Crystal structure of cyclo-sulfamuron.

The title compound (systematic name: 1-{[2-(cyclo-propylcarbon-yl)anilino]sulfon-yl}-3-(4,6-di-meth-oxy-pyrimidin-2-yl)urea), C17H19N5O6S, is a pyrimidinyl-sulfonyl-urea herbicide. The dihedral angles between the mean planes of the central benzene ring and the cyclo-propyl and pyrimidinyl rings are 75.32 (9) and 88.79 (4)°, respectively. The C atoms of the meth-oxy groups lie almost in the plane of the pyrimidine ring [deviations = 0.043 (2) and 0.028 (2) Å] and intra-molecular N-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds all close S(6) rings. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds and weak π-π inter-actions [centroid-centroid distances = 3.6175 (9) and 3.7068 (9) Å] link adjacent mol-ecules, forming a three-dimensional network.

Related literature

For information on the herbicidal properties of the title compound, see: Sarıgül & İnam (2009 ▸). For a related crystal structure, see: Xia et al. (2008 ▸).

Experimental

Crystal data

C17H19N5O6S

M = 421.43

Monoclinic,

a = 12.7019 (4) Å

b = 9.6216 (3) Å

c = 15.6213 (5) Å

β = 93.6194 (12)°

V = 1905.31 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.32 × 0.27 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.934, T max = 0.952

17544 measured reflections

4365 independent reflections

3688 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.05

4365 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.22 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: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015014115/hb7470sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014115/hb7470Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015014115/hb7470Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015014115/hb7470fig1.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.

c . DOI: 10.1107/S2056989015014115/hb7470fig2.tif

Crystal packing viewed along the c axis. The inter­molecular inter­actions are shown as dashed lines.

CCDC reference: 1415211

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

C17H19N5O6S	F(000) = 880
Mr = 421.43	Dx = 1.469 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.7019 (4) Å	Cell parameters from 6977 reflections
b = 9.6216 (3) Å	θ = 2.6–27.4°
c = 15.6213 (5) Å	µ = 0.22 mm−1
β = 93.6194 (12)°	T = 173 K
V = 1905.31 (10) Å3	Block, colourless
Z = 4	0.32 × 0.27 × 0.23 mm

Bruker APEXII CCD diffractometer	3688 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.030
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 27.5°, θmin = 2.0°
Tmin = 0.934, Tmax = 0.952	h = −16→15
17544 measured reflections	k = −12→12
4365 independent reflections	l = −20→20

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.7248P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4365 reflections	Δρmax = 0.22 e Å−3
264 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	1.03274 (3)	0.41778 (4)	0.19915 (2)	0.02564 (12)
O1	1.02757 (11)	0.25129 (16)	−0.03440 (8)	0.0524 (4)
O2	1.12410 (9)	0.48608 (12)	0.17159 (7)	0.0340 (3)
O3	0.95254 (9)	0.49585 (12)	0.23699 (7)	0.0343 (3)
O4	1.19071 (9)	0.18921 (12)	0.19997 (7)	0.0335 (3)
O5	0.94327 (9)	0.31556 (13)	0.52112 (7)	0.0386 (3)
O6	1.17908 (10)	−0.04334 (14)	0.61128 (7)	0.0429 (3)
N1	0.98567 (10)	0.33405 (14)	0.11638 (8)	0.0290 (3)
H1N	1.0187	0.3456	0.0690	0.035*
N2	1.06665 (10)	0.30293 (14)	0.27345 (8)	0.0281 (3)
H2N	1.0317	0.3014	0.3203	0.034*
N3	1.17533 (10)	0.13526 (15)	0.33969 (8)	0.0303 (3)
H3N	1.2279	0.0767	0.3351	0.036*
N4	1.05707 (10)	0.22678 (14)	0.43352 (8)	0.0284 (3)
N5	1.17993 (10)	0.04736 (14)	0.47520 (8)	0.0302 (3)
C1	1.00581 (16)	0.0853 (2)	−0.18258 (11)	0.0418 (4)
H1A	1.0695	0.1442	−0.1740	0.050*
H1B	1.0162	−0.0019	−0.2147	0.050*
C2	0.90252 (18)	0.1560 (2)	−0.19567 (11)	0.0492 (5)
H2A	0.8486	0.1127	−0.2357	0.059*
H2B	0.9019	0.2589	−0.1950	0.059*
C3	0.93094 (14)	0.08205 (17)	−0.11251 (10)	0.0354 (4)
H3	0.8943	−0.0082	−0.1031	0.042*
C4	0.95231 (14)	0.17112 (17)	−0.03618 (10)	0.0334 (4)
C5	0.88087 (12)	0.16383 (17)	0.03524 (10)	0.0301 (3)
C6	0.79319 (14)	0.0755 (2)	0.02989 (12)	0.0415 (4)
H6	0.7797	0.0215	−0.0206	0.050*
C7	0.72575 (15)	0.0639 (2)	0.09523 (13)	0.0462 (5)
H7	0.6672	0.0023	0.0901	0.055*
C8	0.74454 (14)	0.1432 (2)	0.16818 (12)	0.0432 (4)
H8	0.6987	0.1354	0.2137	0.052*
C9	0.82919 (13)	0.23370 (19)	0.17609 (10)	0.0347 (4)
H9	0.8403	0.2886	0.2264	0.042*
C10	0.89805 (12)	0.24451 (16)	0.11062 (9)	0.0267 (3)
C11	1.14737 (12)	0.20858 (16)	0.26595 (9)	0.0267 (3)
C12	1.13446 (12)	0.13831 (16)	0.42007 (9)	0.0272 (3)
C13	1.01967 (12)	0.22237 (17)	0.51212 (9)	0.0294 (3)
C14	1.05796 (13)	0.13144 (18)	0.57482 (9)	0.0325 (4)
H14	1.0303	0.1274	0.6299	0.039*
C15	1.13996 (13)	0.04587 (18)	0.55188 (10)	0.0314 (3)
C16	0.89737 (16)	0.3201 (2)	0.60284 (11)	0.0514 (5)
H16A	0.8605	0.2326	0.6124	0.077*
H16B	0.8472	0.3974	0.6035	0.077*
H16C	0.9531	0.3336	0.6484	0.077*
C17	1.26553 (16)	−0.1300 (2)	0.58797 (12)	0.0463 (5)
H17A	1.2435	−0.1851	0.5372	0.069*
H17B	1.2862	−0.1925	0.6357	0.069*
H17C	1.3256	−0.0714	0.5752	0.069*

	U11	U22	U33	U12	U13	U23
S1	0.0234 (2)	0.0291 (2)	0.02454 (19)	−0.00228 (14)	0.00254 (14)	−0.00382 (13)
O1	0.0535 (9)	0.0729 (10)	0.0323 (6)	−0.0295 (7)	0.0133 (6)	−0.0169 (6)
O2	0.0313 (6)	0.0348 (6)	0.0362 (6)	−0.0109 (5)	0.0052 (5)	−0.0047 (5)
O3	0.0321 (6)	0.0368 (6)	0.0343 (6)	0.0076 (5)	0.0039 (5)	−0.0045 (5)
O4	0.0305 (6)	0.0445 (7)	0.0263 (5)	0.0045 (5)	0.0096 (4)	−0.0049 (5)
O5	0.0368 (7)	0.0544 (8)	0.0255 (6)	0.0162 (6)	0.0090 (5)	−0.0010 (5)
O6	0.0459 (8)	0.0518 (8)	0.0309 (6)	0.0133 (6)	0.0007 (5)	0.0070 (5)
N1	0.0263 (7)	0.0387 (7)	0.0222 (6)	−0.0083 (6)	0.0039 (5)	−0.0029 (5)
N2	0.0243 (7)	0.0385 (7)	0.0221 (6)	0.0048 (5)	0.0055 (5)	−0.0010 (5)
N3	0.0256 (7)	0.0394 (7)	0.0263 (6)	0.0096 (6)	0.0059 (5)	−0.0015 (5)
N4	0.0253 (7)	0.0370 (7)	0.0232 (6)	0.0037 (5)	0.0039 (5)	−0.0023 (5)
N5	0.0263 (7)	0.0368 (7)	0.0274 (6)	0.0026 (6)	0.0016 (5)	−0.0017 (5)
C1	0.0512 (11)	0.0429 (10)	0.0312 (8)	0.0058 (8)	0.0010 (8)	−0.0081 (7)
C2	0.0760 (15)	0.0388 (10)	0.0310 (9)	0.0193 (10)	−0.0112 (9)	−0.0048 (7)
C3	0.0467 (10)	0.0305 (8)	0.0283 (8)	0.0018 (7)	−0.0033 (7)	−0.0030 (6)
C4	0.0368 (9)	0.0366 (9)	0.0262 (7)	−0.0024 (7)	−0.0031 (6)	−0.0015 (6)
C5	0.0270 (8)	0.0333 (8)	0.0292 (7)	−0.0029 (6)	−0.0049 (6)	0.0009 (6)
C6	0.0348 (10)	0.0436 (10)	0.0451 (10)	−0.0099 (8)	−0.0048 (8)	−0.0083 (8)
C7	0.0301 (9)	0.0511 (11)	0.0571 (11)	−0.0163 (8)	−0.0002 (8)	−0.0050 (9)
C8	0.0282 (9)	0.0552 (11)	0.0471 (10)	−0.0093 (8)	0.0086 (7)	0.0018 (9)
C9	0.0255 (8)	0.0450 (10)	0.0338 (8)	−0.0062 (7)	0.0027 (6)	−0.0025 (7)
C10	0.0220 (7)	0.0304 (8)	0.0272 (7)	−0.0022 (6)	−0.0019 (6)	0.0015 (6)
C11	0.0209 (7)	0.0342 (8)	0.0252 (7)	−0.0015 (6)	0.0030 (5)	−0.0046 (6)
C12	0.0234 (7)	0.0346 (8)	0.0238 (7)	−0.0015 (6)	0.0017 (6)	−0.0037 (6)
C13	0.0260 (8)	0.0379 (8)	0.0244 (7)	0.0015 (6)	0.0033 (6)	−0.0057 (6)
C14	0.0328 (9)	0.0429 (9)	0.0220 (7)	0.0020 (7)	0.0036 (6)	−0.0029 (6)
C15	0.0287 (8)	0.0383 (9)	0.0270 (7)	−0.0005 (7)	−0.0013 (6)	−0.0006 (6)
C16	0.0513 (12)	0.0780 (15)	0.0262 (8)	0.0277 (11)	0.0122 (8)	−0.0043 (9)
C17	0.0476 (11)	0.0523 (11)	0.0379 (9)	0.0167 (9)	−0.0058 (8)	0.0016 (8)

S1—O2	1.4237 (11)	C2—C3	1.505 (2)
S1—O3	1.4238 (11)	C2—H2A	0.9900
S1—N1	1.6065 (12)	C2—H2B	0.9900
S1—N2	1.6402 (13)	C3—C4	1.480 (2)
O1—C4	1.227 (2)	C3—H3	1.0000
O4—C11	1.2132 (17)	C4—C5	1.484 (2)
O5—C13	1.3351 (19)	C5—C6	1.399 (2)
O5—C16	1.4372 (19)	C5—C10	1.416 (2)
O6—C15	1.3366 (19)	C6—C7	1.378 (3)
O6—C17	1.444 (2)	C6—H6	0.9500
N1—C10	1.4058 (19)	C7—C8	1.379 (3)
N1—H1N	0.8800	C7—H7	0.9500
N2—C11	1.3799 (19)	C8—C9	1.383 (2)
N2—H2N	0.8800	C8—H8	0.9500
N3—C11	1.378 (2)	C9—C10	1.391 (2)
N3—C12	1.3890 (18)	C9—H9	0.9500
N3—H3N	0.8800	C13—C14	1.379 (2)
N4—C12	1.327 (2)	C14—C15	1.392 (2)
N4—C13	1.3449 (19)	C14—H14	0.9500
N5—C15	1.3303 (19)	C16—H16A	0.9800
N5—C12	1.333 (2)	C16—H16B	0.9800
C1—C2	1.480 (3)	C16—H16C	0.9800
C1—C3	1.495 (2)	C17—H17A	0.9800
C1—H1A	0.9900	C17—H17B	0.9800
C1—H1B	0.9900	C17—H17C	0.9800
O2—S1—O3	120.02 (7)	C7—C6—C5	122.31 (17)
O2—S1—N1	104.90 (7)	C7—C6—H6	118.8
O3—S1—N1	111.04 (7)	C5—C6—H6	118.8
O2—S1—N2	110.02 (7)	C6—C7—C8	118.96 (17)
O3—S1—N2	102.97 (7)	C6—C7—H7	120.5
N1—S1—N2	107.42 (7)	C8—C7—H7	120.5
C13—O5—C16	116.90 (13)	C7—C8—C9	120.99 (17)
C15—O6—C17	116.82 (13)	C7—C8—H8	119.5
C10—N1—S1	127.72 (10)	C9—C8—H8	119.5
C10—N1—H1N	116.1	C8—C9—C10	120.18 (16)
S1—N1—H1N	116.1	C8—C9—H9	119.9
C11—N2—S1	123.13 (10)	C10—C9—H9	119.9
C11—N2—H2N	118.4	C9—C10—N1	122.06 (14)
S1—N2—H2N	118.4	C9—C10—C5	119.97 (14)
C11—N3—C12	130.81 (13)	N1—C10—C5	117.98 (13)
C11—N3—H3N	114.6	O4—C11—N3	121.65 (14)
C12—N3—H3N	114.6	O4—C11—N2	123.54 (14)
C12—N4—C13	115.60 (13)	N3—C11—N2	114.81 (12)
C15—N5—C12	114.47 (13)	N4—C12—N5	127.86 (14)
C2—C1—C3	60.76 (12)	N4—C12—N3	118.65 (14)
C2—C1—H1A	117.7	N5—C12—N3	113.49 (13)
C3—C1—H1A	117.7	O5—C13—N4	112.08 (13)
C2—C1—H1B	117.7	O5—C13—C14	125.27 (14)
C3—C1—H1B	117.7	N4—C13—C14	122.65 (14)
H1A—C1—H1B	114.8	C13—C14—C15	115.36 (14)
C1—C2—C3	60.10 (12)	C13—C14—H14	122.3
C1—C2—H2A	117.8	C15—C14—H14	122.3
C3—C2—H2A	117.8	N5—C15—O6	119.06 (15)
C1—C2—H2B	117.8	N5—C15—C14	124.04 (15)
C3—C2—H2B	117.8	O6—C15—C14	116.89 (14)
H2A—C2—H2B	114.9	O5—C16—H16A	109.5
C4—C3—C1	119.02 (16)	O5—C16—H16B	109.5
C4—C3—C2	116.34 (14)	H16A—C16—H16B	109.5
C1—C3—C2	59.14 (12)	O5—C16—H16C	109.5
C4—C3—H3	116.6	H16A—C16—H16C	109.5
C1—C3—H3	116.6	H16B—C16—H16C	109.5
C2—C3—H3	116.6	O6—C17—H17A	109.5
O1—C4—C3	119.04 (15)	O6—C17—H17B	109.5
O1—C4—C5	121.68 (14)	H17A—C17—H17B	109.5
C3—C4—C5	119.26 (15)	O6—C17—H17C	109.5
C6—C5—C10	117.59 (15)	H17A—C17—H17C	109.5
C6—C5—C4	120.40 (15)	H17B—C17—H17C	109.5
C10—C5—C4	122.01 (14)
O2—S1—N1—C10	176.89 (13)	C4—C5—C10—C9	−179.69 (15)
O3—S1—N1—C10	−52.05 (15)	C6—C5—C10—N1	−179.72 (15)
N2—S1—N1—C10	59.84 (15)	C4—C5—C10—N1	0.3 (2)
O2—S1—N2—C11	−47.34 (14)	C12—N3—C11—O4	−177.90 (15)
O3—S1—N2—C11	−176.41 (12)	C12—N3—C11—N2	1.5 (2)
N1—S1—N2—C11	66.31 (13)	S1—N2—C11—O4	−10.3 (2)
C2—C1—C3—C4	−105.05 (18)	S1—N2—C11—N3	170.31 (11)
C1—C2—C3—C4	109.56 (18)	C13—N4—C12—N5	−0.8 (2)
C1—C3—C4—O1	4.1 (2)	C13—N4—C12—N3	178.68 (14)
C2—C3—C4—O1	−63.6 (2)	C15—N5—C12—N4	1.3 (2)
C1—C3—C4—C5	−177.36 (15)	C15—N5—C12—N3	−178.23 (14)
C2—C3—C4—C5	114.96 (19)	C11—N3—C12—N4	−2.0 (2)
O1—C4—C5—C6	177.40 (17)	C11—N3—C12—N5	177.54 (15)
C3—C4—C5—C6	−1.1 (2)	C16—O5—C13—N4	−179.99 (16)
O1—C4—C5—C10	−2.6 (3)	C16—O5—C13—C14	−0.3 (2)
C3—C4—C5—C10	178.88 (14)	C12—N4—C13—O5	179.06 (13)
C10—C5—C6—C7	−1.0 (3)	C12—N4—C13—C14	−0.6 (2)
C4—C5—C6—C7	179.00 (18)	O5—C13—C14—C15	−178.31 (15)
C5—C6—C7—C8	0.7 (3)	N4—C13—C14—C15	1.3 (2)
C6—C7—C8—C9	0.4 (3)	C12—N5—C15—O6	178.96 (14)
C7—C8—C9—C10	−1.0 (3)	C12—N5—C15—C14	−0.4 (2)
C8—C9—C10—N1	−179.31 (16)	C17—O6—C15—N5	1.8 (2)
C8—C9—C10—C5	0.7 (3)	C17—O6—C15—C14	−178.78 (15)
S1—N1—C10—C9	10.3 (2)	C13—C14—C15—N5	−0.8 (2)
S1—N1—C10—C5	−169.74 (12)	C13—C14—C15—O6	179.85 (15)
C6—C5—C10—C9	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.88	1.86	2.5736 (18)	137
N2—H2N···N4	0.88	1.92	2.6158 (18)	135
C9—H9···O3	0.95	2.45	3.088 (2)	124
N3—H3N···O2i	0.88	2.08	2.9391 (17)	165
C2—H2B···O2ii	0.99	2.51	3.483 (2)	169
C3—H3···O4iii	1.00	2.51	3.286 (2)	135
C8—H8···O3iv	0.95	2.50	3.307 (2)	142

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1NO1	0.88	1.86	2.5736(18)	137
N2H2NN4	0.88	1.92	2.6158(18)	135
C9H9O3	0.95	2.45	3.088(2)	124
N3H3NO2i	0.88	2.08	2.9391(17)	165
C2H2BO2ii	0.99	2.51	3.483(2)	169
C3H3O4iii	1.00	2.51	3.286(2)	135
C8H8O3iv	0.95	2.50	3.307(2)	142

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