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.
Supporting information
CCDC reference: 612861
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (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
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)
top
Crystal data top
[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) Å3 | 0.30 × 0.20 × 0.09 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0313P)2 + 2.0654P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···S2i | 0.86 | 2.60 | 3.448 (3) | 168 |
Symmetry code: (i) −x+2, −y+1, −z+1. |