Crystal structure of flumioxazin.

The title compound {systematic name: 2-[7-fluoro-3,4-di-hydro-3-oxo-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetra-hydro-1H-iso-indole-1,3(2H)-dione}, C19H15FN2O4, is a dicarboximide herbicide. The dihedral angle between the male-imide and benzene ring planes is 66.13 (5)°. In the crystal, C-H⋯O and C-H⋯F hydrogen bonds and weak C-H⋯π inter-actions [3.5601 (19) Å] link adjacent mol-ecules, forming two-dimensional networks extending parallel to the (110) plane.

Related literature

For information on the herbicidal properties of the title compound, see: Saladin et al. (2003 ▸); Geoffroy et al. (2004 ▸). For a related crystal structure, see: Hou et al. (2004 ▸).

Experimental

Crystal data

C19H15FN2O4

M = 354.33

Monoclinic,

a = 8.896 (1) Å

b = 7.1592 (8) Å

c = 25.708 (3) Å

β = 96.039 (6)°

V = 1628.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.50 × 0.26 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.575, T max = 0.746

27372 measured reflections

4067 independent reflections

3277 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.137

S = 1.07

4067 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.27 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/S2056989015017223/hb7502sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017223/hb7502Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015017223/hb7502Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015017223/hb7502fig1.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/S2056989015017223/hb7502fig2.tif

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

CCDC reference: 1424397

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

C19H15FN2O4	F(000) = 736
Mr = 354.33	Dx = 1.445 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.896 (1) Å	Cell parameters from 8497 reflections
b = 7.1592 (8) Å	θ = 2.7–28.2°
c = 25.708 (3) Å	µ = 0.11 mm−1
β = 96.039 (6)°	T = 173 K
V = 1628.2 (3) Å3	Plate, colourless
Z = 4	0.50 × 0.26 × 0.05 mm

Bruker APEXII CCD diffractometer	3277 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.067
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 28.4°, θmin = 1.6°
Tmin = 0.575, Tmax = 0.746	h = −11→11
27372 measured reflections	k = −9→9
4067 independent reflections	l = −34→34

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.9028P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
4067 reflections	Δρmax = 0.32 e Å−3
235 parameters	Δρmin = −0.27 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
F1	0.77768 (12)	0.66568 (18)	0.33755 (5)	0.0431 (3)
O1	1.40190 (15)	0.41585 (19)	0.54636 (5)	0.0359 (3)
O2	1.12467 (13)	0.73087 (17)	0.48786 (4)	0.0273 (3)
O3	0.94166 (16)	0.4892 (2)	0.25135 (5)	0.0459 (4)
O4	0.74322 (15)	0.08897 (18)	0.36415 (5)	0.0331 (3)
N1	1.22083 (15)	0.3652 (2)	0.47885 (5)	0.0235 (3)
N2	0.86942 (16)	0.3094 (2)	0.31951 (5)	0.0276 (3)
C1	1.30559 (18)	0.4767 (3)	0.51371 (6)	0.0265 (4)
C2	1.27631 (19)	0.6824 (3)	0.50845 (7)	0.0291 (4)
H2A	1.2983	0.7410	0.5433	0.035*
H2B	1.3474	0.7360	0.4853	0.035*
C3	1.06753 (17)	0.6259 (2)	0.44577 (6)	0.0226 (3)
C4	1.11458 (17)	0.4423 (2)	0.43988 (6)	0.0217 (3)
C5	1.2461 (2)	0.1636 (2)	0.48166 (6)	0.0272 (4)
H5A	1.1481	0.0987	0.4739	0.033*
H5B	1.2872	0.1300	0.5177	0.033*
C6	1.3508 (2)	0.0983 (2)	0.44508 (7)	0.0284 (4)
C7	1.4371 (2)	0.0447 (3)	0.41648 (7)	0.0357 (4)
H7	1.5064	0.0015	0.3935	0.043*
C8	0.95463 (18)	0.7036 (3)	0.41121 (6)	0.0266 (4)
H8	0.9225	0.8288	0.4154	0.032*
C9	0.89012 (18)	0.5945 (3)	0.37066 (7)	0.0284 (4)
C10	0.93760 (18)	0.4142 (3)	0.36273 (6)	0.0261 (4)
C11	1.05195 (18)	0.3384 (2)	0.39736 (6)	0.0244 (3)
H11	1.0873	0.2154	0.3920	0.029*
C12	0.87139 (19)	0.3604 (3)	0.26659 (7)	0.0298 (4)
C13	0.76914 (17)	0.2264 (3)	0.23609 (6)	0.0252 (4)
C14	0.70932 (18)	0.1121 (2)	0.26880 (6)	0.0246 (4)
C15	0.77039 (17)	0.1593 (2)	0.32346 (6)	0.0235 (3)
C16	0.7429 (2)	0.2189 (3)	0.17802 (6)	0.0338 (4)
H16A	0.8355	0.1746	0.1637	0.041*
H16B	0.7193	0.3457	0.1640	0.041*
C17	0.6125 (2)	0.0878 (3)	0.16111 (7)	0.0430 (5)
H17A	0.5158	0.1542	0.1634	0.052*
H17B	0.6171	0.0519	0.1241	0.052*
C18	0.6158 (3)	−0.0865 (3)	0.19432 (8)	0.0468 (5)
H18A	0.7113	−0.1546	0.1912	0.056*
H18B	0.5311	−0.1690	0.1809	0.056*
C19	0.6033 (2)	−0.0436 (3)	0.25236 (7)	0.0361 (4)
H19A	0.4984	−0.0070	0.2573	0.043*
H19B	0.6297	−0.1559	0.2739	0.043*

	U11	U22	U33	U12	U13	U23
F1	0.0319 (6)	0.0490 (7)	0.0443 (6)	0.0126 (5)	−0.0160 (5)	−0.0011 (5)
O1	0.0353 (7)	0.0380 (8)	0.0310 (6)	−0.0010 (6)	−0.0128 (5)	0.0025 (6)
O2	0.0270 (6)	0.0264 (6)	0.0273 (6)	−0.0010 (5)	−0.0021 (5)	−0.0052 (5)
O3	0.0433 (8)	0.0572 (10)	0.0362 (7)	−0.0243 (7)	−0.0003 (6)	0.0082 (7)
O4	0.0408 (7)	0.0352 (7)	0.0228 (6)	−0.0063 (6)	0.0011 (5)	0.0015 (5)
N1	0.0241 (7)	0.0220 (7)	0.0230 (6)	0.0000 (6)	−0.0034 (5)	0.0015 (5)
N2	0.0235 (7)	0.0368 (8)	0.0213 (6)	−0.0068 (6)	−0.0036 (5)	−0.0004 (6)
C1	0.0234 (8)	0.0334 (9)	0.0222 (7)	−0.0031 (7)	−0.0004 (6)	0.0009 (7)
C2	0.0264 (8)	0.0290 (9)	0.0301 (8)	−0.0042 (7)	−0.0055 (7)	−0.0026 (7)
C3	0.0197 (7)	0.0258 (8)	0.0222 (7)	−0.0031 (6)	0.0012 (6)	−0.0014 (6)
C4	0.0174 (7)	0.0247 (8)	0.0224 (7)	−0.0019 (6)	0.0001 (6)	0.0022 (6)
C5	0.0296 (8)	0.0247 (9)	0.0263 (8)	−0.0005 (7)	−0.0016 (6)	0.0027 (7)
C6	0.0288 (8)	0.0234 (9)	0.0309 (8)	−0.0005 (7)	−0.0065 (7)	0.0005 (7)
C7	0.0341 (10)	0.0369 (11)	0.0354 (9)	−0.0024 (8)	0.0004 (8)	−0.0058 (8)
C8	0.0221 (8)	0.0269 (9)	0.0306 (8)	0.0032 (7)	0.0020 (6)	0.0001 (7)
C9	0.0196 (8)	0.0354 (10)	0.0289 (8)	0.0028 (7)	−0.0041 (6)	0.0036 (7)
C10	0.0208 (8)	0.0332 (9)	0.0235 (7)	−0.0050 (7)	−0.0018 (6)	−0.0023 (7)
C11	0.0220 (8)	0.0263 (8)	0.0245 (7)	−0.0026 (7)	0.0007 (6)	−0.0008 (7)
C12	0.0221 (8)	0.0410 (10)	0.0255 (8)	−0.0046 (8)	−0.0010 (6)	0.0024 (7)
C13	0.0176 (7)	0.0355 (9)	0.0217 (7)	0.0024 (7)	−0.0022 (6)	−0.0006 (7)
C14	0.0204 (7)	0.0300 (9)	0.0221 (7)	0.0014 (7)	−0.0031 (6)	−0.0020 (6)
C15	0.0192 (7)	0.0280 (8)	0.0226 (7)	0.0017 (6)	−0.0013 (6)	−0.0010 (6)
C16	0.0285 (9)	0.0515 (12)	0.0207 (8)	0.0011 (8)	−0.0011 (6)	0.0025 (8)
C17	0.0322 (10)	0.0718 (15)	0.0234 (8)	−0.0059 (10)	−0.0039 (7)	−0.0085 (9)
C18	0.0483 (12)	0.0536 (14)	0.0368 (10)	−0.0122 (10)	−0.0032 (9)	−0.0155 (10)
C19	0.0397 (10)	0.0367 (11)	0.0301 (9)	−0.0123 (9)	−0.0047 (7)	−0.0025 (8)

F1—C9	1.3436 (19)	C7—H7	0.9500
O1—C1	1.215 (2)	C8—C9	1.378 (2)
O2—C3	1.3707 (19)	C8—H8	0.9500
O2—C2	1.439 (2)	C9—C10	1.380 (3)
O3—C12	1.203 (2)	C10—C11	1.390 (2)
O4—C15	1.208 (2)	C11—H11	0.9500
N1—C1	1.366 (2)	C12—C13	1.487 (2)
N1—C4	1.4153 (19)	C13—C14	1.325 (2)
N1—C5	1.461 (2)	C13—C16	1.488 (2)
N2—C15	1.400 (2)	C14—C15	1.491 (2)
N2—C12	1.410 (2)	C14—C19	1.493 (2)
N2—C10	1.422 (2)	C16—C17	1.520 (3)
C1—C2	1.499 (3)	C16—H16A	0.9900
C2—H2A	0.9900	C16—H16B	0.9900
C2—H2B	0.9900	C17—C18	1.511 (3)
C3—C8	1.386 (2)	C17—H17A	0.9900
C3—C4	1.392 (2)	C17—H17B	0.9900
C4—C11	1.390 (2)	C18—C19	1.539 (3)
C5—C6	1.468 (2)	C18—H18A	0.9900
C5—H5A	0.9900	C18—H18B	0.9900
C5—H5B	0.9900	C19—H19A	0.9900
C6—C7	1.182 (3)	C19—H19B	0.9900
C3—O2—C2	114.43 (13)	C4—C11—C10	120.04 (16)
C1—N1—C4	121.20 (14)	C4—C11—H11	120.0
C1—N1—C5	118.24 (14)	C10—C11—H11	120.0
C4—N1—C5	120.54 (13)	O3—C12—N2	124.88 (16)
C15—N2—C12	109.88 (13)	O3—C12—C13	129.26 (16)
C15—N2—C10	124.61 (14)	N2—C12—C13	105.84 (14)
C12—N2—C10	124.73 (15)	C14—C13—C12	109.15 (14)
O1—C1—N1	122.97 (17)	C14—C13—C16	125.71 (16)
O1—C1—C2	121.16 (16)	C12—C13—C16	125.12 (16)
N1—C1—C2	115.85 (14)	C13—C14—C15	109.11 (15)
O2—C2—C1	114.67 (14)	C13—C14—C19	124.47 (15)
O2—C2—H2A	108.6	C15—C14—C19	126.37 (15)
C1—C2—H2A	108.6	O4—C15—N2	124.57 (15)
O2—C2—H2B	108.6	O4—C15—C14	129.44 (16)
C1—C2—H2B	108.6	N2—C15—C14	105.98 (13)
H2A—C2—H2B	107.6	C13—C16—C17	110.12 (15)
O2—C3—C8	117.99 (15)	C13—C16—H16A	109.6
O2—C3—C4	120.85 (14)	C17—C16—H16A	109.6
C8—C3—C4	121.02 (15)	C13—C16—H16B	109.6
C11—C4—C3	119.39 (14)	C17—C16—H16B	109.6
C11—C4—N1	122.06 (15)	H16A—C16—H16B	108.2
C3—C4—N1	118.50 (14)	C18—C17—C16	112.33 (16)
N1—C5—C6	112.80 (14)	C18—C17—H17A	109.1
N1—C5—H5A	109.0	C16—C17—H17A	109.1
C6—C5—H5A	109.0	C18—C17—H17B	109.1
N1—C5—H5B	109.0	C16—C17—H17B	109.1
C6—C5—H5B	109.0	H17A—C17—H17B	107.9
H5A—C5—H5B	107.8	C17—C18—C19	112.57 (18)
C7—C6—C5	178.63 (19)	C17—C18—H18A	109.1
C6—C7—H7	180.0	C19—C18—H18A	109.1
C9—C8—C3	118.25 (16)	C17—C18—H18B	109.1
C9—C8—H8	120.9	C19—C18—H18B	109.1
C3—C8—H8	120.9	H18A—C18—H18B	107.8
F1—C9—C8	119.17 (16)	C14—C19—C18	108.39 (16)
F1—C9—C10	118.68 (15)	C14—C19—H19A	110.0
C8—C9—C10	122.15 (15)	C18—C19—H19A	110.0
C9—C10—C11	119.04 (15)	C14—C19—H19B	110.0
C9—C10—N2	119.79 (15)	C18—C19—H19B	110.0
C11—C10—N2	121.17 (16)	H19A—C19—H19B	108.4
C4—N1—C1—O1	−177.07 (15)	C3—C4—C11—C10	−3.5 (2)
C5—N1—C1—O1	0.9 (2)	N1—C4—C11—C10	173.89 (14)
C4—N1—C1—C2	1.1 (2)	C9—C10—C11—C4	1.4 (2)
C5—N1—C1—C2	179.13 (15)	N2—C10—C11—C4	−178.70 (15)
C3—O2—C2—C1	−44.1 (2)	C15—N2—C12—O3	177.05 (18)
O1—C1—C2—O2	−152.56 (16)	C10—N2—C12—O3	6.8 (3)
N1—C1—C2—O2	29.2 (2)	C15—N2—C12—C13	−1.89 (19)
C2—O2—C3—C8	−154.71 (15)	C10—N2—C12—C13	−172.15 (15)
C2—O2—C3—C4	29.4 (2)	O3—C12—C13—C14	−176.9 (2)
O2—C3—C4—C11	178.59 (14)	N2—C12—C13—C14	1.96 (19)
C8—C3—C4—C11	2.9 (2)	O3—C12—C13—C16	5.0 (3)
O2—C3—C4—N1	1.1 (2)	N2—C12—C13—C16	−176.16 (16)
C8—C3—C4—N1	−174.58 (14)	C12—C13—C14—C15	−1.26 (19)
C1—N1—C4—C11	165.50 (15)	C16—C13—C14—C15	176.84 (16)
C5—N1—C4—C11	−12.5 (2)	C12—C13—C14—C19	−178.74 (16)
C1—N1—C4—C3	−17.1 (2)	C16—C13—C14—C19	−0.6 (3)
C5—N1—C4—C3	164.92 (15)	C12—N2—C15—O4	−178.20 (17)
C1—N1—C5—C6	−95.61 (17)	C10—N2—C15—O4	−7.9 (3)
C4—N1—C5—C6	82.40 (19)	C12—N2—C15—C14	1.17 (18)
O2—C3—C8—C9	−176.00 (15)	C10—N2—C15—C14	171.45 (15)
C4—C3—C8—C9	−0.2 (2)	C13—C14—C15—O4	179.43 (18)
C3—C8—C9—F1	178.24 (15)	C19—C14—C15—O4	−3.2 (3)
C3—C8—C9—C10	−2.0 (3)	C13—C14—C15—N2	0.10 (19)
F1—C9—C10—C11	−178.83 (15)	C19—C14—C15—N2	177.52 (16)
C8—C9—C10—C11	1.4 (3)	C14—C13—C16—C17	11.8 (3)
F1—C9—C10—N2	1.2 (2)	C12—C13—C16—C17	−170.41 (17)
C8—C9—C10—N2	−178.51 (16)	C13—C16—C17—C18	−40.6 (2)
C15—N2—C10—C9	−108.0 (2)	C16—C17—C18—C19	60.9 (2)
C12—N2—C10—C9	60.9 (2)	C13—C14—C19—C18	17.6 (3)
C15—N2—C10—C11	72.1 (2)	C15—C14—C19—C18	−159.46 (17)
C12—N2—C10—C11	−119.05 (19)	C17—C18—C19—C14	−46.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O4i	0.95	2.39	3.178 (2)	140
C19—H19B···F1ii	0.99	2.36	3.289 (2)	155
C16—H16A···Cg1iii	0.99	2.63	3.5601 (19)	157

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C3/C4/C8C11 ring.

DHA	DH	HA	D A	DHA
C7H7O4i	0.95	2.39	3.178(2)	140
C19H19BF1ii	0.99	2.36	3.289(2)	155
C16H16A Cg1iii	0.99	2.63	3.5601(19)	157

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