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The structure of the title compound, C15H8N4Cl2F6OS, a phenyl­pyrazole-based insecticide related to ethiprole, fipronil, and derivatives thereof is presented. The pyrazole ring has four chemically diverse substituents, namely a nitro­gen-bound 2,6-di­chloro-4-tri­fluoro­methyl­phenyl and carbon-bound cyano, ethyl­sulfanyl, and 2,2,2-tri­fluoro­acetamide groups. The pyrazole and phenyl rings are perpendicular, subtending a dihedral angle of 89.80 (5)°. In the crystal, strong N—H...O hydrogen bonds link the mol­ecules into chains that extend parallel to the a-axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989022009653/tx2059sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989022009653/tx2059Isup2.hkl
Contains datablock I

CCDC reference: 2210523

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.064
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B ..F2 . 2.58 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 ..F5 . 2.62 Ang. PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 7 Report
Alert level G PLAT230_ALERT_2_G Hirshfeld Test Diff for C3 --C4 . 5.0 s.u. PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 7 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 2 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 9 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: APEX3 (Bruker, 2016); data reduction: APEX3 (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELX (Sheldrick, 2008) and publCIF (Westrip, 2010).

N-{3-Cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(ethylsulfanyl)-1H-pyrazol-5-yl}-2,2,2-trifluoroacetamide top
Crystal data top
C15H8Cl2F6N4OSDx = 1.697 Mg m3
Mr = 477.21Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 9972 reflections
a = 9.9350 (3) Åθ = 2.5–27.5°
b = 17.5133 (7) ŵ = 0.53 mm1
c = 21.4662 (8) ÅT = 90 K
V = 3735.0 (2) Å3Cut block, colourless
Z = 80.30 × 0.23 × 0.19 mm
F(000) = 1904
Data collection top
Bruker D8 Venture dual source
diffractometer
4271 independent reflections
Radiation source: microsource3893 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm-1Rint = 0.036
φ and ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 1210
Tmin = 0.831, Tmax = 0.958k = 2222
27352 measured reflectionsl = 2727
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.0273P)2 + 2.0142P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4271 reflectionsΔρmax = 0.42 e Å3
267 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0017 (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
Cl10.63935 (3)0.51208 (2)0.40861 (2)0.01864 (8)
Cl20.09945 (3)0.53537 (2)0.40975 (2)0.02419 (9)
S10.32287 (3)0.38515 (2)0.20184 (2)0.01658 (8)
F10.35596 (9)0.62440 (5)0.15112 (4)0.02447 (19)
F20.38608 (8)0.69639 (4)0.23078 (4)0.02336 (18)
F30.18898 (8)0.68747 (5)0.18872 (4)0.02659 (19)
F40.36645 (9)0.70022 (5)0.59601 (4)0.02648 (19)
F50.30334 (10)0.77508 (5)0.52258 (4)0.0323 (2)
F60.51380 (8)0.75448 (5)0.53817 (4)0.02669 (19)
O10.15013 (9)0.55566 (5)0.24758 (4)0.01724 (19)
N10.36297 (11)0.47239 (6)0.36809 (5)0.0145 (2)
N20.35250 (11)0.39898 (6)0.38684 (5)0.0168 (2)
N30.37119 (10)0.55065 (6)0.27566 (5)0.0130 (2)
H3N0.4502 (17)0.5686 (8)0.2699 (7)0.016*
N40.30803 (13)0.21428 (6)0.33539 (6)0.0255 (3)
C10.36015 (12)0.47954 (7)0.30511 (6)0.0131 (2)
C20.34539 (12)0.40781 (7)0.28031 (6)0.0141 (2)
C30.34127 (13)0.36032 (7)0.33357 (6)0.0155 (2)
C40.32423 (14)0.27879 (7)0.33502 (6)0.0185 (3)
C50.49124 (14)0.35383 (9)0.18065 (6)0.0234 (3)
H5A0.5565330.3957460.1872980.028*
H5B0.5183880.3099100.2068270.028*
C60.48964 (15)0.33069 (9)0.11230 (7)0.0275 (3)
H6A0.4603300.3740980.0868830.041*
H6B0.4272630.2879450.1064580.041*
H6C0.5803180.3151480.0995660.041*
C70.26356 (12)0.58029 (6)0.24545 (5)0.0131 (2)
C80.29906 (13)0.64906 (7)0.20371 (6)0.0166 (3)
C90.37120 (13)0.53275 (7)0.41254 (6)0.0141 (2)
C100.49581 (12)0.55813 (7)0.43330 (6)0.0140 (2)
C110.50542 (12)0.61972 (7)0.47388 (5)0.0145 (2)
H110.5905430.6373950.4879650.017*
C120.38740 (13)0.65467 (7)0.49325 (6)0.0143 (2)
C130.26172 (13)0.62922 (7)0.47417 (6)0.0160 (2)
H130.1821360.6536120.4885220.019*
C140.25432 (13)0.56765 (7)0.43387 (6)0.0156 (2)
C150.39317 (13)0.72121 (7)0.53760 (6)0.0176 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01593 (15)0.01905 (15)0.02095 (16)0.00316 (11)0.00349 (11)0.00045 (11)
Cl20.01509 (16)0.02479 (17)0.03269 (19)0.00092 (12)0.00540 (13)0.00730 (13)
S10.01774 (16)0.01755 (15)0.01445 (15)0.00235 (11)0.00419 (12)0.00360 (11)
F10.0328 (5)0.0231 (4)0.0175 (4)0.0014 (3)0.0079 (3)0.0003 (3)
F20.0286 (4)0.0160 (4)0.0255 (4)0.0086 (3)0.0006 (3)0.0001 (3)
F30.0246 (4)0.0215 (4)0.0336 (5)0.0074 (3)0.0018 (4)0.0101 (3)
F40.0389 (5)0.0253 (4)0.0152 (4)0.0056 (4)0.0072 (3)0.0047 (3)
F50.0409 (5)0.0182 (4)0.0378 (5)0.0121 (4)0.0129 (4)0.0102 (4)
F60.0286 (4)0.0231 (4)0.0285 (4)0.0110 (3)0.0052 (4)0.0093 (3)
O10.0122 (4)0.0175 (4)0.0220 (5)0.0002 (3)0.0008 (4)0.0010 (4)
N10.0183 (5)0.0108 (5)0.0143 (5)0.0006 (4)0.0015 (4)0.0007 (4)
N20.0213 (5)0.0118 (5)0.0172 (5)0.0005 (4)0.0025 (4)0.0006 (4)
N30.0104 (5)0.0123 (5)0.0162 (5)0.0011 (4)0.0003 (4)0.0007 (4)
N40.0355 (7)0.0170 (5)0.0239 (6)0.0005 (5)0.0053 (5)0.0002 (4)
C10.0109 (5)0.0138 (5)0.0146 (6)0.0012 (4)0.0017 (4)0.0001 (4)
C20.0131 (5)0.0145 (6)0.0147 (6)0.0012 (4)0.0017 (5)0.0018 (4)
C30.0164 (6)0.0132 (5)0.0168 (6)0.0008 (5)0.0026 (5)0.0006 (4)
C40.0230 (7)0.0172 (6)0.0153 (6)0.0009 (5)0.0040 (5)0.0005 (5)
C50.0188 (6)0.0332 (7)0.0181 (6)0.0040 (6)0.0001 (5)0.0035 (5)
C60.0248 (7)0.0388 (8)0.0190 (7)0.0018 (6)0.0022 (6)0.0067 (6)
C70.0145 (5)0.0116 (5)0.0132 (5)0.0018 (4)0.0006 (5)0.0026 (4)
C80.0180 (6)0.0142 (6)0.0177 (6)0.0007 (5)0.0001 (5)0.0002 (5)
C90.0200 (6)0.0110 (5)0.0115 (6)0.0001 (4)0.0017 (5)0.0004 (4)
C100.0150 (6)0.0139 (5)0.0131 (6)0.0013 (4)0.0014 (5)0.0024 (4)
C110.0161 (6)0.0144 (5)0.0132 (6)0.0024 (4)0.0014 (5)0.0016 (4)
C120.0195 (6)0.0114 (5)0.0120 (5)0.0000 (4)0.0002 (5)0.0013 (4)
C130.0169 (6)0.0144 (5)0.0166 (6)0.0029 (5)0.0003 (5)0.0003 (4)
C140.0151 (6)0.0150 (5)0.0166 (6)0.0003 (5)0.0027 (5)0.0014 (5)
C150.0209 (6)0.0146 (6)0.0173 (6)0.0005 (5)0.0000 (5)0.0012 (5)
Geometric parameters (Å, º) top
Cl1—C101.7219 (12)C1—C21.3722 (16)
Cl2—C141.7191 (13)C2—C31.4143 (17)
S1—C21.7450 (13)C3—C41.4381 (17)
S1—C51.8181 (14)C5—C61.5222 (19)
F1—C81.3342 (15)C5—H5A0.9900
F2—C81.3312 (15)C5—H5B0.9900
F3—C81.3237 (15)C6—H6A0.9800
F4—C151.3333 (15)C6—H6B0.9800
F5—C151.3381 (15)C6—H6C0.9800
F6—C151.3327 (15)C7—C81.5421 (16)
O1—C71.2075 (15)C9—C101.3888 (17)
N1—N21.3511 (14)C9—C141.3898 (17)
N1—C11.3581 (16)C10—C111.3898 (17)
N1—C91.4264 (15)C11—C121.3865 (17)
N2—C31.3337 (16)C11—H110.9500
N3—C71.3540 (16)C12—C131.3877 (18)
N3—C11.4010 (15)C12—C151.5059 (17)
N3—H3N0.855 (16)C13—C141.3843 (17)
N4—C41.1412 (17)C13—H130.9500
C2—S1—C5101.08 (6)N3—C7—C8113.4 (1)
N2—N1—C1112.5 (1)F3—C8—F2109.04 (10)
N2—N1—C9120.69 (10)F3—C8—F1108.0 (1)
C1—N1—C9126.78 (10)F2—C8—F1107.2 (1)
C3—N2—N1103.54 (10)F3—C8—C7110.44 (10)
C7—N3—C1119.68 (10)F2—C8—C7112.41 (10)
C7—N3—H3N121 (1)F1—C8—C7109.61 (10)
C1—N3—H3N117.7 (10)C10—C9—C14119.89 (11)
N1—C1—C2107.7 (1)C10—C9—N1120.19 (11)
N1—C1—N3121.98 (10)C14—C9—N1119.90 (11)
C2—C1—N3130.32 (12)C9—C10—C11120.71 (11)
C1—C2—C3103.17 (11)C9—C10—Cl1119.31 (9)
C1—C2—S1126.61 (10)C11—C10—Cl1119.97 (10)
C3—C2—S1130.01 (9)C12—C11—C10118.20 (11)
N2—C3—C2113.09 (11)C12—C11—H11120.9
N2—C3—C4119.69 (11)C10—C11—H11120.9
C2—C3—C4127.21 (11)C11—C12—C13122.05 (11)
N4—C4—C3178.42 (15)C11—C12—C15119.94 (11)
C6—C5—S1108.17 (10)C13—C12—C15118.00 (11)
C6—C5—H5A110.1C14—C13—C12118.84 (12)
S1—C5—H5A110.1C14—C13—H13120.6
C6—C5—H5B110.1C12—C13—H13120.6
S1—C5—H5B110.1C13—C14—C9120.27 (12)
H5A—C5—H5B108.4C13—C14—Cl2119.47 (10)
C5—C6—H6A109.5C9—C14—Cl2120.26 (9)
C5—C6—H6B109.5F6—C15—F4106.92 (11)
H6A—C6—H6B109.5F6—C15—F5107.08 (10)
C5—C6—H6C109.5F4—C15—F5106.75 (11)
H6A—C6—H6C109.5F6—C15—C12112.23 (11)
H6B—C6—H6C109.5F4—C15—C12111.94 (10)
O1—C7—N3125.59 (11)F5—C15—C12111.58 (11)
O1—C7—C8120.96 (11)
C1—N1—N2—C30.77 (14)N3—C7—C8—F177.52 (13)
C9—N1—N2—C3177.32 (11)N2—N1—C9—C1091.61 (15)
N2—N1—C1—C20.79 (14)C1—N1—C9—C1090.59 (15)
C9—N1—C1—C2177.16 (11)N2—N1—C9—C1490.12 (14)
N2—N1—C1—N3179.23 (11)C1—N1—C9—C1487.67 (16)
C9—N1—C1—N32.82 (19)C14—C9—C10—C111.93 (18)
C7—N3—C1—N1111.17 (13)N1—C9—C10—C11176.34 (11)
C7—N3—C1—C268.80 (18)C14—C9—C10—Cl1177.67 (9)
N1—C1—C2—C30.45 (13)N1—C9—C10—Cl14.06 (16)
N3—C1—C2—C3179.58 (12)C9—C10—C11—C120.37 (18)
N1—C1—C2—S1174.65 (9)Cl1—C10—C11—C12179.23 (9)
N3—C1—C2—S15.3 (2)C10—C11—C12—C131.06 (18)
C5—S1—C2—C1101.74 (12)C10—C11—C12—C15179.53 (11)
C5—S1—C2—C384.50 (13)C11—C12—C13—C140.90 (18)
N1—N2—C3—C20.47 (14)C15—C12—C13—C14179.39 (11)
N1—N2—C3—C4178.34 (12)C12—C13—C14—C90.69 (18)
C1—C2—C3—N20.02 (14)C12—C13—C14—Cl2179.99 (9)
S1—C2—C3—N2174.87 (10)C10—C9—C14—C132.09 (18)
C1—C2—C3—C4178.68 (13)N1—C9—C14—C13176.18 (11)
S1—C2—C3—C43.8 (2)C10—C9—C14—Cl2178.62 (9)
C2—S1—C5—C6179.48 (10)N1—C9—C14—Cl23.11 (16)
C1—N3—C7—O110.00 (18)C11—C12—C15—F620.04 (16)
C1—N3—C7—C8167.28 (10)C13—C12—C15—F6161.43 (11)
O1—C7—C8—F318.96 (16)C11—C12—C15—F4100.19 (13)
N3—C7—C8—F3163.61 (10)C13—C12—C15—F478.33 (14)
O1—C7—C8—F2140.97 (12)C11—C12—C15—F5140.24 (12)
N3—C7—C8—F241.60 (14)C13—C12—C15—F541.23 (16)
O1—C7—C8—F199.91 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O1i0.855 (16)2.034 (16)2.8172 (13)151.9 (14)
C5—H5B···F2ii0.992.583.5641 (16)174
C11—H11···F5iii0.952.623.4873 (15)152
C13—H13···F6iv0.952.393.2071 (15)144
Symmetry codes: (i) x+1/2, y, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x+1/2, y+3/2, z+1; (iv) x1/2, y+3/2, z+1.
Hydrogen bonds and other short contacts (Å, °) in I top
Cg(C9–C14) represents the centroid of C9–C14 benzene ring.
AtomsD—HH···AD···AD—H···A
N3—H3N···O1i0.855 (16)2.034 (16)2.8172 (13)151.9 (14)
C5—H5B···F2ii0.992.583.5641 (16)173.9
C11—H11···F5iii0.952.623.4873 (15)151.8
C13—H13···F6iv0.952.393.2071 (15)143.8
Cl1···Cg(C9–C14)v3.4967 (6)
Symmetry codes: (i) x + 1/2, y, -z + 1/2; (ii) -x + 1, y - 1/2, -z + 1/2; (iii) x + 1/2, -y + 3/2, -z + 1; (iv) x - 1/2, -y + 3/2, -z + 1; (v) -x + 1, -y + 1, -z + 1.
Atom–atom contact coverages (%) in I top
Atom contacts%Atom contacts%
H···F/F···H23.0F···Cl/Cl···F8.3
N···F/F···N7.3C···H/H···C7.1
H···Cl/Cl···H7.1H···N/N···H6.9
H···O/O···H5.9H···H4.8
C···F/F···C3.8C···Cl/Cl···C3.8
C···N/N···C3.4F···S/S···F3.0
S···Cl/Cl···S1.9Cl···Cl1.3
H···S/S···H1.3O···Cl/Cl···O1.2
C···C0.9O···N/N···O0.8
N···Cl/Cl···N0.7N···N0.3
O···F/F···O0.2C···S/S···C0.2
C···O/O···C0.1
All other atom–atom contact coverages are ~0.0 %
Some structures similar to I deposited in the CSD top
All entries have 2,6-dichloro-4-(trifluoromethyl)phenyl and cyano groups attached at the equivalent of N1 and C3 of I, respectively. Substituents R' and R¨ represent groups attached at the equivalent of C1 and C2 in I, respectively.
CSD codeR'R"Reference
DUKVAJNHCOCH2PhSOCF3Chen et al. (2020)
EFIXEZNHCOCHCHPhSOCF3Chen (2019)
PAZFAYNH2SCF3Tang, Zhong, Lin et al. (2005)
TOLFAENHCH2PhOMeSOCF3Chen & Wu (2019)
YEGJAYNH2SOCF3Park et al. (2017)
ZITNAUNHCHPhFSOCF3Chen et al. (2019)
GIXDATNH2ILi et al. (2007)
HILTUSNH2HLuo et al. (2007)
TIDNUPNH2CF3Hainzl & Casida (1996)
 

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