N-(2-Hydroxy­ethyl)-N-(tricyclo­[3.3.1.13,7]dec-2-yl)benzamide

Boyle, G.A.; Govender, T.; Kruger, H.G.; Onajole, O.K.

doi:10.1107/S1600536808013469

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1029

doi:10.1107/S1600536808013469

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N-(2-Hydroxyethyl)-N-(tricyclo[3.3.1.1^3,7]dec-2-yl)benzamide

Grant A. Boyle,^a Thavendran Govender,^b ^* Hendrik G. Kruger ^a and Oluseye K. Onajole ^a

^aSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa, and ^bSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa
^*Correspondence e-mail: govenderthav@ukzn.ac.za

(Received 23 April 2008; accepted 6 May 2008; online 10 May 2008)

The title adamantane derivative, C₁₉H₂₅NO₂, was synthesized as part of a study into potential antituberculosis agents. The adamantane skeleton displays shorter than normal C—C bond lengths ranging between 1.5230 (15) and 1.5329 (16) Å. The structure displays O—H⋯O hydrogen bonding and an interdigitated layered packing structure with distinct hydrophilic and hydrophobic regions.

Related literature

For related literature, see: Bogatcheva et al. (2006 ); Jacobson et al. (1987 ); Lee et al., (2003 )

Experimental

Crystal data

C₁₉H₂₅NO₂
M_r = 299.40
Monoclinic, P 2₁ /c
a = 11.4248 (3) Å
b = 16.0902 (4) Å
c = 8.7211 (2) Å
β = 107.9030 (10)°
V = 1525.55 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 (2) K
0.44 × 0.33 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none
19272 measured reflections
3684 independent reflections
2861 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.109
S = 1.12
3684 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.29 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
O1—H1A⋯O2ⁱ	0.84	1.96	2.7735 (12)	164
Symmetry code: (i) -x+1, -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/S1600536808013469/fl2199sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013469/fl2199Isup2.hkl

checkCIF report

Comment top

Adamantane derivatives have been the subject of much investigation as potential anti-tubercolosis compounds (Bogatcheva et al., 2006, Lee et al., 2003). The novel compound (I) was also synthesized in order to investigate the biological activities of cage amino-alcohol compounds as potential anti-tuberculosis agents. The molecule (I) consists of a polycyclic (lipophilic) hydrocarbon skeleton with polar amine and hydroxyl units (Fig. 1).

The molecule exhibits some C—C bonds that are significantly shorter than the expected C—C bond length of 1.54 Å. These bonds range between 1.5230 (15) Å for C7—C8 to 1.5329 (16) Å for C1—C8 in the adamantane skeleton.

The structure exhibits intermolecular hydrogen bonding interactions between O1 and O2 of adjacent molecules (Fig. 2). There is also a complex network of short contacts between the molecules which result in an interdigitated, layered structure showing distinct hydrophilic and hydrophobic regions (Fig. 2). The hydrophobic region consists of the adamantane skeleton while the hydrophilic layer consists of the polar amine and hydroxyl units.

Related literature top

For related literature, see: Bogatcheva et al. (2006); Jacobson et al. (1987); Lee et al., (2003)

Experimental top

To a stirred solution of 2-(tricyclo[3.3.1.13,7]dec-2-ylamino)-ethanol (1 g, 5.1 mmol) in dichloromethane (30 ml) was added dropwise over 45 minutes a solution of benzoyl chloride (590ul, 5.1 mmol) dissolved in 50 ml of dichloromethane under a nitrogen atmosphere at zero degrees using an external ice salt bath. The reaction was allowed to stir overnight (Jacobson et al., 1987) and then filtered to remove the HCl salt and the solvent was removed in vacuo. The mixture was re-crystallized from methanol to obtain the title compound (I) (0.91 g, 60%) as a colourless microcrystalline solid.

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. ORTEP diagram showing displacement ellipsoids at the 50% probability level.
	Fig. 2. Diagram of the packing viewed down the c axis showing the layered structure and intermolecular hydrogen bonding. Hydrogen atoms have been omitted for clarity.

N-(2-Hydroxyethyl)-N-(tricyclo[3.3.1.1^3,7]dec-2-yl)benzamide top

Crystal data top

C₁₉H₂₅NO₂	F(000) = 648
M_r = 299.40	D_x = 1.304 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5317 reflections
a = 11.4248 (3) Å	θ = 2.3–28.2°
b = 16.0902 (4) Å	µ = 0.08 mm⁻¹
c = 8.7211 (2) Å	T = 173 K
β = 107.903 (1)°	Block, colourless
V = 1525.55 (7) Å³	0.44 × 0.33 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2861 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 28.0°, θ_min = 1.9°
ϕ and ω scans	h = −15→15
19272 measured reflections	k = −21→21
3684 independent reflections	l = −11→11

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0562P)²] where P = (F_o² + 2F_c²)/3
3684 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₂₅NO₂	V = 1525.55 (7) Å³
M_r = 299.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4248 (3) Å	µ = 0.08 mm⁻¹
b = 16.0902 (4) Å	T = 173 K
c = 8.7211 (2) Å	0.44 × 0.33 × 0.16 mm
β = 107.903 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2861 reflections with I > 2σ(I)
19272 measured reflections	R_int = 0.050
3684 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.12	Δρ_max = 0.29 e Å⁻³
3684 reflections	Δρ_min = −0.22 e Å⁻³
200 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
C1	0.26872 (10)	0.12522 (7)	0.22178 (13)	0.0191 (2)
H1	0.2797	0.1396	0.3369	0.023*
C2	0.32356 (10)	0.03827 (6)	0.21268 (13)	0.0170 (2)
H2	0.4145	0.0414	0.2656	0.020*
C3	0.30029 (10)	0.01726 (7)	0.03325 (13)	0.0179 (2)
H3	0.3322	−0.0398	0.0239	0.021*
C4	0.16309 (10)	0.02106 (7)	−0.06201 (14)	0.0215 (3)
H4A	0.1512	0.0068	−0.1762	0.026*
H4B	0.1172	−0.0198	−0.0177	0.026*
C5	0.11394 (11)	0.10846 (7)	−0.05095 (14)	0.0226 (3)
H5	0.0244	0.1109	−0.1128	0.027*
C6	0.18444 (11)	0.17132 (7)	−0.12046 (14)	0.0250 (3)
H6A	0.1522	0.2279	−0.1143	0.030*
H6B	0.1728	0.1583	−0.2352	0.030*
C7	0.32164 (11)	0.16808 (7)	−0.02533 (14)	0.0220 (3)
H7	0.3678	0.2092	−0.0707	0.026*
C8	0.33836 (11)	0.18828 (7)	0.15074 (14)	0.0212 (3)
H8A	0.3071	0.2449	0.1592	0.025*
H8B	0.4269	0.1869	0.2126	0.025*
C9	0.13223 (11)	0.12772 (7)	0.12635 (14)	0.0225 (3)
H9A	0.0986	0.1835	0.1362	0.027*
H9B	0.0872	0.0864	0.1709	0.027*
C10	0.36964 (10)	0.08045 (7)	−0.03724 (13)	0.0210 (3)
H10A	0.4586	0.0778	0.0223	0.025*
H10B	0.3586	0.0668	−0.1515	0.025*
C11	0.27216 (11)	−0.11302 (7)	0.24168 (14)	0.0206 (3)
H11A	0.2282	−0.1153	0.1246	0.025*
H11B	0.2266	−0.1482	0.2972	0.025*
C12	0.40094 (11)	−0.14766 (7)	0.27306 (14)	0.0242 (3)
H12A	0.3964	−0.2032	0.2226	0.029*
H12B	0.4490	−0.1107	0.2243	0.029*
C13	0.29089 (10)	−0.01541 (7)	0.45859 (13)	0.0206 (3)
C14	0.22837 (11)	−0.07451 (7)	0.54113 (13)	0.0206 (2)
C15	0.10237 (11)	−0.08725 (8)	0.48552 (15)	0.0264 (3)
H15	0.0542	−0.0607	0.3896	0.032*
C16	0.04662 (12)	−0.13882 (9)	0.56983 (16)	0.0316 (3)
H16	−0.0399	−0.1468	0.5324	0.038*
C17	0.11626 (12)	−0.17845 (8)	0.70758 (15)	0.0299 (3)
H17	0.0780	−0.2149	0.7635	0.036*
C18	0.24153 (12)	−0.16534 (7)	0.76451 (15)	0.0270 (3)
H18	0.2895	−0.1923	0.8601	0.032*
C19	0.29721 (11)	−0.11306 (7)	0.68239 (14)	0.0231 (3)
H19	0.3833	−0.1034	0.7229	0.028*
N1	0.27326 (8)	−0.02630 (5)	0.29804 (11)	0.0183 (2)
O1	0.46035 (8)	−0.15413 (6)	0.44118 (10)	0.0311 (2)
H1A	0.5219	−0.1226	0.4676	0.047*
O2	0.34988 (8)	0.04282 (5)	0.53714 (10)	0.0301 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0225 (6)	0.0194 (5)	0.0167 (5)	−0.0003 (4)	0.0081 (5)	−0.0023 (4)
C2	0.0180 (5)	0.0183 (5)	0.0157 (5)	−0.0021 (4)	0.0064 (4)	0.0004 (4)
C3	0.0201 (6)	0.0183 (5)	0.0166 (5)	−0.0001 (4)	0.0075 (4)	−0.0018 (4)
C4	0.0212 (6)	0.0250 (6)	0.0177 (6)	−0.0035 (5)	0.0052 (5)	−0.0039 (4)
C5	0.0161 (6)	0.0281 (6)	0.0217 (6)	0.0016 (5)	0.0030 (5)	−0.0006 (5)
C6	0.0282 (7)	0.0261 (6)	0.0199 (6)	0.0028 (5)	0.0060 (5)	0.0034 (5)
C7	0.0244 (6)	0.0218 (6)	0.0214 (6)	−0.0014 (5)	0.0094 (5)	0.0032 (5)
C8	0.0235 (6)	0.0186 (5)	0.0218 (6)	−0.0019 (5)	0.0071 (5)	−0.0007 (4)
C9	0.0208 (6)	0.0240 (6)	0.0248 (6)	0.0013 (5)	0.0102 (5)	−0.0015 (5)
C10	0.0193 (6)	0.0269 (6)	0.0183 (6)	−0.0003 (5)	0.0082 (5)	0.0000 (5)
C11	0.0237 (6)	0.0178 (5)	0.0220 (6)	−0.0031 (4)	0.0094 (5)	−0.0016 (4)
C12	0.0251 (6)	0.0211 (6)	0.0282 (7)	0.0004 (5)	0.0109 (5)	0.0004 (5)
C13	0.0208 (6)	0.0225 (6)	0.0182 (6)	−0.0011 (5)	0.0054 (5)	0.0010 (4)
C14	0.0248 (6)	0.0206 (6)	0.0183 (5)	−0.0017 (5)	0.0097 (5)	−0.0022 (4)
C15	0.0242 (6)	0.0327 (7)	0.0222 (6)	−0.0018 (5)	0.0070 (5)	0.0008 (5)
C16	0.0248 (7)	0.0387 (7)	0.0349 (7)	−0.0082 (5)	0.0142 (6)	−0.0039 (6)
C17	0.0386 (8)	0.0254 (6)	0.0340 (7)	−0.0043 (6)	0.0233 (6)	0.0009 (5)
C18	0.0368 (7)	0.0234 (6)	0.0246 (6)	0.0045 (5)	0.0150 (6)	0.0028 (5)
C19	0.0226 (6)	0.0248 (6)	0.0233 (6)	0.0002 (5)	0.0091 (5)	0.0002 (5)
N1	0.0212 (5)	0.0171 (5)	0.0178 (5)	−0.0024 (4)	0.0078 (4)	−0.0006 (4)
O1	0.0250 (5)	0.0372 (5)	0.0302 (5)	0.0001 (4)	0.0070 (4)	0.0092 (4)
O2	0.0386 (5)	0.0317 (5)	0.0189 (4)	−0.0140 (4)	0.0072 (4)	−0.0028 (4)

Geometric parameters (Å, º) top

C1—C9	1.5258 (15)	C9—H9B	0.9900
C1—C8	1.5329 (16)	C10—H10A	0.9900
C1—C2	1.5450 (15)	C10—H10B	0.9900
C1—H1	1.0000	C11—N1	1.4783 (14)
C2—N1	1.4922 (14)	C11—C12	1.5174 (16)
C2—C3	1.5420 (15)	C11—H11A	0.9900
C2—H2	1.0000	C11—H11B	0.9900
C3—C10	1.5293 (15)	C12—O1	1.4175 (14)
C3—C4	1.5330 (15)	C12—H12A	0.9900
C3—H3	1.0000	C12—H12B	0.9900
C4—C5	1.5283 (16)	C13—O2	1.2319 (13)
C4—H4A	0.9900	C13—N1	1.3632 (14)
C4—H4B	0.9900	C13—C14	1.4996 (16)
C5—C9	1.5270 (16)	C14—C15	1.3858 (16)
C5—C6	1.5295 (17)	C14—C19	1.3876 (16)
C5—H5	1.0000	C15—C16	1.3867 (18)
C6—C7	1.5325 (16)	C15—H15	0.9500
C6—H6A	0.9900	C16—C17	1.3766 (19)
C6—H6B	0.9900	C16—H16	0.9500
C7—C8	1.5230 (15)	C17—C18	1.3793 (18)
C7—C10	1.5280 (16)	C17—H17	0.9500
C7—H7	1.0000	C18—C19	1.3804 (16)
C8—H8A	0.9900	C18—H18	0.9500
C8—H8B	0.9900	C19—H19	0.9500
C9—H9A	0.9900	O1—H1A	0.8400

C9—C1—C8	109.43 (9)	C1—C9—H9A	109.6
C9—C1—C2	111.00 (9)	C5—C9—H9A	109.6
C8—C1—C2	108.03 (9)	C1—C9—H9B	109.6
C9—C1—H1	109.5	C5—C9—H9B	109.6
C8—C1—H1	109.5	H9A—C9—H9B	108.1
C2—C1—H1	109.5	C7—C10—C3	110.19 (9)
N1—C2—C3	112.39 (9)	C7—C10—H10A	109.6
N1—C2—C1	112.35 (9)	C3—C10—H10A	109.6
C3—C2—C1	107.73 (9)	C7—C10—H10B	109.6
N1—C2—H2	108.1	C3—C10—H10B	109.6
C3—C2—H2	108.1	H10A—C10—H10B	108.1
C1—C2—H2	108.1	N1—C11—C12	112.21 (9)
C10—C3—C4	108.99 (9)	N1—C11—H11A	109.2
C10—C3—C2	108.25 (9)	C12—C11—H11A	109.2
C4—C3—C2	111.70 (9)	N1—C11—H11B	109.2
C10—C3—H3	109.3	C12—C11—H11B	109.2
C4—C3—H3	109.3	H11A—C11—H11B	107.9
C2—C3—H3	109.3	O1—C12—C11	110.06 (10)
C5—C4—C3	109.69 (9)	O1—C12—H12A	109.6
C5—C4—H4A	109.7	C11—C12—H12A	109.6
C3—C4—H4A	109.7	O1—C12—H12B	109.6
C5—C4—H4B	109.7	C11—C12—H12B	109.6
C3—C4—H4B	109.7	H12A—C12—H12B	108.2
H4A—C4—H4B	108.2	O2—C13—N1	123.49 (10)
C9—C5—C4	108.18 (9)	O2—C13—C14	118.37 (10)
C9—C5—C6	110.02 (10)	N1—C13—C14	118.02 (10)
C4—C5—C6	109.57 (10)	C15—C14—C19	119.26 (11)
C9—C5—H5	109.7	C15—C14—C13	121.52 (10)
C4—C5—H5	109.7	C19—C14—C13	119.08 (10)
C6—C5—H5	109.7	C14—C15—C16	120.01 (12)
C5—C6—C7	109.79 (9)	C14—C15—H15	120.0
C5—C6—H6A	109.7	C16—C15—H15	120.0
C7—C6—H6A	109.7	C17—C16—C15	120.22 (12)
C5—C6—H6B	109.7	C17—C16—H16	119.9
C7—C6—H6B	109.7	C15—C16—H16	119.9
H6A—C6—H6B	108.2	C16—C17—C18	120.05 (12)
C8—C7—C10	109.21 (9)	C16—C17—H17	120.0
C8—C7—C6	109.21 (10)	C18—C17—H17	120.0
C10—C7—C6	108.86 (9)	C17—C18—C19	119.94 (12)
C8—C7—H7	109.8	C17—C18—H18	120.0
C10—C7—H7	109.8	C19—C18—H18	120.0
C6—C7—H7	109.8	C18—C19—C14	120.48 (11)
C7—C8—C1	110.27 (9)	C18—C19—H19	119.8
C7—C8—H8A	109.6	C14—C19—H19	119.8
C1—C8—H8A	109.6	C13—N1—C11	116.51 (9)
C7—C8—H8B	109.6	C13—N1—C2	117.71 (9)
C1—C8—H8B	109.6	C11—N1—C2	117.16 (9)
H8A—C8—H8B	108.1	C12—O1—H1A	109.5
C1—C9—C5	110.23 (9)

C9—C1—C2—N1	−67.42 (12)	C4—C3—C10—C7	60.22 (11)
C8—C1—C2—N1	172.61 (9)	C2—C3—C10—C7	−61.46 (11)
C9—C1—C2—C3	56.91 (12)	N1—C11—C12—O1	65.78 (12)
C8—C1—C2—C3	−63.06 (11)	O2—C13—C14—C15	121.39 (13)
N1—C2—C3—C10	−172.53 (9)	N1—C13—C14—C15	−54.82 (15)
C1—C2—C3—C10	63.16 (11)	O2—C13—C14—C19	−54.31 (15)
N1—C2—C3—C4	67.48 (11)	N1—C13—C14—C19	129.49 (11)
C1—C2—C3—C4	−56.83 (11)	C19—C14—C15—C16	−0.74 (18)
C10—C3—C4—C5	−59.62 (12)	C13—C14—C15—C16	−176.43 (11)
C2—C3—C4—C5	59.94 (12)	C14—C15—C16—C17	−0.94 (19)
C3—C4—C5—C9	−60.20 (12)	C15—C16—C17—C18	1.6 (2)
C3—C4—C5—C6	59.75 (12)	C16—C17—C18—C19	−0.61 (19)
C9—C5—C6—C7	58.95 (12)	C17—C18—C19—C14	−1.08 (18)
C4—C5—C6—C7	−59.87 (12)	C15—C14—C19—C18	1.75 (17)
C5—C6—C7—C8	−59.44 (12)	C13—C14—C19—C18	177.55 (11)
C5—C6—C7—C10	59.72 (12)	O2—C13—N1—C11	144.02 (12)
C10—C7—C8—C1	−59.05 (12)	C14—C13—N1—C11	−39.99 (14)
C6—C7—C8—C1	59.90 (12)	O2—C13—N1—C2	−2.93 (16)
C9—C1—C8—C7	−59.43 (12)	C14—C13—N1—C2	173.06 (9)
C2—C1—C8—C7	61.54 (11)	C12—C11—N1—C13	−80.57 (12)
C8—C1—C9—C5	58.41 (12)	C12—C11—N1—C2	66.57 (12)
C2—C1—C9—C5	−60.73 (12)	C3—C2—N1—C13	178.49 (9)
C4—C5—C9—C1	61.06 (12)	C1—C2—N1—C13	−59.80 (13)
C6—C5—C9—C1	−58.61 (12)	C3—C2—N1—C11	31.75 (13)
C8—C7—C10—C3	58.96 (12)	C1—C2—N1—C11	153.46 (9)
C6—C7—C10—C3	−60.20 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.84	1.96	2.7735 (12)	164

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₅NO₂
M_r	299.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	11.4248 (3), 16.0902 (4), 8.7211 (2)
β (°)	107.903 (1)
V (Å³)	1525.55 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.44 × 0.33 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19272, 3684, 2861
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.12
No. of reflections	3684
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.22

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
O1—H1A···O2ⁱ	0.84	1.96	2.7735 (12)	163.6

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

We thank Dr Manuel Fernandes of the Jan Boeyens Structural Chemistry Laboratory, University of the Witwatersrand, for his assistance in the acquisition of the crystallographic data. This work was supported by grants from the National Research Foundation (South Africa), GUN 2046819, the University of KwaZulu–Natal and Aspen Pharmacare.

References

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