Bis(N,N-diethyl­dithio­carbamato-κ²S,S′)(3,5-dimethyl­pyrazolato-κN)zinc(II)

The crystal structure of the title compound, [Zn(C₅H₁₀NS₂)₂(C₅H₈N₂)], an adduct of Zn(S₂CNEt₂)₂ and 3,5-dimethyl­pyrazole (DMPZ), has the Zn atom coordinated by one N atom from one DMPZ ligand and four S atoms of two S₂CNEt₂ ligands in a square-pyramidal geometry; the N atom occupies the apical site.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.079
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn1    -   S2      ..       8.44 su

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

   0 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: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(N,N-diethyldithiocarbamato-κ²S,S')(3,5-dimethylpyrazolato-κN)zinc(II)

Crystal data

[Zn(C5H10NS2)2(C5H8N2)]	F(000) = 960
Mr = 458.08	Dx = 1.469 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7229 reflections
a = 14.724 (3) Å	θ = 3.0–25.3°
b = 8.8631 (18) Å	µ = 1.60 mm^−1
c = 17.464 (4) Å	T = 193 K
β = 114.71 (3)°	Block, colourless
V = 2070.4 (9) Å^3	0.30 × 0.20 × 0.09 mm
Z = 4

Data collection

Rigaku Mercury diffractometer	3789 independent reflections
Radiation source: fine-focus sealed tube	3428 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 25.4°, θmin = 3.1°
Absorption correction: multi-scan (Jacobson, 1998)	h = −15→17
Tmin = 0.616, Tmax = 0.866	k = −10→10
19685 measured reflections	l = −21→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0313P)^2 + 2.0654P] where P = (Fo^2 + 2Fc^2)/3
3789 reflections	(Δ/σ)max = 0.001
223 parameters	Δρmax = 0.36 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.

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

	x	y	z	Uiso*/Ueq
Zn1	0.79062 (2)	0.37892 (3)	0.514786 (19)	0.01898 (11)
S1	0.70788 (5)	0.26365 (8)	0.38181 (4)	0.02096 (16)
S2	0.91207 (5)	0.38638 (8)	0.43862 (4)	0.02000 (16)
S3	0.69407 (5)	0.30597 (9)	0.59757 (4)	0.02607 (18)
S4	0.91159 (5)	0.33950 (8)	0.65449 (4)	0.02227 (17)
N1	0.79776 (15)	0.3082 (2)	0.27916 (13)	0.0173 (5)
N2	0.82602 (16)	0.2727 (3)	0.75787 (14)	0.0237 (5)
N3	0.76639 (16)	0.6068 (2)	0.50213 (14)	0.0186 (5)
N4	0.84473 (16)	0.7026 (2)	0.52304 (14)	0.0184 (5)
H4	0.9058	0.6737	0.5397	0.022*
C1	0.80608 (18)	0.3186 (3)	0.35750 (16)	0.0158 (5)
C2	0.7078 (2)	0.2469 (3)	0.20959 (17)	0.0231 (6)
H2A	0.6774	0.1715	0.2317	0.028*
H2B	0.7270	0.1979	0.1689	0.028*
C3	0.6319 (2)	0.3694 (3)	0.16579 (19)	0.0290 (7)
H3A	0.6061	0.4089	0.2039	0.043*
H3B	0.5781	0.3279	0.1172	0.043*
H3C	0.6635	0.4490	0.1486	0.043*
C4	0.8758 (2)	0.3633 (3)	0.25415 (18)	0.0214 (6)
H4A	0.9148	0.4405	0.2935	0.026*
H4B	0.8443	0.4090	0.1987	0.026*
C5	0.9447 (2)	0.2384 (4)	0.2521 (2)	0.0332 (7)
H5A	0.9802	0.1984	0.3079	0.050*
H5B	0.9916	0.2778	0.2322	0.050*
H5C	0.9061	0.1596	0.2151	0.050*
C6	0.81191 (19)	0.3036 (3)	0.67935 (17)	0.0205 (6)
C7	0.7406 (2)	0.2498 (4)	0.78076 (19)	0.0302 (7)
H7A	0.7635	0.1963	0.8340	0.036*
H7B	0.6903	0.1882	0.7381	0.036*
C8	0.6949 (2)	0.3977 (4)	0.7882 (2)	0.0338 (8)
H8A	0.7449	0.4594	0.8298	0.051*
H8B	0.6414	0.3795	0.8047	0.051*
H8C	0.6694	0.4486	0.7348	0.051*
C9	0.9267 (2)	0.2554 (4)	0.82652 (18)	0.0298 (7)
H9A	0.9734	0.2312	0.8022	0.036*
H9B	0.9261	0.1711	0.8617	0.036*
C10	0.9635 (2)	0.3938 (4)	0.8810 (2)	0.0436 (9)
H10A	0.9676	0.4767	0.8472	0.065*
H10B	1.0284	0.3743	0.9251	0.065*
H10C	0.9178	0.4187	0.9053	0.065*
C11	0.5838 (2)	0.6276 (3)	0.45457 (19)	0.0266 (7)
H11A	0.5745	0.5475	0.4150	0.040*
H11B	0.5338	0.7038	0.4289	0.040*
H11C	0.5778	0.5883	0.5034	0.040*
C12	0.68553 (19)	0.6953 (3)	0.48010 (16)	0.0191 (6)
C13	0.71392 (19)	0.8462 (3)	0.48690 (17)	0.0217 (6)
H13	0.6719	0.9295	0.4749	0.026*
C14	0.8163 (2)	0.8483 (3)	0.51475 (16)	0.0198 (6)
C15	0.8908 (2)	0.9729 (3)	0.53667 (18)	0.0241 (6)
H15A	0.8991	1.0170	0.5894	0.036*
H15B	0.8676	1.0484	0.4933	0.036*
H15C	0.9537	0.9336	0.5414	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02295 (18)	0.01795 (18)	0.01619 (18)	−0.00083 (13)	0.00834 (14)	−0.00071 (13)
S1	0.0194 (3)	0.0258 (4)	0.0185 (3)	−0.0055 (3)	0.0088 (3)	−0.0039 (3)
S2	0.0149 (3)	0.0273 (4)	0.0174 (3)	−0.0016 (3)	0.0064 (3)	−0.0044 (3)
S3	0.0187 (3)	0.0387 (4)	0.0190 (4)	−0.0066 (3)	0.0062 (3)	0.0036 (3)
S4	0.0175 (3)	0.0310 (4)	0.0196 (4)	0.0005 (3)	0.0090 (3)	0.0003 (3)
N1	0.0164 (11)	0.0179 (12)	0.0166 (12)	0.0005 (9)	0.0060 (9)	0.0003 (9)
N2	0.0202 (12)	0.0324 (14)	0.0192 (12)	−0.0018 (10)	0.0090 (10)	0.0015 (11)
N3	0.0172 (11)	0.0198 (12)	0.0197 (12)	−0.0025 (9)	0.0087 (9)	−0.0009 (10)
N4	0.0134 (11)	0.0197 (12)	0.0213 (12)	0.0007 (9)	0.0064 (9)	0.0007 (10)
C1	0.0178 (13)	0.0116 (12)	0.0179 (14)	0.0014 (10)	0.0074 (11)	−0.0006 (11)
C2	0.0270 (15)	0.0248 (15)	0.0160 (14)	−0.0036 (12)	0.0075 (12)	−0.0063 (12)
C3	0.0210 (15)	0.0377 (18)	0.0242 (16)	0.0013 (13)	0.0053 (12)	0.0040 (14)
C4	0.0211 (14)	0.0257 (15)	0.0200 (14)	−0.0002 (12)	0.0112 (12)	0.0007 (12)
C5	0.0331 (17)	0.0427 (19)	0.0305 (17)	0.0122 (15)	0.0199 (14)	0.0078 (15)
C6	0.0206 (14)	0.0200 (14)	0.0206 (14)	−0.0010 (11)	0.0085 (11)	−0.0002 (12)
C7	0.0320 (16)	0.0373 (18)	0.0223 (16)	−0.0044 (14)	0.0123 (13)	0.0026 (14)
C8	0.0320 (17)	0.045 (2)	0.0297 (17)	−0.0050 (15)	0.0177 (14)	−0.0029 (15)
C9	0.0249 (15)	0.0426 (19)	0.0190 (15)	0.0036 (14)	0.0063 (12)	0.0070 (14)
C10	0.0287 (17)	0.056 (2)	0.037 (2)	−0.0027 (16)	0.0039 (15)	−0.0092 (17)
C11	0.0181 (14)	0.0357 (17)	0.0266 (16)	0.0004 (13)	0.0100 (12)	0.0011 (14)
C12	0.0185 (13)	0.0261 (15)	0.0135 (13)	0.0034 (12)	0.0072 (11)	0.0018 (11)
C13	0.0210 (14)	0.0225 (15)	0.0217 (15)	0.0078 (11)	0.0090 (12)	0.0027 (12)
C14	0.0290 (15)	0.0168 (14)	0.0143 (14)	0.0020 (12)	0.0098 (12)	0.0008 (11)
C15	0.0305 (15)	0.0181 (14)	0.0238 (15)	−0.0033 (12)	0.0114 (12)	0.0002 (12)

Geometric parameters (Å, º)

Zn1—N3	2.047 (2)	C4—H4B	0.9700
Zn1—S1	2.3570 (10)	C5—H5A	0.9600
Zn1—S4	2.3693 (12)	C5—H5B	0.9600
Zn1—S3	2.4996 (9)	C5—H5C	0.9600
Zn1—S2	2.6384 (9)	C7—C8	1.504 (4)
S1—C1	1.738 (3)	C7—H7A	0.9700
S2—C1	1.719 (3)	C7—H7B	0.9700
S3—C6	1.726 (3)	C8—H8A	0.9600
S4—C6	1.725 (3)	C8—H8B	0.9600
N1—C1	1.325 (3)	C8—H8C	0.9600
N1—C2	1.477 (3)	C9—C10	1.508 (4)
N1—C4	1.473 (3)	C9—H9A	0.9700
N2—C6	1.327 (3)	C9—H9B	0.9700
N2—C9	1.474 (3)	C10—H10A	0.9600
N2—C7	1.484 (4)	C10—H10B	0.9600
N3—C12	1.340 (3)	C10—H10C	0.9600
N3—N4	1.354 (3)	C11—C12	1.498 (4)
N4—C14	1.346 (3)	C11—H11A	0.9600
N4—H4	0.8600	C11—H11B	0.9600
C2—C3	1.516 (4)	C11—H11C	0.9600
C2—H2A	0.9700	C12—C13	1.392 (4)
C2—H2B	0.9700	C13—C14	1.377 (4)
C3—H3A	0.9600	C13—H13	0.9300
C3—H3B	0.9600	C14—C15	1.490 (4)
C3—H3C	0.9600	C15—H15A	0.9600
C4—C5	1.512 (4)	C15—H15B	0.9600
C4—H4A	0.9700	C15—H15C	0.9600
N3—Zn1—S1	109.05 (7)	H5A—C5—H5C	109.5
N3—Zn1—S4	106.18 (6)	H5B—C5—H5C	109.5
S1—Zn1—S4	143.81 (3)	N2—C6—S4	121.1 (2)
N3—Zn1—S3	101.66 (6)	N2—C6—S3	121.8 (2)
S1—Zn1—S3	105.85 (3)	S4—C6—S3	117.13 (16)
S4—Zn1—S3	74.38 (3)	N2—C7—C8	111.4 (2)
N3—Zn1—S2	92.58 (6)	N2—C7—H7A	109.4
S1—Zn1—S2	72.19 (3)	C8—C7—H7A	109.4
S4—Zn1—S2	98.43 (3)	N2—C7—H7B	109.4
S3—Zn1—S2	165.33 (3)	C8—C7—H7B	109.4
C1—S1—Zn1	88.80 (9)	H7A—C7—H7B	108.0
C1—S2—Zn1	80.42 (9)	C7—C8—H8A	109.5
C6—S3—Zn1	82.17 (10)	C7—C8—H8B	109.5
C6—S4—Zn1	86.22 (10)	H8A—C8—H8B	109.5
C1—N1—C2	122.6 (2)	C7—C8—H8C	109.5
C1—N1—C4	122.4 (2)	H8A—C8—H8C	109.5
C2—N1—C4	114.9 (2)	H8B—C8—H8C	109.5
C6—N2—C9	122.1 (2)	N2—C9—C10	113.7 (3)
C6—N2—C7	121.5 (2)	N2—C9—H9A	108.8
C9—N2—C7	116.4 (2)	C10—C9—H9A	108.8
C12—N3—N4	105.4 (2)	N2—C9—H9B	108.8
C12—N3—Zn1	134.56 (18)	C10—C9—H9B	108.8
N4—N3—Zn1	119.96 (16)	H9A—C9—H9B	107.7
C14—N4—N3	112.4 (2)	C9—C10—H10A	109.5
C14—N4—H4	123.8	C9—C10—H10B	109.5
N3—N4—H4	123.8	H10A—C10—H10B	109.5
N1—C1—S2	122.4 (2)	C9—C10—H10C	109.5
N1—C1—S1	120.35 (19)	H10A—C10—H10C	109.5
S2—C1—S1	117.25 (15)	H10B—C10—H10C	109.5
N1—C2—C3	111.7 (2)	C12—C11—H11A	109.5
N1—C2—H2A	109.3	C12—C11—H11B	109.5
C3—C2—H2A	109.3	H11A—C11—H11B	109.5
N1—C2—H2B	109.3	C12—C11—H11C	109.5
C3—C2—H2B	109.3	H11A—C11—H11C	109.5
H2A—C2—H2B	107.9	H11B—C11—H11C	109.5
C2—C3—H3A	109.5	N3—C12—C13	109.8 (2)
C2—C3—H3B	109.5	N3—C12—C11	120.6 (2)
H3A—C3—H3B	109.5	C13—C12—C11	129.6 (2)
C2—C3—H3C	109.5	C14—C13—C12	106.8 (2)
H3A—C3—H3C	109.5	C14—C13—H13	126.6
H3B—C3—H3C	109.5	C12—C13—H13	126.6
N1—C4—C5	112.2 (2)	N4—C14—C13	105.7 (2)
N1—C4—H4A	109.2	N4—C14—C15	121.4 (2)
C5—C4—H4A	109.2	C13—C14—C15	132.9 (3)
N1—C4—H4B	109.2	C14—C15—H15A	109.5
C5—C4—H4B	109.2	C14—C15—H15B	109.5
H4A—C4—H4B	107.9	H15A—C15—H15B	109.5
C4—C5—H5A	109.5	C14—C15—H15C	109.5
C4—C5—H5B	109.5	H15A—C15—H15C	109.5
H5A—C5—H5B	109.5	H15B—C15—H15C	109.5
C4—C5—H5C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···S2^i	0.86	2.60	3.448 (3)	168

Symmetry code: (i) −x+2, −y+1, −z+1.