2-propoxybenzamide.

In the title mol-ecule, C(10)H(13)NO(2), the amide -NH(2) group is oriented toward the prop-oxy substituent and an intra-molecular N-H⋯O hydrogen bond is formed between the N-H group and the prop-oxy O atom. The benzene ring forms dihedral angles of 12.41 (2) and 3.26 (2)° with the amide and prop-oxy group mean planes, respectively. In the crystal, N-H⋯O hydrogen bonds order pairs of mol-ecules with their mol-ecular planes parallel, but at an offset of 0.73 (2) Å to each other. These pairs are ordered into two types of symmetry-related columns extended along the a axis with the mean plane of a pair in one column approximately parallel to (-122) and in the other to (-1-22). The two planes form dihedral angle of 84.40 (1)°. Overall, in a three-dimensional network, the hydrogen-bonded pairs of mol-ecules are either located in (-1-22) or (-122) layers. In one layer, each pair is involved in four C-H⋯O contacts, twice as a donor and twice as an acceptor. Additionally, there is a short C-H⋯C contact between a benzene C-H group and the amide π-system.

Related literature

For crystal structures of similar compounds, see: Pagola & Stephens (2009 ▶); Johnstone et al. (2010 ▶); Pertlik et al. (1990 ▶); Sasada et al. (1964 ▶). For uses of 2-alk­oxy­benzamides, see: van de Waterbeemd & Testa (1983 ▶); Kusunoki & Harada (1984 ▶). For the preparation of the title compound, see: Johnstone & Rose (1979 ▶).

Experimental

Crystal data

C10H13NO2

M = 179.21

Monoclinic,

a = 6.0303 (4) Å

b = 11.1196 (8) Å

c = 14.4140 (11) Å

β = 98.647 (6)°

V = 955.54 (12) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 100 K

0.16 × 0.10 × 0.08 mm

Data collection

Agilent SuperNova Atlas CCD diffractometer

Absorption correction: gaussian (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.810, T max = 1.000

2959 measured reflections

1676 independent reflections

1253 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.099

S = 1.03

1676 reflections

171 parameters

All H-atom parameters refined

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within OLEX2 (Dolomanov et al., 2009 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033326/gk2512sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033326/gk2512Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033326/gk2512Isup3.cml

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

C10H13NO2	Dx = 1.246 Mg m−3
Mr = 179.21	Melting point: 375 K
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
a = 6.0303 (4) Å	Cell parameters from 1037 reflections
b = 11.1196 (8) Å	θ = 3.1–66.6°
c = 14.4140 (11) Å	µ = 0.71 mm−1
β = 98.647 (6)°	T = 100 K
V = 955.54 (12) Å3	Block, colourless
Z = 4	0.16 × 0.10 × 0.08 mm
F(000) = 384

Agilent SuperNova Atlas CCD diffractometer	1676 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1253 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 10.4948 pixels mm-1	θmax = 66.7°, θmin = 5.1°
ω scans	h = −7→7
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2012)	k = −13→13
Tmin = 0.810, Tmax = 1.000	l = −17→15
2959 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)] = 0.040	All H-atom parameters refined
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0471P)2P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1676 reflections	Δρmax = 0.21 e Å−3
171 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0017 (4)

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	0.0319 (3)	0.24260 (15)	0.75450 (12)	0.0205 (4)
C10	0.7095 (3)	0.1142 (2)	0.96172 (14)	0.0319 (5)
C11	−0.0529 (3)	0.13553 (15)	0.59371 (12)	0.0210 (4)
C2	−0.1026 (3)	0.22312 (15)	0.66721 (12)	0.0206 (4)
C3	−0.3032 (3)	0.28748 (16)	0.64722 (13)	0.0246 (4)
C4	−0.3695 (3)	0.36968 (16)	0.70979 (13)	0.0274 (4)
C5	−0.2326 (3)	0.38823 (16)	0.79474 (13)	0.0263 (4)
C6	−0.0335 (3)	0.32574 (16)	0.81744 (13)	0.0240 (4)
C8	0.3557 (3)	0.18715 (17)	0.86630 (12)	0.0240 (4)
C9	0.5534 (3)	0.10404 (17)	0.86848 (13)	0.0245 (4)
H10A	0.766 (3)	0.198 (2)	0.9734 (15)	0.049 (7)*
H10B	0.839 (4)	0.054 (2)	0.9640 (14)	0.047 (6)*
H10C	0.634 (4)	0.092 (2)	1.0150 (17)	0.051 (7)*
H13A	0.256 (3)	0.1050 (18)	0.6538 (15)	0.035 (6)*
H13B	0.175 (3)	0.028 (2)	0.5573 (15)	0.043 (6)*
H3	−0.394 (3)	0.2739 (16)	0.5883 (13)	0.022 (5)*
H4	−0.515 (3)	0.4133 (18)	0.6958 (14)	0.040 (6)*
H5	−0.273 (3)	0.4440 (19)	0.8381 (15)	0.038 (6)*
H6	0.056 (3)	0.3387 (15)	0.8747 (13)	0.020 (5)*
H8A	0.408 (3)	0.2707 (16)	0.8776 (13)	0.019 (4)*
H8B	0.263 (3)	0.1645 (17)	0.9168 (15)	0.034 (5)*
H9A	0.499 (3)	0.0208 (18)	0.8581 (13)	0.031 (5)*
H9B	0.635 (3)	0.1262 (16)	0.8153 (14)	0.027 (5)*
N13	0.1514 (3)	0.08719 (15)	0.60043 (11)	0.0273 (4)
O12	−0.2027 (2)	0.10985 (11)	0.52757 (8)	0.0268 (3)
O7	0.22330 (19)	0.17526 (11)	0.77463 (8)	0.0236 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0192 (8)	0.0205 (9)	0.0215 (9)	−0.0012 (7)	0.0020 (7)	0.0020 (7)
C10	0.0287 (11)	0.0383 (12)	0.0259 (11)	0.0009 (10)	−0.0053 (8)	0.0023 (9)
C11	0.0259 (9)	0.0184 (9)	0.0181 (9)	−0.0040 (7)	0.0012 (7)	0.0020 (7)
C2	0.0230 (9)	0.0191 (9)	0.0197 (9)	−0.0042 (7)	0.0031 (7)	0.0015 (7)
C3	0.0250 (9)	0.0242 (10)	0.0232 (10)	−0.0015 (8)	−0.0014 (8)	0.0037 (7)
C4	0.0259 (10)	0.0260 (10)	0.0305 (11)	0.0034 (8)	0.0048 (8)	0.0037 (8)
C5	0.0302 (11)	0.0218 (10)	0.0272 (10)	0.0009 (8)	0.0057 (8)	−0.0030 (8)
C6	0.0279 (10)	0.0231 (9)	0.0207 (10)	−0.0030 (8)	0.0024 (8)	−0.0034 (8)
C8	0.0233 (10)	0.0301 (11)	0.0171 (9)	−0.0007 (8)	−0.0021 (7)	−0.0034 (8)
C9	0.0247 (10)	0.0268 (10)	0.0210 (10)	0.0005 (8)	0.0003 (7)	−0.0008 (8)
N13	0.0271 (9)	0.0319 (9)	0.0220 (9)	0.0020 (7)	0.0004 (7)	−0.0081 (7)
O12	0.0314 (7)	0.0257 (7)	0.0207 (7)	−0.0001 (6)	−0.0044 (5)	−0.0015 (5)
O7	0.0219 (6)	0.0295 (7)	0.0177 (7)	0.0040 (5)	−0.0025 (5)	−0.0043 (5)

C1—C2	1.407 (2)	C6—H6	0.927 (19)
C1—C6	1.393 (2)	C8—C9	1.505 (3)
C10—H10A	1.00 (2)	C8—H8A	0.987 (18)
C10—H10B	1.03 (2)	C8—H8B	1.01 (2)
C10—H10C	0.98 (2)	C9—C10	1.525 (3)
C2—C11	1.502 (2)	C9—H9A	0.99 (2)
C2—C3	1.398 (2)	N13—C11	1.334 (2)
C3—C4	1.385 (3)	N13—H13A	0.94 (2)
C3—H3	0.951 (18)	N13—H13B	0.93 (2)
C4—H4	0.996 (19)	O12—C11	1.244 (2)
C5—C4	1.386 (3)	O7—C1	1.370 (2)
C5—H5	0.94 (2)	O7—C8	1.444 (2)
C6—C5	1.383 (3)
C1—C6—H6	119.9 (11)	C8—C9—H9A	109.2 (11)
C1—C2—C11	125.52 (15)	C8—C9—C10	110.78 (16)
C1—O7—C8	118.44 (13)	C9—C10—H10C	111.9 (14)
C10—C9—H9B	110.3 (11)	C9—C10—H10B	110.3 (12)
C10—C9—H9A	110.5 (11)	C9—C10—H10A	111.6 (12)
C11—N13—H13B	117.9 (12)	C9—C8—H8B	110.7 (11)
C11—N13—H13A	118.3 (12)	C9—C8—H8A	110.0 (11)
C2—C3—H3	117.9 (11)	H10A—C10—H10C	106.8 (18)
C3—C4—H4	121.4 (12)	H10A—C10—H10B	111.4 (17)
C3—C4—C5	118.80 (17)	H10B—C10—H10C	104.6 (18)
C3—C2—C11	116.41 (15)	H13A—N13—H13B	123.0 (17)
C3—C2—C1	118.04 (16)	H8A—C8—H8B	108.2 (15)
C4—C5—H5	120.5 (12)	H9A—C9—H9B	107.8 (15)
C4—C3—H3	120.2 (11)	N13—C11—C2	119.34 (15)
C4—C3—C2	121.97 (17)	O12—C11—C2	119.37 (15)
C5—C6—H6	120.1 (11)	O12—C11—N13	121.30 (17)
C5—C4—H4	119.7 (12)	O7—C8—H8B	110.2 (11)
C5—C6—C1	120.01 (17)	O7—C8—H8A	110.9 (11)
C6—C5—H5	118.5 (12)	O7—C8—C9	106.87 (14)
C6—C5—C4	121.00 (18)	O7—C1—C6	122.48 (16)
C6—C1—C2	120.17 (16)	O7—C1—C2	117.33 (15)
C8—C9—H9B	108.2 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···O7	0.94 (2)	1.95 (2)	2.669 (2)	132.2 (15)
N13—H13B···O12i	0.93 (2)	1.98 (2)	2.911 (2)	173.5 (19)
C6—H6···O12ii	0.927 (19)	2.517 (18)	3.442 (2)	175.8 (14)
C5—H5···C11iii	0.94 (2)	2.63 (2)	3.528 (2)	160.5 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N13—H13A⋯O7	0.94 (2)	1.95 (2)	2.669 (2)	132.2 (15)
N13—H13B⋯O12i	0.93 (2)	1.98 (2)	2.911 (2)	173.5 (19)
C6—H6⋯O12ii	0.927 (19)	2.517 (18)	3.442 (2)	175.8 (14)
C5—H5⋯C11iii	0.94 (2)	2.63 (2)	3.528 (2)	160.5 (17)

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