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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 67| Part 6| June 2011| Pages o1292-o1293

3,5-Bis(4-fluoro­phen­yl)-4,5-di­hydro-1H-pyrazole-1-carbaldehyde

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 17 April 2011; accepted 26 April 2011; online 7 May 2011)

In the title mol­ecule, C16H12F2N2O, the pyrazole ring adopts a slight envelope conformation with the methyl­ene C atom deviating by 0.114 (3) Å from the mean plane of the other four atoms [maximum deviation = 0.021 (3) Å]. The dihedral angles between the four essentially planar atoms of the pyrazole ring and the fluoro-substituted benzene rings are 2.6 (2) and 82.2 (2)°. The dihedral angle between the two benzene rings is 83.7 (2)°. The crystal packing is stabilized by weak inter­molecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of pyrazolines, see: Hes et al. (1978[Hes, R. V., Wellinga, K. & Grosscurt, A. C. (1978). J. Agric. Food Chem. 26, 915-918.]); Manna et al. (2005[Manna, F., Chimenti, F., Fioravanti, R., Bolasco, A., Secci, D., Chimenti, P., Ferlini, C. & Scambia, G. (2005). Bioorg. Med. Chem. Lett. 15, 4632-4635.]); Amir et al. (2008[Amir, M., Kumar, H. & Khan, S. A. (2008). Bioorg. Med. Chem. Lett. 18, 918-922.]); Regaila et al. (1979[Regaila, H. A., El-Bayonk, A. K. & Hammad, M. (1979). Egypt. J. Chem. 20, 197-202.]); Sarojini et al. (2010[Sarojini, B. K., Vidyagayatri, M., Darshanraj, C. G., Bharath, B. R. & Manjunatha, H. (2010). Lett. Drug Des. Discov. 7, 214-224.]). For their importance in organic synthesis, see: Bhaskarreddy et al. (1997[Bhaskarreddy, D., Chandrasekhar, B. N., Padmavathi, V. & Sumathi, R. P. (1997). Synthesis, pp. 491-494.]); Klimova et al. (1999[Klimova, E. I., Marcos, M., Klimova, T. B., Cecilio, A. T., Ruben, A. T. & Lena, R. R. (1999). J. Organomet. Chem. 585, 106-111.]). For related structures, see: Butcher et al. (2007[Butcher, R. J., Jasinski, J. P., Prasad, D. J., Narayana, B. & Yathirajan, H. S. (2007). Acta Cryst. E63, o4005-o4006.]); Cui & Li (2010[Cui, P. & Li, X.-L. (2010). Acta Cryst. E66, o2351.]); Fun et al. (2010a[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o582-o583.],b[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o864-o865.]); Jasinski et al. (2010a[Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o1948-o1949.],b[Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o2018.]); Baktır et al. (2011[Baktır, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o328-o329.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12F2N2O

  • Mr = 286.28

  • Triclinic, [P \overline 1]

  • a = 6.2141 (9) Å

  • b = 6.7802 (8) Å

  • c = 17.9857 (9) Å

  • α = 96.727 (4)°

  • β = 90.254 (4)°

  • γ = 116.791 (5)°

  • V = 670.39 (13) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 294 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.968, Tmax = 0.989

  • 14070 measured reflections

  • 2736 independent reflections

  • 1011 reflections with I > 2σ(I)

  • Rint = 0.095

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.206

  • S = 0.94

  • 2736 reflections

  • 191 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯O1i 0.93 2.50 3.421 (5) 171
C11—H11⋯O1ii 0.93 2.39 3.296 (5) 165
Symmetry codes: (i) x-2, y-1, z; (ii) x-1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Pyrazolines have been reported to exhibit a broad spectrum of biological activies such as antitumor, antibacterial, antifungal, antiviral, antiparasitic, anti-tubercular and insecticidal activities (Hes et al., 1978; Manna et al., 2005; Amir et al., 2008). Some of these compounds have also antioxidant, anti-diabetic, anaesthetic and analgesic properties (Sarojini et al., 2010; Regaila et al., 1979). In addition, pyrazolines have played a crucial part in the development of theory in heterocyclic chemistry and also used extensively in organic synthesis (Klimova et al., 1999 and Bhaskarreddy et al., 1997).

The crystal structure of some pyrazoline derivatives viz., 3-(4-methylphenyl)-5-[4-(methylthio)phenyl]-4,5-dihydro-1H-pyrazole-1-carbaldehyde (Butcher et al., 2007) and 5-(2-hydroxyphenyl)-3-methyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde (Cui & Li, 2010) have been reported. In view of the importance of pyrazoline derivatives and in continuation of our work on synthesis of various derivatives of 4,4'-diflouro chalcone (Fun et al., 2010a,b; Jasinski et al., 2010a,b; Baktır et al., 2011), the title compound (I) is synthesized and its crystal structure is reported herein.

The molecular structure of the title compound is shown in Fig. 1. The pyrazole ring adopts a slight envelope comformation with the methylene C atom (C8) deviating by 0.114 (3)Å from the mean-plane of the other four atoms (C7/C9/N1/N2 with maximum deviation 0.021 (3)Å for N1). The dihedral angles between the four essentially planar atoms of the pyrazole ring and fluoro-substituted benzene rings are 2.6 (2) and 82.2 (2)°, respectively. The dihedral angle between the two benzene rings is 83.7 (2)°. The crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds (Fig .2).

Related literature top

For the biological activity of pyrazolines, see: Hes et al. (1978); Manna et al. (2005); Amir et al. (2008); Regaila et al. (1979); Sarojini et al. (2010). For their importance in organic synthesis, see: Bhaskarreddy et al. (1997); Klimova et al. (1999). For related structures, see: Butcher et al. (2007); Cui & Li (2010); Fun et al. (2010a,b); Jasinski et al. (2010a,b); Baktır et al. (2011).

Experimental top

A mixture of (2E)-1,3-bis(4-fluorophenyl)prop-2-en-1-one (2.44 g, 0.01 mol) and hydrazine hydrate (0.5 ml, 0.01 mol) in 20 ml formic acid was refluxed for 8 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from DMF by slow evaporation method and yield of the compound was 86%. (m. p.: 408 K).

