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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 73| Part 9| September 2017| Pages 1312-1315
https://doi.org/10.1107/S2056989017011458

Crystal structure of penoxsulam

CROSSMARK_Color_square_no_text.svg
Hyunjin Park,a Jineun Kim,a* Hojae Chianga and Tae Ho Kima*

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

Edited by J. Simpson, University of Otago, New Zealand (Received 29 July 2017; accepted 3 August 2017; online 8 August 2017)

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 asymmetric unit 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

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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[Jabusch, T. W. & Tjeerdema, R. S. (2005). J. Agric. Food Chem. 53, 7179-7183.]; Yasuor et al., 2009[Yasuor, H., Osuna, M. D., Ortiz, A., Saldaín, N. E., Eckert, J. W. & Fischer, A. J. (2009). J. Agric. Food Chem. 57, 3653-3660.]). 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[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.]). We now report here the crystal structure of penoxsulam, 2-(2,2-di­fluoro­eth­oxy)-N-(5,8-dimeth­oxy[1,2,4]triazolo[1,5-c]-pyrim­idin-2-yl)-6-(tri­fluoro­meth­yl)benzene­sulfonamide.

[Scheme 1]

2. Structural commentary

The penoxsulam mol­ecule crystallizes with two independent mol­ecules, A and B in the asymmetric unit, Fig. 1[link]. 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[AboulWafa, O. M., Farghaly, A. M., Teleb, M. & Sinoussy, K. S. (2014). Acta Cryst. E70, o672-o673.]) and triazolo­pyrimidine sulfonamide herbicides (Kumar et al., 2012[Kumar, M., Mallesha, L., Sridhar, M. A., Kapoor, K., Gupta, V. K. & Kant, R. (2012). Acta Cryst. E68, o2800.]).

[Figure 1]
Figure 1
The mol­ecular structures of the title compound with the atom labelling and displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

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[link]). 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[link] and Table 1[link]). 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[link]) and Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

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.
[Figure 2]
Figure 2
C—F⋯π and weak π–π inter­actions, yellow dashed lines, form chain along [001] in the crystal packing. H atoms have been omitted for clarity.
[Figure 3]
Figure 3
A two-dimensional network in the ab plane. Yellow dashed lines indicate weak inter­molecular π–π inter­actions. Red dashed lines indicate C—F⋯π inter­actions and C—H⋯O hydrogen bonds. H atoms have been omitted for clarity.
[Figure 4]
Figure 4
Overall packing showing the three-dimensional network viewed along the a-axis direction, C—H⋯F hydrogen bonds and F⋯F inter­molecular short contacts are shown as black dashed lines. H atoms have been omitted for clarity.

4. Database survey

Crystal structures of sulfonamide (Kang et al., 2015[Kang, G., Kim, J., Jeon, Y. & Kim, T. H. (2015). Acta Cryst. E71, o429.]; Chen, Wu et al., 2005[Chen, Q., Li, Y.-X., Hu, X.-W. & Yang, G.-F. (2005). Acta Cryst. E61, o3842-o3843.]) and triazolo­pyrimidine (Chen, Li et al., 2005[Chen, Q., Li, Y.-X., Hu, X.-W. & Yang, G.-F. (2005). Acta Cryst. E61, o3842-o3843.]) 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[Chen, Q., Li, Y.-X., Hu, X.-W. & Yang, G.-F. (2005). Acta Cryst. E61, o3842-o3843.]) and 5-(4-Chloro­phen­oxy)-6-isopropyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]-pyrimidin-7(6H)-one (Zeng et al., 2009[Zeng, X.-H., Liu, X.-L., Deng, S.-H., Chen, P. & Wang, H.-M. (2009). Acta Cryst. E65, o2583-o2584.]) 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 refinement details are summarized in Table 2[link]. 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.

Table 2
Experimental details

Crystal data
Chemical formula C16H14F5N5O5S
Mr 483.38
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 173
a, b, c (Å) 8.1945 (3), 8.3733 (3), 28.3277 (9)
α, β, γ (°) 82.698 (2), 84.183 (2), 81.814 (2)
V (Å3) 1901.43 (12)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.26
Crystal size (mm) 0.40 × 0.19 × 0.11
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.646, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 24336, 6571, 5503
Rint 0.032
(sin θ/λ)max (Å−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.106, 1.05
No. of reflections 6571
No. of parameters 581
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.47, −0.52
Computer programs: APEX2 and SAINT (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1566461

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989017011458/sj5532sup1.cif

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

checkCIF report


Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: 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).

2-(2,2-Difluoroethoxy)-N-(5,8-dimethoxy-1,2,4-triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide top
Crystal data top
C16H14F5N5O5SZ = 4
Mr = 483.38F(000) = 984
Triclinic, P1Dx = 1.689 Mg m−3
a = 8.1945 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.3733 (3) ÅCell parameters from 9990 reflections
c = 28.3277 (9) Åθ = 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) Å30.40 × 0.19 × 0.11 mm
Data collection top
Bruker APEXII CCD
diffractometer		5503 reflections with I > 2σ(I)
φ and ω scansRint = 0.032
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		θmax = 25.0°, θmin = 1.5°
Tmin = 0.646, Tmax = 0.746h = −9→9
24336 measured reflectionsk = −9→9
6571 independent reflectionsl = −32→33
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-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 reflectionsΔρmax = 0.47 e Å−3
581 parametersΔρmin = −0.52 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.40491 (7)0.27322 (7)0.33986 (2)0.02327 (15)
S21.17808 (7)0.29094 (7)0.15763 (2)0.02404 (15)
F10.6784 (2)−0.21313 (19)0.28932 (6)0.0473 (4)
F20.6798 (2)−0.2261 (2)0.36604 (6)0.0526 (5)
F30.0164 (2)0.53003 (19)0.34514 (6)0.0477 (4)
F40.18482 (19)0.53143 (16)0.28142 (5)0.0326 (3)
F5−0.0713 (2)0.51888 (19)0.27738 (6)0.0465 (4)
F60.6485 (2)0.5512 (2)0.21727 (6)0.0501 (4)
F70.6787 (3)0.5868 (2)0.13991 (7)0.0629 (5)
F81.4342 (2)−0.0947 (2)0.15363 (6)0.0505 (5)
F91.39010 (18)0.03048 (19)0.21686 (5)0.0381 (4)
F101.3647 (2)−0.22070 (19)0.22130 (6)0.0523 (5)
O10.4016 (2)−0.06137 (18)0.33033 (6)0.0292 (4)
O20.3455 (2)0.42426 (19)0.35764 (6)0.0343 (4)
O30.5333 (2)0.2632 (2)0.30221 (6)0.0356 (4)
O40.3555 (3)−0.3031 (3)0.52168 (8)0.0591 (6)
O50.0298 (3)0.3079 (3)0.51945 (7)0.0460 (5)
O60.8254 (2)0.2966 (2)0.17644 (6)0.0309 (4)
O71.1568 (2)0.3944 (2)0.19444 (6)0.0349 (4)
O81.3393 (2)0.2352 (2)0.13777 (6)0.0334 (4)
O90.7015 (3)0.3776 (3)−0.02223 (8)0.0535 (6)
O101.3171 (3)0.0395 (3)−0.02043 (7)0.0449 (5)
N10.4795 (2)0.1502 (2)0.38497 (7)0.0250 (4)
H1N0.58420.10830.38220.030*
N20.4113 (3)−0.0440 (2)0.44874 (8)0.0315 (5)
N30.2718 (3)0.2139 (2)0.44832 (7)0.0293 (5)
N40.2201 (3)0.1158 (3)0.48799 (7)0.0360 (5)
N50.0657 (4)0.0425 (4)0.55905 (8)0.0537 (7)
N61.0775 (3)0.3946 (2)0.11402 (7)0.0273 (5)
H6N1.03150.49450.11750.033*
N70.9191 (3)0.3767 (2)0.05042 (7)0.0313 (5)
N81.1790 (3)0.2324 (3)0.05044 (7)0.0303 (5)
N91.1034 (3)0.2116 (3)0.01107 (7)0.0354 (5)
N101.0719 (3)0.1088 (3)−0.05969 (8)0.0483 (6)
C10.4275 (3)−0.2344 (3)0.33482 (10)0.0319 (6)
H1A0.3768−0.27490.30910.038*
H1B0.3776−0.27970.36610.038*
C20.6090 (4)−0.2821 (3)0.33091 (10)0.0366 (7)
H20.6349−0.40300.33290.044*
C30.2487 (3)0.0195 (3)0.32428 (8)0.0226 (5)
C40.1131 (3)−0.0560 (3)0.31745 (9)0.0283 (6)
H40.1223−0.17100.31980.034*
C5−0.0334 (3)0.0372 (3)0.30731 (9)0.0319 (6)
H5−0.1263−0.01420.30320.038*
C6−0.0480 (3)0.2044 (3)0.30301 (9)0.0291 (6)
H6−0.14880.26710.29440.035*
C70.0837 (3)0.2816 (3)0.31124 (8)0.0219 (5)
C80.2322 (3)0.1891 (3)0.32403 (7)0.0188 (5)
C90.0556 (3)0.4652 (3)0.30368 (9)0.0303 (6)
C100.3842 (3)0.1093 (3)0.42737 (8)0.0264 (5)
C110.3046 (3)−0.0355 (3)0.48755 (9)0.0303 (6)
C120.2670 (4)−0.1556 (4)0.52547 (11)0.0451 (8)
C130.1508 (4)−0.1123 (4)0.55917 (10)0.0472 (8)
H130.1246−0.19190.58480.057*
C140.1007 (4)0.1546 (4)0.52415 (9)0.0400 (7)
C150.3152 (5)−0.4323 (4)0.55754 (13)0.0761 (13)
H15A0.3362−0.40640.58900.114*
H15B0.3837−0.53380.55060.114*
H15C0.1981−0.44480.55750.114*
C16−0.0932 (4)0.3529 (4)0.55773 (11)0.0618 (10)
H16A−0.18760.29270.55800.093*
H16B−0.13090.46970.55260.093*
H16C−0.04430.32660.58840.093*
C170.6501 (3)0.3241 (3)0.17727 (11)0.0388 (7)
H17A0.59960.26400.20620.047*
H17B0.61320.28720.14870.047*
C180.6008 (4)0.5018 (4)0.17763 (12)0.0460 (8)
H180.47820.52840.17670.055*
C190.8998 (3)0.1400 (3)0.17952 (8)0.0244 (5)
C200.8126 (3)0.0072 (3)0.18630 (9)0.0326 (6)
H200.69530.02310.18710.039*
C210.8963 (3)−0.1464 (3)0.19184 (9)0.0350 (6)
H210.8369−0.23720.19480.042*
C221.0651 (3)−0.1711 (3)0.19321 (9)0.0321 (6)
H221.1208−0.27830.19910.039*
C231.1547 (3)−0.0404 (3)0.18604 (8)0.0238 (5)
C241.0729 (3)0.1177 (3)0.17622 (8)0.0203 (5)
C251.3353 (3)−0.0779 (3)0.19369 (9)0.0344 (6)
C261.0613 (3)0.3314 (3)0.07141 (8)0.0257 (5)
C270.9510 (3)0.2979 (3)0.01135 (8)0.0275 (6)
C280.8526 (4)0.2892 (3)−0.02617 (10)0.0407 (7)
C290.9154 (4)0.1956 (4)−0.05974 (9)0.0422 (7)
H290.84980.1880−0.08500.051*
C301.1653 (4)0.1154 (3)−0.02503 (9)0.0369 (7)
C310.5908 (5)0.3640 (5)−0.05730 (12)0.0651 (10)
H31A0.63830.4036−0.08910.098*
H31B0.48410.4291−0.05010.098*
H31C0.57470.2500−0.05670.098*
C321.3861 (4)−0.0568 (4)−0.05853 (11)0.0574 (9)
H32A1.3238−0.1487−0.05800.086*
H32B1.5023−0.0976−0.05400.086*
H32C1.37890.0106−0.08940.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0248 (3)0.0191 (3)0.0273 (3)−0.0096 (2)−0.0074 (2)0.0035 (2)
S20.0227 (3)0.0273 (3)0.0243 (3)−0.0104 (3)−0.0056 (2)−0.0001 (2)
F10.0495 (11)0.0363 (9)0.0517 (10)−0.0063 (8)0.0157 (8)−0.0038 (8)
F20.0434 (11)0.0549 (11)0.0572 (11)0.0058 (8)−0.0152 (9)−0.0032 (9)
F30.0608 (12)0.0387 (9)0.0427 (9)0.0094 (8)−0.0013 (8)−0.0212 (7)
F40.0448 (9)0.0202 (7)0.0334 (8)−0.0065 (6)−0.0109 (7)0.0034 (6)
F50.0383 (10)0.0389 (9)0.0598 (11)0.0152 (7)−0.0215 (8)−0.0052 (8)
F60.0374 (10)0.0509 (10)0.0675 (12)−0.0021 (8)−0.0103 (8)−0.0271 (9)
F70.0708 (14)0.0459 (10)0.0689 (13)0.0095 (10)−0.0230 (11)0.0004 (9)
F80.0353 (10)0.0617 (11)0.0460 (10)0.0086 (8)0.0167 (8)−0.0063 (8)
F90.0239 (8)0.0547 (10)0.0349 (8)−0.0035 (7)−0.0082 (6)0.0007 (7)
F100.0421 (11)0.0414 (9)0.0616 (11)0.0160 (8)−0.0023 (8)0.0140 (8)
O10.0291 (10)0.0136 (8)0.0455 (10)−0.0016 (7)−0.0089 (8)−0.0020 (7)
O20.0486 (12)0.0161 (8)0.0417 (10)−0.0081 (8)−0.0193 (9)−0.0008 (7)
O30.0253 (10)0.0465 (11)0.0347 (10)−0.0149 (8)−0.0016 (8)0.0073 (8)
O40.0559 (15)0.0501 (14)0.0696 (15)−0.0188 (12)−0.0251 (12)0.0290 (11)
O50.0544 (14)0.0528 (13)0.0349 (11)−0.0212 (11)0.0097 (9)−0.0158 (9)
O60.0160 (9)0.0283 (9)0.0490 (11)−0.0019 (7)−0.0057 (8)−0.0056 (8)
O70.0458 (12)0.0342 (10)0.0298 (10)−0.0159 (9)−0.0095 (8)−0.0062 (8)
O80.0191 (9)0.0468 (11)0.0346 (10)−0.0121 (8)−0.0033 (7)0.0041 (8)
O90.0629 (16)0.0460 (12)0.0560 (13)−0.0108 (11)−0.0342 (11)0.0043 (10)
O100.0409 (13)0.0634 (13)0.0343 (11)−0.0178 (11)0.0065 (9)−0.0158 (10)
N10.0177 (11)0.0273 (11)0.0302 (11)−0.0045 (8)−0.0094 (8)0.0041 (9)
N20.0320 (13)0.0284 (11)0.0357 (12)−0.0117 (10)−0.0146 (10)0.0086 (9)
N30.0346 (13)0.0310 (11)0.0249 (11)−0.0144 (10)−0.0046 (9)−0.0004 (9)
N40.0387 (14)0.0455 (14)0.0273 (12)−0.0188 (11)−0.0086 (10)0.0014 (10)
N50.0623 (19)0.079 (2)0.0285 (13)−0.0423 (16)−0.0065 (12)0.0003 (13)
N60.0355 (13)0.0201 (10)0.0276 (11)−0.0067 (9)−0.0086 (9)0.0003 (8)
N70.0346 (13)0.0272 (11)0.0332 (12)−0.0091 (10)−0.0120 (10)0.0055 (9)
N80.0332 (13)0.0358 (12)0.0242 (11)−0.0126 (10)−0.0043 (9)−0.0018 (9)
N90.0446 (15)0.0384 (13)0.0262 (12)−0.0190 (11)−0.0053 (10)0.0026 (10)
N100.0610 (15)0.0614 (17)0.0280 (12)−0.0318 (12)−0.0021 (12)−0.0012 (11)
C10.0404 (16)0.0120 (11)0.0417 (15)−0.0024 (11)−0.0001 (12)−0.0003 (10)
C20.0409 (17)0.0201 (13)0.0451 (17)0.0000 (12)0.0027 (13)0.0004 (12)
C30.0243 (14)0.0218 (12)0.0212 (12)−0.0040 (10)−0.0013 (10)0.0005 (9)
C40.0325 (15)0.0232 (12)0.0317 (14)−0.0128 (11)−0.0013 (11)−0.0039 (10)
C50.0253 (14)0.0408 (15)0.0337 (14)−0.0175 (12)0.0000 (11)−0.0069 (12)
C60.0192 (13)0.0387 (15)0.0300 (13)−0.0029 (11)−0.0016 (10)−0.0075 (11)
C70.0218 (13)0.0239 (12)0.0199 (11)−0.0014 (10)−0.0008 (9)−0.0049 (9)
C80.0214 (13)0.0177 (11)0.0180 (11)−0.0064 (9)−0.0005 (9)−0.0011 (9)
C90.0319 (15)0.0264 (13)0.0319 (14)0.0070 (11)−0.0075 (11)−0.0090 (11)
C100.0281 (14)0.0276 (13)0.0268 (13)−0.0126 (11)−0.0119 (11)0.0021 (10)
C110.0300 (15)0.0359 (15)0.0285 (14)−0.0172 (12)−0.0143 (11)0.0068 (11)
C120.0468 (19)0.0523 (19)0.0403 (17)−0.0251 (16)−0.0251 (15)0.0175 (14)
C130.056 (2)0.065 (2)0.0266 (15)−0.0373 (18)−0.0174 (14)0.0175 (14)
C140.0433 (18)0.059 (2)0.0240 (14)−0.0256 (15)−0.0038 (12)−0.0066 (13)
C150.099 (3)0.062 (2)0.072 (2)−0.043 (2)−0.039 (2)0.0379 (19)
C160.071 (2)0.078 (2)0.0443 (19)−0.036 (2)0.0250 (17)−0.0330 (18)
C170.0167 (14)0.0439 (16)0.0591 (18)−0.0001 (12)−0.0096 (12)−0.0178 (14)
C180.0244 (16)0.0511 (18)0.067 (2)0.0050 (14)−0.0176 (14)−0.0227 (16)
C190.0220 (13)0.0267 (13)0.0252 (12)−0.0033 (10)−0.0033 (10)−0.0045 (10)
C200.0242 (14)0.0402 (15)0.0362 (15)−0.0136 (12)−0.0006 (11)−0.0065 (12)
C210.0431 (18)0.0301 (14)0.0355 (15)−0.0191 (13)0.0012 (12)−0.0059 (11)
C220.0437 (17)0.0238 (13)0.0280 (13)−0.0046 (12)0.0018 (12)−0.0036 (10)
C230.0251 (13)0.0263 (13)0.0185 (11)−0.0025 (10)0.0038 (10)−0.0020 (10)
C240.0182 (12)0.0238 (12)0.0195 (11)−0.0059 (10)−0.0009 (9)−0.0022 (9)
C250.0301 (15)0.0367 (15)0.0312 (14)0.0040 (12)0.0026 (12)0.0019 (12)
C260.0300 (14)0.0230 (12)0.0254 (13)−0.0114 (11)−0.0061 (11)0.0043 (10)
C270.0373 (16)0.0241 (13)0.0230 (13)−0.0144 (11)−0.0087 (11)0.0072 (10)
C280.053 (2)0.0354 (15)0.0367 (16)−0.0185 (14)−0.0211 (14)0.0123 (13)
C290.0613 (17)0.0504 (18)0.0212 (13)−0.0282 (13)−0.0155 (13)0.0046 (12)
C300.0489 (19)0.0424 (16)0.0233 (14)−0.0242 (14)0.0030 (12)−0.0027 (12)
C310.066 (3)0.073 (2)0.062 (2)−0.022 (2)−0.0397 (19)0.0113 (18)
C320.056 (2)0.081 (2)0.0413 (18)−0.0272 (19)0.0199 (16)−0.0260 (17)
Geometric parameters (Å, º) top
S1—O31.4217 (18)N10—C301.316 (4)
S1—O21.4238 (18)N10—C291.381 (4)
S1—N11.6466 (19)C1—C21.481 (4)
S1—C81.787 (2)C1—H1A0.9900
S2—O71.4207 (18)C1—H1B0.9900
S2—O81.4210 (18)C2—H21.0000
S2—N61.640 (2)C3—C41.395 (3)
S2—C241.788 (2)C3—C81.406 (3)
F1—C21.353 (3)C4—C51.371 (4)
F2—C21.364 (3)C4—H40.9500
F3—C91.346 (3)C5—C61.379 (4)
F4—C91.330 (3)C5—H50.9500
F5—C91.333 (3)C6—C71.388 (3)
F6—C181.355 (3)C6—H60.9500
F7—C181.361 (4)C7—C81.401 (3)
F8—C251.336 (3)C7—C91.513 (3)
F9—C251.335 (3)C11—C121.417 (4)
F10—C251.348 (3)C12—C131.324 (5)
O1—C31.353 (3)C13—H130.9500
O1—C11.425 (3)C15—H15A0.9800
O4—C121.351 (4)C15—H15B0.9800
O4—C151.438 (4)C15—H15C0.9800
O5—C141.328 (4)C16—H16A0.9800
O5—C161.452 (3)C16—H16B0.9800
O6—C191.361 (3)C16—H16C0.9800
O6—C171.420 (3)C17—C181.487 (4)
O9—C281.351 (4)C17—H17A0.9900
O9—C311.436 (4)C17—H17B0.9900
O10—C301.324 (4)C18—H181.0000
O10—C321.450 (3)C19—C201.389 (3)
N1—C101.397 (3)C19—C241.399 (3)
N1—H1N0.8800C20—C211.367 (4)
N2—C111.336 (3)C20—H200.9500
N2—C101.346 (3)C21—C221.373 (4)
N3—C101.326 (3)C21—H210.9500
N3—N41.373 (3)C22—C231.386 (3)
N4—C111.355 (3)C22—H220.9500
N4—C141.380 (4)C23—C241.403 (3)
N5—C141.313 (4)C23—C251.501 (4)
N5—C131.382 (4)C27—C281.413 (4)
N6—C261.403 (3)C28—C291.326 (4)
N6—H6N0.8800C29—H290.9500
N7—C271.344 (3)C31—H31A0.9800
N7—C261.346 (3)C31—H31B0.9800
N8—C261.323 (3)C31—H31C0.9800
N8—N91.370 (3)C32—H32A0.9800
N9—C271.350 (3)C32—H32B0.9800
N9—C301.393 (3)C32—H32C0.9800
O3—S1—O2120.60 (11)C12—C13—N5123.4 (3)
O3—S1—N1104.84 (11)C12—C13—H13118.3
O2—S1—N1106.54 (10)N5—C13—H13118.3
O3—S1—C8109.19 (10)N5—C14—O5125.9 (3)
O2—S1—C8108.35 (11)N5—C14—N4119.6 (3)
N1—S1—C8106.43 (10)O5—C14—N4114.5 (2)
O7—S2—O8120.38 (11)O4—C15—H15A109.5
O7—S2—N6104.97 (11)O4—C15—H15B109.5
O8—S2—N6107.16 (11)H15A—C15—H15B109.5
O7—S2—C24109.88 (10)O4—C15—H15C109.5
O8—S2—C24107.92 (11)H15A—C15—H15C109.5
N6—S2—C24105.54 (10)H15B—C15—H15C109.5
C3—O1—C1120.10 (19)O5—C16—H16A109.5
C12—O4—C15116.5 (3)O5—C16—H16B109.5
C14—O5—C16115.5 (2)H16A—C16—H16B109.5
C19—O6—C17117.77 (19)O5—C16—H16C109.5
C28—O9—C31116.7 (3)H16A—C16—H16C109.5
C30—O10—C32115.5 (2)H16B—C16—H16C109.5
C10—N1—S1123.11 (17)O6—C17—C18106.7 (2)
C10—N1—H1N118.4O6—C17—H17A110.4
S1—N1—H1N118.4C18—C17—H17A110.4
C11—N2—C10100.9 (2)O6—C17—H17B110.4
C10—N3—N4100.3 (2)C18—C17—H17B110.4
C11—N4—N3109.7 (2)H17A—C17—H17B108.6
C11—N4—C14121.8 (2)F6—C18—F7105.9 (2)
N3—N4—C14128.4 (2)F6—C18—C17110.2 (3)
C14—N5—C13119.3 (3)F7—C18—C17111.1 (2)
C26—N6—S2123.03 (17)F6—C18—H18109.9
C26—N6—H6N118.5F7—C18—H18109.9
S2—N6—H6N118.5C17—C18—H18109.9
C27—N7—C26100.8 (2)O6—C19—C20123.2 (2)
C26—N8—N9100.1 (2)O6—C19—C24116.2 (2)
C27—N9—N8110.4 (2)C20—C19—C24120.5 (2)
C27—N9—C30121.9 (2)C21—C20—C19119.7 (2)
N8—N9—C30127.7 (2)C21—C20—H20120.1
C30—N10—C29120.1 (3)C19—C20—H20120.1
O1—C1—C2106.3 (2)C20—C21—C22120.8 (2)
O1—C1—H1A110.5C20—C21—H21119.6
C2—C1—H1A110.5C22—C21—H21119.6
O1—C1—H1B110.5C21—C22—C23120.3 (2)
C2—C1—H1B110.5C21—C22—H22119.8
H1A—C1—H1B108.7C23—C22—H22119.8
F1—C2—F2105.6 (2)C22—C23—C24119.8 (2)
F1—C2—C1110.6 (2)C22—C23—C25116.3 (2)
F2—C2—C1110.8 (2)C24—C23—C25123.7 (2)
F1—C2—H2109.9C19—C24—C23118.3 (2)
F2—C2—H2109.9C19—C24—S2118.21 (17)
C1—C2—H2109.9C23—C24—S2123.49 (18)
O1—C3—C4123.6 (2)F9—C25—F8108.1 (2)
O1—C3—C8116.1 (2)F9—C25—F10105.0 (2)
C4—C3—C8120.3 (2)F8—C25—F10105.2 (2)
C5—C4—C3119.5 (2)F9—C25—C23113.5 (2)
C5—C4—H4120.3F8—C25—C23114.2 (2)
C3—C4—H4120.3F10—C25—C23110.2 (2)
C4—C5—C6121.0 (2)N8—C26—N7118.5 (2)
C4—C5—H5119.5N8—C26—N6123.6 (2)
C6—C5—H5119.5N7—C26—N6117.9 (2)
C5—C6—C7120.4 (2)N7—C27—N9110.3 (2)
C5—C6—H6119.8N7—C27—C28131.1 (3)
C7—C6—H6119.8N9—C27—C28118.6 (2)
C6—C7—C8119.8 (2)C29—C28—O9128.1 (3)
C6—C7—C9115.7 (2)C29—C28—C27117.8 (3)
C8—C7—C9124.5 (2)O9—C28—C27114.0 (3)
C7—C8—C3118.7 (2)C28—C29—N10122.9 (3)
C7—C8—S1124.01 (17)C28—C29—H29118.5
C3—C8—S1117.28 (18)N10—C29—H29118.5
F4—C9—F5106.3 (2)N10—C30—O10126.7 (3)
F4—C9—F3107.5 (2)N10—C30—N9118.7 (3)
F5—C9—F3105.6 (2)O10—C30—N9114.6 (2)
F4—C9—C7113.7 (2)O9—C31—H31A109.5
F5—C9—C7111.2 (2)O9—C31—H31B109.5
F3—C9—C7112.0 (2)H31A—C31—H31B109.5
N3—C10—N2118.3 (2)O9—C31—H31C109.5
N3—C10—N1123.7 (2)H31A—C31—H31C109.5
N2—C10—N1118.0 (2)H31B—C31—H31C109.5
N2—C11—N4110.8 (2)O10—C32—H32A109.5
N2—C11—C12130.9 (3)O10—C32—H32B109.5
N4—C11—C12118.2 (3)H32A—C32—H32B109.5
C13—C12—O4128.3 (3)O10—C32—H32C109.5
C13—C12—C11117.6 (3)H32A—C32—H32C109.5
O4—C12—C11114.1 (3)H32B—C32—H32C109.5
O3—S1—N1—C10−171.86 (18)C16—O5—C14—N4−178.4 (2)
O2—S1—N1—C1059.2 (2)C11—N4—C14—N5−0.7 (4)
C8—S1—N1—C10−56.2 (2)N3—N4—C14—N5178.7 (2)
C10—N3—N4—C110.3 (2)C11—N4—C14—O5179.8 (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—C18175.3 (2)
O8—S2—N6—C2654.1 (2)O6—C17—C18—F6−61.3 (3)
C24—S2—N6—C26−60.7 (2)O6—C17—C18—F755.7 (3)
C26—N8—N9—C270.3 (2)C17—O6—C19—C20−4.0 (3)
C26—N8—N9—C30−178.6 (2)C17—O6—C19—C24177.0 (2)
C3—O1—C1—C2168.7 (2)O6—C19—C20—C21−176.2 (2)
O1—C1—C2—F1−56.8 (3)C24—C19—C20—C212.8 (4)
O1—C1—C2—F259.8 (3)C19—C20—C21—C223.3 (4)
C1—O1—C3—C4−6.4 (3)C20—C21—C22—C23−4.0 (4)
C1—O1—C3—C8175.1 (2)C21—C22—C23—C24−1.5 (4)
O1—C3—C4—C5−174.1 (2)C21—C22—C23—C25173.3 (2)
C8—C3—C4—C54.3 (3)O6—C19—C24—C23171.0 (2)
C3—C4—C5—C61.0 (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—C80.0 (3)C20—C19—C24—S2169.70 (19)
C5—C6—C7—C9177.8 (2)C22—C23—C24—C197.4 (3)
C6—C7—C8—C35.3 (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—S215.3 (3)
C9—C7—C8—S17.2 (3)O7—S2—C24—C1971.2 (2)
O1—C3—C8—C7171.1 (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—S1172.95 (18)O8—S2—C24—C2321.9 (2)
O3—S1—C8—C7−107.6 (2)N6—S2—C24—C23136.22 (19)
O2—S1—C8—C725.5 (2)C22—C23—C25—F9−138.3 (2)
N1—S1—C8—C7139.78 (19)C24—C23—C25—F936.3 (3)
O3—S1—C8—C372.01 (19)C22—C23—C25—F897.3 (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—F10153.8 (2)
C8—C7—C9—F439.5 (3)N9—N8—C26—N70.1 (3)
C6—C7—C9—F5−18.2 (3)N9—N8—C26—N6−178.7 (2)
C8—C7—C9—F5159.5 (2)C27—N7—C26—N8−0.5 (3)
C6—C7—C9—F399.7 (3)C27—N7—C26—N6178.4 (2)
C8—C7—C9—F3−82.6 (3)S2—N6—C26—N8−36.0 (3)
N4—N3—C10—N20.0 (3)S2—N6—C26—N7145.19 (18)
N4—N3—C10—N1−178.3 (2)C26—N7—C27—N90.6 (2)
C11—N2—C10—N3−0.2 (3)C26—N7—C27—C28178.6 (2)
C11—N2—C10—N1178.2 (2)N8—N9—C27—N7−0.7 (3)
S1—N1—C10—N3−39.4 (3)C30—N9—C27—N7178.4 (2)
S1—N1—C10—N2142.28 (19)N8—N9—C27—C28−178.9 (2)
C10—N2—C11—N40.4 (3)C30—N9—C27—C280.2 (3)
C10—N2—C11—C12178.9 (3)C31—O9—C28—C293.1 (4)
N3—N4—C11—N2−0.4 (3)C31—O9—C28—C27−175.4 (2)
C14—N4—C11—N2179.0 (2)N7—C27—C28—C29−177.5 (2)
N3—N4—C11—C12−179.2 (2)N9—C27—C28—C290.2 (4)
C14—N4—C11—C120.3 (4)N7—C27—C28—O91.2 (4)
C15—O4—C12—C132.7 (4)N9—C27—C28—O9178.9 (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—C130.1 (4)C30—N10—C29—C280.7 (4)
N2—C11—C12—O40.6 (4)C29—N10—C30—O10−179.7 (2)
N4—C11—C12—O4179.1 (2)C29—N10—C30—N9−0.3 (4)
O4—C12—C13—N5−178.9 (3)C32—O10—C30—N101.5 (4)
C11—C12—C13—N50.0 (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—N10178.7 (2)
C13—N5—C14—N40.7 (4)C27—N9—C30—O10179.4 (2)
C16—O5—C14—N52.0 (4)N8—N9—C30—O10−1.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···F10i0.992.483.293 (3)139
C16—H16C···F3ii0.982.403.185 (3)136
C17—H17B···O8i0.992.403.102 (3)127
C18—H18···F10iii1.002.603.104 (3)111
C20—H20···F9i0.952.553.466 (3)162
C32—H32C···F8iv0.982.363.146 (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

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ISSN: 2056-9890
Volume 73| Part 9| September 2017| Pages 1312-1315
https://doi.org/10.1107/S2056989017011458
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