4-Hydroxy­ethyl-4-methyl­morpholinium chloride

Mei-Ling, W.; Hong-Jun, Z.; Bo-Wen, C.; Song, J.

doi:10.1107/S1600536808030195

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2029

doi:10.1107/S1600536808030195

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4-Hydroxyethyl-4-methylmorpholinium chloride

Wang Mei-Ling,^a Zang Hong-Jun,^a ^* Cheng Bo-Wen ^a and Jun Song ^a

^aSchool of Materials and Chemical Engineering and Key Laboratory of Hollow Fiber Membrane Materials & Membrane Processes, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China
^*Correspondence e-mail: chemhong@126.com

(Received 6 September 2008; accepted 19 September 2008; online 27 September 2008)

In the title compound, C₇H₁₆NO₂⁺·Cl⁻, the asymmetric unit consists of two cation–anion pairs, in which the ion pairs are interconnected by weak C—H⋯Cl hydrogen bonds. Each cation forms a network of weak C—H⋯Cl hydrogen bonds to surrounding chloride ions. The morpholine ring is in a chair conformation. The crystal structure is consolidated by O—H⋯Cl, C—H⋯Cl and C—H⋯O intermolecular hydrogen bonding.

Related literature

For general background, see: Abedin et al. (2004 , 2005 ); Kim et al. (2005 , 2006 ).

Experimental

Crystal data

C₇H₁₆NO₂⁺·Cl⁻
M_r = 181.66
Orthorhombic, P b c a
a = 12.181 (2) Å
b = 12.452 (3) Å
c = 23.856 (5) Å
V = 3618.5 (13) Å³
Z = 16
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 113 (2) K
0.16 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC 2005 ) T_min = 0.942, T_max = 0.963
19758 measured reflections
3198 independent reflections
2938 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.076
S = 1.06
3198 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯Cl2ⁱ	0.82	2.20	3.0222 (13)	178
O4—H4⋯Cl1	0.82	2.24	3.0505 (13)	168
C1—H1B⋯Cl1ⁱⁱ	0.97	2.64	3.5812 (16)	165
C2—H2B⋯O2ⁱⁱⁱ	0.97	2.59	3.335 (2)	134
C4—H4B⋯Cl2^iv	0.97	2.72	3.6390 (17)	158
C5—H5C⋯Cl1^v	0.96	2.71	3.6527 (16)	167
C6—H6A⋯Cl1^iv	0.97	2.77	3.6888 (18)	158
C8—H8A⋯O2	0.97	2.45	3.385 (2)	163
C9—H9B⋯Cl1^iv	0.97	2.80	3.7625 (17)	174
C11—H11A⋯O4	0.97	2.52	3.064 (2)	115
C13—H13A⋯Cl2^vi	0.97	2.80	3.7009 (18)	154
C13—H13B⋯O3^vii	0.97	2.60	3.3013 (19)	130
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ ; (iii) -x+2, -y, -z+2; (iv) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (vii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030195/si2107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030195/si2107Isup2.hkl

checkCIF report

Comment top

Quaternary morpholine halides are valuable precursors for the preparation of ionic liquids (ILs) by ion metathesis (Kim et al.,2005). The excellent conductivity, broad electrochemical window, thermal stability, and low volatility of ILs have made them promising media for electrochemical processes (Abedin et al.,2004; Abedin et al.,2005). In particular, ILs based on the morpholinium cation are favored becaused of their low cost, easy synthesis, and electrochemical stability (Kim et al.,2006). So far, only a few crystallographic studies have been performed on salts. We report here a new example structure of this class.

The molecular structure of (I) is illustrated in Fig. 1. For the title compound two crystallographically independent molecules are present in the asymmetric unit of the cell. The morpholine unit adopts a chair conformation. The bond distances and angles in the cation are normal within experimental error.

The crystal packing of (I) is illustrated in Fig. 2. The Cl^-anion involved in forming weak C—H···Cl hydrogen bonds. Each cation forms a network of weak C—H···Cl hydrogen bonds to surrounding chloride ions. The cation/anion pairs are interconnected by weak H—Cl bonding. The O atom of the hydroxyl group in the molecule involved in forming O—H···Cl and weak C—H···O hydrogen bonds. The crystal structure is consolidated by O—H···Cl, C—H···Cl and C—H···O intermolecular hydrogen bonding.

Related literature top

For general background, see: Abedin et al. (2004, 2005); Kim et al. (2005, 2006).

Experimental top

Under vigorous stirring, 2-chloroethanol(0.12 mol) was added to a solution of 4-methylmorpholine(0.1 mol) in 20 mL of acetonitrile. The mixture was stirred at 85 °C for 35 h. The solvent was removed under reduced pressure. The remaining brownish, viscous liquid crystallized slowly at room temperature in ethanol and acetone [1/20(v/v)]. A single-crystal was obtained by slow evaporation of a solution in ethanol and acetone [1/20(v/v)].

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of (I), showing the atom-numbering scheme. Dispacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A section of the the crystal packing viewed approximately down [010], showing hydrogen-bond interactions as dashed lines. H atoms are shown as small spheres of arbitary radii.

4-Hydroxyethyl-4-methylmorpholinium chloride top

Crystal data top

C₇H₁₆NO₂⁺·Cl⁻	D_x = 1.334 Mg m⁻³
M_r = 181.66	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 8950 reflections
a = 12.181 (2) Å	θ = 1.9–27.9°
b = 12.452 (3) Å	µ = 0.38 mm⁻¹
c = 23.856 (5) Å	T = 113 K
V = 3618.5 (13) Å³	Prism, colorless
Z = 16	0.16 × 0.12 × 0.10 mm
F(000) = 1568

Data collection top

Rigaku Saturn diffractometer	3198 independent reflections
Radiation source: rotating anode	2938 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.036
ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC 2005)	h = −11→14
T_min = 0.942, T_max = 0.963	k = −14→14
19758 measured reflections	l = −23→28

Refinement top

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0348P)² + 1.9139P] where P = (F_o² + 2F_c²)/3
3198 reflections	(Δ/σ)_max = 0.002
203 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₇H₁₆NO₂⁺·Cl⁻	V = 3618.5 (13) Å³
M_r = 181.66	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 12.181 (2) Å	µ = 0.38 mm⁻¹
b = 12.452 (3) Å	T = 113 K
c = 23.856 (5) Å	0.16 × 0.12 × 0.10 mm

Data collection top

Rigaku Saturn diffractometer	3198 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC 2005)	2938 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.963	R_int = 0.036
19758 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
3198 reflections	Δρ_min = −0.22 e Å⁻³
203 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.68479 (3)	0.09749 (3)	0.579742 (15)	0.01752 (11)
Cl2	0.30866 (3)	0.32732 (3)	0.691066 (15)	0.01992 (11)
O1	0.99622 (9)	0.31527 (9)	1.03992 (5)	0.0231 (3)
O2	0.86105 (10)	−0.08159 (9)	0.88818 (5)	0.0231 (3)
H2	0.8137	−0.1060	0.8673	0.035*
O3	1.09148 (9)	0.15192 (9)	0.74353 (4)	0.0211 (3)
O4	0.84900 (10)	−0.08501 (10)	0.59544 (5)	0.0265 (3)
H4	0.8108	−0.0332	0.5870	0.040*
N1	0.87164 (10)	0.18106 (9)	0.96226 (5)	0.0139 (3)
N2	0.91549 (10)	0.00400 (9)	0.71337 (5)	0.0144 (3)
C1	0.92450 (13)	0.13932 (12)	1.01538 (6)	0.0164 (3)
H1A	0.9974	0.1125	1.0068	0.020*
H1B	0.8814	0.0801	1.0300	0.020*
C2	0.93275 (14)	0.22648 (12)	1.05946 (6)	0.0201 (3)
H2A	0.8596	0.2510	1.0692	0.024*
H2B	0.9664	0.1972	1.0930	0.024*
C3	0.94589 (14)	0.36040 (13)	0.99131 (7)	0.0211 (3)
H3A	0.9889	0.4212	0.9785	0.025*
H3B	0.8732	0.3863	1.0009	0.025*
C4	0.93669 (13)	0.27905 (12)	0.94444 (6)	0.0177 (3)
H4A	1.0097	0.2570	0.9330	0.021*
H4B	0.9012	0.3122	0.9124	0.021*
C5	0.75259 (13)	0.20764 (13)	0.97066 (6)	0.0183 (3)
H5A	0.7147	0.1455	0.9846	0.027*
H5B	0.7209	0.2292	0.9356	0.027*
H5C	0.7460	0.2652	0.9972	0.027*
C6	0.88210 (13)	0.09905 (11)	0.91578 (6)	0.0160 (3)
H6A	0.9587	0.0786	0.9125	0.019*
H6B	0.8607	0.1327	0.8808	0.019*
C7	0.81376 (13)	−0.00259 (12)	0.92364 (7)	0.0191 (3)
H7A	0.8160	−0.0259	0.9624	0.023*
H7B	0.7379	0.0104	0.9133	0.023*
C8	0.98190 (13)	−0.00380 (12)	0.76704 (6)	0.0178 (3)
H8A	0.9364	−0.0341	0.7964	0.021*
H8B	1.0436	−0.0518	0.7611	0.021*
C9	1.02402 (13)	0.10464 (12)	0.78564 (6)	0.0197 (3)
H9A	0.9624	0.1516	0.7935	0.024*
H9B	1.0661	0.0965	0.8199	0.024*
C10	1.02888 (14)	0.16834 (12)	0.69399 (6)	0.0204 (3)
H10A	1.0744	0.2029	0.6659	0.024*
H10B	0.9677	0.2157	0.7022	0.024*
C11	0.98544 (13)	0.06294 (12)	0.67078 (6)	0.0180 (3)
H11A	0.9420	0.0772	0.6375	0.022*
H11B	1.0467	0.0177	0.6600	0.022*
C12	0.80896 (13)	0.06048 (13)	0.72421 (7)	0.0188 (3)
H12A	0.8231	0.1282	0.7421	0.028*
H12B	0.7639	0.0170	0.7482	0.028*
H12C	0.7716	0.0724	0.6893	0.028*
C13	0.89419 (14)	−0.11115 (12)	0.69480 (6)	0.0186 (3)
H13A	0.9637	−0.1424	0.6835	0.022*
H13B	0.8683	−0.1513	0.7270	0.022*
C14	0.81313 (14)	−0.12733 (13)	0.64760 (7)	0.0228 (4)
H14A	0.7994	−0.2036	0.6432	0.027*
H14B	0.7442	−0.0934	0.6577	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0183 (2)	0.0171 (2)	0.01717 (19)	−0.00094 (14)	0.00115 (14)	−0.00020 (13)
Cl2	0.0178 (2)	0.0216 (2)	0.0204 (2)	0.00114 (15)	0.00057 (14)	0.00214 (14)
O1	0.0190 (6)	0.0245 (6)	0.0257 (6)	−0.0032 (5)	−0.0024 (5)	−0.0059 (5)
O2	0.0225 (7)	0.0207 (6)	0.0262 (6)	−0.0008 (5)	−0.0019 (5)	−0.0075 (5)
O3	0.0177 (6)	0.0230 (6)	0.0225 (6)	−0.0025 (5)	−0.0016 (4)	−0.0008 (4)
O4	0.0276 (7)	0.0292 (7)	0.0226 (6)	0.0092 (5)	−0.0014 (5)	−0.0059 (5)
N1	0.0131 (7)	0.0147 (6)	0.0138 (6)	−0.0007 (5)	0.0002 (5)	0.0009 (5)
N2	0.0141 (7)	0.0139 (6)	0.0151 (6)	0.0009 (5)	0.0005 (5)	−0.0001 (5)
C1	0.0165 (8)	0.0172 (8)	0.0155 (7)	0.0018 (6)	−0.0024 (6)	0.0021 (6)
C2	0.0197 (9)	0.0225 (8)	0.0183 (8)	0.0014 (7)	−0.0019 (6)	−0.0015 (6)
C3	0.0218 (9)	0.0164 (8)	0.0252 (8)	−0.0022 (7)	0.0028 (7)	−0.0009 (6)
C4	0.0184 (9)	0.0160 (8)	0.0188 (8)	−0.0038 (6)	0.0037 (6)	0.0026 (6)
C5	0.0105 (8)	0.0225 (8)	0.0220 (8)	0.0026 (6)	−0.0005 (6)	−0.0007 (6)
C6	0.0176 (8)	0.0173 (8)	0.0133 (7)	−0.0005 (6)	0.0013 (6)	−0.0026 (6)
C7	0.0188 (9)	0.0196 (8)	0.0188 (8)	−0.0023 (6)	0.0012 (6)	−0.0029 (6)
C8	0.0163 (8)	0.0217 (8)	0.0153 (8)	0.0035 (6)	−0.0011 (6)	0.0042 (6)
C9	0.0177 (9)	0.0259 (8)	0.0154 (7)	0.0024 (7)	−0.0013 (6)	−0.0021 (6)
C10	0.0227 (9)	0.0182 (8)	0.0202 (8)	−0.0023 (7)	0.0006 (6)	0.0026 (6)
C11	0.0217 (9)	0.0189 (8)	0.0135 (7)	−0.0023 (7)	0.0033 (6)	0.0028 (6)
C12	0.0135 (8)	0.0196 (8)	0.0232 (8)	0.0037 (6)	−0.0009 (6)	−0.0029 (6)
C13	0.0195 (9)	0.0128 (7)	0.0236 (8)	0.0002 (6)	0.0014 (6)	0.0002 (6)
C14	0.0217 (9)	0.0174 (8)	0.0293 (9)	−0.0002 (7)	−0.0013 (7)	−0.0062 (7)

Geometric parameters (Å, º) top

O1—C3	1.4271 (19)	C5—H5A	0.9600
O1—C2	1.4273 (19)	C5—H5B	0.9600
O2—C7	1.4196 (19)	C5—H5C	0.9600
O2—H2	0.8200	C6—C7	1.526 (2)
O3—C10	1.4214 (19)	C6—H6A	0.9700
O3—C9	1.4252 (19)	C6—H6B	0.9700
O4—C14	1.420 (2)	C7—H7A	0.9700
O4—H4	0.8200	C7—H7B	0.9700
N1—C5	1.501 (2)	C8—C9	1.511 (2)
N1—C6	1.5128 (18)	C8—H8A	0.9700
N1—C1	1.5133 (18)	C8—H8B	0.9700
N1—C4	1.5157 (19)	C9—H9A	0.9700
N2—C12	1.4985 (19)	C9—H9B	0.9700
N2—C11	1.5155 (19)	C10—C11	1.520 (2)
N2—C8	1.5176 (19)	C10—H10A	0.9700
N2—C13	1.5229 (19)	C10—H10B	0.9700
C1—C2	1.515 (2)	C11—H11A	0.9700
C1—H1A	0.9700	C11—H11B	0.9700
C1—H1B	0.9700	C12—H12A	0.9600
C2—H2A	0.9700	C12—H12B	0.9600
C2—H2B	0.9700	C12—H12C	0.9600
C3—C4	1.513 (2)	C13—C14	1.511 (2)
C3—H3A	0.9700	C13—H13A	0.9700
C3—H3B	0.9700	C13—H13B	0.9700
C4—H4A	0.9700	C14—H14A	0.9700
C4—H4B	0.9700	C14—H14B	0.9700

C3—O1—C2	109.74 (12)	C7—C6—H6B	108.5
C7—O2—H2	109.5	H6A—C6—H6B	107.5
C10—O3—C9	109.65 (12)	O2—C7—C6	106.26 (12)
C14—O4—H4	109.5	O2—C7—H7A	110.5
C5—N1—C6	109.15 (11)	C6—C7—H7A	110.5
C5—N1—C1	112.03 (11)	O2—C7—H7B	110.5
C6—N1—C1	110.24 (11)	C6—C7—H7B	110.5
C5—N1—C4	111.41 (12)	H7A—C7—H7B	108.7
C6—N1—C4	107.08 (11)	C9—C8—N2	111.81 (12)
C1—N1—C4	106.80 (11)	C9—C8—H8A	109.3
C12—N2—C11	112.05 (11)	N2—C8—H8A	109.3
C12—N2—C8	110.24 (11)	C9—C8—H8B	109.3
C11—N2—C8	107.27 (12)	N2—C8—H8B	109.3
C12—N2—C13	110.16 (12)	H8A—C8—H8B	107.9
C11—N2—C13	110.89 (11)	O3—C9—C8	110.97 (12)
C8—N2—C13	106.02 (11)	O3—C9—H9A	109.4
N1—C1—C2	111.31 (12)	C8—C9—H9A	109.4
N1—C1—H1A	109.4	O3—C9—H9B	109.4
C2—C1—H1A	109.4	C8—C9—H9B	109.4
N1—C1—H1B	109.4	H9A—C9—H9B	108.0
C2—C1—H1B	109.4	O3—C10—C11	111.44 (12)
H1A—C1—H1B	108.0	O3—C10—H10A	109.3
O1—C2—C1	111.36 (13)	C11—C10—H10A	109.3
O1—C2—H2A	109.4	O3—C10—H10B	109.3
C1—C2—H2A	109.4	C11—C10—H10B	109.3
O1—C2—H2B	109.4	H10A—C10—H10B	108.0
C1—C2—H2B	109.4	N2—C11—C10	111.70 (12)
H2A—C2—H2B	108.0	N2—C11—H11A	109.3
O1—C3—C4	111.64 (13)	C10—C11—H11A	109.3
O1—C3—H3A	109.3	N2—C11—H11B	109.3
C4—C3—H3A	109.3	C10—C11—H11B	109.3
O1—C3—H3B	109.3	H11A—C11—H11B	107.9
C4—C3—H3B	109.3	N2—C12—H12A	109.5
H3A—C3—H3B	108.0	N2—C12—H12B	109.5
C3—C4—N1	111.74 (12)	H12A—C12—H12B	109.5
C3—C4—H4A	109.3	N2—C12—H12C	109.5
N1—C4—H4A	109.3	H12A—C12—H12C	109.5
C3—C4—H4B	109.3	H12B—C12—H12C	109.5
N1—C4—H4B	109.3	C14—C13—N2	116.97 (13)
H4A—C4—H4B	107.9	C14—C13—H13A	108.1
N1—C5—H5A	109.5	N2—C13—H13A	108.1
N1—C5—H5B	109.5	C14—C13—H13B	108.1
H5A—C5—H5B	109.5	N2—C13—H13B	108.1
N1—C5—H5C	109.5	H13A—C13—H13B	107.3
H5A—C5—H5C	109.5	O4—C14—C13	113.72 (14)
H5B—C5—H5C	109.5	O4—C14—H14A	108.8
N1—C6—C7	115.07 (12)	C13—C14—H14A	108.8
N1—C6—H6A	108.5	O4—C14—H14B	108.8
C7—C6—H6A	108.5	C13—C14—H14B	108.8
N1—C6—H6B	108.5	H14A—C14—H14B	107.7

C5—N1—C1—C2	−68.05 (16)	C12—N2—C8—C9	−69.53 (16)
C6—N1—C1—C2	170.19 (12)	C11—N2—C8—C9	52.72 (16)
C4—N1—C1—C2	54.19 (16)	C13—N2—C8—C9	171.26 (13)
C3—O1—C2—C1	60.35 (16)	C10—O3—C9—C8	61.61 (16)
N1—C1—C2—O1	−59.42 (17)	N2—C8—C9—O3	−58.98 (17)
C2—O1—C3—C4	−59.66 (16)	C9—O3—C10—C11	−61.10 (16)
O1—C3—C4—N1	58.04 (18)	C12—N2—C11—C10	69.22 (16)
C5—N1—C4—C3	69.00 (16)	C8—N2—C11—C10	−51.90 (16)
C6—N1—C4—C3	−171.72 (13)	C13—N2—C11—C10	−167.24 (13)
C1—N1—C4—C3	−53.63 (16)	O3—C10—C11—N2	57.82 (17)
C5—N1—C6—C7	−54.28 (16)	C12—N2—C13—C14	50.60 (17)
C1—N1—C6—C7	69.17 (16)	C11—N2—C13—C14	−74.01 (17)
C4—N1—C6—C7	−175.01 (13)	C8—N2—C13—C14	169.87 (13)
N1—C6—C7—O2	−160.59 (12)	N2—C13—C14—O4	66.19 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl2ⁱ	0.82	2.20	3.0222 (13)	178
O4—H4···Cl1	0.82	2.24	3.0505 (13)	168
C1—H1B···Cl1ⁱⁱ	0.97	2.64	3.5812 (16)	165
C2—H2B···O2ⁱⁱⁱ	0.97	2.59	3.335 (2)	134
C4—H4B···Cl2^iv	0.97	2.72	3.6390 (17)	158
C5—H5C···Cl1^v	0.96	2.71	3.6527 (16)	167
C6—H6A···Cl1^iv	0.97	2.77	3.6888 (18)	158
C8—H8A···O2	0.97	2.45	3.385 (2)	163
C9—H9B···Cl1^iv	0.97	2.80	3.7625 (17)	174
C11—H11A···O4	0.97	2.52	3.064 (2)	115
C13—H13A···Cl2^vi	0.97	2.80	3.7009 (18)	154
C13—H13B···O3^vii	0.97	2.60	3.3013 (19)	130

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+3/2, −y, z+1/2; (iii) −x+2, −y, −z+2; (iv) x+1/2, y, −z+3/2; (v) x, −y+1/2, z+1/2; (vi) −x+3/2, y−1/2, z; (vii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₇H₁₆NO₂⁺·Cl⁻
M_r	181.66
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	113
a, b, c (Å)	12.181 (2), 12.452 (3), 23.856 (5)
V (Å³)	3618.5 (13)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC 2005)
T_min, T_max	0.942, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	19758, 3198, 2938
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.076, 1.06
No. of reflections	3198
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.22

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl2ⁱ	0.82	2.20	3.0222 (13)	177.9
O4—H4···Cl1	0.82	2.24	3.0505 (13)	167.6
C1—H1B···Cl1ⁱⁱ	0.97	2.64	3.5812 (16)	164.8
C2—H2B···O2ⁱⁱⁱ	0.97	2.59	3.335 (2)	134.1
C4—H4B···Cl2^iv	0.97	2.72	3.6390 (17)	158.3
C5—H5C···Cl1^v	0.96	2.71	3.6527 (16)	166.6
C6—H6A···Cl1^iv	0.97	2.77	3.6888 (18)	158.2
C8—H8A···O2	0.97	2.45	3.385 (2)	162.7
C9—H9B···Cl1^iv	0.97	2.80	3.7625 (17)	173.6
C11—H11A···O4	0.97	2.52	3.064 (2)	115.1
C13—H13A···Cl2^vi	0.97	2.80	3.7009 (18)	154.0
C13—H13B···O3^vii	0.97	2.60	3.3013 (19)	129.8

Acknowledgements

The authors thank Tianjin Natural Science Foundation (07JCYBJC02200) for financial support.

References

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