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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 3| March 2012| Pages o565-o566

4-{4-[(E)-(2-Hy­dr­oxy­phen­yl)imino­methyl]phen­­oxy}benzene-1,2-di­carbo­nitrile

aFırat University, Department of Chemistry, 23169 Elazığ, Turkey, and bHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 24 January 2012; accepted 27 January 2012; online 4 February 2012)

The asymmetric unit of the title compound, C21H13N3O2, contains two independent mol­ecules with a similar structure. In one mol­ecule, the central benzene ring is oriented with respect to the terminal benzene rings at 27.23 (7) and 67.96 (7)°; in the other mol­ecule, the corresponding dihedral angles are 12.42 (7) and 64.55 (7)°. In both molecules, there is a short O—H⋯N interaction involving the OH group and the adjacent N atom. In the crystal, there are O—H⋯N hydrogen bonds, and C—H⋯O and N—H⋯O interactions linking the molecules to form a three-dimensional network. ππ stacking between the pyridine and benzene rings and between the benzene rings [centroid–centroid distances = 3.989 (2), 3.705 (2) and 3.607 (2) Å] may further stabilize the structure. A weak C—H⋯π inter­action is present in the crystal.

Related literature

For the use of phthalonitriles for preparing symmetrically and unsymmetrically substituted phthalocyanine complexes, see: Leznoff & Lever (1996[Leznoff, C. C. & Lever, A. B. P. (1996). Editors. Phthalocyanines: Properties and Applications, Vols. 1-4. Weinheim: VHC.]). For the widespread applications of phthalocyanines in photodynamic therapy, see: Kartal et al. (2006[Kartal, A., Ocak Ískeleli, N., Albayrak, C., Ağar, E. & Erdönmez, A. (2006). Acta Cryst. E62, o548-o549.]); Tüfekçi et al. (2009[Tüfekçi, M., Alpaslan, G., Erşahin, F., Ağar, E. & Erdönmez, A. (2009). Acta Cryst. E65, o1032.]). For the fundamental optical and electronic properties of phthalocyanines, see: McKeown (1998[McKeown, N. B. (1998). Phthalocyanine Materials: Synthesis, Structure and Function. Cambridge University Press.]). For related structures, see: Tuncer et al. (2012[Tuncer, H., Görgülü, A. O. & Hökelek, T. (2012). Acta Cryst. E68, o153.]); Tüfekçi et al. (2009[Tüfekçi, M., Alpaslan, G., Erşahin, F., Ağar, E. & Erdönmez, A. (2009). Acta Cryst. E65, o1032.]); Yazıcı et al. (2009[Yazıcı, S., Akkaya, A., Ağar, E., Şenel, İ. & Büyükgüngör, O. (2009). Acta Cryst. E65, o1172.]); Kartal et al. (2006[Kartal, A., Ocak Ískeleli, N., Albayrak, C., Ağar, E. & Erdönmez, A. (2006). Acta Cryst. E62, o548-o549.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C21H13N3O2

  • Mr = 339.34

  • Triclinic, [P \overline 1]

  • a = 9.842 (3) Å

  • b = 13.448 (4) Å

  • c = 14.061 (4) Å

  • α = 109.940 (15)°

  • β = 96.937 (16)°

  • γ = 104.182 (15)°

  • V = 1652.9 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.40 × 0.23 × 0.13 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.988

  • 28993 measured reflections

  • 8180 independent reflections

  • 4415 reflections with I > 2σ(I)

  • Rint = 0.059

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.148

  • S = 1.01

  • 8180 reflections

  • 478 parameters

  • 1 restraint

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

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8–C13 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 0.84 2.24 2.713 (3) 116
O1—H1⋯N2i 0.84 2.50 2.993 (3) 119
O1′—H1′⋯N1′ 0.84 2.18 2.659 (3) 116
O1′—H1′⋯N3i 0.84 2.39 2.948 (3) 125
C3′—H3′⋯N3′ii 0.95 2.52 3.344 (4) 145
C5—H5⋯O1′iii 0.95 2.40 3.180 (3) 139
C12—H12⋯O1iv 0.95 2.35 3.214 (3) 151
C6′—H6′⋯Cgv 0.95 2.93 3.785 (3) 151
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y-1, z; (iii) x, y+1, z; (iv) x+1, y, z; (v) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Phthalonitriles are used for preparing symmetrically and unsymmetrically substituted phthalocyanine complexes (Leznoff & Lever, 1996). Phthalocyanines have been of great interest to chemists, physicists and industrial scientists. Phthalocyanines have currently been the topic of research because of their wide application fields, such as thin film fabrication, organic pigments, chemical sensors, electrochromic display devices, molecular epitaxic deposition and composites, liquid crystals, photovoltaic cells self-assembled materials. In addition to their extensive use as dyes and pigments, phthalocyanines have found widespread application, in photodynamic therapy (Kartal et al., 2006; Tüfekçi et al., 2009). The fundamental optical and electronic properties of these materials are explained and their potential in non-linear optics, optical data storage, electronic sensors, xerography, solar energy conversion, nuclear chemistry, molecular magnetism, electrochromic displays and heterogeneous catalysis is evaulated by McKeown (1998).

