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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 10| October 2013| Pages o1522-o1523

2-{(E)-[(2Z)-2-(1,2-Di­hydro­phthalazin-1-yl­­idene)hydrazinyl­­idene]meth­yl}phenol

aDepartment of Chemistry and Research Centre, PRNSS College, Mattanur 670 702, Kannur, Kerala, India, bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
*Correspondence e-mail: eesans@yahoo.com

(Received 6 August 2013; accepted 29 August 2013; online 7 September 2013)

The title compound, C15H12N4O, adopts an E conformation with respect to the azomethine bond and crystallizes in its hydrazinyl­idene tautomeric form. The dihedral angle between the ring systems is 15.98 (7)°. The phenol O—H group forms an intra­molecular O—H⋯N hydrogen bond. In the crystal, pairs of N—H⋯N and C—H⋯O hydrogen bonds link neighbouring mol­ecules into centrosymmetric dimers. These dimers are inter­connected by means of three types of ππ stacking inter­actions. One, with a centroid–centroid distance of 3.577 (1) Å [inter­planar separation = 3.4673 (6) Å], connects adjacent mol­ecules into centrosymmetric dimers. The other two inter­actions, on the outward facing sides of the dimers, are between phenol rings of neighboring mol­ecules [centroid–centroid separation = 3.7907 (13) Å and inter­planar separation = 3.5071 (8) Å], and between phthalazin units [centroid–centroid separation = 3.6001 (12) Å and inter­planar separation = 3.4891 (7) Å]. In combination, the ππ inter­actions lead to the formation of infinite layers with mol­ecules stacked along [0-11]. These layers are, in turn, connected with neighbouring layers through the N—H⋯N and C—H⋯O hydrogen bonds, yielding a three-dimensional supra­molecular architecture.

Related literature

For biological properties of phthalazine and its derivatives, see: Awadallah et al. (2012[Awadallah, F. M., El-Eraky, W. I. & Saleh, D. O. (2012). Eur. J. Med. Chem. 52, 14-21.]); Minami et al. (1985[Minami, M., Togashi, H., Sano, M., Saito, I., Morii, K., Nomura, A., Yoshioka, M. & Saito, H. (1985). Hokkaido Igaku Zasshi, 60, 856-864.]); Zhang et al. (2010[Zhang, S., Zhao, Y., Liu, Y., Chen, D., Lan, W., Zhao, Q., Dong, C., Xia, L. & Gong, P. (2010). Eur. J. Med. Chem. 45, 3504-3510.]); Bian et al. (2013[Bian, M., Deng, X.-Q., Gong, G.-H., Wei, C.-X. & Quan, Z.-S. (2013). J. Enzyme Inhib. Med. Chem. 28, 792-800.]). For applications of 1-phthalazinyl hydrazones in optoelectronics, see: Caruso et al. (2005[Caruso, U., Centore, R., Panunzi, B., Roviello, A. & Tuzi, A. (2005). Eur. J. Inorg. Chem. 25, 2747-2753.]). For the synthesis of related compounds, see: El-Sherif et al. (2012[El-Sherif, A. A., Shoukry, M. M. & Abd-Elgawad, M. M. A. (2012). Spectrochim. Acta Part A, 98, 307-321.]). For related structures and background references, see: Shafiq et al. (2013[Shafiq, M., Tahir, M. N., Harrison, W. T. A., Bukhari, I. H. & Khan, I. U. (2013). Acta Cryst. E69, o164.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N4O

  • Mr = 264.29

  • Triclinic, [P \overline 1]

  • a = 6.8028 (12) Å

  • b = 8.4263 (13) Å

  • c = 11.868 (2) Å

  • α = 89.774 (9)°

  • β = 83.113 (9)°

  • γ = 70.356 (8)°

  • V = 635.62 (19) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.982

  • 3781 measured reflections

  • 2204 independent reflections

  • 1623 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.117

  • S = 1.03

  • 2204 reflections

  • 175 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3′⋯N4i 0.89 (1) 2.31 (1) 3.0181 (14) 137 (2)
O1—H1A⋯N1 0.85 1.89 2.6362 (15) 147
C15—H15⋯O1i 0.93 2.59 3.224 (3) 125
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Hydralazine, or 1-hydrazinylphthalazine, is a direct-acting smooth muscle relaxant used to treat hypertension by acting as a vasodilator, primarily in arteries and arterioles. Upon condensing with carbonyl compounds hydralazine will form hydrazones, namely 1-phthalazinyl hydrazones, which find use as vasodilating antihypertensive drugs and also application in optoelectronics (Caruso et al., 2005).

The title compound is one such 1-phthalazinyl hydrazone. It crystallizes in the triclinic, P1, space group. The molecule exists in its E configuration with respect to the C7=N1 bond which is confirmed by the torsion angle of 177.11 (12)° of the C6—C7—N1—N2 moiety (Fig. 1). The torsion angle of -5.33 (17)° of the N1—N2—C8—N3 moiety shows that the N1 and N3 atoms are cis to each other. The C7=N1 [1.2859 (16) Å] and C8=N2 [1.3010 (16) Å] bond distances are very close to the formal C=N bond length of reported similar compounds [C=N; 1.282 (4) and 1.288 (3) Å, respectively] (e.g., Shafiq et al., 2013), confirming the azomethine bond formation and the presence of a hydrazinylidene. The phenol, azomethine and phthalazin moieties are nearly planar (rms deviations 0.0041, 0.0000 and 0.0328 Å respectively) and coplanar to each other, with the two moieties at the ends of the molecule slightly twisted away from the central moiety in opposite directions by torsion angles of 7.67 (10) and 8.68 (11)° for the phenol and phthalazin moieties with the central azomethine moiety, respectively. The dihedral angle between phenol and phthalazin moieties is 15.98 (7)°.

The phenolic O–H group forms an intramolecular O–H···N hydrogen bond with a D···A distance of 2.6362 (15) Å, and two intermolecular N–H···N and C–H···O hydrogen bonding interactions are found between the neighbouring molecules with D···A distances of 3.017 (2) and 3.224 (3) Å. These intermolecular hydrogen bonds operate together to form centrosymmetric dimers in the crystal lattice. These dimers are interconnected by means of three types of ππ stacking interactions. One of them connects whole molecules into centrosymmetric dimers with a centroid to centroid distance of 3.577 (1) Å (interplanar separation: 3.4673 (6) Å) (Fig. 3). The other two, on the outward facing sides of the π-stacked dimers, are between phenol rings of neighboring molecules (centroid-centroid 3.7907 (13), interplanar separation: 3.5071 (8) Å), and between phthalazin moieties (centroid-centroid 3.6001 (12), interplanar separation: 3.4891 (7) Å) (Fig. 4). The ππ interactions lead to formation of infinite layers (Fig. 5) with molecules stacked along the [0 -1 1] direction. These layers are in turn connected with neighboring layers through the intermolecular N–H···N and C–H···O H-bonds (Fig. 6) to yield a supramolecular architecture sustained by H-bond interactions and ππ interactions. Fig. 7 shows the packing of the molecules along the a axis.

Related literature top

For biological properties of phthalazine and its derivatives, see: Awadallah et al. (2012); Minami et al. (1985); Zhang et al. (2010); Bian et al. (2013). For applications of 1-phthalazinyl hydrazones in optoelectronics, see: Caruso et al. (2005). For the synthesis of related compounds, see: El-Sherif et al. (2012). For related structures and background references, see: Shafiq et al. (2013).

Experimental top

The title compound was prepared by adapting a reported procedure (El-Sherif et al., 2012). (1Z)-1-Hydrazinylidene-1,2-dihydrophthalazine hydrochloride (0.299 g, 1.5 mmol) was added to an ethanolic solution of salicylaldehyde (0.122 g, 1 mmol) and sodium acetate (0.204 g, 1.5 mmol). The mixture was stirred well with slight heating for 90 minutes upon which the creamy yellow hydralazone precipitates out. The precipitate was collected by filtration, washed with water (10 ml) and then with 10 ml of ethanol water (1:2) mixture by volume (yield = 66%, 0. 174 g, 0.660 mmol). Single crystals suitable for XRD studies were obatined by recrystallization from a (1:1) mixture by volume of methanol and DMF (m.p: 206 °C).

IR (KBr, υ in cm-1): 1613, 3316, 1593, 3100–3200, 1023.1H NMR(400 MHz, DMSO-d6, δ in p.p.m.): 10.385 (s, 1H), 8.9 (s, 1H), 8.584 (s, 1H), 8.502 (s, 1H), 7.332–6.902 (m, 8H).

Refinement top

All H atoms on C were placed in calculated positions, guided by difference maps, with C–H bond distances of 0.93 Å. H atoms were assigned Uiso(H) values of 1.2Ueq(carrier). The phenolic O–H distance was restrained to 0.84 (2) Å. The phenolic H atom was found to be disorderd by tautomerism over two positions: partially bonded to O1 and partially bonded to N1 (where the largest Q peak is located after inclusion of extinction correction) with refined occupancies of 0.80 (3) and 0.20 (3) respectively. Partial occupancy of H1 at O1 was also indicated by a rather large Uiso value for H1A of 0.103 before inclusion of disorder. The Uiso value for H1B was set to 1.2 times of Ueq of the N1 atom. H3', located from a difference map, was refined with an N—H distance restraint of 0.88 (2) Å and has a refined Uiso value of 0.058 Å2. Omitted owing to bad disagreement was reflection (0 0 1).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. ORTEP view of the compound, drawn with 50% probability displacement ellipsoids for the non-H atoms (the minor moiety H atom was omitted for clarity).
[Figure 2] Fig. 2. Graphical representation showing the centrosymmetric dimers by means of hydrogen bonding in the crystal structure of C15H12N4O. The minor disordered H atoms were omitted for clarity.
[Figure 3] Fig. 3. Graphical representation showing ππ interactions between whole molecules into centrosymmetric dimers in the crystal structure of the title compound.
[Figure 4] Fig. 4. Graphical representation showing ππ interactions between phenol and pthalazin rings in the crystal structure of the title compound.
[Figure 5] Fig. 5. Graphical representation showing ππ interactions that lead to formation of infinite layers in the crystal structure of the title compound.
[Figure 6] Fig. 6. Graphical representation showing neighboring layers formed by ππ interactions and connected through intermolecular N–H···N and C–H···O H-bonds
[Figure 7] Fig. 7. Packing diagram showing the molecular assembly of the title compound along the a axis.
2-{(E)-[(2Z)-2-(1,2-Dihydrophthalazin-1-ylidene)hydrazinylidene]methyl}phenol top
Crystal data top
C15H12N4OZ = 2
Mr = 264.29F(000) = 276
Triclinic, P1Dx = 1.381 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8028 (12) ÅCell parameters from 1437 reflections
b = 8.4263 (13) Åθ = 2.6–27.4°
c = 11.868 (2) ŵ = 0.09 mm1
α = 89.774 (9)°T = 296 K
β = 83.113 (9)°Block, colorless
γ = 70.356 (8)°0.25 × 0.20 × 0.20 mm
V = 635.62 (19) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2204 independent reflections
Radiation source: fine-focus sealed tube1623 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 8.33 pixels mm-1θmax = 25.1°, θmin = 3.2°
ω and ϕ scanh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
k = 1010
Tmin = 0.978, Tmax = 0.982l = 1314
3781 measured reflections
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)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0527P)2 + 0.1254P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2204 reflectionsΔρmax = 0.16 e Å3
175 parametersΔρmin = 0.17 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (4)
Crystal data top
C15H12N4Oγ = 70.356 (8)°
Mr = 264.29V = 635.62 (19) Å3
Triclinic, P1Z = 2
a = 6.8028 (12) ÅMo Kα radiation
b = 8.4263 (13) ŵ = 0.09 mm1
c = 11.868 (2) ÅT = 296 K
α = 89.774 (9)°0.25 × 0.20 × 0.20 mm
β = 83.113 (9)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2204 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
1623 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.982Rint = 0.020
3781 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0412 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.16 e Å3
2204 reflectionsΔρmin = 0.17 e Å3
175 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.8932 (2)0.3936 (2)0.68867 (13)0.0707 (5)
N10.55508 (10)0.56322 (8)0.82756 (6)0.0369 (4)
H1B0.69020.52440.82190.044*0.20 (3)
H1A0.82250.46020.74350.044*0.80 (3)
N20.43095 (10)0.68017 (8)0.91179 (6)0.0365 (4)
N30.74379 (10)0.62960 (8)0.99606 (6)0.0393 (4)
N40.85914 (10)0.66505 (8)1.07304 (6)0.0438 (4)
C30.72100 (10)0.18492 (8)0.47512 (6)0.0661 (6)
H30.78020.11080.41270.079*
C20.8484 (3)0.2362 (3)0.53623 (17)0.0630 (6)
H20.99310.19760.51470.076*
C10.7630 (3)0.3452 (2)0.62990 (15)0.0455 (5)
C60.5458 (3)0.40421 (19)0.66211 (14)0.0361 (4)
C70.4493 (3)0.51830 (19)0.75881 (14)0.0356 (4)
H70.30320.56160.77220.043*
C80.5352 (2)0.71106 (18)0.98897 (14)0.0322 (4)
C90.4266 (2)0.84219 (18)1.07626 (13)0.0323 (4)
C100.2102 (3)0.9273 (2)1.08475 (15)0.0430 (4)
H100.13020.89721.03590.052*
C110.1156 (3)1.0551 (2)1.16484 (16)0.0504 (5)
H110.02861.11181.16980.060*
C120.2321 (3)1.1010 (2)1.23860 (16)0.0517 (5)
H120.16641.18921.29190.062*
C50.4208 (3)0.3510 (2)0.59677 (15)0.0472 (5)
H50.27550.39070.61610.057*
C40.5070 (4)0.2413 (3)0.50468 (17)0.0602 (6)
H40.42140.20570.46280.072*
C150.7637 (3)0.7886 (2)1.14463 (15)0.0428 (4)
H150.84210.81711.19510.051*
C140.5434 (3)0.88579 (19)1.15182 (14)0.0363 (4)
C130.4441 (3)1.0164 (2)1.23294 (16)0.0462 (5)
H130.52191.04611.28320.055*
H3'0.811 (3)0.5389 (17)0.9514 (14)0.058 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0336 (7)0.1084 (12)0.0615 (10)0.0118 (7)0.0082 (7)0.0239 (9)
N10.0332 (8)0.0376 (8)0.0384 (8)0.0096 (6)0.0060 (6)0.0029 (6)
N20.0320 (7)0.0349 (7)0.0394 (8)0.0067 (6)0.0056 (6)0.0064 (6)
N30.0299 (7)0.0406 (8)0.0448 (9)0.0073 (6)0.0079 (6)0.0070 (7)
N40.0335 (8)0.0498 (9)0.0486 (9)0.0121 (7)0.0126 (7)0.0038 (7)
C30.0787 (16)0.0594 (13)0.0451 (12)0.0035 (11)0.0081 (11)0.0165 (10)
C20.0452 (11)0.0717 (14)0.0509 (13)0.0066 (10)0.0017 (9)0.0110 (10)
C10.0381 (10)0.0508 (11)0.0408 (10)0.0046 (8)0.0090 (8)0.0008 (8)
C60.0391 (9)0.0337 (9)0.0342 (9)0.0098 (7)0.0067 (7)0.0018 (7)
C70.0307 (8)0.0368 (9)0.0388 (10)0.0101 (7)0.0059 (7)0.0008 (7)
C80.0291 (8)0.0307 (8)0.0370 (9)0.0097 (7)0.0056 (7)0.0025 (7)
C90.0338 (9)0.0295 (8)0.0343 (9)0.0112 (7)0.0057 (7)0.0041 (7)
C100.0344 (9)0.0438 (10)0.0486 (11)0.0085 (8)0.0110 (8)0.0025 (8)
C110.0394 (10)0.0477 (11)0.0534 (12)0.0015 (8)0.0038 (9)0.0080 (9)
C120.0587 (12)0.0429 (10)0.0470 (12)0.0101 (9)0.0015 (9)0.0102 (9)
C50.0475 (11)0.0526 (11)0.0445 (11)0.0197 (9)0.0087 (9)0.0034 (9)
C40.0703 (14)0.0607 (13)0.0509 (13)0.0217 (11)0.0128 (11)0.0132 (10)
C150.0368 (10)0.0492 (10)0.0469 (11)0.0172 (8)0.0141 (8)0.0013 (8)
C140.0392 (9)0.0364 (9)0.0368 (10)0.0159 (7)0.0090 (8)0.0036 (7)
C130.0520 (11)0.0456 (10)0.0431 (11)0.0171 (9)0.0121 (9)0.0059 (8)
Geometric parameters (Å, º) top
O1—C11.353 (2)C7—H70.9300
O1—H1A0.8460C8—C91.455 (2)
N1—C71.2861 (16)C9—C141.393 (2)
N1—N21.3891C9—C101.395 (2)
N1—H1B0.8600C10—C111.368 (2)
N2—C81.3008 (16)C10—H100.9300
N3—C81.3654 (16)C11—C121.385 (2)
N3—N41.3680C11—H110.9300
N3—H3'0.886 (9)C12—C131.371 (3)
N4—C151.2834 (18)C12—H120.9300
C3—C21.367 (2)C5—C41.372 (3)
C3—C41.372 (2)C5—H50.9300
C3—H30.9300C4—H40.9300
C2—C11.383 (3)C15—C141.439 (2)
C2—H20.9300C15—H150.9300
C1—C61.396 (2)C14—C131.395 (2)
C6—C51.394 (2)C13—H130.9300
C6—C71.441 (2)
C1—O1—H1A109.9C14—C9—C10119.33 (15)
C7—N1—N2113.77 (8)C14—C9—C8118.79 (14)
C7—N1—H1B123.1C10—C9—C8121.87 (14)
N2—N1—H1B123.1C11—C10—C9120.02 (16)
C8—N2—N1113.87 (7)C11—C10—H10120.0
C8—N3—N4126.36 (7)C9—C10—H10120.0
C8—N3—H3'118.5 (12)C10—C11—C12120.77 (17)
N4—N3—H3'114.9 (12)C10—C11—H11119.6
C15—N4—N3117.14 (8)C12—C11—H11119.6
C2—C3—C4120.90 (12)C13—C12—C11119.97 (16)
C2—C3—H3119.6C13—C12—H12120.0
C4—C3—H3119.5C11—C12—H12120.0
C3—C2—C1120.24 (17)C4—C5—C6121.54 (18)
C3—C2—H2119.9C4—C5—H5119.2
C1—C2—H2119.9C6—C5—H5119.2
O1—C1—C2118.85 (17)C3—C4—C5119.22 (16)
O1—C1—C6121.08 (15)C3—C4—H4120.4
C2—C1—C6120.06 (17)C5—C4—H4120.4
C5—C6—C1118.02 (16)N4—C15—C14124.22 (14)
C5—C6—C7119.84 (16)N4—C15—H15117.9
C1—C6—C7122.14 (15)C14—C15—H15117.9
N1—C7—C6123.25 (14)C9—C14—C13119.80 (15)
N1—C7—H7118.4C9—C14—C15117.65 (15)
C6—C7—H7118.4C13—C14—C15122.52 (15)
N2—C8—N3125.28 (13)C12—C13—C14120.10 (16)
N2—C8—C9119.19 (13)C12—C13—H13120.0
N3—C8—C9115.53 (12)C14—C13—H13120.0
C7—N1—N2—C8172.44 (12)N3—C8—C9—C10175.18 (14)
C8—N3—N4—C151.23 (12)C14—C9—C10—C111.6 (3)
C4—C3—C2—C10.6 (3)C8—C9—C10—C11177.04 (16)
C3—C2—C1—O1179.96 (16)C9—C10—C11—C120.3 (3)
C3—C2—C1—C60.4 (3)C10—C11—C12—C131.0 (3)
O1—C1—C6—C5179.15 (16)C1—C6—C5—C41.2 (3)
C2—C1—C6—C50.5 (3)C7—C6—C5—C4179.45 (17)
O1—C1—C6—C70.1 (3)C2—C3—C4—C50.1 (3)
C2—C1—C6—C7179.82 (17)C6—C5—C4—C31.1 (3)
N2—N1—C7—C6177.11 (12)N3—N4—C15—C142.9 (2)
C5—C6—C7—N1174.86 (14)C10—C9—C14—C131.6 (2)
C1—C6—C7—N15.9 (2)C8—C9—C14—C13177.10 (15)
N1—N2—C8—N35.34 (17)C10—C9—C14—C15176.45 (15)
N1—N2—C8—C9174.60 (10)C8—C9—C14—C154.8 (2)
N4—N3—C8—N2176.70 (9)N4—C15—C14—C90.2 (2)
N4—N3—C8—C93.25 (16)N4—C15—C14—C13178.22 (15)
N2—C8—C9—C14173.79 (13)C11—C12—C13—C141.0 (3)
N3—C8—C9—C146.2 (2)C9—C14—C13—C120.3 (3)
N2—C8—C9—C104.9 (2)C15—C14—C13—C12177.65 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N4i0.89 (1)2.31 (1)3.0181 (14)137 (2)
O1—H1A···N10.851.892.6362 (15)147
C15—H15···O1i0.932.593.224 (3)125
Symmetry code: (i) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3'···N4i0.886 (9)2.307 (14)3.0181 (14)137.3 (15)
O1—H1A···N10.851.892.6362 (15)146.5
C15—H15···O1i0.932.593.224 (3)125
Symmetry code: (i) x+2, y+1, z+2.
 

Acknowledgements

MKP is thankful to the University Grants Commission, Bangalore, India, for the award of a Teacher Fellowship. MRPK is thankful to the UGC, New Delhi, for a UGC–BSR one-time grant to Faculty. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the diffraction measurements.

References

First citationAwadallah, F. M., El-Eraky, W. I. & Saleh, D. O. (2012). Eur. J. Med. Chem. 52, 14–21.  Web of Science CrossRef CAS PubMed
First citationBian, M., Deng, X.-Q., Gong, G.-H., Wei, C.-X. & Quan, Z.-S. (2013). J. Enzyme Inhib. Med. Chem. 28, 792–800.  Web of Science CrossRef CAS PubMed
First citationBrandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCaruso, U., Centore, R., Panunzi, B., Roviello, A. & Tuzi, A. (2005). Eur. J. Inorg. Chem. 25, 2747–2753.  Web of Science CSD CrossRef
First citationEl-Sherif, A. A., Shoukry, M. M. & Abd-Elgawad, M. M. A. (2012). Spectrochim. Acta Part A, 98, 307–321.  CAS
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationMinami, M., Togashi, H., Sano, M., Saito, I., Morii, K., Nomura, A., Yoshioka, M. & Saito, H. (1985). Hokkaido Igaku Zasshi, 60, 856–864.  CAS PubMed
First citationShafiq, M., Tahir, M. N., Harrison, W. T. A., Bukhari, I. H. & Khan, I. U. (2013). Acta Cryst. E69, o164.  CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals
First citationZhang, S., Zhao, Y., Liu, Y., Chen, D., Lan, W., Zhao, Q., Dong, C., Xia, L. & Gong, P. (2010). Eur. J. Med. Chem. 45, 3504–3510.  Web of Science CrossRef CAS PubMed

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Volume 69| Part 10| October 2013| Pages o1522-o1523
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