(S)-1-(Benzyl­selan­yl)-3-phenyl­propan-2-amine

Prabhu Kumar, K.M.; Palakshamurthy, B.S.; Jasinski, J.P.; Butcher, R.J.; Raghavendra Kumar, P.

doi:10.1107/S2414314619010290

organic compounds

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ISSN: 2414-3146

Volume 4| Part 7| July 2019| x191029

https://doi.org/10.1107/S2414314619010290

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(S)-1-(Benzylselanyl)-3-phenylpropan-2-amine

K. M. Prabhu Kumar,^a B. S. Palakshamurthy,^b J. P. Jasinski,^c R. J. Butcher ^d and P. Raghavendra Kumar ^a ^*

^aDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka-572103, India, ^bDepartment of PG Studies and Research in Physics, Albert Einstein Block, UCS, Tumkur University, Tumkur, Karnataka-572103, India, ^cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^dDepartment of Inorganic & Structural Chemistry, Howard University Washington DC, 20059, USA
^*Correspondence e-mail: raghukp1@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 July 2019; accepted 18 July 2019; online 26 July 2019)

In the title compound, C₁₆H₁₉NSe, the dihedral angle between the benzene rings is 66.49 (12) and a weak intramolecular N—H⋯Se hydrogen bond generates an S(6) ring. In the crystal, weak N—H⋯N hydrogen bonds link the molecules into [100] chains.

Keywords: crystal structure; chiral selenated amine; hybrid ligand.

CCDC reference: 1941535

Structure description

The title compound, C₁₆H₁₉NSe, is a chiral selenated amine that could act as a hybrid ligand of the (N,Se) type. This amine could further be used for the synthesis of chiral Schiff bases with various aldehydes/ketones, which may result in multidentate hybrid ligands (Kostas et al., 2006 ; Kumar et al., 2009 ).

The molecular structure is shown in Fig. 1. The dihedral angle between the benzene rings is 66.49 (12)° and the C7—Se1—C8—C9 torsion angle is 75.3 (5)°. A weak intramolecular N—H⋯Se hydrogen bond (Table 1) generates an S(5) ring. In the crystal, molecules are linked by weak N1—H2N⋯N1 interactions, generating [100] chains (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Se1	0.93 (7)	2.69 (7)	3.239 (7)	119 (5)
N1—H2N⋯N1ⁱ	0.79 (5)	2.56 (5)	3.319 (5)	161 (4)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Figure 2
The packing of the title compound viewed along [010] showing the formation of [100] hydrogen-bonded chains.

Synthesis and crystallization

The title compound was synthesized according to our reported procedure (Rajegowda et al., 2015 ). The light-yellow viscous liquid obtained was dissolved in a 1:1 mixture of dichloromethane and n-hexane, which was kept undisturbed in the refrigerator at 0°C. After four to five days, light-yellow crystals were collected by filtration and dried in air.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₉NSe
M_r	304.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	5.7670 (3), 8.1908 (3), 31.6737 (9)
V (Å³)	1496.15 (10)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	3.24
Crystal size (mm)	0.32 × 0.28 × 0.22

Data collection
Diffractometer	Rigaku Oxford Diffraction CCD
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.403, 0.490
No. of measured, independent and observed [I > 2σ(I)] reflections	9030, 2848, 2501
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.122, 1.09
No. of reflections	2848
No. of parameters	171
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.45
Absolute structure	Flack x determined using 861 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.015 (16)
Computer programs: CrysAlis PRO (Agilent, 2014, SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1941535

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619010290/hb4305sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619010290/hb4305Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619010290/hb4305Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014; cell refinement: CrysAlis PRO (Agilent, 2014; data reduction: CrysAlis PRO (Agilent, 2014; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(S)-1-(Benzylselanyl)-3-phenylpropan-2-amine top

Crystal data top

C₁₆H₁₉NSe	prism
M_r = 304.28	D_x = 1.351 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Melting point: 498 K
Hall symbol: P 2ac 2ab	Cu Kα radiation, λ = 1.54178 Å
a = 5.7670 (3) Å	Cell parameters from 2501 reflections
b = 8.1908 (3) Å	θ = 1–71.8°
c = 31.6737 (9) Å	µ = 3.24 mm⁻¹
V = 1496.15 (10) Å³	T = 295 K
Z = 4	Prism, yellow
F(000) = 624	0.32 × 0.28 × 0.22 mm

Data collection top

Rigaku Oxford Diffraction CCD diffractometer	2848 independent reflections
Radiation source: Cu Kα	2501 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 16.2 pixels mm^-1	θ_max = 71.8°, θ_min = 5.6°
ω scans	h = −7→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −9→6
T_min = 0.403, T_max = 0.490	l = −37→38
9030 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0698P)² + 0.2035P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2848 reflections	Δρ_max = 0.39 e Å⁻³
171 parameters	Δρ_min = −0.45 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 861 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
3 constraints	Absolute structure parameter: −0.015 (16)
Primary atom site location: structure-invariant direct methods

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. The C-bound hydrogen atoms were fixed geometrically and allowed to ride on their parent atoms: C—H = 0.93–0.97Å. The N-bound H atoms were located in difference maps and their positions were freely refined. The constraint U_iso(H) = 1.2U_eq(carrier) was applied in all cases.

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

	x	y	z	U_iso*/U_eq
Se1	0.09270 (14)	0.59847 (9)	0.46926 (2)	0.0991 (3)
N1	0.4997 (11)	0.3335 (8)	0.48563 (15)	0.0909 (14)
H1N	0.447 (12)	0.424 (8)	0.501 (2)	0.10 (2)*
H2N	0.633 (9)	0.313 (6)	0.4892 (14)	0.051 (12)*
C1	0.1443 (9)	0.8034 (5)	0.39473 (16)	0.0771 (12)
C2	−0.0602 (10)	0.8816 (7)	0.3875 (2)	0.0964 (16)
H2A	−0.147323	0.919744	0.410166	0.116*
C3	−0.1392 (12)	0.9046 (9)	0.3468 (3)	0.116 (2)
H3A	−0.277636	0.959867	0.342064	0.139*
C4	−0.0145 (16)	0.8463 (8)	0.3137 (3)	0.113 (2)
H4A	−0.068275	0.861057	0.286291	0.135*
C5	0.1889 (15)	0.7662 (8)	0.3205 (2)	0.106 (2)
H5A	0.273920	0.726206	0.297845	0.127*
C6	0.2680 (10)	0.7449 (6)	0.36081 (18)	0.0823 (13)
H6A	0.407040	0.690101	0.365352	0.099*
C7	0.2370 (15)	0.7833 (7)	0.43881 (19)	0.1000 (18)
H7A	0.209642	0.883106	0.454527	0.120*
H7B	0.403243	0.766115	0.437452	0.120*
C8	0.2155 (9)	0.4239 (6)	0.43435 (13)	0.0699 (11)
H8A	0.125625	0.325788	0.439510	0.084*
H8B	0.194796	0.453309	0.404928	0.084*
C9	0.4694 (8)	0.3857 (6)	0.44176 (13)	0.0690 (10)
H9A	0.562445	0.483726	0.436549	0.083*
C10	0.5504 (10)	0.2484 (6)	0.41261 (17)	0.0816 (13)
H10A	0.710605	0.222685	0.419194	0.098*
H10B	0.458534	0.151699	0.418309	0.098*
C11	0.5328 (9)	0.2881 (6)	0.36655 (15)	0.0719 (11)
C12	0.3552 (11)	0.2271 (7)	0.34193 (17)	0.0865 (14)
H12A	0.244757	0.158538	0.353907	0.104*
C13	0.3404 (13)	0.2668 (8)	0.29984 (19)	0.1018 (19)
H13A	0.220590	0.224179	0.283566	0.122*
C14	0.4997 (12)	0.3684 (9)	0.28164 (18)	0.1019 (19)
H14A	0.487209	0.395894	0.253249	0.122*
C15	0.6758 (12)	0.4286 (10)	0.3052 (2)	0.106 (2)
H15A	0.785360	0.496659	0.292782	0.128*
C16	0.6946 (9)	0.3899 (8)	0.34768 (18)	0.0894 (14)
H16A	0.816131	0.432318	0.363567	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.1124 (5)	0.1187 (5)	0.0661 (3)	0.0105 (4)	0.0205 (3)	−0.0022 (3)
N1	0.092 (3)	0.117 (4)	0.064 (2)	−0.005 (3)	−0.018 (2)	0.022 (2)
C1	0.082 (3)	0.059 (2)	0.091 (3)	−0.004 (2)	0.000 (2)	−0.005 (2)
C2	0.081 (3)	0.081 (3)	0.127 (5)	0.015 (3)	0.003 (3)	−0.007 (3)
C3	0.086 (4)	0.092 (4)	0.170 (7)	0.004 (4)	−0.033 (4)	0.008 (5)
C4	0.139 (6)	0.088 (4)	0.112 (5)	−0.024 (4)	−0.037 (5)	0.015 (3)
C5	0.142 (6)	0.087 (3)	0.089 (4)	−0.007 (4)	0.021 (4)	0.008 (3)
C6	0.080 (3)	0.074 (3)	0.093 (3)	0.005 (2)	0.012 (3)	0.010 (2)
C7	0.135 (5)	0.076 (3)	0.089 (3)	−0.006 (3)	−0.007 (4)	−0.011 (3)
C8	0.076 (3)	0.074 (2)	0.060 (2)	−0.006 (2)	−0.0019 (19)	0.0083 (18)
C9	0.075 (3)	0.076 (2)	0.056 (2)	−0.008 (2)	−0.0111 (17)	0.0117 (19)
C10	0.088 (4)	0.073 (2)	0.083 (3)	0.008 (3)	−0.010 (2)	0.006 (2)
C11	0.075 (3)	0.066 (2)	0.075 (2)	0.012 (2)	−0.003 (2)	−0.0074 (19)
C12	0.095 (4)	0.080 (3)	0.085 (3)	−0.005 (3)	−0.008 (3)	−0.013 (2)
C13	0.115 (5)	0.111 (4)	0.079 (3)	−0.003 (4)	−0.017 (3)	−0.026 (3)
C14	0.118 (4)	0.124 (5)	0.064 (3)	0.015 (4)	0.010 (3)	−0.013 (3)
C15	0.104 (4)	0.131 (5)	0.084 (3)	−0.012 (4)	0.026 (3)	−0.007 (3)
C16	0.074 (3)	0.104 (4)	0.091 (3)	−0.001 (3)	0.000 (2)	−0.011 (3)

Geometric parameters (Å, º) top

Se1—C8	1.942 (5)	C8—C9	1.515 (7)
Se1—C7	1.979 (7)	C8—H8A	0.9700
N1—C9	1.464 (6)	C8—H8B	0.9700
N1—H1N	0.93 (7)	C9—C10	1.528 (7)
N1—H2N	0.79 (5)	C9—H9A	0.9800
C1—C2	1.361 (8)	C10—C11	1.498 (7)
C1—C6	1.376 (7)	C10—H10A	0.9700
C1—C7	1.504 (8)	C10—H10B	0.9700
C2—C3	1.380 (11)	C11—C12	1.381 (7)
C2—H2A	0.9300	C11—C16	1.387 (8)
C3—C4	1.358 (12)	C12—C13	1.375 (8)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.361 (11)	C13—C14	1.367 (9)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.365 (10)	C14—C15	1.354 (10)
C5—H5A	0.9300	C14—H14A	0.9300
C6—H6A	0.9300	C15—C16	1.386 (9)
C7—H7A	0.9700	C15—H15A	0.9300
C7—H7B	0.9700	C16—H16A	0.9300

C8—Se1—C7	97.6 (2)	Se1—C8—H8B	108.6
C9—N1—H1N	103 (4)	H8A—C8—H8B	107.6
C9—N1—H2N	108 (3)	N1—C9—C8	108.8 (4)
H1N—N1—H2N	114 (6)	N1—C9—C10	108.8 (4)
C2—C1—C6	118.8 (5)	C8—C9—C10	110.7 (4)
C2—C1—C7	121.0 (6)	N1—C9—H9A	109.5
C6—C1—C7	120.1 (5)	C8—C9—H9A	109.5
C1—C2—C3	120.5 (6)	C10—C9—H9A	109.5
C1—C2—H2A	119.8	C11—C10—C9	114.1 (4)
C3—C2—H2A	119.8	C11—C10—H10A	108.7
C4—C3—C2	119.9 (6)	C9—C10—H10A	108.7
C4—C3—H3A	120.1	C11—C10—H10B	108.7
C2—C3—H3A	120.1	C9—C10—H10B	108.7
C3—C4—C5	120.2 (7)	H10A—C10—H10B	107.6
C3—C4—H4A	119.9	C12—C11—C16	118.3 (5)
C5—C4—H4A	119.9	C12—C11—C10	121.5 (5)
C4—C5—C6	119.9 (7)	C16—C11—C10	120.3 (5)
C4—C5—H5A	120.1	C13—C12—C11	120.5 (6)
C6—C5—H5A	120.1	C13—C12—H12A	119.7
C5—C6—C1	120.8 (6)	C11—C12—H12A	119.7
C5—C6—H6A	119.6	C14—C13—C12	120.7 (6)
C1—C6—H6A	119.6	C14—C13—H13A	119.6
C1—C7—Se1	112.8 (4)	C12—C13—H13A	119.6
C1—C7—H7A	109.0	C15—C14—C13	119.6 (6)
Se1—C7—H7A	109.0	C15—C14—H14A	120.2
C1—C7—H7B	109.0	C13—C14—H14A	120.2
Se1—C7—H7B	109.0	C14—C15—C16	120.7 (6)
H7A—C7—H7B	107.8	C14—C15—H15A	119.6
C9—C8—Se1	114.6 (3)	C16—C15—H15A	119.6
C9—C8—H8A	108.6	C15—C16—C11	120.2 (5)
Se1—C8—H8A	108.6	C15—C16—H16A	119.9
C9—C8—H8B	108.6	C11—C16—H16A	119.9

C6—C1—C2—C3	−1.4 (8)	N1—C9—C10—C11	−178.8 (4)
C7—C1—C2—C3	177.6 (6)	C8—C9—C10—C11	61.6 (6)
C1—C2—C3—C4	1.2 (10)	C9—C10—C11—C12	−102.5 (6)
C2—C3—C4—C5	−0.5 (11)	C9—C10—C11—C16	76.7 (6)
C3—C4—C5—C6	−0.1 (10)	C16—C11—C12—C13	0.0 (8)
C4—C5—C6—C1	0.0 (9)	C10—C11—C12—C13	179.1 (5)
C2—C1—C6—C5	0.8 (8)	C11—C12—C13—C14	−0.5 (9)
C7—C1—C6—C5	−178.2 (5)	C12—C13—C14—C15	0.9 (10)
C2—C1—C7—Se1	81.1 (6)	C13—C14—C15—C16	−0.8 (11)
C6—C1—C7—Se1	−99.9 (6)	C14—C15—C16—C11	0.2 (10)
Se1—C8—C9—N1	61.1 (5)	C12—C11—C16—C15	0.2 (8)
Se1—C8—C9—C10	−179.4 (3)	C10—C11—C16—C15	−179.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Se1	0.93 (7)	2.69 (7)	3.239 (7)	119 (5)
N1—H2N···N1ⁱ	0.79 (5)	2.56 (5)	3.319 (5)	161 (4)

Symmetry code: (i) x+1/2, −y+1/2, −z+1.

Acknowledgements

We are grateful to the facilities at BSPM Lab, Albert Einstein Block, University College of Science, Tumkur University, for the support related to crystallography work.

Funding information

Funding for this research was provided by: DST–SERB, Government of India, (grant No. DST/SR/S-1/IC76/2010(G) to PRK); NSF-MRI Program (grant No. CHE-1039027 to JPJ).

References

Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Kostas, I. D., Steele, B. R., Terzis, A., Amosova, S. V., Martynov, A. V. & Makhaeva, N. A. (2006). Eur. J. Inorg. Chem. pp. 2642–2646. CSD CrossRef Google Scholar
Kumar, A., Agarwal, M., Singh, A. K. & Butcher, R. J. (2009). Inorg. Chim. Acta, 362, 3208–3218. CSD CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Rajegowda, H. R., Kumar, P. R., Hosamani, A. & Palakshamurthy, B. S. (2015). Organomet. Chem. 61-69,799-800. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar