Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
cross.png
share
Previous article cross.png
Next article cross.png
Previous article cross.png
Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
cross.png
share
Next article cross.png

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 61| Part 10| October 2005| Pages o3133-o3135
doi:10.1107/S1600536805027182

{N-[(S)-1-Phenyl­ethyl]carbamo­yl}methyl­aminium chloride

CROSSMARK_Color_square_no_text.svg
Craig Williamson,a John M. D. Storeya and William T. A. Harrisona*

aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
*Correspondence e-mail: w.harrison@abdn.ac.uk

(Received 24 August 2005; accepted 26 August 2005; online 7 September 2005)

In the title compound, C10H15N2O+·Cl−, the crystal packing is influenced by N—H⋯O and N—H⋯Cl hydrogen bonds, resulting in a layered structure.

Comment

The known title compound, (I)[link] (Fig. 1[link]), was prepared as an inter­mediate in the syntheses of new asymmetric catalysts, following the literature procedure of Ho et al. (2001[Ho, B., Crider, M. & Stables, J. P. (2001). Eur. J. Med. Chem. 36, 265-286.]).

[Scheme 1]

All the geometrical parameters for (I)[link] lie within their expected ranges (Allen et al., 1995[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1995). International Tables for Crystallography, Vol. C, edited by A. J. C. Wilson, pp. 685-706. Dordrecht: Kluwer.]). The absolute configuration of (I)[link] is well defined and atom C7 has S configuration, as expected from the configuration of the equivalent C atom in the (S)-1-phenyl­ethyl­amine starting material. The dihedral angle between the mean planes of the benzene ring (atoms C1–C6) and the C7/C9/C10/N1/O1 grouping is 66.14 (13)°.

The crystal packing in (I)[link] is influenced by hydrogen bonds (Table 1[link]). An N—H⋯O bond arising from the N1 group links the cations into chains propagating in the a direction. The –NH3 group participates in three N—H⋯Cl bonds [mean H⋯Cl = 2.32 Å, mean N⋯Cl = 3.183 (3) Å, mean N—H⋯Cl = 159°], which crosslink the [100] stacks in the b direction. The only inter­molecular inter­actions in the c direction are van der Waals forces (Fig. 2[link]). A PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]) analysis of (I)[link] flagged a short intra­molecular C—H⋯O distance (Fig. 1[link] and Table 1[link]), although its structural significance – an attractive inter­action or a repulsive steric contact – is not clear.

[Figure 1]
Figure 1
View of (I)[link] (50% probability displacement ellipsoids; H atoms are drawn as small spheres of arbitrary radii). The N—H⋯Cl hydrogen bond and possible C—H⋯O inter­action are indicated by dashed lines.
[Figure 2]
Figure 2
The packing of (I)[link], viewed down [010], with all C-bound H atoms omitted for clarity and hydrogen bonds indicated by dashed lines.

Experimental

N-Boc glycine (10 mmol, 1.75 g) was dissolved in dry THF (30 ml) in a dry flask under nitro­gen. The solution was cooled to 195 K, and N-methyl morpholine (10 mmol, 1.01 g, 1.09 ml) was added with stirring. iBu-chloro­formate (10 mmol, 1.36 g, 1.30 ml) was added, and the solution stirred for 30 min. (S)-1-Phenyl­ethyl­amine (10 mmol, 1.21 g, 1.29 ml) was added in one portion and the reaction mixture stirred at room temperature for 18 h. The solvent was removed in vacuo. The residue was taken up in EtOAc (30 ml), washed with 10% aqueous Na2CO3 (20 ml), 0.1 M aqueous HCl (20 ml) and saturated brine (20 ml), then dried over Na2SO4 and filtered, and the solvent was removed in vacuo. The resulting oil (1.37 g, 4.95 mmol) was dissolved in dry dichloromethane (DCM, 15 ml) and cooled to 273 K. Bubbling excess dry HCl through the reaction medium with stirring for 2 h allowed the collection of the desired product as a white precipitate, which was recrystallized from EtOH/Et2O (1.09 g, 89%). Slow evaporation of a DCM solution of the purified material produced colourless needles of (I)[link] suitable for diffraction; m.p. 446–449 K. [α]D = −97.0°, C = 0.6 (MeOH); IR (KBr, cm−1): νmax 3289 (C=O), 2967 (CH), 1660 (C=O), 1561 (C=O); 1H NMR (250 MHz, CD3OD): δH 9.2 (1H, d, J = 8.0 Hz, NH), 8.2 (3H, s, N+H3), 7.3 (5H, m, Ph), 4.9 (1H, q, J = 7.0 Hz, CH), 3.6 (2H, s, CH2), 1.3 (3H, d, J = 7.0 Hz, CH3); 13C NMR (250 MHz, CD3OD): δC 164.9 (C=O), 144.1, 128.3, 126.8, 126.1, 48.5 (CH), 40.1 (CH2), 22.6 (CH3); MS (ESI+): calcualted m/z 179.1179; found 179.1180 [M—Cl]+; (ESI−) 35.4 and 37.4 [Cl]−.

Crystal data

  • C10H15N2O+·Cl−

  • Mr = 214.69

  • Orthorhombic, P 21 21 21

  • a = 4.6309 (3) Å

  • b = 5.8963 (4) Å

  • c = 39.939 (3) Å

  • V = 1090.54 (13) Å3

  • Z = 4

  • Dx = 1.308 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 856 reflections

  • θ = 2.9–27.5°

  • μ = 0.32 mm−1

  • T = 120 (2) K

  • Block cut from needle, colourless

  • 0.30 × 0.24 × 0.16 mm
Data collection

  • Nonius KappaCCD diffractometer

  • ω and φ scans

  • Absorption correction: multi-scan(SADABS; Bruker, 2003[Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])Tmin = 0.910, Tmax = 0.951

  • 3682 measured reflections

  • 1768 independent reflections

  • 1578 reflections with I > 2σ(I)

  • Rint = 0.030

  • θmax = 26.0°

  • h = −5 → 5

  • k = −6 → 7

  • l = −48 → 48
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.127

  • S = 1.14

  • 1768 reflections

  • 129 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0431P)2 + 1.5926P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max = 0.001

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.39 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 439 Friedel pairs

  • Flack parameter: 0.08 (13)

Table 1
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O1i 0.88 2.01 2.839 (4) 156
N2—H2A⋯Cl1 0.91 2.32 3.181 (3) 157
N2—H2B⋯Cl1ii 0.91 2.27 3.146 (3) 162
N2—H2C⋯Cl1iii 0.91 2.36 3.222 (3) 158
C7—H7⋯O1 1.00 2.45 2.809 (5) 101
Symmetry codes: (i) x+1, y, z; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

All H atoms were placed in calculated positions (C—H = 0.95–0.99 Å and N—H = 0.88–0.91 Å) and refined as riding on their carrier atoms, allowing for rotation of the rigid terminal –XH3 groups. The constraint Uiso(H) = 1.2Ueq(carrier) or Uiso(H) = 1.5Ueq(methyl carrier) was applied as applicable.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]), SCALEPACK and SORTAV (Blessing 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536805027182/bt6726sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536805027182/bt6726Isup2.hkl


Comment top

The known title compound, (I) (Fig. 1), was prepared as an intermediate in the syntheses of new asymmetric catalysts, following the literature procedure of Ho et al. (2001).

All the geometrical parameters for (I) lie within their expected ranges (Allen et al., 1995). The absolute structure of (I) is well defined and atom C7 has S conformation, as expected from the conformation of the equivalent C atom in the (S)-1-phenylethylamine starting material. The dihedral angle between the best planes of the benzene ring (atoms C1–C6) and the C7/C9/C10/N1/O1 grouping is 66.14 (13)°.

The crystal packing in (I) is influenced by hydrogen bonds (Table 1). An N—H···O bond arising from the N1 group links the molecules into chains propagating in the a direction. The –NH3 group participates in three N—H···Cl bonds [mean H···Cl = 2.32 Å, mean N···Cl = 3.183 (3) Å, mean N—H···Cl = 159°], which crosslink the [100] stacks in the b direction. The only intermolecular interactions in the c direction are van der Waals forces (Fig. 2). A PLATON (Spek, 2003) analysis of (I) flagged a short intramolecular C—H···O distance (Fig. 1 and Table 1), although its structural significance – an attractive interaction or a repulsive steric contact – is not clear.

Experimental top

N-Boc glycine (10 mmol, 1.75 g) was dissolved in dry THF (30 ml) in a dry flask under nitrogen. The solution was cooled to 195 K, and N-methyl morpholine (10 mmol, 1.01 g, 1.09 ml) was added with stirring. iBu-chloroformate (10 mmol, 1.36 g, 1.30 ml) was added, and the solution stirred for 30 min. (S)-1-Phenylethylamine (10 mmol, 1.21 g, 1.29 ml) was added in one portion and the reaction stirred at room temperature for 18 h. The solvent was removed in vacuo. The residue was taken up in EtOAc (30 ml), washed with 10% aqueous Na2CO3 (20 ml), 0.1 M aqueous HCl (20 ml) and saturated brine (20 ml), then dried over Na2SO4 and filtered, and the solvent was removed in vacuo. The resulting oil (1.37 g, 4.95 mmol) was dissolved in dry DCM (15 ml) and cooled to 273 K. Bubbling excess dry HCl through the reaction medium with stirring for 2 h allowed the collection of the desired product as a white precipitate, which was recrystallized from EtOH/Et2O (1.09 g, 89%). Slow evaporation of a DCM solution of the purified material produced colourless needles of (I) suitable for diffraction; m.p. 446–449 K. [α]D = −97.0°, C = 0.6 (MeOH); IR (KBr, cm−1): νmax 3289 (C═O), 2967 (CH), 1660 (C═O), 1561 (C═ O); 1H NMR (250 MHz, CD3OD): δH 9.2 (1H, d, J = 8.0 Hz, NH), 8.2 (3H, s, N+H3), 7.3 (5H, m, Ph), 4.9 (1H, q, J = 7.0 Hz, CH), 3.6 (2H, s, CH2), 1.3 (3H, d, J = 7.0 Hz, CH3); 13C NMR (250 MHz, CD3OD): δC 164.9 (C═O), 144.1, 128.3, 126.8, 126.1, 48.5 (CH), 40.1 (CH2), 22.6 (CH3); MS (ESI+): calcualted m/z 179.1179; found 179.1180 [M—Cl+]; (ESI−) 35.4 and 37.4 [Cl−].

Refinement top

All H atoms were placed in calculated positions (C—H = 0.95–0.99 Å and N—H = 0.88–0.91 Å) and refined as riding on their carrier atoms, allowing for rotation of the rigid terminal –XH3 groups. The constraint Uiso(H) = 1.2Ueq(carrier) or Uiso(H) = 1.5Ueq(methyl carrier) was applied as applicable.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor 1997), SCALEPACK and SORTAV (Blessing 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of (I) (50% probability displacement ellipsoids; H atoms are drawn as small spheres of arbitrary radii). The N—H···Cl hydrogen bond and possible C—H···O interaction are indicated by dashed lines.
[Figure 2] Fig. 2. Unit-cell packing in (I), viewed down [010], with all C-bound H atoms omitted for clarity and hydrogen bonds indicated by dashed lines.
{N-[(S)-1-Phenylethyl]carbamoyl}methylaminium chloride top
Crystal data top
C10H15N2O+·Cl−F(000) = 456
Mr = 214.69Dx = 1.308 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 856 reflections
a = 4.6309 (3) Åθ = 2.9–27.5°
b = 5.8963 (4) ŵ = 0.32 mm−1
c = 39.939 (3) ÅT = 120 K
V = 1090.54 (13) Å3Block cut from needle, colourless
Z = 40.30 × 0.24 × 0.16 mm
Data collection top
Nonius KappaCCD
diffractometer		1768 independent reflections
Radiation source: fine-focus sealed tube1578 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω and ϕ scansθmax = 26.0°, θmin = 4.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		h = −5→5
Tmin = 0.910, Tmax = 0.951k = −6→7
3682 measured reflectionsl = −48→48
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0431P)2 + 1.5926P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.001
1768 reflectionsΔρmax = 0.41 e Å−3
129 parametersΔρmin = −0.39 e Å−3
0 restraintsAbsolute structure: Flack (1983), 439 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.08 (13)
Crystal data top
C10H15N2O+·Cl−V = 1090.54 (13) Å3
Mr = 214.69Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.6309 (3) ŵ = 0.32 mm−1
b = 5.8963 (4) ÅT = 120 K
c = 39.939 (3) Å0.30 × 0.24 × 0.16 mm
Data collection top
Nonius KappaCCD
diffractometer		1768 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		1578 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 0.951Rint = 0.030
3682 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.127Δρmax = 0.41 e Å−3
S = 1.14Δρmin = −0.39 e Å−3
1768 reflectionsAbsolute structure: Flack (1983), 439 Friedel pairs
129 parametersAbsolute structure parameter: 0.08 (13)
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
C10.3476 (8)0.2857 (6)0.57786 (9)0.0241 (8)
H10.32200.16730.59370.029*
C20.5263 (9)0.2492 (7)0.55044 (10)0.0282 (9)
H20.62200.10790.54770.034*
C30.5636 (9)0.4212 (7)0.52715 (10)0.0286 (9)
H30.68600.39840.50840.034*
C40.4228 (9)0.6256 (7)0.53132 (10)0.0303 (10)
H40.44750.74320.51530.036*
C50.2449 (8)0.6596 (7)0.55885 (9)0.0263 (9)
H50.14850.80070.56140.032*
C60.2054 (8)0.4904 (7)0.58274 (9)0.0222 (8)
C70.0020 (9)0.5204 (7)0.61243 (10)0.0247 (9)
H7−0.18270.44170.60670.030*
C8−0.0733 (10)0.7653 (7)0.62115 (11)0.0368 (11)
H8A−0.20230.76760.64060.055*
H8B−0.16990.83680.60200.055*
H8C0.10390.84890.62640.055*
C9−0.0481 (7)0.3063 (6)0.66460 (8)0.0167 (7)
C100.1047 (7)0.2278 (6)0.69611 (8)0.0192 (7)
H10A0.20410.08190.69190.023*
H10B0.25150.34100.70280.023*
N10.1207 (7)0.4076 (5)0.64230 (7)0.0219 (7)
H1A0.30870.40730.64540.026*
N2−0.1105 (6)0.1991 (5)0.72335 (7)0.0174 (6)
H2A−0.01730.18590.74330.021*
H2B−0.21680.07200.71950.021*
H2C−0.22930.32200.72390.021*
O1−0.3109 (5)0.2796 (5)0.66108 (6)0.0206 (6)
Cl10.36806 (18)0.20605 (14)0.78047 (2)0.0210 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.032 (2)0.0212 (17)0.0196 (16)−0.001 (2)−0.0033 (16)0.0040 (15)
C20.031 (2)0.024 (2)0.030 (2)−0.0001 (17)0.0023 (17)−0.0045 (17)
C30.030 (2)0.035 (2)0.0206 (17)−0.0040 (19)0.0050 (17)0.0005 (18)
C40.033 (2)0.033 (2)0.0248 (19)−0.0061 (19)0.0027 (18)0.0046 (18)
C50.030 (2)0.025 (2)0.0239 (18)0.0029 (17)−0.0003 (16)0.0030 (16)
C60.0155 (18)0.028 (2)0.0230 (17)−0.0033 (16)−0.0024 (15)0.0032 (17)
C70.021 (2)0.028 (2)0.0247 (18)−0.0027 (17)−0.0014 (16)0.0001 (18)
C80.040 (2)0.036 (3)0.035 (2)0.012 (2)0.010 (2)0.011 (2)
C90.0138 (16)0.0141 (16)0.0220 (17)0.0002 (15)0.0023 (14)−0.0001 (17)
C100.0163 (16)0.0221 (18)0.0193 (16)−0.0005 (16)0.0026 (14)0.0041 (15)
N10.0154 (15)0.0284 (16)0.0219 (14)−0.0011 (15)−0.0013 (13)0.0044 (13)
N20.0175 (13)0.0143 (13)0.0202 (13)−0.0001 (15)−0.0020 (12)0.0020 (13)
O10.0152 (12)0.0262 (13)0.0204 (12)0.0005 (11)0.0010 (10)0.0003 (12)
Cl10.0212 (4)0.0177 (4)0.0241 (4)0.0013 (4)−0.0005 (4)0.0003 (4)
Geometric parameters (Å, º) top
C1—C61.389 (5)C7—H71.0000
C1—C21.390 (5)C8—H8A0.9800
C1—H10.9500C8—H8B0.9800
C2—C31.387 (6)C8—H8C0.9800
C2—H20.9500C9—O11.235 (4)
C3—C41.380 (6)C9—N11.327 (4)
C3—H30.9500C9—C101.516 (5)
C4—C51.389 (5)C10—N21.485 (4)
C4—H40.9500C10—H10A0.9900
C5—C61.393 (5)C10—H10B0.9900
C5—H50.9500N1—H1A0.8800
C6—C71.524 (5)N2—H2A0.9100
C7—N11.472 (5)N2—H2B0.9100
C7—C81.526 (6)N2—H2C0.9100
C6—C1—C2121.9 (4)C7—C8—H8A109.5
C6—C1—H1119.1C7—C8—H8B109.5
C2—C1—H1119.1H8A—C8—H8B109.5
C3—C2—C1119.3 (4)C7—C8—H8C109.5
C3—C2—H2120.3H8A—C8—H8C109.5
C1—C2—H2120.3H8B—C8—H8C109.5
C4—C3—C2119.9 (4)O1—C9—N1124.1 (3)
C4—C3—H3120.0O1—C9—C10121.0 (3)
C2—C3—H3120.0N1—C9—C10114.8 (3)
C3—C4—C5120.1 (4)N2—C10—C9109.2 (3)
C3—C4—H4119.9N2—C10—H10A109.8
C5—C4—H4119.9C9—C10—H10A109.8
C4—C5—C6121.1 (4)N2—C10—H10B109.8
C4—C5—H5119.4C9—C10—H10B109.8
C6—C5—H5119.4H10A—C10—H10B108.3
C1—C6—C5117.7 (3)C9—N1—C7121.8 (3)
C1—C6—C7120.2 (4)C9—N1—H1A119.1
C5—C6—C7122.1 (4)C7—N1—H1A119.1
N1—C7—C6110.3 (3)C10—N2—H2A109.5
N1—C7—C8109.1 (3)C10—N2—H2B109.5
C6—C7—C8115.4 (3)H2A—N2—H2B109.5
N1—C7—H7107.2C10—N2—H2C109.5
C6—C7—H7107.2H2A—N2—H2C109.5
C8—C7—H7107.2H2B—N2—H2C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.882.012.839 (4)156
N2—H2A···Cl10.912.323.181 (3)157
N2—H2B···Cl1ii0.912.273.146 (3)162
N2—H2C···Cl1iii0.912.363.222 (3)158
C7—H7···O11.002.452.809 (5)101
Symmetry codes: (i) x+1, y, z; (ii) −x, y−1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC10H15N2O+·Cl−
Mr214.69
Crystal system, space groupOrthorhombic, P212121
Temperature (K)120
a, b, c (Å)4.6309 (3), 5.8963 (4), 39.939 (3)
V (Å3)1090.54 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.32
Crystal size (mm)0.30 × 0.24 × 0.16
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.910, 0.951
No. of measured, independent and
observed [I > 2σ(I)] reflections		3682, 1768, 1578
Rint0.030
(sin θ/λ)max (Å−1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.127, 1.14
No. of reflections1768
No. of parameters129
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.39
Absolute structureFlack (1983), 439 Friedel pairs
Absolute structure parameter0.08 (13)

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor 1997), SCALEPACK and SORTAV (Blessing 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.882.012.839 (4)156
N2—H2A···Cl10.912.323.181 (3)157
N2—H2B···Cl1ii0.912.273.146 (3)162
N2—H2C···Cl1iii0.912.363.222 (3)158
C7—H7···O11.002.452.809 (5)101
Symmetry codes: (i) x+1, y, z; (ii) −x, y−1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2.
 

Acknowledgements

The authors thank the EPSRC National Mass Spectrometry Service (University of Swansea) and the EPSRC National Crystallography Service (University of Southampton) for data collections.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1995). International Tables for Crystallography, Vol. C, edited by A. J. C. Wilson, pp. 685–706. Dordrecht: Kluwer.  Google Scholar
 First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationBruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationHo, B., Crider, M. & Stables, J. P. (2001). Eur. J. Med. Chem. 36, 265–286.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationNonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 61| Part 10| October 2005| Pages o3133-o3135
doi:10.1107/S1600536805027182
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS