organic compounds
N′-[(E)-4-Benzyloxy-2-hydroxybenzylidene]benzohydrazide
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, C21H18N2O3, exists in the E conformation with respect to the azomethane C=N double bond. The central benzene ring is almost coplanar with one of the substituent benzene rings [dihedral angle = 1.74 (5)°] and is approximately orthogonal to the other benzene ring of the molecule [dihedral angle = 86.61 (7)°]. An intramolecular O—H⋯N hydrogen bond occurs. The crystal packing is dominated by N—H⋯O hydrogen bonds, which lead to an infinite chain running parallel to [010].
Related literature
For the biological activity of et al. (2010); Zhang et al. (2010). For the synthesis of related compounds, see: Emmanuel et al. (2011); Mangalam & Kurup (2011). For related structures, see: Lin & Sang (2009); Mohd Lair et al. (2009).
see: PatilExperimental
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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812036306/fj2591sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812036306/fj2591Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812036306/fj2591Isup3.cml
The title compound was prepared by adapting a reported procedure (Emmanuel et al., 2011; Mangalam & Kurup, 2011) by refluxing a mixture of methanolic solutions of benzhydrazide (0.136 g,1 mmol) and 4-benzyloxysalicylaldehyde (0.2282 g,1 mmol) for 4 h. The formed crystals were collected, washed with few drops of methanol and dried over P4O10 in vacuo. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation from its methanolic solution.
All H atoms on C were placed in calculated positions, guided by difference maps, with C—H bond distances 0.93–0.97 Å. H atoms were assigned as Uiso=1.2Ueq. H atoms of O2—H2'' and N2—H2' bonds were located from difference maps and restrained using DFIX instructions with O—H = 0.87 ± 0.02 Å and N—H = 0.85 ± 0.01 Å.
In the absence of significant
effects Friedel pairs have been merged.Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).Fig. 1. ORTEP view of the unique part of the compound, drawn with 50% probability displacement ellipsoids for the non-H atoms. Fig. 2. Graphical representation showing one-dimensional supramolecular hydrogen bonding network in the of C21H18N2O3. Fig. 3. Packing diagram of the compound showing the parallel arrangement of the molecules along b axis. |
C21H18N2O3 | F(000) = 364 |
Mr = 346.37 | Dx = 1.336 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 5951 reflections |
a = 10.8053 (6) Å | θ = 2.4–28.1° |
b = 4.8952 (2) Å | µ = 0.09 mm−1 |
c = 16.3601 (10) Å | T = 296 K |
β = 95.813 (2)° | Block, colorless |
V = 860.90 (8) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 2 |
Bruker Kappa APEXII CCD diffractometer | 1705 independent reflections |
Radiation source: fine-focus sealed tube | 1593 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ω and ϕ scan | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | k = −5→5 |
Tmin = 0.969, Tmax = 0.978 | l = −19→19 |
9033 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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.0573P] where P = (Fo2 + 2Fc2)/3 |
1705 reflections | (Δ/σ)max = 0.005 |
243 parameters | Δρmax = 0.12 e Å−3 |
3 restraints | Δρmin = −0.14 e Å−3 |
C21H18N2O3 | V = 860.90 (8) Å3 |
Mr = 346.37 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.8053 (6) Å | µ = 0.09 mm−1 |
b = 4.8952 (2) Å | T = 296 K |
c = 16.3601 (10) Å | 0.35 × 0.30 × 0.25 mm |
β = 95.813 (2)° |
Bruker Kappa APEXII CCD diffractometer | 1705 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1593 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.978 | Rint = 0.024 |
9033 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 3 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.12 e Å−3 |
1705 reflections | Δρmin = −0.14 e Å−3 |
243 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 | 0.08187 (12) | 0.6299 (3) | 1.18699 (7) | 0.0525 (4) | |
O2 | 0.19313 (15) | 0.4504 (4) | 0.91841 (8) | 0.0610 (4) | |
O3 | 0.43474 (14) | 0.3828 (3) | 0.76116 (9) | 0.0575 (4) | |
N1 | 0.37436 (15) | 0.7368 (4) | 0.87075 (9) | 0.0471 (4) | |
N2 | 0.44743 (17) | 0.8127 (3) | 0.81016 (10) | 0.0458 (4) | |
C1 | −0.1620 (2) | 0.5457 (6) | 1.27899 (13) | 0.0681 (7) | |
H1 | −0.1984 | 0.6716 | 1.2413 | 0.082* | |
C2 | −0.2072 (2) | 0.5169 (8) | 1.35467 (15) | 0.0812 (9) | |
H2A | −0.2737 | 0.6235 | 1.3677 | 0.097* | |
C3 | −0.1550 (3) | 0.3347 (7) | 1.40967 (15) | 0.0779 (8) | |
H3 | −0.1853 | 0.3174 | 1.4607 | 0.093* | |
C4 | −0.0583 (3) | 0.1761 (8) | 1.39081 (16) | 0.0890 (9) | |
H4 | −0.0228 | 0.0501 | 1.4288 | 0.107* | |
C5 | −0.0126 (2) | 0.2025 (7) | 1.31467 (15) | 0.0750 (7) | |
H5 | 0.0528 | 0.0928 | 1.3015 | 0.090* | |
C6 | −0.06386 (17) | 0.3899 (5) | 1.25910 (11) | 0.0500 (5) | |
C7 | −0.01383 (18) | 0.4243 (5) | 1.17735 (11) | 0.0531 (5) | |
H7A | 0.0203 | 0.2531 | 1.1600 | 0.064* | |
H7B | −0.0798 | 0.4808 | 1.1361 | 0.064* | |
C8 | 0.14629 (15) | 0.6828 (4) | 1.12181 (10) | 0.0424 (4) | |
C9 | 0.13243 (17) | 0.5416 (4) | 1.04847 (11) | 0.0464 (5) | |
H9 | 0.0725 | 0.4054 | 1.0401 | 0.056* | |
C10 | 0.20779 (17) | 0.6026 (4) | 0.98724 (10) | 0.0431 (4) | |
C11 | 0.29517 (17) | 0.8163 (4) | 0.99739 (10) | 0.0421 (4) | |
C12 | 0.30438 (17) | 0.9593 (5) | 1.07174 (11) | 0.0501 (5) | |
H12 | 0.3604 | 1.1034 | 1.0794 | 0.060* | |
C13 | 0.23345 (17) | 0.8937 (5) | 1.13355 (11) | 0.0493 (5) | |
H13 | 0.2431 | 0.9886 | 1.1830 | 0.059* | |
C14 | 0.37200 (17) | 0.8897 (5) | 0.93334 (11) | 0.0470 (4) | |
H14 | 0.4195 | 1.0484 | 0.9380 | 0.056* | |
C15 | 0.47098 (17) | 0.6182 (4) | 0.75527 (11) | 0.0427 (4) | |
C16 | 0.54733 (16) | 0.7030 (4) | 0.68911 (11) | 0.0433 (4) | |
C17 | 0.5333 (2) | 0.5618 (5) | 0.61561 (12) | 0.0565 (6) | |
H17 | 0.4738 | 0.4244 | 0.6077 | 0.068* | |
C18 | 0.6065 (2) | 0.6223 (6) | 0.55402 (13) | 0.0671 (6) | |
H18 | 0.5957 | 0.5273 | 0.5046 | 0.080* | |
C19 | 0.6950 (2) | 0.8216 (6) | 0.56521 (14) | 0.0673 (7) | |
H19 | 0.7449 | 0.8610 | 0.5236 | 0.081* | |
C20 | 0.7105 (2) | 0.9643 (6) | 0.63802 (14) | 0.0655 (6) | |
H20 | 0.7709 | 1.0998 | 0.6455 | 0.079* | |
C21 | 0.63653 (18) | 0.9069 (5) | 0.70001 (13) | 0.0532 (5) | |
H21 | 0.6466 | 1.0048 | 0.7489 | 0.064* | |
H2' | 0.4593 (19) | 0.9831 (9) | 0.8048 (13) | 0.047 (6)* | |
H2'' | 0.249 (2) | 0.514 (7) | 0.8883 (16) | 0.100 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0541 (7) | 0.0627 (10) | 0.0425 (6) | −0.0105 (7) | 0.0144 (5) | −0.0043 (7) |
O2 | 0.0859 (10) | 0.0528 (10) | 0.0474 (7) | −0.0177 (8) | 0.0207 (7) | −0.0110 (7) |
O3 | 0.0747 (9) | 0.0345 (8) | 0.0668 (9) | −0.0058 (7) | 0.0238 (7) | 0.0026 (7) |
N1 | 0.0560 (9) | 0.0423 (10) | 0.0454 (8) | 0.0030 (8) | 0.0161 (7) | 0.0061 (8) |
N2 | 0.0602 (9) | 0.0320 (9) | 0.0478 (8) | 0.0002 (7) | 0.0184 (7) | 0.0059 (7) |
C1 | 0.0652 (12) | 0.0807 (18) | 0.0605 (12) | 0.0120 (13) | 0.0162 (10) | 0.0076 (13) |
C2 | 0.0728 (15) | 0.103 (2) | 0.0724 (15) | 0.0086 (16) | 0.0311 (12) | −0.0023 (17) |
C3 | 0.0884 (17) | 0.090 (2) | 0.0604 (13) | −0.0181 (17) | 0.0300 (12) | 0.0016 (15) |
C4 | 0.106 (2) | 0.094 (2) | 0.0688 (15) | 0.0056 (19) | 0.0186 (14) | 0.0313 (17) |
C5 | 0.0768 (15) | 0.0803 (19) | 0.0712 (14) | 0.0118 (14) | 0.0235 (12) | 0.0150 (14) |
C6 | 0.0466 (10) | 0.0556 (12) | 0.0488 (9) | −0.0096 (10) | 0.0094 (8) | −0.0032 (10) |
C7 | 0.0530 (10) | 0.0581 (14) | 0.0497 (10) | −0.0071 (11) | 0.0115 (8) | −0.0053 (10) |
C8 | 0.0418 (9) | 0.0464 (12) | 0.0396 (9) | 0.0028 (8) | 0.0060 (7) | 0.0006 (9) |
C9 | 0.0505 (10) | 0.0439 (11) | 0.0454 (10) | −0.0058 (9) | 0.0078 (8) | 0.0003 (9) |
C10 | 0.0536 (10) | 0.0382 (10) | 0.0377 (8) | 0.0020 (9) | 0.0059 (7) | 0.0002 (8) |
C11 | 0.0447 (9) | 0.0407 (11) | 0.0414 (9) | 0.0028 (8) | 0.0061 (7) | 0.0016 (8) |
C12 | 0.0504 (10) | 0.0492 (13) | 0.0508 (10) | −0.0105 (10) | 0.0055 (8) | −0.0052 (9) |
C13 | 0.0542 (10) | 0.0547 (12) | 0.0391 (9) | −0.0051 (10) | 0.0055 (7) | −0.0061 (10) |
C14 | 0.0487 (9) | 0.0425 (11) | 0.0507 (10) | −0.0011 (9) | 0.0091 (8) | 0.0022 (10) |
C15 | 0.0482 (10) | 0.0349 (10) | 0.0460 (9) | 0.0024 (9) | 0.0089 (7) | 0.0057 (9) |
C16 | 0.0482 (10) | 0.0364 (10) | 0.0465 (9) | 0.0053 (8) | 0.0097 (8) | 0.0052 (8) |
C17 | 0.0673 (12) | 0.0523 (14) | 0.0515 (11) | −0.0063 (11) | 0.0139 (9) | −0.0026 (10) |
C18 | 0.0844 (15) | 0.0710 (17) | 0.0487 (11) | −0.0028 (15) | 0.0210 (10) | −0.0012 (12) |
C19 | 0.0731 (14) | 0.0721 (17) | 0.0613 (13) | 0.0023 (13) | 0.0296 (11) | 0.0135 (13) |
C20 | 0.0601 (12) | 0.0620 (16) | 0.0779 (15) | −0.0129 (12) | 0.0245 (10) | 0.0058 (13) |
C21 | 0.0565 (10) | 0.0488 (12) | 0.0558 (10) | −0.0040 (10) | 0.0131 (8) | 0.0003 (10) |
O1—C8 | 1.356 (2) | C8—C9 | 1.380 (3) |
O1—C7 | 1.440 (3) | C8—C13 | 1.397 (3) |
O2—C10 | 1.346 (2) | C9—C10 | 1.386 (3) |
O2—H2'' | 0.871 (18) | C9—H9 | 0.9300 |
O3—C15 | 1.224 (3) | C10—C11 | 1.407 (3) |
N1—C14 | 1.271 (2) | C11—C12 | 1.398 (3) |
N1—N2 | 1.379 (2) | C11—C14 | 1.447 (2) |
N2—C15 | 1.350 (3) | C12—C13 | 1.367 (3) |
N2—H2' | 0.8500 (11) | C12—H12 | 0.9300 |
C1—C6 | 1.372 (3) | C13—H13 | 0.9300 |
C1—C2 | 1.383 (3) | C14—H14 | 0.9300 |
C1—H1 | 0.9300 | C15—C16 | 1.485 (2) |
C2—C3 | 1.349 (4) | C16—C17 | 1.382 (3) |
C2—H2A | 0.9300 | C16—C21 | 1.386 (3) |
C3—C4 | 1.363 (4) | C17—C18 | 1.375 (3) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.392 (3) | C18—C19 | 1.365 (4) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.369 (4) | C19—C20 | 1.376 (3) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.502 (2) | C20—C21 | 1.382 (3) |
C7—H7A | 0.9700 | C20—H20 | 0.9300 |
C7—H7B | 0.9700 | C21—H21 | 0.9300 |
C8—O1—C7 | 117.87 (14) | O2—C10—C9 | 117.22 (18) |
C10—O2—H2'' | 104 (2) | O2—C10—C11 | 122.05 (16) |
C14—N1—N2 | 118.70 (17) | C9—C10—C11 | 120.73 (17) |
C15—N2—N1 | 116.64 (16) | C12—C11—C10 | 117.55 (16) |
C15—N2—H2' | 125.7 (15) | C12—C11—C14 | 120.68 (18) |
N1—N2—H2' | 116.2 (15) | C10—C11—C14 | 121.77 (17) |
C6—C1—C2 | 120.5 (2) | C13—C12—C11 | 121.99 (19) |
C6—C1—H1 | 119.8 | C13—C12—H12 | 119.0 |
C2—C1—H1 | 119.8 | C11—C12—H12 | 119.0 |
C3—C2—C1 | 120.2 (3) | C12—C13—C8 | 119.49 (17) |
C3—C2—H2A | 119.9 | C12—C13—H13 | 120.3 |
C1—C2—H2A | 119.9 | C8—C13—H13 | 120.3 |
C2—C3—C4 | 120.3 (2) | N1—C14—C11 | 119.8 (2) |
C2—C3—H3 | 119.9 | N1—C14—H14 | 120.1 |
C4—C3—H3 | 119.9 | C11—C14—H14 | 120.1 |
C3—C4—C5 | 120.0 (3) | O3—C15—N2 | 121.87 (17) |
C3—C4—H4 | 120.0 | O3—C15—C16 | 121.75 (18) |
C5—C4—H4 | 120.0 | N2—C15—C16 | 116.34 (18) |
C6—C5—C4 | 120.0 (3) | C17—C16—C21 | 119.04 (17) |
C6—C5—H5 | 120.0 | C17—C16—C15 | 118.32 (18) |
C4—C5—H5 | 120.0 | C21—C16—C15 | 122.54 (18) |
C5—C6—C1 | 119.1 (2) | C18—C17—C16 | 120.6 (2) |
C5—C6—C7 | 120.6 (2) | C18—C17—H17 | 119.7 |
C1—C6—C7 | 120.4 (2) | C16—C17—H17 | 119.7 |
O1—C7—C6 | 107.46 (16) | C19—C18—C17 | 120.2 (2) |
O1—C7—H7A | 110.2 | C19—C18—H18 | 119.9 |
C6—C7—H7A | 110.2 | C17—C18—H18 | 119.9 |
O1—C7—H7B | 110.2 | C18—C19—C20 | 120.06 (19) |
C6—C7—H7B | 110.2 | C18—C19—H19 | 120.0 |
H7A—C7—H7B | 108.5 | C20—C19—H19 | 120.0 |
O1—C8—C9 | 124.68 (17) | C19—C20—C21 | 120.2 (2) |
O1—C8—C13 | 115.18 (16) | C19—C20—H20 | 119.9 |
C9—C8—C13 | 120.13 (16) | C21—C20—H20 | 119.9 |
C8—C9—C10 | 120.04 (18) | C20—C21—C16 | 119.9 (2) |
C8—C9—H9 | 120.0 | C20—C21—H21 | 120.1 |
C10—C9—H9 | 120.0 | C16—C21—H21 | 120.1 |
C14—N1—N2—C15 | 164.71 (18) | C10—C11—C12—C13 | 1.2 (3) |
C6—C1—C2—C3 | −0.1 (4) | C14—C11—C12—C13 | −179.66 (19) |
C1—C2—C3—C4 | −0.6 (5) | C11—C12—C13—C8 | −1.9 (3) |
C2—C3—C4—C5 | 0.3 (5) | O1—C8—C13—C12 | 178.99 (18) |
C3—C4—C5—C6 | 0.7 (5) | C9—C8—C13—C12 | 0.2 (3) |
C4—C5—C6—C1 | −1.4 (4) | N2—N1—C14—C11 | 179.39 (16) |
C4—C5—C6—C7 | 178.8 (3) | C12—C11—C14—N1 | 170.89 (18) |
C2—C1—C6—C5 | 1.0 (4) | C10—C11—C14—N1 | −10.0 (3) |
C2—C1—C6—C7 | −179.1 (3) | N1—N2—C15—O3 | −3.6 (3) |
C8—O1—C7—C6 | 175.83 (17) | N1—N2—C15—C16 | 178.67 (15) |
C5—C6—C7—O1 | −90.4 (3) | O3—C15—C16—C17 | 28.2 (3) |
C1—C6—C7—O1 | 89.8 (2) | N2—C15—C16—C17 | −154.05 (19) |
C7—O1—C8—C9 | −4.4 (3) | O3—C15—C16—C21 | −148.1 (2) |
C7—O1—C8—C13 | 176.89 (17) | N2—C15—C16—C21 | 29.7 (3) |
O1—C8—C9—C10 | −176.51 (17) | C21—C16—C17—C18 | −0.1 (3) |
C13—C8—C9—C10 | 2.1 (3) | C15—C16—C17—C18 | −176.5 (2) |
C8—C9—C10—O2 | 177.42 (18) | C16—C17—C18—C19 | 0.7 (4) |
C8—C9—C10—C11 | −2.9 (3) | C17—C18—C19—C20 | −0.6 (4) |
O2—C10—C11—C12 | −179.1 (2) | C18—C19—C20—C21 | −0.1 (4) |
C9—C10—C11—C12 | 1.2 (3) | C19—C20—C21—C16 | 0.6 (4) |
O2—C10—C11—C14 | 1.8 (3) | C17—C16—C21—C20 | −0.5 (3) |
C9—C10—C11—C14 | −177.93 (18) | C15—C16—C21—C20 | 175.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2′···O3i | 0.85 (1) | 2.09 (1) | 2.903 (2) | 160 (2) |
O2—H2′′···N1 | 0.87 (2) | 1.79 (2) | 2.592 (2) | 152 (3) |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C21H18N2O3 |
Mr | 346.37 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 10.8053 (6), 4.8952 (2), 16.3601 (10) |
β (°) | 95.813 (2) |
V (Å3) | 860.90 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.969, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9033, 1705, 1593 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.082, 1.12 |
No. of reflections | 1705 |
No. of parameters | 243 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.12, −0.14 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 2010), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2'···O3i | 0.8500 (11) | 2.090 (8) | 2.903 (2) | 160 (2) |
O2—H2''···N1 | 0.871 (18) | 1.79 (2) | 2.592 (2) | 152 (3) |
Symmetry code: (i) x, y+1, z. |
Acknowledgements
The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for providing the single-crystal X-ray diffraction data. PRR thanks the Council of Scientific and Industrial Research, New Delhi, India, for a Junior Research Fellowship.
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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.
Hydrazone compounds have received much attention due to their potential applications in biological chemistry (Patil et al., 2010; Zhang et al., 2010). As a continuous work on the hydrazone compounds, a new hydrazone compound, N'-{(E)-[4-(benzyloxy)-2-hydroxyphenyl]methylidene}benzohydrazide, 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. The molecule adopts an E configuration with respect to C14=N1 bond (Lin & Sang 2009; Mohd Lair et al., 2009) and it exists in amido form with C15=O3 bond length of 1.224 (3) Å which is very close to a formal C=O bond length [1.21 Å]. The aromatic ring C8—C13 is almost coplanar with the ring C16—C21 with dihedral angle of 1.74 (5)° whilst the ring C1—C6 is approximately orthogonal (86.61 (7)°) to the ring C16—C21.
While the intramolecular hydrogen bond O(2)—H(2'')···N(1) increases the rigidity of the molecule, intermolecular N(2)—H(2')···O(3) hydrogen bond (Table 1) links the adjacent molecules forming an infinite one-dimensional supramolecular chain running parallel to the [010] direction in the unit cell (Fig. 2). Benzohydrazone molecules within these chains also interact through very weak π···π interactions with a shortest centroid-centroid distance of 4.8950 (15) Å that not only augment the stronger N—H···O hydrogen bond but also interconnects the infinite chains forming three-dimensional network in the lattice. The parallel arrangement of the molecules along b axis is shown in Fig. 3.