N-Benzyl-2-propynamide.

Pale-yellow crystals of the title compound, C(10)H(9)NO, have been obtained by the reaction of benzyl-amine and methyl propiolate. Weak inter-molecular hydrogen bonding is observed between acetyl-enic H and carbonyl O atoms. The crystal packing is stabilized by these C-H⋯O and by N-H⋯O inter-molecular hydrogen-bonding inter-actions.

Related literature

The title compound was synthesized using a similar synthetic method to that described by Williamson et al. (1994 ▶). For the synthesis of triazole derivatives, see: Katritzky & Singh (2002 ▶). For the structure of the methyl analogue of the title compound, see: Leiserowitz & Tuval (1978 ▶). For the program ROTAX, used to investigate possible pseudo-merohedral twinning, see: Parsons & Gould (2003 ▶).

Experimental

Crystal data

C10H9NO

M = 159.18

Monoclinic,

a = 9.495 (2) Å

b = 10.703 (2) Å

c = 8.9120 (19) Å

β = 101.637 (3)°

V = 887.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.57 × 0.30 × 0.30 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.848, T max = 1.000 (expected range = 0.828–0.977)

5825 measured reflections

1550 independent reflections

1510 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.221

S = 1.26

1550 reflections

113 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901455X/zl2187sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901455X/zl2187Isup2.hkl

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

C10H9NO	F(000) = 336
Mr = 159.18	Dx = 1.192 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4373 reflections
a = 9.495 (2) Å	θ = 2.2–28.3°
b = 10.703 (2) Å	µ = 0.08 mm−1
c = 8.9120 (19) Å	T = 173 K
β = 101.637 (3)°	Chunk, pale yellow
V = 887.1 (3) Å3	0.57 × 0.30 × 0.30 mm
Z = 4

Bruker APEX area-detector diffractometer	1550 independent reflections
Radiation source: fine-focus sealed tube	1510 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.848, Tmax = 1.000	k = −12→12
5825 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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ2(Fo2) + (0.0874P)2 + 1.0844P] where P = (Fo2 + 2Fc2)/3
1550 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	0.8163 (2)	0.3454 (2)	0.1877 (2)	0.0356 (6)
N1	0.7947 (3)	0.3179 (2)	0.4330 (3)	0.0323 (7)
H1A	0.8203	0.2728	0.5166	0.039*
C1	1.0048 (4)	0.0859 (3)	0.3289 (4)	0.0401 (8)
C2	0.9317 (3)	0.1756 (3)	0.3242 (3)	0.0317 (7)
C3	0.8422 (3)	0.2867 (3)	0.3095 (3)	0.0290 (7)
C4	0.7008 (4)	0.4254 (3)	0.4350 (4)	0.0365 (8)
H4A	0.7389	0.4971	0.3855	0.044*
H4B	0.7015	0.4487	0.5427	0.044*
C5	0.5485 (3)	0.4009 (3)	0.3545 (3)	0.0323 (7)
C6	0.4870 (4)	0.4688 (3)	0.2258 (4)	0.0413 (8)
H6A	0.5418	0.5309	0.1873	0.050*
C7	0.3471 (4)	0.4469 (4)	0.1532 (4)	0.0483 (9)
H7A	0.3058	0.4943	0.0653	0.058*
C8	0.2665 (4)	0.3569 (4)	0.2069 (4)	0.0466 (9)
H8A	0.1702	0.3415	0.1559	0.056*
C9	0.3268 (4)	0.2895 (3)	0.3353 (4)	0.0464 (9)
H9A	0.2715	0.2277	0.3736	0.056*
C10	0.4673 (4)	0.3113 (3)	0.4089 (4)	0.0411 (8)
H10A	0.5081	0.2643	0.4974	0.049*
H1	1.061 (4)	0.014 (4)	0.328 (4)	0.050 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0461 (13)	0.0335 (12)	0.0286 (12)	−0.0005 (10)	0.0112 (9)	0.0028 (9)
N1	0.0378 (14)	0.0352 (14)	0.0246 (13)	0.0058 (11)	0.0076 (10)	0.0010 (10)
C1	0.0344 (17)	0.0376 (19)	0.049 (2)	0.0016 (16)	0.0091 (14)	−0.0036 (15)
C2	0.0313 (16)	0.0355 (17)	0.0297 (16)	−0.0050 (13)	0.0091 (12)	−0.0018 (12)
C3	0.0285 (15)	0.0301 (15)	0.0275 (15)	−0.0076 (12)	0.0038 (11)	−0.0021 (12)
C4	0.0432 (18)	0.0323 (16)	0.0342 (17)	0.0031 (14)	0.0086 (13)	−0.0064 (13)
C5	0.0406 (17)	0.0284 (15)	0.0292 (15)	0.0061 (13)	0.0104 (12)	−0.0050 (12)
C6	0.050 (2)	0.0380 (18)	0.0368 (18)	0.0070 (15)	0.0116 (15)	0.0024 (14)
C7	0.051 (2)	0.054 (2)	0.0379 (19)	0.0174 (18)	0.0061 (16)	0.0028 (16)
C8	0.0387 (18)	0.053 (2)	0.046 (2)	0.0078 (16)	0.0040 (15)	−0.0089 (16)
C9	0.043 (2)	0.0391 (19)	0.057 (2)	−0.0032 (15)	0.0112 (16)	−0.0014 (16)
C10	0.0459 (19)	0.0358 (17)	0.0412 (18)	0.0040 (14)	0.0080 (15)	0.0049 (14)

O1—C3	1.235 (4)	C5—C6	1.384 (5)
N1—C3	1.314 (4)	C6—C7	1.376 (5)
N1—C4	1.458 (4)	C6—H6A	0.9500
N1—H1A	0.8800	C7—C8	1.374 (6)
C1—C2	1.180 (5)	C7—H7A	0.9500
C1—H1	0.93 (4)	C8—C9	1.376 (5)
C2—C3	1.453 (4)	C8—H8A	0.9500
C4—C5	1.502 (5)	C9—C10	1.383 (5)
C4—H4A	0.9900	C9—H9A	0.9500
C4—H4B	0.9900	C10—H10A	0.9500
C5—C10	1.378 (5)
C3—N1—C4	121.7 (3)	C6—C5—C4	120.6 (3)
C3—N1—H1A	119.2	C7—C6—C5	120.4 (3)
C4—N1—H1A	119.2	C7—C6—H6A	119.8
C2—C1—H1	178 (2)	C5—C6—H6A	119.8
C1—C2—C3	176.9 (3)	C8—C7—C6	120.6 (3)
O1—C3—N1	124.5 (3)	C8—C7—H7A	119.7
O1—C3—C2	120.3 (3)	C6—C7—H7A	119.7
N1—C3—C2	115.2 (3)	C7—C8—C9	119.3 (3)
N1—C4—C5	112.8 (2)	C7—C8—H8A	120.4
N1—C4—H4A	109.0	C9—C8—H8A	120.4
C5—C4—H4A	109.0	C8—C9—C10	120.4 (3)
N1—C4—H4B	109.0	C8—C9—H9A	119.8
C5—C4—H4B	109.0	C10—C9—H9A	119.8
H4A—C4—H4B	107.8	C5—C10—C9	120.4 (3)
C10—C5—C6	119.0 (3)	C5—C10—H10A	119.8
C10—C5—C4	120.4 (3)	C9—C10—H10A	119.8
C4—N1—C3—O1	2.1 (5)	C5—C6—C7—C8	−0.3 (5)
C4—N1—C3—C2	−178.4 (3)	C6—C7—C8—C9	0.6 (5)
C3—N1—C4—C5	76.0 (4)	C7—C8—C9—C10	−0.5 (5)
N1—C4—C5—C10	63.6 (4)	C6—C5—C10—C9	0.3 (5)
N1—C4—C5—C6	−117.3 (3)	C4—C5—C10—C9	179.4 (3)
C10—C5—C6—C7	−0.2 (5)	C8—C9—C10—C5	0.0 (5)
C4—C5—C6—C7	−179.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.88	1.99	2.839 (3)	163
C1—H1···O1ii	0.93 (4)	2.17 (4)	3.105 (4)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.88	1.99	2.839 (3)	163
C1—H1⋯O1ii	0.93 (4)	2.17 (4)	3.105 (4)	176 (3)

Symmetry codes: (i) ; (ii) .