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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 3| March 2012| Pages o674-o675

Ethyl ({5-[5′-(2-eth­­oxy-2-oxoeth­­oxy)-4,4′′-di­fluoro-1,1′:3′,1′′-terphenyl-4′-yl]-1,3,4-oxa­diazol-2-yl}sulfan­yl)acetate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
*Correspondence e-mail: hkfun@usm.my

(Received 26 January 2012; accepted 5 February 2012; online 10 February 2012)

In the title compound, C28H24F2N2O6S, the whole mol­ecule is disordered over two sites with refined occupancies of 0.778 (3) and 0.222 (3). The central benzene ring makes dihedral angles of 56.0 (4), 34.5 (4) and 70.9 (4)°, respectively, with the two terminal benzene rings and the 1,3,4-oxadiazole ring in the major component of the disordered mol­ecule. The corresponding angles in the minor component are 59.7 (16), 25.6 (13) and 75.5 (14)°. In the crystal, mol­ecules are linked via C—H⋯F, C—H⋯N, C—H⋯O and C—H⋯S hydrogen bonds into a three-dimensional network. In addition, C—H⋯π inter­actions are observed.

Related literature

For a related structure and background to terphenyls and their oxadiazole derivatives, see: Fun, Arshad et al. (2011[Fun, H.-K., Arshad, S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3372.]); Fun, Chia et al. (2011[Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3390.]); Fun et al. (2012[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o163.]); Samshuddin et al. (2011[Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Molbank, 2011, M745.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C28H24F2N2O6S

  • Mr = 554.55

  • Triclinic, [P \overline 1]

  • a = 8.2721 (8) Å

  • b = 10.274 (1) Å

  • c = 16.2342 (16) Å

  • α = 81.058 (2)°

  • β = 82.987 (2)°

  • γ = 83.646 (2)°

  • V = 1346.8 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 100 K

  • 0.42 × 0.24 × 0.12 mm

Data collection
  • Bruker SMART APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.928, Tmax = 0.978

  • 25187 measured reflections

  • 7034 independent reflections

  • 5142 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 0.196

  • S = 1.01

  • 7034 reflections

  • 506 parameters

  • 99 restraints

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.66 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C9/C16/C17/C22 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8A⋯F1i 0.95 2.36 3.307 (8) 174
C15—H15A⋯N2ii 0.95 2.45 3.266 (5) 144
C18—H18B⋯O3iii 0.99 2.38 3.200 (11) 140
C25—H25A⋯F2iv 0.99 2.46 3.112 (5) 123
C25—H25A⋯O6v 0.99 2.49 3.158 (9) 125
C27—H27B⋯F2vi 0.99 2.46 3.217 (7) 133
C28—H28C⋯S1v 0.98 2.85 3.700 (10) 146
C5—H5ACg1vii 0.95 2.76 3.579 (6) 145
C18—H18ACg1ii 0.99 2.62 3.456 (10) 142
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+2, -z; (iii) -x+2, -y+2, -z; (iv) x, y, z+1; (v) -x+1, -y+1, -z+1; (vi) x-1, y, z+1; (vii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

In continuation of our work on synthesis of terphenyls and their oxadiazole derivatives (Fun, Arshad et al., 2011; Fun, Chia et al., 2011; Fun et al., 2012), the title compound is prepared and its crystal structure is reported. The starting material of the title compound was prepared from 4,4'-difluoro chalcone by several steps (Samshuddin et al., 2011).

The molecular structure in shown in Fig. 1. The whole molecule of the title compound is disordered over two positions with a refined site-occupancy ratio of 0.778 (3): 0.222 (3). For the major disorder component, the central benzene ring (C7–C9/C16/C17/C22) makes dihedral angles of 56.0 (4), 34.5 (4) and 70.9 (4)° with the terminal benzene rings (C1–C6 & C10–C15) and 1,3,4-oxadiazole ring (O1/N1/N2/C23/C24), respectively. On the other hand, for the minor disorder component, the central benzene ring (C7X–C9X/C16X/C17X/C22X) makes dihedral angles of 59.7 (16), 25.6 (13) and 75.5 (14)° with the terminal benzene rings (C1X–C6X & C10X–C15X) and 1,3,4-oxadiazole ring (O1X/N1X/N2X/C23X/C24X), respectively. Bond lengths (Allen et al., 1987) and angles are within normal range.

In the crystal structure (Fig. 2), the molecules are linked via intermolecular C8—H8A···F1, C15—H15A···N2, C18—H18B···O3, C25—H25A···F2, C25—H25A···O6, C27—H27B···F2 and C28—H28C···S1 hydrogen bonds (Table 1) into a three-dimensional network. The crystal structure are further stabilized by the intermolecular C5—H5A···Cg1 and C18—H18A···Cg1 (Table 1) interactions (Cg1 is the centroid of C7–C9/C16/C17/C22).

Related literature top

For a related structure and background to terphenyls and their oxadiazole derivatives, see: Fun, Arshad et al. (2011); Fun, Chia et al. (2011); Fun et al. (2012); Samshuddin et al. (2011). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental top

To a solution of 5-(4,4''-difluoro-5'-hydroxy-1,1':3',1''-terphenyl-4'-yl)-1,3,4 -oxadiazole-2(3H)-thione (3.82 g, 0.01 mol) in ethanol (20 ml), 10% aqueous sodium hydroxide solution (3.5 ml) was added. Ethyl chloroacetate (1 ml) was then added and heated to reflux for 4 h. The reaction mixture was then poured into ice cold water, filtered and crystallized from ethanol. The single-crystal was grown from DMF by slow evaporation method and the yield of the compound was 72%. (M. p.: 378 K).

Refinement top

The title compound is disordered over two positions with a refined site-occupancy ratio of 0.778 (3): 0.222 (3) and the minor disordered component were refined isotropically. All H atoms were positioned geometrically [C—H = 0.95–0.99 Å] and refined using a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups. The restraints of same geometries were applied for major and minor components. The same Uij parameters were also used for atom pairs C21/C28 and O1X/O6X.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. All disordered components are shown.
[Figure 2] Fig. 2. The crystal packing of the title compound. Dashed lines represent the intermolecular hydrogen bonds. Only major disordered component is shown.
Ethyl ({5-[5'-(2-ethoxy-2-oxoethoxy)-4,4''-difluoro-1,1':3',1''-terphenyl- 4'-yl]-1,3,4-oxadiazol-2-yl}sulfanyl)acetate top
Crystal data top
C28H24F2N2O6SZ = 2
Mr = 554.55F(000) = 576
Triclinic, P1Dx = 1.367 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2721 (8) ÅCell parameters from 9309 reflections
b = 10.274 (1) Åθ = 2.5–30.0°
c = 16.2342 (16) ŵ = 0.18 mm1
α = 81.058 (2)°T = 100 K
β = 82.987 (2)°Block, pink
γ = 83.646 (2)°0.42 × 0.24 × 0.12 mm
V = 1346.8 (2) Å3
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer
7034 independent reflections
Radiation source: fine-focus sealed tube5142 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ϕ and ω scansθmax = 29.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1111
Tmin = 0.928, Tmax = 0.978k = 1313
25187 measured reflectionsl = 2222
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1038P)2 + 1.0279P]
where P = (Fo2 + 2Fc2)/3
7034 reflections(Δ/σ)max < 0.001
506 parametersΔρmax = 0.56 e Å3
99 restraintsΔρmin = 0.66 e Å3
Crystal data top
C28H24F2N2O6Sγ = 83.646 (2)°
Mr = 554.55V = 1346.8 (2) Å3
Triclinic, P1Z = 2
a = 8.2721 (8) ÅMo Kα radiation
b = 10.274 (1) ŵ = 0.18 mm1
c = 16.2342 (16) ÅT = 100 K
α = 81.058 (2)°0.42 × 0.24 × 0.12 mm
β = 82.987 (2)°
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer
7034 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5142 reflections with I > 2σ(I)
Tmin = 0.928, Tmax = 0.978Rint = 0.041
25187 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06199 restraints
wR(F2) = 0.196H-atom parameters constrained
S = 1.01Δρmax = 0.56 e Å3
7034 reflectionsΔρmin = 0.66 e Å3
506 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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*/UeqOcc. (<1)
S10.58917 (13)0.60843 (12)0.37370 (6)0.0401 (3)0.778 (3)
F10.1744 (5)0.4107 (4)0.1802 (3)0.0420 (8)0.778 (3)
F20.6675 (3)0.8297 (3)0.44112 (12)0.0638 (8)0.778 (3)
O10.5304 (3)0.6637 (3)0.21551 (18)0.0289 (5)0.778 (3)
O20.6528 (9)0.8792 (8)0.0945 (4)0.029 (2)0.778 (3)
O30.9649 (11)1.0846 (8)0.1047 (5)0.0337 (17)0.778 (3)
O40.8094 (4)0.9572 (3)0.20113 (16)0.0358 (7)0.778 (3)
O50.2059 (5)0.7253 (4)0.51466 (19)0.0741 (10)0.778 (3)
O60.2572 (10)0.5310 (6)0.4679 (6)0.0668 (17)0.778 (3)
N10.3396 (4)0.7577 (4)0.29952 (17)0.0334 (7)0.778 (3)
N20.3012 (4)0.7960 (4)0.21606 (19)0.0291 (8)0.778 (3)
C10.0796 (5)0.6815 (4)0.1171 (5)0.0250 (12)0.778 (3)
H1A0.07840.77250.12210.030*0.778 (3)
C20.0501 (9)0.6090 (7)0.1563 (6)0.040 (2)0.778 (3)
H2A0.13610.64730.19190.048*0.778 (3)
C30.0484 (7)0.4809 (6)0.1415 (5)0.0319 (13)0.778 (3)
