023*
C26	0.8313 (2)	0.61229 (11)	0.25321 (8)	0.0159 (3)
H26	0.8661	0.5774	0.2186	0.019*
H1	1.167 (4)	0.7369 (10)	0.3206 (13)	0.066 (9)*
H2	1.5176 (19)	0.4328 (14)	0.5163 (8)	0.024 (5)*
H3	1.345 (3)	0.2305 (10)	0.4935 (10)	0.034 (6)*
H4	1.470 (2)	0.2785 (16)	0.5305 (9)	0.041 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01379 (9)	0.01142 (9)	0.01246 (9)	0.00043 (8)	−0.00276 (7)	0.00082 (8)
Cl1	0.0260 (2)	0.0220 (2)	0.0290 (2)	0.00243 (16)	−0.01141 (18)	−0.00098 (17)
S1	0.01566 (18)	0.01508 (18)	0.0210 (2)	−0.00126 (15)	−0.00263 (16)	0.00560 (15)
P1	0.01259 (17)	0.01158 (18)	0.01300 (18)	−0.00005 (16)	−0.00142 (13)	−0.00061 (15)
O1	0.0255 (6)	0.0114 (5)	0.0190 (6)	−0.0023 (5)	−0.0093 (5)	0.0008 (4)
O2	0.0330 (7)	0.0164 (6)	0.0368 (7)	−0.0018 (6)	−0.0196 (6)	0.0063 (5)
N1	0.0150 (6)	0.0171 (7)	0.0126 (6)	0.0033 (5)	−0.0011 (5)	0.0028 (5)
N2	0.0188 (7)	0.0198 (7)	0.0168 (7)	0.0026 (6)	−0.0063 (6)	0.0040 (6)
N3	0.0264 (9)	0.0198 (8)	0.0261 (8)	0.0011 (6)	−0.0061 (7)	0.0075 (7)
C1	0.0125 (7)	0.0153 (7)	0.0148 (7)	−0.0003 (6)	0.0006 (6)	−0.0014 (6)
C2	0.0137 (7)	0.0168 (7)	0.0223 (8)	−0.0001 (6)	−0.0007 (7)	−0.0003 (6)
C3	0.0189 (8)	0.0138 (7)	0.0242 (9)	−0.0015 (6)	0.0055 (7)	−0.0019 (6)
C4	0.0313 (10)	0.0225 (9)	0.0183 (9)	−0.0107 (8)	0.0045 (7)	−0.0054 (7)
C5	0.0259 (9)	0.0244 (8)	0.0140 (8)	−0.0078 (7)	−0.0005 (7)	−0.0015 (7)
C6	0.0142 (7)	0.0183 (8)	0.0139 (8)	−0.0018 (6)	0.0002 (6)	−0.0011 (6)
C7	0.0164 (8)	0.0239 (8)	0.0108 (7)	−0.0009 (6)	−0.0014 (6)	0.0004 (6)
C8	0.0182 (8)	0.0186 (8)	0.0166 (8)	0.0013 (6)	0.0009 (6)	0.0041 (6)
C9	0.0147 (7)	0.0150 (7)	0.0146 (8)	−0.0040 (6)	−0.0027 (6)	−0.0019 (6)
C10	0.0165 (8)	0.0180 (8)	0.0209 (9)	0.0008 (7)	−0.0012 (7)	−0.0018 (6)
C11	0.0238 (9)	0.0143 (8)	0.0268 (9)	−0.0003 (7)	−0.0037 (8)	−0.0026 (7)
C12	0.0225 (9)	0.0226 (9)	0.0249 (9)	−0.0088 (7)	−0.0005 (7)	0.0014 (7)
C13	0.0149 (8)	0.0270 (9)	0.0312 (10)	−0.0025 (7)	0.0042 (7)	−0.0028 (8)
C14	0.0184 (8)	0.0180 (8)	0.0239 (9)	0.0020 (7)	0.0002 (7)	−0.0032 (6)
C15	0.0156 (7)	0.0109 (7)	0.0147 (7)	0.0024 (5)	−0.0006 (6)	−0.0004 (5)
C16	0.0182 (8)	0.0184 (8)	0.0191 (8)	0.0007 (6)	−0.0012 (7)	−0.0032 (6)
C17	0.0301 (10)	0.0252 (9)	0.0175 (8)	0.0055 (8)	−0.0033 (7)	−0.0079 (7)
C18	0.0286 (9)	0.0234 (9)	0.0187 (8)	0.0102 (7)	0.0080 (7)	−0.0007 (6)
C19	0.0176 (8)	0.0186 (8)	0.0286 (9)	0.0015 (7)	0.0051 (7)	0.0007 (7)
C20	0.0180 (8)	0.0157 (7)	0.0200 (7)	0.0011 (6)	−0.0008 (6)	−0.0024 (6)
C21	0.0117 (7)	0.0115 (7)	0.0178 (8)	−0.0005 (6)	−0.0003 (6)	0.0005 (6)
C22	0.0187 (8)	0.0165 (8)	0.0170 (8)	−0.0006 (6)	0.0004 (6)	−0.0002 (6)
C23	0.0200 (9)	0.0176 (7)	0.0237 (9)	0.0017 (7)	0.0073 (7)	−0.0015 (7)
C24	0.0147 (8)	0.0142 (7)	0.0346 (10)	0.0025 (6)	0.0032 (7)	0.0041 (7)
C25	0.0157 (8)	0.0179 (7)	0.0228 (8)	−0.0020 (7)	−0.0031 (7)	0.0041 (6)
C26	0.0156 (7)	0.0154 (7)	0.0169 (7)	−0.0007 (6)	−0.0019 (6)	−0.0001 (6)

Geometric parameters (Å, º) top

Ni1—O1	1.847 (1)	C10—C11	1.381 (2)
Ni1—N1	1.897 (1)	C10—H10	0.9500
Ni1—P1	2.1998 (4)	C11—C12	1.384 (3)
Ni1—S1	2.1416 (4)	C11—H11	0.9500
S1—C8	1.7240 (17)	C12—C13	1.391 (3)
P1—C15	1.8134 (16)	C12—H12	0.9500
P1—C9	1.8176 (17)	C13—C14	1.383 (2)
P1—C21	1.8211 (16)	C13—H13	0.9500
O1—C1	1.3198 (18)	C14—H14	0.9500
O2—C2	1.360 (2)	C15—C16	1.395 (2)
O2—H1	0.839 (10)	C15—C20	1.396 (2)
N1—C7	1.296 (2)	C16—C17	1.385 (2)
N1—N2	1.3904 (19)	C16—H16	0.9500
N2—C8	1.328 (2)	C17—C18	1.390 (3)
N2—H2	0.861 (9)	C17—H17	0.9500
N3—C8	1.319 (2)	C18—C19	1.383 (3)
N3—H3	0.850 (10)	C18—H18	0.9500
N3—H4	0.857 (10)	C19—C20	1.390 (2)
C1—C6	1.405 (2)	C19—H19	0.9500
C1—C2	1.418 (2)	C20—H20	0.9500
C2—C3	1.381 (2)	C21—C26	1.396 (2)
C3—C4	1.398 (2)	C21—C22	1.397 (2)
C3—H3A	0.9500	C22—C23	1.390 (2)
C4—C5	1.373 (3)	C22—H22	0.9500
C4—H4A	0.9500	C23—C24	1.388 (3)
C5—C6	1.416 (2)	C23—H23	0.9500
C5—H5	0.9500	C24—C25	1.391 (2)
C6—C7	1.430 (2)	C24—H24	0.9500
C7—H7	0.9500	C25—C26	1.391 (2)
C9—C10	1.397 (2)	C25—H25	0.9500
C9—C14	1.399 (2)	C26—H26	0.9500

O1—Ni1—N1	94.09 (5)	C11—C10—C9	120.68 (16)
O1—Ni1—S1	176.98 (4)	C11—C10—H10	119.7
N1—Ni1—S1	87.90 (4)	C9—C10—H10	119.7
O1—Ni1—P1	85.66 (4)	C10—C11—C12	119.98 (16)
N1—Ni1—P1	176.19 (4)	C10—C11—H11	120.0
S1—Ni1—P1	92.207 (17)	C12—C11—H11	120.0
C8—S1—Ni1	97.58 (6)	C11—C12—C13	119.74 (17)
C15—P1—C9	106.62 (7)	C11—C12—H12	120.1
C15—P1—C21	105.05 (7)	C13—C12—H12	120.1
C9—P1—C21	104.04 (7)	C14—C13—C12	120.68 (17)
C15—P1—Ni1	109.50 (5)	C14—C13—H13	119.7
C9—P1—Ni1	116.68 (5)	C12—C13—H13	119.7
C21—P1—Ni1	114.07 (5)	C13—C14—C9	119.68 (16)
C1—O1—Ni1	125.06 (10)	C13—C14—H14	120.2
C2—O2—H1	105 (2)	C9—C14—H14	120.2
C7—N1—N2	116.02 (13)	C16—C15—C20	119.55 (15)
C7—N1—Ni1	126.64 (12)	C16—C15—P1	119.83 (12)
N2—N1—Ni1	117.29 (10)	C20—C15—P1	120.34 (12)
C8—N2—N1	117.35 (13)	C17—C16—C15	119.78 (16)
C8—N2—H2	120.6 (14)	C17—C16—H16	120.1
N1—N2—H2	121.7 (14)	C15—C16—H16	120.1
C8—N3—H3	122.9 (16)	C16—C17—C18	120.56 (16)
C8—N3—H4	121.0 (17)	C16—C17—H17	119.7
H3—N3—H4	115 (2)	C18—C17—H17	119.7
O1—C1—C6	125.86 (14)	C19—C18—C17	119.80 (16)
O1—C1—C2	115.72 (14)	C19—C18—H18	120.1
C6—C1—C2	118.42 (14)	C17—C18—H18	120.1
O2—C2—C3	120.53 (15)	C18—C19—C20	120.15 (16)
O2—C2—C1	118.33 (14)	C18—C19—H19	119.9
C3—C2—C1	121.13 (15)	C20—C19—H19	119.9
C2—C3—C4	119.75 (16)	C19—C20—C15	120.09 (15)
C2—C3—H3A	120.1	C19—C20—H20	120.0
C4—C3—H3A	120.1	C15—C20—H20	120.0
C5—C4—C3	120.41 (16)	C26—C21—C22	119.25 (15)
C5—C4—H4A	119.8	C26—C21—P1	121.10 (12)
C3—C4—H4A	119.8	C22—C21—P1	119.55 (13)
C4—C5—C6	120.62 (16)	C23—C22—C21	120.22 (15)
C4—C5—H5	119.7	C23—C22—H22	119.9
C6—C5—H5	119.7	C21—C22—H22	119.9
C1—C6—C5	119.56 (15)	C24—C23—C22	120.38 (16)
C1—C6—C7	121.27 (15)	C24—C23—H23	119.8
C5—C6—C7	119.17 (15)	C22—C23—H23	119.8
N1—C7—C6	123.88 (15)	C23—C24—C25	119.62 (15)
N1—C7—H7	118.1	C23—C24—H24	120.2
C6—C7—H7	118.1	C25—C24—H24	120.2
N3—C8—N2	119.87 (16)	C24—C25—C26	120.36 (16)
N3—C8—S1	121.41 (14)	C24—C25—H25	119.8
N2—C8—S1	118.71 (12)	C26—C25—H25	119.8
C10—C9—C14	119.17 (16)	C25—C26—C21	120.16 (16)
C10—C9—P1	119.88 (13)	C25—C26—H26	119.9
C14—C9—P1	120.69 (13)	C21—C26—H26	119.9

