N-[4-(2-Propyn-1-yl-oxy)phen-yl]acetamide.

The title compound, C(11)H(11)NO(2), was synthesized by chemoselective N-acetyl-ation of 4-amino-phenol followed by reaction with propargyl bromide in the presence of K(2)CO(3). the acetamide and propyn-1-yloxy substituents form dihedral angles of 18.31 (6) and 7.01 (10)°, respectively, with the benzene ring. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into chains along [010]. C-H⋯O and C-H⋯π inter-actions also occur.

Related literature

For background to the development of hybrid drug candidates against tuberculosis, malaria and cancer, see: Morphy et al. (2004 ▶). For details of the synthesis of the title compound, see: Hoogendoorn et al. (2011 ▶); Reppe (1955 ▶).

Experimental

Crystal data

C11H11NO2

M = 189.21

Monoclinic,

a = 13.973 (2) Å

b = 9.1794 (13) Å

c = 7.5105 (11) Å

β = 99.441 (4)°

V = 950.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.3 × 0.26 × 0.23 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.969, T max = 0.981

6753 measured reflections

2388 independent reflections

2103 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.04

2388 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041207/nc2291sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041207/nc2291Isup2.hkl

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

C11H11NO2	F(000) = 400
Mr = 189.21	Dx = 1.323 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3099 reflections
a = 13.973 (2) Å	θ = 2.7–28.4°
b = 9.1794 (13) Å	µ = 0.09 mm−1
c = 7.5105 (11) Å	T = 100 K
β = 99.441 (4)°	Block, pale yellow
V = 950.3 (2) Å3	0.3 × 0.26 × 0.23 mm
Z = 4

Bruker APEX DUO 4K CCD diffractometer	2388 independent reflections
Graphite monochromator	2103 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1	Rint = 0.018
φ and ω scans	θmax = 28.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→18
Tmin = 0.969, Tmax = 0.981	k = −12→11
6753 measured reflections	l = −10→10

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.3049P] where P = (Fo2 + 2Fc2)/3
2388 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 20 s/frame. A total of 735 frames were collected with a frame width of 0.5° covering up to θ = 28.47° with 99.3% completeness accomplished. Analytical data: mp: 110 - 111 °C (Lit. 109 - 111 °C; Reppe, 1955); 1H NMR (CDCl3, 400 MHz): d 7.57 (s, 1H), 7.38 (d, J = 8.4 Hz, 2H), 6.89 (d, J = 8.8 Hz, 2H), 4.63 (s, 2H), 2.49 (s, 1H), 2.12 (s, 3H); 13C NMR (CDCl3,400 MHz): d 168.4, 154.3, 131.9, 121.8, 115.3, 78.5, 75.5, 56.1, 24.4.

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
O1	0.44065 (5)	0.09706 (8)	0.16260 (10)	0.01982 (18)
O2	−0.00853 (5)	0.27539 (8)	−0.14889 (10)	0.02019 (18)
N1	0.05791 (6)	0.05346 (9)	−0.18684 (12)	0.01555 (19)
C1	0.63468 (9)	0.09825 (14)	0.49415 (17)	0.0288 (3)
H1A	0.6943	0.0641	0.5601	0.035*
C2	0.56036 (8)	0.14084 (12)	0.41199 (15)	0.0215 (2)
C3	0.46720 (8)	0.19131 (12)	0.31532 (14)	0.0202 (2)
H3A	0.4174	0.1874	0.395	0.024*
H3B	0.4726	0.2931	0.2748	0.024*
C4	0.34482 (7)	0.09626 (11)	0.08432 (13)	0.0160 (2)
C5	0.27561 (7)	0.19574 (11)	0.12113 (13)	0.0165 (2)
H5	0.2934	0.2712	0.2068	0.02*
C6	0.17996 (7)	0.18471 (11)	0.03218 (13)	0.0160 (2)
H6	0.1327	0.2524	0.0582	0.019*
C7	0.15352 (7)	0.07514 (10)	−0.09429 (13)	0.0143 (2)
C8	−0.01572 (7)	0.15035 (11)	−0.20997 (13)	0.0156 (2)
C9	−0.10956 (7)	0.09587 (11)	−0.31599 (14)	0.0192 (2)
H9A	−0.1605	0.1005	−0.2407	0.029*
H9B	−0.1014	−0.0051	−0.353	0.029*
H9C	−0.1279	0.1568	−0.4233	0.029*
C10	0.22426 (7)	−0.02335 (11)	−0.13094 (14)	0.0169 (2)
H10	0.207	−0.0982	−0.2177	0.02*
C11	0.31883 (7)	−0.01321 (11)	−0.04271 (14)	0.0175 (2)
H11	0.3661	−0.0809	−0.0687	0.021*
H1	0.0464 (10)	−0.0325 (16)	−0.2373 (18)	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0138 (4)	0.0255 (4)	0.0184 (4)	0.0032 (3)	−0.0024 (3)	−0.0051 (3)
O2	0.0192 (4)	0.0149 (3)	0.0248 (4)	0.0026 (3)	−0.0015 (3)	−0.0008 (3)
N1	0.0139 (4)	0.0124 (4)	0.0192 (4)	−0.0008 (3)	−0.0006 (3)	−0.0010 (3)
C1	0.0196 (6)	0.0338 (6)	0.0302 (6)	−0.0025 (5)	−0.0039 (5)	0.0011 (5)
C2	0.0192 (5)	0.0236 (5)	0.0211 (5)	−0.0036 (4)	0.0014 (4)	−0.0027 (4)
C3	0.0190 (5)	0.0213 (5)	0.0189 (5)	0.0002 (4)	−0.0010 (4)	−0.0032 (4)
C4	0.0136 (5)	0.0190 (5)	0.0148 (4)	0.0012 (4)	0.0000 (4)	0.0021 (3)
C5	0.0168 (5)	0.0165 (4)	0.0154 (4)	0.0005 (4)	0.0003 (4)	−0.0022 (3)
C6	0.0162 (5)	0.0150 (4)	0.0168 (5)	0.0020 (4)	0.0022 (4)	0.0000 (3)
C7	0.0140 (5)	0.0138 (4)	0.0146 (4)	−0.0001 (3)	0.0007 (3)	0.0027 (3)
C8	0.0146 (5)	0.0156 (4)	0.0162 (4)	−0.0001 (3)	0.0014 (4)	0.0032 (3)
C9	0.0147 (5)	0.0184 (5)	0.0234 (5)	−0.0007 (4)	−0.0006 (4)	0.0018 (4)
C10	0.0181 (5)	0.0139 (4)	0.0179 (5)	0.0004 (4)	0.0006 (4)	−0.0017 (3)
C11	0.0171 (5)	0.0159 (4)	0.0191 (5)	0.0040 (4)	0.0016 (4)	−0.0002 (4)

O1—C4	1.3713 (12)	C5—C6	1.3965 (14)
O1—C3	1.4360 (12)	C5—H5	0.95
O2—C8	1.2340 (12)	C6—C7	1.3911 (13)
N1—C8	1.3495 (13)	C6—H6	0.95
N1—C7	1.4152 (13)	C7—C10	1.3999 (14)
N1—H1	0.879 (14)	C8—C9	1.5036 (14)
C1—C2	1.1840 (17)	C9—H9A	0.98
C1—H1A	0.95	C9—H9B	0.98
C2—C3	1.4582 (15)	C9—H9C	0.98
C3—H3A	0.99	C10—C11	1.3807 (14)
C3—H3B	0.99	C10—H10	0.95
C4—C5	1.3903 (14)	C11—H11	0.95
C4—C11	1.3922 (14)
C4—O1—C3	116.86 (8)	C5—C6—H6	119.8
C8—N1—C7	127.50 (9)	C6—C7—C10	118.96 (9)
C8—N1—H1	117.0 (9)	C6—C7—N1	124.10 (9)
C7—N1—H1	115.5 (9)	C10—C7—N1	116.92 (9)
C2—C1—H1A	180	O2—C8—N1	123.46 (9)
C1—C2—C3	178.14 (12)	O2—C8—C9	121.13 (9)
O1—C3—C2	107.39 (8)	N1—C8—C9	115.41 (9)
O1—C3—H3A	110.2	C8—C9—H9A	109.5
C2—C3—H3A	110.2	C8—C9—H9B	109.5
O1—C3—H3B	110.2	H9A—C9—H9B	109.5
C2—C3—H3B	110.2	C8—C9—H9C	109.5
H3A—C3—H3B	108.5	H9A—C9—H9C	109.5
O1—C4—C5	124.98 (9)	H9B—C9—H9C	109.5
O1—C4—C11	115.11 (9)	C11—C10—C7	120.87 (9)
C5—C4—C11	119.90 (9)	C11—C10—H10	119.6
C4—C5—C6	119.98 (9)	C7—C10—H10	119.6
C4—C5—H5	120	C10—C11—C4	119.94 (9)
C6—C5—H5	120	C10—C11—H11	120
C7—C6—C5	120.34 (9)	C4—C11—H11	120
C7—C6—H6	119.8
C4—O1—C3—C2	161.20 (9)	C8—N1—C7—C10	−162.01 (10)
C3—O1—C4—C5	11.37 (14)	C7—N1—C8—O2	−0.68 (16)
C3—O1—C4—C11	−169.65 (9)	C7—N1—C8—C9	179.68 (9)
O1—C4—C5—C6	179.65 (9)	C6—C7—C10—C11	0.40 (15)
C11—C4—C5—C6	0.72 (15)	N1—C7—C10—C11	−177.99 (9)
C4—C5—C6—C7	−0.44 (15)	C7—C10—C11—C4	−0.13 (15)
C5—C6—C7—C10	−0.12 (14)	O1—C4—C11—C10	−179.47 (9)
C5—C6—C7—N1	178.15 (9)	C5—C4—C11—C10	−0.44 (15)
C8—N1—C7—C6	19.69 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.879 (14)	1.993 (14)	2.8695 (11)	175.2 (13)
C6—H6···O2	0.95	2.31	2.8816 (13)	118
C9—H9B···O2i	0.98	2.53	3.4043 (14)	148
C5—H5···Cg1ii	0.95	2.69	3.5171 (12)	146
C9—H9A···Cg1iii	0.98	2.94	3.7373 (12)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.879 (14)	1.993 (14)	2.8695 (11)	175.2 (13)
C9—H9B⋯O2i	0.98	2.53	3.4043 (14)	148
C5—H5⋯Cg1ii	0.95	2.69	3.5171 (12)	146
C9—H9A⋯Cg1iii	0.98	2.94	3.7373 (12)	139

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