research communications
of flucetosulfuron
aDepartment of Chemistry (BK21 plus) 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: 1-[3-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]amino}sulfonyl)pyridin-2-yl]-2-fluoropropyl 2-methoxyacetate}, C18H22FN5O8S, is used as a herbicide (pyrimidinylsulfonylurea herbicide). The dihedral angle between the mean planes of the pyridine and pyrimidine rings is 86.90 (7)°. In the crystal, N/C—H⋯O hydrogen bonds, C—H⋯F and C—H⋯π interactions link adjacent molecules, forming a chain along [020]. A further two C—H⋯O hydrogen bonds together with weak π–π interactions [ring centroid separation = 3.7584 (12) Å] further aggregate the structure into a three-dimensional architecture.
CCDC reference: 1572854
1. Chemical context
Flucetosulfuron, a relatively new herbicide, inhibits acetolactate synthase (ALS) in plants, as do other ALS inhibitors such as imidazolinones, pyrimidinyloxybenzoates, triazolopyrimidines, and sulfonylaminocarbonyltriazolinones (Lee et al., 2014). It is a novel post-emergence sulfonylurea herbicide providing excellent control of Galium aparine and other important broadleaf weeds with good safety to cereal crops, wheat and barley (Kim, Lee et al., 2003) In rice, the herbicide provides excellent control of Echinochloa crus-galli, which is not or only marginally controlled by common sulfonylurea products, and also controls annual broadleaf weeds, sedges and perennial weeds of rice with similar efficacy to other sulfonylurea rice herbicides (Kim, Koo et al., 2003). Until now, its had not been reported and we describe it herein.
2. Structural commentary
The structure of flucetosulfuron is shown in Fig. 1. The dihedral angle between the mean planes of the pyridine and pyrimidine rings is 86.90 (7)°. All bond lengths and angles are normal and comparable to those observed in similar crystal structures (Jeon et al., 2015; Chopra et al., 2004).
3. Supramolecular features
In the crystal, molecules are linked by C1—H1A⋯O3i, N3—H3N⋯O8i and C2—H2B⋯F1ii hydrogen bonds [H⋯O = 2.58, 2.01 and H⋯F = 2.53 Å; Table 1] and C1—H1B⋯Cg1i interactions [H⋯π = 2.74 Å], forming a chain structure along [020] (yellow dashed lines in Fig. 2). In addition, the chains are linked by C12—H12⋯O2iii hydrogen bonds [H⋯O =2.42 Å], forming a two-dimensional network structure parallel to (020) (red dashed lines in Fig. 2). The C17—H17⋯O5iv hydrogen bond [H⋯O =2.55 Å] and weak π–π interactions (N1–N2/C3–C6) [Cg2⋯Cg2v= 3.7584 (12) Å; symmetry code: (v) −x + 2, −y + 1, −z + 1] generate a three-dimensional architecture with molecules stacked along the a-axis direction (black dashed lines in Fig. 3).
4. Database survey
We have reported the crystal structures of several pesticides including compounds with pyrimidinylsulfonylurea, dimethoxypyrimidin and sulfonylurea ring (Kang et al., 2015; Jeon et al., 2015; Kwon et al., 2016). Moreover, a database search (CSD Version 5.27, last update February 2017; Groom et al., 2016) yielded other comparable structures, methyl 2-{[3-(4,6-dimethoxypyrimidin-2-yl)ureido]sulfonylmethyl}benzoate (Xia et al., 2008), 2-amino-4,6-dimethoxypyrimidin-1-ium 2,2-dichloroacetate (Lin et al., 2012), N-[(perhydrocyclopenta[c]pyrrol-2-yl)aminocarbonyl]-o-toluenesulfonamide (Wu et al., 2012) and 4-{4-[N-(5,6-dimethoxypyrimidin-4-yl)sulfamoyl]phenylcarbamoyl}-2,6-dimethoxyphenyl acetate (Pan et al., 2012).
5. Synthesis and crystallization
The title compound was purchased from Dr Ehrenstorfer GmbH. Colourless single crystals suitable for X-ray diffraction were obtained from a CH3CN solution by slow evaporation at room temperature.
6. Refinement
Crystal data, data collection and structure . All H atoms were positioned geometrically and refined using a riding model with d(N—H) = 0.88 Å, Uiso = 1.2Ueq(C) for urea N—H, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H, d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for methyl groups, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 group, d(C—H) = 1.00 Å, Uiso = 1.5Ueq(C) for Csp3—H.
details are summarized in Table 2
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Supporting information
CCDC reference: 1572854
https://doi.org/10.1107/S2056989017012737/hg5495sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017012737/hg5495Isup2.hkl
Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).C18H22FN5O8S | Z = 2 |
Mr = 487.46 | F(000) = 508 |
Triclinic, P1 | Dx = 1.504 Mg m−3 |
a = 8.3993 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.1030 (3) Å | Cell parameters from 3325 reflections |
c = 15.6862 (5) Å | θ = 2.5–26.9° |
α = 92.116 (2)° | µ = 0.22 mm−1 |
β = 101.113 (2)° | T = 173 K |
γ = 112.810 (2)° | Needle, colourless |
V = 1076.53 (6) Å3 | 0.36 × 0.06 × 0.05 mm |
Bruker APEXII CCD diffractometer | 3081 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.031 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 25.0°, θmin = 1.3° |
Tmin = 0.702, Tmax = 0.746 | h = −9→9 |
10919 measured reflections | k = −10→10 |
3773 independent reflections | l = −18→18 |
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) = 0.099 | w = 1/[σ2(Fo2) + (0.0439P)2 + 0.337P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3773 reflections | Δρmax = 0.45 e Å−3 |
302 parameters | Δρmin = −0.39 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.39351 (7) | 0.10312 (6) | 0.18674 (3) | 0.02316 (15) | |
F1 | 0.2117 (2) | 0.35690 (17) | −0.01327 (8) | 0.0529 (4) | |
O1 | 1.0327 (2) | 0.78934 (17) | 0.56837 (9) | 0.0345 (4) | |
O2 | 0.97933 (18) | 0.63951 (17) | 0.27393 (9) | 0.0268 (3) | |
O3 | 0.34138 (19) | 0.08587 (18) | 0.37121 (9) | 0.0309 (4) | |
O4 | 0.48165 (18) | 0.18107 (17) | 0.12133 (9) | 0.0278 (4) | |
O5 | 0.3822 (2) | −0.05369 (17) | 0.20150 (10) | 0.0330 (4) | |
O6 | 0.26027 (17) | 0.48834 (16) | 0.21292 (8) | 0.0226 (3) | |
O7 | 0.55822 (19) | 0.62252 (18) | 0.24672 (9) | 0.0302 (4) | |
O8 | 0.53183 (18) | 0.72872 (16) | 0.41130 (9) | 0.0262 (4) | |
N1 | 0.8060 (2) | 0.5524 (2) | 0.49899 (11) | 0.0227 (4) | |
N2 | 0.7821 (2) | 0.4766 (2) | 0.34862 (10) | 0.0213 (4) | |
N3 | 0.5794 (2) | 0.3194 (2) | 0.42532 (11) | 0.0249 (4) | |
H3N | 0.5538 | 0.3064 | 0.4771 | 0.030* | |
N4 | 0.4990 (2) | 0.2289 (2) | 0.27617 (10) | 0.0252 (4) | |
H4N | 0.5839 | 0.3209 | 0.2718 | 0.030* | |
N5 | −0.0364 (2) | 0.2072 (2) | 0.11793 (12) | 0.0310 (4) | |
C1 | 0.9641 (3) | 0.7561 (3) | 0.64590 (14) | 0.0356 (6) | |
H1A | 0.8389 | 0.7393 | 0.6326 | 0.053* | |
H1B | 1.0313 | 0.8472 | 0.6918 | 0.053* | |
H1C | 0.9752 | 0.6593 | 0.6662 | 0.053* | |
C2 | 0.8773 (3) | 0.5257 (3) | 0.19662 (13) | 0.0285 (5) | |
H2A | 0.8717 | 0.4188 | 0.2079 | 0.043* | |
H2B | 0.9342 | 0.5588 | 0.1475 | 0.043* | |
H2C | 0.7571 | 0.5224 | 0.1821 | 0.043* | |
C3 | 0.9464 (3) | 0.6843 (2) | 0.49563 (13) | 0.0238 (5) | |
C4 | 0.7292 (3) | 0.4557 (2) | 0.42344 (13) | 0.0207 (4) | |
C5 | 0.9225 (3) | 0.6125 (2) | 0.34821 (13) | 0.0215 (5) | |
C6 | 1.0123 (3) | 0.7244 (2) | 0.42113 (13) | 0.0253 (5) | |
H6 | 1.1113 | 0.8211 | 0.4205 | 0.030* | |
C7 | 0.4640 (3) | 0.2007 (2) | 0.35825 (13) | 0.0234 (5) | |
C8 | 0.1749 (3) | 0.0953 (2) | 0.16496 (12) | 0.0209 (5) | |
C9 | 0.1326 (3) | 0.2238 (2) | 0.13956 (13) | 0.0229 (5) | |
C10 | −0.1640 (3) | 0.0645 (3) | 0.12140 (15) | 0.0358 (6) | |
H10 | −0.2836 | 0.0525 | 0.1041 | 0.043* | |
C11 | −0.1331 (3) | −0.0655 (3) | 0.14834 (15) | 0.0356 (6) | |
H11 | −0.2283 | −0.1633 | 0.1518 | 0.043* | |
C12 | 0.0406 (3) | −0.0500 (3) | 0.17037 (14) | 0.0303 (5) | |
H12 | 0.0674 | −0.1376 | 0.1889 | 0.036* | |
C13 | 0.2671 (3) | 0.3930 (2) | 0.13829 (12) | 0.0219 (5) | |
H13 | 0.3884 | 0.3942 | 0.1447 | 0.026* | |
C14 | 0.2184 (3) | 0.4629 (3) | 0.05544 (13) | 0.0320 (5) | |
H14 | 0.0981 | 0.4629 | 0.0509 | 0.038* | |
C15 | 0.3463 (3) | 0.6282 (3) | 0.04812 (15) | 0.0416 (6) | |
H15A | 0.3513 | 0.7036 | 0.0959 | 0.062* | |
H15B | 0.3069 | 0.6609 | −0.0082 | 0.062* | |
H15C | 0.4642 | 0.6286 | 0.0519 | 0.062* | |
C16 | 0.4167 (3) | 0.5958 (2) | 0.26289 (13) | 0.0210 (5) | |
C17 | 0.3826 (3) | 0.6730 (3) | 0.34038 (12) | 0.0240 (5) | |
H17A | 0.3527 | 0.7642 | 0.3228 | 0.029* | |
H17B | 0.2799 | 0.5939 | 0.3590 | 0.029* | |
C18 | 0.6598 (3) | 0.8857 (3) | 0.40752 (15) | 0.0316 (5) | |
H18A | 0.7041 | 0.8858 | 0.3541 | 0.047* | |
H18B | 0.7587 | 0.9161 | 0.4588 | 0.047* | |
H18C | 0.6045 | 0.9628 | 0.4071 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0254 (3) | 0.0223 (3) | 0.0209 (3) | 0.0097 (2) | 0.0034 (2) | 0.0019 (2) |
F1 | 0.0876 (12) | 0.0416 (9) | 0.0248 (7) | 0.0235 (8) | 0.0082 (7) | −0.0018 (6) |
O1 | 0.0420 (10) | 0.0256 (9) | 0.0233 (8) | 0.0007 (7) | 0.0076 (7) | −0.0027 (6) |
O2 | 0.0279 (8) | 0.0261 (8) | 0.0212 (8) | 0.0035 (7) | 0.0090 (6) | 0.0038 (6) |
O3 | 0.0267 (8) | 0.0276 (9) | 0.0286 (8) | 0.0001 (7) | 0.0071 (7) | 0.0052 (7) |
O4 | 0.0300 (8) | 0.0334 (9) | 0.0232 (8) | 0.0144 (7) | 0.0096 (6) | 0.0055 (6) |
O5 | 0.0405 (9) | 0.0229 (8) | 0.0371 (9) | 0.0164 (7) | 0.0046 (7) | 0.0044 (7) |
O6 | 0.0216 (7) | 0.0217 (8) | 0.0199 (7) | 0.0049 (6) | 0.0032 (6) | −0.0016 (6) |
O7 | 0.0216 (8) | 0.0325 (9) | 0.0329 (9) | 0.0077 (7) | 0.0056 (7) | −0.0022 (7) |
O8 | 0.0252 (8) | 0.0225 (8) | 0.0203 (7) | 0.0007 (6) | 0.0004 (6) | 0.0015 (6) |
N1 | 0.0227 (9) | 0.0216 (9) | 0.0217 (9) | 0.0069 (8) | 0.0043 (7) | 0.0032 (7) |
N2 | 0.0211 (9) | 0.0224 (9) | 0.0186 (9) | 0.0070 (8) | 0.0040 (7) | 0.0049 (7) |
N3 | 0.0247 (9) | 0.0261 (10) | 0.0169 (9) | 0.0028 (8) | 0.0044 (7) | 0.0040 (7) |
N4 | 0.0259 (10) | 0.0240 (10) | 0.0191 (9) | 0.0034 (8) | 0.0038 (7) | 0.0039 (7) |
N5 | 0.0226 (10) | 0.0291 (11) | 0.0374 (11) | 0.0090 (9) | 0.0027 (8) | −0.0029 (8) |
C1 | 0.0451 (14) | 0.0327 (13) | 0.0241 (12) | 0.0103 (11) | 0.0094 (10) | −0.0029 (10) |
C2 | 0.0318 (12) | 0.0303 (12) | 0.0216 (11) | 0.0106 (10) | 0.0060 (9) | 0.0018 (9) |
C3 | 0.0255 (11) | 0.0194 (11) | 0.0240 (11) | 0.0079 (9) | 0.0028 (9) | 0.0022 (9) |
C4 | 0.0201 (10) | 0.0211 (11) | 0.0212 (11) | 0.0088 (9) | 0.0034 (8) | 0.0062 (9) |
C5 | 0.0217 (11) | 0.0226 (11) | 0.0218 (11) | 0.0098 (9) | 0.0061 (8) | 0.0072 (9) |
C6 | 0.0242 (11) | 0.0212 (11) | 0.0256 (11) | 0.0042 (9) | 0.0046 (9) | 0.0047 (9) |
C7 | 0.0228 (11) | 0.0234 (12) | 0.0231 (11) | 0.0088 (10) | 0.0039 (9) | 0.0045 (9) |
C8 | 0.0233 (11) | 0.0186 (11) | 0.0166 (10) | 0.0054 (9) | 0.0018 (8) | −0.0006 (8) |
C9 | 0.0230 (11) | 0.0237 (11) | 0.0178 (10) | 0.0059 (9) | 0.0030 (8) | −0.0018 (8) |
C10 | 0.0206 (12) | 0.0335 (14) | 0.0439 (14) | 0.0042 (11) | 0.0030 (10) | −0.0089 (11) |
C11 | 0.0285 (13) | 0.0265 (13) | 0.0412 (14) | 0.0001 (11) | 0.0088 (10) | −0.0034 (11) |
C12 | 0.0348 (13) | 0.0212 (12) | 0.0303 (12) | 0.0062 (10) | 0.0077 (10) | 0.0018 (9) |
C13 | 0.0267 (11) | 0.0214 (11) | 0.0187 (10) | 0.0104 (9) | 0.0063 (8) | 0.0004 (8) |
C14 | 0.0467 (14) | 0.0288 (13) | 0.0205 (11) | 0.0157 (11) | 0.0065 (10) | 0.0016 (9) |
C15 | 0.0630 (18) | 0.0304 (14) | 0.0261 (13) | 0.0128 (12) | 0.0096 (12) | 0.0091 (10) |
C16 | 0.0221 (11) | 0.0171 (10) | 0.0213 (11) | 0.0061 (9) | 0.0024 (9) | 0.0063 (8) |
C17 | 0.0206 (11) | 0.0246 (11) | 0.0199 (11) | 0.0028 (9) | 0.0026 (8) | 0.0019 (9) |
C18 | 0.0281 (12) | 0.0224 (12) | 0.0343 (13) | 0.0002 (10) | 0.0058 (10) | 0.0007 (10) |
S1—O5 | 1.4242 (15) | C1—H1C | 0.9800 |
S1—O4 | 1.4295 (15) | C2—H2A | 0.9800 |
S1—N4 | 1.6369 (17) | C2—H2B | 0.9800 |
S1—C8 | 1.774 (2) | C2—H2C | 0.9800 |
F1—C14 | 1.397 (2) | C3—C6 | 1.389 (3) |
O1—C3 | 1.343 (2) | C5—C6 | 1.379 (3) |
O1—C1 | 1.437 (3) | C6—H6 | 0.9500 |
O2—C5 | 1.338 (2) | C8—C12 | 1.385 (3) |
O2—C2 | 1.448 (2) | C8—C9 | 1.398 (3) |
O3—C7 | 1.207 (2) | C9—C13 | 1.520 (3) |
O6—C16 | 1.359 (2) | C10—C11 | 1.371 (3) |
O6—C13 | 1.455 (2) | C10—H10 | 0.9500 |
O7—C16 | 1.197 (2) | C11—C12 | 1.383 (3) |
O8—C17 | 1.412 (2) | C11—H11 | 0.9500 |
O8—C18 | 1.429 (2) | C12—H12 | 0.9500 |
N1—C3 | 1.329 (3) | C13—C14 | 1.522 (3) |
N1—C4 | 1.336 (2) | C13—H13 | 1.0000 |
N2—C4 | 1.328 (2) | C14—C15 | 1.497 (3) |
N2—C5 | 1.339 (2) | C14—H14 | 1.0000 |
N3—C7 | 1.388 (3) | C15—H15A | 0.9800 |
N3—C4 | 1.389 (2) | C15—H15B | 0.9800 |
N3—H3N | 0.8800 | C15—H15C | 0.9800 |
N4—C7 | 1.386 (3) | C16—C17 | 1.510 (3) |
N4—H4N | 0.8800 | C17—H17A | 0.9900 |
N5—C10 | 1.337 (3) | C17—H17B | 0.9900 |
N5—C9 | 1.341 (3) | C18—H18A | 0.9800 |
C1—H1A | 0.9800 | C18—H18B | 0.9800 |
C1—H1B | 0.9800 | C18—H18C | 0.9800 |
O5—S1—O4 | 119.31 (9) | C12—C8—S1 | 116.68 (16) |
O5—S1—N4 | 110.36 (9) | C9—C8—S1 | 123.71 (15) |
O4—S1—N4 | 103.89 (9) | N5—C9—C8 | 121.03 (18) |
O5—S1—C8 | 107.60 (9) | N5—C9—C13 | 113.94 (18) |
O4—S1—C8 | 109.39 (9) | C8—C9—C13 | 124.95 (18) |
N4—S1—C8 | 105.49 (9) | N5—C10—C11 | 124.2 (2) |
C3—O1—C1 | 117.99 (17) | N5—C10—H10 | 117.9 |
C5—O2—C2 | 117.95 (16) | C11—C10—H10 | 117.9 |
C16—O6—C13 | 117.59 (15) | C10—C11—C12 | 118.0 (2) |
C17—O8—C18 | 114.20 (16) | C10—C11—H11 | 121.0 |
C3—N1—C4 | 114.61 (17) | C12—C11—H11 | 121.0 |
C4—N2—C5 | 116.32 (17) | C11—C12—C8 | 118.9 (2) |
C7—N3—C4 | 130.02 (17) | C11—C12—H12 | 120.5 |
C7—N3—H3N | 115.0 | C8—C12—H12 | 120.5 |
C4—N3—H3N | 115.0 | O6—C13—C9 | 105.26 (15) |
C7—N4—S1 | 124.61 (15) | O6—C13—C14 | 108.51 (16) |
C7—N4—H4N | 117.7 | C9—C13—C14 | 111.96 (17) |
S1—N4—H4N | 117.7 | O6—C13—H13 | 110.3 |
C10—N5—C9 | 118.31 (19) | C9—C13—H13 | 110.3 |
O1—C1—H1A | 109.5 | C14—C13—H13 | 110.3 |
O1—C1—H1B | 109.5 | F1—C14—C15 | 108.89 (18) |
H1A—C1—H1B | 109.5 | F1—C14—C13 | 105.03 (17) |
O1—C1—H1C | 109.5 | C15—C14—C13 | 115.37 (19) |
H1A—C1—H1C | 109.5 | F1—C14—H14 | 109.1 |
H1B—C1—H1C | 109.5 | C15—C14—H14 | 109.1 |
O2—C2—H2A | 109.5 | C13—C14—H14 | 109.1 |
O2—C2—H2B | 109.5 | C14—C15—H15A | 109.5 |
H2A—C2—H2B | 109.5 | C14—C15—H15B | 109.5 |
O2—C2—H2C | 109.5 | H15A—C15—H15B | 109.5 |
H2A—C2—H2C | 109.5 | C14—C15—H15C | 109.5 |
H2B—C2—H2C | 109.5 | H15A—C15—H15C | 109.5 |
N1—C3—O1 | 119.08 (18) | H15B—C15—H15C | 109.5 |
N1—C3—C6 | 124.73 (19) | O7—C16—O6 | 124.13 (18) |
O1—C3—C6 | 116.20 (18) | O7—C16—C17 | 126.38 (18) |
N2—C4—N1 | 126.77 (18) | O6—C16—C17 | 109.49 (17) |
N2—C4—N3 | 117.95 (17) | O8—C17—C16 | 111.44 (17) |
N1—C4—N3 | 115.28 (17) | O8—C17—H17A | 109.3 |
O2—C5—N2 | 118.40 (17) | C16—C17—H17A | 109.3 |
O2—C5—C6 | 118.68 (18) | O8—C17—H17B | 109.3 |
N2—C5—C6 | 122.91 (18) | C16—C17—H17B | 109.3 |
C5—C6—C3 | 114.59 (19) | H17A—C17—H17B | 108.0 |
C5—C6—H6 | 122.7 | O8—C18—H18A | 109.5 |
C3—C6—H6 | 122.7 | O8—C18—H18B | 109.5 |
O3—C7—N4 | 123.77 (18) | H18A—C18—H18B | 109.5 |
O3—C7—N3 | 121.97 (18) | O8—C18—H18C | 109.5 |
N4—C7—N3 | 114.23 (18) | H18A—C18—H18C | 109.5 |
C12—C8—C9 | 119.55 (19) | H18B—C18—H18C | 109.5 |
O5—S1—N4—C7 | −48.10 (19) | O4—S1—C8—C9 | −42.99 (19) |
O4—S1—N4—C7 | −177.12 (16) | N4—S1—C8—C9 | 68.21 (18) |
C8—S1—N4—C7 | 67.84 (19) | C10—N5—C9—C8 | 0.1 (3) |
C4—N1—C3—O1 | 179.93 (18) | C10—N5—C9—C13 | −176.75 (18) |
C4—N1—C3—C6 | 0.4 (3) | C12—C8—C9—N5 | −1.9 (3) |
C1—O1—C3—N1 | −2.3 (3) | S1—C8—C9—N5 | 175.19 (15) |
C1—O1—C3—C6 | 177.23 (18) | C12—C8—C9—C13 | 174.60 (19) |
C5—N2—C4—N1 | −3.1 (3) | S1—C8—C9—C13 | −8.3 (3) |
C5—N2—C4—N3 | 177.34 (17) | C9—N5—C10—C11 | 2.1 (3) |
C3—N1—C4—N2 | 2.1 (3) | N5—C10—C11—C12 | −2.4 (3) |
C3—N1—C4—N3 | −178.32 (17) | C10—C11—C12—C8 | 0.5 (3) |
C7—N3—C4—N2 | −4.5 (3) | C9—C8—C12—C11 | 1.6 (3) |
C7—N3—C4—N1 | 175.92 (19) | S1—C8—C12—C11 | −175.75 (16) |
C2—O2—C5—N2 | 4.5 (3) | C16—O6—C13—C9 | 137.43 (16) |
C2—O2—C5—C6 | −176.37 (17) | C16—O6—C13—C14 | −102.57 (19) |
C4—N2—C5—O2 | −179.30 (17) | N5—C9—C13—O6 | 70.7 (2) |
C4—N2—C5—C6 | 1.6 (3) | C8—C9—C13—O6 | −106.1 (2) |
O2—C5—C6—C3 | −178.55 (17) | N5—C9—C13—C14 | −47.0 (2) |
N2—C5—C6—C3 | 0.6 (3) | C8—C9—C13—C14 | 136.2 (2) |
N1—C3—C6—C5 | −1.6 (3) | O6—C13—C14—F1 | −174.62 (16) |
O1—C3—C6—C5 | 178.85 (17) | C9—C13—C14—F1 | −58.9 (2) |
S1—N4—C7—O3 | −6.7 (3) | O6—C13—C14—C15 | 65.5 (2) |
S1—N4—C7—N3 | 175.33 (14) | C9—C13—C14—C15 | −178.77 (19) |
C4—N3—C7—O3 | 177.7 (2) | C13—O6—C16—O7 | 4.0 (3) |
C4—N3—C7—N4 | −4.4 (3) | C13—O6—C16—C17 | −175.72 (16) |
O5—S1—C8—C12 | 3.21 (18) | C18—O8—C17—C16 | 85.3 (2) |
O4—S1—C8—C12 | 134.21 (16) | O7—C16—C17—O8 | −25.1 (3) |
N4—S1—C8—C12 | −114.60 (16) | O6—C16—C17—O8 | 154.58 (15) |
O5—S1—C8—C9 | −173.98 (16) |
Cg1 is the centroid of the N5/C8–C12 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O8i | 0.88 | 2.01 | 2.885 (2) | 174 |
C1—H1A···O3i | 0.98 | 2.58 | 3.368 (3) | 137 |
C2—H2B···F1ii | 0.98 | 2.53 | 3.161 (2) | 122 |
C12—H12···O2iii | 0.95 | 2.42 | 3.229 (3) | 143 |
C17—H17A···O5iv | 0.99 | 2.55 | 3.367 (3) | 139 |
C1—H1B···Cg1i | 0.98 | 2.74 | 3.488 (2) | 134 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y−1, z; (iv) x, y+1, z. |
Funding information
This research was supported by the Basic Science Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2015R1D1A4A01020317 and 2017R1D1A3A03000534).
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