N1—Ni1—S1—C8	−8.42 (7)	C21—P1—C9—C10	162.94 (14)
P1—Ni1—S1—C8	167.76 (6)	Ni1—P1—C9—C10	−70.45 (15)
O1—Ni1—P1—C15	76.20 (7)	C15—P1—C9—C14	−133.63 (14)
S1—Ni1—P1—C15	−101.67 (5)	C21—P1—C9—C14	−22.91 (16)
O1—Ni1—P1—C9	−162.64 (7)	Ni1—P1—C9—C14	103.70 (14)
S1—Ni1—P1—C9	19.49 (6)	C14—C9—C10—C11	−2.2 (3)
O1—Ni1—P1—C21	−41.18 (7)	P1—C9—C10—C11	172.08 (13)
S1—Ni1—P1—C21	140.95 (6)	C9—C10—C11—C12	0.6 (3)
N1—Ni1—O1—C1	−18.45 (13)	C10—C11—C12—C13	1.8 (3)
P1—Ni1—O1—C1	165.37 (13)	C11—C12—C13—C14	−2.7 (3)
O1—Ni1—N1—C7	9.88 (14)	C12—C13—C14—C9	1.2 (3)
S1—Ni1—N1—C7	−172.40 (14)	C10—C9—C14—C13	1.2 (3)
O1—Ni1—N1—N2	−167.58 (11)	P1—C9—C14—C13	−172.98 (14)
S1—Ni1—N1—N2	10.15 (11)	C9—P1—C15—C16	33.87 (15)
C7—N1—N2—C8	174.49 (15)	C21—P1—C15—C16	−76.15 (14)
Ni1—N1—N2—C8	−7.78 (19)	Ni1—P1—C15—C16	160.94 (11)
Ni1—O1—C1—C6	15.1 (2)	C9—P1—C15—C20	−152.17 (12)
Ni1—O1—C1—C2	−165.23 (11)	C21—P1—C15—C20	97.81 (13)
O1—C1—C2—O2	−2.6 (2)	Ni1—P1—C15—C20	−25.10 (13)
C6—C1—C2—O2	177.13 (15)	C20—C15—C16—C17	−2.9 (2)
O1—C1—C2—C3	176.23 (15)	P1—C15—C16—C17	171.13 (13)
C6—C1—C2—C3	−4.0 (2)	C15—C16—C17—C18	1.1 (3)
O2—C2—C3—C4	−178.30 (16)	C16—C17—C18—C19	1.6 (3)
C1—C2—C3—C4	2.9 (3)	C17—C18—C19—C20	−2.4 (3)
C2—C3—C4—C5	0.2 (3)	C18—C19—C20—C15	0.6 (2)
C3—C4—C5—C6	−2.0 (3)	C16—C15—C20—C19	2.0 (2)
O1—C1—C6—C5	−178.13 (16)	P1—C15—C20—C19	−171.93 (12)
C2—C1—C6—C5	2.2 (2)	C15—P1—C21—C26	31.84 (15)
O1—C1—C6—C7	2.8 (3)	C9—P1—C21—C26	−80.02 (14)
C2—C1—C6—C7	−176.86 (16)	Ni1—P1—C21—C26	151.76 (12)
C4—C5—C6—C1	0.8 (3)	C15—P1—C21—C22	−151.69 (13)
C4—C5—C6—C7	179.84 (17)	C9—P1—C21—C22	96.45 (14)
N2—N1—C7—C6	−179.36 (15)	Ni1—P1—C21—C22	−31.77 (14)
Ni1—N1—C7—C6	3.2 (2)	C26—C21—C22—C23	0.1 (2)
C1—C6—C7—N1	−12.3 (3)	P1—C21—C22—C23	−176.48 (13)
C5—C6—C7—N1	168.62 (16)	C21—C22—C23—C24	0.5 (3)
N1—N2—C8—N3	179.62 (15)	C22—C23—C24—C25	−0.5 (3)
N1—N2—C8—S1	−0.9 (2)	C23—C24—C25—C26	−0.2 (3)
Ni1—S1—C8—N3	−173.17 (14)	C24—C25—C26—C21	0.7 (2)
Ni1—S1—C8—N2	7.37 (14)	C22—C21—C26—C25	−0.7 (2)
C15—P1—C9—C10	52.22 (15)	P1—C21—C26—C25	175.82 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1	0.84 (1)	2.11 (3)	2.636 (2)	120 (2)
N2—H2···Cl1	0.86 (1)	2.17 (1)	3.016 (2)	167 (2)
N3—H3···Cl1ⁱ	0.85 (1)	2.46 (1)	3.275 (2)	161 (2)

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₈N₃O₂S)(C₁₈H₁₅P)]Cl
M_r	566.66
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.7902 (4), 14.6791 (7), 21.7410 (11)
V (Å³)	2486.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.07
Crystal size (mm)	0.35 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.707, 0.815
No. of measured, independent and observed [I > 2σ(I)] reflections	24072, 5703, 5490
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.054, 1.02
No. of reflections	5703
No. of parameters	332
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.21
Absolute structure	Flack (1983), 2468 Friedel pairs
Absolute structure parameter	−0.011 (7)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ni1—O1	1.847 (1)	Ni1—P1	2.1998 (4)
Ni1—N1	1.897 (1)	Ni1—S1	2.1416 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1	0.84 (1)	2.11 (3)	2.636 (2)	120 (2)
N2—H2···Cl1	0.86 (1)	2.17 (1)	3.016 (2)	167 (2)
N3—H3···Cl1ⁱ	0.85 (1)	2.46 (1)	3.275 (2)	161 (2)

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Acknowledgements

We thank the University of Malaya (PS354/2009) and MOHE (FRGS-FP001/2009) for supporting this study. HBS also thanks the Libyan People's Bureau in Malaysia for a scholarship.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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García-Reynaldos, P. X., Hernández-Ortega, S., Toscano, R. A. & Valdés-Martínez, J. (2007). Supramol. Chem. 19, 613–619. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
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