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

Maheswari, R.; Manjula, J.; Gunasekaran, B.; Bakiyaraj, G.

doi:10.1107/S2414314616008464

organic compounds

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ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160846

doi:10.1107/S2414314616008464

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

R. Maheswari,^a J. Manjula,^b ^* B. Gunasekaran ^c and G. Bakiyaraj ^c

^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 O_water—H⋯(O,N) hydrogen bonds and N—H⋯O_water and O_water—H⋯O and C—H⋯O hydrogen bonds, forming chains along [100]. The chains are linked by C—H⋯O_water hydrogen bonds, forming slabs parallel to the bc plane. Within the slabs there are offset π–π interactions present [intercentroid distance = 3.7883 (7) Å].

Keywords: crystal structure; benzohydrazide; Schiff base; bifurcated hydrogen bonds; hydrogen bonding.

CCDC reference: 1481890

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Chemical scheme

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 ). 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 C7=N1 bond is E. The dihedral angle between methoxyphenyl ring and trifluorobenzylidene ring is 7.46 (6)°.

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

In the crystal, molecules are linked by bifurcated O_water—H⋯(O,N) hydrogen bonds and N—H⋯O_water and O_water—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⋯O_water hydrogen bonds, forming slabs parallel to the bc plane (Table 1 and Fig. 3). Within the slabs, there are offset π–π 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	D⋯A	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
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
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.

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.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₁F₃N₂O₂·H₂O
M_r	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)
V (Å³)	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 )
T_min, T_max	0.976, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	10841, 3036, 2559
R_int	0.023
(sin θ/λ)_max (Å⁻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
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1481890

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616008464/su4051sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616008464/su4051Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616008464/su4051Isup3.cml

checkCIF report

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%).

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 C7═N1 bond is E. The dihedral angle between methoxyphenyl ring and trifluorobenzylidene ring is 7.46 (6)°.

In the crystal, molecules are linked by bifurcated O_water—H···(O,N) hydrogen bonds and N—H···O_water and O_water—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···O_water hydrogen bonds, forming slabs parallel to the bc plane (Table 1 and Fig. 3). Within the slabs, there are offset π–π 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

	Fig. 1. The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The bifurcated O_water—H···(O,N) hydrogen bonds are shown as dashed lines (see Table 1).
	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.
	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·H₂O	Z = 2
M_r = 326.27	F(000) = 336
Triclinic, P1	D_x = 1.482 Mg m⁻³
a = 6.6872 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9309 (2) Å	Cell parameters from 3036 reflections
c = 13.9723 (4) Å	θ = 1.5–26.6°
α = 82.348 (2)°	µ = 0.13 mm⁻¹
β = 84.783 (1)°	T = 296 K
γ = 88.710 (1)°	Block, colourless
V = 731.35 (4) Å³	0.19 × 0.16 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	3036 independent reflections
Radiation source: fine-focus sealed tube	2559 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 0 pixels mm^-1	θ_max = 26.6°, θ_min = 1.5°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −9→9
T_min = 0.976, T_max = 0.986	l = −17→16
10841 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0587P)² + 0.1124P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3036 reflections	Δρ_max = 0.16 e Å⁻³
218 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.105 (7)

Crystal data top

C₁₅H₁₁F₃N₂O₂·H₂O	γ = 88.710 (1)°
M_r = 326.27	V = 731.35 (4) Å³
Triclinic, P1	Z = 2
a = 6.6872 (2) Å	Mo Kα radiation
b = 7.9309 (2) Å	µ = 0.13 mm⁻¹
c = 13.9723 (4) Å	T = 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)
T_min = 0.976, T_max = 0.986	R_int = 0.023
10841 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.16 e Å⁻³
3036 reflections	Δρ_min = −0.20 e Å⁻³
218 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O2	0.27163 (14)	0.17533 (13)	0.17677 (6)	0.0534 (3)
C15	0.0702 (2)	0.23667 (19)	0.18294 (11)	0.0595 (4)
H15A	−0.0200	0.1425	0.1898	0.089*
H15B	0.0478	0.3119	0.1251	0.089*
H15C	0.0467	0.2971	0.2381	0.089*
O1W	1.07816 (14)	−0.40072 (17)	0.59527 (7)	0.0567 (3)
C9	0.50245 (16)	−0.14171 (14)	0.40181 (8)	0.0360 (3)
N2	0.49491 (14)	−0.31489 (12)	0.55853 (7)	0.0406 (2)
H2	0.3684	−0.2927	0.5657	0.049*
C8	0.60665 (17)	−0.25169 (14)	0.47707 (8)	0.0383 (3)
N1	0.58713 (15)	−0.41549 (12)	0.62992 (7)	0.0412 (3)
C2	0.75138 (18)	−0.64277 (15)	0.77805 (8)	0.0428 (3)
H2A	0.8315	−0.6199	0.7199	0.051*
C12	0.33642 (18)	0.07140 (15)	0.25356 (8)	0.0394 (3)
C1	0.56035 (18)	−0.56972 (15)	0.78779 (8)	0.0401 (3)
C14	0.30309 (17)	−0.08984 (16)	0.41155 (8)	0.0415 (3)
H14	0.2240	−0.1272	0.4683	0.050*
C13	0.21914 (17)	0.01643 (16)	0.33850 (8)	0.0426 (3)
H13	0.0854	0.0506	0.3464	0.051*
C11	0.53540 (19)	0.01912 (17)	0.24265 (9)	0.0471 (3)
H11	0.6139	0.0549	0.1854	0.057*
O1	0.78818 (13)	−0.28143 (12)	0.46533 (7)	0.0538 (3)
F2	0.77810 (17)	−0.89156 (14)	1.01158 (6)	0.0863 (4)
C10	0.61712 (17)	−0.08505 (16)	0.31573 (9)	0.0437 (3)
H10	0.7512	−0.1184	0.3077	0.052*
C7	0.47776 (18)	−0.45989 (15)	0.70817 (8)	0.0420 (3)
H7	0.3451	−0.4224	0.7147	0.050*
F1	1.00444 (13)	−0.82074 (12)	0.84455 (6)	0.0698 (3)
C3	0.82137 (19)	−0.74793 (17)	0.85365 (9)	0.0470 (3)
F3	0.26498 (14)	−0.53644 (14)	0.88906 (7)	0.0779 (3)
C4	0.7048 (2)	−0.78435 (19)	0.93994 (9)	0.0552 (4)
C6	0.4494 (2)	−0.60790 (18)	0.87636 (9)	0.0503 (3)
C5	0.5175 (2)	−0.7150 (2)	0.95292 (9)	0.0613 (4)
H5	0.4386	−0.7390	1.0113	0.074*
H1WA	0.967 (3)	−0.372 (2)	0.5732 (14)	0.079 (5)*
H1WB	1.104 (3)	−0.500 (3)	0.5787 (16)	0.098 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0504 (5)	0.0632 (6)	0.0421 (5)	0.0077 (4)	−0.0084 (4)	0.0111 (4)
C15	0.0544 (8)	0.0629 (9)	0.0585 (8)	0.0126 (6)	−0.0161 (6)	0.0071 (7)
O1W	0.0366 (5)	0.0764 (8)	0.0573 (6)	0.0056 (5)	−0.0114 (4)	−0.0054 (5)
C9	0.0356 (6)	0.0366 (6)	0.0357 (6)	0.0019 (4)	−0.0055 (4)	−0.0028 (5)
N2	0.0345 (5)	0.0445 (5)	0.0405 (5)	0.0045 (4)	−0.0074 (4)	0.0048 (4)
C8	0.0359 (6)	0.0383 (6)	0.0404 (6)	0.0040 (4)	−0.0060 (4)	−0.0029 (5)
N1	0.0417 (5)	0.0398 (5)	0.0412 (5)	0.0021 (4)	−0.0105 (4)	0.0030 (4)
C2	0.0453 (6)	0.0443 (6)	0.0368 (6)	−0.0012 (5)	−0.0033 (5)	0.0016 (5)
C12	0.0425 (6)	0.0401 (6)	0.0351 (6)	0.0006 (5)	−0.0088 (5)	0.0001 (5)
C1	0.0448 (6)	0.0382 (6)	0.0372 (6)	−0.0027 (5)	−0.0077 (5)	−0.0014 (5)
C14	0.0379 (6)	0.0484 (7)	0.0351 (6)	0.0045 (5)	0.0008 (4)	0.0019 (5)
C13	0.0348 (6)	0.0497 (7)	0.0417 (6)	0.0070 (5)	−0.0039 (5)	−0.0006 (5)
C11	0.0410 (6)	0.0597 (8)	0.0368 (6)	−0.0013 (5)	0.0009 (5)	0.0047 (5)
O1	0.0367 (5)	0.0669 (6)	0.0524 (5)	0.0125 (4)	−0.0029 (4)	0.0091 (4)
F2	0.1011 (8)	0.1021 (8)	0.0465 (5)	0.0264 (6)	−0.0128 (5)	0.0238 (5)
C10	0.0324 (6)	0.0540 (7)	0.0423 (6)	0.0037 (5)	−0.0005 (5)	−0.0003 (5)
C7	0.0403 (6)	0.0439 (6)	0.0412 (6)	0.0013 (5)	−0.0076 (5)	−0.0011 (5)
F1	0.0587 (5)	0.0800 (6)	0.0655 (5)	0.0242 (4)	−0.0089 (4)	0.0075 (4)
C3	0.0487 (7)	0.0468 (7)	0.0449 (7)	0.0052 (5)	−0.0089 (5)	−0.0012 (5)
F3	0.0581 (5)	0.1054 (8)	0.0624 (5)	0.0235 (5)	0.0085 (4)	0.0039 (5)
C4	0.0698 (9)	0.0573 (8)	0.0361 (6)	0.0064 (7)	−0.0121 (6)	0.0061 (6)
C6	0.0475 (7)	0.0582 (8)	0.0434 (7)	0.0048 (6)	−0.0013 (5)	−0.0027 (6)
C5	0.0686 (9)	0.0751 (10)	0.0351 (6)	0.0047 (7)	0.0039 (6)	0.0052 (6)

Geometric parameters (Å, º) top

O2—C12	1.3606 (13)	C12—C11	1.3860 (17)
O2—C15	1.4210 (16)	C12—C13	1.3863 (16)
C15—H15A	0.9600	C1—C6	1.3846 (17)
C15—H15B	0.9600	C1—C7	1.4605 (15)
C15—H15C	0.9600	C14—C13	1.3861 (15)
O1W—H1WA	0.84 (2)	C14—H14	0.9300
O1W—H1WB	0.86 (2)	C13—H13	0.9300
C9—C14	1.3865 (16)	C11—C10	1.3713 (17)
C9—C10	1.3930 (16)	C11—H11	0.9300
C9—C8	1.4879 (15)	F2—C4	1.3451 (15)
N2—C8	1.3473 (15)	C10—H10	0.9300
N2—N1	1.3747 (13)	C7—H7	0.9300
N2—H2	0.8600	F1—C3	1.3445 (15)
C8—O1	1.2318 (14)	C3—C4	1.3754 (19)
N1—C7	1.2720 (15)	F3—C6	1.3522 (16)
C2—C3	1.3668 (16)	C4—C5	1.363 (2)
C2—C1	1.3936 (17)	C6—C5	1.3794 (18)
C2—H2A	0.9300	C5—H5	0.9300

C12—O2—C15	118.76 (10)	C13—C14—C9	121.42 (10)
O2—C15—H15A	109.5	C13—C14—H14	119.3
O2—C15—H15B	109.5	C9—C14—H14	119.3
H15A—C15—H15B	109.5	C14—C13—C12	119.40 (11)
O2—C15—H15C	109.5	C14—C13—H13	120.3
H15A—C15—H15C	109.5	C12—C13—H13	120.3
H15B—C15—H15C	109.5	C10—C11—C12	120.36 (11)
H1WA—O1W—H1WB	104.7 (19)	C10—C11—H11	119.8
C14—C9—C10	118.11 (10)	C12—C11—H11	119.8
C14—C9—C8	125.20 (10)	C11—C10—C9	121.02 (11)
C10—C9—C8	116.68 (10)	C11—C10—H10	119.5
C8—N2—N1	118.70 (9)	C9—C10—H10	119.5
C8—N2—H2	120.6	N1—C7—C1	120.07 (11)
N1—N2—H2	120.6	N1—C7—H7	120.0
O1—C8—N2	121.75 (10)	C1—C7—H7	120.0
O1—C8—C9	120.98 (10)	F1—C3—C2	120.63 (11)
N2—C8—C9	117.27 (10)	F1—C3—C4	118.54 (11)
C7—N1—N2	115.79 (10)	C2—C3—C4	120.81 (12)
C3—C2—C1	120.19 (11)	F2—C4—C5	120.24 (12)
C3—C2—H2A	119.9	F2—C4—C3	118.74 (13)
C1—C2—H2A	119.9	C5—C4—C3	121.01 (12)
O2—C12—C11	115.34 (10)	F3—C6—C5	118.01 (12)
O2—C12—C13	124.96 (11)	F3—C6—C1	118.64 (12)
C11—C12—C13	119.69 (10)	C5—C6—C1	123.34 (13)
C6—C1—C2	117.04 (11)	C4—C5—C6	117.59 (12)
C6—C1—C7	120.95 (11)	C4—C5—H5	121.2
C2—C1—C7	122.01 (11)	C6—C5—H5	121.2

N1—N2—C8—O1	−0.19 (18)	C14—C9—C10—C11	0.03 (18)
N1—N2—C8—C9	−179.31 (9)	C8—C9—C10—C11	−178.94 (11)
C14—C9—C8—O1	−174.51 (12)	N2—N1—C7—C1	178.74 (9)
C10—C9—C8—O1	4.38 (17)	C6—C1—C7—N1	174.55 (12)
C14—C9—C8—N2	4.62 (18)	C2—C1—C7—N1	−6.50 (18)
C10—C9—C8—N2	−176.49 (11)	C1—C2—C3—F1	179.14 (11)
C8—N2—N1—C7	174.47 (11)	C1—C2—C3—C4	0.5 (2)
C15—O2—C12—C11	−179.01 (12)	F1—C3—C4—F2	−0.2 (2)
C15—O2—C12—C13	1.29 (19)	C2—C3—C4—F2	178.51 (12)
C3—C2—C1—C6	0.47 (18)	F1—C3—C4—C5	−179.57 (13)
C3—C2—C1—C7	−178.52 (11)	C2—C3—C4—C5	−0.9 (2)
C10—C9—C14—C13	−0.51 (18)	C2—C1—C6—F3	178.65 (12)
C8—C9—C14—C13	178.37 (11)	C7—C1—C6—F3	−2.35 (19)
C9—C14—C13—C12	0.39 (19)	C2—C1—C6—C5	−1.1 (2)
O2—C12—C13—C14	179.90 (11)	C7—C1—C6—C5	177.93 (13)
C11—C12—C13—C14	0.21 (19)	F2—C4—C5—C6	−179.08 (14)
O2—C12—C11—C10	179.60 (11)	C3—C4—C5—C6	0.3 (2)
C13—C12—C11—C10	−0.68 (19)	F3—C6—C5—C4	−179.02 (13)
C12—C11—C10—C9	0.6 (2)	C1—C6—C5—C4	0.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁F₃N₂O₂·H₂O
M_r	326.27
Crystal system, space group	Triclinic, 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)
V (Å³)	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)
T_min, T_max	0.976, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	10841, 3036, 2559
R_int	0.023
(sin θ/λ)_max (Å⁻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
Δρ_max, Δρ_min (e Å⁻³)	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.

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