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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o708.
Published online 2010 February 27. doi:  10.1107/S1600536810006707
PMCID: PMC2983519

N-Benzyl­propan-2-aminium chloride

Abstract

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 [triangle]); Yazdanbakhsh & Sabbaghi (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o708-scheme1.jpg

Experimental

Crystal data

  • C10H16N+·Cl
  • M r = 185.69
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o708-efi1.jpg
  • 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 [triangle]) 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 [triangle]), 1229 Friedel pairs
  • Flack parameter: −0.02 (4)

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.

Crystal data

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

Bruker APEXII CCD diffractometer2720 independent reflections
Radiation source: fine-focus sealed tube2662 reflections with I > 2σ(I)
graphiteRint = 0.023
[var phi] and ω scansθmax = 29.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −13→13
Tmin = 0.818, Tmax = 0.910k = −24→24
11694 measured reflectionsl = −7→7

Refinement

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) = 0.057w = 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 methodsFlack parameter: −0.02 (4)

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. 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)

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)
H5A0.2743−0.04980.65120.023*
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)

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, °)

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—C3−138.75 (10)C5—C6—C7—C2−0.91 (15)
N1—C1—C2—C744.10 (12)C3—C2—C7—C6−0.02 (14)
C7—C2—C3—C40.83 (15)C1—C2—C7—C6177.09 (9)
C1—C2—C3—C4−176.43 (9)C1—N1—C8—C10166.04 (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, °)

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 codes: (i) x+1/2, −y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2732).

References

  • Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Pourayoubi, M. & Sabbaghi, F. (2007). Acta Cryst. E63, o4366.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yazdanbakhsh, M. & Sabbaghi, F. (2007). Acta Cryst. E63, o4318.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography