research communications
of penoxsulam
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, C16H14F5N5O5S [systematic name: 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy-1,2,4-triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide], is used as a herbicide. The of this structure comprises two independent molecules, A and B. The dihedral angles between the ring planes of the triazolopyrimidine ring systems and the benzene rings are 68.84 (7)° for A and 68.05 (6)° for B. In the crystal, weak intermolecular π–π interactions, with centroid–centroid separations of 3.4456 (17) and 3.5289 (15) Å and C—F⋯π [3.5335 (17) Å and 107.92 (13)°] contacts link adjacent molecules into chains along [001]. C—H⋯O and C—H⋯F hydrogen bonds link type B molecules into chains parallel to (100). Additional C—H⋯F hydrogen bonds together with short F⋯F contacts further aggregate the structure into a three-dimensional network.
CCDC reference: 1566461
1. Chemical context
Penxosulam is a triazolopyrimidine sulfonamide herbicide, which is used to control the growth of annual grasses, sedges, and broadleaf weeds in rice agriculture. The compound inhibits the synthesis of acetolactate and targets the biosynthesis of branch-chained amino acids, a metabolic pathway found in plants, fungi, and microorganisms. Acetolactate synthase (ALS) inhibitors are present in most effective herbicides. They are used in agriculture because they show a broad weed control spectrum, crop selectivity, are safe to humans, and can be applied at relatively low usage rates (Jabusch et al., 2005; Yasuor et al., 2009). Moreover, penoxsulam controls a number of troublesome weeds including northern jointvetch, alligatorweed, Texasweed/Mexicanweed, annual sedge, ducksalad, smartweed, and hemp sesbania (Willingham et al., 2008). We now report here the of penoxsulam, 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]-pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide.
2. Structural commentary
The penoxsulam molecule crystallizes with two independent molecules, A and B in the Fig. 1. The triazolopyrimidin unit caries methoxy substituents while the benzene ring of the benzenesulfonamide segment of the molecule carries trifluoro methyl and the unusual difluoroethoxy substituents. The dihedral angles between the planes of the triazolopyrimidine ring systems and the benzene ring planes are 68.84 (7)° in molecule A and 68.05 (6)° in B. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures for triazolopyrimidine (AboulWafa et al., 2014) and triazolopyrimidine sulfonamide herbicides (Kumar et al., 2012).
3. Supramolecular features
In the crystal, there are weak π–π interactions between the pyrimidine rings of neighbouring molecules of type A with Cg1⋯Cg1v = 3.4456 (17), and type B with Cg2⋯Cg2vi = 3.5289 (15) Å [Cg1 and Cg2 are the centroids of the N4/N5/C11–C14 and N9/N10/C28–C30 rings, respectively; symmetry codes: (v) −x, −y, −z + 1; (vi) −x + 2, −y, −z]. These combine with C25—F9⋯Cg3vii interactions involving the C3–C8 benzene ring to form chains along [001] (Fig. 2). C17—H17B⋯O8i and C20—H20⋯F9i hydrogen bonds form chains along the a-axis direction, forming a two-dimensional network in the ab plane (Fig. 3 and Table 1). In addition, short intermolecular F1⋯F5iii and F6⋯F10iii contacts [2.846 (2) and 2.794 (2) Å] together with C1—H1A⋯F10i, C16—H16C⋯F3ii, C18—H18⋯F10iii and C32—H32C⋯F8iv hydrogen bonds generate a three-dimensional network with molecules stacked along the a-axis direction (Fig. 4) and Table 1).
4. Database survey
Crystal structures of sulfonamide (Kang et al., 2015; Chen, Wu et al., 2005) and triazolopyrimidine (Chen, Li et al., 2005) herbicides have been reported previously. Moreover, the crystal structures of compounds with a triazolopyrimidine ring system and a benzene ring in the molecule, ethyl 2-(5,7-dimethyl-1,2,4-triazolo[1,5-a]-pyrimidin-2-yloxy)benzoate (Chen, Li et al., 2005) and 5-(4-Chlorophenoxy)-6-isopropyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]-pyrimidin-7(6H)-one (Zeng et al., 2009) have also been reported.
5. Synthesis and crystallization
The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Single crystals were obtained by slow evaporation of an acetonitrile solution.
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(H) = 1.2Ueq(C) for the N—H group, d(C—H) = 0.95 Å, Uiso(H) = 1.2Ueq(C) for aromatic C—H, d(C—H) = 0.98 Å, Uiso(H) = 1.5Ueq(C) for methyl group, d(C—H) = 0.99 Å, Uiso(H) = 1.2Ueq(C) for Csp3—H, and d(C—H) = 1.00 Å, Uiso(H) = 1.5Ueq(C) for Csp3—H.
