N-Phenyl-N-(3-phenyl­prop-2-yn­yl)aniline

Pang, T.; Sun, Y.; Zhang, J.

doi:10.1107/S1600536809037866

organic compounds

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Volume 65| Part 10| October 2009| Page o2555

doi:10.1107/S1600536809037866

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N-Phenyl-N-(3-phenylprop-2-ynyl)aniline

Tao Pang,^a Yi-chong Sun ^a and Jian-ming Zhang ^a ^*

^aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: leileitaotao6666@163.com

(Received 29 April 2009; accepted 18 September 2009; online 26 September 2009)

In the title compound, C₂₁H₁₇N, synthesized by a three-component coupling reaction in the presence of copper(I) iodide, the N-bound phenyl rings form a dihedral angle of 72.5 (1)° with each other. Thereare no remarkable interactions in the crystal structure.

Related literature

For the preparation of the title compound, see: Nilsson et al. (1992 ). For the biological activity of propargylamines and their use as synthetic intermediates, see: Bieber & da Silva (2004 ); Hattori et al. (1993 ); Huffman et al. (1995 ); Konishi et al. (1990 ).

Experimental

Crystal data

C₂₁H₁₇N
M_r = 283.36
Monoclinic, P 2₁
a = 11.376 (1) Å
b = 5.7287 (5) Å
c = 13.409 (1) Å
β = 111.276 (3)°
V = 814.30 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.23 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
5689 measured reflections
1953 independent reflections
1448 reflections with I > 2σ(I)
R_int = 0.136

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.141
S = 0.91
1953 reflections
199 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809037866/lx2105sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037866/lx2105Isup2.hkl

checkCIF report

Comment top

Propargylamines are compounds of interesting biological properties and important synthetic intermediates (Konishi et al., 1990; Huffman et al., 1995; Hattori et al., 1993; Bieber et al., 2004). The reaction which a three component procedure between terminal alkynes, formaldehyde and secondary amines has been extended to some less activated alkynes by the introduction of copper catalysts. Here we report the crystal structure of the title compound (Fig. 1).

In the molecule of the title compound, the N-bound two phenyl rings form a dihedral angle of 72.5 (1)° with each other.

Related literature top

For the preparation of the title compound, see: Nilsson et al. (1992). For the biological activity of propargylamines and their use as synthetic intermediates, see: Bieber & da Silva (2004); Hattori et al. (1993); Huffman et al. (1995); Konishi et al. (1990).

Experimental top

The title compound was synthesized according to the literature procedure of Nilsson et al. (1992). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in chloroform : methanol (50 : 1) at room temperature.

Computing details top

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

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by spheres of arbitrary radius.

N-Phenyl-N-(3-phenylprop-2-ynyl)aniline top

Crystal data top

C₂₁H₁₇N	F(000) = 300
M_r = 283.36	D_x = 1.156 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1607 reflections
a = 11.376 (1) Å	θ = 2.9–22.6°
b = 5.7287 (5) Å	µ = 0.07 mm⁻¹
c = 13.409 (1) Å	T = 298 K
β = 111.276 (3)°	Block, colorless
V = 814.30 (12) Å³	0.23 × 0.13 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	1448 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.136
Graphite monochromator	θ_max = 27.0°, θ_min = 1.6°
Detector resolution: 10.0 pixels mm^-1	h = −13→14
ϕ and ω scans	k = −7→7
5689 measured reflections	l = −17→10
1953 independent 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)] = 0.055	Hydrogen site location: difference Fourier map
wR(F²) = 0.141	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.074P)²] where P = (F_o² + 2F_c²)/3
1953 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₁H₁₇N	V = 814.30 (12) Å³
M_r = 283.36	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.376 (1) Å	µ = 0.07 mm⁻¹
b = 5.7287 (5) Å	T = 298 K
c = 13.409 (1) Å	0.23 × 0.13 × 0.10 mm
β = 111.276 (3)°

Data collection top

Bruker SMART CCD diffractometer	1448 reflections with I > 2σ(I)
5689 measured reflections	R_int = 0.136
1953 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.141	H-atom parameters constrained
S = 0.91	Δρ_max = 0.15 e Å⁻³
1953 reflections	Δρ_min = −0.19 e Å⁻³
199 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.2341 (2)	0.1972 (5)	0.3674 (2)	0.0541 (7)
C2	0.1912 (3)	0.1537 (7)	0.4505 (2)	0.0716 (9)
H2	0.1255	0.2420	0.4565	0.086*
C3	0.2457 (4)	−0.0199 (7)	0.5240 (3)	0.0859 (11)
H3	0.2158	−0.0466	0.5789	0.103*
C4	0.3427 (3)	−0.1539 (8)	0.5183 (3)	0.0870 (11)
H4	0.3790	−0.2695	0.5688	0.104*
C5	0.3851 (3)	−0.1131 (7)	0.4356 (3)	0.0775 (9)
H5	0.4500	−0.2039	0.4298	0.093*
C6	0.3327 (2)	0.0596 (6)	0.3619 (2)	0.0606 (7)
H6	0.3635	0.0853	0.3074	0.073*
C7	0.1821 (2)	0.3552 (4)	0.1865 (2)	0.0473 (6)
C8	0.1297 (2)	0.1628 (5)	0.1253 (2)	0.0555 (7)
H8	0.0980	0.0420	0.1546	0.067*
C9	0.1235 (3)	0.1472 (6)	0.0206 (2)	0.0646 (8)
H9	0.0885	0.0158	−0.0201	0.078*
C10	0.1692 (3)	0.3265 (6)	−0.0233 (2)	0.0651 (8)
H10	0.1657	0.3167	−0.0936	0.078*
C11	0.2198 (3)	0.5184 (6)	0.0370 (3)	0.0690 (8)
H11	0.2496	0.6407	0.0072	0.083*
C12	0.2273 (3)	0.5334 (5)	0.1416 (2)	0.0606 (7)
H12	0.2632	0.6645	0.1821	0.073*
C13	0.0902 (3)	0.5331 (5)	0.3057 (2)	0.0637 (7)
H13A	0.0843	0.6719	0.2627	0.076*
H13B	0.1166	0.5817	0.3799	0.076*
C14	−0.0356 (3)	0.4259 (6)	0.2741 (2)	0.0611 (7)
C15	−0.1346 (3)	0.3302 (6)	0.2484 (2)	0.0627 (7)
C16	−0.2554 (3)	0.2165 (6)	0.2187 (2)	0.0589 (7)
C17	−0.2702 (4)	0.0104 (7)	0.2656 (3)	0.0808 (9)
H17	−0.2010	−0.0604	0.3170	0.097*
C18	−0.3885 (5)	−0.0912 (9)	0.2361 (4)	0.1097 (16)
H18	−0.3990	−0.2296	0.2681	0.132*
C19	−0.4903 (5)	0.0132 (13)	0.1594 (5)	0.1160 (19)
H19	−0.5697	−0.0548	0.1397	0.139*
C20	−0.4753 (3)	0.2131 (11)	0.1130 (4)	0.1032 (15)
H20	−0.5446	0.2817	0.0607	0.124*
C21	−0.3604 (3)	0.3163 (7)	0.1413 (3)	0.0760 (9)
H21	−0.3518	0.4551	0.1086	0.091*
N1	0.1865 (2)	0.3795 (4)	0.29364 (18)	0.0548 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0509 (14)	0.0643 (16)	0.0386 (12)	−0.0118 (12)	0.0061 (10)	−0.0006 (13)
C2	0.0736 (18)	0.092 (2)	0.0501 (16)	−0.0029 (18)	0.0231 (14)	0.0022 (17)
C3	0.094 (2)	0.114 (3)	0.0463 (16)	−0.006 (2)	0.0216 (17)	0.0205 (19)
C4	0.082 (2)	0.101 (3)	0.061 (2)	0.004 (2)	0.0065 (17)	0.026 (2)
C5	0.0654 (18)	0.086 (2)	0.0677 (19)	0.0086 (16)	0.0085 (15)	0.0125 (19)
C6	0.0503 (14)	0.0747 (19)	0.0496 (15)	−0.0017 (14)	0.0096 (12)	0.0065 (14)
C7	0.0430 (12)	0.0519 (14)	0.0453 (13)	−0.0001 (11)	0.0139 (10)	0.0052 (12)
C8	0.0564 (15)	0.0556 (16)	0.0488 (14)	−0.0085 (12)	0.0120 (11)	0.0017 (13)
C9	0.0681 (18)	0.0638 (18)	0.0508 (15)	−0.0011 (14)	0.0082 (13)	−0.0048 (14)
C10	0.0657 (17)	0.083 (2)	0.0476 (15)	0.0153 (16)	0.0216 (13)	0.0090 (16)
C11	0.0769 (19)	0.0682 (19)	0.071 (2)	−0.0052 (16)	0.0381 (16)	0.0152 (18)
C12	0.0650 (16)	0.0546 (15)	0.0655 (18)	−0.0137 (14)	0.0275 (13)	−0.0015 (15)
C13	0.0715 (18)	0.0593 (16)	0.0621 (17)	0.0007 (15)	0.0265 (14)	−0.0023 (15)
C14	0.0622 (17)	0.0729 (18)	0.0523 (15)	0.0082 (15)	0.0257 (13)	−0.0003 (15)
C15	0.0634 (17)	0.080 (2)	0.0490 (15)	0.0096 (16)	0.0252 (13)	−0.0016 (15)
C16	0.0642 (17)	0.0692 (19)	0.0500 (15)	0.0063 (14)	0.0288 (13)	−0.0089 (15)
C17	0.092 (2)	0.082 (2)	0.072 (2)	−0.0031 (19)	0.0344 (18)	−0.008 (2)
C18	0.141 (4)	0.102 (3)	0.112 (4)	−0.045 (3)	0.077 (4)	−0.033 (3)
C19	0.087 (3)	0.168 (5)	0.110 (4)	−0.052 (3)	0.055 (3)	−0.059 (4)
C20	0.060 (2)	0.149 (5)	0.097 (3)	−0.002 (2)	0.024 (2)	−0.029 (3)
C21	0.0680 (19)	0.085 (2)	0.074 (2)	0.0091 (17)	0.0248 (16)	−0.0135 (18)
N1	0.0555 (12)	0.0624 (13)	0.0476 (12)	−0.0017 (10)	0.0201 (10)	−0.0001 (11)

Geometric parameters (Å, º) top

C1—C2	1.391 (4)	C11—C12	1.377 (4)
C1—C6	1.395 (4)	C11—H11	0.9300
C1—N1	1.405 (4)	C12—H12	0.9300
C2—C3	1.378 (5)	C13—N1	1.459 (3)
C2—H2	0.9300	C13—C14	1.471 (4)
C3—C4	1.368 (5)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.379 (5)	C14—C15	1.185 (4)
C4—H4	0.9300	C15—C16	1.441 (5)
C5—C6	1.372 (5)	C16—C17	1.377 (5)
C5—H5	0.9300	C16—C21	1.390 (4)
C6—H6	0.9300	C17—C18	1.386 (6)
C7—C8	1.374 (4)	C17—H17	0.9300
C7—C12	1.377 (4)	C18—C19	1.376 (8)
C7—N1	1.425 (3)	C18—H18	0.9300
C8—C9	1.383 (4)	C19—C20	1.344 (7)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.377 (5)	C20—C21	1.358 (5)
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.362 (5)	C21—H21	0.9300
C10—H10	0.9300

C2—C1—C6	117.6 (3)	C7—C12—C11	120.3 (3)
C2—C1—N1	122.7 (3)	C7—C12—H12	119.8
C6—C1—N1	119.6 (2)	C11—C12—H12	119.8
C3—C2—C1	120.2 (3)	N1—C13—C14	114.0 (2)
C3—C2—H2	119.9	N1—C13—H13A	108.7
C1—C2—H2	119.9	C14—C13—H13A	108.7
C4—C3—C2	121.8 (3)	N1—C13—H13B	108.7
C4—C3—H3	119.1	C14—C13—H13B	108.7
C2—C3—H3	119.1	H13A—C13—H13B	107.6
C3—C4—C5	118.3 (3)	C15—C14—C13	177.1 (3)
C3—C4—H4	120.9	C14—C15—C16	178.9 (3)
C5—C4—H4	120.9	C17—C16—C21	118.7 (3)
C6—C5—C4	120.9 (3)	C17—C16—C15	121.6 (3)
C6—C5—H5	119.5	C21—C16—C15	119.7 (3)
C4—C5—H5	119.5	C16—C17—C18	119.8 (4)
C5—C6—C1	121.1 (3)	C16—C17—H17	120.1
C5—C6—H6	119.5	C18—C17—H17	120.1
C1—C6—H6	119.5	C19—C18—C17	119.9 (5)
C8—C7—C12	118.9 (2)	C19—C18—H18	120.1
C8—C7—N1	122.0 (2)	C17—C18—H18	120.1
C12—C7—N1	119.1 (2)	C20—C19—C18	120.2 (4)
C7—C8—C9	120.6 (3)	C20—C19—H19	119.9
C7—C8—H8	119.7	C18—C19—H19	119.9
C9—C8—H8	119.7	C19—C20—C21	120.8 (4)
C10—C9—C8	119.9 (3)	C19—C20—H20	119.6
C10—C9—H9	120.1	C21—C20—H20	119.6
C8—C9—H9	120.1	C20—C21—C16	120.6 (4)
C11—C10—C9	119.5 (3)	C20—C21—H21	119.7
C11—C10—H10	120.3	C16—C21—H21	119.7
C9—C10—H10	120.3	C1—N1—C7	120.1 (2)
C10—C11—C12	120.8 (3)	C1—N1—C13	118.9 (2)
C10—C11—H11	119.6	C7—N1—C13	114.6 (2)
C12—C11—H11	119.6

C6—C1—C2—C3	0.1 (4)	C14—C15—C16—C21	90 (18)
N1—C1—C2—C3	−176.6 (3)	C21—C16—C17—C18	−0.8 (4)
C1—C2—C3—C4	0.1 (5)	C15—C16—C17—C18	178.9 (3)
C2—C3—C4—C5	−0.6 (6)	C16—C17—C18—C19	0.6 (5)
C3—C4—C5—C6	0.9 (6)	C17—C18—C19—C20	0.1 (6)
C4—C5—C6—C1	−0.8 (5)	C18—C19—C20—C21	−0.6 (6)
C2—C1—C6—C5	0.2 (4)	C19—C20—C21—C16	0.4 (6)
N1—C1—C6—C5	177.1 (3)	C17—C16—C21—C20	0.3 (5)
C12—C7—C8—C9	0.6 (4)	C15—C16—C21—C20	−179.3 (3)
N1—C7—C8—C9	178.2 (2)	C2—C1—N1—C7	−148.9 (3)
C7—C8—C9—C10	−0.5 (4)	C6—C1—N1—C7	34.4 (3)
C8—C9—C10—C11	−0.2 (4)	C2—C1—N1—C13	1.4 (4)
C9—C10—C11—C12	1.0 (4)	C6—C1—N1—C13	−175.3 (3)
C8—C7—C12—C11	0.1 (4)	C8—C7—N1—C1	50.4 (3)
N1—C7—C12—C11	−177.5 (3)	C12—C7—N1—C1	−132.0 (3)
C10—C11—C12—C7	−0.9 (4)	C8—C7—N1—C13	−101.1 (3)
N1—C13—C14—C15	9 (6)	C12—C7—N1—C13	76.4 (3)
C13—C14—C15—C16	136 (16)	C14—C13—N1—C1	−74.1 (3)
C14—C15—C16—C17	−89 (18)	C14—C13—N1—C7	77.8 (3)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇N
M_r	283.36
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	11.376 (1), 5.7287 (5), 13.409 (1)
β (°)	111.276 (3)
V (Å³)	814.30 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.23 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5689, 1953, 1448
R_int	0.136
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.141, 0.91
No. of reflections	1953
No. of parameters	199
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.19

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The author is grateful to Central China Normal University for support.

References

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