Duloxetine hydro­chloride

Bhadbhade, M.; Hook, J.; Marjo, C.; Rich, A.; Lin, Q.

doi:10.1107/S1600536809033996

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2294

doi:10.1107/S1600536809033996

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Duloxetine hydrochloride

Mohan Bhadbhade,^a ^* James Hook,^a Chris Marjo,^a Anne Rich ^a and Qinghong Lin ^b

^aUNSW Analytical Centre, The University of New South Wales, Sydney, NSW 2052, Australia, and ^bArrow Laboratories Ltd, Croydon South, Victoria 3136, Australia
^*Correspondence e-mail: m.bhadbhade@unsw.edu.au

(Received 31 July 2009; accepted 25 August 2009; online 29 August 2009)

The title compound [systematic name: N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-aminium chloride], C₁₈H₂₀NOS⁺·Cl⁻, was crystallized from 1,4-dioxane. Twofold rotational disorder exhibited by the thiophene ring in a 0.580 (5):0.420 (5) ratio represents two different conformations of the molecule that exist in the same crystal form. The crystal structure contains strong N—H⋯Cl hydrogen bonds.

Related literature

For therapeutic properties of duloxetine hydrochloride, see Waitekus & Kirkpatrick (2004 ). For related structures, see: Brenna et al. (2007 ); Tao et al. (2008 ). The title compound is reported to have different polymorphs on the basis of X-ray powder diffraction data, see: Ini et al. (2006 ).

Experimental

Crystal data

C₁₈H₂₀NOS⁺·Cl⁻
M_r = 333.86
Monoclinic, P 2₁
a = 9.7453 (10) Å
b = 6.9227 (7) Å
c = 13.4247 (16) Å
β = 109.432 (4)°
V = 854.09 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 150 K
0.38 × 0.08 × 0.03 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.879, T_max = 0.990
6386 measured reflections
2947 independent reflections
2255 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.131
S = 0.79
2947 reflections
237 parameters
110 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1309 Friedel pairs
Flack parameter: −0.05 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1ⁱ	0.92	2.23	3.113 (3)	161
N1—H1B⋯Cl1	0.92	2.18	3.087 (3)	170
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033996/bg2289sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033996/bg2289Isup2.hkl

checkCIF report

Comment top

Duloxetine hydrochloride (1) is a new generation drug indicated for the management of major depressive disorders as well as for neuropathic pain (Waitekus, et al., 2004). The compound 1 is reported to have different polymorphs on the basis of X-ray powder diffraction data (Ini et al., 2006), but no single-crystal structure has as yet been presented. The only structures reported are that of a related racemic precursor (Tao, et al., 2008) and of a regioisomer (Brenna et al., 2007). Herein we report the structure of the drug itself (Fig. 1).

In the crystal structure, the thiophene ring is disordered over two positions obtained by 180 degree rotation about C11—C12 bond in a 0.580/0.420 (5) ratio. The same disorder with similar occupancies was also observed in the structure of an impurity (Brenna et al., 2007). These two orientations represent two different molecular conformations that exist in the same crystal structure; in one of them (minor occupancy) the S atom makes a short intramolecular contact with the oxygen atom (S···O = 2.957 Å). The thiophene and naphthyl units are almost perpendicular to each other (angle between their mean planes 87.9 (1) °).

The crystal packing (Fig. 2) shows that both the H-atoms attached to the N atom of the side chain make strong almost linear H-bonding contacts with the chloride ion.

Related literature top

For therapeutic properties of duloxetine hydrochloride, see Waitekus et al. (2004). For related structures, see: Brenna et al. (2007); Tao et al. (2008). The title compound is reported to have different polymorphs on the basis of X-ray powder diffraction data, see: Ini et al. (2006).

Experimental top

Microcrystalline powder of (1) was supplied by Arrow Laboratories Ltd.,Croydon, Australia. Recrystallization of this powder by slow evaporation was attempted in acetonitrile, 1,4-dioxane,chlorobenzene and 2-propanol. Suitable single crystals in the form of thin plates were grown from the first three solvents, crystals from chlorobenzene were very thin silky fibres unsuitable for single-crystal analysis. Crystals from the first three solvents yielded the same monoclinic P2(1) form having unit-cell parameters as given in Table 1. Amongst these, better quality crystals were obtained from 1,4-dioxane, which were used for further structural analysis.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: sAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of 1. Displacement ellipsoids drawn at 50% level.
	Fig. 2. Packing view of1 showing N—H···Cl interactions.

N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-aminium chloride top

Crystal data top

C₁₈H₂₀NOS⁺·Cl⁻	F(000) = 352
M_r = 333.86	D_x = 1.298 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1635 reflections
a = 9.7453 (10) Å	θ = 2.3–22.1°
b = 6.9227 (7) Å	µ = 0.35 mm⁻¹
c = 13.4247 (16) Å	T = 150 K
β = 109.432 (4)°	Thin Plates, colourless
V = 854.09 (16) Å³	0.38 × 0.08 × 0.03 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2947 independent reflections
Radiation source: fine-focus sealed tube	2255 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ scans, and ω scans with κ offsets	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→11
T_min = 0.879, T_max = 0.990	k = −8→8
6386 measured reflections	l = −15→15

Refinement top

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.1P)² + 0.0292P] where P = (F_o² + 2F_c²)/3
S = 0.79	(Δ/σ)_max = 0.005
2947 reflections	Δρ_max = 0.17 e Å⁻³
237 parameters	Δρ_min = −0.21 e Å⁻³
110 restraints	Absolute structure: Flack (1983), 1309 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (10)

Crystal data top

C₁₈H₂₀NOS⁺·Cl⁻	V = 854.09 (16) Å³
M_r = 333.86	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.7453 (10) Å	µ = 0.35 mm⁻¹
b = 6.9227 (7) Å	T = 150 K
c = 13.4247 (16) Å	0.38 × 0.08 × 0.03 mm
β = 109.432 (4)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2947 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2255 reflections with I > 2σ(I)
T_min = 0.879, T_max = 0.990	R_int = 0.058
6386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.131	Δρ_max = 0.17 e Å⁻³
S = 0.79	Δρ_min = −0.21 e Å⁻³
2947 reflections	Absolute structure: Flack (1983), 1309 Friedel pairs
237 parameters	Absolute structure parameter: −0.05 (10)
110 restraints

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	Occ. (<1)
C1	0.7076 (5)	1.0388 (6)	0.3732 (3)	0.0414 (10)
H1	0.6473	1.0546	0.3018	0.050*
C2	0.8113 (5)	1.1721 (7)	0.4181 (3)	0.0559 (13)
H2	0.8222	1.2804	0.3779	0.067*
C3	0.9031 (5)	1.1525 (7)	0.5234 (3)	0.0498 (12)
H3	0.9769	1.2456	0.5538	0.060*
C4	0.8856 (4)	0.9990 (6)	0.5818 (3)	0.0404 (10)
H4	0.9465	0.9877	0.6534	0.048*
C5	0.7784 (4)	0.8557 (6)	0.5376 (2)	0.0333 (8)
C6	0.7619 (5)	0.6944 (7)	0.5957 (3)	0.0488 (12)
H6	0.8217	0.6804	0.6674	0.059*
C7	0.6613 (5)	0.5596 (7)	0.5500 (3)	0.0594 (14)
H7	0.6518	0.4508	0.5904	0.071*
C8	0.5696 (5)	0.5748 (7)	0.4444 (3)	0.0453 (11)
H8	0.5007	0.4764	0.4134	0.054*
C9	0.5811 (4)	0.7331 (5)	0.3870 (3)	0.0302 (9)
C10	0.6874 (4)	0.8761 (5)	0.4309 (3)	0.0285 (8)
C11	0.3962 (4)	0.6244 (5)	0.2248 (3)	0.0287 (8)
H11	0.3506	0.5543	0.2709	0.034*
C16	0.2800 (4)	0.7340 (5)	0.1395 (3)	0.0334 (9)
H16A	0.2233	0.6416	0.0851	0.040*
H16B	0.3277	0.8263	0.1051	0.040*
C17	0.1769 (4)	0.8439 (7)	0.1826 (3)	0.0395 (9)
H17A	0.1988	0.8111	0.2581	0.047*
H17B	0.1925	0.9844	0.1776	0.047*
C18	−0.0810 (4)	0.8802 (6)	0.1698 (3)	0.0449 (10)
H18A	−0.0634	0.8265	0.2405	0.067*
H18B	−0.1802	0.8483	0.1246	0.067*
H18C	−0.0694	1.0209	0.1746	0.067*
Cl1	0.02776 (10)	0.35210 (15)	0.11567 (7)	0.0385 (3)
N1	0.0237 (3)	0.7976 (4)	0.1242 (2)	0.0334 (7)
H1A	0.0015	0.8416	0.0560	0.040*
H1B	0.0131	0.6655	0.1214	0.040*
O1	0.4920 (3)	0.7711 (3)	0.28494 (18)	0.0335 (6)
C12	0.4783 (4)	0.4840 (6)	0.1806 (3)	0.0304 (9)
S1A	0.4000 (4)	0.2836 (6)	0.1112 (4)	0.0390 (8)	0.580 (5)
C13A	0.5587 (15)	0.220 (3)	0.088 (2)	0.043 (2)	0.580 (5)
H13A	0.5703	0.1075	0.0508	0.051*	0.58
C14A	0.6634 (16)	0.353 (2)	0.1292 (18)	0.045 (2)	0.580 (5)
H14A	0.7575	0.3491	0.1227	0.054*	0.58
C15A	0.6158 (17)	0.500 (3)	0.184 (2)	0.042 (4)	0.580 (5)
H15A	0.6774	0.6027	0.2199	0.051*	0.58
S1B	0.6515 (6)	0.5208 (10)	0.1826 (7)	0.0410 (14)	0.420 (5)
C13B	0.656 (2)	0.310 (3)	0.119 (2)	0.042 (3)	0.420 (5)
H13B	0.7390	0.2624	0.1043	0.051*	0.42
C14B	0.526 (2)	0.221 (4)	0.091 (3)	0.045 (3)	0.420 (5)
H14B	0.5030	0.1062	0.0498	0.054*	0.42
C15B	0.427 (2)	0.318 (3)	0.131 (2)	0.053 (5)	0.420 (5)
H15B	0.3325	0.2691	0.1237	0.063*	0.42

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C12	0.030 (2)	0.034 (2)	0.0272 (18)	−0.0013 (18)	0.0086 (16)	0.0036 (16)
S1A	0.0360 (14)	0.0354 (13)	0.0453 (18)	0.0021 (11)	0.0130 (14)	−0.0108 (10)
C13A	0.046 (6)	0.048 (5)	0.038 (5)	0.018 (5)	0.019 (6)	−0.002 (4)
C14A	0.039 (4)	0.060 (7)	0.042 (5)	0.009 (4)	0.021 (4)	−0.001 (5)
C15A	0.044 (9)	0.049 (6)	0.042 (5)	−0.005 (6)	0.025 (6)	−0.001 (4)
S1B	0.024 (2)	0.056 (2)	0.042 (2)	−0.0013 (18)	0.0099 (19)	0.0093 (17)
C13B	0.042 (5)	0.051 (6)	0.037 (7)	0.009 (5)	0.017 (5)	0.015 (5)
C14B	0.045 (7)	0.050 (6)	0.036 (6)	0.005 (6)	0.010 (6)	0.003 (5)
C15B	0.043 (7)	0.062 (12)	0.055 (11)	0.005 (7)	0.018 (8)	0.003 (8)
C1	0.047 (2)	0.038 (2)	0.0303 (19)	−0.007 (2)	0.0003 (18)	0.0082 (18)
C2	0.062 (3)	0.048 (3)	0.043 (2)	−0.020 (3)	−0.002 (2)	0.010 (2)
C3	0.051 (3)	0.045 (3)	0.043 (2)	−0.017 (2)	0.002 (2)	−0.003 (2)
C4	0.040 (2)	0.046 (2)	0.0269 (19)	−0.002 (2)	−0.0007 (17)	−0.0027 (19)
C5	0.034 (2)	0.0372 (19)	0.0269 (17)	−0.003 (2)	0.0081 (15)	−0.001 (2)
C6	0.046 (3)	0.058 (3)	0.032 (2)	−0.010 (2)	−0.0012 (19)	0.019 (2)
C7	0.060 (3)	0.061 (3)	0.042 (2)	−0.020 (3)	−0.004 (2)	0.028 (2)
C8	0.044 (2)	0.043 (2)	0.040 (2)	−0.014 (2)	0.0024 (19)	0.010 (2)
C9	0.032 (2)	0.032 (2)	0.0261 (18)	0.0051 (17)	0.0090 (15)	0.0010 (15)
C10	0.0295 (19)	0.031 (2)	0.0250 (16)	0.0001 (17)	0.0092 (14)	−0.0023 (16)
C11	0.026 (2)	0.031 (2)	0.0268 (18)	−0.0037 (15)	0.0066 (16)	0.0011 (14)
C16	0.029 (2)	0.035 (2)	0.0308 (19)	0.0003 (18)	0.0029 (16)	−0.0060 (16)
C17	0.033 (2)	0.040 (2)	0.0382 (19)	0.002 (2)	0.0021 (16)	−0.015 (2)
C18	0.039 (2)	0.040 (2)	0.060 (2)	0.003 (2)	0.023 (2)	0.000 (2)
Cl1	0.0438 (6)	0.0345 (5)	0.0345 (5)	−0.0070 (5)	0.0095 (4)	0.0009 (4)
N1	0.0348 (17)	0.0295 (17)	0.0335 (16)	−0.0006 (14)	0.0080 (14)	0.0003 (13)
O1	0.0365 (14)	0.0308 (13)	0.0254 (12)	−0.0054 (12)	−0.0003 (11)	−0.0003 (10)

Geometric parameters (Å, º) top

C1—C2	1.353 (6)	C17—H17A	0.9900
C1—C10	1.418 (5)	C17—H17B	0.9900
C1—H1	0.9500	C18—N1	1.469 (5)
C2—C3	1.406 (5)	C18—H18A	0.9800
C2—H2	0.9500	C18—H18B	0.9800
C3—C4	1.364 (6)	C18—H18C	0.9800
C3—H3	0.9500	N1—H1A	0.9200
C4—C5	1.420 (6)	N1—H1B	0.9200
C4—H4	0.9500	C12—C15A	1.332 (14)
C5—C6	1.402 (6)	C12—C15B	1.341 (16)
C5—C10	1.418 (4)	C12—C11	1.501 (5)
C6—C7	1.344 (6)	C12—S1B	1.699 (7)
C6—H6	0.9500	C12—S1A	1.703 (5)
C7—C8	1.406 (5)	S1A—C13A	1.734 (10)
C7—H7	0.9500	C13A—C14A	1.351 (10)
C8—C9	1.365 (5)	C13A—H13A	0.9500
C8—H8	0.9500	C14A—C15A	1.420 (14)
C9—O1	1.381 (4)	C14A—H14A	0.9500
C9—C10	1.413 (5)	C15A—H15A	0.9500
C11—O1	1.433 (4)	S1B—C13B	1.699 (14)
C11—C16	1.519 (5)	C13B—C14B	1.351 (11)
C11—H11	1.0000	C13B—H13B	0.9500
C16—C17	1.520 (5)	C14B—C15B	1.421 (15)
C16—H16A	0.9900	C14B—H14B	0.9500
C16—H16B	0.9900	C15B—H15B	0.9500
C17—N1	1.472 (4)

C2—C1—C10	121.2 (3)	N1—C17—H17B	109.3
C2—C1—H1	119.4	C16—C17—H17B	109.3
C10—C1—H1	119.4	H17A—C17—H17B	107.9
C1—C2—C3	120.9 (4)	N1—C18—H18A	109.5
C1—C2—H2	119.5	N1—C18—H18B	109.5
C3—C2—H2	119.5	H18A—C18—H18B	109.5
C4—C3—C2	119.5 (4)	N1—C18—H18C	109.5
C4—C3—H3	120.2	H18A—C18—H18C	109.5
C2—C3—H3	120.2	H18B—C18—H18C	109.5
C3—C4—C5	121.3 (3)	C18—N1—C17	114.6 (3)
C3—C4—H4	119.3	C18—N1—H1A	108.6
C5—C4—H4	119.3	C17—N1—H1A	108.6
C6—C5—C10	119.5 (4)	C18—N1—H1B	108.6
C6—C5—C4	121.9 (3)	C17—N1—H1B	108.6
C10—C5—C4	118.6 (3)	H1A—N1—H1B	107.6
C7—C6—C5	120.0 (4)	C9—O1—C11	120.0 (3)
C7—C6—H6	120.0	C15A—C12—C15B	107.3 (10)
C5—C6—H6	120.0	C15A—C12—C11	126.5 (7)
C6—C7—C8	122.0 (4)	C15B—C12—C11	126.2 (8)
C6—C7—H7	119.0	C15B—C12—S1B	110.1 (8)
C8—C7—H7	119.0	C11—C12—S1B	123.7 (3)
C9—C8—C7	119.0 (4)	C15A—C12—S1A	110.5 (7)
C9—C8—H8	120.5	C11—C12—S1A	122.9 (3)
C7—C8—H8	120.5	S1B—C12—S1A	113.1 (3)
C8—C9—O1	124.8 (3)	C12—S1A—C13A	92.4 (4)
C8—C9—C10	120.9 (3)	C14A—C13A—S1A	110.4 (8)
O1—C9—C10	114.4 (3)	C14A—C13A—H13A	124.8
C9—C10—C1	123.0 (3)	S1A—C13A—H13A	124.8
C9—C10—C5	118.5 (3)	C13A—C14A—C15A	111.8 (10)
C1—C10—C5	118.5 (3)	C13A—C14A—H14A	124.1
O1—C11—C12	110.4 (3)	C15A—C14A—H14A	124.1
O1—C11—C16	104.7 (3)	C12—C15A—C14A	114.8 (11)
C12—C11—C16	112.8 (3)	C12—C15A—H15A	122.6
O1—C11—H11	109.6	C14A—C15A—H15A	122.6
C12—C11—H11	109.6	C13B—S1B—C12	93.3 (7)
C16—C11—H11	109.6	C14B—C13B—S1B	110.6 (11)
C11—C16—C17	112.6 (3)	C14B—C13B—H13B	124.7
C11—C16—H16A	109.1	S1B—C13B—H13B	124.7
C17—C16—H16A	109.1	C13B—C14B—C15B	112.1 (12)
C11—C16—H16B	109.1	C13B—C14B—H14B	124.0
C17—C16—H16B	109.1	C15B—C14B—H14B	124.0
H16A—C16—H16B	107.8	C12—C15B—C14B	113.7 (12)
N1—C17—C16	111.7 (3)	C12—C15B—H15B	123.2
N1—C17—H17A	109.3	C14B—C15B—H15B	123.2
C16—C17—H17A	109.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.92	2.23	3.113 (3)	161
N1—H1B···Cl1	0.92	2.18	3.087 (3)	170

Symmetry code: (i) −x, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀NOS⁺·Cl⁻
M_r	333.86
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	9.7453 (10), 6.9227 (7), 13.4247 (16)
β (°)	109.432 (4)
V (Å³)	854.09 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.38 × 0.08 × 0.03

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.879, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	6386, 2947, 2255
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.131, 0.79
No. of reflections	2947
No. of parameters	237
No. of restraints	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.21
Absolute structure	Flack (1983), 1309 Friedel pairs
Absolute structure parameter	−0.05 (10)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), sAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.92	2.23	3.113 (3)	161.4
N1—H1B···Cl1	0.92	2.18	3.087 (3)	169.8

Symmetry code: (i) −x, y+1/2, −z.

Acknowledgements

We are grateful to Professor Grainne Moran for her encouragement and interest in this work.

References

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