2-(3,5-Di-tert-butyl-4-hydroxy­benzyl­sulfan­yl)nicotinic acid

Mansor, S.; Yehye, W.A.; Ariffin, A.; Rahman, N.A.; Ng, S.W.

doi:10.1107/S1600536808026056

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1778

doi:10.1107/S1600536808026056

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2-(3,5-Di-tert-butyl-4-hydroxybenzylsulfanyl)nicotinic acid

Shahirah Mansor,^a Wagee A. Yehye,^a Azhar Ariffin,^a Noorsaadah Abdul Rahman ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 11 August 2008; accepted 13 August 2008; online 16 August 2008)

Two molecules of the title compound, C₂₁H₂₇NO₃S, are disposed about a center of inversion, generating an O—H⋯O hydrogen-bonded dimer.

Related literature

For the applications of hindered phenol-based antioxidants, see: Kim & Lee (2003 ); Um & Lee (2005 ).

Experimental

Crystal data

C₂₁H₂₇NO₃S
M_r = 373.50
Triclinic, $[P \overline 1]$
a = 5.6305 (1) Å
b = 9.3489 (2) Å
c = 18.8749 (3) Å
α = 85.505 (1)°
β = 89.453 (1)°
γ = 87.834 (1)°
V = 989.77 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 (2) K
0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.956, T_max = 0.991
12688 measured reflections
4507 independent reflections
3746 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.127
S = 1.18
4507 reflections
239 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2ⁱ	0.85 (1)	1.79 (1)	2.640 (2)	179 (3)
Symmetry code: (i) -x, -y+1, -z+1.

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026056/tk2295sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026056/tk2295Isup2.hkl

checkCIF report

Comment top

The compound (I, Fig. 1) is the precursor for the synthesis of hindered phenol-based antioxidants. Phenol-based antioxidants and their derivative have applications in industries such as pharmaceutical, textiles, plastics, polymers, oils, pesticides,dyestuffs, explosives, fluorescent-brightening industries (Kim & Lee, 2003; Um & Lee, 2005). Molecules are connected into centrosymmetric dimers via the eight- membered {OCOH}₂ synthon (Table 1). The hydroxyl-H projects between the two sterically hindered aromatic rings and is therefore precluded from forming a hydrogen bonding interaction.

Related literature top

For the applications of hindered phenol-based antioxidants, see: Kim & Lee (2003); Um & Lee (2005).

Experimental top

2-Mercaptonicotinic acid (1.50 g, 1 mmol), 2,6-di-t-butylphenol (2.00 g, 1 mmol) and paraformaldehyde (0.291 g,1 mmol) were intimately ground into a powder and to this was added di-n-butylamine (0.09 ml). The slurry was heated to 373–383 K and after an hour, this solidified. The solid was purified by column chromatography, with chloroform as solvent, to give two products, one of which was the expected acid, (I), and the other, the di-n-butylammonium salt of the acid.

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the hydrogen-bonded dimeric structure of (I) drawn at the 70% probability level. Dashed lines denote the hydrogen bonds. Hydrogen atoms are drawn as spheres of arbitrary radius.

2-(3,5-Di-tert-butyl-4-hydroxybenzylsulfanyl)nicotinic acid top

Crystal data top

C₂₁H₂₇NO₃S	Z = 2
M_r = 373.50	F(000) = 400
Triclinic, P1	D_x = 1.253 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6305 (1) Å	Cell parameters from 3920 reflections
b = 9.3489 (2) Å	θ = 2.2–28.4°
c = 18.8749 (3) Å	µ = 0.18 mm⁻¹
α = 85.505 (1)°	T = 100 K
β = 89.453 (1)°	Prism, colorless
γ = 87.834 (1)°	0.25 × 0.15 × 0.05 mm
V = 989.77 (3) Å³

Data collection top

Bruker SMART APEX diffractometer	4507 independent reflections
Radiation source: fine-focus sealed tube	3746 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.956, T_max = 0.991	k = −9→12
12688 measured reflections	l = −24→24

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ²(F_o²) + (0.0642P)² + 0.2102P] where P = (F_o² + 2F_c²)/3
4507 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.75 e Å⁻³
1 restraint	Δρ_min = −0.71 e Å⁻³

