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Two chalcones were synthesized by the aldolic condensation of enolizable aromatic ketones with substituted benzaldehydes under Claisen–Schmidt reaction conditions and then treated with 2,4-dinitrophenylhydrazine to yield their corresponding hydrazones. The two (E,Z)-2,4-dinitrophenylhydrazone structures, namely (Z)-1-(2,4-dinitrophenyl)-2-[(E)-3-(4-methylphenyl)-1-phenylallylidene]hydrazine, C22H18N4O4, (H1), and (Z)-1-[(E)-3-(4-chlorophenyl)-1-(naphthalen-1-yl)allylidene]-2-(2,4-dinitrophenyl)hydrazine, C25H17ClN4O4, (H2), were isolated by recrystallization and characterized by FT–IR, UV–Vis, single-crystal and powder X-ray diffraction methods. The UV–Vis spectra of the hydrazones have been studied in two organic solvents of different polarity. It was found that (H2) has a molar extinction coefficient larger than 40000. Single-crystal X-ray diffraction analysis reveals that the molecular zigzag chains of (H1) and (H2) are interconnected through noncovalent contacts. A quantitative analysis of the intermolecular interactions in the crystal structures has been performed using Hirshfeld surface analysis. All the synthesized chalcones and hydrazones were evaluated for their antibacterial and antioxidant activities. Results indicate that the studied compounds show significant activity against Gram negative Escherichia coli strain and the chalcone 3-(4-methylphenyl)-1-phenylprop-2-en-1-one, (C1), was the most effective. In addition, only hydrazone (H1) displayed a moderate DPPH (2,2-diphenyl-1-picryl hydrazyl) scavenging efficiency.
Supporting information
CCDC references: 1841261; 1841260
For both structures, data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 (Bruker, 2011); data reduction: APEX2 (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and SIR2002 program (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).
(
Z)-1-(2,4-Dinitrophenyl)-2-[(
E)-3-(4-methylphenyl)-1-phenylallylidene]hydrazine (H1)
top
Crystal data top
C22H18N4O4 | F(000) = 840 |
Mr = 402.4 | Dx = 1.335 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2520 (3) Å | Cell parameters from 3232 reflections |
b = 19.7485 (10) Å | θ = 2.8–25.3° |
c = 14.0347 (6) Å | µ = 0.09 mm−1 |
β = 95.058 (2)° | T = 298 K |
V = 2002.17 (16) Å3 | Needle, red |
Z = 4 | 0.12 × 0.05 × 0.04 mm |
Data collection top
Bruker APEXII diffractometer | 3356 independent reflections |
Radiation source: Enraf Nonius FR590 | 2161 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
CCD rotation images, thick slices scans | θmax = 24.7°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −8→8 |
Tmin = 0.986, Tmax = 0.991 | k = −23→23 |
13949 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.17 | w = 1/[σ2(Fo2) + (0.1019P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3356 reflections | Δρmax = 0.23 e Å−3 |
272 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.033 (9) |
Special details top
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. Room-temperature intensity data were collected on an APEXII
Bruker AXS diffractometer with CCD area-detector, Mo Kα radiation (λ=
0.71073 Å) and graphite monochromator. The structure was
solved by direct methods using SIR2002 program (Burla et al., 2005)
and refinement was done by full-matrix least-squares on F2 using the
SHELXL97 program suite (Sheldrick, 2008). All non-hydrogen atoms were refined
anisotropically. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.7474 (2) | 0.55748 (9) | 0.44218 (12) | 0.0559 (5) | |
O1 | 0.5823 (2) | 0.69958 (9) | 0.26075 (11) | 0.0747 (5) | |
N2 | 0.7007 (2) | 0.61835 (8) | 0.39937 (12) | 0.0549 (5) | |
H2 | 0.6448 | 0.6194 | 0.3427 | 0.066* | |
O3 | 0.8710 (3) | 0.91178 (10) | 0.55819 (15) | 0.0961 (6) | |
O2 | 0.6152 (3) | 0.80743 (9) | 0.27526 (12) | 0.0894 (6) | |
N3 | 0.6308 (3) | 0.74993 (10) | 0.30838 (13) | 0.0599 (5) | |
O4 | 0.9572 (3) | 0.85232 (10) | 0.68293 (14) | 0.0939 (6) | |
N4 | 0.8909 (3) | 0.85720 (11) | 0.59987 (16) | 0.0704 (6) | |
C32 | 0.7104 (3) | 0.74143 (10) | 0.40560 (14) | 0.0487 (5) | |
C21 | 0.5486 (3) | 0.50385 (10) | 0.31135 (15) | 0.0531 (6) | |
C22 | 0.3631 (3) | 0.48739 (12) | 0.31576 (19) | 0.0694 (7) | |
H22 | 0.3202 | 0.4745 | 0.3736 | 0.083* | |
C3 | 0.6618 (3) | 0.37896 (11) | 0.42806 (15) | 0.0532 (5) | |
H3 | 0.5863 | 0.3748 | 0.3713 | 0.064* | |
C2 | 0.7254 (3) | 0.44062 (10) | 0.45119 (15) | 0.0563 (6) | |
H2A | 0.8094 | 0.4438 | 0.505 | 0.068* | |
C35 | 0.8694 (3) | 0.73313 (12) | 0.59125 (15) | 0.0578 (6) | |
H35 | 0.9225 | 0.7309 | 0.654 | 0.069* | |
C31 | 0.7433 (2) | 0.67671 (10) | 0.44692 (14) | 0.0471 (5) | |
C16 | 0.6646 (3) | 0.25440 (11) | 0.44172 (17) | 0.0579 (6) | |
H16 | 0.6151 | 0.2521 | 0.3784 | 0.069* | |
C26 | 0.6091 (3) | 0.52153 (11) | 0.22450 (16) | 0.0642 (6) | |
H26 | 0.733 | 0.5324 | 0.2207 | 0.077* | |
C1 | 0.6773 (3) | 0.50320 (10) | 0.40117 (15) | 0.0518 (5) | |
C33 | 0.7566 (3) | 0.80030 (11) | 0.45597 (15) | 0.0534 (6) | |
H33 | 0.7338 | 0.8425 | 0.4278 | 0.064* | |
C11 | 0.7000 (3) | 0.31720 (10) | 0.48404 (15) | 0.0496 (5) | |
C34 | 0.8363 (3) | 0.79536 (11) | 0.54776 (15) | 0.0546 (6) | |
C36 | 0.8241 (3) | 0.67514 (11) | 0.54203 (15) | 0.0545 (6) | |
H36 | 0.8471 | 0.6336 | 0.5719 | 0.065* | |
C23 | 0.2424 (4) | 0.49022 (13) | 0.2338 (2) | 0.0859 (8) | |
H23 | 0.1178 | 0.4801 | 0.2368 | 0.103* | |
C12 | 0.7711 (3) | 0.31786 (11) | 0.57929 (16) | 0.0569 (6) | |
H12 | 0.7952 | 0.3591 | 0.6098 | 0.068* | |
C13 | 0.8066 (3) | 0.25878 (12) | 0.62936 (17) | 0.0654 (6) | |
H13 | 0.8532 | 0.2609 | 0.6932 | 0.078* | |
C24 | 0.3062 (5) | 0.50800 (13) | 0.1479 (2) | 0.0894 (9) | |
H24 | 0.2248 | 0.5095 | 0.0929 | 0.107* | |
C15 | 0.7019 (3) | 0.19520 (12) | 0.4924 (2) | 0.0671 (7) | |
H15 | 0.6778 | 0.1538 | 0.4622 | 0.081* | |
C14 | 0.7743 (3) | 0.19615 (12) | 0.58681 (19) | 0.0672 (7) | |
C25 | 0.4882 (5) | 0.52337 (13) | 0.14312 (18) | 0.0808 (8) | |
H25 | 0.531 | 0.5351 | 0.0848 | 0.097* | |
C4 | 0.8156 (5) | 0.13102 (15) | 0.6417 (2) | 0.1044 (10) | |
H4A | 0.8647 | 0.1415 | 0.7058 | 0.157* | |
H4B | 0.9046 | 0.105 | 0.6106 | 0.157* | |
H4C | 0.7036 | 0.1053 | 0.6436 | 0.157* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0604 (11) | 0.0528 (11) | 0.0529 (11) | 0.0019 (8) | −0.0043 (8) | 0.0035 (8) |
O1 | 0.1048 (14) | 0.0645 (11) | 0.0511 (9) | 0.0063 (9) | −0.0137 (9) | −0.0036 (8) |
N2 | 0.0627 (11) | 0.0516 (11) | 0.0480 (10) | −0.0002 (8) | −0.0089 (8) | 0.0007 (8) |
O3 | 0.1284 (17) | 0.0615 (12) | 0.0962 (14) | −0.0124 (11) | −0.0018 (12) | −0.0074 (10) |
O2 | 0.1351 (17) | 0.0644 (12) | 0.0651 (11) | 0.0033 (10) | −0.0111 (11) | 0.0146 (9) |
N3 | 0.0699 (12) | 0.0614 (13) | 0.0480 (11) | 0.0053 (9) | 0.0028 (9) | 0.0058 (9) |
O4 | 0.1135 (15) | 0.0896 (14) | 0.0739 (13) | −0.0135 (11) | −0.0174 (11) | −0.0211 (10) |
N4 | 0.0724 (13) | 0.0689 (15) | 0.0693 (15) | −0.0090 (11) | 0.0030 (11) | −0.0129 (12) |
C32 | 0.0450 (11) | 0.0575 (13) | 0.0436 (11) | 0.0008 (9) | 0.0037 (9) | 0.0024 (9) |
C21 | 0.0621 (14) | 0.0443 (12) | 0.0511 (13) | 0.0056 (9) | −0.0045 (10) | −0.0027 (9) |
C22 | 0.0680 (16) | 0.0696 (16) | 0.0687 (16) | −0.0014 (12) | −0.0045 (12) | 0.0002 (12) |
C3 | 0.0525 (12) | 0.0594 (14) | 0.0466 (12) | 0.0052 (10) | −0.0015 (9) | −0.0015 (10) |
C2 | 0.0606 (13) | 0.0561 (14) | 0.0500 (12) | 0.0025 (10) | −0.0075 (10) | 0.0019 (10) |
C35 | 0.0508 (12) | 0.0733 (15) | 0.0480 (12) | −0.0068 (11) | −0.0027 (9) | −0.0044 (11) |
C31 | 0.0420 (11) | 0.0546 (13) | 0.0448 (11) | −0.0013 (9) | 0.0036 (9) | −0.0003 (9) |
C16 | 0.0530 (13) | 0.0592 (14) | 0.0605 (13) | −0.0046 (10) | −0.0005 (10) | −0.0042 (11) |
C26 | 0.0807 (16) | 0.0583 (14) | 0.0530 (14) | 0.0071 (11) | 0.0026 (12) | −0.0045 (11) |
C1 | 0.0528 (13) | 0.0533 (13) | 0.0486 (12) | 0.0016 (10) | 0.0011 (9) | −0.0017 (10) |
C33 | 0.0505 (12) | 0.0545 (13) | 0.0561 (14) | −0.0015 (9) | 0.0091 (10) | 0.0037 (10) |
C11 | 0.0427 (11) | 0.0522 (12) | 0.0531 (12) | 0.0006 (9) | 0.0008 (9) | −0.0002 (9) |
C34 | 0.0476 (12) | 0.0596 (14) | 0.0563 (13) | −0.0057 (10) | 0.0036 (10) | −0.0068 (10) |
C36 | 0.0526 (12) | 0.0599 (13) | 0.0498 (12) | −0.0025 (10) | −0.0029 (9) | 0.0061 (10) |
C23 | 0.0727 (17) | 0.0791 (19) | 0.100 (2) | −0.0018 (13) | −0.0257 (15) | −0.0052 (16) |
C12 | 0.0590 (13) | 0.0557 (13) | 0.0543 (13) | −0.0002 (10) | −0.0045 (10) | −0.0003 (10) |
C13 | 0.0598 (14) | 0.0735 (17) | 0.0610 (14) | 0.0025 (11) | −0.0054 (11) | 0.0118 (12) |
C24 | 0.117 (3) | 0.0716 (18) | 0.071 (2) | 0.0090 (16) | −0.0399 (17) | −0.0060 (14) |
C15 | 0.0593 (14) | 0.0513 (14) | 0.0916 (19) | −0.0051 (10) | 0.0109 (13) | −0.0032 (12) |
C14 | 0.0570 (14) | 0.0614 (16) | 0.0840 (18) | 0.0031 (11) | 0.0100 (13) | 0.0170 (13) |
C25 | 0.117 (2) | 0.0716 (17) | 0.0512 (15) | 0.0102 (16) | −0.0093 (14) | −0.0037 (12) |
C4 | 0.114 (2) | 0.0755 (19) | 0.124 (3) | 0.0091 (16) | 0.013 (2) | 0.0379 (18) |
Geometric parameters (Å, º) top
N1—C1 | 1.299 (3) | C31—C36 | 1.410 (3) |
N1—N2 | 1.373 (2) | C16—C15 | 1.383 (3) |
O1—N3 | 1.232 (2) | C16—C11 | 1.389 (3) |
N2—C31 | 1.354 (2) | C16—H16 | 0.93 |
N2—H2 | 0.86 | C26—C25 | 1.377 (4) |
O3—N4 | 1.229 (3) | C26—H26 | 0.93 |
O2—N3 | 1.228 (2) | C33—C34 | 1.368 (3) |
N3—C32 | 1.444 (3) | C33—H33 | 0.93 |
O4—N4 | 1.225 (3) | C11—C12 | 1.390 (3) |
N4—C34 | 1.460 (3) | C36—H36 | 0.93 |
C32—C33 | 1.386 (3) | C23—C24 | 1.374 (4) |
C32—C31 | 1.415 (3) | C23—H23 | 0.93 |
C21—C26 | 1.376 (3) | C12—C13 | 1.375 (3) |
C21—C22 | 1.391 (3) | C12—H12 | 0.93 |
C21—C1 | 1.501 (3) | C13—C14 | 1.384 (3) |
C22—C23 | 1.384 (4) | C13—H13 | 0.93 |
C22—H22 | 0.93 | C24—C25 | 1.362 (4) |
C3—C2 | 1.332 (3) | C24—H24 | 0.93 |
C3—C11 | 1.464 (3) | C15—C14 | 1.382 (4) |
C3—H3 | 0.93 | C15—H15 | 0.93 |
C2—C1 | 1.449 (3) | C14—C4 | 1.516 (3) |
C2—H2A | 0.93 | C25—H25 | 0.93 |
C35—C36 | 1.363 (3) | C4—H4A | 0.96 |
C35—C34 | 1.384 (3) | C4—H4B | 0.96 |
C35—H35 | 0.93 | C4—H4C | 0.96 |
| | | |
C1—N1—N2 | 117.18 (18) | C34—C33—C32 | 118.90 (19) |
C31—N2—N1 | 119.54 (17) | C34—C33—H33 | 120.5 |
C31—N2—H2 | 120.2 | C32—C33—H33 | 120.5 |
N1—N2—H2 | 120.2 | C16—C11—C12 | 117.3 (2) |
O2—N3—O1 | 121.91 (19) | C16—C11—C3 | 119.7 (2) |
O2—N3—C32 | 118.74 (19) | C12—C11—C3 | 123.03 (19) |
O1—N3—C32 | 119.34 (18) | C33—C34—C35 | 121.4 (2) |
O4—N4—O3 | 122.8 (2) | C33—C34—N4 | 119.0 (2) |
O4—N4—C34 | 118.5 (2) | C35—C34—N4 | 119.5 (2) |
O3—N4—C34 | 118.7 (2) | C35—C36—C31 | 121.5 (2) |
C33—C32—C31 | 121.61 (19) | C35—C36—H36 | 119.2 |
C33—C32—N3 | 116.29 (18) | C31—C36—H36 | 119.2 |
C31—C32—N3 | 122.09 (19) | C24—C23—C22 | 120.2 (3) |
C26—C21—C22 | 118.9 (2) | C24—C23—H23 | 119.9 |
C26—C21—C1 | 121.53 (19) | C22—C23—H23 | 119.9 |
C22—C21—C1 | 119.53 (19) | C13—C12—C11 | 121.4 (2) |
C23—C22—C21 | 119.8 (3) | C13—C12—H12 | 119.3 |
C23—C22—H22 | 120.1 | C11—C12—H12 | 119.3 |
C21—C22—H22 | 120.1 | C12—C13—C14 | 121.4 (2) |
C2—C3—C11 | 125.8 (2) | C12—C13—H13 | 119.3 |
C2—C3—H3 | 117.1 | C14—C13—H13 | 119.3 |
C11—C3—H3 | 117.1 | C25—C24—C23 | 120.2 (3) |
C3—C2—C1 | 126.7 (2) | C25—C24—H24 | 119.9 |
C3—C2—H2A | 116.6 | C23—C24—H24 | 119.9 |
C1—C2—H2A | 116.6 | C14—C15—C16 | 121.5 (2) |
C36—C35—C34 | 119.9 (2) | C14—C15—H15 | 119.3 |
C36—C35—H35 | 120.1 | C16—C15—H15 | 119.3 |
C34—C35—H35 | 120.1 | C15—C14—C13 | 117.5 (2) |
N2—C31—C36 | 120.38 (19) | C15—C14—C4 | 121.2 (3) |
N2—C31—C32 | 122.96 (18) | C13—C14—C4 | 121.4 (3) |
C36—C31—C32 | 116.66 (19) | C24—C25—C26 | 120.1 (3) |
C15—C16—C11 | 121.0 (2) | C24—C25—H25 | 119.9 |
C15—C16—H16 | 119.5 | C26—C25—H25 | 119.9 |
C11—C16—H16 | 119.5 | C14—C4—H4A | 109.5 |
C21—C26—C25 | 120.8 (2) | C14—C4—H4B | 109.5 |
C21—C26—H26 | 119.6 | H4A—C4—H4B | 109.5 |
C25—C26—H26 | 119.6 | C14—C4—H4C | 109.5 |
N1—C1—C2 | 114.9 (2) | H4A—C4—H4C | 109.5 |
N1—C1—C21 | 123.73 (18) | H4B—C4—H4C | 109.5 |
C2—C1—C21 | 121.30 (18) | | |
| | | |
C1—N1—N2—C31 | 168.76 (16) | C15—C16—C11—C3 | 179.04 (17) |
O2—N3—C32—C33 | 2.7 (3) | C2—C3—C11—C16 | −164.07 (19) |
O1—N3—C32—C33 | −178.09 (17) | C2—C3—C11—C12 | 16.0 (3) |
O2—N3—C32—C31 | −176.09 (18) | C32—C33—C34—C35 | −0.8 (3) |
O1—N3—C32—C31 | 3.2 (3) | C32—C33—C34—N4 | 177.95 (16) |
C26—C21—C22—C23 | −1.2 (3) | C36—C35—C34—C33 | 0.7 (3) |
C1—C21—C22—C23 | 177.7 (2) | C36—C35—C34—N4 | −177.99 (17) |
C11—C3—C2—C1 | −174.50 (18) | O4—N4—C34—C33 | 177.9 (2) |
N1—N2—C31—C36 | −4.1 (3) | O3—N4—C34—C33 | −3.2 (3) |
N1—N2—C31—C32 | 175.92 (16) | O4—N4—C34—C35 | −3.3 (3) |
C33—C32—C31—N2 | −179.60 (16) | O3—N4—C34—C35 | 175.54 (18) |
N3—C32—C31—N2 | −0.9 (3) | C34—C35—C36—C31 | −0.1 (3) |
C33—C32—C31—C36 | 0.4 (3) | N2—C31—C36—C35 | 179.55 (17) |
N3—C32—C31—C36 | 179.10 (17) | C32—C31—C36—C35 | −0.5 (3) |
C22—C21—C26—C25 | 0.4 (3) | C21—C22—C23—C24 | 1.2 (4) |
C1—C21—C26—C25 | −178.5 (2) | C16—C11—C12—C13 | 0.6 (3) |
N2—N1—C1—C2 | −177.78 (15) | C3—C11—C12—C13 | −179.51 (18) |
N2—N1—C1—C21 | −0.6 (3) | C11—C12—C13—C14 | 0.5 (3) |
C3—C2—C1—N1 | 174.99 (19) | C22—C23—C24—C25 | −0.5 (4) |
C3—C2—C1—C21 | −2.3 (3) | C11—C16—C15—C14 | 0.4 (3) |
C26—C21—C1—N1 | 69.3 (3) | C16—C15—C14—C13 | 0.6 (3) |
C22—C21—C1—N1 | −109.5 (2) | C16—C15—C14—C4 | −179.7 (2) |
C26—C21—C1—C2 | −113.6 (2) | C12—C13—C14—C15 | −1.1 (3) |
C22—C21—C1—C2 | 67.5 (3) | C12—C13—C14—C4 | 179.3 (2) |
C31—C32—C33—C34 | 0.2 (3) | C23—C24—C25—C26 | −0.3 (4) |
N3—C32—C33—C34 | −178.57 (17) | C21—C26—C25—C24 | 0.4 (4) |
C15—C16—C11—C12 | −1.1 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.86 | 1.99 | 2.608 (2) | 128 |
N2—H2···N3 | 0.86 | 2.62 | 2.921 (2) | 102 |
C16—H16···O1i | 0.93 | 2.54 | 3.397 (3) | 154 |
C36—H36···N1 | 0.93 | 2.42 | 2.745 (3) | 100 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
(
Z)-1-[(
E)-3-(4-Chlorophenyl)-1-(naphthalen-1-yl)allylidene]-2-(2,4-dinitrophenyl)hydrazine (H2)
top
Crystal data top
C25H17ClN4O4 | F(000) = 976 |
Mr = 472.88 | Dx = 1.397 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3922 (4) Å | Cell parameters from 2922 reflections |
b = 20.9233 (14) Å | θ = 2.4–22.6° |
c = 14.7828 (9) Å | µ = 0.21 mm−1 |
β = 100.571 (2)° | T = 298 K |
V = 2247.6 (2) Å3 | Needle, red |
Z = 4 | 0.13 × 0.05 × 0.03 mm |
Data collection top
Bruker APEXII diffractometer | 3780 independent reflections |
Radiation source: Enraf Nonius FR590 | 2340 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
CCD rotation images, thick slices scans | θmax = 24.7°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −7→8 |
Tmin = 0.913, Tmax = 0.981 | k = −24→24 |
12563 measured reflections | l = −17→17 |
Refinement top
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) = 0.167 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0932P)2 + 0.1167P] where P = (Fo2 + 2Fc2)/3 |
3780 reflections | (Δ/σ)max < 0.001 |
307 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Special details top
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. Room-temperature intensity data were collected on an APEXII
Bruker AXS diffractometer with CCD area-detector, Mo Kα radiation (λ=
0.71073 Å) and graphite monochromator. The structure was
solved by direct methods using SIR2002 program (Burla et al., 2005)
and refinement was done by full-matrix least-squares on F2 using the
SHELXL97 program suite (Sheldrick, 2008). All non-hydrogen atoms were refined
anisotropically. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.93794 (14) | 0.84936 (4) | 0.40527 (7) | 0.1075 (4) | |
N2 | 0.7184 (3) | 0.37627 (9) | 0.58667 (14) | 0.0560 (6) | |
H2A | 0.7441 | 0.3749 | 0.6458 | 0.067* | |
N1 | 0.7413 (3) | 0.43191 (9) | 0.54119 (14) | 0.0552 (6) | |
O1 | 0.7676 (4) | 0.29844 (11) | 0.72685 (13) | 0.0965 (8) | |
O3 | 0.4168 (4) | 0.11197 (11) | 0.42511 (17) | 0.1062 (8) | |
C32 | 0.6412 (3) | 0.26362 (11) | 0.58022 (16) | 0.0501 (6) | |
C3 | 0.8611 (3) | 0.59650 (11) | 0.58416 (17) | 0.0534 (6) | |
H3 | 0.8831 | 0.5973 | 0.6481 | 0.064* | |
C30 | 0.6663 (3) | 0.50137 (10) | 0.73798 (16) | 0.0497 (6) | |
C34 | 0.5100 (3) | 0.21718 (11) | 0.43665 (18) | 0.0541 (6) | |
C2 | 0.8146 (4) | 0.54067 (12) | 0.54467 (18) | 0.0574 (7) | |
H2 | 0.7970 | 0.5390 | 0.4808 | 0.069* | |
C33 | 0.5674 (3) | 0.21077 (12) | 0.52979 (18) | 0.0542 (6) | |
H33 | 0.5571 | 0.1718 | 0.5586 | 0.065* | |
C11 | 0.8817 (3) | 0.65724 (11) | 0.53786 (17) | 0.0500 (6) | |
C29 | 0.4982 (3) | 0.52450 (12) | 0.68715 (19) | 0.0581 (7) | |
H29 | 0.4791 | 0.5246 | 0.6232 | 0.070* | |
O2 | 0.6936 (4) | 0.20011 (11) | 0.70958 (14) | 0.1084 (9) | |
C22 | 0.9691 (4) | 0.45568 (13) | 0.7485 (2) | 0.0687 (8) | |
H22 | 1.0642 | 0.4412 | 0.7205 | 0.082* | |
C25 | 0.6898 (4) | 0.50055 (12) | 0.83553 (17) | 0.0607 (7) | |
N3 | 0.7035 (4) | 0.25359 (12) | 0.67784 (15) | 0.0708 (7) | |
C36 | 0.5963 (3) | 0.32661 (12) | 0.44216 (17) | 0.0561 (7) | |
H36 | 0.6073 | 0.3649 | 0.4117 | 0.067* | |
C31 | 0.6550 (3) | 0.32353 (11) | 0.53817 (16) | 0.0460 (6) | |
C13 | 0.8484 (4) | 0.72431 (14) | 0.4028 (2) | 0.0668 (8) | |
H13 | 0.8134 | 0.7293 | 0.3395 | 0.080* | |
C1 | 0.7887 (3) | 0.48140 (11) | 0.59293 (17) | 0.0527 (6) | |
C21 | 0.8130 (3) | 0.47949 (11) | 0.69606 (17) | 0.0536 (6) | |
C16 | 0.9550 (4) | 0.70994 (12) | 0.58946 (19) | 0.0596 (7) | |
H16 | 0.9923 | 0.7055 | 0.6527 | 0.072* | |
C15 | 0.9739 (4) | 0.76855 (13) | 0.5493 (2) | 0.0661 (8) | |
H15 | 1.0229 | 0.8031 | 0.5851 | 0.079* | |
C14 | 0.9198 (4) | 0.77515 (12) | 0.4565 (2) | 0.0633 (7) | |
C26 | 0.5464 (6) | 0.52525 (15) | 0.8769 (2) | 0.0852 (10) | |
H26 | 0.5604 | 0.5261 | 0.9407 | 0.102* | |
N4 | 0.4275 (4) | 0.16207 (12) | 0.3849 (2) | 0.0766 (7) | |
C35 | 0.5235 (4) | 0.27449 (12) | 0.39261 (18) | 0.0590 (7) | |
H35 | 0.4834 | 0.2777 | 0.3294 | 0.071* | |
O4 | 0.3693 (4) | 0.16852 (11) | 0.30282 (18) | 0.1181 (10) | |
C12 | 0.8288 (4) | 0.66594 (13) | 0.44310 (18) | 0.0596 (7) | |
H12 | 0.7794 | 0.6318 | 0.4065 | 0.072* | |
C28 | 0.3648 (4) | 0.54648 (14) | 0.7308 (3) | 0.0786 (9) | |
H28 | 0.2545 | 0.5610 | 0.6963 | 0.094* | |
C23 | 0.9876 (5) | 0.45285 (15) | 0.8457 (3) | 0.0900 (11) | |
H23 | 1.0936 | 0.4358 | 0.8812 | 0.108* | |
C27 | 0.3896 (6) | 0.54761 (15) | 0.8252 (3) | 0.0947 (12) | |
H27 | 0.2974 | 0.5640 | 0.8538 | 0.114* | |
C24 | 0.8503 (6) | 0.47504 (16) | 0.8864 (2) | 0.0831 (10) | |
H24 | 0.8638 | 0.4732 | 0.9502 | 0.100* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1236 (8) | 0.0636 (5) | 0.1375 (9) | 0.0011 (5) | 0.0301 (7) | 0.0296 (5) |
N2 | 0.0744 (15) | 0.0485 (12) | 0.0461 (12) | −0.0070 (10) | 0.0139 (11) | −0.0018 (10) |
N1 | 0.0702 (14) | 0.0454 (12) | 0.0532 (13) | −0.0048 (10) | 0.0196 (10) | −0.0006 (10) |
O1 | 0.157 (2) | 0.0730 (14) | 0.0521 (12) | −0.0226 (14) | −0.0005 (13) | 0.0004 (11) |
O3 | 0.145 (2) | 0.0547 (13) | 0.1084 (18) | −0.0221 (13) | −0.0038 (16) | −0.0051 (13) |
C32 | 0.0548 (15) | 0.0514 (14) | 0.0453 (14) | 0.0031 (12) | 0.0126 (11) | 0.0016 (12) |
C3 | 0.0550 (15) | 0.0521 (15) | 0.0524 (14) | −0.0035 (11) | 0.0081 (12) | −0.0024 (12) |
C30 | 0.0605 (16) | 0.0364 (12) | 0.0519 (15) | −0.0075 (11) | 0.0098 (13) | 0.0008 (11) |
C34 | 0.0509 (15) | 0.0486 (15) | 0.0601 (16) | −0.0028 (11) | 0.0036 (12) | −0.0081 (13) |
C2 | 0.0687 (17) | 0.0523 (15) | 0.0538 (15) | −0.0033 (13) | 0.0176 (13) | −0.0006 (12) |
C33 | 0.0559 (16) | 0.0452 (14) | 0.0628 (17) | −0.0013 (12) | 0.0142 (13) | 0.0018 (12) |
C11 | 0.0454 (14) | 0.0477 (14) | 0.0581 (16) | 0.0004 (11) | 0.0131 (12) | −0.0026 (12) |
C29 | 0.0558 (16) | 0.0532 (15) | 0.0662 (17) | −0.0018 (13) | 0.0138 (14) | 0.0069 (13) |
O2 | 0.192 (3) | 0.0673 (14) | 0.0635 (14) | −0.0162 (15) | 0.0169 (14) | 0.0134 (11) |
C22 | 0.0606 (18) | 0.0592 (16) | 0.081 (2) | 0.0042 (13) | −0.0019 (15) | 0.0001 (15) |
C25 | 0.090 (2) | 0.0466 (14) | 0.0440 (15) | −0.0155 (14) | 0.0081 (15) | 0.0001 (12) |
N3 | 0.1024 (19) | 0.0575 (14) | 0.0529 (15) | −0.0068 (13) | 0.0149 (13) | 0.0038 (13) |
C36 | 0.0624 (16) | 0.0501 (14) | 0.0563 (16) | 0.0007 (12) | 0.0120 (13) | 0.0041 (13) |
C31 | 0.0456 (14) | 0.0461 (13) | 0.0484 (14) | 0.0008 (11) | 0.0141 (11) | −0.0019 (11) |
C13 | 0.0678 (18) | 0.0711 (19) | 0.0620 (17) | 0.0052 (15) | 0.0129 (14) | 0.0098 (15) |
C1 | 0.0554 (15) | 0.0494 (14) | 0.0542 (15) | −0.0046 (12) | 0.0129 (12) | −0.0045 (12) |
C21 | 0.0574 (16) | 0.0420 (13) | 0.0590 (16) | −0.0048 (12) | 0.0048 (13) | −0.0013 (12) |
C16 | 0.0577 (16) | 0.0539 (16) | 0.0669 (17) | −0.0036 (13) | 0.0105 (13) | −0.0078 (14) |
C15 | 0.0597 (17) | 0.0495 (16) | 0.089 (2) | −0.0074 (13) | 0.0145 (16) | −0.0082 (15) |
C14 | 0.0537 (17) | 0.0504 (15) | 0.087 (2) | 0.0030 (12) | 0.0171 (15) | 0.0074 (15) |
C26 | 0.135 (3) | 0.0618 (19) | 0.069 (2) | −0.023 (2) | 0.046 (2) | −0.0049 (16) |
N4 | 0.0838 (18) | 0.0639 (17) | 0.0758 (18) | −0.0057 (13) | −0.0023 (14) | −0.0106 (14) |
C35 | 0.0656 (18) | 0.0593 (17) | 0.0498 (15) | 0.0010 (13) | 0.0044 (13) | 0.0006 (13) |
O4 | 0.166 (3) | 0.0887 (17) | 0.0804 (17) | −0.0266 (16) | −0.0271 (17) | −0.0136 (14) |
C12 | 0.0607 (17) | 0.0536 (15) | 0.0645 (18) | −0.0025 (12) | 0.0112 (14) | −0.0050 (13) |
C28 | 0.074 (2) | 0.0643 (18) | 0.106 (3) | 0.0043 (15) | 0.0399 (19) | 0.0164 (18) |
C23 | 0.089 (3) | 0.071 (2) | 0.091 (3) | −0.0050 (18) | −0.034 (2) | 0.0108 (19) |
C27 | 0.112 (3) | 0.0601 (19) | 0.130 (4) | 0.0017 (19) | 0.071 (3) | 0.002 (2) |
C24 | 0.114 (3) | 0.073 (2) | 0.0547 (18) | −0.023 (2) | −0.005 (2) | 0.0013 (16) |
Geometric parameters (Å, º) top
Cl1—C14 | 1.743 (3) | C22—C21 | 1.361 (4) |
N2—C31 | 1.352 (3) | C22—C23 | 1.419 (5) |
N2—N1 | 1.370 (3) | C22—H22 | 0.9300 |
N2—H2A | 0.8600 | C25—C24 | 1.390 (4) |
N1—C1 | 1.297 (3) | C25—C26 | 1.415 (4) |
O1—N3 | 1.226 (3) | C36—C35 | 1.368 (3) |
O3—N4 | 1.215 (3) | C36—C31 | 1.407 (3) |
C32—C33 | 1.388 (3) | C36—H36 | 0.9300 |
C32—C31 | 1.411 (3) | C13—C14 | 1.373 (4) |
C32—N3 | 1.447 (3) | C13—C12 | 1.378 (4) |
C3—C2 | 1.323 (3) | C13—H13 | 0.9300 |
C3—C11 | 1.465 (3) | C1—C21 | 1.503 (3) |
C3—H3 | 0.9300 | C16—C15 | 1.381 (4) |
C30—C29 | 1.415 (3) | C16—H16 | 0.9300 |
C30—C21 | 1.420 (3) | C15—C14 | 1.364 (4) |
C30—C25 | 1.421 (3) | C15—H15 | 0.9300 |
C34—C33 | 1.371 (3) | C26—C27 | 1.349 (5) |
C34—C35 | 1.377 (3) | C26—H26 | 0.9300 |
C34—N4 | 1.455 (3) | N4—O4 | 1.218 (3) |
C2—C1 | 1.461 (3) | C35—H35 | 0.9300 |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C33—H33 | 0.9300 | C28—C27 | 1.374 (5) |
C11—C16 | 1.393 (3) | C28—H28 | 0.9300 |
C11—C12 | 1.395 (3) | C23—C24 | 1.354 (5) |
C29—C28 | 1.354 (4) | C23—H23 | 0.9300 |
C29—H29 | 0.9300 | C27—H27 | 0.9300 |
O2—N3 | 1.221 (3) | C24—H24 | 0.9300 |
| | | |
C31—N2—N1 | 119.68 (19) | C14—C13—C12 | 119.8 (3) |
C31—N2—H2A | 120.2 | C14—C13—H13 | 120.1 |
N1—N2—H2A | 120.2 | C12—C13—H13 | 120.1 |
C1—N1—N2 | 115.7 (2) | N1—C1—C2 | 115.8 (2) |
C33—C32—C31 | 121.6 (2) | N1—C1—C21 | 123.1 (2) |
C33—C32—N3 | 116.2 (2) | C2—C1—C21 | 121.1 (2) |
C31—C32—N3 | 122.2 (2) | C22—C21—C30 | 120.3 (2) |
C2—C3—C11 | 126.9 (2) | C22—C21—C1 | 121.2 (2) |
C2—C3—H3 | 116.5 | C30—C21—C1 | 118.4 (2) |
C11—C3—H3 | 116.5 | C15—C16—C11 | 121.8 (3) |
C29—C30—C21 | 123.1 (2) | C15—C16—H16 | 119.1 |
C29—C30—C25 | 118.4 (2) | C11—C16—H16 | 119.1 |
C21—C30—C25 | 118.6 (2) | C14—C15—C16 | 119.3 (3) |
C33—C34—C35 | 121.6 (2) | C14—C15—H15 | 120.4 |
C33—C34—N4 | 118.3 (2) | C16—C15—H15 | 120.4 |
C35—C34—N4 | 120.1 (2) | C15—C14—C13 | 120.9 (3) |
C3—C2—C1 | 125.5 (2) | C15—C14—Cl1 | 119.7 (2) |
C3—C2—H2 | 117.2 | C13—C14—Cl1 | 119.4 (2) |
C1—C2—H2 | 117.2 | C27—C26—C25 | 121.0 (3) |
C34—C33—C32 | 118.7 (2) | C27—C26—H26 | 119.5 |
C34—C33—H33 | 120.6 | C25—C26—H26 | 119.5 |
C32—C33—H33 | 120.6 | O3—N4—O4 | 122.7 (3) |
C16—C11—C12 | 117.1 (2) | O3—N4—C34 | 119.0 (3) |
C16—C11—C3 | 119.6 (2) | O4—N4—C34 | 118.3 (3) |
C12—C11—C3 | 123.2 (2) | C36—C35—C34 | 119.8 (2) |
C28—C29—C30 | 120.6 (3) | C36—C35—H35 | 120.1 |
C28—C29—H29 | 119.7 | C34—C35—H35 | 120.1 |
C30—C29—H29 | 119.7 | C13—C12—C11 | 121.1 (2) |
C21—C22—C23 | 120.4 (3) | C13—C12—H12 | 119.4 |
C21—C22—H22 | 119.8 | C11—C12—H12 | 119.4 |
C23—C22—H22 | 119.8 | C29—C28—C27 | 121.1 (3) |
C24—C25—C26 | 122.6 (3) | C29—C28—H28 | 119.5 |
C24—C25—C30 | 119.2 (3) | C27—C28—H28 | 119.5 |
C26—C25—C30 | 118.2 (3) | C24—C23—C22 | 119.7 (3) |
O2—N3—O1 | 121.2 (2) | C24—C23—H23 | 120.2 |
O2—N3—C32 | 119.1 (2) | C22—C23—H23 | 120.2 |
O1—N3—C32 | 119.7 (2) | C26—C27—C28 | 120.7 (3) |
C35—C36—C31 | 121.4 (2) | C26—C27—H27 | 119.7 |
C35—C36—H36 | 119.3 | C28—C27—H27 | 119.7 |
C31—C36—H36 | 119.3 | C23—C24—C25 | 121.7 (3) |
N2—C31—C36 | 120.7 (2) | C23—C24—H24 | 119.1 |
N2—C31—C32 | 122.5 (2) | C25—C24—H24 | 119.1 |
C36—C31—C32 | 116.8 (2) | | |
| | | |
C31—N2—N1—C1 | 174.8 (2) | C25—C30—C21—C22 | 2.9 (3) |
C11—C3—C2—C1 | −177.6 (2) | C29—C30—C21—C1 | 0.4 (3) |
C35—C34—C33—C32 | −0.1 (4) | C25—C30—C21—C1 | −179.1 (2) |
N4—C34—C33—C32 | −178.1 (2) | N1—C1—C21—C22 | 79.5 (3) |
C31—C32—C33—C34 | 1.2 (4) | C2—C1—C21—C22 | −101.7 (3) |
N3—C32—C33—C34 | −178.6 (2) | N1—C1—C21—C30 | −98.5 (3) |
C2—C3—C11—C16 | −171.5 (3) | C2—C1—C21—C30 | 80.3 (3) |
C2—C3—C11—C12 | 9.3 (4) | C12—C11—C16—C15 | 0.5 (4) |
C21—C30—C29—C28 | −178.1 (2) | C3—C11—C16—C15 | −178.7 (2) |
C25—C30—C29—C28 | 1.3 (4) | C11—C16—C15—C14 | −0.2 (4) |
C29—C30—C25—C24 | 176.8 (2) | C16—C15—C14—C13 | −0.4 (4) |
C21—C30—C25—C24 | −3.7 (3) | C16—C15—C14—Cl1 | 178.5 (2) |
C29—C30—C25—C26 | −2.4 (3) | C12—C13—C14—C15 | 0.8 (4) |
C21—C30—C25—C26 | 177.0 (2) | C12—C13—C14—Cl1 | −178.17 (19) |
C33—C32—N3—O2 | 2.2 (4) | C24—C25—C26—C27 | −177.7 (3) |
C31—C32—N3—O2 | −177.6 (2) | C30—C25—C26—C27 | 1.6 (4) |
C33—C32—N3—O1 | −178.9 (3) | C33—C34—N4—O3 | −2.0 (4) |
C31—C32—N3—O1 | 1.4 (4) | C35—C34—N4—O3 | −179.9 (3) |
N1—N2—C31—C36 | −5.9 (3) | C33—C34—N4—O4 | 176.9 (3) |
N1—N2—C31—C32 | 175.2 (2) | C35—C34—N4—O4 | −1.1 (4) |
C35—C36—C31—N2 | −176.8 (2) | C31—C36—C35—C34 | −1.3 (4) |
C35—C36—C31—C32 | 2.2 (4) | C33—C34—C35—C36 | 0.2 (4) |
C33—C32—C31—N2 | 176.8 (2) | N4—C34—C35—C36 | 178.1 (2) |
N3—C32—C31—N2 | −3.4 (4) | C14—C13—C12—C11 | −0.5 (4) |
C33—C32—C31—C36 | −2.2 (3) | C16—C11—C12—C13 | −0.1 (4) |
N3—C32—C31—C36 | 177.6 (2) | C3—C11—C12—C13 | 179.0 (2) |
N2—N1—C1—C2 | 179.6 (2) | C30—C29—C28—C27 | 0.8 (4) |
N2—N1—C1—C21 | −1.5 (3) | C21—C22—C23—C24 | −1.2 (4) |
C3—C2—C1—N1 | 179.3 (3) | C25—C26—C27—C28 | 0.5 (5) |
C3—C2—C1—C21 | 0.4 (4) | C29—C28—C27—C26 | −1.7 (5) |
C23—C22—C21—C30 | −0.5 (4) | C22—C23—C24—C25 | 0.3 (5) |
C23—C22—C21—C1 | −178.5 (2) | C26—C25—C24—C23 | −178.6 (3) |
C29—C30—C21—C22 | −177.7 (2) | C30—C25—C24—C23 | 2.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.99 | 2.609 (3) | 128 |
N2—H2A···N3 | 0.86 | 2.61 | 2.911 (3) | 102 |
C23—H23···O3i | 0.93 | 2.56 | 3.452 (4) | 160 |
C36—H36···N1 | 0.93 | 2.43 | 2.751 (3) | 100 |
Symmetry code: (i) x+1, −y+1/2, z+1/2. |
UV–Vis spectral data of 2,4-dinitrophenylhydrazones (H1) and
(H2) in organic solvents of varying polarities top | | Band A | | Band B | | Band C | | Band D | |
Comp. | Solv | λmax | εmax | λmax | εmax | λmax | εmax | λmax | εmax |
H1 | CH2Cl2 | 233 | 3.380 | 265 | 2.762 | 305 | 1.758 | 400 | 2.104 |
| AcOEt | 256 | 2.586 | 273* | - | 305 | 1.390 | 394 | 2.062 |
H2 | CH2Cl2 | 229 | 4.090 | 271 | 1.646 | 305 | 1.490 | 399 | 1.932 |
| AcOEt | 255 | 2.454 | 268* | - | 296 | 1.692 | 392 | 1.916 |
Notes: λmax (nm) and εmax (10 4 l mol-1 cm-1); (*) shoulder. |
Disc diffusion method zones of inhibition (mm) of synthesized compounds and
the antibiotic gentamicin topNo antibacterial activity is indicated by `–'. |
Compounds | Concentrations (mg ml-1) | E. coli | S. aureus | P.aeruginosa |
| 0.5 | 9 | 7 | 8 |
| 1 | 10 | 8 | 7 |
C1 | 2 | 9 | 8 | – |
| 4 | 10 | 8 | 9 |
| 8 | 12 | 8 | – |
| 0.5 | 9 | – | – |
| 1 | 8 | – | – |
C2 | 2 | 10 | – | – |
| 4 | 10 | – | – |
| 8 | 10 | – | – |
| 0.5 | 7 | – | – |
| 1 | 9 | – | – |
H1 | 2 | 9 | – | – |
| 4 | 7 | – | – |
| 8 | 8 | – | – |
| 0.5 | 8 | – | – |
| 1 | 7 | – | – |
H2 | 2 | 7 | – | – |
| 4 | 9 | – | – |
| 8 | 11 | – | – |
Gentamicin | 10 µg ml-1 | 34 | 24 | 30 |
Characteristic IR absorption bands of chalcones (C1) and (C2),
and hydrazone derivatives (H1) and (H2) (cm-1) topIR | NH | C—Hsp2 | C—Hsp3 | C═O | C═N | C═C (alkene) | C═C (aromatic) | NO2 |
C1 | - | 3050.0 | 2920.0 | 1653.4 | - | 1592.0 | 1567.1–1511.7 | - |
C2 | - | 3048.6 | - | 1656.9 | - | 1586.1 | 1564.8–1506.9 | - |
H1 | 3274.8 | 3094.8 | 2914.7 | - | 1610.8 | 1587.0 | 1517.6–1492.2 | 1364.4 |
H2 | 3267.2 | 3097.0 | - | - | 1611.8 | 1590.1 | 1515.5–1505.9 | 1362.1 |
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