(S)-N-(1-Hydroxy-methyl-2-methyl-prop-yl)-2-methoxy-benzamide.

The title compound, C(13)H(19)NO(3), is an important synthetic inter-mediate. Weak O-H⋯O and N-H⋯O hydrogen bonds enhance the stability of the crystal structure.

Related literature

For related literature, see: Ma & You (2007 ▶); Rechavi & Lemaire (2002 ▶).

Experimental

Crystal data

C13H19NO3

M = 237.29

Orthorhombic,

a = 9.015 (4) Å

b = 10.386 (4) Å

c = 14.005 (4) Å

V = 1311.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 291 (2) K

0.50 × 0.44 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

1457 measured reflections

1397 independent reflections

848 reflections with I > 2σ(I)

R int = 0.010

3 standard reflections every 120 reflections intensity decay: 0.4%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.136

S = 1.02

1397 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.14 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801009X/er2052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801009X/er2052Isup2.hkl

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

C13H19NO3	F000 = 512
Mr = 237.29	Dx = 1.202 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.015 (4) Å	θ = 4.5–6.7º
b = 10.386 (4) Å	µ = 0.09 mm−1
c = 14.005 (4) Å	T = 291 (2) K
V = 1311.3 (9) Å3	Block, colourless
Z = 4	0.50 × 0.44 × 0.40 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.010
Radiation source: fine-focus sealed tube	θmax = 25.5º
Monochromator: graphite	θmin = 2.4º
T = 291(2) K	h = −3→10
ω/2θ scans	k = −3→12
Absorption correction: none	l = −5→16
1457 measured reflections	3 standard reflections
1397 independent reflections	every 120 reflections
848 reflections with I > 2σ(I)	intensity decay: 0.4%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.0778P)2 + 0.0096P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.136	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.21 e Å−3
1397 reflections	Δρmin = −0.14 e Å−3
164 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.069 (8)
Secondary atom site location: difference Fourier map

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
O1	0.1432 (3)	0.3872 (3)	0.16126 (19)	0.0666 (8)
O2	0.5192 (3)	0.3286 (3)	−0.00264 (18)	0.0703 (8)
O3	0.2632 (4)	0.0046 (3)	−0.0111 (2)	0.0810 (10)
H3	0.1945	0.0562	−0.0140	0.097*
N1	0.3536 (3)	0.2340 (2)	0.0926 (2)	0.0487 (8)
H1N1	0.2711	0.2433	0.1227	0.058*
C1	0.1842 (4)	0.4786 (3)	0.0963 (3)	0.0514 (9)
C2	0.1074 (5)	0.5935 (4)	0.0851 (3)	0.0709 (12)
H2	0.0240	0.6099	0.1223	0.085*
C3	0.1535 (6)	0.6826 (4)	0.0201 (4)	0.0878 (16)
H3A	0.1009	0.7591	0.0133	0.105*
C4	0.2760 (6)	0.6610 (4)	−0.0355 (4)	0.0929 (18)
H4	0.3078	0.7226	−0.0791	0.112*
C5	0.3519 (5)	0.5457 (4)	−0.0255 (3)	0.0745 (13)
H5	0.4337	0.5300	−0.0642	0.089*
C6	0.3096 (4)	0.4533 (3)	0.0402 (3)	0.0489 (9)
C7	0.0018 (6)	0.3961 (7)	0.2048 (3)	0.109 (2)
H7A	−0.0038	0.4739	0.2416	0.163*
H7B	−0.0130	0.3233	0.2460	0.163*
H7C	−0.0735	0.3970	0.1564	0.163*
C8	0.4020 (4)	0.3328 (3)	0.0425 (2)	0.0459 (9)
C9	0.4288 (4)	0.1097 (3)	0.1012 (2)	0.0456 (8)
H9	0.5050	0.1060	0.0514	0.055*
C10	0.3202 (5)	0.0025 (3)	0.0824 (3)	0.0609 (10)
H10A	0.3691	−0.0794	0.0932	0.073*
H10B	0.2387	0.0091	0.1273	0.073*
C11	0.5075 (5)	0.0978 (4)	0.1981 (3)	0.0632 (11)
H11	0.5515	0.0115	0.2002	0.076*
C12	0.6339 (6)	0.1925 (5)	0.2074 (4)	0.0939 (16)
H12A	0.5957	0.2787	0.2045	0.141*
H12B	0.7031	0.1794	0.1562	0.141*
H12C	0.6832	0.1796	0.2674	0.141*
C13	0.4068 (6)	0.1084 (6)	0.2833 (3)	0.107 (2)
H13A	0.4630	0.0946	0.3406	0.160*
H13B	0.3299	0.0447	0.2788	0.160*
H13C	0.3631	0.1926	0.2849	0.160*

	U11	U22	U33	U12	U13	U23
O1	0.0560 (16)	0.0735 (18)	0.0704 (16)	0.0177 (16)	0.0102 (13)	0.0020 (15)
O2	0.0553 (16)	0.0652 (18)	0.0903 (18)	−0.0022 (15)	0.0249 (16)	0.0137 (16)
O3	0.072 (2)	0.071 (2)	0.099 (2)	0.0007 (16)	−0.0180 (18)	−0.0113 (17)
N1	0.0369 (15)	0.0481 (16)	0.0610 (17)	0.0057 (15)	0.0078 (14)	0.0039 (14)
C1	0.050 (2)	0.046 (2)	0.058 (2)	−0.0001 (18)	−0.0117 (19)	−0.0054 (18)
C2	0.064 (3)	0.060 (3)	0.089 (3)	0.015 (2)	−0.016 (2)	−0.019 (2)
C3	0.070 (3)	0.048 (2)	0.146 (4)	0.002 (2)	−0.043 (3)	0.008 (3)
C4	0.067 (3)	0.059 (3)	0.152 (5)	−0.011 (3)	−0.030 (3)	0.047 (3)
C5	0.053 (2)	0.066 (2)	0.104 (3)	−0.010 (2)	−0.011 (2)	0.031 (3)
C6	0.044 (2)	0.0442 (18)	0.059 (2)	−0.0051 (17)	−0.0149 (17)	0.0013 (17)
C7	0.077 (3)	0.156 (6)	0.094 (3)	0.036 (4)	0.030 (3)	0.020 (4)
C8	0.037 (2)	0.046 (2)	0.054 (2)	−0.0041 (17)	−0.0023 (16)	0.0044 (18)
C9	0.0387 (18)	0.0447 (19)	0.0534 (19)	0.0069 (17)	0.0040 (15)	−0.0004 (17)
C10	0.053 (2)	0.050 (2)	0.080 (3)	0.0044 (19)	0.000 (2)	0.004 (2)
C11	0.062 (3)	0.061 (3)	0.067 (2)	0.016 (2)	−0.009 (2)	0.011 (2)
C12	0.096 (3)	0.093 (3)	0.093 (3)	0.000 (3)	−0.037 (3)	−0.011 (3)
C13	0.120 (4)	0.146 (5)	0.054 (2)	0.031 (5)	0.004 (3)	0.016 (3)

O1—C1	1.365 (4)	C6—C8	1.504 (5)
O1—C7	1.416 (5)	C7—H7A	0.9600
O2—C8	1.232 (4)	C7—H7B	0.9600
O3—C10	1.406 (5)	C7—H7C	0.9600
O3—H3	0.8200	C9—C10	1.506 (5)
N1—C8	1.318 (4)	C9—C11	1.537 (5)
N1—C9	1.463 (4)	C9—H9	0.9800
N1—H1N1	0.8600	C10—H10A	0.9700
C1—C2	1.389 (5)	C10—H10B	0.9700
C1—C6	1.402 (5)	C11—C13	1.503 (6)
C2—C3	1.363 (6)	C11—C12	1.511 (6)
C2—H2	0.9300	C11—H11	0.9800
C3—C4	1.369 (7)	C12—H12A	0.9600
C3—H3A	0.9300	C12—H12B	0.9600
C4—C5	1.386 (6)	C12—H12C	0.9600
C4—H4	0.9300	C13—H13A	0.9600
C5—C6	1.383 (5)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C1—O1—C7	119.1 (4)	N1—C8—C6	118.4 (3)
C10—O3—H3	109.5	N1—C9—C10	109.7 (3)
C8—N1—C9	125.3 (3)	N1—C9—C11	111.0 (3)
C8—N1—H1N1	117.4	C10—C9—C11	113.3 (3)
C9—N1—H1N1	117.4	N1—C9—H9	107.5
O1—C1—C2	122.5 (4)	C10—C9—H9	107.5
O1—C1—C6	117.5 (3)	C11—C9—H9	107.5
C2—C1—C6	120.0 (4)	O3—C10—C9	112.9 (3)
C3—C2—C1	120.4 (4)	O3—C10—H10A	109.0
C3—C2—H2	119.8	C9—C10—H10A	109.0
C1—C2—H2	119.8	O3—C10—H10B	109.0
C2—C3—C4	121.0 (4)	C9—C10—H10B	109.0
C2—C3—H3A	119.5	H10A—C10—H10B	107.8
C4—C3—H3A	119.5	C13—C11—C12	109.8 (4)
C3—C4—C5	118.8 (4)	C13—C11—C9	114.6 (3)
C3—C4—H4	120.6	C12—C11—C9	111.8 (3)
C5—C4—H4	120.6	C13—C11—H11	106.7
C6—C5—C4	122.0 (5)	C12—C11—H11	106.7
C6—C5—H5	119.0	C9—C11—H11	106.7
C4—C5—H5	119.0	C11—C12—H12A	109.5
C5—C6—C1	117.7 (4)	C11—C12—H12B	109.5
C5—C6—C8	116.0 (3)	H12A—C12—H12B	109.5
C1—C6—C8	126.2 (3)	C11—C12—H12C	109.5
O1—C7—H7A	109.5	H12A—C12—H12C	109.5
O1—C7—H7B	109.5	H12B—C12—H12C	109.5
H7A—C7—H7B	109.5	C11—C13—H13A	109.5
O1—C7—H7C	109.5	C11—C13—H13B	109.5
H7A—C7—H7C	109.5	H13A—C13—H13B	109.5
H7B—C7—H7C	109.5	C11—C13—H13C	109.5
O2—C8—N1	122.0 (3)	H13A—C13—H13C	109.5
O2—C8—C6	119.6 (3)	H13B—C13—H13C	109.5
C7—O1—C1—C2	13.4 (5)	C9—N1—C8—C6	179.2 (3)
C7—O1—C1—C6	−167.0 (4)	C5—C6—C8—O2	9.9 (5)
O1—C1—C2—C3	179.3 (3)	C1—C6—C8—O2	−171.7 (3)
C6—C1—C2—C3	−0.3 (6)	C5—C6—C8—N1	−169.6 (3)
C1—C2—C3—C4	−0.0 (6)	C1—C6—C8—N1	8.8 (5)
C2—C3—C4—C5	0.9 (7)	C8—N1—C9—C10	−130.9 (4)
C3—C4—C5—C6	−1.5 (7)	C8—N1—C9—C11	103.2 (4)
C4—C5—C6—C1	1.2 (6)	N1—C9—C10—O3	63.2 (4)
C4—C5—C6—C8	179.7 (4)	C11—C9—C10—O3	−172.2 (3)
O1—C1—C6—C5	−179.8 (3)	N1—C9—C11—C13	59.7 (4)
C2—C1—C6—C5	−0.2 (5)	C10—C9—C11—C13	−64.2 (5)
O1—C1—C6—C8	1.8 (5)	N1—C9—C11—C12	−66.1 (4)
C2—C1—C6—C8	−178.6 (3)	C10—C9—C11—C12	170.0 (3)
C9—N1—C8—O2	−0.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2i	0.82	2.00	2.806 (4)	170
N1—H1N1···O1	0.86	1.96	2.656 (4)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2i	0.82	2.00	2.806 (4)	170
N1—H1N1⋯O1	0.86	1.96	2.656 (4)	137

Symmetry code: (i) .