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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Pages o2659-o2660
https://doi.org/10.1107/S1600536811036889

1,1,1-Tri­fluoro-4-(thio­phen-2-yl)-4-[(2-{[4,4,4-tri­fluoro-3-oxo-1-(thio­phen-2-yl)but-1-en-1-yl]amino}­eth­yl)amino]­but-3-en-2-one

Abdullah M. Asiri,a,b Abdulrahman O. Al-Youbi,a Hassan M. Faidallaha and Seik Weng Ngc,a*

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, bCenter of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 11 September 2011; accepted 11 September 2011; online 17 September 2011)

The asymmetric unit of the diamine compound, C18H14F3N2O2S2, consists of two mol­ecules; the C=C double bond has a Z configuration in the C4H3S—C=C—C(=O)—C segment. The –NH—CH2—CH2—NH chain adopts a twisted U-shape. The amino group is an intra­molecular hydrogen-bond donor to the carbonyl group; the intra­molecular hydrogen bond generates a six-membered ring. In both mol­ecules, the thienyl rings are disordered over two positions; the occupancies of the major components are 0.817 (4) and 0.778 (4) in one mol­ecule and 0.960 (4) and 0.665 (4) in the other. One of the trifluoro­methyl groups is disordered over two positions with the major component having 0.637 (8) occupancy.

Related literature

For the synthesis, see: Wang & Tong (1995[Wang, W. & Tong, J. (1995). J. Natur. Sci. Xiangtan Univ. 17, 52-57.]). For related structures, see: Bresciani-Pahor et al. (1979[Bresciani-Pahor, N., Calligaris, M., Nardin, G., Randaccio, L. & Viterbo, D. (1979). Acta Cryst. B35, 2776-2778.]); Haider et al. (1981[Haider, S. Z., Hashem, A., Malik, K. M. A. & Hursthouse, M. B. (1981). J. Bangaldesh Acad. Sci. 5, 85-92.]).

[Scheme 1]

Experimental

Crystal data

  • C18H14F6N2O2S2

  • Mr = 468.43

  • Orthorhombic, P n a 21

  • a = 20.4520 (4) Å

  • b = 12.5201 (2) Å

  • c = 15.8328 (2) Å

  • V = 4054.16 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.33 mm−1

  • T = 100 K

  • 0.30 × 0.25 × 0.20 mm
Data collection

  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.906, Tmax = 0.936

  • 40183 measured reflections

  • 9198 independent reflections

  • 8265 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.122

  • S = 1.05

  • 9198 reflections

  • 633 parameters

  • 242 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.59 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4340 Friedel pairs

  • Flack parameter: 0.01 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1n⋯O1 0.88 (1) 2.03 (3) 2.741 (3) 138 (3)
N2—H2n⋯O2 0.88 (1) 2.01 (3) 2.726 (3) 138 (3)
N3—H3n⋯O3 0.88 (1) 1.93 (3) 2.668 (3) 140 (3)
N4—H4n⋯O4 0.87 (1) 1.96 (3) 2.677 (3) 139 (3)

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811036889/xu5326sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036889/xu5326Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811036889/xu5326Isup3.cml

checkCIF report


Comment top

Ethylenediamine generally condenses with aldehydes and ketones to yield Schiff bases, which are typically yellow compounds whose coloration arises from the azomethine linkage. For some 1,3-diketones (such as acetylacetone and benzoylmethane), the diamine condenses with the carbony function of two ketone molecules. In the condensation product, the azomethine double-bond isomerizes to result in the formation of a secondary amine, as noted in the diamine, 4-((2-((1-methyl-3-oxo-but-1-enyl)amino)ethyl)amino)pent-3-en-2-one (from the condensation of ethylenediamine with acetylacetone) (Bresciani-Pahor et al., 1979) and the analogous amine from the condensation of ethylenediamine with benzoyacetone (Haider et al., 1981). The product from the condensation with 2-theonyltrifluoroacetone was first reported in 1995, but the authors of the study assigned it as (ethanediyldinitrilo)bis[fluoro(thienyl)butanone as they considered it a Schiff-base-alicyclic type of crown ether (Wang & Tong, 1995). The compound is, in fact, is diamine (Scheme I). The asymmetric unit of the diamine, C16H14F3N2O1S2, consists of two molecules; the C–C double-bond is of a Z-configuration. In the C4H3S–C═C–C(═O)–C segment, the thienyl ring and acetyl fragment are approximately coplanar. The amino group is an intramolecular hydrogen-bond donor to the carbonyl group, and the hydrogen bond generates a six-membered ring (Table 1). In both molecules, their thienyl rings are each disordered over two positions; one trifluoromethyl group is also disordered (Fig. 1 and Fig. 2). Whereas similar diamines are centrosymmetric molecules with the inversion center in the middle of the ethane link, the present compound is not. The –NH–CH2–CH2–NH chain adopts a twisted U-shape.

Related literature top

For the synthesis, see: Wang & Tong (1995). For related structures, see: Bresciani-Pahor et al. (1979); Haider et al. (1981).

Experimental top

Ethylenediamine (0.6 g, 10 mmol) and the 2-theonyltrifluoroacetone (2.2 g, 10 mmol) in benzene (50 ml) were heated in a Dean-Stark trap until no more water was collected (in about 2 h). The solvent was removed and the residue was treated with a little methanol. The solid that separated was recystallized from ethanol to yield light yellow crystals.

Refinement top

Carbon- and nitrogen-bound H-atoms were placed in calculated positions [C–H 0.95–0.99 Å; Uiso(H) 1.2Ueq(C)] and were included in the refinement in the riding model approximation. The amino H-atoms were located in a difference Fourier map and were refined with a distance restraint of N–H 0.88±0.01 Å; their temperature factors were tied by a factor of 1.5.

All four thiophene rings are disordered over two positions in four of the five atoms; their α-carbon atoms are ordered. The formal carbon–carbon single-bond distances were restrained to 1.36 ± 0.01 Å and the double-bond distances to 1.42±0.01 Å wherease the carbon–sulfur distances bond distances were restrained to 1.71±0.01 Å. All 1,3-related sulfur–carbon distances were restrained to within 0.01 Å of each other. The thienyl rings are each restrained to lie on a plane. For the S1/C1/C2/C3/C4 and S1'/C2'/C3'/C4 disordered rings, the isotropic temperature factor of C3' was set to the equivalent anisotropic temperature factor of S1; the S1 atom was allowed to refine anisotropically. The isotropic temperature factors of the atoms of the minor components were similarly restrained to those the anisotropic temperature factors of the atoms of the major components.

One of the trifluoromethyl groups is disordered over two positions. All carbon–fluoroine distances were restrained to within 0.01 Å of each other. The six F-atoms were restrained to lie on a plane; their anisotropic temperature factors were tightly restrained to be nearly isotropic.emperature factors of the primed atoms were set to those of the umprimed ones.

Some atoms (F5, F7, C3 and C29) displayed somewhat elongated ellipsoids, which may be a consequence of the large number of restraints. For the disordered thienyl rings, the S1–C4 and C3–C4 bond distances are show differences in the Hirshfeld test.

Omitted from the refinement owing to bad disagreement was (1 1 -1).

Structure description top

Ethylenediamine generally condenses with aldehydes and ketones to yield Schiff bases, which are typically yellow compounds whose coloration arises from the azomethine linkage. For some 1,3-diketones (such as acetylacetone and benzoylmethane), the diamine condenses with the carbony function of two ketone molecules. In the condensation product, the azomethine double-bond isomerizes to result in the formation of a secondary amine, as noted in the diamine, 4-((2-((1-methyl-3-oxo-but-1-enyl)amino)ethyl)amino)pent-3-en-2-one (from the condensation of ethylenediamine with acetylacetone) (Bresciani-Pahor et al., 1979) and the analogous amine from the condensation of ethylenediamine with benzoyacetone (Haider et al., 1981). The product from the condensation with 2-theonyltrifluoroacetone was first reported in 1995, but the authors of the study assigned it as (ethanediyldinitrilo)bis[fluoro(thienyl)butanone as they considered it a Schiff-base-alicyclic type of crown ether (Wang & Tong, 1995). The compound is, in fact, is diamine (Scheme I). The asymmetric unit of the diamine, C16H14F3N2O1S2, consists of two molecules; the C–C double-bond is of a Z-configuration. In the C4H3S–C═C–C(═O)–C segment, the thienyl ring and acetyl fragment are approximately coplanar. The amino group is an intramolecular hydrogen-bond donor to the carbonyl group, and the hydrogen bond generates a six-membered ring (Table 1). In both molecules, their thienyl rings are each disordered over two positions; one trifluoromethyl group is also disordered (Fig. 1 and Fig. 2). Whereas similar diamines are centrosymmetric molecules with the inversion center in the middle of the ethane link, the present compound is not. The –NH–CH2–CH2–NH chain adopts a twisted U-shape.

