3-[(2-Chloro­phenyl)­sulfonyl­amino]-2-cyano-N-(3,5-di­methoxy­phenyl)-3-methyl­sulfanyl-2-propen­amide

Kennard, C.H.L.; McFadden, H.G.; Byriel, K.A.

doi:10.1107/S1600536803010584

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3-[(2-Chlorophenyl)sulfonylamino]-2-cyano-N-(3,5-dimethoxyphenyl)-3-methylsulfanyl-2-propenamide

C. H. L. Kennard, H. G. McFadden and K. A. Byriel

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)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010584/ob6233sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010584/ob6233Isup2.hkl Contains datablock I

CCDC reference: 217440

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (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


 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)C═C(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

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

C₁₉H₁₈ClN₃O₅S₂	Z = 2
M_r = 467.16	F(000) = 484
Triclinic, P1	D_x = 1.502 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.506 (1) Å	Cell parameters from 25 reflections
b = 9.738 (2) Å	θ = 10–12°
c = 12.572 (2) Å	µ = 0.42 mm⁻¹
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 FR590	R_int = 0.006
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
non–profiled ω scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.958, T_max = 0.980	l = −14→14
3933 measured reflections	3 standard reflections every 120 min
3639 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0478P)² + 0.4158P] where P = (F_o² + 2F_c²)/3
3639 reflections	(Δ/σ)_max < 0.001
279 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₉H₁₈ClN₃O₅S₂	γ = 106.24 (1)°
M_r = 467.16	V = 1034.3 (3) Å³
Triclinic, P1	Z = 2
a = 9.506 (1) Å	Mo Kα radiation
b = 9.738 (2) Å	µ = 0.42 mm⁻¹
c = 12.572 (2) Å	T = 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)	R_int = 0.006
T_min = 0.958, T_max = 0.980	3 standard reflections every 120 min
3933 measured reflections	intensity decay: 1%
3639 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
3639 reflections	Δρ_min = −0.32 e Å⁻³
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

	x	y	z	U_iso*/U_eq
N1	−0.08584 (17)	0.82964 (18)	0.38731 (13)	0.0365 (4)
H1	−0.1484	0.8549	0.3511	0.044*
C11	−0.1374 (2)	0.7766 (2)	0.47440 (14)	0.0329 (4)
C12	−0.0486 (2)	0.7369 (2)	0.54406 (15)	0.0364 (4)
H12	0.0498	0.7451	0.5367	0.044*
C13	−0.1126 (2)	0.6846 (2)	0.62520 (16)	0.0382 (4)
O131	−0.03818 (17)	0.63845 (19)	0.69708 (13)	0.0538 (4)
C132	0.1097 (3)	0.6408 (3)	0.6865 (2)	0.0575 (6)
H13A	0.1115	0.5802	0.6089	0.086*
H13B	0.1452	0.5987	0.7378	0.086*
H13C	0.1726	0.7451	0.7057	0.086*
C14	−0.2578 (2)	0.6745 (2)	0.63797 (16)	0.0412 (5)
H14	−0.2976	0.6412	0.6938	0.049*
C15	−0.3433 (2)	0.7143 (2)	0.56736 (16)	0.0381 (4)
O151	−0.48596 (16)	0.69889 (19)	0.58505 (13)	0.0536 (4)
C152	−0.5791 (2)	0.7376 (3)	0.5135 (2)	0.0587 (6)
H15A	−0.5368	0.8443	0.5246	0.088*
H15B	−0.6765	0.7195	0.5332	0.088*
H15C	−0.5866	0.6749	0.4345	0.088*
C16	−0.2840 (2)	0.7659 (2)	0.48479 (15)	0.0361 (4)
H16	−0.3416	0.7929	0.4372	0.043*
C2	0.0478 (2)	0.8460 (2)	0.35344 (15)	0.0338 (4)
O21	0.15068 (15)	0.81940 (18)	0.39926 (12)	0.0487 (4)
C3	0.0636 (2)	0.8981 (2)	0.25551 (15)	0.0317 (4)
C31	−0.0595 (2)	0.9272 (2)	0.20552 (15)	0.0350 (4)
N32	−0.1619 (2)	0.9449 (2)	0.16672 (16)	0.0512 (5)
C4	0.1915 (2)	0.9196 (2)	0.21046 (15)	0.0314 (4)
S41	0.20466 (5)	0.97368 (6)	0.08981 (4)	0.04022 (14)
C42	0.0678 (3)	0.8099 (3)	−0.01907 (18)	0.0597 (6)
H42A	0.0831	0.7171	−0.0177	0.090*
H42B	0.0774	0.8158	−0.0931	0.090*
H42C	−0.0301	0.8093	−0.0047	0.090*
N5	0.31377 (17)	0.90178 (19)	0.26003 (13)	0.0380 (4)
H5	0.3089	0.8914	0.3251	0.046*
S6	0.47115 (5)	0.89744 (6)	0.21179 (4)	0.03469 (13)
O61	0.54778 (15)	0.85609 (18)	0.29190 (12)	0.0489 (4)
O62	0.53777 (15)	1.03729 (15)	0.19607 (12)	0.0437 (3)
C61	0.4207 (2)	0.7452 (2)	0.07581 (16)	0.0339 (4)
C62	0.3358 (2)	0.5943 (2)	0.05733 (18)	0.0425 (5)
Cl62	0.25793 (7)	0.54419 (7)	0.16499 (6)	0.06352 (19)
C63	0.3103 (3)	0.4804 (3)	−0.0494 (2)	0.0550 (6)
H63	0.2546	0.3795	−0.0615	0.066*
C64	0.3674 (3)	0.5154 (3)	−0.1388 (2)	0.0570 (6)
H64	0.3503	0.4378	−0.2107	0.068*
C65	0.4496 (3)	0.6649 (3)	−0.12176 (18)	0.0501 (5)
H65	0.4867	0.6884	−0.1822	0.060*
C66	0.4764 (2)	0.7790 (2)	−0.01477 (17)	0.0399 (4)
H66	0.5323	0.8796	−0.0031	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0354 (8)	0.0518 (10)	0.0324 (8)	0.0162 (7)	0.0128 (7)	0.0249 (7)
C11	0.0373 (10)	0.0361 (9)	0.0254 (8)	0.0097 (8)	0.0109 (7)	0.0124 (7)
C12	0.0374 (10)	0.0441 (10)	0.0325 (9)	0.0144 (8)	0.0111 (8)	0.0183 (8)
C13	0.0484 (11)	0.0408 (10)	0.0302 (9)	0.0158 (9)	0.0090 (8)	0.0173 (8)
O131	0.0584 (9)	0.0766 (11)	0.0490 (9)	0.0306 (8)	0.0167 (7)	0.0426 (8)
C132	0.0656 (15)	0.0779 (16)	0.0465 (12)	0.0406 (13)	0.0125 (11)	0.0300 (12)
C14	0.0511 (12)	0.0465 (11)	0.0332 (10)	0.0147 (9)	0.0180 (9)	0.0226 (9)
C15	0.0381 (10)	0.0415 (10)	0.0351 (10)	0.0107 (8)	0.0152 (8)	0.0149 (8)
O151	0.0424 (8)	0.0802 (11)	0.0549 (9)	0.0230 (8)	0.0255 (7)	0.0399 (8)
C152	0.0404 (12)	0.0864 (18)	0.0597 (14)	0.0235 (12)	0.0182 (11)	0.0358 (13)
C16	0.0375 (10)	0.0450 (11)	0.0306 (9)	0.0144 (8)	0.0104 (8)	0.0183 (8)
C2	0.0359 (10)	0.0401 (10)	0.0292 (9)	0.0131 (8)	0.0114 (8)	0.0158 (8)
O21	0.0419 (8)	0.0809 (11)	0.0466 (8)	0.0300 (8)	0.0190 (6)	0.0418 (8)
C3	0.0317 (9)	0.0381 (10)	0.0297 (9)	0.0131 (8)	0.0091 (7)	0.0159 (8)
C31	0.0337 (10)	0.0443 (10)	0.0330 (9)	0.0132 (8)	0.0150 (8)	0.0196 (8)
N32	0.0398 (10)	0.0755 (13)	0.0544 (11)	0.0278 (9)	0.0156 (8)	0.0349 (10)
C4	0.0333 (9)	0.0348 (9)	0.0295 (9)	0.0121 (8)	0.0094 (7)	0.0145 (7)
S41	0.0384 (3)	0.0557 (3)	0.0395 (3)	0.0167 (2)	0.0156 (2)	0.0306 (2)
C42	0.0691 (16)	0.0750 (16)	0.0322 (11)	0.0198 (13)	0.0078 (10)	0.0198 (11)
N5	0.0340 (8)	0.0598 (10)	0.0332 (8)	0.0212 (7)	0.0145 (7)	0.0266 (8)
S6	0.0286 (2)	0.0459 (3)	0.0356 (2)	0.0143 (2)	0.00989 (18)	0.0200 (2)
O61	0.0389 (8)	0.0748 (10)	0.0442 (8)	0.0246 (7)	0.0079 (6)	0.0307 (8)
O62	0.0377 (7)	0.0427 (8)	0.0503 (8)	0.0095 (6)	0.0141 (6)	0.0187 (7)
C61	0.0311 (9)	0.0403 (10)	0.0381 (10)	0.0159 (8)	0.0103 (8)	0.0197 (8)
C62	0.0398 (11)	0.0466 (11)	0.0492 (12)	0.0145 (9)	0.0115 (9)	0.0264 (10)
Cl62	0.0737 (4)	0.0579 (4)	0.0681 (4)	0.0103 (3)	0.0264 (3)	0.0409 (3)
C63	0.0554 (14)	0.0414 (12)	0.0618 (14)	0.0100 (10)	0.0073 (11)	0.0166 (11)
C64	0.0630 (15)	0.0569 (14)	0.0443 (12)	0.0245 (12)	0.0060 (11)	0.0070 (11)
C65	0.0561 (13)	0.0639 (14)	0.0415 (11)	0.0285 (11)	0.0195 (10)	0.0238 (11)
C66	0.0411 (11)	0.0453 (11)	0.0431 (11)	0.0185 (9)	0.0171 (9)	0.0227 (9)

Geometric parameters (Å, º) top

N1—C2	1.353 (2)	C3—C31	1.430 (3)
N1—C11	1.422 (2)	C31—N32	1.139 (2)
N1—H1	0.86	C4—N5	1.360 (2)
C11—C16	1.388 (3)	C4—S41	1.7670 (17)
C11—C12	1.390 (3)	S41—C42	1.795 (2)
C12—C13	1.391 (3)	C42—H42A	0.96
C12—H12	0.93	C42—H42B	0.96
C13—O131	1.370 (2)	C42—H42C	0.96
C13—C14	1.381 (3)	N5—S6	1.6604 (15)
O131—C132	1.416 (3)	N5—H5	0.86
C132—H13A	0.96	S6—O62	1.4182 (14)
C132—H13B	0.96	S6—O61	1.4276 (14)
C132—H13C	0.96	S6—C61	1.7689 (19)
C14—C15	1.379 (3)	C61—C66	1.388 (3)
C14—H14	0.93	C61—C62	1.395 (3)
C15—O151	1.365 (2)	C62—C63	1.375 (3)
C15—C16	1.387 (3)	C62—Cl62	1.734 (2)
O151—C152	1.426 (3)	C63—C64	1.384 (3)
C152—H15A	0.96	C63—H63	0.93
C152—H15B	0.96	C64—C65	1.380 (3)
C152—H15C	0.96	C64—H64	0.93
C16—H16	0.93	C65—C66	1.377 (3)
C2—O21	1.232 (2)	C65—H65	0.93
C2—C3	1.483 (2)	C66—H66	0.93
C3—C4	1.371 (2)

C2—N1—C11	129.12 (16)	C31—C3—C2	118.84 (15)
C2—N1—H1	115.4	N32—C31—C3	176.8 (2)
C11—N1—H1	115.4	N5—C4—C3	119.94 (15)
C16—C11—C12	121.96 (16)	N5—C4—S41	118.13 (13)
C16—C11—N1	115.19 (16)	C3—C4—S41	121.92 (14)
C12—C11—N1	122.84 (16)	C4—S41—C42	101.26 (10)
C11—C12—C13	117.39 (17)	S41—C42—H42A	109.5
C11—C12—H12	121.3	S41—C42—H42B	109.5
C13—C12—H12	121.3	H42A—C42—H42B	109.5
O131—C13—C14	115.18 (16)	S41—C42—H42C	109.5
O131—C13—C12	123.12 (18)	H42A—C42—H42C	109.5
C14—C13—C12	121.71 (18)	H42B—C42—H42C	109.5
C13—O131—C132	118.43 (16)	C4—N5—S6	128.68 (13)
O131—C132—H13A	109.5	C4—N5—H5	115.7
O131—C132—H13B	109.5	S6—N5—H5	115.7
H13A—C132—H13B	109.5	O62—S6—O61	120.11 (9)
O131—C132—H13C	109.5	O62—S6—N5	109.12 (8)
H13A—C132—H13C	109.5	O61—S6—N5	102.88 (8)
H13B—C132—H13C	109.5	O62—S6—C61	108.20 (9)
C15—C14—C13	119.55 (17)	O61—S6—C61	109.21 (9)
C15—C14—H14	120.2	N5—S6—C61	106.50 (9)
C13—C14—H14	120.2	C66—C61—C62	119.34 (18)
O151—C15—C14	115.57 (16)	C66—C61—S6	117.05 (15)
O151—C15—C16	123.89 (18)	C62—C61—S6	123.52 (14)
C14—C15—C16	120.55 (18)	C63—C62—C61	119.90 (19)
C15—O151—C152	117.61 (15)	C63—C62—Cl62	118.03 (16)
O151—C152—H15A	109.5	C61—C62—Cl62	122.06 (16)
O151—C152—H15B	109.5	C62—C63—C64	120.2 (2)
H15A—C152—H15B	109.5	C62—C63—H63	119.9
O151—C152—H15C	109.5	C64—C63—H63	119.9
H15A—C152—H15C	109.5	C65—C64—C63	120.4 (2)
H15B—C152—H15C	109.5	C65—C64—H64	119.8
C15—C16—C11	118.83 (18)	C63—C64—H64	119.8
C15—C16—H16	120.6	C66—C65—C64	119.6 (2)
C11—C16—H16	120.6	C66—C65—H65	120.2
O21—C2—N1	123.26 (16)	C64—C65—H65	120.2
O21—C2—C3	121.18 (16)	C65—C66—C61	120.61 (19)
N1—C2—C3	115.56 (16)	C65—C66—H66	119.7
C4—C3—C31	118.31 (16)	C61—C66—H66	119.7
C4—C3—C2	122.85 (16)

C12—C11—N1—C2	2.6 (3)	C3—C4—N5—S6	170.64 (15)
C11—N1—C2—C3	177.31 (17)	C4—N5—S6—C61	−57.85 (19)
N1—C2—C3—C4	−179.67 (17)	N5—S6—C61—C62	−54.47 (18)
C2—C3—C4—N5	−3.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O21	0.85	1.92	2.599 (2)	135

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈ClN₃O₅S₂
M_r	467.16
Crystal system, space group	Triclinic, 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)
V (Å³)	1034.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.3 × 0.05 × 0.05

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.958, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	3933, 3639, 3027
R_int	0.006
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.087, 1.02
No. of reflections	3639
No. of parameters	279
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—C3	1.483 (2)	C3—C31	1.430 (3)
C3—C4	1.371 (2)	C31—N32	1.139 (2)

C12—C11—N1—C2	2.6 (3)	C3—C4—N5—S6	170.64 (15)
C11—N1—C2—C3	177.31 (17)	C4—N5—S6—C61	−57.85 (19)
N1—C2—C3—C4	−179.67 (17)	N5—S6—C61—C62	−54.47 (18)
C2—C3—C4—N5	−3.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O21	0.85	1.92	2.599 (2)	135

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