N-Benzyl-propan-2-aminium chloride.

In the crystal structure of title salt, C(10)H(16)N(+)·Cl(-), the amino H atoms are involved in inter-molecular 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 = 185.69

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.057

S = 1.07

2720 reflections

119 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 1229 Friedel pairs

Flack parameter: −0.02 (4)

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810006707/ng2732sup1.cif

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

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

C10H16N+·Cl−	F(000) = 400
Mr = 185.69	Dx = 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

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

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(Fo2) + (0.0336P)2 + 0.1229P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2720 reflections	Δρmax = 0.25 e Å−3
119 parameters	Δρmin = −0.15 e Å−3
1 restraint	Absolute structure: Flack (1983), 1229 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (4)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .