trans-Bis(1H-indole-3-carbaldehyde thio-semicarbazonato-κN,S)nickel(II).

The Ni atom in the centrosymmetric title compound, [Ni(C(10)H(9)N(4)S)(2)], is N,S-chelated by the deprotonated Schiff bases in a square-planar geometry. The -CH=N-N=C(S)-NH(2) frament is planar. Adjacent mol-ecules are linked by hydrogen bonds between the indolyl -NH (donor) site and the double-bond =N- (acceptor) site of an adjacent mol-ecule, forming a layer motif.

Related literature

For the structure of the neutral Schiff base, see: Rizal et al. (2008 ▶). For background literature on the medicinal activity of metal complexes of the Schiff base and related compounds, see: Husain et al. (2007 ▶); Wilson et al. (2005 ▶).

Experimental

Crystal data

[Ni(C10H9N4S)2]

M = 493.25

Monoclinic,

a = 10.4388 (3) Å

b = 5.2604 (1) Å

c = 19.1122 (5) Å

β = 104.803 (2)°

V = 1014.66 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.19 mm−1

T = 100 (2) K

0.14 × 0.04 × 0.01 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.851, T max = 0.988

12357 measured reflections

2326 independent reflections

1774 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.02

2326 reflections

154 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶; Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014293/sg2241sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014293/sg2241Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C10H9N4S)2]	F000 = 508
Mr = 493.25	Dx = 1.614 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1799 reflections
a = 10.4388 (3) Å	θ = 2.6–24.7º
b = 5.2604 (1) Å	µ = 1.19 mm−1
c = 19.1122 (5) Å	T = 100 (2) K
β = 104.803 (2)º	Plate, orange
V = 1014.66 (4) Å3	0.14 × 0.04 × 0.01 mm
Z = 2

Bruker SMART APEX diffractometer	2326 independent reflections
Radiation source: fine-focus sealed tube	1774 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.062
T = 100(2) K	θmax = 27.5º
φ and ω scans	θmin = 2.0º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.851, Tmax = 0.988	k = −6→6
12357 measured reflections	l = −24→24

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0362P)2 + 0.5143P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2326 reflections	Δρmax = 0.43 e Å−3
154 parameters	Δρmin = −0.30 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	0.5000	0.01261 (12)
S1	0.33444 (6)	0.74950 (12)	0.45463 (3)	0.01747 (15)
N1	0.6654 (2)	1.1528 (4)	0.78929 (11)	0.0171 (5)
H1N	0.637 (3)	1.262 (5)	0.8165 (14)	0.045 (10)*
N2	0.52205 (19)	0.6972 (4)	0.58664 (10)	0.0143 (4)
N3	0.42554 (19)	0.8723 (4)	0.59419 (10)	0.0153 (4)
N4	0.2345 (2)	1.0700 (4)	0.53342 (12)	0.0205 (5)
H4N1	0.240 (3)	1.177 (5)	0.5691 (12)	0.042 (10)*
H4N2	0.184 (3)	1.121 (6)	0.4919 (10)	0.043 (10)*
C1	0.7786 (2)	0.8186 (5)	0.76257 (12)	0.0154 (5)
C2	0.8845 (2)	0.6471 (5)	0.77478 (13)	0.0182 (5)
H2	0.8869	0.5159	0.7410	0.022*
C3	0.9859 (2)	0.6731 (5)	0.83732 (13)	0.0195 (5)
H3	1.0588	0.5590	0.8460	0.023*
C4	0.9830 (2)	0.8646 (5)	0.88809 (13)	0.0190 (5)
H4	1.0538	0.8766	0.9306	0.023*
C5	0.8795 (2)	1.0361 (5)	0.87760 (12)	0.0178 (5)
H5	0.8774	1.1659	0.9118	0.021*
C6	0.7782 (2)	1.0092 (5)	0.81421 (12)	0.0159 (5)
C7	0.5945 (2)	1.0621 (5)	0.72458 (12)	0.0166 (5)
H7	0.5132	1.1309	0.6969	0.020*
C8	0.6586 (2)	0.8537 (5)	0.70493 (12)	0.0166 (5)
C9	0.6276 (2)	0.6972 (5)	0.64112 (12)	0.0163 (5)
H9	0.6935	0.5761	0.6381	0.020*
C10	0.3354 (2)	0.9073 (5)	0.53374 (13)	0.0159 (5)

	U11	U22	U33	U12	U13	U23
Ni1	0.0129 (2)	0.0143 (2)	0.0104 (2)	0.00022 (19)	0.00260 (16)	−0.00047 (18)
S1	0.0180 (3)	0.0207 (3)	0.0124 (3)	0.0042 (3)	0.0014 (2)	−0.0010 (2)
N1	0.0177 (11)	0.0189 (11)	0.0140 (10)	0.0007 (9)	0.0029 (8)	−0.0039 (9)
N2	0.0161 (10)	0.0141 (10)	0.0127 (9)	0.0014 (8)	0.0036 (8)	−0.0004 (8)
N3	0.0155 (11)	0.0171 (11)	0.0137 (10)	0.0021 (9)	0.0047 (8)	−0.0002 (8)
N4	0.0225 (12)	0.0210 (12)	0.0172 (11)	0.0080 (9)	0.0035 (9)	−0.0025 (9)
C1	0.0156 (12)	0.0156 (12)	0.0151 (11)	−0.0034 (10)	0.0042 (10)	0.0002 (9)
C2	0.0190 (13)	0.0192 (13)	0.0177 (12)	−0.0019 (10)	0.0068 (10)	−0.0025 (10)
C3	0.0153 (13)	0.0225 (14)	0.0205 (12)	0.0005 (11)	0.0040 (10)	0.0028 (11)
C4	0.0166 (13)	0.0245 (14)	0.0148 (11)	−0.0037 (11)	0.0018 (10)	−0.0005 (10)
C5	0.0196 (13)	0.0207 (14)	0.0127 (11)	−0.0040 (11)	0.0034 (10)	−0.0005 (10)
C6	0.0172 (12)	0.0167 (12)	0.0151 (11)	−0.0011 (11)	0.0063 (9)	0.0013 (10)
C7	0.0166 (12)	0.0190 (14)	0.0137 (11)	−0.0016 (10)	0.0030 (10)	−0.0003 (9)
C8	0.0191 (13)	0.0177 (13)	0.0135 (11)	−0.0022 (10)	0.0051 (10)	0.0001 (10)
C9	0.0175 (12)	0.0176 (13)	0.0145 (11)	0.0008 (10)	0.0055 (10)	0.0003 (10)
C10	0.0180 (13)	0.0140 (12)	0.0182 (12)	−0.0033 (10)	0.0092 (10)	0.0007 (10)

Ni1—N2i	1.919 (2)	C1—C6	1.408 (3)
Ni1—N2	1.918 (2)	C1—C8	1.453 (3)
Ni1—S1i	2.1669 (6)	C2—C3	1.386 (3)
Ni1—S1	2.1669 (6)	C2—H2	0.9500
S1—C10	1.723 (2)	C3—C4	1.404 (4)
N1—C7	1.355 (3)	C3—H3	0.9500
N1—C6	1.377 (3)	C4—C5	1.382 (4)
N1—H1n	0.88 (3)	C4—H4	0.9500
N2—C9	1.309 (3)	C5—C6	1.397 (3)
N2—N3	1.399 (3)	C5—H5	0.9500
N3—C10	1.303 (3)	C7—C8	1.385 (3)
N4—C10	1.355 (3)	C7—H7	0.9500
N4—H4n1	0.88 (3)	C8—C9	1.438 (3)
N4—H4n2	0.88 (3)	C9—H9	0.9500
C1—C2	1.400 (3)
N2i—Ni1—N2	180.000 (1)	C2—C3—H3	119.3
N2i—Ni1—S1i	85.72 (6)	C4—C3—H3	119.3
N2—Ni1—S1	85.72 (6)	C5—C4—C3	121.5 (2)
N2—Ni1—S1i	94.28 (6)	C5—C4—H4	119.3
N2i—Ni1—S1	94.28 (6)	C3—C4—H4	119.3
S1i—Ni1—S1	180.0	C4—C5—C6	116.8 (2)
C10—S1—Ni1	96.63 (9)	C4—C5—H5	121.6
C7—N1—C6	110.0 (2)	C6—C5—H5	121.6
C7—N1—H1N	126 (2)	N1—C6—C5	129.5 (2)
C6—N1—H1N	123 (2)	N1—C6—C1	107.7 (2)
C9—N2—N3	113.60 (19)	C5—C6—C1	122.9 (2)
C9—N2—Ni1	125.30 (17)	N1—C7—C8	109.7 (2)
N3—N2—Ni1	120.96 (14)	N1—C7—H7	125.1
C10—N3—N2	112.16 (19)	C8—C7—H7	125.1
C10—N4—H4N1	121 (2)	C7—C8—C9	131.6 (2)
C10—N4—H4N2	119 (2)	C7—C8—C1	106.1 (2)
H4N1—N4—H4N2	114 (3)	C9—C8—C1	122.2 (2)
C2—C1—C6	119.1 (2)	N2—C9—C8	129.5 (2)
C2—C1—C8	134.4 (2)	N2—C9—H9	115.3
C6—C1—C8	106.5 (2)	C8—C9—H9	115.3
C3—C2—C1	118.5 (2)	N3—C10—N4	118.5 (2)
C3—C2—H2	120.8	N3—C10—S1	123.44 (19)
C1—C2—H2	120.8	N4—C10—S1	118.03 (18)
C2—C3—C4	121.3 (2)
N2i—Ni1—S1—C10	172.73 (10)	C8—C1—C6—N1	−0.4 (3)
N2—Ni1—S1—C10	−7.27 (10)	C2—C1—C6—C5	0.1 (4)
S1i—Ni1—N2—C9	15.3 (2)	C8—C1—C6—C5	−179.6 (2)
S1—Ni1—N2—C9	−164.7 (2)	C6—N1—C7—C8	0.3 (3)
S1i—Ni1—N2—N3	−169.40 (16)	N1—C7—C8—C9	−177.4 (2)
S1—Ni1—N2—N3	10.60 (16)	N1—C7—C8—C1	−0.5 (3)
C9—N2—N3—C10	166.4 (2)	C2—C1—C8—C7	−179.1 (3)
Ni1—N2—N3—C10	−9.4 (3)	C6—C1—C8—C7	0.6 (3)
C6—C1—C2—C3	−0.5 (4)	C2—C1—C8—C9	−1.8 (4)
C8—C1—C2—C3	179.2 (3)	C6—C1—C8—C9	177.8 (2)
C1—C2—C3—C4	0.6 (4)	N3—N2—C9—C8	−2.0 (4)
C2—C3—C4—C5	−0.4 (4)	Ni1—N2—C9—C8	173.7 (2)
C3—C4—C5—C6	0.1 (4)	C7—C8—C9—N2	−7.0 (5)
C7—N1—C6—C5	179.2 (2)	C1—C8—C9—N2	176.5 (2)
C7—N1—C6—C1	0.1 (3)	N2—N3—C10—N4	179.1 (2)
C4—C5—C6—N1	−178.9 (2)	N2—N3—C10—S1	1.4 (3)
C4—C5—C6—C1	0.1 (4)	Ni1—S1—C10—N3	5.4 (2)
C2—C1—C6—N1	179.3 (2)	Ni1—S1—C10—N4	−172.37 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N3ii	0.88 (3)	2.06 (2)	2.876 (3)	155 (3)

Ni1—N2	1.918 (2)
Ni1—S1	2.1669 (6)

N2—Ni1—S1	85.72 (6)
N2—Ni1—S1i	94.28 (6)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N3ii	0.88 (3)	2.06 (2)	2.876 (3)	155 (3)

Symmetry code: (ii) .