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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 5| May 2015| Page o288
https://doi.org/10.1107/S2056989015006374

Crystal structure of 2-{(E)-[(2-hy­dr­oxy­phen­yl)iminium­yl]meth­yl}-4-methyl­phenolate

Suresh Shalini,a C. R. Girija,b* Mukesh M. Jotani,c C. D. Sathishd and T. V. Venkateshae

aChemistry Research Centre (Affiliated to Kuvempu University), SSMRV Degree College, Jayanagar 4th T Block, Bangalore 560 041, Karnataka, India, bGovt. Science College, Nrupatunga Road, Ambedkar Veedhi, Sampangi Rama Nagar, Bengaluru 560 001, Karnataka, India, cDepartment of Physics, Bhavans Sheth R. A. College of Science, Khanpur, Ahmedabad 380 001, Gujarat, India, dDepartment of Chemistry, PESIT, BSK III Stage, Bangalore 560 085, India, and eDepartment of Chemistry, Jnana Sahyadri, Kuvempu University, Shankaragatta 577 451, India
*Correspondence e-mail: girija.shivakumar@rediffmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 11 February 2015; accepted 29 March 2015; online 9 April 2015)

The title compound, C14H13NO2, exists as a zwitterion in the solid state, with the H atom of the phenol group transferred to the imine N atom. The dihedral angle between the planes of the benzene rings is 10.13 (9)°. Intra­molecular N—H⋯O hydrogen bond generate S(6) and S(5) loops. In the crystal, mol­ecules are connected by O—H⋯O hydrogen bonds, generating C(9) chains propagating in the [010] direction.

CCDC reference: 1005919

Similar articles

1. Related literature

For a related structure, see: Eltayeb et al. (2010[Eltayeb, N. E., Teoh, S. G., Fun, H.-K. & Chantrapromma, S. (2010). Acta Cryst. E66, o1536-o1537.]). For background to Schiff bases and their applications, see: Blagus et al. (2010[Blagus, A., Cincic, D., Friscic, T., Kaitner, B. & Stilinovic, V. (2010). MJCCE, 29, 117-138.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C14H13NO2

  • Mr = 227.25

  • Orthorhombic, P b c a

  • a = 12.9474 (18) Å

  • b = 9.0660 (13) Å

  • c = 19.583 (3) Å

  • V = 2298.7 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.875, Tmax = 1.000

  • 29481 measured reflections

  • 2583 independent reflections

  • 1810 reflections with I > 2σ(I)

  • Rint = 0.059

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.130

  • S = 1.05

  • 2583 reflections

  • 163 parameters

  • 2 restraints

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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H4⋯O1i 0.93 (2) 1.65 (2) 2.5756 (18) 176 (3)
N1—H1⋯O2 0.90 (2) 2.32 (2) 2.6598 (19) 102 (2)
N1—H1⋯O1 0.90 (2) 1.84 (2) 2.5933 (19) 141 (2)
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL2014 and PLATON.

Supporting information

CCDC reference: 1005919

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015006374/hb7370sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015006374/hb7370Isup2.hkl

checkCIF report


Chemical context top

N-substituted imines, also known as Schiff bases represent one of the most widely used families of organic compounds. Schiff bases have been intensively used as synthetic inter­mediates and as ligands for coordinating transition and inner transition metal ions, and recently also for coordinating anions. Schiff base ligands may contain a variety of substituents with different electron-donating or electron-withdrawing groups, and therefore may have inter­esting chemical properties. They have attracted particular inter­est due to their biological activities acting as radiopharmaceuticals for cancer targeting.They have also been used as model systems for biological macromolecules . Besides the biological activity, solid-state thermochromism and photochromism are an another characteristic of these compounds leading to their application in various areas of materials science such as the control and measurement of radiation intensity, display systems and optical memory devices . Schiff bases derived from o-hy­droxy­aromatic aldehydes and ketones are excellent models for the study of keto-enol tautomerism both in solution and in the solid state (Blagus et al., 2010).

Structural commentary top

The structure of the title compound is as shown in Fig.1 is described in terms of three planar subunits,namely two terminal benzene rings and their substituents bridged by a C=N moiety. The molecule has adopted E-configuration about the C8—N1 double bond (1.301 (2)Å) with a C9—N1—C8—C4 torsion angle of 179.90 (16)°. The C4—C8 and N1—C9 bond distances [1.410 (2) and 1.404 (2)Å] confirm π-electron delocalisation between the phenyl rings. The N1—C8—C4[123.26 (15)°] is greater than the normal value of 120°. This may be due to inter­action of iminium H with phenolate O atom. The C6—C5—C4 [116.51 (15)°] is smaller than the normal value of 120° which is due to lengthening of the phenolate C5—O1 [1.304 (2)Å] bond. All other bond distances and bond angles are within the normal range (Eltayeb et al., 2010).

Supra­molecular features top

The iminium H atom is engaged in a strong intra­molecular hydrogen bond with the O atom of the phenolate (N+ —H···O ) to form a S(6) motif. The crystal structure is stabilised by both intra­molecular N1—H1···O1 and inter­molecular O2—H4···O1 hydrogen bonding linking the molecules into infinite one-dimensional chains as shown in the figure.2, table.2, extending along the b-axis of the unit cell.

Synthesis and crystallization top

o-Amino­phenol (5.45g, 0.01mole) was taken in 100mL round bottom flask. Salicyl­aldehyde (6.10g, 0.01mole) was added to the round bottom flask in methanol medium. The resulting mixture was refluxed for about 30 min. The resulting Schiff base was separated as orange crystals. The product was filtered, washed and recrystallized from methanol (M.P.134-135 0C, Yield 75%). Single crystals of the compound were grown by slow evaporation method using ethanol as solvent at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Related literature top

For a related structure, see: Eltayeb et al. (2010). For background to Schiff bases and their applications, see: Blagus et al. (2010).

Structure description top

N-substituted imines, also known as Schiff bases represent one of the most widely used families of organic compounds. Schiff bases have been intensively used as synthetic inter­mediates and as ligands for coordinating transition and inner transition metal ions, and recently also for coordinating anions. Schiff base ligands may contain a variety of substituents with different electron-donating or electron-withdrawing groups, and therefore may have inter­esting chemical properties. They have attracted particular inter­est due to their biological activities acting as radiopharmaceuticals for cancer targeting.They have also been used as model systems for biological macromolecules . Besides the biological activity, solid-state thermochromism and photochromism are an another characteristic of these compounds leading to their application in various areas of materials science such as the control and measurement of radiation intensity, display systems and optical memory devices . Schiff bases derived from o-hy­droxy­aromatic aldehydes and ketones are excellent models for the study of keto-enol tautomerism both in solution and in the solid state (Blagus et al., 2010).

The structure of the title compound is as shown in Fig.1 is described in terms of three planar subunits,namely two terminal benzene rings and their substituents bridged by a C=N moiety. The molecule has adopted E-configuration about the C8—N1 double bond (1.301 (2)Å) with a C9—N1—C8—C4 torsion angle of 179.90 (16)°. The C4—C8 and N1—C9 bond distances [1.410 (2) and 1.404 (2)Å] confirm π-electron delocalisation between the phenyl rings. The N1—C8—C4[123.26 (15)°] is greater than the normal value of 120°. This may be due to inter­action of iminium H with phenolate O atom. The C6—C5—C4 [116.51 (15)°] is smaller than the normal value of 120° which is due to lengthening of the phenolate C5—O1 [1.304 (2)Å] bond. All other bond distances and bond angles are within the normal range (Eltayeb et al., 2010).

The iminium H atom is engaged in a strong intra­molecular hydrogen bond with the O atom of the phenolate (N+ —H···O ) to form a S(6) motif. The crystal structure is stabilised by both intra­molecular N1—H1···O1 and inter­molecular O2—H4···O1 hydrogen bonding linking the molecules into infinite one-dimensional chains as shown in the figure.2, table.2, extending along the b-axis of the unit cell.

For a related structure, see: Eltayeb et al. (2010). For background to Schiff bases and their applications, see: Blagus et al. (2010).

Synthesis and crystallization top

o-Amino­phenol (5.45g, 0.01mole) was taken in 100mL round bottom flask. Salicyl­aldehyde (6.10g, 0.01mole) was added to the round bottom flask in methanol medium. The resulting mixture was refluxed for about 30 min. The resulting Schiff base was separated as orange crystals. The product was filtered, washed and recrystallized from methanol (M.P.134-135 0C, Yield 75%). Single crystals of the compound were grown by slow evaporation method using ethanol as solvent at room temperature.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. ORTEP Plot of (I) drawn at 40% probability level
[Figure 2] Fig. 2. A perspective view of the one-dimensional infinite chain in the title compound, (I), showing N—H···O and O—H···O hydrogen-bnd interactions as dashed lines. H atoms not involved in the interactions have been omitted for the sake of clarity.
2-{(E)-[(2-Hydroxyphenyl)iminiumyl]methyl}-4-methylphenolate top
Crystal data top
C14H13NO2Dx = 1.313 Mg m−3
Mr = 227.25Melting point: 355 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 12.9474 (18) ÅCell parameters from 500 reflections
b = 9.0660 (13) Åθ = 5.0–50.0°
c = 19.583 (3) ŵ = 0.09 mm−1
V = 2298.7 (6) Å3T = 293 K
Z = 8Block, colorless
F(000) = 9600.3 × 0.25 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer		1810 reflections with I > 2σ(I)
Radiation source: graphite monochromatorRint = 0.059
OMEGA–PHI scansθmax = 27.6°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −16→16
Tmin = 0.875, Tmax = 1.000k = −11→8
29481 measured reflectionsl = −25→25
2583 independent reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0467P)2 + 1.0454P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.015
2583 reflectionsΔρmax = 0.21 e Å−3
163 parametersΔρmin = −0.20 e Å−3
Crystal data top
C14H13NO2V = 2298.7 (6) Å3
Mr = 227.25Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.9474 (18) ŵ = 0.09 mm−1
b = 9.0660 (13) ÅT = 293 K
c = 19.583 (3) Å0.3 × 0.25 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer		2583 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		1810 reflections with I > 2σ(I)
Tmin = 0.875, Tmax = 1.000Rint = 0.059
29481 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0502 restraints
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.21 e Å−3
2583 reflectionsΔρmin = −0.20 e Å−3
163 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
H10.6541 (13)0.138 (3)0.2650 (11)0.063 (7)*
H40.5002 (18)0.378 (3)0.1982 (14)0.099 (9)*
N10.71804 (10)0.16956 (16)0.25537 (7)0.0328 (3)
C80.78912 (12)0.1022 (2)0.29051 (8)0.0345 (4)
H80.85790.12540.28190.041*
O10.58630 (9)0.00525 (16)0.31990 (7)0.0465 (4)
C90.73191 (11)0.2767 (2)0.20440 (8)0.0315 (4)
O20.55197 (9)0.31121 (17)0.20963 (7)0.0494 (4)
C140.64308 (12)0.3480 (2)0.18036 (9)0.0350 (4)
C50.66350 (13)−0.0477 (2)0.35492 (9)0.0358 (4)
C100.82779 (13)0.3143 (2)0.17751 (9)0.0389 (4)
H100.88720.26850.19370.047*
C40.76708 (12)−0.0042 (2)0.34097 (8)0.0335 (4)
C20.83378 (15)−0.1684 (2)0.42880 (10)0.0451 (5)
C130.65167 (14)0.4516 (2)0.12897 (9)0.0415 (5)
H130.59280.49820.11240.050*
C60.64951 (14)−0.1513 (2)0.40786 (9)0.0441 (5)
H60.5830−0.18150.41910.053*
C110.83474 (14)0.4189 (2)0.12694 (10)0.0462 (5)
H110.89900.44450.10940.055*
C30.84905 (13)−0.0673 (2)0.37804 (9)0.0418 (5)
H30.9163−0.03900.36760.050*
C70.73159 (15)−0.2085 (2)0.44311 (9)0.0461 (5)
H70.7190−0.27630.47780.055*
C120.74692 (16)0.4864 (2)0.10209 (9)0.0457 (5)
H120.75200.55540.06710.055*
C10.92146 (18)−0.2371 (3)0.46830 (12)0.0691 (7)
H1A0.9742−0.26870.43720.104*
H1B0.8963−0.32050.49350.104*
H1C0.9497−0.16580.49940.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0232 (6)0.0327 (9)0.0425 (8)−0.0010 (6)−0.0004 (6)−0.0013 (6)
C80.0243 (7)0.0355 (11)0.0437 (9)−0.0001 (7)−0.0016 (7)−0.0035 (8)
O10.0253 (6)0.0571 (10)0.0572 (8)−0.0049 (6)−0.0043 (5)0.0051 (7)
C90.0267 (8)0.0304 (10)0.0372 (8)−0.0001 (7)−0.0005 (6)−0.0027 (7)
O20.0249 (6)0.0582 (10)0.0651 (9)0.0050 (6)0.0004 (6)0.0148 (7)
C140.0271 (8)0.0381 (11)0.0398 (9)0.0005 (7)−0.0008 (7)−0.0029 (8)
C50.0305 (8)0.0360 (11)0.0410 (9)−0.0041 (7)0.0000 (7)−0.0059 (8)
C100.0281 (8)0.0410 (12)0.0477 (10)0.0032 (7)0.0011 (7)−0.0013 (8)
C40.0289 (8)0.0332 (10)0.0383 (8)−0.0017 (7)−0.0016 (7)−0.0022 (7)
C20.0450 (10)0.0474 (13)0.0429 (10)0.0017 (9)−0.0054 (8)0.0043 (9)
C130.0381 (9)0.0443 (12)0.0423 (10)0.0050 (8)−0.0062 (8)0.0023 (8)
C60.0378 (9)0.0485 (13)0.0459 (10)−0.0095 (8)0.0057 (8)0.0001 (9)
C110.0377 (10)0.0494 (13)0.0516 (11)−0.0049 (9)0.0109 (8)0.0016 (9)
C30.0288 (8)0.0483 (13)0.0482 (10)0.0004 (8)−0.0034 (7)0.0044 (9)
C70.0528 (11)0.0463 (13)0.0392 (9)−0.0045 (9)0.0019 (8)0.0038 (9)
C120.0516 (11)0.0447 (13)0.0408 (9)−0.0021 (9)0.0033 (9)0.0053 (9)
C10.0560 (13)0.085 (2)0.0662 (14)0.0045 (12)−0.0112 (11)0.0278 (14)
Geometric parameters (Å, º) top
N1—C81.301 (2)C2—C31.367 (3)
N1—C91.404 (2)C2—C71.400 (3)
N1—H10.895 (16)C2—C11.508 (3)
C8—C41.410 (2)C13—C121.377 (3)
C8—H80.9300C13—H130.9300
O1—C51.304 (2)C6—C71.369 (3)
C9—C101.391 (2)C6—H60.9300
C9—C141.401 (2)C11—C121.380 (3)
O2—C141.353 (2)C11—H110.9300
O2—H40.932 (17)C3—H30.9300
C14—C131.381 (3)C7—H70.9300
C5—C61.410 (3)C12—H120.9300
C5—C41.424 (2)C1—H1A0.9600
C10—C111.374 (3)C1—H1B0.9600
C10—H100.9300C1—H1C0.9600
C4—C31.407 (2)
C8—N1—C9127.59 (14)C12—C13—C14120.40 (17)
C8—N1—H1113.3 (15)C12—C13—H13119.8
C9—N1—H1119.1 (15)C14—C13—H13119.8
N1—C8—C4123.26 (15)C7—C6—C5121.52 (17)
N1—C8—H8118.4C7—C6—H6119.2
C4—C8—H8118.4C5—C6—H6119.2
C10—C9—C14119.50 (16)C10—C11—C12120.41 (17)
C10—C9—N1123.55 (15)C10—C11—H11119.8
C14—C9—N1116.95 (14)C12—C11—H11119.8
C14—O2—H4111.4 (18)C2—C3—C4122.59 (17)
O2—C14—C13123.12 (15)C2—C3—H3118.7
O2—C14—C9117.36 (16)C4—C3—H3118.7
C13—C14—C9119.52 (15)C6—C7—C2122.30 (18)
O1—C5—C6122.24 (16)C6—C7—H7118.9
O1—C5—C4121.25 (16)C2—C7—H7118.9
C6—C5—C4116.51 (16)C13—C12—C11120.12 (18)
C11—C10—C9120.02 (16)C13—C12—H12119.9
C11—C10—H10120.0C11—C12—H12119.9
C9—C10—H10120.0C2—C1—H1A109.5
C3—C4—C8119.13 (15)C2—C1—H1B109.5
C3—C4—C5119.91 (16)H1A—C1—H1B109.5
C8—C4—C5120.96 (15)C2—C1—H1C109.5
C3—C2—C7117.15 (17)H1A—C1—H1C109.5
C3—C2—C1122.77 (18)H1B—C1—H1C109.5
C7—C2—C1120.08 (18)
C9—N1—C8—C4179.90 (16)O2—C14—C13—C12178.77 (18)
C8—N1—C9—C108.4 (3)C9—C14—C13—C12−0.9 (3)
C8—N1—C9—C14−171.45 (17)O1—C5—C6—C7178.47 (18)
C10—C9—C14—O2−177.89 (16)C4—C5—C6—C7−1.0 (3)
N1—C9—C14—O22.0 (2)C9—C10—C11—C12−0.6 (3)
C10—C9—C14—C131.8 (3)C7—C2—C3—C40.1 (3)
N1—C9—C14—C13−178.31 (16)C1—C2—C3—C4179.5 (2)
C14—C9—C10—C11−1.1 (3)C8—C4—C3—C2178.41 (19)
N1—C9—C10—C11179.06 (17)C5—C4—C3—C2−1.3 (3)
N1—C8—C4—C3−177.72 (17)C5—C6—C7—C2−0.2 (3)
N1—C8—C4—C52.0 (3)C3—C2—C7—C60.7 (3)
O1—C5—C4—C3−177.76 (17)C1—C2—C7—C6−178.8 (2)
C6—C5—C4—C31.7 (3)C14—C13—C12—C11−0.8 (3)
O1—C5—C4—C82.5 (3)C10—C11—C12—C131.5 (3)
C6—C5—C4—C8−177.99 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H4···O1i0.93 (2)1.65 (2)2.5756 (18)176 (3)
N1—H1···O20.90 (2)2.32 (2)2.6598 (19)102 (2)
N1—H1···O10.90 (2)1.84 (2)2.5933 (19)141 (2)
Symmetry code: (i) −x+1, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H4···O1i0.932 (17)1.645 (17)2.5756 (18)176 (3)
N1—H1···O20.896 (18)2.32 (2)2.6598 (19)102.2 (19)
N1—H1···O10.896 (18)1.84 (2)2.5933 (19)141 (2)
Symmetry code: (i) −x+1, y+1/2, −z+1/2.
 

Acknowledgements

The authors thank SSCU, IISc, Bangalore, India, for the X-ray intensity data collection. SS and CRG thank RSST and the Principal, SSMRV Degree College, Bangalore, for their constant support and encouragement for carrying out research work.

References

First citationBlagus, A., Cincic, D., Friscic, T., Kaitner, B. & Stilinovic, V. (2010). MJCCE, 29, 117–138.  CAS Google Scholar
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ISSN: 2056-9890
Volume 71| Part 5| May 2015| Page o288
https://doi.org/10.1107/S2056989015006374
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