2-(Prop-2-enyloxy)benzamide

Bugenhagen, B.; Al Jasem, Y.; Barkhad, F.; Hindawi, B. al; Thiemann, T.

doi:10.1107/S1600536812042250

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3169-o3170

doi:10.1107/S1600536812042250

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2-(Prop-2-enyloxy)benzamide

Bernhard Bugenhagen,^a Yosef Al Jasem,^b Farah Barkhad,^c Bassam al Hindawi ^d and Thies Thiemann ^d ^*

^aInstitute of Inorganic Chemistry, University of Hamburg, Hamburg, Germany, ^bDepartment of Chemical Engineering, UAE University, AL Ain, Abu Dhabi, United Arab Emirates, ^cDepartment of Petroleum Engineering, UAE University, AL Ain, Abu Dhabi, United Arab Emirates, and ^dDepartment of Chemistry, UAE University, AL Ain, Abu Dhabi, United Arab Emirates
^*Correspondence e-mail: thies@uaeu.ac.ae

(Received 22 September 2012; accepted 9 October 2012; online 20 October 2012)

In the title molecule, C₁₀H₁₁NO₂, the benzene ring forms dihedral angles of 33.15 (2) and 6.20 (2)° with the mean planes of the amide and propenoxy groups, respectively. The amide –NH₂ group is oriented toward the propenoxy substituent and forms a weak intramolecular N—H⋯O hydrogen bond to the propenoxy O atom. The conformation of the propenoxy group at the Csp²—Csp³ and Csp³—O bonds is synperiplanar and antiperiplanar, respectively. In the crystal, N—H⋯O hydrogen bonds involving the amide groups generate C(4) and R²₃(7) motifs that organize the molecules into tapes along the a-axis direction. There are C—H⋯π interactions between the propenoxy –CH₂ group and the aromatic system of neighboring molecules within the tape. The mean planes of the aromatic ring and the propenoxy group belonging to molecules 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_r = 177.20
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.087
S = 1.03
1079 reflections
126 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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⋯Cgⁱⁱ	0.99	2.68	3.461 (2)	137
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) x+1, y, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042250/gk2521sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812042250/gk2521Isup3.cml

checkCIF report

Comment top

In 2-propenoxybenzamide (2-allyloxybenzamide) (Figure 1), the O1—C7—C1—C6 torsion angle characterizing the twist of the benzene ring relative to the amide group is -30.3 (2)° and the corresponding C8—O2—C2—C3 torsion angle for the propoxy group is 5.9 (2)°. There is an intramolecular N1—H1B···O2 bond within each molecule (Table 1). When compared to the structurally comparable 2-propoxybenzamide (Al Jasem et al., 2012), the torsion angle O1—C7—C1—C6 is much larger in the title compound. The amide groups generate C(4) and R²₃(7) hydrogen-bond motifs that organize the molecules into tapes along the a axis. The title compound exhibits a C10—H10A···O2 and a C8—H8··· π (Table 1) close contact, absent in 2-propoxybenzamide (Figure 2). The C4—H4···O1 intermolecular interaction in 2-propenoxybenzamide links the neighboring tapes of molecules along the a axis with each other (Figure 3). However, in 2-propoxybenzamide, where also a C–H···O intermolecular interaction is found, the interaction proceeds from the carbon ortho to the propoxy group, while in the present case, it proceeds from the carbon meta to the propenoxy group. As a result of more close intermolecular contacts in 2-propenoxybenzamide as compared to 2-propoxybenzamide, the difference in the packing between the two compounds is large. The main difference is that while in the 2-propoxybenzamide molecules are arranged into pairs by close contacts, where the pairs in one layer are not associated through close contacts, in the title compound all neighboring molecules form close contacts to each other. Nevertheless, both compounds exhibit particular molecular tapes, each compound with two different directions of tape propagation. In the title compound, the average plane (0 1 - 1) of a tape propagation has an angle of 68.78 (2)° with the corresponding plane (0 1 1) of the neighboring tape propagation. Due to the large dihedral angle between the benzene ring and the amide group in 2-propenoxybenzamide, the average plane (-1 2 2) of the benzene ring and the propenoxy group of a molecule in one stack makes an angle of 83.16 (2)° with the corresponding plane (1 2 2) of a molecule in the opposing motif within one tape.

Related literature top

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 top

To powdered KOH (1.12 g, 20.0 mmol) in DMSO (18 ml) was added salicylamide (2.74 g, 20.0 mmol), and the resulting mixture was stirred for 10 min. at rt. Thereafter, n-propenyl bromide (4.2 g, mmol, 34.7 mmol) was added dropwise. The solution was stirred for 12 h at rt. Then, it was poured into water (200 ml) and extracted with chloroform (3 x 75 ml). The organic phase was dried over anhydrous MgSO₄, concentrated in vacuo, and the residue was subjected to column chromatography on silica gel (CHCl₃/M^tBE/hexane v/v/v 1:1:1) to give 2-propenoxybenzamide (2.76 g, 78%) as colorless crystals (m.p. 377 K). The crystal was grown from CHCl₃/ M^tBE/hexane (v/v/v 1:1:1).IR (KBr) ν_max 3406, 3190, 1631, 1600, 1399, 1243, 996, 921, 757, 643, 627 cm^-1; δ_H (400 MHz, CDCl₃) 4.67 (2H, d, ³J = 5.6 Hz), 5.36 (1H, dd, ³J = 10.4 Hz, ²J = 1.2 Hz), 5.44 (1H, dd, ³J = 17.2 Hz, ²J = 1.2 Hz), 6.03 – 6.13 (1H, dt, ³J = 17.2 Hz, ³J = 10.4 Hz, ³J = 5.6 Hz), 6.25 (1H, bs, NH), 6.96 (1H, d, ³J = 8.0 Hz), 7.07 (1H, dd, ³J = 8.0 Hz, ³J = 8.0 Hz), 7.80 (1H, bs, NH), 8.20 (1H, dd, ³J = 8.0 Hz, ⁴J = 1.6 Hz); δ_C (100.5 MHz, CDCl₃) 69.9, 112.6, 119.4, 121.1, 121.4, 132.0, 132.6, 133.3, 156.9, 167.2.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 (Sheldrick, 2008), PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the title compound molecule with the atom-numbering scheme and the intramolecular interaction within the molecule. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Intermolecular attractions between molecules of the title compound. [Symmetry codes: i: 1+x,y,z; ii: x,y,z; iii: -1/2 + x,1/2 - y,1 - z; iiii: 1/2 + x, 1/2 - y,1 - z]
	Fig. 3. The crystal packing diagram showing the C—H···O intermolecular interactions between tapes formed via amide group interactions.

2-(Prop-2-enyloxy)benzamide top

Crystal data top

C₁₀H₁₁NO₂	D_x = 1.294 Mg m⁻³
M_r = 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

Data collection top

Agilent SuperNova Atlas diffractometer	1079 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1016 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.025
Detector resolution: 10.4127 pixels mm^-1	θ_max = 72.7°, θ_min = 4.8°
ω scans	h = −6→3
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2012)	k = −12→13
T_min = 0.862, T_max = 0.951	l = −19→19
4718 measured reflections

Refinement top

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(F_o²) + (0.0609P)² + 0.1267P] where P = (F_o² + 2F_c²)/3
1079 reflections	(Δ/σ)_max < 0.001
126 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₀H₁₁NO₂	V = 909.48 (5) Å³
M_r = 177.20	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 5.08891 (17) Å	µ = 0.74 mm⁻¹
b = 11.2542 (4) Å	T = 100 K
c = 15.8802 (6) Å	0.30 × 0.09 × 0.08 mm

Data collection top

Agilent SuperNova Atlas diffractometer	1079 independent reflections
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2012)	1016 reflections with I > 2σ(I)
T_min = 0.862, T_max = 0.951	R_int = 0.025
4718 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.17 e Å⁻³
1079 reflections	Δρ_min = −0.18 e Å⁻³
126 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···Cgⁱⁱ	0.99	2.68	3.461 (2)	137

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁NO₂
M_r	177.20
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.08891 (17), 11.2542 (4), 15.8802 (6)
V (Å³)	909.48 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.30 × 0.09 × 0.08

Data collection
Diffractometer	Agilent SuperNova Atlas diffractometer
Absorption correction	Gaussian (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.862, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	4718, 1079, 1016
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.087, 1.03
No. of reflections	1079
No. of parameters	126
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) within OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009); Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···Cgⁱⁱ	0.99	2.68	3.461 (2)	137

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1, y, z.

References

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3169-o3170

doi:10.1107/S1600536812042250

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access