organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(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

(Received 17 October 2012; accepted 22 October 2012; online 31 October 2012)

The asymmetric unit of the title compound, C19H15N3O2, 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.

Related literature

For applications of hydrazones, see: Angell et al. (2006[Angell, S. E., Rogers, C. W., Zhang, Y., Wolf, M. O. & Jones, W. E. Jr (2006). Coord. Chem. Rev. 250, 1829-1841.]); Vicini et al. (2002[Vicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002). Eur. J. Med. Chem. 37, 553-564.]); Rollas et al. (2002[Rollas, S., Gulerman, N. & Erdeniz, H. (2002). Il Farmaco, 57, 171-174.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15N3O2

  • Mr = 317.34

  • Triclinic, [P \overline 1]

  • a = 10.8648 (6) Å

  • b = 11.1477 (6) Å

  • c = 16.2075 (7) Å

  • α = 72.084 (4)°

  • β = 89.037 (4)°

  • γ = 62.084 (6)°

  • V = 1631.47 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.6 × 0.36 × 0.29 mm

Data collection
  • Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer

  • Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.963, Tmax = 0.98

  • 11850 measured reflections

  • 6432 independent reflections

  • 3566 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.100

  • S = 0.89

  • 6432 reflections

  • 434 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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 DA 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.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

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.

Related literature top

For applications of hydrazones, see: Angell et al. (2006); Vicini et al. (2002); Rollas et al. (2002).

Experimental top

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 hydrazones 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%. UV 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.

Refinement top

H 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).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
(E)-1-(4-Nitrobenzylidene)-2,2-diphenylhydrazine top
Crystal data top
C19H15N3O2Z = 4
Mr = 317.34F(000) = 664
Triclinic, P1Dx = 1.292 Mg m3
a = 10.8648 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1477 (6) ÅCell parameters from 4346 reflections
c = 16.2075 (7) Åθ = 3.6–26.0°
α = 72.084 (4)°µ = 0.09 mm1
β = 89.037 (4)°T = 298 K
γ = 62.084 (6)°Prism, yellow
V = 1631.47 (18) Å30.6 × 0.36 × 0.29 mm
Data collection top
Oxford Diffraction Xcalibur (Atlas, Gemini)
diffractometer
6432 independent reflections
Graphite monochromator3566 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1Rint = 0.020
ω scansθmax = 26.1°, θmin = 3.6°
Absorption correction: analytical
(CrysAlis PRO; Oxford Diffraction, 2009)
h = 1312
Tmin = 0.963, Tmax = 0.98k = 1311
11850 measured reflectionsl = 2019
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-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 reflectionsΔρmax = 0.19 e Å3
434 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0160 (12)
Crystal data top
C19H15N3O2γ = 62.084 (6)°
Mr = 317.34V = 1631.47 (18) Å3
Triclinic, P1Z = 4
a = 10.8648 (6) ÅMo Kα radiation
b = 11.1477 (6) ŵ = 0.09 mm1
c = 16.2075 (7) ÅT = 298 K
α = 72.084 (4)°0.6 × 0.36 × 0.29 mm
β = 89.037 (4)°
Data collection top
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 = 0.98Rint = 0.020
11850 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 0.89Δρmax = 0.19 e Å3
6432 reflectionsΔρmin = 0.17 e Å3
434 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N50.37912 (13)0.62485 (13)0.71748 (7)0.0518 (3)
N40.48398 (13)0.55837 (13)0.78710 (7)0.0570 (3)
N20.10818 (12)0.73321 (14)0.28854 (8)0.0526 (3)
N10.00738 (13)0.84107 (14)0.22028 (8)0.0583 (3)
N60.13482 (15)0.81987 (18)0.42567 (8)0.0646 (4)
C10.14313 (15)0.60094 (17)0.30146 (9)0.0516 (4)
H10.09810.57850.26510.062*
C210.20067 (15)0.62924 (15)0.63192 (8)0.0476 (4)
C20.25354 (14)0.48631 (16)0.37320 (9)0.0468 (4)
C200.31425 (15)0.56008 (16)0.70491 (9)0.0533 (4)
H200.340.46760.74290.064*
C270.53186 (15)0.41316 (15)0.84431 (9)0.0466 (4)
C240.01820 (15)0.75367 (16)0.49692 (9)0.0495 (4)
C220.12647 (16)0.55958 (17)0.62402 (9)0.0571 (4)
H220.15130.46940.6650.068*
O40.18158 (13)0.74572 (15)0.41247 (7)0.0865 (4)
C330.54160 (15)0.64120 (16)0.80149 (8)0.0473 (4)
C260.16313 (16)0.76359 (16)0.56908 (9)0.0532 (4)
H260.21230.81150.57290.064*
C250.05410 (16)0.82557 (16)0.50160 (9)0.0550 (4)
H250.02950.91490.45970.066*
C80.06809 (15)0.81009 (15)0.16531 (9)0.0520 (4)
C70.30787 (16)0.34361 (17)0.37839 (9)0.0569 (4)
H70.27160.32220.33670.068*
C30.30811 (15)0.51500 (17)0.43730 (9)0.0557 (4)
H30.27420.610.43440.067*
C340.47117 (17)0.79007 (16)0.76366 (9)0.0542 (4)
H340.3820.83720.73090.065*
C50.46458 (16)0.26540 (17)0.50650 (10)0.0563 (4)
C140.01841 (15)0.98197 (17)0.20603 (10)0.0526 (4)
C380.67299 (16)0.57297 (17)0.85254 (9)0.0565 (4)
H380.72030.47330.87980.068*
O30.17919 (15)0.94622 (16)0.38125 (9)0.0982 (4)
N30.57624 (17)0.14956 (19)0.57804 (11)0.0811 (5)
C230.01649 (16)0.62102 (18)0.55673 (9)0.0575 (4)
H230.03290.57350.55210.069*
C40.41121 (16)0.40499 (18)0.50469 (10)0.0595 (4)
H40.44450.42470.54860.071*
C280.49956 (15)0.38849 (17)0.92809 (9)0.0564 (4)
H280.44570.46570.94720.068*
C150.05885 (17)1.00997 (19)0.25729 (10)0.0625 (4)
H150.12970.93430.30210.075*
C370.73250 (18)0.6538 (2)0.86244 (11)0.0686 (5)
H370.82070.60770.89620.082*
C60.41473 (17)0.23299 (17)0.44433 (10)0.0607 (4)
H60.45220.13790.44640.073*
C350.53307 (19)0.86828 (18)0.77451 (10)0.0659 (4)
H350.48580.96820.74840.079*
C320.60992 (16)0.29899 (18)0.81561 (10)0.0569 (4)
H320.63090.31550.75870.068*
C310.65662 (17)0.16031 (18)0.87176 (12)0.0688 (5)
H310.70960.08270.85280.083*
C120.25571 (18)0.76574 (19)0.13928 (11)0.0705 (5)
H120.33630.76090.15540.085*
C290.54716 (17)0.2492 (2)0.98368 (10)0.0678 (5)
H290.52590.23241.04060.081*
C130.18622 (17)0.80211 (17)0.18977 (10)0.0611 (4)
H130.21950.82110.24010.073*
C90.01978 (17)0.78373 (18)0.09056 (10)0.0669 (5)
H90.05930.79090.07330.08*
O10.60017 (18)0.17750 (16)0.64075 (10)0.1282 (6)
C180.1473 (2)1.2352 (2)0.12438 (13)0.0797 (5)
H180.21681.31140.07910.096*
C190.12189 (17)1.09637 (18)0.13879 (11)0.0664 (4)
H190.17431.07960.10340.08*
C300.62518 (18)0.13607 (19)0.95579 (12)0.0718 (5)
H300.65730.04210.99370.086*
C360.6644 (2)0.8003 (2)0.82365 (12)0.0739 (5)
H360.70610.85370.83030.089*
C160.0311 (2)1.1497 (2)0.24218 (13)0.0757 (5)
H160.08251.16750.27750.091*
O20.64046 (17)0.02998 (17)0.57238 (10)0.1191 (6)
C100.0895 (2)0.7465 (2)0.04114 (11)0.0798 (5)
H100.05680.72790.00930.096*
C170.0716 (2)1.2626 (2)0.17568 (14)0.0809 (5)
H170.08951.35650.16560.097*
C110.2058 (2)0.73704 (19)0.06594 (12)0.0763 (5)
H110.25160.71080.03270.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N50.0556 (8)0.0518 (8)0.0430 (7)0.0262 (7)0.0071 (6)0.0092 (6)
N40.0652 (8)0.0481 (8)0.0504 (7)0.0299 (7)0.0176 (6)0.0023 (6)
N20.0429 (7)0.0548 (9)0.0509 (7)0.0187 (7)0.0022 (6)0.0142 (6)
N10.0501 (8)0.0528 (8)0.0600 (8)0.0181 (7)0.0122 (6)0.0144 (7)
N60.0588 (9)0.0766 (11)0.0497 (8)0.0272 (9)0.0037 (7)0.0193 (8)
C10.0475 (9)0.0592 (11)0.0478 (9)0.0247 (8)0.0018 (7)0.0195 (8)
C210.0536 (9)0.0470 (9)0.0411 (8)0.0247 (8)0.0008 (7)0.0129 (7)
C20.0406 (8)0.0528 (10)0.0449 (8)0.0219 (8)0.0053 (7)0.0151 (7)
C200.0615 (10)0.0488 (9)0.0443 (8)0.0285 (8)0.0058 (7)0.0056 (7)
C270.0457 (8)0.0468 (9)0.0421 (8)0.0218 (7)0.0053 (7)0.0090 (7)
C240.0472 (9)0.0550 (10)0.0402 (8)0.0195 (8)0.0019 (7)0.0170 (8)
C220.0676 (10)0.0580 (10)0.0466 (9)0.0378 (9)0.0011 (8)0.0068 (8)
O40.0908 (9)0.1161 (11)0.0650 (7)0.0651 (9)0.0125 (6)0.0210 (7)
C330.0509 (9)0.0502 (9)0.0422 (8)0.0259 (8)0.0020 (7)0.0151 (7)
C260.0630 (10)0.0475 (9)0.0506 (9)0.0292 (8)0.0043 (8)0.0140 (8)
C250.0665 (10)0.0428 (9)0.0475 (9)0.0212 (8)0.0045 (8)0.0130 (7)
C80.0478 (9)0.0496 (9)0.0476 (9)0.0182 (8)0.0061 (7)0.0106 (7)
C70.0664 (10)0.0591 (11)0.0465 (9)0.0314 (9)0.0041 (8)0.0183 (8)
C30.0507 (9)0.0525 (10)0.0601 (10)0.0208 (8)0.0022 (8)0.0209 (8)
C340.0571 (10)0.0516 (10)0.0507 (9)0.0256 (9)0.0046 (7)0.0142 (8)
C50.0541 (10)0.0544 (10)0.0526 (9)0.0277 (9)0.0044 (7)0.0055 (8)
C140.0430 (9)0.0544 (10)0.0580 (9)0.0202 (8)0.0097 (7)0.0217 (8)
C380.0546 (10)0.0560 (10)0.0563 (9)0.0236 (8)0.0023 (8)0.0206 (8)
O30.0915 (10)0.0763 (10)0.0864 (9)0.0217 (8)0.0377 (8)0.0048 (8)
N30.0853 (12)0.0663 (12)0.0739 (11)0.0364 (10)0.0212 (9)0.0002 (9)
C230.0615 (10)0.0703 (11)0.0501 (9)0.0422 (9)0.0017 (8)0.0155 (9)
C40.0587 (10)0.0658 (12)0.0561 (9)0.0324 (9)0.0049 (8)0.0191 (9)
C280.0526 (9)0.0550 (10)0.0468 (9)0.0148 (8)0.0024 (7)0.0168 (8)
C150.0593 (10)0.0665 (12)0.0648 (10)0.0310 (9)0.0082 (8)0.0257 (9)
C370.0586 (10)0.0853 (14)0.0743 (11)0.0373 (11)0.0047 (9)0.0389 (11)
C60.0704 (11)0.0482 (10)0.0559 (9)0.0256 (9)0.0012 (9)0.0128 (8)
C350.0798 (13)0.0569 (11)0.0693 (11)0.0374 (10)0.0163 (10)0.0254 (9)
C320.0579 (10)0.0623 (11)0.0560 (9)0.0320 (9)0.0119 (8)0.0226 (9)
C310.0585 (10)0.0509 (11)0.0900 (13)0.0186 (9)0.0073 (9)0.0280 (10)
C120.0676 (11)0.0750 (12)0.0608 (11)0.0430 (10)0.0103 (9)0.0020 (9)
C290.0643 (11)0.0710 (13)0.0465 (9)0.0261 (10)0.0008 (8)0.0032 (9)
C130.0571 (10)0.0698 (11)0.0460 (9)0.0299 (9)0.0028 (8)0.0074 (8)
C90.0501 (9)0.0771 (12)0.0603 (10)0.0206 (9)0.0024 (8)0.0233 (9)
O10.1500 (15)0.0965 (11)0.1025 (11)0.0444 (11)0.0683 (10)0.0096 (9)
C180.0667 (12)0.0581 (12)0.0895 (13)0.0163 (10)0.0093 (10)0.0166 (11)
C190.0527 (10)0.0562 (11)0.0771 (11)0.0188 (9)0.0012 (9)0.0179 (9)
C300.0653 (11)0.0499 (11)0.0726 (12)0.0215 (10)0.0104 (9)0.0048 (9)
C360.0821 (14)0.0855 (15)0.0879 (12)0.0570 (12)0.0223 (11)0.0460 (11)
C160.0828 (14)0.0824 (14)0.0848 (13)0.0501 (12)0.0265 (11)0.0419 (12)
O20.1206 (13)0.0599 (9)0.1231 (12)0.0158 (9)0.0382 (10)0.0062 (9)
C100.0748 (13)0.0883 (14)0.0648 (11)0.0240 (12)0.0008 (10)0.0364 (10)
C170.0874 (14)0.0638 (13)0.0968 (15)0.0358 (12)0.0329 (12)0.0368 (12)
C110.0857 (14)0.0690 (12)0.0677 (12)0.0353 (11)0.0172 (10)0.0174 (10)
Geometric parameters (Å, º) top
N5—C201.2774 (17)C14—C151.386 (2)
N5—N41.3632 (15)C14—C191.386 (2)
N4—C331.4062 (17)C38—C371.376 (2)
N4—C271.4335 (17)C38—H380.93
N2—C11.2847 (18)N3—O21.2142 (19)
N2—N11.3633 (16)N3—O11.2154 (18)
N1—C141.4021 (19)C23—H230.93
N1—C81.4368 (18)C4—H40.93
N6—O31.2192 (17)C28—C291.376 (2)
N6—O41.2217 (16)C28—H280.93
N6—C241.4605 (19)C15—C161.380 (2)
C1—C21.4564 (19)C15—H150.93
C1—H10.93C37—C361.365 (2)
C21—C221.3856 (19)C37—H370.93
C21—C261.3966 (19)C6—H60.93
C21—C201.4538 (19)C35—C361.378 (2)
C2—C71.388 (2)C35—H350.93
C2—C31.3914 (19)C32—C311.375 (2)
C20—H200.93C32—H320.93
C27—C281.3738 (19)C31—C301.374 (2)
C27—C321.377 (2)C31—H310.93
C24—C231.370 (2)C12—C111.363 (2)
C24—C251.3762 (19)C12—C131.384 (2)
C22—C231.380 (2)C12—H120.93
C22—H220.93C29—C301.361 (2)
C33—C341.3843 (19)C29—H290.93
C33—C381.3917 (19)C13—H130.93
C26—C251.3745 (19)C9—C101.381 (2)
C26—H260.93C9—H90.93
C25—H250.93C18—C171.369 (2)
C8—C131.371 (2)C18—C191.381 (2)
C8—C91.372 (2)C18—H180.93
C7—C61.379 (2)C19—H190.93
C7—H70.93C30—H300.93
C3—C41.372 (2)C36—H360.93
C3—H30.93C16—C171.372 (2)
C34—C351.375 (2)C16—H160.93
C34—H340.93C10—C111.361 (2)
C5—C61.366 (2)C10—H100.93
C5—C41.373 (2)C17—H170.93
C5—N31.464 (2)C11—H110.93
C20—N5—N4119.59 (12)O1—N3—C5118.34 (17)
N5—N4—C33116.35 (11)C24—C23—C22118.37 (14)
N5—N4—C27122.46 (11)C24—C23—H23120.8
C33—N4—C27121.17 (11)C22—C23—H23120.8
C1—N2—N1120.25 (12)C3—C4—C5119.16 (14)
N2—N1—C14117.33 (12)C3—C4—H4120.4
N2—N1—C8120.82 (12)C5—C4—H4120.4
C14—N1—C8121.85 (12)C27—C28—C29119.80 (15)
O3—N6—O4123.20 (14)C27—C28—H28120.1
O3—N6—C24118.16 (15)C29—C28—H28120.1
O4—N6—C24118.63 (15)C16—C15—C14120.27 (16)
N2—C1—C2119.80 (13)C16—C15—H15119.9
N2—C1—H1120.1C14—C15—H15119.9
C2—C1—H1120.1C36—C37—C38121.16 (16)
C22—C21—C26118.45 (13)C36—C37—H37119.4
C22—C21—C20118.98 (13)C38—C37—H37119.4
C26—C21—C20122.57 (13)C5—C6—C7118.90 (14)
C7—C2—C3118.23 (13)C5—C6—H6120.6
C7—C2—C1119.76 (13)C7—C6—H6120.6
C3—C2—C1122.00 (13)C34—C35—C36120.75 (16)
N5—C20—C21120.75 (13)C34—C35—H35119.6
N5—C20—H20119.6C36—C35—H35119.6
C21—C20—H20119.6C31—C32—C27119.51 (14)
C28—C27—C32120.13 (14)C31—C32—H32120.2
C28—C27—N4119.59 (14)C27—C32—H32120.2
C32—C27—N4120.28 (13)C30—C31—C32120.17 (16)
C23—C24—C25122.04 (13)C30—C31—H31119.9
C23—C24—N6118.78 (14)C32—C31—H31119.9
C25—C24—N6119.18 (14)C11—C12—C13119.87 (16)
C23—C22—C21121.46 (14)C11—C12—H12120.1
C23—C22—H22119.3C13—C12—H12120.1
C21—C22—H22119.3C30—C29—C28120.25 (15)
C34—C33—C38119.20 (13)C30—C29—H29119.9
C34—C33—N4120.96 (12)C28—C29—H29119.9
C38—C33—N4119.82 (13)C8—C13—C12119.74 (15)
C25—C26—C21120.58 (14)C8—C13—H13120.1
C25—C26—H26119.7C12—C13—H13120.1
C21—C26—H26119.7C8—C9—C10119.48 (16)
C26—C25—C24119.09 (14)C8—C9—H9120.3
C26—C25—H25120.5C10—C9—H9120.3
C24—C25—H25120.5C17—C18—C19121.06 (18)
C13—C8—C9120.19 (14)C17—C18—H18119.5
C13—C8—N1119.42 (14)C19—C18—H18119.5
C9—C8—N1120.35 (14)C18—C19—C14120.02 (17)
C6—C7—C2121.11 (14)C18—C19—H19120
C6—C7—H7119.4C14—C19—H19120
C2—C7—H7119.4C29—C30—C31120.14 (16)
C4—C3—C2120.89 (14)C29—C30—H30119.9
C4—C3—H3119.6C31—C30—H30119.9
C2—C3—H3119.6C37—C36—C35119.25 (16)
C35—C34—C33119.97 (14)C37—C36—H36120.4
C35—C34—H34120C35—C36—H36120.4
C33—C34—H34120C17—C16—C15120.79 (18)
C6—C5—C4121.65 (14)C17—C16—H16119.6
C6—C5—N3119.90 (15)C15—C16—H16119.6
C4—C5—N3118.45 (15)C11—C10—C9120.34 (17)
C15—C14—C19118.75 (15)C11—C10—H10119.8
C15—C14—N1121.37 (14)C9—C10—H10119.8
C19—C14—N1119.87 (14)C18—C17—C16119.10 (18)
C37—C38—C33119.64 (15)C18—C17—H17120.4
C37—C38—H38120.2C16—C17—H17120.4
C33—C38—H38120.2C10—C11—C12120.37 (17)
O2—N3—O1122.90 (17)C10—C11—H11119.8
O2—N3—C5118.76 (17)C12—C11—H11119.8
C20—N5—N4—C33174.28 (13)C34—C33—C38—C371.9 (2)
C20—N5—N4—C274.3 (2)N4—C33—C38—C37176.39 (13)
C1—N2—N1—C14175.43 (13)C6—C5—N3—O213.3 (2)
C1—N2—N1—C84.2 (2)C4—C5—N3—O2167.54 (17)
N1—N2—C1—C2178.39 (11)C6—C5—N3—O1166.41 (17)
N2—C1—C2—C7169.14 (13)C4—C5—N3—O112.7 (2)
N2—C1—C2—C310.4 (2)C25—C24—C23—C220.8 (2)
N4—N5—C20—C21179.12 (12)N6—C24—C23—C22179.75 (13)
C22—C21—C20—N5175.58 (14)C21—C22—C23—C240.2 (2)
C26—C21—C20—N54.5 (2)C2—C3—C4—C52.6 (2)
N5—N4—C27—C28108.19 (16)C6—C5—C4—C31.9 (2)
C33—N4—C27—C2870.35 (18)N3—C5—C4—C3178.97 (13)
N5—N4—C27—C3271.90 (19)C32—C27—C28—C290.9 (2)
C33—N4—C27—C32109.55 (15)N4—C27—C28—C29178.97 (13)
O3—N6—C24—C23168.64 (15)C19—C14—C15—C161.1 (2)
O4—N6—C24—C2312.6 (2)N1—C14—C15—C16179.74 (14)
O3—N6—C24—C2511.9 (2)C33—C38—C37—C360.6 (2)
O4—N6—C24—C25166.90 (14)C4—C5—C6—C70.2 (2)
C26—C21—C22—C230.9 (2)N3—C5—C6—C7178.90 (13)
C20—C21—C22—C23179.14 (14)C2—C7—C6—C51.7 (2)
N5—N4—C33—C3417.35 (19)C33—C34—C35—C360.8 (2)
C27—N4—C33—C34161.29 (13)C28—C27—C32—C310.8 (2)
N5—N4—C33—C38160.95 (12)N4—C27—C32—C31179.12 (13)
C27—N4—C33—C3820.4 (2)C27—C32—C31—C300.2 (2)
C22—C21—C26—C250.7 (2)C27—C28—C29—C300.5 (2)
C20—C21—C26—C25179.39 (14)C9—C8—C13—C120.7 (2)
C21—C26—C25—C240.3 (2)N1—C8—C13—C12177.01 (13)
C23—C24—C25—C261.0 (2)C11—C12—C13—C80.5 (2)
N6—C24—C25—C26179.51 (13)C13—C8—C9—C101.2 (2)
N2—N1—C8—C1386.15 (18)N1—C8—C9—C10176.53 (14)
C14—N1—C8—C1394.20 (17)C17—C18—C19—C140.0 (3)
N2—N1—C8—C991.60 (17)C15—C14—C19—C180.6 (2)
C14—N1—C8—C988.05 (18)N1—C14—C19—C18179.78 (14)
C3—C2—C7—C61.1 (2)C28—C29—C30—C310.1 (3)
C1—C2—C7—C6178.45 (13)C32—C31—C30—C290.3 (2)
C7—C2—C3—C41.1 (2)C38—C37—C36—C350.7 (2)
C1—C2—C3—C4179.40 (13)C34—C35—C36—C370.6 (2)
C38—C33—C34—C352.0 (2)C14—C15—C16—C171.0 (3)
N4—C33—C34—C35176.28 (13)C8—C9—C10—C110.5 (3)
N2—N1—C14—C152.2 (2)C19—C18—C17—C160.1 (3)
C8—N1—C14—C15177.42 (13)C15—C16—C17—C180.4 (3)
N2—N1—C14—C19178.56 (12)C9—C10—C11—C120.8 (3)
C8—N1—C14—C191.8 (2)C13—C12—C11—C101.2 (3)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C21–C26, C33–C38 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg1i0.932.923.4080 (18)114
C29—H29···Cg2ii0.932.803.6875 (18)161
C7—H7···Cg20.932.833.4223 (16)123
C30—H30···Cg3iii0.932.843.698 (2)154
C6—H6···O2iv0.932.603.342 (3)138
C15—H15···N20.932.432.750 (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 formulaC19H15N3O2
Mr317.34
Crystal system, space groupTriclinic, 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)
V3)1631.47 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.6 × 0.36 × 0.29
Data collection
DiffractometerOxford Diffraction Xcalibur (Atlas, Gemini)
diffractometer
Absorption correctionAnalytical
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.963, 0.98
No. of measured, independent and
observed [I > 2σ(I)] reflections
11850, 6432, 3566
Rint0.020
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.100, 0.89
No. of reflections6432
No. of parameters434
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C21–C26, C33–C38 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg1i0.932.923.4080 (18)114
C29—H29···Cg2ii0.932.803.6875 (18)161
C7—H7···Cg20.932.833.4223 (16)123
C30—H30···Cg3iii0.932.843.698 (2)154
C6—H6···O2iv0.932.603.342 (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

First citationAngell, 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
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals
First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
First citationRollas, S., Gulerman, N. & Erdeniz, H. (2002). Il Farmaco, 57, 171–174.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationVicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002). Eur. J. Med. Chem. 37, 553–564.  Web of Science CrossRef PubMed CAS

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds