organic compounds
E)-2-[(4-hydroxybenzylidene)azaniumyl]benzoate
of (aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, bDepartment of Pharmacy Services, Jinnah Hospital, Lahore, Pakistan, and cDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
The title Schiff base, C14H11NO3, crystallizes as a zwitterion (i.e. proton transfer from the carboxylic acid group to the imine N atom). The dihedral angle between the aromatic rings is 19.59 (6)° and an intramolecular N—H⋯O hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R24(24) loops. The dimers are linked by C—H⋯O interactions, generating (211) sheets.
CCDC reference: 1018737
1. Related literature
For related structures, see: Hang et al. (2010); Ligtenbarg et al. (1999); Trzesowska-Kruszynska (2010).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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 PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 1018737
10.1107/S1600536814018273/hb7268sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018273/hb7268Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018273/hb7268Isup3.cml
Equimolar quantities of 2-aminobenzoic acid and 4-hydroxybenzaldehyde were refluxed in methanol along with few drops of acetic acid as catalyst for 2 h. The resulting solution was kept at room temperature which afforded yellow needles after two days.
The coordinates of H1 and H3A were refined. The H-atoms were positioned geometrically (C–H = 0.93 Å) and refined as riding with Uiso(H) = xUeq(C, N, O), where x = 1.5 for hydroxy & x = 1.2 for other H-atoms.
Data collection: APEX2 (Bruker, 2007); cell
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, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C14H11NO3 | F(000) = 504 |
Mr = 241.24 | Dx = 1.460 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8612 (5) Å | Cell parameters from 1363 reflections |
b = 15.280 (3) Å | θ = 1.8–26.0° |
c = 18.604 (3) Å | µ = 0.10 mm−1 |
β = 90.347 (8)° | T = 296 K |
V = 1097.6 (3) Å3 | Cut needle, yellow |
Z = 4 | 0.38 × 0.17 × 0.15 mm |
Bruker Kappa APEXII CCD diffractometer | 2089 independent reflections |
Radiation source: fine-focus sealed tube | 1363 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
Detector resolution: 8.00 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −4→4 |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | k = −18→18 |
Tmin = 0.962, Tmax = 0.985 | l = −22→22 |
17364 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0187P)2 + 1.0858P] where P = (Fo2 + 2Fc2)/3 |
2089 reflections | (Δ/σ)max < 0.001 |
169 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C14H11NO3 | V = 1097.6 (3) Å3 |
Mr = 241.24 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.8612 (5) Å | µ = 0.10 mm−1 |
b = 15.280 (3) Å | T = 296 K |
c = 18.604 (3) Å | 0.38 × 0.17 × 0.15 mm |
β = 90.347 (8)° |
Bruker Kappa APEXII CCD diffractometer | 2089 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 1363 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.985 | Rint = 0.065 |
17364 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | Δρmax = 0.18 e Å−3 |
2089 reflections | Δρmin = −0.23 e Å−3 |
169 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1341 (6) | −0.08844 (13) | 0.32981 (10) | 0.0469 (6) | |
O2 | 0.0144 (7) | −0.18735 (14) | 0.24574 (12) | 0.0580 (7) | |
O3 | 0.6380 (6) | 0.22716 (14) | 0.59807 (11) | 0.0489 (6) | |
H3A | 0.701 (9) | 0.177 (2) | 0.6251 (19) | 0.073* | |
N1 | −0.0068 (6) | 0.07058 (16) | 0.30803 (13) | 0.0360 (6) | |
H1 | 0.067 (7) | 0.016 (2) | 0.3337 (15) | 0.043* | |
C1 | 0.0114 (8) | −0.1120 (2) | 0.26817 (16) | 0.0394 (7) | |
C2 | −0.1414 (7) | −0.04003 (18) | 0.22116 (14) | 0.0328 (7) | |
C3 | −0.2813 (8) | −0.0637 (2) | 0.15519 (15) | 0.0398 (7) | |
H3 | −0.2817 | −0.1223 | 0.1417 | 0.048* | |
C4 | −0.4196 (8) | −0.0021 (2) | 0.10915 (16) | 0.0460 (8) | |
H4 | −0.5103 | −0.0192 | 0.0649 | 0.055* | |
C5 | −0.4233 (8) | 0.0847 (2) | 0.12868 (16) | 0.0461 (8) | |
H5 | −0.5171 | 0.1261 | 0.0975 | 0.055* | |
C6 | −0.2890 (8) | 0.1107 (2) | 0.19417 (16) | 0.0416 (8) | |
H6 | −0.2931 | 0.1694 | 0.2074 | 0.050* | |
C7 | −0.1485 (7) | 0.04873 (18) | 0.23973 (14) | 0.0332 (7) | |
C8 | 0.0590 (7) | 0.14802 (19) | 0.33225 (15) | 0.0370 (7) | |
H8 | 0.0125 | 0.1955 | 0.3025 | 0.044* | |
C9 | 0.1993 (7) | 0.16514 (18) | 0.40216 (15) | 0.0342 (7) | |
C10 | 0.2987 (7) | 0.25053 (19) | 0.41916 (16) | 0.0384 (7) | |
H10 | 0.2674 | 0.2947 | 0.3854 | 0.046* | |
C11 | 0.4416 (8) | 0.27050 (19) | 0.48472 (16) | 0.0397 (7) | |
H11 | 0.5063 | 0.3278 | 0.4950 | 0.048* | |
C12 | 0.4901 (8) | 0.20511 (19) | 0.53595 (15) | 0.0365 (7) | |
C13 | 0.3814 (7) | 0.12005 (18) | 0.52047 (15) | 0.0375 (7) | |
H13 | 0.4051 | 0.0764 | 0.5550 | 0.045* | |
C14 | 0.2400 (8) | 0.10038 (19) | 0.45483 (15) | 0.0376 (7) | |
H14 | 0.1700 | 0.0433 | 0.4451 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0702 (15) | 0.0380 (12) | 0.0324 (12) | 0.0036 (11) | −0.0144 (11) | 0.0019 (9) |
O2 | 0.0942 (19) | 0.0323 (12) | 0.0474 (14) | 0.0034 (13) | −0.0117 (13) | −0.0025 (11) |
O3 | 0.0679 (16) | 0.0367 (13) | 0.0419 (13) | −0.0001 (11) | −0.0187 (11) | −0.0015 (10) |
N1 | 0.0437 (15) | 0.0313 (14) | 0.0329 (13) | 0.0036 (11) | −0.0026 (11) | −0.0010 (11) |
C1 | 0.0498 (19) | 0.0336 (17) | 0.0347 (17) | −0.0006 (14) | 0.0009 (15) | 0.0032 (14) |
C2 | 0.0340 (16) | 0.0343 (16) | 0.0300 (15) | 0.0000 (13) | 0.0007 (13) | 0.0007 (12) |
C3 | 0.0438 (18) | 0.0382 (18) | 0.0374 (17) | −0.0019 (14) | −0.0049 (14) | −0.0030 (14) |
C4 | 0.0479 (19) | 0.056 (2) | 0.0344 (18) | 0.0010 (16) | −0.0085 (15) | −0.0005 (15) |
C5 | 0.050 (2) | 0.048 (2) | 0.0400 (18) | 0.0060 (16) | −0.0051 (16) | 0.0115 (16) |
C6 | 0.0443 (19) | 0.0354 (17) | 0.0452 (19) | 0.0038 (14) | −0.0015 (15) | 0.0032 (14) |
C7 | 0.0370 (17) | 0.0347 (17) | 0.0278 (15) | −0.0001 (13) | −0.0005 (13) | 0.0003 (12) |
C8 | 0.0401 (17) | 0.0319 (16) | 0.0390 (17) | 0.0000 (13) | −0.0009 (14) | 0.0033 (14) |
C9 | 0.0350 (16) | 0.0313 (16) | 0.0362 (16) | 0.0019 (13) | −0.0024 (13) | −0.0017 (13) |
C10 | 0.0439 (18) | 0.0305 (16) | 0.0407 (18) | 0.0027 (14) | −0.0066 (14) | 0.0064 (13) |
C11 | 0.0461 (18) | 0.0271 (16) | 0.0457 (19) | −0.0011 (13) | −0.0075 (15) | −0.0018 (14) |
C12 | 0.0389 (17) | 0.0359 (17) | 0.0345 (16) | 0.0020 (13) | −0.0027 (14) | −0.0028 (13) |
C13 | 0.0472 (19) | 0.0289 (16) | 0.0365 (17) | 0.0018 (14) | 0.0006 (14) | 0.0047 (13) |
C14 | 0.0442 (18) | 0.0280 (16) | 0.0404 (17) | −0.0022 (13) | 0.0000 (14) | −0.0035 (13) |
O1—C1 | 1.289 (3) | C5—H5 | 0.9300 |
O2—C1 | 1.225 (3) | C6—C7 | 1.380 (4) |
O3—C12 | 1.329 (3) | C6—H6 | 0.9300 |
O3—H3A | 0.95 (4) | C8—C9 | 1.430 (4) |
N1—C8 | 1.291 (3) | C8—H8 | 0.9300 |
N1—C7 | 1.420 (3) | C9—C10 | 1.396 (4) |
N1—H1 | 1.00 (3) | C9—C14 | 1.401 (4) |
C1—C2 | 1.522 (4) | C10—C11 | 1.370 (4) |
C2—C3 | 1.386 (4) | C10—H10 | 0.9300 |
C2—C7 | 1.400 (4) | C11—C12 | 1.393 (4) |
C3—C4 | 1.378 (4) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.395 (4) |
C4—C5 | 1.375 (4) | C13—C14 | 1.368 (4) |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.380 (4) | C14—H14 | 0.9300 |
C12—O3—H3A | 111 (2) | C6—C7—N1 | 122.4 (3) |
C8—N1—C7 | 127.0 (3) | C2—C7—N1 | 116.1 (2) |
C8—N1—H1 | 122.7 (16) | N1—C8—C9 | 123.9 (3) |
C7—N1—H1 | 109.9 (16) | N1—C8—H8 | 118.0 |
O2—C1—O1 | 124.2 (3) | C9—C8—H8 | 118.0 |
O2—C1—C2 | 119.2 (3) | C10—C9—C14 | 118.2 (3) |
O1—C1—C2 | 116.6 (3) | C10—C9—C8 | 118.6 (3) |
C3—C2—C7 | 117.6 (3) | C14—C9—C8 | 123.2 (3) |
C3—C2—C1 | 117.9 (3) | C11—C10—C9 | 121.2 (3) |
C7—C2—C1 | 124.5 (2) | C11—C10—H10 | 119.4 |
C4—C3—C2 | 121.4 (3) | C9—C10—H10 | 119.4 |
C4—C3—H3 | 119.3 | C10—C11—C12 | 120.1 (3) |
C2—C3—H3 | 119.3 | C10—C11—H11 | 120.0 |
C5—C4—C3 | 119.9 (3) | C12—C11—H11 | 120.0 |
C5—C4—H4 | 120.0 | O3—C12—C11 | 117.9 (3) |
C3—C4—H4 | 120.0 | O3—C12—C13 | 122.9 (3) |
C4—C5—C6 | 120.5 (3) | C11—C12—C13 | 119.2 (3) |
C4—C5—H5 | 119.8 | C14—C13—C12 | 120.5 (3) |
C6—C5—H5 | 119.8 | C14—C13—H13 | 119.8 |
C5—C6—C7 | 119.2 (3) | C12—C13—H13 | 119.8 |
C5—C6—H6 | 120.4 | C13—C14—C9 | 120.8 (3) |
C7—C6—H6 | 120.4 | C13—C14—H14 | 119.6 |
C6—C7—C2 | 121.4 (3) | C9—C14—H14 | 119.6 |
O2—C1—C2—C3 | 1.9 (4) | C8—N1—C7—C6 | −11.1 (5) |
O1—C1—C2—C3 | −178.8 (3) | C8—N1—C7—C2 | 169.5 (3) |
O2—C1—C2—C7 | −177.6 (3) | C7—N1—C8—C9 | 179.4 (3) |
O1—C1—C2—C7 | 1.7 (4) | N1—C8—C9—C10 | 172.3 (3) |
C7—C2—C3—C4 | 0.6 (4) | N1—C8—C9—C14 | −8.1 (5) |
C1—C2—C3—C4 | −179.0 (3) | C14—C9—C10—C11 | 1.9 (4) |
C2—C3—C4—C5 | −0.6 (5) | C8—C9—C10—C11 | −178.6 (3) |
C3—C4—C5—C6 | 0.1 (5) | C9—C10—C11—C12 | 0.0 (5) |
C4—C5—C6—C7 | 0.4 (5) | C10—C11—C12—O3 | 178.3 (3) |
C5—C6—C7—C2 | −0.4 (4) | C10—C11—C12—C13 | −2.1 (4) |
C5—C6—C7—N1 | −179.7 (3) | O3—C12—C13—C14 | −178.0 (3) |
C3—C2—C7—C6 | 0.0 (4) | C11—C12—C13—C14 | 2.3 (4) |
C1—C2—C7—C6 | 179.5 (3) | C12—C13—C14—C9 | −0.5 (4) |
C3—C2—C7—N1 | 179.3 (3) | C10—C9—C14—C13 | −1.6 (4) |
C1—C2—C7—N1 | −1.2 (4) | C8—C9—C14—C13 | 178.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O1i | 0.95 (4) | 1.71 (4) | 2.656 (3) | 173 (3) |
N1—H1···O1 | 1.00 (3) | 1.62 (3) | 2.522 (3) | 148 (2) |
C6—H6···O2ii | 0.93 | 2.51 | 3.397 (4) | 160 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x−1/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O1i | 0.95 (4) | 1.71 (4) | 2.656 (3) | 173 (3) |
N1—H1···O1 | 1.00 (3) | 1.62 (3) | 2.522 (3) | 148 (2) |
C6—H6···O2ii | 0.93 | 2.51 | 3.397 (4) | 160.1 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x−1/2, y+1/2, −z+1/2. |
Acknowledgements
The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.
References
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The title compound (I), (Fig. 1) has been synthesized for forming different metal complexes.
The crystal structures of N-(2-Carboxyphenyl)salicylidenimine (Ligtenbarg et al., 1999), 2-((4-(dimethylamino)benzylidene)ammonio) benzoate pentahydrate (Trzesowska-Kruszynska, 2010) and 2-[(2-hydroxy-4-methoxybenzylidene)azaniumyl]benzoate monohydrate (Hang, et al., 2010) have been published which are related to the title compound (I).
The title compound has been crystalized in the zwitterion form. In (I) the moieties of 2-aminobenzoic acid A (C1—C7/N1/O1/O2) and the 4-hydroxybenzalehyde B (C8—C14/O3) are planar with r.m.s. deviation of 0.0133 and 0.0219 Å, respectively. The dihedral angle between A/B is 19.589 (58)°. In (I), S(6) ring motif is present due to H-bonding of N—H···O type (Table 1, Fig. 1). The molecules are dimerized from end to end due to H-bondings of O—H···O type (Table 1, Fig. 2) and form R24(24) loop. The dimers are further interlinked due to C—H···O bonds.