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

Prasanna, M.K.; Sithambaresan, M.; Pradeepkumar, K.; Kurup, M.R.P.

doi:10.1107/S1600536813024203

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

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

doi:10.1107/S1600536813024203

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

M. K. Prasanna,^a M. Sithambaresan,^b ^* K. Pradeepkumar ^a and M. R. Prathapachandra Kurup ^c

^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 π–π 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 π–π 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 ); 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

Crystal data

C₁₅H₁₂N₄O
M_r = 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 ) T_min = 0.978, T_max = 0.982
3781 measured reflections
2204 independent reflections
1623 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); 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 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813024203/zl2563sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813024203/zl2563Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813024203/zl2563Isup3.cml

checkCIF report

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 π–π 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 π–π 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 π–π 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).

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

	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).
	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.
	Fig. 3. Graphical representation showing π–π interactions between whole molecules into centrosymmetric dimers in the crystal structure of the title compound.
	Fig. 4. Graphical representation showing π–π interactions between phenol and pthalazin rings in the crystal structure of the title compound.
	Fig. 5. Graphical representation showing π–π interactions that lead to formation of infinite layers in the crystal structure of the title compound.
	Fig. 6. Graphical representation showing neighboring layers formed by π–π interactions and connected through intermolecular N–H···N and C–H···O H-bonds
	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

C₁₅H₁₂N₄O	Z = 2
M_r = 264.29	F(000) = 276
Triclinic, P1	D_x = 1.381 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8028 (12) Å	Cell parameters from 1437 reflections
b = 8.4263 (13) Å	θ = 2.6–27.4°
c = 11.868 (2) Å	µ = 0.09 mm⁻¹
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 tube	1623 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.1°, θ_min = 3.2°
ω and ϕ scan	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −10→10
T_min = 0.978, T_max = 0.982	l = −13→14
3781 measured reflections

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0527P)² + 0.1254P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2204 reflections	Δρ_max = 0.16 e Å⁻³
175 parameters	Δρ_min = −0.17 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

Crystal data top

C₁₅H₁₂N₄O	γ = 70.356 (8)°
M_r = 264.29	V = 635.62 (19) Å³
Triclinic, P1	Z = 2
a = 6.8028 (12) Å	Mo Kα radiation
b = 8.4263 (13) Å	µ = 0.09 mm⁻¹
c = 11.868 (2) Å	T = 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)
T_min = 0.978, T_max = 0.982	R_int = 0.020
3781 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	2 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.16 e Å⁻³
2204 reflections	Δρ_min = −0.17 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.8932 (2)	0.3936 (2)	0.68867 (13)	0.0707 (5)
N1	0.55508 (10)	0.56322 (8)	0.82756 (6)	0.0369 (4)
H1B	0.6902	0.5244	0.8219	0.044*	0.20 (3)
H1A	0.8225	0.4602	0.7435	0.044*	0.80 (3)
N2	0.43095 (10)	0.68017 (8)	0.91179 (6)	0.0365 (4)
N3	0.74379 (10)	0.62960 (8)	0.99606 (6)	0.0393 (4)
N4	0.85914 (10)	0.66505 (8)	1.07304 (6)	0.0438 (4)
C3	0.72100 (10)	0.18492 (8)	0.47512 (6)	0.0661 (6)
H3	0.7802	0.1108	0.4127	0.079*
C2	0.8484 (3)	0.2362 (3)	0.53623 (17)	0.0630 (6)
H2	0.9931	0.1976	0.5147	0.076*
C1	0.7630 (3)	0.3452 (2)	0.62990 (15)	0.0455 (5)
C6	0.5458 (3)	0.40421 (19)	0.66211 (14)	0.0361 (4)
C7	0.4493 (3)	0.51830 (19)	0.75881 (14)	0.0356 (4)
H7	0.3032	0.5616	0.7722	0.043*
C8	0.5352 (2)	0.71106 (18)	0.98897 (14)	0.0322 (4)
C9	0.4266 (2)	0.84219 (18)	1.07626 (13)	0.0323 (4)
C10	0.2102 (3)	0.9273 (2)	1.08475 (15)	0.0430 (4)
H10	0.1302	0.8972	1.0359	0.052*
C11	0.1156 (3)	1.0551 (2)	1.16484 (16)	0.0504 (5)
H11	−0.0286	1.1118	1.1698	0.060*
C12	0.2321 (3)	1.1010 (2)	1.23860 (16)	0.0517 (5)
H12	0.1664	1.1892	1.2919	0.062*
C5	0.4208 (3)	0.3510 (2)	0.59677 (15)	0.0472 (5)
H5	0.2755	0.3907	0.6161	0.057*
C4	0.5070 (4)	0.2413 (3)	0.50468 (17)	0.0602 (6)
H4	0.4214	0.2057	0.4628	0.072*
C15	0.7637 (3)	0.7886 (2)	1.14463 (15)	0.0428 (4)
H15	0.8421	0.8171	1.1951	0.051*
C14	0.5434 (3)	0.88579 (19)	1.15182 (14)	0.0363 (4)
C13	0.4441 (3)	1.0164 (2)	1.23294 (16)	0.0462 (5)
H13	0.5219	1.0461	1.2832	0.055*
H3'	0.811 (3)	0.5389 (17)	0.9514 (14)	0.058 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0336 (7)	0.1084 (12)	0.0615 (10)	−0.0118 (7)	−0.0082 (7)	−0.0239 (9)
N1	0.0332 (8)	0.0376 (8)	0.0384 (8)	−0.0096 (6)	−0.0060 (6)	−0.0029 (6)
N2	0.0320 (7)	0.0349 (7)	0.0394 (8)	−0.0067 (6)	−0.0056 (6)	−0.0064 (6)
N3	0.0299 (7)	0.0406 (8)	0.0448 (9)	−0.0073 (6)	−0.0079 (6)	−0.0070 (7)
N4	0.0335 (8)	0.0498 (9)	0.0486 (9)	−0.0121 (7)	−0.0126 (7)	−0.0038 (7)
C3	0.0787 (16)	0.0594 (13)	0.0451 (12)	−0.0035 (11)	−0.0081 (11)	−0.0165 (10)
C2	0.0452 (11)	0.0717 (14)	0.0509 (13)	0.0066 (10)	−0.0017 (9)	−0.0110 (10)
C1	0.0381 (10)	0.0508 (11)	0.0408 (10)	−0.0046 (8)	−0.0090 (8)	−0.0008 (8)
C6	0.0391 (9)	0.0337 (9)	0.0342 (9)	−0.0098 (7)	−0.0067 (7)	0.0018 (7)
C7	0.0307 (8)	0.0368 (9)	0.0388 (10)	−0.0101 (7)	−0.0059 (7)	0.0008 (7)
C8	0.0291 (8)	0.0307 (8)	0.0370 (9)	−0.0097 (7)	−0.0056 (7)	0.0025 (7)
C9	0.0338 (9)	0.0295 (8)	0.0343 (9)	−0.0112 (7)	−0.0057 (7)	0.0041 (7)
C10	0.0344 (9)	0.0438 (10)	0.0486 (11)	−0.0085 (8)	−0.0110 (8)	−0.0025 (8)
C11	0.0394 (10)	0.0477 (11)	0.0534 (12)	−0.0015 (8)	−0.0038 (9)	−0.0080 (9)
C12	0.0587 (12)	0.0429 (10)	0.0470 (12)	−0.0101 (9)	−0.0015 (9)	−0.0102 (9)
C5	0.0475 (11)	0.0526 (11)	0.0445 (11)	−0.0197 (9)	−0.0087 (9)	−0.0034 (9)
C4	0.0703 (14)	0.0607 (13)	0.0509 (13)	−0.0217 (11)	−0.0128 (11)	−0.0132 (10)
C15	0.0368 (10)	0.0492 (10)	0.0469 (11)	−0.0172 (8)	−0.0141 (8)	−0.0013 (8)
C14	0.0392 (9)	0.0364 (9)	0.0368 (10)	−0.0159 (7)	−0.0090 (8)	0.0036 (7)
C13	0.0520 (11)	0.0456 (10)	0.0431 (11)	−0.0171 (9)	−0.0121 (9)	−0.0059 (8)

Geometric parameters (Å, º) top

O1—C1	1.353 (2)	C7—H7	0.9300
O1—H1A	0.8460	C8—C9	1.455 (2)
N1—C7	1.2861 (16)	C9—C14	1.393 (2)
N1—N2	1.3891	C9—C10	1.395 (2)
N1—H1B	0.8600	C10—C11	1.368 (2)
N2—C8	1.3008 (16)	C10—H10	0.9300
N3—C8	1.3654 (16)	C11—C12	1.385 (2)
N3—N4	1.3680	C11—H11	0.9300
N3—H3'	0.886 (9)	C12—C13	1.371 (3)
N4—C15	1.2834 (18)	C12—H12	0.9300
C3—C2	1.367 (2)	C5—C4	1.372 (3)
C3—C4	1.372 (2)	C5—H5	0.9300
C3—H3	0.9300	C4—H4	0.9300
C2—C1	1.383 (3)	C15—C14	1.439 (2)
C2—H2	0.9300	C15—H15	0.9300
C1—C6	1.396 (2)	C14—C13	1.395 (2)
C6—C5	1.394 (2)	C13—H13	0.9300
C6—C7	1.441 (2)

C1—O1—H1A	109.9	C14—C9—C10	119.33 (15)
C7—N1—N2	113.77 (8)	C14—C9—C8	118.79 (14)
C7—N1—H1B	123.1	C10—C9—C8	121.87 (14)
N2—N1—H1B	123.1	C11—C10—C9	120.02 (16)
C8—N2—N1	113.87 (7)	C11—C10—H10	120.0
C8—N3—N4	126.36 (7)	C9—C10—H10	120.0
C8—N3—H3'	118.5 (12)	C10—C11—C12	120.77 (17)
N4—N3—H3'	114.9 (12)	C10—C11—H11	119.6
C15—N4—N3	117.14 (8)	C12—C11—H11	119.6
C2—C3—C4	120.90 (12)	C13—C12—C11	119.97 (16)
C2—C3—H3	119.6	C13—C12—H12	120.0
C4—C3—H3	119.5	C11—C12—H12	120.0
C3—C2—C1	120.24 (17)	C4—C5—C6	121.54 (18)
C3—C2—H2	119.9	C4—C5—H5	119.2
C1—C2—H2	119.9	C6—C5—H5	119.2
O1—C1—C2	118.85 (17)	C3—C4—C5	119.22 (16)
O1—C1—C6	121.08 (15)	C3—C4—H4	120.4
C2—C1—C6	120.06 (17)	C5—C4—H4	120.4
C5—C6—C1	118.02 (16)	N4—C15—C14	124.22 (14)
C5—C6—C7	119.84 (16)	N4—C15—H15	117.9
C1—C6—C7	122.14 (15)	C14—C15—H15	117.9
N1—C7—C6	123.25 (14)	C9—C14—C13	119.80 (15)
N1—C7—H7	118.4	C9—C14—C15	117.65 (15)
C6—C7—H7	118.4	C13—C14—C15	122.52 (15)
N2—C8—N3	125.28 (13)	C12—C13—C14	120.10 (16)
N2—C8—C9	119.19 (13)	C12—C13—H13	120.0
N3—C8—C9	115.53 (12)	C14—C13—H13	120.0

C7—N1—N2—C8	172.44 (12)	N3—C8—C9—C10	−175.18 (14)
C8—N3—N4—C15	−1.23 (12)	C14—C9—C10—C11	1.6 (3)
C4—C3—C2—C1	0.6 (3)	C8—C9—C10—C11	−177.04 (16)
C3—C2—C1—O1	179.96 (16)	C9—C10—C11—C12	−0.3 (3)
C3—C2—C1—C6	−0.4 (3)	C10—C11—C12—C13	−1.0 (3)
O1—C1—C6—C5	179.15 (16)	C1—C6—C5—C4	1.2 (3)
C2—C1—C6—C5	−0.5 (3)	C7—C6—C5—C4	−179.45 (17)
O1—C1—C6—C7	−0.1 (3)	C2—C3—C4—C5	0.1 (3)
C2—C1—C6—C7	−179.82 (17)	C6—C5—C4—C3	−1.1 (3)
N2—N1—C7—C6	177.11 (12)	N3—N4—C15—C14	2.9 (2)
C5—C6—C7—N1	174.86 (14)	C10—C9—C14—C13	−1.6 (2)
C1—C6—C7—N1	−5.9 (2)	C8—C9—C14—C13	177.10 (15)
N1—N2—C8—N3	−5.34 (17)	C10—C9—C14—C15	176.45 (15)
N1—N2—C8—C9	174.60 (10)	C8—C9—C14—C15	−4.8 (2)
N4—N3—C8—N2	176.70 (9)	N4—C15—C14—C9	0.2 (2)
N4—N3—C8—C9	−3.25 (16)	N4—C15—C14—C13	178.22 (15)
N2—C8—C9—C14	−173.79 (13)	C11—C12—C13—C14	1.0 (3)
N3—C8—C9—C14	6.2 (2)	C9—C14—C13—C12	0.3 (3)
N2—C8—C9—C10	4.9 (2)	C15—C14—C13—C12	−177.65 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3'···N4ⁱ	0.886 (9)	2.307 (14)	3.0181 (14)	137.3 (15)
O1—H1A···N1	0.85	1.89	2.6362 (15)	146.5
C15—H15···O1ⁱ	0.93	2.59	3.224 (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

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

doi:10.1107/S1600536813024203

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

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

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Experimental

Crystal data

Data collection

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organic compounds

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