2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-lyxono-1,4-lactone

Jenkinson, S.F.; Rule, S.D.; Booth, K.V.; Fleet, G.W.J.; Watkin, D.J.; Petursson, S.

doi:10.1107/S1600536807059739

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o26

https://doi.org/10.1107/S1600536807059739

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2-O-Benzhydryl-3,4-(S)-O-benzylidene-D-lyxono-1,4-lactone

Sarah F. Jenkinson,^a ^* Sebastian D. Rule,^a Kathrine V. Booth,^a George W. J. Fleet,^a David J. Watkin ^b and Sigthor Petursson ^c

^aDepartment of Organic Chemistry, Chemical Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England, ^bDepartment of Chemical Crystallography, Chemical Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England, and ^cFaculty of Business and Science, University of Akureyri, IS-600 Akureyri, Iceland
^*Correspondence e-mail: sarah.jenkinson@chem.ox.ac.uk

(Received 8 November 2007; accepted 15 November 2007; online 6 December 2008)

X-ray crystallography unequivocally showed that protection of the free hydroxyl group of 3,5-O-benzylidene-D-lyxono-1,4-lactone with diphenyldiazomethane proceeded with retention of configuration to give the title compound, C₂₅H₂₂O₅. The crystal structure consists of layers of interlocked molecules lying parallel to the a axis.

Related literature

For related literature see: Jackson et al. (1982 ); Petursson & Webber (1982 ); Petursson et al. (2007 ); Petursson (2001 , 2003 ); Draths et al. (1992 ); Collins & Ferrier (1995 ); Görbitz (1999 ); Larson (1970 ).

Experimental

Crystal data

C₂₅H₂₂O₅
M_r = 402.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.2805 (2) Å
b = 11.3538 (2) Å
c = 19.2493 (4) Å
V = 2028.28 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.50 × 0.25 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.66, T_max = 0.99
17577 measured reflections
2610 independent reflections
2218 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.077
S = 0.97
2610 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H41⋯O21ⁱ	0.98	2.59	3.502 (2)	155
C24—H242⋯O7ⁱ	0.96	2.59	3.320 (2)	133
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: COLLECT (Nonius, 1997 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807059739/lh2567sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807059739/lh2567Isup2.hkl

checkCIF report

Comment top

Carbohydrates are relatively inexpensive and are useful starting materials for the synthesis of small chiral molecules (Collins & Ferrier, 1995) and chiral building blocks (Draths et al., 1992). Much of their synthetic utility is however dependent on developing successful protecting group strategies. Diazodiphenylmethane has been found to be a useful protecting group in the synthesis of methyl 2,3,6-tri-O-methyl-[α]-D-glucopyranoside and kojibiose octa-acetate (Jackson et al., 1982), and monoalkylations of vicinal diols have been achieved with this reagent and other diaryldiazoalkanes with high regioselectivities (Petursson & Webber, 1982; Petursson et al., 2007; Petursson, 2003; Petursson, 2001). This is of particular interest as the reaction is carried out under neutral conditions.

The utility of the benzhydryl group as a protecting group in carbohydrate chemistry has here been demonstrated with the reaction of 3,5-O-benzylidene-D-lyxono-1,4-lactone 1 with diphenyldiazomethane (Fig. 1). Such lactones are susceptible to epimerization at C-2; however x-ray crystallography unequivocally showed that this had not occurred and the protection had proceeded with retention of stereochemistry (Fig. 2). The crystal structure consists of layers of interlocked molecules (Fig. 3 and Fig. 4), lying parallel to the a-axis. There are no short range intermolecular interactions and no unusual bond lengths or angles. The absolute configuration was determined by the use of D-lyxonolactone as the starting material.

Related literature top

For related literature see: Jackson et al. (1982); Petursson & Webber (1982); Petursson et al. (2007); Petursson (2001, 2003); Draths et al. (1992); Collins & Ferrier (1995); Görbitz (1999); Larson (1970).

Experimental top

The title compound was recrystallized from a 1:1 mixture of ethyl acetate and cyclohexane: m.p.: 461–463 K; [α]_D¹⁹ +75.6 (c, 0.87 in chloroform).

Structure description top

For related literature see: Jackson et al. (1982); Petursson & Webber (1982); Petursson et al. (2007); Petursson (2001, 2003); Draths et al. (1992); Collins & Ferrier (1995); Görbitz (1999); Larson (1970).

Computing details top

Data collection: COLLECT (Nonius, 1997).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

	Fig. 1. Synthesis of the title compound.
	Fig. 2. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
	Fig. 3. The packing of the title compound projected along the b-axis.
	Fig. 4. The crystal structure is comprised of layers of interlocked molecules lying parrallel to the a-axis.

2-O-Benzhydryl-3,4-(S)-O-benzylidene-d-lyxono-1,4-lactone top

Crystal data top

C₂₅H₂₂O₅	D_x = 1.318 Mg m⁻³
M_r = 402.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2585 reflections
a = 9.2805 (2) Å	θ = 5–27°
b = 11.3538 (2) Å	µ = 0.09 mm⁻¹
c = 19.2493 (4) Å	T = 150 K
V = 2028.28 (7) Å³	Plate, colourless
Z = 4	0.50 × 0.25 × 0.10 mm
F(000) = 848

Data collection top

Area diffractometer	2218 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 27.5°, θ_min = 5.1°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −12→12
T_min = 0.66, T_max = 0.99	k = −14→14
17577 measured reflections	l = −24→24
2610 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.031	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.05P)² + 0.05P] , where P = (max(F_o²,0) + 2F_c²)/3
wR(F²) = 0.077	(Δ/σ)_max = 0.001
S = 0.97	Δρ_max = 0.29 e Å⁻³
2610 reflections	Δρ_min = −0.26 e Å⁻³
272 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 450 (70)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₅H₂₂O₅	V = 2028.28 (7) Å³
M_r = 402.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.2805 (2) Å	µ = 0.09 mm⁻¹
b = 11.3538 (2) Å	T = 150 K
c = 19.2493 (4) Å	0.50 × 0.25 × 0.10 mm

Data collection top

Area diffractometer	2610 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	2218 reflections with I > 2σ(I)
T_min = 0.66, T_max = 0.99	R_int = 0.036
17577 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 0.97	Δρ_max = 0.29 e Å⁻³
2610 reflections	Δρ_min = −0.26 e Å⁻³
272 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.56592 (13)	0.07905 (11)	0.41774 (6)	0.0309
C2	0.47068 (18)	0.13932 (14)	0.44062 (8)	0.0235
O3	0.42559 (13)	0.23855 (10)	0.40913 (5)	0.0269
C4	0.31374 (18)	0.29565 (15)	0.45100 (8)	0.0256
C5	0.33742 (17)	0.24620 (13)	0.52366 (8)	0.0217
C6	0.38488 (17)	0.12108 (13)	0.50693 (8)	0.0217
O7	0.47250 (12)	0.06450 (9)	0.55632 (6)	0.0225
C8	0.39489 (18)	0.02870 (14)	0.61807 (8)	0.0231
C9	0.30274 (18)	−0.07850 (14)	0.60446 (7)	0.0226
C10	0.16512 (18)	−0.08515 (15)	0.63305 (8)	0.0268
C11	0.08162 (19)	−0.18516 (17)	0.62452 (9)	0.0330
C12	0.1333 (2)	−0.27901 (16)	0.58623 (9)	0.0343
C13	0.2677 (2)	−0.27227 (15)	0.55607 (9)	0.0317
C14	0.35179 (19)	−0.17234 (14)	0.56436 (8)	0.0256
C15	0.50938 (17)	0.01400 (14)	0.67385 (8)	0.0244
C16	0.5410 (2)	0.11037 (15)	0.71553 (8)	0.0322
C17	0.6506 (2)	0.10513 (18)	0.76443 (9)	0.0411
C18	0.7288 (2)	0.00261 (19)	0.77220 (9)	0.0398
C19	0.6970 (2)	−0.09474 (18)	0.73217 (9)	0.0374
C20	0.58660 (19)	−0.08899 (16)	0.68292 (8)	0.0307
O21	0.45628 (12)	0.30226 (9)	0.55734 (5)	0.0220
C22	0.44412 (18)	0.42778 (13)	0.55495 (8)	0.0222
O23	0.45259 (12)	0.46674 (9)	0.48571 (5)	0.0252
C24	0.33004 (18)	0.42708 (14)	0.44694 (9)	0.0266
C25	0.56836 (17)	0.47882 (14)	0.59490 (7)	0.0215
C26	0.62747 (18)	0.41894 (15)	0.65075 (8)	0.0271
C27	0.7432 (2)	0.46592 (16)	0.68709 (9)	0.0325
C28	0.7986 (2)	0.57411 (16)	0.66872 (8)	0.0324
C29	0.73958 (18)	0.63525 (15)	0.61357 (9)	0.0312
C30	0.62512 (17)	0.58803 (14)	0.57660 (9)	0.0259
H41	0.2201	0.2695	0.4329	0.0329*
H51	0.2482	0.2446	0.5518	0.0264*
H61	0.2989	0.0724	0.4983	0.0229*
H81	0.3272	0.0931	0.6347	0.0229*
H101	0.1291	−0.0182	0.6591	0.0311*
H111	−0.0116	−0.1921	0.6444	0.0416*
H121	0.0759	−0.3458	0.5822	0.0375*
H131	0.3037	−0.3345	0.5304	0.0389*
H141	0.4444	−0.1693	0.5436	0.0295*
H161	0.4895	0.1815	0.7110	0.0385*
H171	0.6701	0.1722	0.7928	0.0503*
H181	0.8027	−0.0007	0.8051	0.0490*
H191	0.7479	−0.1668	0.7368	0.0442*
H201	0.5650	−0.1576	0.6565	0.0324*
H221	0.3486	0.4485	0.5766	0.0278*
H241	0.3431	0.4511	0.3995	0.0304*
H242	0.2454	0.4644	0.4657	0.0301*
H261	0.5900	0.3434	0.6651	0.0326*
H271	0.7810	0.4188	0.7246	0.0403*
H281	0.8757	0.6049	0.6915	0.0371*
H291	0.7803	0.7078	0.6024	0.0400*
H301	0.5885	0.6317	0.5379	0.0304*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0281 (6)	0.0319 (6)	0.0328 (6)	0.0032 (6)	−0.0004 (6)	−0.0061 (6)
C2	0.0221 (8)	0.0219 (8)	0.0267 (8)	−0.0032 (8)	−0.0045 (7)	−0.0031 (7)
O3	0.0295 (6)	0.0255 (6)	0.0259 (5)	−0.0002 (5)	−0.0004 (5)	0.0013 (5)
C4	0.0196 (8)	0.0247 (8)	0.0324 (8)	−0.0007 (7)	−0.0037 (7)	−0.0007 (7)
C5	0.0149 (7)	0.0200 (8)	0.0303 (8)	−0.0027 (7)	−0.0003 (7)	0.0007 (7)
C6	0.0189 (8)	0.0172 (7)	0.0290 (8)	−0.0031 (7)	−0.0036 (7)	0.0015 (7)
O7	0.0193 (6)	0.0208 (5)	0.0274 (5)	−0.0006 (5)	−0.0007 (5)	0.0031 (5)
C8	0.0225 (8)	0.0198 (7)	0.0272 (7)	−0.0021 (7)	0.0016 (7)	−0.0001 (7)
C9	0.0230 (8)	0.0214 (8)	0.0234 (7)	−0.0016 (7)	−0.0039 (7)	0.0035 (7)
C10	0.0242 (9)	0.0301 (9)	0.0262 (8)	−0.0011 (8)	−0.0030 (7)	0.0021 (7)
C11	0.0234 (9)	0.0414 (11)	0.0343 (8)	−0.0109 (9)	−0.0040 (8)	0.0100 (8)
C12	0.0366 (11)	0.0280 (9)	0.0383 (9)	−0.0130 (8)	−0.0142 (9)	0.0106 (8)
C13	0.0401 (10)	0.0211 (8)	0.0340 (8)	0.0005 (8)	−0.0103 (9)	0.0004 (8)
C14	0.0247 (9)	0.0234 (8)	0.0287 (8)	0.0005 (7)	−0.0020 (7)	0.0018 (7)
C15	0.0226 (8)	0.0274 (8)	0.0233 (7)	−0.0059 (7)	0.0007 (7)	0.0016 (7)
C16	0.0424 (11)	0.0264 (9)	0.0280 (8)	−0.0085 (9)	−0.0015 (9)	0.0021 (7)
C17	0.0514 (12)	0.0423 (11)	0.0297 (8)	−0.0159 (11)	−0.0102 (9)	0.0005 (8)
C18	0.0333 (10)	0.0584 (13)	0.0278 (8)	−0.0122 (10)	−0.0072 (8)	0.0076 (9)
C19	0.0290 (9)	0.0475 (12)	0.0358 (9)	0.0027 (10)	−0.0026 (8)	0.0066 (9)
C20	0.0288 (9)	0.0321 (9)	0.0313 (8)	0.0019 (8)	−0.0037 (8)	−0.0036 (8)
O21	0.0221 (6)	0.0156 (5)	0.0283 (5)	−0.0016 (5)	−0.0024 (5)	−0.0003 (5)
C22	0.0226 (8)	0.0158 (7)	0.0283 (8)	0.0007 (7)	0.0033 (7)	0.0007 (7)
O23	0.0260 (6)	0.0223 (5)	0.0272 (5)	−0.0045 (5)	−0.0028 (5)	0.0044 (5)
C24	0.0230 (8)	0.0244 (8)	0.0325 (8)	−0.0016 (8)	−0.0054 (8)	0.0038 (8)
C25	0.0188 (8)	0.0198 (7)	0.0261 (7)	0.0004 (7)	0.0056 (7)	−0.0043 (7)
C26	0.0316 (9)	0.0252 (8)	0.0246 (7)	−0.0035 (8)	0.0042 (8)	−0.0012 (7)
C27	0.0351 (10)	0.0353 (10)	0.0271 (8)	0.0007 (9)	−0.0012 (8)	−0.0033 (8)
C28	0.0261 (9)	0.0366 (10)	0.0345 (9)	−0.0067 (8)	−0.0009 (8)	−0.0098 (8)
C29	0.0266 (9)	0.0240 (9)	0.0428 (9)	−0.0057 (8)	0.0038 (9)	−0.0029 (8)
C30	0.0219 (8)	0.0214 (8)	0.0344 (8)	−0.0001 (7)	0.0038 (7)	−0.0007 (7)

Geometric parameters (Å, º) top

O1—C2	1.2015 (19)	C15—C20	1.382 (2)
C2—O3	1.3461 (19)	C16—C17	1.387 (3)
C2—C6	1.519 (2)	C16—H161	0.942
O3—C4	1.465 (2)	C17—C18	1.380 (3)
C4—C5	1.523 (2)	C17—H171	0.955
C4—C24	1.502 (2)	C18—C19	1.379 (3)
C4—H41	0.982	C18—H181	0.934
C5—C6	1.522 (2)	C19—C20	1.397 (2)
C5—O21	1.4291 (18)	C19—H191	0.948
C5—H51	0.990	C20—H201	0.952
C6—O7	1.4063 (18)	O21—C22	1.4303 (18)
C6—H61	0.984	C22—O23	1.4065 (18)
O7—C8	1.4482 (19)	C22—C25	1.502 (2)
C8—C9	1.510 (2)	C22—H221	1.008
C8—C15	1.520 (2)	O23—C24	1.4329 (19)
C8—H81	1.016	C24—H241	0.961
C9—C10	1.393 (2)	C24—H242	0.962
C9—C14	1.392 (2)	C25—C26	1.385 (2)
C10—C11	1.385 (2)	C25—C30	1.393 (2)
C10—H101	0.970	C26—C27	1.388 (2)
C11—C12	1.382 (3)	C26—H261	0.966
C11—H111	0.949	C27—C28	1.378 (2)
C12—C13	1.377 (3)	C27—H271	0.965
C12—H121	0.930	C28—C29	1.382 (2)
C13—C14	1.386 (2)	C28—H281	0.909
C13—H131	0.925	C29—C30	1.386 (2)
C14—H141	0.949	C29—H291	0.931
C15—C16	1.388 (2)	C30—H301	0.958

O1—C2—O3	122.70 (15)	C16—C15—C20	118.96 (15)
O1—C2—C6	128.04 (15)	C15—C16—C17	120.88 (17)
O3—C2—C6	109.25 (13)	C15—C16—H161	121.0
C2—O3—C4	110.05 (12)	C17—C16—H161	118.1
O3—C4—C5	103.88 (12)	C16—C17—C18	119.71 (17)
O3—C4—C24	109.85 (14)	C16—C17—H171	119.6
C5—C4—C24	113.54 (14)	C18—C17—H171	120.7
O3—C4—H41	107.3	C17—C18—C19	120.16 (17)
C5—C4—H41	110.0	C17—C18—H181	119.6
C24—C4—H41	111.8	C19—C18—H181	120.3
C4—C5—C6	101.04 (12)	C18—C19—C20	119.92 (18)
C4—C5—O21	111.33 (13)	C18—C19—H191	122.1
C6—C5—O21	106.76 (12)	C20—C19—H191	118.0
C4—C5—H51	112.9	C19—C20—C15	120.35 (17)
C6—C5—H51	109.9	C19—C20—H201	118.6
O21—C5—H51	114.0	C15—C20—H201	121.1
C5—C6—C2	101.68 (12)	C5—O21—C22	111.61 (12)
C5—C6—O7	116.79 (13)	O21—C22—O23	109.84 (12)
C2—C6—O7	109.11 (12)	O21—C22—C25	107.90 (13)
C5—C6—H61	109.0	O23—C22—C25	108.72 (13)
C2—C6—H61	111.1	O21—C22—H221	106.8
O7—C6—H61	109.0	O23—C22—H221	111.6
C6—O7—C8	113.30 (11)	C25—C22—H221	111.9
O7—C8—C9	111.43 (12)	C22—O23—C24	110.51 (12)
O7—C8—C15	105.25 (12)	C4—C24—O23	111.41 (13)
C9—C8—C15	115.46 (13)	C4—C24—H241	110.2
O7—C8—H81	111.4	O23—C24—H241	107.8
C9—C8—H81	106.5	C4—C24—H242	109.6
C15—C8—H81	106.8	O23—C24—H242	108.3
C8—C9—C10	119.62 (14)	H241—C24—H242	109.5
C8—C9—C14	121.86 (14)	C22—C25—C26	120.79 (14)
C10—C9—C14	118.52 (15)	C22—C25—C30	120.28 (14)
C9—C10—C11	120.72 (16)	C26—C25—C30	118.92 (15)
C9—C10—H101	118.6	C25—C26—C27	120.58 (16)
C11—C10—H101	120.7	C25—C26—H261	121.1
C10—C11—C12	120.09 (17)	C27—C26—H261	118.4
C10—C11—H111	122.1	C26—C27—C28	120.13 (17)
C12—C11—H111	117.8	C26—C27—H271	116.4
C11—C12—C13	119.76 (17)	C28—C27—H271	123.4
C11—C12—H121	118.3	C27—C28—C29	119.82 (17)
C13—C12—H121	121.9	C27—C28—H281	120.9
C12—C13—C14	120.44 (16)	C29—C28—H281	119.3
C12—C13—H131	120.7	C28—C29—C30	120.25 (16)
C14—C13—H131	118.9	C28—C29—H291	117.4
C9—C14—C13	120.39 (15)	C30—C29—H291	122.3
C9—C14—H141	120.1	C25—C30—C29	120.29 (16)
C13—C14—H141	119.5	C25—C30—H301	121.6
C8—C15—C16	117.99 (15)	C29—C30—H301	118.1
C8—C15—C20	123.00 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H41···O21ⁱ	0.98	2.59	3.502 (2)	155
C24—H242···O7ⁱ	0.96	2.59	3.320 (2)	133

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂O₅
M_r	402.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	9.2805 (2), 11.3538 (2), 19.2493 (4)
V (Å³)	2028.28 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.25 × 0.10

Data collection
Diffractometer	Area
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.66, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	17577, 2610, 2218
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.077, 0.97
No. of reflections	2610
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.26

Computer programs: COLLECT (Nonius, 1997)., DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H41···O21ⁱ	0.98	2.59	3.502 (2)	155
C24—H242···O7ⁱ	0.96	2.59	3.320 (2)	133

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

References

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