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ISSN: 2056-9890

3,3′-[1,2-Phenyl­enebis(methyl­ene)]bis­­(1-ethyl-1H-benzimidazol-1-ium) bis­­(hexa­flourophosphate)

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 26 April 2012; accepted 30 April 2012; online 5 May 2012)

In the title compound, C26H28N42+·2PF6, the complete cation is generated by a crystallographic twofold axis. The benz­imidazole ring is almost planar (r.m.s. deviation = 0.0207 Å) and makes dihedral angles of 50.12 (2)° with its symmetry-related component and 65.81 (2)° with the central benzene ring. In the crystal, mol­ecules are linked into a three-dimensional network by C—H⋯F inter­actions. A ππ inter­action with a centroid–centroid distance of 3.530 (1) Å is observed. Four F atoms of the hexa­fluoro­phosphate anion are disordered over two sets of sites in a 0.889 (6):0.111 (6) ratio.

Related literature

For the biological applications of benzimidazoles, see: Narasimhan et al. (2012[Narasimhan, B., Sharma, D. & Kumar, P. (2012). Med. Chem. Res. 21, 269-283.]). For a related structure, see: Haque et al. (2012[Haque, R. A., Iqbal, M. A., Fun, H.-K. & Arshad, S. (2012). Acta Cryst. E68, o924-o925.]).

[Scheme 1]

Experimental

Crystal data
  • C26H28N42+·2PF6

  • Mr = 686.46

  • Monoclinic, C 2/c

  • a = 23.2016 (5) Å

  • b = 8.1526 (2) Å

  • c = 16.9992 (4) Å

  • β = 121.274 (1)°

  • V = 2748.23 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 100 K

  • 0.26 × 0.26 × 0.14 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.933, Tmax = 0.963

  • 14787 measured reflections

  • 3921 independent reflections

  • 3156 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.098

  • S = 1.05

  • 3921 reflections

  • 217 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1A⋯F6i 0.95 2.42 3.142 (3) 133
C3—H3A⋯F5ii 0.95 2.45 3.374 (2) 166
C5—H5A⋯F5iii 0.95 2.52 3.420 (3) 159
C6—H6A⋯F4iv 0.95 2.53 3.392 (2) 151
C8—H8B⋯F1i 0.99 2.39 3.350 (3) 164
C13—H13C⋯F1v 0.98 2.55 3.523 (2) 174
C13—H13C⋯F5v 0.98 2.50 3.166 (2) 125
Symmetry codes: (i) x-1, y, z; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iv) [-x+1, y, -z+{\script{3\over 2}}]; (v) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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

Benzimidazole-constituted compounds are known as bioactive heterocyclic compounds that are of wide interest for biological and clinical applications (Narasimhan et al., 2012). As a part of our ongoing studies in this area (Haque et al., 2012), we now describe the title compound.

All parameters in the title compound (Fig. 1) are within normal ranges. The complete molecule is generated by a crystallographic two-fold axis. The benzimidazole (N1—N2/C1—C7) ring is planar with the r.m.s 0.0207 Å. It makes a dihedral angle of 50.12 (2)° with its symmetrical component and 65.81 (2) Å with the central benzene ring (C9—C11/C9A—C11A). Four fluorine atoms (F1—F4) of the hexafluorophosphate cation are disordered over two positions with the final refined occupancies of 0.889 (6):0.111 (6).

In the crystal structure, (Fig. 2), the molecules are linked into a three-dimensional network through intermolecular C—H···F hydrogen bonds (Table 1). A π-π interaction with centroid-centroid distance of 3.530 (1) Å is observed (Cg1 = C2—C7).

Related literature top

For the biological applications of benzimidazoles, see: Narasimhan et al. (2012). For a related structure, see: Haque et al. (2012).

Experimental top

A mixture of benzimidazole (1.18 g, 10 mmol) and potassium hydroxide (1.18 g, 15 mmol) in 30 ml of DMSO was stirred at room temperature (27–28°C) for 30 min. Ethyl bromide (0.75 ml, 10 mmol) was added drop-wise into this consistently stirring mixture and it was further stirred for 2 h at same temperature, then poured into water (150 ml) and was extracted by chloroform (3 × 20 ml). The extract was filtered by five plies of filter papers with medium porosity to collect a crystal-clear solution which was evaporated under vacuum to get N-ethylbenzimidazole (I) as a thick yellowish fluid. Then, a mixture of I (0.73 g, 5 mmol) and 1,2- bis(bromomethyl)benzene (0.66 g, 2.5 mmol) in 1,4-dioxane (20 ml) was refluxed at 110°C for 12 h. The bromide salt of title compound appeared as beige-colored precipitates in a dark brown solution. The mixture was filtered and the precipitates were washed by fresh 1,4-dioxane (3 x 5 ml) and dried at room temperature for 24 h. The soft lumps so obtained were dissolved in methanol (30 ml) along with KPF6 (1.84 g, 10 mmol) and stirred for 3 h at room temperature. The white solid that appeared was filtered, washed by fresh methanol followed by water. The compound was dried at room temperature (1.53 g, 89.5%). A saturated solution of 2.2PF6 dissolved in acetonitrile (1 ml) was prepared. The compound was dissolved in it and the solution was evaporated at room temperature to collect colourless blocks of the title compound.

Refinement top

All H atoms attached to C atoms were fixed geometrically and refined as riding with C—H = 0.95–0.99 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C-methyl). A rotating group model was applied to the methyl group. Four fluorine atoms (F1—F4) of the hexafluorophosphate cation are disordered over two positions with the final refined occupancies of 0.889 (6):0.111 (6).The minor component was refined isotropically.

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, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal packing of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.
3,3'-[1,2-Phenylenebis(methylene)]bis(1-ethyl-1H-benzimidazol-1-ium) bis(hexaflourophosphate) top
Crystal data top
C26H28N42+·2PF6F(000) = 1400
Mr = 686.46Dx = 1.659 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3899 reflections
a = 23.2016 (5) Åθ = 2.5–29.7°
b = 8.1526 (2) ŵ = 0.27 mm1
c = 16.9992 (4) ÅT = 100 K
β = 121.274 (1)°Block, colourless
V = 2748.23 (11) Å30.26 × 0.26 × 0.14 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer
3921 independent reflections
Radiation source: fine-focus sealed tube3156 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ϕ and ω scansθmax = 29.8°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 3231
Tmin = 0.933, Tmax = 0.963k = 119
14787 measured reflectionsl = 2323
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0339P)2 + 4.2095P]
where P = (Fo2 + 2Fc2)/3
3921 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C26H28N42+·2PF6V = 2748.23 (11) Å3
Mr = 686.46Z = 4
Monoclinic, C2/cMo Kα radiation
a = 23.2016 (5) ŵ = 0.27 mm1
b = 8.1526 (2) ÅT = 100 K
c = 16.9992 (4) Å0.26 × 0.26 × 0.14 mm
β = 121.274 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3921 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3156 reflections with I > 2σ(I)
Tmin = 0.933, Tmax = 0.963Rint = 0.037
14787 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.05Δρmax = 0.48 e Å3
3921 reflectionsΔρmin = 0.35 e Å3
217 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)
P10.89811 (2)0.80829 (6)0.89390 (3)0.01579 (11)
F50.84112 (5)0.94532 (13)0.83897 (7)0.0220 (2)
F60.95467 (6)0.67136 (15)0.94831 (8)0.0323 (3)
F10.95400 (8)0.92423 (17)0.89472 (17)0.0309 (5)0.889 (6)
F20.91321 (10)0.8889 (2)0.98909 (10)0.0303 (5)0.889 (6)
F30.84260 (11)0.6929 (2)0.8940 (2)0.0311 (5)0.889 (6)
F40.88302 (12)0.7290 (2)0.79927 (10)0.0314 (5)0.889 (6)
F1A0.9350 (7)0.9043 (15)0.8457 (11)0.024 (3)*0.111 (6)
F2A0.9323 (8)0.9133 (18)0.9770 (10)0.032 (4)*0.111 (6)
F4A0.8573 (8)0.7032 (18)0.7950 (10)0.029 (3)*0.111 (6)
F3A0.8547 (9)0.713 (2)0.9237 (11)0.024 (4)*0.111 (6)
N10.16728 (7)0.66335 (17)1.09095 (9)0.0146 (3)
N20.10920 (7)0.67626 (18)0.94040 (9)0.0154 (3)
C10.10867 (8)0.7060 (2)1.01737 (11)0.0157 (3)
H1A0.07170.75131.01920.019*
C20.20844 (8)0.5997 (2)1.06084 (11)0.0142 (3)
C30.27289 (8)0.5312 (2)1.10913 (12)0.0174 (3)
H3A0.29820.52541.17440.021*
C40.29766 (9)0.4723 (2)1.05606 (13)0.0206 (4)
H4A0.34100.42261.08590.025*
C50.26085 (9)0.4833 (2)0.95923 (13)0.0212 (4)
H5A0.28020.44240.92570.025*
C60.19723 (9)0.5525 (2)0.91211 (12)0.0174 (3)
H6A0.17230.56100.84690.021*
C70.17168 (8)0.6091 (2)0.96517 (11)0.0150 (3)
C80.05184 (8)0.6967 (2)0.84619 (11)0.0163 (3)
H8A0.06630.76240.81050.020*
H8B0.01570.75820.84800.020*
C90.02370 (8)0.5336 (2)0.79767 (11)0.0151 (3)
C100.04406 (8)0.3851 (2)0.84445 (12)0.0178 (3)
H10A0.07400.38450.90930.021*
C110.02104 (9)0.2372 (2)0.79734 (12)0.0200 (4)
H11A0.03420.13640.83010.024*
C120.18631 (9)0.6741 (2)1.18835 (11)0.0186 (3)
H12A0.21760.76751.21790.022*
H12B0.21040.57271.22080.022*
C130.12542 (9)0.6968 (2)1.19816 (13)0.0212 (4)
H13A0.14020.70151.26360.032*
H13B0.09440.60441.16920.032*
H13C0.10240.79921.16810.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0129 (2)0.0162 (2)0.0174 (2)0.00054 (16)0.00725 (17)0.00099 (17)
F50.0197 (5)0.0208 (5)0.0221 (5)0.0054 (4)0.0084 (4)0.0053 (4)
F60.0233 (6)0.0279 (6)0.0390 (7)0.0116 (5)0.0115 (5)0.0080 (5)
F10.0212 (8)0.0261 (7)0.0505 (14)0.0047 (6)0.0224 (9)0.0001 (7)
F20.0303 (9)0.0381 (9)0.0169 (6)0.0070 (7)0.0083 (6)0.0039 (6)
F30.0263 (9)0.0207 (8)0.0519 (15)0.0042 (7)0.0244 (11)0.0045 (10)
F40.0382 (11)0.0331 (9)0.0228 (7)0.0058 (8)0.0157 (7)0.0062 (6)
N10.0127 (6)0.0161 (7)0.0134 (6)0.0006 (5)0.0056 (5)0.0010 (5)
N20.0112 (6)0.0185 (7)0.0137 (6)0.0007 (5)0.0044 (5)0.0010 (6)
C10.0122 (7)0.0179 (8)0.0151 (7)0.0008 (6)0.0057 (6)0.0011 (6)
C20.0126 (7)0.0133 (7)0.0157 (7)0.0015 (6)0.0067 (6)0.0014 (6)
C30.0132 (8)0.0175 (8)0.0175 (8)0.0002 (6)0.0051 (7)0.0007 (7)
C40.0131 (8)0.0216 (9)0.0238 (9)0.0034 (7)0.0074 (7)0.0021 (7)
C50.0198 (9)0.0219 (9)0.0268 (9)0.0000 (7)0.0155 (8)0.0023 (8)
C60.0168 (8)0.0189 (8)0.0161 (8)0.0025 (6)0.0082 (7)0.0023 (7)
C70.0112 (7)0.0142 (8)0.0165 (8)0.0017 (6)0.0050 (6)0.0009 (6)
C80.0117 (7)0.0202 (8)0.0114 (7)0.0004 (6)0.0022 (6)0.0006 (6)
C90.0102 (7)0.0201 (8)0.0143 (8)0.0008 (6)0.0059 (6)0.0009 (6)
C100.0117 (8)0.0235 (9)0.0147 (8)0.0010 (6)0.0045 (6)0.0018 (7)
C110.0146 (8)0.0191 (8)0.0227 (9)0.0014 (6)0.0072 (7)0.0042 (7)
C120.0193 (8)0.0216 (9)0.0121 (7)0.0021 (7)0.0062 (7)0.0011 (7)
C130.0260 (9)0.0195 (9)0.0227 (9)0.0017 (7)0.0158 (8)0.0017 (7)
Geometric parameters (Å, º) top
P1—F2A1.481 (14)C4—C51.410 (3)
P1—F3A1.552 (19)C4—H4A0.9500
P1—F41.5947 (14)C5—C61.382 (2)
P1—F31.5957 (18)C5—H5A0.9500
P1—F11.5987 (13)C6—C71.390 (2)
P1—F61.6011 (12)C6—H6A0.9500
P1—F21.6077 (15)C8—C91.522 (2)
P1—F51.6082 (11)C8—H8A0.9900
P1—F1A1.656 (11)C8—H8B0.9900
P1—F4A1.674 (14)C9—C101.390 (2)
N1—C11.330 (2)C9—C9i1.409 (3)
N1—C21.397 (2)C10—C111.391 (3)
N1—C121.478 (2)C10—H10A0.9500
N2—C11.337 (2)C11—C11i1.383 (3)
N2—C71.395 (2)C11—H11A0.9500
N2—C81.467 (2)C12—C131.518 (2)
C1—H1A0.9500C12—H12A0.9900
C2—C71.392 (2)C12—H12B0.9900
C2—C31.395 (2)C13—H13A0.9800
C3—C41.383 (2)C13—H13B0.9800
C3—H3A0.9500C13—H13C0.9800
F2A—P1—F3A95.5 (8)N1—C1—H1A124.8
F2A—P1—F4157.6 (7)N2—C1—H1A124.8
F3A—P1—F4106.7 (6)C7—C2—C3121.92 (15)
F2A—P1—F3111.9 (7)C7—C2—N1106.67 (14)
F4—P1—F390.44 (11)C3—C2—N1131.37 (15)
F2A—P1—F167.6 (7)C4—C3—C2115.88 (16)
F3A—P1—F1162.7 (6)C4—C3—H3A122.1
F4—P1—F190.05 (9)C2—C3—H3A122.1
F3—P1—F1179.50 (11)C3—C4—C5122.29 (16)
F2A—P1—F688.8 (6)C3—C4—H4A118.9
F3A—P1—F686.5 (7)C5—C4—H4A118.9
F4—P1—F689.14 (8)C6—C5—C4121.35 (16)
F3—P1—F690.47 (9)C6—C5—H5A119.3
F1—P1—F689.39 (7)C4—C5—H5A119.3
F3A—P1—F273.4 (6)C5—C6—C7116.48 (16)
F4—P1—F2179.76 (10)C5—C6—H6A121.8
F3—P1—F289.66 (11)C7—C6—H6A121.8
F1—P1—F289.86 (9)C6—C7—C2122.06 (15)
F6—P1—F291.07 (7)C6—C7—N2131.37 (16)
F2A—P1—F591.4 (6)C2—C7—N2106.53 (14)
F3A—P1—F593.4 (7)N2—C8—C9112.54 (14)
F4—P1—F590.69 (7)N2—C8—H8A109.1
F3—P1—F589.39 (9)C9—C8—H8A109.1
F1—P1—F590.75 (7)N2—C8—H8B109.1
F6—P1—F5179.78 (9)C9—C8—H8B109.1
F2—P1—F589.10 (7)H8A—C8—H8B107.8
F2A—P1—F1A92.3 (7)C10—C9—C9i119.25 (10)
F3A—P1—F1A171.2 (7)C10—C9—C8121.89 (14)
F4—P1—F1A65.9 (5)C9i—C9—C8118.85 (9)
F3—P1—F1A154.6 (5)C9—C10—C11120.70 (15)
F6—P1—F1A97.8 (4)C9—C10—H10A119.6
F2—P1—F1A114.0 (5)C11—C10—H10A119.7
F5—P1—F1A82.2 (4)C11i—C11—C10119.87 (10)
F2A—P1—F4A175.5 (8)C11i—C11—H11A120.1
F3A—P1—F4A86.9 (7)C10—C11—H11A120.1
F3—P1—F4A70.3 (5)N1—C12—C13112.13 (14)
F1—P1—F4A110.2 (5)N1—C12—H12A109.2
F6—P1—F4A95.2 (5)C13—C12—H12A109.2
F2—P1—F4A159.0 (6)N1—C12—H12B109.2
F5—P1—F4A84.6 (5)C13—C12—H12B109.2
F1A—P1—F4A85.1 (6)H12A—C12—H12B107.9
C1—N1—C2108.21 (13)C12—C13—H13A109.5
C1—N1—C12127.07 (14)C12—C13—H13B109.5
C2—N1—C12124.68 (14)H13A—C13—H13B109.5
C1—N2—C7108.18 (14)C12—C13—H13C109.5
C1—N2—C8125.72 (14)H13A—C13—H13C109.5
C7—N2—C8125.88 (14)H13B—C13—H13C109.5
N1—C1—N2110.39 (14)
C2—N1—C1—N20.89 (19)N1—C2—C7—C6178.67 (15)
C12—N1—C1—N2178.83 (15)C3—C2—C7—N2177.24 (15)
C7—N2—C1—N10.45 (19)N1—C2—C7—N20.69 (18)
C8—N2—C1—N1175.33 (15)C1—N2—C7—C6177.89 (18)
C1—N1—C2—C70.97 (18)C8—N2—C7—C63.0 (3)
C12—N1—C2—C7178.98 (15)C1—N2—C7—C20.18 (18)
C1—N1—C2—C3176.69 (18)C8—N2—C7—C2174.70 (15)
C12—N1—C2—C31.3 (3)C1—N2—C8—C9109.15 (18)
C7—C2—C3—C40.5 (2)C7—N2—C8—C964.8 (2)
N1—C2—C3—C4176.88 (17)N2—C8—C9—C109.8 (2)
C2—C3—C4—C51.2 (3)N2—C8—C9—C9i169.32 (17)
C3—C4—C5—C60.8 (3)C9i—C9—C10—C113.6 (3)
C4—C5—C6—C70.4 (3)C8—C9—C10—C11175.57 (16)
C5—C6—C7—C21.2 (3)C9—C10—C11—C11i1.8 (3)
C5—C6—C7—N2176.25 (17)C1—N1—C12—C1315.8 (2)
C3—C2—C7—C60.7 (3)C2—N1—C12—C13161.87 (15)
Symmetry code: (i) x, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···F6ii0.952.423.142 (3)133
C3—H3A···F5iii0.952.453.374 (2)166
C5—H5A···F5iv0.952.523.420 (3)159
C6—H6A···F4v0.952.533.392 (2)151
C8—H8B···F1ii0.992.393.350 (3)164
C13—H13C···F1vi0.982.553.523 (2)174
C13—H13C···F5vi0.982.503.166 (2)125
Symmetry codes: (ii) x1, y, z; (iii) x1/2, y+3/2, z+1/2; (iv) x1/2, y1/2, z; (v) x+1, y, z+3/2; (vi) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC26H28N42+·2PF6
Mr686.46
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)23.2016 (5), 8.1526 (2), 16.9992 (4)
β (°) 121.274 (1)
V3)2748.23 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.26 × 0.26 × 0.14
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.933, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
14787, 3921, 3156
Rint0.037
(sin θ/λ)max1)0.700
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.098, 1.05
No. of reflections3921
No. of parameters217
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.35

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···F6i0.952.423.142 (3)133
C3—H3A···F5ii0.952.453.374 (2)166
C5—H5A···F5iii0.952.523.420 (3)159
C6—H6A···F4iv0.952.533.392 (2)151
C8—H8B···F1i0.992.393.350 (3)164
C13—H13C···F1v0.982.553.523 (2)174
C13—H13C···F5v0.982.503.166 (2)125
Symmetry codes: (i) x1, y, z; (ii) x1/2, y+3/2, z+1/2; (iii) x1/2, y1/2, z; (iv) x+1, y, z+3/2; (v) x+1, y+2, z+2.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

RAH thanks Universiti Sains Malaysia (USM) for the Research University (RU) grants (1001/PKIMIA/811157 and 304/PKIMIA/6511123). MAI is grateful to (IPS) USM for financial support [fellowship: USM·IPS/JWT/1/19 (JLD 6)] and the research attachment fund [P-KM0018/10(R) − 308/AIPS/415401]. HKF thanks USM for the Research University Grant No. 1001/PFIZIK/811160.

References

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHaque, R. A., Iqbal, M. A., Fun, H.-K. & Arshad, S. (2012). Acta Cryst. E68, o924–o925.  CSD CrossRef IUCr Journals
First citationNarasimhan, B., Sharma, D. & Kumar, P. (2012). Med. Chem. Res. 21, 269–283.  Web of Science CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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