Refinement top

All H atoms were positioned geometrically [C—H = 0.93 and 0.97 Å] and allowed to ride on their parent C atoms, with Uiso(H) = 1.2Ueq(C). Owing to the large number of weak high-angle reflections, the ratio of observed to unique reflections is low (37%).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The title molecule with displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. Hydrogen bonding of the title compound viewed along the a axis. Hydrogen bonds are shown as dotted lines (symmetry code: (a) x-2, y-1, z).
3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde top
Crystal data top
C16H12F2N2OZ = 2
Mr = 286.28F(000) = 296
Triclinic, P1Dx = 1.418 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2141 (9) ÅCell parameters from 1748 reflections
b = 6.7802 (8) Åθ = 2.3–26.3°
c = 17.9857 (9) ŵ = 0.11 mm1
α = 96.727 (4)°T = 294 K
β = 90.254 (4)°Prism, pale yellow
γ = 116.791 (5)°0.30 × 0.20 × 0.10 mm
V = 670.39 (13) Å3
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
2736 independent reflections
Radiation source: Sealed Tube1011 reflections with I > 2σ(I)
Graphite Monochromator monochromatorRint = 0.095
Detector resolution: 10.0000 pixels mm-1θmax = 26.5°, θmin = 3.4°
dtprofit.ref scansh = 77
Absorption correction: multi-scan
(Blessing, 1995)
k = 88
Tmin = 0.968, Tmax = 0.989l = 2222
14070 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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0812P)2]
where P = (Fo2 + 2Fc2)/3
2736 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C16H12F2N2Oγ = 116.791 (5)°
Mr = 286.28V = 670.39 (13) Å3
Triclinic, P1Z = 2
a = 6.2141 (9) ÅMo Kα radiation
b = 6.7802 (8) ŵ = 0.11 mm1
c = 17.9857 (9) ÅT = 294 K
α = 96.727 (4)°0.30 × 0.20 × 0.10 mm
β = 90.254 (4)°
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
2736 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
1011 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.989Rint = 0.095
14070 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.206H-atom parameters constrained
S = 0.94Δρmax = 0.19 e Å3
2736 reflectionsΔρmin = 0.33 e Å3
191 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
F10.7910 (4)0.0976 (4)0.04914 (14)0.1334 (11)
F20.7113 (5)1.4342 (4)0.49400 (14)0.1284 (11)
O10.9124 (4)0.8903 (4)0.23729 (12)0.0822 (9)
N10.3094 (4)0.6264 (4)0.16479 (13)0.0621 (9)
N20.5069 (4)0.7082 (4)0.21640 (12)0.0621 (9)
C10.1494 (6)0.4185 (7)0.08534 (18)0.1019 (16)
C20.3750 (7)0.3162 (8)0.0481 (2)0.120 (2)
C30.5702 (6)0.1944 (7)0.0858 (2)0.0937 (16)
C40.5512 (6)0.1715 (5)0.1584 (2)0.0798 (14)
C50.3241 (6)0.2737 (5)0.19570 (18)0.0718 (12)
C60.1199 (5)0.3980 (5)0.15912 (16)0.0643 (11)
C70.1190 (5)0.5070 (5)0.19872 (15)0.0583 (11)
C80.1722 (5)0.4922 (5)0.27855 (16)0.0728 (12)
C90.4427 (5)0.6519 (5)0.29283 (15)0.0650 (11)
C100.5095 (5)0.8590 (5)0.34783 (15)0.0637 (11)
C110.3760 (6)0.9769 (6)0.34948 (17)0.0713 (11)
C120.4417 (7)1.1706 (6)0.39825 (19)0.0820 (16)
C130.6424 (7)1.2450 (6)0.4449 (2)0.0873 (16)
C140.7786 (7)1.1343 (6)0.44657 (19)0.0870 (14)
C150.7124 (6)0.9408 (6)0.39679 (17)0.0774 (14)
C160.7313 (6)0.8185 (5)0.19475 (18)0.0696 (12)
H10.015200.502700.060000.1230*
H20.393300.330400.002100.1440*
H40.687600.088700.183100.0960*
H50.308400.258800.245900.0860*
H8A0.138800.341400.285100.0870*
H8B0.077400.539400.312100.0870*
H90.527400.570500.308700.0780*
H110.239200.924300.317000.0850*
H120.350501.248200.399100.0990*
H140.912701.187200.480200.1040*
H150.805400.865000.396300.0930*
H160.750900.841900.144800.0830*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0603 (14)0.164 (2)0.142 (2)0.0304 (15)0.0376 (13)0.0172 (17)
F20.1089 (18)0.1004 (17)0.133 (2)0.0232 (15)0.0018 (15)0.0407 (15)
O10.0474 (13)0.0936 (18)0.0902 (17)0.0222 (13)0.0112 (12)0.0025 (13)
N10.0507 (15)0.0728 (18)0.0553 (14)0.0242 (14)0.0057 (12)0.0030 (12)
N20.0451 (15)0.0734 (18)0.0576 (14)0.0203 (14)0.0060 (11)0.0010 (12)
C10.059 (2)0.159 (4)0.061 (2)0.027 (2)0.0034 (17)0.011 (2)
C20.070 (3)0.187 (5)0.074 (2)0.037 (3)0.015 (2)0.001 (3)
C30.052 (2)0.105 (3)0.107 (3)0.028 (2)0.022 (2)0.016 (2)
C40.051 (2)0.072 (2)0.104 (3)0.0191 (18)0.0005 (18)0.004 (2)
C50.059 (2)0.069 (2)0.080 (2)0.0242 (18)0.0004 (17)0.0038 (17)
C60.053 (2)0.075 (2)0.0613 (18)0.0286 (18)0.0030 (14)0.0025 (15)
C70.0502 (19)0.066 (2)0.0554 (17)0.0254 (16)0.0004 (14)0.0000 (14)
C80.063 (2)0.074 (2)0.068 (2)0.0199 (18)0.0071 (15)0.0074 (16)
C90.061 (2)0.070 (2)0.0583 (17)0.0253 (17)0.0090 (14)0.0073 (15)
C100.0568 (19)0.072 (2)0.0541 (17)0.0232 (17)0.0080 (14)0.0042 (15)
C110.065 (2)0.084 (2)0.0618 (18)0.032 (2)0.0040 (15)0.0066 (17)
C120.085 (3)0.086 (3)0.075 (2)0.040 (2)0.0065 (19)0.0061 (19)
C130.082 (3)0.077 (3)0.080 (2)0.022 (2)0.002 (2)0.0147 (19)
C140.069 (2)0.095 (3)0.078 (2)0.026 (2)0.0154 (18)0.011 (2)
C150.064 (2)0.091 (3)0.066 (2)0.029 (2)0.0137 (16)0.0044 (18)
C160.050 (2)0.081 (2)0.072 (2)0.0268 (18)0.0002 (16)0.0009 (17)
Geometric parameters (Å, º) top
F1—C31.352 (5)C10—C151.385 (5)
F2—C131.358 (4)C11—C121.380 (5)
O1—C161.225 (4)C12—C131.356 (6)
N1—N21.390 (4)C13—C141.363 (6)
N1—C71.299 (4)C14—C151.388 (5)
N2—C91.478 (4)C1—H10.9300
N2—C161.337 (5)C2—H20.9300
C1—C21.379 (6)C4—H40.9300
C1—C61.370 (4)C5—H50.9300
C2—C31.360 (6)C8—H8A0.9700
C3—C41.344 (5)C8—H8B0.9700
C4—C51.387 (5)C9—H90.9800
C5—C61.388 (5)C11—H110.9300
C6—C71.461 (5)C12—H120.9300
C7—C81.497 (4)C14—H140.9300
C8—C91.534 (5)C15—H150.9300
C9—C101.506 (4)C16—H160.9300
C10—C111.386 (5)
N2—N1—C7107.5 (2)C13—C14—C15118.4 (4)
N1—N2—C9113.9 (2)C10—C15—C14120.9 (4)
N1—N2—C16120.5 (2)O1—C16—N2123.4 (3)
C9—N2—C16125.6 (3)C2—C1—H1119.00
C2—C1—C6121.0 (4)C6—C1—H1119.00
C1—C2—C3119.0 (3)C1—C2—H2120.00
F1—C3—C2118.6 (3)C3—C2—H2121.00
F1—C3—C4119.2 (4)C3—C4—H4121.00
C2—C3—C4122.2 (4)C5—C4—H4121.00
C3—C4—C5118.7 (3)C4—C5—H5120.00
C4—C5—C6120.9 (3)C6—C5—H5120.00
C1—C6—C5118.1 (3)C7—C8—H8A111.00
C1—C6—C7121.1 (3)C7—C8—H8B111.00
C5—C6—C7120.8 (3)C9—C8—H8A111.00
N1—C7—C6120.7 (3)C9—C8—H8B111.00
N1—C7—C8113.8 (3)H8A—C8—H8B109.00
C6—C7—C8125.5 (3)N2—C9—H9109.00
C7—C8—C9103.6 (2)C8—C9—H9109.00
N2—C9—C8100.7 (2)C10—C9—H9109.00
N2—C9—C10111.1 (2)C10—C11—H11119.00
C8—C9—C10116.5 (3)C12—C11—H11119.00
C9—C10—C11121.5 (3)C11—C12—H12121.00
C9—C10—C15120.4 (3)C13—C12—H12121.00
C11—C10—C15118.1 (3)C13—C14—H14121.00
C10—C11—C12121.4 (4)C15—C14—H14121.00
C11—C12—C13118.4 (4)C10—C15—H15120.00
F2—C13—C12119.9 (4)C14—C15—H15120.00
F2—C13—C14117.3 (4)O1—C16—H16118.00
C12—C13—C14122.8 (4)N2—C16—H16118.00
C7—N1—N2—C94.2 (3)C5—C6—C7—N1178.8 (3)
C7—N1—N2—C16173.1 (3)C5—C6—C7—C82.3 (5)
N2—N1—C7—C81.3 (4)C1—C6—C7—N10.1 (5)
N2—N1—C7—C6179.7 (3)C6—C7—C8—C9175.2 (3)
C16—N2—C9—C1066.3 (4)N1—C7—C8—C95.9 (4)
C16—N2—C9—C8169.7 (3)C7—C8—C9—N27.3 (3)
C9—N2—C16—O11.5 (5)C7—C8—C9—C10112.8 (3)
N1—N2—C9—C87.4 (3)C8—C9—C10—C1140.0 (4)
N1—N2—C9—C10116.5 (3)C8—C9—C10—C15142.1 (3)
N1—N2—C16—O1178.4 (3)N2—C9—C10—C15103.5 (3)
C2—C1—C6—C7179.8 (4)N2—C9—C10—C1174.4 (4)
C6—C1—C2—C30.3 (7)C9—C10—C15—C14178.6 (3)
C2—C1—C6—C50.9 (6)C9—C10—C11—C12177.9 (3)
C1—C2—C3—C40.5 (7)C15—C10—C11—C120.0 (5)
C1—C2—C3—F1179.0 (4)C11—C10—C15—C140.6 (5)
F1—C3—C4—C5179.3 (3)C10—C11—C12—C130.3 (5)
C2—C3—C4—C50.8 (6)C11—C12—C13—C141.3 (6)
C3—C4—C5—C60.2 (5)C11—C12—C13—F2179.5 (3)
C4—C5—C6—C10.6 (5)F2—C13—C14—C15179.8 (3)
C4—C5—C6—C7179.5 (3)C12—C13—C14—C151.9 (6)
C1—C6—C7—C8178.8 (3)C13—C14—C15—C101.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.932.503.421 (5)171
C11—H11···O1ii0.932.393.296 (5)165
Symmetry codes: (i) x2, y1, z; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC16H12F2N2O
Mr286.28
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)6.2141 (9), 6.7802 (8), 17.9857 (9)
α, β, γ (°)96.727 (4), 90.254 (4), 116.791 (5)
V3)670.39 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID-S
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.968, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
14070, 2736, 1011
Rint0.095
(sin θ/λ)max1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.206, 0.94
No. of reflections2736
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.33

Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.932.503.421 (5)171
C11—H11···O1ii0.932.393.296 (5)165
Symmetry codes: (i) x2, y1, z; (ii) x1, y, z.
 

Acknowledgements

ZB and MA thank the Unit of the Scientific Research Projects of Erciyes University, Turkey, for the research grant FBD-10–2949, and for support of the data collection at Atatürk University, Turkey. SS and BN thank Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. HSY thanks the UOM for sabbatical leave.

References

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Volume 67| Part 6| June 2011| Pages o1292-o1293
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