(2R,3aR,4S,7R,7aS,9R,10aR,11S,14R,14aS)-rel-3a,4,7,7a,10a,11,14,14a-Octa­hydro-4,14:7,11-diep­oxy-2,9-propanona­phtho[1,2-f:5,6-f′]diisoindole-1,3,8,10-tetrone (9CI): a cyclo­phane derived from naphtho[1,2-c:5,6-c]difuran

Thibault, M.E.; Parvez, M.; Dibble, P.W.

doi:10.1107/S1600536808025397

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1837

doi:10.1107/S1600536808025397

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(2R,3aR,4S,7R,7aS,9R,10aR,11S,14R,14aS)-rel-3a,4,7,7a,10a,11,14,14a-Octahydro-4,14:7,11-diepoxy-2,9-propanonaphtho[1,2-f:5,6-f′]diisoindole-1,3,8,10-tetrone (9CI): a cyclophane derived from naphtho[1,2-c:5,6-c]difuran

Michelle E. Thibault,^a Masood Parvez ^b and Peter W. Dibble ^a ^*

^aDepartment of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, Alberta, Canada T1K 3M4, and ^bDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: dibble@uleth.ca

(Received 31 July 2008; accepted 6 August 2008; online 30 August 2008)

The title compound, C₂₅H₁₈N₂O₆, is a naphthalenophane styled in the manner of Warrener's alicyclic cyclophanes or molecular racks wherein a trimethylene tether is perfectly staggered between the two N atoms such that the central methylene H atoms point toward the naphthalene π-system. The dihedral angle between the mean planes of the two benzene rings is 7.61 (7)°.

Related literature

For related literature, see: Butler et al. (2000 ); Thibault et al. (2003 ).

Experimental

Crystal data

C₂₅H₁₈N₂O₆
M_r = 442.41
Tetragonal, P 4₂/n
a = 21.635 (9) Å
c = 8.262 (2) Å
V = 3867 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 173 (2) K
0.35 × 0.12 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.962, T_max = 0.987
7455 measured reflections
4303 independent reflections
3077 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.107
S = 1.02
4303 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025397/lh2675sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025397/lh2675Isup2.hkl

checkCIF report

Comment top

The title compound, (1), was prepared by the Diels-Alder reaction of naphtho[1,2 - c:5,6 - c]difuran (2) and 1,3-bis(maleimido)propane (3) (see Fig. 2). It is a naphthalenophane styled in the manner of Warreners alicyclic cyclophanes or molecular racks. (Butler et al., 2000) The X-ray structure shows that the three carbon methylene tether is perfectly staggered between the two N atoms such that the central methylene protons point toward the naphthalenic π-system. There is a slight 'warp' to the naphthalene rings system with a mean-planes angle between the two benzene rings being 7.61 (7)°. The only anomalous bond angle in the molecule appears in the methylene tether with the central angle (C23—C24—C25) expanded to 115.17 (13)°, evidence of a repulsive interaction with the naphthalene ring.

Related literature top

For related literature, see: Butler et al. (2000); Thibault et al. (2003).

Experimental top

The preparation of the title compound has been reported (Thibault et al., 2003).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of the title compound with displacement ellipsoids plotted at 50% probability level.
	Fig. 2. The formation of the title compound.

(2R,3aR,4S,7R,7aS,9R,10aR, 11S,14R,14aS)-rel-3a,4,7,7a,10a,11,14,14a- Octahydro-4,14:7,11-diepoxy-2,9-propanonaphtho[1,2-f:5,6-f']diisoindole- 1,3,8,10-tetrone top

Crystal data top

C₂₅H₁₈N₂O₆	D_x = 1.520 Mg m⁻³
M_r = 442.41	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₂/n	Cell parameters from 3862 reflections
Hall symbol: -P 4bc	θ = 1.0–27.5°
a = 21.635 (9) Å	µ = 0.11 mm⁻¹
c = 8.262 (2) Å	T = 173 K
V = 3867 (2) Å³	Needle, colorless
Z = 8	0.35 × 0.12 × 0.12 mm
F(000) = 1840

Data collection top

Nonius KappaCCD diffractometer	4303 independent reflections
Radiation source: fine-focus sealed tube	3077 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −27→28
T_min = 0.962, T_max = 0.987	k = −19→19
7455 measured reflections	l = −9→10

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0461P)² + 0.9086P] where P = (F_o² + 2F_c²)/3
4303 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₅H₁₈N₂O₆	Z = 8
M_r = 442.41	Mo Kα radiation
Tetragonal, P4₂/n	µ = 0.11 mm⁻¹
a = 21.635 (9) Å	T = 173 K
c = 8.262 (2) Å	0.35 × 0.12 × 0.12 mm
V = 3867 (2) Å³

Data collection top

Nonius KappaCCD diffractometer	4303 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	3077 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.987	R_int = 0.030
7455 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
4303 reflections	Δρ_min = −0.18 e Å⁻³
298 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
O1	0.22246 (5)	0.13740 (6)	0.23245 (15)	0.0336 (3)
O2	0.01829 (5)	0.13616 (6)	0.36524 (14)	0.0309 (3)
O3	0.16200 (5)	0.15123 (5)	0.75206 (13)	0.0272 (3)
O4	0.19993 (5)	−0.19809 (5)	0.40461 (14)	0.0273 (3)
O5	0.22497 (6)	−0.07494 (6)	−0.02726 (16)	0.0399 (3)
O6	0.03367 (5)	−0.10018 (6)	0.19059 (15)	0.0328 (3)
N1	0.11727 (6)	0.13315 (6)	0.26487 (16)	0.0227 (3)
N2	0.12520 (6)	−0.07665 (6)	0.06537 (16)	0.0244 (3)
C1	0.17687 (7)	0.14753 (7)	0.3135 (2)	0.0244 (4)
C2	0.17425 (7)	0.17364 (7)	0.4820 (2)	0.0235 (4)
H2	0.1943	0.2152	0.4882	0.028*
C3	0.10474 (7)	0.17687 (7)	0.52369 (19)	0.0236 (4)
H3	0.0907	0.2203	0.5420	0.028*
C4	0.07282 (7)	0.14768 (7)	0.38054 (19)	0.0232 (4)
C5	0.19873 (8)	0.12925 (7)	0.6167 (2)	0.0241 (4)
H5	0.2445	0.1302	0.6339	0.029*
C6	0.10185 (7)	0.13748 (7)	0.68267 (19)	0.0240 (4)
H6	0.0657	0.1462	0.7546	0.029*
C7	0.11018 (7)	0.07033 (7)	0.63576 (18)	0.0214 (3)
C8	0.17119 (7)	0.06510 (7)	0.59077 (18)	0.0205 (3)
C9	0.19457 (7)	0.01012 (7)	0.52115 (18)	0.0202 (3)
C10	0.25447 (7)	0.00473 (8)	0.45215 (19)	0.0241 (4)
H10	0.2825	0.0384	0.4612	0.029*
C11	0.27291 (7)	−0.04800 (8)	0.3725 (2)	0.0254 (4)
H11	0.3122	−0.0502	0.3214	0.030*
C12	0.23214 (7)	−0.09846 (7)	0.36885 (19)	0.0232 (4)
C13	0.17471 (7)	−0.09597 (7)	0.44037 (19)	0.0208 (3)
C14	0.15216 (7)	−0.04141 (7)	0.51354 (18)	0.0195 (3)
C15	0.09034 (7)	−0.03480 (7)	0.56703 (18)	0.0212 (3)
H15	0.0635	−0.0695	0.5644	0.025*
C16	0.06846 (7)	0.02078 (7)	0.62255 (18)	0.0215 (3)
H16	0.0262	0.0257	0.6513	0.026*
C17	0.23450 (8)	−0.16132 (8)	0.2891 (2)	0.0257 (4)
H17	0.2769	−0.1769	0.2637	0.031*
C18	0.14564 (7)	−0.15878 (7)	0.4099 (2)	0.0244 (4)
H18	0.1137	−0.1714	0.4910	0.029*
C19	0.18458 (8)	−0.10055 (8)	0.04906 (19)	0.0268 (4)
C20	0.18801 (7)	−0.16089 (8)	0.1424 (2)	0.0263 (4)
H20	0.1949	−0.1969	0.0688	0.032*
C21	0.12505 (8)	−0.16503 (8)	0.2289 (2)	0.0252 (4)
H21	0.1045	−0.2056	0.2082	0.030*
C22	0.08744 (8)	−0.11216 (8)	0.16359 (19)	0.0246 (4)
C23	0.10842 (8)	−0.01442 (7)	0.01244 (19)	0.0260 (4)
H23A	0.0646	−0.0134	−0.0219	0.031*
H23B	0.1344	−0.0019	−0.0805	0.031*
C24	0.11844 (8)	0.02956 (8)	0.1539 (2)	0.0275 (4)
H24A	0.0920	0.0160	0.2451	0.033*
H24B	0.1620	0.0261	0.1896	0.033*
C25	0.10459 (8)	0.09703 (8)	0.1186 (2)	0.0266 (4)
H25A	0.1308	0.1118	0.0284	0.032*
H25B	0.0607	0.1019	0.0868	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0261 (7)	0.0423 (8)	0.0323 (7)	0.0000 (5)	0.0082 (5)	0.0044 (5)
O2	0.0228 (7)	0.0364 (7)	0.0334 (7)	−0.0002 (5)	−0.0026 (5)	0.0081 (5)
O3	0.0297 (7)	0.0280 (7)	0.0240 (6)	−0.0019 (5)	−0.0018 (5)	−0.0028 (5)
O4	0.0274 (7)	0.0232 (6)	0.0313 (7)	0.0046 (5)	0.0033 (5)	0.0054 (5)
O5	0.0330 (7)	0.0468 (8)	0.0399 (8)	0.0089 (6)	0.0131 (6)	0.0141 (6)
O6	0.0237 (7)	0.0353 (7)	0.0394 (7)	0.0039 (5)	0.0034 (5)	−0.0018 (5)
N1	0.0226 (7)	0.0226 (7)	0.0229 (7)	0.0004 (6)	−0.0001 (5)	0.0039 (5)
N2	0.0247 (7)	0.0271 (8)	0.0214 (7)	0.0053 (6)	0.0007 (5)	0.0001 (6)
C1	0.0235 (9)	0.0224 (9)	0.0273 (9)	−0.0010 (7)	0.0014 (7)	0.0081 (7)
C2	0.0228 (9)	0.0205 (8)	0.0273 (9)	−0.0022 (6)	0.0000 (6)	0.0021 (6)
C3	0.0245 (9)	0.0199 (9)	0.0264 (9)	0.0010 (6)	0.0012 (6)	0.0019 (6)
C4	0.0226 (9)	0.0202 (8)	0.0267 (9)	0.0029 (7)	0.0002 (7)	0.0093 (6)
C5	0.0227 (9)	0.0241 (9)	0.0254 (9)	−0.0003 (7)	−0.0014 (7)	0.0003 (6)
C6	0.0225 (9)	0.0264 (9)	0.0231 (8)	−0.0014 (7)	0.0003 (6)	−0.0007 (7)
C7	0.0255 (9)	0.0248 (9)	0.0140 (8)	0.0013 (7)	0.0000 (6)	0.0035 (6)
C8	0.0224 (8)	0.0213 (8)	0.0178 (8)	−0.0006 (6)	−0.0035 (6)	0.0041 (6)
C9	0.0194 (8)	0.0229 (8)	0.0184 (8)	0.0006 (6)	−0.0032 (6)	0.0050 (6)
C10	0.0183 (8)	0.0265 (9)	0.0275 (9)	−0.0018 (7)	−0.0021 (6)	0.0059 (7)
C11	0.0189 (9)	0.0288 (9)	0.0284 (9)	0.0017 (7)	0.0017 (6)	0.0063 (7)
C12	0.0238 (9)	0.0241 (9)	0.0216 (8)	0.0042 (7)	0.0001 (6)	0.0052 (6)
C13	0.0210 (8)	0.0216 (8)	0.0197 (8)	0.0010 (6)	−0.0009 (6)	0.0036 (6)
C14	0.0213 (8)	0.0216 (8)	0.0156 (8)	−0.0006 (6)	−0.0019 (6)	0.0049 (6)
C15	0.0223 (8)	0.0234 (9)	0.0179 (8)	−0.0034 (7)	0.0000 (6)	0.0039 (6)
C16	0.0199 (8)	0.0272 (9)	0.0174 (8)	−0.0007 (6)	0.0009 (6)	0.0029 (6)
C17	0.0226 (9)	0.0268 (9)	0.0277 (9)	0.0060 (7)	0.0037 (7)	0.0036 (7)
C18	0.0249 (9)	0.0232 (9)	0.0251 (9)	0.0020 (7)	0.0024 (7)	0.0027 (6)
C19	0.0261 (9)	0.0330 (10)	0.0213 (8)	0.0059 (7)	0.0030 (7)	−0.0013 (7)
C20	0.0274 (9)	0.0250 (9)	0.0266 (9)	0.0041 (7)	0.0028 (7)	−0.0028 (7)
C21	0.0264 (9)	0.0224 (9)	0.0268 (9)	0.0008 (7)	0.0002 (7)	−0.0030 (7)
C22	0.0248 (9)	0.0269 (9)	0.0220 (8)	0.0010 (7)	−0.0005 (7)	−0.0066 (6)
C23	0.0280 (9)	0.0288 (9)	0.0213 (8)	0.0062 (7)	−0.0018 (7)	0.0034 (7)
C24	0.0339 (10)	0.0275 (9)	0.0210 (9)	0.0040 (7)	−0.0036 (7)	0.0035 (7)
C25	0.0305 (9)	0.0278 (9)	0.0214 (9)	0.0023 (7)	−0.0016 (7)	0.0040 (7)

Geometric parameters (Å, º) top

O1—C1	1.212 (2)	C10—C11	1.376 (2)
O2—C4	1.212 (2)	C10—H10	0.9500
O3—C5	1.452 (2)	C11—C12	1.404 (2)
O3—C6	1.453 (2)	C11—H11	0.9500
O4—C18	1.451 (2)	C12—C13	1.377 (2)
O4—C17	1.450 (2)	C12—C17	1.512 (2)
O5—C19	1.212 (2)	C13—C14	1.413 (2)
O6—C22	1.213 (2)	C13—C18	1.518 (2)
N1—C1	1.386 (2)	C14—C15	1.416 (2)
N1—C4	1.392 (2)	C15—C16	1.371 (2)
N1—C25	1.465 (2)	C15—H15	0.9500
N2—C22	1.384 (2)	C16—H16	0.9500
N2—C19	1.391 (2)	C17—C20	1.575 (2)
N2—C23	1.461 (2)	C17—H17	1.0000
C1—C2	1.503 (2)	C18—C21	1.567 (2)
C2—C3	1.544 (2)	C18—H18	1.0000
C2—C5	1.563 (2)	C19—C20	1.518 (2)
C2—H2	1.0000	C20—C21	1.541 (2)
C3—C4	1.508 (2)	C20—H20	1.0000
C3—C6	1.567 (2)	C21—C22	1.504 (2)
C3—H3	1.0000	C21—H21	1.0000
C5—C8	1.525 (2)	C23—C24	1.523 (2)
C5—H5	1.0000	C23—H23A	0.9900
C6—C7	1.514 (2)	C23—H23B	0.9900
C6—H6	1.0000	C24—C25	1.518 (2)
C7—C8	1.376 (2)	C24—H24A	0.9900
C7—C16	1.406 (2)	C24—H24B	0.9900
C8—C9	1.415 (2)	C25—H25A	0.9900
C9—C10	1.420 (2)	C25—H25B	0.9900
C9—C14	1.445 (2)

C5—O3—C6	96.84 (11)	C14—C13—C18	132.49 (14)
C18—O4—C17	96.65 (11)	C13—C14—C15	122.96 (14)
C1—N1—C4	113.15 (14)	C13—C14—C9	116.35 (14)
C1—N1—C25	122.21 (13)	C15—C14—C9	120.55 (14)
C4—N1—C25	123.88 (13)	C16—C15—C14	121.27 (15)
C22—N2—C19	113.30 (14)	C16—C15—H15	119.4
C22—N2—C23	122.69 (13)	C14—C15—H15	119.4
C19—N2—C23	122.87 (14)	C15—C16—C7	118.23 (14)
O1—C1—N1	123.81 (16)	C15—C16—H16	120.9
O1—C1—C2	127.59 (15)	C7—C16—H16	120.9
N1—C1—C2	108.52 (13)	O4—C17—C12	100.93 (13)
C1—C2—C3	105.10 (13)	O4—C17—C20	100.38 (13)
C1—C2—C5	114.57 (13)	C12—C17—C20	107.96 (13)
C3—C2—C5	101.47 (12)	O4—C17—H17	115.2
C1—C2—H2	111.7	C12—C17—H17	115.2
C3—C2—H2	111.7	C20—C17—H17	115.2
C5—C2—H2	111.7	O4—C18—C13	101.20 (12)
C4—C3—C2	104.59 (13)	O4—C18—C21	98.67 (12)
C4—C3—C6	114.28 (13)	C13—C18—C21	110.69 (13)
C2—C3—C6	101.62 (12)	O4—C18—H18	114.8
C4—C3—H3	111.9	C13—C18—H18	114.8
C2—C3—H3	111.9	C21—C18—H18	114.8
C6—C3—H3	111.9	O5—C19—N2	123.13 (16)
O2—C4—N1	123.67 (15)	O5—C19—C20	128.48 (15)
O2—C4—C3	127.84 (15)	N2—C19—C20	108.39 (14)
N1—C4—C3	108.46 (13)	C19—C20—C21	104.03 (13)
O3—C5—C8	101.09 (12)	C19—C20—C17	115.30 (14)
O3—C5—C2	99.32 (12)	C21—C20—C17	101.97 (13)
C8—C5—C2	109.09 (13)	C19—C20—H20	111.6
O3—C5—H5	115.1	C21—C20—H20	111.6
C8—C5—H5	115.1	C17—C20—H20	111.6
C2—C5—H5	115.1	C22—C21—C20	105.53 (14)
O3—C6—C7	101.01 (12)	C22—C21—C18	115.50 (13)
O3—C6—C3	100.58 (12)	C20—C21—C18	100.74 (13)
C7—C6—C3	107.61 (13)	C22—C21—H21	111.5
O3—C6—H6	115.3	C20—C21—H21	111.5
C7—C6—H6	115.3	C18—C21—H21	111.5
C3—C6—H6	115.3	O6—C22—N2	123.74 (15)
C8—C7—C16	122.16 (15)	O6—C22—C21	128.01 (16)
C8—C7—C6	105.20 (13)	N2—C22—C21	108.25 (14)
C16—C7—C6	132.46 (15)	N2—C23—C24	108.10 (13)
C7—C8—C9	121.47 (14)	N2—C23—H23A	110.1
C7—C8—C5	105.19 (13)	C24—C23—H23A	110.1
C9—C8—C5	133.02 (14)	N2—C23—H23B	110.1
C8—C9—C10	123.95 (15)	C24—C23—H23B	110.1
C8—C9—C14	116.05 (14)	H23A—C23—H23B	108.4
C10—C9—C14	119.89 (15)	C25—C24—C23	115.17 (13)
C11—C10—C9	121.64 (15)	C25—C24—H24A	108.5
C11—C10—H10	119.2	C23—C24—H24A	108.5
C9—C10—H10	119.2	C25—C24—H24B	108.5
C10—C11—C12	118.22 (15)	C23—C24—H24B	108.5
C10—C11—H11	120.9	H24A—C24—H24B	107.5
C12—C11—H11	120.9	N1—C25—C24	108.51 (13)
C13—C12—C11	121.82 (15)	N1—C25—H25A	110.0
C13—C12—C17	104.63 (14)	C24—C25—H25A	110.0
C11—C12—C17	133.45 (15)	N1—C25—H25B	110.0
C12—C13—C14	121.86 (15)	C24—C25—H25B	110.0
C12—C13—C18	105.53 (14)	H25A—C25—H25B	108.4

C4—N1—C1—O1	178.33 (15)	C18—C13—C14—C15	−4.6 (3)
C25—N1—C1—O1	7.9 (2)	C12—C13—C14—C9	−5.0 (2)
C4—N1—C1—C2	1.29 (18)	C18—C13—C14—C9	179.76 (15)
C25—N1—C1—C2	−169.11 (13)	C8—C9—C14—C13	178.42 (13)
O1—C1—C2—C3	179.59 (16)	C10—C9—C14—C13	2.1 (2)
N1—C1—C2—C3	−3.51 (16)	C8—C9—C14—C15	2.7 (2)
O1—C1—C2—C5	−69.9 (2)	C10—C9—C14—C15	−173.62 (14)
N1—C1—C2—C5	106.97 (15)	C13—C14—C15—C16	−173.38 (15)
C1—C2—C3—C4	4.25 (16)	C9—C14—C15—C16	2.0 (2)
C5—C2—C3—C4	−115.36 (13)	C14—C15—C16—C7	−4.3 (2)
C1—C2—C3—C6	123.42 (13)	C8—C7—C16—C15	1.8 (2)
C5—C2—C3—C6	3.80 (15)	C6—C7—C16—C15	176.25 (16)
C1—N1—C4—O2	−176.40 (14)	C18—O4—C17—C12	52.79 (14)
C25—N1—C4—O2	−6.2 (2)	C18—O4—C17—C20	−57.98 (13)
C1—N1—C4—C3	1.60 (18)	C13—C12—C17—O4	−35.42 (15)
C25—N1—C4—C3	171.81 (13)	C11—C12—C17—O4	148.25 (17)
C2—C3—C4—O2	174.23 (15)	C13—C12—C17—C20	69.39 (16)
C6—C3—C4—O2	64.0 (2)	C11—C12—C17—C20	−106.9 (2)
C2—C3—C4—N1	−3.66 (16)	C17—O4—C18—C13	−50.62 (13)
C6—C3—C4—N1	−113.89 (14)	C17—O4—C18—C21	62.61 (13)
C6—O3—C5—C8	−50.90 (13)	C12—C13—C18—O4	30.01 (15)
C6—O3—C5—C2	60.80 (13)	C14—C13—C18—O4	−154.14 (16)
C1—C2—C5—O3	−151.62 (13)	C12—C13—C18—C21	−73.82 (16)
C3—C2—C5—O3	−38.98 (14)	C14—C13—C18—C21	102.04 (19)
C1—C2—C5—C8	−46.38 (18)	C22—N2—C19—O5	−177.28 (16)
C3—C2—C5—C8	66.26 (15)	C23—N2—C19—O5	−9.2 (3)
C5—O3—C6—C7	52.06 (13)	C22—N2—C19—C20	2.06 (18)
C5—O3—C6—C3	−58.41 (13)	C23—N2—C19—C20	170.12 (14)
C4—C3—C6—O3	144.55 (13)	O5—C19—C20—C21	173.59 (18)
C2—C3—C6—O3	32.53 (14)	N2—C19—C20—C21	−5.71 (17)
C4—C3—C6—C7	39.30 (18)	O5—C19—C20—C17	62.8 (2)
C2—C3—C6—C7	−72.71 (15)	N2—C19—C20—C17	−116.47 (15)
O3—C6—C7—C8	−33.94 (15)	O4—C17—C20—C19	142.32 (13)
C3—C6—C7—C8	71.00 (15)	C12—C17—C20—C19	37.14 (18)
O3—C6—C7—C16	150.96 (16)	O4—C17—C20—C21	30.35 (14)
C3—C6—C7—C16	−104.09 (18)	C12—C17—C20—C21	−74.84 (15)
C16—C7—C8—C9	3.1 (2)	C19—C20—C21—C22	7.03 (17)
C6—C7—C8—C9	−172.63 (14)	C17—C20—C21—C22	127.24 (13)
C16—C7—C8—C5	177.36 (13)	C19—C20—C21—C18	−113.47 (14)
C6—C7—C8—C5	1.63 (16)	C17—C20—C21—C18	6.74 (15)
