organic compounds
(E)-1-(4-Nitrobenzylidene)-2,2-diphenylhydrazine
aCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Pue., Mexico, bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Pue., Mexico, and cFacultad de Química, Universidad Nacional Autónoma de México, 04510, México D.F., Mexico
*Correspondence e-mail: angel.mendoza.m@gmail.com
The 19H15N3O2, contains two molecules, both of which show an E conformation of the imine bond. The dihedral angles between the phenyl rings in the phenylhydrazine groups are 86.09 (6) and 83.41 (5)° in the two molecules. The 4-nitrobenzene rings show torsion angles of 4.4 (2) and 10.9 (2)° from the two C=N—N planes. In the crystal, C—H⋯π interactions and C—H⋯O hydrogen bonds are observed growing along the a, b and c axes, resulting in a complex supramolecular array.
of the title compound, CRelated literature
For applications of et al. (2006); Vicini et al. (2002); Rollas et al. (2002).
see: AngellExperimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536812043681/bt6850sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812043681/bt6850Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812043681/bt6850Isup3.cml
Diphenylhydrazine was dissolved in ethanol (1.2 chemical equivalents), a chemical equivalent of aldehyde which was previously dissolved in the same solvent and it was added drop by drop stirring constantly. The reaction mixture was kept at room temperature and was monitored by TLC, and then vacuum filtered. The λmax = 411.51 nm. FT IR (film): (cm-1): 3031 ν(C—H), 1591, 1556 ν(C=N), 1508 ν(Ph—NO2). 1H NMR (400 MHz, (CD3)2CO: (d/p.p.m.): 8.20–8.18 (m, 2H), 7.88–7.86 (m, 2H), 7.51–7.47 (m, 4H), 7.29–7.22 (m, 7H). 13C NMR (400 MHz, (CD3)2CO): (d/p.p.m.): 143.02, 143.01, 142.80, 132.30, 130.03, 126.58, 125.35, 123.88, 122.43. MS—EI: m/z = 317 M+ C19H15N3O2.
were recrystallized by a continuous and controlled process until orange crystals with adequate size and purity were developed in order to obtain X-ray studies. Yield 90%. UVH atoms bonded to C atoms were placed in geometrical idealized positions and were refined as riding on their parent atoms, with C—H = 0.93–0.98 Å and with Uiso(H) = 1.2 Ueq(C).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).Fig. 1. The molecular structure of title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. |
C19H15N3O2 | Z = 4 |
Mr = 317.34 | F(000) = 664 |
Triclinic, P1 | Dx = 1.292 Mg m−3 |
a = 10.8648 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1477 (6) Å | Cell parameters from 4346 reflections |
c = 16.2075 (7) Å | θ = 3.6–26.0° |
α = 72.084 (4)° | µ = 0.09 mm−1 |
β = 89.037 (4)° | T = 298 K |
γ = 62.084 (6)° | Prism, yellow |
V = 1631.47 (18) Å3 | 0.6 × 0.36 × 0.29 mm |
Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer | 6432 independent reflections |
Graphite monochromator | 3566 reflections with I > 2σ(I) |
Detector resolution: 10.4685 pixels mm-1 | Rint = 0.020 |
ω scans | θmax = 26.1°, θmin = 3.6° |
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009) | h = −13→12 |
Tmin = 0.963, Tmax = 0.98 | k = −13→11 |
11850 measured reflections | l = −20→19 |
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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0527P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max = 0.001 |
6432 reflections | Δρmax = 0.19 e Å−3 |
434 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008) |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0160 (12) |
C19H15N3O2 | γ = 62.084 (6)° |
Mr = 317.34 | V = 1631.47 (18) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.8648 (6) Å | Mo Kα radiation |
b = 11.1477 (6) Å | µ = 0.09 mm−1 |
c = 16.2075 (7) Å | T = 298 K |
α = 72.084 (4)° | 0.6 × 0.36 × 0.29 mm |
β = 89.037 (4)° |
Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer | 6432 independent reflections |
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009) | 3566 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.98 | Rint = 0.020 |
11850 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 0.89 | Δρmax = 0.19 e Å−3 |
6432 reflections | Δρmin = −0.17 e Å−3 |
434 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
N5 | 0.37912 (13) | 0.62485 (13) | 0.71748 (7) | 0.0518 (3) | |
N4 | 0.48398 (13) | 0.55837 (13) | 0.78710 (7) | 0.0570 (3) | |
N2 | 0.10818 (12) | 0.73321 (14) | 0.28854 (8) | 0.0526 (3) | |
N1 | 0.00738 (13) | 0.84107 (14) | 0.22028 (8) | 0.0583 (3) | |
N6 | −0.13482 (15) | 0.81987 (18) | 0.42567 (8) | 0.0646 (4) | |
C1 | 0.14313 (15) | 0.60094 (17) | 0.30146 (9) | 0.0516 (4) | |
H1 | 0.0981 | 0.5785 | 0.2651 | 0.062* | |
C21 | 0.20067 (15) | 0.62924 (15) | 0.63192 (8) | 0.0476 (4) | |
C2 | 0.25354 (14) | 0.48631 (16) | 0.37320 (9) | 0.0468 (4) | |
C20 | 0.31425 (15) | 0.56008 (16) | 0.70491 (9) | 0.0533 (4) | |
H20 | 0.34 | 0.4676 | 0.7429 | 0.064* | |
C27 | 0.53186 (15) | 0.41316 (15) | 0.84431 (9) | 0.0466 (4) | |
C24 | −0.01820 (15) | 0.75367 (16) | 0.49692 (9) | 0.0495 (4) | |
C22 | 0.12647 (16) | 0.55958 (17) | 0.62402 (9) | 0.0571 (4) | |
H22 | 0.1513 | 0.4694 | 0.665 | 0.068* | |
O4 | −0.18158 (13) | 0.74572 (15) | 0.41247 (7) | 0.0865 (4) | |
C33 | 0.54160 (15) | 0.64120 (16) | 0.80149 (8) | 0.0473 (4) | |
C26 | 0.16313 (16) | 0.76359 (16) | 0.56908 (9) | 0.0532 (4) | |
H26 | 0.2123 | 0.8115 | 0.5729 | 0.064* | |
C25 | 0.05410 (16) | 0.82557 (16) | 0.50160 (9) | 0.0550 (4) | |
H25 | 0.0295 | 0.9149 | 0.4597 | 0.066* | |
C8 | −0.06809 (15) | 0.81009 (15) | 0.16531 (9) | 0.0520 (4) | |
C7 | 0.30787 (16) | 0.34361 (17) | 0.37839 (9) | 0.0569 (4) | |
H7 | 0.2716 | 0.3222 | 0.3367 | 0.068* | |
C3 | 0.30811 (15) | 0.51500 (17) | 0.43730 (9) | 0.0557 (4) | |
H3 | 0.2742 | 0.61 | 0.4344 | 0.067* | |
C34 | 0.47117 (17) | 0.79007 (16) | 0.76366 (9) | 0.0542 (4) | |
H34 | 0.382 | 0.8372 | 0.7309 | 0.065* | |
C5 | 0.46458 (16) | 0.26540 (17) | 0.50650 (10) | 0.0563 (4) | |
C14 | −0.01841 (15) | 0.98197 (17) | 0.20603 (10) | 0.0526 (4) | |
C38 | 0.67299 (16) | 0.57297 (17) | 0.85254 (9) | 0.0565 (4) | |
H38 | 0.7203 | 0.4733 | 0.8798 | 0.068* | |
O3 | −0.17919 (15) | 0.94622 (16) | 0.38125 (9) | 0.0982 (4) | |
N3 | 0.57624 (17) | 0.14956 (19) | 0.57804 (11) | 0.0811 (5) | |
C23 | 0.01649 (16) | 0.62102 (18) | 0.55673 (9) | 0.0575 (4) | |
H23 | −0.0329 | 0.5735 | 0.5521 | 0.069* | |
C4 | 0.41121 (16) | 0.40499 (18) | 0.50469 (10) | 0.0595 (4) | |
H4 | 0.4445 | 0.4247 | 0.5486 | 0.071* | |
C28 | 0.49956 (15) | 0.38849 (17) | 0.92809 (9) | 0.0564 (4) | |
H28 | 0.4457 | 0.4657 | 0.9472 | 0.068* | |
C15 | 0.05885 (17) | 1.00997 (19) | 0.25729 (10) | 0.0625 (4) | |
H15 | 0.1297 | 0.9343 | 0.3021 | 0.075* | |
C37 | 0.73250 (18) | 0.6538 (2) | 0.86244 (11) | 0.0686 (5) | |
H37 | 0.8207 | 0.6077 | 0.8962 | 0.082* | |
C6 | 0.41473 (17) | 0.23299 (17) | 0.44433 (10) | 0.0607 (4) | |
H6 | 0.4522 | 0.1379 | 0.4464 | 0.073* | |
C35 | 0.53307 (19) | 0.86828 (18) | 0.77451 (10) | 0.0659 (4) | |
H35 | 0.4858 | 0.9682 | 0.7484 | 0.079* | |
C32 | 0.60992 (16) | 0.29899 (18) | 0.81561 (10) | 0.0569 (4) | |
H32 | 0.6309 | 0.3155 | 0.7587 | 0.068* | |
C31 | 0.65662 (17) | 0.16031 (18) | 0.87176 (12) | 0.0688 (5) | |
H31 | 0.7096 | 0.0827 | 0.8528 | 0.083* | |
C12 | −0.25571 (18) | 0.76574 (19) | 0.13928 (11) | 0.0705 (5) | |
H12 | −0.3363 | 0.7609 | 0.1554 | 0.085* | |
C29 | 0.54716 (17) | 0.2492 (2) | 0.98368 (10) | 0.0678 (5) | |
H29 | 0.5259 | 0.2324 | 1.0406 | 0.081* | |
C13 | −0.18622 (17) | 0.80211 (17) | 0.18977 (10) | 0.0611 (4) | |
H13 | −0.2195 | 0.8211 | 0.2401 | 0.073* | |
C9 | −0.01978 (17) | 0.78373 (18) | 0.09056 (10) | 0.0669 (5) | |
H9 | 0.0593 | 0.7909 | 0.0733 | 0.08* | |
O1 | 0.60017 (18) | 0.17750 (16) | 0.64075 (10) | 0.1282 (6) | |
C18 | −0.1473 (2) | 1.2352 (2) | 0.12438 (13) | 0.0797 (5) | |
H18 | −0.2168 | 1.3114 | 0.0791 | 0.096* | |
C19 | −0.12189 (17) | 1.09637 (18) | 0.13879 (11) | 0.0664 (4) | |
H19 | −0.1743 | 1.0796 | 0.1034 | 0.08* | |
C30 | 0.62518 (18) | 0.13607 (19) | 0.95579 (12) | 0.0718 (5) | |
H30 | 0.6573 | 0.0421 | 0.9937 | 0.086* | |
C36 | 0.6644 (2) | 0.8003 (2) | 0.82365 (12) | 0.0739 (5) | |
H36 | 0.7061 | 0.8537 | 0.8303 | 0.089* | |
C16 | 0.0311 (2) | 1.1497 (2) | 0.24218 (13) | 0.0757 (5) | |
H16 | 0.0825 | 1.1675 | 0.2775 | 0.091* | |
O2 | 0.64046 (17) | 0.02998 (17) | 0.57238 (10) | 0.1191 (6) | |
C10 | −0.0895 (2) | 0.7465 (2) | 0.04114 (11) | 0.0798 (5) | |
H10 | −0.0568 | 0.7279 | −0.0093 | 0.096* | |
C17 | −0.0716 (2) | 1.2626 (2) | 0.17568 (14) | 0.0809 (5) | |
H17 | −0.0895 | 1.3565 | 0.1656 | 0.097* | |
C11 | −0.2058 (2) | 0.73704 (19) | 0.06594 (12) | 0.0763 (5) | |
H11 | −0.2516 | 0.7108 | 0.0327 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N5 | 0.0556 (8) | 0.0518 (8) | 0.0430 (7) | −0.0262 (7) | −0.0071 (6) | −0.0092 (6) |
N4 | 0.0652 (8) | 0.0481 (8) | 0.0504 (7) | −0.0299 (7) | −0.0176 (6) | −0.0023 (6) |
N2 | 0.0429 (7) | 0.0548 (9) | 0.0509 (7) | −0.0187 (7) | −0.0022 (6) | −0.0142 (6) |
