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ISSN: 2414-3146

(E)-4-Meth­­oxy-N′-(2,4,5-tri­fluoro­benzyl­­idene)benzohydrazide monohydrate

aDepartment of Chemistry, Saranathan College of Engineering, Tiruchirappalli, Tamilnadu, India, bPG and Research Department of Chemistry, Periyar EVR College, Tiruchirappalli, Tamilnadu, India, and cDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203, Tamil Nadu, India
*Correspondence e-mail: swaroopapranav@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 May 2016; accepted 25 May 2016; online 27 May 2016)

The title Schiff base compound, C15H11F3N2O2·H2O, crystallized as a monohydrate. The conformation about the C=N bond is E. The mol­ecule is almost planar, with the dihedral angle between the planes of the meth­oxy­benzene and tri­fluoro­benzyl­idene rings being 7.46 (6)°. In the crystal, mol­ecules are linked by bifurcated Owater—H⋯(O,N) hydrogen bonds and N—H⋯Owater and Owater—H⋯O and C—H⋯O hydrogen bonds, forming chains along [100]. The chains are linked by C—H⋯Owater hydrogen bonds, forming slabs parallel to the bc plane. Within the slabs there are offset ππ inter­actions present [inter­centroid distance = 3.7883 (7) Å].

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Benzohydrazide Schiff base compounds exhibit a wide range of biological activities and act as a promising lead compounds for the design of more efficient drugs (Negi et al., 2012[Negi, V. J., Sharma, A. K., Negi, J. S. & Ra, V. (2012). Int. J. Pharm. Chem. 4, 100-109.]). Recently, benzohydrazones have attracted attention due to their versatile applications in various fields such as biology (Ibrahim et al., 2016[Ibrahim, H. S., Abou-seri, S. M., Ismail, N. S. M., Elaasser, M. M., Aly, M. H. & Abdel-Aziz, H. A. (2016). Eur. J. Med. Chem. 108, 415-422.]), medicine (Velezheva et al., 2016[Velezheva, V., Brennan, P., Ivanov, P., Kornienko, A., Lyubimov, S., Kazarian, K., Nikonenko, B., Majorov, K. & Apt, A. (2016). Bioorg. Med. Chem. Lett. 26, 978-985.]) and catalysis (Selvamurugan et al., 2016[Selvamurugan, S., Ramachandran, R., Prakash, G., Viswanathamurthi, P., Malecki, J. G. & Endo, A. (2016). J. Organomet. Chem. 803, 119-127.]). These derivatives also exhibit anti­microbial (Pieczonka et al., 2013[Pieczonka, A. M., Strzelczyk, A., Sadowska, B., Mloston, G. & Staczek, P. (2013). J. Organomet. Chem. 64, 389-395.]), anti-proliferative (Yadagiri et al., 2014[Yadagiri, B., Holagunda, U. D., Bantu, R., Nagarapu, L., Guguloth, V., Polepally, S. & Jain, N. (2014). Bioorg. Med. Chem. Lett. 24, 5041-5044.]) and anti­platelet (Mashayekhi et al., 2013[Mashayekhi, V., Haj Mohammad Ebrahim Tehrani, K., Amidi, S. & Kobarfard, F. (2013). Chem. Pharm. Bull. 61, 144-150.]) activities.

The geometric parameters of the title mol­ecule (Fig. 1[link]) agree well with those reported for similar structures (Maheswari et al., 2016[Maheswari, R., Manjula, J. & Gunasekaran, B. (2016). IUCrData, 1, x160304-x160305.]; Nair et al., 2012[Nair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709.]). The conformation about the C7=N1 bond is E. The dihedral angle between meth­oxy­phenyl ring and tri­fluoro­benzyl­idene ring is 7.46 (6)°.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The bifurcated Owater—H⋯(O,N) hydrogen bonds are shown as dashed lines (see Table 1[link]).

