organic compounds
(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
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 π–π interactions present [intercentroid distance = 3.7883 (7) Å].
Keywords: crystal structure; benzohydrazide; Schiff base; bifurcated hydrogen bonds; hydrogen bonding.
CCDC reference: 1481890
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)°.
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 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].
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 .
details are summarized in Table 2
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Structural data
CCDC reference: 1481890
10.1107/S2414314616008464/su4051sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616008464/su4051Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616008464/su4051Isup3.cml
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%).
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 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 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].
Data collection: APEX2 (Bruker, 2008); cell
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).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). | |
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. |
C15H11F3N2O2·H2O | Z = 2 |
Mr = 326.27 | F(000) = 336 |
Triclinic, P1 | Dx = 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 |
Bruker APEXII CCD diffractometer | 3036 independent reflections |
Radiation source: fine-focus sealed tube | 2559 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 0 pixels mm-1 | θmax = 26.6°, θmin = 1.5° |
ω and φ scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | k = −9→9 |
Tmin = 0.976, Tmax = 0.986 | l = −17→16 |
10841 measured reflections |
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(Fo2) + (0.0587P)2 + 0.1124P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3036 reflections | Δρmax = 0.16 e Å−3 |
218 parameters | Δρmin = −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) |
C15H11F3N2O2·H2O | γ = 88.710 (1)° |
Mr = 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)° |
Bruker APEXII CCD diffractometer | 3036 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2559 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.986 | Rint = 0.023 |
10841 measured reflections |
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 | Δρmax = 0.16 e Å−3 |
3036 reflections | Δρmin = −0.20 e Å−3 |
218 parameters |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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) |
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. |
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 |
Mr | 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) |
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 (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 |
Δρmax, Δρmin (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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