The title compound, C
11H
18N
4OS, 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
CCDC reference: 270506
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (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
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(4
H)-one
top
Crystal data top
C11H18N4OS | F(000) = 544 |
Mr = 254.36 | Dx = 1.209 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 750 reflections |
a = 9.797 (2) Å | θ = 1.4–25.4° |
b = 10.290 (3) Å | µ = 0.22 mm−1 |
c = 13.856 (3) Å | T = 290 K |
V = 1396.9 (6) Å3 | Block, colorless |
Z = 4 | 0.45 × 0.42 × 0.37 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2466 independent reflections |
Radiation source: fine-focus sealed tube | 2196 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.876, Tmax = 0.922 | k = −12→12 |
10073 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-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 reflections | Δρmax = 0.19 e Å−3 |
160 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1032 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.94569 (7) | 0.63155 (7) | 0.28738 (5) | 0.0612 (2) | |
N1 | 0.7215 (2) | 0.55751 (18) | 0.37735 (14) | 0.0429 (5) | |
N2 | 0.7076 (2) | 0.6935 (2) | 0.39448 (15) | 0.0525 (6) | |
N3 | 0.8301 (2) | 0.3962 (2) | 0.28632 (14) | 0.0515 (5) | |
N4 | 0.7238 (2) | 0.3125 (2) | 0.30808 (15) | 0.0495 (5) | |
O1 | 0.5309 (2) | 0.51512 (19) | 0.46447 (15) | 0.0681 (6) | |
C1 | 0.8230 (2) | 0.5144 (3) | 0.31743 (17) | 0.0470 (6) | |
C2 | 0.6236 (2) | 0.3476 (2) | 0.36312 (16) | 0.0419 (6) | |
C3 | 0.5086 (3) | 0.2510 (3) | 0.37973 (18) | 0.0526 (7) | |
C4 | 0.3718 (3) | 0.3120 (3) | 0.3495 (3) | 0.0817 (11) | |
C5 | 0.5054 (4) | 0.2119 (3) | 0.4866 (2) | 0.0869 (12) | |
C6 | 0.5301 (3) | 0.1289 (3) | 0.3183 (2) | 0.0666 (7) | |
C7 | 1.0610 (3) | 0.5325 (3) | 0.2188 (3) | 0.0810 (10) | |
C8 | 0.6163 (3) | 0.4763 (3) | 0.40727 (18) | 0.0464 (6) | |
C9 | 0.7417 (3) | 0.7304 (3) | 0.47883 (19) | 0.0494 (6) | |
C10 | 0.7217 (3) | 0.8712 (3) | 0.4983 (3) | 0.0793 (9) | |
C11 | 0.7997 (4) | 0.6494 (4) | 0.5561 (2) | 0.0837 (10) | |
H4A | 0.3522 | 0.3851 | 0.3903 | 0.123* | |
H4B | 0.3004 | 0.2487 | 0.3558 | 0.123* | |
H4C | 0.3773 | 0.3403 | 0.2836 | 0.123* | |
H5A | 0.5921 | 0.1757 | 0.5045 | 0.130* | |
H5B | 0.4350 | 0.1484 | 0.4967 | 0.130* | |
H5C | 0.4871 | 0.2872 | 0.5255 | 0.130* | |
H6A | 0.5300 | 0.1522 | 0.2512 | 0.100* | |
H6B | 0.4578 | 0.0682 | 0.3306 | 0.100* | |
H6C | 0.6161 | 0.0899 | 0.3346 | 0.100* | |
H7A | 1.0931 | 0.4621 | 0.2582 | 0.121* | |
H7B | 1.1372 | 0.5842 | 0.1981 | 0.121* | |
H7C | 1.0146 | 0.4983 | 0.1634 | 0.121* | |
H10A | 0.6660 | 0.9084 | 0.4485 | 0.119* | |
H10B | 0.8087 | 0.9140 | 0.4995 | 0.119* | |
H10C | 0.6774 | 0.8820 | 0.5596 | 0.119* | |
H11A | 0.8264 | 0.5668 | 0.5300 | 0.126* | |
H11B | 0.7326 | 0.6366 | 0.6056 | 0.126* | |
H11C | 0.8781 | 0.6921 | 0.5830 | 0.126* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0521 (4) | 0.0647 (4) | 0.0670 (4) | −0.0144 (4) | 0.0018 (3) | 0.0083 (4) |
N1 | 0.0434 (12) | 0.0417 (12) | 0.0435 (10) | −0.0014 (10) | −0.0027 (10) | 0.0007 (9) |
N2 | 0.0598 (14) | 0.0386 (12) | 0.0590 (13) | 0.0011 (10) | −0.0047 (11) | 0.0008 (10) |
N3 | 0.0465 (12) | 0.0525 (13) | 0.0555 (12) | −0.0049 (10) | 0.0076 (11) | −0.0081 (11) |
N4 | 0.0475 (12) | 0.0492 (11) | 0.0517 (12) | −0.0023 (10) | 0.0057 (11) | −0.0042 (10) |
O1 | 0.0538 (12) | 0.0674 (12) | 0.0830 (13) | −0.0053 (10) | 0.0232 (11) | −0.0245 (10) |
C1 | 0.0405 (15) | 0.0595 (17) | 0.0409 (13) | −0.0015 (12) | −0.0041 (11) | 0.0052 (12) |
C2 | 0.0404 (13) | 0.0463 (15) | 0.0390 (11) | −0.0018 (11) | −0.0008 (11) | −0.0032 (10) |
C3 | 0.0537 (17) | 0.0515 (15) | 0.0525 (14) | −0.0112 (13) | 0.0076 (12) | −0.0090 (12) |
C4 | 0.0490 (19) | 0.080 (2) | 0.116 (3) | −0.0091 (17) | 0.0007 (18) | −0.029 (2) |
C5 | 0.121 (3) | 0.079 (2) | 0.0608 (17) | −0.039 (2) | 0.019 (2) | −0.0033 (16) |
C6 | 0.0713 (19) | 0.0531 (15) | 0.0754 (16) | −0.0186 (16) | 0.0105 (15) | −0.0118 (14) |
C7 | 0.0500 (17) | 0.100 (2) | 0.093 (2) | −0.0152 (18) | 0.0218 (18) | 0.003 (2) |
C8 | 0.0402 (14) | 0.0509 (15) | 0.0481 (14) | 0.0011 (12) | 0.0003 (12) | −0.0034 (11) |
C9 | 0.0387 (15) | 0.0497 (15) | 0.0598 (16) | −0.0089 (12) | 0.0040 (12) | −0.0050 (12) |
C10 | 0.0705 (19) | 0.0570 (19) | 0.110 (2) | −0.0119 (17) | 0.0103 (18) | −0.0253 (18) |
C11 | 0.106 (3) | 0.089 (2) | 0.0567 (16) | −0.001 (2) | −0.0173 (17) | −0.0083 (17) |
Geometric parameters (Å, º) top
C11—C9 | 1.470 (4) | N4—C2 | 1.294 (3) |
C11—H11A | 0.9600 | C2—C3 | 1.520 (3) |
C11—H11B | 0.9600 | C3—C6 | 1.532 (4) |
C11—H11C | 0.9600 | C3—C5 | 1.535 (4) |
C10—C9 | 1.487 (4) | C3—C4 | 1.539 (4) |
C10—H10A | 0.9600 | C6—H6A | 0.9600 |
C10—H10B | 0.9600 | C6—H6B | 0.9600 |
C10—H10C | 0.9600 | C6—H6C | 0.9600 |
C9—N2 | 1.273 (3) | C5—H5A | 0.9600 |
S1—C1 | 1.752 (3) | C5—H5B | 0.9600 |
S1—C7 | 1.794 (3) | C5—H5C | 0.9600 |
N1—C1 | 1.369 (3) | C4—H4A | 0.9600 |
N1—C8 | 1.390 (3) | C4—H4B | 0.9600 |
N1—N2 | 1.426 (3) | C4—H4C | 0.9600 |
N3—C1 | 1.293 (3) | C7—H7A | 0.9600 |
N3—N4 | 1.385 (3) | C7—H7B | 0.9600 |
C8—O1 | 1.219 (3) | C7—H7C | 0.9600 |
C8—C2 | 1.461 (4) | | |
| | | |
C9—C11—H11A | 109.5 | C2—C3—C6 | 110.5 (2) |
C9—C11—H11B | 109.5 | C2—C3—C5 | 109.4 (2) |
H11A—C11—H11B | 109.5 | C6—C3—C5 | 108.9 (2) |
C9—C11—H11C | 109.5 | C2—C3—C4 | 109.8 (2) |
H11A—C11—H11C | 109.5 | C6—C3—C4 | 107.6 (2) |
H11B—C11—H11C | 109.5 | C5—C3—C4 | 110.6 (3) |
C9—C10—H10A | 109.5 | C3—C6—H6A | 109.5 |
C9—C10—H10B | 109.5 | C3—C6—H6B | 109.5 |
H10A—C10—H10B | 109.5 | H6A—C6—H6B | 109.5 |
C9—C10—H10C | 109.5 | C3—C6—H6C | 109.5 |
H10A—C10—H10C | 109.5 | H6A—C6—H6C | 109.5 |
H10B—C10—H10C | 109.5 | H6B—C6—H6C | 109.5 |
N2—C9—C11 | 126.9 (3) | C3—C5—H5A | 109.5 |
N2—C9—C10 | 115.0 (3) | C3—C5—H5B | 109.5 |
C11—C9—C10 | 118.1 (3) | H5A—C5—H5B | 109.5 |
C1—S1—C7 | 99.64 (14) | C3—C5—H5C | 109.5 |
C1—N1—C8 | 121.7 (2) | H5A—C5—H5C | 109.5 |
C1—N1—N2 | 119.2 (2) | H5B—C5—H5C | 109.5 |
C8—N1—N2 | 118.0 (2) | C3—C4—H4A | 109.5 |
C1—N3—N4 | 118.2 (2) | C3—C4—H4B | 109.5 |
O1—C8—N1 | 120.4 (2) | H4A—C4—H4B | 109.5 |
O1—C8—C2 | 127.1 (2) | C3—C4—H4C | 109.5 |
N1—C8—C2 | 112.6 (2) | H4A—C4—H4C | 109.5 |
C2—N4—N3 | 121.7 (2) | H4B—C4—H4C | 109.5 |
C9—N2—N1 | 114.8 (2) | S1—C7—H7A | 109.5 |
N4—C2—C8 | 122.5 (2) | S1—C7—H7B | 109.5 |
N4—C2—C3 | 118.0 (2) | H7A—C7—H7B | 109.5 |
C8—C2—C3 | 119.5 (2) | S1—C7—H7C | 109.5 |
N3—C1—N1 | 123.1 (2) | H7A—C7—H7C | 109.5 |
N3—C1—S1 | 122.08 (19) | H7B—C7—H7C | 109.5 |
N1—C1—S1 | 114.81 (19) | | |
| | | |
C1—N1—C8—O1 | 176.3 (2) | N4—N3—C1—N1 | 5.6 (3) |
N2—N1—C8—O1 | −16.0 (3) | N4—N3—C1—S1 | −175.57 (16) |
C1—N1—C8—C2 | −3.6 (3) | C8—N1—C1—N3 | −1.5 (4) |
N2—N1—C8—C2 | 164.1 (2) | N2—N1—C1—N3 | −169.1 (2) |
C1—N3—N4—C2 | −4.4 (3) | C8—N1—C1—S1 | 179.63 (17) |
C11—C9—N2—N1 | 3.7 (4) | N2—N1—C1—S1 | 12.1 (3) |
C10—C9—N2—N1 | −177.5 (2) | C7—S1—C1—N3 | −3.2 (3) |
C1—N1—N2—C9 | −109.0 (3) | C7—S1—C1—N1 | 175.70 (19) |
C8—N1—N2—C9 | 83.0 (3) | N4—C2—C3—C6 | −4.7 (3) |
N3—N4—C2—C8 | −1.0 (3) | C8—C2—C3—C6 | 173.9 (2) |
N3—N4—C2—C3 | 177.6 (2) | N4—C2—C3—C5 | 115.2 (3) |
O1—C8—C2—N4 | −175.1 (3) | C8—C2—C3—C5 | −66.2 (3) |
N1—C8—C2—N4 | 4.8 (3) | N4—C2—C3—C4 | −123.3 (3) |
O1—C8—C2—C3 | 6.4 (4) | C8—C2—C3—C4 | 55.3 (3) |
N1—C8—C2—C3 | −173.8 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11B···N3i | 0.96 | 2.60 | 3.467 (4) | 150 |
C10—H10B···O1ii | 0.96 | 2.35 | 3.289 (4) | 166 |
Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) x+1/2, −y+3/2, −z+1. |