2-(Prop-2-enyloxy)benzamide.

In the title mol-ecule, C(10)H(11)NO(2), the benzene ring forms dihedral angles of 33.15 (2) and 6.20 (2)° with the mean planes of the amide and propen-oxy groups, respectively. The amide -NH(2) group is oriented toward the propen-oxy substituent and forms a weak intra-molecular N-H⋯O hydrogen bond to the propen-oxy O atom. The conformation of the propen-oxy group at the Csp(2)-Csp(3) and Csp(3)-O bonds is synperiplanar and anti-periplanar, respectively. In the crystal, N-H⋯O hydrogen bonds involving the amide groups generate C(4) and R(2) (3)(7) motifs that organize the mol-ecules into tapes along the a-axis direction. There are C-H⋯π inter-actions between the propen-oxy -CH(2) group and the aromatic system of neighboring mol-ecules within the tape. The mean planes of the aromatic ring and the propen-oxy group belonging to mol-ecules located on opposite sites of the tape form an angle of 83.16 (2)°.

Related literature

For crystal structures of similar compounds, see: Al Jasem et al. (2012 ▶); Pagola & Stephens (2009 ▶); Johnstone et al. (2010 ▶); Pertlik (1990) ▶; Sasada et al. (1964 ▶). For uses of 2-alk­oxy­benzamides, see: van de Waterbeemd & Testa (1983 ▶); Kusunoki & Harada (1984 ▶). For the preparation of a related 2-alk­oxy­benzamide, see: Al Jasem et al. (2012 ▶).

Experimental

Crystal data

C10H11NO2

M = 177.20

Orthorhombic,

a = 5.08891 (17) Å

b = 11.2542 (4) Å

c = 15.8802 (6) Å

V = 909.48 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.74 mm−1

T = 100 K

0.30 × 0.09 × 0.08 mm

Data collection

Agilent SuperNova Atlas diffractometer

Absorption correction: Gaussian (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.862, T max = 0.951

4718 measured reflections

1079 independent reflections

1016 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.087

S = 1.03

1079 reflections

126 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 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 ▶); Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042250/gk2521sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042250/gk2521Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042250/gk2521Isup3.cml

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

C10H11NO2	Dx = 1.294 Mg m−3
Mr = 177.20	Melting point: 377 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
a = 5.08891 (17) Å	Cell parameters from 2824 reflections
b = 11.2542 (4) Å	θ = 3.9–72.6°
c = 15.8802 (6) Å	µ = 0.74 mm−1
V = 909.48 (5) Å3	T = 100 K
Z = 4	Needle, colourless
F(000) = 376	0.30 × 0.09 × 0.08 mm

Agilent SuperNova Atlas diffractometer	1079 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1016 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.4127 pixels mm-1	θmax = 72.7°, θmin = 4.8°
ω scans	h = −6→3
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2012)	k = −12→13
Tmin = 0.862, Tmax = 0.951	l = −19→19
4718 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.1267P] where P = (Fo2 + 2Fc2)/3
1079 reflections	(Δ/σ)max < 0.001
126 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. Numerical absorption correction based on gaussian integration over a multifaceted crystal model

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	0.2397 (4)	0.43317 (15)	0.31664 (10)	0.0181 (4)
C10	0.9389 (4)	0.59453 (19)	0.49447 (12)	0.0289 (4)
C2	0.4129 (3)	0.52840 (15)	0.30222 (11)	0.0188 (4)
C3	0.3949 (4)	0.59415 (17)	0.22777 (12)	0.0238 (4)
C4	0.2055 (4)	0.56545 (18)	0.16826 (11)	0.0262 (4)
C5	0.0314 (4)	0.47271 (17)	0.18190 (11)	0.0244 (4)
C6	0.0478 (4)	0.40808 (16)	0.25658 (11)	0.0208 (4)
C7	0.2401 (3)	0.35748 (15)	0.39466 (11)	0.0181 (4)
C8	0.7520 (4)	0.65550 (15)	0.35506 (12)	0.0231 (4)
C9	0.9255 (4)	0.66806 (17)	0.43007 (12)	0.0268 (4)
H10A	0.8310	0.5257	0.4958	0.035*
H10B	1.0565	0.6104	0.5396	0.035*
H1A	0.484 (5)	0.288 (2)	0.4772 (13)	0.028 (6)*
H1B	0.623 (5)	0.358 (2)	0.4113 (16)	0.040 (7)*
H3	0.5120	0.6584	0.2179	0.029*
H4	0.1950	0.6099	0.1175	0.031*
H5	−0.0975	0.4534	0.1408	0.029*
H6	−0.0741	0.3458	0.2667	0.025*
H8A	0.6389	0.7267	0.3496	0.028*
H8B	0.8604	0.6488	0.3035	0.028*
H9	1.0373	0.7356	0.4316	0.032*
N1	0.4686 (3)	0.33298 (15)	0.43084 (10)	0.0218 (3)
O1	0.0291 (2)	0.31561 (12)	0.42082 (8)	0.0224 (3)
O2	0.5922 (2)	0.55184 (11)	0.36411 (7)	0.0217 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0162 (8)	0.0185 (8)	0.0197 (8)	0.0023 (7)	0.0017 (7)	−0.0006 (6)
C2	0.0149 (8)	0.0194 (8)	0.0221 (8)	0.0015 (7)	0.0019 (7)	0.0001 (7)
C3	0.0226 (9)	0.0230 (8)	0.0259 (9)	0.0029 (8)	0.0040 (7)	0.0037 (7)
C4	0.0309 (10)	0.0275 (10)	0.0202 (8)	0.0076 (9)	0.0018 (8)	0.0044 (7)
C5	0.0245 (9)	0.0280 (9)	0.0207 (8)	0.0049 (8)	−0.0038 (7)	−0.0032 (7)
C6	0.0180 (8)	0.0205 (8)	0.0239 (8)	0.0014 (7)	−0.0004 (8)	−0.0028 (7)
C7	0.0159 (8)	0.0173 (8)	0.0210 (8)	0.0005 (7)	0.0006 (7)	−0.0019 (6)
C8	0.0213 (9)	0.0177 (8)	0.0304 (9)	−0.0038 (8)	0.0011 (8)	0.0008 (7)
C9	0.0211 (9)	0.0240 (9)	0.0353 (10)	−0.0040 (8)	0.0013 (8)	−0.0066 (8)
C10	0.0270 (10)	0.0315 (9)	0.0283 (9)	0.0002 (9)	−0.0022 (9)	−0.0070 (8)
N1	0.0153 (7)	0.0260 (8)	0.0240 (7)	−0.0007 (6)	0.0000 (6)	0.0071 (6)
O1	0.0153 (6)	0.0243 (6)	0.0276 (6)	−0.0017 (5)	0.0006 (5)	0.0053 (5)
O2	0.0195 (6)	0.0210 (6)	0.0246 (6)	−0.0045 (5)	−0.0015 (5)	0.0033 (5)

C1—C2	1.406 (2)	C7—N1	1.326 (2)
C1—C6	1.394 (2)	C7—O1	1.244 (2)
C1—C7	1.504 (2)	C8—H8A	0.9900
C2—C3	1.398 (2)	C8—H8B	0.9900
C2—O2	1.367 (2)	C8—C9	1.489 (3)
C3—H3	0.9500	C8—O2	1.429 (2)
C3—C4	1.388 (3)	C9—H9	0.9500
C4—H4	0.9500	C9—C10	1.317 (3)
C4—C5	1.386 (3)	C10—H10A	0.9500
C5—H5	0.9500	C10—H10B	0.9500
C5—C6	1.394 (2)	N1—H1A	0.90 (2)
C6—H6	0.9500	N1—H1B	0.89 (3)
C1—C6—H6	119.4	C7—N1—H1A	123.2 (16)
C10—C9—C8	126.30 (18)	C7—N1—H1B	124.0 (16)
C10—C9—H9	116.9	C8—C9—H9	116.9
C2—C1—C7	124.39 (15)	C9—C10—H10A	120.0
C2—C3—H3	120.1	C9—C10—H10B	120.0
C2—O2—C8	117.72 (13)	C9—C8—H8A	109.8
C3—C2—C1	120.00 (16)	C9—C8—H8B	109.8
C3—C4—H4	119.6	H10A—C10—H10B	120.0
C4—C3—C2	119.89 (18)	H1A—N1—H1B	113 (2)
C4—C3—H3	120.1	H8A—C8—H8B	108.2
C4—C5—H5	120.4	N1—C7—C1	118.44 (16)
C4—C5—C6	119.20 (17)	O1—C7—C1	119.23 (15)
C5—C4—C3	120.84 (17)	O1—C7—N1	122.25 (16)
C5—C4—H4	119.6	O2—C2—C1	116.64 (14)
C5—C6—C1	121.22 (17)	O2—C2—C3	123.36 (16)
C5—C6—H6	119.4	O2—C8—H8A	109.8
C6—C1—C2	118.81 (15)	O2—C8—H8B	109.8
C6—C1—C7	116.76 (16)	O2—C8—C9	109.54 (15)
C6—C5—H5	120.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.90 (2)	2.01 (2)	2.905 (2)	178 (17)
N1—H1B···O1ii	0.89 (3)	2.12 (3)	2.863 (2)	140 (2)
N1—H1B···O2	0.89 (3)	2.31 (2)	2.754 (2)	110.8 (18)
C8—H8B···Cgii	0.99	2.68	3.461 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.90 (2)	2.01 (2)	2.905 (2)	178 (17)
N1—H1B⋯O1ii	0.89 (3)	2.12 (3)	2.863 (2)	140 (2)
N1—H1B⋯O2	0.89 (3)	2.31 (2)	2.754 (2)	110.8 (18)
C8—H8B⋯Cg ii	0.99	2.68	3.461 (2)	137

Symmetry codes: (i) ; (ii) .