organic compounds
(E)-4-Amino-N′-(2-hydroxy-5-methylbenzylidene)benzohydrazide
aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, I. R. of IRAN, bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and cDepartment of Physics, University of Sargodha, Punjab, Pakistan
*Correspondence e-mail: h.kargar@pnu.ac.ir, dmntahir_uos@yahoo.com
The 15H15N3O2, comprises two crystallographically independent molecules (A and B), each having an E conformation around the C=N bond. In each molecule, there is an intramolecular O—H⋯N hydrogen bond making an S(6) ring motif. The dihedral angles between the substituted phenyl rings are 17.49 (9) and 10.03 (9)°. In the crystal, N—H⋯O hydrogen bonds link neighbouring independent molecules into infinite chains, of the type –A–B–A–B–, along the a axis, enclosing R21(7) ring motifs. The chains are linked by N—H⋯O hydrogen bonds and C—H⋯O interactions, leading to the formation of a three-dimensional network.
of the title compound, CRelated literature
For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006); Karthikeyan et al. (2006). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012); Shi & Li (2012); Bakir & Green (2002); Kargar et al. (2012a,b). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); 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 and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812027948/su2458sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027948/su2458Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812027948/su2458Isup3.cml
The title compound was synthesized by adding 1 mmol of methyl 4-aminobenzoate to a solution of 5-methylsalicylaldehyde (1 mmol) in methanol (30 ml). The mixture was refluxed with stirring for 30 min and after cooling to room temperature a light-yellow precipitate was filtered and washed with diethylether and dried in air. Yellow prismatic crystals of the title compound, suitable for X-ray structure analysis, were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.
The N-bound H-atoms were located in a difference Fourier map and were constrained to ride on their parent N atoms with Uiso(H) = 1.2Ueq(N). The OH and C-bound H atoms were included in calculated positions and treated as riding atoms: O-H = 0.82 Å, C-H = 0.93 and 0.96 Å for CH and CH3 H atoms, respectively, with Uiso(H) = k × Ueq(O,C) where k = 1.5 for OH and CH3 H atoms and = 1.2 for other H atoms.
Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and magnetism, and supramolecular architectures (Karthikeyan et al., 2006; Kucukguzel et al., 2006). Structures of
derived from substituted 4-aminobenzohydrazide have been reported earlier (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002; Kargar et al. (2012a,b). In order to explore the structure of new Schiff base derivatives, the title compound was prepared and characterized crystallographically.The ═N bond. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those reported for related structures (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002; Kargar et al. (2012a,b). In each molecule there is an intramolecular O—H···N hydrogen bond making an S(6) ring motif. The dihedral angles between the substituted phenyl rings (C1-C6/C9-C14 in molecule A and C16-C21/C24-C29 in molecule B) are 17.49 (9) and 10.03 (9)°, respectively.
of the title compound, Fig. 1, comprises two crystallographically independent molecules (A and B) both with an E conformation around the CIn the crystal, N—H···O hydrogen bonds (Table 1 and Fig. 2) link neighbouring independent molecules into infinite chains, of the type -A-B-A-B-, along the a axis, enclosing R12(7) ring motifs (Bernstein et al., 1995). The chains are linked by N-H···O hydrogen bonds and C—H···O interactions leading to the formation of a three-dimensional network (Table 1).
For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006); Karthikeyan et al. (2006). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012); Shi & Li (2012); Bakir & Green (2002); Kargar et al. (2012a,b). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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) and PLATON (Spek, 2009).Fig. 1. A view of the molecular structure of the two independent molecules of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The intramolecular O-H···N hydrogen bonds are shown as dashed lines (see Table 1 for details). | |
Fig. 2. A view along the c axis of the crystal packing of the title compound. The N—H···O hydrogen bonds and the C—H···O interactions are shown as dashed lines (see Table 1 for details; Only the H atoms involved in these interactions are shown). |
C15H15N3O2 | Z = 4 |
Mr = 269.30 | F(000) = 568 |
Triclinic, P1 | Dx = 1.299 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2717 (8) Å | Cell parameters from 1125 reflections |
b = 11.5668 (10) Å | θ = 2.5–27.4° |
c = 11.9152 (9) Å | µ = 0.09 mm−1 |
α = 94.544 (3)° | T = 291 K |
β = 100.583 (3)° | Prism, yellow |
γ = 95.880 (3)° | 0.30 × 0.25 × 0.24 mm |
V = 1377.28 (19) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 6081 independent reflections |
Radiation source: fine-focus sealed tube | 3917 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 27.2°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −13→13 |
Tmin = 0.974, Tmax = 0.979 | k = −14→14 |
21355 measured reflections | l = −15→13 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0572P)2 + 0.2031P] where P = (Fo2 + 2Fc2)/3 |
6081 reflections | (Δ/σ)max < 0.001 |
365 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C15H15N3O2 | γ = 95.880 (3)° |
Mr = 269.30 | V = 1377.28 (19) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.2717 (8) Å | Mo Kα radiation |
b = 11.5668 (10) Å | µ = 0.09 mm−1 |
c = 11.9152 (9) Å | T = 291 K |
α = 94.544 (3)° | 0.30 × 0.25 × 0.24 mm |
β = 100.583 (3)° |
Bruker SMART APEXII CCD area-detector diffractometer | 6081 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3917 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.979 | Rint = 0.028 |
21355 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.19 e Å−3 |
6081 reflections | Δρmin = −0.17 e Å−3 |
365 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
C1 | 0.41397 (14) | 0.93883 (14) | 0.73216 (13) | 0.0416 (4) | |
C2 | 0.34820 (17) | 0.95319 (16) | 0.62200 (14) | 0.0525 (4) | |
H2A | 0.2819 | 0.8953 | 0.5835 | 0.063* | |
C3 | 0.37828 (18) | 1.04928 (17) | 0.56949 (15) | 0.0580 (5) | |
H3A | 0.3332 | 1.0558 | 0.4955 | 0.070* | |
C4 | 0.47549 (17) | 1.13830 (16) | 0.62444 (14) | 0.0505 (4) | |
C5 | 0.54375 (16) | 1.12428 (15) | 0.73354 (14) | 0.0507 (4) | |
H5A | 0.6107 | 1.1819 | 0.7714 | 0.061* | |
C6 | 0.51343 (15) | 1.02622 (15) | 0.78609 (14) | 0.0467 (4) | |
H6A | 0.5604 | 1.0183 | 0.8591 | 0.056* | |
C7 | 0.36676 (14) | 0.83795 (14) | 0.78761 (13) | 0.0426 (4) | |
C8 | 0.48321 (16) | 0.68945 (14) | 1.02368 (14) | 0.0456 (4) | |
H8A | 0.5691 | 0.7281 | 1.0467 | 0.055* | |
C9 | 0.43816 (16) | 0.59517 (14) | 1.08529 (14) | 0.0446 (4) | |
C10 | 0.31463 (17) | 0.52710 (15) | 1.04709 (15) | 0.0515 (4) | |
C11 | 0.2798 (2) | 0.43601 (16) | 1.10815 (19) | 0.0650 (5) | |
H11A | 0.1992 | 0.3889 | 1.0822 | 0.078* | |
C12 | 0.3624 (2) | 0.41382 (16) | 1.20672 (18) | 0.0648 (5) | |
H12A | 0.3353 | 0.3532 | 1.2473 | 0.078* | |
C13 | 0.4847 (2) | 0.47943 (16) | 1.24696 (15) | 0.0584 (5) | |
C14 | 0.51992 (18) | 0.56874 (15) | 1.18424 (15) | 0.0525 (4) | |
H14A | 0.6023 | 0.6134 | 1.2093 | 0.063* | |
C15 | 0.5763 (3) | 0.4523 (2) | 1.35265 (18) | 0.0848 (7) | |
H15A | 0.6484 | 0.4149 | 1.3308 | 0.127* | |
H15B | 0.5276 | 0.4011 | 1.3942 | 0.127* | |
H15C | 0.6115 | 0.5234 | 1.4005 | 0.127* | |
C16 | 0.06408 (16) | 0.30308 (14) | 0.48957 (14) | 0.0469 (4) | |
C17 | −0.05809 (17) | 0.34582 (17) | 0.48283 (16) | 0.0572 (5) | |
H17A | −0.1126 | 0.3465 | 0.4114 | 0.069* | |
C18 | −0.1001 (2) | 0.38722 (18) | 0.57992 (17) | 0.0681 (5) | |
H18A | −0.1829 | 0.4145 | 0.5733 | 0.082* | |
C19 | −0.0209 (2) | 0.38872 (19) | 0.68691 (17) | 0.0691 (5) | |
C20 | 0.1007 (2) | 0.3453 (2) | 0.69390 (17) | 0.0709 (6) | |
H20A | 0.1551 | 0.3446 | 0.7654 | 0.085* | |
C21 | 0.14190 (18) | 0.30375 (17) | 0.59809 (15) | 0.0590 (5) | |
H21A | 0.2241 | 0.2751 | 0.6053 | 0.071* | |
C22 | 0.11833 (16) | 0.26239 (15) | 0.38986 (14) | 0.0466 (4) | |
C23 | −0.00670 (15) | 0.18859 (14) | 0.09605 (14) | 0.0458 (4) | |
H23A | −0.0949 | 0.2024 | 0.0929 | 0.055* | |
C24 | 0.03676 (15) | 0.14797 (14) | −0.00741 (13) | 0.0433 (4) | |
C25 | 0.16631 (15) | 0.12065 (14) | −0.00588 (14) | 0.0454 (4) | |
C26 | 0.20213 (17) | 0.07912 (16) | −0.10588 (16) | 0.0576 (5) | |
H26A | 0.2885 | 0.0610 | −0.1046 | 0.069* | |
C27 | 0.11136 (18) | 0.06414 (16) | −0.20780 (16) | 0.0597 (5) | |
H27A | 0.1376 | 0.0364 | −0.2746 | 0.072* | |
C28 | −0.01883 (18) | 0.08963 (16) | −0.21308 (15) | 0.0557 (5) | |
C29 | −0.05284 (16) | 0.13124 (15) | −0.11215 (14) | 0.0495 (4) | |
H29A | −0.1394 | 0.1490 | −0.1139 | 0.059* | |
C30 | −0.1168 (2) | 0.0702 (2) | −0.32422 (16) | 0.0785 (6) | |
H30A | −0.1578 | 0.1401 | −0.3377 | 0.118* | |
H30B | −0.1841 | 0.0073 | −0.3208 | 0.118* | |
H30C | −0.0715 | 0.0509 | −0.3856 | 0.118* | |
N1 | 0.50273 (18) | 1.23589 (15) | 0.57157 (14) | 0.0716 (5) | |
H1A | 0.4596 | 1.2425 | 0.5038 | 0.086* | |
H1B | 0.5630 | 1.2907 | 0.6060 | 0.086* | |
N2 | 0.45092 (13) | 0.80883 (12) | 0.88017 (11) | 0.0473 (3) | |
H1N2 | 0.5423 | 0.8349 | 0.8962 | 0.057* | |
N3 | 0.40512 (13) | 0.71958 (12) | 0.93778 (12) | 0.0474 (3) | |
N4 | −0.0612 (2) | 0.4296 (2) | 0.78470 (17) | 0.1166 (8) | |
H4A | −0.1376 | 0.4551 | 0.7801 | 0.140* | |
H4B | −0.0101 | 0.4297 | 0.8506 | 0.140* | |
N5 | 0.03008 (13) | 0.24063 (13) | 0.28828 (11) | 0.0509 (4) | |
H1N5 | −0.0634 | 0.2399 | 0.2848 | 0.061* | |
N6 | 0.07587 (12) | 0.20552 (12) | 0.19168 (11) | 0.0464 (3) | |
O1 | 0.25527 (10) | 0.78344 (11) | 0.75600 (10) | 0.0585 (3) | |
O2 | 0.22764 (12) | 0.54605 (12) | 0.95216 (12) | 0.0704 (4) | |
H2 | 0.2591 | 0.6017 | 0.9231 | 0.106* | |
O3 | 0.23698 (11) | 0.24990 (12) | 0.39557 (10) | 0.0596 (3) | |
O4 | 0.25969 (10) | 0.13154 (11) | 0.09292 (10) | 0.0552 (3) | |
H4 | 0.2266 | 0.1546 | 0.1469 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0320 (8) | 0.0510 (10) | 0.0423 (9) | 0.0098 (7) | 0.0070 (7) | 0.0025 (7) |
C2 | 0.0493 (10) | 0.0606 (11) | 0.0427 (10) | 0.0039 (8) | −0.0005 (8) | 0.0006 (8) |
C3 | 0.0627 (11) | 0.0695 (13) | 0.0394 (10) | 0.0108 (9) | 0.0012 (8) | 0.0074 (9) |
C4 | 0.0528 (10) | 0.0540 (11) | 0.0490 (10) | 0.0141 (8) | 0.0146 (8) | 0.0099 (8) |
C5 | 0.0425 (9) | 0.0509 (10) | 0.0554 (11) | 0.0041 (7) | 0.0035 (8) | 0.0024 (8) |
C6 | 0.0385 (8) | 0.0546 (10) | 0.0448 (9) | 0.0091 (7) | 0.0001 (7) | 0.0065 (8) |
C7 | 0.0316 (8) | 0.0521 (10) | 0.0436 (9) | 0.0071 (7) | 0.0065 (7) | −0.0001 (7) |
C8 | 0.0412 (9) | 0.0468 (9) | 0.0474 (9) | −0.0015 (7) | 0.0095 (7) | 0.0034 (7) |
C9 | 0.0476 (9) | 0.0415 (9) | 0.0466 (9) | 0.0020 (7) | 0.0176 (8) | 0.0011 (7) |
C10 | 0.0489 (10) | 0.0495 (10) | 0.0574 (11) | 0.0009 (8) | 0.0183 (9) | 0.0002 (8) |
C11 | 0.0615 (12) | 0.0503 (11) | 0.0861 (15) | −0.0065 (9) | 0.0314 (11) | 0.0020 (10) |
C12 | 0.0815 (14) | 0.0470 (11) | 0.0766 (14) | 0.0047 (10) | 0.0428 (12) | 0.0118 (10) |
C13 | 0.0804 (13) | 0.0466 (10) | 0.0548 (11) | 0.0138 (9) | 0.0259 (10) | 0.0076 (8) |
C14 | 0.0581 (10) | 0.0463 (10) | 0.0529 (10) | 0.0014 (8) | 0.0132 (8) | 0.0041 (8) |
C15 | 0.122 (2) | 0.0713 (14) | 0.0660 (14) | 0.0185 (13) | 0.0191 (13) | 0.0254 (11) |
C16 | 0.0413 (9) | 0.0496 (10) | 0.0476 (10) | −0.0005 (7) | 0.0056 (7) | 0.0073 (8) |
C17 | 0.0481 (10) | 0.0683 (12) | 0.0524 (11) | 0.0077 (9) | 0.0026 (8) | 0.0037 (9) |
C18 | 0.0568 (11) | 0.0783 (14) | 0.0694 (13) | 0.0172 (10) | 0.0118 (10) | −0.0016 (11) |
C19 | 0.0748 (14) | 0.0764 (14) | 0.0577 (12) | 0.0163 (11) | 0.0172 (11) | −0.0033 (10) |
C20 | 0.0685 (13) | 0.0935 (16) | 0.0475 (11) | 0.0181 (11) | 0.0021 (10) | −0.0009 (10) |
C21 | 0.0513 (10) | 0.0749 (13) | 0.0485 (11) | 0.0110 (9) | 0.0023 (8) | 0.0044 (9) |
C22 | 0.0393 (9) | 0.0522 (10) | 0.0464 (10) | −0.0011 (7) | 0.0042 (7) | 0.0109 (8) |
C23 | 0.0337 (8) | 0.0553 (10) | 0.0484 (10) | 0.0044 (7) | 0.0071 (7) | 0.0073 (8) |
C24 | 0.0355 (8) | 0.0450 (9) | 0.0474 (9) | −0.0010 (7) | 0.0053 (7) | 0.0064 (7) |
C25 | 0.0357 (8) | 0.0454 (9) | 0.0523 (10) | −0.0022 (7) | 0.0055 (7) | 0.0050 (7) |
C26 | 0.0436 (9) | 0.0596 (11) | 0.0700 (12) | 0.0034 (8) | 0.0177 (9) | −0.0029 (9) |
C27 | 0.0588 (11) | 0.0628 (12) | 0.0567 (11) | −0.0015 (9) | 0.0187 (9) | −0.0044 (9) |
C28 | 0.0565 (11) | 0.0569 (11) | 0.0494 (10) | −0.0032 (8) | 0.0057 (8) | 0.0024 (8) |
C29 | 0.0377 (8) | 0.0581 (11) | 0.0504 (10) | 0.0030 (7) | 0.0037 (7) | 0.0061 (8) |
C30 | 0.0803 (14) | 0.0929 (17) | 0.0531 (12) | −0.0014 (12) | 0.0007 (11) | −0.0035 (11) |
N1 | 0.0848 (12) | 0.0661 (11) | 0.0637 (10) | 0.0052 (9) | 0.0104 (9) | 0.0193 (8) |
N2 | 0.0338 (7) | 0.0550 (9) | 0.0521 (8) | −0.0008 (6) | 0.0053 (6) | 0.0145 (7) |
N3 | 0.0425 (7) | 0.0497 (8) | 0.0504 (8) | −0.0001 (6) | 0.0121 (7) | 0.0066 (7) |
N4 | 0.1149 (17) | 0.170 (2) | 0.0722 (13) | 0.0597 (17) | 0.0252 (12) | −0.0143 (14) |
N5 | 0.0348 (7) | 0.0746 (10) | 0.0412 (8) | 0.0023 (6) | 0.0060 (6) | 0.0026 (7) |
N6 | 0.0358 (7) | 0.0556 (9) | 0.0475 (8) | 0.0006 (6) | 0.0083 (6) | 0.0077 (6) |
O1 | 0.0343 (6) | 0.0699 (8) | 0.0650 (8) | −0.0040 (5) | −0.0003 (5) | 0.0048 (6) |
O2 | 0.0516 (7) | 0.0749 (10) | 0.0781 (9) | −0.0115 (6) | 0.0052 (7) | 0.0092 (7) |
O3 | 0.0382 (7) | 0.0875 (9) | 0.0533 (7) | 0.0084 (6) | 0.0064 (5) | 0.0136 (6) |
O4 | 0.0332 (6) | 0.0699 (8) | 0.0591 (8) | 0.0054 (5) | 0.0015 (5) | 0.0041 (6) |
C1—C6 | 1.387 (2) | C18—C19 | 1.378 (3) |
C1—C2 | 1.392 (2) | C18—H18A | 0.9300 |
C1—C7 | 1.469 (2) | C19—N4 | 1.372 (3) |
C2—C3 | 1.354 (2) | C19—C20 | 1.384 (3) |
C2—H2A | 0.9300 | C20—C21 | 1.359 (3) |
C3—C4 | 1.389 (2) | C20—H20A | 0.9300 |
C3—H3A | 0.9300 | C21—H21A | 0.9300 |
C4—N1 | 1.365 (2) | C22—O3 | 1.2320 (19) |
C4—C5 | 1.389 (2) | C22—N5 | 1.361 (2) |
C5—C6 | 1.374 (2) | C23—N6 | 1.2773 (19) |
C5—H5A | 0.9300 | C23—C24 | 1.447 (2) |
C6—H6A | 0.9300 | C23—H23A | 0.9300 |
C7—O1 | 1.2274 (18) | C24—C29 | 1.395 (2) |
C7—N2 | 1.3585 (19) | C24—C25 | 1.396 (2) |
C8—N3 | 1.2745 (19) | C25—O4 | 1.3633 (18) |
C8—C9 | 1.446 (2) | C25—C26 | 1.376 (2) |
C8—H8A | 0.9300 | C26—C27 | 1.375 (2) |
C9—C14 | 1.391 (2) | C26—H26A | 0.9300 |
C9—C10 | 1.401 (2) | C27—C28 | 1.390 (3) |
C10—O2 | 1.354 (2) | C27—H27A | 0.9300 |
C10—C11 | 1.381 (3) | C28—C29 | 1.377 (2) |
C11—C12 | 1.375 (3) | C28—C30 | 1.495 (2) |
C11—H11A | 0.9300 | C29—H29A | 0.9300 |
C12—C13 | 1.382 (3) | C30—H30A | 0.9600 |
C12—H12A | 0.9300 | C30—H30B | 0.9600 |
C13—C14 | 1.379 (2) | C30—H30C | 0.9600 |
C13—C15 | 1.503 (3) | N1—H1A | 0.8600 |
C14—H14A | 0.9300 | N1—H1B | 0.8600 |
C15—H15A | 0.9600 | N2—N3 | 1.3746 (18) |
C15—H15B | 0.9600 | N2—H1N2 | 0.9357 |
C15—H15C | 0.9600 | N4—H4A | 0.8600 |
C16—C17 | 1.386 (2) | N4—H4B | 0.8600 |
C16—C21 | 1.389 (2) | N5—N6 | 1.3693 (18) |
C16—C22 | 1.467 (2) | N5—H1N5 | 0.9526 |
C17—C18 | 1.375 (3) | O2—H2 | 0.8200 |
C17—H17A | 0.9300 | O4—H4 | 0.8200 |
C6—C1—C2 | 117.47 (15) | C19—C18—H18A | 119.6 |
C6—C1—C7 | 123.98 (14) | N4—C19—C18 | 121.6 (2) |
C2—C1—C7 | 118.34 (14) | N4—C19—C20 | 120.3 (2) |
C3—C2—C1 | 121.66 (16) | C18—C19—C20 | 118.12 (18) |
C3—C2—H2A | 119.2 | C21—C20—C19 | 121.11 (18) |
C1—C2—H2A | 119.2 | C21—C20—H20A | 119.4 |
C2—C3—C4 | 120.99 (16) | C19—C20—H20A | 119.4 |
C2—C3—H3A | 119.5 | C20—C21—C16 | 121.48 (18) |
C4—C3—H3A | 119.5 | C20—C21—H21A | 119.3 |
N1—C4—C3 | 120.40 (16) | C16—C21—H21A | 119.3 |
N1—C4—C5 | 121.57 (17) | O3—C22—N5 | 120.98 (16) |
C3—C4—C5 | 118.03 (16) | O3—C22—C16 | 122.88 (15) |
C6—C5—C4 | 120.71 (16) | N5—C22—C16 | 116.13 (14) |
C6—C5—H5A | 119.6 | N6—C23—C24 | 120.07 (14) |
C4—C5—H5A | 119.6 | N6—C23—H23A | 120.0 |
C5—C6—C1 | 121.12 (15) | C24—C23—H23A | 120.0 |
C5—C6—H6A | 119.4 | C29—C24—C25 | 117.95 (15) |
C1—C6—H6A | 119.4 | C29—C24—C23 | 120.09 (14) |
O1—C7—N2 | 120.24 (15) | C25—C24—C23 | 121.93 (14) |
O1—C7—C1 | 122.84 (14) | O4—C25—C26 | 118.01 (14) |
N2—C7—C1 | 116.88 (13) | O4—C25—C24 | 122.05 (15) |
N3—C8—C9 | 119.98 (15) | C26—C25—C24 | 119.92 (15) |
N3—C8—H8A | 120.0 | C27—C26—C25 | 120.60 (16) |
C9—C8—H8A | 120.0 | C27—C26—H26A | 119.7 |
C14—C9—C10 | 118.37 (15) | C25—C26—H26A | 119.7 |
C14—C9—C8 | 119.70 (15) | C26—C27—C28 | 121.37 (17) |
C10—C9—C8 | 121.92 (15) | C26—C27—H27A | 119.3 |
O2—C10—C11 | 118.23 (16) | C28—C27—H27A | 119.3 |
O2—C10—C9 | 122.92 (16) | C29—C28—C27 | 117.21 (16) |
C11—C10—C9 | 118.84 (17) | C29—C28—C30 | 122.23 (18) |
C12—C11—C10 | 121.07 (18) | C27—C28—C30 | 120.55 (18) |
C12—C11—H11A | 119.5 | C28—C29—C24 | 122.95 (16) |
C10—C11—H11A | 119.5 | C28—C29—H29A | 118.5 |
C11—C12—C13 | 121.56 (18) | C24—C29—H29A | 118.5 |
C11—C12—H12A | 119.2 | C28—C30—H30A | 109.5 |
C13—C12—H12A | 119.2 | C28—C30—H30B | 109.5 |
C14—C13—C12 | 116.99 (18) | H30A—C30—H30B | 109.5 |
C14—C13—C15 | 121.74 (19) | C28—C30—H30C | 109.5 |
C12—C13—C15 | 121.25 (18) | H30A—C30—H30C | 109.5 |
C13—C14—C9 | 123.14 (17) | H30B—C30—H30C | 109.5 |
C13—C14—H14A | 118.4 | C4—N1—H1A | 120.0 |
C9—C14—H14A | 118.4 | C4—N1—H1B | 120.0 |
C13—C15—H15A | 109.5 | H1A—N1—H1B | 120.0 |
C13—C15—H15B | 109.5 | C7—N2—N3 | 117.71 (13) |
H15A—C15—H15B | 109.5 | C7—N2—H1N2 | 122.5 |
C13—C15—H15C | 109.5 | N3—N2—H1N2 | 118.4 |
H15A—C15—H15C | 109.5 | C8—N3—N2 | 118.76 (13) |
H15B—C15—H15C | 109.5 | C19—N4—H4A | 120.0 |
C17—C16—C21 | 117.31 (16) | C19—N4—H4B | 120.0 |
C17—C16—C22 | 124.35 (15) | H4A—N4—H4B | 120.0 |
C21—C16—C22 | 118.28 (15) | C22—N5—N6 | 118.69 (13) |
C18—C17—C16 | 121.16 (17) | C22—N5—H1N5 | 121.4 |
C18—C17—H17A | 119.4 | N6—N5—H1N5 | 119.5 |
C16—C17—H17A | 119.4 | C23—N6—N5 | 118.36 (13) |
C17—C18—C19 | 120.81 (18) | C10—O2—H2 | 109.5 |
C17—C18—H18A | 119.6 | C25—O4—H4 | 109.5 |
C6—C1—C2—C3 | −0.9 (2) | C17—C18—C19—C20 | −1.3 (3) |
C7—C1—C2—C3 | 174.06 (16) | N4—C19—C20—C21 | 179.6 (2) |
C1—C2—C3—C4 | −0.7 (3) | C18—C19—C20—C21 | 0.9 (3) |
C2—C3—C4—N1 | −178.50 (17) | C19—C20—C21—C16 | 0.0 (3) |
C2—C3—C4—C5 | 1.9 (3) | C17—C16—C21—C20 | −0.4 (3) |
N1—C4—C5—C6 | 178.96 (16) | C22—C16—C21—C20 | 176.92 (18) |
C3—C4—C5—C6 | −1.4 (3) | C17—C16—C22—O3 | 163.12 (17) |
C4—C5—C6—C1 | −0.2 (3) | C21—C16—C22—O3 | −14.1 (3) |
C2—C1—C6—C5 | 1.3 (2) | C17—C16—C22—N5 | −15.7 (2) |
C7—C1—C6—C5 | −173.31 (15) | C21—C16—C22—N5 | 167.10 (15) |
C6—C1—C7—O1 | 155.69 (16) | N6—C23—C24—C29 | −178.99 (15) |
C2—C1—C7—O1 | −18.9 (2) | N6—C23—C24—C25 | 3.2 (2) |
C6—C1—C7—N2 | −21.9 (2) | C29—C24—C25—O4 | −178.41 (14) |
C2—C1—C7—N2 | 163.53 (14) | C23—C24—C25—O4 | −0.5 (2) |
N3—C8—C9—C14 | −174.96 (15) | C29—C24—C25—C26 | 0.3 (2) |
N3—C8—C9—C10 | 6.4 (2) | C23—C24—C25—C26 | 178.13 (16) |
C14—C9—C10—O2 | 179.69 (16) | O4—C25—C26—C27 | 178.73 (15) |
C8—C9—C10—O2 | −1.6 (3) | C24—C25—C26—C27 | 0.0 (3) |
C14—C9—C10—C11 | −0.8 (2) | C25—C26—C27—C28 | −0.4 (3) |
C8—C9—C10—C11 | 177.92 (16) | C26—C27—C28—C29 | 0.4 (3) |
O2—C10—C11—C12 | −178.53 (17) | C26—C27—C28—C30 | −178.63 (17) |
C9—C10—C11—C12 | 1.9 (3) | C27—C28—C29—C24 | −0.1 (3) |
C10—C11—C12—C13 | −1.8 (3) | C30—C28—C29—C24 | 178.90 (17) |
C11—C12—C13—C14 | 0.4 (3) | C25—C24—C29—C28 | −0.2 (2) |
C11—C12—C13—C15 | −178.03 (18) | C23—C24—C29—C28 | −178.10 (16) |
C12—C13—C14—C9 | 0.7 (3) | O1—C7—N2—N3 | −1.8 (2) |
C15—C13—C14—C9 | 179.17 (17) | C1—C7—N2—N3 | 175.79 (13) |
C10—C9—C14—C13 | −0.5 (3) | C9—C8—N3—N2 | −179.45 (14) |
C8—C9—C14—C13 | −179.26 (16) | C7—N2—N3—C8 | 178.80 (14) |
C21—C16—C17—C18 | 0.0 (3) | O3—C22—N5—N6 | −0.6 (2) |
C22—C16—C17—C18 | −177.14 (17) | C16—C22—N5—N6 | 178.23 (14) |
C16—C17—C18—C19 | 0.8 (3) | C24—C23—N6—N5 | −178.08 (14) |
C17—C18—C19—N4 | −179.9 (2) | C22—N5—N6—C23 | −177.96 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N3 | 0.82 | 1.89 | 2.6079 (19) | 145 |
O4—H4···N6 | 0.82 | 1.86 | 2.5826 (17) | 146 |
N2—H1N2···O4i | 0.94 | 2.01 | 2.9342 (18) | 169 |
N5—H1N5···O1ii | 0.95 | 1.93 | 2.8615 (17) | 167 |
N1—H1A···O3iii | 0.86 | 2.42 | 3.149 (2) | 142 |
C12—H12A···O3iv | 0.93 | 2.51 | 3.400 (2) | 160 |
C17—H17A···O1ii | 0.93 | 2.53 | 3.320 (2) | 143 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y+1, z; (iv) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H15N3O2 |
Mr | 269.30 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 10.2717 (8), 11.5668 (10), 11.9152 (9) |
α, β, γ (°) | 94.544 (3), 100.583 (3), 95.880 (3) |
V (Å3) | 1377.28 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.25 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.974, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21355, 6081, 3917 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.642 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.137, 1.05 |
No. of reflections | 6081 |
No. of parameters | 365 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.17 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N3 | 0.82 | 1.89 | 2.6079 (19) | 145 |
O4—H4···N6 | 0.82 | 1.86 | 2.5826 (17) | 146 |
N2—H1N2···O4i | 0.94 | 2.01 | 2.9342 (18) | 169 |
N5—H1N5···O1ii | 0.95 | 1.93 | 2.8615 (17) | 167 |
N1—H1A···O3iii | 0.86 | 2.42 | 3.149 (2) | 142 |
C12—H12A···O3iv | 0.93 | 2.51 | 3.400 (2) | 160 |
C17—H17A···O1ii | 0.93 | 2.53 | 3.320 (2) | 143 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y+1, z; (iv) x, y, z+1. |
Footnotes
‡Present address: Structural Dynamics of (Bio)Chemical Systems, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany.
Acknowledgements
HK thanks PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for the research facility.
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.
Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and magnetism, and supramolecular architectures (Karthikeyan et al., 2006; Kucukguzel et al., 2006). Structures of Schiff bases derived from substituted 4-aminobenzohydrazide have been reported earlier (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002; Kargar et al. (2012a,b). In order to explore the structure of new Schiff base derivatives, the title compound was prepared and characterized crystallographically.
The asymmetric unit of the title compound, Fig. 1, comprises two crystallographically independent molecules (A and B) both with an E conformation around the C═N bond. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those reported for related structures (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002; Kargar et al. (2012a,b). In each molecule there is an intramolecular O—H···N hydrogen bond making an S(6) ring motif. The dihedral angles between the substituted phenyl rings (C1-C6/C9-C14 in molecule A and C16-C21/C24-C29 in molecule B) are 17.49 (9) and 10.03 (9)°, respectively.
In the crystal, N—H···O hydrogen bonds (Table 1 and Fig. 2) link neighbouring independent molecules into infinite chains, of the type -A-B-A-B-, along the a axis, enclosing R12(7) ring motifs (Bernstein et al., 1995). The chains are linked by N-H···O hydrogen bonds and C—H···O interactions leading to the formation of a three-dimensional network (Table 1).