4-Meth­oxy-N-(pyridin-4-ylmeth­yl)-3-(tri­fluoro­meth­yl)benzamide monohydrate

Sreenivasa, S.; Mohan, N.R.; Kumar, V.; Palakshamurthy, B.S.; Arunakumar, D.B.; Suchetan, P.A.

doi:10.1107/S1600536813029103

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages o1717-o1718

doi:10.1107/S1600536813029103

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4-Methoxy-N-(pyridin-4-ylmethyl)-3-(trifluoromethyl)benzamide monohydrate

S. Sreenivasa,^a N. R. Mohan,^a Vijith Kumar,^b B. S. Palakshamurthy,^c D. B. Arunakumar ^a and P. A. Suchetan ^d ^*

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, India, ^cDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and ^dDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: pasuchetan@yahoo.co.in

(Received 17 October 2013; accepted 22 October 2013; online 31 October 2013)

In the title compound, C₁₅H₁₃F₃N₂O₂·H₂O, the dihedral angle between the benzene and pyridine rings is 74.97 (1)°. The –CF₃ group attached to the benzene ring is syn to the C=O bond in the adjacent side chain. In the crystal, molecules are linked to one another through the water molecules by strong N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds, forming a ladder-type network. The benzamide molecules are also linked to one another through C—H⋯F interactions, forming C(6) chains parallel to the b-axis direction. Aromatic π–π stacking interactions [centroid–centroid separations = 3.7150 (1) and 3.7857 (1) Å] between adjacent pairs of pyridine and benzene rings are also observed, resulting in a three-dimensional architecture are also observed.

CCDC reference: 967883

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the biological activity of amides, see: Manojkumar et al. (2013a ,b ); Sreenivasa et al. (2013c ). For the importance of amides containing trifluoromethyl substituents as pharmacophores, see: Sreenivasa et al. (2013a ) and for amides providing structural rigidity to the molecules, see: Sreenivasa et al. (2013b ).

Experimental

Crystal data

C₁₅H₁₃F₃N₂O₂·H₂O
M_r = 328.29
Triclinic, $[P \overline 1]$
a = 7.2687 (13) Å
b = 7.8758 (14) Å
c = 14.177 (3) Å
α = 104.071 (10)°
β = 99.672 (10)°
γ = 97.21 (1)°
V = 764.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.34 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: ψ scan (SADABS; Bruker, 2009 ) T_min = 0.959, T_max = 0.973
11967 measured reflections
11967 independent reflections
9619 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.135
S = 1.06
11967 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O3ⁱ	0.86	2.12	2.9119 (14)	152
O3—H1O⋯N2	0.85	2.01	2.8402 (15)	166
O3—H2O⋯O2ⁱⁱ	0.85	2.20	2.9646 (13)	149
C6—H6⋯F3ⁱⁱⁱ	0.93	2.46	3.3963 (15)	173
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y-1, -z; (iii) x, y+1, z.

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

Supporting information

CCDC reference: 967883

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813029103/sj5360sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029103/sj5360Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813029103/sj5360Isup3.cml

checkCIF report

Comment top

Amides containing trifluoromethyl substituents have been considered as important pharmacophores (Sreenivasa et al. 2013a). Amide groups are very common in nature, form easily and provide structural rigidity to molecules (Sreenivasa et al. 2013b). Amides show a broad spectrum of pharmacological properties, including antibacterial (Manojkumar et al. 2013a), anti-inflammatory, antioxidant, analgesic and antiviral activity (Manojkumar et al. 2013b, Sreenivasa et al. 2013c). Keeping this in mind, the crystal structure of the title compound was determined.

In the title compound, C₁₅H₁₃F₃N₂O₂·H₂O, the dihedral angle between the benzene ring and the pyridine ring is 74.97 (1)°. The –CF₃ group attached to the benzene ring is syn to the C=O bond in the adjacent side chain. Further, the conformation of the N—H bond in the chain is anti with respect to the C=O bond. In the crystal structure, the molecules are linked to one another via water molecules through strong N1—HN1···O3, O3—H2O···O2 and O3—H1O···N2 hydrogen bonds, forming a ladder type network. The benzamide molecules are also linked to one another forming C(6) chains (Bernstein et al., 1995) parallel to the b axis through intermolecular C6—H6···F3 interactions. Further, aromatic π–π stacking interactions [centroid-centroid separations Cg1···Cg1 = 3.7150 (1) Å and Cg2···Cg2 = 3.7857 (1) Å] are also observed in the crystal structure. Cg1 and Cg2 are the centroids of the C11···C13,N2,C14,C15 and C1···C6 rings respectively.

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For the biological activity of amides, see: Manojkumar et al. (2013a,b); Sreenivasa et al. (2013c). For the importance of amides containing trifluoromethyl substituents as pharmacophores, see: Sreenivasa et al. (2013a) and for amides providing structural rigidity to the molecules, see: Sreenivasa et al. (2013b).

Experimental top

3-Tri-fluoromethyl-4-methoxy benzoic acid (1 mmol) and 1,1-carbonyldiimidazole (1.5 mmol) were dissolved in dichloroethane (5 ml) and heated to 45 ^oC for 30 min. 4-Aminomethyl pyridine (1.5 mmol) was added and the heating was continued for 4 h. The reaction was monitored by TLC. The organic layer was washed with sodium bicarbonate, dried using sodium sulfate and concentrated to yield the crude compound. This was further purified by column chromatography using petroleum ether / ethyl acetate (7:3) as eluent. Fine colorless crystals were grown by slow evaporation of the solvent system: petroleum ether / ethyl acetate (4:1) at room temperature.

Computing details top

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

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Linking of molecules in the crystal structure via water molecules, generating a ladder type network. H-atoms not involved in H-bonding are omitted.
	Fig. 3. Linking of molecules into C(6) chains parallel to the b axis through C—H···F interactions.
	Fig. 4. Aromatic π–π stacking interactions observed in the crystal structure.

4-Methoxy-N-(pyridin-4-ylmethyl)-3-(trifluoromethyl)benzamide monohydrate top

Crystal data top

C₁₅H₁₃F₃N₂O₂·H₂O	F(000) = 340
M_r = 328.29	Prism
Triclinic, P1	D_x = 1.427 Mg m⁻³
Hall symbol: -P 1	Melting point: 485 K
a = 7.2687 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8758 (14) Å	Cell parameters from 1167 reflections
c = 14.177 (3) Å	θ = 1.5–25.0°
α = 104.071 (10)°	µ = 0.12 mm⁻¹
β = 99.672 (10)°	T = 296 K
γ = 97.21 (1)°	Prism, colourless
V = 764.2 (2) Å³	0.34 × 0.28 × 0.22 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	11967 independent reflections
Radiation source: fine-focus sealed tube	9619 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: ψ scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.959, T_max = 0.973	k = −9→9
11967 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0568P)² + 0.2647P] where P = (F_o² + 2F_c²)/3
11967 reflections	(Δ/σ)_max = 0.001
212 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₅H₁₃F₃N₂O₂·H₂O	γ = 97.21 (1)°
M_r = 328.29	V = 764.2 (2) Å³
Triclinic, P1	Z = 2
a = 7.2687 (13) Å	Mo Kα radiation
b = 7.8758 (14) Å	µ = 0.12 mm⁻¹
c = 14.177 (3) Å	T = 296 K
α = 104.071 (10)°	0.34 × 0.28 × 0.22 mm
β = 99.672 (10)°

Data collection top

Bruker APEXII CCD diffractometer	11967 independent reflections
Absorption correction: ψ scan (SADABS; Bruker, 2009)	9619 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.973	R_int = 0.000
11967 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	Δρ_max = 0.36 e Å⁻³
11967 reflections	Δρ_min = −0.34 e Å⁻³
212 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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

	x	y	z	U_iso*/U_eq
C4	0.20712 (13)	−0.16715 (12)	0.35758 (7)	0.0408 (2)
C1	0.26262 (13)	0.00741 (12)	0.56032 (7)	0.0417 (3)
C6	0.24913 (15)	0.10202 (13)	0.48940 (8)	0.0468 (3)
H6	0.2589	0.2249	0.5092	0.056*
C5	0.22150 (14)	0.01550 (13)	0.39008 (8)	0.0468 (3)
H5	0.2123	0.0812	0.3437	0.056*
C7	0.2577 (2)	−0.28518 (15)	0.60207 (9)	0.0678 (4)
C3	0.22117 (14)	−0.26116 (13)	0.42910 (8)	0.0471 (3)
H3	0.2120	−0.3840	0.4090	0.057*
C11	0.32767 (14)	−0.24851 (13)	0.04242 (7)	0.0430 (3)
C12	0.49099 (15)	−0.13759 (13)	0.09862 (7)	0.0471 (3)
H12	0.4928	−0.0702	0.1626	0.057*
C9	0.18106 (15)	−0.26938 (14)	0.25155 (8)	0.0488 (3)
C2	0.24823 (14)	−0.17729 (13)	0.52871 (8)	0.0452 (3)
C10	0.14376 (16)	−0.26534 (16)	0.07791 (8)	0.0605 (3)
H10A	0.0539	−0.2148	0.0390	0.073*
H10B	0.0931	−0.3906	0.0649	0.073*
C13	0.65231 (16)	−0.12678 (14)	0.05948 (8)	0.0538 (3)
H13	0.7607	−0.0502	0.0988	0.065*
C8	0.30246 (17)	0.26947 (13)	0.69388 (8)	0.0567 (3)
H8A	0.4111	0.3276	0.6766	0.085*
H8B	0.3154	0.3032	0.7648	0.085*
H8C	0.1901	0.3042	0.6635	0.085*
C14	0.50371 (19)	−0.32623 (15)	−0.08476 (9)	0.0641 (3)
H14	0.5059	−0.3927	−0.1484	0.077*
C15	0.33680 (17)	−0.34444 (14)	−0.05187 (8)	0.0558 (3)
H15	0.2301	−0.4212	−0.0929	0.067*
N1	0.15688 (12)	−0.18044 (12)	0.18228 (6)	0.0520 (2)
HN1	0.1489	−0.0696	0.2003	0.062*
N2	0.66248 (14)	−0.21897 (12)	−0.03090 (7)	0.0586 (3)
O1	0.28861 (11)	0.08100 (9)	0.65917 (5)	0.0556 (2)
O3	0.89123 (14)	−0.17560 (10)	−0.17013 (7)	0.0713 (3)
H1O	0.8411	−0.1809	−0.1207	0.107*
H2O	0.8934	−0.2802	−0.2039	0.107*
O2	0.18367 (14)	−0.43033 (10)	0.22891 (6)	0.0790 (3)
F1	0.12080 (15)	−0.27319 (12)	0.65342 (7)	0.1170 (3)
F2	0.41714 (13)	−0.23917 (11)	0.67010 (6)	0.1046 (3)
F3	0.24329 (18)	−0.45486 (10)	0.55973 (6)	0.1459 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C4	0.0431 (6)	0.0365 (6)	0.0412 (6)	0.0039 (5)	0.0103 (5)	0.0078 (5)
C1	0.0483 (6)	0.0381 (6)	0.0362 (6)	0.0054 (5)	0.0060 (5)	0.0083 (5)
C6	0.0653 (7)	0.0322 (6)	0.0415 (7)	0.0077 (5)	0.0093 (5)	0.0091 (5)
C5	0.0609 (7)	0.0417 (6)	0.0386 (7)	0.0070 (5)	0.0096 (5)	0.0136 (5)
C7	0.1090 (11)	0.0452 (8)	0.0500 (8)	0.0187 (7)	0.0111 (8)	0.0155 (6)
C3	0.0574 (7)	0.0307 (6)	0.0511 (7)	0.0058 (5)	0.0106 (5)	0.0082 (5)
C11	0.0548 (6)	0.0382 (6)	0.0346 (6)	0.0066 (5)	0.0068 (5)	0.0092 (5)
C12	0.0563 (7)	0.0476 (6)	0.0328 (6)	0.0076 (5)	0.0047 (5)	0.0060 (5)
C9	0.0508 (6)	0.0430 (7)	0.0475 (7)	0.0026 (5)	0.0119 (5)	0.0045 (6)
C2	0.0566 (7)	0.0360 (6)	0.0444 (7)	0.0081 (5)	0.0089 (5)	0.0142 (5)
C10	0.0565 (7)	0.0739 (8)	0.0378 (7)	−0.0006 (6)	0.0064 (5)	−0.0013 (6)
C13	0.0532 (7)	0.0541 (7)	0.0490 (7)	0.0039 (5)	0.0024 (6)	0.0124 (6)
C8	0.0814 (8)	0.0411 (6)	0.0421 (7)	0.0100 (6)	0.0077 (6)	0.0048 (5)
C14	0.0830 (9)	0.0553 (8)	0.0476 (7)	0.0037 (7)	0.0236 (7)	−0.0009 (6)
C15	0.0655 (8)	0.0478 (7)	0.0425 (7)	−0.0041 (6)	0.0120 (6)	−0.0029 (5)
N1	0.0636 (6)	0.0506 (5)	0.0366 (5)	0.0064 (4)	0.0126 (4)	0.0026 (4)
N2	0.0638 (6)	0.0549 (6)	0.0572 (7)	0.0086 (5)	0.0185 (5)	0.0120 (5)
O1	0.0865 (6)	0.0409 (4)	0.0364 (4)	0.0108 (4)	0.0067 (4)	0.0091 (3)
O3	0.0933 (6)	0.0590 (5)	0.0690 (6)	0.0117 (5)	0.0364 (5)	0.0185 (4)
O2	0.1277 (8)	0.0419 (5)	0.0609 (6)	0.0138 (5)	0.0235 (5)	−0.0004 (4)
F1	0.1480 (8)	0.1277 (8)	0.1152 (7)	0.0268 (6)	0.0619 (7)	0.0820 (6)
F2	0.1252 (7)	0.1093 (7)	0.0871 (6)	0.0239 (5)	−0.0084 (5)	0.0600 (5)
F3	0.3145 (16)	0.0451 (5)	0.0806 (6)	0.0383 (6)	0.0229 (7)	0.0305 (4)

Geometric parameters (Å, º) top

C4—C5	1.3843 (13)	C12—H12	0.9300
C4—C3	1.3914 (13)	C9—O2	1.2331 (12)
C4—C9	1.4903 (14)	C9—N1	1.3392 (13)
C1—O1	1.3506 (12)	C10—N1	1.4495 (13)
C1—C6	1.3875 (14)	C10—H10A	0.9700
C1—C2	1.3989 (13)	C10—H10B	0.9700
C6—C5	1.3753 (14)	C13—N2	1.3295 (14)
C6—H6	0.9300	C13—H13	0.9300
C5—H5	0.9300	C8—O1	1.4305 (12)
C7—F3	1.3079 (13)	C8—H8A	0.9600
C7—F2	1.3240 (15)	C8—H8B	0.9600
C7—F1	1.3279 (16)	C8—H8C	0.9600
C7—C2	1.4929 (15)	C14—N2	1.3319 (15)
C3—C2	1.3746 (14)	C14—C15	1.3743 (16)
C3—H3	0.9300	C14—H14	0.9300
C11—C12	1.3750 (14)	C15—H15	0.9300
C11—C15	1.3832 (14)	N1—HN1	0.8600
C11—C10	1.5072 (15)	O3—H1O	0.8499
C12—C13	1.3808 (15)	O3—H2O	0.8500

C5—C4—C3	117.63 (9)	C3—C2—C1	119.91 (9)
C5—C4—C9	124.51 (9)	C3—C2—C7	119.49 (9)
C3—C4—C9	117.85 (9)	C1—C2—C7	120.59 (10)
O1—C1—C6	124.57 (9)	N1—C10—C11	115.26 (9)
O1—C1—C2	116.78 (8)	N1—C10—H10A	108.5
C6—C1—C2	118.65 (9)	C11—C10—H10A	108.5
C5—C6—C1	120.53 (9)	N1—C10—H10B	108.5
C5—C6—H6	119.7	C11—C10—H10B	108.5
C1—C6—H6	119.7	H10A—C10—H10B	107.5
C6—C5—C4	121.53 (9)	N2—C13—C12	124.12 (10)
C6—C5—H5	119.2	N2—C13—H13	117.9
C4—C5—H5	119.2	C12—C13—H13	117.9
F3—C7—F2	106.29 (11)	O1—C8—H8A	109.5
F3—C7—F1	105.41 (12)	O1—C8—H8B	109.5
F2—C7—F1	104.90 (11)	H8A—C8—H8B	109.5
F3—C7—C2	112.39 (10)	O1—C8—H8C	109.5
F2—C7—C2	113.54 (11)	H8A—C8—H8C	109.5
F1—C7—C2	113.58 (10)	H8B—C8—H8C	109.5
C2—C3—C4	121.74 (9)	N2—C14—C15	123.86 (11)
C2—C3—H3	119.1	N2—C14—H14	118.1
C4—C3—H3	119.1	C15—C14—H14	118.1
C12—C11—C15	116.65 (10)	C14—C15—C11	119.91 (11)
C12—C11—C10	123.31 (10)	C14—C15—H15	120.0
C15—C11—C10	120.02 (9)	C11—C15—H15	120.0
C11—C12—C13	119.61 (10)	C9—N1—C10	121.98 (10)
C11—C12—H12	120.2	C9—N1—HN1	119.0
C13—C12—H12	120.2	C10—N1—HN1	119.0
O2—C9—N1	121.38 (10)	C13—N2—C14	115.85 (10)
O2—C9—C4	120.76 (10)	C1—O1—C8	118.17 (7)
N1—C9—C4	117.85 (9)	H1O—O3—H2O	109.5

O1—C1—C6—C5	−179.63 (9)	F3—C7—C2—C3	1.81 (18)
C2—C1—C6—C5	0.23 (15)	F2—C7—C2—C3	122.49 (12)
C1—C6—C5—C4	−0.29 (16)	F1—C7—C2—C3	−117.75 (12)
C3—C4—C5—C6	0.15 (15)	F3—C7—C2—C1	−179.53 (12)
C9—C4—C5—C6	−178.73 (10)	F2—C7—C2—C1	−58.85 (15)
C5—C4—C3—C2	0.05 (15)	F1—C7—C2—C1	60.90 (15)
C9—C4—C3—C2	179.00 (9)	C12—C11—C10—N1	−10.41 (15)
C15—C11—C12—C13	0.16 (14)	C15—C11—C10—N1	171.11 (10)
C10—C11—C12—C13	−178.37 (9)	C11—C12—C13—N2	−0.43 (16)
C5—C4—C9—O2	174.51 (10)	N2—C14—C15—C11	−0.26 (18)
C3—C4—C9—O2	−4.36 (15)	C12—C11—C15—C14	0.16 (15)
C5—C4—C9—N1	−4.80 (15)	C10—C11—C15—C14	178.74 (10)
C3—C4—C9—N1	176.33 (9)	O2—C9—N1—C10	−3.73 (16)
C4—C3—C2—C1	−0.10 (16)	C4—C9—N1—C10	175.58 (9)
C4—C3—C2—C7	178.57 (10)	C11—C10—N1—C9	−93.86 (12)
O1—C1—C2—C3	179.83 (9)	C12—C13—N2—C14	0.33 (16)
C6—C1—C2—C3	−0.04 (15)	C15—C14—N2—C13	0.02 (17)
O1—C1—C2—C7	1.17 (15)	C6—C1—O1—C8	0.32 (15)
C6—C1—C2—C7	−178.69 (10)	C2—C1—O1—C8	−179.53 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O3ⁱ	0.86	2.12	2.9119 (14)	152
O3—H1O···N2	0.85	2.01	2.8402 (15)	166
O3—H2O···O2ⁱⁱ	0.85	2.20	2.9646 (13)	149
C6—H6···F3ⁱⁱⁱ	0.93	2.46	3.3963 (15)	173

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y−1, −z; (iii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O3ⁱ	0.86	2.12	2.9119 (14)	152
O3—H1O···N2	0.85	2.01	2.8402 (15)	166
O3—H2O···O2ⁱⁱ	0.85	2.20	2.9646 (13)	149
C6—H6···F3ⁱⁱⁱ	0.93	2.46	3.3963 (15)	173

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y−1, −z; (iii) x, y+1, z.

Acknowledgements

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help and valuable suggestions.

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