N-[2-(Acetamido)-eth-yl]-2-hy-droxy-benzamide.

In the title mol-ecule, C(11)H(14)N(2)O(3), an intra-molecular O-H⋯O hydrogen bond closes an almost planar [maximum deviation = 0.022 (13) Å] six-membered ring and enforces the cis conformation of the keto group with respect to the hy-droxy substituent. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the moleclues into ribbons extended along [10]. Weak inter-molecular C-H⋯O inter-actions further consolidate the crystal packing.

Related literature

For general background to ribonucleic acid, see: Franklin (2001 ▶); Komiyama et al. (1999 ▶); Kuzuya et al. (2006 ▶); Morrow & Iranzo (2004 ▶); Nüttymäki & Lönnberg (2006 ▶). Some crystal structures of similar mol­ecules have been reported, for instance N-salicyloylglycine (Smeets et al., 1985 ▶), 2-(N-(2-(2-hy­droxy­benzamido)­ethyl­ammonio­eth­yl)amino­carbon­yl) phen­ol­ate (Liu et al., 2006 ▶) and N-(2-Amino­eth­yl)-2-hy­droxy­benzamide picrate (Yu et al., 2003 ▶). More crystal structures of analogs can be found in Cambridge Structural Database (Allen, 2002 ▶).

Experimental

Crystal data

C11H14N2O3

M = 222.24

Monoclinic,

a = 8.642 (3) Å

b = 4.9702 (18) Å

c = 24.972 (3) Å

β = 95.14 (2)°

V = 1068.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 90 K

0.3 × 0.2 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.111, T max = 1.000

4347 measured reflections

2439 independent reflections

1504 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.162

S = 1.04

2439 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003680/cv5045sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003680/cv5045Isup2.hkl

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

C11H14N2O3	F(000) = 472
Mr = 222.24	Dx = 1.38 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 990 reflections
a = 8.642 (3) Å	θ = 3.0–29.0°
b = 4.9702 (18) Å	µ = 0.10 mm−1
c = 24.972 (3) Å	T = 90 K
β = 95.14 (2)°	Block, yellow
V = 1068.3 (6) Å3	0.3 × 0.2 × 0.15 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	2439 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1504 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 16.1544 pixels mm-1	θmax = 29.2°, θmin = 3.3°
ω scans	h = −11→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −4→6
Tmin = 0.111, Tmax = 1.000	l = −28→33
4347 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.0266P] where P = (Fo2 + 2Fc2)/3
2439 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.34 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
C1	0.4433 (3)	0.3212 (5)	0.31898 (9)	0.0195 (5)
O1	0.3176 (2)	0.4713 (3)	0.32788 (7)	0.0273 (5)
H1	0.357 (4)	0.597 (7)	0.3630 (15)	0.078 (12)*
C2	0.5847 (3)	0.3520 (4)	0.34941 (9)	0.0163 (5)
C3	0.7073 (3)	0.1857 (5)	0.33760 (10)	0.0211 (6)
H3	0.8049	0.2046	0.3579	0.025*
C4	0.6913 (3)	−0.0051 (5)	0.29741 (10)	0.0237 (6)
H4	0.7763	−0.1170	0.2904	0.028*
C5	0.5507 (3)	−0.0306 (5)	0.26766 (10)	0.0239 (6)
H5	0.5385	−0.1613	0.2398	0.029*
C6	0.4275 (3)	0.1306 (5)	0.27763 (10)	0.0233 (6)
H6	0.3313	0.1127	0.2564	0.028*
C7	0.5993 (3)	0.5583 (4)	0.39258 (9)	0.0165 (5)
O7	0.48629 (18)	0.7039 (3)	0.40218 (6)	0.0215 (4)
N8	0.7353 (2)	0.5851 (4)	0.42095 (8)	0.0191 (5)
H8	0.815 (3)	0.471 (5)	0.4157 (10)	0.030 (8)*
C9	0.7594 (3)	0.7863 (5)	0.46326 (10)	0.0204 (5)
H9A	0.7091	0.9568	0.4508	0.024*
H9B	0.8722	0.8209	0.4706	0.024*
C10	0.6929 (3)	0.6963 (5)	0.51550 (9)	0.0214 (6)
H10A	0.5782	0.6873	0.5095	0.026*
H10B	0.7316	0.5136	0.5251	0.026*
N11	0.7358 (2)	0.8778 (4)	0.55967 (8)	0.0212 (5)
H11	0.666 (3)	0.991 (5)	0.5708 (11)	0.028 (7)*
C12	0.8726 (3)	0.8603 (5)	0.58797 (10)	0.0208 (6)
O12	0.97079 (19)	0.6959 (3)	0.57683 (7)	0.0249 (4)
C13	0.8981 (3)	1.0561 (5)	0.63381 (11)	0.0296 (6)
H13A	0.9890	1.0007	0.6575	0.044*
H13B	0.8062	1.0589	0.6541	0.044*
H13C	0.9157	1.2363	0.6196	0.044*

	U11	U22	U33	U12	U13	U23
C1	0.0211 (12)	0.0222 (13)	0.0154 (12)	0.0028 (10)	0.0029 (10)	0.0010 (10)
O1	0.0243 (10)	0.0317 (10)	0.0247 (10)	0.0087 (8)	−0.0043 (8)	−0.0064 (9)
C2	0.0225 (12)	0.0153 (11)	0.0117 (11)	0.0012 (10)	0.0051 (10)	0.0011 (10)
C3	0.0221 (13)	0.0245 (13)	0.0172 (13)	−0.0004 (10)	0.0038 (10)	−0.0019 (11)
C4	0.0285 (14)	0.0230 (13)	0.0213 (13)	0.0025 (11)	0.0110 (11)	−0.0018 (11)
C5	0.0318 (15)	0.0245 (13)	0.0164 (13)	−0.0070 (12)	0.0081 (11)	−0.0029 (11)
C6	0.0243 (13)	0.0309 (14)	0.0142 (12)	−0.0034 (11)	−0.0005 (10)	0.0009 (11)
C7	0.0206 (12)	0.0162 (12)	0.0130 (12)	0.0003 (10)	0.0043 (9)	0.0038 (10)
O7	0.0210 (9)	0.0265 (9)	0.0170 (9)	0.0046 (7)	0.0022 (7)	−0.0016 (7)
N8	0.0200 (11)	0.0226 (11)	0.0148 (11)	0.0031 (9)	0.0014 (8)	−0.0037 (9)
C9	0.0245 (13)	0.0208 (12)	0.0158 (12)	−0.0018 (10)	0.0015 (10)	−0.0015 (11)
C10	0.0220 (12)	0.0261 (13)	0.0164 (13)	−0.0029 (11)	0.0024 (10)	−0.0027 (11)
N11	0.0184 (11)	0.0301 (12)	0.0152 (11)	0.0051 (9)	0.0019 (9)	−0.0060 (9)
C12	0.0217 (13)	0.0242 (13)	0.0168 (13)	−0.0007 (11)	0.0036 (10)	0.0011 (11)
O12	0.0212 (9)	0.0308 (10)	0.0228 (10)	0.0061 (8)	0.0021 (7)	−0.0068 (8)
C13	0.0240 (14)	0.0373 (15)	0.0262 (15)	0.0070 (12)	−0.0051 (11)	−0.0109 (13)

