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ISSN: 2056-9890

2-[(4-Chloro­benz­yl)sulfanyl]-4-(2-methyl­prop­yl)-6-[3-(tri­fluoro­meth­yl)anilino]­pyrimidine-5-carbo­nitrile

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 10 May 2012; accepted 7 June 2012; online 13 June 2012)

Three independent mol­ecules comprise the asymmetric unit of the title compound, C23H20ClF3N4S. The conformations of the mol­ecules are similar with the chloro­benzene and CF3-benzene rings almost perpendicular to, and almost co-planar with, the pyrimidinyl ring [range of dihedral angles = 80.36 (13)–88.07 (14) and 11.89 (14)–23.30 (14)°, respectively]; the benzene rings are roughly orthogonal to each other [64.81 (16)–72.16 (15)°]. In the crystal, two of the independent mol­ecules associate via weak N—H⋯N(cyano) hydrogen bonds and 12-membered {⋯HNC3N}2 synthons; the third independent mol­ecule self-associates similarly but about a centre of inversion. The sample studied was found to be a non-merohedral twin and the minor twin component refined to 47.16 (7)%.

Related literature

For the chemotherapeutic efficacy of pyrimidine derivatives, see: Al-Safarjalani et al. (2005[Al-Safarjalani, O. N., Zhou, X., Rais, R. H., Shi, J., Schinazi, R. F., Naguib, F. N. M. & El Kouni, M. H. (2005). Cancer Chemother. Pharmacol. 55, 541-551.]); Brunelle et al. (2007[Brunelle, M. N., Lucifora, J., Neyts, J., Villet, S., Holy, A., Trepo, C. & Zoulim, F. (2007). Antimicrob. Agents Chemother. 51, 2240-2243.]); Ding et al. (2006[Ding, Y., Girardet, J.-L., Smith, K. L., Larson, G., Prigaro, B., Wu, J. Z. & Yao, N. (2006). Bioorg. Chem. 34, 26-38.]); Al-Abdullah et al. (2011[Al-Abdullah, E. S., Al-Obaid, A. M., Al-Deeb, O. A., Habib, E. E. & El-Emam, A. A. (2011). Eur. J. Med. Chem. 46, 4642-4647.]). For recent inter­est in the chemical and pharmacological properties of pyrimidine derivatives, see: Al-Omar et al. (2010[Al-Omar, M. A., Al-Obaid, A. M., El-Brollosy, N. R. & El-Emam, A. A. (2010). Synth. Commun. 40, 1530-1538.]); El-Emam et al. (2011[El-Emam, A. A., Al-Deeb, O. A., Al-Turkistani, A. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o3126.]). For the treatment of data from a twinned crystal, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C23H20ClF3N4S

  • Mr = 476.94

  • Triclinic, [P \overline 1]

  • a = 15.3906 (6) Å

  • b = 15.7040 (7) Å

  • c = 15.9129 (7) Å

  • α = 89.568 (3)°

  • β = 74.825 (4)°

  • γ = 62.980 (4)°

  • V = 3278.9 (2) Å3

  • Z = 6

  • Cu Kα radiation

  • μ = 2.83 mm−1

  • T = 100 K

  • 0.35 × 0.15 × 0.03 mm

Data collection
  • Agilent SuperNova Dual diffractometer with Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.437, Tmax = 0.920

  • 38203 measured reflections

  • 25266 independent reflections

  • 18393 reflections with I > 2σ(I)

  • Rint = 0.075

Refinement
  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.190

  • S = 1.02

  • 25266 reflections

  • 866 parameters

  • H-atom parameters constrained

  • Δρmax = 1.44 e Å−3

  • Δρmin = −0.53 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N4—H4n⋯N7i 0.88 2.39 3.227 (3) 159
N8—H8n⋯N3i 0.88 2.38 3.213 (3) 158
N12—H12n⋯N11ii 0.88 2.36 3.206 (3) 160
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]), DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and QMol (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The chemotherapeutic efficacy of pyrimidine derivatives is related to their ability to inhibit vital enzymes responsible for DNA bio-synthesis. Thus, several pyrimidine non-nucleoside derivatives are known to exhibit anti-cancer (Al-Safarjalani et al., 2005), anti-viral (Brunelle et al., 2007; Ding et al., 2006) and anti-bacterial activities (Al-Abdullah et al., 2011). In continuation to our interest in the chemical and pharmacological properties of pyrimidine derivatives (Al-Omar et al., 2010; El-Emam et al. 2011), we synthesized the title compound (I) as potential a chemotherapeutic agent.

In (I), Fig. 1, three independent molecules comprise the asymmetric unit, and these have very similar molecular conformations as seen in the overlay diagram, Fig. 2. With respect to the pyrimidinyl ring, the chlorobenzene and CF3-benzene rings form dihedral angles of 80.36 (13) and 11.89 (14)°, respectively, for the N1-containing molecule; the dihedral angle between the benzene rings is 69.50 (14)°. For the N5-containing molecule the dihedral angles are 88.07 (14), 23.30 (14) and 64.81 (16), respectively, and for the N9-containing molecule, the angles are 85.94 (14), 13.81 (14) and 72.16 (15)°, respectively. In each case, the 2-methylpropyl group is orientated in the same direction as the chlorobenzene ring.

In the crystal structure, the N1- and N5-containing molecules associate to form a two molecule aggregate via NH···N(cyano) hydrogen bonds and 12-membered {···HNC3N}2 synthons, Table 1 and Fig. 3. The N3-containing molecules self-associate similarly but over a centre of inversion, Table 1.

Related literature top

For the chemotherapeutic efficacy of pyrimidine derivatives, see: Al-Safarjalani et al. (2005); Brunelle et al. (2007); Ding et al. (2006); Al-Abdullah et al. (2011). For recent interest in the chemical and pharmacological properties of pyrimidine derivatives, see: Al-Omar et al. (2010); El-Emam et al. (2011). For the treatment of data from a twinned crystal, see: Spek (2009).

Experimental top

To a solution of 2-(4-chlorobenzylsulfanyl)-6-chloro-4-(2-methylpropyl)pyrimidine-5-carbonitrile (705 mg, 2 mmol) in ethanol (8 ml), 3-trifluoromethylaniline (0.002 mol) and anhydrous potassium carbonate (322 mg, 2 mmol) were added and the mixture was heated under reflux for 6 h. On cooling the mixture, the solvent was then distilled in vacuo, and water (10 ml) was added to the residue. The separated precipitate was filtered, washed with cold water, dried and crystallized from ethanol to yield 591 mg (62%) of the title compound as colourless crystals. M.pt: 409–411 K. Colourless prisms were obtained by slow evaporation of its CHCl3:EtOH (1:1, 5 ml) solution held at room temperature. 1H NMR (DMSO-d6, 500.13 MHz): δ 0.92 (d, 6H, CH3, J = 7.0 Hz), 2.08–2.12 (m, 1H, CH), 2.62 (d, 2H, CH2CH, J = 7.0 Hz), 4.24 (s, 2H, CH2S), 7.10–7.25 (m, 4H, Ar—H), 7.45–7.57 (m, 2H, Ar—H), 7.83–7.85 (m, 1H, Ar—H), 8.0 (s, 1H, Ar—H), 10.01 (s, 1H, NH). 13C NMR (DMSO-d6, 125.76 MHz): δ 21.88 (CH3CH), 27.68 (CHCH3), 33.06 (CH2S), 44.92 (CH2CH), 87.66 (C-5), 115.02 (CN), 115.65, 121.23, 124.08, 127.23, 128.65, 129.60, 129.75, 129.90, 131.25, 131.86, 137.23, 139.26 (Ar—C & CF3), 158.90 (C-6), 172.88, 173.28 (C-2 & C-4).

Refinement top

Carbon-bound H-atoms were placed in calculated positions [N—H = 0.88 Å and C—H = 0.95 to 1.00 Å, Uiso(H) = 1.2–1.5Ueq(N, C)] and were included in the refinement in the riding model approximation. The sample studied iss a non-merohedral twin and a full sphere of reflections was measured. As it was not possible to separate the diffraction spots in two domains, the twin domains were separated using the TwinRotMat routine of PLATON (Spek, 2009). The minor twin component refined to 47.16 (7)%. Two reflections,i.e. (11 8 2) and (0 2 4), were omitted owing to poor agreement. The maximum and minimum residual electron density peaks of 1.44 and 0.53 e Å-3, respectively, were located 0.51 Å and 0.81 Å from the H13C and F9 atoms, respectively.

Structure description top

The chemotherapeutic efficacy of pyrimidine derivatives is related to their ability to inhibit vital enzymes responsible for DNA bio-synthesis. Thus, several pyrimidine non-nucleoside derivatives are known to exhibit anti-cancer (Al-Safarjalani et al., 2005), anti-viral (Brunelle et al., 2007; Ding et al., 2006) and anti-bacterial activities (Al-Abdullah et al., 2011). In continuation to our interest in the chemical and pharmacological properties of pyrimidine derivatives (Al-Omar et al., 2010; El-Emam et al. 2011), we synthesized the title compound (I) as potential a chemotherapeutic agent.

In (I), Fig. 1, three independent molecules comprise the asymmetric unit, and these have very similar molecular conformations as seen in the overlay diagram, Fig. 2. With respect to the pyrimidinyl ring, the chlorobenzene and CF3-benzene rings form dihedral angles of 80.36 (13) and 11.89 (14)°, respectively, for the N1-containing molecule; the dihedral angle between the benzene rings is 69.50 (14)°. For the N5-containing molecule the dihedral angles are 88.07 (14), 23.30 (14) and 64.81 (16), respectively, and for the N9-containing molecule, the angles are 85.94 (14), 13.81 (14) and 72.16 (15)°, respectively. In each case, the 2-methylpropyl group is orientated in the same direction as the chlorobenzene ring.

In the crystal structure, the N1- and N5-containing molecules associate to form a two molecule aggregate via NH···N(cyano) hydrogen bonds and 12-membered {···HNC3N}2 synthons, Table 1 and Fig. 3. The N3-containing molecules self-associate similarly but over a centre of inversion, Table 1.

For the chemotherapeutic efficacy of pyrimidine derivatives, see: Al-Safarjalani et al. (2005); Brunelle et al. (2007); Ding et al. (2006); Al-Abdullah et al. (2011). For recent interest in the chemical and pharmacological properties of pyrimidine derivatives, see: Al-Omar et al. (2010); El-Emam et al. (2011). For the treatment of data from a twinned crystal, see: Spek (2009).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structures of the three independent molecules comprising (I) showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Overlay diagram of the three independent molecules comprising the asymmetric unit of (I). The first independent molecule (with the N1 atom) is shown in red, the second (N5) in blue and the third (N9) in green. The N—S—N atoms in each molecule have been overlapped.
[Figure 3] Fig. 3. A view of a supramolecular dimeric aggregate in (I) where the first and second independent molecules are connected via N—H···N hydrogen bonds (dashed lines).
2-[(4-Chlorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-[3- (trifluoromethyl)anilino]pyrimidine-5-carbonitrile top
Crystal data top
C23H20ClF3N4SZ = 6
Mr = 476.94F(000) = 1476
Triclinic, P1Dx = 1.449 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 15.3906 (6) ÅCell parameters from 6525 reflections
b = 15.7040 (7) Åθ = 2.9–76.4°
c = 15.9129 (7) ŵ = 2.83 mm1
α = 89.568 (3)°T = 100 K
β = 74.825 (4)°Prism, colourless
γ = 62.980 (4)°0.35 × 0.15 × 0.03 mm
V = 3278.9 (2) Å3
Data collection top
Agilent SuperNova Dual
diffractometer with Atlas detector
25266 independent reflections
Radiation source: SuperNova (Cu) X-ray Source18393 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.075
Detector resolution: 10.4041 pixels mm-1θmax = 77.2°, θmin = 2.9°
ω scanh = 1914
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
k = 1919
Tmin = 0.437, Tmax = 0.920l = 2020
38203 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1074P)2 + 1.9445P]
where P = (Fo2 + 2Fc2)/3
25266 reflections(Δ/σ)max = 0.001
866 parametersΔρmax = 1.44 e Å3
0 restraintsΔρmin = 0.53 e Å3
Crystal data top
C23H20ClF3N4Sγ = 62.980 (4)°
Mr = 476.94V = 3278.9 (2) Å3
Triclinic, P1Z = 6
a = 15.3906 (6) ÅCu Kα radiation
b = 15.7040 (7) ŵ = 2.83 mm1
c = 15.9129 (7) ÅT = 100 K
α = 89.568 (3)°0.35 × 0.15 × 0.03 mm
β = 74.825 (4)°
Data collection top
Agilent SuperNova Dual
diffractometer with Atlas detector
25266 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
18393 reflections with I > 2σ(I)
Tmin = 0.437, Tmax = 0.920Rint = 0.075
38203 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.190H-atom parameters constrained
S = 1.02Δρmax = 1.44 e Å3
25266 reflectionsΔρmin = 0.53 e Å3
866 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.28241 (5)0.07400 (5)0.46993 (5)0.04104 (17)
Cl20.54081 (6)0.09270 (5)0.45600 (5)0.04320 (17)
Cl30.88514 (6)0.05812 (5)0.48589 (5)0.04180 (17)
S10.09695 (4)0.50003 (4)0.38610 (4)0.02693 (13)
S20.26108 (5)0.55904 (5)0.35580 (4)0.03043 (14)
S30.59118 (4)0.50668 (4)0.36852 (4)0.02694 (13)
F10.17005 (17)0.91092 (16)0.12971 (16)0.0647 (6)
F20.2082 (2)0.9126 (2)0.24916 (15)0.0777 (8)
F30.30080 (15)0.79316 (15)0.14940 (14)0.0566 (5)
F40.48491 (15)0.96664 (14)0.10659 (13)0.0503 (5)
F50.55114 (16)0.98424 (14)0.20327 (12)0.0502 (5)
F60.63952 (13)0.86860 (13)0.09720 (12)0.0467 (4)
F70.7953 (2)0.9366 (2)0.10386 (19)0.0935 (10)
F80.8286 (3)0.9722 (2)0.21371 (15)0.1110 (13)
F90.93890 (18)0.85381 (17)0.12129 (18)0.0814 (8)
N10.03473 (16)0.38490 (15)0.23888 (13)0.0263 (4)
N20.02592 (15)0.53909 (14)0.26904 (13)0.0237 (4)
N30.27750 (16)0.40345 (16)0.01072 (14)0.0296 (5)
N40.12993 (15)0.58965 (15)0.17176 (13)0.0258 (4)
H4n0.17600.57550.12050.031*
N50.38696 (16)0.44653 (16)0.20522 (13)0.0274 (4)
N60.40376 (16)0.58285 (15)0.25038 (13)0.0273 (4)
N70.67800 (18)0.43372 (16)0.01233 (15)0.0344 (5)
N80.53033 (16)0.61660 (15)0.16659 (13)0.0272 (4)
H8n0.58640.59440.12240.033*
N90.73047 (16)0.39133 (15)0.22323 (13)0.0261 (4)
N100.72270 (15)0.54339 (14)0.26119 (13)0.0229 (4)
N110.98810 (17)0.41309 (16)0.00944 (14)0.0316 (5)
N120.83306 (15)0.59339 (14)0.17164 (13)0.0242 (4)
H12n0.88520.57660.12430.029*
C10.00049 (17)0.46909 (17)0.28614 (15)0.0242 (5)
C20.10854 (18)0.36623 (18)0.16294 (16)0.0256 (5)
C30.14142 (18)0.43437 (18)0.13701 (15)0.0249 (5)
C40.09820 (18)0.52258 (17)0.19325 (15)0.0236 (5)
C50.09619 (19)0.38575 (18)0.40321 (16)0.0272 (5)
H5A0.15560.39670.45340.033*
H5B0.10470.36100.35050.033*
C60.00106 (19)0.30952 (18)0.42101 (15)0.0266 (5)
C70.0331 (2)0.21336 (19)0.39186 (17)0.0321 (5)
H70.00400.19720.36140.038*
C80.1204 (2)0.14040 (19)0.40635 (17)0.0328 (6)
H8A0.14310.07490.38620.039*
C90.1735 (2)0.16499 (19)0.45067 (17)0.0310 (5)
C100.1415 (2)0.2598 (2)0.48143 (17)0.0325 (6)
H100.17850.27550.51240.039*
C110.0541 (2)0.33159 (18)0.46595 (17)0.0292 (5)
H110.03150.39700.48640.035*
C120.1518 (2)0.27018 (18)0.10984 (16)0.0292 (5)
H12A0.20770.26390.05810.035*
H12B0.09810.26800.08810.035*
C130.2646 (3)0.1856 (3)0.2067 (3)0.0562 (9)
H13A0.28680.12910.23810.084*
H13B0.23020.24440.24880.084*
H13C0.32410.18450.16390.084*
C140.1932 (2)0.1840 (2)0.1604 (2)0.0395 (6)
H140.13290.18820.20700.047*
C150.2373 (2)0.0905 (2)0.1034 (2)0.0397 (6)
H15A0.26270.03710.13770.060*
H15B0.29360.08520.05370.060*
H15C0.18450.08800.08150.060*
C160.21728 (19)0.41608 (17)0.05535 (16)0.0261 (5)
C170.10026 (19)0.67876 (18)0.21925 (16)0.0266 (5)
C180.0161 (2)0.7249 (2)0.29302 (18)0.0363 (6)
H180.02740.69700.31490.044*
C190.0034 (3)0.8118 (2)0.3341 (2)0.0450 (8)
H190.06020.84240.38480.054*
C200.0572 (2)0.8555 (2)0.30360 (19)0.0421 (7)
H200.04260.91510.33270.051*
C210.1402 (2)0.8094 (2)0.22893 (17)0.0327 (6)
C220.16137 (19)0.72244 (19)0.18721 (16)0.0281 (5)
H220.21800.69210.13630.034*
C230.2036 (2)0.8567 (2)0.1902 (2)0.0416 (7)
C240.36230 (18)0.52357 (18)0.25885 (16)0.0270 (5)
C250.46783 (18)0.42328 (18)0.13324 (16)0.0265 (5)
C260.52042 (18)0.47668 (18)0.12004 (16)0.0251 (5)
C270.48436 (18)0.56034 (18)0.17990 (16)0.0261 (5)
C280.23542 (19)0.4576 (2)0.36258 (17)0.0317 (6)
H28A0.16900.47710.40710.038*
H28B0.22900.44130.30530.038*
C290.31508 (19)0.36827 (19)0.38604 (16)0.0282 (5)
C300.3587 (2)0.2816 (2)0.33236 (19)0.0410 (7)
H300.34050.28050.27990.049*
C310.4279 (3)0.1970 (2)0.35333 (19)0.0432 (7)
H310.45610.13790.31640.052*
C320.4553 (2)0.19952 (19)0.42846 (17)0.0322 (6)
C330.41735 (19)0.28512 (19)0.48200 (17)0.0289 (5)
H330.43930.28640.53230.035*
C340.34619 (18)0.36938 (18)0.46041 (16)0.0267 (5)
H340.31850.42850.49710.032*
C350.4953 (2)0.33835 (19)0.07026 (17)0.0298 (5)
H35A0.54640.33560.01610.036*
H35B0.43370.34820.05410.036*
C360.5468 (3)0.1638 (2)0.0437 (2)0.0517 (9)
H36A0.57280.10240.06790.078*
H36B0.59390.15780.01360.078*
H36C0.47970.18040.03690.078*
C370.5375 (2)0.2426 (2)0.10586 (19)0.0399 (7)
H370.48830.24830.16350.048*
C380.6384 (3)0.2182 (3)0.1213 (3)0.0643 (11)
H38A0.62970.26960.16230.096*
H38B0.68800.21200.06540.096*
H38C0.66300.15720.14610.096*
C390.60785 (19)0.45106 (18)0.04593 (17)0.0280 (5)
C400.50169 (19)0.70637 (18)0.21335 (16)0.0271 (5)
C410.4449 (2)0.73593 (19)0.30145 (17)0.0312 (5)
H410.42190.69540.33410.037*
C420.4221 (2)0.8246 (2)0.34108 (18)0.0377 (6)
H420.38280.84480.40090.045*
C430.4557 (2)0.8845 (2)0.29504 (18)0.0359 (6)
H430.43980.94530.32270.043*
C440.51292 (19)0.85383 (18)0.20761 (17)0.0293 (5)
C450.53599 (19)0.76585 (18)0.16691 (16)0.0280 (5)
H450.57540.74590.10710.034*
C460.5468 (2)0.9177 (2)0.15434 (18)0.0341 (6)
C470.69373 (18)0.47470 (17)0.27320 (16)0.0244 (5)
C480.80934 (19)0.37318 (18)0.15126 (16)0.0253 (5)
C490.84461 (18)0.44015 (17)0.13139 (15)0.0244 (5)
C500.79899 (17)0.52733 (17)0.18920 (15)0.0225 (5)
C510.57135 (19)0.40147 (19)0.37399 (18)0.0301 (5)
H51A0.50330.41960.41520.036*
H51B0.57080.38180.31530.036*
C520.64989 (18)0.31549 (18)0.40284 (16)0.0272 (5)
C530.6869 (2)0.2237 (2)0.36093 (18)0.0326 (6)
H530.66310.21520.31380.039*
C540.7585 (2)0.14369 (19)0.38691 (18)0.0343 (6)
H540.78310.08080.35840.041*
C550.7929 (2)0.15728 (19)0.45457 (17)0.0302 (5)
C560.7568 (2)0.2475 (2)0.49877 (17)0.0322 (5)
H560.78040.25540.54610.039*
C570.68469 (19)0.32682 (19)0.47215 (17)0.0295 (5)
H570.65900.38950.50180.035*
C580.8553 (2)0.27941 (18)0.09367 (17)0.0322 (6)
H58A0.92130.26860.05290.039*
H58B0.80980.28450.05780.039*
C590.9241 (3)0.1005 (2)0.0764 (2)0.0438 (7)
H59A0.88190.10860.03740.066*
H59B0.93120.04460.10740.066*
H59C0.99160.09040.04170.066*
C600.8735 (2)0.19117 (19)0.14328 (17)0.0307 (5)
H600.80570.19910.17900.037*
C610.9363 (2)0.1818 (2)0.2048 (2)0.0437 (7)
H61A0.90210.24050.24690.066*
H61B1.00370.17260.17090.066*
H61C0.94380.12630.23640.066*
C620.92467 (19)0.42335 (17)0.05287 (16)0.0257 (5)
C630.79769 (18)0.68498 (17)0.21762 (16)0.0242 (5)
C640.7342 (2)0.71623 (19)0.30330 (16)0.0303 (5)
H640.71080.67540.33470.036*
C650.7051 (2)0.8073 (2)0.34271 (18)0.0344 (6)
H650.66130.82820.40120.041*
C660.7384 (2)0.86838 (19)0.29861 (17)0.0315 (5)
H660.71740.93090.32600.038*
C670.8028 (2)0.83617 (19)0.21389 (17)0.0297 (5)
C680.83219 (19)0.74554 (18)0.17302 (16)0.0283 (5)
H680.87590.72480.11450.034*
C690.8404 (2)0.8999 (2)0.16351 (18)0.0380 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0405 (4)0.0330 (3)0.0356 (3)0.0047 (3)0.0127 (3)0.0000 (3)
Cl20.0407 (4)0.0286 (3)0.0438 (4)0.0078 (3)0.0023 (3)0.0072 (3)
Cl30.0428 (4)0.0302 (3)0.0434 (4)0.0096 (3)0.0128 (3)0.0082 (3)
S10.0247 (3)0.0270 (3)0.0246 (3)0.0116 (2)0.0014 (2)0.0035 (2)
S20.0274 (3)0.0317 (3)0.0238 (3)0.0099 (2)0.0017 (2)0.0056 (2)
S30.0243 (3)0.0263 (3)0.0262 (3)0.0116 (2)0.0016 (2)0.0036 (2)
F10.0703 (14)0.0676 (14)0.0796 (15)0.0485 (12)0.0286 (12)0.0407 (12)
F20.1067 (19)0.1026 (19)0.0552 (13)0.0886 (17)0.0028 (12)0.0138 (12)
F30.0438 (10)0.0621 (13)0.0698 (13)0.0359 (10)0.0047 (9)0.0128 (10)
F40.0558 (11)0.0463 (10)0.0636 (12)0.0297 (9)0.0300 (10)0.0288 (9)
F50.0718 (13)0.0456 (10)0.0407 (10)0.0399 (10)0.0046 (9)0.0026 (8)
F60.0421 (10)0.0383 (9)0.0470 (10)0.0198 (8)0.0086 (8)0.0023 (8)
F70.121 (2)0.124 (2)0.108 (2)0.098 (2)0.0713 (19)0.0905 (19)
F80.214 (4)0.096 (2)0.0456 (13)0.126 (2)0.0278 (17)0.0165 (12)
F90.0590 (14)0.0630 (14)0.104 (2)0.0338 (12)0.0138 (13)0.0301 (13)
N10.0272 (10)0.0292 (10)0.0217 (10)0.0142 (9)0.0037 (8)0.0032 (8)
N20.0210 (9)0.0258 (10)0.0222 (10)0.0103 (8)0.0044 (8)0.0039 (8)
N30.0290 (11)0.0293 (11)0.0254 (11)0.0117 (9)0.0036 (9)0.0027 (8)
N40.0245 (10)0.0273 (10)0.0223 (10)0.0123 (8)0.0012 (8)0.0018 (8)
N50.0257 (10)0.0318 (11)0.0238 (10)0.0127 (9)0.0074 (8)0.0057 (8)
N60.0259 (10)0.0278 (10)0.0228 (10)0.0096 (8)0.0043 (8)0.0036 (8)
N70.0350 (12)0.0298 (11)0.0294 (12)0.0128 (10)0.0001 (10)0.0012 (9)
N80.0257 (10)0.0262 (10)0.0233 (10)0.0099 (8)0.0012 (8)0.0013 (8)
N90.0269 (10)0.0259 (10)0.0250 (10)0.0124 (8)0.0065 (8)0.0034 (8)
N100.0219 (9)0.0247 (10)0.0217 (10)0.0108 (8)0.0056 (8)0.0034 (8)
N110.0341 (12)0.0277 (11)0.0278 (11)0.0140 (9)0.0016 (9)0.0009 (8)
N120.0252 (10)0.0232 (10)0.0209 (9)0.0115 (8)0.0013 (8)0.0003 (7)
C10.0217 (11)0.0268 (12)0.0222 (11)0.0093 (9)0.0071 (9)0.0064 (9)
C20.0266 (12)0.0269 (12)0.0238 (12)0.0118 (10)0.0095 (10)0.0056 (9)
C30.0238 (11)0.0277 (12)0.0210 (11)0.0102 (10)0.0064 (9)0.0041 (9)
C40.0213 (11)0.0269 (12)0.0228 (11)0.0111 (9)0.0070 (9)0.0061 (9)
C50.0271 (12)0.0275 (12)0.0271 (12)0.0161 (10)0.0016 (10)0.0046 (9)
C60.0295 (12)0.0287 (12)0.0203 (11)0.0150 (10)0.0027 (9)0.0060 (9)
C70.0408 (14)0.0320 (13)0.0271 (13)0.0196 (12)0.0108 (11)0.0057 (10)
C80.0449 (15)0.0256 (12)0.0259 (13)0.0158 (12)0.0085 (11)0.0039 (10)
C90.0337 (13)0.0284 (13)0.0230 (12)0.0103 (11)0.0040 (10)0.0047 (10)
C100.0328 (13)0.0348 (14)0.0291 (13)0.0157 (11)0.0079 (11)0.0019 (10)
C110.0316 (13)0.0262 (12)0.0280 (13)0.0141 (10)0.0047 (10)0.0004 (10)
C120.0330 (13)0.0295 (13)0.0247 (12)0.0164 (11)0.0043 (10)0.0014 (10)
C130.052 (2)0.053 (2)0.061 (2)0.0204 (17)0.0201 (17)0.0047 (17)
C140.0391 (15)0.0330 (14)0.0354 (15)0.0076 (12)0.0114 (12)0.0006 (12)
C150.0395 (15)0.0310 (14)0.0473 (17)0.0174 (12)0.0091 (13)0.0054 (12)
C160.0276 (12)0.0242 (11)0.0254 (12)0.0111 (10)0.0080 (10)0.0033 (9)
C170.0278 (12)0.0278 (12)0.0242 (12)0.0134 (10)0.0067 (10)0.0045 (9)
C180.0393 (15)0.0348 (14)0.0317 (14)0.0214 (12)0.0021 (12)0.0010 (11)
C190.0502 (18)0.0415 (16)0.0342 (15)0.0260 (15)0.0109 (13)0.0085 (12)
C200.0521 (18)0.0383 (16)0.0337 (15)0.0265 (14)0.0017 (13)0.0074 (12)
C210.0390 (14)0.0353 (14)0.0299 (13)0.0237 (12)0.0078 (11)0.0037 (11)
C220.0289 (12)0.0332 (13)0.0228 (12)0.0170 (11)0.0041 (10)0.0042 (10)
C230.0485 (17)0.0475 (17)0.0375 (15)0.0325 (15)0.0073 (13)0.0030 (13)
C240.0219 (11)0.0311 (12)0.0242 (12)0.0096 (10)0.0061 (9)0.0071 (10)
C250.0252 (12)0.0295 (12)0.0222 (11)0.0101 (10)0.0080 (9)0.0055 (9)
C260.0231 (11)0.0285 (12)0.0222 (11)0.0110 (10)0.0062 (9)0.0042 (9)
C270.0244 (11)0.0274 (12)0.0223 (11)0.0085 (10)0.0071 (9)0.0044 (9)
C280.0256 (12)0.0444 (15)0.0261 (13)0.0177 (11)0.0066 (10)0.0093 (11)
C290.0244 (12)0.0364 (14)0.0242 (12)0.0166 (11)0.0035 (9)0.0065 (10)
C300.0520 (18)0.0446 (17)0.0280 (14)0.0248 (15)0.0095 (13)0.0003 (12)
C310.0567 (19)0.0321 (15)0.0314 (15)0.0171 (14)0.0049 (13)0.0048 (11)
C320.0303 (13)0.0297 (13)0.0289 (13)0.0122 (11)0.0001 (10)0.0055 (10)
C330.0270 (12)0.0315 (13)0.0255 (12)0.0144 (10)0.0022 (10)0.0038 (10)
C340.0229 (11)0.0279 (12)0.0263 (12)0.0120 (10)0.0019 (9)0.0018 (9)
C350.0291 (12)0.0367 (14)0.0249 (12)0.0168 (11)0.0073 (10)0.0035 (10)
C360.083 (3)0.0443 (18)0.0380 (17)0.0402 (18)0.0142 (16)0.0065 (14)
C370.0517 (18)0.0362 (15)0.0330 (15)0.0217 (14)0.0122 (13)0.0052 (12)
C380.066 (2)0.0346 (17)0.095 (3)0.0128 (17)0.048 (2)0.0052 (18)
C390.0310 (13)0.0238 (12)0.0280 (13)0.0113 (10)0.0094 (11)0.0034 (9)
C400.0258 (12)0.0279 (12)0.0232 (12)0.0092 (10)0.0065 (9)0.0027 (9)
C410.0360 (14)0.0310 (13)0.0233 (12)0.0155 (11)0.0040 (10)0.0048 (10)
C420.0429 (16)0.0387 (15)0.0245 (13)0.0185 (13)0.0002 (11)0.0021 (11)
C430.0379 (15)0.0293 (13)0.0330 (14)0.0144 (12)0.0011 (11)0.0056 (11)
C440.0284 (12)0.0270 (12)0.0288 (13)0.0113 (10)0.0056 (10)0.0026 (10)
C450.0246 (12)0.0303 (13)0.0238 (12)0.0106 (10)0.0029 (9)0.0026 (9)
C460.0349 (14)0.0308 (13)0.0330 (14)0.0154 (11)0.0040 (11)0.0002 (11)
C470.0231 (11)0.0254 (11)0.0244 (11)0.0103 (9)0.0085 (9)0.0065 (9)
C480.0282 (12)0.0257 (12)0.0232 (11)0.0133 (10)0.0080 (10)0.0054 (9)
C490.0254 (11)0.0238 (11)0.0218 (11)0.0101 (9)0.0060 (9)0.0036 (9)
C500.0209 (11)0.0240 (11)0.0216 (11)0.0094 (9)0.0068 (9)0.0043 (9)
C510.0231 (12)0.0338 (13)0.0336 (14)0.0149 (11)0.0056 (10)0.0082 (11)
C520.0243 (12)0.0290 (12)0.0255 (12)0.0130 (10)0.0022 (9)0.0067 (10)
C530.0355 (14)0.0348 (14)0.0282 (13)0.0186 (12)0.0063 (11)0.0043 (11)
C540.0402 (15)0.0268 (13)0.0312 (14)0.0148 (11)0.0048 (11)0.0014 (10)
C550.0274 (12)0.0290 (13)0.0287 (13)0.0119 (10)0.0021 (10)0.0059 (10)
C560.0334 (13)0.0344 (14)0.0262 (13)0.0150 (11)0.0065 (10)0.0040 (10)
C570.0295 (12)0.0278 (12)0.0276 (12)0.0135 (10)0.0022 (10)0.0005 (10)
C580.0403 (14)0.0265 (13)0.0284 (13)0.0176 (11)0.0042 (11)0.0007 (10)
C590.0546 (19)0.0294 (14)0.0396 (16)0.0208 (14)0.0009 (14)0.0007 (12)
C600.0303 (13)0.0271 (13)0.0332 (13)0.0142 (11)0.0055 (11)0.0033 (10)
C610.0409 (16)0.0335 (15)0.059 (2)0.0153 (13)0.0221 (15)0.0100 (13)
C620.0300 (12)0.0197 (11)0.0262 (12)0.0107 (9)0.0080 (10)0.0022 (9)
C630.0244 (11)0.0235 (11)0.0235 (11)0.0110 (9)0.0058 (9)0.0025 (9)
C640.0373 (14)0.0287 (13)0.0238 (12)0.0182 (11)0.0021 (10)0.0023 (10)
C650.0387 (14)0.0347 (14)0.0255 (13)0.0199 (12)0.0023 (11)0.0010 (10)
C660.0355 (14)0.0277 (13)0.0286 (13)0.0165 (11)0.0022 (11)0.0003 (10)
C670.0324 (13)0.0281 (12)0.0272 (13)0.0159 (11)0.0034 (10)0.0047 (10)
C680.0302 (12)0.0301 (13)0.0211 (11)0.0144 (10)0.0011 (10)0.0017 (9)
C690.0503 (17)0.0345 (14)0.0268 (13)0.0243 (13)0.0008 (12)0.0018 (11)
Geometric parameters (Å, º) top
Cl1—C91.741 (3)C22—H220.9500
Cl2—C321.738 (3)C25—C261.388 (3)
Cl3—C551.743 (3)C25—C351.499 (4)
S1—C11.758 (2)C26—C271.422 (3)
S1—C51.808 (2)C26—C391.431 (3)
S2—C241.756 (2)C28—C291.510 (4)
S2—C281.803 (3)C28—H28A0.9900
S3—C471.756 (2)C28—H28B0.9900
S3—C511.809 (3)C29—C301.385 (4)
F1—C231.328 (4)C29—C341.391 (4)
F2—C231.327 (4)C30—C311.381 (4)
F3—C231.342 (4)C30—H300.9500
F4—C461.334 (3)C31—C321.375 (4)
F5—C461.343 (3)C31—H310.9500
F6—C461.338 (3)C32—C331.385 (4)
F7—C691.300 (4)C33—C341.393 (4)
F8—C691.309 (4)C33—H330.9500
F9—C691.323 (4)C34—H340.9500
N1—C11.326 (3)C35—C371.515 (4)
N1—C21.349 (3)C35—H35A0.9900
N2—C11.338 (3)C35—H35B0.9900
N2—C41.341 (3)C36—C371.521 (4)
N3—C161.153 (3)C36—H36A0.9800
N4—C41.356 (3)C36—H36B0.9800
N4—C171.412 (3)C36—H36C0.9800
N4—H4n0.8800C37—C381.508 (5)
N5—C241.328 (3)C37—H371.0000
N5—C251.357 (3)C38—H38A0.9800
N6—C241.336 (3)C38—H38B0.9800
N6—C271.342 (3)C38—H38C0.9800
N7—C391.145 (3)C40—C451.390 (3)
N8—C271.346 (3)C40—C411.395 (3)
N8—C401.419 (3)C41—C421.383 (4)
N8—H8n0.8800C41—H410.9500
N9—C471.332 (3)C42—C431.387 (4)
N9—C481.352 (3)C42—H420.9500
N10—C501.336 (3)C43—C441.388 (4)
N10—C471.337 (3)C43—H430.9500
N11—C621.147 (3)C44—C451.379 (4)
N12—C501.357 (3)C44—C461.493 (4)
N12—C631.413 (3)C45—H450.9500
N12—H12n0.8800C48—C491.387 (3)
C2—C31.396 (3)C48—C581.498 (3)
C2—C121.498 (3)C49—C501.422 (3)
C3—C41.426 (3)C49—C621.433 (3)
C3—C161.429 (3)C51—C521.514 (3)
C5—C61.509 (3)C51—H51A0.9900
C5—H5A0.9900C51—H51B0.9900
C5—H5B0.9900C52—C531.385 (4)
C6—C71.391 (4)C52—C571.391 (4)
C6—C111.393 (4)C53—C541.391 (4)
C7—C81.389 (4)C53—H530.9500
C7—H70.9500C54—C551.375 (4)
C8—C91.381 (4)C54—H540.9500
C8—H8A0.9500C55—C561.381 (4)
C9—C101.385 (4)C56—C571.394 (4)
C10—C111.391 (4)C56—H560.9500
C10—H100.9500C57—H570.9500
C11—H110.9500C58—C601.539 (4)
C12—C141.534 (4)C58—H58A0.9900
C12—H12A0.9900C58—H58B0.9900
C12—H12B0.9900C59—C601.531 (4)
C13—C141.485 (5)C59—H59A0.9800
C13—H13A0.9800C59—H59B0.9800
C13—H13B0.9800C59—H59C0.9800
C13—H13C0.9800C60—C611.509 (4)
C14—C151.492 (4)C60—H601.0000
C14—H141.0000C61—H61A0.9800
C15—H15A0.9800C61—H61B0.9800
C15—H15B0.9800C61—H61C0.9800
C15—H15C0.9800C63—C641.390 (3)
C17—C221.395 (3)C63—C681.393 (3)
C17—C181.395 (4)C64—C651.386 (4)
C18—C191.385 (4)C64—H640.9500
C18—H180.9500C65—C661.388 (4)
C19—C201.383 (4)C65—H650.9500
C19—H190.9500C66—C671.382 (4)
C20—C211.395 (4)C66—H660.9500
C20—H200.9500C67—C681.389 (4)
C21—C221.381 (4)C67—C691.500 (3)
C21—C231.490 (4)C68—H680.9500
C1—S1—C5101.53 (11)C29—C34—H34119.5
C24—S2—C28102.77 (13)C33—C34—H34119.5
C47—S3—C51103.16 (12)C25—C35—C37114.1 (2)
C1—N1—C2115.7 (2)C25—C35—H35A108.7
C1—N2—C4116.0 (2)C37—C35—H35A108.7
C4—N4—C17129.8 (2)C25—C35—H35B108.7
C4—N4—H4n115.1C37—C35—H35B108.7
C17—N4—H4n115.1H35A—C35—H35B107.6
C24—N5—C25115.1 (2)C37—C36—H36A109.5
C24—N6—C27116.4 (2)C37—C36—H36B109.5
C27—N8—C40129.6 (2)H36A—C36—H36B109.5
C27—N8—H8n115.2C37—C36—H36C109.5
C40—N8—H8n115.2H36A—C36—H36C109.5
C47—N9—C48115.2 (2)H36B—C36—H36C109.5
C50—N10—C47116.3 (2)C38—C37—C35111.0 (3)
C50—N12—C63129.9 (2)C38—C37—C36111.4 (3)
C50—N12—H12n115.0C35—C37—C36110.0 (2)
C63—N12—H12n115.0C38—C37—H37108.1
N1—C1—N2129.3 (2)C35—C37—H37108.1
N1—C1—S1119.08 (18)C36—C37—H37108.1
N2—C1—S1111.62 (18)C37—C38—H38A109.5
N1—C2—C3120.4 (2)C37—C38—H38B109.5
N1—C2—C12116.7 (2)H38A—C38—H38B109.5
C3—C2—C12122.9 (2)C37—C38—H38C109.5
C2—C3—C4119.0 (2)H38A—C38—H38C109.5
C2—C3—C16120.6 (2)H38B—C38—H38C109.5
C4—C3—C16120.4 (2)N7—C39—C26177.3 (3)
N2—C4—N4119.5 (2)C45—C40—C41119.5 (2)
N2—C4—C3119.6 (2)C45—C40—N8116.2 (2)
N4—C4—C3121.0 (2)C41—C40—N8124.3 (2)
C6—C5—S1114.73 (17)C42—C41—C40119.6 (2)
C6—C5—H5A108.6C42—C41—H41120.2
S1—C5—H5A108.6C40—C41—H41120.2
C6—C5—H5B108.6C41—C42—C43121.2 (3)
S1—C5—H5B108.6C41—C42—H42119.4
H5A—C5—H5B107.6C43—C42—H42119.4
C7—C6—C11118.4 (2)C42—C43—C44118.5 (3)
C7—C6—C5119.0 (2)C42—C43—H43120.7
C11—C6—C5122.5 (2)C44—C43—H43120.7
C8—C7—C6121.3 (3)C45—C44—C43121.0 (2)
C8—C7—H7119.3C45—C44—C46118.5 (2)
C6—C7—H7119.3C43—C44—C46120.4 (2)
C9—C8—C7118.7 (2)C44—C45—C40120.1 (2)
C9—C8—H8A120.7C44—C45—H45120.0
C7—C8—H8A120.7C40—C45—H45120.0
C8—C9—C10121.8 (3)F4—C46—F6105.8 (2)
C8—C9—Cl1119.0 (2)F4—C46—F5105.9 (2)
C10—C9—Cl1119.2 (2)F6—C46—F5106.2 (2)
C9—C10—C11118.5 (3)F4—C46—C44112.5 (2)
C9—C10—H10120.8F6—C46—C44112.5 (2)
C11—C10—H10120.8F5—C46—C44113.2 (2)
C10—C11—C6121.3 (2)N9—C47—N10129.1 (2)
C10—C11—H11119.3N9—C47—S3119.56 (18)
C6—C11—H11119.3N10—C47—S3111.38 (18)
C2—C12—C14114.1 (2)N9—C48—C49120.7 (2)
C2—C12—H12A108.7N9—C48—C58117.5 (2)
C14—C12—H12A108.7C49—C48—C58121.7 (2)
C2—C12—H12B108.7C48—C49—C50119.2 (2)
C14—C12—H12B108.7C48—C49—C62120.9 (2)
H12A—C12—H12B107.6C50—C49—C62119.9 (2)
C14—C13—H13A109.5N10—C50—N12120.3 (2)
C14—C13—H13B109.5N10—C50—C49119.4 (2)
H13A—C13—H13B109.5N12—C50—C49120.3 (2)
C14—C13—H13C109.5C52—C51—S3115.19 (18)
H13A—C13—H13C109.5C52—C51—H51A108.5
H13B—C13—H13C109.5S3—C51—H51A108.5
C13—C14—C15111.8 (3)C52—C51—H51B108.5
C13—C14—C12114.2 (3)S3—C51—H51B108.5
C15—C14—C12111.5 (2)H51A—C51—H51B107.5
C13—C14—H14106.2C53—C52—C57119.0 (2)
C15—C14—H14106.2C53—C52—C51120.0 (2)
C12—C14—H14106.2C57—C52—C51121.0 (2)
C14—C15—H15A109.5C52—C53—C54120.8 (3)
C14—C15—H15B109.5C52—C53—H53119.6
H15A—C15—H15B109.5C54—C53—H53119.6
C14—C15—H15C109.5C55—C54—C53118.9 (3)
H15A—C15—H15C109.5C55—C54—H54120.6
H15B—C15—H15C109.5C53—C54—H54120.6
N3—C16—C3178.5 (3)C54—C55—C56122.0 (3)
C22—C17—C18119.2 (2)C54—C55—Cl3119.4 (2)
C22—C17—N4115.5 (2)C56—C55—Cl3118.6 (2)
C18—C17—N4125.3 (2)C55—C56—C57118.4 (3)
C19—C18—C17119.2 (3)C55—C56—H56120.8
C19—C18—H18120.4C57—C56—H56120.8
C17—C18—H18120.4C52—C57—C56120.9 (2)
C20—C19—C18122.2 (3)C52—C57—H57119.5
C20—C19—H19118.9C56—C57—H57119.5
C18—C19—H19118.9C48—C58—C60114.7 (2)
C19—C20—C21118.0 (3)C48—C58—H58A108.6
C19—C20—H20121.0C60—C58—H58A108.6
C21—C20—H20121.0C48—C58—H58B108.6
C22—C21—C20120.8 (2)C60—C58—H58B108.6
C22—C21—C23119.1 (3)H58A—C58—H58B107.6
C20—C21—C23120.0 (3)C60—C59—H59A109.5
C21—C22—C17120.5 (2)C60—C59—H59B109.5
C21—C22—H22119.7H59A—C59—H59B109.5
C17—C22—H22119.7C60—C59—H59C109.5
F2—C23—F1107.0 (3)H59A—C59—H59C109.5
F2—C23—F3105.3 (3)H59B—C59—H59C109.5
F1—C23—F3105.3 (3)C61—C60—C59111.2 (2)
F2—C23—C21113.4 (3)C61—C60—C58112.2 (2)
F1—C23—C21112.4 (3)C59—C60—C58108.9 (2)
F3—C23—C21112.8 (3)C61—C60—H60108.1
N5—C24—N6129.1 (2)C59—C60—H60108.1
N5—C24—S2119.42 (19)C58—C60—H60108.1
N6—C24—S2111.45 (19)C60—C61—H61A109.5
N5—C25—C26120.8 (2)C60—C61—H61B109.5
N5—C25—C35116.2 (2)H61A—C61—H61B109.5
C26—C25—C35123.1 (2)C60—C61—H61C109.5
C25—C26—C27119.1 (2)H61A—C61—H61C109.5
C25—C26—C39121.3 (2)H61B—C61—H61C109.5
C27—C26—C39119.5 (2)N11—C62—C49177.7 (3)
N6—C27—N8120.0 (2)C64—C63—C68119.2 (2)
N6—C27—C26119.3 (2)C64—C63—N12124.5 (2)
N8—C27—C26120.7 (2)C68—C63—N12116.3 (2)
C29—C28—S2114.89 (18)C65—C64—C63119.8 (2)
C29—C28—H28A108.5C65—C64—H64120.1
S2—C28—H28A108.5C63—C64—H64120.1
C29—C28—H28B108.5C64—C65—C66121.4 (2)
S2—C28—H28B108.5C64—C65—H65119.3
H28A—C28—H28B107.5C66—C65—H65119.3
C30—C29—C34118.4 (3)C67—C66—C65118.4 (2)
C30—C29—C28119.3 (2)C67—C66—H66120.8
C34—C29—C28122.3 (2)C65—C66—H66120.8
C31—C30—C29121.6 (3)C66—C67—C68121.0 (2)
C31—C30—H30119.2C66—C67—C69120.3 (2)
C29—C30—H30119.2C68—C67—C69118.7 (2)
C32—C31—C30118.9 (3)C67—C68—C63120.1 (2)
C32—C31—H31120.5C67—C68—H68119.9
C30—C31—H31120.5C63—C68—H68119.9
C31—C32—C33121.6 (3)F7—C69—F8106.7 (3)
C31—C32—Cl2119.0 (2)F7—C69—F9105.5 (3)
C33—C32—Cl2119.4 (2)F8—C69—F9105.2 (3)
C32—C33—C34118.5 (2)F7—C69—C67113.0 (3)
C32—C33—H33120.8F8—C69—C67113.0 (2)
C34—C33—H33120.8F9—C69—C67112.9 (2)
C29—C34—C33121.0 (2)
C2—N1—C1—N20.7 (4)C31—C32—C33—C342.9 (4)
C2—N1—C1—S1179.89 (17)Cl2—C32—C33—C34177.75 (18)
C4—N2—C1—N10.2 (4)C30—C29—C34—C331.7 (4)
C4—N2—C1—S1179.04 (17)C28—C29—C34—C33177.8 (2)
C5—S1—C1—N112.8 (2)C32—C33—C34—C291.1 (4)
C5—S1—C1—N2167.86 (17)N5—C25—C35—C3768.5 (3)
C1—N1—C2—C31.8 (3)C26—C25—C35—C37111.9 (3)
C1—N1—C2—C12178.1 (2)C25—C35—C37—C3865.3 (3)
N1—C2—C3—C42.0 (3)C25—C35—C37—C36170.9 (3)
C12—C2—C3—C4177.9 (2)C27—N8—C40—C45154.6 (2)
N1—C2—C3—C16178.0 (2)C27—N8—C40—C4127.1 (4)
C12—C2—C3—C162.1 (4)C45—C40—C41—C421.0 (4)
C1—N2—C4—N4179.2 (2)N8—C40—C41—C42179.2 (3)
C1—N2—C4—C30.0 (3)C40—C41—C42—C430.7 (4)
C17—N4—C4—N21.9 (4)C41—C42—C43—C440.1 (5)
C17—N4—C4—C3177.3 (2)C42—C43—C44—C450.2 (4)
C2—C3—C4—N21.0 (3)C42—C43—C44—C46177.3 (3)
C16—C3—C4—N2179.0 (2)C43—C44—C45—C400.1 (4)
C2—C3—C4—N4178.2 (2)C46—C44—C45—C40177.0 (2)
C16—C3—C4—N41.8 (4)C41—C40—C45—C440.7 (4)
C1—S1—C5—C667.3 (2)N8—C40—C45—C44179.1 (2)
S1—C5—C6—C7147.4 (2)C45—C44—C46—F480.5 (3)
S1—C5—C6—C1132.8 (3)C43—C44—C46—F496.6 (3)
C11—C6—C7—C80.4 (4)C45—C44—C46—F638.9 (4)
C5—C6—C7—C8179.8 (2)C43—C44—C46—F6143.9 (3)
C6—C7—C8—C90.0 (4)C45—C44—C46—F5159.4 (2)
C7—C8—C9—C100.6 (4)C43—C44—C46—F523.4 (4)
C7—C8—C9—Cl1179.5 (2)C48—N9—C47—N101.4 (4)
C8—C9—C10—C110.7 (4)C48—N9—C47—S3179.95 (17)
Cl1—C9—C10—C11179.6 (2)C50—N10—C47—N90.1 (4)
C9—C10—C11—C60.3 (4)C50—N10—C47—S3178.53 (16)
C7—C6—C11—C100.2 (4)C51—S3—C47—N94.5 (2)
C5—C6—C11—C10180.0 (2)C51—S3—C47—N10176.72 (17)
N1—C2—C12—C1455.0 (3)C47—N9—C48—C492.4 (3)
C3—C2—C12—C14124.8 (3)C47—N9—C48—C58178.7 (2)
C2—C12—C14—C1350.7 (4)N9—C48—C49—C502.0 (4)
C2—C12—C14—C15178.7 (2)C58—C48—C49—C50179.1 (2)
C4—N4—C17—C22167.8 (2)N9—C48—C49—C62176.8 (2)
C4—N4—C17—C1812.9 (4)C58—C48—C49—C622.1 (4)
C22—C17—C18—C191.6 (4)C47—N10—C50—N12179.8 (2)
N4—C17—C18—C19179.1 (3)C47—N10—C50—C490.6 (3)
C17—C18—C19—C201.0 (5)C63—N12—C50—N102.6 (4)
C18—C19—C20—C210.1 (5)C63—N12—C50—C49177.8 (2)
C19—C20—C21—C220.4 (5)C48—C49—C50—N100.4 (3)
C19—C20—C21—C23175.9 (3)C62—C49—C50—N10178.4 (2)
C20—C21—C22—C170.3 (4)C48—C49—C50—N12179.2 (2)
C23—C21—C22—C17176.7 (3)C62—C49—C50—N122.0 (3)
C18—C17—C22—C211.3 (4)C47—S3—C51—C5274.5 (2)
N4—C17—C22—C21179.4 (2)S3—C51—C52—C53138.2 (2)
C22—C21—C23—F2152.7 (3)S3—C51—C52—C5742.9 (3)
C20—C21—C23—F230.9 (4)C57—C52—C53—C540.5 (4)
C22—C21—C23—F185.8 (4)C51—C52—C53—C54179.5 (2)
C20—C21—C23—F190.6 (4)C52—C53—C54—C550.7 (4)
C22—C21—C23—F333.1 (4)C53—C54—C55—C561.6 (4)
C20—C21—C23—F3150.5 (3)C53—C54—C55—Cl3178.3 (2)
C25—N5—C24—N62.4 (4)C54—C55—C56—C571.3 (4)
C25—N5—C24—S2178.31 (17)Cl3—C55—C56—C57178.60 (19)
C27—N6—C24—N53.0 (4)C53—C52—C57—C560.9 (4)
C27—N6—C24—S2177.71 (17)C51—C52—C57—C56179.8 (2)
C28—S2—C24—N511.2 (2)C55—C56—C57—C520.0 (4)
C28—S2—C24—N6169.36 (18)N9—C48—C58—C6044.6 (3)
C24—N5—C25—C261.4 (3)C49—C48—C58—C60136.5 (3)
C24—N5—C25—C35178.2 (2)C48—C58—C60—C6154.3 (3)
N5—C25—C26—C274.2 (4)C48—C58—C60—C59177.9 (2)
C35—C25—C26—C27175.4 (2)C50—N12—C63—C6416.2 (4)
N5—C25—C26—C39177.9 (2)C50—N12—C63—C68165.5 (2)
C35—C25—C26—C392.5 (4)C68—C63—C64—C650.8 (4)
C24—N6—C27—N8179.9 (2)N12—C63—C64—C65179.1 (2)
C24—N6—C27—C260.3 (3)C63—C64—C65—C660.4 (4)
C40—N8—C27—N66.2 (4)C64—C65—C66—C670.6 (4)
C40—N8—C27—C26174.0 (2)C65—C66—C67—C681.2 (4)
C25—C26—C27—N63.6 (3)C65—C66—C67—C69179.7 (3)
C39—C26—C27—N6178.5 (2)C66—C67—C68—C630.7 (4)
C25—C26—C27—N8176.5 (2)C69—C67—C68—C63179.3 (2)
C39—C26—C27—N81.3 (4)C64—C63—C68—C670.3 (4)
C24—S2—C28—C2971.8 (2)N12—C63—C68—C67178.8 (2)
S2—C28—C29—C30126.3 (2)C66—C67—C69—F7104.6 (3)
S2—C28—C29—C3454.1 (3)C68—C67—C69—F774.0 (4)
C34—C29—C30—C313.0 (4)C66—C67—C69—F816.6 (4)
C28—C29—C30—C31176.6 (3)C68—C67—C69—F8164.8 (3)
C29—C30—C31—C321.3 (5)C66—C67—C69—F9135.8 (3)
C30—C31—C32—C331.7 (4)C68—C67—C69—F945.6 (4)
C30—C31—C32—Cl2178.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4n···N7i0.882.393.227 (3)159
N8—H8n···N3i0.882.383.213 (3)158
N12—H12n···N11ii0.882.363.206 (3)160
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z.

Experimental details

Crystal data
Chemical formulaC23H20ClF3N4S
Mr476.94
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)15.3906 (6), 15.7040 (7), 15.9129 (7)
α, β, γ (°)89.568 (3), 74.825 (4), 62.980 (4)
V3)3278.9 (2)
Z6
Radiation typeCu Kα
µ (mm1)2.83
Crystal size (mm)0.35 × 0.15 × 0.03
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.437, 0.920
No. of measured, independent and
observed [I > 2σ(I)] reflections
38203, 25266, 18393
Rint0.075
(sin θ/λ)max1)0.632
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.190, 1.02
No. of reflections25266
No. of parameters866
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.44, 0.53

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4n···N7i0.882.393.227 (3)159
N8—H8n···N3i0.882.383.213 (3)158
N12—H12n···N11ii0.882.363.206 (3)160
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z.
 

Footnotes

Additional correspondence author, e-mail: elemam5@hotmail.com.

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
First citationAl-Abdullah, E. S., Al-Obaid, A. M., Al-Deeb, O. A., Habib, E. E. & El-Emam, A. A. (2011). Eur. J. Med. Chem. 46, 4642–4647.  Web of Science CAS PubMed Google Scholar
First citationAl-Omar, M. A., Al-Obaid, A. M., El-Brollosy, N. R. & El-Emam, A. A. (2010). Synth. Commun. 40, 1530–1538.  CAS Google Scholar
First citationAl-Safarjalani, O. N., Zhou, X., Rais, R. H., Shi, J., Schinazi, R. F., Naguib, F. N. M. & El Kouni, M. H. (2005). Cancer Chemother. Pharmacol. 55, 541–551.  Web of Science PubMed CAS Google Scholar
First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBrunelle, M. N., Lucifora, J., Neyts, J., Villet, S., Holy, A., Trepo, C. & Zoulim, F. (2007). Antimicrob. Agents Chemother. 51, 2240–2243.  Web of Science CrossRef PubMed CAS Google Scholar
First citationDing, Y., Girardet, J.-L., Smith, K. L., Larson, G., Prigaro, B., Wu, J. Z. & Yao, N. (2006). Bioorg. Chem. 34, 26–38.  Web of Science CrossRef PubMed CAS Google Scholar
First citationEl-Emam, A. A., Al-Deeb, O. A., Al-Turkistani, A. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o3126.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationGans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557–559.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals 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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