N1 | 0.0501 (8) | 0.0528 (8) | 0.0600 (8) | −0.0181 (7) | −0.0122 (6) | −0.0144 (7) |
N6 | 0.0588 (9) | 0.0766 (11) | 0.0497 (8) | −0.0272 (9) | −0.0037 (7) | −0.0193 (8) |
C1 | 0.0475 (9) | 0.0592 (11) | 0.0478 (9) | −0.0247 (8) | 0.0018 (7) | −0.0195 (8) |
C21 | 0.0536 (9) | 0.0470 (9) | 0.0411 (8) | −0.0247 (8) | 0.0008 (7) | −0.0129 (7) |
C2 | 0.0406 (8) | 0.0528 (10) | 0.0449 (8) | −0.0219 (8) | 0.0053 (7) | −0.0151 (7) |
C20 | 0.0615 (10) | 0.0488 (9) | 0.0443 (8) | −0.0285 (8) | −0.0058 (7) | −0.0056 (7) |
C27 | 0.0457 (8) | 0.0468 (9) | 0.0421 (8) | −0.0218 (7) | −0.0053 (7) | −0.0090 (7) |
C24 | 0.0472 (9) | 0.0550 (10) | 0.0402 (8) | −0.0195 (8) | −0.0019 (7) | −0.0170 (8) |
C22 | 0.0676 (10) | 0.0580 (10) | 0.0466 (9) | −0.0378 (9) | −0.0011 (8) | −0.0068 (8) |
O4 | 0.0908 (9) | 0.1161 (11) | 0.0650 (7) | −0.0651 (9) | −0.0125 (6) | −0.0210 (7) |
C33 | 0.0509 (9) | 0.0502 (9) | 0.0422 (8) | −0.0259 (8) | 0.0020 (7) | −0.0151 (7) |
C26 | 0.0630 (10) | 0.0475 (9) | 0.0506 (9) | −0.0292 (8) | −0.0043 (8) | −0.0140 (8) |
C25 | 0.0665 (10) | 0.0428 (9) | 0.0475 (9) | −0.0212 (8) | −0.0045 (8) | −0.0130 (7) |
C8 | 0.0478 (9) | 0.0496 (9) | 0.0476 (9) | −0.0182 (8) | −0.0061 (7) | −0.0106 (7) |
C7 | 0.0664 (10) | 0.0591 (11) | 0.0465 (9) | −0.0314 (9) | 0.0041 (8) | −0.0183 (8) |
C3 | 0.0507 (9) | 0.0525 (10) | 0.0601 (10) | −0.0208 (8) | −0.0022 (8) | −0.0209 (8) |
C34 | 0.0571 (10) | 0.0516 (10) | 0.0507 (9) | −0.0256 (9) | 0.0046 (7) | −0.0142 (8) |
C5 | 0.0541 (10) | 0.0544 (10) | 0.0526 (9) | −0.0277 (9) | −0.0044 (7) | −0.0055 (8) |
C14 | 0.0430 (9) | 0.0544 (10) | 0.0580 (9) | −0.0202 (8) | 0.0097 (7) | −0.0217 (8) |
C38 | 0.0546 (10) | 0.0560 (10) | 0.0563 (9) | −0.0236 (8) | −0.0023 (8) | −0.0206 (8) |
O3 | 0.0915 (10) | 0.0763 (10) | 0.0864 (9) | −0.0217 (8) | −0.0377 (8) | −0.0048 (8) |
N3 | 0.0853 (12) | 0.0663 (12) | 0.0739 (11) | −0.0364 (10) | −0.0212 (9) | −0.0002 (9) |
C23 | 0.0615 (10) | 0.0703 (11) | 0.0501 (9) | −0.0422 (9) | 0.0017 (8) | −0.0155 (9) |
C4 | 0.0587 (10) | 0.0658 (12) | 0.0561 (9) | −0.0324 (9) | −0.0049 (8) | −0.0191 (9) |
C28 | 0.0526 (9) | 0.0550 (10) | 0.0468 (9) | −0.0148 (8) | −0.0024 (7) | −0.0168 (8) |
C15 | 0.0593 (10) | 0.0665 (12) | 0.0648 (10) | −0.0310 (9) | 0.0082 (8) | −0.0257 (9) |
C37 | 0.0586 (10) | 0.0853 (14) | 0.0743 (11) | −0.0373 (11) | 0.0047 (9) | −0.0389 (11) |
C6 | 0.0704 (11) | 0.0482 (10) | 0.0559 (9) | −0.0256 (9) | 0.0012 (9) | −0.0128 (8) |
C35 | 0.0798 (13) | 0.0569 (11) | 0.0693 (11) | −0.0374 (10) | 0.0163 (10) | −0.0254 (9) |
C32 | 0.0579 (10) | 0.0623 (11) | 0.0560 (9) | −0.0320 (9) | 0.0119 (8) | −0.0226 (9) |
C31 | 0.0585 (10) | 0.0509 (11) | 0.0900 (13) | −0.0186 (9) | 0.0073 (9) | −0.0280 (10) |
C12 | 0.0676 (11) | 0.0750 (12) | 0.0608 (11) | −0.0430 (10) | −0.0103 (9) | 0.0020 (9) |
C29 | 0.0643 (11) | 0.0710 (13) | 0.0465 (9) | −0.0261 (10) | −0.0008 (8) | −0.0032 (9) |
C13 | 0.0571 (10) | 0.0698 (11) | 0.0460 (9) | −0.0299 (9) | −0.0028 (8) | −0.0074 (8) |
C9 | 0.0501 (9) | 0.0771 (12) | 0.0603 (10) | −0.0206 (9) | 0.0024 (8) | −0.0233 (9) |
O1 | 0.1500 (15) | 0.0965 (11) | 0.1025 (11) | −0.0444 (11) | −0.0683 (10) | −0.0096 (9) |
C18 | 0.0667 (12) | 0.0581 (12) | 0.0895 (13) | −0.0163 (10) | 0.0093 (10) | −0.0166 (11) |
C19 | 0.0527 (10) | 0.0562 (11) | 0.0771 (11) | −0.0188 (9) | −0.0012 (9) | −0.0179 (9) |
C30 | 0.0653 (11) | 0.0499 (11) | 0.0726 (12) | −0.0215 (10) | −0.0104 (9) | 0.0048 (9) |
C36 | 0.0821 (14) | 0.0855 (15) | 0.0879 (12) | −0.0570 (12) | 0.0223 (11) | −0.0460 (11) |
C16 | 0.0828 (14) | 0.0824 (14) | 0.0848 (13) | −0.0501 (12) | 0.0265 (11) | −0.0419 (12) |
O2 | 0.1206 (13) | 0.0599 (9) | 0.1231 (12) | −0.0158 (9) | −0.0382 (10) | −0.0062 (9) |
C10 | 0.0748 (13) | 0.0883 (14) | 0.0648 (11) | −0.0240 (12) | −0.0008 (10) | −0.0364 (10) |
C17 | 0.0874 (14) | 0.0638 (13) | 0.0968 (15) | −0.0358 (12) | 0.0329 (12) | −0.0368 (12) |
C11 | 0.0857 (14) | 0.0690 (12) | 0.0677 (12) | −0.0353 (11) | −0.0172 (10) | −0.0174 (10) |
N5—C20 | 1.2774 (17) | C14—C15 | 1.386 (2) |
N5—N4 | 1.3632 (15) | C14—C19 | 1.386 (2) |
N4—C33 | 1.4062 (17) | C38—C37 | 1.376 (2) |
N4—C27 | 1.4335 (17) | C38—H38 | 0.93 |
N2—C1 | 1.2847 (18) | N3—O2 | 1.2142 (19) |
N2—N1 | 1.3633 (16) | N3—O1 | 1.2154 (18) |
N1—C14 | 1.4021 (19) | C23—H23 | 0.93 |
N1—C8 | 1.4368 (18) | C4—H4 | 0.93 |
N6—O3 | 1.2192 (17) | C28—C29 | 1.376 (2) |
N6—O4 | 1.2217 (16) | C28—H28 | 0.93 |
N6—C24 | 1.4605 (19) | C15—C16 | 1.380 (2) |
C1—C2 | 1.4564 (19) | C15—H15 | 0.93 |
C1—H1 | 0.93 | C37—C36 | 1.365 (2) |
C21—C22 | 1.3856 (19) | C37—H37 | 0.93 |
C21—C26 | 1.3966 (19) | C6—H6 | 0.93 |
C21—C20 | 1.4538 (19) | C35—C36 | 1.378 (2) |
C2—C7 | 1.388 (2) | C35—H35 | 0.93 |
C2—C3 | 1.3914 (19) | C32—C31 | 1.375 (2) |
C20—H20 | 0.93 | C32—H32 | 0.93 |
C27—C28 | 1.3738 (19) | C31—C30 | 1.374 (2) |
C27—C32 | 1.377 (2) | C31—H31 | 0.93 |
C24—C23 | 1.370 (2) | C12—C11 | 1.363 (2) |
C24—C25 | 1.3762 (19) | C12—C13 | 1.384 (2) |
C22—C23 | 1.380 (2) | C12—H12 | 0.93 |
C22—H22 | 0.93 | C29—C30 | 1.361 (2) |
C33—C34 | 1.3843 (19) | C29—H29 | 0.93 |
C33—C38 | 1.3917 (19) | C13—H13 | 0.93 |
C26—C25 | 1.3745 (19) | C9—C10 | 1.381 (2) |
C26—H26 | 0.93 | C9—H9 | 0.93 |
C25—H25 | 0.93 | C18—C17 | 1.369 (2) |
C8—C13 | 1.371 (2) | C18—C19 | 1.381 (2) |
C8—C9 | 1.372 (2) | C18—H18 | 0.93 |
C7—C6 | 1.379 (2) | C19—H19 | 0.93 |
C7—H7 | 0.93 | C30—H30 | 0.93 |
C3—C4 | 1.372 (2) | C36—H36 | 0.93 |
C3—H3 | 0.93 | C16—C17 | 1.372 (2) |
C34—C35 | 1.375 (2) | C16—H16 | 0.93 |
C34—H34 | 0.93 | C10—C11 | 1.361 (2) |
C5—C6 | 1.366 (2) | C10—H10 | 0.93 |
C5—C4 | 1.373 (2) | C17—H17 | 0.93 |
C5—N3 | 1.464 (2) | C11—H11 | 0.93 |
C20—N5—N4 | 119.59 (12) | O1—N3—C5 | 118.34 (17) |
N5—N4—C33 | 116.35 (11) | C24—C23—C22 | 118.37 (14) |
N5—N4—C27 | 122.46 (11) | C24—C23—H23 | 120.8 |
C33—N4—C27 | 121.17 (11) | C22—C23—H23 | 120.8 |
C1—N2—N1 | 120.25 (12) | C3—C4—C5 | 119.16 (14) |
N2—N1—C14 | 117.33 (12) | C3—C4—H4 | 120.4 |
N2—N1—C8 | 120.82 (12) | C5—C4—H4 | 120.4 |
C14—N1—C8 | 121.85 (12) | C27—C28—C29 | 119.80 (15) |
O3—N6—O4 | 123.20 (14) | C27—C28—H28 | 120.1 |
O3—N6—C24 | 118.16 (15) | C29—C28—H28 | 120.1 |
O4—N6—C24 | 118.63 (15) | C16—C15—C14 | 120.27 (16) |
N2—C1—C2 | 119.80 (13) | C16—C15—H15 | 119.9 |
N2—C1—H1 | 120.1 | C14—C15—H15 | 119.9 |
C2—C1—H1 | 120.1 | C36—C37—C38 | 121.16 (16) |
C22—C21—C26 | 118.45 (13) | C36—C37—H37 | 119.4 |
C22—C21—C20 | 118.98 (13) | C38—C37—H37 | 119.4 |
C26—C21—C20 | 122.57 (13) | C5—C6—C7 | 118.90 (14) |
C7—C2—C3 | 118.23 (13) | C5—C6—H6 | 120.6 |
C7—C2—C1 | 119.76 (13) | C7—C6—H6 | 120.6 |
C3—C2—C1 | 122.00 (13) | C34—C35—C36 | 120.75 (16) |
N5—C20—C21 | 120.75 (13) | C34—C35—H35 | 119.6 |
N5—C20—H20 | 119.6 | C36—C35—H35 | 119.6 |
C21—C20—H20 | 119.6 | C31—C32—C27 | 119.51 (14) |
C28—C27—C32 | 120.13 (14) | C31—C32—H32 | 120.2 |
C28—C27—N4 | 119.59 (14) | C27—C32—H32 | 120.2 |
C32—C27—N4 | 120.28 (13) | C30—C31—C32 | 120.17 (16) |
C23—C24—C25 | 122.04 (13) | C30—C31—H31 | 119.9 |
C23—C24—N6 | 118.78 (14) | C32—C31—H31 | 119.9 |
C25—C24—N6 | 119.18 (14) | C11—C12—C13 | 119.87 (16) |
C23—C22—C21 | 121.46 (14) | C11—C12—H12 | 120.1 |
C23—C22—H22 | 119.3 | C13—C12—H12 | 120.1 |
C21—C22—H22 | 119.3 | C30—C29—C28 | 120.25 (15) |
C34—C33—C38 | 119.20 (13) | C30—C29—H29 | 119.9 |
C34—C33—N4 | 120.96 (12) | C28—C29—H29 | 119.9 |
C38—C33—N4 | 119.82 (13) | C8—C13—C12 | 119.74 (15) |
C25—C26—C21 | 120.58 (14) | C8—C13—H13 | 120.1 |
C25—C26—H26 | 119.7 | C12—C13—H13 | 120.1 |
C21—C26—H26 | 119.7 | C8—C9—C10 | 119.48 (16) |
C26—C25—C24 | 119.09 (14) | C8—C9—H9 | 120.3 |
C26—C25—H25 | 120.5 | C10—C9—H9 | 120.3 |
C24—C25—H25 | 120.5 | C17—C18—C19 | 121.06 (18) |
C13—C8—C9 | 120.19 (14) | C17—C18—H18 | 119.5 |
C13—C8—N1 | 119.42 (14) | C19—C18—H18 | 119.5 |
C9—C8—N1 | 120.35 (14) | C18—C19—C14 | 120.02 (17) |
C6—C7—C2 | 121.11 (14) | C18—C19—H19 | 120 |
C6—C7—H7 | 119.4 | C14—C19—H19 | 120 |
C2—C7—H7 | 119.4 | C29—C30—C31 | 120.14 (16) |
C4—C3—C2 | 120.89 (14) | C29—C30—H30 | 119.9 |
C4—C3—H3 | 119.6 | C31—C30—H30 | 119.9 |
C2—C3—H3 | 119.6 | C37—C36—C35 | 119.25 (16) |
C35—C34—C33 | 119.97 (14) | C37—C36—H36 | 120.4 |
C35—C34—H34 | 120 | C35—C36—H36 | 120.4 |
C33—C34—H34 | 120 | C17—C16—C15 | 120.79 (18) |
C6—C5—C4 | 121.65 (14) | C17—C16—H16 | 119.6 |
C6—C5—N3 | 119.90 (15) | C15—C16—H16 | 119.6 |
C4—C5—N3 | 118.45 (15) | C11—C10—C9 | 120.34 (17) |
C15—C14—C19 | 118.75 (15) | C11—C10—H10 | 119.8 |
C15—C14—N1 | 121.37 (14) | C9—C10—H10 | 119.8 |
C19—C14—N1 | 119.87 (14) | C18—C17—C16 | 119.10 (18) |
C37—C38—C33 | 119.64 (15) | C18—C17—H17 | 120.4 |
C37—C38—H38 | 120.2 | C16—C17—H17 | 120.4 |
C33—C38—H38 | 120.2 | C10—C11—C12 | 120.37 (17) |
O2—N3—O1 | 122.90 (17) | C10—C11—H11 | 119.8 |
O2—N3—C5 | 118.76 (17) | C12—C11—H11 | 119.8 |
C20—N5—N4—C33 | −174.28 (13) | C34—C33—C38—C37 | −1.9 (2) |
C20—N5—N4—C27 | 4.3 (2) | N4—C33—C38—C37 | 176.39 (13) |
C1—N2—N1—C14 | −175.43 (13) | C6—C5—N3—O2 | 13.3 (2) |
C1—N2—N1—C8 | 4.2 (2) | C4—C5—N3—O2 | −167.54 (17) |
N1—N2—C1—C2 | 178.39 (11) | C6—C5—N3—O1 | −166.41 (17) |
N2—C1—C2—C7 | −169.14 (13) | C4—C5—N3—O1 | 12.7 (2) |
N2—C1—C2—C3 | 10.4 (2) | C25—C24—C23—C22 | 0.8 (2) |
N4—N5—C20—C21 | 179.12 (12) | N6—C24—C23—C22 | −179.75 (13) |
C22—C21—C20—N5 | −175.58 (14) | C21—C22—C23—C24 | 0.2 (2) |
C26—C21—C20—N5 | 4.5 (2) | C2—C3—C4—C5 | 2.6 (2) |
N5—N4—C27—C28 | −108.19 (16) | C6—C5—C4—C3 | −1.9 (2) |
C33—N4—C27—C28 | 70.35 (18) | N3—C5—C4—C3 | 178.97 (13) |
N5—N4—C27—C32 | 71.90 (19) | C32—C27—C28—C29 | 0.9 (2) |
C33—N4—C27—C32 | −109.55 (15) | N4—C27—C28—C29 | −178.97 (13) |
O3—N6—C24—C23 | 168.64 (15) | C19—C14—C15—C16 | 1.1 (2) |
O4—N6—C24—C23 | −12.6 (2) | N1—C14—C15—C16 | −179.74 (14) |
O3—N6—C24—C25 | −11.9 (2) | C33—C38—C37—C36 | 0.6 (2) |
O4—N6—C24—C25 | 166.90 (14) | C4—C5—C6—C7 | −0.2 (2) |
C26—C21—C22—C23 | −0.9 (2) | N3—C5—C6—C7 | 178.90 (13) |
C20—C21—C22—C23 | 179.14 (14) | C2—C7—C6—C5 | 1.7 (2) |
N5—N4—C33—C34 | 17.35 (19) | C33—C34—C35—C36 | −0.8 (2) |
C27—N4—C33—C34 | −161.29 (13) | C28—C27—C32—C31 | −0.8 (2) |
N5—N4—C33—C38 | −160.95 (12) | N4—C27—C32—C31 | 179.12 (13) |
C27—N4—C33—C38 | 20.4 (2) | C27—C32—C31—C30 | 0.2 (2) |
C22—C21—C26—C25 | 0.7 (2) | C27—C28—C29—C30 | −0.5 (2) |
C20—C21—C26—C25 | −179.39 (14) | C9—C8—C13—C12 | 0.7 (2) |
C21—C26—C25—C24 | 0.3 (2) | N1—C8—C13—C12 | −177.01 (13) |
C23—C24—C25—C26 | −1.0 (2) | C11—C12—C13—C8 | 0.5 (2) |
N6—C24—C25—C26 | 179.51 (13) | C13—C8—C9—C10 | −1.2 (2) |
N2—N1—C8—C13 | 86.15 (18) | N1—C8—C9—C10 | 176.53 (14) |
C14—N1—C8—C13 | −94.20 (17) | C17—C18—C19—C14 | 0.0 (3) |
N2—N1—C8—C9 | −91.60 (17) | C15—C14—C19—C18 | −0.6 (2) |
C14—N1—C8—C9 | 88.05 (18) | N1—C14—C19—C18 | −179.78 (14) |
C3—C2—C7—C6 | −1.1 (2) | C28—C29—C30—C31 | −0.1 (3) |
C1—C2—C7—C6 | 178.45 (13) | C32—C31—C30—C29 | 0.3 (2) |
C7—C2—C3—C4 | −1.1 (2) | C38—C37—C36—C35 | 0.7 (2) |
C1—C2—C3—C4 | 179.40 (13) | C34—C35—C36—C37 | −0.6 (2) |
C38—C33—C34—C35 | 2.0 (2) | C14—C15—C16—C17 | −1.0 (3) |
N4—C33—C34—C35 | −176.28 (13) | C8—C9—C10—C11 | 0.5 (3) |
N2—N1—C14—C15 | 2.2 (2) | C19—C18—C17—C16 | 0.1 (3) |
C8—N1—C14—C15 | −177.42 (13) | C15—C16—C17—C18 | 0.4 (3) |
N2—N1—C14—C19 | −178.56 (12) | C9—C10—C11—C12 | 0.8 (3) |
C8—N1—C14—C19 | 1.8 (2) | C13—C12—C11—C10 | −1.2 (3) |
Cg1, Cg2 and Cg3 are the centroids of the C21–C26, C33–C38 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···Cg1i | 0.93 | 2.92 | 3.4080 (18) | 114 |
C29—H29···Cg2ii | 0.93 | 2.80 | 3.6875 (18) | 161 |
C7—H7···Cg2 | 0.93 | 2.83 | 3.4223 (16) | 123 |
C30—H30···Cg3iii | 0.93 | 2.84 | 3.698 (2) | 154 |
C6—H6···O2iv | 0.93 | 2.60 | 3.342 (3) | 138 |
C15—H15···N2 | 0.93 | 2.43 | 2.750 (2) | 100 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x, −y+2, −z; (iv) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C19H15N3O2 |
Mr | 317.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 10.8648 (6), 11.1477 (6), 16.2075 (7) |
α, β, γ (°) | 72.084 (4), 89.037 (4), 62.084 (6) |
V (Å3) | 1631.47 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.6 × 0.36 × 0.29 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer |
Absorption correction | Analytical (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.963, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11850, 6432, 3566 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.100, 0.89 |
No. of reflections | 6432 |
No. of parameters | 434 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.17 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Cg1, Cg2 and Cg3 are the centroids of the C21–C26, C33–C38 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···Cg1i | 0.93 | 2.92 | 3.4080 (18) | 114 |
C29—H29···Cg2ii | 0.93 | 2.80 | 3.6875 (18) | 161 |
C7—H7···Cg2 | 0.93 | 2.83 | 3.4223 (16) | 123 |
C30—H30···Cg3iii | 0.93 | 2.84 | 3.698 (2) | 154 |
C6—H6···O2iv | 0.93 | 2.60 | 3.342 (3) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x, −y+2, −z; (iv) −x+1, −y, −z+1. |
Acknowledgements
We are grateful for financial support (project No. CAVB-NAT11-I, VIEP-BUAP).
References
Angell, S. E., Rogers, C. W., Zhang, Y., Wolf, M. O. & Jones, W. E. Jr (2006). Coord. Chem. Rev. 250, 1829–1841. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Rollas, S., Gulerman, N. & Erdeniz, H. (2002). Il Farmaco, 57, 171–174. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002). Eur. J. Med. Chem. 37, 553–564. Web of Science CrossRef PubMed CAS Google Scholar
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.
Hydrazones have had diverse applications in pharmacology, microbiology and the industry; some of them are used in analytical tests, which serve to detect chemical and biological species (Angell, et al., 2006). Some hydrazones with functional groups like NO2 and Cl, have been studied to have potential antimicrobial agents and were tested for their antibacterial and antifungal activities against (Vicini, et al., 2002 and Rollas et al., 2002). In the industry, hydrazones are used as plasticizing agents, polymerization initiators and antioxidants.
In the title compound C19H15N3O2, the ASU contains two molecules showing an E configuration on each of the C=N groups with diphenylhydrazine group opposite to p-nitrophenyl ring. The dihedral angle for phenyl rings C8—C13 and C14—C19 is 86.09 (6)° for molecule 1 and that between C27—C32 and C33—C38 rings is 83.41 (5)° for molecule 2. The dihedral angle for p-nitrophenyl rings and C=N—N planes are 10.89 (20) and 4.43 (23)° for molecule 1 and 2 respectively. The imine bond distances [N2—C1 1.2847 (18) Å and N5—C20 1.2774 (17) Å] are typical C=N bond. The crystal packing present four intermolecular interactions of the type C—H···π (table 1). Moreover, there is one intermolecular interaction of type hydrogen bond: C6—H6···O2, and an intramolecular interaction of type hydrogen bond, C15—H15···N2.