(6-Hydroxy-2-{[2-(N-methyl­carbamo­thiol­yl)hydrazin-1-yl­idene-κ2N1,S]meth­yl}­phenolato-κO1)(triphenyl­phosphane-κP)nickel(II) chloride

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

doi:10.1107/S1600536810039292

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1366

https://doi.org/10.1107/S1600536810039292

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(6-Hydroxy-2-{[2-(N-methylcarbamothiolyl)hydrazin-1-ylidene-κ²N¹,S]methyl}phenolato-κO¹)(triphenylphosphane-κP)nickel(II) chloride

Hana Bashir Shawish,^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 September 2010; accepted 1 October 2010; online 9 October 2010)

The deprotonated Schiff base ligand in the title salt, [Ni(C₉H₁₀N₃O₂S)(C₁₈H₁₅P)]Cl, functions as an N,O,S-chelating anion to the phosphine-coordinated nickel(II) 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

The only report of this Schiff base is that of a study of its organotin derivatives; see: Swesi et al. (2007 ). For a related nickel Schiff-base adduct of triphenylphosphine, see: Shawish et al. (2010 ).

Experimental

Crystal data

[Ni(C₉H₁₀N₃O₂S)(C₁₈H₁₅P)]Cl
M_r = 580.69
Monoclinic, P 2₁ /n
a = 15.7781 (15) Å
b = 10.6306 (10) Å
c = 17.0020 (15) Å
β = 113.961 (1)°
V = 2606.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.785, T_max = 0.951
23696 measured reflections
5971 independent reflections
4428 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.177
S = 1.05
5971 reflections
338 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.60 e Å⁻³
Δρ_min = −1.06 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N1	1.895 (3)
Ni1—O1	1.849 (2)
Ni1—P1	2.216 (1)
Ni1—S1	2.150 (1)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1	0.84 (5)	2.10 (4)	2.640 (4)	122 (4)
N2—H2N⋯Cl1	0.86 (4)	2.19 (4)	3.046 (3)	172 (5)
N3—H3N⋯Cl1ⁱ	0.86 (4)	2.28 (4)	3.111 (3)	164 (5)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536810039292/xu5041sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039292/xu5041Isup2.hkl

checkCIF report

Related literature top

The only report of the Schiff base is that of a study of its organotin derivatives; see: Swesi et al. (2007). For a related nickel Schiff-base adduct of triphenylphosphine, see: Shawish et al. (2010).

Experimental top

2,3-Dihydroxybenzaldehyde 4-methylthiosemicarbazone hemihydrate (Swesi et al., 2007) (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

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. Thermal ellipsoid plot (Barbour, 2001) of Ni(C₉H₁₀N₃O₂S)(C₁₈H₁₅P)^.Cl at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain motif.

(6-Hydroxy-2-{[2-(N-methylcarbamothiolyl)hydrazin-1-ylidene- κ²N¹,S]methyl}phenolato-κO¹)(triphenylphosphane- κP)nickel(II) chloride top

Crystal data top

[Ni(C₉H₁₀N₃O₂S)(C₁₈H₁₅P)]Cl	F(000) = 1200
M_r = 580.69	D_x = 1.480 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3978 reflections
a = 15.7781 (15) Å	θ = 2.3–27.6°
b = 10.6306 (10) Å	µ = 1.02 mm⁻¹
c = 17.0020 (15) Å	T = 100 K
β = 113.961 (1)°	Triangular block, brown
V = 2606.0 (4) Å³	0.25 × 0.15 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5971 independent reflections
Radiation source: fine-focus sealed tube	4428 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
T_min = 0.785, T_max = 0.951	k = −13→13
23696 measured reflections	l = −22→21

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.1036P)² + 0.1986P] where P = (F_o² + 2F_c²)/3
5971 reflections	(Δ/σ)_max = 0.001
338 parameters	Δρ_max = 1.60 e Å⁻³
3 restraints	Δρ_min = −1.06 e Å⁻³

Crystal data top

[Ni(C₉H₁₀N₃O₂S)(C₁₈H₁₅P)]Cl	V = 2606.0 (4) Å³
M_r = 580.69	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.7781 (15) Å	µ = 1.02 mm⁻¹
b = 10.6306 (10) Å	T = 100 K
c = 17.0020 (15) Å	0.25 × 0.15 × 0.05 mm
β = 113.961 (1)°

Data collection top

Bruker SMART APEX diffractometer	5971 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4428 reflections with I > 2σ(I)
T_min = 0.785, T_max = 0.951	R_int = 0.096
23696 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	3 restraints
wR(F²) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 1.60 e Å⁻³
5971 reflections	Δρ_min = −1.06 e Å⁻³
338 parameters

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

	x	y	z	U_iso*/U_eq
Ni1	0.41946 (3)	0.54484 (4)	0.60995 (3)	0.01585 (16)
Cl1	0.66145 (6)	0.16147 (8)	0.61950 (6)	0.0205 (2)
S1	0.55028 (6)	0.62917 (8)	0.68921 (6)	0.0200 (2)
P1	0.34464 (6)	0.68668 (9)	0.65317 (6)	0.0162 (2)
O1	0.30452 (17)	0.4812 (2)	0.53950 (17)	0.0194 (6)
O2	0.12753 (18)	0.4272 (3)	0.45169 (19)	0.0268 (6)
H2O	0.159 (3)	0.481 (4)	0.488 (3)	0.047 (16)*
N1	0.4861 (2)	0.4179 (3)	0.58096 (19)	0.0170 (6)
N2	0.5828 (2)	0.4237 (3)	0.6177 (2)	0.0183 (6)
H2N	0.609 (3)	0.353 (3)	0.616 (4)	0.060 (18)*
N3	0.7127 (2)	0.5302 (3)	0.7092 (2)	0.0194 (7)
H3N	0.739 (3)	0.577 (4)	0.753 (2)	0.042 (15)*
C1	0.2882 (2)	0.3775 (3)	0.4925 (2)	0.0185 (7)
C2	0.1937 (2)	0.3465 (3)	0.4458 (2)	0.0194 (8)
C3	0.1667 (3)	0.2402 (4)	0.3963 (3)	0.0226 (8)
H3	0.1027	0.2211	0.3665	0.027*
C4	0.2342 (3)	0.1597 (3)	0.3899 (3)	0.0230 (8)
H4	0.2156	0.0854	0.3561	0.028*
C5	0.3271 (3)	0.1876 (3)	0.4321 (2)	0.0208 (8)
H5	0.3723	0.1340	0.4262	0.025*
C6	0.3553 (2)	0.2978 (3)	0.4851 (2)	0.0178 (7)
C7	0.4516 (3)	0.3234 (3)	0.5293 (2)	0.0187 (7)
H7	0.4938	0.2674	0.5205	0.022*
C8	0.6223 (2)	0.5188 (3)	0.6721 (2)	0.0180 (7)
C9	0.7785 (3)	0.4427 (4)	0.6972 (3)	0.0231 (8)
H9A	0.8413	0.4775	0.7242	0.035*
H9B	0.7618	0.4306	0.6356	0.035*
H9C	0.7763	0.3617	0.7238	0.035*
C10	0.3352 (3)	0.6414 (3)	0.7521 (2)	0.0197 (8)
C11	0.3826 (3)	0.5350 (3)	0.7982 (3)	0.0236 (8)
H11	0.4201	0.4865	0.7778	0.028*
C12	0.3746 (3)	0.5011 (4)	0.8736 (3)	0.0325 (10)
H12	0.4075	0.4300	0.9052	0.039*
C13	0.3190 (3)	0.5697 (4)	0.9031 (3)	0.0342 (10)
H13	0.3130	0.5445	0.9542	0.041*
C14	0.2719 (3)	0.6755 (4)	0.8584 (3)	0.0299 (9)
H14	0.2345	0.7233	0.8793	0.036*
C15	0.2798 (3)	0.7105 (4)	0.7838 (3)	0.0242 (8)
H15	0.2473	0.7825	0.7532	0.029*
C16	0.3967 (2)	0.8436 (3)	0.6713 (2)	0.0187 (7)
C17	0.4240 (2)	0.8905 (4)	0.6092 (2)	0.0208 (8)
H17	0.4146	0.8416	0.5596	0.025*
C18	0.4653 (3)	1.0087 (4)	0.6187 (3)	0.0229 (8)
H18	0.4827	1.0410	0.5753	0.028*
C19	0.4808 (3)	1.0785 (4)	0.6917 (3)	0.0253 (8)
H19	0.5093	1.1588	0.6988	0.030*
C20	0.4549 (3)	1.0321 (4)	0.7544 (3)	0.0249 (9)
H20	0.4655	1.0810	0.8043	0.030*
C21	0.4132 (2)	0.9143 (4)	0.7454 (2)	0.0205 (8)
H21	0.3963	0.8824	0.7892	0.025*
C22	0.2247 (2)	0.7088 (3)	0.5762 (2)	0.0186 (7)
C23	0.1512 (3)	0.6499 (4)	0.5882 (3)	0.0219 (8)
H23	0.1636	0.5983	0.6373	0.026*
C24	0.0605 (3)	0.6665 (4)	0.5290 (3)	0.0255 (9)
H24	0.0110	0.6277	0.5380	0.031*
C25	0.0422 (3)	0.7399 (4)	0.4563 (3)	0.0250 (9)
H25	−0.0199	0.7524	0.4159	0.030*
C26	0.1149 (3)	0.7950 (4)	0.4429 (3)	0.0279 (9)
H26	0.1023	0.8435	0.3924	0.033*
C27	0.2057 (3)	0.7801 (4)	0.5021 (2)	0.0218 (8)
H27	0.2549	0.8185	0.4922	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0167 (3)	0.0092 (3)	0.0194 (3)	−0.00037 (16)	0.0050 (2)	−0.00177 (17)
Cl1	0.0221 (4)	0.0127 (4)	0.0235 (5)	0.0019 (3)	0.0060 (4)	0.0012 (3)
S1	0.0185 (4)	0.0130 (4)	0.0248 (5)	−0.0006 (3)	0.0051 (4)	−0.0051 (4)
P1	0.0178 (4)	0.0110 (4)	0.0183 (5)	−0.0007 (3)	0.0058 (4)	−0.0012 (4)
O1	0.0177 (12)	0.0122 (13)	0.0250 (14)	−0.0008 (10)	0.0054 (11)	−0.0056 (10)
O2	0.0198 (13)	0.0210 (15)	0.0362 (17)	−0.0019 (11)	0.0080 (12)	−0.0132 (13)
N1	0.0157 (14)	0.0116 (14)	0.0200 (16)	−0.0006 (11)	0.0034 (12)	0.0024 (12)
N2	0.0172 (15)	0.0120 (15)	0.0227 (17)	0.0010 (12)	0.0049 (13)	−0.0024 (13)
N3	0.0180 (15)	0.0152 (16)	0.0213 (17)	−0.0026 (12)	0.0041 (13)	0.0000 (13)
C1	0.0243 (18)	0.0105 (17)	0.0180 (18)	−0.0020 (14)	0.0057 (15)	0.0001 (14)
C2	0.0174 (17)	0.0165 (18)	0.0221 (19)	−0.0011 (14)	0.0058 (15)	−0.0016 (15)
C3	0.0205 (17)	0.0198 (19)	0.023 (2)	−0.0044 (15)	0.0041 (15)	−0.0044 (16)
C4	0.029 (2)	0.0123 (18)	0.024 (2)	−0.0029 (15)	0.0067 (16)	−0.0063 (15)
C5	0.0253 (19)	0.0107 (17)	0.024 (2)	0.0030 (14)	0.0070 (16)	−0.0024 (15)
C6	0.0205 (17)	0.0145 (18)	0.0170 (18)	−0.0014 (13)	0.0063 (15)	−0.0001 (14)
C7	0.0236 (18)	0.0126 (17)	0.0176 (19)	0.0026 (14)	0.0058 (15)	0.0006 (14)
C8	0.0203 (17)	0.0131 (17)	0.0186 (18)	0.0006 (14)	0.0057 (15)	0.0047 (14)
C9	0.0187 (18)	0.0173 (19)	0.030 (2)	0.0020 (14)	0.0070 (16)	−0.0015 (16)
C10	0.0255 (18)	0.0146 (18)	0.0196 (19)	−0.0047 (14)	0.0098 (16)	−0.0039 (15)
C11	0.031 (2)	0.0152 (19)	0.023 (2)	−0.0004 (15)	0.0088 (17)	−0.0022 (15)
C12	0.046 (3)	0.019 (2)	0.031 (2)	−0.0069 (19)	0.014 (2)	0.0020 (18)
C13	0.052 (3)	0.028 (2)	0.027 (2)	−0.016 (2)	0.021 (2)	−0.0039 (19)
C14	0.037 (2)	0.030 (2)	0.027 (2)	−0.0101 (18)	0.0175 (19)	−0.0093 (18)
C15	0.0259 (19)	0.019 (2)	0.027 (2)	−0.0037 (15)	0.0105 (17)	−0.0042 (16)
C16	0.0175 (17)	0.0104 (17)	0.024 (2)	0.0028 (13)	0.0037 (15)	0.0021 (14)
C17	0.0222 (18)	0.0151 (19)	0.023 (2)	−0.0037 (14)	0.0070 (16)	−0.0021 (15)
C18	0.0255 (19)	0.0163 (19)	0.026 (2)	−0.0020 (15)	0.0091 (16)	0.0058 (16)
C19	0.0246 (19)	0.0144 (18)	0.033 (2)	−0.0032 (15)	0.0083 (17)	−0.0002 (17)
C20	0.027 (2)	0.018 (2)	0.027 (2)	−0.0009 (15)	0.0078 (17)	−0.0056 (16)
C21	0.0233 (18)	0.0164 (18)	0.022 (2)	−0.0010 (14)	0.0088 (15)	−0.0021 (15)
C22	0.0183 (17)	0.0152 (18)	0.0187 (19)	0.0013 (14)	0.0039 (14)	−0.0060 (14)
C23	0.0232 (18)	0.0143 (18)	0.028 (2)	0.0011 (14)	0.0107 (16)	−0.0017 (16)
C24	0.0212 (19)	0.022 (2)	0.033 (2)	−0.0039 (15)	0.0106 (17)	−0.0085 (17)
C25	0.0175 (17)	0.025 (2)	0.025 (2)	0.0038 (15)	0.0007 (15)	−0.0066 (17)
C26	0.030 (2)	0.022 (2)	0.024 (2)	0.0044 (16)	0.0042 (17)	0.0000 (17)
C27	0.0228 (18)	0.021 (2)	0.020 (2)	0.0019 (15)	0.0077 (15)	0.0003 (15)

Geometric parameters (Å, º) top

Ni1—N1	1.895 (3)	C10—C15	1.406 (5)
Ni1—O1	1.849 (2)	C11—C12	1.385 (6)
Ni1—P1	2.216 (1)	C11—H11	0.9500
Ni1—S1	2.150 (1)	C12—C13	1.382 (7)
S1—C8	1.738 (4)	C12—H12	0.9500
P1—C10	1.813 (4)	C13—C14	1.391 (7)
P1—C22	1.826 (4)	C13—H13	0.9500
P1—C16	1.830 (4)	C14—C15	1.376 (6)
O1—C1	1.324 (4)	C14—H14	0.9500
O2—C2	1.386 (4)	C15—H15	0.9500
O2—H2O	0.84 (5)	C16—C17	1.385 (5)
N1—C7	1.299 (5)	C16—C21	1.397 (5)
N1—N2	1.396 (4)	C17—C18	1.394 (5)
N2—C8	1.341 (5)	C17—H17	0.9500
N2—H2N	0.86 (4)	C18—C19	1.380 (6)
N3—C8	1.311 (5)	C18—H18	0.9500
N3—C9	1.468 (5)	C19—C20	1.378 (6)
N3—H3N	0.86 (4)	C19—H19	0.9500
C1—C6	1.401 (5)	C20—C21	1.393 (5)
C1—C2	1.415 (5)	C20—H20	0.9500
C2—C3	1.369 (5)	C21—H21	0.9500
C3—C4	1.405 (5)	C22—C27	1.395 (5)
C3—H3	0.9500	C22—C23	1.405 (5)
C4—C5	1.377 (5)	C23—C24	1.386 (5)
C4—H4	0.9500	C23—H23	0.9500
C5—C6	1.434 (5)	C24—C25	1.389 (6)
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.422 (5)	C25—C26	1.387 (6)
C7—H7	0.9500	C25—H25	0.9500
C9—H9A	0.9800	C26—C27	1.385 (5)
C9—H9B	0.9800	C26—H26	0.9500
C9—H9C	0.9800	C27—H27	0.9500
C10—C11	1.406 (5)

O1—Ni1—N1	94.19 (12)	C11—C10—C15	118.6 (4)
O1—Ni1—S1	176.80 (9)	C11—C10—P1	120.4 (3)
N1—Ni1—S1	88.09 (9)	C15—C10—P1	121.0 (3)
O1—Ni1—P1	87.10 (8)	C12—C11—C10	119.9 (4)
N1—Ni1—P1	175.83 (10)	C12—C11—H11	120.1
S1—Ni1—P1	90.78 (4)	C10—C11—H11	120.1
C8—S1—Ni1	98.04 (13)	C13—C12—C11	120.5 (4)
C10—P1—C22	104.30 (17)	C13—C12—H12	119.7
C10—P1—C16	106.66 (18)	C11—C12—H12	119.7
C22—P1—C16	105.45 (17)	C12—C13—C14	120.3 (4)
C10—P1—Ni1	112.48 (13)	C12—C13—H13	119.8
C22—P1—Ni1	112.74 (12)	C14—C13—H13	119.8
C16—P1—Ni1	114.42 (12)	C15—C14—C13	119.6 (4)
C1—O1—Ni1	126.5 (2)	C15—C14—H14	120.2
C2—O2—H2O	104 (4)	C13—C14—H14	120.2
C7—N1—N2	114.7 (3)	C14—C15—C10	121.0 (4)
C7—N1—Ni1	127.0 (3)	C14—C15—H15	119.5
N2—N1—Ni1	118.3 (2)	C10—C15—H15	119.5
C8—N2—N1	117.3 (3)	C17—C16—C21	119.4 (3)
C8—N2—H2N	125 (4)	C17—C16—P1	117.2 (3)
N1—N2—H2N	114 (4)	C21—C16—P1	123.3 (3)
C8—N3—C9	124.6 (3)	C16—C17—C18	120.8 (4)
C8—N3—H3N	121 (3)	C16—C17—H17	119.6
C9—N3—H3N	112 (3)	C18—C17—H17	119.6
O1—C1—C6	126.1 (3)	C19—C18—C17	119.4 (4)
O1—C1—C2	115.8 (3)	C19—C18—H18	120.3
C6—C1—C2	118.1 (3)	C17—C18—H18	120.3
C3—C2—O2	120.0 (3)	C20—C19—C18	120.3 (4)
C3—C2—C1	122.1 (3)	C20—C19—H19	119.9
O2—C2—C1	118.0 (3)	C18—C19—H19	119.9
C2—C3—C4	119.6 (3)	C19—C20—C21	120.7 (4)
C2—C3—H3	120.2	C19—C20—H20	119.6
C4—C3—H3	120.2	C21—C20—H20	119.6
C5—C4—C3	120.5 (3)	C20—C21—C16	119.3 (4)
C5—C4—H4	119.7	C20—C21—H21	120.3
C3—C4—H4	119.7	C16—C21—H21	120.3
C4—C5—C6	119.8 (3)	C27—C22—C23	119.1 (3)
C4—C5—H5	120.1	C27—C22—P1	119.8 (3)
C6—C5—H5	120.1	C23—C22—P1	121.0 (3)
C1—C6—C7	121.4 (3)	C24—C23—C22	120.5 (4)
C1—C6—C5	119.8 (3)	C24—C23—H23	119.8
C7—C6—C5	118.8 (3)	C22—C23—H23	119.8
N1—C7—C6	124.8 (3)	C23—C24—C25	119.9 (4)
N1—C7—H7	117.6	C23—C24—H24	120.0
C6—C7—H7	117.6	C25—C24—H24	120.0
N3—C8—N2	120.7 (3)	C26—C25—C24	119.7 (3)
N3—C8—S1	121.0 (3)	C26—C25—H25	120.1
N2—C8—S1	118.2 (3)	C24—C25—H25	120.1
N3—C9—H9A	109.5	C27—C26—C25	120.8 (4)
N3—C9—H9B	109.5	C27—C26—H26	119.6
H9A—C9—H9B	109.5	C25—C26—H26	119.6
N3—C9—H9C	109.5	C26—C27—C22	119.9 (4)
H9A—C9—H9C	109.5	C26—C27—H27	120.0
H9B—C9—H9C	109.5	C22—C27—H27	120.0

N1—Ni1—S1—C8	−1.59 (15)	C22—P1—C10—C11	130.3 (3)
P1—Ni1—S1—C8	174.39 (13)	C16—P1—C10—C11	−118.5 (3)
O1—Ni1—P1—C10	95.87 (15)	Ni1—P1—C10—C11	7.8 (3)
S1—Ni1—P1—C10	−86.52 (13)	C22—P1—C10—C15	−49.1 (3)
O1—Ni1—P1—C22	−21.73 (16)	C16—P1—C10—C15	62.2 (3)
S1—Ni1—P1—C22	155.87 (14)	Ni1—P1—C10—C15	−171.6 (3)
O1—Ni1—P1—C16	−142.22 (16)	C15—C10—C11—C12	−0.5 (6)
S1—Ni1—P1—C16	35.38 (14)	P1—C10—C11—C12	−179.8 (3)
N1—Ni1—O1—C1	2.5 (3)	C10—C11—C12—C13	1.1 (6)
P1—Ni1—O1—C1	−173.5 (3)	C11—C12—C13—C14	−1.4 (7)
O1—Ni1—N1—C7	−1.3 (3)	C12—C13—C14—C15	1.0 (6)
S1—Ni1—N1—C7	−179.0 (3)	C13—C14—C15—C10	−0.3 (6)
O1—Ni1—N1—N2	178.6 (3)	C11—C10—C15—C14	0.1 (6)
S1—Ni1—N1—N2	0.8 (2)	P1—C10—C15—C14	179.4 (3)
C7—N1—N2—C8	−179.4 (3)	C10—P1—C16—C17	170.3 (3)
Ni1—N1—N2—C8	0.7 (4)	C22—P1—C16—C17	−79.2 (3)
Ni1—O1—C1—C6	−2.1 (5)	Ni1—P1—C16—C17	45.3 (3)
Ni1—O1—C1—C2	178.1 (3)	C10—P1—C16—C21	−6.8 (4)
O1—C1—C2—C3	−178.3 (4)	C22—P1—C16—C21	103.7 (3)
C6—C1—C2—C3	2.0 (6)	Ni1—P1—C16—C21	−131.9 (3)
O1—C1—C2—O2	1.3 (5)	C21—C16—C17—C18	−1.9 (5)
C6—C1—C2—O2	−178.5 (3)	P1—C16—C17—C18	−179.2 (3)
O2—C2—C3—C4	179.2 (4)	C16—C17—C18—C19	1.4 (6)
C1—C2—C3—C4	−1.2 (6)	C17—C18—C19—C20	−0.5 (6)
C2—C3—C4—C5	−0.7 (6)	C18—C19—C20—C21	0.3 (6)
C3—C4—C5—C6	1.8 (6)	C19—C20—C21—C16	−0.8 (6)
O1—C1—C6—C7	−0.4 (6)	C17—C16—C21—C20	1.6 (5)
C2—C1—C6—C7	179.3 (3)	P1—C16—C21—C20	178.7 (3)
O1—C1—C6—C5	179.4 (3)	C10—P1—C22—C27	160.2 (3)
C2—C1—C6—C5	−0.9 (5)	C16—P1—C22—C27	48.1 (3)
C4—C5—C6—C1	−0.9 (6)	Ni1—P1—C22—C27	−77.4 (3)
C4—C5—C6—C7	178.8 (4)	C10—P1—C22—C23	−23.0 (3)
N2—N1—C7—C6	179.6 (3)	C16—P1—C22—C23	−135.1 (3)
Ni1—N1—C7—C6	−0.6 (5)	Ni1—P1—C22—C23	99.4 (3)
C1—C6—C7—N1	1.8 (6)	C27—C22—C23—C24	−2.6 (5)
C5—C6—C7—N1	−178.0 (3)	P1—C22—C23—C24	−179.4 (3)
C9—N3—C8—N2	−1.2 (6)	C22—C23—C24—C25	1.2 (6)
C9—N3—C8—S1	−178.9 (3)	C23—C24—C25—C26	0.8 (6)
N1—N2—C8—N3	179.9 (3)	C24—C25—C26—C27	−1.5 (6)
N1—N2—C8—S1	−2.3 (4)	C25—C26—C27—C22	0.1 (6)
Ni1—S1—C8—N3	−179.7 (3)	C23—C22—C27—C26	1.9 (6)
Ni1—S1—C8—N2	2.5 (3)	P1—C22—C27—C26	178.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.84 (5)	2.10 (4)	2.640 (4)	122 (4)
N2—H2N···Cl1	0.86 (4)	2.19 (4)	3.046 (3)	172 (5)
N3—H3N···Cl1ⁱ	0.86 (4)	2.28 (4)	3.111 (3)	164 (5)

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₁₀N₃O₂S)(C₁₈H₁₅P)]Cl
M_r	580.69
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	15.7781 (15), 10.6306 (10), 17.0020 (15)
β (°)	113.961 (1)
V (Å³)	2606.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.25 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.785, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	23696, 5971, 4428
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.177, 1.05
No. of reflections	5971
No. of parameters	338
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.60, −1.06

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—N1	1.895 (3)	Ni1—P1	2.216 (1)
Ni1—O1	1.849 (2)	Ni1—S1	2.150 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.84 (5)	2.10 (4)	2.640 (4)	122 (4)
N2—H2N···Cl1	0.86 (4)	2.19 (4)	3.046 (3)	172 (5)
N3—H3N···Cl1ⁱ	0.86 (4)	2.28 (4)	3.111 (3)	164 (5)

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.

Acknowledgements

We thank the University of Malaya (PS354/2009) and MOHE (FRGS-FP001/2009) for supporting this study. HBS 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
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Shawish, H. B., Tan, K. W., Maah, M. J. & Ng, S. W. (2010). Acta Cryst. E66, m1074. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Swesi, A. T., Farina, Y. & Baba, I. (2007). Sains Malaysiana, 36, 21–26. CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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