4-Hy­droxy-N-methyl­benzamide

Jerry P Jasinski; Joel P St John; Ray J Butcher; B Narayana; H S Yathirajan; B K Sarojini

doi:10.1107/S1600536813009781

. 2013 Apr 17;69(Pt 5):o738. doi: 10.1107/S1600536813009781

4-Hydroxy-N-methylbenzamide

Jerry P Jasinski ^a,^*, Joel P St John ^a, Ray J Butcher ^b, B Narayana ^c, H S Yathirajan ^d, B K Sarojini ^e

PMCID: PMC3648269 PMID: 23723889

Abstract

Three independent molecules comprise the asymmetric unit of the title compound, C₈H₉NO₂, in which the dihedral angles between the amide group and the benzene ring are 3.0 (2), 4.0 (3) and 3.3 (9)°. In the crystal, O—H⋯O hydrogen bonds and weak C—H⋯N interactions are observed, forming infinite chains along [101].

Related literature

For background to the biological activity of aromatic amides, see: Saeed et al. (2008 ▶); Brunsveld et al. (2001 ▶); Prins et al. (2001 ▶). For the anti-emetic activity of N-substituted benzamides, see: Vega-Noverola et al. (1989 ▶). For related structures, see: Escalada et al. (2004 ▶); Pertlik (1992 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). graphic file with name e-69-0o738-scheme1.jpg

Experimental

Crystal data

C₈H₉NO₂
M _r = 151.16
Monoclinic,
a = 13.576 (3) Å
b = 16.964 (3) Å
c = 11.025 (2) Å
β = 120.11 (3)°
V = 2196.5 (10) Å³
Z = 12
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.42 × 0.28 × 0.22 mm

Data collection

Agilent Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T _min = 0.634, T _max = 1.000
4810 measured reflections
2802 independent reflections
2545 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.192
S = 1.10
2802 reflections
305 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Click here for additional data file.^{(170KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009781/hg5306sup1.cif

e-69-0o738-sup1.cif^{(170KB, cif)}

Click here for additional data file.^{(154KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009781/hg5306Isup2.hkl

e-69-0o738-Isup2.hkl^{(154KB, hkl)}

Click here for additional data file.^{(3.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813009781/hg5306Isup3.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
O1A—H1A⋯O2C ⁱ	0.82	1.94	2.749 (5)	170
C2A—H2A⋯N1A ⁱⁱ	0.93	2.66	3.267 (5)	124
C4A—H4A⋯N1B ⁱ	0.93	2.60	3.371 (5)	141
O1B—H1B⋯O2B ⁱⁱⁱ	0.82	1.98	2.784 (5)	166
C2B—H2B⋯N1C ⁱⁱⁱ	0.93	2.63	3.404 (5)	142
O1C—H1C⋯O2A	0.82	1.96	2.750 (5)	163

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

BN thanks Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. HSY thanks the UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Aromatic amides have found extensive application in synthetic organic chemistry and have a wide range of biological activities (Saeed et al., 2008, Brunsveld et al., 2001; Prins et al., 2001). Various N-substituted benzamides exhibit potent antiemetic activity (Vega-Noverola et al., 1989). The crystal structure of N-methylbenzamide, viz., 2,3-dihydroxy-N-methylbenzamide monohydrate has been reported (Escalada et al., 2004). Also the crystal structures of 2-hydroxy-N-methylbenzamide and 2-hydroxy-N-methylthiobenzamide have been published (Pertlik, 1992). In view of the importance of aromatic amides, we report the crystal structure of the title compound, C₈H₉NO₂, (I).

In (I), three independent molecules (A, B. C) crystallize in the asymmetric unit (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987). The dihedral angle between the amide group and the benzene ring is 3.0 (2)°, 4.0 (3)° and 3.3 (9)°, respectively. In the crystal, O—H···O hydrogen bonds and weak C—H···N intermolecular interactions are observed (Table 1) forming infinite 1-D chains along (101) and contribute to packing stability (Fig. 2). The closest intercentroid distance between two π-ring systems is 5.214 (6) Å.

Experimental

4-Hydroxybenzoyl chloride (1.56 g, 0.01 mole) and methylamine (0.31 g, 0.01 mole) were dissolved in 20 ml methanol and stirred at room temperature for 3 h (Fig. 3). Then the reaction mass was poured into 50 ml ice cold water. The solid obtained was filtered and dried. Single crystals were grown from acetone by the slow evaporation method with a yield of 76%. (m.p. 395 K). Analytical data: Found (Calculated): C % : 63.54 (63.56); H% : 5.98 (6.00) ; N% : 9.21 (9.27).