Bis(N-phenyl­pyrazole-1-carboximidothio­ato-κ2N2,S)nickel(II)

Hossaini Sadr, M.; Sardroodi, J.; Shagagi, Z.; Ng, S.W.

doi:10.1107/S1600536805027960

Bis(N-phenylpyrazole-1-carboximidothioato-κ²N²,S)nickel(II)

M. Hossaini Sadr, J. Sardroodi, Z. Shagagi and S. W. Ng

The Ni atom in the title compound, [Ni(C₁₀H₈N₃S)₂], is N,S-chelated by two C₁₀H₈N₃S anions in a square-planar geometry. The Ni atom lies on a special position of $\overline{1}$ site symmetry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027960/xu6054sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027960/xu6054Isup2.hkl Contains datablock I

CCDC reference: 287764

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
R factor = 0.065
wR factor = 0.173
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.453     0.919
            Tmin(prime) and Tmax expected:      0.587     0.918
            RR(prime) =      0.770
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.77

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The crystal structure of a Cu^II complex, bis(N-phenylpyrazole-1-carboximidothioato)copper(II), has been reported recently by us (Hossain Sadr et al., 2005). The title Ni^II complex, (I), is isostructural with the Cu^II complex.

The molecular structure of (I) is shown in Fig. 1. The Ni^II atom exists in a square-planar N₂S₂Ni geometry with normal coordination bond distances and angles (Table 1) (Reference for standard values?). The metal atom lies on a centre of inversion.

Experimental top

Nickel chloride (0.13 g, 1 mmol) and sodium N-phenyl-2-pyrazolyl-1-carboximidothioate (0.50 g 2.2 mmol) were stirred in methanol (50 ml) for several hours to yield a precipitate; this was collected and recrystallized from tetrahydrofuran (30 ml) to yield needle crystals of (I).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: atomic coordinates taken from the isostructural Cu analogue (Hossain Sadr et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. A plot of (I), with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i) 1 − x, 1 − y, 1 − z.]

Bis(N-phenylpyrazole-1-carboximidothioato-κ²N²,S)nickel(II) top

Crystal data top

[Ni(C₁₀H₈N₃S)₂]	F(000) = 476
M_r = 463.22	D_x = 1.573 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2454 reflections
a = 5.9847 (5) Å	θ = 2.8–27.0°
b = 21.365 (2) Å	µ = 1.23 mm⁻¹
c = 7.8700 (6) Å	T = 295 K
β = 103.605 (1)°	Needle, red-brown
V = 978.05 (14) Å³	0.43 × 0.16 × 0.07 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2147 independent reflections
Radiation source: fine-focus sealed tube	1655 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 27.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.453, T_max = 0.919	k = −25→27
6319 measured reflections	l = −9→10

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.1055P)² + 0.0972P] where P = (F_o² + 2F_c²)/3
2147 reflections	(Δ/σ)_max = 0.001
133 parameters	Δρ_max = 1.40 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[Ni(C₁₀H₈N₃S)₂]	V = 978.05 (14) Å³
M_r = 463.22	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.9847 (5) Å	µ = 1.23 mm⁻¹
b = 21.365 (2) Å	T = 295 K
c = 7.8700 (6) Å	0.43 × 0.16 × 0.07 mm
β = 103.605 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2147 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1655 reflections with I > 2σ(I)
T_min = 0.453, T_max = 0.919	R_int = 0.052
6319 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.10	Δρ_max = 1.40 e Å⁻³
2147 reflections	Δρ_min = −0.83 e Å⁻³
133 parameters

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	0.0296 (3)
S1	0.4840 (2)	0.43071 (5)	0.2917 (1)	0.0397 (3)
N1	0.7254 (5)	0.5414 (1)	0.4137 (4)	0.031 (1)
N2	0.8069 (6)	0.5146 (1)	0.2833 (4)	0.029 (1)
N3	0.8311 (6)	0.4288 (1)	0.1175 (4)	0.034 (1)
C1	0.8425 (7)	0.5947 (2)	0.4503 (5)	0.037 (1)
C2	0.9996 (7)	0.6019 (2)	0.3453 (5)	0.039 (1)
C3	0.9727 (7)	0.5500 (2)	0.2417 (5)	0.036 (1)
C4	0.7205 (6)	0.4550 (2)	0.2165 (5)	0.029 (1)
C5	0.7699 (7)	0.3687 (2)	0.0416 (5)	0.033 (1)
C6	0.9465 (8)	0.3261 (2)	0.0502 (6)	0.040 (1)
C7	0.9025 (9)	0.2681 (2)	−0.0276 (6)	0.051 (1)
C8	0.6819 (9)	0.2521 (2)	−0.1166 (7)	0.055 (1)
C9	0.5085 (8)	0.2948 (2)	−0.1272 (6)	0.055 (1)
C10	0.5498 (8)	0.3534 (2)	−0.0500 (5)	0.045 (1)
H1	0.8223	0.6234	0.5345	0.044*
H2	1.1007	0.6350	0.3460	0.047*
H3	1.0540	0.5408	0.1576	0.043*
H6	1.0955	0.3365	0.1089	0.048*
H7	1.0219	0.2396	−0.0203	0.061*
H8	0.6519	0.2129	−0.1684	0.066*
H9	0.3601	0.2844	−0.1874	0.066*
H10	0.4306	0.3821	−0.0597	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0341 (4)	0.0312 (4)	0.0241 (4)	−0.0041 (3)	0.0079 (3)	−0.0040 (3)
S1	0.0428 (6)	0.0424 (6)	0.0385 (6)	−0.0132 (4)	0.0187 (5)	−0.0150 (4)
N1	0.037 (2)	0.032 (2)	0.024 (2)	−0.003 (1)	0.007 (1)	−0.004 (1)
N2	0.034 (2)	0.030 (2)	0.025 (2)	−0.002 (1)	0.009 (1)	−0.004 (1)
N3	0.038 (2)	0.037 (2)	0.029 (2)	−0.004 (1)	0.012 (1)	−0.006 (1)
C1	0.043 (2)	0.034 (2)	0.031 (2)	−0.004 (2)	0.004 (2)	−0.005 (2)
C2	0.043 (2)	0.039 (2)	0.033 (2)	−0.008 (2)	0.006 (2)	0.000 (2)
C3	0.038 (2)	0.038 (2)	0.033 (2)	−0.006 (2)	0.014 (2)	0.002 (2)
C4	0.031 (2)	0.030 (2)	0.023 (2)	−0.002 (1)	0.003 (2)	0.001 (1)
C5	0.041 (2)	0.035 (2)	0.024 (2)	−0.002 (2)	0.011 (2)	0.000 (2)
C6	0.039 (2)	0.043 (2)	0.040 (2)	0.001 (2)	0.012 (2)	−0.001 (2)
C7	0.065 (3)	0.041 (2)	0.051 (3)	0.011 (2)	0.022 (2)	−0.001 (2)
C8	0.078 (4)	0.038 (2)	0.052 (3)	−0.010 (2)	0.021 (3)	−0.014 (2)
C9	0.057 (3)	0.061 (3)	0.043 (3)	−0.009 (2)	0.004 (2)	−0.019 (2)
C10	0.047 (3)	0.051 (3)	0.032 (2)	0.004 (2)	0.002 (2)	−0.009 (2)

Geometric parameters (Å, º) top

Ni1—N1	1.869 (3)	C5—C6	1.385 (5)
Ni1—N1ⁱ	1.869 (3)	C6—C7	1.379 (6)
Ni1—S1	2.194 (1)	C7—C8	1.384 (7)
Ni1—S1ⁱ	2.194 (1)	C8—C9	1.370 (7)
S1—C4	1.737 (4)	C9—C10	1.387 (6)
N1—C1	1.334 (5)	C1—H1	0.93
N1—N2	1.362 (4)	C2—H2	0.93
N2—C3	1.349 (5)	C3—H3	0.93
N2—C4	1.426 (5)	C6—H6	0.93
N3—C4	1.266 (5)	C7—H7	0.93
N3—C5	1.426 (5)	C8—H8	0.93
C1—C2	1.398 (5)	C9—H9	0.93
C2—C3	1.363 (6)	C10—H10	0.93
C5—C10	1.384 (6)

N1—Ni1—N1ⁱ	180	C6—C5—N3	117.0 (4)
N1—Ni1—S1	87.45 (9)	C7—C6—C5	120.4 (4)
N1—Ni1—S1ⁱ	92.55 (9)	C6—C7—C8	120.4 (4)
N1ⁱ—Ni1—S1	92.55 (9)	C9—C8—C7	119.0 (4)
N1ⁱ—Ni1—S1ⁱ	87.45 (9)	C8—C9—C10	121.3 (4)
S1—Ni1—S1ⁱ	180	C5—C10—C9	119.4 (4)
C4—S1—Ni1	99.03 (13)	N1—C1—H1	124.5
C1—N1—N2	105.0 (3)	C2—C1—H1	124.5
C1—N1—Ni1	135.5 (3)	C3—C2—H2	127.4
N2—N1—Ni1	119.5 (2)	C1—C2—H2	127.4
C3—N2—N1	111.2 (3)	N2—C3—H3	126.2
C3—N2—C4	129.4 (3)	C2—C3—H3	126.2
N1—N2—C4	119.3 (3)	C7—C6—H6	119.8
C4—N3—C5	122.4 (3)	C5—C6—H6	119.8
N1—C1—C2	111.0 (3)	C6—C7—H7	119.8
C3—C2—C1	105.3 (3)	C8—C7—H7	119.8
N2—C3—C2	107.5 (3)	C9—C8—H8	120.5
N3—C4—N2	115.2 (3)	C7—C8—H8	120.5
N3—C4—S1	131.5 (3)	C8—C9—H9	119.3
N2—C4—S1	113.3 (2)	C10—C9—H9	119.3
C10—C5—C6	119.4 (4)	C5—C10—H10	120.3
C10—C5—N3	123.4 (4)	C9—C10—H10	120.3

N1—Ni1—S1—C4	9.2 (2)	C5—N3—C4—S1	1.0 (6)
N1ⁱ—Ni1—S1—C4	−170.8 (2)	C3—N2—C4—N3	8.1 (6)
S1—Ni1—N1—C1	175.3 (4)	N1—N2—C4—N3	−168.7 (3)
S1ⁱ—Ni1—N1—C1	−4.7 (4)	C3—N2—C4—S1	−173.4 (3)
S1—Ni1—N1—N2	−6.2 (3)	N1—N2—C4—S1	9.8 (4)
S1ⁱ—Ni1—N1—N2	173.8 (3)	Ni1—S1—C4—N3	166.1 (4)
C1—N1—N2—C3	0.8 (4)	Ni1—S1—C4—N2	−12.0 (3)
Ni1—N1—N2—C3	−178.1 (3)	C4—N3—C5—C10	51.3 (6)
C1—N1—N2—C4	178.2 (3)	C4—N3—C5—C6	−133.9 (4)
Ni1—N1—N2—C4	−0.8 (5)	C10—C5—C6—C7	−1.7 (6)
N2—N1—C1—C2	−0.6 (4)	N3—C5—C6—C7	−176.8 (4)
Ni1—N1—C1—C2	178.2 (3)	C5—C6—C7—C8	0.6 (7)
N1—C1—C2—C3	0.1 (5)	C6—C7—C8—C9	0.5 (7)
N1—N2—C3—C2	−0.8 (5)	C7—C8—C9—C10	−0.3 (8)
C4—N2—C3—C2	−177.8 (4)	C6—C5—C10—C9	1.9 (6)
C1—C2—C3—N2	0.4 (5)	N3—C5—C10—C9	176.6 (4)
C5—N3—C4—N2	179.1 (3)	C8—C9—C10—C5	−0.8 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₀H₈N₃S)₂]
M_r	463.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	5.9847 (5), 21.365 (2), 7.8700 (6)
β (°)	103.605 (1)
V (Å³)	978.05 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.43 × 0.16 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.453, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	6319, 2147, 1655
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.643

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.173, 1.10
No. of reflections	2147
No. of parameters	133
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.40, −0.83

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, atomic coordinates taken from the isostructural Cu analogue (Hossain Sadr et al., 2005), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) top

Ni1—N1	1.869 (3)	Ni1—S1	2.194 (1)

N1—Ni1—S1	87.45 (9)

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