Crystal structure of S-n-octyl 3-(1-phenyl­ethyl­idene)di­thio­carbazate and of its bis-chelated nickel(II) complex

A bis-chelated mononuclear nickel(II) complex with a di­thio­carbazate ligand bearing a long saturated alkyl chain exhibits a distorted cis square planar coordination of the metal with two ligands conformationally different from the proligand.

Computing details

S-n-Octyl 3-(1-phenylethylidene)dithiocarbazate (HL)

Crystal data

C17H26N2S2	Z = 2
Mr = 322.52	F(000) = 348
Triclinic, P1	Dx = 1.162 Mg m^−3
a = 4.9925 (6) Å	Mo Kα radiation, λ = 0.71075 Å
b = 12.4283 (16) Å	Cell parameters from 6282 reflections
c = 15.0643 (19) Å	θ = 2.0–27.5°
α = 98.420 (7)°	µ = 0.28 mm^−1
β = 94.302 (7)°	T = 173 K
γ = 91.150 (6)°	Plate, colorless
V = 921.6 (2) Å^3	0.19 × 0.10 × 0.07 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	3093 reflections with I > 2σ(I)
ω scans	Rint = 0.037
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	θmax = 27.5°, θmin = 2.3°
Tmin = 0.410, Tmax = 0.980	h = −6→5
8449 measured reflections	k = −16→16
4181 independent reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.196	w = 1/[σ^2(Fo^2) + (0.0649P)^2 + 1.6447P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
4181 reflections	Δρmax = 0.55 e Å^−3
242 parameters	Δρmin = −0.32 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	−0.1043 (6)	0.7323 (2)	0.1266 (2)	0.0401 (7)
N2	−0.2090 (6)	0.6296 (2)	0.0940 (2)	0.0409 (7)
H2N	−0.344 (7)	0.616 (3)	0.053 (2)	0.031 (9)*
S1	−0.20157 (19)	0.41740 (7)	0.08485 (6)	0.0432 (3)
S2	0.16745 (18)	0.58140 (7)	0.20863 (6)	0.0431 (3)
C1	−0.0902 (7)	0.9225 (3)	0.1334 (3)	0.0423 (8)
C2A	−0.2308 (19)	1.0181 (6)	0.1290 (6)	0.0504 (19)	0.5
H2A	−0.412706	1.013940	0.104862	0.060*	0.5
C3A	−0.107 (2)	1.1189 (7)	0.1597 (7)	0.056 (2)	0.5
H3A	−0.196708	1.183166	0.149810	0.067*	0.5
C2	−0.1086 (16)	1.0104 (6)	0.0810 (6)	0.0461 (17)	0.5
H2	−0.190437	0.998522	0.021250	0.055*	0.5
C3	−0.0052 (18)	1.1128 (7)	0.1190 (7)	0.049 (2)	0.5
H3	−0.031247	1.173157	0.087547	0.058*	0.5
C4	0.1357 (10)	1.1268 (3)	0.2027 (3)	0.0619 (12)
H4	0.221191	1.194944	0.226559	0.074*
C5A	0.283 (2)	1.0330 (8)	0.2134 (7)	0.060 (2)	0.5
H5A	0.460126	1.039291	0.241511	0.072*	0.5
C6A	0.1629 (19)	0.9312 (8)	0.1820 (7)	0.049 (2)	0.5
H6A	0.252208	0.867290	0.193560	0.059*	0.5
C5	0.151 (2)	1.0410 (8)	0.2510 (7)	0.057 (2)	0.5
H5	0.230184	1.052526	0.311120	0.068*	0.5
C6	0.053 (2)	0.9385 (8)	0.2135 (6)	0.046 (2)	0.5
H6	0.087011	0.878548	0.244745	0.055*	0.5
C7	−0.2107 (8)	0.8138 (3)	0.0956 (3)	0.0471 (9)
C8A	−0.477 (4)	0.804 (2)	0.0421 (15)	0.062 (5)	0.5
H8A	−0.457921	0.763747	−0.017873	0.075*	0.5
H8B	−0.540448	0.877297	0.036156	0.075*	0.5
H8C	−0.606766	0.765985	0.072809	0.075*	0.5
C8	−0.405 (4)	0.7988 (19)	0.0111 (15)	0.067 (6)	0.5
H8D	−0.329965	0.748035	−0.036166	0.081*	0.5
H8E	−0.430501	0.869171	−0.009852	0.081*	0.5
H8F	−0.577752	0.769499	0.024940	0.081*	0.5
C9	−0.0943 (7)	0.5445 (3)	0.1251 (2)	0.0363 (7)
C10	0.2629 (7)	0.4508 (3)	0.2385 (2)	0.0406 (8)
H10A	0.105264	0.412724	0.257139	0.049*
H10B	0.330537	0.404971	0.185987	0.049*
C11	0.4822 (7)	0.4701 (3)	0.3158 (2)	0.0421 (8)
H11A	0.637148	0.509765	0.297023	0.051*
H11B	0.412573	0.515802	0.368017	0.051*
C12	0.5748 (7)	0.3632 (3)	0.3436 (2)	0.0433 (8)
H12A	0.651622	0.319515	0.291733	0.052*
H12B	0.416427	0.321934	0.358284	0.052*
C13	0.7831 (8)	0.3763 (3)	0.4239 (2)	0.0458 (8)
H13A	0.941383	0.417864	0.409574	0.055*
H13B	0.706096	0.419128	0.476121	0.055*
C14	0.8745 (8)	0.2683 (3)	0.4499 (3)	0.0479 (9)
H14A	0.714985	0.226115	0.462490	0.057*
H14B	0.954852	0.226428	0.398009	0.057*
C15	1.0773 (8)	0.2790 (4)	0.5313 (3)	0.0520 (9)
H15A	1.237728	0.320556	0.518707	0.062*
H15B	0.997681	0.321188	0.583283	0.062*
C16	1.1647 (10)	0.1709 (4)	0.5568 (3)	0.0652 (12)
H16A	1.244326	0.128450	0.504959	0.078*
H16B	1.004888	0.129348	0.569939	0.078*
C17	1.3697 (11)	0.1840 (5)	0.6387 (4)	0.0820 (16)
H17A	1.429776	0.112155	0.649602	0.098*
H17B	1.286255	0.219771	0.691591	0.098*
H17C	1.524302	0.228373	0.627259	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0423 (16)	0.0350 (14)	0.0419 (16)	−0.0025 (12)	−0.0012 (13)	0.0052 (12)
N2	0.0427 (16)	0.0373 (15)	0.0416 (16)	−0.0035 (12)	−0.0029 (14)	0.0062 (13)
S1	0.0482 (5)	0.0357 (4)	0.0442 (5)	−0.0042 (4)	−0.0046 (4)	0.0053 (4)
S2	0.0441 (5)	0.0387 (5)	0.0449 (5)	−0.0039 (4)	−0.0062 (4)	0.0064 (4)
C1	0.0404 (18)	0.0364 (17)	0.049 (2)	0.0006 (14)	−0.0064 (16)	0.0067 (15)
C2A	0.053 (5)	0.042 (4)	0.054 (5)	0.006 (4)	−0.011 (4)	0.003 (4)
C3A	0.073 (7)	0.032 (4)	0.061 (6)	0.005 (4)	−0.009 (5)	0.003 (4)
C2	0.043 (4)	0.043 (4)	0.048 (4)	0.004 (3)	−0.012 (4)	0.001 (4)
C3	0.045 (5)	0.037 (4)	0.065 (6)	−0.002 (4)	−0.005 (4)	0.017 (4)
C4	0.075 (3)	0.038 (2)	0.067 (3)	−0.0090 (19)	−0.016 (2)	0.0005 (19)
C5A	0.060 (6)	0.050 (5)	0.064 (6)	−0.004 (5)	−0.020 (5)	0.002 (5)
C6A	0.045 (5)	0.044 (4)	0.058 (6)	−0.007 (4)	−0.008 (4)	0.011 (4)
C5	0.061 (6)	0.053 (5)	0.050 (5)	0.000 (5)	−0.013 (4)	−0.004 (4)
C6	0.053 (6)	0.039 (4)	0.045 (5)	−0.002 (4)	−0.007 (4)	0.006 (4)
C7	0.0436 (19)	0.0381 (18)	0.057 (2)	−0.0040 (15)	−0.0158 (17)	0.0091 (16)
C8A	0.046 (8)	0.047 (6)	0.089 (15)	−0.002 (5)	−0.026 (7)	0.007 (9)
C8	0.075 (14)	0.035 (5)	0.083 (13)	−0.001 (8)	−0.039 (9)	0.006 (7)
C9	0.0375 (17)	0.0376 (17)	0.0341 (16)	−0.0016 (13)	0.0065 (14)	0.0047 (13)
C10	0.0409 (18)	0.0404 (18)	0.0407 (18)	0.0006 (14)	0.0001 (15)	0.0080 (15)
C11	0.0419 (19)	0.0436 (19)	0.0394 (18)	−0.0007 (15)	−0.0022 (15)	0.0045 (15)
C12	0.0411 (19)	0.047 (2)	0.0403 (19)	−0.0044 (15)	−0.0051 (15)	0.0073 (15)
C13	0.046 (2)	0.052 (2)	0.0380 (19)	−0.0030 (16)	−0.0043 (16)	0.0056 (16)
C14	0.0417 (19)	0.057 (2)	0.044 (2)	−0.0016 (16)	−0.0046 (16)	0.0084 (17)
C15	0.046 (2)	0.065 (3)	0.045 (2)	0.0032 (18)	−0.0029 (17)	0.0120 (19)
C16	0.059 (3)	0.076 (3)	0.065 (3)	0.008 (2)	−0.004 (2)	0.027 (2)
C17	0.069 (3)	0.114 (5)	0.067 (3)	0.018 (3)	−0.010 (3)	0.034 (3)

Geometric parameters (Å, º)

N1—C7	1.284 (4)	C8A—H8A	0.9800
N1—N2	1.377 (4)	C8A—H8B	0.9800
N2—C9	1.340 (4)	C8A—H8C	0.9800
N2—H2N	0.87 (4)	C8—H8D	0.9800
S1—C9	1.669 (3)	C8—H8E	0.9800
S2—C9	1.750 (3)	C8—H8F	0.9800
S2—C10	1810 (3)	C10—C11	1.526 (5)
C1—C6	1.342 (10)	C10—H10A	0.9900
C1—C2A	1.399 (9)	C10—H10B	0.9900
C1—C6A	1.407 (10)	C11—C12	1.521 (5)
C1—C2	1.438 (9)	C11—H11A	0.9900
C1—C7	1.484 (5)	C11—H11B	0.9900
C2A—C3A	1.387 (12)	C12—C13	1.523 (5)
C2A—H2A	0.9500	C12—H12A	0.9900
C3A—C4	1.323 (11)	C12—H12B	0.9900
C3A—H3A	0.9500	C13—C14	1.521 (5)
C2—C3	1.390 (12)	C13—H13A	0.9900
C2—H2	0.9500	C13—H13B	0.9900
C3—C4	1.382 (10)	C14—C15	1.519 (5)
C3—H3	0.9500	C14—H14A	0.9900
C4—C5	1.377 (11)	C14—H14B	0.9900
C4—C5A	1.413 (11)	C15—C16	1.513 (6)
C4—H4	0.9500	C15—H15A	0.9900
C5A—C6A	1.390 (13)	C15—H15B	0.9900
C5A—H5A	0.9500	C16—C17	1.530 (6)
C6A—H6A	0.9500	C16—H16A	0.9900
C5—C6	1.380 (13)	C16—H16B	0.9900
C5—H5	0.9500	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C7—C8A	1.50 (2)	C17—H17C	0.9800
C7—C8	1.53 (2)
C7—N1—N2	118.4 (3)	H8D—C8—H8F	109.5
C9—N2—N1	118.4 (3)	H8E—C8—H8F	109.5
C9—N2—H2N	117 (2)	N2—C9—S1	120.8 (3)
N1—N2—H2N	124 (2)	N2—C9—S2	113.6 (2)
C9—S2—C10	102.08 (16)	S1—C9—S2	125.6 (2)
C2A—C1—C6A	117.8 (6)	C11—C10—S2	108.4 (2)
C6—C1—C2	119.0 (6)	C11—C10—H10A	110.0
C6—C1—C7	120.9 (5)	S2—C10—H10A	110.0
C2A—C1—C7	121.9 (4)	C11—C10—H10B	110.0
C6A—C1—C7	120.1 (5)	S2—C10—H10B	110.0
C2—C1—C7	119.9 (4)	H10A—C10—H10B	108.4
C3A—C2A—C1	120.5 (8)	C12—C11—C10	111.2 (3)
C3A—C2A—H2A	119.8	C12—C11—H11A	109.4
C1—C2A—H2A	119.8	C10—C11—H11A	109.4
C4—C3A—C2A	121.0 (8)	C12—C11—H11B	109.4
C4—C3A—H3A	119.5	C10—C11—H11B	109.4
C2A—C3A—H3A	119.5	H11A—C11—H11B	108.0
C3—C2—C1	119.1 (7)	C11—C12—C13	114.1 (3)
C3—C2—H2	120.4	C11—C12—H12A	108.7
C1—C2—H2	120.4	C13—C12—H12A	108.7
C4—C3—C2	119.9 (8)	C11—C12—H12B	108.7
C4—C3—H3	120.1	C13—C12—H12B	108.7
C2—C3—H3	120.1	H12A—C12—H12B	107.6
C5—C4—C3	119.4 (6)	C14—C13—C12	113.2 (3)
C3A—C4—C5A	121.0 (6)	C14—C13—H13A	108.9
C5—C4—H4	120.3	C12—C13—H13A	108.9
C3—C4—H4	120.3	C14—C13—H13B	108.9
C6A—C5A—C4	118.9 (8)	C12—C13—H13B	108.9
C6A—C5A—H5A	120.6	H13A—C13—H13B	107.8
C4—C5A—H5A	120.6	C15—C14—C13	114.3 (3)
C5A—C6A—C1	120.2 (9)	C15—C14—H14A	108.7
C5A—C6A—H6A	119.9	C13—C14—H14A	108.7
C1—C6A—H6A	119.9	C15—C14—H14B	108.7
C4—C5—C6	121.0 (8)	C13—C14—H14B	108.7
C4—C5—H5	119.5	H14A—C14—H14B	107.6
C6—C5—H5	119.5	C16—C15—C14	113.7 (4)
C1—C6—C5	120.8 (8)	C16—C15—H15A	108.8
C1—C6—H6	119.6	C14—C15—H15A	108.8
C5—C6—H6	119.6	C16—C15—H15B	108.8
N1—C7—C1	116.1 (3)	C14—C15—H15B	108.8
N1—C7—C8A	122.2 (10)	H15A—C15—H15B	107.7
C1—C7—C8A	120.2 (10)	C15—C16—C17	112.6 (4)
N1—C7—C8	121.7 (9)	C15—C16—H16A	109.1
C1—C7—C8	120.9 (9)	C17—C16—H16A	109.1
C7—C8A—H8A	109.5	C15—C16—H16B	109.1
C7—C8A—H8B	109.5	C17—C16—H16B	109.1
H8A—C8A—H8B	109.5	H16A—C16—H16B	107.8
C7—C8A—H8C	109.5	C16—C17—H17A	109.5
H8A—C8A—H8C	109.5	C16—C17—H17B	109.5
H8B—C8A—H8C	109.5	H17A—C17—H17B	109.5
C7—C8—H8D	109.5	C16—C17—H17C	109.5
C7—C8—H8E	109.5	H17A—C17—H17C	109.5
H8D—C8—H8E	109.5	H17B—C17—H17C	109.5
C7—C8—H8F	109.5
C7—N1—N2—C9	178.7 (3)	C6—C1—C7—N1	−21.6 (7)
C6A—C1—C2A—C3A	9.7 (13)	C2A—C1—C7—N1	−159.1 (6)
C7—C1—C2A—C3A	−175.8 (8)	C6A—C1—C7—N1	15.2 (7)
C1—C2A—C3A—C4	−7.6 (16)	C2—C1—C7—N1	153.7 (5)
C6—C1—C2—C3	−7.5 (12)	C2A—C1—C7—C8A	7.0 (11)
C7—C1—C2—C3	177.2 (7)	C6A—C1—C7—C8A	−178.7 (10)
C1—C2—C3—C4	6.1 (13)	C6—C1—C7—C8	171.6 (10)
C2A—C3A—C4—C5A	4.2 (15)	C2—C1—C7—C8	−13.2 (11)
C2—C3—C4—C5	−5.9 (13)	N1—N2—C9—S1	−177.0 (2)
C3A—C4—C5A—C6A	−3.3 (15)	N1—N2—C9—S2	3.0 (4)
C4—C5A—C6A—C1	5.7 (16)	C10—S2—C9—N2	177.4 (3)
C2A—C1—C6A—C5A	−8.9 (13)	C10—S2—C9—S1	−2.6 (3)
C7—C1—C6A—C5A	176.6 (8)	C9—S2—C10—C11	−176.7 (2)
C3—C4—C5—C6	7.0 (14)	S2—C10—C11—C12	−179.2 (3)
C2—C1—C6—C5	8.6 (13)	C10—C11—C12—C13	−176.8 (3)
C7—C1—C6—C5	−176.0 (8)	C11—C12—C13—C14	−179.5 (3)
C4—C5—C6—C1	−8.6 (16)	C12—C13—C14—C15	−178.6 (3)
N2—N1—C7—C1	179.8 (3)	C13—C14—C15—C16	179.6 (4)
N2—N1—C7—C8A	14.0 (10)	C14—C15—C16—C17	179.8 (4)
N2—N1—C7—C8	−13.4 (10)

Bis[S-n-octyl 3-(1-phenylethylidene)dithiocarbazato]nickel(II) (NiL2)

Crystal data

[Ni(C17H25N2S2)2]	F(000) = 1496
Mr = 701.73	Dx = 1.264 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 13.6399 (3) Å	Cell parameters from 26150 reflections
b = 17.6532 (5) Å	θ = 1.8–27.5°
c = 16.7596 (3) Å	µ = 0.78 mm^−1
β = 114.000 (8)°	T = 173 K
V = 3686.6 (3) Å^3	Needle, green
Z = 4	0.27 × 0.09 × 0.03 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	6674 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.038
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.737, Tmax = 0.977	k = −22→22
35807 measured reflections	l = −20→21
8419 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 1.4889P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
8419 reflections	Δρmax = 0.60 e Å^−3
392 parameters	Δρmin = −0.25 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.74039 (2)	0.25330 (2)	0.25385 (2)	0.03168 (8)
S1	0.84963 (5)	0.16206 (3)	0.31516 (4)	0.04322 (14)
S2	1.08344 (5)	0.17784 (3)	0.40403 (4)	0.05019 (16)
S3	0.61639 (5)	0.17236 (3)	0.18452 (4)	0.04295 (14)
S4	0.38828 (5)	0.20819 (3)	0.08597 (4)	0.04600 (14)
N1	0.84293 (13)	0.31828 (8)	0.34158 (10)	0.0311 (3)
N2	0.95110 (13)	0.29419 (9)	0.37651 (10)	0.0357 (4)
N3	0.65212 (13)	0.32728 (8)	0.17072 (10)	0.0301 (3)
N4	0.54030 (13)	0.31270 (9)	0.13143 (10)	0.0345 (4)
C1	0.71951 (16)	0.41247 (10)	0.34871 (12)	0.0313 (4)
C2	0.63589 (16)	0.36389 (11)	0.34242 (12)	0.0353 (4)
H2	0.649382	0.311221	0.352804	0.042*
C3	0.53335 (17)	0.39187 (12)	0.32114 (14)	0.0423 (5)
H3	0.476887	0.358265	0.316505	0.051*
C4	0.51303 (18)	0.46818 (13)	0.30670 (15)	0.0455 (5)
H4	0.442648	0.487096	0.292229	0.055*
C5	0.59488 (19)	0.51736 (12)	0.31323 (15)	0.0456 (5)
H5	0.580546	0.569943	0.302850	0.055*
C6	0.69736 (17)	0.49012 (10)	0.33480 (13)	0.0369 (4)
H6	0.753509	0.524340	0.340292	0.044*
C7	0.82927 (16)	0.38357 (10)	0.37186 (12)	0.0316 (4)
C8	0.92187 (17)	0.43050 (11)	0.43057 (14)	0.0405 (5)
H8A	0.967649	0.400021	0.480793	0.049*
H8B	0.894927	0.474549	0.451068	0.049*
H8C	0.963667	0.447671	0.398296	0.049*
C9	0.95825 (17)	0.22217 (11)	0.36603 (13)	0.0367 (4)
C10	1.17362 (18)	0.25061 (14)	0.46973 (15)	0.0509 (6)
H10A	1.140263	0.275184	0.505639	0.061*
H10B	1.240558	0.225943	0.510265	0.061*
C11	1.20302 (19)	0.31163 (14)	0.41984 (15)	0.0513 (6)
H11A	1.138161	0.341163	0.384373	0.062*
H11B	1.230706	0.287810	0.379651	0.062*
C12	1.2880 (2)	0.36459 (17)	0.48235 (18)	0.0684 (8)
H12A	1.261218	0.385392	0.524572	0.082*
H12B	1.353331	0.334666	0.515807	0.082*
C13	1.3188 (2)	0.43029 (17)	0.4382 (2)	0.0740 (8)
H13A	1.389438	0.450271	0.478590	0.089*
H13B	1.326489	0.411161	0.385544	0.089*
C14	1.2390 (2)	0.49362 (15)	0.41222 (17)	0.0594 (7)
H14A	1.239582	0.517821	0.465697	0.071*
H14B	1.166457	0.472263	0.379554	0.071*
C15	1.2602 (2)	0.55481 (15)	0.35546 (16)	0.0587 (7)
H15A	1.269751	0.529466	0.306412	0.070*
H15B	1.195840	0.587481	0.330127	0.070*
C16	1.3558 (2)	0.60421 (18)	0.40216 (18)	0.0683 (7)
H16A	1.420947	0.572151	0.424799	0.082*
H16B	1.348212	0.627938	0.452884	0.082*
C17	1.3710 (3)	0.66657 (19)	0.3449 (2)	0.0846 (9)
H17A	1.432010	0.698486	0.380235	0.102*
H17B	1.305876	0.697621	0.320527	0.102*
H17C	1.384727	0.643577	0.297226	0.102*
C18	0.79429 (16)	0.40675 (10)	0.17028 (12)	0.0311 (4)
C19	0.86459 (16)	0.34878 (11)	0.17231 (12)	0.0341 (4)
H19	0.838889	0.298260	0.159744	0.041*
C20	0.97162 (17)	0.36419 (13)	0.19250 (13)	0.0414 (5)
H20	1.019032	0.324289	0.193909	0.050*
C21	1.00957 (18)	0.43770 (14)	0.21063 (14)	0.0455 (5)
H21	1.082960	0.448151	0.224205	0.055*
C22	0.94112 (19)	0.49591 (13)	0.20904 (14)	0.0457 (5)
H22	0.967704	0.546150	0.222558	0.055*
C23	0.83347 (17)	0.48093 (11)	0.18769 (13)	0.0372 (4)
H23	0.786094	0.521277	0.184876	0.045*
C24	0.67924 (16)	0.39092 (10)	0.14602 (12)	0.0309 (4)
C25	0.59705 (17)	0.44680 (11)	0.09090 (14)	0.0386 (5)
H25A	0.553452	0.423904	0.034202	0.046*
H25B	0.633169	0.491993	0.082072	0.046*
H25C	0.550715	0.461094	0.120355	0.046*
C26	0.52026 (17)	0.24162 (11)	0.13485 (13)	0.0358 (4)
C27	0.31613 (18)	0.29143 (12)	0.02909 (14)	0.0436 (5)
H27A	0.358150	0.316283	0.000245	0.052*
H27B	0.246964	0.275151	−0.017279	0.052*
C28	0.29357 (18)	0.34919 (12)	0.08641 (14)	0.0436 (5)
H28A	0.245687	0.326397	0.111130	0.052*
H28B	0.361711	0.363080	0.135586	0.052*
C29	0.24138 (18)	0.41999 (12)	0.03573 (14)	0.0437 (5)
H29A	0.290487	0.443173	0.012497	0.052*
H29B	0.174836	0.405413	−0.014688	0.052*
C30	0.2140 (2)	0.47840 (13)	0.08941 (15)	0.0488 (5)
H30A	0.170690	0.453715	0.117230	0.059*
H30B	0.281430	0.496272	0.136649	0.059*
C31	0.15295 (19)	0.54626 (12)	0.03832 (15)	0.0456 (5)
H31A	0.197589	0.572328	0.012675	0.055*
H31B	0.087024	0.528287	−0.010493	0.055*
C32	0.1218 (2)	0.60272 (13)	0.09154 (15)	0.0516 (6)
H32A	0.083050	0.575616	0.121678	0.062*
H32B	0.187996	0.624210	0.136973	0.062*
C33	0.0526 (2)	0.66669 (14)	0.03960 (17)	0.0542 (6)
H33A	−0.013476	0.645405	−0.006231	0.065*
H33B	0.091524	0.694443	0.010095	0.065*
C34	0.0215 (2)	0.72192 (17)	0.0943 (2)	0.0741 (8)
H34A	−0.018940	0.695217	0.122478	0.089*
H34B	−0.023206	0.762201	0.056803	0.089*
H34C	0.086370	0.744135	0.139102	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.04200 (15)	0.01830 (12)	0.03551 (14)	0.00075 (10)	0.01657 (11)	0.00046 (9)
S1	0.0548 (3)	0.0224 (2)	0.0521 (3)	0.0068 (2)	0.0213 (3)	0.0038 (2)
S2	0.0516 (4)	0.0419 (3)	0.0579 (4)	0.0196 (3)	0.0231 (3)	0.0148 (3)
S3	0.0504 (3)	0.0206 (2)	0.0551 (3)	−0.0034 (2)	0.0186 (3)	−0.0014 (2)
S4	0.0446 (3)	0.0315 (3)	0.0624 (4)	−0.0102 (2)	0.0223 (3)	−0.0078 (2)
N1	0.0366 (9)	0.0239 (7)	0.0340 (9)	0.0022 (6)	0.0156 (7)	0.0030 (6)
N2	0.0384 (9)	0.0319 (9)	0.0361 (9)	0.0075 (7)	0.0142 (7)	0.0052 (7)
N3	0.0372 (9)	0.0213 (7)	0.0337 (8)	−0.0018 (6)	0.0164 (7)	−0.0028 (6)
N4	0.0381 (9)	0.0254 (8)	0.0395 (9)	−0.0036 (7)	0.0155 (7)	−0.0018 (6)
C1	0.0429 (11)	0.0253 (9)	0.0295 (10)	0.0009 (8)	0.0187 (8)	−0.0022 (7)
C2	0.0466 (12)	0.0269 (9)	0.0363 (11)	−0.0003 (8)	0.0207 (9)	0.0015 (8)
C3	0.0435 (12)	0.0420 (12)	0.0464 (12)	−0.0015 (9)	0.0235 (10)	0.0030 (9)
C4	0.0449 (13)	0.0489 (13)	0.0487 (13)	0.0112 (10)	0.0252 (10)	0.0052 (10)
C5	0.0617 (15)	0.0316 (11)	0.0521 (13)	0.0112 (10)	0.0318 (11)	0.0041 (9)
C6	0.0501 (12)	0.0250 (9)	0.0437 (12)	−0.0003 (8)	0.0274 (10)	−0.0025 (8)
C7	0.0400 (11)	0.0256 (9)	0.0318 (10)	−0.0012 (8)	0.0174 (8)	0.0012 (7)
C8	0.0437 (12)	0.0318 (10)	0.0455 (12)	−0.0057 (9)	0.0175 (10)	−0.0067 (9)
C9	0.0453 (12)	0.0318 (10)	0.0353 (11)	0.0084 (9)	0.0189 (9)	0.0084 (8)
C10	0.0429 (13)	0.0663 (16)	0.0394 (12)	0.0159 (11)	0.0127 (10)	0.0135 (11)
C11	0.0460 (14)	0.0620 (15)	0.0448 (13)	0.0089 (11)	0.0173 (11)	0.0091 (11)
C12	0.0576 (17)	0.0686 (19)	0.0663 (17)	0.0020 (14)	0.0123 (14)	0.0031 (14)
C13	0.0522 (17)	0.072 (2)	0.093 (2)	0.0032 (14)	0.0239 (15)	0.0015 (16)
C14	0.0557 (16)	0.0690 (18)	0.0522 (15)	0.0069 (13)	0.0204 (12)	−0.0060 (12)
C15	0.0654 (17)	0.0623 (16)	0.0492 (14)	0.0117 (13)	0.0242 (13)	−0.0067 (12)
C16	0.0590 (17)	0.083 (2)	0.0584 (17)	0.0056 (15)	0.0191 (13)	−0.0046 (14)
C17	0.078 (2)	0.081 (2)	0.095 (2)	−0.0064 (18)	0.0353 (19)	−0.0062 (18)
C18	0.0414 (11)	0.0269 (9)	0.0277 (9)	−0.0020 (8)	0.0170 (8)	0.0014 (7)
C19	0.0444 (12)	0.0314 (10)	0.0276 (10)	0.0006 (8)	0.0159 (8)	0.0001 (7)
C20	0.0425 (12)	0.0505 (13)	0.0335 (11)	0.0057 (10)	0.0177 (9)	0.0017 (9)
C21	0.0420 (12)	0.0617 (15)	0.0364 (12)	−0.0125 (11)	0.0196 (10)	−0.0019 (10)
C22	0.0565 (14)	0.0423 (12)	0.0443 (13)	−0.0175 (10)	0.0268 (11)	−0.0056 (9)
C23	0.0487 (12)	0.0283 (10)	0.0413 (11)	−0.0049 (9)	0.0252 (10)	−0.0011 (8)
C24	0.0405 (11)	0.0219 (9)	0.0324 (10)	−0.0012 (8)	0.0168 (8)	−0.0029 (7)
C25	0.0452 (12)	0.0241 (9)	0.0453 (12)	0.0017 (8)	0.0172 (10)	0.0036 (8)
C26	0.0444 (12)	0.0273 (10)	0.0397 (11)	−0.0045 (8)	0.0213 (9)	−0.0047 (8)
C27	0.0408 (12)	0.0426 (12)	0.0443 (12)	−0.0029 (10)	0.0140 (10)	−0.0072 (9)
C28	0.0453 (13)	0.0436 (12)	0.0464 (13)	0.0002 (10)	0.0231 (10)	−0.0001 (9)
C29	0.0476 (13)	0.0458 (13)	0.0416 (12)	0.0006 (10)	0.0222 (10)	0.0012 (9)
C30	0.0579 (15)	0.0465 (13)	0.0435 (13)	0.0084 (11)	0.0221 (11)	0.0030 (10)
C31	0.0491 (13)	0.0419 (12)	0.0484 (13)	0.0033 (10)	0.0224 (11)	−0.0014 (10)
C32	0.0588 (15)	0.0465 (13)	0.0504 (14)	0.0055 (11)	0.0231 (11)	−0.0037 (10)
C33	0.0506 (15)	0.0472 (14)	0.0673 (16)	0.0037 (11)	0.0267 (12)	−0.0052 (11)
C34	0.072 (2)	0.0666 (18)	0.084 (2)	0.0144 (15)	0.0318 (16)	−0.0169 (16)

Geometric parameters (Å, º)

Ni1—N3	1.9318 (15)	C15—H15A	0.9900
Ni1—N1	1.9392 (16)	C15—H15B	0.9900
Ni1—S1	2.1506 (6)	C16—C17	1.529 (4)
Ni1—S3	2.1573 (6)	C16—H16A	0.9900
S1—C9	1.738 (2)	C16—H16B	0.9900
S2—C9	1.746 (2)	C17—H17A	0.9800
S2—C10	1.809 (3)	C17—H17B	0.9800
S3—C26	1.738 (2)	C17—H17C	0.9800
S4—C26	1.749 (2)	C18—C19	1.393 (3)
S4—C27	1.809 (2)	C18—C23	1.400 (3)
N1—C7	1.303 (2)	C18—C24	1.479 (3)
N1—N2	1.414 (2)	C19—C20	1.385 (3)
N2—C9	1.293 (3)	C19—H19	0.9500
N3—C24	1.302 (2)	C20—C21	1.384 (3)
N3—N4	1.417 (2)	C20—H20	0.9500
N4—C26	1.290 (2)	C21—C22	1.381 (3)
C1—C2	1.396 (3)	C21—H21	0.9500
C1—C6	1.403 (3)	C22—C23	1.388 (3)
C1—C7	1.476 (3)	C22—H22	0.9500
C2—C3	1.386 (3)	C23—H23	0.9500
C2—H2	0.9500	C24—C25	1.497 (3)
C3—C4	1.377 (3)	C25—H25A	0.9800
C3—H3	0.9500	C25—H25B	0.9800
C4—C5	1.383 (3)	C25—H25C	0.9800
C4—H4	0.9500	C27—C28	1.516 (3)
C5—C6	1.380 (3)	C27—H27A	0.9900
C5—H5	0.9500	C27—H27B	0.9900
C6—H6	0.9500	C28—C29	1.516 (3)
C7—C8	1.496 (3)	C28—H28A	0.9900
C8—H8A	0.9800	C28—H28B	0.9900
C8—H8B	0.9800	C29—C30	1.512 (3)
C8—H8C	0.9800	C29—H29A	0.9900
C10—C11	1.514 (3)	C29—H29B	0.9900
C10—H10A	0.9900	C30—C31	1.510 (3)
C10—H10B	0.9900	C30—H30A	0.9900
C11—C12	1.526 (4)	C30—H30B	0.9900
C11—H11A	0.9900	C31—C32	1.509 (3)
C11—H11B	0.9900	C31—H31A	0.9900
C12—C13	1.523 (4)	C31—H31B	0.9900
C12—H12A	0.9900	C32—C33	1.502 (3)
C12—H12B	0.9900	C32—H32A	0.9900
C13—C14	1.496 (4)	C32—H32B	0.9900
C13—H13A	0.9900	C33—C34	1.513 (3)
C13—H13B	0.9900	C33—H33A	0.9900
C14—C15	1.542 (4)	C33—H33B	0.9900
C14—H14A	0.9900	C34—H34A	0.9800
C14—H14B	0.9900	C34—H34B	0.9800
C15—C16	1.498 (4)	C34—H34C	0.9800
N3—Ni1—N1	101.11 (7)	C15—C16—H16B	108.8
N3—Ni1—S1	163.41 (5)	C17—C16—H16B	108.8
N1—Ni1—S1	86.26 (5)	H16A—C16—H16B	107.7
N3—Ni1—S3	86.40 (5)	C16—C17—H17A	109.5
N1—Ni1—S3	164.97 (5)	C16—C17—H17B	109.5
S1—Ni1—S3	90.02 (2)	H17A—C17—H17B	109.5
C9—S1—Ni1	93.66 (7)	C16—C17—H17C	109.5
C9—S2—C10	103.05 (10)	H17A—C17—H17C	109.5
C26—S3—Ni1	93.75 (7)	H17B—C17—H17C	109.5
C26—S4—C27	102.03 (10)	C19—C18—C23	118.78 (18)
C7—N1—N2	113.29 (16)	C19—C18—C24	120.72 (17)
C7—N1—Ni1	130.19 (14)	C23—C18—C24	120.44 (17)
N2—N1—Ni1	116.46 (11)	C20—C19—C18	120.55 (19)
C9—N2—N1	111.31 (16)	C20—C19—H19	119.7
C24—N3—N4	113.59 (15)	C18—C19—H19	119.7
C24—N3—Ni1	129.67 (14)	C21—C20—C19	120.0 (2)
N4—N3—Ni1	116.71 (11)	C21—C20—H20	120.0
C26—N4—N3	111.30 (16)	C19—C20—H20	120.0
C2—C1—C6	118.27 (18)	C22—C21—C20	120.2 (2)
C2—C1—C7	121.16 (16)	C22—C21—H21	119.9
C6—C1—C7	120.55 (18)	C20—C21—H21	119.9
C3—C2—C1	120.55 (18)	C21—C22—C23	119.9 (2)
C3—C2—H2	119.7	C21—C22—H22	120.0
C1—C2—H2	119.7	C23—C22—H22	120.0
C4—C3—C2	120.3 (2)	C22—C23—C18	120.4 (2)
C4—C3—H3	119.9	C22—C23—H23	119.8
C2—C3—H3	119.9	C18—C23—H23	119.8
C3—C4—C5	120.1 (2)	N3—C24—C18	118.85 (17)
C3—C4—H4	119.9	N3—C24—C25	121.78 (18)
C5—C4—H4	119.9	C18—C24—C25	119.33 (16)
C6—C5—C4	120.1 (2)	C24—C25—H25A	109.5
C6—C5—H5	120.0	C24—C25—H25B	109.5
C4—C5—H5	120.0	H25A—C25—H25B	109.5
C5—C6—C1	120.72 (19)	C24—C25—H25C	109.5
C5—C6—H6	119.6	H25A—C25—H25C	109.5
C1—C6—H6	119.6	H25B—C25—H25C	109.5
N1—C7—C1	119.58 (17)	N4—C26—S3	124.99 (16)
N1—C7—C8	121.99 (18)	N4—C26—S4	120.22 (16)
C1—C7—C8	118.42 (16)	S3—C26—S4	114.79 (11)
C7—C8—H8A	109.5	C28—C27—S4	114.80 (15)
C7—C8—H8B	109.5	C28—C27—H27A	108.6
H8A—C8—H8B	109.5	S4—C27—H27A	108.6
C7—C8—H8C	109.5	C28—C27—H27B	108.6
H8A—C8—H8C	109.5	S4—C27—H27B	108.6
H8B—C8—H8C	109.5	H27A—C27—H27B	107.5
N2—C9—S1	124.81 (16)	C29—C28—C27	111.69 (18)
N2—C9—S2	120.52 (16)	C29—C28—H28A	109.3
S1—C9—S2	114.67 (11)	C27—C28—H28A	109.3
C11—C10—S2	115.86 (17)	C29—C28—H28B	109.3
C11—C10—H10A	108.3	C27—C28—H28B	109.3
S2—C10—H10A	108.3	H28A—C28—H28B	107.9
C11—C10—H10B	108.3	C30—C29—C28	113.72 (18)
S2—C10—H10B	108.3	C30—C29—H29A	108.8
H10A—C10—H10B	107.4	C28—C29—H29A	108.8
C10—C11—C12	110.8 (2)	C30—C29—H29B	108.8
C10—C11—H11A	109.5	C28—C29—H29B	108.8
C12—C11—H11A	109.5	H29A—C29—H29B	107.7
C10—C11—H11B	109.5	C31—C30—C29	114.60 (18)
C12—C11—H11B	109.5	C31—C30—H30A	108.6
H11A—C11—H11B	108.1	C29—C30—H30A	108.6
C13—C12—C11	114.6 (2)	C31—C30—H30B	108.6
C13—C12—H12A	108.6	C29—C30—H30B	108.6
C11—C12—H12A	108.6	H30A—C30—H30B	107.6
C13—C12—H12B	108.6	C32—C31—C30	114.30 (19)
C11—C12—H12B	108.6	C32—C31—H31A	108.7
H12A—C12—H12B	107.6	C30—C31—H31A	108.7
C14—C13—C12	113.5 (2)	C32—C31—H31B	108.7
C14—C13—H13A	108.9	C30—C31—H31B	108.7
C12—C13—H13A	108.9	H31A—C31—H31B	107.6
C14—C13—H13B	108.9	C33—C32—C31	114.56 (19)
C12—C13—H13B	108.9	C33—C32—H32A	108.6
H13A—C13—H13B	107.7	C31—C32—H32A	108.6
C13—C14—C15	114.0 (2)	C33—C32—H32B	108.6
C13—C14—H14A	108.8	C31—C32—H32B	108.6
C15—C14—H14A	108.8	H32A—C32—H32B	107.6
C13—C14—H14B	108.8	C32—C33—C34	113.5 (2)
C15—C14—H14B	108.8	C32—C33—H33A	108.9
H14A—C14—H14B	107.7	C34—C33—H33A	108.9
C16—C15—C14	115.3 (2)	C32—C33—H33B	108.9
C16—C15—H15A	108.5	C34—C33—H33B	108.9
C14—C15—H15A	108.5	H33A—C33—H33B	107.7
C16—C15—H15B	108.5	C33—C34—H34A	109.5
C14—C15—H15B	108.5	C33—C34—H34B	109.5
H15A—C15—H15B	107.5	H34A—C34—H34B	109.5
C15—C16—C17	113.7 (2)	C33—C34—H34C	109.5
C15—C16—H16A	108.8	H34A—C34—H34C	109.5
C17—C16—H16A	108.8	H34B—C34—H34C	109.5
C7—N1—N2—C9	161.19 (16)	C13—C14—C15—C16	−71.2 (3)
Ni1—N1—N2—C9	−21.57 (19)	C14—C15—C16—C17	−177.2 (2)
C24—N3—N4—C26	159.67 (17)	C23—C18—C19—C20	1.0 (3)
Ni1—N3—N4—C26	−22.02 (19)	C24—C18—C19—C20	178.05 (17)
C6—C1—C2—C3	1.3 (3)	C18—C19—C20—C21	−0.2 (3)
C7—C1—C2—C3	179.60 (18)	C19—C20—C21—C22	0.3 (3)
C1—C2—C3—C4	−0.6 (3)	C20—C21—C22—C23	−1.1 (3)
C2—C3—C4—C5	0.1 (3)	C21—C22—C23—C18	1.9 (3)
C3—C4—C5—C6	−0.4 (3)	C19—C18—C23—C22	−1.8 (3)
C4—C5—C6—C1	1.2 (3)	C24—C18—C23—C22	−178.93 (18)
C2—C1—C6—C5	−1.7 (3)	N4—N3—C24—C18	−169.77 (15)
C7—C1—C6—C5	−179.93 (18)	Ni1—N3—C24—C18	12.2 (3)
N2—N1—C7—C1	−173.58 (15)	N4—N3—C24—C25	7.7 (2)
Ni1—N1—C7—C1	9.7 (3)	Ni1—N3—C24—C25	−170.32 (13)
N2—N1—C7—C8	5.9 (2)	C19—C18—C24—N3	36.4 (3)
Ni1—N1—C7—C8	−170.90 (14)	C23—C18—C24—N3	−146.61 (18)
C2—C1—C7—N1	38.0 (3)	C19—C18—C24—C25	−141.20 (18)
C6—C1—C7—N1	−143.77 (19)	C23—C18—C24—C25	35.8 (3)
C2—C1—C7—C8	−141.45 (19)	N3—N4—C26—S3	2.3 (2)
C6—C1—C7—C8	36.8 (3)	N3—N4—C26—S4	−176.86 (13)
N1—N2—C9—S1	0.3 (2)	Ni1—S3—C26—N4	14.51 (18)
N1—N2—C9—S2	−179.64 (13)	Ni1—S3—C26—S4	−166.32 (10)
Ni1—S1—C9—N2	16.87 (17)	C27—S4—C26—N4	7.20 (19)
Ni1—S1—C9—S2	−163.16 (10)	C27—S4—C26—S3	−172.01 (11)
C10—S2—C9—N2	10.39 (19)	C26—S4—C27—C28	−78.59 (18)
C10—S2—C9—S1	−169.58 (11)	S4—C27—C28—C29	175.22 (15)
C9—S2—C10—C11	−78.20 (19)	C27—C28—C29—C30	178.15 (19)
S2—C10—C11—C12	−174.06 (18)	C28—C29—C30—C31	−174.7 (2)
C10—C11—C12—C13	−177.1 (2)	C29—C30—C31—C32	177.5 (2)
C11—C12—C13—C14	78.4 (3)	C30—C31—C32—C33	−174.7 (2)
C12—C13—C14—C15	−171.3 (2)	C31—C32—C33—C34	179.3 (2)