organic compounds
(2E)-2-[1-(2-Hydroxy-4-methoxyphenyl)ethylidene]-N-phenylhydrazinecarboxamide monohydrate
aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
*Correspondence e-mail: eesans@yahoo.com
The title compound, C16H17N3O3·H2O, exists in the E conformation with respect to the azomethine C=N double bond. While the phenyl ring is almost coplanar with the central hydrazinecarboxamide group [dihedral angle = 14.18 (11)°], it is twisted slightly with respect to the other aromatic ring in the molecule, with a dihedral angle of 22.88 (13)°. The packing is dominated by O—H⋯O, N—H⋯O and C—H⋯O hydrogen-bond interactions, forming a three-dimensional supramolecular structure which is augmented by two types of C—H⋯π interactions. An intramolecular O—H⋯N interaction is also present in the molecule.
Related literature
For the application of hydrazinecarboxamides as enzyme inhibitors and as a source of self-complementary bidirectional hydrogen-bonding motifs, see: Lam et al. (1994); Chorev & Goodman (1993); Zhao et al. (1990). For the synthesis of related compounds, see: Sreekanth et al. (2004). For standard bond-length data, see: Allen et al. (1987). For related structures, see: Sithambaresan & Kurup (2011); Siji et al. (2010).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536812039414/bv2210sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039414/bv2210Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812039414/bv2210Isup3.cml
The title compound was prepared by adapting a reported procedure (Sreekanth et al., 2004). To a warm ethanolic solution of N-phenylsemicarbazide (0.302 g, 2 mmol), an ethanolic solution of 1-(2-hydroxy-4-methoxyphenyl)ethanone (0.332 g, 2 mmol) was added and the resulting solution was refluxed for 3 h after adding three drops of glacial acetic acid. On cooling the solution colorless crystals were separated out. Single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from its ethanolic solution.
All H atoms on C were placed in calculated positions, guided by difference maps, with C—H bond distances 0.93–0.96 Å. H atoms were assigned as Uiso = 1.2Ueq. H1A and H1B atoms of O1S were located from difference maps and restrained using DFIX and DANG instructions with O—H = 0.86 (2) and H···H = 1.36 (2) Å respectively. N2—H2N, N3—H3 and O2—H2' atoms were located from difference maps and restrained using DFIX instructions with bond distance of 0.88 (1) Å.
Hydrazinecarboxamides have gained considerable importance in recent years in the design of enzyme inhibitors (Lam et al., 1994), as replacement for the amide (–CO–NH–) bond in peptidomimetics (Chorev & Goodman, 1993) and as sources of self-complementary bidirectional hydrogen bonding motif in supramolecular chemistry (Zhao et al., 1990). As a continuous work on the hydrazinecarboxamide compounds, a new hydrazinecarboxamide compound, (2E)-2-[1-(2-hydroxy-4-methoxyphenyl)ethylidene]-N-phenylhydrazinecarboxamide monohydrate, was prepared and structurally characterized. The ORTEP view of the title compound is shown in Fig. 1.
The compound crystallizes in monoclinic ═N1 bond (Sithambaresan & Kurup, 2011; Siji et al., 2010) and it exists in amido form with C9═O3 bond length of 1.212 (3) Å which is very close to a formal C═O bond length [1.21 Å] (Allen et al., 1987). The phenyl ring is almost coplanar with the central hydrazinecarboxamide moiety with maximum deviation of -0.060 (3) Å for the C1 atom. The two aromatic rings are twisted with dihedral angle of 22.88 (13)°.
P21/c. The molecule adopts an E configuration with respect to C7While the intramolecular O—H···N and C—H···O hydrogen bonds increase the rigidity of the molecule, intermolecular O—H···O, N—H···O, C—H···O hydrogen bonding interactions (Table 1) links the adjacent molecules directly and through water molecule forming an infinite three-dimensional supramolecular structure in the lattice (Fig. 2). Phenylhydrazinecarboxamide molecules also interact through two types of C—H···π interactions (Fig. 3) with the H···π distances of 2.92 and 2.79 Å and very weak π–π interactions with a shortest centroid–centroid distance of 5.0552 (18) Å. The parallel arrangement of the molecules along b axis is shown in Fig. 4.
For the application of hydrazinecarboxamides as enzyme inhibitors and as a source of self-complementary bidirectional hydrogen-bonding motifs, see: Lam et al. (1994); Chorev & Goodman (1993); Zhao et al. (1990). For the synthesis of related compounds, see: Sreekanth et al. (2004). For standard bond-length data, see: Allen et al. (1987). For related structures, see: Sithambaresan & Kurup (2011); Siji et al. (2010).
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).Fig. 1. ORTEP view of the compound, drawn with 50% probability displacement ellipsoids for the non-H atoms. | |
Fig. 2. Graphical representation showing three-dimensional supramolecular hydrogen bonding network in the crystal structure of C16H17N3O3.H2O. | |
Fig. 3. C—H···π interactions present in the compound C16H17N3O3.H2O. | |
Fig. 4. Packing diagram of the compound showing the parallel arrangement of the molecules along b axis. |
C16H17N3O3·H2O | F(000) = 672 |
Mr = 317.34 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2335 reflections |
a = 12.4020 (18) Å | θ = 2.6–28.5° |
b = 13.7808 (19) Å | µ = 0.10 mm−1 |
c = 9.3919 (10) Å | T = 296 K |
β = 96.813 (7)° | Block, light yellow |
V = 1593.8 (4) Å3 | 0.50 × 0.30 × 0.25 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 2809 independent reflections |
Radiation source: fine-focus sealed tube | 1807 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.6° |
ω and φ scans | h = −14→14 |
Absorption correction: multi-scan (SADABS (Bruker, 2004) | k = −15→16 |
Tmin = 0.966, Tmax = 0.976 | l = −11→11 |
12097 measured reflections |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0711P)2 + 0.2072P] where P = (Fo2 + 2Fc2)/3 |
2809 reflections | (Δ/σ)max = 0.002 |
230 parameters | Δρmax = 0.22 e Å−3 |
6 restraints | Δρmin = −0.19 e Å−3 |
C16H17N3O3·H2O | V = 1593.8 (4) Å3 |
Mr = 317.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.4020 (18) Å | µ = 0.10 mm−1 |
b = 13.7808 (19) Å | T = 296 K |
c = 9.3919 (10) Å | 0.50 × 0.30 × 0.25 mm |
β = 96.813 (7)° |
Bruker Kappa APEXII CCD diffractometer | 2809 independent reflections |
Absorption correction: multi-scan (SADABS (Bruker, 2004) | 1807 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.976 | Rint = 0.083 |
12097 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 6 restraints |
wR(F2) = 0.172 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.22 e Å−3 |
2809 reflections | Δρmin = −0.19 e Å−3 |
230 parameters |
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 | 0.00919 (16) | 0.45528 (15) | 0.7326 (2) | 0.0873 (6) | |
O2 | 0.28586 (14) | 0.46101 (12) | 0.42646 (18) | 0.0649 (5) | |
O3 | 0.48111 (13) | 0.39835 (12) | 0.18956 (17) | 0.0673 (5) | |
O1S | 0.46607 (17) | 0.43758 (13) | 0.6547 (2) | 0.0782 (6) | |
N1 | 0.34225 (14) | 0.30092 (14) | 0.32720 (19) | 0.0550 (5) | |
N2 | 0.41511 (16) | 0.25435 (15) | 0.2542 (2) | 0.0579 (5) | |
N3 | 0.55055 (16) | 0.25697 (15) | 0.1149 (2) | 0.0595 (5) | |
C1 | 0.1243 (2) | 0.26313 (19) | 0.5438 (3) | 0.0665 (7) | |
H1 | 0.1149 | 0.1964 | 0.5341 | 0.080* | |
C2 | 0.0592 (2) | 0.3136 (2) | 0.6243 (3) | 0.0721 (7) | |
H2 | 0.0057 | 0.2814 | 0.6674 | 0.087* | |
C3 | 0.07267 (18) | 0.41231 (19) | 0.6422 (3) | 0.0632 (6) | |
C4 | 0.14813 (18) | 0.46014 (18) | 0.5735 (2) | 0.0605 (6) | |
H4 | 0.1560 | 0.5270 | 0.5831 | 0.073* | |
C5 | 0.21263 (16) | 0.40877 (17) | 0.4898 (2) | 0.0525 (6) | |
C6 | 0.20481 (17) | 0.30831 (17) | 0.4753 (2) | 0.0527 (6) | |
C7 | 0.27824 (18) | 0.25124 (17) | 0.3976 (2) | 0.0549 (6) | |
C8 | 0.2817 (2) | 0.14371 (19) | 0.4067 (3) | 0.0725 (7) | |
H8A | 0.2911 | 0.1172 | 0.3145 | 0.109* | |
H8B | 0.2149 | 0.1202 | 0.4363 | 0.109* | |
H8C | 0.3413 | 0.1242 | 0.4754 | 0.109* | |
C9 | 0.48365 (17) | 0.31043 (17) | 0.1865 (2) | 0.0528 (5) | |
C10 | 0.63021 (18) | 0.29082 (16) | 0.0333 (2) | 0.0544 (6) | |
C11 | 0.6348 (2) | 0.38417 (19) | −0.0166 (3) | 0.0703 (7) | |
H11 | 0.5839 | 0.4297 | 0.0053 | 0.084* | |
C12 | 0.7142 (2) | 0.4102 (2) | −0.0987 (3) | 0.0797 (8) | |
H12 | 0.7167 | 0.4735 | −0.1323 | 0.096* | |
C13 | 0.7897 (2) | 0.3447 (2) | −0.1319 (3) | 0.0858 (9) | |
H13 | 0.8439 | 0.3628 | −0.1870 | 0.103* | |
C14 | 0.7843 (3) | 0.2526 (3) | −0.0828 (4) | 0.0974 (11) | |
H14 | 0.8355 | 0.2074 | −0.1046 | 0.117* | |
C15 | 0.7047 (2) | 0.2249 (2) | −0.0017 (3) | 0.0787 (8) | |
H15 | 0.7016 | 0.1611 | 0.0295 | 0.094* | |
C16 | 0.0259 (3) | 0.5537 (2) | 0.7664 (3) | 0.0955 (10) | |
H16A | 0.1001 | 0.5636 | 0.8055 | 0.143* | |
H16B | −0.0211 | 0.5728 | 0.8357 | 0.143* | |
H16C | 0.0100 | 0.5920 | 0.6812 | 0.143* | |
H1A | 0.424 (3) | 0.459 (3) | 0.583 (3) | 0.141 (16)* | |
H1B | 0.486 (3) | 0.4887 (17) | 0.698 (3) | 0.109 (12)* | |
H3 | 0.548 (2) | 0.1938 (8) | 0.126 (3) | 0.089 (9)* | |
H2' | 0.318 (2) | 0.4169 (16) | 0.378 (3) | 0.094 (10)* | |
H2N | 0.4174 (19) | 0.1907 (8) | 0.245 (2) | 0.063 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0817 (13) | 0.0877 (15) | 0.1018 (14) | 0.0039 (10) | 0.0499 (10) | 0.0000 (11) |
O2 | 0.0673 (11) | 0.0548 (11) | 0.0776 (11) | −0.0040 (8) | 0.0296 (8) | 0.0036 (8) |
O3 | 0.0756 (11) | 0.0487 (10) | 0.0802 (12) | 0.0015 (8) | 0.0203 (8) | −0.0082 (8) |
O1S | 0.0866 (13) | 0.0528 (11) | 0.0914 (14) | −0.0062 (10) | −0.0048 (11) | −0.0055 (10) |
N1 | 0.0542 (11) | 0.0577 (13) | 0.0540 (11) | 0.0038 (9) | 0.0097 (8) | −0.0022 (8) |
N2 | 0.0619 (12) | 0.0503 (13) | 0.0637 (12) | 0.0046 (9) | 0.0178 (9) | −0.0037 (9) |
N3 | 0.0641 (12) | 0.0469 (12) | 0.0710 (13) | 0.0047 (9) | 0.0225 (10) | −0.0005 (9) |
C1 | 0.0627 (15) | 0.0601 (16) | 0.0788 (17) | −0.0095 (12) | 0.0176 (13) | 0.0023 (12) |
C2 | 0.0637 (15) | 0.0726 (19) | 0.0847 (18) | −0.0111 (13) | 0.0283 (13) | 0.0069 (14) |
C3 | 0.0536 (14) | 0.0717 (18) | 0.0668 (15) | 0.0032 (12) | 0.0176 (11) | 0.0055 (12) |
C4 | 0.0558 (13) | 0.0601 (15) | 0.0673 (15) | 0.0026 (11) | 0.0138 (11) | 0.0012 (11) |
C5 | 0.0459 (12) | 0.0585 (15) | 0.0536 (13) | −0.0029 (10) | 0.0077 (9) | 0.0074 (10) |
C6 | 0.0494 (12) | 0.0576 (15) | 0.0505 (12) | −0.0026 (10) | 0.0037 (9) | 0.0044 (10) |
C7 | 0.0519 (13) | 0.0595 (15) | 0.0518 (13) | −0.0010 (10) | −0.0001 (10) | 0.0014 (10) |
C8 | 0.0812 (18) | 0.0603 (16) | 0.0766 (17) | −0.0002 (13) | 0.0116 (13) | −0.0021 (12) |
C9 | 0.0521 (13) | 0.0493 (14) | 0.0560 (14) | 0.0013 (10) | 0.0023 (10) | −0.0033 (10) |
C10 | 0.0536 (13) | 0.0552 (15) | 0.0548 (13) | 0.0017 (10) | 0.0076 (10) | −0.0023 (10) |
C11 | 0.0765 (17) | 0.0573 (16) | 0.0808 (17) | 0.0057 (13) | 0.0251 (13) | 0.0006 (13) |
C12 | 0.097 (2) | 0.0648 (18) | 0.0831 (19) | −0.0106 (15) | 0.0328 (15) | 0.0019 (13) |
C13 | 0.0797 (19) | 0.095 (2) | 0.089 (2) | −0.0092 (16) | 0.0368 (15) | −0.0005 (17) |
C14 | 0.093 (2) | 0.089 (2) | 0.120 (3) | 0.0294 (17) | 0.0550 (19) | 0.0167 (18) |
C15 | 0.0864 (19) | 0.0643 (18) | 0.091 (2) | 0.0191 (14) | 0.0335 (15) | 0.0115 (14) |
C16 | 0.100 (2) | 0.091 (3) | 0.103 (2) | 0.0114 (18) | 0.0410 (18) | −0.0163 (18) |
O1—C3 | 1.360 (3) | C4—H4 | 0.9300 |
O1—C16 | 1.403 (3) | C5—C6 | 1.393 (3) |
O2—C5 | 1.351 (3) | C6—C7 | 1.462 (3) |
O2—H2' | 0.881 (10) | C7—C8 | 1.485 (3) |
O3—C9 | 1.212 (3) | C8—H8A | 0.9600 |
O1S—H1A | 0.857 (18) | C8—H8B | 0.9600 |
O1S—H1B | 0.837 (18) | C8—H8C | 0.9600 |
N1—C7 | 1.289 (3) | C10—C15 | 1.363 (3) |
N1—N2 | 1.358 (3) | C10—C11 | 1.373 (3) |
N2—C9 | 1.361 (3) | C11—C12 | 1.368 (3) |
N2—H2N | 0.882 (10) | C11—H11 | 0.9300 |
N3—C9 | 1.348 (3) | C12—C13 | 1.363 (4) |
N3—C10 | 1.400 (3) | C12—H12 | 0.9300 |
N3—H3 | 0.878 (10) | C13—C14 | 1.354 (4) |
C1—C2 | 1.360 (4) | C13—H13 | 0.9300 |
C1—C6 | 1.397 (3) | C14—C15 | 1.370 (4) |
C1—H1 | 0.9300 | C14—H14 | 0.9300 |
C2—C3 | 1.379 (4) | C15—H15 | 0.9300 |
C2—H2 | 0.9300 | C16—H16A | 0.9600 |
C3—C4 | 1.368 (3) | C16—H16B | 0.9600 |
C4—C5 | 1.381 (3) | C16—H16C | 0.9600 |
C3—O1—C16 | 118.8 (2) | C7—C8—H8B | 109.5 |
C5—O2—H2' | 103 (2) | H8A—C8—H8B | 109.5 |
H1A—O1S—H1B | 102 (3) | C7—C8—H8C | 109.5 |
C7—N1—N2 | 119.7 (2) | H8A—C8—H8C | 109.5 |
N1—N2—C9 | 117.21 (19) | H8B—C8—H8C | 109.5 |
N1—N2—H2N | 123.3 (16) | O3—C9—N3 | 125.3 (2) |
C9—N2—H2N | 119.4 (16) | O3—C9—N2 | 122.5 (2) |
C9—N3—C10 | 127.4 (2) | N3—C9—N2 | 112.2 (2) |
C9—N3—H3 | 117 (2) | C15—C10—C11 | 119.0 (2) |
C10—N3—H3 | 115 (2) | C15—C10—N3 | 116.9 (2) |
C2—C1—C6 | 122.1 (2) | C11—C10—N3 | 124.0 (2) |
C2—C1—H1 | 118.9 | C12—C11—C10 | 120.0 (2) |
C6—C1—H1 | 118.9 | C12—C11—H11 | 120.0 |
C1—C2—C3 | 120.0 (2) | C10—C11—H11 | 120.0 |
C1—C2—H2 | 120.0 | C13—C12—C11 | 121.0 (3) |
C3—C2—H2 | 120.0 | C13—C12—H12 | 119.5 |
O1—C3—C4 | 124.3 (2) | C11—C12—H12 | 119.5 |
O1—C3—C2 | 115.8 (2) | C14—C13—C12 | 118.6 (3) |
C4—C3—C2 | 119.9 (2) | C14—C13—H13 | 120.7 |
C3—C4—C5 | 119.8 (2) | C12—C13—H13 | 120.7 |
C3—C4—H4 | 120.1 | C13—C14—C15 | 121.2 (3) |
C5—C4—H4 | 120.1 | C13—C14—H14 | 119.4 |
O2—C5—C4 | 116.3 (2) | C15—C14—H14 | 119.4 |
O2—C5—C6 | 121.9 (2) | C10—C15—C14 | 120.1 (3) |
C4—C5—C6 | 121.8 (2) | C10—C15—H15 | 119.9 |
C5—C6—C1 | 116.3 (2) | C14—C15—H15 | 119.9 |
C5—C6—C7 | 122.9 (2) | O1—C16—H16A | 109.5 |
C1—C6—C7 | 120.8 (2) | O1—C16—H16B | 109.5 |
N1—C7—C6 | 115.4 (2) | H16A—C16—H16B | 109.5 |
N1—C7—C8 | 123.0 (2) | O1—C16—H16C | 109.5 |
C6—C7—C8 | 121.6 (2) | H16A—C16—H16C | 109.5 |
C7—C8—H8A | 109.5 | H16B—C16—H16C | 109.5 |
C7—N1—N2—C9 | −177.41 (18) | C5—C6—C7—N1 | −8.6 (3) |
C6—C1—C2—C3 | −1.0 (4) | C1—C6—C7—N1 | 173.59 (19) |
C16—O1—C3—C4 | −4.5 (4) | C5—C6—C7—C8 | 168.3 (2) |
C16—O1—C3—C2 | 174.0 (2) | C1—C6—C7—C8 | −9.5 (3) |
C1—C2—C3—O1 | −175.5 (2) | C10—N3—C9—O3 | 1.1 (4) |
C1—C2—C3—C4 | 3.0 (4) | C10—N3—C9—N2 | 179.5 (2) |
O1—C3—C4—C5 | 176.5 (2) | N1—N2—C9—O3 | −0.1 (3) |
C2—C3—C4—C5 | −1.8 (4) | N1—N2—C9—N3 | −178.56 (18) |
C3—C4—C5—O2 | −179.4 (2) | C9—N3—C10—C15 | 165.1 (2) |
C3—C4—C5—C6 | −1.4 (3) | C9—N3—C10—C11 | −17.3 (4) |
O2—C5—C6—C1 | −178.8 (2) | C15—C10—C11—C12 | −0.8 (4) |
C4—C5—C6—C1 | 3.3 (3) | N3—C10—C11—C12 | −178.4 (2) |
O2—C5—C6—C7 | 3.4 (3) | C10—C11—C12—C13 | −0.2 (4) |
C4—C5—C6—C7 | −174.6 (2) | C11—C12—C13—C14 | 0.5 (5) |
C2—C1—C6—C5 | −2.1 (3) | C12—C13—C14—C15 | 0.1 (5) |
C2—C1—C6—C7 | 175.8 (2) | C11—C10—C15—C14 | 1.5 (4) |
N2—N1—C7—C6 | 178.56 (17) | N3—C10—C15—C14 | 179.2 (3) |
N2—N1—C7—C8 | 1.7 (3) | C13—C14—C15—C10 | −1.2 (5) |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2′···N1 | 0.88 (1) | 1.71 (2) | 2.526 (2) | 154 (3) |
N2—H2N···O1Si | 0.88 (1) | 2.08 (1) | 2.900 (3) | 154 (2) |
N3—H3···O1Si | 0.88 (1) | 2.11 (2) | 2.918 (3) | 153 (3) |
O1S—H1A···O2 | 0.86 (2) | 2.12 (2) | 2.925 (3) | 156 (3) |
O1S—H1B···O3ii | 0.84 (2) | 1.90 (2) | 2.730 (3) | 174 (3) |
C8—H8C···O3iii | 0.96 | 2.51 | 3.457 (3) | 167 |
C11—H11···O3 | 0.93 | 2.31 | 2.881 (3) | 119 |
C13—H13···O1iv | 0.93 | 2.60 | 3.489 (3) | 160 |
C8—H8A···Cg1v | 0.96 | 2.92 | 3.543 (3) | 123 |
C16—H16C···Cg1vi | 0.96 | 2.79 | 3.645 (4) | 148 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z+1/2; (iv) x+1, y, z−1; (v) x, −y−1/2, z−3/2; (vi) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H17N3O3·H2O |
Mr | 317.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 12.4020 (18), 13.7808 (19), 9.3919 (10) |
β (°) | 96.813 (7) |
V (Å3) | 1593.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.50 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS (Bruker, 2004) |
Tmin, Tmax | 0.966, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12097, 2809, 1807 |
Rint | 0.083 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.172, 1.02 |
No. of reflections | 2809 |
No. of parameters | 230 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.19 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2010), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2'···N1 | 0.881 (10) | 1.706 (16) | 2.526 (2) | 154 (3) |
N2—H2N···O1Si | 0.882 (10) | 2.082 (14) | 2.900 (3) | 154 (2) |
N3—H3···O1Si | 0.878 (10) | 2.110 (16) | 2.918 (3) | 153 (3) |
O1S—H1A···O2 | 0.857 (18) | 2.12 (2) | 2.925 (3) | 156 (3) |
O1S—H1B···O3ii | 0.837 (18) | 1.896 (18) | 2.730 (3) | 174 (3) |
C8—H8C···O3iii | 0.96 | 2.51 | 3.457 (3) | 167.1 |
C11—H11···O3 | 0.93 | 2.31 | 2.881 (3) | 119.3 |
C13—H13···O1iv | 0.93 | 2.60 | 3.489 (3) | 160.0 |
C8—H8A···Cg1v | 0.96 | 2.92 | 3.543 (3) | 123 |
C16—H16C···Cg1vi | 0.96 | 2.79 | 3.645 (4) | 148 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z+1/2; (iv) x+1, y, z−1; (v) x, −y−1/2, z−3/2; (vi) −x, −y+1, −z+1. |
Acknowledgements
CFA is grateful to the University Grants Commission, New Delhi, India, for the award of a Teacher Fellowship. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi 22, India, for the single-crystal X-ray diffraction measurements.
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.
Hydrazinecarboxamides have gained considerable importance in recent years in the design of enzyme inhibitors (Lam et al., 1994), as replacement for the amide (–CO–NH–) bond in peptidomimetics (Chorev & Goodman, 1993) and as sources of self-complementary bidirectional hydrogen bonding motif in supramolecular chemistry (Zhao et al., 1990). As a continuous work on the hydrazinecarboxamide compounds, a new hydrazinecarboxamide compound, (2E)-2-[1-(2-hydroxy-4-methoxyphenyl)ethylidene]-N-phenylhydrazinecarboxamide monohydrate, was prepared and structurally characterized. The ORTEP view of the title compound is shown in Fig. 1.
The compound crystallizes in monoclinic space group P21/c. The molecule adopts an E configuration with respect to C7═N1 bond (Sithambaresan & Kurup, 2011; Siji et al., 2010) and it exists in amido form with C9═O3 bond length of 1.212 (3) Å which is very close to a formal C═O bond length [1.21 Å] (Allen et al., 1987). The phenyl ring is almost coplanar with the central hydrazinecarboxamide moiety with maximum deviation of -0.060 (3) Å for the C1 atom. The two aromatic rings are twisted with dihedral angle of 22.88 (13)°.
While the intramolecular O—H···N and C—H···O hydrogen bonds increase the rigidity of the molecule, intermolecular O—H···O, N—H···O, C—H···O hydrogen bonding interactions (Table 1) links the adjacent molecules directly and through water molecule forming an infinite three-dimensional supramolecular structure in the lattice (Fig. 2). Phenylhydrazinecarboxamide molecules also interact through two types of C—H···π interactions (Fig. 3) with the H···π distances of 2.92 and 2.79 Å and very weak π–π interactions with a shortest centroid–centroid distance of 5.0552 (18) Å. The parallel arrangement of the molecules along b axis is shown in Fig. 4.