Abstract
In the title molecule, C10H12O3, all non-H atoms lie in a common plane (r.m.s deviation = 0.010 Å). The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond.
Related literature
For the biological activity of methylbenzene derivatives, see: Anbarasan et al. (2011 ▶); Chan & Daniels (2007 ▶). For related structures see: Wang et al. (2011 ▶); Kılıç et al. (2009 ▶); For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶).
Experimental
Crystal data
C10H12O3
M r = 180.20
Monoclinic,
a = 13.899 (3) Å
b = 8.9184 (19) Å
c = 7.5043 (16) Å
β = 94.098 (6)°
V = 927.8 (3) Å3
Z = 4
Mo Kα radiation
μ = 0.10 mm−1
T = 295 K
0.30 × 0.24 × 0.20 mm
Data collection
Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.981
10089 measured reflections
2329 independent reflections
1213 reflections with I > 2σ(I)
R int = 0.050
Refinement
R[F 2 > 2σ(F 2)] = 0.054
wR(F 2) = 0.181
S = 1.03
2329 reflections
121 parameters
H-atom parameters constrained
Δρmax = 0.24 e Å−3
Δρmin = −0.22 e Å−3
Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002845/bt6886sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002845/bt6886Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536813002845/bt6886Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O2—H2⋯O1 | 0.82 | 1.91 | 2.628 (3) | 146 |
Acknowledgments
The authors wish to acknowledge the SAIF, IIT, Madras for the data collection.
supplementary crystallographic information
Comment
In recent days methylbenzene (toluene) and substituted methylbenzene have become very important on account of their wide range of applications in medicine and industry (Anbarasan et al., 2011). For example 3-chloro-2-methylbenzene-1-sulfonylchloride shows the biological activity of hydroxysteriod dehydrogenase inhibitors (Chan & Daniels, 2007).
The geometric parameters of the compound (I), (Fig. 1) agree well with those of a reported similar structure (Wang et al., 2011; Kılıç et al., 2009) The molecular structure is stabilized by an intramolecular O-H..O interaction generating a six-membered ring S(6) graph-set motif (Bernstein et al., 1995).
Experimental
To a methanolic solution of 2-hydroxy-5-methyl-1,3-benzenedicarboxaldehyde (1g, 6mmol) decarborane (0.37, 3 mmol) was added slowly with constant stirring at room temperature in nitrogen atmosphere for 24 hours. A pale yellow solution formed after 24h and was concentrated to get the crude product. The crude product was washed well with methanol and dried in vacuum. The product was recrystallized in chloroform to get pale yellow coloured crystals suitable for single crystal XRD. yield 0.96g, 80% .
Refinement
H atoms were positioned geometrically and refined using riding model with C-H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic C-H, C-H = 0.97Å and Uiso(H) = 1.2Ueq(C) for CH2, C-H = 0.96Å and Uiso(H) = 1.5Ueq(C) for CH3 and O-H = 0.82Å and Uiso(H) = 1.2Ueq(C) for OH.
Figures
Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Crystal data
| C10H12O3 | F(000) = 384 |
| Mr = 180.20 | Dx = 1.290 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 3221 reflections |
| a = 13.899 (3) Å | θ = 2.7–24.8° |
| b = 8.9184 (19) Å | µ = 0.10 mm−1 |
| c = 7.5043 (16) Å | T = 295 K |
| β = 94.098 (6)° | Block, yellow |
| V = 927.8 (3) Å3 | 0.30 × 0.24 × 0.20 mm |
| Z = 4 |
Data collection
| Bruker Kappa APEXII diffractometer | 2329 independent reflections |
| Radiation source: fine-focus sealed tube | 1213 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.050 |
| ω and φ scans | θmax = 28.7°, θmin = 2.7° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→18 |
| Tmin = 0.972, Tmax = 0.981 | k = −11→12 |
| 10089 measured reflections | l = −9→9 |
Refinement
| 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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.181 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0625P)2 + 0.4641P] where P = (Fo2 + 2Fc2)/3 |
| 2329 reflections | (Δ/σ)max < 0.001 |
| 121 parameters | Δρmax = 0.24 e Å−3 |
| 0 restraints | Δρmin = −0.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C8 | 0.92734 (18) | 1.0908 (3) | 0.1482 (4) | 0.0617 (7) | |
| H8 | 0.9842 | 1.1345 | 0.1959 | 0.074* | |
| C1 | 0.85176 (16) | 1.1898 (2) | 0.0792 (3) | 0.0459 (6) | |
| C6 | 0.86550 (16) | 1.3446 (3) | 0.0868 (3) | 0.0497 (6) | |
| H6 | 0.9241 | 1.3825 | 0.1349 | 0.060* | |
| C5 | 0.79476 (17) | 1.4420 (2) | 0.0250 (3) | 0.0479 (6) | |
| C4 | 0.70806 (16) | 1.3801 (2) | −0.0467 (3) | 0.0457 (6) | |
| H4 | 0.6595 | 1.4449 | −0.0906 | 0.055* | |
| C3 | 0.69089 (16) | 1.2288 (2) | −0.0558 (3) | 0.0426 (5) | |
| C2 | 0.76424 (16) | 1.1324 (2) | 0.0081 (3) | 0.0438 (5) | |
| C9 | 0.59741 (17) | 1.1631 (3) | −0.1290 (3) | 0.0536 (6) | |
| H9A | 0.6088 | 1.0965 | −0.2275 | 0.064* | |
| H9B | 0.5690 | 1.1049 | −0.0370 | 0.064* | |
| C10 | 0.4451 (2) | 1.2195 (3) | −0.2637 (4) | 0.0741 (9) | |
| H10A | 0.4569 | 1.1579 | −0.3648 | 0.111* | |
| H10B | 0.4030 | 1.3006 | −0.3012 | 0.111* | |
| H10C | 0.4155 | 1.1602 | −0.1759 | 0.111* | |
| C7 | 0.8079 (2) | 1.6091 (3) | 0.0330 (4) | 0.0687 (8) | |
| H7A | 0.7929 | 1.6451 | 0.1483 | 0.103* | |
| H7B | 0.7657 | 1.6556 | −0.0576 | 0.103* | |
| H7C | 0.8736 | 1.6336 | 0.0132 | 0.103* | |
| O1 | 0.92264 (14) | 0.9535 (2) | 0.1490 (3) | 0.0772 (6) | |
| O2 | 0.74664 (13) | 0.98329 (17) | 0.0006 (3) | 0.0618 (5) | |
| H2 | 0.7946 | 0.9376 | 0.0410 | 0.093* | |
| O3 | 0.53348 (12) | 1.27783 (19) | −0.1888 (3) | 0.0638 (5) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C8 | 0.0507 (15) | 0.0628 (17) | 0.0718 (19) | 0.0088 (12) | 0.0061 (12) | 0.0047 (13) |
| C1 | 0.0469 (13) | 0.0412 (12) | 0.0500 (14) | 0.0053 (10) | 0.0060 (10) | 0.0027 (9) |
| C6 | 0.0463 (13) | 0.0475 (14) | 0.0549 (15) | −0.0047 (10) | 0.0020 (10) | −0.0034 (11) |
| C5 | 0.0530 (14) | 0.0374 (11) | 0.0532 (14) | −0.0033 (10) | 0.0039 (10) | −0.0027 (10) |
| C4 | 0.0475 (13) | 0.0361 (11) | 0.0535 (14) | 0.0042 (9) | 0.0028 (10) | 0.0029 (10) |
| C3 | 0.0475 (12) | 0.0357 (11) | 0.0449 (13) | −0.0051 (9) | 0.0059 (9) | 0.0007 (9) |
| C2 | 0.0515 (13) | 0.0319 (11) | 0.0487 (13) | −0.0005 (9) | 0.0086 (10) | 0.0017 (9) |
| C9 | 0.0560 (14) | 0.0406 (12) | 0.0638 (16) | −0.0052 (11) | 0.0027 (12) | 0.0040 (11) |
| C10 | 0.0586 (17) | 0.0758 (19) | 0.085 (2) | −0.0147 (14) | −0.0139 (14) | 0.0095 (16) |
| C7 | 0.0728 (18) | 0.0374 (13) | 0.095 (2) | −0.0071 (12) | −0.0003 (15) | −0.0078 (13) |
| O1 | 0.0704 (13) | 0.0538 (12) | 0.1080 (18) | 0.0216 (9) | 0.0109 (11) | 0.0142 (11) |
| O2 | 0.0665 (12) | 0.0333 (9) | 0.0858 (14) | 0.0009 (7) | 0.0063 (10) | 0.0045 (8) |
| O3 | 0.0500 (10) | 0.0528 (10) | 0.0858 (13) | −0.0075 (8) | −0.0136 (9) | 0.0087 (9) |
Geometric parameters (Å, º)
| C8—O1 | 1.227 (3) | C2—O2 | 1.352 (2) |
| C8—C1 | 1.440 (3) | C9—O3 | 1.407 (3) |
| C8—H8 | 0.9300 | C9—H9A | 0.9700 |
| C1—C2 | 1.391 (3) | C9—H9B | 0.9700 |
| C1—C6 | 1.394 (3) | C10—O3 | 1.413 (3) |
| C6—C5 | 1.368 (3) | C10—H10A | 0.9600 |
| C6—H6 | 0.9300 | C10—H10B | 0.9600 |
| C5—C4 | 1.398 (3) | C10—H10C | 0.9600 |
| C5—C7 | 1.503 (3) | C7—H7A | 0.9600 |
| C4—C3 | 1.372 (3) | C7—H7B | 0.9600 |
| C4—H4 | 0.9300 | C7—H7C | 0.9600 |
| C3—C2 | 1.392 (3) | O2—H2 | 0.8200 |
| C3—C9 | 1.494 (3) | ||
| O1—C8—C1 | 125.2 (3) | O3—C9—C3 | 110.18 (18) |
| O1—C8—H8 | 117.4 | O3—C9—H9A | 109.6 |
| C1—C8—H8 | 117.4 | C3—C9—H9A | 109.6 |
| C2—C1—C6 | 119.6 (2) | O3—C9—H9B | 109.6 |
| C2—C1—C8 | 120.5 (2) | C3—C9—H9B | 109.6 |
| C6—C1—C8 | 119.9 (2) | H9A—C9—H9B | 108.1 |
| C5—C6—C1 | 121.5 (2) | O3—C10—H10A | 109.5 |
| C5—C6—H6 | 119.3 | O3—C10—H10B | 109.5 |
| C1—C6—H6 | 119.3 | H10A—C10—H10B | 109.5 |
| C6—C5—C4 | 117.3 (2) | O3—C10—H10C | 109.5 |
| C6—C5—C7 | 122.3 (2) | H10A—C10—H10C | 109.5 |
| C4—C5—C7 | 120.4 (2) | H10B—C10—H10C | 109.5 |
| C3—C4—C5 | 123.3 (2) | C5—C7—H7A | 109.5 |
| C3—C4—H4 | 118.3 | C5—C7—H7B | 109.5 |
| C5—C4—H4 | 118.3 | H7A—C7—H7B | 109.5 |
| C4—C3—C2 | 118.0 (2) | C5—C7—H7C | 109.5 |
| C4—C3—C9 | 123.2 (2) | H7A—C7—H7C | 109.5 |
| C2—C3—C9 | 118.74 (19) | H7B—C7—H7C | 109.5 |
| O2—C2—C1 | 121.9 (2) | C2—O2—H2 | 109.5 |
| O2—C2—C3 | 117.8 (2) | C9—O3—C10 | 111.7 (2) |
| C1—C2—C3 | 120.25 (19) | ||
| O1—C8—C1—C2 | 0.9 (4) | C8—C1—C2—O2 | −0.1 (3) |
| O1—C8—C1—C6 | 179.6 (2) | C6—C1—C2—C3 | 0.2 (3) |
| C2—C1—C6—C5 | −0.3 (3) | C8—C1—C2—C3 | 179.0 (2) |
| C8—C1—C6—C5 | −179.0 (2) | C4—C3—C2—O2 | 179.3 (2) |
| C1—C6—C5—C4 | −0.2 (3) | C9—C3—C2—O2 | −0.1 (3) |
| C1—C6—C5—C7 | 179.6 (2) | C4—C3—C2—C1 | 0.2 (3) |
| C6—C5—C4—C3 | 0.7 (3) | C9—C3—C2—C1 | −179.2 (2) |
| C7—C5—C4—C3 | −179.1 (2) | C4—C3—C9—O3 | 1.4 (3) |
| C5—C4—C3—C2 | −0.8 (3) | C2—C3—C9—O3 | −179.2 (2) |
| C5—C4—C3—C9 | 178.7 (2) | C3—C9—O3—C10 | 178.3 (2) |
| C6—C1—C2—O2 | −178.8 (2) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2···O1 | 0.82 | 1.91 | 2.628 (3) | 146 |
| C4—H4···O3 | 0.93 | 2.38 | 2.736 (3) | 103 |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6886).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002845/bt6886sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002845/bt6886Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536813002845/bt6886Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report