organic compounds
N′-[(E)-(3-Phenyl-1H-pyrazol-4-yl)methylidene]naphtho[2,1-b]furan-2-carbohydrazide monohydrate
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bMedicinal Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
*Correspondence e-mail: hkfun@usm.my
In the title hydrate, C23H16N4O2·H2O, the pyrazole ring is approximately planar, with a maximum deviation of 0.023 (1) Å, and makes dihedral angles of 28.63 (6) and 46.44 (7)° with the naphtho[2,1-b]furan ring system and the benzene ring, respectively, In the crystal, O—H⋯N, O—H⋯O, N—H⋯O, N—H⋯N, C—H⋯O and C—H⋯N hydrogen bonds link the molecules, forming sheets lying parallel to the ab plane. The also features C—H⋯π interactions involving the centroids of the pyrazole and benzene rings.
Related literature
For the biological activity of et al. (1990); Cavier & Rips (1965); Silva et al. (2005); Eissa & Soliman (2009). For a related structure, see: Choi et al. (2009). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986).
and their adducts, see: JahagirdarExperimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536811050239/hb6529sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050239/hb6529Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811050239/hb6529Isup3.cml
A mixture of naphtho[2,1-b]furan-2-carbohydrazide (0.226 g, 0.001 mol) and 3-phenyl-1H-pyrazole-4-carbaldehyde (0.189 g, 0.0011 mol) was refluxed in ethanol for 4 h in the presence of a catalytic amount of acetic acid. The mixture was then cooled to room temperature and the resulting solid was filtered and dried to get the title compound. Yield: 0.28 g, 73.68%. M.p.: 524–526 K.
The O– and N-bound hydrogen atoms were located from the difference Fourier map. N-bound hydrogen atoms were refined freely and O-bound hydrogen atoms were fixed at their found positions with a riding model with Uiso(H) = 1.2 Ueq(O) [N–H= 0.94 (2) and 0.96 (2) Å; O–H = 0.8628 and 0.8895 Å]. The remaining hydrogen atoms were positioned geometrically and were refined with a riding model with Uiso(H) = 1.2 Ueq(C) [C–H = 0.95 Å].
Acidhydrazones and their condensation products possessing an azometine –NHN═ CH– proton constitute an important class of compounds for new drug development. In the past several years, numerous compounds with diverse structural features have been reported. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. and their adducts have displayed diverse range of biological properties such as anti-viral (Jahagirdar et al., 1990), anti-tuberculosis (Cavier et al., 1965) and anti-inflammatory activities (Silva et al., 2005; Eissa et al., 2009). We have synthesized the title compound to study its and evaluate its biological activities.
The title compound (Fig. 1) consists of one molecule of N'-[(E)-(3-phenyl-1H-pyrazol-4-yl)methylidene]naphtho [2,1-b]furan-2-carbohydrazide and a water molecule. The pyrazole ring (N3/N4/C15–C17) is approximately planar with a maximum deviation of 0.023 (1) Å at atom C17. This ring makes dihedral angles of 28.63 (6)° with the naphtho[2,1-b]furan ring system (O1/C1–C12; maximum deviation of 0.016 (1) Å at atom C10) and 46.44 (7)° with the benzene ring (C18–C23; maximum deviation of 0.012 (1) Å at atom C18). Bond lengths and angles are comparable to a related structure (Choi et al., 2009).
In the crystal, (Fig. 2), O1W—H1W1···N4, O1W—H2W1···O2, N3—H1N3···O2, N3—H1N3···N2, N1—H1N1···O1W C14—H14A···O1W, C16—H16A···N4 and C21—H21A···O2 hydrogen bonds (Table 1) link the molecules to form sheets parallel to the ab plane. The π interactions (Table 1) involving the centroids of pyrazole (Cg1) and benzene (Cg2) rings.
is further stabilized by C—H···For the biological activity of
and their adducts, see: Jahagirdar et al. (1990); Cavier & Rips (1965); Silva et al. (2005); Eissa & Soliman (2009). For a related structure, see: Choi et al. (2009). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986).Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. | |
Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing the sheets parallel to the ab plane. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity. |
C23H16N4O2·H2O | F(000) = 832 |
Mr = 398.41 | Dx = 1.399 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3650 reflections |
a = 7.1383 (1) Å | θ = 2.3–29.5° |
b = 9.3928 (1) Å | µ = 0.10 mm−1 |
c = 28.4200 (4) Å | T = 100 K |
β = 96.864 (1)° | Block, colourless |
V = 1891.86 (4) Å3 | 0.31 × 0.25 × 0.18 mm |
Z = 4 |
Bruker SMART APEXII CCD diffractometer | 5516 independent reflections |
Radiation source: fine-focus sealed tube | 3857 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
φ and ω scans | θmax = 30.1°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −9→10 |
Tmin = 0.971, Tmax = 0.983 | k = −13→13 |
21248 measured reflections | l = −39→40 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0566P)2 + 0.4389P] where P = (Fo2 + 2Fc2)/3 |
5516 reflections | (Δ/σ)max < 0.001 |
279 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C23H16N4O2·H2O | V = 1891.86 (4) Å3 |
Mr = 398.41 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.1383 (1) Å | µ = 0.10 mm−1 |
b = 9.3928 (1) Å | T = 100 K |
c = 28.4200 (4) Å | 0.31 × 0.25 × 0.18 mm |
β = 96.864 (1)° |
Bruker SMART APEXII CCD diffractometer | 5516 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3857 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.983 | Rint = 0.058 |
21248 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.27 e Å−3 |
5516 reflections | Δρmin = −0.27 e Å−3 |
279 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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 | ||
O1 | 0.43329 (14) | 1.04167 (12) | 0.06904 (4) | 0.0190 (2) | |
O2 | 0.91817 (15) | 1.01592 (13) | 0.11647 (4) | 0.0251 (3) | |
N1 | 0.65264 (19) | 0.90451 (14) | 0.13601 (4) | 0.0177 (3) | |
N2 | 0.75457 (18) | 0.82808 (14) | 0.17263 (4) | 0.0177 (3) | |
N3 | 0.93853 (18) | 0.49668 (15) | 0.27204 (5) | 0.0196 (3) | |
N4 | 0.78932 (17) | 0.40748 (14) | 0.26062 (5) | 0.0196 (3) | |
C1 | 0.3524 (2) | 1.12767 (17) | 0.03335 (5) | 0.0183 (3) | |
C2 | 0.1589 (2) | 1.13360 (19) | 0.01844 (6) | 0.0232 (3) | |
H2A | 0.0711 | 1.0769 | 0.0327 | 0.028* | |
C3 | 0.1027 (2) | 1.22541 (19) | −0.01779 (6) | 0.0245 (4) | |
H3A | −0.0275 | 1.2308 | −0.0294 | 0.029* | |
C4 | 0.2337 (2) | 1.31378 (18) | −0.03878 (6) | 0.0212 (3) | |
C5 | 0.1705 (2) | 1.41189 (19) | −0.07502 (6) | 0.0242 (4) | |
H5A | 0.0398 | 1.4178 | −0.0861 | 0.029* | |
C6 | 0.2963 (2) | 1.49881 (18) | −0.09438 (6) | 0.0248 (4) | |
H6A | 0.2514 | 1.5661 | −0.1180 | 0.030* | |
C7 | 0.4909 (2) | 1.48864 (18) | −0.07936 (6) | 0.0238 (3) | |
H7A | 0.5772 | 1.5474 | −0.0934 | 0.029* | |
C8 | 0.5563 (2) | 1.39364 (17) | −0.04433 (6) | 0.0210 (3) | |
H8A | 0.6878 | 1.3874 | −0.0343 | 0.025* | |
C9 | 0.4303 (2) | 1.30561 (17) | −0.02320 (5) | 0.0185 (3) | |
C10 | 0.4875 (2) | 1.20827 (16) | 0.01465 (5) | 0.0170 (3) | |
C11 | 0.6639 (2) | 1.17157 (17) | 0.04153 (5) | 0.0188 (3) | |
H11A | 0.7846 | 1.2095 | 0.0377 | 0.023* | |
C12 | 0.6241 (2) | 1.07205 (17) | 0.07342 (5) | 0.0175 (3) | |
C13 | 0.7456 (2) | 0.99555 (17) | 0.11028 (5) | 0.0184 (3) | |
C14 | 0.6704 (2) | 0.71368 (16) | 0.18341 (5) | 0.0167 (3) | |
H14A | 0.5497 | 0.6931 | 0.1669 | 0.020* | |
C15 | 0.7500 (2) | 0.61507 (16) | 0.21930 (5) | 0.0166 (3) | |
C16 | 0.9210 (2) | 0.61994 (17) | 0.24849 (5) | 0.0185 (3) | |
H16A | 1.0087 | 0.6965 | 0.2512 | 0.022* | |
C17 | 0.6738 (2) | 0.47933 (16) | 0.22852 (5) | 0.0168 (3) | |
C18 | 0.4979 (2) | 0.41425 (16) | 0.20556 (5) | 0.0169 (3) | |
C19 | 0.4996 (2) | 0.27495 (17) | 0.18791 (5) | 0.0197 (3) | |
H19A | 0.6122 | 0.2203 | 0.1927 | 0.024* | |
C20 | 0.3376 (2) | 0.21643 (18) | 0.16353 (6) | 0.0229 (3) | |
H20A | 0.3396 | 0.1219 | 0.1517 | 0.027* | |
C21 | 0.1728 (2) | 0.29580 (19) | 0.15644 (6) | 0.0236 (4) | |
H21A | 0.0629 | 0.2564 | 0.1391 | 0.028* | |
C22 | 0.1685 (2) | 0.43245 (18) | 0.17454 (5) | 0.0209 (3) | |
H22A | 0.0550 | 0.4862 | 0.1700 | 0.025* | |
C23 | 0.3301 (2) | 0.49127 (17) | 0.19929 (5) | 0.0187 (3) | |
H23A | 0.3259 | 0.5846 | 0.2120 | 0.022* | |
O1W | 0.25339 (16) | 0.83476 (13) | 0.13979 (4) | 0.0270 (3) | |
H1W1 | 0.2518 | 0.8380 | 0.1701 | 0.041* | |
H2W1 | 0.1460 | 0.8694 | 0.1251 | 0.041* | |
H1N3 | 1.036 (3) | 0.467 (3) | 0.2959 (9) | 0.064 (8)* | |
H1N1 | 0.523 (4) | 0.888 (3) | 0.1276 (9) | 0.061 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0172 (5) | 0.0208 (6) | 0.0183 (5) | −0.0003 (4) | −0.0002 (4) | 0.0029 (4) |
O2 | 0.0196 (6) | 0.0262 (6) | 0.0277 (6) | −0.0049 (5) | −0.0040 (4) | 0.0068 (5) |
N1 | 0.0180 (6) | 0.0176 (6) | 0.0168 (6) | −0.0007 (5) | −0.0016 (5) | 0.0038 (5) |
N2 | 0.0193 (6) | 0.0173 (6) | 0.0158 (6) | 0.0009 (5) | −0.0011 (5) | 0.0011 (5) |
N3 | 0.0163 (6) | 0.0231 (7) | 0.0185 (6) | −0.0006 (5) | −0.0014 (5) | 0.0028 (6) |
N4 | 0.0175 (6) | 0.0204 (7) | 0.0203 (7) | 0.0000 (5) | 0.0005 (5) | 0.0027 (5) |
C1 | 0.0208 (7) | 0.0189 (7) | 0.0150 (7) | 0.0015 (6) | 0.0013 (6) | 0.0009 (6) |
C2 | 0.0181 (8) | 0.0287 (9) | 0.0229 (8) | −0.0027 (7) | 0.0024 (6) | 0.0043 (7) |
C3 | 0.0189 (8) | 0.0305 (9) | 0.0238 (8) | 0.0017 (7) | 0.0017 (6) | 0.0034 (7) |
C4 | 0.0222 (8) | 0.0233 (8) | 0.0178 (7) | 0.0020 (7) | 0.0017 (6) | 0.0003 (6) |
C5 | 0.0240 (8) | 0.0289 (9) | 0.0191 (8) | 0.0053 (7) | 0.0004 (6) | 0.0024 (7) |
C6 | 0.0334 (9) | 0.0234 (8) | 0.0176 (8) | 0.0068 (7) | 0.0025 (6) | 0.0032 (7) |
C7 | 0.0299 (9) | 0.0229 (8) | 0.0192 (8) | −0.0009 (7) | 0.0055 (6) | 0.0010 (7) |
C8 | 0.0238 (8) | 0.0203 (8) | 0.0193 (8) | 0.0000 (6) | 0.0047 (6) | 0.0010 (6) |
C9 | 0.0207 (8) | 0.0195 (8) | 0.0151 (7) | 0.0011 (6) | 0.0024 (6) | −0.0006 (6) |
C10 | 0.0175 (7) | 0.0181 (7) | 0.0152 (7) | 0.0011 (6) | 0.0013 (5) | −0.0003 (6) |
C11 | 0.0173 (7) | 0.0194 (8) | 0.0195 (7) | 0.0003 (6) | 0.0011 (6) | 0.0002 (6) |
C12 | 0.0161 (7) | 0.0181 (7) | 0.0179 (7) | −0.0015 (6) | 0.0002 (5) | −0.0006 (6) |
C13 | 0.0195 (7) | 0.0176 (7) | 0.0176 (7) | −0.0015 (6) | −0.0004 (6) | 0.0001 (6) |
C14 | 0.0166 (7) | 0.0170 (7) | 0.0164 (7) | 0.0011 (6) | 0.0009 (5) | −0.0014 (6) |
C15 | 0.0177 (7) | 0.0169 (7) | 0.0153 (7) | 0.0015 (6) | 0.0022 (5) | −0.0008 (6) |
C16 | 0.0180 (7) | 0.0202 (8) | 0.0173 (7) | −0.0004 (6) | 0.0028 (6) | 0.0008 (6) |
C17 | 0.0182 (7) | 0.0173 (7) | 0.0150 (7) | 0.0024 (6) | 0.0029 (5) | −0.0001 (6) |
C18 | 0.0193 (7) | 0.0173 (7) | 0.0141 (7) | −0.0024 (6) | 0.0020 (5) | 0.0027 (6) |
C19 | 0.0223 (8) | 0.0179 (8) | 0.0194 (8) | 0.0008 (6) | 0.0039 (6) | 0.0021 (6) |
C20 | 0.0292 (9) | 0.0193 (8) | 0.0213 (8) | −0.0066 (7) | 0.0075 (6) | −0.0027 (6) |
C21 | 0.0230 (8) | 0.0291 (9) | 0.0190 (8) | −0.0091 (7) | 0.0035 (6) | −0.0016 (7) |
C22 | 0.0162 (7) | 0.0268 (9) | 0.0195 (8) | −0.0004 (6) | 0.0015 (6) | 0.0003 (7) |
C23 | 0.0191 (7) | 0.0185 (8) | 0.0186 (7) | 0.0004 (6) | 0.0021 (6) | −0.0007 (6) |
O1W | 0.0273 (6) | 0.0292 (7) | 0.0257 (6) | 0.0054 (5) | 0.0076 (5) | 0.0018 (5) |
O1—C1 | 1.3692 (18) | C8—H8A | 0.9500 |
O1—C12 | 1.3826 (17) | C9—C10 | 1.433 (2) |
O2—C13 | 1.2383 (18) | C10—C11 | 1.435 (2) |
N1—C13 | 1.3499 (19) | C11—C12 | 1.356 (2) |
N1—N2 | 1.3954 (17) | C11—H11A | 0.9500 |
N1—H1N1 | 0.94 (2) | C12—C13 | 1.466 (2) |
N2—C14 | 1.2860 (19) | C14—C15 | 1.443 (2) |
N3—C16 | 1.336 (2) | C14—H14A | 0.9500 |
N3—N4 | 1.3636 (18) | C15—C16 | 1.392 (2) |
N3—H1N3 | 0.96 (2) | C15—C17 | 1.423 (2) |
N4—C17 | 1.3372 (19) | C16—H16A | 0.9500 |
C1—C10 | 1.381 (2) | C17—C18 | 1.476 (2) |
C1—C2 | 1.397 (2) | C18—C23 | 1.393 (2) |
C2—C3 | 1.366 (2) | C18—C19 | 1.402 (2) |
C2—H2A | 0.9500 | C19—C20 | 1.389 (2) |
C3—C4 | 1.433 (2) | C19—H19A | 0.9500 |
C3—H3A | 0.9500 | C20—C21 | 1.387 (2) |
C4—C5 | 1.415 (2) | C20—H20A | 0.9500 |
C4—C9 | 1.422 (2) | C21—C22 | 1.384 (2) |
C5—C6 | 1.376 (2) | C21—H21A | 0.9500 |
C5—H5A | 0.9500 | C22—C23 | 1.392 (2) |
C6—C7 | 1.407 (2) | C22—H22A | 0.9500 |
C6—H6A | 0.9500 | C23—H23A | 0.9500 |
C7—C8 | 1.376 (2) | O1W—H1W1 | 0.8628 |
C7—H7A | 0.9500 | O1W—H2W1 | 0.8895 |
C8—C9 | 1.408 (2) | ||
C1—O1—C12 | 105.57 (12) | C12—C11—H11A | 126.8 |
C13—N1—N2 | 118.93 (13) | C10—C11—H11A | 126.8 |
C13—N1—H1N1 | 119.8 (15) | C11—C12—O1 | 111.43 (13) |
N2—N1—H1N1 | 121.1 (15) | C11—C12—C13 | 131.48 (14) |
C14—N2—N1 | 113.00 (12) | O1—C12—C13 | 117.09 (13) |
C16—N3—N4 | 112.94 (13) | O2—C13—N1 | 124.46 (14) |
C16—N3—H1N3 | 128.8 (15) | O2—C13—C12 | 121.30 (14) |
N4—N3—H1N3 | 118.2 (15) | N1—C13—C12 | 114.24 (13) |
C17—N4—N3 | 104.65 (13) | N2—C14—C15 | 123.27 (14) |
O1—C1—C10 | 110.89 (13) | N2—C14—H14A | 118.4 |
O1—C1—C2 | 124.22 (14) | C15—C14—H14A | 118.4 |
C10—C1—C2 | 124.89 (14) | C16—C15—C17 | 104.31 (13) |
C3—C2—C1 | 116.37 (15) | C16—C15—C14 | 130.05 (14) |
C3—C2—H2A | 121.8 | C17—C15—C14 | 125.31 (14) |
C1—C2—H2A | 121.8 | N3—C16—C15 | 107.04 (14) |
C2—C3—C4 | 122.18 (15) | N3—C16—H16A | 126.5 |
C2—C3—H3A | 118.9 | C15—C16—H16A | 126.5 |
C4—C3—H3A | 118.9 | N4—C17—C15 | 111.07 (13) |
C5—C4—C9 | 118.60 (15) | N4—C17—C18 | 121.01 (14) |
C5—C4—C3 | 120.88 (15) | C15—C17—C18 | 127.84 (13) |
C9—C4—C3 | 120.51 (14) | C23—C18—C19 | 118.89 (14) |
C6—C5—C4 | 120.73 (15) | C23—C18—C17 | 120.96 (14) |
C6—C5—H5A | 119.6 | C19—C18—C17 | 120.10 (14) |
C4—C5—H5A | 119.6 | C20—C19—C18 | 120.38 (15) |
C5—C6—C7 | 120.41 (15) | C20—C19—H19A | 119.8 |
C5—C6—H6A | 119.8 | C18—C19—H19A | 119.8 |
C7—C6—H6A | 119.8 | C21—C20—C19 | 120.06 (15) |
C8—C7—C6 | 120.04 (15) | C21—C20—H20A | 120.0 |
C8—C7—H7A | 120.0 | C19—C20—H20A | 120.0 |
C6—C7—H7A | 120.0 | C22—C21—C20 | 120.04 (15) |
C7—C8—C9 | 120.71 (15) | C22—C21—H21A | 120.0 |
C7—C8—H8A | 119.6 | C20—C21—H21A | 120.0 |
C9—C8—H8A | 119.6 | C21—C22—C23 | 120.13 (15) |
C8—C9—C4 | 119.48 (14) | C21—C22—H22A | 119.9 |
C8—C9—C10 | 123.75 (14) | C23—C22—H22A | 119.9 |
C4—C9—C10 | 116.75 (14) | C22—C23—C18 | 120.45 (15) |
C1—C10—C9 | 119.27 (14) | C22—C23—H23A | 119.8 |
C1—C10—C11 | 105.79 (13) | C18—C23—H23A | 119.8 |
C9—C10—C11 | 134.91 (14) | H1W1—O1W—H2W1 | 110.0 |
C12—C11—C10 | 106.30 (13) | ||
C13—N1—N2—C14 | −157.33 (14) | C1—O1—C12—C11 | −0.81 (17) |
C16—N3—N4—C17 | −0.15 (17) | C1—O1—C12—C13 | 178.90 (13) |
C12—O1—C1—C10 | 1.37 (17) | N2—N1—C13—O2 | 0.8 (2) |
C12—O1—C1—C2 | −177.96 (15) | N2—N1—C13—C12 | −178.86 (13) |
O1—C1—C2—C3 | −179.88 (15) | C11—C12—C13—O2 | −0.6 (3) |
C10—C1—C2—C3 | 0.9 (3) | O1—C12—C13—O2 | 179.70 (14) |
C1—C2—C3—C4 | −1.5 (3) | C11—C12—C13—N1 | 178.97 (16) |
C2—C3—C4—C5 | −177.51 (16) | O1—C12—C13—N1 | −0.7 (2) |
C2—C3—C4—C9 | 1.8 (3) | N1—N2—C14—C15 | 178.31 (13) |
C9—C4—C5—C6 | −0.8 (2) | N2—C14—C15—C16 | 0.5 (3) |
C3—C4—C5—C6 | 178.56 (16) | N2—C14—C15—C17 | −171.90 (14) |
C4—C5—C6—C7 | 1.8 (3) | N4—N3—C16—C15 | 0.06 (17) |
C5—C6—C7—C8 | −1.5 (3) | C17—C15—C16—N3 | 0.06 (16) |
C6—C7—C8—C9 | 0.1 (2) | C14—C15—C16—N3 | −173.53 (15) |
C7—C8—C9—C4 | 0.9 (2) | N3—N4—C17—C15 | 0.18 (16) |
C7—C8—C9—C10 | −177.53 (15) | N3—N4—C17—C18 | 177.03 (13) |
C5—C4—C9—C8 | −0.6 (2) | C16—C15—C17—N4 | −0.15 (17) |
C3—C4—C9—C8 | −179.93 (15) | C14—C15—C17—N4 | 173.83 (14) |
C5—C4—C9—C10 | 177.97 (14) | C16—C15—C17—C18 | −176.73 (14) |
C3—C4—C9—C10 | −1.4 (2) | C14—C15—C17—C18 | −2.8 (2) |
O1—C1—C10—C9 | −179.87 (13) | N4—C17—C18—C23 | 136.78 (15) |
C2—C1—C10—C9 | −0.5 (2) | C15—C17—C18—C23 | −46.9 (2) |
O1—C1—C10—C11 | −1.39 (17) | N4—C17—C18—C19 | −45.9 (2) |
C2—C1—C10—C11 | 177.93 (15) | C15—C17—C18—C19 | 130.41 (16) |
C8—C9—C10—C1 | 179.24 (15) | C23—C18—C19—C20 | 1.6 (2) |
C4—C9—C10—C1 | 0.8 (2) | C17—C18—C19—C20 | −175.76 (14) |
C8—C9—C10—C11 | 1.3 (3) | C18—C19—C20—C21 | 0.1 (2) |
C4—C9—C10—C11 | −177.16 (16) | C19—C20—C21—C22 | −1.4 (2) |
C1—C10—C11—C12 | 0.84 (17) | C20—C21—C22—C23 | 0.9 (2) |
C9—C10—C11—C12 | 178.97 (17) | C21—C22—C23—C18 | 0.8 (2) |
C10—C11—C12—O1 | −0.02 (18) | C19—C18—C23—C22 | −2.1 (2) |
C10—C11—C12—C13 | −179.69 (16) | C17—C18—C23—C22 | 175.28 (14) |
Cg1 and Cg2 are the centroids of the C18–C23 and N3/N4/C17/C15/C16 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···N4i | 0.86 | 2.13 | 2.9625 (18) | 163 |
O1W—H2W1···O2ii | 0.89 | 2.12 | 2.9465 (16) | 154 |
N3—H1N3···O2iii | 0.95 (2) | 2.52 (3) | 3.2162 (18) | 130.4 (19) |
N3—H1N3···N2iii | 0.95 (2) | 2.10 (3) | 2.9927 (19) | 155 (2) |
N1—H1N1···O1W | 0.94 (3) | 2.06 (3) | 2.9388 (18) | 155 (2) |
C14—H14A···O1W | 0.95 | 2.54 | 3.2877 (18) | 136 |
C16—H16A···N4iv | 0.95 | 2.50 | 3.430 (2) | 167 |
C21—H21A···O2v | 0.95 | 2.53 | 3.318 (2) | 140 |
C7—H7A···Cg2vi | 0.95 | 2.80 | 3.6022 (18) | 142 |
C22—H22A···Cg1ii | 0.95 | 2.93 | 3.5274 (16) | 122 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+2, y+1/2, −z+1/2; (v) x−1, y−1, z; (vi) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C23H16N4O2·H2O |
Mr | 398.41 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 7.1383 (1), 9.3928 (1), 28.4200 (4) |
β (°) | 96.864 (1) |
V (Å3) | 1891.86 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.31 × 0.25 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.971, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21248, 5516, 3857 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.129, 1.03 |
No. of reflections | 5516 |
No. of parameters | 279 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.27 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 and Cg2 are the centroids of the C18–C23 and N3/N4/C17/C15/C16 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···N4i | 0.86 | 2.13 | 2.9625 (18) | 163 |
O1W—H2W1···O2ii | 0.89 | 2.12 | 2.9465 (16) | 154 |
N3—H1N3···O2iii | 0.95 (2) | 2.52 (3) | 3.2162 (18) | 130.4 (19) |
N3—H1N3···N2iii | 0.95 (2) | 2.10 (3) | 2.9927 (19) | 155 (2) |
N1—H1N1···O1W | 0.94 (3) | 2.06 (3) | 2.9388 (18) | 155 (2) |
C14—H14A···O1W | 0.95 | 2.54 | 3.2877 (18) | 136 |
C16—H16A···N4iv | 0.95 | 2.50 | 3.430 (2) | 167 |
C21—H21A···O2v | 0.95 | 2.53 | 3.318 (2) | 140 |
C7—H7A···Cg2vi | 0.95 | 2.80 | 3.6022 (18) | 142 |
C22—H22A···Cg1ii | 0.95 | 2.93 | 3.5274 (16) | 122 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+2, y+1/2, −z+1/2; (v) x−1, y−1, z; (vi) −x+1, −y+2, −z. |
Acknowledgements
HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). AMI thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Acidhydrazones and their condensation products possessing an azometine –NHN═ CH– proton constitute an important class of compounds for new drug development. In the past several years, numerous compounds with diverse structural features have been reported. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. Hydrazides, hydrazones and their adducts have displayed diverse range of biological properties such as anti-viral (Jahagirdar et al., 1990), anti-tuberculosis (Cavier et al., 1965) and anti-inflammatory activities (Silva et al., 2005; Eissa et al., 2009). We have synthesized the title compound to study its crystal structure and evaluate its biological activities.
The title compound (Fig. 1) consists of one molecule of N'-[(E)-(3-phenyl-1H-pyrazol-4-yl)methylidene]naphtho [2,1-b]furan-2-carbohydrazide and a water molecule. The pyrazole ring (N3/N4/C15–C17) is approximately planar with a maximum deviation of 0.023 (1) Å at atom C17. This ring makes dihedral angles of 28.63 (6)° with the naphtho[2,1-b]furan ring system (O1/C1–C12; maximum deviation of 0.016 (1) Å at atom C10) and 46.44 (7)° with the benzene ring (C18–C23; maximum deviation of 0.012 (1) Å at atom C18). Bond lengths and angles are comparable to a related structure (Choi et al., 2009).
In the crystal, (Fig. 2), O1W—H1W1···N4, O1W—H2W1···O2, N3—H1N3···O2, N3—H1N3···N2, N1—H1N1···O1W C14—H14A···O1W, C16—H16A···N4 and C21—H21A···O2 hydrogen bonds (Table 1) link the molecules to form sheets parallel to the ab plane. The crystal structure is further stabilized by C—H···π interactions (Table 1) involving the centroids of pyrazole (Cg1) and benzene (Cg2) rings.