organic compounds
N′-[(E)-2,3-Dihydroxybenzylidene]-2-methoxybenzohydrazide
aAtta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E. Malaysia, bFaculty of Applied Science, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Malaysia, cFaculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam, 42300, Selangor, Malaysia, and dH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: dr.sammer.yousuf@gmail.com
The title compound, C15H14N2O4 adopts an E conformation about the azomethine double bond. Intramolecular N—H⋯O and O—H⋯N hydrogen bonds generate S(6) rings and help to establish the The dihedral angle between the benzene rings is 17.84 (10)°. In the crystal, molecules are linked by O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensional network with a herring-bone pattern arranged parallel to the bc plane.
Related literature
For applications and the biological activity of et al. (2009); Khan et al. (2009); Jarahpour et al. (2007). For related structures, see: Baharudin et al. (2012); Taha et al. (2012); Promdet et al. (2011).
see: PanneerselvamExperimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812042390/pv2594sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042390/pv2594Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812042390/pv2594Isup3.cml
The title compound was synthesized by refluxing a mixture of 2-methoxybenzohydrazide (0.332 g, 2 mmol) and 2,3-dihydroxybenzaldehyde (0.276 g, 2 mmol) in methanol (40 ml) along with a catalytical amount of acetic acid for 3 hr. The progress of reaction was monitored by TLC. After completion of reaction, the solvent was evaporated under reduced vacuum to afford crude product which was recrystallized by dissolving in methanol at room temperature to obtain pure needles (0.458 g, 80% yield). All chemicals were purchased by sigma Aldrich Germany.
H atoms on methyl and phenyl C-atoms were positioned geometrically with C—H = 0.96 and 0.93 Å, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.5Ueq(methyl) 1.2Ueq(aryl). The H atoms on the nitrogen and oxygen atoms were located from difference Fourier maps and refined isotropically. A rotating group model was applied to the methyl groups.
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).C15H14N2O4 | F(000) = 1200 |
Mr = 286.28 | Dx = 1.376 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1873 reflections |
a = 14.1479 (17) Å | θ = 2.9–22.2° |
b = 8.6567 (11) Å | µ = 0.10 mm−1 |
c = 22.570 (3) Å | T = 273 K |
V = 2764.2 (6) Å3 | Plate, colorles |
Z = 8 | 0.56 × 0.18 × 0.04 mm |
Bruker SMART APEX CCD area-detector diffractometer | 2574 independent reflections |
Radiation source: fine-focus sealed tube | 1658 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω scan | θmax = 25.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −15→17 |
Tmin = 0.945, Tmax = 0.996 | k = −10→10 |
15288 measured reflections | l = −27→26 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.050P)2 + 0.1101P] where P = (Fo2 + 2Fc2)/3 |
2574 reflections | (Δ/σ)max < 0.001 |
203 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C15H14N2O4 | V = 2764.2 (6) Å3 |
Mr = 286.28 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 14.1479 (17) Å | µ = 0.10 mm−1 |
b = 8.6567 (11) Å | T = 273 K |
c = 22.570 (3) Å | 0.56 × 0.18 × 0.04 mm |
Bruker SMART APEX CCD area-detector diffractometer | 2574 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1658 reflections with I > 2σ(I) |
Tmin = 0.945, Tmax = 0.996 | Rint = 0.042 |
15288 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.14 e Å−3 |
2574 reflections | Δρmin = −0.15 e Å−3 |
203 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 | 0.14939 (10) | −0.02998 (18) | 0.40701 (6) | 0.0774 (5) | |
O2 | 0.43755 (10) | −0.00963 (18) | 0.38297 (7) | 0.0813 (5) | |
O3 | −0.04853 (10) | 0.35880 (19) | 0.18114 (7) | 0.0812 (5) | |
H3A | −0.0756 (18) | 0.407 (3) | 0.1500 (12) | 0.124 (11)* | |
O4 | 0.04345 (10) | 0.21110 (17) | 0.26425 (7) | 0.0705 (4) | |
H4A | 0.0826 (17) | 0.178 (3) | 0.2896 (11) | 0.106 (9)* | |
N1 | 0.26779 (14) | 0.08816 (19) | 0.35803 (7) | 0.0591 (5) | |
H1A | 0.3313 (16) | 0.098 (3) | 0.3523 (9) | 0.087 (8)* | |
N2 | 0.20663 (11) | 0.16136 (18) | 0.31942 (7) | 0.0569 (4) | |
C1 | 0.26911 (17) | −0.1677 (2) | 0.48710 (9) | 0.0752 (6) | |
H1B | 0.2044 | −0.1659 | 0.4943 | 0.090* | |
C2 | 0.3267 (2) | −0.2513 (3) | 0.52416 (10) | 0.0900 (7) | |
H2B | 0.3011 | −0.3049 | 0.5560 | 0.108* | |
C3 | 0.4220 (2) | −0.2550 (3) | 0.51384 (11) | 0.0924 (8) | |
H3B | 0.4611 | −0.3115 | 0.5389 | 0.111* | |
C4 | 0.46035 (17) | −0.1762 (3) | 0.46702 (10) | 0.0793 (7) | |
H4B | 0.5252 | −0.1801 | 0.4603 | 0.095* | |
C5 | 0.40271 (15) | −0.0908 (2) | 0.42963 (9) | 0.0628 (5) | |
C6 | 0.30501 (15) | −0.0859 (2) | 0.43918 (8) | 0.0575 (5) | |
C7 | 0.23441 (15) | −0.0071 (2) | 0.40039 (8) | 0.0576 (5) | |
C8 | 0.24524 (13) | 0.2483 (2) | 0.28070 (8) | 0.0572 (5) | |
H8A | 0.3106 | 0.2591 | 0.2809 | 0.069* | |
C9 | 0.19093 (12) | 0.3307 (2) | 0.23652 (8) | 0.0498 (5) | |
C10 | 0.23670 (14) | 0.4340 (2) | 0.19876 (8) | 0.0623 (5) | |
H10A | 0.3015 | 0.4492 | 0.2026 | 0.075* | |
C11 | 0.18796 (15) | 0.5134 (2) | 0.15615 (9) | 0.0661 (6) | |
H11A | 0.2194 | 0.5829 | 0.1317 | 0.079* | |
C12 | 0.09193 (14) | 0.4901 (2) | 0.14946 (8) | 0.0585 (5) | |
H12A | 0.0588 | 0.5437 | 0.1204 | 0.070* | |
C13 | 0.04530 (13) | 0.3880 (2) | 0.18569 (8) | 0.0532 (5) | |
C14 | 0.09401 (12) | 0.3093 (2) | 0.23002 (7) | 0.0494 (5) | |
C15 | 0.53330 (16) | −0.0285 (3) | 0.36517 (11) | 0.0872 (7) | |
H15A | 0.5444 | 0.0292 | 0.3295 | 0.131* | |
H15B | 0.5458 | −0.1359 | 0.3581 | 0.131* | |
H15C | 0.5743 | 0.0086 | 0.3959 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0578 (10) | 0.1019 (12) | 0.0724 (10) | −0.0083 (8) | −0.0062 (7) | −0.0100 (8) |
O2 | 0.0576 (10) | 0.0926 (11) | 0.0937 (11) | 0.0069 (8) | 0.0005 (8) | 0.0279 (9) |
O3 | 0.0449 (9) | 0.1000 (12) | 0.0987 (12) | −0.0024 (7) | −0.0091 (8) | 0.0351 (10) |
O4 | 0.0515 (9) | 0.0821 (10) | 0.0779 (10) | −0.0071 (7) | 0.0010 (7) | 0.0256 (8) |
N1 | 0.0526 (11) | 0.0636 (11) | 0.0611 (10) | 0.0055 (9) | −0.0122 (9) | −0.0064 (9) |
N2 | 0.0563 (10) | 0.0587 (10) | 0.0558 (10) | 0.0057 (8) | −0.0112 (8) | −0.0083 (8) |
C1 | 0.0884 (17) | 0.0784 (15) | 0.0588 (13) | −0.0058 (13) | 0.0001 (12) | −0.0060 (12) |
C2 | 0.123 (2) | 0.0840 (17) | 0.0635 (15) | 0.0011 (17) | −0.0016 (15) | 0.0123 (13) |
C3 | 0.120 (2) | 0.0834 (17) | 0.0741 (16) | 0.0164 (17) | −0.0178 (15) | 0.0069 (14) |
C4 | 0.0828 (17) | 0.0764 (15) | 0.0787 (15) | 0.0075 (12) | −0.0191 (13) | 0.0026 (14) |
C5 | 0.0692 (15) | 0.0594 (12) | 0.0597 (12) | −0.0002 (11) | −0.0112 (11) | −0.0026 (11) |
C6 | 0.0672 (14) | 0.0543 (11) | 0.0512 (12) | −0.0023 (10) | −0.0087 (10) | −0.0108 (10) |
C7 | 0.0594 (14) | 0.0605 (12) | 0.0528 (12) | −0.0033 (10) | −0.0059 (10) | −0.0153 (10) |
C8 | 0.0467 (11) | 0.0611 (11) | 0.0638 (12) | −0.0008 (10) | −0.0078 (10) | −0.0143 (11) |
C9 | 0.0457 (11) | 0.0503 (10) | 0.0533 (11) | −0.0015 (8) | 0.0004 (8) | −0.0113 (9) |
C10 | 0.0489 (12) | 0.0679 (13) | 0.0700 (13) | −0.0115 (10) | 0.0054 (10) | −0.0082 (11) |
C11 | 0.0723 (14) | 0.0613 (13) | 0.0648 (13) | −0.0153 (11) | 0.0126 (11) | 0.0012 (11) |
C12 | 0.0644 (13) | 0.0547 (11) | 0.0565 (11) | 0.0022 (10) | 0.0021 (10) | 0.0014 (10) |
C13 | 0.0439 (11) | 0.0541 (11) | 0.0616 (12) | 0.0017 (9) | 0.0016 (9) | 0.0011 (10) |
C14 | 0.0465 (11) | 0.0487 (10) | 0.0531 (11) | −0.0023 (8) | 0.0063 (9) | −0.0007 (9) |
C15 | 0.0601 (15) | 0.0902 (17) | 0.1112 (19) | 0.0038 (12) | 0.0052 (13) | 0.0059 (15) |
O1—C7 | 1.228 (2) | C4—C5 | 1.387 (3) |
O2—C5 | 1.359 (2) | C4—H4B | 0.9300 |
O2—C15 | 1.422 (2) | C5—C6 | 1.400 (3) |
O3—C13 | 1.355 (2) | C6—C7 | 1.493 (3) |
O3—H3A | 0.90 (3) | C8—C9 | 1.447 (2) |
O4—C14 | 1.353 (2) | C8—H8A | 0.9300 |
O4—H4A | 0.85 (2) | C9—C14 | 1.392 (2) |
N1—C7 | 1.348 (2) | C9—C10 | 1.395 (2) |
N1—N2 | 1.382 (2) | C10—C11 | 1.368 (3) |
N1—H1A | 0.91 (2) | C10—H10A | 0.9300 |
N2—C8 | 1.276 (2) | C11—C12 | 1.382 (3) |
C1—C2 | 1.373 (3) | C11—H11A | 0.9300 |
C1—C6 | 1.389 (3) | C12—C13 | 1.373 (2) |
C1—H1B | 0.9300 | C12—H12A | 0.9300 |
C2—C3 | 1.368 (3) | C13—C14 | 1.393 (2) |
C2—H2B | 0.9300 | C15—H15A | 0.9600 |
C3—C4 | 1.370 (3) | C15—H15B | 0.9600 |
C3—H3B | 0.9300 | C15—H15C | 0.9600 |
C5—O2—C15 | 120.34 (17) | N2—C8—C9 | 122.37 (17) |
C13—O3—H3A | 113.0 (17) | N2—C8—H8A | 118.8 |
C14—O4—H4A | 104.7 (17) | C9—C8—H8A | 118.8 |
C7—N1—N2 | 120.55 (18) | C14—C9—C10 | 118.61 (17) |
C7—N1—H1A | 120.2 (14) | C14—C9—C8 | 122.01 (16) |
N2—N1—H1A | 119.1 (14) | C10—C9—C8 | 119.38 (17) |
C8—N2—N1 | 115.74 (17) | C11—C10—C9 | 121.16 (19) |
C2—C1—C6 | 121.7 (2) | C11—C10—H10A | 119.4 |
C2—C1—H1B | 119.1 | C9—C10—H10A | 119.4 |
C6—C1—H1B | 119.1 | C10—C11—C12 | 119.95 (18) |
C3—C2—C1 | 119.5 (2) | C10—C11—H11A | 120.0 |
C3—C2—H2B | 120.2 | C12—C11—H11A | 120.0 |
C1—C2—H2B | 120.2 | C13—C12—C11 | 120.08 (18) |
C2—C3—C4 | 120.7 (2) | C13—C12—H12A | 120.0 |
C2—C3—H3B | 119.7 | C11—C12—H12A | 120.0 |
C4—C3—H3B | 119.7 | O3—C13—C12 | 123.07 (17) |
C3—C4—C5 | 120.1 (2) | O3—C13—C14 | 116.58 (17) |
C3—C4—H4B | 119.9 | C12—C13—C14 | 120.34 (17) |
C5—C4—H4B | 119.9 | O4—C14—C9 | 123.01 (16) |
O2—C5—C4 | 122.3 (2) | O4—C14—C13 | 117.13 (16) |
O2—C5—C6 | 117.50 (17) | C9—C14—C13 | 119.84 (16) |
C4—C5—C6 | 120.2 (2) | O2—C15—H15A | 109.5 |
C1—C6—C5 | 117.72 (19) | O2—C15—H15B | 109.5 |
C1—C6—C7 | 116.4 (2) | H15A—C15—H15B | 109.5 |
C5—C6—C7 | 125.77 (19) | O2—C15—H15C | 109.5 |
O1—C7—N1 | 121.88 (19) | H15A—C15—H15C | 109.5 |
O1—C7—C6 | 120.7 (2) | H15B—C15—H15C | 109.5 |
N1—C7—C6 | 117.45 (19) | ||
C7—N1—N2—C8 | −179.58 (16) | C5—C6—C7—N1 | −11.4 (3) |
C6—C1—C2—C3 | −0.2 (3) | N1—N2—C8—C9 | 178.90 (14) |
C1—C2—C3—C4 | 0.0 (4) | N2—C8—C9—C14 | −6.0 (3) |
C2—C3—C4—C5 | 0.4 (4) | N2—C8—C9—C10 | 174.56 (16) |
C15—O2—C5—C4 | 9.8 (3) | C14—C9—C10—C11 | 0.1 (3) |
C15—O2—C5—C6 | −170.20 (18) | C8—C9—C10—C11 | 179.55 (16) |
C3—C4—C5—O2 | 179.4 (2) | C9—C10—C11—C12 | −0.9 (3) |
C3—C4—C5—C6 | −0.6 (3) | C10—C11—C12—C13 | 0.3 (3) |
C2—C1—C6—C5 | −0.1 (3) | C11—C12—C13—O3 | −179.38 (18) |
C2—C1—C6—C7 | 176.70 (19) | C11—C12—C13—C14 | 1.1 (3) |
O2—C5—C6—C1 | −179.52 (17) | C10—C9—C14—O4 | 179.63 (16) |
C4—C5—C6—C1 | 0.5 (3) | C8—C9—C14—O4 | 0.2 (3) |
O2—C5—C6—C7 | 4.1 (3) | C10—C9—C14—C13 | 1.2 (2) |
C4—C5—C6—C7 | −175.94 (17) | C8—C9—C14—C13 | −178.16 (16) |
N2—N1—C7—O1 | −1.4 (3) | O3—C13—C14—O4 | 0.1 (2) |
N2—N1—C7—C6 | 178.09 (14) | C12—C13—C14—O4 | 179.65 (16) |
C1—C6—C7—O1 | −8.4 (3) | O3—C13—C14—C9 | 178.57 (16) |
C5—C6—C7—O1 | 168.06 (18) | C12—C13—C14—C9 | −1.9 (3) |
C1—C6—C7—N1 | 172.13 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.91 (2) | 1.90 (2) | 2.608 (2) | 133 (2) |
O3—H3A···O1i | 0.90 (3) | 1.75 (3) | 2.631 (2) | 167 (2) |
O4—H4A···N2 | 0.85 (2) | 1.89 (2) | 2.658 (2) | 151 (2) |
C8—H8A···O3ii | 0.93 | 2.33 | 3.189 (2) | 153 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x+1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H14N2O4 |
Mr | 286.28 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 273 |
a, b, c (Å) | 14.1479 (17), 8.6567 (11), 22.570 (3) |
V (Å3) | 2764.2 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.56 × 0.18 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.945, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15288, 2574, 1658 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.115, 1.03 |
No. of reflections | 2574 |
No. of parameters | 203 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.15 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.91 (2) | 1.90 (2) | 2.608 (2) | 133 (2) |
O3—H3A···O1i | 0.90 (3) | 1.75 (3) | 2.631 (2) | 167 (2) |
O4—H4A···N2 | 0.85 (2) | 1.89 (2) | 2.658 (2) | 151 (2) |
C8—H8A···O3ii | 0.93 | 2.33 | 3.189 (2) | 152.6 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x+1/2, y, −z+1/2. |
References
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Schiff bases represent an important group of organic compounds with a wide range of medicinal applications (Panneerselvam et al., 2009; Khan et al., 2009; Jarahpour et al., 2007). The title Schiff base was synthesize as a part of our ongoing resaerch to study different bioactive organic compounds.
The bond lengths and angle in the title compound (Fig. 1) are similar to the corresponding bond lengths and bond angles reported in structurally realted Schiff bases (Taha et al., 2012; Promdet et al., 2011). The E configuration of azomethine oelfinic bond is stabilized by two intramolecular N1—H1A···O2, O4—H4A···N2 hydrogen bonds. O3—H3A···O1 and C8—H8A···O3 hydrogen bonds play important roles in stabilizing the crystal structure by forming a two-dimensional-network arranged parallel to the bc plane in a zig zag fashion (Table 2 and Fig. 2).