N-Benzyl­propan-2-aminium chloride

Pourayoubi, M.; Negari, M.

doi:10.1107/S1600536810006707

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o708

doi:10.1107/S1600536810006707

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N-Benzylpropan-2-aminium chloride

Mehrdad Pourayoubi ^a ^* and Monireh Negari ^a

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 11 February 2010; accepted 22 February 2010; online 27 February 2010)

In the crystal structure of title salt, C₁₀H₁₆N⁺·Cl⁻, the amino H atoms are involved in intermolecular N—H⋯Cl hydrogen bonding, generating a zigzag chain propagating in [100].

Related literature

For related structures, see: Pourayoubi & Sabbaghi (2007 ); Yazdanbakhsh & Sabbaghi (2007 ).

Experimental

Crystal data

C₁₀H₁₆N⁺·Cl⁻
M_r = 185.69
Orthorhombic, P n a 2₁
a = 9.9666 (6) Å
b = 18.0379 (11) Å
c = 5.7307 (4) Å
V = 1030.25 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 K
0.50 × 0.40 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.818, T_max = 0.910
11694 measured reflections
2720 independent reflections
2662 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.057
S = 1.07
2720 reflections
119 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ), 1229 Friedel pairs
Flack parameter: −0.02 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.853 (13)	2.288 (13)	3.1296 (9)	168.8 (11)
N1—H2⋯Cl1ⁱ	0.877 (14)	2.255 (14)	3.1257 (9)	171.9 (13)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S1600536810006707/ng2732sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006707/ng2732Isup2.hkl

checkCIF report

Comment top

In the previous works, the structure determination of [NH₂(CH₂C₆H₅)(CH(CH₃)₂)][CCl₃C(O)NHP(O)(O)(OCH₃)] (Pourayoubi & Sabbaghi, 2007) and [NH₂(CH₂C₆H₅)(CH(CH₃)₂)] [CF₃C(O)NHP(O)(O)(N(CH₂C₆H₅)(CH(CH₃)₂)] (Yazdanbakhsh & Sabbaghi, 2007) have been investigated; we report here on the crystal structure of title compound, the chloride salt of N-benzyl-2-propanaminium cation (Fig. 1). Both hydrogen atoms of NH₂ groups are involved in intermolecular N—H···Cl hydrogen bonding with neighbouring Cl^- anions [N1···Cl1 = 3.1296 (9) Å, N1···Cl2 = 3.1257 (9) Å] into an extended 1-D zigzag chain (Fig. 2).

Related literature top

For related structures, see: Pourayoubi & Sabbaghi (2007); Yazdanbakhsh & Sabbaghi (2007).

Experimental top

The title compound is a by-product of the preparation of P(O)[OC₆H₅][N(CH₂C₆H₅)(CH(CH₃)₂)]₂ [from the reaction between P(O)[OC₆H₅]Cl₂ and NH(CH₂C₆H₅)(CH(CH₃)₂), with 1:4 mole ratio] which is crystallized in CH₃C(O)CH₃.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. The molecular structure of the title salt, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50 % probability level.
	Fig. 2. Fragment of crystal packing (projection along c crystal axis), the hydrogen bonds are shown by dash line.

N-Benzylpropan-2-aminium chloride top

Crystal data top

C₁₀H₁₆N⁺·Cl⁻	F(000) = 400
M_r = 185.69	D_x = 1.197 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8636 reflections
a = 9.9666 (6) Å	θ = 2.3–34.0°
b = 18.0379 (11) Å	µ = 0.32 mm⁻¹
c = 5.7307 (4) Å	T = 100 K
V = 1030.25 (11) Å³	Prism, colourless
Z = 4	0.50 × 0.40 × 0.30 mm

Data collection top

Bruker APEXII CCD diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	2662 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 29.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.818, T_max = 0.910	k = −24→24
11694 measured reflections	l = −7→7

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0336P)² + 0.1229P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2720 reflections	Δρ_max = 0.25 e Å⁻³
119 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1229 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (4)

Crystal data top

C₁₀H₁₆N⁺·Cl⁻	V = 1030.25 (11) Å³
M_r = 185.69	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.9666 (6) Å	µ = 0.32 mm⁻¹
b = 18.0379 (11) Å	T = 100 K
c = 5.7307 (4) Å	0.50 × 0.40 × 0.30 mm

Data collection top

Bruker APEXII CCD diffractometer	2720 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2662 reflections with I > 2σ(I)
T_min = 0.818, T_max = 0.910	R_int = 0.023
11694 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.057	Δρ_max = 0.25 e Å⁻³
S = 1.07	Δρ_min = −0.15 e Å⁻³
2720 reflections	Absolute structure: Flack (1983), 1229 Friedel pairs
119 parameters	Absolute structure parameter: −0.02 (4)
1 restraint

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 > 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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.212804 (19)	0.282008 (11)	0.24289 (5)	0.01590 (6)
N1	0.47016 (8)	0.26697 (4)	0.55218 (15)	0.01274 (15)
H1	0.3950 (14)	0.2666 (7)	0.481 (2)	0.013 (3)*
H2	0.5322 (12)	0.2517 (7)	0.455 (3)	0.014 (3)*
C1	0.47024 (10)	0.21793 (5)	0.7630 (2)	0.01667 (19)
H1A	0.4181	0.2423	0.8884	0.020*
H1B	0.5636	0.2123	0.8190	0.020*
C2	0.41198 (9)	0.14208 (5)	0.71879 (19)	0.01422 (17)
C3	0.32866 (10)	0.11207 (6)	0.88949 (19)	0.01721 (19)
H3A	0.3064	0.1405	1.0235	0.021*
C4	0.27777 (10)	0.04055 (6)	0.8647 (2)	0.0205 (2)
H4A	0.2218	0.0202	0.9826	0.025*
C5	0.30877 (11)	−0.00100 (6)	0.6679 (2)	0.0192 (2)
H5A	0.2743	−0.0498	0.6512	0.023*
C6	0.39045 (10)	0.02910 (5)	0.49499 (19)	0.0188 (2)
H6A	0.4105	0.0010	0.3591	0.023*
C7	0.44277 (10)	0.10012 (5)	0.52059 (18)	0.01675 (18)
H7A	0.4995	0.1202	0.4033	0.020*
C8	0.50162 (11)	0.34699 (5)	0.6084 (2)	0.0195 (2)
H8A	0.5825	0.3487	0.7116	0.023*
C9	0.38428 (13)	0.38228 (5)	0.7366 (2)	0.0281 (2)
H9A	0.3631	0.3530	0.8758	0.042*
H9B	0.3059	0.3837	0.6335	0.042*
H9C	0.4083	0.4329	0.7830	0.042*
C10	0.53322 (12)	0.38753 (6)	0.3829 (2)	0.0256 (2)
H10A	0.6057	0.3617	0.3007	0.038*
H10B	0.5613	0.4384	0.4184	0.038*
H10C	0.4530	0.3887	0.2840	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01334 (10)	0.01922 (10)	0.01515 (10)	0.00008 (7)	−0.00118 (9)	0.00016 (10)
N1	0.0131 (4)	0.0111 (3)	0.0140 (4)	−0.0004 (3)	−0.0017 (3)	0.0011 (3)
C1	0.0237 (4)	0.0127 (4)	0.0136 (5)	−0.0013 (3)	−0.0044 (4)	0.0014 (3)
C2	0.0155 (4)	0.0114 (4)	0.0157 (4)	0.0011 (3)	−0.0018 (4)	0.0034 (4)
C3	0.0181 (4)	0.0173 (4)	0.0162 (4)	0.0020 (3)	0.0013 (4)	0.0012 (4)
C4	0.0197 (5)	0.0199 (5)	0.0221 (6)	−0.0024 (4)	0.0022 (4)	0.0062 (4)
C5	0.0189 (4)	0.0143 (4)	0.0243 (5)	−0.0027 (4)	−0.0041 (4)	0.0029 (3)
C6	0.0209 (4)	0.0163 (4)	0.0192 (5)	−0.0003 (4)	−0.0018 (4)	−0.0021 (4)
C7	0.0187 (4)	0.0154 (4)	0.0162 (4)	−0.0016 (3)	0.0008 (4)	0.0003 (4)
C8	0.0234 (5)	0.0113 (4)	0.0238 (5)	−0.0048 (4)	−0.0083 (4)	0.0010 (4)
C9	0.0512 (6)	0.0125 (4)	0.0205 (5)	0.0038 (4)	0.0042 (6)	−0.0007 (5)
C10	0.0241 (5)	0.0171 (5)	0.0355 (6)	−0.0021 (4)	0.0051 (5)	0.0084 (4)

Geometric parameters (Å, º) top

N1—C1	1.4974 (13)	C5—H5A	0.9500
N1—C8	1.5118 (13)	C6—C7	1.3910 (14)
N1—H1	0.853 (14)	C6—H6A	0.9500
N1—H2	0.877 (14)	C7—H7A	0.9500
C1—C2	1.5076 (12)	C8—C10	1.5178 (16)
C1—H1A	0.9900	C8—C9	1.5207 (17)
C1—H1B	0.9900	C8—H8A	1.0000
C2—C3	1.3927 (14)	C9—H9A	0.9800
C2—C7	1.3990 (14)	C9—H9B	0.9800
C3—C4	1.3934 (15)	C9—H9C	0.9800
C3—H3A	0.9500	C10—H10A	0.9800
C4—C5	1.3892 (16)	C10—H10B	0.9800
C4—H4A	0.9500	C10—H10C	0.9800
C5—C6	1.3925 (15)

C1—N1—C8	113.08 (8)	C7—C6—C5	120.21 (10)
C1—N1—H1	112.4 (9)	C7—C6—H6A	119.9
C8—N1—H1	107.0 (8)	C5—C6—H6A	119.9
C1—N1—H2	109.1 (9)	C6—C7—C2	120.11 (9)
C8—N1—H2	106.8 (8)	C6—C7—H7A	119.9
H1—N1—H2	108.2 (14)	C2—C7—H7A	119.9
N1—C1—C2	113.60 (9)	N1—C8—C10	108.76 (9)
N1—C1—H1A	108.8	N1—C8—C9	110.07 (8)
C2—C1—H1A	108.8	C10—C8—C9	111.67 (9)
N1—C1—H1B	108.8	N1—C8—H8A	108.8
C2—C1—H1B	108.8	C10—C8—H8A	108.8
H1A—C1—H1B	107.7	C9—C8—H8A	108.8
C3—C2—C7	119.39 (8)	C8—C9—H9A	109.5
C3—C2—C1	117.67 (9)	C8—C9—H9B	109.5
C7—C2—C1	122.88 (9)	H9A—C9—H9B	109.5
C2—C3—C4	120.36 (9)	C8—C9—H9C	109.5
C2—C3—H3A	119.8	H9A—C9—H9C	109.5
C4—C3—H3A	119.8	H9B—C9—H9C	109.5
C5—C4—C3	120.08 (9)	C8—C10—H10A	109.5
C5—C4—H4A	120.0	C8—C10—H10B	109.5
C3—C4—H4A	120.0	H10A—C10—H10B	109.5
C4—C5—C6	119.83 (9)	C8—C10—H10C	109.5
C4—C5—H5A	120.1	H10A—C10—H10C	109.5
C6—C5—H5A	120.1	H10B—C10—H10C	109.5

C8—N1—C1—C2	168.17 (8)	C4—C5—C6—C7	1.03 (16)
N1—C1—C2—C3	−138.75 (10)	C5—C6—C7—C2	−0.91 (15)
N1—C1—C2—C7	44.10 (12)	C3—C2—C7—C6	−0.02 (14)
C7—C2—C3—C4	0.83 (15)	C1—C2—C7—C6	177.09 (9)
C1—C2—C3—C4	−176.43 (9)	C1—N1—C8—C10	166.04 (8)
C2—C3—C4—C5	−0.71 (16)	C1—N1—C8—C9	−71.33 (11)
C3—C4—C5—C6	−0.22 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.853 (13)	2.288 (13)	3.1296 (9)	168.8 (11)
N1—H2···Cl1ⁱ	0.877 (14)	2.255 (14)	3.1257 (9)	171.9 (13)

Symmetry code: (i) x+1/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₆N⁺·Cl⁻
M_r	185.69
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	9.9666 (6), 18.0379 (11), 5.7307 (4)
V (Å³)	1030.25 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.50 × 0.40 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.818, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	11694, 2720, 2662
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.057, 1.07
No. of reflections	2720
No. of parameters	119
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.15
Absolute structure	Flack (1983), 1229 Friedel pairs
Absolute structure parameter	−0.02 (4)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.853 (13)	2.288 (13)	3.1296 (9)	168.8 (11)
N1—H2···Cl1ⁱ	0.877 (14)	2.255 (14)	3.1257 (9)	171.9 (13)

Symmetry code: (i) x+1/2, −y+1/2, z.

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Pourayoubi, M. & Sabbaghi, F. (2007). Acta Cryst. E63, o4366. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yazdanbakhsh, M. & Sabbaghi, F. (2007). Acta Cryst. E63, o4318. Web of Science CSD CrossRef IUCr Journals Google Scholar