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In the title compound, C12H20N4OS2, the dihedral angle between the plane of the N,N-di­methyl­di­thio­carbamate group and the plane of the triazole moiety is 9.96 (2)°. There are weak C—H...N intermolecular interactions in the crystal structure, contributing to its stability.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023055/na6258sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023055/na6258Isup2.hkl
Contains datablock I

CCDC reference: 226995

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.114
  • Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.17 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.90 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C9 = 5.62 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C5 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: R-AXIS Software (Rigaku, 1997); cell refinement: R-AXIS Software; data reduction: R-AXIS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC; software used to prepare material for publication: WinGX (Farrugia, 1999).

4,4-Dimethyl-3-oxo-1-(1,2,4-triazol-1-yl)pentan-2-yl N,N-dimethyldithiocarbamate top
Crystal data top
C12H20N4OS2F(000) = 640
Mr = 300.44Dx = 1.221 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2y bcCell parameters from 20 reflections
a = 12.315 (3) Åθ = 2–11°
b = 12.057 (2) ŵ = 0.32 mm1
c = 12.532 (3) ÅT = 293 K
β = 118.55 (3)°Pillar, colorless
V = 1634.5 (8) Å30.25 × 0.20 × 0.15 mm
Z = 4
Data collection top
Oxford Instruments point-detector
diffractometer
Rint = 0.025
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 1.9°
Graphite monochromatorh = 150
ω/2θ scansk = 1515
5132 measured reflectionsl = 1316
3130 independent reflections3 standard reflections every 100 reflections
2189 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0601P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3130 reflectionsΔρmax = 0.24 e Å3
173 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0164 (16)
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.

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 (Å2) top
xyzUiso*/Ueq
S10.19508 (6)0.30704 (5)0.15133 (5)0.0499 (2)
S20.28853 (8)0.24256 (6)0.41476 (6)0.0664 (3)
O10.19319 (17)0.55544 (15)0.06702 (15)0.0615 (5)
N10.2103 (2)0.10543 (15)0.2283 (2)0.0550 (5)
N20.09057 (19)0.58687 (15)0.25521 (18)0.0474 (5)
N30.1408 (2)0.60743 (19)0.3759 (2)0.0716 (7)
N40.0813 (3)0.7659 (2)0.2684 (3)0.0811 (8)
C10.2368 (3)0.0129 (2)0.3117 (3)0.0891 (10)
H1A0.27010.04050.39320.134*
H1B0.29590.03560.30640.134*
H1C0.16200.02720.29070.134*
C20.1589 (3)0.0774 (2)0.0999 (3)0.0808 (9)
H2A0.14590.14410.05330.121*
H2B0.08160.03970.07290.121*
H2C0.21560.03000.08900.121*
C30.2316 (2)0.20907 (18)0.2702 (2)0.0418 (6)
C40.2115 (2)0.43895 (17)0.22616 (19)0.0404 (5)
H4B0.26990.43190.31300.049*
C50.2633 (2)0.51837 (18)0.1657 (2)0.0448 (6)
C60.3985 (3)0.5502 (2)0.2333 (3)0.0687 (8)
C70.4794 (3)0.4465 (3)0.2816 (4)0.1170 (14)
H7A0.47010.40150.21470.175*
H7B0.45440.40490.33160.175*
H7C0.56430.46800.32900.175*
C80.4335 (3)0.6142 (3)0.1503 (4)0.1227 (15)
H8A0.38320.67960.12130.184*
H8B0.42060.56850.08260.184*
H8C0.51900.63500.19430.184*
C90.4128 (3)0.6235 (3)0.3377 (4)0.1276 (16)
H9A0.36210.68840.30590.191*
H9B0.49770.64520.38480.191*
H9C0.38760.58320.38830.191*
C100.0855 (2)0.47617 (18)0.2084 (2)0.0479 (6)
H10A0.02620.47490.12250.058*
H10B0.05750.42470.24970.058*
C110.0566 (3)0.6814 (2)0.1953 (3)0.0670 (8)
H11A0.01940.68730.11120.080*
C120.1319 (3)0.7169 (3)0.3768 (3)0.0814 (10)
H12A0.15910.75680.44850.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0706 (5)0.0394 (3)0.0392 (3)0.0002 (3)0.0258 (3)0.0043 (3)
S20.0912 (6)0.0635 (5)0.0442 (4)0.0060 (4)0.0321 (4)0.0057 (3)
O10.0556 (12)0.0675 (12)0.0558 (11)0.0043 (9)0.0221 (10)0.0175 (9)
N10.0601 (14)0.0384 (11)0.0736 (14)0.0054 (10)0.0376 (12)0.0031 (10)
N20.0510 (13)0.0361 (10)0.0586 (12)0.0027 (9)0.0290 (11)0.0054 (9)
N30.099 (2)0.0564 (14)0.0670 (15)0.0011 (13)0.0453 (15)0.0133 (12)
N40.0787 (19)0.0432 (13)0.118 (2)0.0056 (12)0.0440 (18)0.0150 (15)
C10.117 (3)0.0454 (15)0.129 (3)0.0008 (17)0.079 (3)0.0144 (18)
C20.091 (2)0.0516 (16)0.095 (2)0.0153 (16)0.041 (2)0.0310 (16)
C30.0378 (14)0.0420 (13)0.0506 (13)0.0003 (10)0.0251 (12)0.0011 (10)
C40.0465 (14)0.0343 (11)0.0376 (11)0.0030 (10)0.0179 (11)0.0026 (9)
C50.0438 (16)0.0392 (12)0.0495 (13)0.0008 (11)0.0209 (12)0.0014 (11)
C60.0448 (17)0.096 (2)0.112 (2)0.0033 (13)0.0284 (16)0.0133 (17)
C70.046 (2)0.126 (3)0.159 (4)0.014 (2)0.033 (2)0.036 (3)
C80.070 (3)0.147 (4)0.151 (4)0.034 (2)0.053 (3)0.031 (3)
C90.079 (3)0.143 (4)0.130 (3)0.058 (3)0.024 (3)0.062 (3)
C100.0525 (16)0.0369 (12)0.0598 (14)0.0100 (11)0.0311 (13)0.0085 (10)
C110.0645 (19)0.0465 (16)0.082 (2)0.0096 (14)0.0281 (16)0.0056 (14)
C120.090 (3)0.064 (2)0.094 (2)0.0022 (17)0.047 (2)0.0326 (18)
Geometric parameters (Å, º) top
S1—C31.780 (2)C4—C51.535 (3)
S1—C41.810 (2)C4—H4B0.9800
S2—C31.651 (2)C5—C61.514 (4)
O1—C51.205 (3)C6—C81.513 (4)
N1—C31.333 (3)C6—C91.519 (4)
N1—C11.453 (3)C6—C71.530 (4)
N1—C21.461 (4)C7—H7A0.9600
N2—C111.317 (3)C7—H7B0.9600
N2—N31.357 (3)C7—H7C0.9600
N2—C101.448 (3)C8—H8A0.9600
N3—C121.324 (4)C8—H8B0.9600
N4—C111.306 (3)C8—H8C0.9600
N4—C121.331 (4)C9—H9A0.9600
C1—H1A0.9600C9—H9B0.9600
C1—H1B0.9600C9—H9C0.9600
C1—H1C0.9600C10—H10A0.9700
C2—H2A0.9600C10—H10B0.9700
C2—H2B0.9600C11—H11A0.9300
C2—H2C0.9600C12—H12A0.9300
C4—C101.525 (3)
C3—S1—C4103.16 (10)C5—C6—C9105.9 (2)
C3—N1—C1120.1 (2)C8—C6—C7110.0 (3)
C3—N1—C2123.6 (2)C5—C6—C7110.3 (2)
C1—N1—C2116.4 (2)C9—C6—C7110.5 (3)
C11—N2—N3109.1 (2)C6—C7—H7A109.5
C11—N2—C10128.7 (2)C6—C7—H7B109.5
N3—N2—C10122.1 (2)H7A—C7—H7B109.5
C12—N3—N2101.4 (2)C6—C7—H7C109.5
C11—N4—C12102.1 (2)H7A—C7—H7C109.5
N1—C1—H1A109.5H7B—C7—H7C109.5
N1—C1—H1B109.5C6—C8—H8A109.5
H1A—C1—H1B109.5C6—C8—H8B109.5
N1—C1—H1C109.5H8A—C8—H8B109.5
H1A—C1—H1C109.5C6—C8—H8C109.5
H1B—C1—H1C109.5H8A—C8—H8C109.5
N1—C2—H2A109.5H8B—C8—H8C109.5
N1—C2—H2B109.5C6—C9—H9A109.5
H2A—C2—H2B109.5C6—C9—H9B109.5
N1—C2—H2C109.5H9A—C9—H9B109.5
H2A—C2—H2C109.5C6—C9—H9C109.5
H2B—C2—H2C109.5H9A—C9—H9C109.5
N1—C3—S2124.36 (18)H9B—C9—H9C109.5
N1—C3—S1111.57 (17)N2—C10—C4111.56 (18)
S2—C3—S1124.05 (13)N2—C10—H10A109.3
C10—C4—C5112.26 (18)C4—C10—H10A109.3
C10—C4—S1109.17 (15)N2—C10—H10B109.3
C5—C4—S1105.23 (14)C4—C10—H10B109.3
C10—C4—H4B110.0H10A—C10—H10B108.0
C5—C4—H4B110.0N4—C11—N2111.8 (3)
S1—C4—H4B110.0N4—C11—H11A124.1
O1—C5—C6122.5 (2)N2—C11—H11A124.1
O1—C5—C4118.2 (2)N3—C12—N4115.6 (3)
C6—C5—C4119.2 (2)N3—C12—H12A122.2
C8—C6—C5110.1 (3)N4—C12—H12A122.2
C8—C6—C9110.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···S20.962.452.995 (3)116
C2—H2A···S10.962.242.831 (3)119
C4—H4B···S20.982.573.154 (2)118
 

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