Bis(methyl 2-pyridylmethyl­idenedrazinecarbodithio­ato)nickel(II)

Brown crystals of the title compound, [Ni(C₈H₈N₃S₂)₂], were formed by reaction of methyl 2-pyridylmethyl­idene­hydrazinecarbodithio­ate with nickel(II) perchlorate at 323 K and recrystallization from ethanol at room temperature. The coordination geometry about nickel is distorted octa­hedral with the two ligands in the mer configuration. The azomethine N atoms are trans to each other, and the S and pyridine N atom are cis to each other.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.029
• wR factor = 0.079
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       5.70 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   S1      ..       6.11 su

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
   0 ALERT level B = Potentially serious problem
   2 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(methyl 2-pyridylmethylidenedrazinecarbodithioato)nickel(II)

Crystal data

[Ni(C8H8N3S2)2]	F(000) = 984
Mr = 479.30	Dx = 1.545 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 3615 reflections
a = 11.638 (2) Å	θ = 2.5–25.9°
b = 14.012 (3) Å	µ = 1.36 mm^−1
c = 13.130 (3) Å	T = 293 K
β = 105.795 (11)°	Block, brown
V = 2060.2 (7) Å^3	0.18 × 0.16 × 0.13 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3682 independent reflections
Radiation source: fine-focus sealed tube	2680 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 25.2°, θmin = 2.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→13
Tmin = 0.792, Tmax = 0.843	k = −16→16
11406 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0225P)^2 + 1.8004P] where P = (Fo^2 + 2Fc^2)/3
3682 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Ni1	0.72286 (3)	0.21510 (3)	0.53766 (3)	0.03318 (12)
S1	0.55878 (7)	0.26038 (6)	0.61149 (7)	0.0432 (2)
S2	0.31024 (8)	0.17702 (8)	0.53708 (9)	0.0641 (3)
S3	0.72108 (8)	0.35662 (7)	0.43041 (7)	0.0487 (2)
S4	0.84031 (10)	0.53621 (7)	0.49927 (9)	0.0625 (3)
N1	0.8179 (2)	0.13914 (19)	0.4465 (2)	0.0404 (6)
N2	0.5940 (2)	0.13027 (18)	0.44992 (19)	0.0346 (6)
N3	0.4782 (2)	0.12652 (19)	0.4585 (2)	0.0406 (7)
N4	0.7837 (2)	0.11715 (18)	0.66179 (19)	0.0339 (6)
N5	0.8531 (2)	0.29097 (17)	0.63681 (19)	0.0340 (6)
N6	0.8850 (2)	0.38423 (18)	0.6205 (2)	0.0408 (7)
C1	0.9320 (3)	0.1463 (3)	0.4460 (3)	0.0566 (10)
H1	0.9810	0.1884	0.4931	0.068*
C2	0.9807 (4)	0.0940 (3)	0.3790 (4)	0.0716 (12)
H2	1.0607	0.1012	0.3809	0.086*
C3	0.9093 (4)	0.0314 (3)	0.3097 (3)	0.0712 (12)
H3A	0.9400	−0.0049	0.2639	0.085*
C4	0.7912 (3)	0.0229 (3)	0.3090 (3)	0.0556 (10)
H4	0.7411	−0.0189	0.2623	0.067*
C5	0.7476 (3)	0.0775 (2)	0.3786 (2)	0.0402 (8)
C6	0.6240 (3)	0.0739 (2)	0.3840 (2)	0.0425 (8)
H6	0.5689	0.0325	0.3415	0.051*
C7	0.4604 (3)	0.1848 (2)	0.5320 (3)	0.0369 (7)
C8	0.3034 (4)	0.2469 (3)	0.6491 (4)	0.0734 (12)
H8A	0.3587	0.2220	0.7115	0.110*
H8B	0.2240	0.2445	0.6573	0.110*
H8C	0.3238	0.3119	0.6386	0.110*
C9	0.7491 (3)	0.0275 (2)	0.6708 (3)	0.0385 (8)
H9	0.6925	0.0004	0.6141	0.046*
C10	0.7935 (3)	−0.0261 (2)	0.7601 (3)	0.0470 (9)
H10	0.7704	−0.0894	0.7624	0.056*
C11	0.8722 (3)	0.0147 (3)	0.8457 (3)	0.0491 (9)
H11	0.9013	−0.0198	0.9079	0.059*
C12	0.9078 (3)	0.1080 (2)	0.8387 (2)	0.0419 (8)
H12	0.9601	0.1376	0.8963	0.050*
C13	0.8645 (3)	0.1563 (2)	0.7447 (2)	0.0349 (7)
C14	0.9015 (3)	0.2527 (2)	0.7266 (3)	0.0384 (8)
H14	0.9583	0.2853	0.7786	0.046*
C15	0.8234 (3)	0.4159 (2)	0.5284 (3)	0.0405 (8)
C16	0.9380 (4)	0.5844 (3)	0.6183 (3)	0.0775 (13)
H16A	0.9025	0.5763	0.6757	0.116*
H16B	0.9505	0.6512	0.6085	0.116*
H16C	1.0132	0.5516	0.6343	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0318 (2)	0.0342 (2)	0.0305 (2)	−0.00342 (18)	0.00341 (16)	−0.00299 (18)
S1	0.0400 (5)	0.0435 (5)	0.0452 (5)	−0.0045 (4)	0.0102 (4)	−0.0122 (4)
S2	0.0386 (5)	0.0711 (7)	0.0853 (8)	−0.0089 (5)	0.0217 (5)	−0.0205 (6)
S3	0.0494 (5)	0.0492 (6)	0.0417 (5)	−0.0029 (4)	0.0027 (4)	0.0097 (4)
S4	0.0827 (7)	0.0395 (6)	0.0665 (7)	−0.0058 (5)	0.0223 (6)	0.0119 (5)
N1	0.0391 (15)	0.0454 (17)	0.0350 (15)	0.0000 (13)	0.0074 (12)	−0.0030 (13)
N2	0.0324 (14)	0.0374 (15)	0.0309 (14)	−0.0014 (12)	0.0032 (11)	−0.0005 (12)
N3	0.0319 (14)	0.0430 (17)	0.0424 (16)	−0.0025 (13)	0.0023 (12)	−0.0047 (13)
N4	0.0339 (14)	0.0335 (15)	0.0319 (14)	0.0012 (12)	0.0049 (11)	−0.0007 (12)
N5	0.0357 (14)	0.0307 (14)	0.0346 (14)	−0.0022 (12)	0.0076 (12)	−0.0016 (12)
N6	0.0475 (16)	0.0319 (15)	0.0421 (16)	−0.0101 (13)	0.0106 (13)	0.0001 (13)
C1	0.045 (2)	0.066 (3)	0.059 (2)	−0.0011 (19)	0.0157 (19)	−0.008 (2)
C2	0.054 (2)	0.086 (3)	0.086 (3)	−0.001 (2)	0.037 (2)	−0.012 (3)
C3	0.076 (3)	0.079 (3)	0.069 (3)	0.007 (3)	0.038 (2)	−0.018 (2)
C4	0.065 (3)	0.055 (2)	0.049 (2)	0.004 (2)	0.019 (2)	−0.0108 (18)
C5	0.0463 (19)	0.0400 (19)	0.0334 (17)	0.0033 (16)	0.0092 (15)	−0.0020 (15)
C6	0.0444 (19)	0.044 (2)	0.0356 (18)	−0.0022 (16)	0.0045 (15)	−0.0127 (16)
C7	0.0319 (16)	0.0331 (18)	0.0435 (19)	−0.0017 (14)	0.0063 (14)	0.0055 (15)
C8	0.067 (3)	0.079 (3)	0.085 (3)	0.006 (2)	0.039 (2)	−0.010 (2)
C9	0.0394 (18)	0.0297 (18)	0.046 (2)	−0.0103 (15)	0.0118 (16)	−0.0024 (15)
C10	0.052 (2)	0.037 (2)	0.055 (2)	0.0007 (17)	0.0195 (19)	0.0067 (17)
C11	0.049 (2)	0.056 (2)	0.043 (2)	0.0128 (18)	0.0148 (18)	0.0155 (18)
C12	0.0400 (18)	0.046 (2)	0.0351 (18)	−0.0036 (16)	0.0032 (15)	0.0025 (15)
C13	0.0321 (16)	0.0361 (18)	0.0331 (17)	0.0011 (14)	0.0032 (14)	−0.0032 (14)
C14	0.0385 (18)	0.0320 (18)	0.0393 (19)	−0.0088 (15)	0.0015 (15)	−0.0053 (14)
C15	0.0422 (18)	0.0348 (19)	0.049 (2)	−0.0052 (15)	0.0205 (16)	0.0027 (16)
C16	0.103 (3)	0.046 (3)	0.085 (3)	−0.028 (2)	0.030 (3)	−0.008 (2)

Geometric parameters (Å, º)

Ni1—N5	2.012 (2)	C2—C3	1.371 (5)
Ni1—N2	2.012 (2)	C2—H2	0.9300
Ni1—N4	2.101 (2)	C3—C4	1.376 (5)
Ni1—N1	2.123 (3)	C3—H3A	0.9300
Ni1—S3	2.4289 (10)	C4—C5	1.389 (4)
Ni1—S1	2.4487 (10)	C4—H4	0.9300
S1—C7	1.694 (3)	C5—C6	1.461 (4)
S2—C7	1.771 (3)	C6—H6	0.9300
S2—C8	1.787 (4)	C8—H8A	0.9600
S3—C15	1.711 (3)	C8—H8B	0.9600
S4—C15	1.752 (3)	C8—H8C	0.9600
S4—C16	1.795 (4)	C9—C10	1.370 (4)
N1—C1	1.333 (4)	C9—H9	0.9300
N1—C5	1.346 (4)	C10—C11	1.367 (5)
N2—C6	1.287 (4)	C10—H10	0.9300
N2—N3	1.383 (3)	C11—C12	1.381 (5)
N3—C7	1.323 (4)	C11—H11	0.9300
N4—C9	1.334 (4)	C12—C13	1.376 (4)
N4—C13	1.347 (4)	C12—H12	0.9300
N5—C14	1.278 (4)	C13—C14	1.458 (4)
N5—N6	1.391 (3)	C14—H14	0.9300
N6—C15	1.304 (4)	C16—H16A	0.9600
C1—C2	1.379 (5)	C16—H16B	0.9600
C1—H1	0.9300	C16—H16C	0.9600
N5—Ni1—N2	174.51 (10)	C5—C4—H4	120.3
N5—Ni1—N4	78.92 (10)	N1—C5—C4	121.6 (3)
N2—Ni1—N4	95.71 (10)	N1—C5—C6	114.7 (3)
N5—Ni1—N1	102.31 (10)	C4—C5—C6	123.7 (3)
N2—Ni1—N1	78.61 (10)	N2—C6—C5	117.5 (3)
N4—Ni1—N1	89.58 (10)	N2—C6—H6	121.2
N5—Ni1—S3	80.20 (8)	C5—C6—H6	121.2
N2—Ni1—S3	105.24 (8)	N3—C7—S1	128.4 (2)
N4—Ni1—S3	158.61 (7)	N3—C7—S2	110.0 (2)
N1—Ni1—S3	90.35 (8)	S1—C7—S2	121.6 (2)
N5—Ni1—S1	97.96 (7)	S2—C8—H8A	109.5
N2—Ni1—S1	80.77 (8)	S2—C8—H8B	109.5
N4—Ni1—S1	89.80 (7)	H8A—C8—H8B	109.5
N1—Ni1—S1	159.21 (8)	S2—C8—H8C	109.5
S3—Ni1—S1	97.67 (4)	H8A—C8—H8C	109.5
C7—S1—Ni1	93.63 (11)	H8B—C8—H8C	109.5
C7—S2—C8	105.23 (18)	N4—C9—C10	122.7 (3)
C15—S3—Ni1	93.76 (11)	N4—C9—H9	118.7
C15—S4—C16	104.73 (18)	C10—C9—H9	118.7
C1—N1—C5	118.1 (3)	C11—C10—C9	119.1 (3)
C1—N1—Ni1	129.6 (2)	C11—C10—H10	120.5
C5—N1—Ni1	112.3 (2)	C9—C10—H10	120.5
C6—N2—N3	118.7 (3)	C10—C11—C12	119.1 (3)
C6—N2—Ni1	116.8 (2)	C10—C11—H11	120.4
N3—N2—Ni1	124.50 (19)	C12—C11—H11	120.4
C7—N3—N2	112.7 (2)	C13—C12—C11	118.8 (3)
C9—N4—C13	118.2 (3)	C13—C12—H12	120.6
C9—N4—Ni1	129.6 (2)	C11—C12—H12	120.6
C13—N4—Ni1	112.0 (2)	N4—C13—C12	122.0 (3)
C14—N5—N6	117.9 (3)	N4—C13—C14	114.7 (3)
C14—N5—Ni1	116.1 (2)	C12—C13—C14	123.4 (3)
N6—N5—Ni1	125.61 (19)	N5—C14—C13	117.7 (3)
C15—N6—N5	111.1 (3)	N5—C14—H14	121.2
N1—C1—C2	123.1 (4)	C13—C14—H14	121.2
N1—C1—H1	118.4	N6—C15—S3	128.8 (2)
C2—C1—H1	118.4	N6—C15—S4	117.6 (2)
C3—C2—C1	118.9 (4)	S3—C15—S4	113.51 (19)
C3—C2—H2	120.6	S4—C16—H16A	109.5
C1—C2—H2	120.6	S4—C16—H16B	109.5
C2—C3—C4	118.9 (4)	H16A—C16—H16B	109.5
C2—C3—H3A	120.5	S4—C16—H16C	109.5
C4—C3—H3A	120.5	H16A—C16—H16C	109.5
C3—C4—C5	119.4 (4)	H16B—C16—H16C	109.5
C3—C4—H4	120.3
N5—Ni1—S1—C7	−174.43 (13)	S3—Ni1—N5—N6	6.0 (2)
N2—Ni1—S1—C7	0.17 (13)	S1—Ni1—N5—N6	−90.5 (2)
N4—Ni1—S1—C7	−95.64 (13)	C14—N5—N6—C15	−175.9 (3)
N1—Ni1—S1—C7	−7.4 (2)	Ni1—N5—N6—C15	−3.5 (4)
S3—Ni1—S1—C7	104.46 (11)	C5—N1—C1—C2	0.4 (6)
N5—Ni1—S3—C15	−5.31 (13)	Ni1—N1—C1—C2	−177.6 (3)
N2—Ni1—S3—C15	173.96 (13)	N1—C1—C2—C3	−0.3 (7)
N4—Ni1—S3—C15	−18.0 (2)	C1—C2—C3—C4	0.2 (7)
N1—Ni1—S3—C15	−107.75 (13)	C2—C3—C4—C5	−0.3 (6)
S1—Ni1—S3—C15	91.49 (11)	C1—N1—C5—C4	−0.5 (5)
N5—Ni1—N1—C1	−6.4 (3)	Ni1—N1—C5—C4	177.8 (3)
N2—Ni1—N1—C1	179.2 (3)	C1—N1—C5—C6	−180.0 (3)
N4—Ni1—N1—C1	−84.9 (3)	Ni1—N1—C5—C6	−1.7 (3)
S3—Ni1—N1—C1	73.7 (3)	C3—C4—C5—N1	0.5 (6)
S1—Ni1—N1—C1	−173.2 (2)	C3—C4—C5—C6	179.9 (4)
N5—Ni1—N1—C5	175.6 (2)	N3—N2—C6—C5	−178.4 (3)
N2—Ni1—N1—C5	1.1 (2)	Ni1—N2—C6—C5	−0.5 (4)
N4—Ni1—N1—C5	97.0 (2)	N1—C5—C6—N2	1.5 (4)
S3—Ni1—N1—C5	−104.4 (2)	C4—C5—C6—N2	−178.0 (3)
S1—Ni1—N1—C5	8.7 (4)	N2—N3—C7—S1	0.7 (4)
N4—Ni1—N2—C6	−88.7 (2)	N2—N3—C7—S2	179.29 (19)
N1—Ni1—N2—C6	−0.3 (2)	Ni1—S1—C7—N3	−0.6 (3)
S3—Ni1—N2—C6	86.9 (2)	Ni1—S1—C7—S2	−178.98 (18)
S1—Ni1—N2—C6	−177.6 (2)	C8—S2—C7—N3	173.0 (3)
N4—Ni1—N2—N3	89.0 (2)	C8—S2—C7—S1	−8.3 (3)
N1—Ni1—N2—N3	177.4 (2)	C13—N4—C9—C10	−0.8 (5)
S3—Ni1—N2—N3	−95.4 (2)	Ni1—N4—C9—C10	−176.5 (2)
S1—Ni1—N2—N3	0.1 (2)	N4—C9—C10—C11	3.2 (5)
C6—N2—N3—C7	177.2 (3)	C9—C10—C11—C12	−2.1 (5)
Ni1—N2—N3—C7	−0.5 (4)	C10—C11—C12—C13	−1.2 (5)
N5—Ni1—N4—C9	−177.5 (3)	C9—N4—C13—C12	−2.7 (4)
N2—Ni1—N4—C9	3.7 (3)	Ni1—N4—C13—C12	173.7 (2)
N1—Ni1—N4—C9	−74.8 (3)	C9—N4—C13—C14	177.3 (3)
S3—Ni1—N4—C9	−164.72 (19)	Ni1—N4—C13—C14	−6.3 (3)
S1—Ni1—N4—C9	84.4 (3)	C11—C12—C13—N4	3.7 (5)
N5—Ni1—N4—C13	6.7 (2)	C11—C12—C13—C14	−176.3 (3)
N2—Ni1—N4—C13	−172.2 (2)	N6—N5—C14—C13	177.8 (3)
N1—Ni1—N4—C13	109.3 (2)	Ni1—N5—C14—C13	4.6 (4)
S3—Ni1—N4—C13	19.4 (3)	N4—C13—C14—N5	1.4 (4)
S1—Ni1—N4—C13	−91.5 (2)	C12—C13—C14—N5	−178.6 (3)
N4—Ni1—N5—C14	−6.1 (2)	N5—N6—C15—S3	−3.7 (4)
N1—Ni1—N5—C14	−93.3 (2)	N5—N6—C15—S4	173.7 (2)
S3—Ni1—N5—C14	178.5 (2)	Ni1—S3—C15—N6	6.9 (3)
S1—Ni1—N5—C14	82.1 (2)	Ni1—S3—C15—S4	−170.54 (16)
N4—Ni1—N5—N6	−178.7 (2)	C16—S4—C15—N6	−3.9 (3)
N1—Ni1—N5—N6	94.2 (2)	C16—S4—C15—S3	173.8 (2)