Ethyl N-[3-(N,N-dimethyl­carbamo­yl)pyridin-2-ylsulfon­yl]carbamate

Hou, Y.-J.; Chu, W.-Y.; Sui, J.; Sun, Z.-Z.

doi:10.1107/S160053681000663X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o707

doi:10.1107/S160053681000663X

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Ethyl N-[3-(N,N-dimethylcarbamoyl)pyridin-2-ylsulfonyl]carbamate

Yan-Jun Hou,^a Wen-Yi Chu,^a Jun Sui ^a and Zhi-Zhong Sun ^a ^*

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hljusunzhizhong@163.com

(Received 29 January 2010; accepted 21 February 2010; online 27 February 2010)

In the molecular structure of the title compound, C₁₁H₁₅N₃O₅S, the amide group is nearly perpendicular to the pyridine ring, making a dihedral angle of 86.30 (13)°. The terminal ethyl group is disordered over two sites of equal occupancy. Intermolecular N—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

The title compound is used in the preparation of nicosulfuron, a member of the sulfonylurea family of herbicides, see: Green & Ulrich (1993 ). For the synthesis, see: Murai et al. (1992 ).

Experimental

Crystal data

C₁₁H₁₅N₃O₅S
M_r = 301.32
Monoclinic, P 2₁ /n
a = 8.4370 (11) Å
b = 11.1141 (15) Å
c = 15.074 (2) Å
β = 100.594 (2)°
V = 1389.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.17 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.958, T_max = 0.963
7979 measured reflections
3036 independent reflections
2384 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.129
S = 1.04
3036 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.87 (2)	1.91 (3)	2.773 (2)	172 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000663X/xu2723sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000663X/xu2723Isup2.hkl

checkCIF report

Comment top

The ethyl 3-(dimethylcarbamoyl)pyridin-2-ylsulfonylcarbamate is used for preparation of nicosulfuron, which is a member of the sulfonylurea family of herbicides (Green et al., 1993).

The molecular structure is shown in Fig. 1. In the molecular structure the amide group is nearly perpendicular to the pyridine ring, the dihedral angle being 86.30 (13)°. Intermolecular N—H···O hydrogen bonding (Table 1) helps to stabilize the crystal structure.

Related literature top

Thetitle compound is used in the preparation of nicosulfuron, a member of the sulfonylurea family of herbicides, see: Green & Ulrich (1993). For the synthesis, see: Murai et al. (1992).

Experimental top

To a solution of N,N-dimethyl-2-sulfamoylnicotinamide (10 mmol) and NaOH (12 mmol) in anhydrous toluene (50 ml) was added ethyl carbonochloridate (12 mmol). After stirring the mixture for 10 h at room temperature, the solvent was removed and 100 ml water was added. The oil after separation was concentrated under reduced pressure and the residue was recrystallized from methanol to give the title compound in a yield of 90% (Murai et al. 1992). Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from ethanol at room temperature in a yield of 60%. Analysis found: C 43.9, H 4.9, N 13.9%; C₁₁H₁₅N₃O₅S requires: C 43.9, H 5.0, N 14.0%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. The disorder is shown.
	Fig. 2. A part of packing of the crystal structure of the title compound, viewed down the a direction. Dashed lines indicate hydrogen bonds.

Ethyl N-[3-(N,N-dimethylcarbamoyl)pyridin-2-ylsulfonyl]carbamate top

Crystal data top

C₁₁H₁₅N₃O₅S	F(000) = 632
M_r = 301.32	D_x = 1.441 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 436–437 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.4370 (11) Å	Cell parameters from 2785 reflections
b = 11.1141 (15) Å	θ = 2.3–26.9°
c = 15.074 (2) Å	µ = 0.26 mm⁻¹
β = 100.594 (2)°	T = 296 K
V = 1389.4 (3) Å³	Prism, colorless
Z = 4	0.17 × 0.16 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3036 independent reflections
Radiation source: fine-focus sealed tube	2384 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 27.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.958, T_max = 0.963	k = −13→14
7979 measured reflections	l = −19→18

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0732P)² + 0.3548P] where P = (F_o² + 2F_c²)/3
3036 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₁H₁₅N₃O₅S	V = 1389.4 (3) Å³
M_r = 301.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4370 (11) Å	µ = 0.26 mm⁻¹
b = 11.1141 (15) Å	T = 296 K
c = 15.074 (2) Å	0.17 × 0.16 × 0.15 mm
β = 100.594 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3036 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2384 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.963	R_int = 0.026
7979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.29 e Å⁻³
3036 reflections	Δρ_min = −0.47 e Å⁻³
195 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	U_iso*/U_eq	Occ. (<1)
S1	0.81078 (6)	0.56615 (4)	0.24067 (3)	0.03700 (17)
O1	1.05540 (17)	0.28321 (14)	0.28830 (10)	0.0475 (4)
O2	0.97802 (19)	0.58254 (14)	0.27370 (11)	0.0526 (4)
O3	0.7045 (2)	0.54186 (15)	0.30175 (11)	0.0554 (4)
O4	0.90004 (19)	0.68423 (15)	0.08036 (11)	0.0539 (4)
O5	0.6813 (2)	0.80460 (14)	0.06652 (12)	0.0552 (4)
N1	0.6502 (2)	0.45464 (16)	0.10014 (12)	0.0432 (4)
N2	1.19984 (19)	0.39369 (16)	0.20603 (12)	0.0407 (4)
N3	0.7342 (2)	0.68519 (15)	0.18467 (12)	0.0379 (4)
H3	0.641 (3)	0.709 (2)	0.1945 (16)	0.045 (6)*
C1	0.6257 (3)	0.37404 (19)	0.03341 (15)	0.0480 (5)
H1A	0.5289	0.3764	−0.0076	0.058*
C2	0.7368 (3)	0.28809 (19)	0.02256 (15)	0.0490 (5)
H2A	0.7162	0.2340	−0.0253	0.059*
C3	0.8789 (3)	0.28309 (19)	0.08340 (15)	0.0434 (5)
H3A	0.9543	0.2239	0.0778	0.052*
C4	0.9110 (2)	0.36615 (16)	0.15349 (12)	0.0315 (4)
C5	0.7912 (2)	0.45025 (16)	0.15719 (12)	0.0313 (4)
C6	1.0625 (2)	0.34801 (17)	0.22302 (13)	0.0341 (4)
C7	1.2086 (3)	0.4806 (2)	0.13467 (18)	0.0538 (6)
H7A	1.1029	0.4929	0.0995	0.081*
H7B	1.2790	0.4505	0.0965	0.081*
H7C	1.2498	0.5555	0.1610	0.081*
C8	1.3496 (3)	0.3661 (3)	0.26777 (18)	0.0624 (7)
H8A	1.3293	0.3065	0.3105	0.094*
H8B	1.3907	0.4378	0.2993	0.094*
H8C	1.4273	0.3357	0.2342	0.094*
C9	0.7842 (2)	0.72299 (17)	0.10698 (14)	0.0381 (4)
C10A	0.698 (2)	0.8377 (11)	−0.0234 (15)	0.068 (3)	0.50
H10A	0.5943	0.8591	−0.0591	0.082*	0.50
H10B	0.7428	0.7715	−0.0528	0.082*	0.50
C11A	0.8134 (12)	0.9468 (6)	−0.0135 (5)	0.0974 (19)	0.50
H11A	0.8150	0.9806	−0.0720	0.146*	0.50
H11B	0.9201	0.9212	0.0133	0.146*	0.50
H11C	0.7768	1.0063	0.0242	0.146*	0.50
C10B	0.734 (2)	0.8705 (11)	−0.0110 (16)	0.068 (3)	0.50
H10C	0.8457	0.8953	0.0046	0.082*	0.50
H10D	0.7203	0.8205	−0.0646	0.082*	0.50
C11B	0.6287 (12)	0.9729 (6)	−0.0249 (5)	0.0974 (19)	0.50
H11D	0.6625	1.0259	−0.0682	0.146*	0.50
H11E	0.6330	1.0147	0.0312	0.146*	0.50
H11F	0.5203	0.9466	−0.0471	0.146*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0368 (3)	0.0411 (3)	0.0317 (3)	0.0050 (2)	0.00264 (19)	−0.00259 (19)
O1	0.0327 (8)	0.0603 (9)	0.0480 (9)	−0.0012 (7)	0.0035 (6)	0.0214 (7)
O2	0.0417 (9)	0.0563 (9)	0.0520 (10)	0.0039 (7)	−0.0116 (7)	−0.0142 (7)
O3	0.0664 (11)	0.0635 (10)	0.0407 (9)	0.0091 (8)	0.0214 (8)	0.0056 (7)
O4	0.0500 (10)	0.0582 (10)	0.0589 (10)	0.0103 (8)	0.0243 (8)	0.0051 (8)
O5	0.0601 (11)	0.0493 (9)	0.0592 (10)	0.0162 (8)	0.0191 (8)	0.0155 (8)
N1	0.0331 (9)	0.0446 (10)	0.0461 (10)	0.0040 (7)	−0.0076 (7)	−0.0011 (8)
N2	0.0248 (8)	0.0466 (9)	0.0516 (10)	0.0009 (7)	0.0094 (7)	0.0087 (8)
N3	0.0364 (9)	0.0384 (9)	0.0401 (9)	0.0081 (7)	0.0098 (7)	−0.0021 (7)
C1	0.0455 (12)	0.0434 (12)	0.0472 (12)	−0.0058 (10)	−0.0125 (10)	−0.0005 (10)
C2	0.0632 (15)	0.0402 (11)	0.0406 (12)	−0.0055 (10)	0.0010 (10)	−0.0050 (9)
C3	0.0483 (12)	0.0385 (10)	0.0444 (11)	0.0060 (9)	0.0115 (10)	−0.0015 (9)
C4	0.0283 (9)	0.0337 (9)	0.0334 (9)	0.0000 (7)	0.0079 (7)	0.0058 (7)
C5	0.0280 (9)	0.0332 (9)	0.0316 (9)	−0.0002 (7)	0.0025 (7)	0.0013 (7)
C6	0.0274 (9)	0.0363 (9)	0.0390 (10)	0.0040 (7)	0.0071 (8)	0.0045 (8)
C7	0.0412 (13)	0.0582 (14)	0.0667 (16)	−0.0022 (10)	0.0219 (11)	0.0172 (12)
C8	0.0280 (11)	0.0805 (18)	0.0759 (17)	0.0020 (11)	0.0024 (11)	0.0118 (14)
C9	0.0383 (11)	0.0310 (9)	0.0453 (11)	−0.0002 (8)	0.0087 (9)	−0.0025 (8)
C10A	0.083 (7)	0.044 (6)	0.083 (6)	0.002 (4)	0.030 (5)	0.026 (6)
C11A	0.170 (6)	0.059 (2)	0.069 (3)	0.005 (3)	0.036 (4)	0.007 (2)
C10B	0.083 (7)	0.044 (6)	0.083 (6)	0.002 (4)	0.030 (5)	0.026 (6)
C11B	0.170 (6)	0.059 (2)	0.069 (3)	0.005 (3)	0.036 (4)	0.007 (2)

Geometric parameters (Å, º) top

S1—O2	1.4191 (16)	C3—H3A	0.9300
S1—O3	1.4241 (16)	C4—C5	1.385 (3)
S1—N3	1.6369 (18)	C4—C6	1.510 (3)
S1—C5	1.7871 (19)	C7—H7A	0.9600
O1—C6	1.230 (2)	C7—H7B	0.9600
O4—C9	1.202 (2)	C7—H7C	0.9600
O5—C9	1.324 (2)	C8—H8A	0.9600
O5—C10A	1.44 (2)	C8—H8B	0.9600
O5—C10B	1.51 (2)	C8—H8C	0.9600
N1—C1	1.334 (3)	C10A—C11A	1.544 (11)
N1—C5	1.335 (2)	C10A—H10A	0.9700
N2—C6	1.332 (2)	C10A—H10B	0.9700
N2—C7	1.458 (3)	C11A—H11A	0.9600
N2—C8	1.457 (3)	C11A—H11B	0.9600
N3—C9	1.381 (3)	C11A—H11C	0.9600
N3—H3	0.87 (2)	C10B—C11B	1.434 (19)
C1—C2	1.369 (3)	C10B—H10C	0.9700
C1—H1A	0.9300	C10B—H10D	0.9700
C2—C3	1.370 (3)	C11B—H11D	0.9600
C2—H2A	0.9300	C11B—H11E	0.9600
C3—C4	1.392 (3)	C11B—H11F	0.9600

O2—S1—O3	120.07 (11)	N2—C7—H7A	109.5
O2—S1—N3	110.48 (10)	N2—C7—H7B	109.5
O3—S1—N3	104.54 (9)	H7A—C7—H7B	109.5
O2—S1—C5	107.25 (9)	N2—C7—H7C	109.5
O3—S1—C5	109.34 (10)	H7A—C7—H7C	109.5
N3—S1—C5	104.06 (9)	H7B—C7—H7C	109.5
C9—O5—C10A	116.1 (8)	N2—C8—H8A	109.5
C9—O5—C10B	115.3 (7)	N2—C8—H8B	109.5
C10A—O5—C10B	18.8 (10)	H8A—C8—H8B	109.5
C1—N1—C5	117.19 (18)	N2—C8—H8C	109.5
C6—N2—C7	123.95 (18)	H8A—C8—H8C	109.5
C6—N2—C8	118.64 (18)	H8B—C8—H8C	109.5
C7—N2—C8	117.07 (18)	O4—C9—O5	126.6 (2)
C9—N3—S1	122.01 (14)	O4—C9—N3	124.59 (19)
C9—N3—H3	118.8 (16)	O5—C9—N3	108.80 (17)
S1—N3—H3	116.1 (16)	O5—C10A—C11A	106.2 (12)
N1—C1—C2	123.0 (2)	O5—C10A—H10A	110.5
N1—C1—H1A	118.5	C11A—C10A—H10A	110.5
C2—C1—H1A	118.5	O5—C10A—H10B	110.5
C1—C2—C3	118.8 (2)	C11A—C10A—H10B	110.5
C1—C2—H2A	120.6	H10A—C10A—H10B	108.7
C3—C2—H2A	120.6	C11B—C10B—O5	103.6 (13)
C2—C3—C4	120.37 (19)	C11B—C10B—H10C	111.0
C2—C3—H3A	119.8	O5—C10B—H10C	111.0
C4—C3—H3A	119.8	C11B—C10B—H10D	111.0
C5—C4—C3	115.90 (18)	O5—C10B—H10D	111.0
C5—C4—C6	126.36 (17)	H10C—C10B—H10D	109.0
C3—C4—C6	117.39 (17)	C10B—C11B—H11D	109.5
N1—C5—C4	124.70 (17)	C10B—C11B—H11E	109.5
N1—C5—S1	112.53 (14)	H11D—C11B—H11E	109.5
C4—C5—S1	122.77 (14)	C10B—C11B—H11F	109.5
O1—C6—N2	123.32 (18)	H11D—C11B—H11F	109.5
O1—C6—C4	118.27 (16)	H11E—C11B—H11F	109.5
N2—C6—C4	118.10 (17)

O2—S1—N3—C9	62.57 (18)	N3—S1—C5—C4	138.92 (16)
O3—S1—N3—C9	−166.94 (17)	C7—N2—C6—O1	−173.2 (2)
C5—S1—N3—C9	−52.26 (18)	C8—N2—C6—O1	−0.1 (3)
C5—N1—C1—C2	0.9 (3)	C7—N2—C6—C4	13.3 (3)
N1—C1—C2—C3	0.9 (4)	C8—N2—C6—C4	−173.57 (19)
C1—C2—C3—C4	−1.7 (3)	C5—C4—C6—O1	85.0 (3)
C2—C3—C4—C5	0.7 (3)	C3—C4—C6—O1	−87.8 (2)
C2—C3—C4—C6	174.29 (19)	C5—C4—C6—N2	−101.2 (2)
C1—N1—C5—C4	−2.0 (3)	C3—C4—C6—N2	86.0 (2)
C1—N1—C5—S1	177.97 (16)	C10A—O5—C9—O4	8.8 (6)
C3—C4—C5—N1	1.2 (3)	C10B—O5—C9—O4	−12.0 (7)
C6—C4—C5—N1	−171.70 (18)	C10A—O5—C9—N3	−169.1 (6)
C3—C4—C5—S1	−178.77 (14)	C10B—O5—C9—N3	170.0 (7)
C6—C4—C5—S1	8.3 (3)	S1—N3—C9—O4	−10.6 (3)
O2—S1—C5—N1	−158.18 (15)	S1—N3—C9—O5	167.38 (14)
O3—S1—C5—N1	70.14 (16)	C9—O5—C10A—C11A	−91.5 (10)
N3—S1—C5—N1	−41.09 (16)	C10B—O5—C10A—C11A	1 (4)
O2—S1—C5—C4	21.83 (18)	C9—O5—C10B—C11B	−164.2 (7)
O3—S1—C5—C4	−109.86 (17)	C10A—O5—C10B—C11B	99 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.87 (2)	1.91 (3)	2.773 (2)	172 (2)

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅N₃O₅S
M_r	301.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.4370 (11), 11.1141 (15), 15.074 (2)
β (°)	100.594 (2)
V (Å³)	1389.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.17 × 0.16 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.958, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	7979, 3036, 2384
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.129, 1.04
No. of reflections	3036
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.47

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.87 (2)	1.91 (3)	2.773 (2)	172 (2)

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

We thank the National Natural Science Foundation of China (No. 20872030) and Heilongjiang University of China for supporting this study.

References

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