Methyl 2-{[3-(4,6-dimethoxy-pyrimidin-2-yl)ureido]sulfonyl-meth-yl}benzoate.

In the title compound, C(16)H(18)N(4)O(7)S, a synthetic sulfonyl-urea herbicide, there are intra-molecular N-H⋯N and C-H⋯O hydrogen bonds. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds form centrosymmetric dimers. The dihedral angle between the two rings is 50.00 (15)°.

Related literature

For related literature, see: Kong et al. (1990 ▶); Lee et al. (2002 ▶); Sabadie (1996 ▶).

Experimental

Crystal data

C16H18N4O7S

M = 410.41

Monoclinic,

a = 33.831 (7) Å

b = 6.9020 (14) Å

c = 16.021 (3) Å

β = 104.48 (3)°

V = 3622.1 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 298 (2) K

0.40 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.914, T max = 0.978

3325 measured reflections

3265 independent reflections

2421 reflections with I > 2σ(I)

R int = 0.035

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.156

S = 1.03

3265 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005011/cf2185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005011/cf2185Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H18N4O7S	F000 = 1712
Mr = 410.41	Dx = 1.505 Mg m−3
Monoclinic, C2/c	Melting point = 450–451 K
Hall symbol: -C 2yc	Mo Kα radiation λ = 0.71073 Å
a = 33.831 (7) Å	Cell parameters from 25 reflections
b = 6.9020 (14) Å	θ = 10–13º
c = 16.021 (3) Å	µ = 0.23 mm−1
β = 104.48 (3)º	T = 298 (2) K
V = 3622.1 (13) Å3	Needle, colorless
Z = 8	0.40 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.035
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 1.2º
T = 298(2) K	h = −40→38
ω/2θ scans	k = 0→8
Absorption correction: ψ scan(North et al., 1968)	l = 0→19
Tmin = 0.914, Tmax = 0.978	3 standard reflections
3325 measured reflections	every 200 reflections
3265 independent reflections	intensity decay: none
2421 reflections with I > 2σ(I)

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.08P)2 + 5P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3265 reflections	Δρmax = 0.26 e Å−3
253 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
S	0.12664 (2)	0.14338 (13)	0.69392 (5)	0.0401 (2)
N1	0.07804 (7)	0.1705 (4)	0.64572 (16)	0.0424 (7)
H1A	0.0719	0.1836	0.5906	0.051*
O1	0.15578 (7)	0.0798 (4)	0.92720 (16)	0.0557 (7)
C1	0.19376 (12)	−0.2563 (5)	0.9629 (3)	0.0570 (10)
H1B	0.2121	−0.3646	0.9704	0.085*
H1C	0.1676	−0.2946	0.9278	0.085*
H1D	0.1909	−0.2139	1.0182	0.085*
O2	0.20987 (7)	−0.0991 (3)	0.92109 (16)	0.0484 (6)
N2	0.00822 (7)	0.1970 (4)	0.63164 (16)	0.0388 (6)
H2A	−0.0114	0.1857	0.6565	0.047*
C2	0.18727 (9)	0.0615 (5)	0.90655 (19)	0.0379 (7)
N3	0.02372 (7)	0.2300 (4)	0.49733 (16)	0.0363 (6)
O3	0.13329 (8)	−0.0390 (4)	0.73670 (16)	0.0576 (7)
C3	0.20669 (9)	0.2172 (5)	0.86550 (18)	0.0356 (7)
O4	0.14650 (7)	0.1838 (4)	0.62677 (15)	0.0542 (7)
N4	−0.04352 (7)	0.2765 (4)	0.51521 (16)	0.0375 (6)
C4	0.24906 (9)	0.2405 (5)	0.8922 (2)	0.0432 (8)
H4C	0.2647	0.1513	0.9300	0.052*
O5	0.05149 (7)	0.1570 (4)	0.76305 (14)	0.0509 (6)
C5	0.26803 (10)	0.3949 (5)	0.8631 (2)	0.0470 (8)
H5A	0.2962	0.4101	0.8819	0.056*
O6	0.03580 (7)	0.2645 (4)	0.36258 (15)	0.0531 (6)
C6	0.24518 (11)	0.5258 (6)	0.8063 (2)	0.0505 (9)
H6A	0.2578	0.6302	0.7870	0.061*
O7	−0.09468 (7)	0.3699 (4)	0.39861 (15)	0.0508 (6)
C7	0.20337 (10)	0.5023 (5)	0.7779 (2)	0.0468 (8)
H7A	0.1883	0.5896	0.7382	0.056*
C8	0.18338 (9)	0.3511 (5)	0.80731 (19)	0.0363 (7)
C9	0.13757 (9)	0.3323 (5)	0.7722 (2)	0.0406 (8)
H9A	0.1264	0.4537	0.7460	0.049*
H9B	0.1249	0.3034	0.8188	0.049*
C10	0.04638 (9)	0.1743 (5)	0.6850 (2)	0.0369 (7)
C11	−0.00401 (9)	0.2356 (4)	0.54321 (19)	0.0341 (7)
C12	0.00998 (10)	0.2704 (5)	0.4133 (2)	0.0388 (7)
C13	−0.03018 (10)	0.3179 (5)	0.3764 (2)	0.0438 (8)
H13A	−0.0395	0.3469	0.3181	0.053*
C14	−0.05548 (9)	0.3198 (5)	0.4314 (2)	0.0391 (7)
C15	−0.12294 (10)	0.3408 (6)	0.4504 (2)	0.0573 (10)
H15A	−0.1496	0.3834	0.4193	0.086*
H15B	−0.1143	0.4138	0.5028	0.086*
H15C	−0.1239	0.2056	0.4639	0.086*
C16	0.07680 (10)	0.1963 (6)	0.3980 (2)	0.0597 (10)
H16A	0.0918	0.2013	0.3545	0.090*
H16B	0.0760	0.0652	0.4175	0.090*
H16C	0.0899	0.2770	0.4457	0.090*

	U11	U22	U33	U12	U13	U23
S	0.0287 (4)	0.0485 (5)	0.0398 (4)	0.0025 (3)	0.0022 (3)	−0.0034 (4)
N1	0.0293 (13)	0.0636 (19)	0.0332 (14)	−0.0023 (13)	0.0057 (11)	0.0033 (13)
O1	0.0422 (14)	0.0684 (17)	0.0634 (15)	0.0099 (12)	0.0260 (12)	0.0167 (13)
C1	0.067 (2)	0.041 (2)	0.065 (2)	−0.0069 (18)	0.0199 (19)	0.0080 (19)
O2	0.0434 (13)	0.0434 (14)	0.0610 (15)	0.0055 (10)	0.0178 (11)	0.0100 (11)
N2	0.0292 (13)	0.0450 (16)	0.0394 (14)	0.0004 (11)	0.0035 (11)	0.0083 (12)
C2	0.0350 (17)	0.0447 (18)	0.0313 (15)	0.0025 (14)	0.0032 (13)	−0.0006 (14)
N3	0.0344 (14)	0.0381 (15)	0.0353 (14)	−0.0032 (11)	0.0069 (11)	−0.0003 (11)
O3	0.0556 (16)	0.0440 (15)	0.0620 (16)	0.0068 (12)	−0.0061 (12)	0.0009 (12)
C3	0.0359 (16)	0.0420 (18)	0.0281 (14)	−0.0003 (14)	0.0067 (12)	−0.0035 (13)
O4	0.0377 (13)	0.0835 (19)	0.0434 (13)	−0.0003 (12)	0.0140 (10)	−0.0076 (12)
N4	0.0319 (13)	0.0339 (14)	0.0419 (15)	−0.0018 (11)	0.0001 (11)	0.0019 (12)
C4	0.0339 (16)	0.055 (2)	0.0373 (17)	0.0008 (15)	0.0018 (13)	−0.0002 (16)
O5	0.0351 (12)	0.0769 (18)	0.0383 (13)	0.0013 (12)	0.0046 (10)	0.0061 (12)
C5	0.0336 (17)	0.062 (2)	0.0423 (18)	−0.0094 (16)	0.0041 (14)	−0.0014 (17)
O6	0.0460 (14)	0.0707 (17)	0.0428 (13)	0.0023 (12)	0.0117 (11)	0.0010 (12)
C6	0.049 (2)	0.057 (2)	0.0463 (19)	−0.0161 (17)	0.0120 (16)	0.0005 (17)
O7	0.0359 (12)	0.0585 (15)	0.0513 (14)	0.0048 (11)	−0.0016 (10)	0.0134 (12)
C7	0.0469 (19)	0.050 (2)	0.0393 (17)	0.0003 (16)	0.0035 (15)	0.0036 (16)
C8	0.0306 (15)	0.0397 (17)	0.0360 (16)	−0.0009 (13)	0.0035 (12)	−0.0060 (14)
C9	0.0344 (16)	0.0445 (19)	0.0406 (17)	0.0049 (14)	0.0050 (13)	−0.0014 (15)
C10	0.0304 (15)	0.0371 (17)	0.0412 (18)	−0.0007 (13)	0.0052 (13)	0.0015 (14)
C11	0.0312 (15)	0.0291 (16)	0.0389 (16)	−0.0024 (12)	0.0028 (13)	0.0013 (13)
C12	0.0439 (18)	0.0330 (17)	0.0385 (17)	−0.0033 (14)	0.0083 (14)	−0.0030 (14)
C13	0.0460 (19)	0.045 (2)	0.0340 (16)	−0.0047 (15)	−0.0020 (14)	0.0006 (14)
C14	0.0363 (17)	0.0323 (17)	0.0433 (18)	−0.0011 (13)	−0.0001 (14)	0.0054 (14)
C15	0.0384 (19)	0.068 (3)	0.062 (2)	0.0021 (18)	0.0057 (17)	0.011 (2)
C16	0.0396 (19)	0.081 (3)	0.057 (2)	−0.0040 (19)	0.0105 (16)	−0.009 (2)

S—O3	1.424 (3)	O5—C10	1.224 (4)
S—O4	1.431 (2)	C5—C6	1.374 (5)
S—N1	1.643 (3)	C5—H5A	0.930
S—C9	1.782 (3)	O6—C12	1.334 (4)
N1—C10	1.372 (4)	O6—C16	1.440 (4)
N1—H1A	0.860	C6—C7	1.383 (5)
O1—C2	1.199 (4)	C6—H6A	0.930
C1—O2	1.451 (4)	O7—C14	1.344 (4)
C1—H1B	0.960	O7—C15	1.428 (4)
C1—H1C	0.960	C7—C8	1.388 (5)
C1—H1D	0.960	C7—H7A	0.930
O2—C2	1.333 (4)	C8—C9	1.516 (4)
N2—C10	1.368 (4)	C9—H9A	0.970
N2—C11	1.399 (4)	C9—H9B	0.970
N2—H2A	0.860	C12—C13	1.379 (4)
C2—C3	1.495 (5)	C13—C14	1.373 (5)
N3—C11	1.329 (4)	C13—H13A	0.930
N3—C12	1.339 (4)	C15—H15A	0.960
C3—C4	1.399 (4)	C15—H15B	0.960
C3—C8	1.406 (4)	C15—H15C	0.960
N4—C11	1.330 (4)	C16—H16A	0.960
N4—C14	1.336 (4)	C16—H16B	0.960
C4—C5	1.384 (5)	C16—H16C	0.960
C4—H4C	0.930
O3—S—O4	119.13 (17)	C6—C7—H7A	119.3
O3—S—N1	110.25 (15)	C8—C7—H7A	119.3
O4—S—N1	103.13 (14)	C7—C8—C3	118.6 (3)
O3—S—C9	109.17 (16)	C7—C8—C9	118.5 (3)
O4—S—C9	109.40 (16)	C3—C8—C9	122.8 (3)
N1—S—C9	104.73 (15)	C8—C9—S	109.7 (2)
C10—N1—S	126.2 (2)	C8—C9—H9A	109.7
C10—N1—H1A	116.9	S—C9—H9A	109.7
S—N1—H1A	116.9	C8—C9—H9B	109.7
O2—C1—H1B	109.5	S—C9—H9B	109.7
O2—C1—H1C	109.5	H9A—C9—H9B	108.2
H1B—C1—H1C	109.5	O5—C10—N2	121.3 (3)
O2—C1—H1D	109.5	O5—C10—N1	122.7 (3)
H1B—C1—H1D	109.5	N2—C10—N1	116.0 (3)
H1C—C1—H1D	109.5	N3—C11—N4	127.5 (3)
C2—O2—C1	115.9 (3)	N3—C11—N2	118.9 (3)
C10—N2—C11	130.5 (3)	N4—C11—N2	113.6 (3)
C10—N2—H2A	114.8	O6—C12—N3	119.4 (3)
C11—N2—H2A	114.8	O6—C12—C13	118.1 (3)
O1—C2—O2	123.4 (3)	N3—C12—C13	122.5 (3)
O1—C2—C3	124.3 (3)	C14—C13—C12	115.6 (3)
O2—C2—C3	112.2 (3)	C14—C13—H13A	122.2
C11—N3—C12	115.7 (3)	C12—C13—H13A	122.2
C4—C3—C8	119.3 (3)	N4—C14—O7	118.1 (3)
C4—C3—C2	118.5 (3)	N4—C14—C13	124.2 (3)
C8—C3—C2	121.9 (3)	O7—C14—C13	117.7 (3)
C11—N4—C14	114.4 (3)	O7—C15—H15A	109.5
C5—C4—C3	120.8 (3)	O7—C15—H15B	109.5
C5—C4—H4C	119.6	H15A—C15—H15B	109.5
C3—C4—H4C	119.6	O7—C15—H15C	109.5
C6—C5—C4	119.8 (3)	H15A—C15—H15C	109.5
C6—C5—H5A	120.1	H15B—C15—H15C	109.5
C4—C5—H5A	120.1	O6—C16—H16A	109.5
C12—O6—C16	118.8 (3)	O6—C16—H16B	109.5
C5—C6—C7	120.1 (3)	H16A—C16—H16B	109.5
C5—C6—H6A	120.0	O6—C16—H16C	109.5
C7—C6—H6A	120.0	H16A—C16—H16C	109.5
C14—O7—C15	118.4 (3)	H16B—C16—H16C	109.5
C6—C7—C8	121.4 (3)
O3—S—N1—C10	61.5 (3)	N1—S—C9—C8	−167.4 (2)
O4—S—N1—C10	−170.2 (3)	C11—N2—C10—O5	173.7 (3)
C9—S—N1—C10	−55.8 (3)	C11—N2—C10—N1	−6.9 (5)
C1—O2—C2—O1	1.1 (5)	S—N1—C10—O5	−0.1 (5)
C1—O2—C2—C3	178.5 (3)	S—N1—C10—N2	−179.5 (2)
O1—C2—C3—C4	139.0 (3)	C12—N3—C11—N4	0.0 (5)
O2—C2—C3—C4	−38.4 (4)	C12—N3—C11—N2	−179.3 (3)
O1—C2—C3—C8	−34.9 (5)	C14—N4—C11—N3	−1.4 (5)
O2—C2—C3—C8	147.7 (3)	C14—N4—C11—N2	178.0 (3)
C8—C3—C4—C5	1.0 (5)	C10—N2—C11—N3	8.8 (5)
C2—C3—C4—C5	−173.1 (3)	C10—N2—C11—N4	−170.6 (3)
C3—C4—C5—C6	−0.9 (5)	C16—O6—C12—N3	6.0 (5)
C4—C5—C6—C7	−0.5 (5)	C16—O6—C12—C13	−173.8 (3)
C5—C6—C7—C8	1.9 (5)	C11—N3—C12—O6	−178.8 (3)
C6—C7—C8—C3	−1.7 (5)	C11—N3—C12—C13	1.0 (5)
C6—C7—C8—C9	−179.0 (3)	O6—C12—C13—C14	179.3 (3)
C4—C3—C8—C7	0.3 (4)	N3—C12—C13—C14	−0.5 (5)
C2—C3—C8—C7	174.2 (3)	C11—N4—C14—O7	−177.5 (3)
C4—C3—C8—C9	177.5 (3)	C11—N4—C14—C13	1.9 (5)
C2—C3—C8—C9	−8.7 (5)	C15—O7—C14—N4	−11.2 (4)
C7—C8—C9—S	102.8 (3)	C15—O7—C14—C13	169.4 (3)
C3—C8—C9—S	−74.3 (3)	C12—C13—C14—N4	−1.0 (5)
O3—S—C9—C8	74.5 (3)	C12—C13—C14—O7	178.4 (3)
O4—S—C9—C8	−57.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	1.94	2.648 (4)	138
N2—H2A···O5i	0.86	2.10	2.951 (3)	170
C9—H9B···O1	0.97	2.36	2.970 (4)	120
C15—H15C···O1i	0.96	2.43	3.068 (4)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3	0.86	1.94	2.648 (4)	138
N2—H2A⋯O5i	0.86	2.10	2.951 (3)	170
C9—H9B⋯O1	0.97	2.36	2.970 (4)	120
C15—H15C⋯O1i	0.96	2.43	3.068 (4)	124

Symmetry code: (i) .