organic compounds
of flumioxazin
aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 52828, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr
The title compound {systematic name: 2-[7-fluoro-3,4-dihydro-3-oxo-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione}, C19H15FN2O4, is a dicarboximide herbicide. The dihedral angle between the maleimide 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 interactions [3.5601 (19) Å] link adjacent molecules, forming two-dimensional networks extending parallel to the (110) plane.
Keywords: crystal structure; dicarboximide herbicide; flumioxazin; 1H-isoindole; 1,4-benzoxazine; C—H⋯F hydrogen bonds.
CCDC reference: 1424397
1. Related literature
For information on the herbicidal properties of the title compound, see: Saladin et al. (2003); Geoffroy et al. (2004). For a related see: Hou et al. (2004).
2. Experimental
2.1. Crystal data
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2.3. Refinement
|
Data collection: APEX2 (Bruker, 2013); cell 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).
Supporting information
CCDC reference: 1424397
10.1107/S2056989015017223/hb7502sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015017223/hb7502Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015017223/hb7502Isup3.cml
The title compound was purchased from the Dr Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH3CN gave single crystals suitable for X-ray analysis.
All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 group, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H aromatic C—H and Csp—H.
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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).Fig. 1. 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. | |
Fig. 2. Crystal packing viewed along the c axis. The intermolecular interactions are shown as dashed lines. |
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 |
C19H15FN2O4 | V = 1628.2 (3) Å3 |
Mr = 354.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.896 (1) Å | µ = 0.11 mm−1 |
b = 7.1592 (8) Å | T = 173 K |
c = 25.708 (3) Å | 0.50 × 0.26 × 0.05 mm |
β = 96.039 (6)° |
Bruker APEXII CCD diffractometer | 4067 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 3277 reflections with I > 2σ(I) |
Tmin = 0.575, Tmax = 0.746 | Rint = 0.067 |
27372 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.32 e Å−3 |
4067 reflections | Δρmin = −0.27 e Å−3 |
235 parameters |
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) |
Cg1 is the centroid of the C3/C4/C8–C11 ring. |
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 |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z; (iii) −x+2, y−1/2, −z+1/2. |
Cg1 is the centroid of the C3/C4/C8–C11 ring. |
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 |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z; (iii) −x+2, y−1/2, −z+1/2. |
Acknowledgements
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2015R1D1A4A01020317).
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Flumioxazin [systematic name: 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione] is a soil applied pre-emergent herbicide used to inhibit development of redroot pigweed. (Geoffroy et al., 2004; Saladin et al., 2003). However, its crystal structure has not been reported until now. In the title compound (Fig. 1), the dihedral angle between pyrrole and benzne rings is 66.13 (5)°. All bond lengths and bond angles are normal and comparable to those observed in a similar crystal structure (Hou et al., 2004).
In the crystal structure (Fig. 2), C—H···O and C—H···F hydrogen bonds and weak C–H···π interactions are observed (Table 1). Two-dimensional networks are formed by the hydrogen bonds and weak C–H···π interactions.