N-(4-Methoxy-phen-yl)pivalamide.

In the title mol-ecule, C(12)H(17)NO(2), the amide (N-C=O) plane is oriented at an angle of 33.9 (1)° with respect to the aromatic ring. This is accompanied by an intra-molecular C-H⋯O hydrogen bond. The meth-oxy group lies almost in the plane of the benzene ring [C-O-C-C torsion angle = 2.7 (2)°]. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along [010].

Related literature

For details of the biological activity of benzanilides, see: Olsson et al. (2002 ▶); Lindgren et al. (2001 ▶); Calderone et al. (2006 ▶). For the use of benzamides in organic synthesis, see: Zhichkin et al. (2007 ▶); Beccalli et al. (2005 ▶). For related structures see: Gowda et al. (2007a ▶,b ▶); Saeed et al. (2008 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C12H17NO2

M = 207.27

Orthorhombic,

a = 9.5547 (13) Å

b = 10.0657 (15) Å

c = 24.575 (4) Å

V = 2363.5 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.40 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.969, T max = 0.984

17959 measured reflections

2817 independent reflections

2158 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.120

S = 1.02

2817 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029535/fl2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029535/fl2254Isup2.hkl

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

C12H17NO2	F(000) = 896
Mr = 207.27	Dx = 1.165 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 778 reflections
a = 9.5547 (13) Å	θ = 2.7–27.0°
b = 10.0657 (15) Å	µ = 0.08 mm−1
c = 24.575 (4) Å	T = 120 K
V = 2363.5 (6) Å3	Block, colourless
Z = 8	0.40 × 0.25 × 0.20 mm

Bruker SMART APEX diffractometer	2817 independent reflections
Radiation source: sealed tube	2158 reflections with I > 2σ(I)
graphite	Rint = 0.053
φ and ω scans	θmax = 27.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→12
Tmin = 0.969, Tmax = 0.984	k = −13→13
17959 measured reflections	l = −31→32

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.120	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.8944P] where P = (Fo2 + 2Fc2)/3
2817 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.19 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
O1	0.23114 (10)	0.78822 (9)	0.15214 (4)	0.0261 (2)
O2	−0.30713 (11)	0.99245 (12)	0.02439 (5)	0.0353 (3)
N1	0.18414 (12)	1.00795 (11)	0.14651 (5)	0.0221 (3)
H1A	0.2122	1.0875	0.1566	0.027*
C1	0.26370 (14)	0.90357 (13)	0.16238 (5)	0.0196 (3)
C2	0.05959 (14)	1.00104 (13)	0.11504 (5)	0.0203 (3)
C3	−0.03786 (15)	0.89929 (13)	0.12087 (6)	0.0233 (3)
H3A	−0.0213	0.8293	0.1460	0.028*
C4	−0.15869 (15)	0.90042 (14)	0.09003 (6)	0.0264 (3)
H4A	−0.2249	0.8307	0.0940	0.032*
C5	−0.18439 (15)	1.00250 (15)	0.05324 (6)	0.0253 (3)
C6	−0.08911 (16)	1.10480 (14)	0.04785 (6)	0.0270 (3)
H6A	−0.1068	1.1757	0.0233	0.032*
C7	0.03299 (15)	1.10322 (13)	0.07865 (6)	0.0249 (3)
H7A	0.0991	1.1731	0.0747	0.030*
C8	−0.33901 (18)	1.09944 (18)	−0.01185 (7)	0.0375 (4)
H8A	−0.3448	1.1826	0.0088	0.056*
H8B	−0.4289	1.0823	−0.0298	0.056*
H8C	−0.2652	1.1067	−0.0394	0.056*
C9	0.39771 (15)	0.93998 (13)	0.19354 (6)	0.0227 (3)
C10	0.36095 (17)	1.02511 (15)	0.24320 (7)	0.0313 (4)
H10A	0.4468	1.0479	0.2629	0.047*
H10B	0.2983	0.9752	0.2672	0.047*
H10C	0.3143	1.1067	0.2312	0.047*
C11	0.46851 (17)	0.81265 (15)	0.21301 (7)	0.0337 (4)
H11A	0.5542	0.8351	0.2329	0.050*
H11B	0.4920	0.7571	0.1816	0.050*
H11C	0.4048	0.7640	0.2371	0.050*
C12	0.49651 (16)	1.01588 (16)	0.15543 (7)	0.0328 (4)
H12A	0.5824	1.0391	0.1751	0.049*
H12B	0.4504	1.0972	0.1428	0.049*
H12C	0.5199	0.9599	0.1241	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0257 (5)	0.0146 (5)	0.0380 (6)	−0.0001 (4)	−0.0074 (4)	−0.0020 (4)
O2	0.0262 (6)	0.0441 (7)	0.0356 (6)	−0.0021 (5)	−0.0122 (5)	0.0052 (5)
N1	0.0226 (6)	0.0141 (5)	0.0297 (6)	−0.0008 (4)	−0.0065 (5)	−0.0017 (5)
C1	0.0211 (7)	0.0177 (6)	0.0201 (6)	0.0008 (5)	−0.0003 (5)	0.0001 (5)
C2	0.0201 (7)	0.0184 (6)	0.0223 (6)	0.0026 (5)	−0.0026 (5)	−0.0024 (5)
C3	0.0237 (7)	0.0197 (6)	0.0266 (7)	0.0008 (5)	−0.0012 (6)	0.0018 (5)
C4	0.0226 (7)	0.0253 (7)	0.0315 (8)	−0.0035 (6)	−0.0006 (6)	−0.0012 (6)
C5	0.0195 (7)	0.0324 (8)	0.0240 (7)	0.0026 (6)	−0.0019 (5)	−0.0040 (6)
C6	0.0275 (8)	0.0269 (7)	0.0267 (8)	0.0040 (6)	−0.0023 (6)	0.0056 (6)
C7	0.0241 (7)	0.0201 (7)	0.0307 (8)	−0.0009 (5)	−0.0029 (6)	0.0026 (6)
C8	0.0318 (9)	0.0506 (10)	0.0301 (9)	0.0057 (8)	−0.0106 (7)	0.0047 (7)
C9	0.0230 (7)	0.0172 (6)	0.0278 (7)	0.0001 (5)	−0.0058 (6)	0.0009 (5)
C10	0.0346 (9)	0.0283 (7)	0.0310 (8)	−0.0007 (6)	−0.0095 (7)	−0.0052 (6)
C11	0.0326 (9)	0.0231 (7)	0.0453 (10)	0.0035 (6)	−0.0177 (7)	0.0017 (7)
C12	0.0209 (7)	0.0365 (8)	0.0409 (9)	−0.0025 (6)	−0.0036 (7)	0.0071 (7)

O1—C1	1.2282 (16)	C7—H7A	0.9500
O2—C5	1.3741 (17)	C8—H8A	0.9800
O2—C8	1.4304 (19)	C8—H8B	0.9800
N1—C1	1.3542 (17)	C8—H8C	0.9800
N1—C2	1.4209 (17)	C9—C11	1.5262 (19)
N1—H1A	0.8800	C9—C10	1.532 (2)
C1—C9	1.5362 (19)	C9—C12	1.534 (2)
C2—C7	1.3866 (19)	C10—H10A	0.9800
C2—C3	1.3916 (19)	C10—H10B	0.9800
C3—C4	1.381 (2)	C10—H10C	0.9800
C3—H3A	0.9500	C11—H11A	0.9800
C4—C5	1.391 (2)	C11—H11B	0.9800
C4—H4A	0.9500	C11—H11C	0.9800
C5—C6	1.381 (2)	C12—H12A	0.9800
C6—C7	1.391 (2)	C12—H12B	0.9800
C6—H6A	0.9500	C12—H12C	0.9800
C5—O2—C8	116.59 (12)	O2—C8—H8C	109.5
C1—N1—C2	126.08 (11)	H8A—C8—H8C	109.5
C1—N1—H1A	117.0	H8B—C8—H8C	109.5
C2—N1—H1A	117.0	C11—C9—C10	108.76 (12)
O1—C1—N1	122.16 (13)	C11—C9—C12	109.69 (13)
O1—C1—C9	122.60 (12)	C10—C9—C12	110.42 (12)
N1—C1—C9	115.24 (11)	C11—C9—C1	108.99 (11)
C7—C2—C3	119.32 (13)	C10—C9—C1	109.84 (12)
C7—C2—N1	117.92 (12)	C12—C9—C1	109.12 (11)
C3—C2—N1	122.71 (12)	C9—C10—H10A	109.5
C4—C3—C2	119.79 (13)	C9—C10—H10B	109.5
C4—C3—H3A	120.1	H10A—C10—H10B	109.5
C2—C3—H3A	120.1	C9—C10—H10C	109.5
C3—C4—C5	120.70 (13)	H10A—C10—H10C	109.5
C3—C4—H4A	119.6	H10B—C10—H10C	109.5
C5—C4—H4A	119.6	C9—C11—H11A	109.5
O2—C5—C6	124.62 (13)	C9—C11—H11B	109.5
O2—C5—C4	115.58 (13)	H11A—C11—H11B	109.5
C6—C5—C4	119.80 (13)	C9—C11—H11C	109.5
C5—C6—C7	119.50 (13)	H11A—C11—H11C	109.5
C5—C6—H6A	120.3	H11B—C11—H11C	109.5
C7—C6—H6A	120.3	C9—C12—H12A	109.5
C2—C7—C6	120.88 (13)	C9—C12—H12B	109.5
C2—C7—H7A	119.6	H12A—C12—H12B	109.5
C6—C7—H7A	119.6	C9—C12—H12C	109.5
O2—C8—H8A	109.5	H12A—C12—H12C	109.5
O2—C8—H8B	109.5	H12B—C12—H12C	109.5
H8A—C8—H8B	109.5
C2—N1—C1—O1	−2.7 (2)	O2—C5—C6—C7	−178.91 (13)
C2—N1—C1—C9	176.75 (12)	C4—C5—C6—C7	1.2 (2)
C1—N1—C2—C7	−145.49 (14)	C3—C2—C7—C6	−0.3 (2)
C1—N1—C2—C3	37.0 (2)	N1—C2—C7—C6	−177.94 (13)
C7—C2—C3—C4	0.7 (2)	C5—C6—C7—C2	−0.6 (2)
N1—C2—C3—C4	178.23 (13)	O1—C1—C9—C11	−5.65 (19)
C2—C3—C4—C5	−0.2 (2)	N1—C1—C9—C11	174.89 (13)
C8—O2—C5—C6	−2.7 (2)	O1—C1—C9—C10	−124.71 (14)
C8—O2—C5—C4	177.17 (13)	N1—C1—C9—C10	55.83 (16)
C3—C4—C5—O2	179.31 (13)	O1—C1—C9—C12	114.12 (15)
C3—C4—C5—C6	−0.8 (2)	N1—C1—C9—C12	−65.34 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.88	2.09	2.9382 (15)	160
C3—H3A···O1	0.95	2.45	2.9063 (17)	109

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.88	2.09	2.9382 (15)	160
C3—H3A⋯O1	0.95	2.45	2.9063 (17)	109

Symmetry code: (i) .