Benzyl­tri­methyl­ammonium tris­(pyrimidine-2-thiol­ato-κ²N,S)­nickelate(II)

The title compound, cis-[C₆H₅CH₂N(CH₃)₃][Ni(pymt)₃], (pymt = pyrimidine-2-thiol­ate, C₄H₃N₂S) consists of discrete cations and anions. The coordination geometry around nickel is highly distorted octahedral due to the presence of three four-membered N,S-chelate rings in a cis configuration. The Ni—S distances are in the range 2.4617 (5)–2.5290 (5) Å and the Ni—N bond distances range from 2.0490 (14) to 2.0689 (14) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.070
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Ni1    -   S1      ..      10.24 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   S2      ..       9.57 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   S3      ..       8.48 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N5      ..       5.41 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C10 H16 N

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

(I)

Crystal data

(C10H16N)[Ni(C4H3N2S)3]	Z = 2
Mr = 542.38	F(000) = 564
Triclinic, P1	Dx = 1.467 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5730 (8) Å	Cell parameters from 3472 reflections
b = 12.4729 (14) Å	θ = 1.5–28.3°
c = 13.5236 (13) Å	µ = 1.07 mm^−1
α = 90.205 (4)°	T = 293 K
β = 101.633 (5)°	Prism, green
γ = 100.889 (6)°	0.20 × 0.20 × 0.20 mm
V = 1227.5 (2) Å^3

Data collection

Mercury CCD diffractometer	5984 independent reflections
Radiation source: fine-focus sealed tube	5426 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan CrystalClear (Rigaku, 2000)	h = −10→9
Tmin = 0.746, Tmax = 0.807	k = −15→16
10173 measured reflections	l = −17→18

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0287P)^2 + 0.6691P] where P = (Fo^2 + 2Fc^2)/3
5984 reflections	(Δ/σ)max = 0.002
293 parameters	Δρmax = 0.66 e Å^−3
0 restraints	Δρmin = −0.49 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	0.55178 (3)	0.750189 (16)	0.720911 (16)	0.01366 (6)
S1	0.22450 (6)	0.66261 (3)	0.68577 (3)	0.01794 (9)
S2	0.67683 (6)	0.64298 (3)	0.86262 (3)	0.01655 (9)
S3	0.55564 (6)	0.92518 (3)	0.81706 (3)	0.02025 (10)
N1	0.41420 (19)	0.79524 (11)	0.58400 (10)	0.0159 (3)
N2	0.0934 (2)	0.74802 (12)	0.50896 (11)	0.0220 (3)
N3	0.65082 (19)	0.62154 (11)	0.67038 (10)	0.0152 (3)
N4	0.7986 (2)	0.49042 (12)	0.76515 (11)	0.0187 (3)
N5	0.79084 (19)	0.86165 (11)	0.72782 (11)	0.0163 (3)
N6	0.8974 (2)	1.03614 (13)	0.81414 (12)	0.0259 (3)*
N7	0.77060 (19)	1.26891 (11)	0.99198 (10)	0.0159 (3)
C1	0.2393 (2)	0.74043 (13)	0.58264 (12)	0.0160 (3)
C2	0.1281 (3)	0.81372 (15)	0.43428 (14)	0.0247 (4)
H2A	0.0281	0.8208	0.3812	0.030*
C3	0.3008 (3)	0.87196 (15)	0.42979 (14)	0.0241 (4)
H3A	0.3205	0.9180	0.3757	0.029*
C4	0.4430 (3)	0.85963 (14)	0.50811 (13)	0.0202 (3)
H4A	0.5640	0.8979	0.5079	0.024*
C5	0.7144 (2)	0.57666 (13)	0.75904 (12)	0.0148 (3)
C6	0.8196 (2)	0.44934 (14)	0.67784 (14)	0.0209 (4)
H6A	0.8782	0.3882	0.6799	0.025*
C7	0.7612 (2)	0.49029 (14)	0.58474 (13)	0.0206 (4)
H7A	0.7788	0.4593	0.5240	0.025*
C8	0.6758 (2)	0.57883 (14)	0.58491 (13)	0.0184 (3)
H8A	0.6339	0.6100	0.5226	0.022*
C9	0.7679 (2)	0.94579 (13)	0.78562 (13)	0.0173 (3)
C10	0.9469 (2)	0.86963 (15)	0.69466 (14)	0.0215 (4)
H10A	0.9632	0.8121	0.6533	0.026*
C11	1.0855 (3)	0.96107 (17)	0.71992 (16)	0.0285 (4)
H11A	1.1969	0.9682	0.6963	0.034*
C12	1.0541 (3)	1.04107 (16)	0.78077 (16)	0.0291 (4)
H12A	1.1489	1.1035	0.8004	0.035*
C13	0.7778 (3)	1.37935 (15)	1.03821 (14)	0.0236 (4)
H13A	0.9058	1.4131	1.0670	0.035*
H13B	0.7067	1.3717	1.0917	0.035*
H13C	0.7255	1.4255	0.9862	0.035*
C14	0.8424 (3)	1.19674 (16)	1.07283 (14)	0.0261 (4)
H14A	0.9694	1.2294	1.1047	0.039*
H14B	0.8387	1.1246	1.0427	0.039*
H14C	0.7659	1.1891	1.1238	0.039*
C15	0.8899 (2)	1.28093 (15)	0.91508 (13)	0.0207 (4)
H15A	1.0150	1.3170	0.9472	0.031*
H15B	0.8404	1.3251	0.8603	0.031*
H15C	0.8921	1.2085	0.8875	0.031*
C16	0.5735 (2)	1.21341 (14)	0.94570 (13)	0.0179 (3)
H16A	0.5738	1.1378	0.9234	0.021*
H16B	0.5000	1.2088	0.9989	0.021*
C17	0.4798 (2)	1.26935 (13)	0.85734 (12)	0.0159 (3)
C18	0.3853 (2)	1.35207 (14)	0.87108 (13)	0.0196 (3)
H18A	0.3848	1.3768	0.9375	0.023*
C19	0.2921 (2)	1.39864 (15)	0.78868 (14)	0.0213 (4)
H19A	0.2292	1.4555	0.7989	0.026*
C20	0.2902 (2)	1.36252 (15)	0.69149 (14)	0.0221 (4)
H20A	0.2263	1.3945	0.6350	0.027*
C21	0.3820 (3)	1.27934 (15)	0.67693 (13)	0.0229 (4)
H21A	0.3802	1.2540	0.6104	0.027*
C22	0.4764 (2)	1.23317 (14)	0.75928 (13)	0.0194 (3)
H22A	0.5392	1.1764	0.7487	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.01325 (11)	0.01303 (10)	0.01471 (11)	0.00287 (8)	0.00259 (8)	0.00043 (7)
S1	0.0162 (2)	0.0180 (2)	0.0184 (2)	0.00125 (16)	0.00240 (16)	0.00297 (15)
S2	0.0174 (2)	0.0193 (2)	0.01275 (19)	0.00365 (16)	0.00248 (15)	0.00004 (14)
S3	0.0196 (2)	0.0175 (2)	0.0254 (2)	0.00370 (16)	0.00867 (18)	−0.00287 (16)
N1	0.0170 (7)	0.0146 (7)	0.0164 (7)	0.0040 (5)	0.0032 (5)	−0.0005 (5)
N2	0.0203 (8)	0.0235 (8)	0.0201 (7)	0.0051 (6)	−0.0015 (6)	0.0006 (6)
N3	0.0165 (7)	0.0140 (6)	0.0147 (7)	0.0024 (5)	0.0026 (5)	0.0014 (5)
N4	0.0186 (7)	0.0168 (7)	0.0204 (7)	0.0052 (6)	0.0018 (6)	0.0014 (5)
N5	0.0150 (7)	0.0175 (7)	0.0174 (7)	0.0053 (6)	0.0036 (6)	0.0024 (5)
N6	0.0240 (8)	0.0185 (7)	0.0299 (8)	−0.0036 (6)	−0.0001 (7)	−0.0005 (6)
N7	0.0141 (7)	0.0187 (7)	0.0141 (7)	0.0022 (5)	0.0017 (5)	0.0033 (5)
C1	0.0178 (8)	0.0142 (7)	0.0163 (8)	0.0047 (6)	0.0024 (6)	−0.0029 (6)
C2	0.0297 (10)	0.0243 (9)	0.0177 (9)	0.0084 (8)	−0.0040 (7)	−0.0002 (7)
C3	0.0348 (11)	0.0212 (9)	0.0180 (9)	0.0091 (8)	0.0057 (8)	0.0047 (7)
C4	0.0252 (9)	0.0166 (8)	0.0197 (8)	0.0046 (7)	0.0063 (7)	0.0017 (6)
C5	0.0118 (8)	0.0142 (7)	0.0166 (8)	0.0004 (6)	0.0010 (6)	0.0006 (6)
C6	0.0185 (9)	0.0162 (8)	0.0283 (9)	0.0060 (7)	0.0032 (7)	−0.0024 (7)
C7	0.0218 (9)	0.0196 (8)	0.0206 (9)	0.0030 (7)	0.0060 (7)	−0.0057 (6)
C8	0.0198 (8)	0.0184 (8)	0.0154 (8)	0.0012 (7)	0.0024 (6)	−0.0002 (6)
C9	0.0171 (8)	0.0158 (8)	0.0175 (8)	0.0029 (6)	0.0006 (6)	0.0028 (6)
C10	0.0164 (8)	0.0265 (9)	0.0242 (9)	0.0090 (7)	0.0054 (7)	0.0089 (7)
C11	0.0146 (9)	0.0346 (11)	0.0371 (11)	0.0038 (8)	0.0072 (8)	0.0153 (9)
C12	0.0178 (9)	0.0256 (10)	0.0365 (11)	−0.0060 (7)	−0.0021 (8)	0.0082 (8)
C13	0.0218 (9)	0.0238 (9)	0.0228 (9)	0.0026 (7)	0.0011 (7)	−0.0061 (7)
C14	0.0199 (9)	0.0317 (10)	0.0244 (9)	0.0043 (8)	−0.0004 (7)	0.0132 (8)
C15	0.0182 (9)	0.0260 (9)	0.0198 (9)	0.0057 (7)	0.0074 (7)	0.0033 (7)
C16	0.0147 (8)	0.0186 (8)	0.0176 (8)	−0.0009 (6)	0.0009 (6)	0.0033 (6)
C17	0.0128 (8)	0.0167 (8)	0.0156 (8)	−0.0014 (6)	0.0012 (6)	0.0019 (6)
C18	0.0192 (9)	0.0235 (9)	0.0152 (8)	0.0031 (7)	0.0028 (7)	−0.0023 (6)
C19	0.0194 (9)	0.0226 (9)	0.0222 (9)	0.0068 (7)	0.0027 (7)	−0.0003 (7)
C20	0.0199 (9)	0.0264 (9)	0.0188 (8)	0.0045 (7)	0.0011 (7)	0.0044 (7)
C21	0.0268 (10)	0.0274 (9)	0.0147 (8)	0.0050 (8)	0.0048 (7)	−0.0015 (7)
C22	0.0188 (8)	0.0193 (8)	0.0198 (8)	0.0041 (7)	0.0033 (7)	−0.0016 (6)

Geometric parameters (Å, º)

Ni1—N5	2.0492 (14)	C7—C8	1.381 (2)
Ni1—N3	2.0635 (14)	C7—H7A	0.9500
Ni1—N1	2.0689 (14)	C8—H8A	0.9500
Ni1—S1	2.4617 (5)	C10—C11	1.386 (3)
Ni1—S2	2.4743 (5)	C10—H10A	0.9500
Ni1—S3	2.5290 (5)	C11—C12	1.375 (3)
S1—C1	1.7122 (17)	C11—H11A	0.9500
S2—C5	1.7232 (17)	C12—H12A	0.9500
S3—C9	1.7179 (17)	C13—H13A	0.9800
N1—C4	1.333 (2)	C13—H13B	0.9800
N1—C1	1.367 (2)	C13—H13C	0.9800
N2—C2	1.339 (2)	C14—H14A	0.9800
N2—C1	1.349 (2)	C14—H14B	0.9800
N3—C8	1.333 (2)	C14—H14C	0.9800
N3—C5	1.363 (2)	C15—H15A	0.9800
N4—C6	1.336 (2)	C15—H15B	0.9800
N4—C5	1.345 (2)	C15—H15C	0.9800
N5—C10	1.333 (2)	C16—C17	1.506 (2)
N5—C9	1.364 (2)	C16—H16A	0.9900
N6—C12	1.343 (3)	C16—H16B	0.9900
N6—C9	1.344 (2)	C17—C22	1.393 (2)
N7—C13	1.498 (2)	C17—C18	1.394 (2)
N7—C15	1.500 (2)	C18—C19	1.386 (2)
N7—C14	1.501 (2)	C18—H18A	0.9500
N7—C16	1.526 (2)	C19—C20	1.384 (3)
C2—C3	1.384 (3)	C19—H19A	0.9500
C2—H2A	0.9500	C20—C21	1.387 (3)
C3—C4	1.382 (3)	C20—H20A	0.9500
C3—H3A	0.9500	C21—C22	1.386 (2)
C4—H4A	0.9500	C21—H21A	0.9500
C6—C7	1.381 (3)	C22—H22A	0.9500
C6—H6A	0.9500
N5—Ni1—N3	94.69 (6)	N3—C8—C7	121.57 (16)
N5—Ni1—N1	96.66 (6)	N3—C8—H8A	119.2
N3—Ni1—N1	99.25 (5)	C7—C8—H8A	119.2
N5—Ni1—S1	162.19 (4)	N6—C9—N5	123.44 (15)
N3—Ni1—S1	97.38 (4)	N6—C9—S3	123.45 (13)
N1—Ni1—S1	68.52 (4)	N5—C9—S3	113.10 (12)
N5—Ni1—S2	95.47 (4)	N5—C10—C11	120.66 (18)
N3—Ni1—S2	68.50 (4)	N5—C10—H10A	119.7
N1—Ni1—S2	163.43 (4)	C11—C10—H10A	119.7
S1—Ni1—S2	101.113 (16)	C12—C11—C10	116.84 (17)
N5—Ni1—S3	67.63 (4)	C12—C11—H11A	121.6
N3—Ni1—S3	158.31 (4)	C10—C11—H11A	121.6
N1—Ni1—S3	95.37 (4)	N6—C12—C11	123.89 (18)
S1—Ni1—S3	102.858 (17)	N6—C12—H12A	118.1
S2—Ni1—S3	99.663 (18)	C11—C12—H12A	118.1
C1—S1—Ni1	77.83 (6)	N7—C13—H13A	109.5
C5—S2—Ni1	77.37 (6)	N7—C13—H13B	109.5
C9—S3—Ni1	76.34 (6)	H13A—C13—H13B	109.5
C4—N1—C1	118.37 (15)	N7—C13—H13C	109.5
C4—N1—Ni1	140.66 (13)	H13A—C13—H13C	109.5
C1—N1—Ni1	100.86 (10)	H13B—C13—H13C	109.5
C2—N2—C1	115.99 (16)	N7—C14—H14A	109.5
C8—N3—C5	118.31 (14)	N7—C14—H14B	109.5
C8—N3—Ni1	140.16 (12)	H14A—C14—H14B	109.5
C5—N3—Ni1	101.40 (10)	N7—C14—H14C	109.5
C6—N4—C5	116.22 (15)	H14A—C14—H14C	109.5
C10—N5—C9	119.05 (15)	H14B—C14—H14C	109.5
C10—N5—Ni1	138.16 (13)	N7—C15—H15A	109.5
C9—N5—Ni1	102.77 (10)	N7—C15—H15B	109.5
C12—N6—C9	116.08 (17)	H15A—C15—H15B	109.5
C13—N7—C15	108.94 (13)	N7—C15—H15C	109.5
C13—N7—C14	109.30 (14)	H15A—C15—H15C	109.5
C15—N7—C14	108.97 (13)	H15B—C15—H15C	109.5
C13—N7—C16	111.31 (13)	C17—C16—N7	115.15 (13)
C15—N7—C16	111.59 (13)	C17—C16—H16A	108.5
C14—N7—C16	106.67 (13)	N7—C16—H16A	108.5
N2—C1—N1	123.78 (15)	C17—C16—H16B	108.5
N2—C1—S1	123.47 (13)	N7—C16—H16B	108.5
N1—C1—S1	112.73 (12)	H16A—C16—H16B	107.5
N2—C2—C3	123.91 (17)	C22—C17—C18	118.77 (15)
N2—C2—H2A	118.0	C22—C17—C16	119.61 (15)
C3—C2—H2A	118.0	C18—C17—C16	121.47 (15)
C4—C3—C2	116.53 (16)	C19—C18—C17	120.60 (16)
C4—C3—H3A	121.7	C19—C18—H18A	119.7
C2—C3—H3A	121.7	C17—C18—H18A	119.7
N1—C4—C3	121.41 (17)	C20—C19—C18	120.20 (17)
N1—C4—H4A	119.3	C20—C19—H19A	119.9
C3—C4—H4A	119.3	C18—C19—H19A	119.9
N4—C5—N3	123.68 (15)	C19—C20—C21	119.68 (17)
N4—C5—S2	123.63 (13)	C19—C20—H20A	120.2
N3—C5—S2	112.69 (12)	C21—C20—H20A	120.2
N4—C6—C7	124.00 (16)	C22—C21—C20	120.18 (16)
N4—C6—H6A	118.0	C22—C21—H21A	119.9
C7—C6—H6A	118.0	C20—C21—H21A	119.9
C6—C7—C8	116.22 (16)	C21—C22—C17	120.54 (16)
C6—C7—H7A	121.9	C21—C22—H22A	119.7
C8—C7—H7A	121.9	C17—C22—H22A	119.7