d-Mannitol-1,2,6-tribenzoate

Carr, J.M.; Draffin, S.P.; Duggan, P.J.; Fallon, G.D.; Humphrey, D.G.

doi:10.1107/S1600536801018074

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D-Mannitol-1,2,6-tribenzoate

J. M. Carr, S. P. Draffin, P. J. Duggan, G. D. Fallon and D. G. Humphrey

D-Mannitol-1,2,6-tribenzoate, C₂₇H₂₆O₉, was obtained as a side product from the reaction of D-mannitol with benzoyl chloride in hot pyridine. The major product of the reaction was D-mannitol-1,6-dibenzoate.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018074/bt6091sup1.cif Contains datablocks trib, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018074/bt6091Isup2.hkl Contains datablock I

CCDC reference: 176041

checkCIF report

Key indicators

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R factor = 0.036
wR factor = 0.087
Data-to-parameter ratio = 10.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.30
         From the CIF: _reflns_number_total               3347
         Count of symmetry unique reflns         3381
         Completeness (_total/calc)             98.99%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

Comment top

The application of boronic acids as labile protective agents in the selective functionalization of poly-ols is currently one of the focus areas of our research (Bhaskar et al., 2001). The title compound, (I), was obtained from a control experiment, which was performed in order to determine the yield and selectivity of the reaction of D-mannitol with benzoyl chloride in the absence of a boronic acid. It is interesting to note that the third acylation of D-mannitol occurs at 2-OH, rather than 3-OH.

Experimental top

D-Mannitol (20.03 g, 0.11 mol) was treated with benzoyl chloride (12.30 ml, 0.11 mol) in hot pyridine (75 ml), following the procedure of Morpain & Tisserand (1979). After the reaction mixture was cooled, a white precipitate was obtained which was recrystallized from hot methanol to afford pure D-mannitol-1,6-dibenzoate (4.29 g, 20%) (Bhaskar et al., 2001). The addition of water to the recrystallization filtrate, followed by prolonged cooling, produced a crop of colourless needles that were collected by filtration, washed with diethyl ether and dried in air. Spectroscopic and X-ray crystallographic characterization of the needles revealed the second product to be D-mannitol-1,2,6-tribenzoate (0.31 g, 2%). m.p. 438–441 K [literature 439–440 K (Hockett & Fletcher, 1944)].

Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. View of (I) (50% probability displacement ellipsoids).

(I) top

Crystal data top

C₂₇H₂₆O₉	D_x = 1.394 Mg m⁻³
M_r = 494.48	Melting point = 165–168 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 5.572 (1) Å	Cell parameters from 35667 reflections
b = 15.530 (1) Å	θ = 2.6–28.3°
c = 27.221 (2) Å	µ = 0.11 mm⁻¹
V = 2355.5 (5) Å³	T = 123 K
Z = 4	Acicular, colourless
F(000) = 1040	0.3 × 0.22 × 0.18 mm

Data collection top

KappaCCD diffractometer	R_int = 0.042
CCD scans	θ_max = 28.3°, θ_min = 2.6°
26379 measured reflections	h = −7→7
3347 independent reflections	k = −20→17
2894 reflections with I > 2σ(I)	l = −36→36

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.0433P)² + 0.3834P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.087	(Δ/σ)_max = 0.008
S = 1.08	Δρ_max = 0.24 e Å⁻³
3347 reflections	Δρ_min = −0.17 e Å⁻³
328 parameters

Crystal data top

C₂₇H₂₆O₉	V = 2355.5 (5) Å³
M_r = 494.48	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.572 (1) Å	µ = 0.11 mm⁻¹
b = 15.530 (1) Å	T = 123 K
c = 27.221 (2) Å	0.3 × 0.22 × 0.18 mm

Data collection top

KappaCCD diffractometer	2894 reflections with I > 2σ(I)
26379 measured reflections	R_int = 0.042
3347 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.24 e Å⁻³
3347 reflections	Δρ_min = −0.17 e Å⁻³
328 parameters

Special details top

Experimental. IR (KBr): 3523 cm^-1(s), 3464(s), 1721(s), 1702(s), 1698(s), 1693(s), 1602(w), 1585(w), 1492(w), 1452(m), 1341(m), 1321(m), 1286(s), 1248(s), 1180(w), 1124(s), 1112(s), 1095(m), 1073(m), 1055(m), 1028(m), 973(w), 937(w), 914(w), 890(w), 876(w), 843(w), 817(w), 733(w), 710(s), 690(w), 676(w).

APCI MS (MeCN/H₂O/MeOH): 517 (M+Na⁺).

¹H n.m.r. (300 MHz, DMSO): δ 3.63 (t, J8 Hz, 1H), 3.91 (m, 1H), 4.28 (m, 2H), 4.48 (dd, J1.2 Hz, 1H), 4.59 (dd, J6.6 Hz, 1H), 4.93 (m, 2H), 5.16 (m, 2H), 5.43 (dt, J3.2 Hz, 1H), 7.41 (t, J8 Hz, 3H), 7.51 (q, J5.1 Hz, 4H), 7.64 (m, 3H), and 7.95 (m, 5H).

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
C1	0.6532 (3)	0.90581 (10)	1.02859 (5)	0.0257 (3)
H1A	0.6655	0.8453	1.0397	0.031*
H1B	0.8118	0.9236	1.0157	0.031*
C2	0.4672 (3)	0.91269 (9)	0.98835 (5)	0.0200 (3)
H2	0.3029	0.9055	1.0026	0.024*
C3	0.5040 (3)	0.84870 (9)	0.94622 (5)	0.0182 (3)
H3	0.6498	0.8649	0.9269	0.022*
C4	0.2836 (2)	0.84831 (10)	0.91264 (5)	0.0184 (3)
H4	0.2605	0.9086	0.9007	0.022*
C5	0.3221 (2)	0.79167 (10)	0.86725 (5)	0.0197 (3)
H5	0.3839	0.7339	0.8774	0.024*
C6	0.0906 (3)	0.78130 (10)	0.83890 (5)	0.0225 (3)
H6A	−0.0383	0.7601	0.8608	0.027*
H6B	0.04	0.8372	0.8248	0.027*
C7	0.4023 (3)	0.93413 (10)	1.09772 (5)	0.0250 (3)
C8	0.3493 (3)	0.99616 (10)	1.13791 (5)	0.0257 (3)
C9	0.5071 (3)	1.06237 (11)	1.14897 (6)	0.0339 (4)
H9	0.6529	1.0679	1.1312	0.041*
C10	0.4529 (4)	1.12046 (12)	1.18587 (7)	0.0427 (5)
H10	0.562	1.1655	1.1935	0.051*
C11	0.2404 (4)	1.11297 (13)	1.21156 (6)	0.0425 (5)
H11	0.2029	1.153	1.2368	0.051*
C12	0.0832 (4)	1.04767 (13)	1.20063 (6)	0.0416 (5)
H12	−0.0638	1.0432	1.2181	0.05*
C13	0.1375 (3)	0.98793 (11)	1.16409 (6)	0.0338 (4)
H13	0.0302	0.942	1.1572	0.041*
C14	0.3296 (3)	1.05813 (10)	0.97932 (6)	0.0256 (3)
C15	0.3858 (3)	1.14201 (10)	0.95574 (6)	0.0249 (3)
C16	0.5947 (3)	1.15360 (11)	0.92828 (6)	0.0286 (4)
H16	0.7069	1.1079	0.9251	0.034*
C17	0.6380 (3)	1.23234 (11)	0.90562 (6)	0.0348 (4)
H17	0.7785	1.24	0.8864	0.042*
C18	0.4773 (3)	1.29942 (12)	0.91100 (6)	0.0358 (4)
H18	0.5087	1.3534	0.8959	0.043*
C19	0.2694 (3)	1.28784 (12)	0.93855 (6)	0.0344 (4)
H19	0.1585	1.3339	0.9421	0.041*
C20	0.2239 (3)	1.20951 (11)	0.96073 (6)	0.0289 (4)
H20	0.0816	1.2018	0.9795	0.035*
C21	−0.0454 (3)	0.70303 (10)	0.76941 (5)	0.0228 (3)
C22	0.0142 (3)	0.64023 (10)	0.73013 (5)	0.0226 (3)
C23	−0.1537 (3)	0.62648 (11)	0.69305 (6)	0.0288 (4)
H23	−0.2989	0.6586	0.6926	0.035*
C24	−0.1089 (3)	0.56595 (11)	0.65676 (6)	0.0326 (4)
H24	−0.2229	0.5568	0.6313	0.039*
C25	0.1006 (3)	0.51906 (10)	0.65753 (6)	0.0295 (4)
H25	0.1289	0.4767	0.633	0.035*
C26	0.2700 (3)	0.53307 (11)	0.69369 (6)	0.0329 (4)
H26	0.4151	0.5009	0.6938	0.04*
C27	0.2283 (3)	0.59416 (11)	0.72993 (6)	0.0306 (4)
H27	0.3457	0.6045	0.7545	0.037*
O1	0.58698 (19)	0.96051 (7)	1.06978 (4)	0.0265 (3)
O2	0.48923 (18)	0.99710 (6)	0.96617 (4)	0.0233 (2)
O3	0.53636 (17)	0.76484 (6)	0.96754 (4)	0.0206 (2)
H1	0.6303	0.7359	0.9499	0.031*
O4	0.07167 (17)	0.82501 (7)	0.93867 (4)	0.0247 (2)
H2A	0.1079	0.7928	0.9623	0.037*
O5	0.49849 (19)	0.83535 (7)	0.83905 (4)	0.0273 (2)
H3A	0.5638	0.8005	0.8196	0.041*
O6	0.13745 (18)	0.71908 (7)	0.79978 (4)	0.0235 (2)
O7	0.2927 (2)	0.86750 (7)	1.09080 (4)	0.0322 (3)
O8	0.1615 (2)	1.04522 (7)	1.00639 (5)	0.0404 (3)
O9	−0.24122 (19)	0.73684 (8)	0.77320 (4)	0.0320 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0264 (7)	0.0291 (9)	0.0217 (7)	0.0052 (7)	−0.0034 (6)	−0.0100 (7)
C2	0.0198 (7)	0.0195 (8)	0.0207 (7)	0.0014 (6)	−0.0005 (5)	−0.0003 (6)
C3	0.0164 (6)	0.0205 (8)	0.0176 (6)	0.0002 (6)	0.0009 (5)	0.0008 (6)
C4	0.0173 (6)	0.0213 (8)	0.0167 (6)	0.0012 (6)	0.0006 (5)	−0.0005 (6)
C5	0.0169 (7)	0.0237 (8)	0.0186 (7)	0.0004 (6)	0.0007 (6)	0.0000 (6)
C6	0.0204 (7)	0.0280 (9)	0.0191 (7)	0.0017 (6)	0.0007 (6)	−0.0054 (6)
C7	0.0283 (8)	0.0265 (9)	0.0202 (7)	0.0010 (7)	−0.0045 (6)	0.0012 (6)
C8	0.0335 (8)	0.0242 (8)	0.0194 (7)	−0.0008 (7)	−0.0014 (6)	0.0010 (6)
C9	0.0364 (9)	0.0351 (9)	0.0303 (8)	−0.0049 (8)	0.0036 (8)	−0.0064 (7)
C10	0.0510 (12)	0.0390 (11)	0.0381 (10)	−0.0137 (9)	0.0025 (9)	−0.0151 (8)
C11	0.0579 (12)	0.0434 (11)	0.0263 (8)	−0.0032 (10)	0.0050 (8)	−0.0122 (8)
C12	0.0457 (10)	0.0485 (12)	0.0306 (9)	−0.0043 (9)	0.0115 (8)	−0.0042 (8)
C13	0.0406 (10)	0.0320 (10)	0.0289 (8)	−0.0086 (8)	0.0050 (7)	−0.0033 (7)
C14	0.0227 (8)	0.0266 (9)	0.0274 (8)	0.0016 (6)	−0.0007 (6)	−0.0042 (7)
C15	0.0239 (7)	0.0256 (9)	0.0252 (8)	−0.0007 (7)	−0.0035 (6)	−0.0022 (6)
C16	0.0248 (8)	0.0281 (9)	0.0330 (8)	0.0009 (7)	0.0019 (7)	−0.0004 (7)
C17	0.0262 (8)	0.0392 (11)	0.0391 (10)	−0.0007 (8)	0.0048 (7)	0.0046 (8)
C18	0.0383 (10)	0.0309 (10)	0.0381 (9)	−0.0012 (8)	−0.0041 (8)	0.0093 (8)
C19	0.0348 (9)	0.0296 (10)	0.0387 (9)	0.0085 (7)	−0.0019 (8)	0.0033 (8)
C20	0.0252 (8)	0.0312 (9)	0.0301 (8)	0.0030 (7)	0.0011 (7)	−0.0011 (7)
C21	0.0215 (7)	0.0272 (8)	0.0198 (7)	−0.0036 (6)	0.0001 (6)	0.0008 (6)
C22	0.0248 (7)	0.0247 (8)	0.0183 (7)	−0.0029 (6)	0.0005 (6)	−0.0006 (6)
C23	0.0266 (8)	0.0330 (10)	0.0267 (8)	0.0011 (7)	−0.0044 (6)	−0.0026 (7)
C24	0.0375 (9)	0.0368 (10)	0.0233 (8)	−0.0041 (8)	−0.0086 (7)	−0.0055 (7)
C25	0.0374 (9)	0.0258 (9)	0.0254 (8)	−0.0074 (7)	0.0043 (7)	−0.0064 (7)
C26	0.0307 (8)	0.0336 (10)	0.0346 (9)	0.0042 (7)	−0.0006 (7)	−0.0084 (8)
C27	0.0274 (8)	0.0377 (10)	0.0268 (8)	0.0016 (7)	−0.0058 (7)	−0.0086 (7)
O1	0.0298 (6)	0.0271 (6)	0.0227 (5)	−0.0015 (5)	−0.0017 (5)	−0.0064 (4)
O2	0.0243 (5)	0.0198 (6)	0.0258 (5)	0.0013 (5)	0.0031 (5)	−0.0019 (4)
O3	0.0214 (5)	0.0208 (5)	0.0197 (5)	0.0039 (4)	−0.0001 (4)	−0.0004 (4)
O4	0.0165 (5)	0.0383 (7)	0.0193 (5)	0.0005 (4)	0.0016 (4)	0.0008 (5)
O5	0.0238 (5)	0.0348 (6)	0.0232 (5)	−0.0039 (5)	0.0083 (5)	−0.0053 (5)
O6	0.0214 (5)	0.0297 (6)	0.0195 (5)	0.0014 (4)	−0.0015 (4)	−0.0072 (4)
O7	0.0451 (7)	0.0245 (7)	0.0270 (6)	−0.0085 (5)	−0.0026 (5)	−0.0014 (5)
O8	0.0347 (7)	0.0308 (7)	0.0556 (8)	0.0063 (5)	0.0203 (6)	0.0037 (6)
O9	0.0224 (5)	0.0461 (8)	0.0275 (6)	0.0040 (5)	−0.0014 (5)	−0.0110 (5)

Geometric parameters (Å, º) top

C1—O1	1.4543 (17)	C13—H13	0.95
C1—C2	1.5117 (19)	C14—O8	1.2085 (19)
C1—H1A	0.99	C14—O2	1.3481 (18)
C1—H1B	0.99	C14—C15	1.485 (2)
C2—O2	1.4484 (17)	C15—C20	1.390 (2)
C2—C3	1.5312 (19)	C15—C16	1.395 (2)
C2—H2	1	C16—C17	1.391 (2)
C3—O3	1.4371 (17)	C16—H16	0.95
C3—C4	1.5309 (18)	C17—C18	1.381 (2)
C3—H3	1	C17—H17	0.95
C4—O4	1.4237 (16)	C18—C19	1.392 (2)
C4—C5	1.5319 (19)	C18—H18	0.95
C4—H4	1	C19—C20	1.382 (2)
C5—O5	1.4197 (17)	C19—H19	0.95
C5—C6	1.512 (2)	C20—H20	0.95
C5—H5	1	C21—O9	1.2155 (18)
C6—O6	1.4616 (17)	C21—O6	1.3353 (17)
C6—H6A	0.99	C21—C22	1.485 (2)
C6—H6B	0.99	C22—C27	1.391 (2)
C7—O7	1.2162 (19)	C22—C23	1.393 (2)
C7—O1	1.3434 (19)	C23—C24	1.386 (2)
C7—C8	1.487 (2)	C23—H23	0.95
C8—C13	1.384 (2)	C24—C25	1.376 (2)
C8—C9	1.386 (2)	C24—H24	0.95
C9—C10	1.383 (2)	C25—C26	1.381 (2)
C9—H9	0.95	C25—H25	0.95
C10—C11	1.380 (3)	C26—C27	1.388 (2)
C10—H10	0.95	C26—H26	0.95
C11—C12	1.372 (3)	C27—H27	0.95
C11—H11	0.95	O3—H1	0.84
C12—C13	1.393 (2)	O4—H2A	0.84
C12—H12	0.95	O5—H3A	0.84

O1—C1—C2	110.08 (12)	C13—C12—H12	119.7
O1—C1—H1A	109.6	C8—C13—C12	119.42 (16)
C2—C1—H1A	109.6	C8—C13—H13	120.3
O1—C1—H1B	109.6	C12—C13—H13	120.3
C2—C1—H1B	109.6	O8—C14—O2	123.81 (14)
H1A—C1—H1B	108.2	O8—C14—C15	124.90 (14)
O2—C2—C1	107.93 (12)	O2—C14—C15	111.28 (13)
O2—C2—C3	105.30 (11)	C20—C15—C16	119.78 (15)
C1—C2—C3	113.89 (11)	C20—C15—C14	118.86 (14)
O2—C2—H2	109.9	C16—C15—C14	121.36 (14)
C1—C2—H2	109.9	C17—C16—C15	119.73 (15)
C3—C2—H2	109.9	C17—C16—H16	120.1
O3—C3—C4	109.77 (11)	C15—C16—H16	120.1
O3—C3—C2	107.61 (10)	C18—C17—C16	120.25 (16)
C4—C3—C2	110.02 (11)	C18—C17—H17	119.9
O3—C3—H3	109.8	C16—C17—H17	119.9
C4—C3—H3	109.8	C17—C18—C19	119.94 (16)
C2—C3—H3	109.8	C17—C18—H18	120
O4—C4—C3	111.66 (11)	C19—C18—H18	120
O4—C4—C5	111.82 (11)	C20—C19—C18	120.13 (16)
C3—C4—C5	111.80 (11)	C20—C19—H19	119.9
O4—C4—H4	107.1	C18—C19—H19	119.9
C3—C4—H4	107.1	C19—C20—C15	120.16 (16)
C5—C4—H4	107.1	C19—C20—H20	119.9
O5—C5—C6	111.44 (11)	C15—C20—H20	119.9
O5—C5—C4	105.01 (12)	O9—C21—O6	123.48 (14)
C6—C5—C4	110.69 (11)	O9—C21—C22	123.06 (13)
O5—C5—H5	109.9	O6—C21—C22	113.45 (12)
C6—C5—H5	109.9	C27—C22—C23	119.63 (14)
C4—C5—H5	109.9	C27—C22—C21	122.16 (14)
O6—C6—C5	106.87 (11)	C23—C22—C21	118.19 (14)
O6—C6—H6A	110.3	C24—C23—C22	119.95 (15)
C5—C6—H6A	110.3	C24—C23—H23	120
O6—C6—H6B	110.3	C22—C23—H23	120
C5—C6—H6B	110.3	C25—C24—C23	120.06 (15)
H6A—C6—H6B	108.6	C25—C24—H24	120
O7—C7—O1	123.81 (14)	C23—C24—H24	120
O7—C7—C8	124.41 (15)	C24—C25—C26	120.49 (15)
O1—C7—C8	111.78 (13)	C24—C25—H25	119.8
C13—C8—C9	119.82 (15)	C26—C25—H25	119.8
C13—C8—C7	119.22 (14)	C25—C26—C27	119.96 (16)
C9—C8—C7	120.96 (15)	C25—C26—H26	120
C10—C9—C8	120.21 (17)	C27—C26—H26	120
C10—C9—H9	119.9	C26—C27—C22	119.87 (15)
C8—C9—H9	119.9	C26—C27—H27	120.1
C11—C10—C9	120.01 (18)	C22—C27—H27	120.1
C11—C10—H10	120	C3—O3—H1	109.5
C9—C10—H10	120	C4—O4—H2A	109.5
C12—C11—C10	119.98 (17)	C5—O5—H3A	109.5
C12—C11—H11	120	C7—O1—C1	116.91 (12)
C10—C11—H11	120	C14—O2—C2	118.02 (11)
C11—C12—C13	120.55 (17)	C21—O6—C6	116.00 (11)
C11—C12—H12	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O7ⁱ	0.84	2.15	2.9641 (19)	163
O4—H2A···O3ⁱⁱ	0.84	2.15	2.9164 (18)	152
O4—H2A···O3	0.84	2.43	2.8636 (18)	113
O5—H3A···O9ⁱⁱⁱ	0.84	1.94	2.7668 (19)	169

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₆O₉
M_r	494.48
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	123
a, b, c (Å)	5.572 (1), 15.530 (1), 27.221 (2)
V (Å³)	2355.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.3 × 0.22 × 0.18

Data collection
Diffractometer	KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	26379, 3347, 2894
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.087, 1.08
No. of reflections	3347
No. of parameters	328
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.17

Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O7ⁱ	0.84	2.15	2.9641 (19)	162.9
O4—H2A···O3ⁱⁱ	0.84	2.15	2.9164 (18)	152.1
O4—H2A···O3	0.84	2.43	2.8636 (18)	112.8
O5—H3A···O9ⁱⁱⁱ	0.84	1.94	2.7668 (19)	169.4

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

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