(1R,2R)-4-Benzoyl-2-benzo­yloxy-1-phenyl­butyl imidazole-1-carboxyl­ate

Fox, D.J.; Parris, S.; Pedersen, D.S.; Warren, S.

doi:10.1107/S1600536808004364

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o619

doi:10.1107/S1600536808004364

Open

access

(1R,2R)-4-Benzoyl-2-benzoyloxy-1-phenylbutyl imidazole-1-carboxylate

David J. Fox,^a ^*‡ Sean Parris,^a § Daniel Sejer Pedersen ^a ¶ and Stuart Warren ^a

^aDepartment of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, England
^*Correspondence e-mail: d.j.fox@warwick.ac.uk

(Received 21 January 2008; accepted 13 February 2008; online 22 February 2008)

The title compound, C₂₈H₂₄N₂O₅, was prepared from (E)-2-cinnamyl-1,3-diphenylpropane-1,3-dione using standard Sharpless asymmetric dihydroxylation conditions, followed by treatment with 1,1′-carbonyl diimidazole. In the crystal structure, the phenyl rings form intermolecular face-to-face π–π contacts, with an interplanar angle of 15.5 (2)° and a centroid–centroid distance of 4.73 (1) Å. One phenyl ring also forms a C—H⋯π contact to an adjacent imidazole ring, with an H⋯centroid distance of 3.18 Å.

Related literature

For related literature, see: Fox et al. (2006 ); Kolb et al. (1994 ).

Experimental

Crystal data

C₂₈H₂₄N₂O₅
M_r = 468.49
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.9512 (2) Å
b = 18.1330 (7) Å
c = 22.4612 (12) Å
V = 2423.86 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 180 (2) K
0.37 × 0.05 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.767, T_max = 0.998
7293 measured reflections
1416 independent reflections
1230 reflections with I > 2σ(I)
R_int = 0.076
θ_max = 20.4°

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.080
S = 1.12
1416 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the imidazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26A⋯Cg1	0.95	3.18	4.07 (1)	155

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004364/pk2082sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004364/pk2082Isup2.hkl

checkCIF report

Comment top

We recently reported a method for the preparation of optically active dihydrofurans starting from β-keto-diphenylphosphine oxides by intramolecular ring opening of cyclic carbonates (Fox et al., 2006). Currently we are investigating this synthetic concept in more detail to include other anion-stabilizing groups. Seeking to extend the methodology to diketones we performed the Sharpless asymmetric dihydroxylation (Kolb et al., 1994) on (E)-2-cinnamyl-1,3-diphenylpropane-1,3-dione, followed by treatment with 1,1'-carbonyl diimidazole. Surprisingly, this produced the title compound and the regioisomer (4R,5R)-5-benzoyloxy-1,5-diphenyl-4-imidazoyloxy-pentanone in a combined 50% yield. Presumably these products are formed by intramolecular acyl transfer during the asymmetric dihydroxylation step.

Related literature top

For related literature, see: Fox et al. (2006); Kolb et al. (1994).

Experimental top

The synthetic procedure is summarized in Fig. 2. By the method of Sharpless and co-workers (Kolb et al., 1994), olefin 1 (0.14 g, 0.41 mmol), was partially dissolved in t-BuOH (5 ml) with heating, and water (5 ml) was added. A freshly made mixture of OsCl₃.xH₂O (1 mol%), K₃Fe(CN)₆ (3 equiv.), K₂CO₃ (3 equiv.), MeSO₂NH₂ (1 equiv.) and hydroquinidine 1,4-phthalazinediyl diether (denoted (DHQD)₂PHAL, 2 mol%) was added to the cooled solution (282 K) in one portion and it was stirred vigorously for 26 d. Sodium sulfite (ca 10 equiv.) was added and the reaction allowed to warm to room temperature with vigorous stirring. The reaction mixture was transferred to a separatory funnel and the organic layer separated, and concentrated in vacuo. The concentrated organic layer was partitioned between dichloromethane (20 ml) and water (20 ml), and the aqueous phase extracted with more dichloromethane (2 × 20 ml). The organic extracts were combined and washed with brine (20 ml), dried (Na₂SO₄), filtered and concentrated in vacuo. The residue was dissolved in anhydrous dichloromethane (5 ml) and 1,1'-carbonyldiimidazole (97 mg, 0.60 mmol) was added. After 7 h, the reaction was quenched with 1M aqueous hydrochloric acid (20 ml) and extracted with dichloromethane (3 × 25 ml). The combined organic phases were washed with saturated aqueous NaHCO₃ (10 ml), dried (Na₂SO₄), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (25–100% EtOAc in hexanes, v/v) to give a mixture of the title compound and the regioisomer 2 as a yellow oil (92 mg, 50%).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure with displacement parameters drawn at the 30% probability level for non-H atoms.
	Fig. 2. Summary of the synthetic procedure. CDI = 1,1'-carbonyldiimidazole, (DHQD)₂PHAL = Hydroquinidine 1,4-phthalazinediyl diether.

(1R,2R)-4-Benzoyl-2-benzoyloxy-1-phenylbutyl imidazole-1-carboxylate top

Crystal data top

C₂₈H₂₄N₂O₅	F(000) = 984
M_r = 468.49	D_x = 1.284 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7747 reflections
a = 5.9512 (2) Å	θ = 1.0–20.4°
b = 18.1330 (7) Å	µ = 0.09 mm⁻¹
c = 22.4612 (12) Å	T = 180 K
V = 2423.86 (18) Å³	Block, colourless
Z = 4	0.37 × 0.05 × 0.02 mm

Data collection top

Nonius KappaCCD diffractometer	1230 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.076
ω and ϕ scans	θ_max = 20.4°, θ_min = 3.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −5→5
T_min = 0.767, T_max = 0.998	k = −17→17
7293 measured reflections	l = −21→22
1416 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)] = 0.036	w = 1/[σ²(F_o²) + (0.0295P)² + 0.6591P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.080	(Δ/σ)_max < 0.001
S = 1.12	Δρ_max = 0.20 e Å⁻³
1416 reflections	Δρ_min = −0.18 e Å⁻³
317 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0071 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: In the absence of significant anomalous scattering effects, 961 Friedel pairs have been merged as equivalent data.
Secondary atom site location: difference Fourier map

Crystal data top

C₂₈H₂₄N₂O₅	V = 2423.86 (18) Å³
M_r = 468.49	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.9512 (2) Å	µ = 0.09 mm⁻¹
b = 18.1330 (7) Å	T = 180 K
c = 22.4612 (12) Å	0.37 × 0.05 × 0.02 mm

Data collection top

Nonius KappaCCD diffractometer	1416 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	1230 reflections with I > 2σ(I)
T_min = 0.767, T_max = 0.998	R_int = 0.076
7293 measured reflections	θ_max = 20.4°

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.12	Δρ_max = 0.20 e Å⁻³
1416 reflections	Δρ_min = −0.18 e Å⁻³
317 parameters	Absolute structure: In the absence of significant anomalous scattering effects, 961 Friedel pairs have been merged as equivalent data.

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 > 2σ(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
O1	0.4514 (6)	−0.04408 (18)	0.45568 (15)	0.0606 (10)
O2	0.2125 (4)	0.04215 (14)	0.29114 (12)	0.0370 (7)
O3	0.5837 (5)	0.06215 (19)	0.29436 (15)	0.0627 (10)
O4	0.1450 (4)	0.17552 (15)	0.33765 (13)	0.0397 (8)
O5	−0.1887 (6)	0.23422 (17)	0.33492 (17)	0.0663 (10)
N1	0.1272 (6)	0.28828 (19)	0.29753 (17)	0.0397 (10)
N2	0.4070 (6)	0.3576 (2)	0.26476 (18)	0.0477 (11)
C1	0.4404 (8)	−0.0913 (3)	0.4173 (2)	0.0412 (12)
C2	0.2591 (7)	−0.0889 (2)	0.3705 (2)	0.0411 (12)
H2B	0.1717	−0.1353	0.3723	0.049*
H2C	0.3303	−0.0861	0.3308	0.049*
C3	0.0990 (7)	−0.0239 (2)	0.3779 (2)	0.0408 (12)
H3A	−0.0419	−0.0347	0.3562	0.049*
H3B	0.0611	−0.0186	0.4206	0.049*
C4	0.1935 (7)	0.0484 (2)	0.35549 (18)	0.0338 (11)
H4	0.3449	0.0574	0.3734	0.041*
C5	0.0401 (7)	0.1133 (2)	0.3679 (2)	0.0367 (11)
H5	−0.1116	0.1037	0.3503	0.044*
C6	0.0092 (8)	0.2308 (3)	0.3247 (2)	0.0441 (12)
C7	0.3534 (7)	0.2942 (3)	0.2878 (2)	0.0424 (12)
H7	0.4588	0.2565	0.2968	0.051*
C8	0.2059 (8)	0.3948 (3)	0.2583 (2)	0.0491 (13)
H8	0.1919	0.4429	0.2419	0.059*
C9	0.0327 (8)	0.3542 (3)	0.2781 (2)	0.0509 (13)
H9	−0.1215	0.3677	0.2787	0.061*
C10	0.4159 (8)	0.0525 (2)	0.2659 (2)	0.0393 (11)
C11	0.4072 (7)	0.0490 (2)	0.20012 (19)	0.0348 (11)
C12	0.5986 (8)	0.0679 (3)	0.1689 (2)	0.0578 (14)
H12	0.7282	0.0843	0.1898	0.069*
C13	0.6024 (9)	0.0632 (3)	0.1082 (3)	0.0734 (17)
H13	0.7352	0.0757	0.0870	0.088*
C14	0.4156 (10)	0.0405 (3)	0.0778 (2)	0.0636 (15)
H14	0.4179	0.0385	0.0356	0.076*
C15	0.2263 (9)	0.0207 (2)	0.1080 (2)	0.0547 (14)
H15	0.0979	0.0038	0.0869	0.066*
C16	0.2217 (7)	0.0254 (2)	0.1696 (2)	0.0441 (12)
H16	0.0893	0.0121	0.1906	0.053*
C17	0.6070 (8)	−0.1529 (2)	0.41677 (18)	0.0374 (11)
C18	0.7758 (8)	−0.1535 (3)	0.4594 (2)	0.0466 (12)
H18	0.7844	−0.1145	0.4875	0.056*
C19	0.9307 (8)	−0.2095 (3)	0.4615 (3)	0.0601 (14)
H19	1.0444	−0.2094	0.4912	0.072*
C20	0.9211 (10)	−0.2657 (3)	0.4207 (3)	0.0641 (15)
H20	1.0288	−0.3043	0.4220	0.077*
C21	0.7573 (10)	−0.2660 (3)	0.3785 (2)	0.0646 (15)
H21	0.7515	−0.3052	0.3504	0.077*
C22	0.5981 (8)	−0.2100 (2)	0.3758 (2)	0.0513 (13)
H22	0.4843	−0.2109	0.3462	0.062*
C23	0.0174 (7)	0.1293 (2)	0.4332 (2)	0.0373 (12)
C24	−0.1753 (8)	0.1095 (2)	0.4643 (3)	0.0546 (13)
H24	−0.2968	0.0868	0.4439	0.066*
C25	−0.1905 (11)	0.1227 (3)	0.5249 (3)	0.0722 (17)
H25	−0.3217	0.1085	0.5461	0.087*
C26	−0.0174 (14)	0.1563 (4)	0.5544 (3)	0.080 (2)
H26	−0.0293	0.1653	0.5959	0.097*
