{4-Bromo-2-[(2-sulfido­phen­yl)imino­meth­yl]phenolato-κ3S,N,O}(triphenyl­phosphane-κP)nickel(II)

Tamizh, M.M.; Karvembu, R.; Varghese, B.; Tiekink, E.R.T.

doi:10.1107/S1600536811008907

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page m441

doi:10.1107/S1600536811008907

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{4-Bromo-2-[(2-sulfidophenyl)iminomethyl]phenolato-κ³S,N,O}(triphenylphosphane-κP)nickel(II)

M. Muthu Tamizh,^a R. Karvembu,^a ‡ B. Varghese ^b and Edward R. T. Tiekink ^c ^*

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, ^bSophisticated Analytical Instruments Facility, Indian Institute of Technology-Madras, Chennai 600 036, India, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 March 2011; accepted 9 March 2011; online 12 March 2011)

The Ni^II atom in the title complex, [Ni(C₁₃H₈BrNOS)(C₁₈H₁₅P)], is coordinated by the N, O and S atoms of the dianionic tridentate ligand, and its square-planar geometry is completed by a phosphane P atom. The dihedral angle between the aromatic rings in the 4-bromo-2-[(2-sulfidophenyl)iminomethyl]phenolate ligand is 2.01 (14)°. The most prominent feature of the packing is the presence of supramolecular chains aligned along the a axis, mediated by C—H⋯S interactions.

Related literature

For chemical background and related structures, see: Muthu Tamizh et al. (2009 ).

Experimental

Crystal data

[Ni(C₁₃H₈BrNOS)(C₁₈H₁₅P)]
M_r = 627.15
Orthorhombic, P b c a
a = 9.7197 (2) Å
b = 18.7729 (6) Å
c = 29.8372 (7) Å
V = 5444.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 2.34 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.592, T_max = 0.720
31370 measured reflections
6260 independent reflections
4184 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.092
S = 1.03
6260 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni—S1	2.1219 (7)
Ni—P1	2.1975 (7)
Ni—O1	1.8494 (18)
Ni—N1	1.900 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯S1ⁱ	0.93	2.84	3.620 (3)	142
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (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: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008907/hb5813sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008907/hb5813Isup2.hkl

checkCIF report

Comment top

The title complex, (I), was investigated as part of a wider investigation of complexes of interest owing to their relationship to Ni/Fe hydrogenases (Muthu Tamizh et al., 2009). The Ni^II atom exists within a square planar donor set defined by the N,O,S atoms of the dinegative tridentate ligand, and a P atom derived from the phosphane ligand. The S1, P1, O1 and N1 atoms deviate -0.0535 (7), 0.0556 (8), -0.0609 (8) and 0.0588 (8) Å, from their least-squares plane, respectively (r.m.s. deviation = 0.0573 Å), and the Ni atom lies 0.0548 (9) Å out of the plane. The geometric parameters about the Ni^II atom, Table 1, match closely those in the parent complex (Muthu Tamizh et al., 2009).

The most prominent interactions in the crystal structure are of the type C—H···S, Table 2. These connect molecules into linear supramolecular chains along the a axis, Fig. 2.

Related literature top

For chemical background and related structures, see: Muthu Tamizh et al. (2009).

Experimental top

Complex (I) was prepared from the reaction between [NiCl₂(PPh₃)₂] and N-(2-mercaptophenyl)-4-bromosalicylideneimine in ethanol solution following the literature procedure (Muthu Tamizh et al., 2009). Brown prisms of (I) were obtained by the diffusion of diethyl ether vapour into its dichloromethane solution. Characterization data are as given in Muthu Tamizh et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.
	Fig. 2. Supramolecular chain aligned along the a axis in (I) mediated by C—H···S contacts shown as orange dashed lines.

{4-Bromo-2-[(2-sulfidophenyl)iminomethyl]phenolato- κ³S,N,O}(triphenylphosphane-κP)nickel(II) top

Crystal data top

[Ni(C₁₃H₈BrNOS)(C₁₈H₁₅P)]	F(000) = 2544
M_r = 627.15	D_x = 1.530 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5504 reflections
a = 9.7197 (2) Å	θ = 2.2–25.0°
b = 18.7729 (6) Å	µ = 2.34 mm⁻¹
c = 29.8372 (7) Å	T = 293 K
V = 5444.3 (2) Å³	Prism, brown
Z = 8	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	6260 independent reflections
Radiation source: fine-focus sealed tube	4184 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω and ϕ scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.592, T_max = 0.720	k = −13→24
31370 measured reflections	l = −31→38

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0435P)² + 0.9841P] where P = (F_o² + 2F_c²)/3
6260 reflections	(Δ/σ)_max = 0.002
334 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ni(C₁₃H₈BrNOS)(C₁₈H₁₅P)]	V = 5444.3 (2) Å³
M_r = 627.15	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.7197 (2) Å	µ = 2.34 mm⁻¹
b = 18.7729 (6) Å	T = 293 K
c = 29.8372 (7) Å	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	6260 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4184 reflections with I > 2σ(I)
T_min = 0.592, T_max = 0.720	R_int = 0.050
31370 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
6260 reflections	Δρ_min = −0.43 e Å⁻³
334 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Ni	0.70528 (3)	0.093546 (17)	0.666881 (10)	0.02872 (9)
Br1	0.89896 (5)	−0.08458 (2)	0.874812 (12)	0.07450 (14)
P1	0.79107 (6)	0.06542 (4)	0.60108 (2)	0.02893 (15)
S1	0.57705 (7)	0.17098 (4)	0.63624 (2)	0.04198 (18)
O1	0.83786 (18)	0.03231 (10)	0.68907 (6)	0.0403 (5)
N1	0.6293 (2)	0.11848 (11)	0.72343 (7)	0.0298 (5)
C1	0.8475 (3)	0.00804 (14)	0.73001 (8)	0.0337 (6)
C2	0.7685 (3)	0.03472 (14)	0.76579 (8)	0.0344 (6)
C3	0.7875 (3)	0.00663 (16)	0.80893 (9)	0.0463 (7)
H3	0.7363	0.0244	0.8327	0.056*
C4	0.8795 (3)	−0.04598 (16)	0.81620 (9)	0.0465 (7)
C5	0.9575 (3)	−0.07331 (16)	0.78142 (10)	0.0466 (7)
H5	1.0204	−0.1096	0.7868	0.056*
C6	0.9417 (3)	−0.04669 (16)	0.73927 (9)	0.0441 (7)
H6	0.9945	−0.0652	0.7161	0.053*
C7	0.6686 (3)	0.08912 (15)	0.76043 (9)	0.0393 (7)
H7	0.6266	0.1055	0.7865	0.047*
C8	0.5279 (2)	0.17371 (13)	0.72504 (8)	0.0309 (6)
C9	0.4973 (3)	0.20480 (14)	0.68419 (9)	0.0357 (6)
C10	0.4033 (3)	0.26043 (16)	0.68227 (11)	0.0488 (8)
H10	0.3848	0.2825	0.6550	0.059*
C11	0.3372 (3)	0.28300 (17)	0.72053 (12)	0.0523 (8)
H11	0.2738	0.3200	0.7191	0.063*
C12	0.3653 (3)	0.25079 (16)	0.76073 (11)	0.0491 (8)
H12	0.3195	0.2656	0.7865	0.059*
C13	0.4604 (3)	0.19692 (15)	0.76332 (10)	0.0435 (7)
H13	0.4796	0.1759	0.7908	0.052*
C14	0.7096 (3)	0.10195 (14)	0.55127 (8)	0.0320 (6)
C15	0.5778 (3)	0.07925 (18)	0.54121 (10)	0.0488 (8)
H15	0.5358	0.0448	0.5589	0.059*
C16	0.5086 (4)	0.1074 (2)	0.50515 (11)	0.0619 (10)
H16	0.4202	0.0915	0.4986	0.074*
C17	0.5675 (4)	0.1582 (2)	0.47883 (10)	0.0582 (9)
H17	0.5187	0.1778	0.4550	0.070*
C18	0.6985 (4)	0.18015 (19)	0.48761 (10)	0.0607 (9)
H18	0.7402	0.2139	0.4693	0.073*
C19	0.7700 (3)	0.15220 (16)	0.52392 (9)	0.0456 (7)
H19	0.8592	0.1675	0.5298	0.055*
C20	0.9652 (3)	0.10013 (14)	0.59933 (8)	0.0329 (6)
C21	0.9851 (3)	0.17007 (17)	0.61177 (9)	0.0460 (7)
H21	0.9106	0.1974	0.6212	0.055*
C22	1.1149 (3)	0.1999 (2)	0.61037 (11)	0.0600 (9)
H22	1.1273	0.2474	0.6184	0.072*
C23	1.2250 (3)	0.1599 (2)	0.59722 (11)	0.0605 (10)
H23	1.3123	0.1801	0.5962	0.073*
C24	1.2070 (3)	0.0902 (2)	0.58564 (11)	0.0566 (9)
H24	1.2824	0.0630	0.5768	0.068*
C25	1.0773 (3)	0.05948 (17)	0.58688 (9)	0.0429 (7)
H25	1.0659	0.0118	0.5794	0.052*
C26	0.8064 (2)	−0.02845 (14)	0.58757 (9)	0.0333 (6)
C27	0.8427 (3)	−0.04952 (16)	0.54450 (9)	0.0444 (7)
H27	0.8529	−0.0155	0.5221	0.053*
C28	0.8637 (3)	−0.12050 (18)	0.53468 (11)	0.0544 (8)
H28	0.8893	−0.1342	0.5059	0.065*
C29	0.8465 (4)	−0.17076 (19)	0.56755 (12)	0.0638 (9)
H29	0.8622	−0.2186	0.5612	0.077*
C30	0.8064 (4)	−0.15059 (18)	0.60965 (12)	0.0675 (10)
H30	0.7932	−0.1851	0.6316	0.081*
C31	0.7852 (3)	−0.07989 (16)	0.61992 (10)	0.0500 (8)
H31	0.7567	−0.0669	0.6485	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.03059 (18)	0.03009 (19)	0.02548 (16)	0.00211 (14)	0.00219 (13)	0.00157 (13)
Br1	0.1097 (3)	0.0692 (3)	0.0446 (2)	0.0162 (2)	−0.01411 (19)	0.02072 (17)
P1	0.0301 (3)	0.0312 (4)	0.0255 (3)	0.0001 (3)	0.0013 (3)	0.0021 (3)
S1	0.0511 (4)	0.0426 (4)	0.0323 (3)	0.0150 (3)	−0.0035 (3)	0.0012 (3)
O1	0.0441 (11)	0.0478 (12)	0.0289 (10)	0.0149 (9)	0.0042 (8)	0.0023 (9)
N1	0.0296 (11)	0.0289 (12)	0.0309 (11)	−0.0015 (9)	0.0043 (9)	0.0000 (9)
C1	0.0369 (15)	0.0320 (15)	0.0323 (14)	−0.0011 (12)	−0.0036 (11)	−0.0001 (11)
C2	0.0415 (15)	0.0318 (15)	0.0300 (13)	0.0036 (12)	−0.0003 (11)	0.0014 (11)
C3	0.0606 (19)	0.0489 (19)	0.0295 (14)	0.0086 (16)	0.0009 (13)	0.0012 (13)
C4	0.0621 (19)	0.0423 (18)	0.0351 (15)	−0.0011 (15)	−0.0110 (14)	0.0101 (13)
C5	0.0507 (18)	0.0383 (18)	0.0508 (18)	0.0080 (14)	−0.0128 (14)	0.0050 (14)
C6	0.0450 (17)	0.0453 (18)	0.0421 (16)	0.0120 (14)	0.0007 (13)	0.0014 (13)
C7	0.0464 (17)	0.0430 (17)	0.0285 (14)	0.0029 (13)	0.0079 (12)	−0.0016 (12)
C8	0.0274 (13)	0.0264 (14)	0.0389 (14)	0.0000 (11)	0.0035 (11)	−0.0038 (11)
C9	0.0341 (14)	0.0324 (15)	0.0407 (15)	0.0030 (12)	−0.0017 (12)	−0.0062 (12)
C10	0.0487 (18)	0.0434 (19)	0.0544 (18)	0.0142 (15)	−0.0116 (14)	−0.0030 (15)
C11	0.0397 (17)	0.0408 (19)	0.076 (2)	0.0116 (14)	−0.0040 (16)	−0.0111 (17)
C12	0.0431 (17)	0.0450 (19)	0.059 (2)	0.0051 (15)	0.0163 (14)	−0.0118 (16)
C13	0.0432 (17)	0.0424 (18)	0.0448 (16)	0.0031 (14)	0.0110 (13)	−0.0004 (13)
C14	0.0357 (14)	0.0366 (15)	0.0235 (12)	0.0051 (12)	0.0001 (10)	−0.0026 (10)
C15	0.0418 (17)	0.063 (2)	0.0418 (16)	−0.0044 (15)	−0.0043 (13)	0.0031 (15)
C16	0.0436 (18)	0.096 (3)	0.0466 (19)	0.0106 (18)	−0.0128 (15)	−0.0068 (19)
C17	0.072 (2)	0.075 (3)	0.0278 (15)	0.028 (2)	−0.0132 (15)	−0.0050 (16)
C18	0.084 (3)	0.061 (2)	0.0368 (17)	0.006 (2)	−0.0048 (16)	0.0128 (15)
C19	0.0537 (18)	0.049 (2)	0.0337 (15)	−0.0011 (15)	−0.0042 (13)	0.0062 (13)
C20	0.0323 (14)	0.0420 (17)	0.0244 (12)	−0.0034 (12)	−0.0006 (10)	0.0085 (11)
C21	0.0437 (17)	0.0475 (19)	0.0469 (17)	−0.0077 (15)	−0.0032 (13)	0.0015 (14)
C22	0.059 (2)	0.059 (2)	0.062 (2)	−0.0223 (18)	−0.0125 (17)	0.0061 (17)
C23	0.0377 (19)	0.087 (3)	0.057 (2)	−0.0201 (19)	−0.0117 (15)	0.0171 (19)
C24	0.0297 (16)	0.087 (3)	0.0533 (19)	0.0026 (17)	0.0003 (13)	0.0175 (18)
C25	0.0379 (16)	0.0512 (19)	0.0397 (16)	0.0019 (14)	0.0009 (12)	0.0086 (14)
C26	0.0319 (14)	0.0318 (15)	0.0363 (14)	0.0014 (11)	−0.0003 (11)	−0.0012 (11)
C27	0.0550 (18)	0.0418 (19)	0.0363 (15)	0.0096 (14)	−0.0010 (13)	−0.0039 (13)
C28	0.070 (2)	0.053 (2)	0.0401 (16)	0.0139 (17)	−0.0052 (15)	−0.0130 (16)
C29	0.091 (3)	0.0376 (19)	0.063 (2)	0.0076 (19)	−0.013 (2)	−0.0117 (17)
C30	0.109 (3)	0.0338 (19)	0.060 (2)	−0.0059 (19)	0.001 (2)	0.0049 (16)
C31	0.070 (2)	0.0369 (18)	0.0434 (17)	−0.0061 (16)	0.0073 (15)	−0.0029 (13)

Geometric parameters (Å, º) top

Ni—S1	2.1219 (7)	C14—C19	1.378 (4)
Ni—P1	2.1975 (7)	C14—C15	1.383 (4)
Ni—O1	1.8494 (18)	C15—C16	1.374 (4)
Ni—N1	1.900 (2)	C15—H15	0.9300
Br1—C4	1.902 (3)	C16—C17	1.362 (5)
P1—C26	1.814 (3)	C16—H16	0.9300
P1—C20	1.815 (3)	C17—C18	1.364 (4)
P1—C14	1.818 (2)	C17—H17	0.9300
S1—C9	1.747 (3)	C18—C19	1.390 (4)
O1—C1	1.307 (3)	C18—H18	0.9300
N1—C7	1.292 (3)	C19—H19	0.9300
N1—C8	1.431 (3)	C20—C21	1.378 (4)
C1—C6	1.404 (4)	C20—C25	1.381 (4)
C1—C2	1.407 (3)	C21—C22	1.381 (4)
C2—C3	1.403 (4)	C21—H21	0.9300
C2—C7	1.418 (4)	C22—C23	1.365 (5)
C3—C4	1.350 (4)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.365 (5)
C4—C5	1.384 (4)	C23—H23	0.9300
C5—C6	1.362 (4)	C24—C25	1.387 (4)
C5—H5	0.9300	C24—H24	0.9300
C6—H6	0.9300	C25—H25	0.9300
C7—H7	0.9300	C26—C31	1.381 (4)
C8—C9	1.384 (4)	C26—C27	1.390 (4)
C8—C13	1.388 (3)	C27—C28	1.379 (4)
C9—C10	1.389 (4)	C27—H27	0.9300
C10—C11	1.376 (4)	C28—C29	1.371 (5)
C10—H10	0.9300	C28—H28	0.9300
C11—C12	1.371 (4)	C29—C30	1.369 (5)
C11—H11	0.9300	C29—H29	0.9300
C12—C13	1.372 (4)	C30—C31	1.377 (4)
C12—H12	0.9300	C30—H30	0.9300
C13—H13	0.9300	C31—H31	0.9300

O1—Ni—N1	96.09 (8)	C8—C13—H13	119.9
O1—Ni—S1	171.63 (6)	C19—C14—C15	118.5 (3)
N1—Ni—S1	89.17 (7)	C19—C14—P1	123.8 (2)
O1—Ni—P1	84.61 (6)	C15—C14—P1	117.7 (2)
N1—Ni—P1	179.29 (7)	C16—C15—C14	120.3 (3)
S1—Ni—P1	90.14 (3)	C16—C15—H15	119.8
C26—P1—C20	105.42 (12)	C14—C15—H15	119.8
C26—P1—C14	102.74 (12)	C17—C16—C15	121.0 (3)
C20—P1—C14	104.33 (12)	C17—C16—H16	119.5
C26—P1—Ni	117.59 (9)	C15—C16—H16	119.5
C20—P1—Ni	107.06 (9)	C16—C17—C18	119.6 (3)
C14—P1—Ni	118.32 (8)	C16—C17—H17	120.2
C9—S1—Ni	99.01 (9)	C18—C17—H17	120.2
C1—O1—Ni	126.94 (16)	C17—C18—C19	120.1 (3)
C7—N1—C8	118.9 (2)	C17—C18—H18	119.9
C7—N1—Ni	122.61 (18)	C19—C18—H18	119.9
C8—N1—Ni	118.41 (16)	C14—C19—C18	120.5 (3)
O1—C1—C6	119.1 (2)	C14—C19—H19	119.8
O1—C1—C2	123.1 (2)	C18—C19—H19	119.8
C6—C1—C2	117.8 (2)	C21—C20—C25	119.2 (3)
C3—C2—C1	119.4 (2)	C21—C20—P1	117.7 (2)
C3—C2—C7	117.7 (2)	C25—C20—P1	123.0 (2)
C1—C2—C7	123.0 (2)	C20—C21—C22	120.4 (3)
C4—C3—C2	120.7 (3)	C20—C21—H21	119.8
C4—C3—H3	119.7	C22—C21—H21	119.8
C2—C3—H3	119.7	C23—C22—C21	120.1 (3)
C3—C4—C5	120.9 (3)	C23—C22—H22	120.0
C3—C4—Br1	119.5 (2)	C21—C22—H22	120.0
C5—C4—Br1	119.6 (2)	C22—C23—C24	120.0 (3)
C6—C5—C4	119.6 (3)	C22—C23—H23	120.0
C6—C5—H5	120.2	C24—C23—H23	120.0
C4—C5—H5	120.2	C23—C24—C25	120.5 (3)
C5—C6—C1	121.6 (3)	C23—C24—H24	119.7
C5—C6—H6	119.2	C25—C24—H24	119.7
C1—C6—H6	119.2	C20—C25—C24	119.7 (3)
N1—C7—C2	127.3 (2)	C20—C25—H25	120.2
N1—C7—H7	116.4	C24—C25—H25	120.2
C2—C7—H7	116.4	C31—C26—C27	119.0 (3)
C9—C8—C13	119.4 (2)	C31—C26—P1	120.8 (2)
C9—C8—N1	115.1 (2)	C27—C26—P1	120.2 (2)
C13—C8—N1	125.5 (2)	C28—C27—C26	120.6 (3)
C8—C9—C10	119.7 (2)	C28—C27—H27	119.7
C8—C9—S1	118.2 (2)	C26—C27—H27	119.7
C10—C9—S1	122.1 (2)	C29—C28—C27	119.7 (3)
C11—C10—C9	120.3 (3)	C29—C28—H28	120.2
C11—C10—H10	119.9	C27—C28—H28	120.2
C9—C10—H10	119.9	C30—C29—C28	120.0 (3)
C12—C11—C10	119.8 (3)	C30—C29—H29	120.0
C12—C11—H11	120.1	C28—C29—H29	120.0
C10—C11—H11	120.1	C29—C30—C31	120.9 (3)
C11—C12—C13	120.6 (3)	C29—C30—H30	119.6
C11—C12—H12	119.7	C31—C30—H30	119.6
C13—C12—H12	119.7	C30—C31—C26	119.7 (3)
C12—C13—C8	120.3 (3)	C30—C31—H31	120.1
C12—C13—H13	119.9	C26—C31—H31	120.1

O1—Ni—P1—C26	52.43 (11)	C8—C9—C10—C11	−2.2 (4)
N1—Ni—P1—C26	−120 (6)	S1—C9—C10—C11	176.5 (2)
S1—Ni—P1—C26	−134.10 (9)	C9—C10—C11—C12	0.5 (5)
O1—Ni—P1—C20	−65.88 (11)	C10—C11—C12—C13	1.1 (5)
N1—Ni—P1—C20	122 (6)	C11—C12—C13—C8	−0.9 (5)
S1—Ni—P1—C20	107.59 (9)	C9—C8—C13—C12	−0.8 (4)
O1—Ni—P1—C14	176.78 (12)	N1—C8—C13—C12	179.7 (3)
N1—Ni—P1—C14	5 (6)	C26—P1—C14—C19	−117.6 (2)
S1—Ni—P1—C14	−9.76 (10)	C20—P1—C14—C19	−7.8 (3)
O1—Ni—S1—C9	−127.2 (4)	Ni—P1—C14—C19	111.0 (2)
N1—Ni—S1—C9	1.92 (11)	C26—P1—C14—C15	64.3 (2)
P1—Ni—S1—C9	−178.25 (9)	C20—P1—C14—C15	174.2 (2)
N1—Ni—O1—C1	11.1 (2)	Ni—P1—C14—C15	−67.1 (2)
S1—Ni—O1—C1	139.8 (4)	C19—C14—C15—C16	−1.1 (4)
P1—Ni—O1—C1	−168.8 (2)	P1—C14—C15—C16	177.0 (3)
O1—Ni—N1—C7	−5.1 (2)	C14—C15—C16—C17	−0.4 (5)
S1—Ni—N1—C7	−178.6 (2)	C15—C16—C17—C18	1.8 (5)
P1—Ni—N1—C7	167 (25)	C16—C17—C18—C19	−1.7 (5)
O1—Ni—N1—C8	172.73 (18)	C15—C14—C19—C18	1.2 (4)
S1—Ni—N1—C8	−0.74 (17)	P1—C14—C19—C18	−176.9 (2)
P1—Ni—N1—C8	−15 (6)	C17—C18—C19—C14	0.3 (5)
Ni—O1—C1—C6	170.00 (19)	C26—P1—C20—C21	−175.2 (2)
Ni—O1—C1—C2	−10.7 (4)	C14—P1—C20—C21	77.0 (2)
O1—C1—C2—C3	−178.6 (3)	Ni—P1—C20—C21	−49.2 (2)
C6—C1—C2—C3	0.7 (4)	C26—P1—C20—C25	3.8 (2)
O1—C1—C2—C7	1.7 (4)	C14—P1—C20—C25	−104.0 (2)
C6—C1—C2—C7	−179.0 (3)	Ni—P1—C20—C25	129.8 (2)
C1—C2—C3—C4	−0.7 (4)	C25—C20—C21—C22	2.2 (4)
C7—C2—C3—C4	179.0 (3)	P1—C20—C21—C22	−178.8 (2)
C2—C3—C4—C5	0.2 (5)	C20—C21—C22—C23	−0.9 (5)
C2—C3—C4—Br1	−178.3 (2)	C21—C22—C23—C24	−0.3 (5)
C3—C4—C5—C6	0.2 (5)	C22—C23—C24—C25	0.3 (5)
Br1—C4—C5—C6	178.7 (2)	C21—C20—C25—C24	−2.1 (4)
C4—C5—C6—C1	−0.1 (5)	P1—C20—C25—C24	178.9 (2)
O1—C1—C6—C5	179.0 (3)	C23—C24—C25—C20	0.9 (4)
C2—C1—C6—C5	−0.3 (4)	C20—P1—C26—C31	109.3 (2)
C8—N1—C7—C2	−179.0 (3)	C14—P1—C26—C31	−141.7 (2)
Ni—N1—C7—C2	−1.2 (4)	Ni—P1—C26—C31	−9.8 (3)
C3—C2—C7—N1	−175.1 (3)	C20—P1—C26—C27	−69.3 (2)
C1—C2—C7—N1	4.5 (5)	C14—P1—C26—C27	39.7 (2)
C7—N1—C8—C9	176.7 (2)	Ni—P1—C26—C27	171.56 (19)
Ni—N1—C8—C9	−1.2 (3)	C31—C26—C27—C28	−3.0 (4)
C7—N1—C8—C13	−3.7 (4)	P1—C26—C27—C28	175.6 (2)
Ni—N1—C8—C13	178.4 (2)	C26—C27—C28—C29	1.0 (5)
C13—C8—C9—C10	2.3 (4)	C27—C28—C29—C30	1.2 (5)
N1—C8—C9—C10	−178.1 (2)	C28—C29—C30—C31	−1.2 (6)
C13—C8—C9—S1	−176.5 (2)	C29—C30—C31—C26	−0.9 (5)
N1—C8—C9—S1	3.2 (3)	C27—C26—C31—C30	3.0 (5)
Ni—S1—C9—C8	−3.3 (2)	P1—C26—C31—C30	−175.6 (3)
Ni—S1—C9—C10	178.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···S1ⁱ	0.93	2.84	3.620 (3)	142

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₃H₈BrNOS)(C₁₈H₁₅P)]
M_r	627.15
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	9.7197 (2), 18.7729 (6), 29.8372 (7)
V (Å³)	5444.3 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.34
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.592, 0.720
No. of measured, independent and observed [I > 2σ(I)] reflections	31370, 6260, 4184
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.092, 1.03
No. of reflections	6260
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.43

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ni—S1	2.1219 (7)	Ni—O1	1.8494 (18)
Ni—P1	2.1975 (7)	Ni—N1	1.900 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···S1ⁱ	0.93	2.84	3.620 (3)	142

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

Footnotes

‡Additional correspondence author, e-mail: kar@nitt.edu.

Acknowledgements

RK and MMT gratefully acknowledge the CSIR [01 (2137)/07/EMR-II] for financial support. We also thank the SAIF, IIT-Madras, for the crystallographic data.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Muthu Tamizh, M., Mereiter, K., Kirchner, K., Ramachandra Bhat, B. & Karvembu, R. (2009). Polyhedron, 28, 2157–2164. CrossRef CAS 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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