1,10-Phenanthrolin-1-ium hydrogen d,l-tartrate dihydrate

Cheng, S.F.; Ng, S.W.

doi:10.1107/S1600536811015972

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1306

doi:10.1107/S1600536811015972

Open

access

1,10-Phenanthrolin-1-ium hydrogen D,L-tartrate dihydrate

Sit Foon Cheng ^a and Seik Weng Ng ^a ^*

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

(Received 27 April 2011; accepted 27 April 2011; online 7 May 2011)

In the title hydrated molecular salt, C₁₂H₉N₂⁺·C₄H₅O₆⁻·2H₂O, the cation is almost planar (r.m.s. deviation = 0.014 Å); the carbon skeleton of the anion assumes a trans conformation [C—C—C—C torsion angle = −179.86 (14)°]. The carboxyl end of one hydrogen tartrate anion forms a short hydrogen bond to the carboxylate end of another anion [O⋯O = 2.508 (2) Å] in a head-to-tail manner, forming a chain; the chains and water molecules interact, generating an O—H⋯O hydrogen-bonded layer. The cation binds to the layer by an N—H⋯O hydrogen bond.

Related literature

For the trihydrated 1,10-phenanthrolin-1-ium salts of D- and L-tartaric acid, see: Derikvand & Olmstead (2010 ); Wang et al. (2006 ).

Experimental

Crystal data

C₁₂H₉N₂⁺·C₄H₅O₆⁻·2H₂O
M_r = 366.32
Triclinic, $[P \overline 1]$
a = 7.0933 (7) Å
b = 10.5849 (11) Å
c = 11.4694 (11) Å
α = 98.081 (1)°
β = 100.350 (1)°
γ = 103.903 (1)°
V = 806.95 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
7610 measured reflections
3635 independent reflections
2880 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.160
S = 1.04
3635 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 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
O3—H3⋯O1wⁱ	0.89 (3)	1.82 (3)	2.709 (2)	175 (3)
O4—H4⋯O2wⁱⁱ	0.90 (3)	1.84 (3)	2.739 (2)	172 (3)
O5—H5⋯O2ⁱⁱⁱ	0.99 (3)	1.52 (3)	2.508 (2)	169 (3)
O1w—H12⋯O1	0.93 (3)	1.97 (3)	2.846 (2)	157 (3)
O1w—H11⋯O1^iv	0.90 (4)	1.86 (4)	2.753 (2)	173 (4)
O2w—H21⋯O2	0.84 (4)	1.93 (4)	2.764 (2)	168 (3)
O2w—H22⋯O6^v	0.87 (3)	1.97 (3)	2.835 (2)	176 (3)
N1—H1⋯O1w	0.93 (3)	1.89 (3)	2.753 (2)	153 (3)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x, -y+2, -z; (iii) x+1, y, z; (iv) -x, -y+2, -z+1; (v) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015972/bt5536sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015972/bt5536Isup2.hkl

checkCIF report

Comment top

D-tartaric acid transfers one proton to 1,10-phenanthroline to yield 1,10-phenanthroline hydrogen D-tartrate, which separates from solution as a trihydrate. The hydrogen D-tartrate anions are connected in a head-to-tail fashion by an O–H_{carboxylic acid}···O_carboxyl hydrogen bond [O···O 2.455 (1) Å] (Derikvand & Olmstead, 2010). The identical feature should be presented in the L analog (Wang et al., 2006). The anion and water molecules are linked by extensive O–H···O hydrogen bonds into a three-dimensional network, with the cations occupying the cavities. Racemic tartaric furnishes the corresponding dihydrate. In C₁₂H₉N₂⁺ C₄H₅O₄^-.2H₂O (Scheme I, Fig. 1), the carboxylic acid –CO₂H end of one hydrogen (D,L)-tartrate anion forms a short hydrogen bond to the carboxylate –CO₂^- end of another anion [O···O 2.508 (2) Å] in a head-to-tail manner to form a chain; the chains and water molecules interact to generate an O–H···O hydrogen-bonded layer. The cation binds to the layer by an N–H···O hydrogen bond (Table 1).

Related literature top

For the trihydrated 1,10-phenanthrolin-1-ium salts of D- and L-tartaric acid, see: Derikvand & Olmstead (2010); Wang et al. (2006).

Experimental top

D,L-Tartaric acid (2 mmol, 0.30 g) and 1,10-phenanthroline (0.33 mmol, 0.06 g) were dissolved in water (5 ml). The solution was heated briefly to dissolve the reactants. The solution was set aside for the growth of colorless crystals, which were isolated after 10 days. The bulk crystals were faintly tinted a shade of pink.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2010).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₂H₉N₂⁺ C₄H₅O₆^-.2H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded layer structure arising from tartrate–water interactions.

1,10-Phenanthrolin-1-ium hydrogen D,L-tartrate dihydrate top

Crystal data top

C₁₂H₉N₂⁺·C₄H₅O₆⁻·2H₂O	Z = 2
M_r = 366.32	F(000) = 384
Triclinic, P1	D_x = 1.508 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0933 (7) Å	Cell parameters from 2722 reflections
b = 10.5849 (11) Å	θ = 2.5–28.2°
c = 11.4694 (11) Å	µ = 0.12 mm⁻¹
α = 98.081 (1)°	T = 100 K
β = 100.350 (1)°	Prism, colorless
γ = 103.903 (1)°	0.40 × 0.10 × 0.10 mm
V = 806.95 (14) Å³

Data collection top

Bruker SMART APEX diffractometer	2880 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 27.5°, θ_min = 1.8°
ω scans	h = −9→9
7610 measured reflections	k = −13→13
3635 independent reflections	l = −14→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.1012P)² + 0.1854P] where P = (F_o² + 2F_c²)/3
3635 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₂H₉N₂⁺·C₄H₅O₆⁻·2H₂O	γ = 103.903 (1)°
M_r = 366.32	V = 806.95 (14) Å³
Triclinic, P1	Z = 2
a = 7.0933 (7) Å	Mo Kα radiation
b = 10.5849 (11) Å	µ = 0.12 mm⁻¹
c = 11.4694 (11) Å	T = 100 K
α = 98.081 (1)°	0.40 × 0.10 × 0.10 mm
β = 100.350 (1)°

Data collection top

Bruker SMART APEX diffractometer	2880 reflections with I > 2σ(I)
7610 measured reflections	R_int = 0.028
3635 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.35 e Å⁻³
3635 reflections	Δρ_min = −0.31 e Å⁻³
267 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.0272 (2)	0.97612 (14)	0.33939 (12)	0.0172 (3)
O2	0.00294 (19)	1.04199 (14)	0.16223 (12)	0.0167 (3)
O3	0.3922 (2)	0.95680 (14)	0.34847 (12)	0.0163 (3)
O4	0.1832 (2)	0.78094 (13)	0.12086 (12)	0.0154 (3)
O5	0.6410 (2)	1.02428 (13)	0.15147 (12)	0.0153 (3)
O6	0.5609 (2)	0.80301 (14)	0.09605 (13)	0.0192 (3)
O1W	0.2228 (2)	0.90933 (13)	0.55174 (12)	0.0145 (3)
O2W	0.1595 (2)	1.23818 (15)	0.04324 (13)	0.0174 (3)
N1	0.2289 (2)	0.65380 (16)	0.46822 (15)	0.0143 (3)
N2	0.2713 (2)	0.66417 (16)	0.71074 (15)	0.0171 (4)
C1	0.0952 (3)	1.00580 (17)	0.25142 (16)	0.0125 (4)
C2	0.3085 (3)	1.00188 (18)	0.24666 (16)	0.0124 (4)
H2A	0.3902	1.0934	0.2475	0.015*
C3	0.3050 (3)	0.91028 (18)	0.12952 (16)	0.0115 (4)
H3A	0.2505	0.9473	0.0594	0.014*
C4	0.5161 (3)	0.90552 (18)	0.12418 (16)	0.0122 (4)
C5	0.2130 (3)	0.6578 (2)	0.35202 (18)	0.0184 (4)
H5A	0.2027	0.7366	0.3240	0.022*
C6	0.2114 (3)	0.5459 (2)	0.27087 (19)	0.0220 (5)
H6	0.2015	0.5487	0.1876	0.026*
C7	0.2243 (3)	0.4319 (2)	0.31181 (19)	0.0213 (4)
H7	0.2216	0.3552	0.2567	0.026*
C8	0.2417 (3)	0.42852 (19)	0.43589 (19)	0.0178 (4)
C9	0.2446 (3)	0.54419 (18)	0.51418 (17)	0.0138 (4)
C10	0.2550 (3)	0.3129 (2)	0.4856 (2)	0.0220 (5)
H10	0.2530	0.2340	0.4337	0.026*
C11	0.2704 (3)	0.3145 (2)	0.6049 (2)	0.0224 (5)
H11A	0.2778	0.2366	0.6356	0.027*
C12	0.2757 (3)	0.43249 (19)	0.68601 (19)	0.0173 (4)
C13	0.2645 (3)	0.54791 (18)	0.64134 (18)	0.0149 (4)
C14	0.2935 (3)	0.4390 (2)	0.8110 (2)	0.0227 (5)
H14	0.3004	0.3633	0.8456	0.027*
C15	0.3006 (3)	0.5558 (2)	0.8818 (2)	0.0236 (5)
H15	0.3135	0.5626	0.9665	0.028*
C16	0.2888 (3)	0.6661 (2)	0.82806 (18)	0.0210 (4)
H16	0.2936	0.7464	0.8787	0.025*
H3	0.517 (5)	1.006 (3)	0.381 (3)	0.048 (9)*
H4	0.066 (4)	0.767 (3)	0.067 (3)	0.032 (7)*
H5	0.781 (5)	1.020 (3)	0.156 (3)	0.057 (10)*
H11	0.145 (5)	0.944 (4)	0.593 (4)	0.067 (11)*
H12	0.195 (4)	0.938 (3)	0.480 (3)	0.039 (8)*
H21	0.120 (5)	1.172 (4)	0.074 (3)	0.052 (10)*
H22	0.247 (5)	1.223 (3)	0.003 (3)	0.037 (8)*
H1	0.233 (5)	0.731 (3)	0.520 (3)	0.046 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0162 (7)	0.0231 (7)	0.0161 (7)	0.0078 (6)	0.0087 (5)	0.0054 (5)
O2	0.0131 (7)	0.0224 (7)	0.0178 (7)	0.0070 (5)	0.0060 (5)	0.0070 (6)
O3	0.0120 (7)	0.0243 (7)	0.0118 (7)	0.0032 (6)	0.0015 (5)	0.0055 (5)
O4	0.0139 (7)	0.0137 (7)	0.0165 (7)	0.0017 (5)	0.0018 (5)	0.0020 (5)
O5	0.0123 (7)	0.0156 (7)	0.0197 (7)	0.0047 (5)	0.0058 (5)	0.0036 (5)
O6	0.0187 (7)	0.0173 (7)	0.0250 (8)	0.0097 (6)	0.0070 (6)	0.0042 (6)
O1W	0.0160 (7)	0.0181 (7)	0.0111 (7)	0.0070 (5)	0.0038 (5)	0.0037 (5)
O2W	0.0167 (7)	0.0191 (7)	0.0168 (7)	0.0047 (6)	0.0053 (6)	0.0034 (6)
N1	0.0141 (8)	0.0146 (8)	0.0132 (8)	0.0028 (6)	0.0023 (6)	0.0017 (6)
N2	0.0195 (8)	0.0153 (8)	0.0154 (8)	0.0040 (6)	0.0017 (7)	0.0033 (6)
C1	0.0139 (9)	0.0108 (8)	0.0123 (9)	0.0027 (7)	0.0044 (7)	−0.0003 (7)
C2	0.0105 (8)	0.0153 (9)	0.0120 (9)	0.0034 (7)	0.0039 (7)	0.0027 (7)
C3	0.0115 (8)	0.0142 (8)	0.0101 (8)	0.0042 (7)	0.0035 (7)	0.0041 (7)
C4	0.0146 (9)	0.0153 (8)	0.0083 (8)	0.0053 (7)	0.0036 (7)	0.0041 (7)
C5	0.0159 (9)	0.0225 (10)	0.0166 (10)	0.0039 (8)	0.0040 (7)	0.0051 (8)
C6	0.0196 (10)	0.0278 (11)	0.0169 (10)	0.0038 (8)	0.0059 (8)	0.0009 (8)
C7	0.0148 (9)	0.0226 (10)	0.0229 (11)	0.0041 (8)	0.0051 (8)	−0.0062 (8)
C8	0.0110 (9)	0.0167 (9)	0.0230 (10)	0.0016 (7)	0.0039 (7)	−0.0015 (8)
C9	0.0107 (8)	0.0125 (8)	0.0178 (10)	0.0037 (7)	0.0020 (7)	0.0015 (7)
C10	0.0184 (10)	0.0128 (9)	0.0330 (12)	0.0042 (8)	0.0063 (9)	−0.0019 (8)
C11	0.0201 (10)	0.0122 (9)	0.0354 (12)	0.0058 (8)	0.0042 (9)	0.0065 (8)
C12	0.0131 (9)	0.0145 (9)	0.0239 (11)	0.0038 (7)	0.0020 (8)	0.0050 (8)
C13	0.0113 (8)	0.0134 (9)	0.0189 (10)	0.0029 (7)	0.0016 (7)	0.0031 (7)
C14	0.0227 (10)	0.0194 (10)	0.0282 (11)	0.0068 (8)	0.0026 (9)	0.0137 (9)
C15	0.0270 (11)	0.0248 (11)	0.0188 (10)	0.0056 (9)	0.0016 (8)	0.0105 (8)
C16	0.0262 (11)	0.0180 (10)	0.0164 (10)	0.0047 (8)	0.0016 (8)	0.0017 (8)

Geometric parameters (Å, º) top

O1—C1	1.241 (2)	C3—H3A	1.0000
O2—C1	1.269 (2)	C5—C6	1.395 (3)
O3—C2	1.410 (2)	C5—H5A	0.9500
O3—H3	0.89 (3)	C6—C7	1.372 (3)
O4—C3	1.412 (2)	C6—H6	0.9500
O4—H4	0.91 (3)	C7—C8	1.412 (3)
O5—C4	1.311 (2)	C7—H7	0.9500
O5—H5	1.00 (3)	C8—C9	1.406 (3)
O6—C4	1.219 (2)	C8—C10	1.437 (3)
O1W—H11	0.90 (4)	C9—C13	1.434 (3)
O1W—H12	0.92 (3)	C10—C11	1.350 (3)
O2W—H21	0.84 (4)	C10—H10	0.9500
O2W—H22	0.87 (3)	C11—C12	1.437 (3)
N1—C5	1.325 (3)	C11—H11A	0.9500
N1—C9	1.360 (3)	C12—C13	1.403 (3)
N1—H1	0.93 (3)	C12—C14	1.407 (3)
N2—C16	1.326 (3)	C14—C15	1.365 (3)
N2—C13	1.354 (2)	C14—H14	0.9500
C1—C2	1.534 (2)	C15—C16	1.407 (3)
C2—C3	1.535 (2)	C15—H15	0.9500
C2—H2A	1.0000	C16—H16	0.9500
C3—C4	1.522 (2)

C2—O3—H3	111 (2)	C5—C6—H6	120.1
C3—O4—H4	110.2 (17)	C6—C7—C8	119.99 (19)
C4—O5—H5	111.6 (19)	C6—C7—H7	120.0
H11—O1W—H12	101 (3)	C8—C7—H7	120.0
H21—O2W—H22	109 (3)	C9—C8—C7	118.09 (19)
C5—N1—C9	122.93 (18)	C9—C8—C10	118.62 (19)
C5—N1—H1	117.6 (19)	C7—C8—C10	123.30 (19)
C9—N1—H1	119.4 (19)	N1—C9—C8	119.30 (18)
C16—N2—C13	116.48 (17)	N1—C9—C13	119.82 (17)
O1—C1—O2	125.36 (18)	C8—C9—C13	120.88 (18)
O1—C1—C2	119.50 (17)	C11—C10—C8	121.05 (19)
O2—C1—C2	115.13 (16)	C11—C10—H10	119.5
O3—C2—C1	109.60 (14)	C8—C10—H10	119.5
O3—C2—C3	110.78 (15)	C10—C11—C12	120.86 (19)
C1—C2—C3	109.30 (14)	C10—C11—H11A	119.6
O3—C2—H2A	109.0	C12—C11—H11A	119.6
C1—C2—H2A	109.0	C13—C12—C14	117.29 (18)
C3—C2—H2A	109.0	C13—C12—C11	119.93 (19)
O4—C3—C4	109.91 (14)	C14—C12—C11	122.78 (18)
O4—C3—C2	111.42 (14)	N2—C13—C12	124.24 (18)
C4—C3—C2	109.66 (14)	N2—C13—C9	117.11 (17)
O4—C3—H3A	108.6	C12—C13—C9	118.65 (18)
C4—C3—H3A	108.6	C15—C14—C12	118.92 (19)
C2—C3—H3A	108.6	C15—C14—H14	120.5
O6—C4—O5	124.72 (17)	C12—C14—H14	120.5
O6—C4—C3	123.46 (17)	C14—C15—C16	119.4 (2)
O5—C4—C3	111.81 (15)	C14—C15—H15	120.3
N1—C5—C6	119.94 (19)	C16—C15—H15	120.3
N1—C5—H5A	120.0	N2—C16—C15	123.7 (2)
C6—C5—H5A	120.0	N2—C16—H16	118.1
C7—C6—C5	119.74 (19)	C15—C16—H16	118.1
C7—C6—H6	120.1

O1—C1—C2—O3	2.5 (2)	C10—C8—C9—C13	1.3 (3)
O2—C1—C2—O3	−178.33 (15)	C9—C8—C10—C11	−0.1 (3)
O1—C1—C2—C3	124.08 (18)	C7—C8—C10—C11	−179.65 (19)
O2—C1—C2—C3	−56.7 (2)	C8—C10—C11—C12	−0.6 (3)
O3—C2—C3—O4	62.92 (19)	C10—C11—C12—C13	0.1 (3)
C1—C2—C3—O4	−57.94 (19)	C10—C11—C12—C14	−179.4 (2)
O3—C2—C3—C4	−58.99 (19)	C16—N2—C13—C12	−0.3 (3)
C1—C2—C3—C4	−179.86 (14)	C16—N2—C13—C9	179.70 (17)
O4—C3—C4—O6	11.4 (2)	C14—C12—C13—N2	0.6 (3)
C2—C3—C4—O6	134.17 (19)	C11—C12—C13—N2	−178.96 (18)
O4—C3—C4—O5	−169.64 (14)	C14—C12—C13—C9	−179.49 (17)
C2—C3—C4—O5	−46.8 (2)	C11—C12—C13—C9	1.0 (3)
C9—N1—C5—C6	0.1 (3)	N1—C9—C13—N2	−1.5 (3)
N1—C5—C6—C7	0.7 (3)	C8—C9—C13—N2	178.28 (17)
C5—C6—C7—C8	−0.8 (3)	N1—C9—C13—C12	178.54 (17)
C6—C7—C8—C9	0.2 (3)	C8—C9—C13—C12	−1.7 (3)
C6—C7—C8—C10	179.72 (19)	C13—C12—C14—C15	−0.6 (3)
C5—N1—C9—C8	−0.8 (3)	C11—C12—C14—C15	178.92 (19)
C5—N1—C9—C13	179.01 (18)	C12—C14—C15—C16	0.4 (3)
C7—C8—C9—N1	0.6 (3)	C13—N2—C16—C15	0.1 (3)
C10—C8—C9—N1	−178.97 (17)	C14—C15—C16—N2	−0.2 (3)
C7—C8—C9—C13	−179.19 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1wⁱ	0.89 (3)	1.82 (3)	2.709 (2)	175 (3)
O4—H4···O2wⁱⁱ	0.90 (3)	1.84 (3)	2.739 (2)	172 (3)
O5—H5···O2ⁱⁱⁱ	0.99 (3)	1.52 (3)	2.508 (2)	169 (3)
O1w—H12···O1	0.93 (3)	1.97 (3)	2.846 (2)	157 (3)
O1w—H11···O1^iv	0.90 (4)	1.86 (4)	2.753 (2)	173 (4)
O2w—H21···O2	0.84 (4)	1.93 (4)	2.764 (2)	168 (3)
O2w—H22···O6^v	0.87 (3)	1.97 (3)	2.835 (2)	176 (3)
N1—H1···O1w	0.93 (3)	1.89 (3)	2.753 (2)	153 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₂⁺·C₄H₅O₆⁻·2H₂O
M_r	366.32
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.0933 (7), 10.5849 (11), 11.4694 (11)
α, β, γ (°)	98.081 (1), 100.350 (1), 103.903 (1)
V (Å³)	806.95 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7610, 3635, 2880
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.160, 1.04
No. of reflections	3635
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.31

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1wⁱ	0.89 (3)	1.82 (3)	2.709 (2)	175 (3)
O4—H4···O2wⁱⁱ	0.90 (3)	1.84 (3)	2.739 (2)	172 (3)
O5—H5···O2ⁱⁱⁱ	0.99 (3)	1.52 (3)	2.508 (2)	169 (3)
O1w—H12···O1	0.93 (3)	1.97 (3)	2.846 (2)	157 (3)
O1w—H11···O1^iv	0.90 (4)	1.86 (4)	2.753 (2)	173 (4)
O2w—H21···O2	0.84 (4)	1.93 (4)	2.764 (2)	168 (3)
O2w—H22···O6^v	0.87 (3)	1.97 (3)	2.835 (2)	176 (3)
N1—H1···O1w	0.93 (3)	1.89 (3)	2.753 (2)	153 (3)

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

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Derikvand, Z. & Olmstead, M. M. (2010). Acta Cryst. E66, o185. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Z.-L., Li, M.-X., Wei, L.-H. & Wang, J.-P. (2006). Acta Cryst. E62, o2508–o2509. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar