N-Isopropyl-benzamide.

In the title compound, C(10)H(13)NO, the dihedral angle between the amide group and the phenyl ring is 30.0 (3)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link mol-ecules into one-dimensional chains along the a axis.

Related literature

For related literature, see: Clayden et al. (2006 ▶); Kopka et al. (2005 ▶); Smart (2001 ▶); Van Waarde et al. (2004 ▶); Stephenson, Wilson et al. (2008 ▶); Stephenson, van Oosten et al. (2008 ▶).

Experimental

Crystal data

C10H13NO

M = 163.21

Monoclinic,

a = 5.0093 (7) Å

b = 10.1250 (13) Å

c = 9.6714 (14) Å

β = 104.133 (7)°

V = 475.68 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 150 (1) K

0.14 × 0.13 × 0.08 mm

Data collection

Bruker Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing 1995 ▶) T min = 0.954, T max = 0.996

2462 measured reflections

887 independent reflections

621 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.148

S = 1.06

887 reflections

114 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012804/hb2729sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012804/hb2729Isup2.hkl

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

C10H13NO	F000 = 176
Mr = 163.21	Dx = 1.140 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2462 reflections
a = 5.0093 (7) Å	θ = 3.0–25.0º
b = 10.1250 (13) Å	µ = 0.07 mm−1
c = 9.6714 (14) Å	T = 150 (1) K
β = 104.133 (7)º	Block, colourless
V = 475.68 (11) Å3	0.14 × 0.13 × 0.08 mm
Z = 2

Bruker Nonius KappaCCD diffractometer	887 independent reflections
Radiation source: fine-focus sealed tube	621 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.061
Detector resolution: 9 pixels mm-1	θmax = 25.0º
T = 150(1) K	θmin = 3.0º
φ scans and ω scans with κ offsets	h = −5→5
Absorption correction: multi-scan(SORTAV; Blessing 1995)	k = −12→10
Tmin = 0.954, Tmax = 0.996	l = −11→11
2462 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0784P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
887 reflections	Δρmax = 0.18 e Å−3
114 parameters	Δρmin = −0.21 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.6751 (6)	0.1703 (3)	0.8045 (3)	0.0424 (8)
N1	0.2696 (8)	0.1717 (4)	0.8673 (4)	0.0411 (10)
H1N	0.103 (11)	0.188 (5)	0.839 (5)	0.049*
C1	0.3226 (9)	0.3127 (4)	0.6749 (5)	0.0350 (11)
C2	0.4247 (10)	0.3165 (5)	0.5544 (5)	0.0452 (13)
H2A	0.5601	0.2545	0.5432	0.054*
C3	0.3286 (11)	0.4116 (6)	0.4493 (5)	0.0535 (14)
H3A	0.3957	0.4126	0.3655	0.064*
C4	0.1377 (10)	0.5034 (5)	0.4666 (6)	0.0516 (14)
H4A	0.0734	0.5682	0.3951	0.062*
C5	0.0391 (11)	0.5014 (5)	0.5883 (6)	0.0523 (14)
H5A	−0.0912	0.5656	0.6010	0.063*
C6	0.1296 (9)	0.4064 (5)	0.6915 (5)	0.0451 (13)
H6A	0.0597	0.4051	0.7744	0.054*
C7	0.4356 (8)	0.2117 (4)	0.7864 (4)	0.0362 (12)
C8	0.3461 (10)	0.0743 (5)	0.9808 (5)	0.0474 (13)
H8A	0.5489	0.0586	0.9996	0.057*
C9	0.1984 (13)	−0.0561 (5)	0.9351 (6)	0.0648 (16)
H9A	0.2525	−0.0903	0.8512	0.097*
H9B	−0.0011	−0.0417	0.9116	0.097*
H9C	0.2488	−0.1200	1.0132	0.097*
C10	0.2833 (11)	0.1271 (6)	1.1160 (5)	0.0556 (15)
H10A	0.3743	0.2126	1.1400	0.083*
H10B	0.3510	0.0647	1.1942	0.083*
H10C	0.0839	0.1380	1.1013	0.083*

	U11	U22	U33	U12	U13	U23
O1	0.0319 (17)	0.0442 (18)	0.0515 (17)	0.0024 (15)	0.0112 (13)	0.0032 (16)
N1	0.0326 (19)	0.046 (2)	0.047 (2)	0.003 (2)	0.0149 (18)	0.012 (2)
C1	0.033 (2)	0.035 (2)	0.039 (3)	−0.006 (2)	0.012 (2)	0.000 (2)
C2	0.049 (3)	0.044 (3)	0.046 (3)	0.001 (2)	0.019 (2)	0.003 (2)
C3	0.057 (3)	0.061 (3)	0.046 (3)	−0.003 (3)	0.019 (3)	0.012 (3)
C4	0.049 (3)	0.051 (3)	0.050 (3)	−0.002 (3)	0.004 (3)	0.020 (3)
C5	0.053 (3)	0.040 (3)	0.066 (3)	0.007 (3)	0.017 (3)	0.013 (3)
C6	0.046 (3)	0.042 (3)	0.051 (3)	0.003 (2)	0.017 (2)	0.005 (3)
C7	0.035 (3)	0.034 (3)	0.037 (2)	−0.004 (2)	0.005 (2)	−0.008 (2)
C8	0.041 (3)	0.054 (3)	0.048 (3)	0.012 (3)	0.012 (2)	0.017 (3)
C9	0.085 (4)	0.043 (3)	0.064 (3)	0.010 (3)	0.014 (3)	0.012 (3)
C10	0.062 (3)	0.062 (4)	0.044 (3)	−0.001 (3)	0.015 (2)	0.012 (3)

O1—C7	1.242 (5)	C5—C6	1.380 (7)
N1—C7	1.337 (6)	C5—H5A	0.9500
N1—C8	1.455 (6)	C6—H6A	0.9500
N1—H1N	0.83 (5)	C8—C10	1.516 (7)
C1—C2	1.383 (6)	C8—C9	1.525 (8)
C1—C6	1.392 (6)	C8—H8A	1.0000
C1—C7	1.493 (6)	C9—H9A	0.9800
C2—C3	1.398 (8)	C9—H9B	0.9800
C2—H2A	0.9500	C9—H9C	0.9800
C3—C4	1.373 (7)	C10—H10A	0.9800
C3—H3A	0.9500	C10—H10B	0.9800
C4—C5	1.384 (7)	C10—H10C	0.9800
C4—H4A	0.9500
C7—N1—C8	124.0 (4)	O1—C7—N1	122.2 (4)
C7—N1—H1N	118 (4)	O1—C7—C1	121.0 (4)
C8—N1—H1N	117 (4)	N1—C7—C1	116.7 (4)
C2—C1—C6	119.2 (4)	N1—C8—C10	109.9 (4)
C2—C1—C7	118.3 (4)	N1—C8—C9	110.4 (4)
C6—C1—C7	122.4 (4)	C10—C8—C9	111.5 (4)
C1—C2—C3	120.0 (5)	N1—C8—H8A	108.3
C1—C2—H2A	120.0	C10—C8—H8A	108.3
C3—C2—H2A	120.0	C9—C8—H8A	108.3
C4—C3—C2	120.3 (5)	C8—C9—H9A	109.5
C4—C3—H3A	119.9	C8—C9—H9B	109.5
C2—C3—H3A	119.9	H9A—C9—H9B	109.5
C3—C4—C5	119.8 (5)	C8—C9—H9C	109.5
C3—C4—H4A	120.1	H9A—C9—H9C	109.5
C5—C4—H4A	120.1	H9B—C9—H9C	109.5
C6—C5—C4	120.2 (5)	C8—C10—H10A	109.5
C6—C5—H5A	119.9	C8—C10—H10B	109.5
C4—C5—H5A	119.9	H10A—C10—H10B	109.5
C5—C6—C1	120.5 (4)	C8—C10—H10C	109.5
C5—C6—H6A	119.8	H10A—C10—H10C	109.5
C1—C6—H6A	119.8	H10B—C10—H10C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (5)	2.10 (5)	2.890 (5)	160 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (5)	2.10 (5)	2.890 (5)	160 (5)

Symmetry code: (i) .