C40.0733 (5)0.4176 (4)0.0933 (5)0.0280 (9)0.778 (3)
H4A0.06920.32840.08530.034*0.778 (3)
C50.2037 (5)0.4891 (4)0.0563 (7)0.0252 (12)0.778 (3)
H5A0.28870.44930.02100.030*0.778 (3)
C60.2101 (8)0.6188 (7)0.0708 (5)0.028 (3)0.778 (3)
C70.3507 (10)0.6935 (10)0.0303 (4)0.027 (3)0.778 (3)
C80.3921 (8)0.7060 (7)0.0551 (3)0.023 (2)0.778 (3)
H8A0.33130.66560.08860.027*0.778 (3)
C90.5218 (13)0.7769 (12)0.0929 (3)0.0246 (17)0.778 (3)
C100.5623 (4)0.7890 (4)0.1843 (2)0.0263 (8)0.778 (3)
C110.5427 (4)0.6849 (3)0.22762 (19)0.0378 (7)0.778 (3)
H11A0.50440.60540.19750.045*0.778 (3)
C120.5784 (5)0.6968 (4)0.3139 (2)0.0501 (9)0.778 (3)
H12A0.56660.62610.34340.060*0.778 (3)
C130.6326 (5)0.8162 (4)0.35627 (19)0.0443 (8)0.778 (3)
C140.6569 (5)0.9188 (3)0.31574 (18)0.0382 (7)0.778 (3)
H14A0.69740.99760.34580.046*0.778 (3)
C150.6203 (4)0.9036 (3)0.22892 (17)0.0336 (6)0.778 (3)
H15A0.63550.97360.19960.040*0.778 (3)
C160.6144 (12)0.8387 (11)0.0458 (3)0.023 (2)0.778 (3)
H16A0.70080.88910.07250.028*0.778 (3)
C170.5768 (12)0.8244 (12)0.0398 (4)0.026 (3)0.778 (3)
C180.7831 (10)0.9574 (9)0.0570 (4)0.0192 (17)0.778 (3)
H18A0.74001.03240.01710.023*0.778 (3)
H18B0.86740.90270.02540.023*0.778 (3)
C190.8586 (8)1.0093 (7)0.1238 (3)0.0250 (13)0.778 (3)
C200.9103 (8)0.9863 (6)0.2664 (2)0.0642 (17)0.778 (3)
H20A1.02810.96530.24910.077*0.778 (3)
H20B0.89161.08120.27270.077*0.778 (3)
C210.8614 (12)0.9047 (10)0.3464 (3)0.134 (3)0.778 (3)
H21A0.90640.93640.39200.202*0.778 (3)
H21B0.90340.81230.34370.202*0.778 (3)
H21C0.74180.91120.35690.202*0.778 (3)
C220.4441 (7)0.7530 (7)0.0782 (4)0.0209 (15)0.778 (3)
C230.4165 (5)0.7381 (5)0.1686 (3)0.0258 (10)0.778 (3)
C240.4733 (4)0.6828 (4)0.2944 (2)0.0294 (6)0.778 (3)
C250.4750 (5)0.6811 (4)0.4553 (2)0.0464 (8)0.778 (3)
H25A0.53520.66100.50550.056*0.778 (3)
H25B0.46480.77840.43890.056*0.778 (3)
C260.3012 (7)0.6343 (5)0.4787 (2)0.0499 (10)0.778 (3)
C270.0381 (8)0.6954 (8)0.5440 (3)0.097 (2)0.778 (3)
H27A0.00170.64560.50420.117*0.778 (3)
H27B0.03330.77920.54550.117*0.778 (3)
C280.0273 (12)0.6142 (10)0.6312 (3)0.134 (3)0.778 (3)
H28A0.08720.59980.65040.202*0.778 (3)
H28B0.07040.66190.67020.202*0.778 (3)
H28C0.09170.52860.62890.202*0.778 (3)
S1X0.5488 (5)0.6512 (4)0.3949 (2)0.0423 (9)*0.222 (3)
F1X0.1874 (19)0.4273 (16)0.1937 (10)0.038 (3)*0.222 (3)
F2X0.6240 (7)0.9223 (7)0.4532 (3)0.0348 (14)*0.222 (3)
O1X0.5170 (16)0.6877 (13)0.2335 (7)0.038 (3)*0.222 (3)
O2X0.659 (3)0.878 (2)0.0940 (11)0.013 (5)*0.222 (3)
O3X0.955 (4)1.093 (3)0.1106 (17)0.024 (4)*0.222 (3)
O4X0.8537 (13)0.9319 (12)0.2057 (7)0.032 (3)*0.222 (3)
O5X0.1312 (13)0.7237 (9)0.5181 (6)0.038 (2)*0.222 (3)
O6X0.254 (3)0.5344 (17)0.4657 (16)0.038 (3)*0.222 (3)
N1X0.3157 (13)0.7979 (11)0.3061 (6)0.025 (3)*0.222 (3)
N2X0.2928 (17)0.8299 (13)0.2189 (7)0.027 (3)*0.222 (3)
C1X0.087 (3)0.681 (3)0.125 (2)0.059 (11)*0.222 (3)
H1XA0.10530.76050.14430.071*0.222 (3)
C2X0.058 (3)0.623 (2)0.1543 (15)0.020 (5)*0.222 (3)
H2XA0.15430.67420.17280.024*0.222 (3)
C3X0.055 (3)0.489 (2)0.1552 (18)0.027 (5)*0.222 (3)
C4X0.069 (3)0.422 (2)0.1104 (15)0.034 (6)*0.222 (3)
H4XA0.06840.33020.10840.041*0.222 (3)
C5X0.197 (4)0.491 (2)0.068 (3)0.049 (10)*0.222 (3)
H5XA0.28250.44420.03660.058*0.222 (3)
C6X0.207 (3)0.625 (2)0.0680 (17)0.025 (9)*0.222 (3)
C7X0.355 (3)0.695 (3)0.0340 (11)0.020 (8)*0.222 (3)
C8X0.399 (4)0.712 (4)0.0541 (12)0.042 (11)*0.222 (3)
H8XA0.34040.66680.08570.051*0.222 (3)
C9X0.518 (5)0.789 (4)0.1000 (8)0.022 (6)*0.222 (3)
C10X0.5499 (15)0.8212 (14)0.1947 (7)0.020 (3)*0.222 (3)
C11X0.4290 (9)0.8101 (8)0.2467 (4)0.0184 (15)*0.222 (3)
H11B0.32740.78030.22130.022*0.222 (3)
C12X0.4523 (9)0.8412 (8)0.3336 (5)0.0244 (17)*0.222 (3)
H12B0.37010.83110.36760.029*0.222 (3)
C13X0.5997 (10)0.8870 (11)0.3683 (5)0.0262 (19)*0.222 (3)
C14X0.7297 (12)0.8863 (10)0.3221 (5)0.026 (2)*0.222 (3)
H14B0.83490.90530.34890.031*0.222 (3)
C15X0.7017 (11)0.8567 (9)0.2352 (5)0.0212 (16)*0.222 (3)
H15B0.78800.86070.20230.025*0.222 (3)
C16X0.602 (4)0.847 (4)0.0455 (11)0.026 (8)*0.222 (3)
H16B0.68730.89980.07000.031*0.222 (3)
C17X0.568 (4)0.830 (4)0.0420 (9)0.010 (5)*0.222 (3)
C18X0.788 (5)0.958 (4)0.0629 (15)0.038 (10)*0.222 (3)
H18C0.74161.03940.02940.046*0.222 (3)
H18D0.86640.91000.02450.046*0.222 (3)
C19X0.879 (3)0.997 (2)0.1281 (9)0.018 (4)*0.222 (3)
C20X0.8684 (16)1.0238 (13)0.2688 (8)0.028 (3)*0.222 (3)
H20C0.98431.03590.27230.033*0.222 (3)
H20D0.80821.11150.25370.033*0.222 (3)
C21X0.7923 (11)0.9531 (9)0.3500 (6)0.0228 (17)*0.222 (3)
H21D0.84350.97500.39680.034*0.222 (3)
H21E0.80900.85730.34920.034*0.222 (3)
H21F0.67480.98080.35690.034*0.222 (3)
C22X0.443 (4)0.753 (4)0.0873 (10)0.034 (8)*0.222 (3)
C23X0.4077 (19)0.7599 (16)0.1786 (7)0.014 (3)*0.222 (3)
C24X0.4470 (15)0.7199 (12)0.3081 (6)0.024 (3)*0.222 (3)
C25X0.4106 (13)0.7118 (12)0.4705 (7)0.031 (2)*0.222 (3)
H25C0.45960.69680.52420.037*0.222 (3)
H25D0.38750.80850.45460.037*0.222 (3)
C26X0.2475 (15)0.6464 (14)0.4832 (11)0.038 (4)*0.222 (3)
C27X0.0292 (17)0.6719 (14)0.5411 (9)0.046 (3)*0.222 (3)
H27C0.05130.61900.49840.055*0.222 (3)
H27D0.11600.74620.54340.055*0.222 (3)
C28X0.0306 (17)0.5858 (14)0.6262 (8)0.047 (3)*0.222 (3)
H28D0.14270.56530.64660.071*0.222 (3)
H28E0.01080.63320.66600.071*0.222 (3)
H28F0.03930.50340.62100.071*0.222 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0406 (5)0.0444 (6)0.0347 (4)0.0170 (4)0.0120 (4)0.0121 (4)
F10.0311 (13)0.0526 (19)0.0462 (19)0.0355 (13)0.0006 (11)0.0007 (15)
F20.0891 (17)0.0798 (19)0.0308 (10)0.0392 (14)0.0001 (10)0.0166 (10)
O10.0228 (10)0.0285 (13)0.0334 (13)0.0101 (8)0.0010 (9)0.0052 (11)
O20.027 (3)0.026 (2)0.036 (3)0.0186 (13)0.0023 (8)0.0027 (8)
O30.028 (2)0.032 (2)0.044 (2)0.0204 (17)0.0029 (14)0.0094 (15)
O40.0421 (17)0.0432 (17)0.0271 (11)0.0278 (15)0.0051 (11)0.0023 (10)
O50.064 (2)0.112 (3)0.0458 (16)0.008 (2)0.0025 (15)0.0131 (16)
O60.075 (3)0.074 (3)0.052 (2)0.0416 (19)0.0190 (14)0.0242 (15)
N10.0375 (17)0.0317 (18)0.0322 (13)0.0117 (13)0.0028 (10)0.0031 (12)
N20.0320 (15)0.0225 (17)0.0340 (15)0.0092 (12)0.0042 (9)0.0024 (12)
C10.0150 (14)0.0199 (17)0.040 (2)0.0085 (9)0.0064 (12)0.0024 (10)
C20.0196 (19)0.044 (4)0.056 (3)0.0138 (19)0.0043 (14)0.001 (2)
C30.024 (2)0.038 (2)0.035 (3)0.0233 (15)0.0083 (14)0.0075 (17)
C40.0262 (18)0.0204 (18)0.039 (3)0.0147 (11)0.0128 (15)0.0070 (15)
C50.0162 (18)0.0155 (18)0.043 (3)0.0077 (9)0.0080 (12)0.0054 (12)
C60.016 (2)0.019 (3)0.049 (4)0.0078 (11)0.0094 (13)0.0092 (13)
C70.017 (2)0.012 (2)0.052 (5)0.0049 (9)0.0065 (13)0.0023 (12)
C80.0141 (18)0.0118 (18)0.044 (3)0.0050 (9)0.0056 (10)0.0058 (10)
C90.0191 (18)0.016 (3)0.040 (3)0.0044 (17)0.0022 (17)0.0075 (18)
C100.0220 (14)0.0211 (19)0.0380 (17)0.0051 (13)0.0039 (11)0.0083 (14)
C110.0444 (16)0.0318 (15)0.0413 (15)0.0176 (12)0.0054 (12)0.0068 (12)
C120.072 (2)0.0443 (19)0.0417 (16)0.0276 (17)0.0056 (15)0.0150 (14)
C130.0555 (19)0.050 (2)0.0308 (14)0.0179 (17)0.0036 (13)0.0092 (14)
C140.051 (2)0.0296 (15)0.0348 (15)0.0127 (15)0.0040 (13)0.0025 (11)
C150.0415 (16)0.0253 (14)0.0361 (14)0.0120 (13)0.0018 (11)0.0063 (11)
C160.015 (2)0.018 (2)0.038 (3)0.0062 (17)0.0027 (10)0.0092 (12)
C170.020 (3)0.017 (3)0.043 (3)0.0065 (18)0.0002 (11)0.0050 (11)
C180.0174 (19)0.0148 (19)0.026 (2)0.0112 (10)0.0008 (11)0.0011 (11)
C190.020 (2)0.019 (2)0.036 (2)0.0044 (18)0.0009 (13)0.0046 (11)
C200.103 (5)0.071 (4)0.0313 (17)0.056 (4)0.003 (2)0.015 (2)
C210.171 (6)0.202 (7)0.0420 (19)0.102 (5)0.012 (3)0.006 (3)
C220.0150 (17)0.0121 (17)0.035 (2)0.0049 (8)0.0023 (12)0.0024 (13)
C230.0229 (16)0.018 (2)0.0369 (19)0.0097 (12)0.0026 (12)0.0002 (14)
C240.0331 (15)0.0274 (17)0.0285 (15)0.0162 (13)0.0012 (11)0.0018 (13)
C250.056 (2)0.044 (2)0.0436 (18)0.0117 (18)0.0193 (17)0.0051 (15)
C260.055 (3)0.069 (3)0.0245 (16)0.013 (2)0.0090 (18)0.0073 (14)
C270.063 (4)0.171 (7)0.049 (2)0.012 (4)0.004 (3)0.010 (3)
C280.171 (6)0.202 (7)0.0420 (19)0.102 (5)0.012 (3)0.006 (3)
Geometric parameters (Å, º) top
S1—C241.730 (3)S1X—C25X1.714 (10)
S1—C251.746 (4)S1X—C24X1.744 (10)
F1—C31.366 (4)F1X—C3X1.365 (14)
F2—C131.361 (3)F2X—C13X1.365 (9)
O1—C241.346 (5)O1X—C24X1.350 (12)
O1—C231.373 (4)O1X—C23X1.415 (13)
O2—C171.367 (5)O2X—C17X1.376 (12)
O2—C181.434 (5)O2X—C18X1.411 (15)
O3—C191.215 (5)O3X—C19X1.212 (15)
O4—C191.320 (5)O4X—C19X1.333 (14)
O4—C201.510 (5)O4X—C20X1.521 (13)
O5—C261.315 (6)O5X—C26X1.309 (13)
O5—C271.461 (7)O5X—C27X1.469 (13)
O6—C261.203 (6)O6X—C26X1.222 (14)
N1—C241.277 (5)N1X—C24X1.277 (12)
N1—N21.415 (4)N1X—N2X1.434 (12)
N2—C231.301 (5)N2X—C23X1.301 (13)
C1—C61.394 (5)C1X—C2X1.394 (16)
C1—C21.405 (5)C1X—C6X1.413 (15)
C1—H1A0.9500C1X—H1XA0.9500
C2—C31.372 (7)C2X—C3X1.372 (15)
C2—H2A0.9500C2X—H2XA0.9500
C3—C41.367 (6)C3X—C4X1.369 (15)
C4—C51.394 (4)C4X—C5X1.391 (16)
C4—H4A0.9500C4X—H4XA0.9500
C5—C61.396 (6)C5X—C6X1.385 (16)
C5—H5A0.9500C5X—H5XA0.9500
C6—C71.492 (4)C6X—C7X1.493 (13)
C7—C81.376 (5)C7X—C8X1.420 (14)
C7—C221.406 (6)C7X—C22X1.429 (14)
C8—C91.390 (5)C8X—C9X1.400 (15)
C8—H8A0.9500C8X—H8XA0.9500
C9—C161.405 (5)C9X—C16X1.419 (15)
C9—C101.470 (6)C9X—C10X1.519 (13)
C10—C151.384 (5)C10X—C15X1.402 (12)
C10—C111.401 (4)C10X—C11X1.409 (12)
C11—C121.385 (4)C11X—C12X1.392 (9)
C11—H11A0.9500C11X—H11B0.9500
C12—C131.401 (5)C12X—C13X1.380 (10)
C12—H12A0.9500C12X—H12B0.9500
C13—C141.371 (4)C13X—C14X1.383 (11)
C14—C151.393 (4)C14X—C15X1.393 (10)
C14—H14A0.9500C14X—H14B0.9500
C15—H15A0.9500C15X—H15B0.9500
C16—C171.375 (5)C16X—C17X1.402 (13)
C16—H16A0.9500C16X—H16B0.9500
C17—C221.415 (5)C17X—C22X1.434 (14)
C18—C191.507 (6)C18X—C19X1.500 (15)
C18—H18A0.9900C18X—H18C0.9900
C18—H18B0.9900C18X—H18D0.9900
C20—C211.470 (7)C20X—C21X1.504 (13)
C20—H20A0.9900C20X—H20C0.9900
C20—H20B0.9900C20X—H20D0.9900
C21—H21A0.9800C21X—H21D0.9800
C21—H21B0.9800C21X—H21E0.9800
C21—H21C0.9800C21X—H21F0.9800
C22—C231.444 (6)C22X—C23X1.486 (14)
C25—C261.551 (7)C25X—C26X1.550 (14)
C25—H25A0.9900C25X—H25C0.9900
C25—H25B0.9900C25X—H25D0.9900
C27—C281.526 (7)C27X—C28X1.520 (14)
C27—H27A0.9900C27X—H27C0.9900
C27—H27B0.9900C27X—H27D0.9900
C28—H28A0.9800C28X—H28D0.9800
C28—H28B0.9800C28X—H28E0.9800
C28—H28C0.9800C28X—H28F0.9800
C24—S1—C2597.3 (2)C23X—N2X—N1X106.6 (10)
C24—O1—C23103.0 (3)C2X—C1X—C6X121.8 (18)
C17—O2—C18115.4 (5)C2X—C1X—H1XA119.1
C19—O4—C20114.1 (3)C6X—C1X—H1XA119.1
C26—O5—C27116.8 (5)C3X—C2X—C1X117.2 (18)
C24—N1—N2105.7 (3)C3X—C2X—H2XA121.4
C23—N2—N1106.4 (3)C1X—C2X—H2XA121.4
C6—C1—C2119.5 (4)F1X—C3X—C4X120.6 (16)
C6—C1—H1A120.3F1X—C3X—C2X118.2 (15)
C2—C1—H1A120.3C4X—C3X—C2X120.7 (15)
C3—C2—C1117.7 (5)C3X—C4X—C5X118.6 (17)
C3—C2—H2A121.1C3X—C4X—H4XA120.7
C1—C2—H2A121.1C5X—C4X—H4XA120.7
F1—C3—C4118.0 (5)C6X—C5X—C4X123.9 (18)
F1—C3—C2117.5 (5)C6X—C5X—H5XA118.0
C4—C3—C2124.5 (4)C4X—C5X—H5XA118.0
C3—C4—C5117.4 (4)C5X—C6X—C1X113.3 (16)
C3—C4—H4A121.3C5X—C6X—C7X123.8 (19)
C5—C4—H4A121.3C1X—C6X—C7X120.2 (16)
C4—C5—C6120.5 (5)C8X—C7X—C22X120.4 (14)
C4—C5—H5A119.8C8X—C7X—C6X118.3 (16)
C6—C5—H5A119.8C22X—C7X—C6X121.1 (14)
C1—C6—C5120.1 (4)C9X—C8X—C7X127.7 (17)
C1—C6—C7120.2 (5)C9X—C8X—H8XA116.2
C5—C6—C7119.5 (5)C7X—C8X—H8XA116.2
C8—C7—C22118.3 (4)C8X—C9X—C16X110.6 (14)
C8—C7—C6120.8 (5)C8X—C9X—C10X127.2 (15)
C22—C7—C6120.9 (5)C16X—C9X—C10X121.9 (15)
C7—C8—C9120.7 (4)C15X—C10X—C11X116.6 (8)
C7—C8—H8A119.6C15X—C10X—C9X122.2 (13)
C9—C8—H8A119.6C11X—C10X—C9X121.1 (13)
C8—C9—C16121.5 (5)C12X—C11X—C10X122.7 (7)
C8—C9—C10119.4 (4)C12X—C11X—H11B118.7
C16—C9—C10119.1 (4)C10X—C11X—H11B118.7
C15—C10—C11119.0 (3)C13X—C12X—C11X117.2 (7)
C15—C10—C9120.4 (4)C13X—C12X—H12B121.4
C11—C10—C9120.6 (5)C11X—C12X—H12B121.4
C12—C11—C10120.7 (3)F2X—C13X—C12X118.5 (7)
C12—C11—H11A119.7F2X—C13X—C14X118.3 (7)
C10—C11—H11A119.7C12X—C13X—C14X122.8 (8)
C11—C12—C13118.0 (3)C13X—C14X—C15X117.9 (8)
C11—C12—H12A121.0C13X—C14X—H14B121.1
C13—C12—H12A121.0C15X—C14X—H14B121.1
F2—C13—C14118.4 (3)C14X—C15X—C10X122.0 (8)
F2—C13—C12118.7 (3)C14X—C15X—H15B119.0
C14—C13—C12122.9 (3)C10X—C15X—H15B119.0
C13—C14—C15117.7 (3)C17X—C16X—C9X124.4 (16)
C13—C14—H14A121.2C17X—C16X—H16B117.8
C15—C14—H14A121.2C9X—C16X—H16B117.8
C10—C15—C14121.7 (3)O2X—C17X—C16X123.4 (15)
C10—C15—H15A119.2O2X—C17X—C22X112.6 (13)
C14—C15—H15A119.2C16X—C17X—C22X123.8 (14)
C17—C16—C9118.3 (5)O2X—C18X—C19X115.3 (17)
C17—C16—H16A120.8O2X—C18X—H18C108.4
C9—C16—H16A120.8C19X—C18X—H18C108.4
O2—C17—C16125.8 (5)O2X—C18X—H18D108.4
O2—C17—C22114.0 (5)C19X—C18X—H18D108.4
C16—C17—C22120.1 (5)H18C—C18X—H18D107.5
O2—C18—C19110.1 (5)O3X—C19X—O4X123.5 (17)
O2—C18—H18A109.6O3X—C19X—C18X119.1 (17)
C19—C18—H18A109.6O4X—C19X—C18X116.8 (15)
O2—C18—H18B109.6C21X—C20X—O4X103.4 (10)
C19—C18—H18B109.6C21X—C20X—H20C111.1
H18A—C18—H18B108.2O4X—C20X—H20C111.1
O3—C19—O4125.1 (6)C21X—C20X—H20D111.1
O3—C19—C18120.5 (5)O4X—C20X—H20D111.1
O4—C19—C18114.2 (4)H20C—C20X—H20D109.0
C21—C20—O4108.4 (4)C20X—C21X—H21D109.5
C21—C20—H20A110.0C20X—C21X—H21E109.5
O4—C20—H20A110.0H21D—C21X—H21E109.5
C21—C20—H20B110.0C20X—C21X—H21F109.5
O4—C20—H20B110.0H21D—C21X—H21F109.5
H20A—C20—H20B108.4H21E—C21X—H21F109.5
C7—C22—C17120.9 (5)C7X—C22X—C17X113.0 (12)
C7—C22—C23122.2 (4)C7X—C22X—C23X129.5 (14)
C17—C22—C23116.8 (4)C17X—C22X—C23X116.9 (14)
N2—C23—O1111.2 (4)N2X—C23X—O1X111.3 (10)
N2—C23—C22129.0 (4)N2X—C23X—C22X130.0 (18)
O1—C23—C22119.5 (5)O1X—C23X—C22X118.6 (17)
N1—C24—O1113.8 (3)N1X—C24X—O1X116.0 (9)
N1—C24—S1128.9 (3)N1X—C24X—S1X128.2 (9)
O1—C24—S1117.4 (3)O1X—C24X—S1X115.8 (9)
C26—C25—S1114.0 (3)C26X—C25X—S1X112.8 (8)
C26—C25—H25A108.7C26X—C25X—H25C109.0
S1—C25—H25A108.7S1X—C25X—H25C109.0
C26—C25—H25B108.7C26X—C25X—H25D109.0
S1—C25—H25B108.7S1X—C25X—H25D109.0
H25A—C25—H25B107.6H25C—C25X—H25D107.8
O6—C26—O5123.9 (6)O6X—C26X—O5X133.4 (14)
O6—C26—C25126.9 (6)O6X—C26X—C25X116.7 (14)
O5—C26—C25109.2 (4)O5X—C26X—C25X109.7 (10)
O5—C27—C28111.3 (5)O5X—C27X—C28X109.4 (10)
O5—C27—H27A109.4O5X—C27X—H27C109.8
C28—C27—H27A109.4C28X—C27X—H27C109.8
O5—C27—H27B109.4O5X—C27X—H27D109.8
C28—C27—H27B109.4C28X—C27X—H27D109.8
H27A—C27—H27B108.0H27C—C27X—H27D108.2
C25X—S1X—C24X97.8 (6)C27X—C28X—H28D109.5
C24X—O1X—C23X101.1 (9)C27X—C28X—H28E109.5
C17X—O2X—C18X122.3 (15)H28D—C28X—H28E109.5
C19X—O4X—C20X109.4 (12)C27X—C28X—H28F109.5
C26X—O5X—C27X116.9 (10)H28D—C28X—H28F109.5
C24X—N1X—N2X104.8 (9)H28E—C28X—H28F109.5
C24—N1—N2—C230.7 (4)C24X—N1X—N2X—C23X4.3 (16)
C6—C1—C2—C35.1 (13)C6X—C1X—C2X—C3X26 (5)
C1—C2—C3—F1179.6 (8)C1X—C2X—C3X—F1X171 (3)
C1—C2—C3—C42.1 (14)C1X—C2X—C3X—C4X16 (4)
F1—C3—C4—C5178.0 (7)F1X—C3X—C4X—C5X176 (3)
C2—C3—C4—C50.6 (12)C2X—C3X—C4X—C5X4 (5)
C3—C4—C5—C62.0 (12)C3X—C4X—C5X—C6X0 (6)
C2—C1—C6—C56.7 (14)C4X—C5X—C6X—C1X8 (6)
C2—C1—C6—C7178.7 (8)C4X—C5X—C6X—C7X170 (3)
C4—C5—C6—C15.1 (14)C2X—C1X—C6X—C5X22 (5)
C4—C5—C6—C7179.8 (8)C2X—C1X—C6X—C7X176 (3)
C1—C6—C7—C8121.1 (10)C5X—C6X—C7X—C8X69 (5)
C5—C6—C7—C853.6 (13)C1X—C6X—C7X—C8X130 (4)
C1—C6—C7—C2258.9 (13)C5X—C6X—C7X—C22X116 (4)
C5—C6—C7—C22126.5 (11)C1X—C6X—C7X—C22X44 (5)
C22—C7—C8—C90.7 (15)C22X—C7X—C8X—C9X3 (7)
C6—C7—C8—C9179.2 (10)C6X—C7X—C8X—C9X171 (4)
C7—C8—C9—C160.3 (18)C7X—C8X—C9X—C16X3 (7)
C7—C8—C9—C10179.7 (9)C7X—C8X—C9X—C10X172 (4)
C8—C9—C10—C15145.6 (8)C8X—C9X—C10X—C15X157 (4)
C16—C9—C10—C1533.8 (14)C16X—C9X—C10X—C15X29 (6)
C8—C9—C10—C1134.3 (14)C8X—C9X—C10X—C11X20 (6)
C16—C9—C10—C11146.3 (10)C16X—C9X—C10X—C11X154 (4)
C15—C10—C11—C120.9 (5)C15X—C10X—C11X—C12X4.3 (16)
C9—C10—C11—C12179.0 (6)C9X—C10X—C11X—C12X179 (2)
C10—C11—C12—C130.8 (6)C10X—C11X—C12X—C13X1.4 (14)
C11—C12—C13—F2179.7 (3)C11X—C12X—C13X—F2X177.9 (8)
C11—C12—C13—C142.4 (6)C11X—C12X—C13X—C14X8.8 (15)
F2—C13—C14—C15179.9 (3)F2X—C13X—C14X—C15X176.8 (9)
C12—C13—C14—C152.2 (6)C12X—C13X—C14X—C15X9.9 (16)
C11—C10—C15—C141.1 (6)C13X—C14X—C15X—C10X3.6 (16)
C9—C10—C15—C14178.8 (6)C11X—C10X—C15X—C14X3.2 (17)
C13—C14—C15—C100.4 (6)C9X—C10X—C15X—C14X180 (2)
C8—C9—C16—C172 (2)C8X—C9X—C16X—C17X1 (7)
C10—C9—C16—C17178.8 (11)C10X—C9X—C16X—C17X174 (4)
C18—O2—C17—C160.3 (18)C18X—O2X—C17X—C16X6 (6)
C18—O2—C17—C22177.3 (9)C18X—O2X—C17X—C22X179 (4)
C9—C16—C17—O2179.0 (12)C9X—C16X—C17X—O2X174 (4)
C9—C16—C17—C222.2 (19)C9X—C16X—C17X—C22X0 (8)
C17—O2—C18—C19178.8 (9)C17X—O2X—C18X—C19X178 (3)
C20—O4—C19—O36.6 (11)C20X—O4X—C19X—O3X23 (3)
C20—O4—C19—C18167.6 (7)C20X—O4X—C19X—C18X148 (3)
O2—C18—C19—O3175.5 (9)O2X—C18X—C19X—O3X159 (3)
O2—C18—C19—O410.0 (11)O2X—C18X—C19X—O4X13 (5)
C19—O4—C20—C21170.4 (7)C19X—O4X—C20X—C21X164.7 (14)
C8—C7—C22—C170.3 (15)C8X—C7X—C22X—C17X2 (6)
C6—C7—C22—C17179.7 (9)C6X—C7X—C22X—C17X172 (3)
C8—C7—C22—C23176.0 (8)C8X—C7X—C22X—C23X173 (3)
C6—C7—C22—C234.1 (13)C6X—C7X—C22X—C23X1 (6)
O2—C17—C22—C7178.4 (10)O2X—C17X—C22X—C7X175 (3)
C16—C17—C22—C71.2 (17)C16X—C17X—C22X—C7X0 (6)
O2—C17—C22—C235.1 (14)O2X—C17X—C22X—C23X13 (5)
C16—C17—C22—C23177.7 (10)C16X—C17X—C22X—C23X172 (4)
N1—N2—C23—O10.2 (5)N1X—N2X—C23X—O1X4.4 (18)
N1—N2—C23—C22173.9 (4)N1X—N2X—C23X—C22X179.8 (17)
