organic compounds
N-(2-Benzoylethyl)propan-2-aminium chloride
aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Atatürk University, 25240 Erzurum, Turkey, and dDepartment of Chemistry, Faculty of Sciences, Atatürk University, 25240 Erzurum, Turkey
*Correspondence e-mail: aaydin@kastamonu.edu.tr
In the title salt, C12H18NO+·Cl−, N—H⋯Cl interactions between the free chloride anions and the organic cations connect the molecules into hydrogen-bond dimers, forming a R22(8) motif. The dimers are linked by C—H⋯O hydrogen bonds into chains extending along [301]. The carbonyl group is co-planar with the phenyl ring [C—C—C=O torsion angle = −3.3 (7)°]. The side chain has an E conformation.
Related literature
For the details of the pharmacological effects of Mannich bases and for their synthesis, see: Dimmock & Kumar (1997); Gul et al. (2004, 2005a,b, 2009); Mete et al. (2011a,b); Kucukoglu et al. (2011); Canturk et al. (2008); Chen et al. (1991); Gul (2005); Suleyman et al. (2007); Plati et al. (1949). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter (1990). For some related structures, see: Abonia et al. (2011); Tuzina et al. (2006).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536812035106/qm2079sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035106/qm2079Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035106/qm2079Isup3.cml
A mixture of the appropriate ketone (50 mmol), paraformaldehyde (50 mmol), and isopropylamine hydrochloride (27 mmol) was heated in an oil bath at 403 K. The reaction vessel was then removed from the oil bath and when the temperature of the mixture dropped to 338 K, ethyl acetate (40–80 ml) was added. The mixture was stirred at room temperature for 24 h and the resultant precipitate was collected and recrystallized from ether/methanol. The melting point was 445–447 K (lit. Plati et al., 1949 m.p. 447–449 K) and the yield was 55% (Mete et al., 2011b).
1H-NMR δ 1.49 (d, J = 6.6 Hz, 6H, CH(CH3)2), 3.36–3.42 (m, 3H, CH(CH3)2 and 2 x H-2), 3.77 (t, J = 7.5 Hz, 2H, 2 x H-3), 7.36 (t, J = 7.3 Hz, 2H, H-3'/5'), 7.51 (t, J = 7.3 Hz, 1H, H-4'), 7.90 (d, J = 7.3 Hz, 2H, H-2'/6'), 9.56 (brs, 2H, NH2+); 13C-NMR δ 19.4 (CH(CH3)2), 35.2, 40.3, 51.2, 128.3, 128.9, 134.0, 136.0, 196.9; MS (EI) m/z (%): 176.2 (M–CH3)+, 192.1 (M+H)+. IR (KBr, cm-1): 2453 (NH2+), 1678 (CO). Calcd for C12H18ClNO (227.73): C, 63.29; H, 7.97; N, 6.15. Found: C, 63.26; H, 8.18; N, 6.23.
H atoms of the NH2 group were located in a difference Fourier map. Their positions refined with restraints on the N—H bond lengths of 0.86 (2) Å, while their thermal parameters were refined as riding with Uiso(H) = 1.2Ueq(N). H atoms bound to C atoms were positioned geometrically, with C—H = 0.93(aromatic), 0.97(methylene) and 0.98 Å (methine), and refined as riding with Uiso(H) = 1.5Ueq(O) for methyl H and 1.2Ueq(C) for the others.
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).C12H18NO+·Cl− | F(000) = 488 |
Mr = 227.72 | Dx = 1.191 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3090 reflections |
a = 8.036 (5) Å | θ = 2.2–26.4° |
b = 8.656 (5) Å | µ = 0.28 mm−1 |
c = 18.403 (5) Å | T = 294 K |
β = 97.174 (5)° | Block, white |
V = 1270.1 (11) Å3 | 0.16 × 0.13 × 0.12 mm |
Z = 4 |
Rigaku R-AXIS RAPID-S diffractometer | 2334 independent reflections |
Radiation source: Sealed Tube | 1204 reflections with I > 2σ(I) |
Graphite Monochromator monochromator | Rint = 0.116 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 25.5°, θmin = 2.2° |
dtprofit.ref scans | h = −9→9 |
Absorption correction: multi-scan (Blessing, 1995) | k = −9→10 |
Tmin = 0.958, Tmax = 0.967 | l = −22→22 |
15799 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.224 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0971P)2 + 0.2008P] where P = (Fo2 + 2Fc2)/3 |
2334 reflections | (Δ/σ)max = 0.001 |
145 parameters | Δρmax = 0.49 e Å−3 |
2 restraints | Δρmin = −0.19 e Å−3 |
C12H18NO+·Cl− | V = 1270.1 (11) Å3 |
Mr = 227.72 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.036 (5) Å | µ = 0.28 mm−1 |
b = 8.656 (5) Å | T = 294 K |
c = 18.403 (5) Å | 0.16 × 0.13 × 0.12 mm |
β = 97.174 (5)° |
Rigaku R-AXIS RAPID-S diffractometer | 2334 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 1204 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.967 | Rint = 0.116 |
15799 measured reflections |
R[F2 > 2σ(F2)] = 0.075 | 2 restraints |
wR(F2) = 0.224 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.49 e Å−3 |
2334 reflections | Δρmin = −0.19 e Å−3 |
145 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
O1 | 0.2324 (5) | 0.4012 (5) | 1.02649 (18) | 0.1262 (18) | |
N1 | 0.3982 (4) | 0.4236 (4) | 0.8222 (2) | 0.0689 (14) | |
C1 | −0.1184 (6) | 0.1831 (6) | 0.9398 (3) | 0.090 (2) | |
C2 | −0.2586 (7) | 0.1067 (7) | 0.9575 (4) | 0.114 (3) | |
C3 | −0.2887 (7) | 0.0999 (7) | 1.0303 (4) | 0.110 (3) | |
C4 | −0.1824 (7) | 0.1686 (8) | 1.0833 (3) | 0.103 (3) | |
C5 | −0.0433 (7) | 0.2458 (6) | 1.0658 (3) | 0.088 (2) | |
C6 | −0.0099 (6) | 0.2528 (5) | 0.9940 (2) | 0.0722 (17) | |
C7 | 0.1440 (6) | 0.3359 (6) | 0.9778 (3) | 0.0828 (19) | |
C8 | 0.1897 (5) | 0.3369 (5) | 0.9007 (2) | 0.0749 (17) | |
C9 | 0.3548 (5) | 0.4217 (5) | 0.8982 (2) | 0.0772 (17) | |
C10 | 0.5624 (6) | 0.5009 (5) | 0.8146 (3) | 0.0850 (19) | |
C11 | 0.6181 (8) | 0.4545 (7) | 0.7460 (4) | 0.133 (3) | |
C12 | 0.5461 (6) | 0.6727 (6) | 0.8219 (3) | 0.109 (3) | |
Cl1 | 0.40593 (14) | 0.07597 (13) | 0.77578 (6) | 0.0828 (5) | |
H1 | −0.09700 | 0.18770 | 0.89130 | 0.1080* | |
H1N | 0.321 (5) | 0.453 (5) | 0.788 (2) | 0.0990* | |
H2 | −0.33240 | 0.06020 | 0.92100 | 0.1370* | |
H2N | 0.402 (6) | 0.332 (3) | 0.803 (2) | 0.0990* | |
H3 | −0.38260 | 0.04780 | 1.04250 | 0.1320* | |
H4 | −0.20350 | 0.16370 | 1.13180 | 0.1240* | |
H5 | 0.02880 | 0.29350 | 1.10240 | 0.1060* | |
H8A | 0.10170 | 0.38750 | 0.86830 | 0.0900* | |
H8B | 0.19980 | 0.23160 | 0.88380 | 0.0900* | |
H9A | 0.34510 | 0.52680 | 0.91550 | 0.0930* | |
H9B | 0.44310 | 0.37050 | 0.93010 | 0.0930* | |
H10 | 0.64530 | 0.46460 | 0.85460 | 0.1020* | |
H11A | 0.53580 | 0.48440 | 0.70610 | 0.1990* | |
H11B | 0.63260 | 0.34440 | 0.74560 | 0.1990* | |
H11C | 0.72290 | 0.50400 | 0.74080 | 0.1990* | |
H12A | 0.65050 | 0.72110 | 0.81500 | 0.1630* | |
H12B | 0.51800 | 0.69720 | 0.86970 | 0.1630* | |
H12C | 0.45930 | 0.70980 | 0.78540 | 0.1630* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.151 (3) | 0.161 (4) | 0.065 (2) | −0.063 (3) | 0.007 (2) | −0.016 (2) |
N1 | 0.065 (2) | 0.066 (2) | 0.076 (3) | −0.0063 (19) | 0.0105 (16) | 0.0006 (18) |
C1 | 0.093 (4) | 0.099 (4) | 0.083 (3) | −0.006 (3) | 0.027 (3) | −0.010 (3) |
C2 | 0.082 (4) | 0.143 (6) | 0.119 (5) | −0.017 (3) | 0.022 (3) | −0.019 (4) |
C3 | 0.087 (4) | 0.138 (5) | 0.113 (5) | 0.003 (3) | 0.039 (4) | 0.015 (4) |
C4 | 0.091 (4) | 0.136 (5) | 0.086 (4) | 0.025 (4) | 0.028 (3) | 0.020 (3) |
C5 | 0.094 (4) | 0.102 (4) | 0.069 (3) | 0.013 (3) | 0.012 (3) | 0.003 (3) |
C6 | 0.078 (3) | 0.072 (3) | 0.068 (3) | 0.009 (2) | 0.015 (2) | −0.002 (2) |
C7 | 0.097 (4) | 0.086 (3) | 0.065 (3) | 0.002 (3) | 0.009 (2) | −0.003 (2) |
C8 | 0.084 (3) | 0.075 (3) | 0.067 (3) | −0.007 (2) | 0.015 (2) | −0.001 (2) |
C9 | 0.081 (3) | 0.078 (3) | 0.072 (3) | −0.004 (2) | 0.007 (2) | 0.002 (2) |
C10 | 0.069 (3) | 0.069 (3) | 0.118 (4) | −0.005 (2) | 0.016 (3) | 0.003 (3) |
C11 | 0.127 (5) | 0.131 (5) | 0.151 (6) | −0.037 (4) | 0.061 (4) | −0.027 (4) |
C12 | 0.090 (4) | 0.069 (3) | 0.168 (6) | −0.015 (3) | 0.021 (3) | 0.002 (3) |
Cl1 | 0.0792 (8) | 0.0703 (8) | 0.0974 (9) | 0.0004 (6) | 0.0050 (6) | −0.0080 (6) |
O1—C7 | 1.212 (6) | C1—H1 | 0.9300 |
N1—C9 | 1.483 (5) | C2—H2 | 0.9300 |
N1—C10 | 1.502 (6) | C3—H3 | 0.9300 |
N1—H1N | 0.87 (4) | C4—H4 | 0.9300 |
N1—H2N | 0.87 (3) | C5—H5 | 0.9300 |
C1—C2 | 1.380 (8) | C8—H8A | 0.9700 |
C1—C6 | 1.379 (7) | C8—H8B | 0.9700 |
C2—C3 | 1.392 (10) | C9—H9A | 0.9700 |
C3—C4 | 1.352 (9) | C9—H9B | 0.9700 |
C4—C5 | 1.375 (8) | C10—H10 | 0.9800 |
C5—C6 | 1.382 (7) | C11—H11A | 0.9600 |
C6—C7 | 1.493 (7) | C11—H11B | 0.9600 |
C7—C8 | 1.509 (7) | C11—H11C | 0.9600 |
C8—C9 | 1.522 (6) | C12—H12A | 0.9600 |
C10—C12 | 1.500 (7) | C12—H12B | 0.9600 |
C10—C11 | 1.448 (9) | C12—H12C | 0.9600 |
C9—N1—C10 | 113.9 (3) | C5—C4—H4 | 120.00 |
C10—N1—H1N | 111 (3) | C4—C5—H5 | 120.00 |
C9—N1—H1N | 117 (3) | C6—C5—H5 | 120.00 |
C9—N1—H2N | 113 (2) | C7—C8—H8A | 110.00 |
C10—N1—H2N | 107 (3) | C7—C8—H8B | 110.00 |
H1N—N1—H2N | 92 (4) | C9—C8—H8A | 110.00 |
C2—C1—C6 | 120.0 (5) | C9—C8—H8B | 110.00 |
C1—C2—C3 | 119.5 (6) | H8A—C8—H8B | 108.00 |
C2—C3—C4 | 120.4 (5) | N1—C9—H9A | 110.00 |
C3—C4—C5 | 120.3 (5) | N1—C9—H9B | 110.00 |
C4—C5—C6 | 120.4 (5) | C8—C9—H9A | 110.00 |
C5—C6—C7 | 118.5 (4) | C8—C9—H9B | 110.00 |
C1—C6—C7 | 122.1 (4) | H9A—C9—H9B | 108.00 |
C1—C6—C5 | 119.4 (5) | N1—C10—H10 | 108.00 |
O1—C7—C6 | 120.1 (5) | C11—C10—H10 | 108.00 |
C6—C7—C8 | 119.7 (4) | C12—C10—H10 | 108.00 |
O1—C7—C8 | 120.2 (4) | C10—C11—H11A | 109.00 |
C7—C8—C9 | 110.3 (3) | C10—C11—H11B | 109.00 |
N1—C9—C8 | 110.0 (3) | C10—C11—H11C | 109.00 |
N1—C10—C12 | 110.2 (4) | H11A—C11—H11B | 110.00 |
C11—C10—C12 | 113.1 (5) | H11A—C11—H11C | 109.00 |
N1—C10—C11 | 109.2 (4) | H11B—C11—H11C | 109.00 |
C2—C1—H1 | 120.00 | C10—C12—H12A | 109.00 |
C6—C1—H1 | 120.00 | C10—C12—H12B | 110.00 |
C1—C2—H2 | 120.00 | C10—C12—H12C | 109.00 |
C3—C2—H2 | 120.00 | H12A—C12—H12B | 110.00 |
C2—C3—H3 | 120.00 | H12A—C12—H12C | 109.00 |
C4—C3—H3 | 120.00 | H12B—C12—H12C | 109.00 |
C3—C4—H4 | 120.00 | ||
C10—N1—C9—C8 | −178.2 (3) | C4—C5—C6—C1 | 0.7 (8) |
C9—N1—C10—C11 | 161.9 (4) | C4—C5—C6—C7 | −179.1 (5) |
C9—N1—C10—C12 | −73.3 (5) | C5—C6—C7—C8 | 176.1 (4) |
C2—C1—C6—C7 | 179.6 (5) | C1—C6—C7—O1 | 176.9 (5) |
C6—C1—C2—C3 | −0.4 (8) | C1—C6—C7—C8 | −3.7 (7) |
C2—C1—C6—C5 | −0.2 (8) | C5—C6—C7—O1 | −3.3 (7) |
C1—C2—C3—C4 | 0.6 (9) | O1—C7—C8—C9 | 2.1 (6) |
C2—C3—C4—C5 | −0.1 (10) | C6—C7—C8—C9 | −177.3 (4) |
C3—C4—C5—C6 | −0.6 (9) | C7—C8—C9—N1 | −179.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl1i | 0.87 (4) | 2.30 (4) | 3.141 (4) | 163 (4) |
N1—H2N···Cl1 | 0.87 (3) | 2.27 (3) | 3.131 (4) | 169 (4) |
C10—H10···O1ii | 0.98 | 2.56 | 3.284 (7) | 130 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C12H18NO+·Cl− |
Mr | 227.72 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 8.036 (5), 8.656 (5), 18.403 (5) |
β (°) | 97.174 (5) |
V (Å3) | 1270.1 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.16 × 0.13 × 0.12 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID-S diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.958, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15799, 2334, 1204 |
Rint | 0.116 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.075, 0.224, 1.05 |
No. of reflections | 2334 |
No. of parameters | 145 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.49, −0.19 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl1i | 0.87 (4) | 2.30 (4) | 3.141 (4) | 163 (4) |
N1—H2N···Cl1 | 0.87 (3) | 2.27 (3) | 3.131 (4) | 169 (4) |
C10—H10···O1ii | 0.98 | 2.56 | 3.284 (7) | 130. |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2. |
Acknowledgements
The authors are indebted to the Department of Chemistry, Atatürk University, Erzurum, Turkey, for use of the X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund.
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Mannich bases are generally formed by the reaction between formaldehyde, a secondary amine and a compound containing reactive hydrogen atoms. On occasion, aldehydes other than formaldehyde may be employed and the secondary amine may be replaced by ammonia and primary amines. This process is known as the Mannich reaction (Dimmock & Kumar, 1997).
Mannich bases display varied biological activities such as antimicrobial (Gul et al., 2005; Mete et al., 2011a), cytotoxic (Gul et al., 2005; Mete et al., 2011b; Kucukoglu et al., 2011; Canturk et al., 2008), anticancer (Dimmock & Kumar, 1997; Chen et al., 1991; Gul, 2005), antiinflammatory (Suleyman et al., 2007; Gul et al., 2009), anticonvulsant (Gul et al., 2004) and DNA topoisomerase I inhibiting properties (Canturk et al., 2008).
The geometric parameters of the title salt (I) in Fig. 1 are within the range of expected values for this type of compound (Allen et al.,1987; Abonia et al., 2011; Tuzina et al., 2006).
The N—H···Cl hydrogen-bonding interactions between the free chloride anion and the organic cation link the molecules into hydrogen-bond dimers, forming an R22(8) motif (Bernstein et al., 1995; Etter, 1990). The dimers are linked by C—H···O hydrogen bonds, into chains extended along the [301] direction (Table 1, Fig. 2).