4-Hy-droxy-N-methyl-benzamide.

Three independent mol-ecules 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 inter-actions 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 ▶).

Experimental

Crystal data

C8H9NO2

M = 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

Δρmax = 0.58 e Å−3

Δρmin = −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.

Click here for additional data file.

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

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009781/hg5306Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H9NO2	F(000) = 960
Mr = 151.16	Dx = 1.371 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 13.576 (3) Å	Cell parameters from 3483 reflections
b = 16.964 (3) Å	θ = 4.6–77.5°
c = 11.025 (2) Å	µ = 0.10 mm−1
β = 120.11 (3)°	T = 100 K
V = 2196.5 (10) Å3	Block, colourless
Z = 12	0.42 × 0.28 × 0.22 mm

Agilent Xcalibur diffractometer with a Ruby (Gemini Cu) detector	2545 reflections with I > 2σ(I)
Detector resolution: 10.5081 pixels mm-1	Rint = 0.015
ω scans	θmax = 26.8°, θmin = 2.1°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −17→12
Tmin = 0.634, Tmax = 1.000	k = −21→20
4810 measured reflections	l = −13→13
2802 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059	w = 1/[σ2(Fo2) + (0.1461P)2 + 0.3673P], where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.192	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.58 e Å−3
2802 reflections	Δρmin = −0.56 e Å−3
305 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.020 (6)

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.

	x	y	z	Uiso*/Ueq
O1A	−0.1230 (3)	0.69501 (19)	0.1817 (4)	0.0616 (8)
H1A	−0.1628	0.7033	0.0974	0.092*
O2A	0.2475 (3)	0.42236 (17)	0.4097 (3)	0.0612 (8)
N1A	0.1573 (2)	0.39940 (16)	0.1817 (3)	0.0404 (6)
H1AA	0.1024	0.4109	0.0992	0.048*
C1A	0.0968 (3)	0.5501 (2)	0.3666 (4)	0.0471 (8)
H1AB	0.1499	0.5376	0.4589	0.056*
C2A	0.0254 (4)	0.6130 (3)	0.3400 (4)	0.0504 (9)
H2A	0.0306	0.6425	0.4141	0.060*
C3A	−0.0548 (3)	0.6331 (2)	0.2026 (4)	0.0452 (8)
C4A	−0.0623 (3)	0.5876 (2)	0.0918 (4)	0.0468 (8)
H4A	−0.1158	0.6002	−0.0004	0.056*
C5A	0.0102 (3)	0.5240 (2)	0.1201 (4)	0.0439 (8)
H5A	0.0048	0.4938	0.0467	0.053*
C6A	0.0917 (3)	0.5048 (2)	0.2590 (3)	0.0402 (7)
C7A	0.1730 (3)	0.4393 (2)	0.2940 (4)	0.0431 (8)
C8A	0.2365 (5)	0.3355 (3)	0.2037 (6)	0.0549 (9)
H8AA	0.2520	0.3063	0.2861	0.082*
H8AB	0.3062	0.3570	0.2156	0.082*
H8AC	0.2034	0.3010	0.1239	0.082*
O1B	1.1116 (3)	0.8638 (2)	0.7338 (3)	0.0617 (9)
H1B	1.1397	0.8800	0.8145	0.093*
O2B	0.7422 (3)	0.58944 (17)	0.5125 (3)	0.0576 (8)
N1B	0.8321 (3)	0.56916 (17)	0.7436 (3)	0.0406 (7)
H1BA	0.8845	0.5830	0.8261	0.049*
C1B	0.9770 (3)	0.6941 (2)	0.7987 (4)	0.0455 (8)
H1BB	0.9815	0.6651	0.8729	0.055*
C2B	1.0491 (3)	0.7578 (2)	0.8255 (4)	0.0464 (9)
H2B	1.1014	0.7717	0.9175	0.056*
C3B	1.0433 (3)	0.8006 (2)	0.7158 (4)	0.0466 (9)
C4B	0.9661 (4)	0.7791 (3)	0.5779 (5)	0.0540 (10)
H4B	0.9628	0.8074	0.5038	0.065*
C5B	0.8946 (3)	0.7156 (2)	0.5518 (4)	0.0486 (9)
H5B	0.8434	0.7010	0.4598	0.058*
C6B	0.8987 (3)	0.6735 (2)	0.6626 (4)	0.0422 (8)
C7B	0.8164 (3)	0.6074 (2)	0.6300 (4)	0.0437 (9)
C8B	0.7582 (4)	0.5039 (2)	0.7230 (5)	0.0562 (11)
H8BA	0.7827	0.4587	0.6927	0.084*
H8BB	0.6817	0.5173	0.6530	0.084*
H8BC	0.7606	0.4919	0.8096	0.084*
O1C	0.3742 (3)	0.4691 (2)	0.6850 (4)	0.0665 (9)
H1C	0.3295	0.4643	0.6007	0.100*
O2C	0.7454 (3)	0.74129 (17)	0.9069 (3)	0.0630 (8)
N1C	0.6574 (3)	0.76016 (17)	0.6775 (3)	0.0433 (7)
H1CA	0.6057	0.7459	0.5949	0.052*
C1C	0.5934 (4)	0.6151 (3)	0.8683 (4)	0.0532 (9)
H1CB	0.6448	0.6298	0.9601	0.064*
C2C	0.5220 (4)	0.5522 (3)	0.8445 (4)	0.0558 (10)
H2C	0.5255	0.5244	0.9193	0.067*
C3C	0.4443 (3)	0.5305 (2)	0.7068 (4)	0.0484 (9)
C4C	0.4387 (4)	0.5731 (2)	0.5946 (4)	0.0522 (9)
H4C	0.3865	0.5590	0.5027	0.063*
C5C	0.5114 (4)	0.6359 (2)	0.6212 (4)	0.0491 (9)
H5C	0.5075	0.6644	0.5469	0.059*
C6C	0.5906 (3)	0.6570 (2)	0.7589 (4)	0.0434 (8)
C7C	0.6724 (3)	0.7228 (2)	0.7924 (4)	0.0463 (8)
C8C	0.7327 (5)	0.8257 (2)	0.6993 (6)	0.0567 (10)
H8CA	0.7403	0.8575	0.7756	0.085*
H8CB	0.7016	0.8571	0.6156	0.085*
H8CC	0.8061	0.8061	0.7211	0.085*

	U11	U22	U33	U12	U13	U23
O1A	0.068 (2)	0.0641 (17)	0.0477 (17)	0.0157 (15)	0.0253 (16)	−0.0002 (14)
O2A	0.0643 (19)	0.0652 (17)	0.0364 (15)	0.0055 (14)	0.0122 (13)	−0.0009 (13)
N1A	0.0413 (15)	0.0462 (13)	0.0254 (13)	0.0085 (12)	0.0107 (11)	0.0014 (11)
C1A	0.050 (2)	0.057 (2)	0.0305 (16)	−0.0027 (16)	0.0168 (16)	0.0005 (14)
C2A	0.051 (2)	0.062 (2)	0.0323 (19)	−0.0003 (18)	0.0161 (17)	−0.0064 (17)
C3A	0.047 (2)	0.0462 (18)	0.039 (2)	−0.0024 (14)	0.0196 (17)	0.0009 (14)
C4A	0.048 (2)	0.055 (2)	0.0309 (17)	0.0003 (17)	0.0146 (15)	0.0058 (15)
C5A	0.050 (2)	0.0504 (18)	0.0297 (18)	−0.0048 (15)	0.0187 (16)	−0.0044 (14)
C6A	0.0413 (17)	0.0466 (16)	0.0304 (17)	−0.0068 (14)	0.0161 (14)	−0.0005 (13)
C7A	0.0399 (17)	0.0477 (18)	0.0364 (18)	−0.0064 (13)	0.0152 (15)	0.0020 (14)
C8A	0.055 (2)	0.0538 (18)	0.050 (2)	0.0078 (16)	0.0221 (17)	0.0012 (16)
O1B	0.061 (2)	0.0612 (18)	0.053 (2)	−0.0118 (15)	0.0207 (17)	0.0036 (14)
O2B	0.0545 (17)	0.0564 (16)	0.0410 (17)	−0.0079 (13)	0.0084 (13)	−0.0068 (13)
N1B	0.0472 (17)	0.0416 (14)	0.0294 (14)	−0.0108 (13)	0.0165 (12)	−0.0029 (12)
C1B	0.046 (2)	0.0509 (19)	0.038 (2)	0.0015 (16)	0.0199 (17)	0.0043 (15)
C2B	0.0418 (19)	0.055 (2)	0.037 (2)	−0.0008 (16)	0.0159 (17)	−0.0020 (16)
C3B	0.044 (2)	0.0481 (19)	0.046 (2)	0.0016 (16)	0.0217 (18)	0.0039 (16)
C4B	0.060 (3)	0.058 (2)	0.039 (2)	0.0001 (19)	0.021 (2)	0.0109 (17)
C5B	0.048 (2)	0.055 (2)	0.0306 (18)	0.0001 (17)	0.0108 (17)	0.0027 (15)
C6B	0.0440 (19)	0.0419 (16)	0.038 (2)	0.0047 (14)	0.0188 (17)	0.0015 (14)
C7B	0.048 (2)	0.0435 (18)	0.036 (2)	0.0085 (15)	0.0189 (17)	0.0025 (14)
C8B	0.057 (2)	0.049 (2)	0.065 (3)	−0.0082 (19)	0.032 (2)	−0.009 (2)
O1C	0.069 (2)	0.0711 (19)	0.0519 (19)	−0.0204 (17)	0.0249 (16)	0.0013 (15)
O2C	0.070 (2)	0.0558 (15)	0.0412 (17)	−0.0042 (14)	0.0114 (14)	0.0022 (13)
N1C	0.0464 (16)	0.0442 (13)	0.0334 (14)	−0.0093 (12)	0.0156 (12)	−0.0013 (12)
C1C	0.053 (2)	0.059 (2)	0.0360 (19)	0.0029 (17)	0.0141 (17)	0.0029 (16)
C2C	0.055 (3)	0.066 (2)	0.037 (2)	−0.0010 (19)	0.0153 (19)	0.0130 (18)
C3C	0.044 (2)	0.0509 (19)	0.045 (2)	0.0008 (15)	0.0184 (17)	0.0005 (16)
C4C	0.053 (2)	0.059 (2)	0.037 (2)	0.0008 (18)	0.0176 (18)	−0.0027 (16)
C5C	0.055 (2)	0.053 (2)	0.034 (2)	0.0017 (17)	0.0187 (18)	0.0030 (15)
C6C	0.0439 (18)	0.0445 (16)	0.039 (2)	0.0077 (15)	0.0185 (16)	0.0020 (14)
C7C	0.046 (2)	0.0417 (17)	0.047 (2)	0.0048 (14)	0.0198 (17)	−0.0018 (14)
C8C	0.063 (3)	0.0435 (18)	0.066 (3)	−0.0039 (17)	0.034 (2)	0.0017 (18)

O1A—H1A	0.8200	C2B—C3B	1.379 (5)
O1A—C3A	1.341 (5)	C3B—C4B	1.395 (6)
O2A—C7A	1.199 (5)	C4B—H4B	0.9300
N1A—H1AA	0.8600	C4B—C5B	1.379 (6)
N1A—C7A	1.331 (5)	C5B—H5B	0.9300
N1A—C8A	1.460 (5)	C5B—C6B	1.393 (5)
C1A—H1AB	0.9300	C6B—C7B	1.493 (5)
C1A—C2A	1.371 (6)	C8B—H8BA	0.9600
C1A—C6A	1.386 (5)	C8B—H8BB	0.9600
C2A—H2A	0.9300	C8B—H8BC	0.9600
C2A—C3A	1.394 (6)	O1C—H1C	0.8200
C3A—C4A	1.405 (5)	O1C—C3C	1.349 (5)
C4A—H4A	0.9300	O2C—C7C	1.191 (5)
C4A—C5A	1.386 (5)	N1C—H1CA	0.8600
C5A—H5A	0.9300	N1C—C7C	1.338 (5)
C5A—C6A	1.405 (5)	N1C—C8C	1.446 (5)
C6A—C7A	1.474 (5)	C1C—H1CB	0.9300
C8A—H8AA	0.9600	C1C—C2C	1.376 (6)
C8A—H8AB	0.9600	C1C—C6C	1.385 (5)
C8A—H8AC	0.9600	C2C—H2C	0.9300
O1B—H1B	0.8200	C2C—C3C	1.395 (6)
O1B—C3B	1.364 (5)	C3C—C4C	1.402 (6)
O2B—C7B	1.215 (5)	C4C—H4C	0.9300
N1B—H1BA	0.8600	C4C—C5C	1.380 (6)
N1B—C7B	1.330 (5)	C5C—H5C	0.9300
N1B—C8B	1.434 (5)	C5C—C6C	1.397 (5)
C1B—H1BB	0.9300	C6C—C7C	1.484 (5)
C1B—C2B	1.387 (6)	C8C—H8CA	0.9600
C1B—C6B	1.380 (6)	C8C—H8CB	0.9600
C2B—H2B	0.9300	C8C—H8CC	0.9600
C3A—O1A—H1A	109.5	C4B—C5B—H5B	119.9
C7A—N1A—H1AA	121.2	C4B—C5B—C6B	120.2 (4)
C7A—N1A—C8A	117.5 (4)	C6B—C5B—H5B	119.9
C8A—N1A—H1AA	121.2	C1B—C6B—C5B	119.6 (4)
C2A—C1A—H1AB	119.2	C1B—C6B—C7B	121.8 (3)
C2A—C1A—C6A	121.5 (4)	C5B—C6B—C7B	118.6 (4)
C6A—C1A—H1AB	119.2	O2B—C7B—N1B	122.5 (4)
C1A—C2A—H2A	119.8	O2B—C7B—C6B	124.4 (4)
C1A—C2A—C3A	120.4 (3)	N1B—C7B—C6B	113.1 (3)
C3A—C2A—H2A	119.8	N1B—C8B—H8BA	109.5
O1A—C3A—C2A	118.2 (3)	N1B—C8B—H8BB	109.5
O1A—C3A—C4A	122.6 (4)	N1B—C8B—H8BC	109.5
C2A—C3A—C4A	119.2 (3)	H8BA—C8B—H8BB	109.5
C3A—C4A—H4A	120.1	H8BA—C8B—H8BC	109.5
C5A—C4A—C3A	119.8 (4)	H8BB—C8B—H8BC	109.5
C5A—C4A—H4A	120.1	C3C—O1C—H1C	109.5
C4A—C5A—H5A	119.7	C7C—N1C—H1CA	121.7
C4A—C5A—C6A	120.6 (3)	C7C—N1C—C8C	116.6 (4)
C6A—C5A—H5A	119.7	C8C—N1C—H1CA	121.7
C1A—C6A—C5A	118.5 (3)	C2C—C1C—H1CB	119.2
C1A—C6A—C7A	119.0 (3)	C2C—C1C—C6C	121.6 (4)
C5A—C6A—C7A	122.5 (3)	C6C—C1C—H1CB	119.2
O2A—C7A—N1A	121.6 (4)	C1C—C2C—H2C	120.4
O2A—C7A—C6A	125.4 (4)	C1C—C2C—C3C	119.2 (4)
N1A—C7A—C6A	113.0 (3)	C3C—C2C—H2C	120.4
N1A—C8A—H8AA	109.5	O1C—C3C—C2C	118.6 (4)
N1A—C8A—H8AB	109.5	O1C—C3C—C4C	121.3 (4)
N1A—C8A—H8AC	109.5	C2C—C3C—C4C	120.1 (4)
H8AA—C8A—H8AB	109.5	C3C—C4C—H4C	120.2
H8AA—C8A—H8AC	109.5	C5C—C4C—C3C	119.6 (4)
H8AB—C8A—H8AC	109.5	C5C—C4C—H4C	120.2
C3B—O1B—H1B	109.5	C4C—C5C—H5C	119.7
C7B—N1B—H1BA	121.3	C4C—C5C—C6C	120.6 (3)
C7B—N1B—C8B	117.3 (3)	C6C—C5C—H5C	119.7
C8B—N1B—H1BA	121.3	C1C—C6C—C5C	119.0 (4)
C2B—C1B—H1BB	119.8	C1C—C6C—C7C	118.6 (4)
C6B—C1B—H1BB	119.8	C5C—C6C—C7C	122.4 (3)
C6B—C1B—C2B	120.4 (4)	O2C—C7C—N1C	122.0 (4)
C1B—C2B—H2B	120.0	O2C—C7C—C6C	125.6 (4)
C3B—C2B—C1B	120.0 (4)	N1C—C7C—C6C	112.4 (3)
C3B—C2B—H2B	120.0	N1C—C8C—H8CA	109.5
O1B—C3B—C2B	123.4 (4)	N1C—C8C—H8CB	109.5
O1B—C3B—C4B	116.7 (4)	N1C—C8C—H8CC	109.5
C2B—C3B—C4B	119.9 (4)	H8CA—C8C—H8CB	109.5
C3B—C4B—H4B	120.1	H8CA—C8C—H8CC	109.5
C5B—C4B—C3B	119.9 (4)	H8CB—C8C—H8CC	109.5
C5B—C4B—H4B	120.1
O1A—C3A—C4A—C5A	−179.7 (3)	C3B—C4B—C5B—C6B	0.5 (6)
C1A—C2A—C3A—O1A	179.9 (4)	C4B—C5B—C6B—C1B	−1.8 (6)
C1A—C2A—C3A—C4A	0.6 (6)	C4B—C5B—C6B—C7B	177.3 (3)
C1A—C6A—C7A—O2A	−2.4 (5)	C5B—C6B—C7B—O2B	−3.0 (6)
C1A—C6A—C7A—N1A	178.5 (3)	C5B—C6B—C7B—N1B	176.9 (4)
C2A—C1A—C6A—C5A	−0.7 (5)	C6B—C1B—C2B—C3B	−0.5 (6)
C2A—C1A—C6A—C7A	178.3 (3)	C8B—N1B—C7B—O2B	0.8 (6)
C2A—C3A—C4A—C5A	−0.3 (5)	C8B—N1B—C7B—C6B	−179.1 (3)
C3A—C4A—C5A—C6A	−0.4 (5)	O1C—C3C—C4C—C5C	179.6 (4)
C4A—C5A—C6A—C1A	0.9 (5)	C1C—C2C—C3C—O1C	−179.6 (4)
C4A—C5A—C6A—C7A	−178.0 (3)	C1C—C2C—C3C—C4C	−0.6 (6)
C5A—C6A—C7A—O2A	176.5 (4)	C1C—C6C—C7C—O2C	3.7 (6)
C5A—C6A—C7A—N1A	−2.6 (4)	C1C—C6C—C7C—N1C	−177.5 (3)
C6A—C1A—C2A—C3A	0.0 (6)	C2C—C1C—C6C—C5C	1.6 (6)
C8A—N1A—C7A—O2A	−1.9 (6)	C2C—C1C—C6C—C7C	−178.3 (4)
C8A—N1A—C7A—C6A	177.2 (3)	C2C—C3C—C4C—C5C	0.6 (6)
O1B—C3B—C4B—C5B	179.8 (4)	C3C—C4C—C5C—C6C	0.4 (6)
C1B—C2B—C3B—O1B	−179.7 (4)	C4C—C5C—C6C—C1C	−1.5 (6)
C1B—C2B—C3B—C4B	−0.9 (6)	C4C—C5C—C6C—C7C	178.4 (3)
C1B—C6B—C7B—O2B	176.1 (4)	C5C—C6C—C7C—O2C	−176.2 (4)
C1B—C6B—C7B—N1B	−3.9 (5)	C5C—C6C—C7C—N1C	2.7 (5)
C2B—C1B—C6B—C5B	1.8 (6)	C6C—C1C—C2C—C3C	−0.5 (7)
C2B—C1B—C6B—C7B	−177.3 (3)	C8C—N1C—C7C—O2C	−1.5 (6)
C2B—C3B—C4B—C5B	0.9 (6)	C8C—N1C—C7C—C6C	179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2Ci	0.82	1.94	2.749 (5)	170
C2A—H2A···N1Aii	0.93	2.66	3.267 (5)	124
C4A—H4A···N1Bi	0.93	2.60	3.371 (5)	141
O1B—H1B···O2Biii	0.82	1.98	2.784 (5)	166
C2B—H2B···N1Ciii	0.93	2.63	3.404 (5)	142
O1C—H1C···O2A	0.82	1.96	2.750 (5)	163

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

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