C1—O1	1.352 (3)	N8—C9	1.456 (3)
C1—C2	1.389 (3)	N8—H8	0.91 (3)
C1—C6	1.399 (3)	C9—C10	1.538 (4)
O1—H1	1.11 (4)	C9—H9A	0.9900
C2—C3	1.395 (3)	C9—H9B	0.9900
C2—C7	1.485 (3)	C10—N11	1.447 (3)
C3—C4	1.379 (3)	C10—H10A	0.9900
C3—H3	0.9500	C10—H10B	0.9900
C4—C5	1.372 (4)	N11—C12	1.325 (3)
C4—H4	0.9500	N11—H11	0.89 (3)
C5—C6	1.373 (3)	C12—O12	1.228 (3)
C5—H5	0.9500	C12—C13	1.504 (3)
C6—H6	0.9500	C13—H13A	0.9800
C7—O7	1.255 (3)	C13—H13B	0.9800
C7—N8	1.323 (3)	C13—H13C	0.9800
O1—C1—C2	122.0 (2)	N8—C9—C10	112.0 (2)
O1—C1—C6	117.9 (2)	N8—C9—H9A	109.2
C2—C1—C6	120.1 (2)	C10—C9—H9A	109.2
C1—O1—H1	104.2 (18)	N8—C9—H9B	109.2
C1—C2—C3	117.8 (2)	C10—C9—H9B	109.2
C1—C2—C7	119.1 (2)	H9A—C9—H9B	107.9
C3—C2—C7	123.1 (2)	N11—C10—C9	112.1 (2)
C4—C3—C2	122.2 (2)	N11—C10—H10A	109.2
C4—C3—H3	118.9	C9—C10—H10A	109.2
C2—C3—H3	118.9	N11—C10—H10B	109.2
C5—C4—C3	118.9 (2)	C9—C10—H10B	109.2
C5—C4—H4	120.5	H10A—C10—H10B	107.9
C3—C4—H4	120.5	C12—N11—C10	121.4 (2)
C4—C5—C6	120.8 (2)	C12—N11—H11	118.2 (17)
C4—C5—H5	119.6	C10—N11—H11	120.0 (18)
C6—C5—H5	119.6	O12—C12—N11	121.6 (2)
C5—C6—C1	120.2 (2)	O12—C12—C13	123.1 (2)
C5—C6—H6	119.9	N11—C12—C13	115.2 (2)
C1—C6—H6	119.9	C12—C13—H13A	109.5
O7—C7—N8	120.6 (2)	C12—C13—H13B	109.5
O7—C7—C2	121.3 (2)	H13A—C13—H13B	109.5
N8—C7—C2	118.1 (2)	C12—C13—H13C	109.5
C7—N8—C9	121.4 (2)	H13A—C13—H13C	109.5
C7—N8—H8	120.5 (16)	H13B—C13—H13C	109.5
C9—N8—H8	118.1 (17)
O1—C1—C2—C3	179.3 (2)	C1—C2—C7—O7	0.3 (3)
C6—C1—C2—C3	−0.8 (3)	C3—C2—C7—O7	−179.8 (2)
O1—C1—C2—C7	−0.8 (3)	C1—C2—C7—N8	−179.7 (2)
C6—C1—C2—C7	179.1 (2)	C3—C2—C7—N8	0.2 (3)
C1—C2—C3—C4	−0.2 (3)	O7—C7—N8—C9	−1.2 (3)
C7—C2—C3—C4	179.9 (2)	C2—C7—N8—C9	178.81 (19)
C2—C3—C4—C5	0.7 (4)	C7—N8—C9—C10	78.9 (3)
C3—C4—C5—C6	−0.1 (4)	N8—C9—C10—N11	171.87 (19)
C4—C5—C6—C1	−0.9 (4)	C9—C10—N11—C12	−82.2 (3)
O1—C1—C6—C5	−178.7 (2)	C10—N11—C12—O12	2.5 (4)
C2—C1—C6—C5	1.4 (4)	C10—N11—C12—C13	−177.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O7	1.11 (4)	1.51 (4)	2.534 (3)	150 (3)
N8—H8···O12i	0.91 (3)	2.02 (3)	2.895 (3)	160 (2)
N11—H11···O7ii	0.89 (3)	2.16 (3)	3.040 (3)	174 (2)
C3—H3···O12i	0.95	2.47	3.404 (4)	169.
C6—H6···O1iii	0.95	2.47	3.325 (4)	150.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O7	1.11 (4)	1.51 (4)	2.534 (3)	150 (3)
N8—H8⋯O12i	0.91 (3)	2.02 (3)	2.895 (3)	160 (2)
N11—H11⋯O7ii	0.89 (3)	2.16 (3)	3.040 (3)	174 (2)
C3—H3⋯O12i	0.95	2.47	3.404 (4)	169
C6—H6⋯O1iii	0.95	2.47	3.325 (4)	150

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