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ISSN: 2056-9890

N-Benzyl­propan-2-aminium chloride

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[Pourayoubi, M. & Sabbaghi, F. (2007). Acta Cryst. E63, o4366.]); Yazdanbakhsh & Sabbaghi (2007[Yazdanbakhsh, M. & Sabbaghi, F. (2007). Acta Cryst. E63, o4318.]).

[Scheme 1]

Experimental

Crystal data
  • C10H16N+·Cl

  • Mr = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.818, Tmax = 0.910

  • 11694 measured reflections

  • 2720 independent reflections

  • 2662 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.15 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1229 Friedel pairs

  • Flack parameter: −0.02 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

The H atoms of the NH2 group were located from the difference Fourier synthesis and refined isotropically, no restraints were used. Finally, the geometrical and thermal parameters obtained for these H-atoms, as well as parameters of the hydrogen bonds for these H-atoms included, were rather realistic. The H(C) atom positions were calculated and refined in isotropic approximation in riding model with the Uiso(H) parameters equal to 1.2 Ueq(Ci), for methyl groups equal to 1.5 Ueq(Cii), where U(Ci) and U(Cii) are respectively the equivalent thermal parameters of the carbon atoms to which corresponding H atoms are bonded.

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
[Figure 1] Fig. 1. The molecular structure of the title salt, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50 % probability level.
[Figure 2] 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+·ClF(000) = 400
Mr = 185.69Dx = 1.197 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 8636 reflections
a = 9.9666 (6) Åθ = 2.3–34.0°
b = 18.0379 (11) ŵ = 0.32 mm1
c = 5.7307 (4) ÅT = 100 K
V = 1030.25 (11) Å3Prism, colourless
Z = 40.50 × 0.40 × 0.30 mm
Data collection top
Bruker APEXII CCD
diffractometer
2720 independent reflections
Radiation source: fine-focus sealed tube2662 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ϕ and ω scansθmax = 29.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1313
Tmin = 0.818, Tmax = 0.910k = 2424
11694 measured reflectionsl = 77
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021H 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 reflectionsΔρmax = 0.25 e Å3
119 parametersΔρmin = 0.15 e Å3
1 restraintAbsolute structure: Flack (1983), 1229 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (4)
Crystal data top
C10H16N+·ClV = 1030.25 (11) Å3
Mr = 185.69Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 9.9666 (6) ŵ = 0.32 mm1
b = 18.0379 (11) ÅT = 100 K
c = 5.7307 (4) Å0.50 × 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)
Tmin = 0.818, Tmax = 0.910Rint = 0.023
11694 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.057Δρmax = 0.25 e Å3
S = 1.07Δρmin = 0.15 e Å3
2720 reflectionsAbsolute structure: Flack (1983), 1229 Friedel pairs
119 parametersAbsolute 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
xyzUiso*/Ueq
Cl10.212804 (19)0.282008 (11)0.24289 (5)0.01590 (6)
N10.47016 (8)0.26697 (4)0.55218 (15)0.01274 (15)
H10.3950 (14)0.2666 (7)0.481 (2)0.013 (3)*
H20.5322 (12)0.2517 (7)0.455 (3)0.014 (3)*
C10.47024 (10)0.21793 (5)0.7630 (2)0.01667 (19)
H1A0.41810.24230.88840.020*
H1B0.56360.21230.81900.020*
C20.41198 (9)0.14208 (5)0.71879 (19)0.01422 (17)
C30.32866 (10)0.11207 (6)0.88949 (19)0.01721 (19)
H3A0.30640.14051.02350.021*
C40.27777 (10)0.04055 (6)0.8647 (2)0.0205 (2)
H4A0.22180.02020.98260.025*
C50.30877 (11)0.00100 (6)0.6679 (2)0.0192 (2)
H5A0.27430.04980.65120.023*
C60.39045 (10)0.02910 (5)0.49499 (19)0.0188 (2)
H6A0.41050.00100.35910.023*
C70.44277 (10)0.10012 (5)0.52059 (18)0.01675 (18)
H7A0.49950.12020.40330.020*
C80.50162 (11)0.34699 (5)0.6084 (2)0.0195 (2)
H8A0.58250.34870.71160.023*
C90.38428 (13)0.38228 (5)0.7366 (2)0.0281 (2)
H9A0.36310.35300.87580.042*
H9B0.30590.38370.63350.042*
H9C0.40830.43290.78300.042*
C100.53322 (12)0.38753 (6)0.3829 (2)0.0256 (2)
H10A0.60570.36170.30070.038*
H10B0.56130.43840.41840.038*
H10C0.45300.38870.28400.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01334 (10)0.01922 (10)0.01515 (10)0.00008 (7)0.00118 (9)0.00016 (10)
N10.0131 (4)0.0111 (3)0.0140 (4)0.0004 (3)0.0017 (3)0.0011 (3)
C10.0237 (4)0.0127 (4)0.0136 (5)0.0013 (3)0.0044 (4)0.0014 (3)
C20.0155 (4)0.0114 (4)0.0157 (4)0.0011 (3)0.0018 (4)0.0034 (4)
C30.0181 (4)0.0173 (4)0.0162 (4)0.0020 (3)0.0013 (4)0.0012 (4)
C40.0197 (5)0.0199 (5)0.0221 (6)0.0024 (4)0.0022 (4)0.0062 (4)
C50.0189 (4)0.0143 (4)0.0243 (5)0.0027 (4)0.0041 (4)0.0029 (3)
C60.0209 (4)0.0163 (4)0.0192 (5)0.0003 (4)0.0018 (4)0.0021 (4)
C70.0187 (4)0.0154 (4)0.0162 (4)0.0016 (3)0.0008 (4)0.0003 (4)
C80.0234 (5)0.0113 (4)0.0238 (5)0.0048 (4)0.0083 (4)0.0010 (4)
C90.0512 (6)0.0125 (4)0.0205 (5)0.0038 (4)0.0042 (6)0.0007 (5)
C100.0241 (5)0.0171 (5)0.0355 (6)0.0021 (4)0.0051 (5)0.0084 (4)
Geometric parameters (Å, º) top
N1—C11.4974 (13)C5—H5A0.9500
N1—C81.5118 (13)C6—C71.3910 (14)
N1—H10.853 (14)C6—H6A0.9500
N1—H20.877 (14)C7—H7A0.9500
C1—C21.5076 (12)C8—C101.5178 (16)
C1—H1A0.9900C8—C91.5207 (17)
C1—H1B0.9900C8—H8A1.0000
C2—C31.3927 (14)C9—H9A0.9800
C2—C71.3990 (14)C9—H9B0.9800
C3—C41.3934 (15)C9—H9C0.9800
C3—H3A0.9500C10—H10A0.9800
C4—C51.3892 (16)C10—H10B0.9800
C4—H4A0.9500C10—H10C0.9800
C5—C61.3925 (15)
C1—N1—C8113.08 (8)C7—C6—C5120.21 (10)
C1—N1—H1112.4 (9)C7—C6—H6A119.9
C8—N1—H1107.0 (8)C5—C6—H6A119.9
C1—N1—H2109.1 (9)C6—C7—C2120.11 (9)
C8—N1—H2106.8 (8)C6—C7—H7A119.9
H1—N1—H2108.2 (14)C2—C7—H7A119.9
N1—C1—C2113.60 (9)N1—C8—C10108.76 (9)
N1—C1—H1A108.8N1—C8—C9110.07 (8)
C2—C1—H1A108.8C10—C8—C9111.67 (9)
N1—C1—H1B108.8N1—C8—H8A108.8
C2—C1—H1B108.8C10—C8—H8A108.8
H1A—C1—H1B107.7C9—C8—H8A108.8
C3—C2—C7119.39 (8)C8—C9—H9A109.5
C3—C2—C1117.67 (9)C8—C9—H9B109.5
C7—C2—C1122.88 (9)H9A—C9—H9B109.5
C2—C3—C4120.36 (9)C8—C9—H9C109.5
C2—C3—H3A119.8H9A—C9—H9C109.5
C4—C3—H3A119.8H9B—C9—H9C109.5
C5—C4—C3120.08 (9)C8—C10—H10A109.5
C5—C4—H4A120.0C8—C10—H10B109.5
C3—C4—H4A120.0H10A—C10—H10B109.5
C4—C5—C6119.83 (9)C8—C10—H10C109.5
C4—C5—H5A120.1H10A—C10—H10C109.5
C6—C5—H5A120.1H10B—C10—H10C109.5
C8—N1—C1—C2168.17 (8)C4—C5—C6—C71.03 (16)
N1—C1—C2—C3138.75 (10)C5—C6—C7—C20.91 (15)
N1—C1—C2—C744.10 (12)C3—C2—C7—C60.02 (14)
C7—C2—C3—C40.83 (15)C1—C2—C7—C6177.09 (9)
C1—C2—C3—C4176.43 (9)C1—N1—C8—C10166.04 (8)
C2—C3—C4—C50.71 (16)C1—N1—C8—C971.33 (11)
C3—C4—C5—C60.22 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.853 (13)2.288 (13)3.1296 (9)168.8 (11)
N1—H2···Cl1i0.877 (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 formulaC10H16N+·Cl
Mr185.69
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)100
a, b, c (Å)9.9666 (6), 18.0379 (11), 5.7307 (4)
V3)1030.25 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.50 × 0.40 × 0.30
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.818, 0.910
No. of measured, independent and
observed [I > 2σ(I)] reflections
11694, 2720, 2662
Rint0.023
(sin θ/λ)max1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.057, 1.07
No. of reflections2720
No. of parameters119
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.15
Absolute structureFlack (1983), 1229 Friedel pairs
Absolute structure parameter0.02 (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···AD—HH···AD···AD—H···A
N1—H1···Cl10.853 (13)2.288 (13)3.1296 (9)168.8 (11)
N1—H2···Cl1i0.877 (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

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

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
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