(1R,2S,3R,5S)-5-(1H-Benzimidazol-2-yl)cyclo­hexane-1,2,3,5-tetraol mono­hydrate

Cai, Y.

doi:10.1107/S1600536809037957

organic compounds

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Volume 65| Part 10| October 2009| Page o2547

doi:10.1107/S1600536809037957

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(1R,2S,3R,5S)-5-(1H-Benzimidazol-2-yl)cyclohexane-1,2,3,5-tetraol monohydrate

Ying Cai ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: cyik@163.com

(Received 20 August 2009; accepted 19 September 2009; online 26 September 2009)

In the crystal structure of the title compound, C₁₃H₁₆N₂O₄·H₂O, intermolecular N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds form an extensive three-dimensional network, consolidating the crystal packing. The cyclohexane ring adopts a chair conformation.

Related literature

For the crystal structures of related compounds, see: Li et al. (1998 ); Gallagher et al. (2001 ); Howarth & Hanlon (2001 ); Huang et al. (2003 ); Kazak et al. (2006 ). For ring-puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₃H₁₆N₂O₄·H₂O
M_r = 282.29
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.9684 (14) Å
b = 9.4809 (15) Å
c = 15.278 (4) Å
V = 1299.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.30 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.817, T_max = 0.906
12121 measured reflections
1716 independent reflections
1646 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.079
S = 1.08
1716 reflections
253 parameters
All H-atom parameters refined
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H6⋯O1ⁱ	0.90 (3)	2.11 (3)	2.983 (2)	164 (2)
O3—H12⋯O5ⁱⁱ	0.83 (3)	2.00 (3)	2.831 (2)	176 (3)
O4—H13⋯O2	0.89 (3)	1.87 (3)	2.660 (2)	148 (3)
O2—H14⋯O5ⁱⁱⁱ	0.84 (3)	1.93 (3)	2.743 (2)	163 (3)
O1—H15⋯O3^iv	0.86 (3)	2.21 (3)	3.066 (2)	172 (3)
O5—H17⋯O4^v	0.88 (3)	1.96 (4)	2.827 (2)	169 (3)
O5—H18⋯N1	0.93 (4)	1.81 (4)	2.740 (2)	176 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) x-1, y, z; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809037957/bx2237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037957/bx2237Isup2.hkl

checkCIF report

Comment top

It has been generally accepted that benzimidazole systems continue to attract much attention due to applications in : chemical synthesis, structural science, applied biological and coordination chemistry (Gallagher et al., 2001; Huang et al., 2003; Kazak et al., 2006). We report here the crystal structure of the title compound (Fig.1). The cyclohexane ring adopt a chair conformation as shown by the Cremer and Pople (1975) puckering parameters [Q_T= 0.573 (2) Å, θ =174.2 (2) ° and

ϕ=136 (2)°] and has the same configuration as the cyclohexane ring of (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid, used as started material . The crystal is stabilized by hydrogen bonds of N—H···O, O—H···O and hydrogen bond of O—H ···N, resulting in an extensive three-dimensional network (Fig. 2).

Related literature top

For the crystal structures of related compounds, see: Li et al. (1998); Gallagher et al. (2001); Howarth & Hanlon (2001); Huang et al. (2003); Kazak et al. (2006).

For related literature, see: Cremer & Pople (1975).

Experimental top

(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid (0.02 mol, 3.84 g) and benzene-1,2-diamine (0.02 mol, 2.16 g) were dissolved in 5.5 N HCl (20 ml) at 110°C with stirring for 24 h at 110°C. After the solution was cooled to room temperature, the pH was adjusted to 8–9 with NaOH solution. The product formed was filtered, washed with ethanol and dried. Further purification was done by recrystallization from methanol. Single crystals suitable for X-ray analysis were obtained with about 50% yield.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of compound (1) with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis and all water molecules were omitted for clarity.

(1R,2S,3R,5S)-5-(1H-Benzimidazol-2- yl)cyclohexane-1,2,3,5-tetraol monohydrate top

Crystal data top

C₁₃H₁₆N₂O₄·H₂O	F(000) = 600
M_r = 282.29	D_x = 1.443 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3450 reflections
a = 8.9684 (14) Å	θ = 2.6–27.4°
b = 9.4809 (15) Å	µ = 0.11 mm⁻¹
c = 15.278 (4) Å	T = 293 K
V = 1299.0 (4) Å³	Prism, pink
Z = 4	0.30 × 0.30 × 0.30 mm

Data collection top

Rigaku Mercury CCD diffractometer	1716 independent reflections
Radiation source: fine-focus sealed tube	1646 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.817, T_max = 0.906	l = −18→19
12121 measured reflections

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)] = 0.033	All H-atom parameters refined
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0412P)² + 0.2437P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
1716 reflections	Δρ_max = 0.14 e Å⁻³
253 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0476 (15)

Crystal data top

C₁₃H₁₆N₂O₄·H₂O	V = 1299.0 (4) Å³
M_r = 282.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.9684 (14) Å	µ = 0.11 mm⁻¹
b = 9.4809 (15) Å	T = 293 K
c = 15.278 (4) Å	0.30 × 0.30 × 0.30 mm

Data collection top

Rigaku Mercury CCD diffractometer	1716 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1646 reflections with I > 2σ(I)
T_min = 0.817, T_max = 0.906	R_int = 0.030
12121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.079	All H-atom parameters refined
S = 1.08	Δρ_max = 0.14 e Å⁻³
1716 reflections	Δρ_min = −0.18 e Å⁻³
253 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
O5	0.72771 (16)	0.24370 (18)	0.64625 (9)	0.0354 (3)
C11	0.6615 (2)	0.3526 (2)	0.86815 (13)	0.0301 (4)
O3	0.07767 (15)	0.25080 (16)	0.51676 (10)	0.0348 (3)
O1	0.31588 (16)	0.45480 (17)	0.50248 (9)	0.0356 (3)
N1	0.57765 (19)	0.33374 (19)	0.79210 (11)	0.0348 (4)
N2	0.43215 (18)	0.42648 (18)	0.89530 (10)	0.0292 (3)
O2	0.01088 (17)	0.3204 (2)	0.69454 (10)	0.0435 (4)
C1	0.1920 (2)	0.2640 (2)	0.58171 (12)	0.0276 (4)
C2	0.4434 (2)	0.3787 (2)	0.81175 (12)	0.0286 (4)
C3	0.3703 (2)	0.4282 (2)	0.65804 (12)	0.0280 (4)
C4	0.5722 (2)	0.41153 (19)	0.93338 (12)	0.0264 (4)
C5	0.2540 (2)	0.4136 (2)	0.58515 (11)	0.0258 (4)
C6	0.3142 (2)	0.3786 (2)	0.74770 (12)	0.0266 (4)
C7	0.2462 (3)	0.2298 (2)	0.74082 (13)	0.0347 (4)
C8	0.6284 (2)	0.4454 (2)	1.01561 (13)	0.0332 (4)
C9	0.8684 (2)	0.3580 (2)	0.96474 (15)	0.0368 (5)
C10	0.7779 (2)	0.4184 (2)	1.02923 (14)	0.0351 (4)
C12	0.8121 (2)	0.3239 (2)	0.88366 (15)	0.0371 (5)
C13	0.1264 (2)	0.2240 (2)	0.66954 (13)	0.0340 (4)
O4	0.20679 (15)	0.47505 (16)	0.78330 (10)	0.0363 (3)
H1	0.272 (2)	0.196 (2)	0.5665 (14)	0.029 (5)*
H2	0.328 (3)	0.161 (3)	0.7259 (17)	0.045 (7)*
H3	0.456 (3)	0.376 (2)	0.6402 (15)	0.033 (6)*
H4	0.976 (3)	0.341 (2)	0.9775 (15)	0.038 (6)*
H5	0.173 (3)	0.477 (2)	0.5973 (13)	0.026 (5)*
H6	0.347 (3)	0.459 (3)	0.9186 (16)	0.042 (7)*
H7	0.824 (3)	0.440 (3)	1.0846 (16)	0.041 (6)*
H8	0.875 (3)	0.290 (3)	0.8364 (19)	0.061 (8)*
H9	0.198 (3)	0.206 (3)	0.8007 (16)	0.042 (6)*
H10	0.401 (3)	0.527 (3)	0.6663 (15)	0.043 (7)*
H11	0.567 (3)	0.488 (3)	1.0588 (18)	0.045 (7)*
H12	0.126 (3)	0.252 (3)	0.4704 (19)	0.058 (9)*
H13	0.119 (3)	0.445 (3)	0.7643 (18)	0.054 (8)*
H14	−0.069 (3)	0.299 (3)	0.6691 (18)	0.055 (8)*
H15	0.393 (3)	0.403 (3)	0.4937 (18)	0.055 (8)*
H16	0.088 (3)	0.123 (2)	0.6650 (14)	0.029 (6)*
H17	0.745 (4)	0.156 (4)	0.661 (2)	0.074 (10)*
H18	0.673 (4)	0.272 (4)	0.695 (2)	0.077 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0314 (7)	0.0459 (9)	0.0290 (7)	0.0014 (7)	0.0037 (6)	−0.0055 (6)
C11	0.0283 (9)	0.0381 (10)	0.0239 (9)	0.0032 (8)	−0.0024 (7)	−0.0007 (7)
O3	0.0279 (7)	0.0504 (8)	0.0260 (7)	−0.0044 (7)	−0.0035 (6)	−0.0059 (7)
O1	0.0302 (7)	0.0533 (9)	0.0235 (7)	−0.0023 (7)	−0.0003 (6)	0.0087 (6)
N1	0.0289 (8)	0.0517 (10)	0.0238 (8)	0.0084 (8)	−0.0033 (7)	−0.0078 (7)
N2	0.0233 (7)	0.0420 (9)	0.0224 (8)	0.0030 (7)	−0.0015 (6)	−0.0036 (7)
O2	0.0236 (7)	0.0740 (11)	0.0330 (8)	−0.0094 (7)	0.0042 (6)	−0.0140 (8)
C1	0.0251 (8)	0.0350 (9)	0.0226 (8)	0.0022 (8)	−0.0019 (7)	−0.0036 (7)
C2	0.0266 (9)	0.0364 (9)	0.0228 (9)	0.0013 (8)	0.0000 (7)	−0.0028 (7)
C3	0.0236 (8)	0.0362 (10)	0.0240 (9)	−0.0015 (8)	−0.0020 (7)	−0.0011 (7)
C4	0.0247 (8)	0.0320 (8)	0.0224 (9)	−0.0004 (7)	−0.0013 (7)	0.0006 (7)
C5	0.0223 (8)	0.0359 (9)	0.0192 (8)	0.0004 (8)	0.0002 (7)	0.0010 (7)
C6	0.0239 (8)	0.0362 (9)	0.0197 (8)	0.0016 (7)	−0.0004 (7)	−0.0047 (7)
C7	0.0413 (11)	0.0391 (10)	0.0239 (9)	−0.0045 (10)	−0.0038 (8)	0.0038 (8)
C8	0.0332 (9)	0.0429 (10)	0.0235 (9)	0.0001 (9)	−0.0019 (8)	−0.0028 (8)
C9	0.0264 (9)	0.0447 (11)	0.0394 (11)	0.0008 (9)	−0.0063 (8)	0.0066 (9)
C10	0.0341 (10)	0.0412 (10)	0.0300 (10)	−0.0045 (9)	−0.0109 (8)	0.0034 (8)
C12	0.0273 (9)	0.0486 (12)	0.0355 (11)	0.0068 (9)	0.0003 (8)	−0.0015 (9)
C13	0.0353 (10)	0.0387 (11)	0.0281 (10)	−0.0111 (9)	−0.0022 (8)	−0.0012 (8)
O4	0.0248 (7)	0.0507 (8)	0.0335 (8)	0.0058 (7)	−0.0027 (6)	−0.0141 (6)

Geometric parameters (Å, º) top

O5—H17	0.88 (3)	C3—C6	1.533 (3)
O5—H18	0.93 (4)	C3—H3	0.95 (2)
C11—C4	1.395 (3)	C3—H10	0.98 (3)
C11—N1	1.395 (2)	C4—C8	1.391 (3)
C11—C12	1.398 (3)	C5—H5	0.96 (2)
O3—C1	1.432 (2)	C6—O4	1.435 (2)
O3—H12	0.83 (3)	C6—C7	1.540 (3)
O1—C5	1.434 (2)	C7—C13	1.531 (3)
O1—H15	0.86 (3)	C7—H2	1.01 (3)
N1—C2	1.312 (2)	C7—H9	1.04 (2)
N2—C2	1.358 (2)	C8—C10	1.381 (3)
N2—C4	1.392 (2)	C8—H11	0.95 (3)
N2—H6	0.90 (3)	C9—C12	1.376 (3)
O2—C13	1.434 (3)	C9—C10	1.399 (3)
O2—H14	0.84 (3)	C9—H4	1.00 (2)
C1—C13	1.514 (3)	C10—H7	0.96 (2)
C1—C5	1.524 (3)	C12—H8	0.97 (3)
C1—H1	0.99 (2)	C13—H16	1.02 (2)
C2—C6	1.517 (3)	O4—H13	0.89 (3)
C3—C5	1.532 (2)

H17—O5—H18	99 (3)	C1—C5—H5	108.0 (13)
C4—C11—N1	109.71 (16)	C3—C5—H5	108.7 (12)
C4—C11—C12	120.72 (19)	O4—C6—C2	105.52 (14)
N1—C11—C12	129.55 (19)	O4—C6—C3	111.29 (16)
C1—O3—H12	102.6 (19)	C2—C6—C3	109.00 (15)
C5—O1—H15	107.0 (19)	O4—C6—C7	110.09 (16)
C2—N1—C11	105.19 (16)	C2—C6—C7	110.33 (15)
C2—N2—C4	106.96 (16)	C3—C6—C7	110.49 (15)
C2—N2—H6	123.3 (16)	C13—C7—C6	111.08 (16)
C4—N2—H6	129.7 (16)	C13—C7—H2	109.1 (15)
C13—O2—H14	110 (2)	C6—C7—H2	108.6 (15)
O3—C1—C13	108.30 (15)	C13—C7—H9	109.1 (15)
O3—C1—C5	111.52 (15)	C6—C7—H9	107.7 (13)
C13—C1—C5	110.17 (15)	H2—C7—H9	111 (2)
O3—C1—H1	107.5 (12)	C10—C8—C4	116.39 (19)
C13—C1—H1	109.1 (12)	C10—C8—H11	122.5 (16)
C5—C1—H1	110.2 (12)	C4—C8—H11	121.1 (16)
N1—C2—N2	113.06 (17)	C12—C9—C10	121.11 (19)
N1—C2—C6	123.58 (17)	C12—C9—H4	119.5 (14)
N2—C2—C6	123.37 (16)	C10—C9—H4	119.4 (14)
C5—C3—C6	113.48 (15)	C8—C10—C9	122.24 (19)
C5—C3—H3	107.0 (14)	C8—C10—H7	120.5 (16)
C6—C3—H3	111.0 (14)	C9—C10—H7	117.3 (16)
C5—C3—H10	111.7 (14)	C9—C12—C11	117.5 (2)
C6—C3—H10	105.6 (14)	C9—C12—H8	122.3 (17)
H3—C3—H10	107.9 (19)	C11—C12—H8	120.0 (17)
C8—C4—N2	132.89 (18)	O2—C13—C1	110.91 (17)
C8—C4—C11	122.02 (17)	O2—C13—C7	107.13 (16)
N2—C4—C11	105.07 (16)	C1—C13—C7	110.40 (16)
O1—C5—C1	111.36 (15)	O2—C13—H16	111.8 (13)
O1—C5—C3	110.63 (14)	C1—C13—H16	107.9 (13)
C1—C5—C3	110.96 (15)	C7—C13—H16	108.7 (13)
O1—C5—H5	107.1 (12)	C6—O4—H13	105.7 (18)

C4—C11—N1—C2	−0.5 (2)	N1—C2—C6—C7	79.5 (2)
C12—C11—N1—C2	−179.1 (2)	N2—C2—C6—C7	−101.0 (2)
C11—N1—C2—N2	0.2 (2)	C5—C3—C6—O4	−71.7 (2)
C11—N1—C2—C6	179.75 (17)	C5—C3—C6—C2	172.34 (15)
C4—N2—C2—N1	0.2 (2)	C5—C3—C6—C7	50.9 (2)
C4—N2—C2—C6	−179.36 (17)	O4—C6—C7—C13	69.8 (2)
C2—N2—C4—C8	178.1 (2)	C2—C6—C7—C13	−174.09 (16)
C2—N2—C4—C11	−0.5 (2)	C3—C6—C7—C13	−53.5 (2)
N1—C11—C4—C8	−178.15 (18)	N2—C4—C8—C10	−178.0 (2)
C12—C11—C4—C8	0.6 (3)	C11—C4—C8—C10	0.4 (3)
N1—C11—C4—N2	0.6 (2)	C4—C8—C10—C9	−1.0 (3)
C12—C11—C4—N2	179.4 (2)	C12—C9—C10—C8	0.7 (3)
O3—C1—C5—O1	−59.24 (19)	C10—C9—C12—C11	0.3 (3)
C13—C1—C5—O1	−179.53 (15)	C4—C11—C12—C9	−0.9 (3)
O3—C1—C5—C3	177.05 (15)	N1—C11—C12—C9	177.6 (2)
C13—C1—C5—C3	56.76 (19)	O3—C1—C13—O2	−64.01 (19)
C6—C3—C5—O1	−177.00 (16)	C5—C1—C13—O2	58.20 (19)
C6—C3—C5—C1	−52.9 (2)	O3—C1—C13—C7	177.41 (16)
N1—C2—C6—O4	−161.58 (19)	C5—C1—C13—C7	−60.4 (2)
N2—C2—C6—O4	17.9 (2)	C6—C7—C13—O2	−61.7 (2)
N1—C2—C6—C3	−42.0 (3)	C6—C7—C13—C1	59.1 (2)
N2—C2—C6—C3	137.55 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H6···O1ⁱ	0.90 (3)	2.11 (3)	2.983 (2)	164 (2)
O3—H12···O5ⁱⁱ	0.83 (3)	2.00 (3)	2.831 (2)	176 (3)
O4—H13···O2	0.89 (3)	1.87 (3)	2.660 (2)	148 (3)
O2—H14···O5ⁱⁱⁱ	0.84 (3)	1.93 (3)	2.743 (2)	163 (3)
O1—H15···O3^iv	0.86 (3)	2.21 (3)	3.066 (2)	172 (3)
O5—H17···O4^v	0.88 (3)	1.96 (4)	2.827 (2)	169 (3)
O5—H18···N1	0.93 (4)	1.81 (4)	2.740 (2)	176 (3)

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) x−1/2, −y+1/2, −z+1; (iii) x−1, y, z; (iv) x+1/2, −y+1/2, −z+1; (v) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₂O₄·H₂O
M_r	282.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.9684 (14), 9.4809 (15), 15.278 (4)
V (Å³)	1299.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.817, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	12121, 1716, 1646
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.079, 1.08
No. of reflections	1716
No. of parameters	253
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H6···O1ⁱ	0.90 (3)	2.11 (3)	2.983 (2)	164 (2)
O3—H12···O5ⁱⁱ	0.83 (3)	2.00 (3)	2.831 (2)	176 (3)
O4—H13···O2	0.89 (3)	1.87 (3)	2.660 (2)	148 (3)
O2—H14···O5ⁱⁱⁱ	0.84 (3)	1.93 (3)	2.743 (2)	163 (3)
O1—H15···O3^iv	0.86 (3)	2.21 (3)	3.066 (2)	172 (3)
O5—H17···O4^v	0.88 (3)	1.96 (4)	2.827 (2)	169 (3)
O5—H18···N1	0.93 (4)	1.81 (4)	2.740 (2)	176 (3)

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) x−1/2, −y+1/2, −z+1; (iii) x−1, y, z; (iv) x+1/2, −y+1/2, −z+1; (v) −x+1, y−1/2, −z+3/2.

References

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Gallagher, J. F., Hanlon, K. & Howarth, J. (2001). Acta Cryst. C57, 1410–1414. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Howarth, J. & Hanlon, K. (2001). Tetrahedron Lett. 42, 271–274. Google Scholar
Huang, X.-C., Zhang, J.-P. & Chen, X.-M. (2003). Chin. Sci. Bull. 48, 1531– 1534. Web of Science CSD CrossRef CAS Google Scholar
Kazak, C., Yilmaz, V. T., Goker, H. & Kus, C. (2006). Cryst. Res. Technol. 5, 528–532. Web of Science CSD CrossRef Google Scholar
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Volume 65| Part 10| October 2009| Page o2547

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