Bis[N,N'-bis­(octylsulfanyl)glyoximato]nickel(II)

In the title compound, [Ni(C₁₈H₃₅N₂O₂S₂)₂], the coordination geometry around the Ni atom, lying on a centre of symmetry, is square planar, consisting of four N atoms from the two vic-dioxime ligands. The O atoms are intra­molecularly hydrogen bonded, as is usually observed for anti-isomer metal complexes of vic-dioximes.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.059
• wR factor = 0.066
• Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.21 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.28 Ratio

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.122
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: DIAMOND (Brandenburg, 1996); software used to prepare material for publication: CRYSTALS.

Bis[N,N'-bis(octylsulfanyl)glyoximato]nickel(II)

Crystal data

[Ni(C18H35N2O2S2)2]	F(000) = 1752
Mr = 809.95	Dx = 1.232 Mg m^−3
Monoclinic, C2/c	Melting point: 360 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 50.248 (5) Å	Cell parameters from 11791 reflections
b = 5.322 (5) Å	θ = 0.4–27.9°
c = 16.944 (5) Å	µ = 0.68 mm^−1
β = 105.536 (5)°	T = 293 K
V = 4366 (4) Å^3	Needle, red
Z = 4	0.43 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer	5083 independent reflections
Radiation source: sealed tube	2297 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.122
φ and ω scans	θmax = 27.9°, θmin = 0.8°
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	h = −65→64
Tmin = 0.77, Tmax = 0.97	k = −6→6
14667 measured reflections	l = −22→13

Refinement

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.066	w = (weight)[1-(ΔF/6σ(F))^2]^2, where weight = 1.0/[0.737T0(x) + 0.674T1(x) + 0.412Tn-1(x)], where Ti are the Chebychev polynomials and x = F /Fmax (Watkin, 1994; Prince, 1982)
S = 1.06	(Δ/σ)max = 0.0004
2297 reflections	Δρmax = 0.71 e Å^−3
223 parameters	Δρmin = −0.60 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
Ni1	0.7500	0.2500	0.5000	0.0425
S2	0.66594 (3)	0.5659 (3)	0.41459 (9)	0.0610
S1	0.71175 (3)	0.8852 (3)	0.34216 (7)	0.0511
O2	0.69680 (7)	0.1586 (7)	0.5244 (2)	0.0575
O1	0.76633 (7)	0.6313 (6)	0.40631 (19)	0.0487
N1	0.74559 (8)	0.5310 (8)	0.4309 (2)	0.0434
N2	0.71232 (7)	0.3015 (8)	0.4889 (2)	0.0448
C2	0.70104 (10)	0.4873 (10)	0.4410 (3)	0.0443
C5	0.67373 (11)	0.5637 (11)	0.1797 (3)	0.0560
C1	0.72075 (10)	0.6245 (9)	0.4075 (3)	0.0444
C3	0.72019 (10)	0.7670 (11)	0.2504 (3)	0.0503
C6	0.65941 (12)	0.3200 (12)	0.1461 (3)	0.0669
C12	0.61967 (11)	0.3002 (12)	0.3391 (4)	0.0691
C4	0.70484 (10)	0.5341 (10)	0.2142 (3)	0.0503
C11	0.64923 (11)	0.2634 (12)	0.3901 (4)	0.0670
C13	0.60572 (11)	0.0518 (13)	0.3115 (4)	0.0700
C14	0.57586 (12)	0.0773 (14)	0.2612 (4)	0.0811
C7	0.62879 (12)	0.3521 (12)	0.1016 (4)	0.0688
C8	0.61403 (13)	0.1088 (13)	0.0706 (4)	0.0782
C9	0.58404 (14)	0.1391 (15)	0.0246 (5)	0.0936
C15	0.56196 (13)	−0.1750 (15)	0.2329 (5)	0.0920
C18	0.48917 (17)	−0.373 (3)	0.0981 (8)	0.1870
C16	0.53226 (15)	−0.1499 (16)	0.1797 (6)	0.1079
C10	0.56999 (16)	−0.1103 (17)	−0.0036 (5)	0.1118
C17	0.51882 (17)	−0.4003 (19)	0.1509 (7)	0.1401
H51	0.6705	0.6852	0.1352	0.0668*
H52	0.6660	0.6281	0.2225	0.0672*
H31	0.7398	0.7334	0.2641	0.0598*
H32	0.7159	0.8986	0.2106	0.0598*
H61	0.6688	0.2482	0.1078	0.0781*
H62	0.6608	0.2049	0.1912	0.0780*
H121	0.6196	0.4004	0.2917	0.0804*
H122	0.6094	0.3883	0.3722	0.0798*
H41	0.7125	0.4747	0.1713	0.0602*
H42	0.7080	0.4059	0.2566	0.0601*
H111	0.6589	0.1653	0.3586	0.0795*
H112	0.6494	0.1766	0.4398	0.0793*
H131	0.6160	−0.0400	0.2799	0.0812*
H132	0.6056	−0.0454	0.3596	0.0811*
H141	0.5755	0.1779	0.2135	0.0930*
H142	0.5656	0.1610	0.2938	0.0931*
H71	0.6276	0.4637	0.0556	0.0810*
H72	0.6197	0.4288	0.1390	0.0813*
H81	0.6233	0.0288	0.0340	0.0920*
H82	0.6151	−0.0009	0.1169	0.0922*
H91	0.5829	0.2459	−0.0226	0.1081*
H92	0.5744	0.2195	0.0603	0.1080*
H151	0.5729	−0.2645	0.2021	0.1039*
H152	0.5616	−0.2725	0.2813	0.1040*
H181	0.4815	−0.5367	0.0828	0.2560*
H182	0.4891	−0.2785	0.0499	0.2560*
H183	0.4785	−0.2864	0.1290	0.2560*
H161	0.5323	−0.0483	0.1324	0.1220*
H162	0.5214	−0.0654	0.2115	0.1220*
H101	0.5507	−0.0817	−0.0281	0.1609*
H102	0.5780	−0.1861	−0.0432	0.1610*
H103	0.5721	−0.2217	0.0425	0.1609*
H171	0.5295	−0.4860	0.1190	0.1550*
H172	0.5186	−0.5006	0.1988	0.1550*
H3	0.7087	0.0547	0.5479	0.0875*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0417 (4)	0.0520 (6)	0.0331 (4)	−0.0039 (5)	0.0087 (3)	0.0031 (4)
S2	0.0462 (7)	0.0595 (9)	0.0743 (9)	0.0020 (7)	0.0111 (6)	0.0055 (7)
S1	0.0624 (8)	0.0445 (8)	0.0464 (7)	0.0015 (6)	0.0144 (6)	0.0008 (6)
O2	0.0506 (18)	0.072 (3)	0.0519 (19)	−0.0012 (18)	0.0168 (16)	0.0195 (18)
O1	0.0510 (18)	0.050 (2)	0.0468 (17)	−0.0078 (17)	0.0156 (15)	0.0092 (16)
N1	0.050 (2)	0.048 (2)	0.0332 (18)	−0.005 (2)	0.0135 (17)	0.0008 (18)
N2	0.0428 (19)	0.056 (3)	0.0353 (18)	0.000 (2)	0.0104 (16)	0.0026 (18)
C2	0.047 (2)	0.047 (3)	0.038 (2)	−0.002 (2)	0.0094 (19)	−0.007 (2)
C5	0.059 (3)	0.055 (3)	0.052 (3)	0.000 (3)	0.013 (2)	−0.005 (3)
C1	0.049 (3)	0.048 (3)	0.034 (2)	−0.004 (2)	0.0062 (19)	−0.005 (2)
C3	0.054 (3)	0.059 (3)	0.038 (2)	0.006 (3)	0.0122 (19)	0.004 (3)
C6	0.067 (3)	0.073 (4)	0.055 (3)	0.000 (3)	0.007 (3)	−0.004 (3)
C12	0.051 (3)	0.075 (5)	0.073 (3)	−0.003 (3)	0.004 (3)	0.003 (3)
C4	0.060 (3)	0.051 (3)	0.040 (2)	0.009 (3)	0.014 (2)	−0.003 (2)
C11	0.056 (3)	0.068 (4)	0.073 (3)	0.000 (3)	0.012 (3)	0.006 (3)
C13	0.055 (3)	0.066 (4)	0.081 (4)	−0.001 (3)	0.006 (3)	0.000 (3)
C14	0.055 (3)	0.087 (5)	0.090 (4)	0.002 (4)	−0.001 (3)	−0.002 (4)
C7	0.071 (4)	0.067 (4)	0.065 (3)	0.000 (3)	0.013 (3)	−0.005 (3)
C8	0.076 (4)	0.077 (5)	0.077 (4)	−0.001 (4)	0.012 (3)	−0.007 (4)
C9	0.069 (4)	0.102 (6)	0.100 (5)	−0.012 (4)	0.006 (4)	−0.015 (5)
C15	0.062 (4)	0.095 (6)	0.103 (5)	−0.007 (4)	−0.007 (4)	−0.011 (4)
C18	0.080 (6)	0.190 (13)	0.242 (14)	−0.019 (7)	−0.042 (7)	−0.069 (11)
C16	0.069 (4)	0.107 (6)	0.128 (7)	−0.004 (5)	−0.008 (4)	−0.012 (5)
C10	0.085 (5)	0.113 (7)	0.124 (7)	−0.024 (5)	0.006 (5)	−0.022 (6)
C17	0.093 (6)	0.129 (9)	0.167 (9)	−0.019 (6)	−0.020 (6)	−0.034 (7)

Geometric parameters (Å, º)

Ni1—N1^i	1.876 (4)	C11—H112	0.958
Ni1—N2^i	1.872 (4)	C13—C14	1.520 (7)
Ni1—N1	1.876 (4)	C13—H131	0.972
Ni1—N2	1.872 (4)	C13—H132	0.965
S2—C2	1.750 (5)	C14—C15	1.530 (9)
S2—C11	1.812 (7)	C14—H141	0.967
S1—C1	1.757 (5)	C14—H142	0.959
S1—C3	1.829 (5)	C7—C8	1.514 (9)
O2—N2	1.341 (5)	C7—H71	0.968
O2—H3	0.832	C7—H72	0.966
O1—N1	1.333 (5)	C8—C9	1.508 (8)
N1—C1	1.303 (6)	C8—H81	0.969
N2—C2	1.308 (6)	C8—H82	0.968
C2—C1	1.463 (7)	C9—C10	1.519 (10)
C5—C6	1.518 (8)	C9—H91	0.970
C5—C4	1.523 (7)	C9—H92	0.971
C5—H51	0.973	C15—C16	1.529 (9)
C5—H52	0.971	C15—H151	0.977
C3—C4	1.502 (8)	C15—H152	0.975
C3—H31	0.966	C18—C17	1.525 (10)
C3—H32	0.956	C18—H181	0.960
C6—C7	1.531 (8)	C18—H182	0.958
C6—H61	0.975	C18—H183	0.960
C6—H62	0.967	C16—C17	1.515 (11)
C12—C11	1.518 (7)	C16—H161	0.968
C12—C13	1.510 (9)	C16—H162	0.972
C12—H121	0.963	C10—H101	0.959
C12—H122	0.977	C10—H102	0.959
C4—H41	0.963	C10—H103	0.964
C4—H42	0.972	C17—H171	0.972
C11—H111	0.966	C17—H172	0.974
N1^i—Ni1—N2^i	82.73 (17)	C14—C13—H131	109.1
N1^i—Ni1—N1	179.994	C12—C13—H132	108.4
N2^i—Ni1—N1	97.27 (17)	C14—C13—H132	107.1
N1^i—Ni1—N2	97.27 (17)	H131—C13—H132	108.6
N2^i—Ni1—N2	179.994	C13—C14—C15	113.4 (6)
N1—Ni1—N2	82.73 (17)	C13—C14—H141	108.2
C2—S2—C11	102.7 (3)	C15—C14—H141	108.6
C1—S1—C3	100.7 (2)	C13—C14—H142	108.6
N2—O2—H3	99.4	C15—C14—H142	108.5
O1—N1—Ni1	122.9 (3)	H141—C14—H142	109.4
O1—N1—C1	121.2 (4)	C6—C7—C8	114.2 (5)
Ni1—N1—C1	116.0 (3)	C6—C7—H71	107.7
O2—N2—Ni1	124.5 (3)	C8—C7—H71	109.0
O2—N2—C2	119.9 (4)	C6—C7—H72	108.3
Ni1—N2—C2	115.6 (3)	C8—C7—H72	108.3
S2—C2—N2	125.4 (4)	H71—C7—H72	109.2
S2—C2—C1	121.5 (4)	C7—C8—C9	114.6 (6)
N2—C2—C1	113.1 (4)	C7—C8—H81	108.8
C6—C5—C4	113.0 (5)	C9—C8—H81	107.6
C6—C5—H51	108.3	C7—C8—H82	108.6
C4—C5—H51	107.7	C9—C8—H82	108.3
C6—C5—H52	109.7	H81—C8—H82	108.8
C4—C5—H52	108.9	C8—C9—C10	112.6 (7)
H51—C5—H52	109.1	C8—C9—H91	108.6
C2—C1—S1	123.5 (4)	C10—C9—H91	109.5
C2—C1—N1	112.6 (4)	C8—C9—H92	108.7
S1—C1—N1	123.9 (4)	C10—C9—H92	108.3
S1—C3—C4	114.9 (3)	H91—C9—H92	109.1
S1—C3—H31	108.3	C14—C15—C16	113.6 (6)
C4—C3—H31	108.9	C14—C15—H151	108.7
S1—C3—H32	106.7	C16—C15—H151	109.1
C4—C3—H32	108.7	C14—C15—H152	108.3
H31—C3—H32	109.2	C16—C15—H152	107.8
C5—C6—C7	113.7 (5)	H151—C15—H152	109.3
C5—C6—H61	108.7	C17—C18—H181	109.3
C7—C6—H61	108.3	C17—C18—H182	109.4
C5—C6—H62	108.6	H181—C18—H182	109.6
C7—C6—H62	108.0	C17—C18—H183	109.0
H61—C6—H62	109.4	H181—C18—H183	109.9
C11—C12—C13	111.4 (5)	H182—C18—H183	109.6
C11—C12—H121	109.2	C15—C16—C17	113.2 (7)
C13—C12—H121	109.3	C15—C16—H161	108.6
C11—C12—H122	108.7	C17—C16—H161	108.9
C13—C12—H122	109.0	C15—C16—H162	108.5
H121—C12—H122	109.2	C17—C16—H162	108.5
C5—C4—C3	115.7 (4)	H161—C16—H162	109.0
C5—C4—H41	108.8	C9—C10—H101	109.2
C3—C4—H41	108.2	C9—C10—H102	109.9
C5—C4—H42	107.5	H101—C10—H102	109.3
C3—C4—H42	108.3	C9—C10—H103	109.9
H41—C4—H42	108.0	H101—C10—H103	109.2
C12—C11—S2	109.8 (4)	H102—C10—H103	109.3
C12—C11—H111	108.4	C18—C17—C16	112.7 (9)
S2—C11—H111	109.6	C18—C17—H171	108.5
C12—C11—H112	109.9	C16—C17—H171	109.1
S2—C11—H112	109.4	C18—C17—H172	108.2
H111—C11—H112	109.7	C16—C17—H172	108.5
C12—C13—C14	113.7 (5)	H171—C17—H172	109.8
C12—C13—H131	109.8

Symmetry code: (i) −x+3/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H3···O1^i	0.83	1.62	2.455 (5)	175

Symmetry code: (i) −x+3/2, −y+1/2, −z+1.