C27	0.1732 (11)	0.1770 (3)	0.5245 (3)	0.0692 (16)
H27	0.2924	0.2006	0.5451	0.083*
C28	0.1910 (8)	0.1634 (2)	0.4642 (2)	0.0498 (13)
H28	0.3237	0.1775	0.4436	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.077 (2)	0.052 (2)	0.052 (2)	0.0064 (19)	−0.0150 (19)	−0.015 (2)
O2	0.0302 (18)	0.0434 (17)	0.0374 (19)	−0.0031 (14)	−0.0014 (15)	−0.0026 (15)
O3	0.0305 (18)	0.104 (3)	0.053 (2)	−0.0117 (19)	−0.0072 (19)	−0.005 (2)
O4	0.0301 (16)	0.0336 (17)	0.055 (2)	0.0057 (15)	−0.0016 (15)	0.0084 (16)
O5	0.034 (2)	0.058 (2)	0.107 (3)	0.0085 (17)	0.001 (2)	0.021 (2)
N1	0.034 (2)	0.036 (2)	0.049 (2)	0.003 (2)	−0.0054 (19)	0.006 (2)
N2	0.043 (3)	0.047 (3)	0.053 (3)	−0.002 (2)	0.001 (2)	0.004 (2)
C1	0.051 (3)	0.033 (3)	0.039 (3)	−0.005 (3)	0.005 (3)	−0.001 (3)
C2	0.046 (3)	0.035 (2)	0.042 (3)	−0.004 (2)	0.000 (3)	0.002 (2)
C3	0.042 (3)	0.039 (3)	0.041 (3)	−0.002 (2)	−0.003 (2)	0.003 (2)
C4	0.031 (2)	0.039 (3)	0.031 (3)	−0.001 (2)	−0.002 (2)	−0.002 (2)
C5	0.027 (2)	0.036 (3)	0.046 (3)	−0.002 (2)	−0.004 (2)	0.006 (2)
C6	0.034 (3)	0.042 (3)	0.056 (3)	0.002 (3)	−0.005 (2)	0.002 (3)
C7	0.030 (3)	0.052 (3)	0.046 (3)	0.008 (2)	−0.004 (2)	−0.001 (3)
C8	0.044 (3)	0.040 (3)	0.064 (4)	0.006 (3)	−0.002 (3)	0.008 (3)
C9	0.044 (3)	0.043 (3)	0.066 (4)	0.008 (3)	0.000 (3)	0.011 (3)
C10	0.028 (3)	0.034 (3)	0.056 (3)	−0.002 (2)	0.000 (3)	0.003 (2)
C11	0.035 (3)	0.035 (2)	0.034 (3)	0.001 (2)	0.003 (3)	0.004 (2)
C12	0.043 (3)	0.085 (4)	0.045 (4)	−0.013 (3)	0.001 (3)	0.010 (3)
C13	0.049 (4)	0.113 (5)	0.059 (4)	−0.003 (3)	0.006 (3)	0.020 (4)
C14	0.066 (4)	0.079 (4)	0.047 (4)	0.007 (3)	0.014 (4)	0.007 (3)
C15	0.060 (4)	0.054 (3)	0.050 (4)	−0.008 (3)	0.000 (3)	−0.008 (3)
C16	0.040 (3)	0.047 (3)	0.046 (3)	−0.011 (2)	0.003 (3)	−0.004 (2)
C17	0.050 (3)	0.035 (3)	0.028 (3)	−0.004 (2)	0.002 (2)	0.006 (2)
C18	0.051 (3)	0.046 (3)	0.043 (3)	−0.011 (3)	−0.002 (3)	0.010 (2)
C19	0.051 (3)	0.062 (4)	0.067 (4)	−0.001 (3)	−0.008 (3)	0.018 (3)
C20	0.062 (4)	0.055 (4)	0.075 (4)	0.009 (3)	−0.002 (4)	0.011 (3)
C21	0.085 (4)	0.043 (3)	0.066 (4)	0.009 (3)	−0.004 (4)	−0.006 (3)
C22	0.063 (3)	0.042 (3)	0.049 (3)	0.005 (3)	−0.006 (3)	0.005 (3)
C23	0.035 (3)	0.035 (3)	0.042 (3)	0.005 (2)	−0.001 (2)	0.001 (2)
C24	0.050 (3)	0.052 (3)	0.062 (4)	0.008 (3)	0.010 (3)	−0.001 (3)
C25	0.091 (5)	0.064 (4)	0.062 (5)	0.017 (4)	0.034 (4)	0.007 (3)
C26	0.122 (6)	0.072 (4)	0.047 (4)	0.030 (4)	−0.001 (5)	−0.012 (4)
C27	0.083 (4)	0.064 (4)	0.061 (5)	0.012 (3)	−0.017 (4)	−0.021 (3)
C28	0.053 (3)	0.048 (3)	0.049 (4)	0.004 (3)	−0.008 (3)	−0.006 (3)

Geometric parameters (Å, º) top

O1—C1	1.217 (5)	C12—C13	1.368 (7)
O2—C10	1.350 (5)	C12—H12	0.950
O2—C4	1.454 (5)	C13—C14	1.367 (7)
O3—C10	1.199 (5)	C13—H13	0.950
O4—C6	1.321 (5)	C14—C15	1.363 (7)
O4—C5	1.458 (5)	C14—H14	0.950
O5—C6	1.201 (5)	C15—C16	1.386 (6)
N1—C7	1.368 (5)	C15—H15	0.950
N1—C9	1.392 (5)	C16—H16	0.950
N1—C6	1.397 (5)	C17—C22	1.386 (6)
N2—C7	1.300 (5)	C17—C18	1.387 (6)
N2—C8	1.382 (5)	C18—C19	1.373 (6)
C1—C17	1.494 (6)	C18—H18	0.950
C1—C2	1.506 (6)	C19—C20	1.370 (7)
C2—C3	1.526 (5)	C19—H19	0.950
C2—H2B	0.990	C20—C21	1.360 (7)
C2—H2C	0.990	C20—H20	0.950
C3—C4	1.512 (5)	C21—C22	1.390 (6)
C3—H3A	0.990	C21—H21	0.950
C3—H3B	0.990	C22—H22	0.950
C4—C5	1.515 (5)	C23—C24	1.390 (6)
C4—H4	1.000	C23—C28	1.391 (6)
C5—C23	1.501 (6)	C24—C25	1.386 (8)
C5—H5	1.000	C24—H24	0.950
C7—H7	0.950	C25—C26	1.367 (8)
C8—C9	1.342 (6)	C25—H25	0.950
C8—H8	0.950	C26—C27	1.371 (8)
C9—H9	0.950	C26—H26	0.950
C10—C11	1.479 (6)	C27—C28	1.379 (7)
C11—C16	1.368 (6)	C27—H27	0.950
C11—C12	1.381 (6)	C28—H28	0.950