C24—O1—C23—N20.3 (4)C24X—O1X—C23X—N2X2.7 (18)
C24—O1—C23—C22174.1 (4)C24X—O1X—C23X—C22X179.1 (16)
C7—C22—C23—N276.8 (10)C7X—C22X—C23X—N2X72 (5)
C17—C22—C23—N2106.8 (9)C17X—C22X—C23X—N2X98 (3)
C7—C22—C23—O1110.0 (8)C7X—C22X—C23X—O1X112 (4)
C17—C22—C23—O166.4 (10)C17X—C22X—C23X—O1X77 (4)
N2—N1—C24—O10.9 (4)N2X—N1X—C24X—O1X2.8 (16)
N2—N1—C24—S1177.4 (3)N2X—N1X—C24X—S1X176.4 (10)
C23—O1—C24—N10.8 (4)C23X—O1X—C24X—N1X0.3 (18)
C23—O1—C24—S1177.7 (3)C23X—O1X—C24X—S1X179.0 (11)
C25—S1—C24—N15.1 (3)C25X—S1X—C24X—N1X4.1 (14)
C25—S1—C24—O1173.2 (3)C25X—S1X—C24X—O1X176.7 (11)
C24—S1—C25—C2668.0 (3)C24X—S1X—C25X—C26X69.8 (11)
C27—O5—C26—O61.2 (8)C27X—O5X—C26X—O6X1 (3)
C27—O5—C26—C25177.7 (3)C27X—O5X—C26X—C25X175.0 (11)
S1—C25—C26—O625.1 (8)S1X—C25X—C26X—O6X27 (2)
S1—C25—C26—O5156.0 (3)S1X—C25X—C26X—O5X158.5 (11)
C26—O5—C27—C2884.4 (7)C26X—O5X—C27X—C28X83.6 (15)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C7–C9/C16/C17/C22 ring.
D—H···AD—HH···AD···AD—H···A
C8—H8A···F1i0.952.363.307 (8)174
C15—H15A···N2ii0.952.453.266 (5)144
C18—H18B···O3iii0.992.383.200 (11)140
C25—H25A···F2iv0.992.463.112 (5)123
C25—H25A···O6v0.992.493.158 (9)125
C27—H27B···F2vi0.992.463.217 (7)133
C28—H28C···S1v0.982.853.700 (10)146
C5—H5A···Cg1vii0.952.763.579 (6)145
C18—H18A···Cg1ii0.992.623.456 (10)142
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+2, z; (iii) x+2, y+2, z; (iv) x, y, z+1; (v) x+1, y+1, z+1; (vi) x1, y, z+1; (vii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC28H24F2N2O6S
Mr554.55
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)8.2721 (8), 10.274 (1), 16.2342 (16)
α, β, γ (°)81.058 (2), 82.987 (2), 83.646 (2)
V3)1346.8 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.42 × 0.24 × 0.12
Data collection
DiffractometerBruker SMART APEXII DUO CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.928, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections
25187, 7034, 5142
Rint0.041
(sin θ/λ)max1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.196, 1.01
No. of reflections7034
No. of parameters506
No. of restraints99
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.66

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C7–C9/C16/C17/C22 ring.
D—H···AD—HH···AD···AD—H···A
C8—H8A···F1i0.95002.36003.307 (8)174.00
C15—H15A···N2ii0.95002.45003.266 (5)144.00
C18—H18B···O3iii0.99002.38003.200 (11)140.00
C25—H25A···F2iv0.99002.46003.112 (5)123.00
C25—H25A···O6v0.99002.49003.158 (9)125.00
C27—H27B···F2vi0.99002.46003.217 (7)133.00
C28—H28C···S1v0.98002.85003.700 (10)146.00
C5—H5A···Cg1vii0.95002.76003.579 (6)145.00
C18—H18A···Cg1ii0.99002.62003.456 (10)142.00
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+2, z; (iii) x+2, y+2, z; (iv) x, y, z+1; (v) x+1, y+1, z+1; (vi) x1, y, z+1; (vii) x+1, y+1, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and SA thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). SA thanks the Malaysian government and USM for the award of Academic Staff Training Scheme (ASTS). BN thanks the University Grants Commission (UGC) for financial assistance through SAP and BSR one time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

References

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Volume 68| Part 3| March 2012| Pages o674-o675
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