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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 5| May 2008| Page o940
doi:10.1107/S1600536808011550

Redetermination of (+)-methamphetamine hydro­chloride at 90 K

Patrick Hakey,a Wayne Ouellette,a Jon Zubietaa and Timothy Kortera*

aDepartment of Chemistry, Syracuse University, Syracuse, New York 13244, USA
*Correspondence e-mail: tmkorter@syr.edu

(Received 20 March 2008; accepted 22 April 2008; online 30 April 2008)

The title crystal structure (systematic name: N-methyl-1-phenyl­propan-2-aminium chloride), C10H16N+·Cl−, was orginally determined by Simon, Bocskei & Torok [Acta Pharm. Hung. (1992). 62, 225–230] and Yao, Kan & Wang [Huaxue Shijie (1999). 40, 568–570] at room temperature but no atomic coordinates are available for these determinations. The mol­ecule has inter­est with respect to biological activity. In the crystal structure, inter­molecular N—H⋯Cl hydrogen bonds form one-dimensional chains.

Related literature

For related literature, see: Cho (1990[Cho, A. K. (1990). Science, 249, 631-634.]); Cho & Melega (2002[Cho, A. K. & Melega, W. P. (2002). J. Addict. Dis. 21, 21-34.]); Davis & Swalwell (1994[Davis, G. G. & Swalwell, C. I. (1994). J. Forensic Sci. 39, 1481-1485.]); O'Neil et al. (2001[O'Neil, M. J., Smith, A., Heckelman, P. E. & Budavari, S. (2001). Editors. The Merck Index, 13th ed., entry 5975. Whitehouse Station, NJ: Merck & Co.]); Simon et al. (1992[Simon, K., Bocskei, Z. & Torok, Z. (1992). Acta Pharm. Hung. 62, 225-230.]); Yao et al. (1999[Yao, Y., Kan, Y. & Wang, S. (1999). Huaxue Shijie, 40, 568-570.]); Yu et al. (2003[Yu, Q., Larson, D. F. & Watson, R. R. (2003). Life Sci. 73, 129-140.]).

[Scheme 1]

Experimental

Crystal data

  • C10H16N+·Cl−

  • Mr = 185.69

  • Monoclinic, P 21

  • a = 7.1022 (11) Å

  • b = 7.2949 (11) Å

  • c = 10.8121 (17) Å

  • β = 97.293 (4)°

  • V = 555.64 (15) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 90 (2) K

  • 0.28 × 0.14 × 0.10 mm
Data collection

  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.922, Tmax = 0.971

  • 5892 measured reflections

  • 2720 independent reflections

  • 2379 reflections with I > 2σ(I)

  • Rint = 0.047
Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.117

  • S = 1.05

  • 2720 reflections

  • 174 parameters

  • 1 restraint

  • All H-atom parameters refined

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.46 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1235 Freidel pairs

  • Flack parameter: 0.00 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1D⋯Cl1i 0.93 (4) 2.14 (4) 3.069 (2) 179 (4)
N1—H1E⋯Cl1ii 0.90 (3) 2.22 (3) 3.116 (2) 176 (3)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+1]; (ii) x+1, y, z.

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, 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: CrystalMaker (Palmer, 2006[Palmer, D. (2006). CrystalMaker. CrystalMaker Software Ltd, Yarnton, Oxfordshire, England.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808011550/lh2608sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011550/lh2608Isup2.hkl

checkCIF report


Comment top

The compound, (+)-methamphetamine hydrochloride has been reinvestigated in this study by single-crystal x-ray diffraction to provide a complete determination of the atomic coordinates and lattice dimensions at 90 (2) K. Earlier structural studies on this compound by Simon et al. (1992) and by Yanhong et al. (1999) were performed at or near room temperature and did not include atomic coordinates. The determination of crystallographic data at cryogenic temperatures improves the precision of the atomic coordinates and also provides insight into temperature-induced lattice changes. This information is important in the complete understanding of the molecular solid and is particularly useful for validation of first-principles solid-state modeling.

The compound studied is a synthetic sympathomimetic drug and is specified as a controlled substance by the United States Federal government (O'Neil et al., 2001). The substance is a strong stimulant that affects the central nervous system (CNS) and contributes cardiactoxicity (Yu et al., 2003). The use of methamphetamine has increased substantially and is becoming a problem nation wide with its use increasing across all age groups (Cho & Melega, 2002). The compound has a more potent effect on the CNS than structurally similar amphetamine due to its increased penetration of the CNS (Davis & Swalwell,1994). The potency of methamphetamine is also dependent upon its chirality, as its dextrorotatory enantiomer exhibits an effect roughly fives times greater than that provided by the levorotatory enantiomer (Cho, 1990). The stimulant effects of methamphetamine can be compared to the effects brought on by the use of cocaine, however, the duration of the effects can be much greater for the methamphetamine than for cocaine (Cho, 1990).

The (+)-methamphetamine hydrochloride form of methamphetamine has become the primary form used (Cho & Melega, 2002). This highlights the importance of complete characterization of the substance. Knowledge of the solid-state Crystal Structure of this compound is imperative for its identification and detection via various spectroscopic methods, such as solid-state NMR and terahertz. The unit-cell dimensions determined by this study are slightly smaller than those published by Simon et al., (1992) leading to a reduction in the unit cell volume of approximately 2.4% from the previously calculated value. Overall the basic structural parameters, such as the space group, P21, are in agreement with earlier work (Simon et al., 1992).

Related literature top

For related literature, see: Cho (1990); Cho & Melega (2002); Davis & Swalwell (1994); O'Neil et al. (2001); Simon et al. (1992); Yao et al. (1999); Yu et al. (2003).

Experimental top

The material for this work was purchased from Sigma-Aldrich and was used without any further purification.

Refinement top

H atoms were located in a difference map and refined freely.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atom numbering scheme and thermal ellipsoids drawn at 50% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed in the ac plane, showing hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
[Figure 3] Fig. 3. The crystal packing of the title compound, showing hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
(+)-methamphetamine hydrochloride top
Crystal data top
C10H16N+·Cl−F(000) = 200
Mr = 185.69Dx = 1.110 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 964 reflections
a = 7.1022 (11) Åθ = 2.9–22.5°
b = 7.2949 (11) ŵ = 0.30 mm−1
c = 10.8121 (17) ÅT = 90 K
β = 97.293 (4)°Block, colorless
V = 555.64 (15) Å30.28 × 0.14 × 0.10 mm
Z = 2
Data collection top
Bruker APEX CCD area-detector
diffractometer		2720 independent reflections
Radiation source: fine-focus sealed tube2379 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 512 pixels mm-1θmax = 28.2°, θmin = 1.9°
ϕ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		k = −9→9
Tmin = 0.922, Tmax = 0.971l = −14→14
5892 measured reflections
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)] = 0.051All H-atom parameters refined
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0575P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2720 reflectionsΔρmax = 0.43 e Å−3
174 parametersΔρmin = −0.46 e Å−3
1 restraintAbsolute structure: Flack (1983), 1235 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (10)
Crystal data top
C10H16N+·Cl−V = 555.64 (15) Å3
Mr = 185.69Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.1022 (11) ŵ = 0.30 mm−1
b = 7.2949 (11) ÅT = 90 K
c = 10.8121 (17) Å0.28 × 0.14 × 0.10 mm
β = 97.293 (4)°
Data collection top
Bruker APEX CCD area-detector
diffractometer		2720 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		2379 reflections with I > 2σ(I)
Tmin = 0.922, Tmax = 0.971Rint = 0.047
5892 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051All H-atom parameters refined
wR(F2) = 0.117Δρmax = 0.43 e Å−3
S = 1.05Δρmin = −0.46 e Å−3
2720 reflectionsAbsolute structure: Flack (1983), 1235 Freidel pairs
174 parametersAbsolute structure parameter: 0.00 (10)
1 restraint
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
Cl10.23185 (8)0.78305 (9)0.55574 (6)0.02213 (16)
N10.8031 (3)0.6811 (3)0.5363 (2)0.0172 (4)
C10.6896 (4)0.7867 (6)0.4357 (2)0.0224 (5)
C20.7510 (5)0.8922 (5)0.7083 (3)0.0256 (6)
C30.7409 (4)0.6944 (4)0.6644 (3)0.0187 (5)
C40.8700 (4)0.5637 (4)0.7481 (3)0.0236 (6)
C50.8089 (4)0.5381 (4)0.8763 (2)0.0202 (5)
C60.8940 (4)0.6384 (4)0.9782 (3)0.0228 (6)
C70.8402 (4)0.6117 (4)1.0956 (3)0.0249 (6)
C80.7005 (4)0.4842 (4)1.1138 (3)0.0262 (6)
C90.6134 (4)0.3862 (4)1.0127 (3)0.0281 (6)
C100.6678 (4)0.4130 (4)0.8947 (3)0.0248 (6)
H1A0.718 (5)0.908 (6)0.446 (3)0.039 (10)*
H1D0.791 (4)0.560 (5)0.509 (3)0.024 (8)*
H1B0.558 (4)0.754 (4)0.436 (2)0.018 (7)*
H1E0.925 (4)0.717 (4)0.541 (3)0.020 (8)*
H1C0.733 (4)0.747 (5)0.356 (3)0.027 (9)*
H2A0.650 (5)0.967 (5)0.659 (3)0.026 (9)*
H2B0.880 (5)0.945 (5)0.718 (3)0.030 (10)*
H2C0.724 (5)0.895 (5)0.791 (3)0.034 (9)*
H3A0.622 (5)0.651 (5)0.654 (3)0.023 (8)*
H4A0.863 (4)0.446 (4)0.701 (3)0.017 (7)*
H4B0.996 (4)0.626 (4)0.757 (3)0.013 (7)*
H60.980 (4)0.725 (4)0.965 (3)0.017 (7)*
H70.900 (4)0.680 (4)1.164 (3)0.021 (7)*
H80.681 (5)0.457 (5)1.193 (3)0.027 (9)*
H90.521 (4)0.278 (7)1.025 (3)0.030 (7)*
H100.611 (4)0.337 (4)0.827 (3)0.017 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0193 (3)0.0208 (3)0.0275 (3)−0.0001 (3)0.0077 (2)0.0022 (3)
N10.0186 (11)0.0200 (12)0.0139 (10)−0.0016 (9)0.0064 (8)0.0003 (9)
C10.0263 (12)0.0248 (12)0.0166 (11)−0.0002 (17)0.0055 (9)0.0004 (15)
C20.0345 (17)0.0268 (15)0.0167 (14)0.0038 (13)0.0082 (12)−0.0019 (11)
C30.0191 (13)0.0265 (14)0.0114 (12)−0.0008 (11)0.0052 (10)0.0006 (11)
C40.0268 (14)0.0282 (16)0.0172 (13)0.0038 (12)0.0076 (11)0.0011 (11)
C50.0193 (12)0.0226 (13)0.0192 (13)0.0032 (10)0.0049 (10)0.0024 (10)
C60.0222 (13)0.0260 (14)0.0205 (13)−0.0036 (12)0.0041 (10)0.0017 (11)
C70.0266 (14)0.0293 (15)0.0184 (13)−0.0006 (11)0.0016 (11)−0.0043 (11)
C80.0280 (14)0.0352 (16)0.0172 (13)0.0045 (12)0.0094 (11)0.0061 (11)
C90.0267 (15)0.0294 (16)0.0292 (15)−0.0050 (12)0.0070 (12)0.0057 (12)
C100.0254 (14)0.0270 (14)0.0222 (13)−0.0025 (11)0.0034 (11)−0.0017 (11)
Geometric parameters (Å, º) top
N1—C11.485 (4)C4—H4A1.00 (3)
N1—C31.510 (3)C4—H4B1.00 (3)
N1—H1D0.93 (3)C5—C101.388 (4)
N1—H1E0.90 (3)C5—C61.395 (4)
C1—H1A0.91 (4)C6—C71.386 (4)
C1—H1B0.97 (3)C6—H60.90 (3)
C1—H1C0.99 (3)C7—C81.392 (4)
C2—C31.518 (4)C7—H70.95 (3)
C2—H2A1.00 (3)C8—C91.384 (4)
C2—H2B0.99 (4)C8—H80.90 (3)
C2—H2C0.94 (3)C9—C101.393 (4)
C3—C41.536 (4)C9—H91.05 (4)
C3—H3A0.89 (3)C10—H100.96 (3)
C4—C51.515 (4)
C1—N1—C3116.4 (2)C5—C4—C3113.4 (2)
C1—N1—H1D104 (2)C5—C4—H4A111.2 (18)
C3—N1—H1D109 (2)C3—C4—H4A104.2 (17)
C1—N1—H1E108.9 (19)C5—C4—H4B109.2 (17)
C3—N1—H1E108.5 (19)C3—C4—H4B103.6 (16)
H1D—N1—H1E110 (3)H4A—C4—H4B115 (2)
N1—C1—H1A109 (2)C10—C5—C6118.7 (2)
N1—C1—H1B107.8 (17)C10—C5—C4120.5 (3)
H1A—C1—H1B116 (3)C6—C5—C4120.8 (2)
N1—C1—H1C106.5 (18)C7—C6—C5120.5 (3)
H1A—C1—H1C108 (3)C7—C6—H6120.9 (19)
H1B—C1—H1C110 (2)C5—C6—H6118.5 (19)
C3—C2—H2A110 (2)C6—C7—C8120.5 (3)
C3—C2—H2B114 (2)C6—C7—H7119.6 (19)
H2A—C2—H2B116 (3)C8—C7—H7119.8 (19)
C3—C2—H2C108 (2)C9—C8—C7119.3 (3)
H2A—C2—H2C106 (3)C9—C8—H8122 (2)
H2B—C2—H2C101 (3)C7—C8—H8119 (2)
N1—C3—C2109.9 (2)C8—C9—C10120.2 (3)
N1—C3—C4106.2 (2)C8—C9—H9120.9 (16)
C2—C3—C4113.9 (3)C10—C9—H9118.3 (17)
N1—C3—H3A104 (2)C5—C10—C9120.8 (3)
C2—C3—H3A113 (2)C5—C10—H10120.6 (17)
C4—C3—H3A109 (2)C9—C10—H10118.4 (18)
C1—N1—C3—C2−60.4 (3)C4—C5—C6—C7−178.7 (3)
C1—N1—C3—C4176.0 (3)C5—C6—C7—C80.1 (4)
N1—C3—C4—C5−171.5 (2)C6—C7—C8—C9−1.1 (4)
C2—C3—C4—C567.5 (3)C7—C8—C9—C101.2 (5)
C3—C4—C5—C1082.9 (3)C6—C5—C10—C9−0.8 (4)
C3—C4—C5—C6−97.6 (3)C4—C5—C10—C9178.8 (3)
C10—C5—C6—C70.8 (4)C8—C9—C10—C5−0.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···Cl1i0.93 (4)2.14 (4)3.069 (2)179 (4)
N1—H1E···Cl1ii0.90 (3)2.22 (3)3.116 (2)176 (3)
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC10H16N+·Cl−
Mr185.69
Crystal system, space groupMonoclinic, P21
Temperature (K)90
a, b, c (Å)7.1022 (11), 7.2949 (11), 10.8121 (17)
β (°) 97.293 (4)
V (Å3)555.64 (15)
Z2
Radiation typeMo Kα
µ (mm−1)0.30
Crystal size (mm)0.28 × 0.14 × 0.10
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.922, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections		5892, 2720, 2379
Rint0.047
(sin θ/λ)max (Å−1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.117, 1.05
No. of reflections2720
No. of parameters174
No. of restraints1
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.43, −0.46
Absolute structureFlack (1983), 1235 Freidel pairs
Absolute structure parameter0.00 (10)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalMaker (Palmer, 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···Cl1i0.93 (4)2.14 (4)3.069 (2)179 (4)
N1—H1E···Cl1ii0.90 (3)2.22 (3)3.116 (2)176 (3)
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x+1, y, z.
 

Acknowledgements

The authors gratefully acknowledge the support of the National Geospatial–Intelligence Agency (HM1582-05-1-2024) and the National Science Foundation (CHE-0604527). PMH expresses his gratitude to the Syracuse University and STEM Fellowship programs.

References

First citationBruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCho, A. K. (1990). Science, 249, 631–634.  CrossRef PubMed CAS Web of Science Google Scholar
 First citationCho, A. K. & Melega, W. P. (2002). J. Addict. Dis. 21, 21–34.  CrossRef PubMed Google Scholar
 First citationDavis, G. G. & Swalwell, C. I. (1994). J. Forensic Sci. 39, 1481–1485.  CAS PubMed Web of Science Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationO'Neil, M. J., Smith, A., Heckelman, P. E. & Budavari, S. (2001). Editors. The Merck Index, 13th ed., entry 5975. Whitehouse Station, NJ: Merck & Co.  Google Scholar
 First citationPalmer, D. (2006). CrystalMaker. CrystalMaker Software Ltd, Yarnton, Oxfordshire, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSimon, K., Bocskei, Z. & Torok, Z. (1992). Acta Pharm. Hung. 62, 225–230.  PubMed CAS Google Scholar
 First citationYao, Y., Kan, Y. & Wang, S. (1999). Huaxue Shijie, 40, 568–570.  CAS Google Scholar
 First citationYu, Q., Larson, D. F. & Watson, R. R. (2003). Life Sci. 73, 129–140.  Web of Science CrossRef PubMed CAS Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 5| May 2008| Page o940
doi:10.1107/S1600536808011550
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