Crystal structure of azimsulfuron.

The title compound {systematic name: 1-(4,6-di-meth-oxy-pyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetra-zol-5-yl)pyrazol-5-ylsulfon-yl]urea}, C13H16N10O5S, is a sulfonyl-urea herbicide. In this compound, the dihedral angles between the planes of the central pyrazole and the terminal di-meth-oxy-pyrimidine and tetra-zole rings are 79.10 (8) and 17.21 (16)°, respectively. In the crystal, N-H⋯O hydrogen bonds link adjacent mol-ecules, forming R 2 (2)(8) inversion dimers. In addition, weak C-H⋯O and C-H⋯N hydrogen bonds and weak π-π inter-actions [ring centroid separation = 3.8255 (12) Å] are present, resulting in a three-dimensional architecture.

Related literature

For information on the herbicidal properties of the title compound, see: Valle et al. (2006 ▸); Boschin et al. (2007 ▸). For a related crystal structure, see: Chopra et al. (2004 ▸).

Experimental

Crystal data

C13H16N10O5S

M = 424.42

Triclinic,

a = 8.5884 (7) Å

b = 9.9165 (7) Å

c = 12.2788 (13) Å

α = 73.190 (5)°

β = 75.819 (4)°

γ = 66.374 (3)°

V = 907.16 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.42 × 0.10 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.909, T max = 0.979

16122 measured reflections

4123 independent reflections

3357 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.118

S = 1.04

4123 reflections

266 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015010968/hg5444sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010968/hg5444Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015010968/hg5444Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015010968/hg5444fig1.tif

The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Click here for additional data file.

b . DOI: 10.1107/S2056989015010968/hg5444fig2.tif

Crystal packing viewed along the b axis. The hydrogen bonds are shown as dashed lines.

CCDC reference: 1405357

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H16N10O5S	Z = 2
Mr = 424.42	F(000) = 440
Triclinic, P1	Dx = 1.554 Mg m−3
a = 8.5884 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9165 (7) Å	Cell parameters from 4687 reflections
c = 12.2788 (13) Å	θ = 2.3–26.9°
α = 73.190 (5)°	µ = 0.23 mm−1
β = 75.819 (4)°	T = 173 K
γ = 66.374 (3)°	Block, colourless
V = 907.16 (14) Å3	0.42 × 0.10 × 0.09 mm

Bruker APEXII CCD diffractometer	3357 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.036
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 27.5°, θmin = 1.8°
Tmin = 0.909, Tmax = 0.979	h = −11→11
16122 measured reflections	k = −12→12
4123 independent reflections	l = −15→15

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.5222P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4123 reflections	Δρmax = 0.56 e Å−3
266 parameters	Δρmin = −0.49 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.74797 (6)	0.79478 (5)	0.73248 (4)	0.02370 (14)
O1	1.10371 (18)	−0.02315 (15)	1.11503 (12)	0.0280 (3)
O2	1.32890 (18)	0.30498 (17)	0.81805 (13)	0.0356 (4)
O3	0.53148 (17)	0.65412 (16)	0.91451 (13)	0.0326 (4)
O4	0.6527 (2)	0.91670 (16)	0.78851 (14)	0.0379 (4)
O5	0.90400 (19)	0.79382 (17)	0.65785 (14)	0.0361 (4)
N1	0.9372 (2)	0.21202 (18)	1.04786 (14)	0.0236 (4)
N2	1.0436 (2)	0.38255 (18)	0.89699 (14)	0.0238 (4)
N3	0.7525 (2)	0.44579 (18)	0.97760 (14)	0.0254 (4)
H3N	0.6779	0.4182	1.0336	0.031*
N4	0.8032 (2)	0.63736 (17)	0.82771 (13)	0.0214 (3)
H4N	0.9133	0.5838	0.8284	0.026*
N5	0.4566 (2)	0.88624 (18)	0.63630 (16)	0.0303 (4)
N6	0.3789 (2)	0.8477 (2)	0.57414 (18)	0.0394 (5)
N7	0.7377 (2)	0.40229 (17)	0.58472 (14)	0.0247 (4)
N8	0.8855 (2)	0.28937 (17)	0.59920 (14)	0.0243 (4)
N9	0.9977 (2)	0.32420 (18)	0.63093 (16)	0.0298 (4)
N10	0.9232 (2)	0.46781 (18)	0.63767 (15)	0.0280 (4)
C1	1.2673 (3)	−0.1457 (2)	1.11176 (19)	0.0308 (5)
H1A	1.3074	−0.1629	1.0333	0.046*
H1B	1.2544	−0.2373	1.1643	0.046*
H1C	1.3512	−0.1201	1.1355	0.046*
C2	1.0957 (2)	0.1075 (2)	1.04081 (16)	0.0228 (4)
C3	1.2338 (2)	0.1330 (2)	0.96351 (17)	0.0262 (4)
H3	1.3452	0.0575	0.9589	0.031*
C4	1.1988 (2)	0.2757 (2)	0.89353 (17)	0.0244 (4)
C5	0.9207 (2)	0.3420 (2)	0.97398 (16)	0.0215 (4)
C6	1.2928 (3)	0.4514 (3)	0.7412 (2)	0.0393 (6)
H6A	1.2067	0.4667	0.6948	0.059*
H6B	1.3985	0.4573	0.6904	0.059*
H6C	1.2486	0.5297	0.7861	0.059*
C7	0.6855 (2)	0.5842 (2)	0.90723 (16)	0.0231 (4)
C8	0.6097 (2)	0.7766 (2)	0.65845 (16)	0.0215 (4)
C9	0.4833 (3)	0.7125 (2)	0.5569 (2)	0.0316 (5)
H9	0.4601	0.6571	0.5153	0.038*
C10	0.6314 (2)	0.6612 (2)	0.60716 (16)	0.0212 (4)
C11	0.3620 (3)	1.0278 (3)	0.6757 (3)	0.0496 (7)
H11A	0.2815	1.0973	0.6224	0.074*
H11B	0.4431	1.0732	0.6783	0.074*
H11C	0.2981	1.0074	0.7527	0.074*
C12	0.7652 (2)	0.5127 (2)	0.60905 (16)	0.0204 (4)
C13	0.9157 (3)	0.1370 (2)	0.5897 (2)	0.0326 (5)
H13A	1.0396	0.0807	0.5778	0.049*
H13B	0.8653	0.1424	0.5244	0.049*
H13C	0.8625	0.0857	0.6606	0.049*

	U11	U22	U33	U12	U13	U23
S1	0.0261 (3)	0.0177 (2)	0.0299 (3)	−0.00848 (19)	−0.0094 (2)	−0.00349 (18)
O1	0.0263 (7)	0.0221 (7)	0.0311 (8)	−0.0045 (6)	−0.0073 (6)	−0.0024 (6)
O2	0.0173 (7)	0.0365 (8)	0.0414 (9)	−0.0065 (6)	−0.0006 (6)	0.0009 (7)
O3	0.0177 (7)	0.0287 (7)	0.0380 (8)	−0.0007 (6)	0.0005 (6)	−0.0025 (6)
O4	0.0478 (10)	0.0220 (7)	0.0494 (9)	−0.0038 (7)	−0.0234 (8)	−0.0146 (7)
O5	0.0301 (8)	0.0364 (8)	0.0425 (9)	−0.0205 (7)	−0.0075 (7)	0.0047 (7)
N1	0.0213 (8)	0.0249 (8)	0.0240 (8)	−0.0068 (7)	−0.0050 (7)	−0.0050 (6)
N2	0.0176 (8)	0.0255 (8)	0.0253 (8)	−0.0046 (7)	−0.0039 (7)	−0.0049 (7)
N3	0.0174 (8)	0.0254 (8)	0.0260 (8)	−0.0041 (7)	0.0002 (7)	−0.0024 (7)
N4	0.0162 (7)	0.0200 (7)	0.0251 (8)	−0.0028 (6)	−0.0050 (6)	−0.0042 (6)
N5	0.0265 (9)	0.0225 (8)	0.0423 (10)	0.0018 (7)	−0.0164 (8)	−0.0132 (7)
N6	0.0336 (10)	0.0331 (10)	0.0538 (12)	0.0015 (8)	−0.0243 (9)	−0.0174 (9)
N7	0.0234 (8)	0.0194 (7)	0.0312 (9)	−0.0041 (7)	−0.0068 (7)	−0.0078 (7)
N8	0.0260 (8)	0.0182 (7)	0.0293 (9)	−0.0047 (7)	−0.0063 (7)	−0.0087 (6)
N9	0.0252 (9)	0.0236 (8)	0.0411 (10)	−0.0021 (7)	−0.0102 (8)	−0.0131 (7)
N10	0.0233 (8)	0.0212 (8)	0.0409 (10)	−0.0024 (7)	−0.0103 (8)	−0.0121 (7)
C1	0.0283 (11)	0.0193 (9)	0.0403 (12)	−0.0001 (8)	−0.0127 (9)	−0.0055 (8)
C2	0.0234 (10)	0.0227 (9)	0.0236 (9)	−0.0058 (8)	−0.0094 (8)	−0.0056 (7)
C3	0.0180 (9)	0.0271 (10)	0.0298 (10)	−0.0027 (8)	−0.0066 (8)	−0.0060 (8)
C4	0.0165 (9)	0.0297 (10)	0.0262 (10)	−0.0071 (8)	−0.0042 (8)	−0.0056 (8)
C5	0.0173 (9)	0.0246 (9)	0.0228 (9)	−0.0049 (8)	−0.0044 (7)	−0.0076 (7)
C6	0.0283 (11)	0.0411 (13)	0.0386 (13)	−0.0145 (10)	0.0007 (10)	0.0043 (10)
C7	0.0200 (9)	0.0242 (9)	0.0230 (9)	−0.0051 (8)	−0.0010 (8)	−0.0075 (7)
C8	0.0213 (9)	0.0172 (8)	0.0249 (9)	−0.0028 (7)	−0.0079 (8)	−0.0050 (7)
C9	0.0297 (11)	0.0264 (10)	0.0419 (12)	−0.0028 (9)	−0.0170 (10)	−0.0124 (9)
C10	0.0209 (9)	0.0187 (9)	0.0237 (9)	−0.0057 (7)	−0.0056 (8)	−0.0040 (7)
C11	0.0405 (14)	0.0317 (12)	0.0737 (18)	0.0128 (11)	−0.0255 (13)	−0.0302 (12)
C12	0.0206 (9)	0.0198 (8)	0.0219 (9)	−0.0056 (7)	−0.0053 (7)	−0.0066 (7)
C13	0.0393 (12)	0.0181 (9)	0.0415 (12)	−0.0063 (9)	−0.0074 (10)	−0.0125 (8)

S1—O4	1.4201 (15)	N8—N9	1.314 (2)
S1—O5	1.4243 (16)	N8—C13	1.462 (2)
S1—N4	1.6284 (16)	N9—N10	1.325 (2)
S1—C8	1.751 (2)	N10—C12	1.350 (2)
O1—C2	1.338 (2)	C1—H1A	0.9800
O1—C1	1.444 (2)	C1—H1B	0.9800
O2—C4	1.337 (2)	C1—H1C	0.9800
O2—C6	1.444 (3)	C2—C3	1.387 (3)
O3—C7	1.217 (2)	C3—C4	1.383 (3)
N1—C5	1.321 (2)	C3—H3	0.9500
N1—C2	1.341 (2)	C6—H6A	0.9800
N2—C4	1.330 (2)	C6—H6B	0.9800
N2—C5	1.342 (2)	C6—H6C	0.9800
N3—C7	1.373 (2)	C8—C10	1.389 (3)
N3—C5	1.397 (2)	C9—C10	1.393 (3)
N3—H3N	0.8800	C9—H9	0.9500
N4—C7	1.378 (2)	C10—C12	1.459 (2)
N4—H4N	0.8800	C11—H11A	0.9800
N5—N6	1.340 (3)	C11—H11B	0.9800
N5—C8	1.358 (2)	C11—H11C	0.9800
N5—C11	1.466 (3)	C13—H13A	0.9800
N6—C9	1.325 (3)	C13—H13B	0.9800
N7—N8	1.324 (2)	C13—H13C	0.9800
N7—C12	1.332 (2)
O4—S1—O5	119.58 (10)	N2—C4—C3	123.37 (18)
O4—S1—N4	109.86 (9)	O2—C4—C3	117.43 (17)
O5—S1—N4	104.30 (9)	N1—C5—N2	127.89 (17)
O4—S1—C8	107.79 (9)	N1—C5—N3	114.04 (17)
O5—S1—C8	109.46 (10)	N2—C5—N3	118.05 (16)
N4—S1—C8	104.90 (9)	O2—C6—H6A	109.5
C2—O1—C1	117.09 (16)	O2—C6—H6B	109.5
C4—O2—C6	118.04 (16)	H6A—C6—H6B	109.5
C5—N1—C2	114.99 (17)	O2—C6—H6C	109.5
C4—N2—C5	114.96 (16)	H6A—C6—H6C	109.5
C7—N3—C5	129.98 (17)	H6B—C6—H6C	109.5
C7—N3—H3N	115.0	O3—C7—N3	121.66 (18)
C5—N3—H3N	115.0	O3—C7—N4	122.49 (17)
C7—N4—S1	123.00 (13)	N3—C7—N4	115.85 (16)
C7—N4—H4N	118.5	N5—C8—C10	107.00 (17)
S1—N4—H4N	118.5	N5—C8—S1	122.90 (14)
N6—N5—C8	111.29 (16)	C10—C8—S1	130.02 (14)
N6—N5—C11	117.40 (17)	N6—C9—C10	111.85 (19)
C8—N5—C11	131.12 (18)	N6—C9—H9	124.1
C9—N6—N5	105.78 (17)	C10—C9—H9	124.1
N8—N7—C12	101.76 (15)	C8—C10—C9	104.07 (16)
N9—N8—N7	113.84 (15)	C8—C10—C12	131.15 (18)
N9—N8—C13	123.11 (16)	C9—C10—C12	124.59 (18)
N7—N8—C13	122.87 (17)	N5—C11—H11A	109.5
N8—N9—N10	106.55 (15)	N5—C11—H11B	109.5
N9—N10—C12	105.48 (16)	H11A—C11—H11B	109.5
O1—C1—H1A	109.5	N5—C11—H11C	109.5
O1—C1—H1B	109.5	H11A—C11—H11C	109.5
H1A—C1—H1B	109.5	H11B—C11—H11C	109.5
O1—C1—H1C	109.5	N7—C12—N10	112.36 (16)
H1A—C1—H1C	109.5	N7—C12—C10	121.13 (17)
H1B—C1—H1C	109.5	N10—C12—C10	126.48 (17)
O1—C2—N1	112.43 (17)	N8—C13—H13A	109.5
O1—C2—C3	124.43 (17)	N8—C13—H13B	109.5
N1—C2—C3	123.14 (18)	H13A—C13—H13B	109.5
C4—C3—C2	115.60 (17)	N8—C13—H13C	109.5
C4—C3—H3	122.2	H13A—C13—H13C	109.5
C2—C3—H3	122.2	H13B—C13—H13C	109.5
N2—C4—O2	119.19 (17)
O4—S1—N4—C7	59.80 (18)	C5—N3—C7—N4	−7.5 (3)
O5—S1—N4—C7	−170.87 (15)	S1—N4—C7—O3	−2.7 (3)
C8—S1—N4—C7	−55.81 (17)	S1—N4—C7—N3	176.66 (13)
C8—N5—N6—C9	0.1 (3)	N6—N5—C8—C10	0.1 (2)
C11—N5—N6—C9	−175.4 (2)	C11—N5—C8—C10	174.9 (2)
C12—N7—N8—N9	0.4 (2)	N6—N5—C8—S1	177.18 (16)
C12—N7—N8—C13	175.78 (18)	C11—N5—C8—S1	−8.1 (3)
N7—N8—N9—N10	−0.4 (2)	O4—S1—C8—N5	15.8 (2)
C13—N8—N9—N10	−175.73 (18)	O5—S1—C8—N5	−115.78 (18)
N8—N9—N10—C12	0.2 (2)	N4—S1—C8—N5	132.80 (17)
C1—O1—C2—N1	177.72 (17)	O4—S1—C8—C10	−167.94 (18)
C1—O1—C2—C3	−1.3 (3)	O5—S1—C8—C10	60.5 (2)
C5—N1—C2—O1	−178.07 (16)	N4—S1—C8—C10	−50.9 (2)
C5—N1—C2—C3	1.0 (3)	N5—N6—C9—C10	−0.4 (3)
O1—C2—C3—C4	179.64 (18)	N5—C8—C10—C9	−0.3 (2)
N1—C2—C3—C4	0.7 (3)	S1—C8—C10—C9	−177.09 (17)
C5—N2—C4—O2	178.90 (17)	N5—C8—C10—C12	−175.5 (2)
C5—N2—C4—C3	−0.2 (3)	S1—C8—C10—C12	7.8 (3)
C6—O2—C4—N2	−1.7 (3)	N6—C9—C10—C8	0.4 (3)
C6—O2—C4—C3	177.50 (19)	N6—C9—C10—C12	176.0 (2)
C2—C3—C4—N2	−1.1 (3)	N8—N7—C12—N10	−0.3 (2)
C2—C3—C4—O2	179.76 (18)	N8—N7—C12—C10	−178.32 (17)
C2—N1—C5—N2	−2.7 (3)	N9—N10—C12—N7	0.1 (2)
C2—N1—C5—N3	175.99 (17)	N9—N10—C12—C10	177.97 (18)
C4—N2—C5—N1	2.3 (3)	C8—C10—C12—N7	159.2 (2)
C4—N2—C5—N3	−176.29 (17)	C9—C10—C12—N7	−15.0 (3)
C7—N3—C5—N1	−173.08 (19)	C8—C10—C12—N10	−18.5 (3)
C7—N3—C5—N2	5.7 (3)	C9—C10—C12—N10	167.3 (2)
C5—N3—C7—O3	171.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3i	0.88	2.09	2.877 (2)	149
C1—H1A···O3ii	0.98	2.55	3.381 (3)	143
C1—H1C···O4iii	0.98	2.44	3.225 (3)	137
C11—H11A···N9iv	0.98	2.57	3.357 (3)	137
C13—H13B···N6v	0.98	2.62	3.533 (3)	155

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N3H3NO3i	0.88	2.09	2.877(2)	149
C1H1AO3ii	0.98	2.55	3.381(3)	143
C1H1CO4iii	0.98	2.44	3.225(3)	137
C11H11AN9iv	0.98	2.57	3.357(3)	137
C13H13BN6v	0.98	2.62	3.533(3)	155

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .