Bis[benzyl N'-(1H-indol-3-ylmethyl-ene)hydrazinecarbodithio-ato-κN',S]nickel(II) N,N-dimethyl-formamide disolvate.

In the title compound, [Ni(C(17)H(14)N(3)S(2))(2)]·2C(3)H(7)NO, the Ni atom (site symmetry ) is N,S-chelated by two deprotonated Schiff base anions in a distorted square-planar geometry. The dihedral angle between the aromatic ring planes within the ligand is 86.37 (13)°. In the crystal structure, an N-H⋯O hydrogen bond links the complex to the dimethyl-formamide solvent mol-ecule.

Related literature

For other square-planar nickel dithio­carbaza­tes, see: Ali et al. (2000 ▶); Tian et al. (1996a ▶,b ▶); Xue et al. (2003 ▶); Zhang et al. (2004 ▶); Zhu et al. (2000 ▶).

Experimental

Crystal data

[Ni(C17H14N3S2)2]·2C3H7NO

M = 853.77

Monoclinic,

a = 10.3808 (3) Å

b = 20.0219 (7) Å

c = 10.7831 (3) Å

β = 117.921 (2)°

V = 1980.3 (1) Å3

Z = 2

Mo Kα radiation

μ = 0.75 mm−1

T = 100 (2) K

0.12 × 0.12 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.916, T max = 0.957

13342 measured reflections

3481 independent reflections

2615 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.094

S = 1.03

3481 reflections

252 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.29 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 ▶); software used to prepare material for publication: pubCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038580/hb2849sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038580/hb2849Isup2.hkl

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

[Ni(C17H14N3S2)2]·2C3H7NO	F000 = 892
Mr = 853.77	Dx = 1.432 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1450 reflections
a = 10.3808 (3) Å	θ = 2.2–22.7º
b = 20.0219 (7) Å	µ = 0.75 mm−1
c = 10.7831 (3) Å	T = 100 (2) K
β = 117.921 (2)º	Block, brown
V = 1980.3 (1) Å3	0.12 × 0.12 × 0.06 mm
Z = 2

Bruker SMART APEX CCD diffractometer	3481 independent reflections
Radiation source: fine-focus sealed tube	2615 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.062
T = 100(2) K	θmax = 25.0º
ω scans	θmin = 2.0º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.916, Tmax = 0.957	k = −23→23
13342 measured reflections	l = −12→12

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0396P)2 + 0.2888P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3481 reflections	Δρmax = 0.50 e Å−3
252 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	0.5000	0.01710 (15)
S1	0.48640 (8)	0.60841 (4)	0.48343 (8)	0.0236 (2)
S2	0.38426 (8)	0.70431 (4)	0.62163 (8)	0.0234 (2)
O1	0.1755 (3)	0.56685 (12)	1.1091 (2)	0.0472 (7)
N1	0.2818 (3)	0.49406 (11)	0.9618 (2)	0.0220 (6)
H1	0.2520	0.5191	1.0105	0.026*
N2	0.4331 (2)	0.51020 (11)	0.6371 (2)	0.0182 (5)
N3	0.3953 (2)	0.57357 (11)	0.6685 (2)	0.0192 (5)
N4	0.0849 (3)	0.57529 (12)	1.2634 (2)	0.0252 (6)
C1	0.2942 (3)	0.42563 (14)	0.9707 (3)	0.0192 (6)
C2	0.2658 (3)	0.38131 (15)	1.0548 (3)	0.0232 (7)
H2	0.2351	0.3967	1.1200	0.028*
C3	0.2842 (3)	0.31463 (15)	1.0393 (3)	0.0260 (7)
H3	0.2647	0.2832	1.0945	0.031*
C4	0.3308 (3)	0.29162 (15)	0.9445 (3)	0.0250 (7)
H4	0.3412	0.2450	0.9354	0.030*
C5	0.3621 (3)	0.33626 (15)	0.8636 (3)	0.0219 (7)
H5	0.3955	0.3205	0.8005	0.026*
C6	0.3437 (3)	0.40438 (14)	0.8763 (3)	0.0187 (6)
C7	0.3625 (3)	0.46401 (14)	0.8099 (3)	0.0188 (6)
C8	0.3220 (3)	0.51697 (15)	0.8678 (3)	0.0223 (7)
H8	0.3227	0.5627	0.8443	0.027*
C9	0.4138 (3)	0.46239 (15)	0.7091 (3)	0.0198 (7)
H9	0.4382	0.4191	0.6907	0.024*
C10	0.4193 (3)	0.62076 (14)	0.6009 (3)	0.0191 (6)
C11	0.3353 (3)	0.70343 (15)	0.7620 (3)	0.0245 (7)
H11A	0.4028	0.6726	0.8354	0.029*
H11B	0.3535	0.7487	0.8039	0.029*
C12	0.1817 (3)	0.68378 (14)	0.7277 (3)	0.0206 (7)
C13	0.0673 (3)	0.68232 (15)	0.5927 (3)	0.0259 (7)
H13	0.0838	0.6939	0.5159	0.031*
C14	−0.0716 (3)	0.66398 (16)	0.5687 (3)	0.0309 (8)
H14	−0.1490	0.6622	0.4754	0.037*
C15	−0.0977 (3)	0.64846 (16)	0.6793 (3)	0.0320 (8)
H15	−0.1930	0.6364	0.6627	0.038*
C16	0.0152 (3)	0.65049 (15)	0.8139 (3)	0.0291 (8)
H16	−0.0020	0.6398	0.8908	0.035*
C17	0.1540 (3)	0.66816 (15)	0.8379 (3)	0.0243 (7)
H17	0.2312	0.6696	0.9313	0.029*
C18	0.1381 (4)	0.54196 (18)	1.1919 (3)	0.0376 (9)
H18	0.1485	0.4950	1.2054	0.045*
C19	0.0701 (3)	0.64730 (15)	1.2501 (3)	0.0289 (8)
H19A	0.0755	0.6616	1.1658	0.043*
H19B	0.1489	0.6684	1.3329	0.043*
H19C	−0.0241	0.6606	1.2427	0.043*
C20	0.0490 (3)	0.54232 (15)	1.3634 (3)	0.0293 (7)
H20A	0.0590	0.4939	1.3579	0.044*
H20B	−0.0516	0.5531	1.3412	0.044*
H20C	0.1154	0.5578	1.4584	0.044*

	U11	U22	U33	U12	U13	U23
Ni1	0.0178 (3)	0.0178 (3)	0.0192 (3)	−0.0001 (2)	0.0116 (2)	−0.0001 (2)
S1	0.0326 (5)	0.0197 (4)	0.0292 (4)	0.0005 (3)	0.0234 (4)	0.0002 (3)
S2	0.0297 (5)	0.0183 (4)	0.0296 (4)	−0.0010 (3)	0.0201 (4)	−0.0016 (3)
O1	0.0752 (19)	0.0443 (17)	0.0405 (14)	0.0204 (13)	0.0424 (14)	0.0058 (12)
N1	0.0274 (14)	0.0212 (15)	0.0242 (13)	−0.0007 (11)	0.0178 (11)	−0.0028 (11)
N2	0.0186 (13)	0.0152 (14)	0.0220 (12)	0.0001 (10)	0.0106 (10)	−0.0005 (10)
N3	0.0197 (13)	0.0175 (14)	0.0223 (13)	0.0009 (10)	0.0114 (11)	−0.0031 (10)
N4	0.0265 (15)	0.0263 (16)	0.0239 (13)	0.0015 (11)	0.0129 (12)	−0.0056 (11)
C1	0.0192 (16)	0.0213 (17)	0.0180 (14)	−0.0012 (13)	0.0094 (12)	0.0003 (12)
C2	0.0225 (17)	0.0289 (19)	0.0212 (15)	−0.0016 (14)	0.0128 (13)	0.0023 (13)
C3	0.0232 (17)	0.030 (2)	0.0264 (16)	0.0009 (14)	0.0128 (14)	0.0100 (14)
C4	0.0229 (17)	0.0197 (17)	0.0319 (17)	0.0021 (13)	0.0123 (14)	0.0079 (13)
C5	0.0188 (16)	0.0253 (18)	0.0229 (15)	0.0023 (13)	0.0110 (13)	0.0003 (13)
C6	0.0129 (15)	0.0237 (18)	0.0205 (15)	0.0019 (12)	0.0088 (12)	0.0023 (12)
C7	0.0172 (16)	0.0200 (17)	0.0203 (15)	−0.0010 (12)	0.0098 (13)	−0.0001 (12)
C8	0.0243 (17)	0.0242 (18)	0.0217 (15)	−0.0019 (13)	0.0134 (13)	0.0033 (12)
C9	0.0172 (16)	0.0201 (18)	0.0237 (16)	0.0008 (12)	0.0107 (13)	−0.0002 (12)
C10	0.0162 (16)	0.0222 (17)	0.0183 (14)	−0.0012 (12)	0.0076 (12)	−0.0008 (12)
C11	0.0304 (18)	0.0232 (18)	0.0263 (16)	−0.0054 (14)	0.0186 (14)	−0.0074 (13)
C12	0.0251 (17)	0.0148 (16)	0.0282 (16)	0.0002 (13)	0.0177 (14)	−0.0055 (12)
C13	0.0301 (19)	0.0247 (18)	0.0265 (17)	0.0025 (14)	0.0164 (15)	−0.0007 (13)
C14	0.0224 (18)	0.032 (2)	0.0314 (18)	0.0053 (14)	0.0071 (15)	−0.0008 (15)
C15	0.0232 (18)	0.031 (2)	0.044 (2)	0.0045 (14)	0.0177 (16)	0.0048 (15)
C16	0.0322 (19)	0.0273 (19)	0.0366 (19)	0.0018 (14)	0.0234 (16)	0.0042 (14)
C17	0.0246 (18)	0.0256 (18)	0.0264 (16)	−0.0007 (14)	0.0150 (14)	−0.0043 (13)
C18	0.048 (2)	0.034 (2)	0.0333 (19)	0.0081 (17)	0.0206 (18)	−0.0021 (16)
C19	0.034 (2)	0.028 (2)	0.0260 (17)	0.0037 (15)	0.0150 (15)	−0.0037 (14)
C20	0.0300 (18)	0.029 (2)	0.0324 (18)	−0.0026 (14)	0.0177 (15)	−0.0049 (14)

Ni1—N2i	1.916 (2)	C6—C7	1.451 (4)
Ni1—N2	1.916 (2)	C7—C8	1.391 (4)
Ni1—S1	2.1770 (7)	C7—C9	1.418 (4)
Ni1—S1i	2.1770 (7)	C8—H8	0.9500
S1—C10	1.725 (3)	C9—H9	0.9500
S2—C10	1.748 (3)	C11—C12	1.511 (4)
S2—C11	1.808 (3)	C11—H11A	0.9900
O1—C18	1.233 (4)	C11—H11B	0.9900
N1—C8	1.346 (3)	C12—C17	1.383 (4)
N1—C1	1.375 (3)	C12—C13	1.382 (4)
N1—H1	0.8800	C13—C14	1.390 (4)
N2—C9	1.306 (3)	C13—H13	0.9500
N2—N3	1.416 (3)	C14—C15	1.377 (4)
N3—C10	1.287 (3)	C14—H14	0.9500
N4—C18	1.321 (4)	C15—C16	1.375 (4)
N4—C20	1.454 (4)	C15—H15	0.9500
N4—C19	1.450 (4)	C16—C17	1.385 (4)
C1—C2	1.395 (4)	C16—H16	0.9500
C1—C6	1.404 (4)	C17—H17	0.9500
C2—C3	1.370 (4)	C18—H18	0.9500
C2—H2	0.9500	C19—H19A	0.9800
C3—C4	1.398 (4)	C19—H19B	0.9800
C3—H3	0.9500	C19—H19C	0.9800
C4—C5	1.390 (4)	C20—H20A	0.9800
C4—H4	0.9500	C20—H20B	0.9800
C5—C6	1.393 (4)	C20—H20C	0.9800
C5—H5	0.9500
N2i—Ni1—N2	180.0	C7—C9—H9	114.5
N2i—Ni1—S1	94.36 (7)	N3—C10—S1	124.2 (2)
N2—Ni1—S1	85.64 (7)	N3—C10—S2	121.5 (2)
N2i—Ni1—S1i	85.64 (7)	S1—C10—S2	114.26 (16)
N2—Ni1—S1i	94.36 (7)	C12—C11—S2	118.4 (2)
S1—Ni1—S1i	180.0	C12—C11—H11A	107.7
C10—S1—Ni1	96.64 (10)	S2—C11—H11A	107.7
C10—S2—C11	104.76 (13)	C12—C11—H11B	107.7
C8—N1—C1	109.9 (2)	S2—C11—H11B	107.7
C8—N1—H1	125.1	H11A—C11—H11B	107.1
C1—N1—H1	125.1	C17—C12—C13	118.5 (3)
C9—N2—N3	112.2 (2)	C17—C12—C11	118.0 (2)
C9—N2—Ni1	126.4 (2)	C13—C12—C11	123.5 (3)
N3—N2—Ni1	121.46 (17)	C12—C13—C14	120.4 (3)
C10—N3—N2	111.9 (2)	C12—C13—H13	119.8
C18—N4—C20	121.8 (3)	C14—C13—H13	119.8
C18—N4—C19	119.9 (3)	C15—C14—C13	120.4 (3)
C20—N4—C19	118.2 (2)	C15—C14—H14	119.8
N1—C1—C2	129.6 (3)	C13—C14—H14	119.8
N1—C1—C6	107.8 (2)	C14—C15—C16	119.4 (3)
C2—C1—C6	122.6 (3)	C14—C15—H15	120.3
C3—C2—C1	117.2 (3)	C16—C15—H15	120.3
C3—C2—H2	121.4	C15—C16—C17	120.2 (3)
C1—C2—H2	121.4	C15—C16—H16	119.9
C2—C3—C4	121.7 (3)	C17—C16—H16	119.9
C2—C3—H3	119.2	C12—C17—C16	121.0 (3)
C4—C3—H3	119.2	C12—C17—H17	119.5
C5—C4—C3	120.7 (3)	C16—C17—H17	119.5
C5—C4—H4	119.7	O1—C18—N4	125.3 (3)
C3—C4—H4	119.7	O1—C18—H18	117.3
C4—C5—C6	119.0 (3)	N4—C18—H18	117.3
C4—C5—H5	120.5	N4—C19—H19A	109.5
C6—C5—H5	120.5	N4—C19—H19B	109.5
C5—C6—C1	118.8 (3)	H19A—C19—H19B	109.5
C5—C6—C7	134.5 (3)	N4—C19—H19C	109.5
C1—C6—C7	106.7 (2)	H19A—C19—H19C	109.5
C8—C7—C9	131.5 (3)	H19B—C19—H19C	109.5
C8—C7—C6	105.5 (2)	N4—C20—H20A	109.5
C9—C7—C6	123.0 (3)	N4—C20—H20B	109.5
N1—C8—C7	110.1 (3)	H20A—C20—H20B	109.5
N1—C8—H8	125.0	N4—C20—H20C	109.5
C7—C8—H8	125.0	H20A—C20—H20C	109.5
N2—C9—C7	131.1 (3)	H20B—C20—H20C	109.5
N2—C9—H9	114.5
N2i—Ni1—S1—C10	177.84 (11)	C9—C7—C8—N1	−179.2 (3)
N2—Ni1—S1—C10	−2.16 (11)	C6—C7—C8—N1	0.2 (3)
S1—Ni1—N2—C9	−177.9 (2)	N3—N2—C9—C7	0.1 (4)
S1i—Ni1—N2—C9	2.1 (2)	Ni1—N2—C9—C7	−178.5 (2)
S1—Ni1—N2—N3	3.52 (18)	C8—C7—C9—N2	−2.8 (5)
S1i—Ni1—N2—N3	−176.48 (18)	C6—C7—C9—N2	177.9 (3)
C9—N2—N3—C10	177.8 (2)	N2—N3—C10—S1	1.1 (3)
Ni1—N2—N3—C10	−3.5 (3)	N2—N3—C10—S2	−179.25 (17)
C8—N1—C1—C2	179.3 (3)	Ni1—S1—C10—N3	1.2 (2)
C8—N1—C1—C6	−0.5 (3)	Ni1—S1—C10—S2	−178.47 (13)
N1—C1—C2—C3	178.4 (3)	C11—S2—C10—N3	6.4 (3)
C6—C1—C2—C3	−1.9 (4)	C11—S2—C10—S1	−173.95 (15)
C1—C2—C3—C4	0.7 (4)	C10—S2—C11—C12	−80.3 (2)
C2—C3—C4—C5	0.8 (4)	S2—C11—C12—C17	165.3 (2)
C3—C4—C5—C6	−1.2 (4)	S2—C11—C12—C13	−16.5 (4)
C4—C5—C6—C1	0.0 (4)	C17—C12—C13—C14	−1.5 (4)
C4—C5—C6—C7	−178.9 (3)	C11—C12—C13—C14	−179.7 (3)
N1—C1—C6—C5	−178.6 (2)	C12—C13—C14—C15	1.4 (5)
C2—C1—C6—C5	1.5 (4)	C13—C14—C15—C16	−0.7 (5)
N1—C1—C6—C7	0.6 (3)	C14—C15—C16—C17	0.1 (5)
C2—C1—C6—C7	−179.3 (3)	C13—C12—C17—C16	0.9 (4)
C5—C6—C7—C8	178.6 (3)	C11—C12—C17—C16	179.2 (3)
C1—C6—C7—C8	−0.5 (3)	C15—C16—C17—C12	−0.2 (5)
C5—C6—C7—C9	−2.0 (5)	C20—N4—C18—O1	−177.4 (3)
C1—C6—C7—C9	179.0 (2)	C19—N4—C18—O1	−1.6 (5)
C1—N1—C8—C7	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.86	2.739 (3)	175

Table 1

Selected bond lengths (Å)

Ni1—N2	1.916 (2)
Ni1—S1	2.1770 (7)