The structures of some phthalonitrile derivatives, C13H8N2O2 (Tuncer et al., 2012), C21H12ClN3O (Tüfekçi et al., 2009), C23H17N3O2 (Yazıcı et al., 2009) and C15H8N2O2 (Kartal et al., 2006) have also been determined.

The asymmetric unit of the title compound, (Fig. 1) contains two crystallographically independent molecules, and the bond lengths are close to standard values (Allen et al., 1987).

The dihedral angles between the hydroxyphenyl rings [A (C1—C6) and A' (C1'—C6')] and the benzene [B (C8—C13), C (C14—C19) and B' (C8'—C13'), C' (C14'—C19')] rings are A/B = 27.23 (7), A/C = 41.88 (7) and A'/B' = 12.42 (7), A'/C' = 73.19 (7) °, while those between the benzene rings B, C and B', C' are B/C = 67.96 (7) and B'/C' = 64.55 (7) °.

In the crystal, intermolecular O—H···N, C—H···O and C—H···N hydrogen bonds (Table 1) link the molecules into a three-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. ππ Contacts between the pyridine and benzene rings and between the benzene rings, Cg1—Cg2i, Cg1—Cg6 and Cg5—Cg5ii [symmetry codes: (i) 1 - x, 1 - y, 1 - z, (ii) -x, -y, -z, where Cg1, Cg2, Cg5 and Cg6 are the centroids of the rings A (C1—C6), B (C8—C13), B' (C8'—C13') and C' (C14'—C19'), respectively] may further stabilize the structure, with centroid-centroid distances of 3.989 (2), 3.705 (2) and 3.607 (2) Å]. There also exists a weak C—H···π interaction (Table 1).

Related literature top

For the use of phthalonitriles for preparing symmetrically and unsymmetrically substituted phthalocyanine complexes, see: Leznoff & Lever (1996). For the widespread applications of phthalocyanines in photodynamic therapy, see: Kartal et al. (2006); Tüfekçi et al. (2009). For the fundamental optical and electronic properties of phthalocyanines, see: McKeown (1998). For related structures, see: Tuncer et al. (2012); Tüfekçi et al. (2009); Yazıcı et al. (2009); Kartal et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound has been prepared in two steps. In the first step; 4-hydroxybenzaldehyde (1.86 g, 15.2 mmol) and 4-nitrophthalonitrile (2.64 g, 15.2 mmol) were heated at 353 K in dry DMF (20 ml) with stirring under argon atmosphere. Then, dry fine powdered potassium carbonate (6.00 g, 43.47 mmol) was added in portions (14 × 3.1 mmol) every 10 min. The mixture was heated for a further 18 h. After cooling, the mixture was added into ice-water (200 g). The product was filtered off and washed with NaOH solution (10% w/w) and water until the filtrate was neutral. In the second step; 4-(4-formylphenoxy)benzene-1,2-dicarbonitrile (1.88 g, 7.6 mmol), the product obtained in the first step, and 2-hydroxyaniline (0.83 g, 7.6 mmol) were reacted at 333 K for 4 h in absolute ethanol (50 ml). Recrystallization from absolute ethanol gave a yellow product (yield: 1.55 g, 60%). Single crystals suitable for X-ray diffraction measurement were obtained by slow evaporation of the solution in ethanol (m.p. 433 K).

Refinement top

Atoms H7 and H7' (for CH) were located in a difference Fourier map and were refined by applying restraints. The remaining H-atoms were positioned geometrically with O—H = 0.84 Å for OH H-atoms, and C—H = 0.95 Å for aromatic H-atoms, and constrained to ride on their parent atoms, with Uiso(H) = k × Ueq(C,O), where k = 1.5 for OH H-atoms and k = 1.2 for aromatic H-atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.
4-{4-[(E)-(2-Hydroxyphenyl)iminomethyl]phenoxy}benzene-1,2-dicarbonitrile top
Crystal data top
C21H13N3O2Z = 4
Mr = 339.34F(000) = 704
Triclinic, P1Dx = 1.364 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.842 (3) ÅCell parameters from 4598 reflections
b = 13.448 (4) Åθ = 2.3–23.5°
c = 14.061 (4) ŵ = 0.09 mm1
α = 109.940 (15)°T = 100 K
β = 96.937 (16)°Block, yellow
γ = 104.182 (15)°0.40 × 0.23 × 0.13 mm
V = 1652.9 (9) Å3
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
8180 independent reflections
Radiation source: fine-focus sealed tube4415 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ϕ and ω scansθmax = 28.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1213
Tmin = 0.975, Tmax = 0.988k = 1717
28993 measured reflectionsl = 1818
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)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0581P)2 + 0.3399P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
8180 reflectionsΔρmax = 0.25 e Å3
478 parametersΔρmin = 0.26 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0067 (11)
Crystal data top
C21H13N3O2γ = 104.182 (15)°
Mr = 339.34V = 1652.9 (9) Å3
Triclinic, P1Z = 4
a = 9.842 (3) ÅMo Kα radiation
b = 13.448 (4) ŵ = 0.09 mm1
c = 14.061 (4) ÅT = 100 K
α = 109.940 (15)°0.40 × 0.23 × 0.13 mm
β = 96.937 (16)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
8180 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
4415 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.988Rint = 0.059
28993 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.25 e Å3
8180 reflectionsΔρmin = 0.26 e Å3
478 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.18465 (16)0.42838 (13)0.39648 (13)0.0415 (4)
H10.23410.38470.39020.062*
O20.81989 (17)0.09971 (13)0.27981 (12)0.0363 (4)
N10.4497 (2)0.44136 (14)0.35611 (13)0.0307 (4)
N20.8274 (2)0.23636 (18)0.53937 (17)0.0523 (6)
N30.6366 (2)0.00505 (17)0.62696 (17)0.0470 (6)
C10.3989 (2)0.53409 (17)0.36774 (16)0.0296 (5)
C20.2600 (2)0.52160 (18)0.38515 (16)0.0315 (5)
C30.1965 (3)0.60425 (19)0.39298 (17)0.0342 (6)
H30.10240.59530.40540.041*
C40.2708 (3)0.69943 (19)0.38268 (17)0.0376 (6)
H40.22740.75630.38780.045*
C50.4085 (3)0.71348 (19)0.36498 (18)0.0396 (6)
H50.45920.77980.35840.048*
C60.4720 (3)0.63074 (18)0.35691 (17)0.0351 (6)
H60.56590.64000.34390.042*
C70.5842 (3)0.45413 (19)0.37209 (17)0.0312 (5)
H70.655 (2)0.5282 (18)0.3985 (16)0.028 (6)*
C80.6422 (2)0.36070 (18)0.35210 (16)0.0295 (5)
C90.5531 (2)0.25160 (18)0.31442 (17)0.0338 (5)
H90.45190.23700.30450.041*
C100.6099 (2)0.16393 (19)0.29116 (18)0.0348 (6)
H100.54860.08940.26390.042*
C110.7580 (2)0.18678 (19)0.30826 (17)0.0305 (5)
C120.8491 (2)0.29320 (19)0.34658 (17)0.0339 (5)
H120.95030.30730.35840.041*
C130.7904 (2)0.37987 (19)0.36777 (17)0.0344 (5)
H130.85250.45410.39360.041*
C140.8182 (2)0.03424 (18)0.33583 (16)0.0290 (5)
C150.8887 (2)0.04502 (18)0.30548 (17)0.0334 (5)
H150.93540.05050.24940.040*
C160.8912 (2)0.11571 (18)0.35649 (17)0.0345 (6)
H160.93890.17030.33510.041*
C170.8244 (2)0.10786 (17)0.43904 (17)0.0300 (5)
C180.7555 (2)0.02651 (17)0.47002 (16)0.0285 (5)
C190.7513 (2)0.04448 (17)0.41867 (16)0.0282 (5)
H190.70360.09910.43970.034*
C200.8271 (3)0.18017 (19)0.49414 (19)0.0373 (6)
C210.6881 (3)0.01535 (18)0.55668 (18)0.0332 (5)
O1'0.48536 (19)0.14517 (14)0.22704 (13)0.0492 (5)
H1'0.44790.09490.22880.074*
O2'0.00214 (16)0.24585 (12)0.13213 (12)0.0353 (4)
N1'0.37253 (18)0.08750 (14)0.07998 (14)0.0281 (4)
N2'0.1000 (2)0.76703 (18)0.15817 (17)0.0486 (6)
N3'0.2416 (2)0.60508 (18)0.22270 (19)0.0549 (6)
C1'0.4335 (2)0.17435 (18)0.04730 (17)0.0304 (5)
C2'0.4886 (2)0.20314 (19)0.12727 (18)0.0354 (6)
C3'0.5463 (3)0.2899 (2)0.1072 (2)0.0429 (6)
H3'0.58340.30860.16210.052*
C4'0.5493 (3)0.3490 (2)0.0066 (2)0.0422 (6)
H4'0.58650.41010.00790.051*
C5'0.4992 (2)0.3211 (2)0.0738 (2)0.0402 (6)
H5'0.50440.36140.14270.048*
C6'0.4417 (2)0.23440 (19)0.05337 (18)0.0364 (6)
H6'0.40710.21530.10870.044*
C7'0.3167 (2)0.05176 (18)0.01768 (18)0.0292 (5)
H7'0.317 (2)0.0807 (17)0.0559 (13)0.040 (7)*
C8'0.2428 (2)0.03159 (17)0.05018 (16)0.0263 (5)
C9'0.2161 (2)0.06816 (17)0.14996 (16)0.0293 (5)
H9'0.25040.04100.19910.035*
C10'0.1404 (2)0.14318 (18)0.17726 (17)0.0309 (5)
H10'0.12380.16900.24540.037*
C11'0.0888 (2)0.18043 (17)0.10454 (17)0.0293 (5)
C12'0.1125 (2)0.14594 (18)0.00537 (17)0.0333 (5)
H12'0.07660.17270.04360.040*
C13'0.1897 (2)0.07143 (17)0.02080 (17)0.0310 (5)
H13'0.20700.04690.08880.037*
C14'0.0287 (2)0.34959 (17)0.12998 (16)0.0286 (5)
C15'0.1547 (2)0.40575 (18)0.11284 (17)0.0321 (5)
H15'0.22740.37120.09870.038*
C16'0.1749 (2)0.51264 (18)0.11636 (17)0.0326 (5)
H16'0.26080.55060.10300.039*
C17'0.0709 (2)0.56471 (17)0.13924 (16)0.0294 (5)
C18'0.0559 (2)0.50719 (18)0.15786 (16)0.0291 (5)
C19'0.0774 (2)0.39984 (18)0.15198 (16)0.0295 (5)
H19'0.16440.36050.16290.035*
C20'0.0907 (2)0.6771 (2)0.14833 (17)0.0355 (6)
C21'0.1606 (3)0.56133 (19)0.19089 (19)0.0372 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0353 (10)0.0367 (9)0.0574 (11)0.0106 (8)0.0084 (8)0.0249 (8)
O20.0479 (10)0.0463 (10)0.0352 (9)0.0280 (8)0.0222 (8)0.0265 (8)
N10.0350 (11)0.0306 (10)0.0283 (10)0.0125 (9)0.0059 (8)0.0123 (8)
N20.0672 (16)0.0409 (12)0.0511 (14)0.0164 (12)0.0019 (12)0.0245 (11)
N30.0592 (15)0.0501 (14)0.0409 (13)0.0184 (12)0.0200 (11)0.0246 (11)
C10.0345 (13)0.0285 (12)0.0237 (11)0.0095 (10)0.0015 (9)0.0092 (9)
C20.0344 (13)0.0310 (12)0.0268 (12)0.0073 (11)0.0007 (10)0.0124 (10)
C30.0359 (13)0.0378 (13)0.0296 (12)0.0149 (11)0.0034 (10)0.0125 (11)
C40.0513 (16)0.0330 (13)0.0265 (12)0.0179 (12)0.0017 (11)0.0089 (10)
C50.0459 (15)0.0337 (13)0.0389 (14)0.0082 (12)0.0024 (11)0.0188 (11)
C60.0336 (13)0.0362 (13)0.0344 (13)0.0083 (11)0.0029 (10)0.0155 (11)
C70.0371 (14)0.0294 (13)0.0250 (12)0.0082 (11)0.0038 (10)0.0105 (10)
C80.0331 (13)0.0341 (13)0.0252 (11)0.0109 (10)0.0080 (9)0.0152 (10)
C90.0296 (13)0.0374 (13)0.0350 (13)0.0111 (11)0.0053 (10)0.0147 (11)
C100.0354 (14)0.0316 (13)0.0385 (14)0.0094 (11)0.0093 (11)0.0151 (11)
C110.0398 (14)0.0383 (13)0.0267 (12)0.0208 (11)0.0160 (10)0.0197 (10)
C120.0281 (12)0.0452 (14)0.0359 (13)0.0124 (11)0.0113 (10)0.0226 (11)
C130.0327 (13)0.0349 (13)0.0350 (13)0.0066 (11)0.0062 (10)0.0160 (11)
C140.0317 (12)0.0344 (12)0.0253 (12)0.0118 (10)0.0068 (9)0.0156 (10)
C150.0372 (13)0.0386 (13)0.0277 (12)0.0179 (11)0.0104 (10)0.0113 (10)
C160.0395 (14)0.0311 (12)0.0334 (13)0.0180 (11)0.0055 (11)0.0090 (10)
C170.0322 (12)0.0271 (12)0.0284 (12)0.0073 (10)0.0006 (10)0.0111 (10)
C180.0297 (12)0.0294 (12)0.0244 (11)0.0062 (10)0.0044 (9)0.0105 (10)
C190.0319 (12)0.0293 (12)0.0266 (12)0.0124 (10)0.0090 (9)0.0117 (10)
C200.0418 (15)0.0303 (13)0.0370 (14)0.0103 (11)0.0020 (11)0.0123 (11)
C210.0400 (14)0.0315 (13)0.0314 (13)0.0114 (11)0.0073 (11)0.0160 (11)
O1'0.0714 (13)0.0581 (11)0.0373 (10)0.0373 (10)0.0189 (9)0.0272 (9)
O2'0.0333 (9)0.0301 (9)0.0484 (10)0.0135 (7)0.0155 (7)0.0175 (8)
N1'0.0276 (10)0.0278 (10)0.0324 (10)0.0103 (8)0.0067 (8)0.0143 (8)
N2'0.0527 (14)0.0440 (13)0.0553 (14)0.0165 (11)0.0085 (11)0.0265 (11)
N3'0.0510 (14)0.0489 (14)0.0791 (18)0.0283 (12)0.0234 (13)0.0299 (13)
C1'0.0257 (12)0.0319 (12)0.0361 (13)0.0086 (10)0.0071 (10)0.0160 (11)
C2'0.0382 (14)0.0411 (14)0.0343 (14)0.0165 (12)0.0145 (11)0.0184 (11)
C3'0.0486 (16)0.0497 (15)0.0513 (16)0.0271 (13)0.0208 (13)0.0327 (13)
C4'0.0396 (15)0.0397 (14)0.0575 (17)0.0180 (12)0.0202 (13)0.0238 (13)
C5'0.0368 (14)0.0396 (14)0.0420 (15)0.0158 (12)0.0111 (11)0.0094 (12)
C6'0.0341 (13)0.0390 (14)0.0348 (13)0.0137 (11)0.0045 (10)0.0119 (11)
C7'0.0280 (12)0.0303 (12)0.0284 (12)0.0081 (10)0.0057 (10)0.0110 (10)
C8'0.0235 (11)0.0253 (11)0.0279 (12)0.0052 (9)0.0026 (9)0.0104 (9)
C9'0.0276 (12)0.0340 (12)0.0275 (12)0.0087 (10)0.0040 (9)0.0147 (10)
C10'0.0288 (12)0.0334 (12)0.0290 (12)0.0086 (10)0.0079 (10)0.0105 (10)
C11'0.0253 (12)0.0253 (11)0.0356 (13)0.0088 (10)0.0067 (10)0.0088 (10)
C12'0.0363 (13)0.0334 (13)0.0311 (13)0.0116 (11)0.0032 (10)0.0144 (10)
C13'0.0359 (13)0.0300 (12)0.0271 (12)0.0122 (10)0.0067 (10)0.0097 (10)
C14'0.0308 (12)0.0263 (12)0.0274 (12)0.0090 (10)0.0034 (9)0.0095 (9)
C15'0.0291 (13)0.0331 (13)0.0332 (13)0.0117 (10)0.0074 (10)0.0101 (10)
C16'0.0322 (13)0.0334 (13)0.0305 (12)0.0071 (11)0.0088 (10)0.0116 (10)
C17'0.0338 (13)0.0309 (12)0.0246 (11)0.0107 (10)0.0049 (9)0.0119 (10)
C18'0.0298 (12)0.0322 (12)0.0264 (12)0.0124 (10)0.0026 (9)0.0117 (10)
C19'0.0253 (12)0.0317 (12)0.0304 (12)0.0079 (10)0.0053 (9)0.0116 (10)
C20'0.0397 (14)0.0377 (14)0.0321 (13)0.0133 (11)0.0052 (10)0.0171 (11)
C21'0.0366 (14)0.0345 (13)0.0455 (15)0.0155 (12)0.0092 (11)0.0183 (12)
Geometric parameters (Å, º) top
O1—C21.362 (3)O1'—C2'1.362 (3)
O1—H10.8400O1'—H1'0.8400
O2—C111.411 (2)O2'—C14'1.365 (3)
O2—C141.366 (2)O2'—C11'1.401 (2)
N1—C11.420 (3)N1'—C1'1.407 (3)
N1—C71.274 (3)N1'—C7'1.265 (3)
N2—C201.142 (3)C1'—C6'1.393 (3)
C1—C21.398 (3)C2'—C1'1.400 (3)
C1—C61.390 (3)C3'—C2'1.379 (3)
C3—C21.382 (3)C3'—H3'0.9500
C3—H30.9500C4'—C3'1.374 (3)
C4—C31.374 (3)C4'—C5'1.381 (3)
C4—H40.9500C4'—H4'0.9500
C5—C41.387 (3)C5'—C6'1.377 (3)
C5—H50.9500C5'—H5'0.9500
C6—C51.383 (3)C6'—H6'0.9500
C6—H60.9500C7'—C8'1.457 (3)
C7—H70.98 (2)C7'—H7'0.974 (16)
C8—C71.461 (3)C8'—C9'1.401 (3)
C8—C91.389 (3)C8'—C13'1.390 (3)
C9—C101.383 (3)C9'—C10'1.376 (3)
C9—H90.9500C9'—H9'0.9500
C10—H100.9500C10'—C11'1.379 (3)
C11—C121.368 (3)C10'—H10'0.9500
C11—C101.386 (3)C11'—C12'1.380 (3)
C12—C131.384 (3)C12'—H12'0.9500
C12—H120.9500C13'—C12'1.381 (3)
C13—C81.393 (3)C13'—H13'0.9500
C13—H130.9500C14'—C15'1.379 (3)
C14—C151.387 (3)C14'—C19'1.387 (3)
C15—C161.375 (3)C15'—C16'1.385 (3)
C15—H150.9500C15'—H15'0.9500
C16—H160.9500C16'—C17'1.385 (3)
C17—C161.388 (3)C16'—H16'0.9500
C18—C171.398 (3)C17'—C18'1.402 (3)
C18—C191.384 (3)C17'—C20'1.434 (3)
C18—C211.437 (3)C18'—C19'1.379 (3)
C19—C141.389 (3)C18'—C21'1.436 (3)
C19—H190.9500C19'—H19'0.9500
C20—C171.438 (3)C20'—N2'1.148 (3)
C21—N31.147 (3)C21'—N3'1.148 (3)
C2—O1—H1109.5C2'—O1'—H1'109.5
C14—O2—C11120.14 (16)C14'—O2'—C11'121.23 (17)
C7—N1—C1120.25 (19)C7'—N1'—C1'122.54 (19)
C2—C1—N1115.60 (19)C2'—C1'—N1'114.24 (19)
C6—C1—N1125.4 (2)C6'—C1'—N1'127.7 (2)
C6—C1—C2118.8 (2)C6'—C1'—C2'118.0 (2)
O1—C2—C1120.78 (19)O1'—C2'—C1'119.9 (2)
O1—C2—C3118.4 (2)O1'—C2'—C3'118.8 (2)
C3—C2—C1120.8 (2)C3'—C2'—C1'121.3 (2)
C2—C3—H3120.3C2'—C3'—H3'120.5
C4—C3—C2119.4 (2)C4'—C3'—C2'119.1 (2)
C4—C3—H3120.3C4'—C3'—H3'120.5
C3—C4—C5120.7 (2)C3'—C4'—C5'121.2 (2)
C3—C4—H4119.6C3'—C4'—H4'119.4
C5—C4—H4119.6C5'—C4'—H4'119.4
C4—C5—H5120.1C4'—C5'—H5'120.2
C6—C5—C4119.9 (2)C6'—C5'—C4'119.5 (2)
C6—C5—H5120.1C6'—C5'—H5'120.2
C1—C6—H6119.9C1'—C6'—H6'119.5
C5—C6—C1120.3 (2)C5'—C6'—C1'120.9 (2)
C5—C6—H6119.9C5'—C6'—H6'119.5
N1—C7—C8122.6 (2)N1'—C7'—C8'122.4 (2)
N1—C7—H7121.4 (12)N1'—C7'—H7'121.7 (13)
C8—C7—H7116.0 (12)C8'—C7'—H7'115.8 (13)
C9—C8—C7121.7 (2)C9'—C8'—C7'121.56 (19)
C9—C8—C13118.4 (2)C13'—C8'—C7'119.66 (19)
C13—C8—C7119.9 (2)C13'—C8'—C9'118.66 (19)
C8—C9—H9119.6C8'—C9'—H9'119.8
C10—C9—C8120.8 (2)C10'—C9'—C8'120.5 (2)
C10—C9—H9119.6C10'—C9'—H9'119.8
C9—C10—C11118.8 (2)C9'—C10'—C11'119.2 (2)
C9—C10—H10120.6C9'—C10'—H10'120.4
C11—C10—H10120.6C11'—C10'—H10'120.4
C10—C11—O2120.6 (2)C10'—C11'—O2'116.81 (19)
C12—C11—O2117.4 (2)C10'—C11'—C12'122.0 (2)
C12—C11—C10121.9 (2)C12'—C11'—O2'120.9 (2)
C11—C12—C13118.5 (2)C11'—C12'—C13'118.3 (2)
C11—C12—H12120.8C11'—C12'—H12'120.9
C13—C12—H12120.8C13'—C12'—H12'120.9
C8—C13—H13119.3C8'—C13'—H13'119.3
C12—C13—C8121.5 (2)C12'—C13'—C8'121.4 (2)
C12—C13—H13119.3C12'—C13'—H13'119.3
O2—C14—C15115.88 (19)O2'—C14'—C15'125.50 (19)
O2—C14—C19123.40 (19)O2'—C14'—C19'113.92 (19)
C15—C14—C19120.7 (2)C15'—C14'—C19'120.5 (2)
C14—C15—H15120.0C14'—C15'—C16'119.8 (2)
C16—C15—C14120.1 (2)C14'—C15'—H15'120.1
C16—C15—H15120.0C16'—C15'—H15'120.1
C15—C16—C17120.4 (2)C15'—C16'—C17'120.5 (2)
C15—C16—H16119.8C15'—C16'—H16'119.7
C17—C16—H16119.8C17'—C16'—H16'119.7
C16—C17—C18119.0 (2)C16'—C17'—C18'119.0 (2)
C16—C17—C20121.3 (2)C16'—C17'—C20'122.2 (2)
C18—C17—C20119.7 (2)C18'—C17'—C20'118.8 (2)
C19—C18—C17121.0 (2)C17'—C18'—C21'120.8 (2)
C17—C18—C21120.0 (2)C19'—C18'—C17'120.43 (19)
C19—C18—C21118.97 (19)C19'—C18'—C21'118.6 (2)
C14—C19—H19120.6C14'—C19'—H19'120.2
C18—C19—C14118.72 (19)C18'—C19'—C14'119.6 (2)
C18—C19—H19120.6C18'—C19'—H19'120.2
N2—C20—C17178.4 (3)N2'—C20'—C17'176.1 (3)
N3—C21—C18178.8 (3)N3'—C21'—C18'176.3 (3)
C14—O2—C11—C1072.6 (3)C14'—O2'—C11'—C10'123.8 (2)
C14—O2—C11—C12111.6 (2)C14'—O2'—C11'—C12'62.8 (3)
C11—O2—C14—C15176.49 (19)C11'—O2'—C14'—C15'7.5 (3)
C11—O2—C14—C193.3 (3)C11'—O2'—C14'—C19'175.44 (18)
C7—N1—C1—C2158.2 (2)C7'—N1'—C1'—C2'179.4 (2)
C7—N1—C1—C626.0 (3)C7'—N1'—C1'—C6'0.9 (3)
C1—N1—C7—C8174.19 (19)C1'—N1'—C7'—C8'174.67 (19)
N1—C1—C2—O14.0 (3)N1'—C1'—C6'—C5'176.9 (2)
N1—C1—C2—C3177.04 (19)C2'—C1'—C6'—C5'1.5 (3)
C6—C1—C2—O1179.83 (19)O1'—C2'—C1'—N1'2.7 (3)
C6—C1—C2—C30.9 (3)O1'—C2'—C1'—C6'178.7 (2)
N1—C1—C6—C5176.8 (2)C3'—C2'—C1'—N1'177.1 (2)
C2—C1—C6—C51.0 (3)C3'—C2'—C1'—C6'1.5 (3)
C4—C3—C2—O1179.47 (19)C4'—C3'—C2'—O1'179.7 (2)
C4—C3—C2—C10.5 (3)C4'—C3'—C2'—C1'0.1 (4)
C5—C4—C3—C20.2 (3)C5'—C4'—C3'—C2'1.7 (4)
C6—C5—C4—C30.4 (3)C3'—C4'—C5'—C6'1.7 (4)
C1—C6—C5—C40.8 (3)C4'—C5'—C6'—C1'0.1 (4)
C9—C8—C7—N10.2 (3)N1'—C7'—C8'—C9'7.0 (3)
C13—C8—C7—N1177.8 (2)N1'—C7'—C8'—C13'176.9 (2)
C7—C8—C9—C10176.8 (2)C7'—C8'—C9'—C10'177.02 (19)
C13—C8—C9—C101.2 (3)C13'—C8'—C9'—C10'0.9 (3)
C8—C9—C10—C111.4 (3)C7'—C8'—C13'—C12'176.5 (2)
O2—C11—C10—C9176.21 (19)C9'—C8'—C13'—C12'0.3 (3)
C12—C11—C10—C90.5 (3)C8'—C9'—C10'—C11'1.2 (3)
O2—C11—C12—C13175.25 (19)C9'—C10'—C11'—O2'172.43 (18)
C10—C11—C12—C130.6 (3)C9'—C10'—C11'—C12'0.9 (3)
C11—C12—C13—C80.8 (3)O2'—C11'—C12'—C13'172.77 (19)
C12—C13—C8—C7178.0 (2)C10'—C11'—C12'—C13'0.3 (3)
C12—C13—C8—C90.1 (3)C8'—C13'—C12'—C11'0.0 (3)
O2—C14—C15—C16179.2 (2)O2'—C14'—C15'—C16'177.6 (2)
C19—C14—C15—C161.0 (3)C19'—C14'—C15'—C16'0.8 (3)
C14—C15—C16—C170.5 (3)O2'—C14'—C19'—C18'176.48 (18)
C18—C17—C16—C150.5 (3)C15'—C14'—C19'—C18'0.7 (3)
C20—C17—C16—C15179.3 (2)C14'—C15'—C16'—C17'1.4 (3)
C19—C18—C17—C161.0 (3)C15'—C16'—C17'—C18'0.6 (3)
C19—C18—C17—C20179.9 (2)C15'—C16'—C17'—C20'177.1 (2)
C21—C18—C17—C16178.7 (2)C16'—C17'—C18'—C19'0.9 (3)
C21—C18—C17—C200.1 (3)C16'—C17'—C18'—C21'174.4 (2)
C17—C18—C19—C140.6 (3)C20'—C17'—C18'—C19'178.65 (19)
C21—C18—C19—C14179.2 (2)C20'—C17'—C18'—C21'3.3 (3)
C18—C19—C14—O2179.77 (19)C17'—C18'—C19'—C14'1.6 (3)
C18—C19—C14—C150.4 (3)C21'—C18'—C19'—C14'173.8 (2)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C8-ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.842.242.713 (3)116
O1—H1···N2i0.842.502.993 (3)119
O1—H1···N10.842.182.659 (3)116
O1—H1···N3i0.842.392.948 (3)125
C3—H3···N3ii0.952.523.344 (4)145
C5—H5···O1iii0.952.403.180 (3)139
C12—H12···O1iv0.952.353.214 (3)151
C6—H6···Cgv0.952.933.785 (3)151
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y1, z; (iii) x, y+1, z; (iv) x+1, y, z; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC21H13N3O2
Mr339.34
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.842 (3), 13.448 (4), 14.061 (4)
α, β, γ (°)109.940 (15), 96.937 (16), 104.182 (15)
V3)1652.9 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.23 × 0.13
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.975, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
28993, 8180, 4415
Rint0.059
(sin θ/λ)max1)0.672
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.148, 1.01
No. of reflections8180
No. of parameters478
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C8-ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.842.242.713 (3)116
O1—H1···N2i0.842.502.993 (3)119
O1'—H1'···N1'0.842.182.659 (3)116
O1'—H1'···N3i0.842.392.948 (3)125
C3'—H3'···N3'ii0.952.523.344 (4)145
C5—H5···O1'iii0.952.403.180 (3)139
C12—H12···O1iv0.952.353.214 (3)151
C6'—H6'···Cgv0.952.933.785 (3)151
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y1, z; (iii) x, y+1, z; (iv) x+1, y, z; (v) x+1, y, z.
 

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationKartal, A., Ocak Ískeleli, N., Albayrak, C., Ağar, E. & Erdönmez, A. (2006). Acta Cryst. E62, o548–o549.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLeznoff, C. C. & Lever, A. B. P. (1996). Editors. Phthalocyanines: Properties and Applications, Vols. 1-4. Weinheim: VHC.  Google Scholar
First citationMcKeown, N. B. (1998). Phthalocyanine Materials: Synthesis, Structure and Function. Cambridge University Press.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTüfekçi, M., Alpaslan, G., Erşahin, F., Ağar, E. & Erdönmez, A. (2009). Acta Cryst. E65, o1032.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationTuncer, H., Görgülü, A. O. & Hökelek, T. (2012). Acta Cryst. E68, o153.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYazıcı, S., Akkaya, A., Ağar, E., Şenel, İ. & Büyükgüngör, O. (2009). Acta Cryst. E65, o1172.  Web of Science CSD CrossRef IUCr Journals 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 3| March 2012| Pages o565-o566
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds