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

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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.041
• wR factor = 0.122
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT245_ALERT_2_C U(iso) H2N       Smaller than U(eq) N1        by      0.040 Ang   2
PLAT331_ALERT_2_C Small Aver Phenyl C-C Dist C1        -C6       .       1.37 Ang.
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00894 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT791_ALERT_4_G Model has Chirality at C9          (Chiral SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         18 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         10 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 511
              The constraint U~iso@(H) = 1.2U~eq~(carrier) was applied in all cases.
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

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

Crystal data

C16H19NSe	prism
Mr = 304.28	Dx = 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) Å^3	T = 295 K
Z = 4	Prism, yellow
F(000) = 624	0.32 × 0.28 × 0.22 mm

Data collection

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

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0698P)^2 + 0.2035P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2848 reflections	Δρmax = 0.39 e Å^−3
171 parameters	Δρmin = −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

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···N1^i	0.79 (5)	2.56 (5)	3.319 (5)	161 (4)

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