C10—O2—C4	118.5 (3)	C13—C12—C11	120.3 (5)
C6—O4—C5	115.4 (3)	C13—C12—H12	119.9
C7—N1—C9	106.2 (4)	C11—C12—H12	119.9
C7—N1—C6	128.6 (4)	C14—C13—C12	120.2 (5)
C9—N1—C6	125.1 (4)	C14—C13—H13	119.9
C7—N2—C8	105.1 (4)	C12—C13—H13	119.9
O1—C1—C17	119.7 (4)	C15—C14—C13	120.2 (5)
O1—C1—C2	120.8 (4)	C15—C14—H14	119.9
C17—C1—C2	119.4 (4)	C13—C14—H14	119.9
C1—C2—C3	113.2 (3)	C14—C15—C16	119.8 (5)
C1—C2—H2B	108.9	C14—C15—H15	120.1
C3—C2—H2B	108.9	C16—C15—H15	120.1
C1—C2—H2C	108.9	C11—C16—C15	120.3 (4)
C3—C2—H2C	108.9	C11—C16—H16	119.9
H2B—C2—H2C	107.7	C15—C16—H16	119.9
C4—C3—C2	113.7 (3)	C22—C17—C18	118.6 (4)
C4—C3—H3A	108.8	C22—C17—C1	122.6 (4)
C2—C3—H3A	108.8	C18—C17—C1	118.8 (4)
C4—C3—H3B	108.8	C19—C18—C17	121.1 (5)
C2—C3—H3B	108.8	C19—C18—H18	119.5
H3A—C3—H3B	107.7	C17—C18—H18	119.5
O2—C4—C3	107.0 (3)	C20—C19—C18	119.9 (5)
O2—C4—C5	106.9 (3)	C20—C19—H19	120.1
C3—C4—C5	112.8 (3)	C18—C19—H19	120.1
O2—C4—H4	110.0	C21—C20—C19	120.0 (5)
C3—C4—H4	110.0	C21—C20—H20	120.0
C5—C4—H4	110.0	C19—C20—H20	120.0
O4—C5—C23	110.1 (3)	C20—C21—C22	121.0 (5)
O4—C5—C4	104.9 (3)	C20—C21—H21	119.5
C23—C5—C4	112.6 (3)	C22—C21—H21	119.5
O4—C5—H5	109.7	C17—C22—C21	119.4 (4)
C23—C5—H5	109.7	C17—C22—H22	120.3
C4—C5—H5	109.7	C21—C22—H22	120.3
O5—C6—O4	126.6 (4)	C24—C23—C28	118.4 (4)
O5—C6—N1	122.6 (4)	C24—C23—C5	121.0 (4)
O4—C6—N1	110.8 (4)	C28—C23—C5	120.6 (4)
N2—C7—N1	112.0 (4)	C25—C24—C23	120.2 (5)
N2—C7—H7	124.0	C25—C24—H24	119.9
N1—C7—H7	124.0	C23—C24—H24	119.9
C9—C8—N2	111.3 (4)	C26—C25—C24	120.2 (5)
C9—C8—H8	124.4	C26—C25—H25	119.9
N2—C8—H8	124.4	C24—C25—H25	119.9
C8—C9—N1	105.4 (4)	C25—C26—C27	120.5 (5)
C8—C9—H9	127.3	C25—C26—H26	119.7
N1—C9—H9	127.3	C27—C26—H26	119.7
O3—C10—O2	122.9 (4)	C26—C27—C28	119.7 (5)
O3—C10—C11	124.7 (4)	C26—C27—H27	120.1
O2—C10—C11	112.5 (4)	C28—C27—H27	120.1
C16—C11—C12	119.3 (4)	C27—C28—C23	120.9 (5)
C16—C11—C10	122.9 (4)	C27—C28—H28	119.5
C12—C11—C10	117.8 (4)	C23—C28—H28	119.5

