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In the title compound, C19H18ClN3O5S2, which is a represent­ative of a class of inactive acetolactate synthase inhibitors, the dihedral angle between the two aromatic groups is 85.9 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010584/ob6233sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010584/ob6233Isup2.hkl
Contains datablock I

CCDC reference: 217440

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.087
  • Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(3) - C(31) = 1.43 Ang. PLAT_420 Alert C D-H Without Acceptor N(1) - H(1) ? PLAT_725 Alert C D-H Calc 0.86026, Rep 0.85000, Dev. 0.01 Ang. N5 -H5 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Comment top

The title compound, (I), is a representative of a class of acetolactate inhibitors (McFadden et al., 1993). Present paper reports the relevant bond distances and angles for this compound.

The C3—C31 bond length of 1.430 (3) Å is much longer than expected for the Csp2—Csp bond (Fig. 1 and Table 1). A general survey of this type of bond (S)(N)CC(C)—CN using well determined structures from the Cambridge Structural Database (September 2002 update; Allen, 2002) gave a mean of 1.43 (1) Å. This search was restricted to compounds with coordinates, no disorder, no polymers, R less than 0.10, and error free. The dihedral angle between the two aromatic groups is 85.9 (1)°. There is an intramolecular N5—H5···O21 hydrogen bonding (Table 2).

Experimental top

The synthesis of (I) has been reported by McFadden et al. (1993).

Computing details top

Data collection: Data Collection Package (Frenz & Enraf-Nonius, 1985); cell refinement: Data Collection Package; data reduction: WinGX (Version 1.64.02; Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEP plot (Spek, 1988) of the title compound, (I), with displacement ellipsoids at the 50% probability level.
3-[(2-Chlorophenyl)sulfonylamino]-2-cyano-N-(3,5-dimethoxyphenyl)- 3-methylsulfanyl-2-propenamide top
Crystal data top
C19H18ClN3O5S2Z = 2
Mr = 467.16F(000) = 484
Triclinic, P1Dx = 1.502 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.506 (1) ÅCell parameters from 25 reflections
b = 9.738 (2) Åθ = 10–12°
c = 12.572 (2) ŵ = 0.42 mm1
α = 109.65 (1)°T = 293 K
β = 94.14 (1)°Needle, colourless
γ = 106.24 (1)°0.3 × 0.05 × 0.05 mm
V = 1034.3 (3) Å3
Data collection top
Enraf-Nonius CAD-4
diffractometer
3027 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590Rint = 0.006
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
non–profiled ω scansh = 011
Absorption correction: ψ scan
(North et al., 1968)
k = 1111
Tmin = 0.958, Tmax = 0.980l = 1414
3933 measured reflections3 standard reflections every 120 min
3639 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.4158P]
where P = (Fo2 + 2Fc2)/3
3639 reflections(Δ/σ)max < 0.001
279 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C19H18ClN3O5S2γ = 106.24 (1)°
Mr = 467.16V = 1034.3 (3) Å3
Triclinic, P1Z = 2
a = 9.506 (1) ÅMo Kα radiation
b = 9.738 (2) ŵ = 0.42 mm1
c = 12.572 (2) ÅT = 293 K
α = 109.65 (1)°0.3 × 0.05 × 0.05 mm
β = 94.14 (1)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
3027 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.006
Tmin = 0.958, Tmax = 0.9803 standard reflections every 120 min
3933 measured reflections intensity decay: 1%
3639 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å3
3639 reflectionsΔρmin = 0.32 e Å3
279 parameters
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. Data were collected on a CAD4, and were corrected for absorption using the psi scan method (North, Phillips, & Mathews, 1968).

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.

Alert_230 Type 2 failure: This data fails the Hirshfeld Test for C(3)—C(31) =5.85 su. This is shown with the skewness for the Principal mean square atomic displacements U: C(3) 0.0385 0.0309 0.0256 C(31) 0.0450 0.0386 0.0213 N(32) 0.0774 0.0434 0.0329 and can not be explained. Alert_371 Type_2 Indicator failed C(sp2)-C(sp1) Bond C(3)—C(31) = 1.43 A ng. Cambridge data base C=C(-c)-CN indicates for 4452 observations C—C bond of 1.428 A ng. see Graph. Alert_420 Type_2 CN crowds out H(1) and prevents H bond forming.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.08584 (17)0.82964 (18)0.38731 (13)0.0365 (4)
H10.14840.85490.35110.044*
C110.1374 (2)0.7766 (2)0.47440 (14)0.0329 (4)
C120.0486 (2)0.7369 (2)0.54406 (15)0.0364 (4)
H120.04980.74510.53670.044*
C130.1126 (2)0.6846 (2)0.62520 (16)0.0382 (4)
O1310.03818 (17)0.63845 (19)0.69708 (13)0.0538 (4)
C1320.1097 (3)0.6408 (3)0.6865 (2)0.0575 (6)
H13A0.11150.58020.60890.086*
H13B0.14520.59870.73780.086*
H13C0.17260.74510.70570.086*
C140.2578 (2)0.6745 (2)0.63797 (16)0.0412 (5)
H140.29760.64120.69380.049*
C150.3433 (2)0.7143 (2)0.56736 (16)0.0381 (4)
O1510.48596 (16)0.69889 (19)0.58505 (13)0.0536 (4)
C1520.5791 (2)0.7376 (3)0.5135 (2)0.0587 (6)
H15A0.53680.84430.52460.088*
H15B0.67650.71950.53320.088*
H15C0.58660.67490.43450.088*
C160.2840 (2)0.7659 (2)0.48479 (15)0.0361 (4)
H160.34160.79290.43720.043*
C20.0478 (2)0.8460 (2)0.35344 (15)0.0338 (4)
O210.15068 (15)0.81940 (18)0.39926 (12)0.0487 (4)
C30.0636 (2)0.8981 (2)0.25551 (15)0.0317 (4)
C310.0595 (2)0.9272 (2)0.20552 (15)0.0350 (4)
N320.1619 (2)0.9449 (2)0.16672 (16)0.0512 (5)
C40.1915 (2)0.9196 (2)0.21046 (15)0.0314 (4)
S410.20466 (5)0.97368 (6)0.08981 (4)0.04022 (14)
C420.0678 (3)0.8099 (3)0.01907 (18)0.0597 (6)
H42A0.08310.71710.01770.090*
H42B0.07740.81580.09310.090*
H42C0.03010.80930.00470.090*
N50.31377 (17)0.90178 (19)0.26003 (13)0.0380 (4)
H50.30890.89140.32510.046*
S60.47115 (5)0.89744 (6)0.21179 (4)0.03469 (13)
O610.54778 (15)0.85609 (18)0.29190 (12)0.0489 (4)
O620.53777 (15)1.03729 (15)0.19607 (12)0.0437 (3)
C610.4207 (2)0.7452 (2)0.07581 (16)0.0339 (4)
C620.3358 (2)0.5943 (2)0.05733 (18)0.0425 (5)
Cl620.25793 (7)0.54419 (7)0.16499 (6)0.06352 (19)
C630.3103 (3)0.4804 (3)0.0494 (2)0.0550 (6)
H630.25460.37950.06150.066*
C640.3674 (3)0.5154 (3)0.1388 (2)0.0570 (6)
H640.35030.43780.21070.068*
C650.4496 (3)0.6649 (3)0.12176 (18)0.0501 (5)
H650.48670.68840.18220.060*
C660.4764 (2)0.7790 (2)0.01477 (17)0.0399 (4)
H660.53230.87960.00310.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0354 (8)0.0518 (10)0.0324 (8)0.0162 (7)0.0128 (7)0.0249 (7)
C110.0373 (10)0.0361 (9)0.0254 (8)0.0097 (8)0.0109 (7)0.0124 (7)
C120.0374 (10)0.0441 (10)0.0325 (9)0.0144 (8)0.0111 (8)0.0183 (8)
C130.0484 (11)0.0408 (10)0.0302 (9)0.0158 (9)0.0090 (8)0.0173 (8)
O1310.0584 (9)0.0766 (11)0.0490 (9)0.0306 (8)0.0167 (7)0.0426 (8)
C1320.0656 (15)0.0779 (16)0.0465 (12)0.0406 (13)0.0125 (11)0.0300 (12)
C140.0511 (12)0.0465 (11)0.0332 (10)0.0147 (9)0.0180 (9)0.0226 (9)
C150.0381 (10)0.0415 (10)0.0351 (10)0.0107 (8)0.0152 (8)0.0149 (8)
O1510.0424 (8)0.0802 (11)0.0549 (9)0.0230 (8)0.0255 (7)0.0399 (8)
C1520.0404 (12)0.0864 (18)0.0597 (14)0.0235 (12)0.0182 (11)0.0358 (13)
C160.0375 (10)0.0450 (11)0.0306 (9)0.0144 (8)0.0104 (8)0.0183 (8)
C20.0359 (10)0.0401 (10)0.0292 (9)0.0131 (8)0.0114 (8)0.0158 (8)
O210.0419 (8)0.0809 (11)0.0466 (8)0.0300 (8)0.0190 (6)0.0418 (8)
C30.0317 (9)0.0381 (10)0.0297 (9)0.0131 (8)0.0091 (7)0.0159 (8)
C310.0337 (10)0.0443 (10)0.0330 (9)0.0132 (8)0.0150 (8)0.0196 (8)
N320.0398 (10)0.0755 (13)0.0544 (11)0.0278 (9)0.0156 (8)0.0349 (10)
C40.0333 (9)0.0348 (9)0.0295 (9)0.0121 (8)0.0094 (7)0.0145 (7)
S410.0384 (3)0.0557 (3)0.0395 (3)0.0167 (2)0.0156 (2)0.0306 (2)
C420.0691 (16)0.0750 (16)0.0322 (11)0.0198 (13)0.0078 (10)0.0198 (11)
N50.0340 (8)0.0598 (10)0.0332 (8)0.0212 (7)0.0145 (7)0.0266 (8)
S60.0286 (2)0.0459 (3)0.0356 (2)0.0143 (2)0.00989 (18)0.0200 (2)
O610.0389 (8)0.0748 (10)0.0442 (8)0.0246 (7)0.0079 (6)0.0307 (8)
O620.0377 (7)0.0427 (8)0.0503 (8)0.0095 (6)0.0141 (6)0.0187 (7)
C610.0311 (9)0.0403 (10)0.0381 (10)0.0159 (8)0.0103 (8)0.0197 (8)
C620.0398 (11)0.0466 (11)0.0492 (12)0.0145 (9)0.0115 (9)0.0264 (10)
Cl620.0737 (4)0.0579 (4)0.0681 (4)0.0103 (3)0.0264 (3)0.0409 (3)
C630.0554 (14)0.0414 (12)0.0618 (14)0.0100 (10)0.0073 (11)0.0166 (11)
C640.0630 (15)0.0569 (14)0.0443 (12)0.0245 (12)0.0060 (11)0.0070 (11)
C650.0561 (13)0.0639 (14)0.0415 (11)0.0285 (11)0.0195 (10)0.0238 (11)
C660.0411 (11)0.0453 (11)0.0431 (11)0.0185 (9)0.0171 (9)0.0227 (9)
Geometric parameters (Å, º) top
N1—C21.353 (2)C3—C311.430 (3)
N1—C111.422 (2)C31—N321.139 (2)
N1—H10.86C4—N51.360 (2)
C11—C161.388 (3)C4—S411.7670 (17)
C11—C121.390 (3)S41—C421.795 (2)
C12—C131.391 (3)C42—H42A0.96
C12—H120.93C42—H42B0.96
C13—O1311.370 (2)C42—H42C0.96
C13—C141.381 (3)N5—S61.6604 (15)
O131—C1321.416 (3)N5—H50.86
C132—H13A0.96S6—O621.4182 (14)
C132—H13B0.96S6—O611.4276 (14)
C132—H13C0.96S6—C611.7689 (19)
C14—C151.379 (3)C61—C661.388 (3)
C14—H140.93C61—C621.395 (3)
C15—O1511.365 (2)C62—C631.375 (3)
C15—C161.387 (3)C62—Cl621.734 (2)
O151—C1521.426 (3)C63—C641.384 (3)
C152—H15A0.96C63—H630.93
C152—H15B0.96C64—C651.380 (3)
C152—H15C0.96C64—H640.93
C16—H160.93C65—C661.377 (3)
C2—O211.232 (2)C65—H650.93
C2—C31.483 (2)C66—H660.93
C3—C41.371 (2)
C2—N1—C11129.12 (16)C31—C3—C2118.84 (15)
C2—N1—H1115.4N32—C31—C3176.8 (2)
C11—N1—H1115.4N5—C4—C3119.94 (15)
C16—C11—C12121.96 (16)N5—C4—S41118.13 (13)
C16—C11—N1115.19 (16)C3—C4—S41121.92 (14)
C12—C11—N1122.84 (16)C4—S41—C42101.26 (10)
C11—C12—C13117.39 (17)S41—C42—H42A109.5
C11—C12—H12121.3S41—C42—H42B109.5
C13—C12—H12121.3H42A—C42—H42B109.5
O131—C13—C14115.18 (16)S41—C42—H42C109.5
O131—C13—C12123.12 (18)H42A—C42—H42C109.5
C14—C13—C12121.71 (18)H42B—C42—H42C109.5
C13—O131—C132118.43 (16)C4—N5—S6128.68 (13)
O131—C132—H13A109.5C4—N5—H5115.7
O131—C132—H13B109.5S6—N5—H5115.7
H13A—C132—H13B109.5O62—S6—O61120.11 (9)
O131—C132—H13C109.5O62—S6—N5109.12 (8)
H13A—C132—H13C109.5O61—S6—N5102.88 (8)
H13B—C132—H13C109.5O62—S6—C61108.20 (9)
C15—C14—C13119.55 (17)O61—S6—C61109.21 (9)
C15—C14—H14120.2N5—S6—C61106.50 (9)
C13—C14—H14120.2C66—C61—C62119.34 (18)
O151—C15—C14115.57 (16)C66—C61—S6117.05 (15)
O151—C15—C16123.89 (18)C62—C61—S6123.52 (14)
C14—C15—C16120.55 (18)C63—C62—C61119.90 (19)
C15—O151—C152117.61 (15)C63—C62—Cl62118.03 (16)
O151—C152—H15A109.5C61—C62—Cl62122.06 (16)
O151—C152—H15B109.5C62—C63—C64120.2 (2)
H15A—C152—H15B109.5C62—C63—H63119.9
O151—C152—H15C109.5C64—C63—H63119.9
H15A—C152—H15C109.5C65—C64—C63120.4 (2)
H15B—C152—H15C109.5C65—C64—H64119.8
C15—C16—C11118.83 (18)C63—C64—H64119.8
C15—C16—H16120.6C66—C65—C64119.6 (2)
C11—C16—H16120.6C66—C65—H65120.2
O21—C2—N1123.26 (16)C64—C65—H65120.2
O21—C2—C3121.18 (16)C65—C66—C61120.61 (19)
N1—C2—C3115.56 (16)C65—C66—H66119.7
C4—C3—C31118.31 (16)C61—C66—H66119.7
C4—C3—C2122.85 (16)
C12—C11—N1—C22.6 (3)C3—C4—N5—S6170.64 (15)
C11—N1—C2—C3177.31 (17)C4—N5—S6—C6157.85 (19)
N1—C2—C3—C4179.67 (17)N5—S6—C61—C6254.47 (18)
C2—C3—C4—N53.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O210.851.922.599 (2)135

Experimental details

Crystal data
Chemical formulaC19H18ClN3O5S2
Mr467.16
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.506 (1), 9.738 (2), 12.572 (2)
α, β, γ (°)109.65 (1), 94.14 (1), 106.24 (1)
V3)1034.3 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.3 × 0.05 × 0.05
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.958, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
3933, 3639, 3027
Rint0.006
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.087, 1.02
No. of reflections3639
No. of parameters279
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.32

Computer programs: Data Collection Package (Frenz & Enraf-Nonius, 1985), Data Collection Package, WinGX (Version 1.64.02; Farrugia, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON98 (Spek, 1998), SHELXL97.

Selected geometric parameters (Å, º) top
C2—C31.483 (2)C3—C311.430 (3)
C3—C41.371 (2)C31—N321.139 (2)
C12—C11—N1—C22.6 (3)C3—C4—N5—S6170.64 (15)
C11—N1—C2—C3177.31 (17)C4—N5—S6—C6157.85 (19)
N1—C2—C3—C4179.67 (17)N5—S6—C61—C6254.47 (18)
C2—C3—C4—N53.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O210.851.922.599 (2)135
 

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