O3—C5—C8—C7	31.17 (15)	O4—C18—C21—C22	−154.94 (13)
C2—C5—C8—C7	−72.85 (16)	C13—C18—C21—C22	−49.42 (18)
O3—C5—C8—C9	−155.52 (16)	O4—C18—C21—C20	−41.83 (14)
C2—C5—C8—C9	100.45 (19)	C13—C18—C21—C20	63.69 (15)
C7—C8—C9—C10	170.97 (14)	C19—N2—C22—O6	−178.31 (15)
C5—C8—C9—C10	−1.5 (3)	C23—N2—C22—O6	13.6 (2)
C7—C8—C9—C14	−5.2 (2)	C19—N2—C22—C21	2.70 (19)
C5—C8—C9—C14	−177.62 (15)	C23—N2—C22—C21	−165.38 (13)
C8—C9—C10—C11	−173.83 (15)	C20—C21—C22—O6	174.90 (16)
C14—C9—C10—C11	2.2 (2)	C18—C21—C22—O6	−74.8 (2)
C9—C10—C11—C12	−3.7 (2)	C20—C21—C22—N2	−6.16 (17)
C10—C11—C12—C13	0.8 (2)	C18—C21—C22—N2	104.13 (16)
C10—C11—C12—C17	176.65 (16)	C22—N2—C23—C24	76.48 (19)
C11—C12—C13—C14	3.6 (2)	C19—N2—C23—C24	−90.46 (18)
C17—C12—C13—C14	−173.23 (14)	N2—C23—C24—C25	178.61 (14)
C11—C12—C13—C18	−179.96 (14)	C1—N1—C25—C24	76.11 (19)
C17—C12—C13—C18	3.17 (16)	C4—N1—C25—C24	−93.24 (17)
C12—C13—C14—C15	170.65 (15)	C23—C24—C25—N1	−179.18 (14)

Experimental details

Crystal data
Chemical formula	C₂₅H₁₈N₂O₆
M_r	442.41
Crystal system, space group	Tetragonal, P4₂/n
Temperature (K)	173
a, c (Å)	21.635 (9), 8.262 (2)
V (Å³)	3867 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.35 × 0.12 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.962, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	7455, 4303, 3077
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 1.02
No. of reflections	4303
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

References

Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
Butler, D. N., Shang, M. & Warrener, R. N. (2000). Tetrahedron Lett. 41, 5985–5989. Web of Science CSD CrossRef CAS Google Scholar
Fan, H.-F. (1991). SAPI91. Rigaku Corporation, Tokyo, Japan. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hooft, R. (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
Thibault, M. E., Closson, T. L. L., Manning, S. C. & Dibble, P. W. (2003). J. Org. Chem. 68, 8373–8378. Web of Science CrossRef PubMed CAS Google Scholar

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