Crystal data top

C₂₁H₂₇NO₃S	γ = 87.834 (1)°
M_r = 373.50	V = 989.77 (3) Å³
Triclinic, P1	Z = 2
a = 5.6305 (1) Å	Mo Kα radiation
b = 9.3489 (2) Å	µ = 0.18 mm⁻¹
c = 18.8749 (3) Å	T = 100 K
α = 85.505 (1)°	0.25 × 0.15 × 0.05 mm
β = 89.453 (1)°

Data collection top

Bruker SMART APEX diffractometer	4507 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3746 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.991	R_int = 0.028
12688 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.75 e Å⁻³
4507 reflections	Δρ_min = −0.71 e Å⁻³
239 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.58009 (7)	0.68988 (5)	0.60316 (2)	0.01722 (13)
O1	0.0857 (2)	0.63037 (14)	0.42620 (6)	0.0211 (3)
H1O	−0.014 (4)	0.566 (2)	0.4379 (14)	0.053 (8)*
O2	0.2215 (2)	0.56848 (14)	0.53598 (6)	0.0222 (3)
O3	0.8816 (2)	0.54828 (13)	0.92906 (6)	0.0161 (3)
H3O	0.7848	0.4934	0.9503	0.024*
N1	0.7549 (3)	0.87163 (16)	0.50351 (7)	0.0177 (3)
C1	0.2358 (3)	0.64038 (19)	0.47879 (9)	0.0184 (4)
C2	0.4212 (3)	0.74553 (19)	0.46400 (8)	0.0176 (4)
C3	0.4393 (3)	0.8192 (2)	0.39715 (9)	0.0203 (4)
H3	0.3316	0.8015	0.3607	0.024*
C4	0.6135 (3)	0.9179 (2)	0.38393 (9)	0.0214 (4)
H4	0.6284	0.9689	0.3386	0.026*
C5	0.7661 (3)	0.9404 (2)	0.43878 (9)	0.0203 (4)
H5	0.8856	1.0087	0.4299	0.024*
C6	0.5857 (3)	0.77544 (19)	0.51655 (8)	0.0165 (3)
C7	0.8320 (3)	0.7718 (2)	0.64204 (8)	0.0171 (3)
H7A	0.9800	0.7489	0.6159	0.021*
H7B	0.8070	0.8775	0.6397	0.021*
C8	0.8498 (3)	0.71171 (19)	0.71821 (8)	0.0149 (3)
C9	0.9743 (3)	0.58333 (19)	0.73576 (8)	0.0152 (3)
H9	1.0514	0.5350	0.6990	0.018*
C10	0.9903 (3)	0.52279 (18)	0.80543 (8)	0.0131 (3)
C11	0.8749 (3)	0.59945 (18)	0.85839 (8)	0.0126 (3)
C12	0.7483 (3)	0.73030 (18)	0.84288 (8)	0.0126 (3)
C13	0.7379 (3)	0.78302 (18)	0.77173 (8)	0.0148 (3)
H13	0.6514	0.8706	0.7595	0.018*
C14	1.1234 (3)	0.37706 (18)	0.82171 (8)	0.0151 (3)
C15	1.3288 (3)	0.38746 (19)	0.87432 (9)	0.0184 (4)
H15A	1.4089	0.2930	0.8832	0.028*
H15B	1.2653	0.4196	0.9192	0.028*
H15C	1.4426	0.4564	0.8541	0.028*
C16	0.9495 (3)	0.2627 (2)	0.85004 (10)	0.0213 (4)
H16A	0.8223	0.2563	0.8155	0.032*
H16B	0.8807	0.2896	0.8952	0.032*
H16C	1.0347	0.1695	0.8575	0.032*
C17	1.2390 (3)	0.3219 (2)	0.75437 (9)	0.0233 (4)
H17A	1.1158	0.3097	0.7193	0.035*
H17B	1.3224	0.2295	0.7665	0.035*
H17C	1.3525	0.3914	0.7345	0.035*
C18	0.6287 (3)	0.81640 (18)	0.90074 (8)	0.0141 (3)
C19	0.8187 (3)	0.8637 (2)	0.95129 (9)	0.0188 (4)
H19A	0.9064	0.7789	0.9727	0.028*
H19B	0.7415	0.9159	0.9888	0.028*
H19C	0.9291	0.9265	0.9245	0.028*
C20	0.4410 (3)	0.72805 (19)	0.94254 (8)	0.0164 (3)
H20A	0.3226	0.6979	0.9096	0.025*
H20B	0.3625	0.7869	0.9773	0.025*
H20C	0.5184	0.6431	0.9674	0.025*
C21	0.4985 (3)	0.95322 (19)	0.86854 (9)	0.0197 (4)
H21A	0.3753	0.9272	0.8361	0.029*
H21B	0.6123	1.0145	0.8423	0.029*
H21C	0.4250	1.0053	0.9067	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0224 (2)	0.0166 (2)	0.0123 (2)	−0.00013 (16)	−0.00189 (15)	0.00089 (15)
O1	0.0269 (7)	0.0187 (7)	0.0178 (6)	−0.0001 (5)	−0.0059 (5)	−0.0022 (5)
O2	0.0291 (7)	0.0214 (7)	0.0161 (6)	−0.0030 (5)	−0.0045 (5)	−0.0001 (5)
O3	0.0184 (6)	0.0173 (6)	0.0118 (5)	0.0002 (5)	0.0019 (4)	0.0032 (5)
N1	0.0214 (7)	0.0164 (8)	0.0147 (6)	0.0038 (6)	0.0009 (5)	0.0005 (6)
C1	0.0240 (8)	0.0151 (9)	0.0164 (8)	0.0056 (7)	−0.0031 (6)	−0.0053 (7)
C2	0.0233 (8)	0.0145 (9)	0.0149 (8)	0.0050 (7)	−0.0009 (6)	−0.0034 (6)
C3	0.0278 (9)	0.0192 (10)	0.0135 (8)	0.0066 (7)	−0.0025 (6)	−0.0030 (7)
C4	0.0301 (9)	0.0202 (10)	0.0131 (7)	0.0047 (7)	0.0015 (7)	0.0012 (7)
C5	0.0236 (9)	0.0190 (9)	0.0176 (8)	0.0021 (7)	0.0029 (7)	0.0012 (7)
C6	0.0217 (8)	0.0140 (9)	0.0134 (7)	0.0051 (7)	0.0010 (6)	−0.0015 (6)
C7	0.0193 (8)	0.0175 (9)	0.0143 (7)	0.0010 (7)	−0.0013 (6)	0.0004 (6)
C8	0.0156 (7)	0.0154 (9)	0.0135 (7)	−0.0001 (6)	−0.0003 (6)	−0.0001 (6)
C9	0.0154 (7)	0.0163 (9)	0.0143 (7)	0.0008 (6)	0.0003 (6)	−0.0035 (6)
C10	0.0129 (7)	0.0115 (8)	0.0153 (7)	−0.0007 (6)	−0.0012 (6)	−0.0017 (6)
C11	0.0123 (7)	0.0132 (8)	0.0122 (7)	−0.0018 (6)	−0.0013 (5)	0.0000 (6)
C12	0.0121 (7)	0.0125 (8)	0.0135 (7)	−0.0013 (6)	−0.0003 (5)	−0.0020 (6)
C13	0.0152 (7)	0.0126 (8)	0.0162 (8)	0.0014 (6)	−0.0009 (6)	0.0004 (6)
C14	0.0154 (7)	0.0125 (8)	0.0172 (8)	0.0013 (6)	−0.0008 (6)	−0.0016 (6)
C15	0.0145 (8)	0.0162 (9)	0.0242 (9)	0.0035 (7)	−0.0031 (6)	−0.0011 (7)
C16	0.0190 (8)	0.0137 (9)	0.0312 (9)	−0.0008 (7)	−0.0021 (7)	0.0000 (7)
C17	0.0285 (9)	0.0186 (10)	0.0224 (9)	0.0108 (8)	−0.0003 (7)	−0.0045 (7)
C18	0.0155 (7)	0.0120 (8)	0.0147 (7)	0.0009 (6)	0.0011 (6)	−0.0014 (6)
C19	0.0186 (8)	0.0194 (9)	0.0191 (8)	−0.0016 (7)	0.0014 (6)	−0.0061 (7)
C20	0.0141 (7)	0.0173 (9)	0.0180 (8)	−0.0001 (6)	0.0020 (6)	−0.0027 (7)
C21	0.0238 (9)	0.0144 (9)	0.0202 (8)	0.0068 (7)	0.0032 (7)	−0.0017 (7)

Geometric parameters (Å, º) top

S1—C6	1.7634 (16)	C12—C13	1.395 (2)
S1—C7	1.8239 (17)	C12—C18	1.542 (2)
O1—C1	1.321 (2)	C13—H13	0.9500
O1—H1O	0.850 (10)	C14—C17	1.538 (2)
O2—C1	1.230 (2)	C14—C16	1.538 (2)
O3—C11	1.3817 (18)	C14—C15	1.542 (2)
O3—H3O	0.8400	C15—H15A	0.9800
N1—C5	1.337 (2)	C15—H15B	0.9800
N1—C6	1.342 (2)	C15—H15C	0.9800
C1—C2	1.471 (3)	C16—H16A	0.9800
C2—C3	1.394 (2)	C16—H16B	0.9800
C2—C6	1.415 (2)	C16—H16C	0.9800
C3—C4	1.380 (3)	C17—H17A	0.9800
C3—H3	0.9500	C17—H17B	0.9800
C4—C5	1.385 (2)	C17—H17C	0.9800
C4—H4	0.9500	C18—C21	1.536 (2)
C5—H5	0.9500	C18—C19	1.540 (2)
C7—C8	1.505 (2)	C18—C20	1.539 (2)
C7—H7A	0.9900	C19—H19A	0.9800
C7—H7B	0.9900	C19—H19B	0.9800
C8—C9	1.386 (2)	C19—H19C	0.9800
C8—C13	1.387 (2)	C20—H20A	0.9800
C9—C10	1.393 (2)	C20—H20B	0.9800
C9—H9	0.9500	C20—H20C	0.9800
C10—C11	1.414 (2)	C21—H21A	0.9800
C10—C14	1.541 (2)	C21—H21B	0.9800
C11—C12	1.405 (2)	C21—H21C	0.9800

C6—S1—C7	100.24 (8)	C17—C14—C10	111.47 (13)
C1—O1—H1O	109.8 (18)	C16—C14—C10	110.37 (13)
C11—O3—H3O	126.6	C17—C14—C15	105.58 (13)
C5—N1—C6	118.43 (15)	C16—C14—C15	110.68 (14)
O2—C1—O1	122.91 (17)	C10—C14—C15	111.98 (14)
O2—C1—C2	122.32 (15)	C14—C15—H15A	109.5
O1—C1—C2	114.77 (15)	C14—C15—H15B	109.5
C3—C2—C6	117.92 (17)	H15A—C15—H15B	109.5
C3—C2—C1	120.55 (15)	C14—C15—H15C	109.5
C6—C2—C1	121.54 (15)	H15A—C15—H15C	109.5
C4—C3—C2	120.04 (16)	H15B—C15—H15C	109.5
C4—C3—H3	120.0	C14—C16—H16A	109.5
C2—C3—H3	120.0	C14—C16—H16B	109.5
C3—C4—C5	117.91 (16)	H16A—C16—H16B	109.5
C3—C4—H4	121.0	C14—C16—H16C	109.5
C5—C4—H4	121.0	H16A—C16—H16C	109.5
N1—C5—C4	123.84 (17)	H16B—C16—H16C	109.5
N1—C5—H5	118.1	C14—C17—H17A	109.5
C4—C5—H5	118.1	C14—C17—H17B	109.5
N1—C6—C2	121.87 (15)	H17A—C17—H17B	109.5
N1—C6—S1	115.97 (12)	C14—C17—H17C	109.5
C2—C6—S1	122.16 (14)	H17A—C17—H17C	109.5
C8—C7—S1	107.24 (11)	H17B—C17—H17C	109.5
C8—C7—H7A	110.3	C21—C18—C19	107.13 (14)
S1—C7—H7A	110.3	C21—C18—C20	106.49 (13)
C8—C7—H7B	110.3	C19—C18—C20	110.50 (13)
S1—C7—H7B	110.3	C21—C18—C12	111.61 (13)
H7A—C7—H7B	108.5	C19—C18—C12	109.74 (13)
C9—C8—C13	119.07 (14)	C20—C18—C12	111.26 (14)
C9—C8—C7	120.60 (15)	C18—C19—H19A	109.5
C13—C8—C7	120.31 (15)	C18—C19—H19B	109.5
C8—C9—C10	122.24 (15)	H19A—C19—H19B	109.5
C8—C9—H9	118.9	C18—C19—H19C	109.5
C10—C9—H9	118.9	H19A—C19—H19C	109.5
C9—C10—C11	116.84 (15)	H19B—C19—H19C	109.5
C9—C10—C14	120.15 (14)	C18—C20—H20A	109.5
C11—C10—C14	122.99 (14)	C18—C20—H20B	109.5
O3—C11—C12	116.25 (13)	H20A—C20—H20B	109.5
O3—C11—C10	121.08 (14)	C18—C20—H20C	109.5
C12—C11—C10	122.67 (14)	H20A—C20—H20C	109.5
C13—C12—C11	117.06 (14)	H20B—C20—H20C	109.5
C13—C12—C18	120.13 (14)	C18—C21—H21A	109.5
C11—C12—C18	122.80 (14)	C18—C21—H21B	109.5
C8—C13—C12	122.10 (15)	H21A—C21—H21B	109.5
C8—C13—H13	118.9	C18—C21—H21C	109.5
C12—C13—H13	118.9	H21A—C21—H21C	109.5
C17—C14—C16	106.52 (15)	H21B—C21—H21C	109.5

O2—C1—C2—C3	176.46 (16)	C9—C10—C11—O3	−179.75 (14)
O1—C1—C2—C3	−4.1 (2)	C14—C10—C11—O3	1.8 (2)
O2—C1—C2—C6	−3.6 (3)	C9—C10—C11—C12	0.3 (2)
O1—C1—C2—C6	175.85 (15)	C14—C10—C11—C12	−178.16 (15)
C6—C2—C3—C4	−0.1 (2)	O3—C11—C12—C13	−179.46 (13)
C1—C2—C3—C4	179.83 (16)	C10—C11—C12—C13	0.5 (2)
C2—C3—C4—C5	−0.1 (3)	O3—C11—C12—C18	1.9 (2)
C6—N1—C5—C4	−0.3 (3)	C10—C11—C12—C18	−178.11 (14)
C3—C4—C5—N1	0.3 (3)	C9—C8—C13—C12	0.6 (2)
C5—N1—C6—C2	0.0 (2)	C7—C8—C13—C12	179.43 (15)
C5—N1—C6—S1	−179.54 (12)	C11—C12—C13—C8	−1.0 (2)
C3—C2—C6—N1	0.2 (3)	C18—C12—C13—C8	177.73 (15)
C1—C2—C6—N1	−179.77 (15)	C9—C10—C14—C17	3.8 (2)
C3—C2—C6—S1	179.70 (12)	C11—C10—C14—C17	−177.85 (15)
C1—C2—C6—S1	−0.2 (2)	C9—C10—C14—C16	−114.38 (17)
C7—S1—C6—N1	−1.21 (15)	C11—C10—C14—C16	64.0 (2)
C7—S1—C6—C2	179.23 (14)	C9—C10—C14—C15	121.83 (16)
C6—S1—C7—C8	178.80 (11)	C11—C10—C14—C15	−59.8 (2)
S1—C7—C8—C9	85.94 (17)	C13—C12—C18—C21	2.6 (2)
S1—C7—C8—C13	−92.91 (16)	C11—C12—C18—C21	−178.80 (15)
C13—C8—C9—C10	0.3 (2)	C13—C12—C18—C19	−116.01 (16)
C7—C8—C9—C10	−178.57 (15)	C11—C12—C18—C19	62.6 (2)
C8—C9—C10—C11	−0.7 (2)	C13—C12—C18—C20	121.40 (16)
C8—C9—C10—C14	177.77 (15)	C11—C12—C18—C20	−60.00 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.85 (1)	1.79 (1)	2.640 (2)	179 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₇NO₃S
M_r	373.50
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.6305 (1), 9.3489 (2), 18.8749 (3)
α, β, γ (°)	85.505 (1), 89.453 (1), 87.834 (1)
V (Å³)	989.77 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.25 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.956, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	12688, 4507, 3746
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.127, 1.18
No. of reflections	4507
No. of parameters	239
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.71

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.85 (1)	1.79 (1)	2.640 (2)	179 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

We thank the University of Malaya (grant No. FS338/2008A) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kim, T. H. & Lee, N. (2003). Bull. Kor. Chem. Soc., 24, 1809–1813. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Um, S.-I. & Lee, J.-Y. (2005). Dyes Pigm. 64, 93–99. Web of Science CrossRef CAS Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar