(4-Hydr­oxy-3-nitro­benz­yl)methyl­ammonium chloride

Boyle, G.A.; Kruger, H.G.; Maguire, G.E.M.; Paraskevopoulos, J.

doi:10.1107/S160053680800473X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o625

doi:10.1107/S160053680800473X

Open

access

(4-Hydroxy-3-nitrobenzyl)methylammonium chloride

Grant A. Boyle,^a Hendrik G. Kruger,^a Glenn E. M. Maguire ^a ^* and Jason Paraskevopoulos ^a

^aSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
^*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 30 November 2007; accepted 18 February 2008; online 27 February 2008)

The title compound, C₈H₁₁N₂O₃⁺·Cl⁻, was synthesized as an intermediate in the development of a new sugar sensor. The structure displays N—H⋯Cl and O—H⋯O hydrogen bonding, as well as weak O—H⋯Cl interactions and π–π stacking (3.298 Å). There are two formula units in the asymmetric unit.

Related literature

For related literature, see: James et al. (1995 ).

Experimental

Crystal data

C₈H₁₁N₂O₃⁺·Cl⁻
M_r = 218.64
Triclinic, $[P \overline 1]$
a = 7.7650 (2) Å
b = 10.5922 (3) Å
c = 13.5987 (4) Å
α = 70.262 (1)°
β = 78.368 (1)°
γ = 76.459 (1)°
V = 1014.27 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 173 (2) K
0.48 × 0.39 × 0.36 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none
11798 measured reflections
4901 independent reflections
4057 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.094
S = 1.06
4901 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2A⋯Cl1A	0.92	2.23	3.1301 (11)	167
N2A—H2B⋯Cl1B	0.92	2.18	3.0898 (11)	173
O1A—H1A⋯O2A	0.84	1.89	2.5917 (14)	140
O1A—H1A⋯Cl1Bⁱ	0.84	2.87	3.3918 (10)	122
N2B—H2C⋯Cl1Aⁱⁱ	0.92	2.17	3.0775 (11)	168
N2B—H2D⋯Cl1Bⁱⁱⁱ	0.92	2.26	3.1671 (10)	168
O1B—H1B⋯O2B	0.84	1.88	2.5860 (14)	141
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 1999 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2006 ) and WinGX (Farrugia, 1999 ); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800473X/hg2362sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800473X/hg2362Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was synthesized as an intermediate in the development of a new sugar sensor (James et al., 1995). The compound itself is also novel and is being reported for the first time.

The structure consists of two molecules in the asymmetric unit (Figure 1). The cation consists of a planar nitro phenol ring with a methylaminomethyl group in the para position with respect to the hydroxy group (O1) on the ring. The methylammonium groups attached to the methylene carbon (C7) deviate from the plane of the ring with a torsion angle of -121.52 (13)° for C3A—C4A—C7A—N2A and -46.81 (16)° for C3B—C4B—C7B—N2B.

The structure exhibits both intermolecular (N1—H1···Cl) and intramolecular (O1—H1···O2) hydrogen bonding interactions (Table 1, Figure 2). The chloride ions act as hydrogen bond acceptors between adjacent molecules. Weak interactions are also observed between O1—H1···Cl1. These interactions, with a bond length of 2.87Å (O1A—H1A···Cl1Bⁱ), are more likely weak Van der Waals interactions rather than true hydrogen bonds. See Table 1 for a full list of all hydrogen bond interactions. An interdigitated, layered structure is observed with the aromatic groups π–π stacking above each other and the methylaminomethyl group interacting with the chloride ions in hydrogen bonded layers (Figure 3).

Related literature top

For related literature, see: James et al. (1995).

Experimental top

4-Chloromethyl-2-nitrophenol, 3.8 g (20 mmol), was dissolved in DMF (30 ml). To this was added triethylamine (3 ml) followed by 40% methylamine in H₂O (5 ml, 58 mmol). The reaction was heated to 333 K and left to stir overnight. The solvent was removed under vacuum to afford an orange solid, which was recrystallized from methanol at room temperature. Yield 3.49 g (80%). Decomposition point 373–375 K.

¹H-NMR (400 MHz, D₂O): p.p.m. = 0.00 (TMS), 2.62 (s, 3H, CH₃), 4.12 (s, 2H, CH₂), 7.14 (d, J = 8.5 Hz, 1H, H5), 7.60 (d, J = 8.5 Hz, 1H, H6), 8.13 (s, 1H, H3).¹³C-NMR(100 MHz, D₂O): p.p.m. = 0.00 (TMS), 32.58 (CH₃), 51.50 (CH₂),121.30 (C6), 123.50 (C4), 127.75 (C3), 136.86 (C2), 139.04 (C5), 154.76 (C1).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and WinGX (Farrugia, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit showing ellipsoids at the 50% probability level and the numbering scheme employed.
	Fig. 2. Diagram of the inter- and intramolecular hydrogen bonding. Hydrogen atoms have been omitted for clarity.
	Fig. 3. Depiction of the packing. Hydrogen atoms have been omitted for clarity.

(4-Hydroxy-3-nitrobenzyl)methylammonium chloride top

Crystal data top

C₈H₁₁N₂O₃⁺·Cl⁻	Z = 4
M_r = 218.64	F(000) = 456
Triclinic, P1	D_x = 1.432 Mg m⁻³ D_m = 1.432 Mg m⁻³ D_m measured by not measured
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7650 (2) Å	Cell parameters from 6008 reflections
b = 10.5922 (3) Å	θ = 4.6–28.4°
c = 13.5987 (4) Å	µ = 0.36 mm⁻¹
α = 70.262 (1)°	T = 173 K
β = 78.368 (1)°	Block, orange
γ = 76.459 (1)°	0.48 × 0.39 × 0.36 mm
V = 1014.27 (5) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4057 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 28.0°, θ_min = 1.6°
ϕ and ω scans	h = −10→10
11798 measured reflections	k = −13→13
4901 independent reflections	l = −17→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0542P)² + 0.0174P] where P = (F_o² + 2F_c²)/3
4901 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₈H₁₁N₂O₃⁺·Cl⁻	γ = 76.459 (1)°
M_r = 218.64	V = 1014.27 (5) Å³
Triclinic, P1	Z = 4
a = 7.7650 (2) Å	Mo Kα radiation
b = 10.5922 (3) Å	µ = 0.36 mm⁻¹
c = 13.5987 (4) Å	T = 173 K
α = 70.262 (1)°	0.48 × 0.39 × 0.36 mm
β = 78.368 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4057 reflections with I > 2σ(I)
11798 measured reflections	R_int = 0.034
4901 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	Δρ_max = 0.24 e Å⁻³
4901 reflections	Δρ_min = −0.31 e Å⁻³
257 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
C1A	0.07924 (17)	0.64421 (12)	0.39067 (10)	0.0280 (3)
C2A	−0.05629 (16)	0.60295 (12)	0.36161 (10)	0.0266 (3)
C3A	−0.02230 (17)	0.54096 (12)	0.28266 (10)	0.0277 (3)
H3A	−0.1168	0.5129	0.2652	0.033*
C4A	0.14689 (17)	0.52009 (12)	0.22990 (10)	0.0272 (3)
C5A	0.28403 (17)	0.55999 (13)	0.25897 (11)	0.0311 (3)
H5A	0.4022	0.5452	0.2238	0.037*
C6A	0.25051 (17)	0.61995 (13)	0.33725 (11)	0.0318 (3)
H6A	0.3462	0.6456	0.3556	0.038*
C7A	0.17964 (18)	0.46001 (13)	0.14103 (11)	0.0328 (3)
H7A	0.0658	0.4412	0.1318	0.039*
H7B	0.2224	0.5269	0.0749	0.039*
C8A	0.3333 (2)	0.26316 (15)	0.07972 (12)	0.0408 (3)
H8A	0.2200	0.2359	0.0819	0.061*
H8B	0.4277	0.1822	0.0934	0.061*
H8C	0.3646	0.3263	0.0100	0.061*
N1A	−0.23762 (14)	0.62436 (11)	0.41284 (10)	0.0339 (3)
N2A	0.31439 (14)	0.33107 (10)	0.16086 (8)	0.0270 (2)
H2A	0.4233	0.3503	0.1621	0.032*
H2B	0.2807	0.2726	0.2259	0.032*
O1A	0.06011 (13)	0.70500 (10)	0.46491 (8)	0.0388 (2)
H1A	−0.0465	0.7123	0.4939	0.058*
O2A	−0.27172 (14)	0.68749 (10)	0.47848 (9)	0.0457 (3)
O3A	−0.35065 (13)	0.58060 (12)	0.39075 (10)	0.0518 (3)
C1B	0.08090 (17)	0.14787 (12)	0.89457 (10)	0.0271 (3)
C2B	−0.03119 (15)	0.10203 (12)	0.85044 (10)	0.0248 (3)
C3B	0.03195 (16)	0.04521 (12)	0.76886 (10)	0.0256 (3)
H3B	−0.0483	0.0164	0.7401	0.031*
C4B	0.21073 (16)	0.03066 (12)	0.72966 (10)	0.0251 (3)
C5B	0.32453 (17)	0.07415 (13)	0.77435 (11)	0.0294 (3)
H5B	0.4486	0.0636	0.7488	0.035*
C6B	0.26146 (17)	0.13157 (13)	0.85399 (11)	0.0317 (3)
H6B	0.3423	0.1608	0.8821	0.038*
C7B	0.28683 (17)	−0.02588 (12)	0.63923 (10)	0.0285 (3)
H7C	0.2538	0.0440	0.5729	0.034*
H7D	0.4189	−0.0455	0.6340	0.034*
C8B	0.3304 (2)	−0.22269 (14)	0.57491 (11)	0.0383 (3)
H8D	0.3227	−0.1618	0.5028	0.057*
H8E	0.2844	−0.3051	0.5841	0.057*
H8F	0.4554	−0.2478	0.5879	0.057*
N1B	−0.22054 (14)	0.11494 (11)	0.88843 (9)	0.0311 (3)
N2B	0.22290 (13)	−0.15229 (10)	0.65039 (9)	0.0260 (2)
H2C	0.2293	−0.2100	0.7180	0.031*
H2D	0.1052	−0.1306	0.6391	0.031*
O1B	0.03022 (13)	0.20461 (10)	0.97277 (8)	0.0357 (2)
H1B	−0.0805	0.2095	0.9912	0.054*
O2B	−0.28171 (13)	0.17175 (11)	0.95706 (8)	0.0424 (3)
O3B	−0.31379 (13)	0.06993 (12)	0.85167 (10)	0.0492 (3)
Cl1A	0.70902 (4)	0.37097 (3)	0.13787 (3)	0.03519 (10)
Cl1B	0.18542 (4)	0.12266 (3)	0.36875 (2)	0.03163 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.0284 (6)	0.0254 (6)	0.0266 (7)	−0.0009 (5)	−0.0051 (5)	−0.0051 (5)
C2A	0.0210 (6)	0.0246 (6)	0.0276 (7)	−0.0023 (5)	−0.0007 (5)	−0.0024 (5)
C3A	0.0258 (6)	0.0239 (6)	0.0309 (7)	−0.0044 (5)	−0.0065 (5)	−0.0039 (5)
C4A	0.0286 (6)	0.0240 (6)	0.0247 (6)	−0.0008 (5)	−0.0042 (5)	−0.0041 (5)
C5A	0.0213 (6)	0.0327 (7)	0.0350 (7)	−0.0018 (5)	−0.0002 (5)	−0.0087 (6)
C6A	0.0238 (6)	0.0334 (7)	0.0394 (8)	−0.0037 (5)	−0.0074 (6)	−0.0119 (6)
C7A	0.0336 (7)	0.0331 (7)	0.0283 (7)	0.0017 (6)	−0.0063 (6)	−0.0088 (6)
C8A	0.0502 (9)	0.0437 (8)	0.0341 (8)	−0.0092 (7)	−0.0013 (7)	−0.0208 (7)
N1A	0.0250 (6)	0.0310 (6)	0.0382 (7)	−0.0029 (5)	0.0015 (5)	−0.0055 (5)
N2A	0.0277 (5)	0.0285 (5)	0.0241 (5)	−0.0061 (4)	−0.0002 (4)	−0.0083 (4)
O1A	0.0370 (5)	0.0461 (6)	0.0373 (6)	−0.0035 (5)	−0.0040 (5)	−0.0213 (5)
O2A	0.0373 (6)	0.0484 (6)	0.0471 (7)	−0.0046 (5)	0.0121 (5)	−0.0213 (5)
O3A	0.0232 (5)	0.0635 (7)	0.0721 (8)	−0.0122 (5)	0.0004 (5)	−0.0258 (6)
C1B	0.0277 (6)	0.0275 (6)	0.0248 (6)	−0.0024 (5)	−0.0058 (5)	−0.0066 (5)
C2B	0.0207 (6)	0.0238 (6)	0.0269 (6)	−0.0030 (5)	−0.0032 (5)	−0.0045 (5)
C3B	0.0236 (6)	0.0245 (6)	0.0287 (7)	−0.0049 (5)	−0.0061 (5)	−0.0065 (5)
C4B	0.0244 (6)	0.0231 (6)	0.0251 (6)	−0.0025 (5)	−0.0046 (5)	−0.0044 (5)
C5B	0.0211 (6)	0.0338 (7)	0.0320 (7)	−0.0029 (5)	−0.0052 (5)	−0.0085 (6)
C6B	0.0258 (6)	0.0382 (7)	0.0353 (7)	−0.0063 (5)	−0.0100 (6)	−0.0128 (6)
C7B	0.0292 (6)	0.0286 (6)	0.0264 (7)	−0.0069 (5)	−0.0011 (5)	−0.0072 (5)
C8B	0.0434 (8)	0.0395 (8)	0.0332 (8)	−0.0029 (6)	0.0012 (6)	−0.0193 (6)
N1B	0.0233 (5)	0.0322 (6)	0.0359 (7)	−0.0050 (5)	−0.0010 (5)	−0.0098 (5)
N2B	0.0232 (5)	0.0282 (5)	0.0255 (5)	−0.0020 (4)	−0.0036 (4)	−0.0084 (4)
O1B	0.0335 (5)	0.0462 (6)	0.0327 (5)	−0.0062 (4)	−0.0038 (4)	−0.0200 (4)
O2B	0.0322 (5)	0.0554 (6)	0.0411 (6)	−0.0068 (5)	0.0061 (4)	−0.0237 (5)
O3B	0.0251 (5)	0.0671 (7)	0.0690 (8)	−0.0133 (5)	−0.0015 (5)	−0.0376 (6)
Cl1A	0.02968 (17)	0.0419 (2)	0.02772 (18)	−0.00866 (14)	−0.00213 (13)	−0.00206 (14)
Cl1B	0.02849 (17)	0.03788 (18)	0.02609 (18)	−0.00808 (13)	−0.00452 (13)	−0.00475 (13)

Geometric parameters (Å, º) top

C1A—O1A	1.3378 (15)	C1B—O1B	1.3413 (15)
C1A—C6A	1.3924 (18)	C1B—C6B	1.3925 (18)
C1A—C2A	1.3981 (18)	C1B—C2B	1.3996 (17)
C2A—C3A	1.3908 (18)	C2B—C3B	1.3882 (17)
C2A—N1A	1.4425 (16)	C2B—N1B	1.4473 (15)
C3A—C4A	1.3713 (18)	C3B—C4B	1.3755 (17)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.4008 (18)	C4B—C5B	1.3994 (17)
C4A—C7A	1.5000 (18)	C4B—C7B	1.5030 (17)
C5A—C6A	1.3682 (19)	C5B—C6B	1.3691 (18)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—N2A	1.4928 (16)	C7B—N2B	1.4852 (15)
C7A—H7A	0.9900	C7B—H7C	0.9900
C7A—H7B	0.9900	C7B—H7D	0.9900
C8A—N2A	1.4759 (16)	C8B—N2B	1.4788 (16)
C8A—H8A	0.9800	C8B—H8D	0.9800
C8A—H8B	0.9800	C8B—H8E	0.9800
C8A—H8C	0.9800	C8B—H8F	0.9800
N1A—O3A	1.2109 (15)	N1B—O3B	1.2125 (14)
N1A—O2A	1.2406 (15)	N1B—O2B	1.2350 (14)
N2A—H2A	0.9200	N2B—H2C	0.9200
N2A—H2B	0.9200	N2B—H2D	0.9200
O1A—H1A	0.8400	O1B—H1B	0.8400

O1A—C1A—C6A	116.81 (12)	O1B—C1B—C6B	117.37 (11)
O1A—C1A—C2A	126.21 (12)	O1B—C1B—C2B	125.88 (12)
C6A—C1A—C2A	116.98 (12)	C6B—C1B—C2B	116.74 (11)
C3A—C2A—C1A	121.68 (12)	C3B—C2B—C1B	122.28 (11)
C3A—C2A—N1A	117.71 (11)	C3B—C2B—N1B	117.56 (11)
C1A—C2A—N1A	120.61 (11)	C1B—C2B—N1B	120.15 (11)
C4A—C3A—C2A	120.34 (12)	C4B—C3B—C2B	119.98 (11)
C4A—C3A—H3A	119.8	C4B—C3B—H3B	120.0
C2A—C3A—H3A	119.8	C2B—C3B—H3B	120.0
C3A—C4A—C5A	118.47 (12)	C3B—C4B—C5B	118.22 (11)
C3A—C4A—C7A	119.74 (12)	C3B—C4B—C7B	122.67 (11)
C5A—C4A—C7A	121.76 (12)	C5B—C4B—C7B	119.08 (11)
C6A—C5A—C4A	121.07 (12)	C6B—C5B—C4B	121.63 (12)
C6A—C5A—H5A	119.5	C6B—C5B—H5B	119.2
C4A—C5A—H5A	119.5	C4B—C5B—H5B	119.2
C5A—C6A—C1A	121.45 (12)	C5B—C6B—C1B	121.13 (12)
C5A—C6A—H6A	119.3	C5B—C6B—H6B	119.4
C1A—C6A—H6A	119.3	C1B—C6B—H6B	119.4
N2A—C7A—C4A	111.77 (10)	N2B—C7B—C4B	113.02 (10)
N2A—C7A—H7A	109.3	N2B—C7B—H7C	109.0
C4A—C7A—H7A	109.3	C4B—C7B—H7C	109.0
N2A—C7A—H7B	109.3	N2B—C7B—H7D	109.0
C4A—C7A—H7B	109.3	C4B—C7B—H7D	109.0
H7A—C7A—H7B	107.9	H7C—C7B—H7D	107.8
N2A—C8A—H8A	109.5	N2B—C8B—H8D	109.5
N2A—C8A—H8B	109.5	N2B—C8B—H8E	109.5
H8A—C8A—H8B	109.5	H8D—C8B—H8E	109.5
N2A—C8A—H8C	109.5	N2B—C8B—H8F	109.5
H8A—C8A—H8C	109.5	H8D—C8B—H8F	109.5
H8B—C8A—H8C	109.5	H8E—C8B—H8F	109.5
O3A—N1A—O2A	122.35 (12)	O3B—N1B—O2B	122.23 (11)
O3A—N1A—C2A	119.40 (12)	O3B—N1B—C2B	118.92 (11)
O2A—N1A—C2A	118.25 (11)	O2B—N1B—C2B	118.84 (10)
C8A—N2A—C7A	112.24 (11)	C8B—N2B—C7B	111.57 (10)
C8A—N2A—H2A	109.2	C8B—N2B—H2C	109.3
C7A—N2A—H2A	109.2	C7B—N2B—H2C	109.3
C8A—N2A—H2B	109.2	C8B—N2B—H2D	109.3
C7A—N2A—H2B	109.2	C7B—N2B—H2D	109.3
H2A—N2A—H2B	107.9	H2C—N2B—H2D	108.0
C1A—O1A—H1A	109.5	C1B—O1B—H1B	109.5

O1A—C1A—C2A—C3A	179.66 (12)	O1B—C1B—C2B—C3B	179.51 (12)
C6A—C1A—C2A—C3A	−0.25 (19)	C6B—C1B—C2B—C3B	−1.17 (19)
O1A—C1A—C2A—N1A	0.0 (2)	O1B—C1B—C2B—N1B	0.5 (2)
C6A—C1A—C2A—N1A	−179.92 (11)	C6B—C1B—C2B—N1B	179.83 (11)
C1A—C2A—C3A—C4A	−0.80 (19)	C1B—C2B—C3B—C4B	0.92 (19)
N1A—C2A—C3A—C4A	178.87 (11)	N1B—C2B—C3B—C4B	179.94 (11)
C2A—C3A—C4A—C5A	1.30 (18)	C2B—C3B—C4B—C5B	0.13 (18)
C2A—C3A—C4A—C7A	−176.71 (11)	C2B—C3B—C4B—C7B	−178.01 (11)
C3A—C4A—C5A—C6A	−0.77 (19)	C3B—C4B—C5B—C6B	−0.89 (19)
C7A—C4A—C5A—C6A	177.19 (12)	C7B—C4B—C5B—C6B	177.32 (12)
C4A—C5A—C6A—C1A	−0.3 (2)	C4B—C5B—C6B—C1B	0.6 (2)
O1A—C1A—C6A—C5A	−179.13 (12)	O1B—C1B—C6B—C5B	179.78 (12)
C2A—C1A—C6A—C5A	0.8 (2)	C2B—C1B—C6B—C5B	0.4 (2)
C3A—C4A—C7A—N2A	−121.52 (13)	C3B—C4B—C7B—N2B	−46.81 (16)
C5A—C4A—C7A—N2A	60.54 (16)	C5B—C4B—C7B—N2B	135.07 (12)
C3A—C2A—N1A—O3A	4.67 (18)	C3B—C2B—N1B—O3B	3.65 (18)
C1A—C2A—N1A—O3A	−175.66 (12)	C1B—C2B—N1B—O3B	−177.30 (12)
C3A—C2A—N1A—O2A	−175.38 (12)	C3B—C2B—N1B—O2B	−176.18 (11)
C1A—C2A—N1A—O2A	4.30 (18)	C1B—C2B—N1B—O2B	2.86 (18)
C4A—C7A—N2A—C8A	173.76 (12)	C4B—C7B—N2B—C8B	−166.60 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···Cl1A	0.92	2.23	3.1301 (11)	167
N2A—H2B···Cl1B	0.92	2.18	3.0898 (11)	173
O1A—H1A···O2A	0.84	1.89	2.5917 (14)	140
O1A—H1A···Cl1Bⁱ	0.84	2.87	3.3918 (10)	122
N2B—H2C···Cl1Aⁱⁱ	0.92	2.17	3.0775 (11)	168
N2B—H2D···Cl1Bⁱⁱⁱ	0.92	2.26	3.1671 (10)	168
O1B—H1B···O2B	0.84	1.88	2.5860 (14)	141

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₈H₁₁N₂O₃⁺·Cl⁻
M_r	218.64
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.7650 (2), 10.5922 (3), 13.5987 (4)
α, β, γ (°)	70.262 (1), 78.368 (1), 76.459 (1)
V (Å³)	1014.27 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.48 × 0.39 × 0.36

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11798, 4901, 4057
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.094, 1.06
No. of reflections	4901
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.31

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 1999), Mercury (Macrae et al., 2006) and WinGX (Farrugia, 1999), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···Cl1A	0.92	2.23	3.1301 (11)	166.7
N2A—H2B···Cl1B	0.92	2.18	3.0898 (11)	172.6
O1A—H1A···O2A	0.84	1.89	2.5917 (14)	140.2
O1A—H1A···Cl1Bⁱ	0.84	2.87	3.3918 (10)	122.4
N2B—H2C···Cl1Aⁱⁱ	0.92	2.17	3.0775 (11)	168.0
N2B—H2D···Cl1Bⁱⁱⁱ	0.92	2.26	3.1671 (10)	168.2
O1B—H1B···O2B	0.84	1.88	2.5860 (14)	141.1

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z+1.

Acknowledgements

We thank Dr Manuel Fernandes of the Jan Boeyens Structural Chemistry Laboratory at the University of the Witwatersrand for his assistance in the acquisition of the crystallographic data. Aspen Pharmacare is acknowledged for their financial support.

References

Bruker (1999). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
James, T. D., Sandanayake, K. R. A. S., Iuguchi, R. & Shinkai, S. (1995). J. Am. Chem. Soc. 117, 8982–8987. CrossRef CAS Web of Science Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar