Experimental
Crystal data
C15H13NO4 Mr = 271.26 Monoclinic, P 21 /c a = 13.4369 (12) Å b = 8.5619 (8) Å c = 12.6653 (11) Å β = 118.004 (3)° V = 1286.5 (2) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 296 K 0.26 × 0.20 × 0.18 mm
|
Data collection
Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ) Tmin = 0.982, Tmax = 0.987 9561 measured reflections 2320 independent reflections 1583 reflections with I > 2σ(I) Rint = 0.031
|
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | O3—H3⋯O1 | 0.90 | 1.62 | 2.4816 (19) | 159 | N1—H1⋯O2i | 0.86 | 1.90 | 2.7408 (19) | 166 | C8—H8⋯O1ii | 0.93 | 2.47 | 3.179 (2) | 133 | C14—H14⋯O2i | 0.93 | 2.30 | 3.183 (2) | 159 | C15—H15A⋯O3iii | 0.96 | 2.56 | 3.393 (3) | 145 | Symmetry codes: (i) ; (ii) ; (iii) x+1, y-1, z. | |
Cg⋯Cg | centroid–centroid distance | mean interplanar distancea | slippage angleb | Cg1⋯Cg1i | 3.7848 (13) | 3.428 (1) | 25.1 | Cg1⋯Cg2ii | 3.8456 (13) | 3.567 (1) | 22.0 | Symmetry codes: (i) −x, 1 − y, −z, (ii) −x, −y, −z. Notes: (a) distance from one plane to the neighbouring centroid; (b) angle subtended by the intercentroid vector to the plane normal. For details, see: Janiak (2000 ). | |
Data collection: APEX2 (Bruker, 2009
); cell refinement: SAINT (Bruker, 2009
); 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, 1997
) and PLATON (Spek, 2009
); software used to prepare material for publication: WinGX (Farrugia, 1999
) and PLATON.
Supporting information
Equimolar quantities of 5-aminosalicylic acid and 4-anisaldehyde were refluxed in methanol for 30 min resulting in clear brown solution. The solution was kept at room temperature which affoarded light brown prisms after 72 h.
All H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.95 Å (methyl) or 0.93 Å (aromatic) and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(Caromatic or N) or Uiso(H) = 1.5Ueq(Cmethyl). H atoms of the hydroxyl group was located in difference Fourier maps and included in the subsequent refinement using restraints (O—H = 0.85 (1) Å) with Uiso(H) = 1.5Ueq(O). In the last cycles of refinement this hydrogen was treated as riding on its parent O atom.
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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
2-Hydroxy-5-{[(
E)-4-methoxybenzylidene]azaniumyl}benzoate
top Crystal data top C15H13NO4 | F(000) = 568 |
Mr = 271.26 | Dx = 1.401 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1583 reflections |
a = 13.4369 (12) Å | θ = 2.9–25.3° |
b = 8.5619 (8) Å | µ = 0.10 mm−1 |
c = 12.6653 (11) Å | T = 296 K |
β = 118.004 (3)° | Prism, light brown |
V = 1286.5 (2) Å3 | 0.26 × 0.20 × 0.18 mm |
Z = 4 | |
Data collection top Bruker Kappa APEXII CCD diffractometer | 2320 independent reflections |
Radiation source: fine-focus sealed tube | 1583 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 8.10 pixels mm-1 | θmax = 25.3°, θmin = 2.9° |
ω scans | h = −15→16 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −10→10 |
Tmin = 0.982, Tmax = 0.987 | l = −15→10 |
9561 measured reflections | |
Refinement top 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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0831P)2 + 0.1187P] where P = (Fo2 + 2Fc2)/3 |
2320 reflections | (Δ/σ)max < 0.001 |
182 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Crystal data top C15H13NO4 | V = 1286.5 (2) Å3 |
Mr = 271.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.4369 (12) Å | µ = 0.10 mm−1 |
b = 8.5619 (8) Å | T = 296 K |
c = 12.6653 (11) Å | 0.26 × 0.20 × 0.18 mm |
β = 118.004 (3)° | |
Data collection top Bruker Kappa APEXII CCD diffractometer | 2320 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1583 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.987 | Rint = 0.031 |
9561 measured reflections | |
Refinement top R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.28 e Å−3 |
2320 reflections | Δρmin = −0.18 e Å−3 |
182 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 > 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 | Uiso*/Ueq | |
O1 | −0.19046 (12) | 0.62390 (19) | 0.15961 (12) | 0.0667 (5) | |
O2 | −0.03306 (11) | 0.49725 (16) | 0.27753 (10) | 0.0510 (4) | |
O3 | −0.29868 (11) | 0.56256 (18) | −0.05677 (12) | 0.0613 (5) | |
H3 | −0.2728 | 0.6015 | 0.0176 | 0.092* | |
O4 | 0.50744 (13) | −0.1897 (2) | 0.09919 (15) | 0.0857 (6) | |
N1 | 0.04782 (11) | 0.17725 (17) | −0.01733 (13) | 0.0405 (4) | |
H1 | 0.0329 | 0.1255 | −0.0813 | 0.049* | |
C1 | −0.11320 (15) | 0.5260 (2) | 0.17761 (15) | 0.0406 (5) | |
C2 | −0.11993 (13) | 0.4447 (2) | 0.06936 (14) | 0.0353 (4) | |
C3 | −0.21322 (15) | 0.4691 (2) | −0.04323 (16) | 0.0437 (5) | |
C4 | −0.21754 (16) | 0.3965 (3) | −0.14312 (17) | 0.0548 (6) | |
H4 | −0.2793 | 0.4128 | −0.2178 | 0.066* | |
C5 | −0.13155 (15) | 0.3009 (2) | −0.13273 (16) | 0.0507 (5) | |
H5 | −0.1350 | 0.2530 | −0.2002 | 0.061* | |
C6 | −0.03929 (14) | 0.2756 (2) | −0.02139 (15) | 0.0382 (4) | |
C7 | −0.03399 (13) | 0.3462 (2) | 0.07921 (15) | 0.0371 (4) | |
H7 | 0.0273 | 0.3276 | 0.1537 | 0.044* | |
C8 | 0.14683 (14) | 0.1574 (2) | 0.07203 (16) | 0.0421 (5) | |
H8 | 0.1627 | 0.2105 | 0.1423 | 0.051* | |
C9 | 0.23438 (14) | 0.0614 (2) | 0.07311 (16) | 0.0413 (5) | |
C10 | 0.33683 (16) | 0.0561 (3) | 0.17828 (17) | 0.0548 (6) | |
H10 | 0.3447 | 0.1116 | 0.2449 | 0.066* | |
C11 | 0.42584 (16) | −0.0289 (3) | 0.18534 (18) | 0.0633 (7) | |
H11 | 0.4934 | −0.0315 | 0.2562 | 0.076* | |
C12 | 0.41467 (16) | −0.1115 (3) | 0.08600 (18) | 0.0547 (6) | |
C13 | 0.31336 (17) | −0.1093 (3) | −0.01877 (18) | 0.0541 (5) | |
H13 | 0.3056 | −0.1665 | −0.0846 | 0.065* | |
C14 | 0.22442 (16) | −0.0231 (2) | −0.02569 (17) | 0.0476 (5) | |
H14 | 0.1570 | −0.0209 | −0.0967 | 0.057* | |
C15 | 0.5007 (2) | −0.2741 (4) | −0.0010 (3) | 0.1025 (10) | |
H15A | 0.5716 | −0.3243 | 0.0206 | 0.154* | |
H15B | 0.4836 | −0.2032 | −0.0660 | 0.154* | |
H15C | 0.4424 | −0.3515 | −0.0250 | 0.154* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0623 (9) | 0.0904 (12) | 0.0448 (8) | 0.0283 (9) | 0.0230 (7) | −0.0037 (8) |
O2 | 0.0533 (8) | 0.0604 (9) | 0.0315 (7) | 0.0028 (7) | 0.0135 (6) | 0.0023 (6) |
O3 | 0.0447 (8) | 0.0827 (11) | 0.0461 (8) | 0.0220 (7) | 0.0127 (7) | −0.0035 (7) |
O4 | 0.0628 (10) | 0.1237 (15) | 0.0748 (11) | 0.0473 (10) | 0.0358 (9) | 0.0216 (11) |
N1 | 0.0403 (8) | 0.0448 (9) | 0.0360 (8) | 0.0020 (7) | 0.0176 (7) | −0.0029 (7) |
C1 | 0.0401 (10) | 0.0465 (11) | 0.0365 (10) | −0.0018 (9) | 0.0189 (9) | 0.0033 (8) |
C2 | 0.0337 (9) | 0.0390 (10) | 0.0332 (9) | −0.0022 (8) | 0.0157 (8) | 0.0026 (8) |
C3 | 0.0361 (9) | 0.0522 (12) | 0.0392 (10) | 0.0055 (9) | 0.0147 (8) | 0.0013 (9) |
C4 | 0.0436 (11) | 0.0728 (14) | 0.0321 (10) | 0.0118 (11) | 0.0046 (9) | −0.0036 (10) |
C5 | 0.0472 (11) | 0.0620 (13) | 0.0345 (10) | 0.0066 (10) | 0.0120 (9) | −0.0085 (9) |
C6 | 0.0360 (9) | 0.0402 (10) | 0.0388 (10) | 0.0019 (8) | 0.0177 (8) | 0.0009 (8) |
C7 | 0.0320 (9) | 0.0417 (10) | 0.0332 (9) | −0.0005 (8) | 0.0118 (8) | 0.0050 (8) |
C8 | 0.0408 (10) | 0.0478 (11) | 0.0362 (10) | −0.0014 (9) | 0.0168 (8) | −0.0032 (8) |
C9 | 0.0369 (10) | 0.0465 (11) | 0.0385 (10) | 0.0012 (8) | 0.0161 (8) | 0.0009 (8) |
C10 | 0.0445 (11) | 0.0755 (15) | 0.0372 (11) | 0.0052 (10) | 0.0131 (9) | −0.0055 (10) |
C11 | 0.0399 (11) | 0.0946 (18) | 0.0445 (12) | 0.0129 (11) | 0.0108 (10) | 0.0063 (12) |
C12 | 0.0457 (11) | 0.0698 (14) | 0.0526 (13) | 0.0199 (11) | 0.0264 (10) | 0.0174 (11) |
C13 | 0.0569 (12) | 0.0628 (13) | 0.0435 (11) | 0.0120 (11) | 0.0243 (10) | 0.0011 (10) |
C14 | 0.0393 (10) | 0.0557 (12) | 0.0399 (10) | 0.0071 (9) | 0.0120 (9) | −0.0008 (9) |
C15 | 0.103 (2) | 0.123 (2) | 0.107 (2) | 0.0604 (19) | 0.0700 (18) | 0.0201 (19) |
Geometric parameters (Å, º) top O1—C1 | 1.269 (2) | C6—C7 | 1.381 (2) |
O2—C1 | 1.242 (2) | C7—H7 | 0.9300 |
O3—C3 | 1.343 (2) | C8—C9 | 1.430 (2) |
O3—H3 | 0.9015 | C8—H8 | 0.9300 |
O4—C12 | 1.354 (2) | C9—C10 | 1.396 (2) |
O4—C15 | 1.426 (3) | C9—C14 | 1.396 (3) |
N1—C8 | 1.291 (2) | C10—C11 | 1.367 (3) |
N1—C6 | 1.423 (2) | C10—H10 | 0.9300 |
N1—H1 | 0.8600 | C11—C12 | 1.389 (3) |
C1—C2 | 1.502 (2) | C11—H11 | 0.9300 |
C2—C7 | 1.388 (2) | C12—C13 | 1.385 (3) |
C2—C3 | 1.404 (2) | C13—C14 | 1.372 (3) |
C3—C4 | 1.386 (3) | C13—H13 | 0.9300 |
C4—C5 | 1.371 (3) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—H15A | 0.9600 |
C5—C6 | 1.390 (2) | C15—H15B | 0.9600 |
C5—H5 | 0.9300 | C15—H15C | 0.9600 |
| | | |
C3—O3—H3 | 101.5 | N1—C8—H8 | 117.0 |
C12—O4—C15 | 118.07 (18) | C9—C8—H8 | 117.0 |
C8—N1—C6 | 126.96 (16) | C10—C9—C14 | 118.36 (17) |
C8—N1—H1 | 116.5 | C10—C9—C8 | 117.77 (17) |
C6—N1—H1 | 116.5 | C14—C9—C8 | 123.85 (16) |
O2—C1—O1 | 123.99 (17) | C11—C10—C9 | 121.33 (19) |
O2—C1—C2 | 119.34 (16) | C11—C10—H10 | 119.3 |
O1—C1—C2 | 116.65 (15) | C9—C10—H10 | 119.3 |
C7—C2—C3 | 119.37 (16) | C10—C11—C12 | 119.54 (18) |
C7—C2—C1 | 120.59 (15) | C10—C11—H11 | 120.2 |
C3—C2—C1 | 120.04 (15) | C12—C11—H11 | 120.2 |
O3—C3—C4 | 118.93 (16) | O4—C12—C13 | 124.0 (2) |
O3—C3—C2 | 121.38 (16) | O4—C12—C11 | 115.99 (18) |
C4—C3—C2 | 119.68 (16) | C13—C12—C11 | 120.05 (18) |
C5—C4—C3 | 120.52 (17) | C14—C13—C12 | 120.22 (19) |
C5—C4—H4 | 119.7 | C14—C13—H13 | 119.9 |
C3—C4—H4 | 119.7 | C12—C13—H13 | 119.9 |
C4—C5—C6 | 120.05 (17) | C13—C14—C9 | 120.49 (17) |
C4—C5—H5 | 120.0 | C13—C14—H14 | 119.8 |
C6—C5—H5 | 120.0 | C9—C14—H14 | 119.8 |
C7—C6—C5 | 120.18 (16) | O4—C15—H15A | 109.5 |
C7—C6—N1 | 122.70 (15) | O4—C15—H15B | 109.5 |
C5—C6—N1 | 117.12 (16) | H15A—C15—H15B | 109.5 |
C6—C7—C2 | 120.18 (15) | O4—C15—H15C | 109.5 |
C6—C7—H7 | 119.9 | H15A—C15—H15C | 109.5 |
C2—C7—H7 | 119.9 | H15B—C15—H15C | 109.5 |
N1—C8—C9 | 126.07 (17) | | |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1 | 0.90 | 1.62 | 2.4816 (19) | 159 |
N1—H1···O2i | 0.86 | 1.90 | 2.7408 (19) | 166 |
C8—H8···O1ii | 0.93 | 2.47 | 3.179 (2) | 133 |
C14—H14···O2i | 0.93 | 2.30 | 3.183 (2) | 159 |
C15—H15A···O3iii | 0.96 | 2.56 | 3.393 (3) | 145 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y−1/2, −z+1/2; (iii) x+1, y−1, z. |
Experimental details
Crystal data |
Chemical formula | C15H13NO4 |
Mr | 271.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 13.4369 (12), 8.5619 (8), 12.6653 (11) |
β (°) | 118.004 (3) |
V (Å3) | 1286.5 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.26 × 0.20 × 0.18 |
|
Data collection |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.982, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9561, 2320, 1583 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.600 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.143, 1.02 |
No. of reflections | 2320 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.18 |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1 | 0.90 | 1.62 | 2.4816 (19) | 158.6 |
N1—H1···O2i | 0.86 | 1.90 | 2.7408 (19) | 166.4 |
C8—H8···O1ii | 0.93 | 2.47 | 3.179 (2) | 133.0 |
C14—H14···O2i | 0.93 | 2.30 | 3.183 (2) | 158.9 |
C15—H15A···O3iii | 0.96 | 2.56 | 3.393 (3) | 145.4 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y−1/2, −z+1/2; (iii) x+1, y−1, z. |
π–π stacking interactions (Å, °) topCg1 and Cg2 are the centroids of the C2–C7 and C9–C14 rings, respectively. |
Cg···Cg | centroid–centroid distance | mean interplanar distancea | slippage angleb |
Cg1···Cg1i | 3.7848 (13) | 3.428 (1) | 25.1 |
Cg1···Cg2ii | 3.8456 (13) | 3.567 (1) | 22.0 |
Symmetry codes: (i) -x, 1-y, -z, (ii) -x, -y, -z. Notes: (a) distance from one plane to the neighbouring centroid; (b) angle subtended by the intercentroid vector to the plane normal. For details, see: Janiak (2000). |
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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 | CRYSTALLOGRAPHIC COMMUNICATIONS |
ISSN: 2056-9890
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The title compound (I) has been synthesized as a potential ligand which could be used with various metals.
The title compound (I) is a Zwitterion. In (I), the group A (C2—C7/N1/O3) of 5-aminosalicylic acid moiety and the 4-methoxybenzaldehyde moiety B (C8—C15/O4) are planar with r. m. s. deviations of 0.0076 and 0.0255 Å, respectively. The dihedral angle between A/B is 10.37 (7)°. The carboxylate group C (O1/C1/O2) is oriented at a dihedral angle of 5.73 (24)° with the parent group A (Fig. 1). The title molecule is closely related to p-[(p-methoxybenzylidene)amino]phenol (Bryan et al., 1978) and N-benzyl-N'-{6- [(4-carboxylatobenzyl)aminocarbonyl]-2-pyridylmethyl}guanidinium (Ashiq et al., 2010)
The values of the C═O bond [1.241 (2), 1.269 (3) Å] are in agreement with the value, 1.235 (3)–1.261 (3) Å, reported for the N-benzyl-N'-{6- [(4-carboxylatobenzyl)aminocarbonyl]-2-pyridylmethyl}guanidinium (Ashiq et al., 2010). In the title compound S(6) ring motifs (Bernstein et al., 1995), is formed due to intramolecular H-bondings of O—H···O type (Table 1, Fig. 2). There exist R21(7) ring motif due to intermolecular H-bondings of C—H···O and N—H···O types linking the molecules to form infinite one dimensional chains extending along the crystallographic c-axis.
The occurence of slippest π–π stacking (Janiak, 2000) between symmetry related aromatic rings play an important role in stabilizing the packing.