N-(3-Hy-droxy-phen-yl)nicotinamide.

In the title mol-ecule, C(12)H(10)N(2)O(2), the benzene and pyridine rings form a dihedral angle of 5.01 (8)°. The amide group is twisted by 33.54 (7)° from the plane of the pyridine ring. In the crystal, mol-ecules are linked into centrosymmetric dimers via pairs of O-H⋯N hydrogen bonds. N-H⋯O hydrogen bonds further link dimers related into chains along the b axis.

Related literature

For related structures, see: Mocilac & Gallagher (2011 ▶); Roopan et al. (2009 ▶). For modern aspects of boronic acid derivatives, see: Hall (2005 ▶).

Experimental

Crystal data

C12H10N2O2

M = 214.22

Monoclinic,

a = 12.1741 (13) Å

b = 5.2613 (6) Å

c = 15.3113 (16) Å

β = 94.428 (2)°

V = 977.79 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.952, T max = 0.988

5813 measured reflections

1928 independent reflections

1572 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.04

1928 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015620/cv5281sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015620/cv5281Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015620/cv5281Isup3.cml

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

C12H10N2O2	F(000) = 448
Mr = 214.22	Dx = 1.455 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 82 reflections
a = 12.1741 (13) Å	θ = 2.2–23.3°
b = 5.2613 (6) Å	µ = 0.10 mm−1
c = 15.3113 (16) Å	T = 293 K
β = 94.428 (2)°	Block, colourless
V = 977.79 (18) Å3	0.35 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1928 independent reflections
Radiation source: fine-focus sealed tube	1572 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 26.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.952, Tmax = 0.988	k = −6→4
5813 measured reflections	l = −18→18

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.3178P] where P = (Fo2 + 2Fc2)/3
1928 reflections	(Δ/σ)max < 0.001
150 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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
O2	0.10112 (9)	0.0774 (2)	0.89614 (8)	0.0393 (3)
H2B	0.1369	−0.0179	0.9298	0.059*
N2	0.46607 (10)	0.4089 (3)	0.86950 (8)	0.0293 (3)
C12	0.28388 (12)	0.2438 (3)	0.88031 (10)	0.0289 (3)
H12	0.3155	0.1113	0.9137	0.035*
O1	0.51225 (9)	0.8283 (2)	0.87911 (8)	0.0403 (3)
C5	0.73908 (12)	0.6822 (3)	0.88082 (10)	0.0309 (4)
H5	0.7221	0.8299	0.8493	0.037*
N1	0.79027 (10)	0.2474 (3)	0.97897 (9)	0.0327 (3)
C11	0.17038 (12)	0.2524 (3)	0.86264 (10)	0.0310 (4)
C6	0.53822 (12)	0.6020 (3)	0.88392 (10)	0.0279 (3)
C2	0.86888 (13)	0.3961 (3)	0.95025 (10)	0.0339 (4)
H2	0.9420	0.3493	0.9632	0.041*
C9	0.19122 (13)	0.6308 (3)	0.77876 (10)	0.0354 (4)
H9	0.1596	0.7605	0.7441	0.042*
C8	0.30484 (13)	0.6289 (3)	0.79759 (10)	0.0310 (4)
H8	0.3490	0.7560	0.7767	0.037*
C4	0.65565 (12)	0.5257 (3)	0.90684 (9)	0.0267 (3)
C7	0.35048 (12)	0.4310 (3)	0.84863 (9)	0.0267 (3)
C1	0.84752 (13)	0.6154 (3)	0.90241 (11)	0.0349 (4)
H1	0.9048	0.7159	0.8851	0.042*
C3	0.68548 (12)	0.3122 (3)	0.95639 (10)	0.0307 (4)
H3	0.6298	0.2087	0.9749	0.037*
C10	0.12390 (13)	0.4454 (3)	0.81013 (10)	0.0349 (4)
H10	0.0482	0.4501	0.7962	0.042*
H2A	0.4898 (13)	0.261 (4)	0.8741 (10)	0.030 (5)*

	U11	U22	U33	U12	U13	U23
O2	0.0341 (6)	0.0315 (7)	0.0528 (8)	0.0008 (5)	0.0074 (5)	0.0036 (5)
N2	0.0292 (7)	0.0198 (7)	0.0385 (8)	0.0021 (6)	−0.0012 (5)	0.0000 (6)
C12	0.0318 (8)	0.0221 (8)	0.0323 (8)	0.0038 (6)	−0.0013 (6)	−0.0014 (6)
O1	0.0347 (6)	0.0231 (6)	0.0624 (8)	0.0011 (5)	−0.0004 (5)	−0.0003 (5)
C5	0.0350 (8)	0.0266 (8)	0.0311 (8)	−0.0025 (7)	0.0027 (6)	0.0010 (6)
N1	0.0306 (7)	0.0273 (7)	0.0396 (7)	0.0001 (6)	−0.0012 (6)	−0.0012 (6)
C11	0.0303 (8)	0.0270 (8)	0.0360 (8)	−0.0001 (7)	0.0037 (6)	−0.0074 (7)
C6	0.0301 (8)	0.0238 (8)	0.0298 (8)	0.0004 (6)	0.0027 (6)	−0.0003 (6)
C2	0.0276 (8)	0.0333 (9)	0.0402 (9)	0.0008 (7)	−0.0006 (7)	−0.0051 (7)
C9	0.0422 (9)	0.0320 (9)	0.0311 (8)	0.0121 (8)	−0.0025 (7)	−0.0001 (7)
C8	0.0366 (8)	0.0268 (8)	0.0294 (8)	0.0010 (7)	0.0007 (6)	−0.0011 (6)
C4	0.0299 (8)	0.0228 (8)	0.0274 (7)	0.0000 (6)	0.0023 (6)	−0.0049 (6)
C7	0.0283 (7)	0.0229 (8)	0.0284 (7)	0.0021 (6)	−0.0002 (6)	−0.0044 (6)
C1	0.0301 (8)	0.0372 (9)	0.0381 (9)	−0.0065 (7)	0.0062 (7)	−0.0026 (7)
C3	0.0295 (8)	0.0266 (8)	0.0360 (8)	−0.0034 (6)	0.0021 (6)	−0.0018 (7)
C10	0.0289 (8)	0.0383 (10)	0.0370 (9)	0.0070 (7)	−0.0010 (7)	−0.0069 (7)

O2—C11	1.3741 (19)	C11—C10	1.388 (2)
O2—H2B	0.8200	C6—C4	1.500 (2)
N2—C6	1.350 (2)	C2—C1	1.381 (2)
N2—C7	1.4234 (19)	C2—H2	0.9300
N2—H2A	0.831 (18)	C9—C10	1.384 (2)
C12—C7	1.387 (2)	C9—C8	1.391 (2)
C12—C11	1.388 (2)	C9—H9	0.9300
C12—H12	0.9300	C8—C7	1.391 (2)
O1—C6	1.2325 (18)	C8—H8	0.9300
C5—C1	1.381 (2)	C4—C3	1.388 (2)
C5—C4	1.389 (2)	C1—H1	0.9300
C5—H5	0.9300	C3—H3	0.9300
N1—C2	1.336 (2)	C10—H10	0.9300
N1—C3	1.3396 (19)
C11—O2—H2B	109.5	C10—C9—H9	119.0
C6—N2—C7	126.48 (14)	C8—C9—H9	119.0
C6—N2—H2A	118.2 (12)	C9—C8—C7	117.99 (15)
C7—N2—H2A	115.3 (11)	C9—C8—H8	121.0
C7—C12—C11	120.56 (14)	C7—C8—H8	121.0
C7—C12—H12	119.7	C3—C4—C5	118.02 (14)
C11—C12—H12	119.7	C3—C4—C6	123.28 (13)
C1—C5—C4	119.16 (15)	C5—C4—C6	118.62 (14)
C1—C5—H5	120.4	C12—C7—C8	120.59 (14)
C4—C5—H5	120.4	C12—C7—N2	117.24 (13)
C2—N1—C3	117.27 (14)	C8—C7—N2	122.16 (14)
O2—C11—C12	122.38 (14)	C2—C1—C5	118.47 (15)
O2—C11—C10	118.15 (14)	C2—C1—H1	120.8
C12—C11—C10	119.47 (14)	C5—C1—H1	120.8
O1—C6—N2	123.82 (14)	N1—C3—C4	123.40 (14)
O1—C6—C4	120.52 (14)	N1—C3—H3	118.3
N2—C6—C4	115.67 (13)	C4—C3—H3	118.3
N1—C2—C1	123.60 (15)	C9—C10—C11	119.38 (14)
N1—C2—H2	118.2	C9—C10—H10	120.3
C1—C2—H2	118.2	C11—C10—H10	120.3
C10—C9—C8	121.96 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···N1i	0.82	2.00	2.817 (2)	173
N2—H2A···O1ii	0.83 (2)	2.29 (2)	3.107 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯N1i	0.82	2.00	2.817 (2)	173
N2—H2A⋯O1ii	0.83 (2)	2.29 (2)	3.107 (2)	166

Symmetry codes: (i) ; (ii) .