For the synthesis, see: Wang & Tong (1995). For related structures, see: Bresciani-Pahor et al. (1979); Haider et al. (1981).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of one of the two independent molecules of C16H14F3N2O1S2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
[Figure 2] Fig. 2. Thermal ellipsoid plot (Barbour, 2001) of second independent molecule of C16H14F3N2O1S2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
1,1,1-Trifluoro-4-(thiophen-2-yl)-4-[(2-{[4,4,4-trifluoro-3-oxo-1-(thiophen-2- yl)but-1-en-1-yl]amino}ethyl)amino]but-3-en-2-one top
Crystal data top
C18H14F6N2O2S2F(000) = 1904
Mr = 468.43Dx = 1.535 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 16458 reflections
a = 20.4520 (4) Åθ = 2.3–27.5°
b = 12.5201 (2) ŵ = 0.33 mm−1
c = 15.8328 (2) ÅT = 100 K
V = 4054.16 (11) Å3Block, light-yellow
Z = 80.30 × 0.25 × 0.20 mm
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector		9198 independent reflections
Radiation source: SuperNova (Mo) X-ray Source8265 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.037
Detector resolution: 10.4041 pixels mm-1θmax = 27.6°, θmin = 2.3°
ω scansh = −26→24
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)		k = −16→15
Tmin = 0.906, Tmax = 0.936l = −20→20
40183 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0629P)2 + 2.3648P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
9198 reflectionsΔρmax = 0.61 e Å−3
633 parametersΔρmin = −0.59 e Å−3
242 restraintsAbsolute structure: Flack (1983), 4340 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (7)
Crystal data top
C18H14F6N2O2S2V = 4054.16 (11) Å3
Mr = 468.43Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 20.4520 (4) ŵ = 0.33 mm−1
b = 12.5201 (2) ÅT = 100 K
c = 15.8328 (2) Å0.30 × 0.25 × 0.20 mm
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector		9198 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)		8265 reflections with I > 2σ(I)
Tmin = 0.906, Tmax = 0.936Rint = 0.037
40183 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122Δρmax = 0.61 e Å−3
S = 1.05Δρmin = −0.59 e Å−3
9198 reflectionsAbsolute structure: Flack (1983), 4340 Friedel pairs
633 parametersAbsolute structure parameter: 0.01 (7)
242 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.81914 (6)0.35483 (9)0.50113 (16)0.0299 (3)0.817 (4)
C3'0.8183 (5)0.3618 (12)0.4772 (9)0.030*0.183 (4)
H3'0.85820.40000.47180.036*0.183 (4)
S20.77950 (7)0.40257 (11)0.05479 (16)0.0309 (4)0.778 (4)
C13'0.7645 (6)0.4026 (14)0.0719 (9)0.031*0.222 (4)
H13'0.80730.37950.05750.037*0.222 (4)
S30.52193 (5)0.51039 (8)0.63447 (16)0.0349 (3)0.960 (4)
C21'0.5388 (9)0.502 (3)0.617 (4)0.035*0.040 (4)
H21'0.49870.47430.63800.042*0.040 (4)
S40.63026 (8)0.23117 (13)0.98065 (17)0.0337 (4)0.665 (4)
C31'0.6224 (5)0.2405 (11)0.9654 (7)0.034*0.335 (4)
H31'0.66050.26960.99090.040*0.335 (4)
C10.7728 (2)0.2583 (3)0.5476 (3)0.0292 (10)0.817 (4)
H10.78560.21980.59660.035*0.817 (4)
C2'0.8064 (7)0.2803 (13)0.5393 (9)0.029*0.183 (4)
H2'0.83710.25740.58050.035*0.183 (4)
C20.71492 (19)0.2427 (3)0.5062 (3)0.0273 (9)0.817 (4)
H20.68310.19070.52100.033*0.817 (4)
C1'0.7452 (8)0.2410 (12)0.5305 (9)0.027*0.183 (4)
H1'0.72760.18630.56530.033*0.183 (4)
C30.7094 (3)0.3148 (5)0.4387 (4)0.0270 (14)0.817 (4)
H30.67120.31960.40470.032*0.817 (4)
S1'0.7030 (3)0.3001 (8)0.4502 (6)0.027*0.183 (4)
C110.7226 (3)0.4923 (5)0.0199 (4)0.0344 (13)0.778 (4)
H110.72730.5338−0.03000.041*0.778 (4)
C12'0.7283 (10)0.478 (2)0.0239 (13)0.034*0.222 (4)
H12'0.74430.5110−0.02610.041*0.222 (4)
C120.6696 (3)0.4975 (5)0.0719 (3)0.0329 (12)0.778 (4)
H120.63340.54390.06340.039*0.778 (4)
C11'0.6679 (10)0.4979 (18)0.0575 (11)0.033*0.222 (4)
H11'0.63700.54600.03390.039*0.222 (4)
C130.6751 (3)0.4259 (4)0.1393 (4)0.0283 (12)0.778 (4)
H130.64220.41870.18120.034*0.778 (4)
S2'0.6554 (2)0.4254 (6)0.1468 (4)0.028*0.222 (4)
C190.5478 (2)0.6236 (3)0.5854 (3)0.0439 (12)0.960 (4)
H190.52090.68440.57610.053*0.960 (4)
C20'0.545 (2)0.600 (5)0.573 (6)0.044*0.040 (4)
H20'0.50890.64630.56160.053*0.040 (4)
C200.6113 (2)0.6170 (3)0.5612 (3)0.0374 (10)0.960 (4)
H200.63430.67230.53270.045*0.960 (4)
C19'0.607 (2)0.621 (4)0.549 (5)0.037*0.040 (4)
H19'0.62050.68340.51930.045*0.040 (4)
C210.6388 (2)0.5186 (4)0.5835 (3)0.0277 (8)0.960 (4)
H210.68280.50020.57110.033*0.960 (4)
S3'0.6590 (11)0.521 (2)0.580 (2)0.028*0.040 (4)
C290.5823 (3)0.1198 (5)0.9760 (5)0.0365 (17)0.665 (4)
H290.58940.05841.01010.044*0.665 (4)
C30'0.5976 (7)0.1367 (11)0.9825 (8)0.037*0.335 (4)
H30'0.61710.08791.02100.044*0.335 (4)
C300.5329 (3)0.1272 (5)0.9190 (5)0.0352 (15)0.665 (4)
H300.50290.07150.90630.042*0.665 (4)
C29'0.5429 (7)0.1157 (11)0.9377 (8)0.035*0.335 (4)
H29'0.51930.05050.94070.042*0.335 (4)
C310.5325 (5)0.2282 (8)0.8817 (8)0.039 (2)0.665 (4)
H310.49990.25030.84270.046*0.665 (4)
S4'0.5213 (3)0.2209 (6)0.8748 (4)0.039*0.335 (4)
F10.58969 (11)0.6069 (2)0.3032 (3)0.0653 (9)
F20.63964 (14)0.7449 (2)0.3477 (3)0.0697 (9)
F30.63082 (13)0.7177 (3)0.2175 (2)0.0758 (11)
F40.58607 (10)0.10854 (18)0.2800 (3)0.0557 (7)
F50.63759 (19)0.0490 (4)0.3863 (2)0.1062 (16)
F60.64439 (12)−0.02908 (19)0.2702 (3)0.0724 (10)
F70.4634 (2)0.1221 (3)0.5841 (4)0.0691 (19)0.637 (8)
F80.5383 (3)0.0168 (6)0.5542 (5)0.118 (3)0.637 (8)
F90.4967 (3)0.0071 (5)0.6696 (4)0.088 (2)0.637 (8)
F7'0.4514 (3)0.1011 (7)0.6466 (7)0.087 (3)0.363 (8)
F8'0.5011 (5)0.0915 (7)0.5354 (4)0.071 (3)0.363 (8)
F9'0.5227 (3)−0.0136 (4)0.6325 (6)0.050 (2)0.363 (8)
F100.50376 (13)0.7510 (2)0.9026 (2)0.0550 (7)
F110.46071 (15)0.6715 (3)0.7974 (2)0.0724 (9)
F120.44353 (12)0.6167 (2)0.9230 (3)0.0645 (8)
O10.74885 (10)0.63817 (17)0.2411 (2)0.0245 (5)
O20.75368 (11)0.10238 (17)0.3191 (2)0.0255 (5)
O30.61131 (12)0.11162 (18)0.6867 (2)0.0287 (5)
O40.59885 (11)0.62983 (18)0.8317 (2)0.0281 (5)
N10.81933 (13)0.4767 (2)0.3145 (2)0.0214 (5)
H1N0.8150 (17)0.526 (2)0.2758 (18)0.026*
N20.80754 (13)0.2661 (2)0.2295 (2)0.0227 (5)
H2N0.8117 (18)0.210 (2)0.263 (2)0.027*
N30.66015 (13)0.3092 (2)0.6906 (2)0.0206 (5)
H3N0.6634 (19)0.2397 (11)0.699 (2)0.025*
N40.65239 (12)0.4362 (2)0.8506 (2)0.0188 (5)
H4N0.6551 (18)0.5034 (12)0.836 (2)0.023*
C40.76321 (17)0.3778 (2)0.4254 (2)0.0273 (7)
C50.76608 (15)0.4627 (2)0.3615 (2)0.0218 (6)
C60.71094 (15)0.5277 (3)0.3520 (2)0.0244 (6)
H60.67490.51640.38870.029*
C70.70615 (15)0.6077 (2)0.2919 (2)0.0223 (6)
C80.64054 (16)0.6680 (3)0.2888 (3)0.0308 (7)
C90.87353 (15)0.4019 (2)0.3033 (2)0.0231 (6)
H9A0.87600.35360.35270.028*
H9B0.91520.44200.29980.028*
C100.86425 (15)0.3358 (3)0.2227 (2)0.0230 (6)
H10A0.85850.38440.17390.028*
H10B0.90380.29220.21250.028*
C140.73144 (15)0.3671 (2)0.1403 (2)0.0243 (6)
C150.74753 (16)0.2808 (2)0.2002 (2)0.0218 (6)
C160.69566 (16)0.2139 (3)0.2243 (2)0.0250 (6)
H160.65400.22520.19940.030*
C170.70247 (15)0.1316 (3)0.2830 (3)0.0238 (6)
C180.64150 (18)0.0659 (3)0.3048 (3)0.0358 (8)
C220.59719 (15)0.4511 (2)0.6247 (2)0.0248 (6)
C230.60659 (15)0.3393 (2)0.6502 (2)0.0213 (6)
C240.55877 (15)0.2635 (3)0.6291 (2)0.0256 (6)
H240.52030.28650.60080.031*
C250.56605 (16)0.1554 (3)0.6486 (3)0.0274 (7)
C260.51242 (19)0.0802 (3)0.6161 (3)0.0467 (11)
C270.71201 (15)0.3739 (2)0.7275 (2)0.0200 (6)
H27A0.70790.44870.70800.024*
H27B0.75520.34650.70920.024*
C280.70705 (15)0.3695 (2)0.8237 (2)0.0194 (6)
H28A0.70000.29500.84240.023*
H28B0.74820.39580.84940.023*
C320.58421 (15)0.2942 (2)0.9067 (2)0.0237 (6)
C330.59499 (15)0.4057 (2)0.8802 (2)0.0195 (6)
C340.54391 (16)0.4786 (3)0.8887 (2)0.0243 (6)
H340.50390.45540.91320.029*
C350.54967 (15)0.5854 (3)0.8622 (2)0.0238 (6)
C360.48897 (16)0.6564 (3)0.8712 (3)0.0331 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0389 (6)0.0307 (6)0.0202 (5)0.0018 (4)−0.0086 (4)0.0065 (4)
S20.0444 (8)0.0286 (6)0.0196 (6)−0.0034 (5)−0.0023 (4)0.0044 (4)
S30.0345 (5)0.0312 (5)0.0388 (5)0.0102 (4)−0.0073 (4)−0.0019 (4)
S40.0385 (8)0.0278 (7)0.0347 (8)−0.0062 (6)−0.0076 (6)0.0157 (6)
C10.052 (3)0.0195 (19)0.0158 (17)0.0066 (19)0.0069 (18)0.0055 (14)
C20.034 (2)0.0191 (18)0.029 (2)0.0017 (16)0.0095 (18)0.0034 (16)
C30.028 (2)0.009 (2)0.044 (3)−0.0054 (16)0.021 (2)0.0011 (19)
C110.064 (4)0.017 (3)0.022 (2)−0.009 (2)−0.019 (2)0.0030 (16)
C120.052 (3)0.020 (2)0.027 (3)−0.0032 (19)−0.022 (2)0.0014 (19)
C130.037 (3)0.024 (2)0.025 (2)−0.009 (3)−0.003 (3)−0.0018 (17)
C190.071 (3)0.0204 (19)0.040 (2)0.0077 (19)−0.025 (2)−0.0027 (17)
C200.066 (3)0.0229 (18)0.0238 (19)−0.0040 (18)−0.0130 (18)0.0034 (14)
C210.030 (2)0.031 (2)0.0221 (16)−0.004 (2)−0.002 (2)−0.0017 (13)
C290.040 (4)0.018 (3)0.051 (4)−0.007 (2)0.011 (3)0.019 (3)
C300.031 (3)0.024 (3)0.050 (4)−0.010 (2)0.001 (3)0.004 (3)
C310.039 (5)0.018 (3)0.058 (5)0.002 (3)−0.012 (3)0.008 (3)
F10.0253 (11)0.0377 (14)0.133 (3)0.0008 (10)0.0128 (14)0.0210 (15)
F20.0597 (17)0.0509 (16)0.098 (2)0.0229 (14)−0.0003 (17)−0.0277 (16)
F30.0454 (15)0.115 (3)0.0672 (18)0.0397 (16)0.0135 (13)0.0494 (18)
F40.0242 (10)0.0285 (12)0.114 (2)0.0029 (8)0.0065 (13)0.0132 (13)
F50.083 (2)0.180 (4)0.0556 (18)−0.080 (3)0.0037 (16)0.037 (2)
F60.0357 (12)0.0205 (12)0.161 (3)−0.0042 (9)0.0048 (17)−0.0111 (15)
F70.041 (2)0.052 (2)0.115 (4)−0.0208 (19)−0.053 (3)0.029 (3)
F80.105 (4)0.119 (5)0.131 (5)−0.029 (4)−0.014 (3)−0.083 (4)
F90.057 (3)0.096 (4)0.110 (4)−0.052 (3)−0.032 (3)0.056 (3)
F7'0.055 (4)0.083 (5)0.122 (6)−0.022 (4)0.018 (4)−0.015 (4)
F8'0.097 (5)0.064 (5)0.052 (4)−0.038 (4)−0.033 (4)0.009 (3)
F9'0.039 (4)0.029 (3)0.081 (5)−0.009 (3)−0.030 (3)0.000 (3)
F100.0432 (13)0.0328 (13)0.089 (2)0.0075 (10)0.0100 (13)−0.0235 (13)
F110.0778 (19)0.081 (2)0.0579 (16)0.0553 (18)−0.0245 (15)−0.0128 (16)
F120.0347 (13)0.0500 (15)0.109 (2)0.0131 (11)0.0295 (15)0.0152 (16)
O10.0239 (11)0.0206 (11)0.0291 (11)−0.0008 (8)0.0029 (9)0.0048 (9)
O20.0278 (11)0.0187 (11)0.0299 (11)0.0014 (9)0.0003 (9)0.0029 (9)
O30.0288 (12)0.0240 (12)0.0332 (12)−0.0046 (9)−0.0100 (10)0.0038 (10)
O40.0264 (11)0.0207 (11)0.0373 (12)−0.0001 (9)0.0027 (10)0.0046 (9)
N10.0242 (12)0.0166 (12)0.0233 (13)0.0012 (10)−0.0013 (10)0.0016 (10)
N20.0296 (14)0.0164 (12)0.0220 (12)−0.0012 (10)0.0006 (11)0.0006 (10)
N30.0246 (13)0.0159 (12)0.0213 (12)−0.0027 (10)−0.0020 (10)0.0002 (10)
N40.0206 (11)0.0141 (12)0.0219 (12)−0.0004 (10)0.0001 (10)0.0007 (9)
C40.0436 (19)0.0223 (16)0.0159 (14)0.0046 (14)0.0039 (13)0.0016 (12)
C50.0270 (15)0.0193 (15)0.0190 (13)−0.0017 (12)−0.0008 (12)−0.0005 (11)
C60.0280 (15)0.0221 (15)0.0230 (15)−0.0001 (13)0.0070 (12)0.0017 (12)
C70.0225 (14)0.0201 (15)0.0242 (14)−0.0023 (11)0.0001 (12)−0.0018 (12)
C80.0259 (16)0.0235 (16)0.0429 (19)0.0013 (13)0.0060 (15)0.0049 (15)
C90.0209 (14)0.0219 (15)0.0264 (15)0.0024 (12)−0.0025 (12)0.0037 (12)
C100.0234 (14)0.0211 (15)0.0245 (14)0.0008 (12)0.0021 (12)0.0037 (12)
C140.0333 (16)0.0196 (14)0.0199 (14)−0.0010 (12)−0.0051 (13)−0.0011 (12)
C150.0295 (16)0.0189 (15)0.0170 (13)0.0006 (12)−0.0016 (12)−0.0032 (11)
C160.0263 (15)0.0236 (16)0.0251 (15)0.0018 (12)−0.0044 (13)−0.0019 (12)
C170.0258 (15)0.0177 (14)0.0279 (15)−0.0011 (11)0.0029 (13)−0.0011 (12)
C180.0297 (17)0.0284 (18)0.049 (2)−0.0022 (14)−0.0015 (16)0.0045 (16)
C220.0311 (16)0.0238 (15)0.0194 (14)0.0014 (13)−0.0072 (12)0.0007 (12)
C230.0242 (14)0.0215 (14)0.0184 (13)−0.0006 (12)0.0000 (11)0.0001 (11)
C240.0248 (15)0.0259 (16)0.0262 (15)−0.0018 (12)−0.0076 (13)0.0019 (12)
C250.0268 (15)0.0299 (17)0.0255 (15)−0.0051 (13)−0.0056 (13)0.0022 (13)
C260.048 (2)0.032 (2)0.060 (3)−0.0172 (18)−0.023 (2)0.0123 (19)
C270.0207 (14)0.0177 (14)0.0217 (14)−0.0024 (11)−0.0018 (12)−0.0019 (11)
C280.0207 (14)0.0157 (13)0.0219 (13)0.0017 (11)−0.0008 (11)0.0002 (11)
C320.0250 (15)0.0206 (15)0.0256 (15)−0.0001 (12)0.0029 (12)0.0034 (12)
C330.0215 (14)0.0208 (14)0.0163 (13)−0.0045 (11)−0.0008 (11)−0.0004 (11)
C340.0207 (14)0.0241 (16)0.0279 (15)−0.0020 (12)0.0013 (12)0.0044 (12)
C350.0223 (14)0.0227 (16)0.0264 (15)0.0017 (12)−0.0008 (12)0.0002 (12)
C360.0260 (16)0.0271 (18)0.046 (2)0.0035 (14)0.0005 (15)−0.0016 (15)
Geometric parameters (Å, º) top
S1—C41.682 (3)S4'—C321.659 (6)
S1—C11.704 (4)F1—C81.311 (4)
C3'—C41.408 (10)F2—C81.340 (5)
C3'—C2'1.438 (11)F3—C81.304 (4)
C3'—H3'0.9500F4—C181.313 (4)
S2—C111.710 (5)F5—C181.310 (5)
S2—C141.731 (3)F6—C181.310 (5)
C13'—C141.351 (10)F7—C261.240 (5)
C13'—C12'1.421 (11)F8—C261.368 (6)
C13'—H13'0.9500F9—C261.288 (5)
S3—C191.701 (4)F7'—C261.363 (6)
S3—C221.716 (3)F8'—C261.306 (6)
C21'—C221.357 (12)F9'—C261.222 (6)
C21'—C20'1.420 (12)F10—C361.318 (4)
C21'—H21'0.9500F11—C361.317 (5)
S4—C321.697 (3)F12—C361.336 (5)
S4—C291.707 (5)O1—C71.248 (4)
C31'—C321.387 (9)O2—C171.248 (4)
C31'—C30'1.422 (11)O3—C251.233 (4)
C31'—H31'0.9500O4—C351.247 (4)
C1—C21.367 (6)N1—C51.331 (4)
C1—H10.9500N1—C91.462 (4)
C2'—C1'1.352 (11)N1—H1N0.875 (12)
C2'—H2'0.9500N2—C151.325 (4)
C2—C31.404 (6)N2—C101.455 (4)
C2—H20.9500N2—H2N0.878 (12)
C1'—S1'1.705 (11)N3—C231.323 (4)
C1'—H1'0.9500N3—C271.457 (4)
C3—C41.371 (5)N3—H3N0.882 (12)
C3—H30.9500N4—C331.321 (4)
S1'—C41.618 (7)N4—C281.459 (4)
C11—C121.362 (6)N4—H4N0.874 (12)
C11—H110.9500C4—C51.468 (4)
C12'—C11'1.368 (11)C5—C61.399 (4)
C12'—H12'0.9500C6—C71.385 (4)
C12—C131.398 (6)C6—H60.9500
C12—H120.9500C7—C81.541 (4)
C11'—S2'1.701 (11)C9—C101.533 (4)
C11'—H11'0.9500C9—H9A0.9900
C13—C141.367 (6)C9—H9B0.9900
C13—H130.9500C10—H10A0.9900
S2'—C141.722 (6)C10—H10B0.9900
C19—C201.358 (6)C14—C151.476 (4)
C19—H190.9500C15—C161.405 (4)
C20'—C19'1.360 (12)C16—C171.394 (5)
C20'—H20'0.9500C16—H160.9500
C20—C211.400 (5)C17—C181.533 (5)
C20—H200.9500C22—C231.470 (4)
C19'—S3'1.709 (12)C23—C241.402 (4)
C19'—H19'0.9500C24—C251.397 (5)
C21—C221.364 (5)C24—H240.9500
C21—H210.9500C25—C261.534 (5)
S3'—C221.697 (11)C27—C281.528 (4)
C29—C301.357 (7)C27—H27A0.9900
C29—H290.9500C27—H27B0.9900
C30'—C29'1.351 (11)C28—H28A0.9900
C30'—H30'0.9500C28—H28B0.9900
C30—C311.396 (9)C32—C331.474 (4)
C30—H300.9500C33—C341.394 (4)
C29'—S4'1.708 (10)C34—C351.406 (4)
C29'—H29'0.9500C34—H340.9500
C31—C321.399 (7)C35—C361.534 (4)
C31—H310.9500
C4—S1—C192.9 (2)C5—C6—H6118.3
C4—C3'—C2'111.3 (7)O1—C7—C6128.0 (3)
C4—C3'—H3'124.3O1—C7—C8116.0 (3)
C2'—C3'—H3'124.3C6—C7—C8116.0 (3)
C11—S2—C1492.0 (2)F3—C8—F1107.9 (3)
C14—C13'—C12'112.7 (7)F3—C8—F2104.9 (3)
C14—C13'—H13'123.6F1—C8—F2106.7 (3)
C12'—C13'—H13'123.6F3—C8—C7113.2 (3)
C19—S3—C2292.3 (2)F1—C8—C7113.6 (3)
C22—C21'—C20'112.0 (9)F2—C8—C7110.0 (3)
C22—C21'—H21'124.0N1—C9—C10110.7 (2)
C20'—C21'—H21'124.0N1—C9—H9A109.5
C32—S4—C2991.8 (2)C10—C9—H9A109.5
C30'—C31'—H31'124.2N1—C9—H9B109.5
C2—C1—S1112.0 (3)C10—C9—H9B109.5
C2—C1—H1124.0H9A—C9—H9B108.1
S1—C1—H1124.0N2—C10—C9111.1 (2)
C1'—C2'—C3'110.2 (8)N2—C10—H10A109.4
C1'—C2'—H2'124.9C9—C10—H10A109.4
C3'—C2'—H2'124.9N2—C10—H10B109.4
C1—C2—C3110.1 (4)C9—C10—H10B109.4
C1—C2—H2124.9H10A—C10—H10B108.0
C3—C2—H2124.9C13'—C14—C15130.1 (7)
C2'—C1'—S1'112.8 (10)C13—C14—C15126.1 (3)
C2'—C1'—H1'123.6C13'—C14—S2'111.2 (7)
S1'—C1'—H1'123.6C15—C14—S2'118.2 (3)
C4—C3—C2114.9 (4)C13—C14—S2109.4 (3)
C4—C3—H3122.5C15—C14—S2124.3 (2)
C2—C3—H3122.5N2—C15—C16121.5 (3)
C4—S1'—C1'93.3 (6)N2—C15—C14122.2 (3)
C12—C11—S2112.1 (4)C16—C15—C14116.3 (3)
C12—C11—H11123.9C17—C16—C15123.1 (3)
S2—C11—H11123.9C17—C16—H16118.5
C11'—C12'—C13'112.5 (9)C15—C16—H16118.5
C11'—C12'—H12'123.7O2—C17—C16127.3 (3)
C13'—C12'—H12'123.7O2—C17—C18115.0 (3)
C11—C12—C13111.6 (4)C16—C17—C18117.7 (3)
C11—C12—H12124.2F6—C18—F5105.6 (4)
C13—C12—H12124.2F6—C18—F4106.4 (3)
C12'—C11'—S2'111.3 (10)F5—C18—F4107.9 (4)
C12'—C11'—H11'124.4F6—C18—C17110.9 (3)
S2'—C11'—H11'124.4F5—C18—C17111.0 (3)
C14—C13—C12115.0 (4)F4—C18—C17114.6 (3)
C14—C13—H13122.5C21—C22—C23129.7 (3)
C12—C13—H13122.5C23—C22—S3'120.8 (11)
C11'—S2'—C1492.3 (6)C21—C22—S3109.5 (3)
C20—C19—S3112.1 (3)C23—C22—S3120.3 (2)
C20—C19—H19124.0N3—C23—C24120.0 (3)
S3—C19—H19124.0N3—C23—C22120.8 (3)
C19'—C20'—C21'112.6 (9)C24—C23—C22119.2 (3)
C19'—C20'—H20'123.7C25—C24—C23121.9 (3)
C21'—C20'—H20'123.7C25—C24—H24119.0
C19—C20—C21111.4 (4)C23—C24—H24119.0
C19—C20—H20124.3O3—C25—C24128.2 (3)
C21—C20—H20124.3O3—C25—C26115.3 (3)
C20'—C19'—S3'111.2 (11)C24—C25—C26116.4 (3)
C20'—C19'—H19'124.4F7—C26—F9111.5 (4)
S3'—C19'—H19'124.4F9'—C26—F8'110.0 (5)
C22—C21—C20114.6 (4)F9'—C26—F7'105.6 (5)
C22—C21—H21122.7F7—C26—F8105.4 (4)
C20—C21—H21122.7F9—C26—F898.9 (4)
C30—C29—S4113.6 (4)F9'—C26—C25113.3 (3)
C30—C29—H29123.2F7—C26—C25117.1 (3)
S4—C29—H29123.2F9—C26—C25113.3 (3)
C29'—C30'—C31'111.9 (8)F8'—C26—C25112.8 (4)
C29'—C30'—H30'124.0F7'—C26—C25114.7 (4)
C31'—C30'—H30'124.0F8—C26—C25108.6 (4)
C29—C30—C31110.3 (5)N3—C27—C28109.4 (2)
C29—C30—H30124.8N3—C27—H27A109.8
C31—C30—H30124.8C28—C27—H27A109.8
C30'—C29'—S4'111.7 (10)N3—C27—H27B109.8
C30'—C29'—H29'124.1C28—C27—H27B109.8
S4'—C29'—H29'124.1H27A—C27—H27B108.2
C30—C31—C32114.2 (5)N4—C28—C27108.7 (2)
C30—C31—H31122.9N4—C28—H28A109.9
C32—C31—H31122.9C27—C28—H28A109.9
C32—S4'—C29'92.8 (6)N4—C28—H28B109.9
C5—N1—C9127.1 (3)C27—C28—H28B109.9
C5—N1—H1N114 (2)H28A—C28—H28B108.3
C9—N1—H1N116 (2)C31'—C32—C33124.4 (6)
C15—N2—C10129.0 (3)C31—C32—C33126.2 (4)
C15—N2—H2N114 (2)C33—C32—S4'123.6 (3)
C10—N2—H2N116 (2)C31—C32—S4109.9 (4)
C23—N3—C27129.7 (3)C33—C32—S4123.6 (2)
C23—N3—H3N114 (3)S4'—C32—S4112.5 (3)
C27—N3—H3N116 (3)N4—C33—C34120.7 (3)
C33—N4—C28128.2 (3)N4—C33—C32120.6 (3)
C33—N4—H4N115 (2)C34—C33—C32118.7 (3)
C28—N4—H4N115 (3)C33—C34—C35122.1 (3)
C3—C4—C5123.7 (4)C33—C34—H34119.0
C3'—C4—C5118.2 (7)C35—C34—H34119.0
C3'—C4—S1'112.4 (7)O4—C35—C34127.4 (3)
C5—C4—S1'129.3 (4)O4—C35—C36115.5 (3)
C3—C4—S1109.8 (3)C34—C35—C36117.1 (3)
C5—C4—S1126.0 (3)F10—C36—F11107.8 (3)
N1—C5—C6121.5 (3)F10—C36—F12105.3 (3)
N1—C5—C4120.9 (3)F11—C36—F12107.0 (3)
C6—C5—C4117.6 (3)F10—C36—C35111.7 (3)
C7—C6—C5123.5 (3)F11—C36—C35110.8 (3)
C7—C6—H6118.3F12—C36—C35113.8 (3)
C4—S1—C1—C20.1 (3)C14—C15—C16—C17−177.3 (3)
C4—C3'—C2'—C1'0.2 (5)C15—C16—C17—O2−3.3 (5)
S1—C1—C2—C3−2.5 (5)C15—C16—C17—C18178.9 (3)
C3'—C2'—C1'—S1'−0.1 (2)O2—C17—C18—F6−72.0 (4)
C1—C2—C3—C44.4 (7)C16—C17—C18—F6106.1 (4)
C2'—C1'—S1'—C4−0.1 (2)O2—C17—C18—F545.0 (5)
C14—S2—C11—C121.4 (4)C16—C17—C18—F5−136.9 (4)
C14—C13'—C12'—C11'−0.1 (5)O2—C17—C18—F4167.5 (3)
S2—C11—C12—C13−1.4 (5)C16—C17—C18—F4−14.3 (5)
C13'—C12'—C11'—S2'0.0 (2)C20'—C21'—C22—C21−1.4 (16)
C11—C12—C13—C140.7 (6)C20'—C21'—C22—C23−166 (3)
C12'—C11'—S2'—C140.02 (18)C20'—C21'—C22—S3'0.0 (6)
C22—S3—C19—C200.7 (3)C20—C21—C22—C23173.5 (3)
C22—C21'—C20'—C19'0.0 (5)C20—C21—C22—S3'−163 (9)
S3—C19—C20—C21−0.3 (4)C20—C21—C22—S30.9 (4)
C21'—C20'—C19'—S3'0.0 (2)C19'—S3'—C22—C21'0.0 (4)
C19—C20—C21—C22−0.4 (5)C19—S3—C22—C21−0.9 (3)
C20'—C19'—S3'—C22−0.01 (19)C19—S3—C22—C23−174.3 (3)
C32—S4—C29—C301.2 (5)C19—S3—C22—S3'2.1 (15)
C32—C31'—C30'—C29'0.0 (5)C27—N3—C23—C24−171.8 (3)
S4—C29—C30—C31−3.1 (8)C27—N3—C23—C229.9 (5)
C31'—C30'—C29'—S4'0.0 (2)C21'—C22—C23—N3−150 (3)
C29—C30—C31—C324.0 (12)C21—C22—C23—N348.7 (5)
C30'—C29'—S4'—C320.00 (19)S3'—C22—C23—N344.2 (15)
C2—C3—C4—C3'2.3 (11)S3—C22—C23—N3−139.5 (3)
C2—C3—C4—C5−176.2 (4)C21'—C22—C23—C2431 (3)
C2—C3—C4—S1'−12 (6)C21—C22—C23—C24−129.6 (4)
C2—C3—C4—S1−4.3 (6)S3'—C22—C23—C24−134.1 (15)
C2'—C3'—C4—C3−1.9 (9)S3—C22—C23—C2442.2 (4)
C2'—C3'—C4—C5176.7 (5)N3—C23—C24—C25−0.9 (5)
C2'—C3'—C4—S1'−0.2 (6)C22—C23—C24—C25177.4 (3)
C1'—S1'—C4—C3'0.2 (4)C23—C24—C25—O32.1 (6)
C1'—S1'—C4—C5−176.4 (5)C23—C24—C25—C26−175.6 (3)
C1'—S1'—C4—S1−6.0 (5)O3—C25—C26—F9'−0.5 (7)
C1—S1—C4—C32.3 (4)C24—C25—C26—F9'177.5 (6)
C1—S1—C4—C5174.0 (3)O3—C25—C26—F7173.8 (5)
C1—S1—C4—S1'3.2 (4)C24—C25—C26—F7−8.2 (6)
C9—N1—C5—C6−164.6 (3)O3—C25—C26—F941.8 (6)
C9—N1—C5—C415.3 (5)C24—C25—C26—F9−140.1 (5)
C3—C4—C5—N1−138.4 (5)O3—C25—C26—F8'−126.4 (6)
C3'—C4—C5—N143.1 (7)C24—C25—C26—F8'51.7 (7)
S1'—C4—C5—N1−140.6 (5)O3—C25—C26—F7'120.8 (7)
S1—C4—C5—N151.0 (4)C24—C25—C26—F7'−61.2 (7)
C3—C4—C5—C641.4 (6)O3—C25—C26—F8−67.0 (6)
C3'—C4—C5—C6−137.1 (7)C24—C25—C26—F8111.0 (5)
S1'—C4—C5—C639.3 (6)C23—N3—C27—C28108.1 (3)
S1—C4—C5—C6−129.1 (3)C33—N4—C28—C27107.6 (3)
N1—C5—C6—C72.6 (5)N3—C27—C28—N4−75.1 (3)
C4—C5—C6—C7−177.3 (3)C30'—C31'—C32—C31−0.5 (10)
C5—C6—C7—O1−3.7 (5)C30'—C31'—C32—C33175.9 (6)
C5—C6—C7—C8177.7 (3)C30'—C31'—C32—S4'0.0 (6)
O1—C7—C8—F320.9 (5)C30'—C31'—C32—S4112 (20)
C6—C7—C8—F3−160.3 (3)C30—C31—C32—C31'−1.4 (14)
O1—C7—C8—F1144.5 (3)C30—C31—C32—C33−177.7 (6)
C6—C7—C8—F1−36.8 (4)C30—C31—C32—S4'−171 (20)
O1—C7—C8—F2−96.0 (4)C30—C31—C32—S4−3.1 (12)
C6—C7—C8—F282.7 (4)C29'—S4'—C32—C31'0.0 (4)
C5—N1—C9—C1096.2 (4)C29'—S4'—C32—C33−175.9 (5)
C15—N2—C10—C998.3 (4)C29'—S4'—C32—S4−1.7 (5)
N1—C9—C10—N2−65.9 (3)C29—S4—C32—C311.0 (7)
C12'—C13'—C14—C13−4.0 (7)C29—S4—C32—C33175.8 (4)
C12'—C13'—C14—C15172.0 (10)C29—S4—C32—S4'1.6 (4)
C12'—C13'—C14—S2'0.1 (6)C28—N4—C33—C34−168.3 (3)
C12—C13—C14—C13'1.0 (11)C28—N4—C33—C3213.1 (4)
C12—C13—C14—C15−175.2 (4)C31'—C32—C33—N454.7 (7)
C12—C13—C14—S20.4 (6)C31—C32—C33—N4−129.5 (8)
C11'—S2'—C14—C13'−0.1 (4)S4'—C32—C33—N4−129.9 (4)
C11'—S2'—C14—C15−173.0 (9)S4—C32—C33—N456.6 (4)
C11'—S2'—C14—S2−1.2 (9)C31'—C32—C33—C34−123.9 (6)
C11—S2—C14—C13−1.0 (4)C31—C32—C33—C3451.9 (9)
C11—S2—C14—C15174.7 (3)S4'—C32—C33—C3451.5 (5)
C11—S2—C14—S2'3.4 (4)S4—C32—C33—C34−122.1 (3)
C10—N2—C15—C16−169.2 (3)N4—C33—C34—C353.6 (5)
C10—N2—C15—C1411.3 (5)C32—C33—C34—C35−177.8 (3)
C13'—C14—C15—N241.9 (11)C33—C34—C35—O4−2.6 (5)
C13—C14—C15—N2−142.9 (4)C33—C34—C35—C36177.2 (3)
S2'—C14—C15—N2−146.6 (4)O4—C35—C36—F10−44.5 (4)
S2—C14—C15—N242.2 (4)C34—C35—C36—F10135.7 (3)
C13'—C14—C15—C16−137.6 (11)O4—C35—C36—F1175.8 (4)
C13—C14—C15—C1637.6 (5)C34—C35—C36—F11−104.0 (4)
S2'—C14—C15—C1633.9 (4)O4—C35—C36—F12−163.5 (3)
S2—C14—C15—C16−137.3 (3)C34—C35—C36—F1216.6 (5)
N2—C15—C16—C173.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O10.88 (1)2.03 (3)2.741 (3)138 (3)
N2—H2n···O20.88 (1)2.01 (3)2.726 (3)138 (3)
N3—H3n···O30.88 (1)1.93 (3)2.668 (3)140 (3)
N4—H4n···O40.87 (1)1.96 (3)2.677 (3)139 (3)

Experimental details

Crystal data
Chemical formulaC18H14F6N2O2S2
Mr468.43
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)100
a, b, c (Å)20.4520 (4), 12.5201 (2), 15.8328 (2)
V (Å3)4054.16 (11)
Z8
Radiation typeMo Kα
µ (mm−1)0.33
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.906, 0.936
No. of measured, independent and
observed [I > 2σ(I)] reflections		40183, 9198, 8265
Rint0.037
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.122, 1.05
No. of reflections9198
No. of parameters633
No. of restraints242
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.61, −0.59
Absolute structureFlack (1983), 4340 Friedel pairs
Absolute structure parameter0.01 (7)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O10.88 (1)2.03 (3)2.741 (3)138 (3)
N2—H2n···O20.88 (1)2.01 (3)2.726 (3)138 (3)
N3—H3n···O30.88 (1)1.93 (3)2.668 (3)140 (3)
N4—H4n···O40.87 (1)1.96 (3)2.677 (3)139 (3)
 

Acknowledgements

We thank King Abdulaziz University and the University of Malaya for supporting this study.

References

First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
 First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBresciani-Pahor, N., Calligaris, M., Nardin, G., Randaccio, L. & Viterbo, D. (1979). Acta Cryst. B35, 2776–2778.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationHaider, S. Z., Hashem, A., Malik, K. M. A. & Hursthouse, M. B. (1981). J. Bangaldesh Acad. Sci. 5, 85–92.  CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, W. & Tong, J. (1995). J. Natur. Sci. Xiangtan Univ. 17, 52–57.  CAS Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Pages o2659-o2660
https://doi.org/10.1107/S1600536811036889
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