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The title compound, C15H19N3O2S, is one of the thio­urea herbicides in which 1-tert-butyl­urea replaces 4,6-disubstituted pyrimidine. The crystal structure reveals intra­molecular N—H...O and N—H...S hydrogen bonds that form six-membered rings, whereas inter­molecular N—H...O hydrogen bonds connect mol­ecules along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602280X/kp2028sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602280X/kp2028Isup2.hkl
Contains datablock I

CCDC reference: 618253

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.076
  • wR factor = 0.172
  • Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.29 Sigma
Alert level C STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.200 From the CIF: _refine_ls_abs_structure_Flack_su 1.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 1.00 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 3309.00 Ang-3 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.00 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT350_ALERT_3_C Short C-H Bond (0.96A) C14 - H14C ... 0.83 Ang. PLAT390_ALERT_3_C Deviating Methyl C15 X-C-H Bond Angle ...... 117.00 Deg.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998) and SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(E)-5-tert-Butyl-1-cinnamoylthiobiuret top
Crystal data top
C15H19N3O2SDx = 1.226 Mg m3
Mr = 305.39Melting point: 457 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2644 reflections
a = 7.898 (2) Åθ = 2.8–21.6°
b = 11.910 (5) ŵ = 0.20 mm1
c = 35.170 (16) ÅT = 298 K
V = 3309 (2) Å3Prism, yellow
Z = 80.35 × 0.10 × 0.05 mm
F(000) = 1296
Data collection top
Bruker SMART CCD area-detector
diffractometer
2908 independent reflections
Radiation source: fine-focus sealed tube2209 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
φ and ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 98
Tmin = 0.932, Tmax = 0.990k = 1214
12822 measured reflectionsl = 3641
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.076 w = 1/[σ2(Fo2) + (0.051P)2 + 4.2027P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.172(Δ/σ)max = 0.001
S = 1.15Δρmax = 0.34 e Å3
2908 reflectionsΔρmin = 0.21 e Å3
267 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0009 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.2 (10)
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
S10.16144 (15)0.73310 (10)0.32335 (4)0.0739 (5)
O10.4501 (3)0.9575 (2)0.40536 (8)0.0610 (8)
O20.0025 (3)1.0721 (2)0.36750 (8)0.0570 (7)
N10.3883 (4)0.7959 (3)0.37290 (9)0.0470 (8)
H1A0.423 (5)0.719 (4)0.3702 (11)0.066 (12)*
N20.1803 (4)0.9276 (3)0.36252 (9)0.0481 (8)
H2A0.232 (5)0.965 (3)0.3817 (10)0.056 (11)*
N30.0327 (4)0.9544 (3)0.31710 (10)0.0529 (8)
H3A0.006 (5)0.877 (4)0.3112 (11)0.063 (12)*
C11.0301 (5)0.9040 (4)0.45964 (12)0.0599 (11)
H10.992 (5)0.982 (4)0.4634 (12)0.071 (13)*
C21.1865 (6)0.8699 (5)0.47467 (13)0.0677 (13)
H21.247 (6)0.925 (4)0.4890 (13)0.090 (16)*
C31.2404 (6)0.7622 (5)0.46988 (13)0.0711 (13)
H31.353 (6)0.737 (4)0.4811 (13)0.087 (15)*
C41.1430 (6)0.6864 (4)0.45010 (14)0.0729 (13)
H41.175 (6)0.605 (4)0.4481 (13)0.088 (15)*
C50.9878 (6)0.7183 (4)0.43555 (13)0.0636 (12)
H50.932 (5)0.663 (4)0.4219 (11)0.062 (12)*
C60.9292 (5)0.8279 (3)0.44034 (10)0.0482 (9)
C70.7641 (5)0.8663 (4)0.42626 (11)0.0522 (10)
H70.737 (5)0.943 (3)0.4332 (10)0.055 (11)*
C80.6464 (5)0.8061 (3)0.40861 (11)0.0514 (10)
H80.658 (5)0.728 (4)0.4032 (11)0.064 (12)*
C90.4872 (5)0.8613 (3)0.39656 (11)0.0488 (9)
C100.2406 (5)0.8256 (3)0.35380 (10)0.0472 (9)
C110.0373 (4)0.9894 (3)0.34902 (11)0.0458 (9)
C120.1769 (5)1.0081 (4)0.29738 (12)0.0572 (11)
C130.1352 (10)1.1288 (5)0.2880 (2)0.096 (2)
H13A0.217 (9)1.149 (6)0.2695 (18)0.14 (3)*
H13B0.128 (7)1.179 (5)0.3123 (16)0.102 (19)*
H13C0.036 (8)1.133 (6)0.2762 (17)0.12 (3)*
C140.3350 (7)0.9975 (8)0.3221 (2)0.089 (2)
H14A0.315 (5)1.042 (4)0.3488 (13)0.072 (13)*
H14B0.343 (12)0.929 (9)0.329 (3)0.22 (5)*
H14C0.418 (7)1.023 (5)0.3103 (15)0.10 (2)*
C150.2018 (7)0.9414 (6)0.26092 (16)0.0758 (15)
H15A0.294 (6)0.974 (4)0.2448 (13)0.084 (14)*
H15B0.105 (7)0.931 (4)0.2455 (15)0.097 (18)*
H15C0.238 (8)0.867 (5)0.2692 (15)0.11 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0714 (7)0.0471 (7)0.1032 (9)0.0106 (5)0.0323 (7)0.0271 (6)
O10.0536 (16)0.0470 (16)0.0825 (19)0.0052 (13)0.0082 (14)0.0223 (14)
O20.0541 (16)0.0374 (15)0.0796 (19)0.0013 (12)0.0068 (14)0.0106 (13)
N10.0450 (17)0.0296 (16)0.066 (2)0.0008 (14)0.0069 (15)0.0052 (14)
N20.0456 (18)0.0388 (18)0.060 (2)0.0047 (14)0.0055 (15)0.0122 (15)
N30.0459 (18)0.046 (2)0.067 (2)0.0080 (15)0.0034 (15)0.0050 (17)
C10.056 (3)0.054 (3)0.069 (3)0.003 (2)0.006 (2)0.006 (2)
C20.062 (3)0.075 (3)0.067 (3)0.011 (3)0.012 (2)0.013 (2)
C30.061 (3)0.084 (4)0.068 (3)0.008 (3)0.011 (2)0.002 (3)
C40.075 (3)0.060 (3)0.084 (3)0.014 (3)0.013 (3)0.007 (3)
C50.065 (3)0.054 (3)0.071 (3)0.002 (2)0.013 (2)0.013 (2)
C60.051 (2)0.044 (2)0.049 (2)0.0028 (18)0.0002 (17)0.0045 (17)
C70.051 (2)0.044 (2)0.061 (2)0.0018 (19)0.0030 (19)0.0112 (19)
C80.053 (2)0.040 (2)0.062 (2)0.0015 (18)0.0055 (19)0.0073 (19)
C90.045 (2)0.044 (2)0.057 (2)0.0032 (17)0.0016 (17)0.0103 (18)
C100.045 (2)0.040 (2)0.058 (2)0.0019 (16)0.0032 (18)0.0070 (17)
C110.041 (2)0.036 (2)0.060 (2)0.0015 (16)0.0072 (17)0.0047 (18)
C120.039 (2)0.061 (3)0.071 (3)0.0044 (19)0.0014 (19)0.004 (2)
C130.097 (5)0.069 (4)0.120 (6)0.001 (4)0.032 (5)0.024 (4)
C140.044 (3)0.137 (7)0.086 (4)0.015 (3)0.008 (3)0.001 (4)
C150.050 (3)0.098 (5)0.080 (4)0.006 (3)0.009 (3)0.003 (3)
Geometric parameters (Å, º) top
S1—C101.659 (4)C4—H41.01 (5)
O1—C91.222 (4)C5—C61.395 (6)
O2—C111.222 (4)C5—H50.92 (4)
N1—C91.382 (5)C6—C71.468 (5)
N1—C101.392 (5)C7—C81.328 (5)
N1—H1A0.97 (4)C7—H70.97 (4)
N2—C101.341 (5)C8—C91.480 (5)
N2—C111.429 (5)C8—H80.95 (4)
N2—H2A0.90 (4)C12—C131.511 (7)
N3—C111.319 (5)C12—C151.522 (7)
N3—C121.479 (5)C12—C141.526 (7)
N3—H3A0.97 (4)C13—H13A0.95 (7)
C1—C61.385 (5)C13—H13B1.04 (6)
C1—C21.403 (6)C13—H13C0.89 (6)
C1—H10.99 (5)C14—H14A1.09 (5)
C2—C31.363 (7)C14—H14B0.86 (10)
C2—H20.95 (5)C14—H14C0.83 (6)
C3—C41.376 (7)C15—H15A1.00 (5)
C3—H31.02 (5)C15—H15B0.94 (5)
C4—C51.382 (6)C15—H15C0.98 (6)
C9—N1—C10128.4 (3)O1—C9—N1123.0 (4)
C9—N1—H1A116 (2)O1—C9—C8123.2 (3)
C10—N1—H1A116 (2)N1—C9—C8113.7 (3)
C10—N2—C11132.2 (3)N2—C10—N1114.7 (3)
C10—N2—H2A117 (3)N2—C10—S1128.0 (3)
C11—N2—H2A111 (3)N1—C10—S1117.3 (3)
C11—N3—C12125.9 (3)O2—C11—N3126.8 (4)
C11—N3—H3A113 (2)O2—C11—N2116.2 (3)
C12—N3—H3A119 (2)N3—C11—N2116.9 (3)
C6—C1—C2120.1 (4)N3—C12—C13110.2 (4)
C6—C1—H1120 (3)N3—C12—C15105.6 (4)
C2—C1—H1119 (3)C13—C12—C15109.9 (5)
C3—C2—C1120.1 (4)N3—C12—C14109.1 (4)
C3—C2—H2124 (3)C13—C12—C14112.4 (6)
C1—C2—H2116 (3)C15—C12—C14109.3 (4)
C2—C3—C4120.4 (5)C12—C13—H13A104 (4)
C2—C3—H3120 (3)C12—C13—H13B112 (3)
C4—C3—H3119 (3)H13A—C13—H13B117 (5)
C3—C4—C5120.2 (5)C12—C13—H13C111 (5)
C3—C4—H4122 (3)H13A—C13—H13C105 (6)
C5—C4—H4118 (3)H13B—C13—H13C108 (5)
C4—C5—C6120.5 (4)C12—C14—H14A109 (2)
C4—C5—H5115 (3)C12—C14—H14B108 (6)
C6—C5—H5125 (3)H14A—C14—H14B102 (7)
C1—C6—C5118.7 (4)C12—C14—H14C109 (4)
C1—C6—C7118.2 (4)H14A—C14—H14C111 (5)
C5—C6—C7123.1 (4)H14B—C14—H14C116 (8)
C8—C7—C6127.7 (4)C12—C15—H15A111 (3)
C8—C7—H7118 (2)C12—C15—H15B117 (3)
C6—C7—H7114 (2)H15A—C15—H15B108 (4)
C7—C8—C9119.2 (4)C12—C15—H15C105 (3)
C7—C8—H8124 (2)H15A—C15—H15C108 (4)
C9—C8—H8117 (2)H15B—C15—H15C107 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···S10.97 (4)2.21 (4)3.058 (4)146 (3)
N2—H2A···O10.90 (4)1.92 (4)2.634 (4)135 (3)
N1—H1A···O2i0.97 (4)1.86 (5)2.820 (4)176 (4)
Symmetry code: (i) x+1/2, y1/2, z.
 

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