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The title compound, C11H18N4OS, a herbicide, crystallizes in an orthorhombic non-centrosymmetric space group. The crystal structure is stabilized by C—H...N and C—H...O intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008585/ob6495sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008585/ob6495Isup2.hkl
Contains datablock I

CCDC reference: 270506

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.106
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C1 .. 6.84 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.10
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2466 Count of symmetry unique reflns 1435 Completeness (_total/calc) 171.85% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1031 Fraction of Friedel pairs measured 0.718 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

6-tert-Butyl-4-isopropylideneamino-3-methylsulfanyl-1,2,4-triazin-5(4H)-one top
Crystal data top
C11H18N4OSF(000) = 544
Mr = 254.36Dx = 1.209 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 750 reflections
a = 9.797 (2) Åθ = 1.4–25.4°
b = 10.290 (3) ŵ = 0.22 mm1
c = 13.856 (3) ÅT = 290 K
V = 1396.9 (6) Å3Block, colorless
Z = 40.45 × 0.42 × 0.37 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2466 independent reflections
Radiation source: fine-focus sealed tube2196 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.876, Tmax = 0.922k = 1212
10073 measured reflectionsl = 1616
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)] = 0.047H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0545P)2 + 0.0414P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.012
2466 reflectionsΔρmax = 0.19 e Å3
160 parametersΔρmin = 0.12 e Å3
0 restraintsAbsolute structure: Flack (1983), 1032 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.002 (99)
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
S10.94569 (7)0.63155 (7)0.28738 (5)0.0612 (2)
N10.7215 (2)0.55751 (18)0.37735 (14)0.0429 (5)
N20.7076 (2)0.6935 (2)0.39448 (15)0.0525 (6)
N30.8301 (2)0.3962 (2)0.28632 (14)0.0515 (5)
N40.7238 (2)0.3125 (2)0.30808 (15)0.0495 (5)
O10.5309 (2)0.51512 (19)0.46447 (15)0.0681 (6)
C10.8230 (2)0.5144 (3)0.31743 (17)0.0470 (6)
C20.6236 (2)0.3476 (2)0.36312 (16)0.0419 (6)
C30.5086 (3)0.2510 (3)0.37973 (18)0.0526 (7)
C40.3718 (3)0.3120 (3)0.3495 (3)0.0817 (11)
C50.5054 (4)0.2119 (3)0.4866 (2)0.0869 (12)
C60.5301 (3)0.1289 (3)0.3183 (2)0.0666 (7)
C71.0610 (3)0.5325 (3)0.2188 (3)0.0810 (10)
C80.6163 (3)0.4763 (3)0.40727 (18)0.0464 (6)
C90.7417 (3)0.7304 (3)0.47883 (19)0.0494 (6)
C100.7217 (3)0.8712 (3)0.4983 (3)0.0793 (9)
C110.7997 (4)0.6494 (4)0.5561 (2)0.0837 (10)
H4A0.35220.38510.39030.123*
H4B0.30040.24870.35580.123*
H4C0.37730.34030.28360.123*
H5A0.59210.17570.50450.130*
H5B0.43500.14840.49670.130*
H5C0.48710.28720.52550.130*
H6A0.53000.15220.25120.100*
H6B0.45780.06820.33060.100*
H6C0.61610.08990.33460.100*
H7A1.09310.46210.25820.121*
H7B1.13720.58420.19810.121*
H7C1.01460.49830.16340.121*
H10A0.66600.90840.44850.119*
H10B0.80870.91400.49950.119*
H10C0.67740.88200.55960.119*
H11A0.82640.56680.53000.126*
H11B0.73260.63660.60560.126*
H11C0.87810.69210.58300.126*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0521 (4)0.0647 (4)0.0670 (4)0.0144 (4)0.0018 (3)0.0083 (4)
N10.0434 (12)0.0417 (12)0.0435 (10)0.0014 (10)0.0027 (10)0.0007 (9)
N20.0598 (14)0.0386 (12)0.0590 (13)0.0011 (10)0.0047 (11)0.0008 (10)
N30.0465 (12)0.0525 (13)0.0555 (12)0.0049 (10)0.0076 (11)0.0081 (11)
N40.0475 (12)0.0492 (11)0.0517 (12)0.0023 (10)0.0057 (11)0.0042 (10)
O10.0538 (12)0.0674 (12)0.0830 (13)0.0053 (10)0.0232 (11)0.0245 (10)
C10.0405 (15)0.0595 (17)0.0409 (13)0.0015 (12)0.0041 (11)0.0052 (12)
C20.0404 (13)0.0463 (15)0.0390 (11)0.0018 (11)0.0008 (11)0.0032 (10)
C30.0537 (17)0.0515 (15)0.0525 (14)0.0112 (13)0.0076 (12)0.0090 (12)
C40.0490 (19)0.080 (2)0.116 (3)0.0091 (17)0.0007 (18)0.029 (2)
C50.121 (3)0.079 (2)0.0608 (17)0.039 (2)0.019 (2)0.0033 (16)
C60.0713 (19)0.0531 (15)0.0754 (16)0.0186 (16)0.0105 (15)0.0118 (14)
C70.0500 (17)0.100 (2)0.093 (2)0.0152 (18)0.0218 (18)0.003 (2)
C80.0402 (14)0.0509 (15)0.0481 (14)0.0011 (12)0.0003 (12)0.0034 (11)
C90.0387 (15)0.0497 (15)0.0598 (16)0.0089 (12)0.0040 (12)0.0050 (12)
C100.0705 (19)0.0570 (19)0.110 (2)0.0119 (17)0.0103 (18)0.0253 (18)
C110.106 (3)0.089 (2)0.0567 (16)0.001 (2)0.0173 (17)0.0083 (17)
Geometric parameters (Å, º) top
C11—C91.470 (4)N4—C21.294 (3)
C11—H11A0.9600C2—C31.520 (3)
C11—H11B0.9600C3—C61.532 (4)
C11—H11C0.9600C3—C51.535 (4)
C10—C91.487 (4)C3—C41.539 (4)
C10—H10A0.9600C6—H6A0.9600
C10—H10B0.9600C6—H6B0.9600
C10—H10C0.9600C6—H6C0.9600
C9—N21.273 (3)C5—H5A0.9600
S1—C11.752 (3)C5—H5B0.9600
S1—C71.794 (3)C5—H5C0.9600
N1—C11.369 (3)C4—H4A0.9600
N1—C81.390 (3)C4—H4B0.9600
N1—N21.426 (3)C4—H4C0.9600
N3—C11.293 (3)C7—H7A0.9600
N3—N41.385 (3)C7—H7B0.9600
C8—O11.219 (3)C7—H7C0.9600
C8—C21.461 (4)
C9—C11—H11A109.5C2—C3—C6110.5 (2)
C9—C11—H11B109.5C2—C3—C5109.4 (2)
H11A—C11—H11B109.5C6—C3—C5108.9 (2)
C9—C11—H11C109.5C2—C3—C4109.8 (2)
H11A—C11—H11C109.5C6—C3—C4107.6 (2)
H11B—C11—H11C109.5C5—C3—C4110.6 (3)
C9—C10—H10A109.5C3—C6—H6A109.5
C9—C10—H10B109.5C3—C6—H6B109.5
H10A—C10—H10B109.5H6A—C6—H6B109.5
C9—C10—H10C109.5C3—C6—H6C109.5
H10A—C10—H10C109.5H6A—C6—H6C109.5
H10B—C10—H10C109.5H6B—C6—H6C109.5
N2—C9—C11126.9 (3)C3—C5—H5A109.5
N2—C9—C10115.0 (3)C3—C5—H5B109.5
C11—C9—C10118.1 (3)H5A—C5—H5B109.5
C1—S1—C799.64 (14)C3—C5—H5C109.5
C1—N1—C8121.7 (2)H5A—C5—H5C109.5
C1—N1—N2119.2 (2)H5B—C5—H5C109.5
C8—N1—N2118.0 (2)C3—C4—H4A109.5
C1—N3—N4118.2 (2)C3—C4—H4B109.5
O1—C8—N1120.4 (2)H4A—C4—H4B109.5
O1—C8—C2127.1 (2)C3—C4—H4C109.5
N1—C8—C2112.6 (2)H4A—C4—H4C109.5
C2—N4—N3121.7 (2)H4B—C4—H4C109.5
C9—N2—N1114.8 (2)S1—C7—H7A109.5
N4—C2—C8122.5 (2)S1—C7—H7B109.5
N4—C2—C3118.0 (2)H7A—C7—H7B109.5
C8—C2—C3119.5 (2)S1—C7—H7C109.5
N3—C1—N1123.1 (2)H7A—C7—H7C109.5
N3—C1—S1122.08 (19)H7B—C7—H7C109.5
N1—C1—S1114.81 (19)
C1—N1—C8—O1176.3 (2)N4—N3—C1—N15.6 (3)
N2—N1—C8—O116.0 (3)N4—N3—C1—S1175.57 (16)
C1—N1—C8—C23.6 (3)C8—N1—C1—N31.5 (4)
N2—N1—C8—C2164.1 (2)N2—N1—C1—N3169.1 (2)
C1—N3—N4—C24.4 (3)C8—N1—C1—S1179.63 (17)
C11—C9—N2—N13.7 (4)N2—N1—C1—S112.1 (3)
C10—C9—N2—N1177.5 (2)C7—S1—C1—N33.2 (3)
C1—N1—N2—C9109.0 (3)C7—S1—C1—N1175.70 (19)
C8—N1—N2—C983.0 (3)N4—C2—C3—C64.7 (3)
N3—N4—C2—C81.0 (3)C8—C2—C3—C6173.9 (2)
N3—N4—C2—C3177.6 (2)N4—C2—C3—C5115.2 (3)
O1—C8—C2—N4175.1 (3)C8—C2—C3—C566.2 (3)
N1—C8—C2—N44.8 (3)N4—C2—C3—C4123.3 (3)
O1—C8—C2—C36.4 (4)C8—C2—C3—C455.3 (3)
N1—C8—C2—C3173.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11B···N3i0.962.603.467 (4)150
C10—H10B···O1ii0.962.353.289 (4)166
Symmetry codes: (i) x+3/2, y+1, z+1/2; (ii) x+1/2, y+3/2, z+1.
 

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