O1—C1—C2—C3	−0.8 (6)	C16—C11—C12—C13	0.1 (7)
C17—C1—C2—C3	178.6 (4)	C10—C11—C12—C13	177.7 (5)
C1—C2—C3—C4	78.5 (4)	C11—C12—C13—C14	0.8 (8)
C10—O2—C4—C3	−122.7 (4)	C12—C13—C14—C15	−1.6 (9)
C10—O2—C4—C5	116.2 (4)	C13—C14—C15—C16	1.5 (8)
C2—C3—C4—O2	67.6 (4)	C12—C11—C16—C15	−0.1 (7)
C2—C3—C4—C5	−175.2 (4)	C10—C11—C16—C15	−177.6 (4)
C6—O4—C5—C23	−80.9 (4)	C14—C15—C16—C11	−0.7 (7)
C6—O4—C5—C4	157.7 (3)	O1—C1—C17—C22	177.3 (4)
O2—C4—C5—O4	−56.5 (4)	C2—C1—C17—C22	−2.1 (6)
C3—C4—C5—O4	−173.8 (3)	O1—C1—C17—C18	−2.0 (6)
O2—C4—C5—C23	−176.2 (3)	C2—C1—C17—C18	178.6 (4)
C3—C4—C5—C23	66.5 (4)	C22—C17—C18—C19	−0.5 (6)
C5—O4—C6—O5	−0.5 (7)	C1—C17—C18—C19	178.8 (4)
C5—O4—C6—N1	178.2 (3)	C17—C18—C19—C20	0.7 (7)
C7—N1—C6—O5	174.1 (5)	C18—C19—C20—C21	−0.5 (8)
C9—N1—C6—O5	−1.6 (8)	C19—C20—C21—C22	0.1 (8)
C7—N1—C6—O4	−4.7 (7)	C18—C17—C22—C21	0.1 (6)
C9—N1—C6—O4	179.6 (4)	C1—C17—C22—C21	−179.2 (4)
C8—N2—C7—N1	−0.9 (5)	C20—C21—C22—C17	0.1 (7)
C9—N1—C7—N2	0.6 (6)	O4—C5—C23—C24	139.4 (4)
C6—N1—C7—N2	−175.8 (4)	C4—C5—C23—C24	−103.9 (4)
C7—N2—C8—C9	0.9 (5)	O4—C5—C23—C28	−41.8 (5)
N2—C8—C9—N1	−0.5 (5)	C4—C5—C23—C28	74.9 (5)
C7—N1—C9—C8	0.0 (5)	C28—C23—C24—C25	−0.8 (7)
C6—N1—C9—C8	176.5 (4)	C5—C23—C24—C25	178.0 (4)
C4—O2—C10—O3	4.6 (6)	C23—C24—C25—C26	0.8 (7)
C4—O2—C10—C11	−176.5 (3)	C24—C25—C26—C27	−0.2 (8)
O3—C10—C11—C16	168.4 (4)	C25—C26—C27—C28	−0.5 (8)
O2—C10—C11—C16	−10.6 (6)	C26—C27—C28—C23	0.5 (7)
O3—C10—C11—C12	−9.1 (7)	C24—C23—C28—C27	0.2 (7)
O2—C10—C11—C12	172.0 (4)	C5—C23—C28—C27	−178.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26A···Cg1	0.95	3.18	4.07 (1)	155

Experimental details

Crystal data
Chemical formula	C₂₈H₂₄N₂O₅
M_r	468.49
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	180
a, b, c (Å)	5.9512 (2), 18.1330 (7), 22.4612 (12)
V (Å³)	2423.86 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.37 × 0.05 × 0.02

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.767, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	7293, 1416, 1230
R_int	0.076
θ_max (°)	20.4
(sin θ/λ)_max (Å⁻¹)	0.490

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.080, 1.12
No. of reflections	1416
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18
Absolute structure	In the absence of significant anomalous scattering effects, 961 Friedel pairs have been merged as equivalent data.

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26A···Cg1	0.95	3.18	4.07 (1)	155

Footnotes

‡Current address: Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry CV4 7AL, England.

§Current address: School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, England.

¶Current address: Department of Chemistry, University of Adelaide, SA 5005, Australia.

Acknowledgements

We are grateful to Dr John E. Davies (University of Cambridge) for collecting the X-ray data.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435–???. Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fox, D. J., Parris, S., Pedersen, D. S., Tyzack, C. R. & Warren, S. (2006). Org. Biomol. Chem. 4, 3108–3112. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kolb, H., VanNiewenhze, M. S. & Sharpless, K. B. (1994). Chem. Rev. 94, 2483–2547. CrossRef CAS Web of Science Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar