2-(4-Meth-oxy-phenyl)-2-oxoethan-aminium chloride.

In the cation of the title compound, C(9)H(12)NO(2) (+)·Cl(-), the dihedral angle between the 2-oxoethanaminium N-C-C(=O)- plane [maximum deviation = 0.0148 (12) Å] and the benzene ring is 7.98 (8)°. The meth-oxy group is approximately in-plane with the benzene ring, with a C-O-C-C torsion angle of -2.91 (18)°. In the crystal, the cations and chloride anions are connected by N-H⋯Cl and C-H⋯Cl hydrogen bonds, forming a layer parallel to the bc plane. A C-H⋯π inter-action further links the layers.

Related literature

For syntheses and applications of nitro­gen-containing heterocyclic compounds, see: Alvarez-Builla et al. (2011 ▶); Katritzky et al. (2010 ▶); Chen et al. (2011 ▶). For a related structure, see: Zhang et al. (2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C9H12NO2 +·Cl−

M = 201.65

Monoclinic,

a = 12.2822 (8) Å

b = 7.1605 (4) Å

c = 11.1226 (7) Å

β = 92.435 (1)°

V = 977.31 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 100 K

0.40 × 0.24 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.870, T max = 0.942

10764 measured reflections

2871 independent reflections

2622 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.099

S = 1.08

2871 reflections

132 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039645/is5194sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039645/is5194Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039645/is5194Isup3.cml

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

C9H12NO2+·Cl−	F(000) = 424
Mr = 201.65	Dx = 1.370 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6587 reflections
a = 12.2822 (8) Å	θ = 3.3–30.1°
b = 7.1605 (4) Å	µ = 0.36 mm−1
c = 11.1226 (7) Å	T = 100 K
β = 92.435 (1)°	Block, yellow
V = 977.31 (10) Å3	0.40 × 0.24 × 0.17 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	2871 independent reflections
Radiation source: fine-focus sealed tube	2622 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 30.2°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.870, Tmax = 0.942	k = −10→10
10764 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.5579P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2871 reflections	Δρmax = 0.66 e Å−3
132 parameters	Δρmin = −0.31 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (3)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.31506 (8)	0.43288 (14)	0.83094 (9)	0.0240 (2)
O2	0.77620 (8)	0.12046 (16)	1.02231 (9)	0.0271 (2)
N1	0.93861 (9)	0.16996 (19)	0.87460 (10)	0.0224 (2)
C1	0.22952 (11)	0.3669 (2)	0.90447 (13)	0.0252 (3)
H1A	0.1601	0.4227	0.8767	0.038*
H1B	0.2457	0.4023	0.9884	0.038*
H1C	0.2245	0.2306	0.8984	0.038*
C2	0.41825 (10)	0.37782 (18)	0.86212 (11)	0.0187 (2)
C3	0.49898 (10)	0.43820 (18)	0.78563 (11)	0.0198 (2)
H3A	0.4795	0.5137	0.7179	0.024*
C4	0.60660 (10)	0.38863 (18)	0.80810 (11)	0.0191 (2)
H4A	0.6607	0.4297	0.7555	0.023*
C5	0.63640 (10)	0.27779 (17)	0.90828 (11)	0.0176 (2)
C6	0.55558 (10)	0.22213 (17)	0.98526 (11)	0.0186 (2)
H6A	0.5754	0.1504	1.0546	0.022*
C7	0.44689 (11)	0.26912 (17)	0.96292 (11)	0.0192 (2)
H7A	0.3928	0.2280	1.0154	0.023*
C8	0.74917 (10)	0.21092 (17)	0.93292 (11)	0.0189 (2)
C9	0.83234 (11)	0.25722 (18)	0.84067 (11)	0.0202 (2)
H9A	0.8064	0.2111	0.7606	0.024*
H9B	0.8412	0.3944	0.8355	0.024*
Cl1	1.05551 (2)	0.22239 (4)	0.63026 (2)	0.01705 (10)
H1N1	0.9649 (18)	0.215 (3)	0.952 (2)	0.041 (6)*
H2N1	0.9365 (14)	0.037 (3)	0.8780 (16)	0.029 (5)*
H3N1	0.9882 (18)	0.196 (3)	0.810 (2)	0.040 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0205 (4)	0.0274 (5)	0.0244 (4)	0.0012 (4)	0.0030 (3)	0.0044 (4)
O2	0.0252 (5)	0.0328 (5)	0.0232 (5)	0.0012 (4)	0.0017 (4)	0.0083 (4)
N1	0.0209 (5)	0.0255 (6)	0.0210 (5)	0.0000 (4)	0.0023 (4)	0.0003 (4)
C1	0.0207 (6)	0.0270 (7)	0.0281 (6)	−0.0017 (5)	0.0041 (5)	0.0015 (5)
C2	0.0211 (5)	0.0171 (5)	0.0180 (5)	0.0001 (4)	0.0018 (4)	−0.0018 (4)
C3	0.0242 (6)	0.0186 (6)	0.0166 (5)	0.0008 (4)	0.0026 (4)	0.0019 (4)
C4	0.0231 (6)	0.0184 (5)	0.0161 (5)	−0.0016 (4)	0.0040 (4)	0.0010 (4)
C5	0.0200 (5)	0.0171 (5)	0.0157 (5)	−0.0016 (4)	0.0015 (4)	−0.0010 (4)
C6	0.0235 (6)	0.0175 (5)	0.0150 (5)	−0.0013 (4)	0.0018 (4)	0.0004 (4)
C7	0.0223 (6)	0.0189 (6)	0.0168 (5)	−0.0021 (4)	0.0043 (4)	−0.0002 (4)
C8	0.0215 (5)	0.0178 (5)	0.0176 (5)	−0.0022 (4)	0.0018 (4)	−0.0005 (4)
C9	0.0209 (6)	0.0209 (6)	0.0189 (5)	−0.0001 (4)	0.0028 (4)	0.0010 (4)
Cl1	0.02011 (15)	0.01794 (16)	0.01333 (15)	0.00302 (9)	0.00337 (9)	0.00102 (9)

O1—C2	1.3582 (15)	C3—C4	1.3812 (17)
O1—C1	1.4384 (16)	C3—H3A	0.9500
O2—C8	1.2208 (16)	C4—C5	1.4039 (17)
N1—C9	1.4814 (17)	C4—H4A	0.9500
N1—H1N1	0.96 (2)	C5—C6	1.3962 (17)
N1—H2N1	0.95 (2)	C5—C8	1.4800 (17)
N1—H3N1	0.98 (2)	C6—C7	1.3888 (18)
C1—H1A	0.9800	C6—H6A	0.9500
C1—H1B	0.9800	C7—H7A	0.9500
C1—H1C	0.9800	C8—C9	1.5150 (18)
C2—C7	1.3975 (17)	C9—H9A	0.9900
C2—C3	1.4020 (17)	C9—H9B	0.9900
C2—O1—C1	117.11 (10)	C3—C4—H4A	119.9
C9—N1—H1N1	110.3 (13)	C5—C4—H4A	119.9
C9—N1—H2N1	114.0 (11)	C6—C5—C4	118.68 (11)
H1N1—N1—H2N1	107.7 (16)	C6—C5—C8	118.57 (11)
C9—N1—H3N1	107.4 (13)	C4—C5—C8	122.70 (11)
H1N1—N1—H3N1	113.7 (19)	C7—C6—C5	121.61 (11)
H2N1—N1—H3N1	103.8 (17)	C7—C6—H6A	119.2
O1—C1—H1A	109.5	C5—C6—H6A	119.2
O1—C1—H1B	109.5	C6—C7—C2	119.06 (11)
H1A—C1—H1B	109.5	C6—C7—H7A	120.5
O1—C1—H1C	109.5	C2—C7—H7A	120.5
H1A—C1—H1C	109.5	O2—C8—C5	122.85 (11)
H1B—C1—H1C	109.5	O2—C8—C9	119.99 (12)
O1—C2—C7	124.53 (11)	C5—C8—C9	117.16 (10)
O1—C2—C3	115.59 (11)	N1—C9—C8	110.32 (10)
C7—C2—C3	119.88 (12)	N1—C9—H9A	109.6
C4—C3—C2	120.47 (11)	C8—C9—H9A	109.6
C4—C3—H3A	119.8	N1—C9—H9B	109.6
C2—C3—H3A	119.8	C8—C9—H9B	109.6
C3—C4—C5	120.27 (11)	H9A—C9—H9B	108.1
C1—O1—C2—C7	−2.91 (18)	C5—C6—C7—C2	−1.25 (19)
C1—O1—C2—C3	177.42 (11)	O1—C2—C7—C6	−179.90 (12)
O1—C2—C3—C4	−179.30 (11)	C3—C2—C7—C6	−0.23 (18)
C7—C2—C3—C4	1.01 (19)	C6—C5—C8—O2	−5.45 (19)
C2—C3—C4—C5	−0.31 (19)	C4—C5—C8—O2	177.16 (12)
C3—C4—C5—C6	−1.13 (18)	C6—C5—C8—C9	173.82 (11)
C3—C4—C5—C8	176.25 (11)	C4—C5—C8—C9	−3.57 (17)
C4—C5—C6—C7	1.93 (19)	O2—C8—C9—N1	3.06 (17)
C8—C5—C6—C7	−175.56 (11)	C5—C8—C9—N1	−176.23 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N1···Cl1i	0.95 (2)	2.26 (2)	3.2061 (14)	173.6 (15)
N1—H3N1···Cl1	0.99 (2)	2.19 (2)	3.1496 (12)	162.6 (19)
N1—H1N1···Cl1ii	0.97 (2)	2.27 (2)	3.2240 (12)	168.4 (19)
C9—H9B···Cl1iii	0.99	2.69	3.6135 (13)	156
C3—H3A···Cg1iv	0.95	2.53	3.3909 (14)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N1⋯Cl1i	0.95 (2)	2.26 (2)	3.2061 (14)	173.6 (15)
N1—H3N1⋯Cl1	0.99 (2)	2.19 (2)	3.1496 (12)	162.6 (19)
N1—H1N1⋯Cl1ii	0.97 (2)	2.27 (2)	3.2240 (12)	168.4 (19)
C9—H9B⋯Cl1iii	0.99	2.69	3.6135 (13)	156
C3—H3A⋯Cg1iv	0.95	2.53	3.3909 (14)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .