N-Methyl-2-oxo-1-phenyl-propan-1-aminium chloride.

In the structure of the title compound, C(10)H(14)NO(+)·Cl(-), both H atoms bound to nitro-gen are involved in N-H⋯Cl hydrogen-bonding inter-actions. These inter-actions join the cations and anions into dimeric units (two cations and two anions) with R(4) (2)(8) motifs lying about inversion centers.

Related literature

For the screening of mol­ecular salts with physicochemical properties, see: Tong & Whitesell et al. (1998 ▶); Shanker (1994 ▶). Over 40% of commercially available salts are hydro­chlorides (Gould et al., 1986 ▶), and this trend is reflected in the available set of salt structures included in the Cambridge Structural Database (Allen et al., 2002 ▶). For a closely related structure, see: Au & Tafeenko (1986 ▶).

Experimental

Crystal data

C10H14NO+·Cl−

M = 199.67

Monoclinic,

a = 12.631 (3) Å

b = 8.2564 (17) Å

c = 11.423 (2) Å

β = 114.63 (3)°

V = 1082.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury 2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2002 ▶) T min = 0.825, T max = 1.000

10899 measured reflections

2486 independent reflections

1858 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.172

S = 1.12

2486 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024032/yk2004sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024032/yk2004Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024032/yk2004Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H14NO+·Cl−	F(000) = 424
Mr = 199.67	Dx = 1.225 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2486 reflections
a = 12.631 (3) Å	θ = 2.6–27.5°
b = 8.2564 (17) Å	µ = 0.32 mm−1
c = 11.423 (2) Å	T = 293 K
β = 114.63 (3)°	Prism, colorless
V = 1082.9 (4) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku Mercury 2 diffractometer	2486 independent reflections
Radiation source: fine-focus sealed tube	1858 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scans	h = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	k = −10→10
Tmin = 0.825, Tmax = 1.000	l = −14→14
10899 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.1P)2 + 0.0P] where P = (Fo2 + 2Fc2)/3
2486 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.84648 (5)	0.60715 (7)	1.05463 (5)	0.0477 (2)
N1	0.88712 (14)	0.4261 (2)	0.83566 (16)	0.0372 (4)
H1A	0.8633	0.4628	0.8949	0.045*
H1E	0.9638	0.4049	0.8764	0.045*
C4	0.6325 (2)	0.3894 (3)	0.7610 (2)	0.0557 (7)
H4A	0.6721	0.4438	0.8384	0.067*
C5	0.82470 (17)	0.2721 (2)	0.78105 (19)	0.0371 (5)
H5A	0.8544	0.2286	0.7207	0.045*
C7	0.85316 (19)	0.1511 (3)	0.8920 (2)	0.0429 (5)
C8	0.69366 (18)	0.2949 (3)	0.7093 (2)	0.0396 (5)
C9	0.5129 (2)	0.4023 (4)	0.6973 (3)	0.0725 (9)
H9A	0.4724	0.4663	0.7317	0.087*
C10	0.8142 (3)	−0.0187 (3)	0.8562 (3)	0.0646 (8)
H10A	0.8363	−0.0829	0.9329	0.097*
H10B	0.8501	−0.0618	0.8036	0.097*
H10C	0.7311	−0.0212	0.8091	0.097*
C11	0.6337 (2)	0.2185 (3)	0.5944 (2)	0.0606 (7)
H11A	0.6737	0.1578	0.5574	0.073*
C12	0.5143 (3)	0.2308 (4)	0.5332 (3)	0.0782 (10)
H12A	0.4746	0.1759	0.4561	0.094*
C13	0.4533 (2)	0.3214 (4)	0.5833 (3)	0.0747 (9)
H13A	0.3727	0.3286	0.5412	0.090*
C1	0.8697 (2)	0.5566 (3)	0.7395 (2)	0.0535 (6)
H1B	0.9126	0.6511	0.7824	0.080*
H1C	0.7884	0.5826	0.6970	0.080*
H1D	0.8970	0.5202	0.6771	0.080*
O2	0.90399 (18)	0.1954 (2)	1.00174 (16)	0.0685 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0439 (4)	0.0545 (4)	0.0443 (4)	0.0016 (2)	0.0181 (3)	−0.0090 (2)
N1	0.0367 (10)	0.0430 (10)	0.0320 (9)	0.0007 (7)	0.0144 (8)	0.0012 (7)
C4	0.0402 (13)	0.081 (2)	0.0412 (14)	0.0042 (12)	0.0126 (11)	−0.0107 (12)
C5	0.0380 (11)	0.0403 (11)	0.0351 (11)	0.0030 (9)	0.0174 (9)	0.0010 (9)
C7	0.0411 (12)	0.0458 (12)	0.0444 (13)	0.0062 (10)	0.0206 (10)	0.0087 (10)
C8	0.0359 (11)	0.0461 (13)	0.0330 (11)	−0.0001 (9)	0.0106 (9)	0.0020 (9)
C9	0.0463 (15)	0.104 (3)	0.0649 (18)	0.0143 (15)	0.0204 (14)	−0.0088 (16)
C10	0.0814 (19)	0.0464 (15)	0.0628 (18)	−0.0013 (13)	0.0269 (15)	0.0096 (12)
C11	0.0575 (16)	0.0673 (17)	0.0466 (14)	0.0056 (13)	0.0114 (12)	−0.0156 (12)
C12	0.0593 (18)	0.091 (2)	0.0570 (17)	−0.0015 (16)	−0.0033 (14)	−0.0222 (16)
C13	0.0389 (15)	0.103 (2)	0.0652 (19)	0.0037 (15)	0.0045 (13)	−0.0044 (18)
C1	0.0651 (16)	0.0445 (13)	0.0481 (14)	−0.0040 (12)	0.0208 (12)	0.0077 (10)
O2	0.0939 (15)	0.0638 (13)	0.0361 (10)	0.0005 (10)	0.0155 (9)	0.0099 (8)

N1—C1	1.488 (3)	C9—C13	1.375 (4)
N1—C5	1.489 (3)	C9—H9A	0.9300
N1—H1A	0.9000	C10—H10A	0.9600
N1—H1E	0.9000	C10—H10B	0.9600
C4—C9	1.380 (3)	C10—H10C	0.9600
C4—C8	1.391 (3)	C11—C12	1.376 (4)
C4—H4A	0.9300	C11—H11A	0.9300
C5—C8	1.522 (3)	C12—C13	1.359 (4)
C5—C7	1.534 (3)	C12—H12A	0.9300
C5—H5A	0.9800	C13—H13A	0.9300
C7—O2	1.203 (3)	C1—H1B	0.9600
C7—C10	1.486 (4)	C1—H1C	0.9600
C8—C11	1.366 (3)	C1—H1D	0.9600
C1—N1—C5	114.80 (17)	C4—C9—H9A	119.7
C1—N1—H1A	108.6	C7—C10—H10A	109.5
C5—N1—H1A	108.6	C7—C10—H10B	109.5
C1—N1—H1E	108.6	H10A—C10—H10B	109.5
C5—N1—H1E	108.6	C7—C10—H10C	109.5
H1A—N1—H1E	107.5	H10A—C10—H10C	109.5
C9—C4—C8	119.9 (2)	H10B—C10—H10C	109.5
C9—C4—H4A	120.0	C8—C11—C12	120.4 (3)
C8—C4—H4A	120.0	C8—C11—H11A	119.8
N1—C5—C8	112.75 (17)	C12—C11—H11A	119.8
N1—C5—C7	108.00 (17)	C13—C12—C11	121.3 (3)
C8—C5—C7	110.70 (17)	C13—C12—H12A	119.3
N1—C5—H5A	108.4	C11—C12—H12A	119.3
C8—C5—H5A	108.4	C12—C13—C9	118.9 (3)
C7—C5—H5A	108.4	C12—C13—H13A	120.6
O2—C7—C10	123.0 (2)	C9—C13—H13A	120.6
O2—C7—C5	120.2 (2)	N1—C1—H1B	109.5
C10—C7—C5	116.8 (2)	N1—C1—H1C	109.5
C11—C8—C4	118.9 (2)	H1B—C1—H1C	109.5
C11—C8—C5	120.2 (2)	N1—C1—H1D	109.5
C4—C8—C5	120.9 (2)	H1B—C1—H1D	109.5
C13—C9—C4	120.6 (3)	H1C—C1—H1D	109.5
C13—C9—H9A	119.7

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	0.90	2.26	3.1345 (19)	163
N1—H1E···Cl1i	0.90	2.19	3.0747 (19)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	0.90	2.26	3.1345 (19)	163
N1—H1E⋯Cl1i	0.90	2.19	3.0747 (19)	167

Symmetry code: (i) .