Bis[S-octyl 3-(4-meth­oxy­benzyl­idene)di­thio­carbazato-κ²N³,S]nickel(II)

The nickel(II) cation of the title complex, [Ni(C₁₇H₂₅N₂OS₂)₂], is located on a crystallographic inversion centre. It has a square-planar coordination geometry, with a trans configuration of the N,S-chelating ligands, as imposed by the crystal symmetry.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.112
• Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.16 Report
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........     Please Do !
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT794_ALERT_5_G Tentative Bond Valency for Ni        (II)      .       2.24 Info
PLAT882_ALERT_1_G No Datum for _diffrn_reflns_av_unetI/netI ......     Please Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1999); cell refinement: RAPID-AUTO (Rigaku, 1999); data reduction: RAPID-AUTO (Rigaku, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Bis[S-octyl 3-(4-methoxybenzylidene)dithiocarbazato-\ κ²N³,S]nickel(II)

Crystal data

[Ni(C17H25N2OS2)2]	Z = 1
Mr = 733.73	F(000) = 390.00
Triclinic, P1	Dx = 1.369 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 4.55302 (14) Å	Cell parameters from 8264 reflections
b = 11.5641 (3) Å	θ = 3.1–27.5°
c = 17.5075 (5) Å	µ = 0.82 mm^−1
α = 84.1436 (7)°	T = 173 K
β = 85.6165 (10)°	Platelet, orange
γ = 76.4084 (10)°	0.27 × 0.12 × 0.07 mm
V = 890.00 (5) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	3705 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.025
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −5→5
Tmin = 0.866, Tmax = 0.944	k = −14→14
8899 measured reflections	l = −22→21
4041 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0566P)^2 + 0.5813P] where P = (Fo^2 + 2Fc^2)/3
4041 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 1.17 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

The H atoms were located geometrically and treated as riding atoms: C—H = 0.95–0.99 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

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

	x	y	z	Uiso*/Ueq
Ni	0.5000	0.5000	0.5000	0.02291 (12)
S1	0.53959 (14)	0.35043 (5)	0.58802 (3)	0.03236 (15)
S2	0.72806 (13)	0.33241 (4)	0.74527 (3)	0.02987 (14)
O1	1.3002 (4)	0.96865 (14)	0.71096 (9)	0.0387 (4)
N1	0.6922 (4)	0.57294 (15)	0.57058 (9)	0.0247 (4)
N2	0.7284 (4)	0.52311 (15)	0.64734 (9)	0.0256 (4)
C1	0.9372 (5)	0.73725 (17)	0.59923 (11)	0.0249 (4)
C2	1.0441 (5)	0.82953 (18)	0.55700 (12)	0.0292 (5)
C3	1.1693 (5)	0.90850 (18)	0.59111 (12)	0.0302 (5)
C4	1.1880 (5)	0.89570 (18)	0.67074 (12)	0.0283 (4)
C5	1.0869 (6)	0.8034 (2)	0.71388 (13)	0.0353 (5)
C6	0.9640 (6)	0.72470 (19)	0.67942 (12)	0.0314 (5)
C7	1.3781 (6)	1.0717 (2)	0.66998 (15)	0.0397 (6)
C8	0.8008 (5)	0.66685 (18)	0.55359 (11)	0.0264 (4)
C9	0.6696 (5)	0.41906 (17)	0.65734 (11)	0.0243 (4)
C10	0.8698 (5)	0.42720 (18)	0.80277 (11)	0.0282 (4)
C11	0.6211 (5)	0.51742 (19)	0.84182 (12)	0.0291 (4)
C12	0.7464 (5)	0.58919 (19)	0.89491 (12)	0.0293 (5)
C13	0.5011 (5)	0.6716 (2)	0.94072 (12)	0.0314 (5)
C14	0.6261 (5)	0.73863 (19)	0.99649 (12)	0.0306 (5)
C15	0.3830 (5)	0.82086 (19)	1.04283 (12)	0.0305 (5)
C16	0.5078 (6)	0.8927 (2)	1.09547 (13)	0.0335 (5)
C17	0.2620 (6)	0.9785 (2)	1.13894 (14)	0.0418 (6)
H1	1.0306	0.8386	0.5028	0.0351*
H2	1.2411	0.9701	0.5608	0.0362*
H3	1.1027	0.7943	0.7681	0.0423*
H4	0.8974	0.6620	0.7099	0.0377*
H5	1.5416	1.0465	0.6312	0.0476*
H6	1.4452	1.1184	0.7060	0.0476*
H7	1.2007	1.1208	0.6446	0.0476*
H8	0.7894	0.6958	0.5009	0.0316*
H9	0.9957	0.3763	0.8426	0.0338*
H10	1.0013	0.4706	0.7693	0.0338*
H11	0.4799	0.4749	0.8721	0.0349*
H12	0.5055	0.5730	0.8021	0.0349*
H13	0.8793	0.5331	0.9312	0.0352*
H14	0.8718	0.6376	0.8636	0.0352*
H15	0.3694	0.6238	0.9700	0.0377*
H16	0.3744	0.7304	0.9045	0.0377*
H17	0.7537	0.6798	1.0325	0.0367*
H18	0.7571	0.7866	0.9671	0.0367*
H19	0.2587	0.7722	1.0744	0.0366*
H20	0.2485	0.8769	1.0069	0.0366*
H21	0.6347	0.8368	1.1330	0.0402*
H22	0.6391	0.9388	1.0643	0.0402*
H23	0.1296	1.0319	1.1022	0.0501*
H24	0.3557	1.0259	1.1689	0.0501*
H25	0.1426	0.9331	1.1737	0.0501*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0282 (2)	0.02338 (19)	0.02004 (18)	−0.01005 (13)	−0.00419 (13)	−0.00357 (13)
S1	0.0511 (4)	0.0275 (3)	0.0245 (3)	−0.0186 (3)	−0.0109 (2)	−0.00139 (19)
S2	0.0432 (3)	0.0257 (3)	0.0235 (3)	−0.0124 (2)	−0.0073 (2)	−0.00067 (18)
O1	0.0545 (11)	0.0323 (8)	0.0371 (9)	−0.0207 (7)	−0.0132 (8)	−0.0064 (7)
N1	0.0302 (9)	0.0249 (8)	0.0207 (8)	−0.0086 (7)	−0.0036 (7)	−0.0027 (6)
N2	0.0322 (9)	0.0259 (8)	0.0206 (8)	−0.0089 (7)	−0.0047 (7)	−0.0030 (6)
C1	0.0266 (10)	0.0241 (9)	0.0258 (10)	−0.0070 (7)	−0.0046 (7)	−0.0053 (7)
C2	0.0362 (11)	0.0285 (10)	0.0250 (10)	−0.0103 (8)	−0.0045 (8)	−0.0035 (8)
C3	0.0355 (11)	0.0258 (10)	0.0318 (11)	−0.0118 (8)	−0.0018 (9)	−0.0034 (8)
C4	0.0287 (10)	0.0251 (9)	0.0335 (11)	−0.0070 (8)	−0.0077 (8)	−0.0075 (8)
C5	0.0517 (14)	0.0316 (11)	0.0266 (10)	−0.0142 (10)	−0.0113 (10)	−0.0037 (8)
C6	0.0444 (13)	0.0281 (10)	0.0256 (10)	−0.0148 (9)	−0.0067 (9)	−0.0015 (8)
C7	0.0493 (14)	0.0314 (11)	0.0456 (14)	−0.0196 (10)	−0.0076 (11)	−0.0095 (10)
C8	0.0305 (10)	0.0280 (10)	0.0227 (9)	−0.0097 (8)	−0.0047 (8)	−0.0032 (7)
C9	0.0258 (10)	0.0268 (10)	0.0211 (9)	−0.0056 (7)	−0.0027 (7)	−0.0050 (7)
C10	0.0336 (11)	0.0297 (10)	0.0235 (10)	−0.0096 (8)	−0.0085 (8)	−0.0024 (8)
C11	0.0310 (11)	0.0335 (11)	0.0261 (10)	−0.0119 (8)	−0.0043 (8)	−0.0060 (8)
C12	0.0304 (11)	0.0364 (11)	0.0251 (10)	−0.0133 (9)	−0.0042 (8)	−0.0059 (8)
C13	0.0309 (11)	0.0374 (11)	0.0291 (10)	−0.0108 (9)	−0.0048 (8)	−0.0083 (9)
C14	0.0330 (11)	0.0353 (11)	0.0272 (10)	−0.0130 (9)	−0.0047 (8)	−0.0057 (8)
C15	0.0350 (11)	0.0316 (10)	0.0277 (10)	−0.0118 (9)	−0.0050 (8)	−0.0041 (8)
C16	0.0396 (12)	0.0345 (11)	0.0300 (11)	−0.0125 (9)	−0.0078 (9)	−0.0057 (9)
C17	0.0534 (15)	0.0356 (12)	0.0375 (13)	−0.0065 (11)	−0.0114 (11)	−0.0104 (10)

Geometric parameters (Å, º)

Ni—S1	2.1796 (6)	C2—H1	0.950
Ni—S1^i	2.1796 (6)	C3—H2	0.950
Ni—N1	1.9310 (19)	C5—H3	0.950
Ni—N1^i	1.9310 (19)	C6—H4	0.950
S1—C9	1.726 (3)	C7—H5	0.980
S2—C9	1.7514 (19)	C7—H6	0.980
S2—C10	1.813 (3)	C7—H7	0.980
O1—C4	1.359 (3)	C8—H8	0.950
O1—C7	1.430 (3)	C10—H9	0.990
N1—N2	1.413 (3)	C10—H10	0.990
N1—C8	1.295 (3)	C11—H11	0.990
N2—C9	1.285 (3)	C11—H12	0.990
C1—C2	1.397 (3)	C12—H13	0.990
C1—C6	1.408 (3)	C12—H14	0.990
C1—C8	1.461 (4)	C13—H15	0.990
C2—C3	1.387 (4)	C13—H16	0.990
C3—C4	1.394 (3)	C14—H17	0.990
C4—C5	1.391 (4)	C14—H18	0.990
C5—C6	1.381 (4)	C15—H19	0.990
C10—C11	1.520 (3)	C15—H20	0.990
C11—C12	1.530 (4)	C16—H21	0.990
C12—C13	1.523 (3)	C16—H22	0.990
C13—C14	1.524 (4)	C17—H23	0.980
C14—C15	1.521 (3)	C17—H24	0.980
C15—C16	1.523 (4)	C17—H25	0.980
C16—C17	1.523 (4)
S1—Ni—S1^i	180	H5—C7—H7	109.469
S1—Ni—N1	85.67 (5)	H6—C7—H7	109.468
S1—Ni—N1^i	94.33 (5)	N1—C8—H8	113.566
S1^i—Ni—N1	94.33 (5)	C1—C8—H8	113.564
S1^i—Ni—N1^i	85.67 (5)	S2—C10—H9	108.878
N1—Ni—N1^i	180	S2—C10—H10	108.867
Ni—S1—C9	96.01 (7)	C11—C10—H9	108.875
C9—S2—C10	102.83 (10)	C11—C10—H10	108.870
C4—O1—C7	117.90 (18)	H9—C10—H10	107.715
Ni—N1—N2	120.42 (14)	C10—C11—H11	109.150
Ni—N1—C8	125.18 (14)	C10—C11—H12	109.154
N2—N1—C8	114.39 (18)	C12—C11—H11	109.156
N1—N2—C9	111.78 (18)	C12—C11—H12	109.148
C2—C1—C6	117.6 (2)	H11—C11—H12	107.871
C2—C1—C8	114.61 (18)	C11—C12—H13	108.897
C6—C1—C8	127.8 (2)	C11—C12—H14	108.908
C1—C2—C3	122.6 (2)	C13—C12—H13	108.898
C2—C3—C4	118.7 (2)	C13—C12—H14	108.904
O1—C4—C3	124.3 (2)	H13—C12—H14	107.731
O1—C4—C5	116.1 (2)	C12—C13—H15	108.904
C3—C4—C5	119.7 (3)	C12—C13—H16	108.898
C4—C5—C6	121.2 (2)	C14—C13—H15	108.903
C1—C6—C5	120.2 (2)	C14—C13—H16	108.909
N1—C8—C1	132.87 (18)	H15—C13—H16	107.731
S1—C9—S2	114.13 (12)	C13—C14—H17	108.794
S1—C9—N2	124.92 (15)	C13—C14—H18	108.791
S2—C9—N2	120.93 (17)	C15—C14—H17	108.796
S2—C10—C11	113.48 (16)	C15—C14—H18	108.799
C10—C11—C12	112.26 (18)	H17—C14—H18	107.675
C11—C12—C13	113.35 (18)	C14—C15—H19	108.797
C12—C13—C14	113.35 (19)	C14—C15—H20	108.794
C13—C14—C15	113.81 (19)	C16—C15—H19	108.799
C14—C15—C16	113.81 (19)	C16—C15—H20	108.804
C15—C16—C17	113.3 (2)	H19—C15—H20	107.669
C1—C2—H1	118.691	C15—C16—H21	108.921
C3—C2—H1	118.690	C15—C16—H22	108.918
C2—C3—H2	120.632	C17—C16—H21	108.926
C4—C3—H2	120.627	C17—C16—H22	108.913
C4—C5—H3	119.383	H21—C16—H22	107.738
C6—C5—H3	119.378	C16—C17—H23	109.473
C1—C6—H4	119.926	C16—C17—H24	109.467
C5—C6—H4	119.914	C16—C17—H25	109.462
O1—C7—H5	109.474	H23—C17—H24	109.479
O1—C7—H6	109.474	H23—C17—H25	109.474
O1—C7—H7	109.472	H24—C17—H25	109.472
H5—C7—H6	109.470
S1—Ni—N1—N2	−11.14 (10)	C8—N1—N2—C9	−167.88 (15)
S1—Ni—N1—C8	167.80 (12)	N1—N2—C9—S1	−3.7 (3)
N1—Ni—S1—C9	6.77 (5)	N1—N2—C9—S2	174.53 (13)
S1—Ni—N1^i—N2^i	−168.86 (10)	C2—C1—C6—C5	1.2 (3)
S1—Ni—N1^i—C8^i	12.20 (12)	C6—C1—C2—C3	−0.9 (3)
N1^i—Ni—S1—C9	−173.23 (5)	C2—C1—C8—N1	176.14 (18)
S1^i—Ni—N1—N2	168.86 (10)	C8—C1—C2—C3	177.33 (15)
S1^i—Ni—N1—C8	−12.20 (12)	C6—C1—C8—N1	−5.8 (4)
N1—Ni—S1^i—C9^i	173.23 (5)	C8—C1—C6—C5	−176.73 (17)
S1^i—Ni—N1^i—N2^i	11.14 (10)	C1—C2—C3—C4	−0.3 (3)
S1^i—Ni—N1^i—C8^i	−167.80 (12)	C2—C3—C4—O1	−178.68 (17)
N1^i—Ni—S1^i—C9^i	−6.77 (5)	C2—C3—C4—C5	1.2 (3)
Ni—S1—C9—S2	177.99 (9)	O1—C4—C5—C6	179.01 (17)
Ni—S1—C9—N2	−3.64 (16)	C3—C4—C5—C6	−0.9 (3)
C9—S2—C10—C11	84.61 (13)	C4—C5—C6—C1	−0.4 (3)
C10—S2—C9—S1	178.65 (11)	S2—C10—C11—C12	175.43 (11)
C10—S2—C9—N2	0.21 (17)	C10—C11—C12—C13	−174.38 (15)
C7—O1—C4—C3	6.1 (3)	C11—C12—C13—C14	177.19 (15)
C7—O1—C4—C5	−173.77 (16)	C12—C13—C14—C15	−179.74 (15)
Ni—N1—N2—C9	11.17 (19)	C13—C14—C15—C16	−176.95 (15)
Ni—N1—C8—C1	176.31 (13)	C14—C15—C16—C17	177.52 (15)
N2—N1—C8—C1	−4.7 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.