details are summarized in Table 2
|
Supporting information
CCDC reference: 1566461
https://doi.org/10.1107/S2056989017011458/sj5532sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017011458/sj5532Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989017011458/sj5532Isup3.cml
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).C16H14F5N5O5S | Z = 4 |
Mr = 483.38 | F(000) = 984 |
Triclinic, P1 | Dx = 1.689 Mg m−3 |
a = 8.1945 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.3733 (3) Å | Cell parameters from 9990 reflections |
c = 28.3277 (9) Å | θ = 2.5–27.3° |
α = 82.698 (2)° | µ = 0.26 mm−1 |
β = 84.183 (2)° | T = 173 K |
γ = 81.814 (2)° | Plate, colourless |
V = 1901.43 (12) Å3 | 0.40 × 0.19 × 0.11 mm |
Bruker APEXII CCD diffractometer | 5503 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.032 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 25.0°, θmin = 1.5° |
Tmin = 0.646, Tmax = 0.746 | h = −9→9 |
24336 measured reflections | k = −9→9 |
6571 independent reflections | l = −32→33 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0438P)2 + 1.5689P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
6571 reflections | Δρmax = 0.47 e Å−3 |
581 parameters | Δρmin = −0.52 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 | 0.40491 (7) | 0.27322 (7) | 0.33986 (2) | 0.02327 (15) | |
S2 | 1.17808 (7) | 0.29094 (7) | 0.15763 (2) | 0.02404 (15) | |
F1 | 0.6784 (2) | −0.21313 (19) | 0.28932 (6) | 0.0473 (4) | |
F2 | 0.6798 (2) | −0.2261 (2) | 0.36604 (6) | 0.0526 (5) | |
F3 | 0.0164 (2) | 0.53003 (19) | 0.34514 (6) | 0.0477 (4) | |
F4 | 0.18482 (19) | 0.53143 (16) | 0.28142 (5) | 0.0326 (3) | |
F5 | −0.0713 (2) | 0.51888 (19) | 0.27738 (6) | 0.0465 (4) | |
F6 | 0.6485 (2) | 0.5512 (2) | 0.21727 (6) | 0.0501 (4) | |
F7 | 0.6787 (3) | 0.5868 (2) | 0.13991 (7) | 0.0629 (5) | |
F8 | 1.4342 (2) | −0.0947 (2) | 0.15363 (6) | 0.0505 (5) | |
F9 | 1.39010 (18) | 0.03048 (19) | 0.21686 (5) | 0.0381 (4) | |
F10 | 1.3647 (2) | −0.22070 (19) | 0.22130 (6) | 0.0523 (5) | |
O1 | 0.4016 (2) | −0.06137 (18) | 0.33033 (6) | 0.0292 (4) | |
O2 | 0.3455 (2) | 0.42426 (19) | 0.35764 (6) | 0.0343 (4) | |
O3 | 0.5333 (2) | 0.2632 (2) | 0.30221 (6) | 0.0356 (4) | |
O4 | 0.3555 (3) | −0.3031 (3) | 0.52168 (8) | 0.0591 (6) | |
O5 | 0.0298 (3) | 0.3079 (3) | 0.51945 (7) | 0.0460 (5) | |
O6 | 0.8254 (2) | 0.2966 (2) | 0.17644 (6) | 0.0309 (4) | |
O7 | 1.1568 (2) | 0.3944 (2) | 0.19444 (6) | 0.0349 (4) | |
O8 | 1.3393 (2) | 0.2352 (2) | 0.13777 (6) | 0.0334 (4) | |
O9 | 0.7015 (3) | 0.3776 (3) | −0.02223 (8) | 0.0535 (6) | |
O10 | 1.3171 (3) | 0.0395 (3) | −0.02043 (7) | 0.0449 (5) | |
N1 | 0.4795 (2) | 0.1502 (2) | 0.38497 (7) | 0.0250 (4) | |
H1N | 0.5842 | 0.1083 | 0.3822 | 0.030* | |
N2 | 0.4113 (3) | −0.0440 (2) | 0.44874 (8) | 0.0315 (5) | |
N3 | 0.2718 (3) | 0.2139 (2) | 0.44832 (7) | 0.0293 (5) | |
N4 | 0.2201 (3) | 0.1158 (3) | 0.48799 (7) | 0.0360 (5) | |
N5 | 0.0657 (4) | 0.0425 (4) | 0.55905 (8) | 0.0537 (7) | |
N6 | 1.0775 (3) | 0.3946 (2) | 0.11402 (7) | 0.0273 (5) | |
H6N | 1.0315 | 0.4945 | 0.1175 | 0.033* | |
N7 | 0.9191 (3) | 0.3767 (2) | 0.05042 (7) | 0.0313 (5) | |
N8 | 1.1790 (3) | 0.2324 (3) | 0.05044 (7) | 0.0303 (5) | |
N9 | 1.1034 (3) | 0.2116 (3) | 0.01107 (7) | 0.0354 (5) | |
N10 | 1.0719 (3) | 0.1088 (3) | −0.05969 (8) | 0.0483 (6) | |
C1 | 0.4275 (3) | −0.2344 (3) | 0.33482 (10) | 0.0319 (6) | |
H1A | 0.3768 | −0.2749 | 0.3091 | 0.038* | |
H1B | 0.3776 | −0.2797 | 0.3661 | 0.038* | |
C2 | 0.6090 (4) | −0.2821 (3) | 0.33091 (10) | 0.0366 (7) | |
H2 | 0.6349 | −0.4030 | 0.3329 | 0.044* | |
C3 | 0.2487 (3) | 0.0195 (3) | 0.32428 (8) | 0.0226 (5) | |
C4 | 0.1131 (3) | −0.0560 (3) | 0.31745 (9) | 0.0283 (6) | |
H4 | 0.1223 | −0.1710 | 0.3198 | 0.034* | |
C5 | −0.0334 (3) | 0.0372 (3) | 0.30731 (9) | 0.0319 (6) | |
H5 | −0.1263 | −0.0142 | 0.3032 | 0.038* | |
C6 | −0.0480 (3) | 0.2044 (3) | 0.30301 (9) | 0.0291 (6) | |
H6 | −0.1488 | 0.2671 | 0.2944 | 0.035* | |
C7 | 0.0837 (3) | 0.2816 (3) | 0.31124 (8) | 0.0219 (5) | |
C8 | 0.2322 (3) | 0.1891 (3) | 0.32403 (7) | 0.0188 (5) | |
C9 | 0.0556 (3) | 0.4652 (3) | 0.30368 (9) | 0.0303 (6) | |
C10 | 0.3842 (3) | 0.1093 (3) | 0.42737 (8) | 0.0264 (5) | |
C11 | 0.3046 (3) | −0.0355 (3) | 0.48755 (9) | 0.0303 (6) | |
C12 | 0.2670 (4) | −0.1556 (4) | 0.52547 (11) | 0.0451 (8) | |
C13 | 0.1508 (4) | −0.1123 (4) | 0.55917 (10) | 0.0472 (8) | |
H13 | 0.1246 | −0.1919 | 0.5848 | 0.057* | |
C14 | 0.1007 (4) | 0.1546 (4) | 0.52415 (9) | 0.0400 (7) | |
C15 | 0.3152 (5) | −0.4323 (4) | 0.55754 (13) | 0.0761 (13) | |
H15A | 0.3362 | −0.4064 | 0.5890 | 0.114* | |
H15B | 0.3837 | −0.5338 | 0.5506 | 0.114* | |
H15C | 0.1981 | −0.4448 | 0.5575 | 0.114* | |
C16 | −0.0932 (4) | 0.3529 (4) | 0.55773 (11) | 0.0618 (10) | |
H16A | −0.1876 | 0.2927 | 0.5580 | 0.093* | |
H16B | −0.1309 | 0.4697 | 0.5526 | 0.093* | |
H16C | −0.0443 | 0.3266 | 0.5884 | 0.093* | |
C17 | 0.6501 (3) | 0.3241 (3) | 0.17727 (11) | 0.0388 (7) | |
H17A | 0.5996 | 0.2640 | 0.2062 | 0.047* | |
H17B | 0.6132 | 0.2872 | 0.1487 | 0.047* | |
C18 | 0.6008 (4) | 0.5018 (4) | 0.17763 (12) | 0.0460 (8) | |
H18 | 0.4782 | 0.5284 | 0.1767 | 0.055* | |
C19 | 0.8998 (3) | 0.1400 (3) | 0.17952 (8) | 0.0244 (5) | |
C20 | 0.8126 (3) | 0.0072 (3) | 0.18630 (9) | 0.0326 (6) | |
H20 | 0.6953 | 0.0231 | 0.1871 | 0.039* | |
C21 | 0.8963 (3) | −0.1464 (3) | 0.19184 (9) | 0.0350 (6) | |
H21 | 0.8369 | −0.2372 | 0.1948 | 0.042* | |
C22 | 1.0651 (3) | −0.1711 (3) | 0.19321 (9) | 0.0321 (6) | |
H22 | 1.1208 | −0.2783 | 0.1991 | 0.039* | |
C23 | 1.1547 (3) | −0.0404 (3) | 0.18604 (8) | 0.0238 (5) | |
C24 | 1.0729 (3) | 0.1177 (3) | 0.17622 (8) | 0.0203 (5) | |
C25 | 1.3353 (3) | −0.0779 (3) | 0.19369 (9) | 0.0344 (6) | |
C26 | 1.0613 (3) | 0.3314 (3) | 0.07141 (8) | 0.0257 (5) | |
C27 | 0.9510 (3) | 0.2979 (3) | 0.01135 (8) | 0.0275 (6) | |
C28 | 0.8526 (4) | 0.2892 (3) | −0.02617 (10) | 0.0407 (7) | |
C29 | 0.9154 (4) | 0.1956 (4) | −0.05974 (9) | 0.0422 (7) | |
H29 | 0.8498 | 0.1880 | −0.0850 | 0.051* | |
C30 | 1.1653 (4) | 0.1154 (3) | −0.02503 (9) | 0.0369 (7) | |
C31 | 0.5908 (5) | 0.3640 (5) | −0.05730 (12) | 0.0651 (10) | |
H31A | 0.6383 | 0.4036 | −0.0891 | 0.098* | |
H31B | 0.4841 | 0.4291 | −0.0501 | 0.098* | |
H31C | 0.5747 | 0.2500 | −0.0567 | 0.098* | |
C32 | 1.3861 (4) | −0.0568 (4) | −0.05853 (11) | 0.0574 (9) | |
H32A | 1.3238 | −0.1487 | −0.0580 | 0.086* | |
H32B | 1.5023 | −0.0976 | −0.0540 | 0.086* | |
H32C | 1.3789 | 0.0106 | −0.0894 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0248 (3) | 0.0191 (3) | 0.0273 (3) | −0.0096 (2) | −0.0074 (2) | 0.0035 (2) |
S2 | 0.0227 (3) | 0.0273 (3) | 0.0243 (3) | −0.0104 (3) | −0.0056 (2) | −0.0001 (2) |
F1 | 0.0495 (11) | 0.0363 (9) | 0.0517 (10) | −0.0063 (8) | 0.0157 (8) | −0.0038 (8) |
F2 | 0.0434 (11) | 0.0549 (11) | 0.0572 (11) | 0.0058 (8) | −0.0152 (9) | −0.0032 (9) |
F3 | 0.0608 (12) | 0.0387 (9) | 0.0427 (9) | 0.0094 (8) | −0.0013 (8) | −0.0212 (7) |
F4 | 0.0448 (9) | 0.0202 (7) | 0.0334 (8) | −0.0065 (6) | −0.0109 (7) | 0.0034 (6) |
F5 | 0.0383 (10) | 0.0389 (9) | 0.0598 (11) | 0.0152 (7) | −0.0215 (8) | −0.0052 (8) |
F6 | 0.0374 (10) | 0.0509 (10) | 0.0675 (12) | −0.0021 (8) | −0.0103 (8) | −0.0271 (9) |
F7 | 0.0708 (14) | 0.0459 (10) | 0.0689 (13) | 0.0095 (10) | −0.0230 (11) | 0.0004 (9) |
F8 | 0.0353 (10) | 0.0617 (11) | 0.0460 (10) | 0.0086 (8) | 0.0167 (8) | −0.0063 (8) |
F9 | 0.0239 (8) | 0.0547 (10) | 0.0349 (8) | −0.0035 (7) | −0.0082 (6) | 0.0007 (7) |
F10 | 0.0421 (11) | 0.0414 (9) | 0.0616 (11) | 0.0160 (8) | −0.0023 (8) | 0.0140 (8) |
O1 | 0.0291 (10) | 0.0136 (8) | 0.0455 (10) | −0.0016 (7) | −0.0089 (8) | −0.0020 (7) |
O2 | 0.0486 (12) | 0.0161 (8) | 0.0417 (10) | −0.0081 (8) | −0.0193 (9) | −0.0008 (7) |
O3 | 0.0253 (10) | 0.0465 (11) | 0.0347 (10) | −0.0149 (8) | −0.0016 (8) | 0.0073 (8) |
O4 | 0.0559 (15) | 0.0501 (14) | 0.0696 (15) | −0.0188 (12) | −0.0251 (12) | 0.0290 (11) |
O5 | 0.0544 (14) | 0.0528 (13) | 0.0349 (11) | −0.0212 (11) | 0.0097 (9) | −0.0158 (9) |
O6 | 0.0160 (9) | 0.0283 (9) | 0.0490 (11) | −0.0019 (7) | −0.0057 (8) | −0.0056 (8) |
O7 | 0.0458 (12) | 0.0342 (10) | 0.0298 (10) | −0.0159 (9) | −0.0095 (8) | −0.0062 (8) |
O8 | 0.0191 (9) | 0.0468 (11) | 0.0346 (10) | −0.0121 (8) | −0.0033 (7) | 0.0041 (8) |
O9 | 0.0629 (16) | 0.0460 (12) | 0.0560 (13) | −0.0108 (11) | −0.0342 (11) | 0.0043 (10) |
O10 | 0.0409 (13) | 0.0634 (13) | 0.0343 (11) | −0.0178 (11) | 0.0065 (9) | −0.0158 (10) |
N1 | 0.0177 (11) | 0.0273 (11) | 0.0302 (11) | −0.0045 (8) | −0.0094 (8) | 0.0041 (9) |
N2 | 0.0320 (13) | 0.0284 (11) | 0.0357 (12) | −0.0117 (10) | −0.0146 (10) | 0.0086 (9) |
N3 | 0.0346 (13) | 0.0310 (11) | 0.0249 (11) | −0.0144 (10) | −0.0046 (9) | −0.0004 (9) |
N4 | 0.0387 (14) | 0.0455 (14) | 0.0273 (12) | −0.0188 (11) | −0.0086 (10) | 0.0014 (10) |
N5 | 0.0623 (19) | 0.079 (2) | 0.0285 (13) | −0.0423 (16) | −0.0065 (12) | 0.0003 (13) |
N6 | 0.0355 (13) | 0.0201 (10) | 0.0276 (11) | −0.0067 (9) | −0.0086 (9) | 0.0003 (8) |
N7 | 0.0346 (13) | 0.0272 (11) | 0.0332 (12) | −0.0091 (10) | −0.0120 (10) | 0.0055 (9) |
N8 | 0.0332 (13) | 0.0358 (12) | 0.0242 (11) | −0.0126 (10) | −0.0043 (9) | −0.0018 (9) |
N9 | 0.0446 (15) | 0.0384 (13) | 0.0262 (12) | −0.0190 (11) | −0.0053 (10) | 0.0026 (10) |
N10 | 0.0610 (15) | 0.0614 (17) | 0.0280 (12) | −0.0318 (12) | −0.0021 (12) | −0.0012 (11) |
C1 | 0.0404 (16) | 0.0120 (11) | 0.0417 (15) | −0.0024 (11) | −0.0001 (12) | −0.0003 (10) |
C2 | 0.0409 (17) | 0.0201 (13) | 0.0451 (17) | 0.0000 (12) | 0.0027 (13) | 0.0004 (12) |
C3 | 0.0243 (14) | 0.0218 (12) | 0.0212 (12) | −0.0040 (10) | −0.0013 (10) | 0.0005 (9) |
C4 | 0.0325 (15) | 0.0232 (12) | 0.0317 (14) | −0.0128 (11) | −0.0013 (11) | −0.0039 (10) |
C5 | 0.0253 (14) | 0.0408 (15) | 0.0337 (14) | −0.0175 (12) | 0.0000 (11) | −0.0069 (12) |
C6 | 0.0192 (13) | 0.0387 (15) | 0.0300 (13) | −0.0029 (11) | −0.0016 (10) | −0.0075 (11) |
C7 | 0.0218 (13) | 0.0239 (12) | 0.0199 (11) | −0.0014 (10) | −0.0008 (9) | −0.0049 (9) |
C8 | 0.0214 (13) | 0.0177 (11) | 0.0180 (11) | −0.0064 (9) | −0.0005 (9) | −0.0011 (9) |
C9 | 0.0319 (15) | 0.0264 (13) | 0.0319 (14) | 0.0070 (11) | −0.0075 (11) | −0.0090 (11) |
C10 | 0.0281 (14) | 0.0276 (13) | 0.0268 (13) | −0.0126 (11) | −0.0119 (11) | 0.0021 (10) |
C11 | 0.0300 (15) | 0.0359 (15) | 0.0285 (14) | −0.0172 (12) | −0.0143 (11) | 0.0068 (11) |
C12 | 0.0468 (19) | 0.0523 (19) | 0.0403 (17) | −0.0251 (16) | −0.0251 (15) | 0.0175 (14) |
C13 | 0.056 (2) | 0.065 (2) | 0.0266 (15) | −0.0373 (18) | −0.0174 (14) | 0.0175 (14) |
C14 | 0.0433 (18) | 0.059 (2) | 0.0240 (14) | −0.0256 (15) | −0.0038 (12) | −0.0066 (13) |
C15 | 0.099 (3) | 0.062 (2) | 0.072 (2) | −0.043 (2) | −0.039 (2) | 0.0379 (19) |
C16 | 0.071 (2) | 0.078 (2) | 0.0443 (19) | −0.036 (2) | 0.0250 (17) | −0.0330 (18) |
C17 | 0.0167 (14) | 0.0439 (16) | 0.0591 (18) | −0.0001 (12) | −0.0096 (12) | −0.0178 (14) |
C18 | 0.0244 (16) | 0.0511 (18) | 0.067 (2) | 0.0050 (14) | −0.0176 (14) | −0.0227 (16) |
C19 | 0.0220 (13) | 0.0267 (13) | 0.0252 (12) | −0.0033 (10) | −0.0033 (10) | −0.0045 (10) |
C20 | 0.0242 (14) | 0.0402 (15) | 0.0362 (15) | −0.0136 (12) | −0.0006 (11) | −0.0065 (12) |
C21 | 0.0431 (18) | 0.0301 (14) | 0.0355 (15) | −0.0191 (13) | 0.0012 (12) | −0.0059 (11) |
C22 | 0.0437 (17) | 0.0238 (13) | 0.0280 (13) | −0.0046 (12) | 0.0018 (12) | −0.0036 (10) |
C23 | 0.0251 (13) | 0.0263 (13) | 0.0185 (11) | −0.0025 (10) | 0.0038 (10) | −0.0020 (10) |
C24 | 0.0182 (12) | 0.0238 (12) | 0.0195 (11) | −0.0059 (10) | −0.0009 (9) | −0.0022 (9) |
C25 | 0.0301 (15) | 0.0367 (15) | 0.0312 (14) | 0.0040 (12) | 0.0026 (12) | 0.0019 (12) |
C26 | 0.0300 (14) | 0.0230 (12) | 0.0254 (13) | −0.0114 (11) | −0.0061 (11) | 0.0043 (10) |
C27 | 0.0373 (16) | 0.0241 (13) | 0.0230 (13) | −0.0144 (11) | −0.0087 (11) | 0.0072 (10) |
C28 | 0.053 (2) | 0.0354 (15) | 0.0367 (16) | −0.0185 (14) | −0.0211 (14) | 0.0123 (13) |
C29 | 0.0613 (17) | 0.0504 (18) | 0.0212 (13) | −0.0282 (13) | −0.0155 (13) | 0.0046 (12) |
C30 | 0.0489 (19) | 0.0424 (16) | 0.0233 (14) | −0.0242 (14) | 0.0030 (12) | −0.0027 (12) |
C31 | 0.066 (3) | 0.073 (2) | 0.062 (2) | −0.022 (2) | −0.0397 (19) | 0.0113 (18) |
C32 | 0.056 (2) | 0.081 (2) | 0.0413 (18) | −0.0272 (19) | 0.0199 (16) | −0.0260 (17) |
S1—O3 | 1.4217 (18) | N10—C30 | 1.316 (4) |
S1—O2 | 1.4238 (18) | N10—C29 | 1.381 (4) |
S1—N1 | 1.6466 (19) | C1—C2 | 1.481 (4) |
S1—C8 | 1.787 (2) | C1—H1A | 0.9900 |
S2—O7 | 1.4207 (18) | C1—H1B | 0.9900 |
S2—O8 | 1.4210 (18) | C2—H2 | 1.0000 |
S2—N6 | 1.640 (2) | C3—C4 | 1.395 (3) |
S2—C24 | 1.788 (2) | C3—C8 | 1.406 (3) |
F1—C2 | 1.353 (3) | C4—C5 | 1.371 (4) |
F2—C2 | 1.364 (3) | C4—H4 | 0.9500 |
F3—C9 | 1.346 (3) | C5—C6 | 1.379 (4) |
F4—C9 | 1.330 (3) | C5—H5 | 0.9500 |
F5—C9 | 1.333 (3) | C6—C7 | 1.388 (3) |
F6—C18 | 1.355 (3) | C6—H6 | 0.9500 |
F7—C18 | 1.361 (4) | C7—C8 | 1.401 (3) |
F8—C25 | 1.336 (3) | C7—C9 | 1.513 (3) |
F9—C25 | 1.335 (3) | C11—C12 | 1.417 (4) |
F10—C25 | 1.348 (3) | C12—C13 | 1.324 (5) |
O1—C3 | 1.353 (3) | C13—H13 | 0.9500 |
O1—C1 | 1.425 (3) | C15—H15A | 0.9800 |
O4—C12 | 1.351 (4) | C15—H15B | 0.9800 |
O4—C15 | 1.438 (4) | C15—H15C | 0.9800 |
O5—C14 | 1.328 (4) | C16—H16A | 0.9800 |
O5—C16 | 1.452 (3) | C16—H16B | 0.9800 |
O6—C19 | 1.361 (3) | C16—H16C | 0.9800 |
O6—C17 | 1.420 (3) | C17—C18 | 1.487 (4) |
O9—C28 | 1.351 (4) | C17—H17A | 0.9900 |
O9—C31 | 1.436 (4) | C17—H17B | 0.9900 |
O10—C30 | 1.324 (4) | C18—H18 | 1.0000 |
O10—C32 | 1.450 (3) | C19—C20 | 1.389 (3) |
N1—C10 | 1.397 (3) | C19—C24 | 1.399 (3) |
N1—H1N | 0.8800 | C20—C21 | 1.367 (4) |
N2—C11 | 1.336 (3) | C20—H20 | 0.9500 |
N2—C10 | 1.346 (3) | C21—C22 | 1.373 (4) |
N3—C10 | 1.326 (3) | C21—H21 | 0.9500 |
N3—N4 | 1.373 (3) | C22—C23 | 1.386 (3) |
N4—C11 | 1.355 (3) | C22—H22 | 0.9500 |
N4—C14 | 1.380 (4) | C23—C24 | 1.403 (3) |
N5—C14 | 1.313 (4) | C23—C25 | 1.501 (4) |
N5—C13 | 1.382 (4) | C27—C28 | 1.413 (4) |
N6—C26 | 1.403 (3) | C28—C29 | 1.326 (4) |
N6—H6N | 0.8800 | C29—H29 | 0.9500 |
N7—C27 | 1.344 (3) | C31—H31A | 0.9800 |
N7—C26 | 1.346 (3) | C31—H31B | 0.9800 |
N8—C26 | 1.323 (3) | C31—H31C | 0.9800 |
N8—N9 | 1.370 (3) | C32—H32A | 0.9800 |
N9—C27 | 1.350 (3) | C32—H32B | 0.9800 |
N9—C30 | 1.393 (3) | C32—H32C | 0.9800 |
O3—S1—O2 | 120.60 (11) | C12—C13—N5 | 123.4 (3) |
O3—S1—N1 | 104.84 (11) | C12—C13—H13 | 118.3 |
O2—S1—N1 | 106.54 (10) | N5—C13—H13 | 118.3 |
O3—S1—C8 | 109.19 (10) | N5—C14—O5 | 125.9 (3) |
O2—S1—C8 | 108.35 (11) | N5—C14—N4 | 119.6 (3) |
N1—S1—C8 | 106.43 (10) | O5—C14—N4 | 114.5 (2) |
O7—S2—O8 | 120.38 (11) | O4—C15—H15A | 109.5 |
O7—S2—N6 | 104.97 (11) | O4—C15—H15B | 109.5 |
O8—S2—N6 | 107.16 (11) | H15A—C15—H15B | 109.5 |
O7—S2—C24 | 109.88 (10) | O4—C15—H15C | 109.5 |
O8—S2—C24 | 107.92 (11) | H15A—C15—H15C | 109.5 |
N6—S2—C24 | 105.54 (10) | H15B—C15—H15C | 109.5 |
C3—O1—C1 | 120.10 (19) | O5—C16—H16A | 109.5 |
C12—O4—C15 | 116.5 (3) | O5—C16—H16B | 109.5 |
C14—O5—C16 | 115.5 (2) | H16A—C16—H16B | 109.5 |
C19—O6—C17 | 117.77 (19) | O5—C16—H16C | 109.5 |
C28—O9—C31 | 116.7 (3) | H16A—C16—H16C | 109.5 |
C30—O10—C32 | 115.5 (2) | H16B—C16—H16C | 109.5 |
C10—N1—S1 | 123.11 (17) | O6—C17—C18 | 106.7 (2) |
C10—N1—H1N | 118.4 | O6—C17—H17A | 110.4 |
S1—N1—H1N | 118.4 | C18—C17—H17A | 110.4 |
C11—N2—C10 | 100.9 (2) | O6—C17—H17B | 110.4 |
C10—N3—N4 | 100.3 (2) | C18—C17—H17B | 110.4 |
C11—N4—N3 | 109.7 (2) | H17A—C17—H17B | 108.6 |
C11—N4—C14 | 121.8 (2) | F6—C18—F7 | 105.9 (2) |
N3—N4—C14 | 128.4 (2) | F6—C18—C17 | 110.2 (3) |
C14—N5—C13 | 119.3 (3) | F7—C18—C17 | 111.1 (2) |
C26—N6—S2 | 123.03 (17) | F6—C18—H18 | 109.9 |
C26—N6—H6N | 118.5 | F7—C18—H18 | 109.9 |
S2—N6—H6N | 118.5 | C17—C18—H18 | 109.9 |
C27—N7—C26 | 100.8 (2) | O6—C19—C20 | 123.2 (2) |
C26—N8—N9 | 100.1 (2) | O6—C19—C24 | 116.2 (2) |
C27—N9—N8 | 110.4 (2) | C20—C19—C24 | 120.5 (2) |
C27—N9—C30 | 121.9 (2) | C21—C20—C19 | 119.7 (2) |
N8—N9—C30 | 127.7 (2) | C21—C20—H20 | 120.1 |
C30—N10—C29 | 120.1 (3) | C19—C20—H20 | 120.1 |
O1—C1—C2 | 106.3 (2) | C20—C21—C22 | 120.8 (2) |
O1—C1—H1A | 110.5 | C20—C21—H21 | 119.6 |
C2—C1—H1A | 110.5 | C22—C21—H21 | 119.6 |
O1—C1—H1B | 110.5 | C21—C22—C23 | 120.3 (2) |
C2—C1—H1B | 110.5 | C21—C22—H22 | 119.8 |
H1A—C1—H1B | 108.7 | C23—C22—H22 | 119.8 |
F1—C2—F2 | 105.6 (2) | C22—C23—C24 | 119.8 (2) |
F1—C2—C1 | 110.6 (2) | C22—C23—C25 | 116.3 (2) |
F2—C2—C1 | 110.8 (2) | C24—C23—C25 | 123.7 (2) |
F1—C2—H2 | 109.9 | C19—C24—C23 | 118.3 (2) |
F2—C2—H2 | 109.9 | C19—C24—S2 | 118.21 (17) |
C1—C2—H2 | 109.9 | C23—C24—S2 | 123.49 (18) |
O1—C3—C4 | 123.6 (2) | F9—C25—F8 | 108.1 (2) |
O1—C3—C8 | 116.1 (2) | F9—C25—F10 | 105.0 (2) |
C4—C3—C8 | 120.3 (2) | F8—C25—F10 | 105.2 (2) |
C5—C4—C3 | 119.5 (2) | F9—C25—C23 | 113.5 (2) |
C5—C4—H4 | 120.3 | F8—C25—C23 | 114.2 (2) |
C3—C4—H4 | 120.3 | F10—C25—C23 | 110.2 (2) |
C4—C5—C6 | 121.0 (2) | N8—C26—N7 | 118.5 (2) |
C4—C5—H5 | 119.5 | N8—C26—N6 | 123.6 (2) |
C6—C5—H5 | 119.5 | N7—C26—N6 | 117.9 (2) |
C5—C6—C7 | 120.4 (2) | N7—C27—N9 | 110.3 (2) |
C5—C6—H6 | 119.8 | N7—C27—C28 | 131.1 (3) |
C7—C6—H6 | 119.8 | N9—C27—C28 | 118.6 (2) |
C6—C7—C8 | 119.8 (2) | C29—C28—O9 | 128.1 (3) |
C6—C7—C9 | 115.7 (2) | C29—C28—C27 | 117.8 (3) |
C8—C7—C9 | 124.5 (2) | O9—C28—C27 | 114.0 (3) |
C7—C8—C3 | 118.7 (2) | C28—C29—N10 | 122.9 (3) |
C7—C8—S1 | 124.01 (17) | C28—C29—H29 | 118.5 |
C3—C8—S1 | 117.28 (18) | N10—C29—H29 | 118.5 |
F4—C9—F5 | 106.3 (2) | N10—C30—O10 | 126.7 (3) |
F4—C9—F3 | 107.5 (2) | N10—C30—N9 | 118.7 (3) |
F5—C9—F3 | 105.6 (2) | O10—C30—N9 | 114.6 (2) |
F4—C9—C7 | 113.7 (2) | O9—C31—H31A | 109.5 |
F5—C9—C7 | 111.2 (2) | O9—C31—H31B | 109.5 |
F3—C9—C7 | 112.0 (2) | H31A—C31—H31B | 109.5 |
N3—C10—N2 | 118.3 (2) | O9—C31—H31C | 109.5 |
N3—C10—N1 | 123.7 (2) | H31A—C31—H31C | 109.5 |
N2—C10—N1 | 118.0 (2) | H31B—C31—H31C | 109.5 |
N2—C11—N4 | 110.8 (2) | O10—C32—H32A | 109.5 |
N2—C11—C12 | 130.9 (3) | O10—C32—H32B | 109.5 |
N4—C11—C12 | 118.2 (3) | H32A—C32—H32B | 109.5 |
C13—C12—O4 | 128.3 (3) | O10—C32—H32C | 109.5 |
C13—C12—C11 | 117.6 (3) | H32A—C32—H32C | 109.5 |
O4—C12—C11 | 114.1 (3) | H32B—C32—H32C | 109.5 |
O3—S1—N1—C10 | −171.86 (18) | C16—O5—C14—N4 | −178.4 (2) |
O2—S1—N1—C10 | 59.2 (2) | C11—N4—C14—N5 | −0.7 (4) |
C8—S1—N1—C10 | −56.2 (2) | N3—N4—C14—N5 | 178.7 (2) |
C10—N3—N4—C11 | 0.3 (2) | C11—N4—C14—O5 | 179.8 (2) |
C10—N3—N4—C14 | −179.1 (2) | N3—N4—C14—O5 | −0.9 (4) |
O7—S2—N6—C26 | −176.81 (19) | C19—O6—C17—C18 | 175.3 (2) |
O8—S2—N6—C26 | 54.1 (2) | O6—C17—C18—F6 | −61.3 (3) |
C24—S2—N6—C26 | −60.7 (2) | O6—C17—C18—F7 | 55.7 (3) |
C26—N8—N9—C27 | 0.3 (2) | C17—O6—C19—C20 | −4.0 (3) |
C26—N8—N9—C30 | −178.6 (2) | C17—O6—C19—C24 | 177.0 (2) |
C3—O1—C1—C2 | 168.7 (2) | O6—C19—C20—C21 | −176.2 (2) |
O1—C1—C2—F1 | −56.8 (3) | C24—C19—C20—C21 | 2.8 (4) |
O1—C1—C2—F2 | 59.8 (3) | C19—C20—C21—C22 | 3.3 (4) |
C1—O1—C3—C4 | −6.4 (3) | C20—C21—C22—C23 | −4.0 (4) |
C1—O1—C3—C8 | 175.1 (2) | C21—C22—C23—C24 | −1.5 (4) |
O1—C3—C4—C5 | −174.1 (2) | C21—C22—C23—C25 | 173.3 (2) |
C8—C3—C4—C5 | 4.3 (3) | O6—C19—C24—C23 | 171.0 (2) |
C3—C4—C5—C6 | 1.0 (4) | C20—C19—C24—C23 | −8.1 (3) |
C4—C5—C6—C7 | −3.2 (4) | O6—C19—C24—S2 | −11.3 (3) |
C5—C6—C7—C8 | 0.0 (3) | C20—C19—C24—S2 | 169.70 (19) |
C5—C6—C7—C9 | 177.8 (2) | C22—C23—C24—C19 | 7.4 (3) |
C6—C7—C8—C3 | 5.3 (3) | C25—C23—C24—C19 | −167.0 (2) |
C9—C7—C8—C3 | −172.4 (2) | C22—C23—C24—S2 | −170.27 (18) |
C6—C7—C8—S1 | −175.15 (17) | C25—C23—C24—S2 | 15.3 (3) |
C9—C7—C8—S1 | 7.2 (3) | O7—S2—C24—C19 | 71.2 (2) |
O1—C3—C8—C7 | 171.1 (2) | O8—S2—C24—C19 | −155.77 (18) |
C4—C3—C8—C7 | −7.5 (3) | N6—S2—C24—C19 | −41.5 (2) |
O1—C3—C8—S1 | −8.5 (3) | O7—S2—C24—C23 | −111.1 (2) |
C4—C3—C8—S1 | 172.95 (18) | O8—S2—C24—C23 | 21.9 (2) |
O3—S1—C8—C7 | −107.6 (2) | N6—S2—C24—C23 | 136.22 (19) |
O2—S1—C8—C7 | 25.5 (2) | C22—C23—C25—F9 | −138.3 (2) |
N1—S1—C8—C7 | 139.78 (19) | C24—C23—C25—F9 | 36.3 (3) |
O3—S1—C8—C3 | 72.01 (19) | C22—C23—C25—F8 | 97.3 (3) |
O2—S1—C8—C3 | −154.89 (17) | C24—C23—C25—F8 | −88.1 (3) |
N1—S1—C8—C3 | −40.7 (2) | C22—C23—C25—F10 | −20.8 (3) |
C6—C7—C9—F4 | −138.2 (2) | C24—C23—C25—F10 | 153.8 (2) |
C8—C7—C9—F4 | 39.5 (3) | N9—N8—C26—N7 | 0.1 (3) |
C6—C7—C9—F5 | −18.2 (3) | N9—N8—C26—N6 | −178.7 (2) |
C8—C7—C9—F5 | 159.5 (2) | C27—N7—C26—N8 | −0.5 (3) |
C6—C7—C9—F3 | 99.7 (3) | C27—N7—C26—N6 | 178.4 (2) |
C8—C7—C9—F3 | −82.6 (3) | S2—N6—C26—N8 | −36.0 (3) |
N4—N3—C10—N2 | 0.0 (3) | S2—N6—C26—N7 | 145.19 (18) |
N4—N3—C10—N1 | −178.3 (2) | C26—N7—C27—N9 | 0.6 (2) |
C11—N2—C10—N3 | −0.2 (3) | C26—N7—C27—C28 | 178.6 (2) |
C11—N2—C10—N1 | 178.2 (2) | N8—N9—C27—N7 | −0.7 (3) |
S1—N1—C10—N3 | −39.4 (3) | C30—N9—C27—N7 | 178.4 (2) |
S1—N1—C10—N2 | 142.28 (19) | N8—N9—C27—C28 | −178.9 (2) |
C10—N2—C11—N4 | 0.4 (3) | C30—N9—C27—C28 | 0.2 (3) |
C10—N2—C11—C12 | 178.9 (3) | C31—O9—C28—C29 | 3.1 (4) |
N3—N4—C11—N2 | −0.4 (3) | C31—O9—C28—C27 | −175.4 (2) |
C14—N4—C11—N2 | 179.0 (2) | N7—C27—C28—C29 | −177.5 (2) |
N3—N4—C11—C12 | −179.2 (2) | N9—C27—C28—C29 | 0.2 (4) |
C14—N4—C11—C12 | 0.3 (4) | N7—C27—C28—O9 | 1.2 (4) |
C15—O4—C12—C13 | 2.7 (4) | N9—C27—C28—O9 | 178.9 (2) |
C15—O4—C12—C11 | −176.1 (2) | O9—C28—C29—N10 | −179.1 (2) |
N2—C11—C12—C13 | −178.4 (3) | C27—C28—C29—N10 | −0.7 (4) |
N4—C11—C12—C13 | 0.1 (4) | C30—N10—C29—C28 | 0.7 (4) |
N2—C11—C12—O4 | 0.6 (4) | C29—N10—C30—O10 | −179.7 (2) |
N4—C11—C12—O4 | 179.1 (2) | C29—N10—C30—N9 | −0.3 (4) |
O4—C12—C13—N5 | −178.9 (3) | C32—O10—C30—N10 | 1.5 (4) |
C11—C12—C13—N5 | 0.0 (4) | C32—O10—C30—N9 | −178.0 (2) |
C14—N5—C13—C12 | −0.4 (4) | C27—N9—C30—N10 | −0.2 (4) |
C13—N5—C14—O5 | −179.8 (3) | N8—N9—C30—N10 | 178.7 (2) |
C13—N5—C14—N4 | 0.7 (4) | C27—N9—C30—O10 | 179.4 (2) |
C16—O5—C14—N5 | 2.0 (4) | N8—N9—C30—O10 | −1.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···F10i | 0.99 | 2.48 | 3.293 (3) | 139 |
C16—H16C···F3ii | 0.98 | 2.40 | 3.185 (3) | 136 |
C17—H17B···O8i | 0.99 | 2.40 | 3.102 (3) | 127 |
C18—H18···F10iii | 1.00 | 2.60 | 3.104 (3) | 111 |
C20—H20···F9i | 0.95 | 2.55 | 3.466 (3) | 162 |
C32—H32C···F8iv | 0.98 | 2.36 | 3.146 (3) | 137 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1; (iii) x−1, y+1, z; (iv) −x+3, −y, −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).
References
AboulWafa, O. M., Farghaly, A. M., Teleb, M. & Sinoussy, K. S. (2014). Acta Cryst. E70, o672–o673. CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Q., Li, Y.-X., Hu, X.-W. & Yang, G.-F. (2005). Acta Cryst. E61, o3842–o3843. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chen, Q., Li, Y.-X., Hu, X.-W. & Yang, G.-F. (2005). Acta Cryst. E61, o3842–o3843. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jabusch, T. W. & Tjeerdema, R. S. (2005). J. Agric. Food Chem. 53, 7179–7183. Web of Science CrossRef PubMed CAS Google Scholar
Kang, G., Kim, J., Jeon, Y. & Kim, T. H. (2015). Acta Cryst. E71, o429. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kumar, M., Mallesha, L., Sridhar, M. A., Kapoor, K., Gupta, V. K. & Kant, R. (2012). Acta Cryst. E68, o2800. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Willingham, S. D., McCauley, G. N., Senseman, S. A., Chandler, J. M., Richburg, J. S., Lassiter, R. B. & Mann, R. K. (2008). Weed Technol. 22, 114–118. Web of Science CrossRef CAS Google Scholar
Yasuor, H., Osuna, M. D., Ortiz, A., Saldaín, N. E., Eckert, J. W. & Fischer, A. J. (2009). J. Agric. Food Chem. 57, 3653–3660. Web of Science CrossRef PubMed CAS Google Scholar
Zeng, X.-H., Liu, X.-L., Deng, S.-H., Chen, P. & Wang, H.-M. (2009). Acta Cryst. E65, o2583–o2584. Web of Science CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.