4-Meth-oxy-N-(pyridin-4-ylmeth-yl)-3-(tri-fluoro-meth-yl)benzamide monohydrate.

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, mol-ecules are linked to one another through the water mol-ecules by strong N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds, forming a ladder-type network. The benzamide mol-ecules are also linked to one another through C-H⋯F inter-actions, forming C(6) chains parallel to the b-axis direction. Aromatic π-π stacking inter-actions [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.

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 = 328.29

Triclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.135

S = 1.06

11967 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.34 e Å−3

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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813029103/sj5360sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029103/sj5360Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H13F3N2O2·H2O	F(000) = 340
Mr = 328.29	Prism
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0568P)2 + 0.2647P] where P = (Fo2 + 2Fc2)/3
11967 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) ; (iii) .