In the crystal, mol­ecules are linked by bifurcated Owater—H⋯(O,N) hydrogen bonds and N—H⋯Owater and Owater—H⋯O and C—H⋯O hydrogen bonds, forming chains along [100]; see Table 1[link] and Fig. 2[link]. The chains are linked by C—H⋯Owater hydrogen bonds, forming slabs parallel to the bc plane (Table 1[link] and Fig. 3[link]). Within the slabs, there are offset ππ inter­actions present [Cg1⋯Cg2i = 3. 7883 (3) Å,, inter­planar distance = 3.5156 (6) Å, slippage = 1.746 Å; Cg1 and Cg2 are the centroids of rings C1–C6 and C9–C14, respectively; symmetry code: (i) − x + 1, − y − 1, − z + 1].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1WA⋯O1 0.85 (2) 2.05 (2) 2.8376 (13) 154 (2)
O1W—H1WA⋯N1 0.85 (2) 2.61 (2) 3.2777 (14) 137 (2)
N2—H2⋯O1Wi 0.86 2.12 2.8681 (14) 145
O1W—H1WB⋯O1ii 0.86 (2) 2.01 (2) 2.8635 (16) 170 (2)
C5—H5⋯O2iii 0.93 2.49 3.4128 (15) 172
C7—H7⋯O1Wi 0.93 2.54 3.2191 (15) 130
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y-1, -z+1; (iii) x, y-1, z+1.
[Figure 2]
Figure 2
A partial view along the c axis of the crystal packing of the title compound. The hydrogen bonds (see Table 1[link]) are shown as dashed lines and, for clarity, only the H atoms involved in these inter­actions are included.
[Figure 3]
Figure 3
A view along the a axis of the crystal packing of the title compound. The hydrogen bonds (see Table 1[link]) are shown as dashed lines and, for clarity, only the H atoms involved in these inter­actions are included.

Synthesis and crystallization

To mixture of 4-meth­oxy­benzohydrazide (1.6 g, 0.01 mol) and 2,4,5-tri­fluoro­benzaldehyde (1.6 ml, 0.01 mol) in ethanol (10 ml) were added a few drops of concentrated HCl. The reaction mixture was stirred for 30 min at room temperature. The insoluble solid that gradually formed was filtered and washed with petroleum ether and dried in a vacuum desiccator. The crude solid was recrystallized from DMSO solution, giving colourless block-like crystals (yield 96%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C15H11F3N2O2·H2O
Mr 326.27
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 296
a, b, c (Å) 6.6872 (2), 7.9309 (2), 13.9723 (4)
α, β, γ (°) 82.348 (2), 84.783 (1), 88.710 (1)
V3) 731.35 (4)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.13
Crystal size (mm) 0.19 × 0.16 × 0.11
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.976, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections 10841, 3036, 2559
Rint 0.023
(sin θ/λ)max−1) 0.629
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.111, 1.04
No. of reflections 3036
No. of parameters 218
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.16, −0.20
Computer programs: APEX2 and SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data


Experimental top

To mixture of 4-methoxybenzohydrazide (1.6 g, 0.01 mol) and 2,4,5-trifluorobenzaldehyde (1.6 ml, 0.01 mol) in ethanol (? ml) were added a few drops of concentrated HCl. The reaction mixture was stirred for 30 min at room temperature. The insoluble solid that gradually formed was filtered and washed with petroleum ether and dried in a vacuum desiccator. The crude solid was recrystallized from DMSO, giving colourless block-like crystals (yield 96%).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2.

Structure description top

Benzohydrazide Schiff base compounds exhibit a wide range of biological activities and act as a promising lead compounds for the design of more efficient drugs (Negi et al., 2012). Recently, benzohydrazones have attracted attention due to their versatile applications in various fields such as biology (Ibrahim et al., 2016), medicine (Velezheva et al., 2016) and catalysis (Selvamurugan et al., 2016). These derivatives also exhibit antimicrobial (Pieczonka et al., 2013), anti-proliferative (Yadagiri et al., 2014) and antiplatelet (Mashayekhi et al., 2013) activities.

The geometric parameters of the title molecule (Fig. 1) agree well with those reported for similar structures (Maheswari et al., 2016; Nair et al., 2012). The conformation about the C7N1 bond is E. The dihedral angle between methoxyphenyl ring and trifluorobenzylidene ring is 7.46 (6)°.

In the crystal, molecules are linked by bifurcated Owater—H···(O,N) hydrogen bonds and N—H···Owater and Owater—H···O and C—H···O hydrogen bonds, forming chains along [100]; see Table 1 and Fig. 2. The chains are linked by C—H···Owater hydrogen bonds, forming slabs parallel to the bc plane (Table 1 and Fig. 3). Within the slabs, there are offset ππ interactions present [Cg1···Cg2i = 3. 7883 (3) Å, , interplanar distance = 3.5156 (6) Å, slippage = 1.746 Å; Cg1 and Cg2 are the centroids of rings C1–C6 and C9–C14, respectively; symmetry code: (i) - x + 1, - y - 1, - z + 1].

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The bifurcated Owater—H···(O,N) hydrogen bonds are shown as dashed lines (see Table 1).
[Figure 2] Fig. 2. A partial view along the c axis of the crystal packing of the title compound. The hydrogen bonds (see Table 1) are shown as dashed lines and, for clarity, only the H atoms involved in these interactions are included.
[Figure 3] Fig. 3. A view along the a axis of the crystal packing of the title compound. The hydrogen bonds (see Table 1) are shown as dashed lines and, for clarity, only the H atoms involved in these interactions are included.
(E)-4-Methoxy-N'-(2,4,5-trifluorobenzylidene)benzohydrazide monohydrate top
Crystal data top
C15H11F3N2O2·H2OZ = 2
Mr = 326.27F(000) = 336
Triclinic, P1Dx = 1.482 Mg m3
a = 6.6872 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.9309 (2) ÅCell parameters from 3036 reflections
c = 13.9723 (4) Åθ = 1.5–26.6°
α = 82.348 (2)°µ = 0.13 mm1
β = 84.783 (1)°T = 296 K
γ = 88.710 (1)°Block, colourless
V = 731.35 (4) Å30.19 × 0.16 × 0.11 mm
Data collection top
Bruker APEXII CCD
diffractometer
3036 independent reflections
Radiation source: fine-focus sealed tube2559 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 0 pixels mm-1θmax = 26.6°, θmin = 1.5°
ω and φ scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
k = 99
Tmin = 0.976, Tmax = 0.986l = 1716
10841 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1124P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3036 reflectionsΔρmax = 0.16 e Å3
218 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.105 (7)
Crystal data top
C15H11F3N2O2·H2Oγ = 88.710 (1)°
Mr = 326.27V = 731.35 (4) Å3
Triclinic, P1Z = 2
a = 6.6872 (2) ÅMo Kα radiation
b = 7.9309 (2) ŵ = 0.13 mm1
c = 13.9723 (4) ÅT = 296 K
α = 82.348 (2)°0.19 × 0.16 × 0.11 mm
β = 84.783 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
3036 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
2559 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.986Rint = 0.023
10841 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.16 e Å3
3036 reflectionsΔρmin = 0.20 e Å3
218 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.27163 (14)0.17533 (13)0.17677 (6)0.0534 (3)
C150.0702 (2)0.23667 (19)0.18294 (11)0.0595 (4)
H15A0.02000.14250.18980.089*
H15B0.04780.31190.12510.089*
H15C0.04670.29710.23810.089*
O1W1.07816 (14)0.40072 (17)0.59527 (7)0.0567 (3)
C90.50245 (16)0.14171 (14)0.40181 (8)0.0360 (3)
N20.49491 (14)0.31489 (12)0.55853 (7)0.0406 (2)
H20.36840.29270.56570.049*
C80.60665 (17)0.25169 (14)0.47707 (8)0.0383 (3)
N10.58713 (15)0.41549 (12)0.62992 (7)0.0412 (3)
C20.75138 (18)0.64277 (15)0.77805 (8)0.0428 (3)
H2A0.83150.61990.71990.051*
C120.33642 (18)0.07140 (15)0.25356 (8)0.0394 (3)
C10.56035 (18)0.56972 (15)0.78779 (8)0.0401 (3)
C140.30309 (17)0.08984 (16)0.41155 (8)0.0415 (3)
H140.22400.12720.46830.050*
C130.21914 (17)0.01643 (16)0.33850 (8)0.0426 (3)
H130.08540.05060.34640.051*
C110.53540 (19)0.01912 (17)0.24265 (9)0.0471 (3)
H110.61390.05490.18540.057*
O10.78818 (13)0.28143 (12)0.46533 (7)0.0538 (3)
F20.77810 (17)0.89156 (14)1.01158 (6)0.0863 (4)
C100.61712 (17)0.08505 (16)0.31573 (9)0.0437 (3)
H100.75120.11840.30770.052*
C70.47776 (18)0.45989 (15)0.70817 (8)0.0420 (3)
H70.34510.42240.71470.050*
F11.00444 (13)0.82074 (12)0.84455 (6)0.0698 (3)
C30.82137 (19)0.74793 (17)0.85365 (9)0.0470 (3)
F30.26498 (14)0.53644 (14)0.88906 (7)0.0779 (3)
C40.7048 (2)0.78435 (19)0.93994 (9)0.0552 (4)
C60.4494 (2)0.60790 (18)0.87636 (9)0.0503 (3)
C50.5175 (2)0.7150 (2)0.95292 (9)0.0613 (4)
H50.43860.73901.01130.074*
H1WA0.967 (3)0.372 (2)0.5732 (14)0.079 (5)*
H1WB1.104 (3)0.500 (3)0.5787 (16)0.098 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0504 (5)0.0632 (6)0.0421 (5)0.0077 (4)0.0084 (4)0.0111 (4)
C150.0544 (8)0.0629 (9)0.0585 (8)0.0126 (6)0.0161 (6)0.0071 (7)
O1W0.0366 (5)0.0764 (8)0.0573 (6)0.0056 (5)0.0114 (4)0.0054 (5)
C90.0356 (6)0.0366 (6)0.0357 (6)0.0019 (4)0.0055 (4)0.0028 (5)
N20.0345 (5)0.0445 (5)0.0405 (5)0.0045 (4)0.0074 (4)0.0048 (4)
C80.0359 (6)0.0383 (6)0.0404 (6)0.0040 (4)0.0060 (4)0.0029 (5)
N10.0417 (5)0.0398 (5)0.0412 (5)0.0021 (4)0.0105 (4)0.0030 (4)
C20.0453 (6)0.0443 (6)0.0368 (6)0.0012 (5)0.0033 (5)0.0016 (5)
C120.0425 (6)0.0401 (6)0.0351 (6)0.0006 (5)0.0088 (5)0.0001 (5)
C10.0448 (6)0.0382 (6)0.0372 (6)0.0027 (5)0.0077 (5)0.0014 (5)
C140.0379 (6)0.0484 (7)0.0351 (6)0.0045 (5)0.0008 (4)0.0019 (5)
C130.0348 (6)0.0497 (7)0.0417 (6)0.0070 (5)0.0039 (5)0.0006 (5)
C110.0410 (6)0.0597 (8)0.0368 (6)0.0013 (5)0.0009 (5)0.0047 (5)
O10.0367 (5)0.0669 (6)0.0524 (5)0.0125 (4)0.0029 (4)0.0091 (4)
F20.1011 (8)0.1021 (8)0.0465 (5)0.0264 (6)0.0128 (5)0.0238 (5)
C100.0324 (6)0.0540 (7)0.0423 (6)0.0037 (5)0.0005 (5)0.0003 (5)
C70.0403 (6)0.0439 (6)0.0412 (6)0.0013 (5)0.0076 (5)0.0011 (5)
F10.0587 (5)0.0800 (6)0.0655 (5)0.0242 (4)0.0089 (4)0.0075 (4)
C30.0487 (7)0.0468 (7)0.0449 (7)0.0052 (5)0.0089 (5)0.0012 (5)
F30.0581 (5)0.1054 (8)0.0624 (5)0.0235 (5)0.0085 (4)0.0039 (5)
C40.0698 (9)0.0573 (8)0.0361 (6)0.0064 (7)0.0121 (6)0.0061 (6)
C60.0475 (7)0.0582 (8)0.0434 (7)0.0048 (6)0.0013 (5)0.0027 (6)
C50.0686 (9)0.0751 (10)0.0351 (6)0.0047 (7)0.0039 (6)0.0052 (6)
Geometric parameters (Å, º) top
O2—C121.3606 (13)C12—C111.3860 (17)
O2—C151.4210 (16)C12—C131.3863 (16)
C15—H15A0.9600C1—C61.3846 (17)
C15—H15B0.9600C1—C71.4605 (15)
C15—H15C0.9600C14—C131.3861 (15)
O1W—H1WA0.84 (2)C14—H140.9300
O1W—H1WB0.86 (2)C13—H130.9300
C9—C141.3865 (16)C11—C101.3713 (17)
C9—C101.3930 (16)C11—H110.9300
C9—C81.4879 (15)F2—C41.3451 (15)
N2—C81.3473 (15)C10—H100.9300
N2—N11.3747 (13)C7—H70.9300
N2—H20.8600F1—C31.3445 (15)
C8—O11.2318 (14)C3—C41.3754 (19)
N1—C71.2720 (15)F3—C61.3522 (16)
C2—C31.3668 (16)C4—C51.363 (2)
C2—C11.3936 (17)C6—C51.3794 (18)
C2—H2A0.9300C5—H50.9300
C12—O2—C15118.76 (10)C13—C14—C9121.42 (10)
O2—C15—H15A109.5C13—C14—H14119.3
O2—C15—H15B109.5C9—C14—H14119.3
H15A—C15—H15B109.5C14—C13—C12119.40 (11)
O2—C15—H15C109.5C14—C13—H13120.3
H15A—C15—H15C109.5C12—C13—H13120.3
H15B—C15—H15C109.5C10—C11—C12120.36 (11)
H1WA—O1W—H1WB104.7 (19)C10—C11—H11119.8
C14—C9—C10118.11 (10)C12—C11—H11119.8
C14—C9—C8125.20 (10)C11—C10—C9121.02 (11)
C10—C9—C8116.68 (10)C11—C10—H10119.5
C8—N2—N1118.70 (9)C9—C10—H10119.5
C8—N2—H2120.6N1—C7—C1120.07 (11)
N1—N2—H2120.6N1—C7—H7120.0
O1—C8—N2121.75 (10)C1—C7—H7120.0
O1—C8—C9120.98 (10)F1—C3—C2120.63 (11)
N2—C8—C9117.27 (10)F1—C3—C4118.54 (11)
C7—N1—N2115.79 (10)C2—C3—C4120.81 (12)
C3—C2—C1120.19 (11)F2—C4—C5120.24 (12)
C3—C2—H2A119.9F2—C4—C3118.74 (13)
C1—C2—H2A119.9C5—C4—C3121.01 (12)
O2—C12—C11115.34 (10)F3—C6—C5118.01 (12)
O2—C12—C13124.96 (11)F3—C6—C1118.64 (12)
C11—C12—C13119.69 (10)C5—C6—C1123.34 (13)
C6—C1—C2117.04 (11)C4—C5—C6117.59 (12)
C6—C1—C7120.95 (11)C4—C5—H5121.2
C2—C1—C7122.01 (11)C6—C5—H5121.2
N1—N2—C8—O10.19 (18)C14—C9—C10—C110.03 (18)
N1—N2—C8—C9179.31 (9)C8—C9—C10—C11178.94 (11)
C14—C9—C8—O1174.51 (12)N2—N1—C7—C1178.74 (9)
C10—C9—C8—O14.38 (17)C6—C1—C7—N1174.55 (12)
C14—C9—C8—N24.62 (18)C2—C1—C7—N16.50 (18)
C10—C9—C8—N2176.49 (11)C1—C2—C3—F1179.14 (11)
C8—N2—N1—C7174.47 (11)C1—C2—C3—C40.5 (2)
C15—O2—C12—C11179.01 (12)F1—C3—C4—F20.2 (2)
C15—O2—C12—C131.29 (19)C2—C3—C4—F2178.51 (12)
C3—C2—C1—C60.47 (18)F1—C3—C4—C5179.57 (13)
C3—C2—C1—C7178.52 (11)C2—C3—C4—C50.9 (2)
C10—C9—C14—C130.51 (18)C2—C1—C6—F3178.65 (12)
C8—C9—C14—C13178.37 (11)C7—C1—C6—F32.35 (19)
C9—C14—C13—C120.39 (19)C2—C1—C6—C51.1 (2)
O2—C12—C13—C14179.90 (11)C7—C1—C6—C5177.93 (13)
C11—C12—C13—C140.21 (19)F2—C4—C5—C6179.08 (14)
O2—C12—C11—C10179.60 (11)C3—C4—C5—C60.3 (2)
C13—C12—C11—C100.68 (19)F3—C6—C5—C4179.02 (13)
C12—C11—C10—C90.6 (2)C1—C6—C5—C40.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O10.85 (2)2.05 (2)2.8376 (13)154 (2)
O1W—H1WA···N10.85 (2)2.61 (2)3.2777 (14)137 (2)
N2—H2···O1Wi0.862.122.8681 (14)145
O1W—H1WB···O1ii0.86 (2)2.01 (2)2.8635 (16)170 (2)
C5—H5···O2iii0.932.493.4128 (15)172
C7—H7···O1Wi0.932.543.2191 (15)130
Symmetry codes: (i) x1, y, z; (ii) x+2, y1, z+1; (iii) x, y1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O10.85 (2)2.05 (2)2.8376 (13)154 (2)
O1W—H1WA···N10.85 (2)2.61 (2)3.2777 (14)137 (2)
N2—H2···O1Wi0.862.122.8681 (14)145
O1W—H1WB···O1ii0.86 (2)2.01 (2)2.8635 (16)170 (2)
C5—H5···O2iii0.932.493.4128 (15)172
C7—H7···O1Wi0.932.543.2191 (15)130
Symmetry codes: (i) x1, y, z; (ii) x+2, y1, z+1; (iii) x, y1, z+1.

Experimental details

Crystal data
Chemical formulaC15H11F3N2O2·H2O
Mr326.27
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)6.6872 (2), 7.9309 (2), 13.9723 (4)
α, β, γ (°)82.348 (2), 84.783 (1), 88.710 (1)
V3)731.35 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.19 × 0.16 × 0.11
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.976, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
10841, 3036, 2559
Rint0.023
(sin θ/λ)max1)0.629
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.111, 1.04
No. of reflections3036
No. of parameters218
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.20

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008).

 

Acknowledgements

The authors express their thanks to the authorities of Saranathan College of Engineering, Tiruchirappalli, for providing laboratory facilities, and to the CAS in Crystallography and Biophysics, University of Madras, Chennai, for the single-crystal XRD data collection.

References

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